Adventures of Sara: Evolving into femininity

What does summer camp, college, the Caribbean and cross-dressing have in common? Sara! "As a young boy there were no boys in our rural neighborhood."

Story revision - I felt bad about leaving Sara hanging at the end of the story so I added 7,100 words to tie up loose ends. Rather than adding a LONG edit post script I improved story to help Sara. Sara had an adventure I hadn't counted on in addition to a new ending. Thank you for your understanding. Regards, Dee - 8/29/2021

Adventures of Sara: Evolving Deeper into femininity

As a young boy there were no boys my age in our rural neighborhood. Twin daughters of our closes neighbors were my only play pals. Connie and Sue innocently introduced me to cross-dressing so they could have a ‘young sister’ to play house and dress-up with. They dressed me in the same skirts, dresses and panties that they wore. We sang and danced in a pretend ‘girl band’, we played beauty shop, coiffed our hair and painted our nails. We also played less femme games; we were just little girls having fun. I was seven years old and they were nine; I loved the attention they gave me. We were close friends for many years. They named me Sara. My boy name is Steve Upton.

Mom and Dad were aware of Sara but they never formally acknowledged her. In return I never flaunted Sara’s existence outside our home except for my choice of underwear and constantly painted toe nails. In public I always presented as male… an androgynous male. The subject of my sexual orientation was never brought up.

I was always discreet and cleaned up well; which meant removal of all traces of makeup and nail polish. In return Sara and I were never criticized or judged. Oddly enough on my birthday mom always made sure there was a token present for Sara!

For years I routinely wore Connie’s and Sue’s hand-me-down camisoles, leggings, clothes and sandals at home, in addition to boy’s clothes, with no objections from my parents. “Heck, it’s only clothing; nobody cares as long as you get good grades and cause no trouble” they said. Their attitude opened my world, and choices in clothing. I made sure to always get good grades; I caused no trouble. It was an unspoken understanding.

By the time I was twelve I had absorbed and adopted the mannerisms and vocal inflections of Connie and Sue; a feminine demeanor, sometimes to my embarrassment, was automatic and deeply ingrained.

By age thirteen I was adept with makeup and had a sense for fashion like most prepubescent girls. I routinely wore female clothing when I wanted and had added a few girly accessories like bracelets and hair clips. My panties and camisoles evolved from being cotton with bunnies to more mature satin, silk, nylon and organza fabrics. Based on advice from my mother I found that I prefer French cut or high waist panties.

Connie and Sue relocated to a different state a few months after I turned thirteen; we had just become semi-proficient at applying false eyelashes. Their moving wasn’t as devastating as it could have been. They had discovered boys and their mindset and needs had changed. My discovery of boys came later.

Summer camp: becoming more girly

To console my loss of friends my parents sent me to a ‘boys only’ summer camp for half of the summer. Thankfully they sent me to the same camp for four summers in a row. It amazes me to think of all the things Sara and I learned at camp.

My summer camp offered the same activities that most summer camps offer. Unlike other camps mine had a theater arts component in which campers did evening skits and singing around a campfire. Last week of camp always consisted of a 30 minute play which was written and performed by us campers. The plays required costumes, makeup and “females”.

Female roles were filled by volunteers. I and three or four other boys always volunteered to be a female. I did everyone’s makeup and I taught them how to make fake breasts using bird seed and an old stocking (which had been taught to me by Connie and Sue years earlier). I made close friends with several of the volunteer cuties; we addressed each other by our femme names.

Camp became an annual coming out event. It was fun watching the newbie girls discover and explore what they already suspected about themselves. It was nice having more ‘volunteers’.

My knowledge of makeup and my girly mannerisms insured me of many opportunities to dress as Sara in order to stay ‘in character’; I wasn’t fooling anyone. It was at camp that I perfected my female voice and walk. I sound and walk feminine when I want to and sometimes it happens automatically by mistake.

I found it odd that some of the butchest camp boys that said “no” so adamantly about playing a girl were the ones that eagerly sought to buddy up with us girls after lights out. More than one boy had begged me, in private, to make him look ‘pretty’ but only if no one would find out. And, over the four years I went to camp, more than one boy (and a virile camp counselor) took me to a secluded grove of trees to show me their ‘lumber’.

Camp is where I discovered the beauty of same sex love

I learned that there is no ‘wrong way’ to pleasure yourself or your consenting partner.

It was on a bed of pine needles amongst the trees where I received my first blowjobs (not on the same day). Sometimes I just backed up against a tree, dropped my pants and let the boys have their way with me. There were many eager cocksuckers at camp. The “no, not me” kids were well represented in giving blowjobs.

Eventually I found myself on my knees reciprocating what I had learned. I enjoyed hearing lovers moaning my name…’Sara’; it inspired me to be better at what I was doing. I discovered wearing lipstick prevents chapped lips when fellating someone and that leaving lipstick rings on your partner’s penis is very erotic for everyone involved. It seems that my red lip prints on their cocks were a badge of honor. These liaisons and opportunities contributed to me happily returning to camp for many years.

Going to camp ended when I entered college. I had learned a lot at camp. I moved on to a different type of education; I was going to be on a college CAMP-us.

College: girly Sara blossoms

A few months after beginning college I found a compatible roommate. In truth it was my soon-to-be roommate that found me.

By chance the two of us were studying in the college library. He had blonde hair like mine and was sitting and reading at one end of a long study table. I walked by him to a chair at the opposite end of his table. As I was sitting down he looked up and all around; he began sniffing the air.

“Wow, I smell a very pretty perfume… it’s like being at the beach!” he said to no one in general. I sat down and opened my reference book. He was looking directly at me in a thoughtful way. “Is that beautiful aroma coming from you?” he asked.

In an effort to remain quiet in the library I whispered, “It could be the tiny bit of musk body accent I’m wearing; it’s called ‘Tropical Breeze’. It reminds me of sunscreen at the beach on a nice summer day.” My sultry whisper sounded a lot like Sara.

‘Blondie’ intently stared at me and pondered my reply a moment and then moved to a chair two places away from me. ‘Blondie’ sat down without taking his eyes off me. He sniffed in my direction. “Yes, you look and sound beautiful… like a woman.” he gushed.

Sara’s voice responded with a purposely sensual, “Thank you.” Sara’s voice coming from my mouth had him confused and interested.

I consciously moved my long blonde hair behind my ears exposing my gold studs for ‘Blondie’ to see. I regretted not having worn my matching delicate gold chain. In an attempt to appear disinterested I flipped my hair and turned the page of my book; I was a Theatrical Arts major. I waited for his next move.

Now that ‘Blondie’ was closer I looked up and checked him out. He was very attractive! Well groomed, nice smile, nice clothes and kind eyes; eyes that had obvious traces of mascara and eye shadow! His fingernails cuticles bore traces of nail polish.

There’s an old maxim that proclaims that “It takes one to know one.” I knew that ‘Blondie’ and I had a lot in common.

I closed my book and placed my hand on top of it so he could see my shaped and manicured nails. I saw him checking them out. He appeared puzzled and leaned back in his chair. With a perplexed look on his face he asked, “No offense intended but are you… are you a girl?” I decided to see if I could rattle his nerves a bit. “I am when I want to be… what about you?” I replied.

‘Blondie’ was taken aback but managed to say, “I like your voice; it’s delightfully feminine and so natural.” ‘Blondie’ was interested in me.

“Thank you again” I repeated. I smiled sweetly at him. I hoped my gaze conveyed my interest in him.

In an obtuse reference to an old Kinks song I asked, “Well, Lola, would you care to try some of my musk? Wouldn’t you like to smell as pretty as your eye shadow looks?” I asked. ‘Blondie’ appeared shocked at my observations. I handed him a tissue.

“You need to be more thorough when you remove your eye makeup, Princess. You should use the remover that I use; it’s effective and gentle.” I didn’t mention his well groomed eye brows.

My comments and voice had startled ‘Blondie’; they also kicked open the door to an honest conversation. After several minutes of candid talk we mutually decided to move to a local coffee shop. My new admirer apparently wanted to ‘Take a Talk on the Wild Side’.

‘Blondie’s’ boy name was Allen. He was a college junior; I was a freshman. In terms of cross-dressing Allen was ‘entry level’ and I was an experienced ‘senior level’ panty wearer. Allen confessed that his feminine side made it difficult to find non-judgmental friends.

After several dates and serious bouts of petting Allen asked me to be his roommate. He brought up his bi-sexuality; a term I thought was for others but not me. I was obviously, when I think back about summer camp, in very deep denial.

With that in mind I gave into a nagging curiosity that I had been struggling with for a long time; I allowed myself to begin a relationship with a man. After mutually agreed upon HIV & STD blood tests I happily moved into Allen’s off campus apartment. It was great to be out of the dorm; it was even greater to be out of the proverbial closet.

For almost two years Allen and I were domestic partners. We maintained an apartment and behaved as couples do. He was charming and I was me. It was delightful. We engaged in harmless mutual sexual exploration between two consenting (and curious) adult males. For me it was a glorious expansion of Sara and my femme self.

We each, to varying degrees, let our inner girl out whenever it felt right. We weren’t mandated to be sissies all the time; we were a true functioning couple. It felt right.

I helped Allen become a prettier Stacy. Her skill with the application AND removal of makeup became flawless under my guidance. I taught her how to tuck and tape, how to hook her bra behind her back, etc. I took Stacy to get her ears pierced. For Christmas we bought each other breast forms. Life was good.

When Stacy graduated with a bachelor’s degree she transferred to a different university for her post grad advanced degree. Stacy gifted me her apartment until my graduation. When she was in town Stacy always stayed with me. We remain close friends to this day exchanging greeting cards, emails and phone calls. If fate would allow it I would eagerly welcome a return to the companionship and life we had shared.

Following graduation with a degree in Theater Arts I moved back with my parents and prepared for the extended vacation to Tres Palmas Resort that they had gifted me. I had the option of extending my stay if wanted. I would worry about finding a job when I returned.

Tres Palmas is why I came; The Convent is where I wound up

Tres Palmas was the newest tourist vacation spot for the hip and horny people of the world. Famous for their fine un-crowded Caribbean beaches they also are known for a thriving sex tourism industry similar to Thailand. Their tolerant sex trade is relegated to a nearby former convent. The state owned brothel is called The Convent.

The Convent: “We have women but they aren’t female.”

Being away from home, whether it was camp, university or vacation, gave me the chance to more fully indulge my cross-dressed alter ego. When I reached my vacation destination Sara could be around as long as she wanted to be; Sara would be allowed out more than usual.

On the day before departure I re-shaved my legs, arm pits and pubes. I moisturized. It always feels wonderfully liberating. I indulged myself with a basic manicure. I shaped my nails, applied a subtle pale pink clear coat on my fingernails and a bolder Tropical Coral polish to my toes. Coral lipstick looks good with my fair complexion and my shoulder length blonde hair. The lipstick would have to wait.

Sara goes on vacation

I was excited about the new adventures I would soon be experiencing. My ‘get out of town’ clothes included an attractive blue tropical themed print shirt; parrots, palms, etc. which looked very nice with my new Khaki slacks. Black thigh high stay up stockings under my slacks had me feeling decadent! My stocking covered feet felt wonderful in my gender neutral Ashland Bubble Loafers (with a 1 ½ inch heel – nothing too drastic). My shoe heels brought my height up to about 5 foot 10 inches.

As always I wore a Light Days Panty liner with my white Spanx Hi-Hipster support panty; the lace trim made them extra special for me. They felt great under my slacks; pleasantly slippery! If I got aroused it would not be obvious to others; no visible ‘boy bump’.

I was bringing a stylish form fitting blazer for warmth. I added a cute hummingbird LGBQT Rainbow brooch to the lapel as a fashion statement. A Michael Kors brown leather shoulder strap valise completed my travel ensemble; the shiny gold colored MK medallion logo was a sporty accent. It could be argued that in reality my ‘valise’ was actually a purse.

I wondered how a customs official would react if I was selected for a random search of my luggage or, heaven forbid, a strip search. The fear and excitement of being discovered provided a certain excitement.

My mother brought me to the airport. We hugged goodbye and she gave me a few words of motherly advice. “Don’t let some cute guy take advantage of you but if it happens use protection.” Her comment took me by surprise. The thought of being intimate with a man had not crossed my mind in a long time. “I’ll be extra careful, Mom” I replied.

Mom continued: “Please don’t come home from vacation with a Caribbean vagina from an offshore clinic; your dad would not understand.” We kissed goodbye. “Have a good time, Sara” she said. I leaned into the car and kissed her. I entered the terminal.

I hadn’t thought about hooking up while on vacation until mom mentioned it. I was going to be a long way from home for a long time in a place where nobody knew me or my parents. If I was going to date someone what better place could there be? Hmmm… I had things to ponder during my flight.

I paid extra to check a bag for Sara that contained a few panties, bras, sleepwear, a jumper, denim ‘Daisy Duke’ short-short pants, makeup, panty liners and other female essentials. I planned on buying nail polish, polish remover, hair spray, Nair and other womanly necessities, including a pair of pretty sandals, upon arrival. Airlines are strict on traveling with liquids and flammables.

Sara finds a friend in the men’s room

After being checked in and assigned a boarding pass I had time to kill before departure. I went to the men’s room, entered a stall, slid down my slacks and support panty, sat down and peed. My shoulder bag hung from a hook on the stall door. When I was finished I flushed but remained seated. I closed my eyes and willed myself to breathe deeply and totally relax. It felt good. The flushing of a toilet in the stall next to me returned me to reality.

I remained seated, took a deep breath and slowly exhaled. I felt refreshed. I stood, flushed again, made sure my panty liner was fine and pulled myself together. I grabbed my bag, exited the stall and went to wash my hands.

While looking at my reflection in the sink mirror I decided that a pony tail bump would not be comfortable when I leaned back in the airline seat during my 8 hour flight. I dried my hands, removed the hair tie from my pony tail and shook my hair out.

As I was brushing my shoulder length hair into an acceptable appearance I noticed a well dressed (and handsome) businessman watching me. My spectator appeared to be 4 or 5 years older, and several inches taller, than me. He smiled and joined me at the wash basin. “I think wearing your hair down is a prettier look for you especially with your floral blouse; a flower behind your right ear would complement your tropical look. You look lovely.” The significance of a flower behind my RIGHT ear did not escape my notice; it would mean I was ‘available’.

I was taken aback by his comments and his brashness. I felt an involuntarily blush and an increase in my pulse rate. A memory of a summer camp experience briefly flitted through my mind. I smiled weakly and finished brushing my hair. I put my brush back into my shoulder bag.

Taking a business card from inside his sport coat pocket he wrote on the backside and tucked it into my blazer pocket. Looking directly at me he tapped my Rainbow brooch with a finger and said, “My name is Dan Richards.” Looking around to confirm we were alone Dan continued, “When you’re with friends what do you call yourself, Sweetie?” he asked. I softly replied “Sara”.

Dan replied, “That’s a lovely name. I wrote my private phone number and email on my card. I’d like to become better acquainted with you. I travel a lot for business but I live locally. Give me a call when the time is right for you. We could meet at a café for coffee and conversation.”

I wasn’t expecting a hand shake but he took my hand and shook it in a firm masculine way. In contrast I held his hand softly like a woman being helped out of a car. It was a subtle yet pleasant moment. It stirred me and made me feel very demure… very Sara like. Did I detect a Stacy like quality in Dan?

Dan looked at my manicured fingernails. “Nails say a lot about a person. I find boys that care for their nails, like you do, are more intellectually stimulating; and more willing to experience all of what life has to offer.” He made sure that I saw that his nails were also nicely manicured.

Dan smiled, winked and let go of my hand. “You’re very attractive ‘Sara Lovely’. Where in the world is a pretty young thing like you flying off to? Spain? The Riviera?”

“Tres Palmas. It’s a resort in Central America.” I kept my reply short.

“I know about Tres Palmas; it’s on the Caribbean. They market to certain open minded lifestyles. What a nudist colony is to a nudist is what Tres Palmas is for cross-dressers. There is no harm in indulging in either activity. People say it’s both exotic and erotic.”

“I’m going for their beaches.”

“I hope to hear from you in the near future Sara Lovely. Life is strange; perhaps we’ll bump into each other again in an airport somewhere. I won’t forget having met you, Miss Sara.” There was a moment of hesitation on Dan’s part. He was staring down into my eyes. I thought he was going to kiss me on my cheek; a kiss I would have welcomed. Dan turned and left.

I continued standing at the wash basin and tried to process what had just happened. I hadn’t even left on my vacation and I had already been hit on… by an attractive man! In fact I had become aroused during the few minutes that he was speaking with me. As I stood there, re-considering the implications of Dan’s advances, I became more aroused.

Stepping back into a vacant bathroom stall I loosened my slacks and pulled down my panties. I was smart enough to realize that this was not the time or place to seek the relief I wanted. I reached into my valise and swapped out my damp panty liner for a dry one. After rearranging my penis and panties I pulled up and buttoned my slacks. I left the restroom and went to a nearby air terminal bar.

Vodka 7 (with a lime) alleviated the dryness in my mouth but did nothing in terms of eradicating the thoughts of exciting new experiences that await me upon my return and, perhaps, during my vacation. I let my mind wander.

My flight would be boarding soon so I finished my beverage and made a quick visit to the airport gift shop. I picked out three magazines: Elle, Vogue and Glamour. The store had a display of hair accessories including combs, brushes and pretty barrettes. I selected two decorative barrettes and two behind-the-ear fashion flowers; a perfectly sized bright yellow daisy and a delicate pink rose. I wondered which flower Dan would like best. I paid for my items and made my way to my boarding area.

The flight

My fight was less than 50% full. I found my assigned window seat and was glad I didn’t have anyone sitting next to me. I laid my magazines and blazer on the seat next to me, placed my bag on the floor, sat down, buckled my seat belt and awaited takeoff.

Once we were aloft I settled in for the 8 hour flight. Prior to reading my magazines I retrieved Dan Richard’s business card. “Castle Research, Dan Richards, VP, International Trade Development”. Very impressive I thought. I flipped the card over: ‘Sara Lovely, contact me when you get back or sooner if the mood strikes you. We have very mutual interests.’ His cell phone number and email were listed. Before I tucked Dan’s card into my wallet I entered his info into my cell. It gave me options.

Reaching into my pants pocket I retrieved ¼ inch cubic zirconium stud earrings. Without the need for a mirror and with well practiced ease I inserted them into my ears. They sparkled like real diamonds. I was now officially on vacation. Sara was pleased.

I was awakened by the cabin steward. He wondered if I would like a snack and beverage. “Would you like a snack, Miss?” he asked. I noticed a puzzled look on his face as he studied my appearance. I nodded yes.

Noticing the brooch on my blazer (and my magazines) he commented, “There’s a very good article on hypoallergenic eye makeup in your Elle; I’ve found Almay and Tart are some of the best mascaras.” Looking at his eyelashes I knew he knew about mascara. “Thank you” I said. He left.

I woke from a nap and discovered that the flight attendant had left complimentary zippered amenity travel bags with all passengers. My gift bag was pink with a wrist strap and had the airlines logo on it. It would make a fine makeup bag. I noticed that the men were given a grey bag. I briefly wondered what was in their bags.

My bag contained a sewing kit, red satin sleep mask (with silk screened feminine eye lashes), ear plugs, nail care packet, tweezers, a sample sized lipstick, a very pleasant Passion Fruit fragrance, a packet of tissues and a small purse mirror.

I gave the fragrance a whiff and applied a dot of it behind an ear and on both wrist pulse points. It had an exotic feminine tropical aroma similar to the scent that had attracted Stacy.

The lipstick sample was Ripe Cherry (not my best shade). I used my new pocket mirror and gave it a try. It looked nicely different. The sample noted that it was “long lasting”; it wasn’t coming off until I found remover or cold cream. I went back to reading my magazine.

Sara Arrives

I immediately went to the restroom and peed. It felt great to be sitting on a non-moving toilet. I washed the grime and sweat of travel from my face. My lips were chapped and dry from airline re-circulated air. I applied L’Oreal glossy chap-stick on top of the Ripe Cherry lipstick sample and smacked my lips. I put on my blazer, adjusted the brooch, hung my bag on my shoulder and left.

Knowing that I had to wait for my luggage I went to an airport gift shop to look around. I selected three shades of nail polish, remover and a nice pair of ladies oversized Tortoise Shell sunglasses. I found the large feminine straw sun hat that I needed. I continued shopping.

I felt it was an omen when I found women’s bathing suits on sale. I took the 70% discount as an additional excuse. I bought a modest yellow hipster bikini. The string top and skimpy bottom would give me the tan lines I dreamed of. I was glad Tres Palmas had a pool and semi-private sun decks. I could tan and swim and tan without going to a crowded public beach.

I put on my new sunglasses and straw hat, took my new purchases and made my way to the baggage claim area. My image tilted way beyond basic androgynous.

I easily found my luggage and headed to Customs. Things were going well for me and I hadn’t even left the air terminal.

I entered the shortest line for customs and made sure to have my travel documents and ID ready. I knew my ride to the resort was waiting just outside the terminal.

When it was my turn I handed my documents to the Customs Officer. He was a stern looking official that came across as a no nonsense sort of guy.

“Please take off your hat Miss and set it on the counter” he ordered. His request and his tone startled me. I removed my hat; my long hair and zirconium earrings stood out. His eyes went back and forth from me to my travel documents and back to me. “Remove your sunglasses too, MISS” he directed. I did as I was told.

I couldn’t believe my stupidity! Of course he was confused. My clothing and my loafers with a 1 ½ heels weren’t very masculine. I was wearing a fitted unisex blazer with a Rainbow brooch and a MK purse. And we shouldn’t forget my shiny red lipstick; my manicured nails or the Passion Fruit perfume. I put my dark glasses on top of my head…just like women do.

He snapped his fingers and pointed to my luggage. A burley custom’s official was quickly ransacking my belongings. Upon inspecting Sara’s suitcase the agent walked over and whispered into his boss’s ear. This was not going well.

“Pass me your shoulder purse” the boss ordered. He dumped the contents onto the counter. Laying out for the world to see was all sorts of feminine items; barrettes, nail polish, lipstick, eye lash curler, etc. I was praying that I wouldn’t have to submit to a strip search in which Sara’s stockings and panties would be revealed. I was a long way from home and far from any friend.

“Tell me MISS, what is your name and where are you going?” he asked. I managed to stammer out “My name is Steve. Steve Upton. I’m going to Tres Palmas for vacation.” I said nervously. Unfortunately my reply came out in Sara’s voice!

“Tres Palmas, eh? That figures.” He rolled his eyes and scraped all my belongings back into my ‘purse’. After stamping my passport and visa he used a different rubber stamp and re-stamped them. The word “Travisti” (cross-dresser/transvestite) were now stamped on all my travel documents.

“Enjoy your stay in my country MISS Stephanie. Stay out of trouble MISS as certain life styles can find life difficult here. Take your belongings and exit the terminal. Now!”

I exited the terminal and found the Tres Palmas resort shuttle. The resort logo was on the doors. The van was painted like a North Hollywood rainbow; its image screamed Gay Pride. A short but pleasant older man stowed my baggage and helped me into the van. As we left the driver called ahead to say we’d be there soon.

Check in at Tres Palmas

The front desk clerk greeted me with a friendly, “Good afternoon Miss Upton, welcome to Tres Palmas, we’re pleased to have you stay with us.” I smiled at her use of the feminine pronoun for me. After all that is part of the resorts charm and a prime reason why I selected Tres Palmas.

She continued, “What a beautiful sunhat you have, it’s gorgeous as is your blouse. You look so very tropical already and yet you have just arrived. Be sure to check the sarongs and blouses in our gift shop. I know they will look great on you.”

Check-in went smoothly. The front desk clerk gave a general overview of the resort and local surroundings. Daily breakfast was included as was a resort Happy Hour. The lobby was open 24 hours a day with free cold beverages, tropical punch, coffee and tea available at a self-serve kiosk in the lobby. A similar free beverage kiosk was in the pool area 24/7. Pool hours were from 9 AM until 11 PM. No glass allowed near the pool. A complementary resort shuttle goes to town and the Convent. Shopping, restaurants, bars, beaches and night life is nearby.

I mentioned that there was a good chance that I’d extend my stay and that I’d let them know. A staff member brought me a cold glass of their tropical punch (with a paper umbrella and pineapple slice) as I listened to the front desk clerk. The cool punch was pleasant.

I asked about sunbathing and if it was clothing optional. “Nude bathing is allowed at a designated nearby beach but you may tan in the skimpiest bathing suit that you are comfortable with right here at our beautiful pool. We also have private tanning decks” she said. She passed me my room key and added, “Feel free to wear whatever gender bathing suit or clothing that you wish while at Tres Palmas and our amazing beaches.”

As an afterthought the front desk clerk said, “I see that the senorita is checking in alone. Perhaps you will find a companion during your stay. If not we can arrange for a companion. We have a nearby adult resort designed to provide special companions that can fill your vacation fantasies. It’s called the Convent. They are very discreet and their shuttle is always at your disposal. Call the front desk if you would like a date.” She looked me up and down and smiled slyly.

I thanked her, poured myself another punch and walked to my room taking note of the pool area, beverage kiosk and ice machine.

The moment I left the lobby the desk clerk made a phone call.

My suite

I stepped into my suite and was immediately impressed. It was a 900 square foot two room luxury suite. My large bedroom had a king size bed and an opulent bathroom with a bidet. The living room was large too. Large OLED TVs were in both rooms; the furniture and decorations looked very high end.

The room was every cross-dressers fantasy. The décor, satin sheets, makeup table, bathroom, mirror on the ceiling above the bed and toiletries were perfect.

I wanted to relax and get comfortable. I could foresee a nice hot shower in my immediate future. I tossed my blazer on the bed, kicked out of my shoes, removed my slacks, Spanx and blouse which joined my blazer on the bed.

I was naked except for my thigh high black ‘stay up’ stockings. After such a long and arduous day the fresh air on my naked pubes felt tremendous. I pulled my stockings back into place and continued to explore my suite.

The closet was stocked with a variety of sexy chemises, night gowns, baby dolls, teddies, loungers and ‘shorty’ robes for the use of guests. There was two of each item in case there were guests. I slipped into a slinky Royal Blue satin kimono robe and pulled it closed with a sash. A large mirror confirmed that I made an interesting image.

Tres Palmas had placed a white gift box with a blue ribbon bow on one of my bed pillows. The box was labeled ‘Your Breast Friend’. I opened the box and removed a cute six ounce blue bottle. “A luxury breast enhancement solution when a girl needs a little help.” It certainly sounded interesting and it was free. I knew these creams are reported as not being very effective but I had nothing to lose. Maybe Sara would get lucky.

My Breast Friend

I needed to pee and needed reading material. I took the blue bottle with me into the bathroom, sat down and read while peeing.

“Product contains: prolactin, aloe vera, xenoestrogens, sesame oil, essence of peppermint, Fenugreek seeds, Kukui oils, trace amounts of oestrogen and Finasteride. Made in Thailand.”

I kept peeing and I kept reading. “‘Massage cream into each breast, around the nipple and areola area with circular motions until fully absorbed. Use once in the morning and again before retiring at night.”

Still sitting on the toilet I opened the bottle and put some of the cream on two finger tips. I slipped my hand inside my kimono and applied the cream to my left breast, nipple and areola as directed. It felt great. The peppermint was pleasantly cooling. My nipple became erect. I did the same to my other breast. The cream was odorless. Twice a day breast massage treatments became my daily regimen.

I finished my business, put the cream on the counter, blotted, stood up and washed my hands. Looking around I noticed there was a makeup table, Jacuzzi tub and luxurious walk-in shower. The counters and makeup table were well stocked with depilatories, razors, shaving foam, makeup & polish removers, tissue, cleansing pads, cotton swabs, tweezers, moisturizers, condoms and lube. I made a mental note to Veet my legs smooth. I went back to exploring.

Strappy high heeled sandals and a pair of pumps with three inch heels (in my size) had been placed beside my bed for my use just as I had pre-ordered. I was in fetish heaven. I thought about Stacy and wished that she was with me.

My suite had a kitchenette with a refrigerator. Hotel staff kept it well stocked with tropical punch and ice.

First month – perfect!

My first month was delightful. It took a few days of Sara being in public before I relaxed into the freedom of being me whenever I wanted; I let go of all traces of Steve and embraced Sara fully.

The resort, the rooms and the beaches were gorgeous and very tropical as promised in their marketing brochures. I swam, toured, explored and tanned. I loved wearing a sundress, makeup and pretty sandals in public.

I wore my yellow hipster bikini at every chance. The tan I was so anxious about upon arrival was coming along quite well. I enjoyed seeing the stark white outline of my bikini on my dark tanned body; I was “branded” by the sun as being a bikini wearing girly boy. When naked there was no way to hide my fetish. The effect was thrilling to me; which is exactly why I came to Tres Palmas. I was just one of the girls. I felt normal.

Most of Tres Palmas clientele were like me. Our clique often met for breakfast in the hotel or went to dinner in town en femme. We spoke, interacted, laughed, ate, shopped and went for spa treatments together like long time girl friends. We’d sit on the beach or under a palm frond covered cabana, paint our nails, work on our tans and listen to the surf.

There was occasional harmless flirting between us girls but there was no intimacy at Tres Palmas that involved me; strictly platonic while at the resort. My new found friend Lauren decided that she and I needed to go to town and ‘get away’ for some fun. Both of us had the experience and confidence in our femme selves to go forage.

A dinner dalliance I didn’t plan for

Lauren and I were in town for dinner and cocktails at a seafood restaurant located in the upscale hotel Blue Iguana. We were both decked out in our feminine finery and were enjoying the freedom of being two girls out on the town. I was wearing a form fitting ‘buttons-up-the-back’ party dress. I sensed that Lauren was on the prowl for male companionship. We finished our meal and adjourned to the trendy Los Caballeros hotel bar where a dozen or so patrons were gathered. A local acoustic trio was playing.

We had been seated and had just touched up our lipstick when two handsome British gentlemen began chatting us up and buying us drinks. They wore nice looking tropical shirts, khaki pants, ear-to-ear smiles and large wallets. Their hair was stylishly full; almost a dyke shag. Their accent and intentions were intriguing.

Jack and William joined us at our table; they were unmarried ‘mates’ on vacation from damp and foggy London and were looking for fun times with no hometown consequences. They were eager for companionship and towards that end bought us Mai Tai’s. Thank goodness Lauren and I had eaten.

Lauren eventually asked why they had selected this resort for their vacation. William said they were interested in the local ‘culture’. I chuckled and asked, “By ‘local culture’ do you mean the Convent? It is closer and cheaper than Thailand.” They both nodded in the affirmative.

“Do you boys like ‘chicks with dicks’?” I asked. Again they indicated yes. “Does that explain why you both have nicely manicured and clear lacquered fingernails? They’re very pretty in an effeminate way.” William clenched his fists to hide his nails. There was no denial and I probed no further; Lauren and I had seen what we had seen. ‘It takes one to know one.’ I would wait and see how the evening evolved. Lauren immediately asked, “So you’re sissies on a Sissy Search vacation?” William said, “Yes, we’re looking for something different; activities you don’t find in Soho or on Carnaby Street.” “Jack added, “Our travel agent says the Convent checks all our boxes.”

Now that the ice was broken they became more talkative.

Both men reached into their wallets to show us the health cards mandated by the Convent. “We’re not sure if we’ll visit the Convent but we came prepared” William announced. Lauren read his certificate and reevaluated his manicured nails. “This says you’re in great health and your blood is squeaky clean; no STDs. This is all well and fine but did you sissies bring your stockings and panties?”

Taken aback William confessed, “We figured we’d buy some pretties once we got here.” Lauren discreetly gave me the ‘thumbs up’ sign. The four of us continued our conversation while listening to the band. Jack took me out on the dance floor several times. Lauren and William danced to the slower songs.

The alcohol and dancing made for a fun evening; I was pleased that I danced so well in heels. Our slow dancing was the highlight of the evening. Jack made a point of holding me close so I could feel his hardness bulging in his pants. I wasn’t impressed; ‘Just another average cock’ I thought.

Eventually Jack got around to cupping my crotch and found something he had hoped to find. I smiled and asked, “Do you like what you found, Sweetie? Is my cock bigger than Wilma’s?” Jack pulled me tighter, smiled and kissed me on my lips; “I love what I found!” he exclaimed. “Most Sissies do” I whispered into his ear. He ignored my reference to Wilma’s cock size. I sensed a strong submissive vibe in Jackie.

The dance ended and with one hand on my butt Jack guided me back to our table. “What about Lauren? Is she a… ?” Jack almost asked. “I think it best that you ask her or maybe ask your boyfriend. They’ve been slow dancing close enough that he should know. Rest easy Sweetie, everyone at our table has the same plumbing.” Jack and William’s vacation was about to get more interesting. They were glad to have met us.

Their flirting and flattery was well received; it reinforced our feelings of femininity and desirability. As we sat at the table Jack found my inner thigh and was lightly teasing me while we all made ‘table talk’. I quietly told him that Sissies should never be so bold as to grope their Mistress. Jackie quickly jerked his hand away. “I apologize; I don’t mean to offend you.” I smiled sweetly and said, “You have a lot to learn Sweetie.” I moved his hand back to my thigh. Lauren’s smile confirmed that she was getting the same treatment from William.

Having confirmed that I was a chick-with-a-dick (and two or three Mai Tai’s later) I allowed Jackie to seduce me to his hotel room for a nightcap. Jackie knew what he wanted; he wanted a homosexual sissy experience while on vacation and I wanted sex. It was a good match for the moment.

I spent the night with Jackie. Lauren hooked up with Wilma.

Jackie’s stamina and willingness to try new things made for a mutually erotic evening. I had been chaste for a very long time; Jackie was desperate to suck his first vacation cock and I was in dire need of carnal release. I was a willing participant and teacher; just like summer camp. I had lube, condoms, experience and a spare panty in my purse. I decided to start referring to Jackie in the feminine form; I wanted to affirm my dominance over her. I was going to be her domme.

Once in her room I turned around and ordered Jackie to remove my dress. She unbuttoned me and helped me carefully step out of it. “Now be a good girl and hang it up.” Jackie complied instantly like a good submissive should. She dutifully hung it neatly on a hanger in the closet.

When she turned around I was standing with my legs slightly apart, hands on my hips and only wearing panties, bra, black stockings, earrings and heels. Jackie stood motionless and stared at me like a love struck school girl. My nipples were hard.

As we faced each other I reached behind myself in a sultry manner and unhooked my bra tossing it casually onto a nearby table. My perky titties and pretty areoles were on full display; and my high beams were on. My dark brown bikini tan contrasted in a very exotic way. “Do you like what you see, Sweetie?” I asked. Jackie nodded energetically ‘yes’.

“You’re beautiful! You look so feminine, so authentic!” she stammered. I tried to smile seductively and asked, “Isn’t that the idea, Sweetie? Would you like to look pretty too? It is so exciting. Isn’t that’s why you came to visit the Convent?” Her unspoken answer was the growing bulge in her slacks.

Still standing apart I asked, “Does my sweet sissy want me to take my panties off? You’ll love my panty tan; it matches my tittie tan.”

“Take off your panties” Jackie said.

I instantly assumed an angry demeanor. “Did you just ORDER me to do something? Let’s get something straight right now, Missy. You, my little sissy, NEVER tell me what to do. I order you, you don’t order me.” Jackie was shaken by the anger in my voice.

“Listen to me Missy! You will always ask me nicely for any favors. I may, as your Mistress, allow you those favors. If this isn’t where your mind set is I’ll get dressed and leave you to jerk off alone or find your relief in a dark alley somewhere. Do we understand each other, Precious?”

Jackie was initially shocked at my outburst. She wavered a moment and then nodded ‘yes’.

“Jackie darling a mere nod is no good; I want to hear you say it; say it like the submissive sissy you are! I am always to be addressed as Mistress or Miss Sara.”
Jackie composed herself. “Yes Mistress. I am a sissy. I’ve been one in my dreams for years; I wear stockings and panties at home. I’m very sorry I was so rude. It will never happen again. I will always be respectful and do as you say. Please forgive me!” Her tone seemed sincere.

“Very well: we have an agreement. So what does my sissy want to like to ask me?”

“Miss Sara, please take off your panties? Please.”

I inwardly smiled at my psychological victory. I replied, “No Sweetie, I will not remove my panties.” I waited for her look of disappointment to appear. Her dejection quickly showed. I pointed at her and announced; “YOU will remove my panties as soon as you get undressed. We have many fun things to do and I want you naked.”

In less than a minute Jackie had her thumbs hooked into the sides of my panties. She quickly slid them down my legs; I carefully stepped out of them. I was nude except for my stockings, high heels, dangling gold earrings and bikini tan. I fluffed out my hair and shook it loose. I then swayed my penis to further tease Jackie.

Jackie stepped back and stared longingly in admiration. Her eyes alternated back and forth from my tits to my dick. She was trembling with lust. Her appendage began to make its presence obvious. She involuntarily licked her lips.

Repeating myself from earlier in the evening I asked, “Do you like what you see, Sweetie? Is my cock bigger than Wilma’s?”

“My God Mistress your nakedness and tan are beautiful. Your budding breasts excite me. You are a real dream.” After a short pause she asked, “Miss Sara, may I please kiss you on your lips?”

“You’re such an eager and polite sissy! I’ll let you kiss me anywhere you want… including my penis.”

We kissed and fondled; Jackie explored what my body had to offer

Jackie progressed from sucking my budding titties to sensuously stroking my erect penis. I did the same for her. I gave Jackie free access to what she desired most. Jackie held my dick and gave it a tentative kiss. Her mouth took in my cockhead as she began to fulfill her cock sucking fantasy; she claimed I was her first. It took great will power but I made her stop; she needed to refine her techniques.

“Sweetie, before Miss Sara allows you to suck her off you obviously need to learn a few things. Watch and learn how to be a good Sissy cock sucker. Remember, no teeth!” I had Jackie sit naked in a chair while I dropped to my knees between her legs. It’s difficult to explain oral technique when your mouth is filled with a penis.

To Jackie’s delight I demonstrated on her the basics of cock sucking but not to the point of ejaculation; when I gently tickled her anus Jackie gasped and clenched in pleasure. “A good sissy uses their tongue to pleasure their Mistress’s back hole. Do you understand?” “Yes, Miss Sara I understand” Jackie replied softly. I ordered her to switch places. “Show me what a good sissy cock sucker you are.”

I sat naked in the in the chair, my erection pointed to the ceiling. I looked down into Jackie’s pleading eyes. She was kneeling at my feet with her hands on my knees. Her eyes were fixated on my erect penis. She scooted closer and gently tried to pry my knees apart. I refused her.

“If you want to suck me Sweetie, you must wear my lipstick, you must swallow what I give you and you must ask me nicely. Will you do these things for Mistress?” Jackie instantly said, ‘yes’. Her hands quivered on my knees. I handed her my tube of lipstick and she expertly applied it to her lips. She capped the tube and set it down.

“Please Mistress Sara. I’ve always been a sissy. I’ve been a sissy for William but I want to be your sissy and do what you ask. Please let me suck your beautiful cock; it’s so nice. Please” Jackie softly pleaded. She was in sexual animal heat. She blew me a kiss.

“Tonight is very special for you and your sissy training. Your lips look very pretty and therefore you may make love to my penis; I want to see three bright red lip prints on my penis when you are done. If you spill so much as one drop of my sperm there will be hell to pay.” I then allowed her to part my knees and live her dream.

“Thank you Miss Sara. I’m very grateful.” Jackie tenderly took hold of my penis and guided it to her lips. Like a good sissy she kissed the tip and left a nice lip print. “That kiss print doesn’t count!” I warned. Where did she learn this etiquette? From Wilma?

I let Jackie spend a few minutes becoming familiar with what a cock in her mouth feels and tastes like before reminding her to slide her lips and tongue up and down my shaft. “Pay attention!” I sternly admonished; Jackie complied perfectly. She was doing a fine job and had found my testicles with her free hand. I was hoping she would probe my sphincter; I moved to the edge of the chair and spread my legs wider. I was not disappointed in her lustful and deep fingering. She was not an amateur.

As a courtesy I alerted Jackie just before “it” happened. I gripped her head snuggly between my legs; her lips, and a red ring, were positioned half way down my shaft. I ejaculated 3 or 4 times and then slid my dick deeper toward the back of her throat and squirted 2 more times. Jackie controlled her gag reflex very well. I felt her trying to swallow my seed.

“I won’t let you go until you swallow all!” I threatened. It turned out that I didn’t need to ‘force’ Jackie to swallow; she was very eager. I relaxed my grip on her head and she continued to slowly swallow. Jackie took her time in releasing my flaccid cock from her warm mouth; she was savoring my sperm. She opened her mouth, showed me the last puddle of sperm and did a final swallow. She was smiling. “Does Mistress want a fourth red ring on her cock… or elsewhere?” “No Sissy Jackie. You gave me an excellent blowjob. I can tell that you enjoy being a cock sucker. I’m pleased with you.”

Still on her knees Jackie licked her lips several times. “Thank you Mistress. I really enjoyed pleasing you. You were delicious. May I pleasure you again once you’ve recovered?”

Jackie wasn’t in London, her shyness had vanished and she wanted more of what my penis had to offer her mouth and man-pussy.

I leaned over and rewarded her with a kiss on her lips. “There’s no going back; you’re a cocksucker now Sweetie. Do you and Wilma suck each other off?” Jackie softly said “Yes, Miss Sara we do; we came here to experience new things.” Jackie composed herself and without being asked reapplied my lipstick to her lips. She was more sissy-femme than I thought.

We adjourned from the chair to the bed so we could further explore her other sexual fantasies. I made a point of praising all her efforts.

Jackie had no apparent interest in mounting me; she was an enthusiastic cocksucker and a perfect submissive bottom. Jackie was aching to be pegged; it was her vacation fantasy.

I was happy to help a new girl out but I demanded to wear a condom despite her having a health card. Assuming my domme attitude I ordered Jackie to place the condom onto my penis using only her mouth, lips and tongue to smooth it snugly down my shaft. We both had seen it done on porn sites. She eagerly obeyed my commands like a natural born sissy. Jackie was having fun. Her red lip prints on my penis were visible through the ultra thin condom. Her immediate compliance and skill impressed me.

Jackie lubed my penis and her boy-pussy. She lay on her back with her legs on my shoulders and positioned my penis to where she wanted it. Taking a deep breath she begged, “Please fuck me Miss Sara; I want to feel you in me.” She wiggled and thrust her hips to her advantage. I slowly slid deep inside her. Jackie took being penetrated very well; I varied my thrusts and speed to provide different sensations for both of us. In return she clamped and milked my penis to maximize our pleasure. Was this really her first anal fuck? Her moves and moans said “no”.

When I orgasmed deep inside her Jackie spontaneously ejaculated too; she squirted several times onto her chin and chest. She used two fingers and tasted herself. It was pleasurable for me too. She asked if being fucked would feel different without a condom; if she would be able to feel me squirting. Jackie’s comment was more of a request than a question. “If you’re a good sissy and if you make your boy-pussy squeaky clean I might fuck you bare back. Ask me nicely tomorrow.” “Thank you Miss Sara.”

We eventually called it a night. We removed our lipstick and my makeup before going to bed. We slept nude. It felt comforting to be snuggling with someone.

I woke up naked, in a man’s bed

I woke up naked, in a man’s bed and found the ‘man’ sensually suckling on my tit while gently playing with my growing cock. Jackie was also sporting a morning woody that was lying in the crack of my ass. I reached behind me and felt her cock. I wiggled back against it. I was disappointed that Jackie didn’t take the opportunity to experience fucking a man.

I briefly wondered if I should get her very erect and then sit down and impale myself on her prick and see what would happen. Jackie is definitely a submissive sissy bottom and the world can always use a few more. She didn’t care that she didn’t know what she was missing.

I did a mental recap of the last few hours: I was dressed and made-up as a woman, had been ‘picked up’ in a bar by a man who liked sissies, took me dancing, plied me with alcohol, blew me and then begged me to fuck her. I reveled in my decadence.

I explained to Jackie that I don’t do mornings well without coffee and a little food. If there was no coffee there would be no sex. I was in command of the situation; I had something that she wanted!

Before Jackie ordered room service I told her to have two flower scented enemas sent up from the gift store. “You are going to douche yourself twice, right? Squeaky clean enemas; if I find any ‘dirt’ on my dick you will lick it away. Do you understand!?” Jackie understood perfectly. She understood that she wanted to be pegged au natural. Jackie ordered 3 bottles of ‘Convent Cleanse’ floral enema from the gift shop to be sent up with the breakfast.

“Jackie, we have seen that you and Wilma have no problem with indulging in pretty manicures, right? So now it’s time to make your toes look girly too.” I handed her a bottle of Coral Red nail polish (it matches my lipstick) and ordered her to paint her toe nails while we waited for the food and enemas to arrive. It was another nudge into sissy hood. I’m sure she loved being ‘commanded’ to do it. She shook the bottle twice and immediately began doing what Mistress had ordered.

“Wear socks or shoes and no one will know. It’s our sissy secret. It will remind you that you’re sissy. You need to keep your toe nails painted even if it’s a less vibrant shade. Her nails were dry by the time the food arrived. “Maybe you can get a paying job at the Convent!” I joked.

After a leisurely in-room English muffin and coffee breakfast, and before resuming where we had left off last night, Jackie excused herself to prepare her pussy for her ultimate vacation fantasy of experiencing bareback sex. I had decided to accommodate her because of her medical records, her promise to have a clean pussy; actually it was her need to be further sissified that was the deciding factor; I was doing the new kid a favor. It was like summer camp all over again.

I kicked out of my panties and tossed Jackie a tube of KY jelly. I ordered her to lube my shaft. “Yes Mistress, it’s my pleasure!” she said. She lovingly greased the shaft of flesh that what was about to be deep inside of her. She kissed it for luck.

When she was done with me I told her to lube herself. “Put this where it will do the most good” I admonished. Jackie eagerly did what needed to be done. She lay back on the foot of the bed and raised her legs high in eager acceptance of what was about to happen.

I stood at the foot of the bed wearing only my high heels; they raised me to a level of entry that would better allow my penis to stroke her prostate. Leverage can be good. And just like last night Jackie used her hand to position my penis. She lustily smeared my pre-cum on the entrance to her hole and then spent time diddling herself with my rigid dick before inserting my cockhead into herself.

Jackie controlled my slow slide into her man-pussy by clenching tight and then relaxing so I would slip deeper into her a little at a time; she knew what she wanted. Her pussy smelled like a florist shop.

“Thrust deeper!” she pleaded

After accepting penetration Jackie wrapped her strong legs snuggly around my waist and pulled me deeper into her; she wanted to feel the impact and heat of my ejaculation. “Deeper!” Jackie pleaded. I began energetically impaling her as deep as I could. She clenched my penis when it suited her.

I erupted multiple times deep inside her; she let out a guttural moan and spasmed in carnal ecstasy. She used her legs to keep me deep inside of her while using inner muscles to milk me dry; it was toe curling superb!

“I felt you come… it was warm and nice! Thank you Mistress. It was beautiful!” Jackie exclaimed. When she was done with my penis I withdrew and lay beside her on my back. She thoughtfully used a warn wash cloth to clean my prick. The pleasant aroma of her pussy cleanse filled the room. She brushed her shaggy hair, applied my lipstick and lay next to me. She held my hand as we made small talk.

“I’m going to leak?”

I warned Jackie to expect sperm leakage from her man-pussy. The look on her face was priceless. I explained; “Love, if you have bareback sex you must expect leakage. If you don’t want wet spots on your panties or furniture take precautions. Wet spots are awkward; they don’t feel nice, they call attention that you just had anal sex and passing dogs will sniff your butt.”

“Look, Missy, you’ve just been inseminated; fucked, bred...I’m not sure which term is used these days. I pumped several loads of my ‘swimmers’ deep inside of you. They have to go somewhere. Eventually they will seep out. Be prepared for it every time you bareback fuck.”

Jackie appeared confused. “Precautions? Bred?” she asked.

I rolled over, grabbed my purse from the nightstand, and retrieved a Light Days panty shield and two tampons; “It’s your choice…I use them both at the same time.” She took them and put them on her night stand. “Thank you” she softly said. “No problem, Sweetie. If you want I’ll help you with your first tampon after we shower. You may want to wear underwear tonight.” She pulled on a pair of men’s jockey shorts and fell asleep. It turned out to be a wise decision.

Showering together presented more opportunities to guide Jackie toward accepting her queerness and inner feminine self. I tucked my hair into a complimentary shower cap to protect my hair. Jackie was very eager to suck me to orgasm again. I refused to let her blow me until she shaved her pubes and legs. “All my Sissies shave their legs and pubes” I told her. I partially shaved one of her legs to inspire her. She dutifully shaved the rest of her body.

Without being asked she also shaved her arm pits and around her tits. She set the razor down. “That’s a good sissy-girl; we like being smooth because it makes giving a sex more pleasant” I cooed softly. “Your boyfriends will love it.”

“Now it’s my turn for a shave.” I handed the razor back to her and said, “After you shave away the stubble around my pubes then you may suck my cock; I want your lips sealed around the hairless base of my dick.” Jackie lathered me up, gently held my penis and began shaving my crotch area. She held my cock more firmly in order to maneuver me to the areas that needed shaving. I softly moaned “I love the way you’re stroking me.” Jackie placed a lingering kiss on my cockhead and continued with her task.

Without being asked Jackie grabbed my hips and turned me around and lathered my man-pussy. “Mistress Sara, may I please tidy up your love hole?” Jackie pleaded. I answered by bending slightly over and spreading my cheeks. “Do a good job Sissy because I want you to use your tongue to penetrate me back there; a Sissy must be willing to pleasure their lovers in many ways. Show me how deep your sissy tongue can go.”

Jackie did a fine job on all accounts. She lathered, shaved, washed, rinsed and lovingly fingered me and then tongued me in a magnificent manner. “Thank you Miss Sara!”

As soon as Jackie had finished with my backside I sat on the built-in shower seat with my legs spread. Jackie dropped happily to her knees; Jackie was like a bee collecting pollen; she couldn’t get enough of the nectar that my “flower” had to offer.

While drying off I tossed her a tube of the hotel moisturizer. I placed a towel on the bed and ordered her to moisturize my legs. I explained the need to crème your legs after shaving. Jackie did a fine and sensuous job. When she was done with me she sat on towel and moisturized her own legs. “Good girl” I praised.

Jackie smiled and said “Thank you Miss Sara.” When she stood up her smile turned into a frown. There was large wet spot on her towel. “Mistress, I’m leaking just like you said I would! I need help inserting my first tampon. Please!” Jackie quickly grabbed a tampon from the night stand and handed it to me. She clearly was stressing out. “Yes, Sweetie, let Aunt Sara help you. It gets easier after you’ve done it a few times.” I tore open the wrapper.

After showing Jackie how a tampon works I handed it back so she could inspect it closely. The plunger and braided removal string fascinated her. “I always use Tampax Pearl Lites because they are skinny and slide in easier; a bit of lubricant on the tip of the applicator helps.” I explained how and what needed to be done.

I took the tampon from her hand. “Put your hands on the bed, bend over, spread your cheeks and relax, Sweetie.” I twirled the applicator against her sphincter as a diversion to gaining entrance. Once I was past her outer sphincter I slowly inserted the applicator to avoid discomfort. When I got past her second muscle ring I positioned the tampon, pushed the plunger, removed the applicator and announced, “It’s done.” I made her tug the removal string to show her that the tampon was not going to accidentally fall out.

“Your leakage will be absorbed by the tampon. Be sure to change them every few hours. They feel odd at first but so does your first bra; you get accustomed to them. There are on-line videos that show how to do this; watch them with Wilma.”

“Some sissies prefer a solid butt plug to prevent leakage; some sissies enjoy wearing a butt plug even when they are not filled with cum. The gift store has many styles. The ones with fake jewels are pretty; it’s like having a large ruby plugging your butt.”

“Okay, Sweetie there one more thing you need to know. Watch and learn.” I picked up yesterdays panties and showed Jackie how panty liners work. I peeled a liner open and stuck it to the crotch of the panty. “Be sure to place the liner further to the back… where your boy-pussy is.” I held the panty open and had Jackie step into them. I pulled them into place and she wiggled to make the unfamiliar pad get seated and feel more comfortable.

“Now you’re double protected. A day after being bred a panty liner is usually all the protection you need. Always be prepared; carry both. You may keep my panty.” It was clear that Jackie was enthralled with her gifts and the knowledge I had given her. “Thank you Miss Sara, you’re a life saver.”

After she had my panty on, and was smiling, I gave her a reward kiss while rubbing her firm erection through my old panties. “You look so sexy Jackie; you definitely need a few more panties. Do you promise to buy yourself some?”

Jackie was getting all hot and bothered. “Yes, Mistress I promise. I saw some in the gift store and I have a few at home.”

“Yes, for being a hotel gift shop they have an excellent selection. Being so close to the Convent they have an entire line of intimates, lingerie, cosmetics and sex toys. I’m sure they have everything that you fantasize about. All items have the Convent logo; what lovely souvenirs to take home!”

This had been another learning opportunity to reinforce Jackie’s repressed sissy tendencies. I know a lot about sissy tendencies; the urges can be very compelling. I ordered her to reapply her lipstick. There was no hesitation.

Time to go

It was getting late and I wanted to get back to my suite. I hadn’t had my daily breast therapy. Although I could have managed by myself I had Jackie help me get dressed. I figured she needed the practice and deserved a little excitement.

I sat in a chair with my fresh panties on and handed her my thigh high stay up stockings. She dropped to her knees and efficiently rolled them into pace. Still kneeling she looked into my eyes and asked, “May I Miss Sara?” I nodded approval and Jackie tugged my panties open and kissed the tip of my dick. “That’s a very pretty lip print Sissy” I said. She smiled and then firmly pressed her lips around my cockhead leaving a vibrant red ring. She let my panties snap back into place and said, “Thank you Mistress” before standing up. She reapplied her lipstick.

Jackie hooked my bra and helped me into my dress making sure to button me up properly. “You really are a good sissy Jackie. You have so much potential. I wish I could take you home with me and continue your training.” She was thrilled at my praise.

While Jackie arranged for a taxi to take me back to Tres Palmas I stepped into the bathroom to brush my hair, apply my mascara and lipstick. I had just finished with my lips when I noticed Jackie was intently observing what I was doing. I turned to face her and smiled mischievously. “If you are going to look like a woman you should smell like one. Every time you smell Plumeria you’ll be reminded of being a sissy.”

I applied a small amount of ‘Tropical Plumeria’ perfume to our throats, our inner wrist and behind our ears. “If you are going on a date you apply a nice scent on your inner thigh or bikini line. The scent drives dates crazy with lust; it confirms your femininity to them and enhances the sexual moment. Never overdue it; less is more.”

“Thank you Mistress. I want to smell girly like you.”

I grabbed Jackie’s chin and applied a light coat of mascara to her eyelashes; there was no resistance. “You don’t need a lot to make your eyes stand out; just a few light strokes. Take a look, Sweetie.” Jackie peered into the mirror and agreed, “Yes, Miss Sara I do look better.”

“No, Missy,” I corrected, “you look prettier.” Jackie nodded in agreement. “It sure makes a difference.” She took my mascara and applied a heavier coat.

Since she was in a willing mood I handed Jackie my eyelash curler. “Always curl your pretty lashes, Sweetie” I said. She did. Eagerly darkening her lashes and willingly curling her lashes further acknowledged Jackie’s desires; it made me smile.

Taking every opportunity that I could to guide Jackie into being pretty I mentioned the importance of lipstick.

“Jackie darling you should always add a little color to your cute lips. Lipstick does so much for a girl’s image. It also works as a soothing lip balm when you’re been blowing your ‘dates’.” I sensed a mental light bulb going on in her mind.

“I have one more tip for my eager sissy.” I lightly kissed both of her cheek bones transferring a little of my lip color to her cheeks. Holding her head in my hands I used my thumbs to blend the color into an acceptable blush. “Take a look, Sweetie, you now have a last minute sexy blush. There are many ways to easily enhance your beauty.” Jackie looked at her image again and nodded. “Lipstick makes a nice difference”; she agreed. I cupped her crotch and kissed her as positive reinforcement.

“And…?” I asked. “And it makes me prettier!” she added. “It also makes you sexually attractive.” I rewarded her with a lingering kiss.

I handed Jackie my lipstick, nail polish and mascara. “Keep these, Precious, and use them when you want to feel pretty. Show Wilma how pretty you can be. Better yet show her how well you suck cock; she’ll be jealous.”

“Thank you, Mistress Sara. May I see you again?”

“Jackie, you need time to reflect on what we’ve done; you need to reflect on your femininity and the fact that you are an accomplished cocksucker. I’ll ring your room in a day or two and perhaps we can arrange a date. I’d love to watch you and Wilma having sex! I would even bring Lauren. Wouldn’t that make for some great vacation memories… if you could afford us.”

“William, er… Wilma, has lots of money Miss Sara. Once I tell her what’s in store for her I’m sure she’d welcome ‘dating’ you and Lauren. Would you please make her blow me when we get together?”

“Yes, I’ll make her leave pretty lipstick prints all over your cock!” I replied. Jackie smiled at the thought of that happening. “When I return I want you to show me two girly items you’ve bought from the boutique, OK?” She eagerly nodded ‘yes’.

By the time we got to the lobby the cab was waiting. Jackie held the taxi door open for me and we passionately kissed goodbye. As we were hugging Jackie slipped three $100 bills into my bra. “Thank you for a memorable time Mistress Sara. I’ll never forget you or last night. Please call me. I’ll let Wilma know what to expect.” She discreetly caressed my crotch. “And I’ll have her go to an ATM!”

“Well Sweetie, if that happens I would extend a ‘favored customer’ rate to you. Maybe we’d all spend the night together again.”

I whispered, “Jackie darling, I’m glad I was your first blowjob; you are a natural. Never forget that you’re now a panty wearing, leg shaving, pegged, tampon using cocksucker. Model your pretty panties for Wilma, show her your tampon string and it’ll be a race to see who blows who first. If you are not currently sex partners (and I believe you are) I predict you will be lovers before you leave town.” Jackie blushed and didn’t deny my comment.

I closed the taxi door and was driven home. I wondered if Jackie and Wilma would visit the Convent; or would they satisfy their curiosity and needs in the privacy of their hotel room?

I took Jackie’s money from my bra and put it in my purse. A man had just paid me for sex; does that make me a prostitute? My dictionary says yes.

“Pros-ti-tute (noun); somebody who is paid to provide sexual intercourse or other sex acts.”

I was happy to check off ‘have sex’ from my mental vacation check list. Had I evolved deeper into femininity?

Back at the hotel

Later that day Lauren and I lounged beside the hotel swimming pool sipping the hotels delicious tropical punch as we recounted our evening with our new ‘girl friends’. We were having a lot of fun gossiping about our deviant dalliances.

Lauren said she had picked up ‘girly vibes’ from Wilma from the very start. Wilma didn’t display any reluctance or confusion as they made same sex love. They both got laid and they both got blown; Wilma knew her way around a man’s body and how to quench a man’s carnal needs.

“Wilma showed me photos of her and Jackie dressed as women at several adult parties at an exclusive London swingers club; they make a cute couple but they need a little guidance to look more realistic femme.” I agreed with her and briefly explained how I had ‘educated’ Jackie. “You certainly are creative!” Lauren said.

Lauren mentioned that Wilma had called her just before I got back to the hotel. Wilma was raving about what a gorgeous bikini tan I had and what a wonderful time Jackie had with me. “Whatever you and Jackie did Wilma wants us all to do the same thing; all four of us.”

“That makes sense. I left Jackie wearing panties, with shaved legs and pubes, wearing mascara, lipstick, perfume and a tampon. You can’t make this stuff up; it’s like those adult porn sites.” Lauren commented; “Stuff like this never happens in real life.” We shared a good laugh.

After relating how she had been fucked and sucked last night Lauren pressed me for the details of my tryst. I covered most of the action and mentioned that I had earned ‘a few dollars’ by being a ‘personal trainer’. “It was easy money and there’s more to be had for both of us; we would be providing a service, right? Would you like to make a couple hundred dollars for a few hours of work while enjoying yourself on vacation?”

“They are medically approved for sex at the Convent; get back to me with the details; it could be fun” Lauren replied. “Whenever you want sex just call their hotel and ask for room 1115.” I was glad I had given Lauren Jackie’s room numbered because I felt that she would gain more confidence by being with a different ‘chick-with-a-dick’.

I mentioned that Jackie loved sucking my titties and that now my tits were tender and puffy; my nipples were always on “high beams”. When I got back to my suite I used My Breast Friend to make them feel better; the aloe vera helped.

The itching of my breasts diminished a bit but the puffiness and erect nipples did not. What had Jackie done to my tits?

Two days after my date with Jackie - I’m arrested!

Partially due to my dalliance with Jackie a few days earlier I had fully evolved into being Sara; it felt right. I had decided to give Jackie a call and see if she and Wilma would like to take Lauren and I to dinner.

It was also the start of my second month at Tres Palmas. I was toying with the idea of remaining Sara when my vacation was over; I was wondering how to break the news to my mom.

When I notified the front desk that I would not be extending my stay I was told my resort charges and payments were being denied by my credit card company and I was weeks in arrears on my resort bill. My loud and animated dispute with the hotel manager became my downfall. He said I owed rent and other resort charges; I said I did not. He threatened to report me to the authorities. I told him to buzz off and to go fuck himself. The manager called the hotel’s owner.

The owner of Tres Palmas was also the Minister of Agriculture for the country; he ruled the province and was well connected. He would make sure his police and judicial friends taught me a lesson. I was going to be “volunteered”.

A day later

The police came to interview me just as I returned from the beach. I was in full Sara mode; earrings, makeup, yellow bikini, leopard print high heels and a sheer blue print beach cover-up. I was carrying a beach purse and wearing my large straw sunhat. I had just unlocked my door when the police arrived; we met on my porch. I was shocked; so were the police. They claimed my travel visa had expired and I owed money all over town and at the resort. Rather than debate in public we stepped into my suite.

Credit card fraud

They claimed that I had been defrauding merchants by using a bogus credit card and that my travel visa had expired weeks ago. I knew this was not true. I was asked, “Why are you still in country?”

During their half hour “visit” to my suite the police relentlessly interrogated me. Perhaps my smug, “I’m an American with rights” attitude pissed them off. My big mouth set in motion a sad state of affairs; the arrogant rich American kid (me) with a big mouth (me) definitely needed to be taught a lesson.

Anger can make a person say very stupid things. In hindsight I should not have verbally disparaged them, their families, their mothers or their soccer team.

Still in my bikini I was told to remain seated. The police huddled in the kitchen and discussed my fate. I overheard an animated discussion; they were talking about me, my travel documents and those ‘special’ words that the Customs Official had marked on my documents; travisti.

I overheard the police saying the Convent, just like summer camp, was in need of ‘volunteer women’. The recent release of three Convent ‘women’ created a need for replacements and they were tasked to quickly “recruit” more.

The front desk had explained that the Convent is a state run brothel that caters to wealthy clients that enjoy anonymous sex with chicks-with-dicks. The Convent is why Wilma and Jackie were vacationing here.

One policeman stepped out of the room and continued his telephone conversation with his superior. The call ended.

My premises were searched again and this time a small amount of marijuana was magically “found” which was odd because I don’t smoke anything!

Travisti (transvestite)

I was arrested and taken into custody. I was not allowed to change clothes; I was only allowed to pull a sundress over my bikini. My leopard pumps were my footwear. My makeup and painted nails were funny to the authorities. My hands were cuffed in front of me.

I was charged with violation of immigration laws by being in-country without a valid visa, defrauding an inn keeper and local merchants, international credit card fraud, drug possession and a few other things. It was stated that I had engaged in acts of prostitution with a British citizen. I knew Jackie would never do or say anything that would prevent her from being with me again. My travel documents and ID were seized. I politely asked for a lawyer.

My first booking photos were of me as Steve that required the removal of my makeup and earrings. Front and side views were taken. A second set of photos of Sara were needed. A cosmetologist in a white lab coat with “The Convent” on it quickly did my hair and makeup. The cosmologist went for a “Smokey-eyed evening glamour” look with ratted hair and dangling earrings. I looked more feminine (slutty) afterwards than when I was arrested. I thought I looked hot. Connie, Sue and Stacy would be impressed.

The cosmetologist stood back and admired her work. “Very pretty for a travisti” she said. She took a couple photos of her handiwork with her cell phone. “You will do well at the Convent; I’d love to work on your brows but we’re out of time. My name is Tina. See you soon, Princess.” She left.

The word ‘travisti’ (transvestite) was embedded at the bottom of ALL my mug shots.

My file folders also bore that term and my arrest folder was pink. My paper work listed an alias of ‘Sara’. I’m not sure how the authorities were aware of my femme name. I was a marked ‘woman’ for sure. My court day would be in the morning.

I asked for a lawyer again.

Going to court

I was taken to court in full Sara mode complete with vivid mug shot makeup, sundress and bikini from the day before.

At the end of a three hour whirlwind “trial” I stood before a judge. I had been found guilty. “We have a special facility for arrogant foreign scoff laws such as you. You are sentenced to our state run brothel to atone for your crimes and earn your keep. A stay at the Convent will help you focus.”

“Adapt and your stay will not be unpleasant. Sissy inmates with your youthful look do well at the Convent. Failure to cooperate will not go well for you.”

I was being shanghaied, incarcerated and ‘volunteered’ to fill the need for sex travisti at the Convent.

I asked for a lawyer.

Upon being convicted and sentenced I was immediately led to a secure locker room just off the court room. A female police officer was waiting.

“Well Steve, you are now a travisti convict. You will comply, without question, with all prison rules.” She passed me a basket of prison female clothing. “Take off your pretty clothes, put these on and give me what you’re wearing” she commanded. The officer admired my sundress and bikini I had just been wearing.

Prison clothes, prison bra

“Accepting and adapting to your punishment begins immediately. You will dress as a woman, including a bra and high heels, until your release. Red plumping lipstick and nail polish must be worn at all times.” She paused and stared at me awhile before continuing. “It certainly looks like this is not going to be a problem for you Sissy; you brought your own high heels! We’re going to teach you how to be a travisti whore.”

I was standing in a short yellow low cut floral prison mini sundress with puff shoulders, a pair of grey cotton panties and a red balconette prison bra. My leopard print pumps were my footwear. A small cross body denim prison purse, with “Travisti” embroidered on it, hung on my shoulder. Lip-plumping lipstick and a brush were inside. I looked like a cheap whore.

The officer remarked, “For a boy you sure fill your bra well. No fake tits for Miss Sara, eh?” I didn’t understand what she meant.

Reaching into my purse the officer handed me the brush. “Brush your hair, Sweetie and color your lips so we can get you to the processing facility. We have much to do and you have much to learn prior to your first date at the Convent.”

I did as I was told. I applied the lipstick, smacked my lips and dropped the lipstick and brush back into my purse. The officer rolled her eyes and went back to completing her paper work.

“Your dossier says you have been cross-dressing for years and already have pierced ears. Is that correct, Steve?” I nodded and said, “Yes, my ears are pierced.”

“Great, that saves us from having to do it; it makes installing these much easier.” The officer held up a pair of three inch gold colored hoop earrings. “Come closer, Stevie dear,” she directed. The officer replaced my earrings with non-removable prison I.D. ones; I heard them click closed. I was ear tagged like a cow.

“The Convent will unlock these in a few days and give you different styles if you’re a good girl.” She pocketed my earrings, shook her head and chuckled. “My, aren’t you cute Steve! You walk in heels with no problem; you even sound like a woman. I’ve heard that you have a sexy bikini tan. Is that true, Precious?”

I said nothing.

“I’ll take that as a yes. You’ll be pleased to know that we have one more piece of prison jewelry for pretty sissy boys like you. It marks you as being a Convent whore. Have a seat cupcake.”

I sat as instructed; my knees pressed together in a subconscious girly way.

A jail trustee knelt in front of me and locked a feminine, non-removable, shiny gold colored metal anklet on my left ankle. The anklet had “Travisti” inscribed on it.

Before standing up the trustee who had just locked the anklet on me rubbed my legs. He began grinning and announced to the officer, “There is stubble but no hair on her legs.” He turned to me and said, “If my pretty puta (whore) needs help I will gladly shave your pretty legs; I know where you sleep.” He winked, blew me a kiss, stood and left the room. A wave of fear rippled over me.

My police officer ordered me to standup. She closely inspected me. “For a soon to be prostitute you look fine. You have pretty legs and your female voice is spot on. You’re going to be very popular, especially with our clients from the Mid East. They love puffy lipped sissy boys.”

I was given a light weight pink sweater for warmth. Like a badge “Travisti” was stitched on the front left breast area. I stuffed it into my purse. My no-nonsense police officer grabbed my arm and firmly marched me to a floor to ceiling mirror. “Stand here and take a good look at yourself, Mary. Perhaps we should send a photo to your family so they know how good their pretty daughter is looking. Do they know how pretty you are, Stevie? I’m sure they would be very proud.”

Her comments reinforced the dire situation I was in. She had also called me a sissy.

The officer left me standing in front of the large mirror as she took care of paperwork. As I stared at my reflection with the heavy makeup I felt my penis come to life. I was getting aroused over my own image! This was not going well. I prayed we’d leave before I fully tented my sundress.

Before I got too worked up the officer handcuffed my hands behind my back and led me to the front door of the court house. As we stood in the bright sunlight my officer pulled one shoulder of my dress partially down exposing my red bra strap. “The Convent likes to show off their new whores; having the press see your bra is good for business.”

I saw that there were news and video photographers patiently waiting for us. “Well, Sara, it looks like you may make the evening news. Perhaps your debut will be broadcast to the US.” A mental image of my parents glancing up to their TV tonight and seeing me doing a ‘perp walk’ made me shiver!

“Smile, Princess, here’s your big opportunity to get discovered.” She grabbed my arm and held me on the sidewalk until the news crews could get closer. Holding me firmly the officer announced, “Meet Sara, she’s the Convent’s newest girly-boy prostitute. She’ll be available at the Convent in a couple of weeks. If her pretty plumped lips are any indication she has a lot to offer if you have a lot to give. Check our website in a few days and see her brothel beauty photos. Sara’s bound to be one of our most requested ‘ladies’. Get in line and place your order.”

I was twisted and turned by her so photos could be taken from various angles. “Be sure to take a photo of her pretty prison anklet. It marks her as Convent property.” The clicking of the cameras was surreal. “Look at her sexy red toe nails sticking out of her open toed high heels. When we arrested her Sara was wearing a skimpy yellow bikini and these heels; she’s a boy that’s hot for sex.” I was becoming mentally overwhelmed… and scared.

Done with the photographers the officer loudly popped my bra strap (which elicited laughs) and said, “OK, Honey, let’s go.” I was nudged in the direction of the van.

The jail transport van had been purposely parked further down the street than it needed to be. The officer slow walked me so the public and press could see my shame. My heels clicked loudly on the sidewalk as we walked. Cat calls and obscene remarks were loud, non-stop and frightening.

Because I was handcuffed the officer and driver helped me into the van. I sat on the bench seat and they hooked my seatbelt. Ankle restraints with a 13 inch chain were snapped on. My hands remained cuffed behind me. We drove to the prison facility where I would be processed, feminized and trained.

Before I was assisted out of the van the officer used stretch hair ties to create two ‘young girl’ pigtails in my hair and gave me some bangs. “The little-girl waif look is very popular with our inmates and clients; there’s a strong demand for pretty boys that look like you.” She smirked. Still in hand and ankle cuffs I was taken inside. I was paraded through the administrative area of the jail first and then past the main lockup area.

The ankle chain made me take short mincing steps; my hips swayed with every step. Everybody came to look at the shackled new ‘puta’ (whore) in her pigtails and open toed pumps mincing and clicking her heels around the facility.

I asked for a lawyer.

I was told to sit in a straight backed wooden chair while paperwork took place. They left me cuffed and chained as a show of their dominance; it was a message to me. About a half hour later my restraints were finally removed and I was brought to a cafeteria to eat. I didn’t bother to brush away my pigtails or bangs; I thought they were cute.

The jail food was adequate. Their tropical punch tasted amazingly like the punch at Tres Palmas; large glasses and unlimited refills. I made sure to hydrate myself. After eating I was taken to a cell by a stern looking prison matron. There was no solid door at the front of the cell; just bars. There was no privacy; just grim iron bars and a tiny slit of a window on the far wall.

Before being shoved into the cell the matron pointed at a small shelf in my cell and announced; “There are cosmetics and other items on that shelf. You will use all of them before you are allowed breakfast. I usually give the new girls an instruction pamphlet but after looking at you, Sweetheart, I don’t think you need one.”

“You can disregard having to use the tampons for the next few days if you want.” She paused to wait for a reaction or outburst from me. I remained silent. The matron continued her welcoming speech. “After breakfast Sara will shower and shave her legs before going to wardrobe for additional clothes.” I was pushed inside. The door slammed shut.

On my cot were my travisti sleeping clothes; a black two piece women’s pajama set that consisted of a short sleeved top and a matching tap pant bottom. The material was cotton with red trim piping. A matching short cotton kimono robe completed the set.

“Travisti” was stitched on both cheeks of the tap pants; my sleeping top and the robe had “Travisti” embroidered where my left breast would be. Of course the stitching was bold and pink.

I changed out of my short prison dress and into the provided night clothes. I removed my pony tails and brushed my hair. I don’t know why but I kept my bra on. I folded my dress and laid it neatly on a built in shelf. The cement floor was cold so I kept my heels on and explored my cell. My heels echoed on the cement floor.

One end of my cell had a stainless steel toilet bolted to the floor; there wasn’t a toilet seat. When you used the toilet you squat, in public view, on the metal. There was a small stainless steel wash basin, a similar unbreakable mirror and shelf. There was a single towel and wash cloth. I saw a half roll of toilet tissue.

The cosmetics the matron had mentioned were on the shelf; mascara, eye lash curler, a four color palette of eye shadow, red nail polish, nail file, tweezers and a sample size perfume. A small wicker basket held a dozen tampons. Three pink cotton panties in individual clear packaging had been provided. I absent mindedly picked up the polish and began shaking the bottle.

I sat on the edge of my cot, began painting my nails and pondered my plight. I must find a way out of this nightmare. I would hold back my tears until the lights were turned off. I didn’t want anyone to think I was a sissy; especially a prison sissy.

A brief moment later the incredulity of that thought made me laugh. I was in a foreign prison, dressed as a woman, with long hair, wearing lipstick, hoop earrings, a red bra and an anklet while painting my nails; and I recently had a sexual liaison, dressed as a woman, with a guy named Jack and I was lamenting that people would “think” I was a sissy! Damn comical. I was like a character in an XXX story that’s on adult cross-dressers porn websites.

Everything has a price and payment does not always involve money.

The next morning

I was awakened before dawn. A man in a suit and a corrections officer were staring at me through the bars. The suit spoke. “We’ve arranged for you to meet with a prisoner’s right advocate. Maya is a paralegal and is aware of your situation. She has copies of your files.”

“I want a lawyer.”

“Maya is very experienced; she has skills and has helped many people… even travisti. You should be happy that Maya will speak with you.”

“When will I meet this Maya person?” I asked. It was an effort to remain calm in demeanor and calm in speech. I need help… lots of help.

The Suit said, “It will be soon; perhaps today or perhaps tomorrow. She has an office in this building. Get dressed! You have much to do and you are keeping this officer waiting.” He turned and left.

The officer watched me use the toilet. Then she watched me get dressed and take care of my lips. She obviously wanted to see my tan.

Wearing black pajamas, red bra, kimono, three inch pumps, anklet and hoop earrings I was led to an open bay communal shower room. My plumped lips remained a bright red; it seems their lipstick is really a lip stain. I was given a cheap shower cap. I was allowed 20 minutes to bathe and shave my legs. My bikini tan was appreciated by many.

Shaving my legs would not have been a big deal except I was made to do it while sitting on a stool, with a bucket of water, in the center of the two story prisoner day room. I was going to be prison entertainment. The upper railings were packed shoulder to shoulder; I had an audience of admirers that all wanted to be my friend. With every stroke of my razor I received applause.

I finished shaving, rinsed and was drying my legs when a trustee walked over and gave me a travel sized bottle of moisturizer; it was the same guy that had attached my anklet yesterday. “I was thinking of you mi linda putita (my cute little whore).” He gave me a wink and quickly moved on. The spectators gave him a round of applause.

Still sitting in plain view I carefully moisturized each leg. Whoops and hollers came as I was doing it. Two hair barrettes, a tampon, half dozen cigarettes, a condom and a few coins were tossed at me.

I stood, slipped into my heels and retrieved the barrettes; I left the other ‘gifts’ on the floor. I returned to my cell to get ready for the rest of the day.

Yes, I am a travisti! But am I a sissy? Or am I a Sissy? I think so

Despite not wanting to be thought of as a sissy yesterday I applied the makeup left for me. In fact I used a tiny bit of the red lipstick on my cheekbones and rubbed it into an acceptable blush. I used the eye shadow lightly and the mascara liberally. The eyelash curler gave me nicer looking eyes; a dot of perfume and I was done. Is this how my mornings will begin?

I was allowed a very basic breakfast. Every breakfast included vitamin supplements; one to retard facial hair growth and the other to maintain health. There was always coffee and tropical punch for a beverage.

Wearing yesterday’s short sundress, three inch pumps and makeup I was taken to an area to get additional female clothes. Measurements, weight, height, shoe size, etc. were taken. I was sized for bras and silicon bra inserts. A staff member with a name tag saying “Toni, Wardrobe Mistress” would be selecting my clothes. I stepped up to her desk.

After scrutinizing me, for what seemed like a long time, Toni glanced at her large man’s wristwatch before speaking. “Are you Sara, Princess?” she asked. “Yes, I’m Sara.” My feminine voice surprised her. Toni took her time in checking me out again from head to toe. Toni stared at my fingernails and my plumped red lips. She looked puzzled. “You’re cuter that I expected… what’s your favorite color, Sweetie?”

“Robin Egg Blue” I replied. She snorted but said nothing; she began filling my bag with clothes.

Toni wore no makeup, her hair was short cropped and slicked back; her demeanor screamed dyke. The billfold in her back pocket confirmed it. Toni glanced at me several times. She wanted me to know that she was mentally grading me; I knew. I sat there and tried to look pretty for Toni.

Her name tag proclaimed her as ‘Wardrobe Mistress’. Someone had taken a black felt tip marker and had drawn a line through the word ‘Wardrobe’. ‘Mistress’ seemed to define her and her attitude. I took note.

Mistress put my new clothes into a large clear trash bag; a smaller black bag was rolled up within the main bag. Mistress dropped the clear ‘suitcase’ onto the table where I was sitting. I thought I saw her wink at me. I saw an ugly plain white bra was inside my bag.

Noticing what I was looking at Toni smiled and sat down across from me. “Look, Sweetie, let me explain a few things. These clothes are just to get you by until the more appropriate clothes of your new profession can be arranged.”

“I’ve included something in the black bag that I think will look good on you. When you are moved to the Convent your clothing options get better.”

I must have appeared surprised

Mistress was staring at my crossed legs and red toenails. “Cute legs like yours look even better with stockings and nice heels… but I’m pretty sure a cute travisti like you has been told that more than once. Isn’t that right, Missy? I bet you’ve have a lot of boyfriends; all sissies do. Do you have girlfriends too? I do.”

I changed the subject by asking, “What about shoes? These pumps don’t seem right for the job.”

“There must something about women’s shoes that excites travisti; all you girls ask about shoes. What sissy-boy wouldn’t be happy wearing pumps like you’re wearing now? You get nicer shoes and stockings when you get to the Convent.”

I grabbed my bag and stood to leave. “Thank you, Mistress, for your help.” I curtseyed for her pleasure. Toni smiled broadly. “Wait a minute, Sweetie.” She quickly returned with a smaller plastic bag. It contained a 34B light blue underwire pushup bra; definitely not standard issue. “Here you go, girly. Mistress wants to make you happy.”

I blushed but quickly took the bra. I was truly appreciative. I quickly looked around and then did a half curtsey. “Oh, Mistress that’s so sweet of you!” I gushed.

Mistress continued, “The white bra in your bag is only an A up. One look at you, Missy, and I can tell that you’re easily a B. In fact the food and punch at the Convent will have you spilling out of a B cup within two months. You will need a larger bra soon. Come visit me and I’ll fit you myself.”

My mind pondered on her reference to tropical punch and me needing a larger bra soon.

Mistress was still contemplating things. “Come back when you have the time so you can try on a couple of things. I’m very good at fastening stockings to garter straps Precious; I get on my knees.”

I knew better than to go down that rabbit hole.

“Yes, Mistress, but I have an appointment now” I replied. I tried to look a bit sad.

“No problem, Sara. Maybe I can see your bikini tan sometime… soon?”

I said nothing but I did a full curtsy, held it a moment and left.

I took my new clothes and retreated to my cell. I needed to get changed but first I needed to lie down and relax; deep inhales and long exhales. It worked.

An officer loudly shook my cell door to get my attention. “Pull your sissy-self together Sweetie; you have an appointment with Maya in 30 minutes. I even brought you some punch.”

I opened the black bag that Mistress had given me. The items were perfect! I held a blouse to my chest. For a few moments I was happy again. I was so grateful for her selections that I was tempted to take me and my bikini tan back for a visit.

I wore the items that Mistress had selected for me

Mistress had selected a cute denim romper and a puff sleeve v-neck peasant blouse. It had a pretty ruffled neckline. My shoes were the same three inch leopard pumps from yesterday. I wore my hair in a high ponytail and was able to use both of my new barrettes. I brushed my bangs and reapplied my plumping lip stain. My cross body purse held my essentials. I was ready for my meeting with inmate’s rights representative Maya.

I was taken to Maya’s office

I knocked and Maya opened the door to her office and stared. “Steven?” she asked. She was clearly shocked at my appearance. I think my clothing, nail polish, makeup and heels had her confused. “Steven Upton?” she asked again. I nodded my head in the affirmative, dropped my voice to ‘Steve’ mode and replied, “Yes Maya, its Steve.” I then reverted to my Sara voice and continued, “Under the present circumstances it would be best to refer to me as Sara.”

Still staring Maya managed a “Wow! You look so… ”. I completed her sentence with, “I look so feminine; like a woman… like a sissy? I’m pretty sure that’s their plan.”

Composing herself she agreed, “Yes, all of those things…and more; Sissy comes to mind. Are you sure you’re a boy? Your voice is so very femme.”

“Yeah, I’m sure but I don’t think I’ll be so sure if I stay here much longer. What were you expecting?”

Still taking in my image she passed me an 8x10 booking photo of Steve. “This is what I was expecting.”

Pointing at the photo I lamented, “I don’t even know that guy anymore.” I shook my head.

Maya’s eyes were following my swaying ponytail.
“Yes, please come in and have a seat.” Giving me a prolonged visual inspection Maya said, “Cute dress, nice hair, pretty heels, nice makeup, large hoop earrings and wearing perfume…. you are one hot babe aren’t you? Are those tits real? It usually takes longer.”

I shook off her comments and said, “I’m a boy that’s about to become a state owned whore. In a few days I’ll be a working girl at the Convent. The clock is ticking. I need a lot of help.”

I hung my purse on the back of my chair and sat down, intentionally crossing my legs like Sharon Stone did in Basic Instinct. “It’s damn ironic that this is happening to me.”

Maya spoke. “We have a lot to do before they transfer you to the Convent.”

Set Up?

As Maya was sitting down she was mentally evaluating her client (me). “Sara, it seems that looking like a woman is nothing new for you. My sources inside and outside of jail say you that you’re sporting a pretty bikini tan. Is that true?”

“Yes, it’s true.”

“I want you to know that the mental image of your bikini tan endeared you with the Convent’s recruitment committee. You, Princess, brought attention on yourself starting at the airport. You made yourself the perfect fall ‘girl’ for their needs. I think that you were set up.”

“Set up?” I asked.

“Your situation is pretty interesting. I’ve been reading your file and several things don’t seem right. Their expired visa claim makes no sense. Your credit card is good but someone put a security hold on all charges. Tres Palmas and their satellite shops kept submitting your bills, knowing that they would not be paid. After a few attempts they claimed you’re a dead beat American scam artist. And there are other irregularities about your conviction.”

“Irregularities?” I asked. A faint glimmer of hope had been sparked.

“Yes. Before I go on you have to do something for me.”

“Oh, you mean we need to discuss your retainer and fees?” I asked.

“No. You need to sit and cross your legs like a respectable woman. You’re distracting my train of thought; and pull your hem down for god’s sake! Save that demeanor for the first sweaty rich guy that will be pawing you in a week. As you just said the clock is ticking, girly.”

“Sorry.” I smiled sheepishly and complied with her request.

“I have your cell phone and have been discreetly contacting your friends in an effort to see who may be able to help us; who could vouch for your character, write letters, etc. Too bad there’s not a US Senator among your friends.”

Maya would continue to make calls and send emails to friends and advocate organizations while we explored my options to be pardoned, acquitted and released. “Avoid any contact with my parents for now” I implored. “I’ve never caused them any trouble; we have a mutual agreement. Always have, always will.”

I had a little more than a week before being prostituted at the Convent.

A knock at the door

There was a knock at Maya’s door. She signaled me to shut up. A correctional officer stuck her head in and said, “Sara has her medical exam in 30 minutes. Wind things up and send her out.” The office door closed.

“Sara I’m not sure how your case will go. We may have to resort to extreme measures.”

“You mean like sending me a cake with a file in it?”

“This is no time to be joking. We’ll explore all legal resolutions but I am not ruling anything out.”

“You need to be aware of what you’ll be going through while you’re here. I’ll send an associate to explain things. We’ll get back together soon. Go to your exam.”

Maya obviously knew the subtleties of how to get things done for inmates. As a prisoner rights activist she could help me. I had to trust her.

The Medical exam

I expected to be subjected to a full body cavity search and a total head shave. All of these things happened except the haircut. It was explained that facial hair was forbidden and long hair was mandatory for travisti whores; I had to look and act feminine at all times.

Blood, urine and sperm samples were taken to check for STDs. Inoculations and injections were given.

“Travisti receive weekly injections that block facial hair growth while stimulating certain feminine attributes. Our clients are expecting a cute Americano boy travisti. There are no women prostitutes at the Convent only chicks-with-dicks.”

“No females?” I asked.

“There are ‘women’ here but there are no females.”

I was given a hospital gown and told to strip and put it on. “Lie on your back and put your feet into the OB/GYN stirrups.” The tech was pointing at a steel exam table.

I donned the gown and lay down on the table as instructed.

The technician walked to the foot of the exam table, gloved up, lubed several fingers and grabbed a flashlight. “Why are you doing this?” I weakly asked.

“We need to inspect your rectum and collect a semen sample. Relax and let it happen.” The technician got his samples. The tech made notes on a clip board.

The examination progressed to my chest. I was ordered to stand up and open my gown. As soon as I did the tech stared and smiled. “My, what do we have here? I could swear I’m looking at a 16 year old girl; your titties are pleasantly puffy.” He pressed his hand to my right breast and cupped it; I filled his hand.

The tech stepped back and took in my infamous bikini tan. “Your tan makes it look like you’re wearing a bikini even though you’re naked! It’s a very sexy image especially on a boy.” The tech was staring… and becoming “distracted”.

He collected himself and resumed his examination of my breasts. He gently rubbed my nipple and it erected instantly. “Good physical response to nipple stimulation.” He softly pinched my nipple. “Your nipple feels just like a nursing woman’s teat; if you start to drip or seep from your nipples see a doctor immediately” he advised. He got the same response from my other breast. Picking up a cloth measuring tape he performed the traditional bra fitting routine. More notes.

I began to put the gown back on and was told, “Wait a minute, I’m not done yet.” I looked puzzled. He stroked my nipples to get them as erect as they could be and measured how far they extended. His touching had me squirming; an erection was beginning on both of us. The tech noticed and smiled. “My, it appears that Sara likes having her pretty titties touched, is that right?” More notes were added.

“We’re almost done Sweetheart, just one more thing. We need to see how big your areoles have become.” I was measured. “Your areolas are a respectable 1.5 inches in diameter and are a very nice brown; they contrast nicely with your tan. Your nipple size, length and responsiveness would be normal for a 16 - 18 year old girl.”

I looked down at my tits. Yes, they were puffy and pert; my areolas were 1 ½ inches wide; the diameter of an old silver dollar. My nipples seemed engorged. I was surprised and pleased at the same time. Why didn’t this happen to me at home?

I asked for the findings of my exam

“You are disease free. No contraband was found. The puffiness of your breasts is encouraging as are your large areolas. Your bra size is 34 with a B+ cup size. Your titties are that of a young woman. You are progressing nicely. The Convent will be pleased. I’ll pass your measurements to our wardrobe department. You’re going to need a larger bra in the near future. You will do well at The Convent.”

A larger bra? Facial hair suppressant? Progressing nicely?

I was very confused. I was healthy but I had breasts. It made no sense. Was my breast growth solely related to the breast cream at Tres Palmas? Why didn’t somebody say something? Why didn’t Lauren say something? How could I have missed noticing that my tits were growing?

I grabbed my purse and left.

The day after meeting Maya: in-processing, education and marketing

A photo shoot (much different than mug shots) was needed for Convent marketing needs. It resulted in 4 or 5 photos of me in various feminine clothing, lingerie and poses being added to my profile on the Convent’s online menu; a menu of all the girls. The Convent has an app and website where you can pre-order whoever and whatever you desired. I was told their website gets many views from all over the world. I could be recognized wherever I traveled based on my Convent marketing photos.

Explanations

True to her word Maya sent her associate, Juana, to explain Convent life. My womanly voice flabbergasted her. “You sound so femme! How do you sound so real?”

“I practiced a lot for many years; what you hear is now my normal voice.” I impatiently asked if Maya was making progress on my case.

“Maya is exploring many things including loop holes in your arrest. She’s also exploring other options including contact with International Prison Rights organizations. We may start a ‘Free Sara’ movement. We’re looking into paying a fine or posting a bond. You may have to attempt an escape. We just don’t know. An opportunity may arise with little or no notice. Be prepared, Sweetie. Keep your purse close.”

Juana then went on to clearly explain what I was about to go through. She passed on a lot of information that I won’t bore you with. Here are the basics.

Processing takes about 7 days. I would be shown travisti sex training videos and get coaching from Convent girls before beginning my whoring at the Convent. I am to be an actress, making each customer believe that I truly enjoyed pleasuring him/her.

Rules, procedures and what to expect

Clients, John’s, tricks, customers are serviced 24/7; customer needs and satisfaction determine everyone’s work day. Prison whores have no days off. Free time, if any, would most likely be mid-week.

Boundaries, safety and health

Pretty simple: No pain, no blood, no hard drugs, no BDSM, no sex acts involving urine-fecal, no bullies, no choking, don’t cause trouble, no cameras, everyone disease free, everything mutually consensual, yada yada.

Monday’s are medical day where all girls are tested for disease and given their weekly shots. Thursdays are salon days where girls have their hair and nails done before the rush of weekend John’s.

Once a date is over whores are to return to their room and report that they are available for the next customer. Girls would be told when a pre-booked client arrived.

Usually a girl is allowed 90 minutes of free time between ‘dates’ to refresh, shave, douche, gargle, shower, change panties, etc. Makeup and nails must be impeccable 24 hours a day. You could always work on maintaining your tan.

The date form

Juana explained what a Date Card was. Girls usually receive a Date Card the day before their ‘John’ arrived so his or her needs can be met. A Date Card could request a variety of things: Clothes, costume, sex acts. They could request a brunette travisti in overalls and pink hair or they may request French maid attire for themselves; the Convent offers many options and fantasies to pre-schedule and pre-pay online.

Juana handed me a Date Card. “Take a close at THIS card Sweetie and tell me what you think.” I took the card and said, “So? What am I looking for?” I asked.

“I’d look real close because this Date Card is for you. You’re up to bat in three days, Sweets! It seems you already have a following; perhaps due to the TV news clip of your ‘perp walk’. You looked so … sexy and desirable.” Juana blushed. “We pulled a lot of strings just so you could get advance notice.”

I went mentally numb; my hand began to shake. I read the card twice. In exchange for money I was going to be fucked by a stranger in three days whether I like it or not.

“The Convent will give you your actual date card the day before the big event; act surprised.”

With my luck my first trick would probably be Wilma, Jackie or Juana!

My first ‘date’ form

My date wanted me beginning at 12 noon.

I was to wear a mini sundress with a very short hem line. The dress would have puff sleeves; ruffle trim would be nice but was not mandatory. I must wear open toed black patent leather pumps with a minimum 3 inch heel. Black garter belt with black stockings, gold drop earrings with a matching gold neck chain were required.

My hair was to worn down with a flower behind an ear. The client specified heavier evening glamour makeup. Lipstick and nails were to be bright red. Red panties were to be brought but not worn when my ‘date’ arrived. I was to make a point of sitting with my legs spread wide so my ‘trick’ could see my penis; I was to ‘flash’ him.

My date wants oral pleasuring and wants to shower with me. He paid extra for bareback sex. He paid for a three hour date.

Juana and I talked for awhile and then she left. I told her how grateful I was for her information. Knowledge takes the edge off of the unknown. I puckered my painted lips and blew her a kiss. She blushed again.

A couple of days passed without any word from Maya. I was very nervous.

Just as Juana had said one morning, after breakfast, a corrections officer came to my cell and handed me the Date Card that Juana had shown me. With a smirk on her face the officer said, “Well, Girly, you are finally going to earn your keep beginning tomorrow; report to the salon in 30 minutes for your date prep.”

Pre-date prep: The day before my first ‘date’

I was taken to the Convent beauty salon for last minute refinement. I had come to like off the shoulder peasant blouses and was wearing one with a romper for my salon appointment. I wanted to be comfortable. The salon was a nice break.

A Convent cosmologist evaluated my face to see what was needed. She gazed at me intently. “You may not remember me but I helped with your mug shots. I recognize your eyebrows. My name is Tina and you are Sara.”

“I do remember you; you were aching to fix my eyebrows.”

“Sara, you are prettier now than the first time we met; your bust looks amazingly larger than when we first met. The Convent vitamins are truly impressive. I’m glad that I was assigned to work on you today. We have lots of time to make you prettier. Your date requested a bold evening makeup. That is a “Trick-speak” term for ‘hooker look’. Do you have any preference?” Tina asked.

“No. You can choose whatever best suits my skin tones; just make sure I look sultry when you’re done.”

“No problem Sara, sultry it will be. When I’m done don’t waste your time with makeup remover. You won’t need to redo your eyes, brows or lips for a couple months.”

Tina went to work. I sat still and let her do her job.

My brows were thinned, shaped and dyed. She also died my eye lashes. She told me to not try curling them for a few hours. Next was semi-permanent eye shadow and eye liner with the ‘winged cat-eye’ effect that was all the rage. Tina applied my facial makeup and plumped my lips.

When she was done Tina handed me a mirror.

The effect was impressive. The eye shadow in combination with everything else completed the provocative look my ‘John’ wanted. I was pleased. I looked hot! I was about to say that I looked like a call girl but why state the obvious?

“What do you think, Sweetie?”

“You did a fine job Tina. My mother wouldn’t recognize me.” We both laughed at the irony of the situation.”

“Your date will be impressed.” Tina came over and took a selfie with me. “By the way your makeup can’t be removed; it will fade in a few months and we can start over.”

Hair styling and a mani-pedi

My hair was now below my shoulders; I was given a long lasting perm with a medium curl. My stylist insisted on adding highlights. We both thought my hair and my first acrylic nails looked sexily beautiful.

I stood to leave. I tugged my skirt into place, grabbed my purse and was about to leave when the salon manager approached me with another glass of the punch I had been drinking all day.

“We just got in a few new magazines, Honey, so why don’t you have a seat in the lounge, catch up on the latest fashions and let your makeup set. I’ll make sure that you don’t get in trouble. Besides you sitting in the lounge and looking so pretty will be good for our business. Help yourself to snacks… and punch.”

“Thanks” I said. I went to the lounge and began reading. There were tasty tea cakes and incredible petits fours at a self serve wet bar. I stayed for two hours.

My first “date”

My ‘date’ was scheduled for 12 noon. I was led to a sex suite for my first act of prostitution thirty minutes before my ‘appointment’ by a well seasoned old travisti named Maria. She was acting as a reassuring and experienced guide. Maria had serviced many clients but was getting too old for some clients and had been assigned to help us new ‘girls’.

I needed the time to settle my nerves and to get into my role of being a travisti hooker. Like a good whore I had read my Date Card and knew what I had to do. I had to give a stranger a blowjob, massage his prostate, allow him to sodomize me without a condom, shower with him and make him believe I was happy to be with him. There were other requests but I decided to let my ‘John’ guide me.

All I had to do was look pretty, dress in a specific manner, with no panties, wear a flower in my hair, spread my legs and flash my ‘date’ a look at my penis whenever I could. I planned to be flaccid at first.

Maria made a quick inspection of the suite to insure all was in order; condoms, lube, lounging robes, ice, glasses, mini-bar and working panic buttons. She produced a pretty pink and white carnation from a box and pinned it behind my right ear as I requested. Giving me a final inspection she said, “Your John will be pleased. You’ll do well. Use the panic button if you feel threatened and I’ll come and kick his ass! When your date is over be sure to report in that you’re available for your next trick.”

“My next trick?” I asked incredulously. “Yes, Honey, you are not on vacation. You are a paid puta (whore) and there will always be a “next” date.” Her comments were humbling. She patted me on my ass and left.

I was left staring at a king size bed knowing I would soon be lying on my back and guiding a cock into me. I had pre-lubed my boy-pussy as part of the Convents routine protocols. Time would be spent on my knees satisfying my John.

I poured myself a soft drink filled with lots of ice and walked to a sitting area near a floor to ceiling window that looked out on a beautiful swimming pool. I like rooms with a view. Since I had been paid for I sat so the sunlight from the window would let my date have a better view of me.

After placing my beverage on a coaster I removed my panties, put them in my purse and sat down on a fabric covered Queen Anne wing back chair. My sundress would serve to keep the chair cushion clean. I closed my eyes, sat back and waited. I made an effort to calm myself; almost dozing off.

A firm knock followed by a clicking sound at the entry door to the suite snapped me back to reality. It was a few minutes before 12 noon. My heart began to race. I resisted the urge to freshen my lipstick. “Be a classy cock sucker” I told myself. In order to tease my ‘date’ I did the Sharon Stone leg-cross as an affectation so I could ‘accidently’ expose my boy bits at an opportune time. I was his ‘chick-with-a dick’.

The door opened and my ‘date’ came in. He didn’t see me at first because the sitting area was tucked around a corner about ten feet from the bed. He had no luggage. My ‘Daddy’ looked at his wrist watch; his back was towards me. I remained silent. He was wearing a large cowboy hat, dark glasses and a mustache (yeech!). He looked tall.

He sat down on the bed, looked around and finally made eye contact with me. He froze but continued evaluating what he had ordered. The game was on.

I opened with: “Hello darling. I’m glad to see you. I’ve been dreaming about you for days. It’s been a long time since I’ve been with a handsome man like you.” I remained seated; with legs crossed at the knees I absentmindedly toyed with the flower behind my ear. My date remained silent.

I let one high heel dangle from my foot. I leisurely flipped it about like I had seen in a movie; I thought it was a sexy move. My legs remained tightly crossed. His dark glasses and hat kept his face in shadows; it was difficult for me to read him. I was hoping for a ‘tell’.

Remaining seated on the bed he firmly said, “Stand up.” His voice didn’t sound mean.

I remained seated and uncrossed my legs and slowly spread my legs. I placed my hands with their bright red nails on the inside of each thigh and spread my legs wider; red nails and a white cock. He nodded his approval.

I stood and did a slow 360 degree turn. Facing him I spread my legs about two feet apart. I did not approach closer. Ever so slowly I pulled the hem of my sundress up allowing about three inches of my cock to be seen. I swayed my hips just enough to have my dick slowly swing back and forth like a flesh pendulum. That got his attention.

‘Daddy’ remained seated. “Remove your dress, honey” he ordered. I tried to do a sultry strip tease. I tossed my dress onto the chair I had been seated on. I was left wearing the requested garter belt, stockings, red bra, hooker makeup, drop earrings and a flower. My hairless dick was dangling.

I made a show of adjusting my garter belt and straightening my stockings for the benefit of my ‘John’. ‘Daddy’ smiled and gave his crotch a few rubs. I knew he was repositioning his penis. I’ve done the same thing before in a different time and in a different world.

“Very sexy, very pretty Sara; I like hairless cocks” he said.

“I shaved everywhere just for you” I lied. I lifted the hem of my dress and swayed my penis again for his viewing pleasure. He rubbed his bulge again.

“Remove your bra.” Maintaining eye contact I unhooked my bra from behind. I dangled it for a few seconds and without looking tossed it, over my shoulder, directly on top of my dress. He appeared surprised at my accuracy.

Seeing my puffy teenage tits and large areoles pleased him. I licked a finger and began rubbing a nipple. I cupped my perky breast and offered it to him; I was being an actress. He was becoming restless.

I waited for his next command

My ‘John’, stood up and called my name. “Sara, come here” he softly said. “Yes, Daddy” I said. I met him at the end of the bed. He was tall. I reached up and kissed him passionately on the lips. His dark glasses and hat were beginning to annoy me. I needed to see his eyes.

“Slowly unzip me, Sara”. It seemed more like a request and not a demand. I stepped closer and took hold of his fly. I stood on my toes and kissed him again before beginning to lowering his zipper. I cupped his crotch with my other hand and gave his cock a gentle squeeze. I continued opening his fly. He definitely had a hard on; and so did I.

His zipper was open. He began French kissing me. I reciprocated. ‘Daddy’ was finding his passion. ‘Daddy’ definitely likes travisti. He cupped my testicles and then took hold of my growing erection. He stroked my shaft sensuously which increased my erection. I do believe he was trying to warm me up. It was working very well; a drop of pre-com appeared. I still had not touched his cock.

Without being asked I unbuckled his pants and they dropped to the floor. ‘Daddy’ stepped out of them. He was wearing black silk boxer shorts (or were they women’s tap pants?) with a dark wet spot.

My date continued stroking my penis. It was marvelous. I twitched for him. I felt decadently and gloriously slutty. Releasing his grip on my cock he put his hands on my shoulders and guided me to my knees. My face was level with his crotch. I didn’t move or say anything. I waited. ‘Daddy’ glanced at his watch.

Looking down at me he said, “Your online photos don’t do you justice, Sara. You’re the prettiest boy I’ve ever been with.” I said “Thank you, lover”. My gaze returned to his crotch. I was so damn excited that I reached over and stroked his rigid penis through his silk boxers. It felt marvelous for both of us.

“Don’t let my boxers get in your way, darling. Pull them down.” I didn’t need a second request. I eagerly pulled his boxers down to his ankles and was now staring at a beautiful eight inch circumcised erect cock; it was everything I had hoped for. I licked my lips.

Looking into ‘Daddy’s’ eyes I leaned forward, and gave a prolonged kiss to the tip of his dick. I leaned back. We both admired the red lip print I had left. I wanted more than the tip; I wanted all of it.

‘Daddy’ sat on the edge of the bed, kicked out of his boxers and spread his legs. I eagerly scooted between his legs and began teasing his hairless testicles. Oddly enough his legs and pubes were hairless. I shrugged it off.

I wrapped my hand around his vibrant penis and started to stroke his shaft like he had done for me. I softly said, “Look how sexy my red nails look holding your cock. It looks yummy to me.” ‘Daddy’ throbbed.

I pulled his erection to my lips and kissed it again. I spread his pre-cum with my thumb before running my tongue around his pee-hole and frenulum. I stopped. I wanted ‘Daddy’ to ask me to do what I was about to do. Both of our breathing rates were above normal.

‘Daddy’ reached down and gave my cheek an affectionate rub. “Sara, do what you’re aching to do.” And with great pleasure I became a paid cock sucker; a travisti puta.

I licked, sucked and made love to ‘Daddy’s’ penis. I was wondering if I should start on his anus; after all it was on my Date Card. I began slowly bobbing up and down his shaft while tickling his testicles.

I was beginning to extend my middle finger to his boy-pussy when I stopped and let his rigid cock pop free from my lips; a clear strand of precum ran from his dick to my lips. I wiped it free with a finger and for his enjoyment I licked his wetness off my finger tip and smiled at him. He said and did nothing. Maybe I should have offered him some.

“Did I do something wrong? Should I have offered you…” ‘Daddy’ cut me off in mid sentence. “No Sara, you were perfect. It’s me.” He helped me to my feet. I was puzzled and I was erect.

Still sitting on the edge of the bed ‘Daddy’ grabbed my hips and pulled me closer. My high heels elevated me enough so that my erect dick was level with his face; a clear droplet awaited him. Looking at my erection he pulled me closer. “It would be a shame to let this get away from me. I’ve been thinking about this moment for a long time.” I was puzzled even more.

‘Daddy’ kissed the tip of my dick and licked off my pre-cum droplet. To my great surprise and delight, he took my cock into his warm and eager wet mouth. My knees almost buckled. It became obvious that he was an experienced cocksucker. His mustache at the base of my shaft felt strange. I spread my legs. ‘Daddy’ took the hint. It felt so good that my legs began to shake.

‘Daddy’ stopped and withdrew his finger; neither of us had orgasmed. Instead he kissed me on my neck. “Put your dress on Sara and pull yourself together” he instructed. By the time I had gotten dressed he was also dressed.

“Sit with me on the bed. We need to talk.” The customer is always right. “Yes, Daddy” I said. I brought my purse and sat cross legged on the bed facing my client. He watched intently as I reapplied my lipstick and brushed my hair. I made sure to spread my legs. My now flaccid penis was in plain sight. I wiggled my hips and made my penis flop about. It was like fishing for trout; twitch the lure if you want to catch fish.

“Is there something I can do for you, lover?” I asked. “You certainly did all the right things for me.” ‘Daddy’ shook his head and laughed. It was a sincere laugh.

‘Daddy’ looked at wrist watch. We’d only been together for an hour and he’d looked at his watch four times. Maybe he had another ‘date’.

‘Daddy’ patted my inner thigh and began, “Sara, life can be strange”. ‘Daddy’ finally removed his damn cowboy hat and sunglasses and stared at me. Getting no reaction from me ‘Daddy’ reached up and peeled off what turned out to be a fake mustache.

I was puzzled but not impressed. I was searching my memory for something from a long time ago; summer camp perhaps?

Seeing that I hadn’t connected the dots he reached into his billfold and took out a business card. He handed it to me. “Castle Research, Dan Richards, VP, International Trade Development.”

“Sara, I’ve come to take you home.”

I immediately passed out.

I’ve come to take you home

When I regained consciousness there was a cold damp wash cloth on my forehead. I lay on the bed motionless; my eyes were fluttering in confusion. I didn’t know where I was. The last thing I remember was sucking a man’s dick, in a foreign country; in a hotel room, without panties; wearing a garter belt. My memory was returning.

Dan was patting my hands and talking soothingly to me; “It’s going to be alright Sara; you’re safe now.” He helped me sit up. My eyes focused and my brain cleared.

“My god!” I exclaimed. “I met you at an airport a long time ago… you were the guy that said my hair would look nicer without a pony tail… you had nice fingernails…you like boys like me…your name is Dan!”

He nodded and said, “Yes, Sara that was me. I’ve come to take you home.”

My eyes got big with surprise. I lunged for him and hugged him tightly. I began crying and sobbing uncontrollably; my body shook. Dan hugged back and was gently rocking me as I sobbed.

“It’s going to be alright Sara but we need to get moving if we want to escape this nightmare. You need to compose yourself. I’ll explain as time permits. Dan looked at his watch. “Splash some cold water on your face, redo your makeup and we’ll go; there’s no time to dawdle.” My sobbing had died down as had my post sobbing quivers.

Before getting off the bed I kissed Dan deep and passionately. My nightmare would be over if we could get out of the country. I used the cold wash cloth to refresh myself. I quickly returned to Dan. I felt a relief that’s unimaginable. I kissed Dan again. I grabbed my purse and said, “Tell me what we have to do.”

We sat at the table where I was seated when Dan first arrived.

“First off I’m sorry to have fooled you in such a shocking way. Since I first saw you at the airport I’ve been consumed with finding you. Maya found you for me. She explained that you were sentenced to be a whore. I wondered how far you would go; you clearly showed me. Before flying here I planned that if you went down on me that I would reciprocate. I’m attracted to chicks-with-dicks.”

I nodded. “Neither of us had an orgasm,” I whined. “There’ll be plenty of time for that once we get out of here” Dan said.

“Listen close. My presence here is primarily due to a phone call from Maya. She said that you had been set up. We discussed the few options we had that could free you. I used my position, money and a bluff to bribe those that had the authority to free you. That was done a week ago.”

“What gained your freedom was when I brokered a lucrative import/export deal between the Minister of Agriculture and an offshore investment cartel. The Minister wields a lot of clout. He made your arrest ‘go away’. I earned a nice commission too.”

“We need to be in the air within two hours or all my work and your freedom will be forfeited. My corporate jet is fueled and waiting 30 minutes from here. Leaving the country dressed and looking like you do will be impossible with your current passport. I lifted one of the Convent’s photos of you from their website and had forged documents made for a ‘Miss Sara Lovely’. If asked you are my fiancé. Do you understand what I’ve said?”

I nodded and said “Yes”.

His reference to ‘Sara Lovely’ stirred distant memories. Heck, I was willing to becoming Sara Richards!

“Good. There’s more to it. I’ve arranged for all of your belongings to be put aboard my jet. This includes everything from your apartment and all your stuff from the Convent; it all fits in a large cardboard box. In fact a tough old bird named Toni was a great help in getting your files and belongings out of the prison. Apparently you made an impression on her.”

“She liked that I called her Mistress and gave her some respect. She was very nice to me.”

“Did you really curtsey to her?”

I chuckled at the memory. “Yes. She deserved a curtsey. I’ll tell you more when we’re safe.”

“Put your panties on and let’s go. We certainly don’t want to call attention to ourselves. Until we get to Mexico City we must look and act like a couple. We’ll hold hands, kiss, whatever it takes. If we do it right we’ll just casually breeze out of here, past security and into my waiting town car. If we fail we’ll both be wearing short dresses and working here for a long time.” I smiled at the image of Dan in a dress.

“I want to see that someday; you in a dress. Maybe that explains your shaved legs.” Dan ignored my comment.

I retrieved my red panties from my purse and quickly put them on. I wanted no problems now that freedom was so close.

Dan put his arm around me like lovers do and walked us through the lobby, out of the Convent and into his limo with no problems. He held the door open for me like a gentleman and closed it once I was inside. He went to the other side of the limo and was soon sitting next to me. We held hands and snuggled. This was not play acting. He began kissing my neck. “Damn you smell good Sara Lovely. Your hair is gorgeous. The flower behind your ear signals that you are available. Are you?” We kissed. I was definitely available.

We were soon at a private airport. We parked, in the shade, near the waiting jet. Dan wouldn’t let us board until a courier brought him a package. Time was getting short.

Dan explained that that all of my luggage had been retrieved from Tres Palmas and the Convent and was already on board the jet. We would be spending three or four days in Mexico City while he conducted business; International Trade Development. We would need those days to figure out what passport I would be using to re-enter the US. Would I enter as Sara? Do I need a ladies passport? Will I go through withdrawals

If Steve was re-entering I would need time to de-femme. My eyebrows, makeup, puffy red lips and obvious tits would not work if I tried entering the US as Steve. Things needed to be well thought out.

A distant car horn announced the arrival of Dan’s courier. Dan stepped out of our air conditioned limo and greeted the courier. The two spoke briefly. Dan was handed a brief case. Placing the brief case on the hood of the courier’s car Dan opened it. He poked around inside, nodded his head and closed it. I saw Dan hand the courier an envelope containing $100 US dollars.

Dan climbed back into the limo with a huge smile on his face. “Are we ready to leave, ‘Daddy’?” I asked. He nodded in the affirmative. “That worked out quite well.” Dan gave me a kiss and exited the limo; he walked around and opened my door. He took my hand and helped me out gave me another kiss. His kisses made me happy. I was about to be a free woman. “It’s time to go, darling; we have a seven hour flight.” We boarded the corporate jet.

I kicked off my heels, reached under my dress, released my stockings from my garter belt before taking a seat on a nice leather love seat; I would remove my stockings and garter belt later. Dan knelt and rolled my stockings off my legs; he briefly massaged my toes and feet before sitting down next to me. His massage was delicious. He placed his hand on my inner thigh.

I leaned my head on Dan’s shoulder like a young woman with her boyfriend at a movie theater. I closed my eyes and tried to mentally shed all that I had been through. Silent, but happy, tears ran down my cheeks. Dan put his arm around me and gave me a hug. It was very calming. I felt safe. It was a secure feeling sitting and relaxing next to my man. I briefly nodded out.

I awoke about twenty minutes into the flight. Dan was still beside me; his hand still on my thigh. He leaned over and kissed me on my forehead. “Did you have a nice nap baby doll?” he asked. I squeezed his arm, smiled and softly said “Yes it was a good nap.” I placed my hand on his inner thigh. Dan spread his legs. I resisted caressing his crotch. There would plenty of opportunity for that later.

“What did the courier bring you?” I asked. Dan reached under our seat and put the briefcase on his lap. Opening the briefcase he removed a large sealed envelope and handed it to me. “Open it” he said.

I tore open the envelope and my passport, visa, driver’s license and cell phone dropped into the lap of my sundress. “What a great relief! Our lives will be so much simpler now.” I began to cry again. “Damn hormones!” I said. Dan patted my leg, leaned over and kissed me.

“Does this mean I won’t need a passport for Sara? I’ll be allowed back into the US as Steve Upton? Must I become Steve again?”

Dan became serious and thought before he answered

“Sara, I’m not sure how this will play out; there are lots of loose strings and variables over which we have no control. We’re not going to fly into US airspace until we have a plan. Are there warrants out for you, Steve, me or this aircraft? Have documents been revoked? Can we butch you up enough so you look like Steve? There’s not a trace of maleness when I look at you.” He tapped my closest puffy breast.

“We need to resolve your living arrangements. I personally like pretty boys with puffy tits. Maybe I’ll have to take you home with me for a few months before you see your parents. I could tell Customs you are my fiancée and you could tell your parents that I am your fiancée. I doubt you’ll want to see your parents until they can accept your appearance and my presence.”

My heart began to race at those possibilities. I would welcome becoming the submissive companion/wife to such a warm and protective person. I was feeling very fragile and vulnerable.

“Tres Palmas and the Convent have been feeding you female hormones since you arrived in country. I’m sure you’ve noticed that your tits are puffy, your nipples and your areoles are large and brown; your permed long hair is beautiful feminine. Quite frankly I’m jealous; I love your look. Luckily we have a few days in Mexico City to sort you out. We need a plan before your mom sees you.”

Dan was correct. We need to do something before mom sees me. We need to think things through. It would take a long time for the lip stain and semi-permanent eye makeup to fade. In the interim I would need everyday go-out-in-public ‘normal’ women’s clothes in order to get by. Dressing all the time the way I looked now would not be wise.

“I’ll need some new girl clothes” I thought.

My mom had been worried that I’d come home from vacation with a Caribbean vagina from an offshore clinic so, by comparison, “only” having tits and wearing makeup should be no big deal. I knew I would never let my tits and areoles revert. Explaining Dan would be more problematic. Perhaps this is the ideal time for Steve to go and Sara to stay; that event is inevitable.

Noting that I was despondent over his last statement Dan held up a very thick, official looking 8x10 envelope. “This, my dear, contains all your original court and Convent records; it’s as if you never existed! Mistress Toni was huge help. I had to leave her a booking photo of Sara though.” I felt much better with this knowledge.

I told Dan that I was feeling chilly and asked if he could get me a blanket or jacket. My sundress was not very warm. Dan went to the rear of the jet. I could hear him ratting through boxes.

When Dan returned he was holding a large clear plastic bag that contained something pink and something yellow. I gave him a puzzled look. He reached into the bag and to my amazement handed me the yellow bikini I was wearing when I was arrested. “Oh, my gosh! I was hoping to get this back someday; it fits so nice.”

The last item in the bag was the pink “Travisti” sweater that was given to me upon my conviction. I began laughing. “I think I’ll tell people that “Travisti” is a very elite fashion line.” We both laughed.

Breast friends

After our laughter had died, still snuggling side by side, Dan passed me a white box with a blue ribbon. It was an item from my Tres Palmas suite.

“I found a source for your ‘Your Breast Friend’ cream in case we decide to order more. This product cannot be sold in the US… it appears there may be side effects!”

I opened the cream and gathered a good amount on my fingers. I reached over and unbuttoned Dan’s shirt; I pulled it open and began rubbing the cream over and around his closest nipple. Dan’s body stiffened momentarily but relaxed; he let me have my fun. I rubbed until there was no more cream.

Putting more cream on my fingertips I extended my hand and looked at Dan in a playful way. It took a moment for him to process what I had in mind. Finally he grasped my intent. Dan leaned closer and transferred the crème from my fingers tips to his. Opening his shirt wider he began creaming his other nipple. I got additional cream and helped him out.

As he was beginning to respond to my ministrations I coyly asked, “Dan darling, I picked up on something when we were in bed at the Convent. I have three questions for you.”

Dan loaded up with more tittie cream and began circling and rubbing his original nipple; it was clear that Dan enjoys nipple play.

“Ask me anything darling.”

“OK, Sweetums; how big is your house? Do you already have a roommate? How long have you been shaving your legs and pubes? Why do you wear silk panties?”

Dan answered by hugging me closer and giving me a lingering passionate kiss. He slid his hand under my dress and began caressing my penis through my panties. I soon had a throbbing and urgent erection. I unbuckled Dan’s belt and undid his zipper. I melted into the moment and let my man have his way with me. It felt right.

Forty-five minutes later we had become members of the Mile High Club.

I’m well and intact

About an hour before touchdown in Mexico City, with Dan sitting beside me, I called my mom to let her know that I was ok. My call went immediately to auto answer; perhaps that was best.

“Hello, mom, this is Sara. I want you to know that all is well. I met a very nice boyfriend and I’ll be spending time with him before coming home. Don’t worry I’m still fully intact and I’m very happy that I met Dan; you’ll love him. I’ll call again in a day or two. Hug daddy for me. I love you both.” I ended the call. I let out a long “Whew!” of relief.

Dan gave me a hug and a nice kiss. “OK, Sweetheart, besides shopping for new clothes and lingerie what do you want to do tomorrow?” he asked.

“I’ve been under lock and key for a long time. I want to savor my freedom, sleep in an unlocked room and casually enjoy the day. I wonder what other adventures are coming our way over the next few days.” Time and circumstances would tell.

About an hour before arrival Dan called his housekeeper and told her to get the house ready for a guest. “Carla, ready the master suite, set the temperature to a comfortable level and prepare a light meal for two. We’ll be there in an hour.” They spoke a few minutes longer before ending the call.

“You have a house keeper!?” I asked.

“Carla works for my company. Years ago her family kicked her out. She had been living on the streets for about a year when I rescued her. In exchange for a safe place to live she also receives a monthly salary. She takes care of this compound and she’s always on call. It works out well for everyone. She lives onsite or in the big house when it’s vacant. She’s never let me down.”

Touchdown, Mexico City!

Dan instructed the crew to time our arrival at Benito Juarez International airport for 30 minutes after sunset. Airport elevation is 7,342 feet. I was told some people become easily tired for the first few days at this elevation. It’s called acclimation. No jogging.

Our jet taxied to a remote area of the airport. An aircraft tug moved our jet into a huge protective hanger; protection from the hot midday sun and protection from prying eyes. The large hanger doors slammed securely shut.

The crew did their post flight routine and completed their logs. Dan let them know that the craft was to be inspected and fueled by 2 PM tomorrow even though they would not be needed again for 2 or 3 days. They were to have their phones on in case something urgent came up. The crew was used to being on standby for Dan.

Before allowing Dan to escort me off the jet I freshened up and redid my makeup. This feminine endeavor had become a necessary routine for me; I had evolved deeper into femininity than I would have ever predicted. We each carried a piece of luggage down the Gulfstream’s steps.

A large two bedroom apartment with a larger master suite had been built into the corner of the hanger. Dan’s housekeeper, Carla, greeted us at the door dressed in what I’d call a casual below the knee black and white hotel maid’s uniform; there were no stockings. Her heels were a modest two inch; functionality over fashion. Carla was about 5 feet 2 inches with longer than shoulder length black hair. Despite her gold stud earrings and red lipstick there was something out of the ordinary about her; perhaps it was her shoulders or the way she carried herself. It simply did not matter to me.

We stepped inside and went through basic introductions. I noticed Carla intently scrutinizing me before saying, “Welcome Seniorita Sara; you are very pretty. Mr. Dan has a talent in finding beautiful women.” Her Spanish accent was delightful and easily understood.

Carla took my bag and showed me to the master suite. It looked very comfortable. I was looking forward to a hot shower and a restful, non-incarcerated, sleep. Carla showed me the luxurious bath room and set out a stack of bath towels and a pretty feminine pink bathrobe with matching slippers. Returning to the sleeping area Carla turned down the bed for me.

Dinner was grilled chicken tacos, a green salad, a cup of tortilla soup and white wine. The food was light and tasteful.

When we had finished eating Carla cleared the table and was about to go to her room. “Carla”, said Dan, “Senorita left a box of her things on the aircraft. After breakfast tomorrow please get them and put them in our closet.” She nodded in agreement.

Dan and I talked about many things including what needed to be done to get me back into the US with no trouble. He brought up the very real need for me to seek medical care regarding the hormones and ‘blockers’ that I had been fed for such a long time; I may need help in being safely weaned off the “juice”.

“Maybe you should keep taking one or two hormones if you don’t want your titties to dry up and go away. A comprehensive exam and blood test is needed for you well being.”

I agreed. “I don’t want withdrawals.”

“I have several ‘suit and tie’ meetings tomorrow involving trade opportunities and briefings. I’ll be gone by the time you get out of bed and I’m not sure when I’ll get home.”

“Do what needs to be done. I understand.”

“I’m also working on a way to get you safely back in the US without creating an international incident. Your ultra feminine appearance creates a few challenges for us. I think we will fly to Las Vegas as a decoy strategy. I have contacts there. Life will get less complicated once we’re back in the US. Be prepared to fly out of here with short notice.”

Dan laid out his clothes for the morning. We shared a soothing uneventful shower and were soon in bed and asleep.

Morning

I awoke at 8:30 AM; as predicted Dan was gone. I leisurely got out of bed and washed my face with cold water to help wake up. I brushed my hair, slipped into the pink robe and slippers and scuffed my way to the dining room.

Carla must have heard me because a hot cup of coffee was waiting for me. She greeted me with a friendly smile. “Did Seniorita Sara sleep well?” she politely asked. I said that my sleep was delicious. My comment made her laugh.

“I don’t do mornings well without an English muffin and coffee for breakfast” I quipped. I remembered telling Jackie the exact same thing. I felt an odd sadness about an old memory. I wished I knew how she was faring. The feeling passed.

“What would you like to eat this morning Seniorita? Bacon and eggs perhaps?”

“A toasted English muffin with butter and honey would be perfect.” Carla had all the goods. The muffins and coffee left me satiated and functional for the day.

I went to clean up and get ready for the day. I did my makeup and Breast Friend treatment while Carla retrieved my box from the aircraft.

Carla was putting the box into a closet when my pink prison file folder slid out of the box and onto the floor. The Sara/Steve booking photos were in plain view.

Carla read a few pages of the court report and then reexamined the photos. She checked the content of the box closely. She held up my pink sweater that had “Travisti” stitched on the front left breast area. Her other hand held my cross body denim prison purse that also had “Travisti” embroidered on it. What’s a girl that reads Spanish going to think about this? My secret was no longer a secret.

I entered the bedroom and immediately recognized what Carla was holding; our eyes met. She held out my pink prison sweater. “Travisti? Eres una travesti?” (Transvestite? Are you a transvestite?) Carla plaintively asked. I understood her question perfectly.

Carla plopped herself in a chair and shook her head in disbelief. I sat in an adjacent chair and said, “Let me explain what’s going on.” I reached over and held her hand and tried to reassure her. I explained that Dan had rescued me from a ‘miserable’ situation and was returning me back to the US. Carla was very worried about there being two travisti in the house.

Carla asked polite but pointed questions about how my presence would impact her employment and living arrangements with Dan; was I a threat? Would Dan replace her with me? “Carla, I’ll be gone and out of your way very soon. I am not a threat.” Carla’s tense body demeanor immediately relaxed. The topic of Dan and I being lovers was never mentioned.

How long have you been dressing as a woman?

“How long have you been dressing and presenting as a woman? I’ve explained my situation to you and it’s only right that you explain your circumstances to me.” The boldness of my question shocked her.

Carla’s eyes became wide in surprise and fear. “Don’t be afraid Carla you look and act very feminine; only another travisti would know. Our conversation is our secret. There’s no need for Mr. Richards or anyone to know what we’ve discussed.”

Carla answered me. “I knew I was travisti since I was 5 years old. My family tolerated me until I was age 15. At this age I became too public in my dressing, my makeup and my mannerisms; they said I was an embarrassment to the family. They threw me out of their house and told me to never return.” I could tell that Carla was becoming stressed out.

I told Carla to relax a moment and that I’d be right back with some water. I wanted her to compose herself. I also wanted to hear her story. I returned and handed her a bottle of cool water. “And then what happened; where did you go; what did you do?” I probed.

“Sometimes I hid and slept in people’s cars or in vacant buildings. Sometimes I stayed with others like myself. I made friends. They taught me how to survive on the streets. Sometimes I made money in dishonorable ways in order to eat.”

“And then you met Dan?” I asked.

“Yes. By chance I met Mr. Richards. I was cleaning tables and washing dishes at a local bar that caters to travisti; Dan has a fondness for girls like us. He rescued me and gave me this job. I am able to pay for the medicine that gives me breasts. Because of Dan I finished high school. I will be indebted to him forever.” “Me too!” I added.

We talked for another 10 minutes before remembering that today was shopping day. We both felt pleased about our conversation.

Carla stood up and we hugged. “Seniorita Sara I promise our secrets will go no further.” I echoed her words, “I promise too.”

“I’ll get the car. Meet me at the front door in 15 minutes.” I peed, applied my lipstick, grabbed my purse and we were on our way.

We were on a shopping mission; we stayed focused. Carla had us shopping by 10 AM and eating lunch by 1:30 PM. She knew the area well and she had Dan’s corporate charge card. During lunch we enjoyed idle chatter like longtime girlfriends.

I bought comfortable walking shoes, a skirt, a very cute romper, two pairs of casual slacks and 3 blouses that could be worn with anything. I replenished my cosmetics and, as Dan requested, my lingerie. I bought him a cute pair of Emerald Green silk tap pants and matching camisole that he could wear under his suits. The pretty lace waist band and centered red heart would make him smile. I showed them to Carla and she said, “Perfecto! He wears pretty things but he doesn’t have anything like those.”

Carla had unwittingly confirmed that Dan wears lingerie around the house. I made sure that Carla picked up a few ‘pretties’ for herself.

Dinner without Dan

Dinner for Carla and I was takeout pizza and salad. Dan called around 5 PM to check on us and to let us know he would be late. I was to go to bed without him. The good news was that he didn’t have to go to the office tomorrow; he would be on-call all day. I was relieved and happy at the same time.

Carla went to her bedroom. I wound down by sipping wine and watching junk TV with English subtitles and applying My Breast Friend before going to bed.

Morning

When I awoke I could tell that Dan had made it home during the night; his side of the bed had been slept on. I hurriedly took care of my morning bathroom duties and rushed with my Breast Friend.

I joined Dan at the dining table and gave him a good morning kiss and greeting. Dan patted my butt like lovers do and said ‘good morning, darling’. I massaged his shoulders and neck briefly before giving him his pretty camisole and tap pants. He held them up and showed them to Carla. She smiled and said, “Que bonita!” She gave me the ‘thumbs up’ sign and brought me coffee and an English muffin. “Muchas gracias, Carla” I said.

As I enjoyed my muffin Dan handed me the latest version of my old cell phone.

“I had our IT person obtain a new phone for you; she increased the memory, transferred your photos and contacts and added a pink ‘Hello Kitty’ protective case. You have a new phone number that has an Alaskan ‘907’ area code to confuse any ‘bad guys’ that may be out there. We’re not taking any chances of there being any tracking bugs in your old phone so I destroyed it. You’ll need to notify key contacts that you have a new phone number.”

“I feel like I’m living in a spy movie!”

“By the way, I’ve found you a job if you want it.” The shock on my face was obvious. Dan let out a soft laugh. “Relax, baby doll, it’s only a strategy; a ploy to get you back in the US. There is no actual job although I feel my plan could turn into a very lucrative opportunity for you.”

“So what’s the plan?”

“We’ll leave for Las Vegas tomorrow morning. A close friend and business associate owns and operates the well known, members only, ‘Rosie Garter Club’ that is similar in many ways to the Convent except that everyone who works or visits the club does so willingly. It’s a social club similar to a nudist club except instead of not wearing ANY clothes the member wears clothes of the opposite gender during their visit; most members are men that dress and present as women. The same is true for the staff; all waitresses are men. Rose provides dressing rooms and clothes storage.”

My heart was racing as I tried to make sense of what I had just been told; I was trembling. Dan made us two large vodka & Sprite beverages. We adjourned to the couch. “Have a sip or two and let me explain my plan. Our goal is to get you back into the US.”

I sat next to him. My mouth was dry and I savored my first sip; it was refreshing and calming. I took another swig and calmly said, “Explain what is happening and what I need to do.”

“Ross is the name of the guy who owns the club. He calls himself Rose when he’s in femme mode which is about 99% of the time. From time to time I bring her promising people and business suggestions that could enhance Rosie Garter Enterprises. I’m on their Board of Directors. Rose will vouch for anything we say.”

“You amaze me Dan. You are so… diversified. International trade, jet setter, hero and cross-dressing advocate and practitioner.” He managed and impish grin.

“Travel dressed as Steve or Sara. If questioned we will say you’re feminine appearance is related to your new job at the ‘Rosie Garter’. Alternative lifestyles and flamboyant show people are the norm in Vegas; you will go unnoticed. Customs and Immigration will wave you through.”

“We’ll check you into my corporate suite at an off Strip casino. Once you’ve adjusted you can then get on with your life; return home, visit family, find a job, etc. Maybe move to Vegas.”

“I feel that once Rosie meets you that a job opportunity will come your way. You’re a natural for Sales & Marketing, staff training, Client Retention… With your background and firsthand experience you could pitch Rosie a business proposition to create new money making opportunities. How does becoming VP of Operations sound; a six figure income with perks and bonuses?”

“You sure know how to confuse a girl. For the last few months my life has been a roller coaster. This is so overwhelming… so much to consider” I said.

“Let me make things simpler.” Dan got down on one knee, reached over and held my hand. “Sara darling would become my life partner and live with me? Let me take care of you. If you want the Vegas job I will relocate so you can have a career. We have a lot in common.” He kissed me tenderly and awaited a reply.

“Yes” I said. “We both love good times and we both love chicks-with-dicks. Let’s see where this relationship takes us.” I kissed him passionately. My fate and future had brightened considerably on several levels.

Dan notified the flight crew of tomorrow’s plans.

On to Las Vegas

After breakfast (coffee and a muffin for me) we said goodbye to Carla. Dan gave her last minute instructions and an envelope with cash. I gave Carla a hug, a sisterly kiss and my cell phone number.

I boarded the jet wearing my short yellow low cut floral mini sundress with puff shoulders, a red balconette bra with matching red high cut panty and leopard print pumps. Movie star oversized tortoise shell sunglasses and large gold hoop earrings and a gold ankle bracelet completed my image; I was traveling as Steve Upton and using my own passport while looking like a pretty travisti puta (shemale whore). Arrival formalities would be very interesting.

We were in the air by 10 AM with an ETA into McCarran Airport (LAS) in four hours. New adventures and a promising life awaited us.

(PS - I felt bad about leaving Sara hanging at the end of the story so I added 7,100 words to this story in order to tie up loose ends 8/29/2021)