Lyle, or Lindsey to his close friends and special acquaintances, was retired and celebrating his 50th birthday with lunch with two long time friends. It was a fairly low key gathering at the rustic Mount Baldy Buckhorn Lodge & Café in the nearby San Gabriel Mountains. The Lodge held many memories for their group because of the many special occasions held there.

The 5,000 foot elevation provided a perfect temperature while the view and pleasant aroma of pine trees added a special ambience. Large picture windows and a shaded outdoor patio made for a perfect setting. ‘Good old days’ at The Lodge stretched back more than 30 years.

No one had seen much of Lyle since his wife, Megan, had passed away two years ago. After her passing Lyle withdrew into himself; avoiding people, social events and haircuts.

Jack and Bill were helping Lyle celebrate becoming another year older. Due to work and other commitments several of Lyle’s friends could not attend, but had sent gifts and well wishes with Jack and Bill. The trio reminisced and shared stories and exploits from as long ago as grade school. Jack was two years older than Lyle and Bill.

Bill owned a home contracting business. Jack was a Navy veteran, a bachelor and a semi-retired hair stylist. Lyle had been a regional payroll service firm executive for a company that was acquired by a prominent national company. Lyle got a sweetheart buyout deal and no longer needed to work. Megan had owned and operated an independent hair and beauty salon. Her untimely passing provided Lyle a substantial amount of insurance money.

The trio sat at a table with the largest picture window to insure a great view. A stylish leather ‘man-bag’ emblazoned with a circular gold “MK” medallion hung from the back of Lyle’s chair. It didn’t matter that the bag was a cross-body purse; it held everything a woman, or Lyle, would need to look their best. And it was pretty.

Lyle had stopped cutting his already long hair before Megan had passed away. Perhaps it was because Megan took great pleasure in styling Lindsey’s hair and in applying cosmetics on her; it was Megan’s profession and fetish.

Megan had suspected Lyle’s feminine inclinations before they first dated. Megan knew about Lindsey before their marriage. Megan actively encouraged Lindsey’s development much to Lyle’s delight. Lyle was a very willing model for Megan and her salon. Lyle became proficient in the art of self-glamour and routinely used heated curlers, clips and lotions when Megan was busy elsewhere. Highlights, soft curls and occasion specific cosmetics were his specialty. If Lyle didn’t have his blonde hair in a man bun today it would extend below his shoulders.

The birthday trio shared a solemn toast to Lyle’s dead wife Megan who had passed away shortly after Lyle’s 47th birthday. Her passing left Lyle alone in their 4 bedroom 2700 square foot home. One bedroom had been converted into a functioning beauty salon. The home had many memories for Lyle to be lonely in. Collectively Lyle’s friends thought that he should move to a new and smaller place without old memories. At the very least the group thought that Lyle should get a roommate.

The three friends celebrated with Ortega chili burgers with Swiss cheese and mushrooms. They shared a plate of sautéed mushrooms and a side order of onion rings. There were adult beverages and pleasant conversation. The group reminisced and shared stories about their exploits from as long ago as grade school.

Lyle spoke about possible vacations to the Big Sur area of California or maybe an excursion to San Francisco adult specialty clubs. He was torn between road trips and staying home. Vacations and life in general didn’t seem as much fun since his wife had died.

Lyle grabbed his man bag and excused himself to use the restroom. As soon as Lyle was out of sight Jack and Bill placed a large gift bag on the table where Lyle had been sitting. The decorative bag was a feminine pink and lavender. It was adorned with pretty flowers, unicorns and glitter. Bill leaned over to Jack and asked, “Do you think Lyle will freak out when he sees his presents?”

“Hell no,” snorted Jack. “Everyone knows that Lyle’s has always been ‘special’ in certain feminine ways. Megan told us this over 20 years ago. She swore us to secrecy so we’d keep a eye out for her Lyle and make sure he didn’t get into any trouble due to his special inclination. He’s only 5 foot 8 inches tall and maybe weighs 135 pounds after a thanksgiving meal. His long blonde hair doesn’t exactly ‘butch him up’ enough to deter bullies and jerks. I don’t think I’ll ever get used to his man bun hairstyle. I think a perky ponytail would better suit him.”

“A medium shag cut would look pretty… nice” suggested Bill.

Bill chuckled as he took a sip from his vodka and seven. “Yeah, you’re right. I can’t recall a Halloween, or any party for that matter, in which Lyle didn’t use it as an excuse to get dolled up. I know for a fact, from being in gym class with him, that he was shaving his legs in high school.”

Jack nodded in agreement and added, “Nature doesn’t gift a person, male or female, with such well defined and feminine eyebrows; that doesn’t just happen by random chance. His brows have always been well shaped and maintained. Those arches aren’t accidental and neither are his manicured and shaped fingernails. For a man Lyle sure makes an attractive woman.”

“Jack, I think you’ve been a bachelor far too long to be having those thoughts. Just for the record your nails have always looked less than manly” said Bill.

“I take care of my nails due to being a hairstylist. Grubby nails are a turn off” Jack retorted.

Sipping from his drink Jack smiled broadly and commented, “We’ve all seen his panties or bra strap over the years as he bent over or reached for something. We’ve overlooked the tell tale residue of nail polish around his cuticles and the left over black flecks of mascara and eyeliner. My only regret is that Lyle doesn’t feel secure enough in his femininity, or himself, to confide his ‘secret’ with us. Once he sees his gifts that may change. We were, and still are, his friends.”

Returning to the table Lyle was surprised to see a gift bag where his plate had been. As he was sitting down Lyle flicked the bag with his finger and rhetorically asked, “What’s up with the bag, dudes? Is it somebody’s birthday?” They all broke into laughter.

As Lyle was staring at his gift bag Bill stood up, picked up his drink glass and proposed a toast. “On behalf of our group of friends, many that unfortunately could not be here today, here’s to Lyle: A true and unconditional friend; happy birthday. We salute you.” The friends clinked their glasses together and took a sip.

With his drink in hand Jack stood up as Bill was sitting down and announced, “And here’s a toast for another good friend. Always reclusive, never seen but always loved… here’s to Lindsey!”

At the mention of his femme persona, “Lindsey”, Lyle momentarily froze and visibly gasped. His face flushed warm. He nervously looked back and forth between his two friends for a reaction to his reaction. There was none.

“Speech, speech!” encouraged Jack and Bill.

Jack broke the tenseness of the moment by quietly telling Lyle that the existence of Lindsey had been well known to their group of friends for a long time; that Lindsey was like a distant aunt that everyone knew about but who never visited. Jack continued, “In high school your manicured nails and shaved legs were a definite hint to us that there was another side to you; a feminine side.”

“You removed all doubts in high school when you had BOTH of your ears pierced” said Bill. “Through the years at various parties we’ve all seen glimpses of Lindsey.”

As Lyle reached for his gift bag Jack spoke up: “Lyle, as you open your gifts please be assured they were carefully chosen and are given with our deepest respect for you, Lindsey and Megan. Lindsey and you have always been good friends to us all… unconditionally.”

In a halfhearted effort to explain about Lindsey Lyle said, “My older sister’s made me… they practiced on me!” Inhaling deeply Lyle gave up on his fake explanation and sat back in his chair. He exhaled and continued in a much softer voice, “And just maybe they practiced other things on me, too. Megan, Lindsey and I enjoyed special times together. No harm ever came from anything we did… or wore. That was how Lindsey came into my life. My Megan, my sisters, Lindsey… and a certain male friend, (Lyle paused and looked directly at Jack), all knew each other and we all had interest in feminine things.” Jack squirmed a bit at Lyle’s admission about him having an interest in feminine things.

“Exactly! Your sisters told my sisters”, Bill interjected. “Undoubtedly your ‘secret’ made its way among our other friends too. About 20 years ago Megan confided in us about Lindsey and your feminine side. She asked that we keep an eye on you so you didn’t get into any problems. So we have.”

“Remember on a ski trip we asked you about the reinforced toes of black nylons stockings we saw when you took your ski boots off? You became flustered but said you wore pantyhose under your ski pants instead of thermal underwear to keep warm? And another time you tried to convince us that the sports bra you were wearing under your shirt was a special high tech posture brace? And another time you explained away an obvious camisole that you were wearing as a ‘special thin strap designer undershirt’! Your tinted ‘lip gloss’ was always Megan’s chap stick that you were forced to use. Nice try, girly, but we were only as dumb as what Megan wanted us to be. It was sort of a ‘don’t ask, don’t tell’ agreement.”

“We did everything we could to keep you and your ‘hobby’ out of trouble. We’ve all made up excuses to cover up your goofs over the years” Jack added.

“Yeah” Bill said. “We’re letting you know that we all support you and your femme twin. You’ve been a recluse ever since Megan passed. You need to socialize more. Maybe you need a roommate. So relax, open your gifts and start living life again.”
All three friends nodded their mutual agreement and leaned back in their chairs. Lyle got the attention of their waiter and ordered another round of drinks so he could relax and appreciate what ‘the gang’ had just told him.

Lyle thanked his friends for their friendship and support. “I’m glad that we finally got this out in the open. After all these years it appears my secret was obviously not so secret. Keeping that secret weighed heavily on me. Megan knew of Lindsey before our marriage. In fact she encouraged Lindsey and frequently practiced salon stuff on me. I was thrilled to be accepted by her and I was thrilled to be able look so pretty. Lindsey always got special gifts from Megan on birthdays and Christmas. You should see my exotic sleep wear!”

“I’d really like to see them someday… soon,” said Jack. Bill nodded in agreement but added “As long as Amy was there too.”

Lindsey: “During the last month of her life Megan confided to me that she had explained about Lindsey to several of our group during a visit to the hospital. I knew the day of the ‘big reveal’ would happen sometime. I’m glad it’s done. I thank you all for your understanding and support.”

Their fresh drinks arrived and there was good natured banter between the friends. Lyle took a sip of his beverage and said, “I want to show you guys something.” Reaching into his pants pocket Lyle pulled out his dead wife’s diamond wedding ring and displayed it in the palm of his hand. “Megan was so supportive of Lindsey that she made me promise to have her wedding ring enlarged to fit Lindsey’s ring finger. Whenever Lindsey is around she always wears this ring. It’s beautiful and it keeps the riff-raff from hitting on me.” Picking up the ring Lindsey easily slid the diamond ring onto the proper finger and held her hand up so that Bill and Jack could appreciate Megan’s gesture of approval.

Jack gently picked up Lindsey’s hand, pulled it closer and inspected the ring. “The ring and the thought behind the ring are beautiful.” Jack looked Lindsey in her eyes, gave her a sly wink and gave her hand a gentle kiss before letting go. Jack had known about Lindsey before Megan knew. Truth be known Jack knew about Lindsey before Lindsey knew about Lindsey.

Reaching back into his gift bag Lindsey pulled out a tube of ‘Rosebud Red’ lipstick and a matching bottle of nail polish. Removing the security wrapper from the lipstick Lindsey opened the tube, twisted it out and delighted in the aroma. She stroked a small streak on the back of her hand to check how ‘Rosebud Red’ would look with her skin tone. The color was a perfect match. Bill leaned forward and softly suggested, “Why don’t you try it on now? No one will say anything.”

Lindsey blushed, smiled sweetly and glanced around. The closest customers were seated on the far side of the lodge and were busy eating. The bartender was busy chatting up a lone customer at the bar but was obviously keeping a watchful eye on everything and everyone.

Lindsey brought out her compact mirror from her purse and deftly applied the ‘Rosebud Red’. She pressed her lips together to even the coverage. Applying a dot of color to each cheek bone she quickly blended it into an attractive make shift blush. “Nice…” Jack began. Lindsey cut Jack off and said, “Before anyone points out that my eyes are washed out …” Lindsey reached back into her purse and retrieved her mascara. Twisting it open she expertly coated her eyelashes. Replacing the mascara wand in its tube Lindsey brought out an eyelash curler that she just “happened” to have. Quickly crimping her lashes Lindsey dropped the mascara, curler and mirror back into her “man-bag”. In a matter of moments Lindsey was sitting where Lyle had been. Leaning back in her seat Lindsey looked for any adverse reaction from her friends. There wasn’t any.

Bill: “You make it look so easy.”

Lindsey: “I’ve had a lot of practice.”

Jack: “Lindsey the lipstick suits you perfectly; may as well try the polish too. You’ve come this far so why not?“

NAIL POLISH

Reaching for the matching nail polish Lindsey shook the bottle and applied a coat of color to the finger that wore Megan’s ring and set the bottle down. Jack reached over, picked up her hand and gave Lindsey another wink. He began gently blowing her nail dry while maintaining eye contact. Once her nail was dry Lindsey displayed the finger that wore Megan’s ring. The dark red of the polish set off the ring perfectly.

Without asking permission Jack opened the polish, took hold of Lindsey’s hand again and proceeded to paint Lindsey’s other four fingers. Lindsey didn’t resist. As he worked Jack said, “You can finish them when you get home. Or I can stop by later to complete the job. As you know I specialize in toes.” Before setting the bottle down Jack painted one of his nails too as a symbol of support.

Wanting to be part of this show of support for Lindsey Bill took Lindsey’s right hand and carefully colored all of her remaining nails. All of Lindsey’s well shaped finger nails matched her lipstick; very feminine looking. Copying Jack Bill blew Lindsey’s nails dry; it somehow felt different when Bill blew on her wet nails! Lindsey’s heartbeat went up and a very pleasant spark was lit. Was she attracted to Bill? A subtle ‘Mona Lisa’ smile graced Lindsey’s face. Like Jack had done Bill painted one of his nails and set the bottle back on the table.

The three sat quietly and waited for their nails to dry. Lindsey, with her ‘Mona Lisa’ smile, squirmed until the “Bill” reaction that her crotch was having resolved itself.

“Let’s see what else is in your bag,” Jack suggested.

“You really want to meet Lindsey?”

“You really want to meet Lindsey?” Lindsey asked. Her two companions enthusiastically nodded “yes”.

So Lindsey continued “coming out” of her male cocoon. She undid her man bun and shook out her hair. A few strokes from her brush and Lindsey had a feminine shoulder length hairstyle with bangs. Her hair framed her pretty face perfectly. Her blonde hair and hairstyle accented her femininity. For emphasis Lindsey used her hand and did the girly hair ‘flip’ move. Everyone chuckled and Bill and Jack nodded their approval. They both gave her the ‘two thumbs up’ sign.

Lindsey’s next gifts

Reaching back into her gift bag Lindsey withdrew a small jewelry box which she promptly opened, revealing a pair of three inch gold pierced hoop ear rings. “Oh! How cute. I always wanted a pair of large hoops!” she said. Lindsey removed the two 10 mm gold ball studs she was currently wearing and with well practiced ease, and without a mirror, tilted her head and expertly inserted the new hoops into her ears. She gave each hoop a gentle tug to ensure they were secure. Lindsey tucked her hair behind her ears and turned towards Bill. “How do they look?” she asked excitedly. Bill gave her the ‘thumbs up’ gesture of approval. Lindsey fought the impulse to give her friend a kiss of thanks.

Delving back into her purse Lindsey produced two three inch long tortoise shell hair clips. Each clip had three cute ‘accent pearls’. Deft use of the hair clips instantly controlled where her hair lay. The gold hoops became prominent.

The last item in the bag was a small bottle of perfume. The label indicated ‘Cashmere Mist’. “This smells absolutely divine,” Lindsey announced as she passed the bottle to Jack and Bill for their evaluation. “My Amy picked it out,” Bill said. Bill handed the perfume back to Lindsey who promptly put a small drop behind her right ear, another on her left wrist and a tiny bit on her hair brush. Lindsey briefly stroked her hair. “Please tell Amy thank you for me. It smells lovely” Lindsey said.

Lindsey put the lipstick, perfume, gifts boxes and wrappings into her ornate gift bag and sat it on the floor next to her chair. Lipstick marks on her empty cocktail glass were pointed at by Bill and produced a group chuckle.

“Thank you for being so thoughtful. I’ve been a hermit for so long... it feels wonderful to be around friends again. Be sure to relay my appreciation to the rest of the gang please. You gave Lindsey a great day out… a ‘coming out’ party you might say. Thank you for everything.”

Picking up on the ‘being a hermit’ theme Bill queried, “Maybe you should get out more often…or get a roommate. Good friends are difficult to find. You need to find a new companion to share your life with and maybe fill certain physical needs at the same time.”

Lindsey blushed and flashed a pretty smile. “I’d need to find a very special and understanding person that would tolerate my quirks, clothing and the dates I’d bring home. My preferences might be awkward to some people. They’d need to be very open minded to say the least.” Jack and Bill nodded their heads in agreement. “Then I’m your man. Think of the money you’d save by having me cut and style your hair. I’m licensed” Jack offered.

Lindsey: “A guy I know has already asked to move in. I told him that I’m in no rush and that I would get back to him. I don’t think mixing business with personal life is a good thing. I’ve known him for about two years.”

Jack: “Two years? Business? I’ve known you for thirty years! I should have priority over a stranger!”

In a way Lindsey was flattered… two men were jealous for her. “Yes, it’s a long story. I’d have no problem in kicking him out. Kicking you out would be more difficult because I’ve known you longer… but I would if things didn’t work out.”

Jack scowled and asked, “What’s this guy’s name? Maybe I know him.”

“He likes it when I call him Princess.” Bill rolled his eyes in response.

Bill gives Jack and Lindsey privacy

The topic of conversation was getting out of Bill’s comfort zone. Deciding that he didn’t want to be in the middle of such a personal conversation Bill took a sip of his beverage and excused himself to go to the restroom. On his way Bill stopped briefly and spoke to the bartender. Concluding his conversation Bill gave the bartender a $10 bill and went into the Men’s room.

While Bill was gone Lindsey and Jackie had a serious and very personal conversation about topics and past events that no one else needed to know about. It was good that Bill had left the table.

The TALK that Bill never heard. The conversation gets graphic. Their X-rated conversation is found a few paragraphs below.

Mild version

As Bill disappeared down the hallway Lindsey Jack leaned over and gave Lindsey’s lightly perfumed hair a prolonged sniff. “That scent suits you perfectly… it’s womanly.”

Holding Lindsey’s hand Jack continued; “Lindsey, you know I’m an open minded person. I can help you in many ways. I could help with rent, move furniture, hang pictures, style your hair, paint your nails…and take care of your physical needs. We made it work when we were young. We have history; history that no one knows about but us. Why don’t you call me sometime?”

Lindsey’s heart raced as she processed what one of her best friends had just said. Had she just been propositioned? Her mind recalled when in grade school how Jack had befriended him… multiple times. And Lindsey had reciprocated being befriended… multiple times. Was she and Jackie destined to be a couple again? Would Princess be a better roommate?

Bill returns and the conversation becomes guarded

Not knowing what to say or how to respond Lindsey was spared having to say or do anything by the return of Bill. Thankfully Bill had been spared the intimate personal conversation that had just ended. He pulled out his chair and sat down.

“Heck, I’m gone for a few minutes and I come back and find you two holding hands. I’d tell you to knock it off and get a room but I think you would!” Bill joked.

Lindsey quickly pulled her hand away from Jack and grabbed her drink glass. “No, absolutely not…it’s not like that at all. Jack was only admiring my ring” she said. Glaring at Jack Lindsey continued, “Isn’t that right, Jack?” Jack nodded his head in the affirmative and said “I was offering her my help when she needs it.” Bill sat down and the awkward moment passed.

Bill said, “Well, let’s wind this party down and head for home with a promise to do it again soon. I think it’d be a great idea if Lindsey hosted a get together in a couple of weeks. She has a comfortable home with a fine backyard and patio. Personally, I’d prefer Lindsey to be the hostess. And I know our group would be pleased to finally meet the elusive Lindsey after so many years of rumors. What do you think?”

“I think that’s a fine idea!” Jack said.

“Your interest and acceptance of Lindsey is greatly appreciated. I need to give it some thought as I’m having a minor out-patient medical procedure soon. I’ll get back to everyone about having a BBQ at my house in a few weeks.”

The trio was about to stand and leave. Bill was being slow about leaving.

A moment later the bartender walked over with a tray of shots and a cupcake with a candle. He set the shots in front of Lindsey, Bill and Jack. The cupcake was placed in front of the birthday girl. As he lit the candle the bartender said, “My name is Joel. I couldn’t help but notice a remarkable transition take place today. The cupcake is from an admirer and the tequila shots are from me. My husband Dan and I bought The Lodge a couple of years ago.” Taking a pretty cloisonne rainbow pin from his shirt pocket Joel handed the pin to Lindsey. “Happy birthday, Ms. Lindsey… Happy ‘acceptance’ and happy ‘coming out’! You’re very beautiful. I’m glad you made The Lodge part of your special day.” Bill and Jack applauded.

Offering his cell phone to Joel Bill asked, “Please take a photo of us.” Jack and Lindsey also passed their cell phones to Joel. Joel directed the group to get close. “Let’s have the two men on each side of the pretty lady with the beautiful hair.” A few photos later Joel and his tray retreated back to the bar. Lindsey and her smile were radiant. “This photo may wind up being my Christmas card this year. Megan would really like this photo.”

Their extended lunch was winding down

Glancing around the table Lindsey made sure everyone had their tequila shot at the ready for a last toast. Standing, Lindsey said, “I know that meeting Lindsey has been of great interest to you all. I hope your curiosity has been satisfied and that you are not disappointed.”

Lindsey continues: “Tell our friends that Lindsey was a bit late but I gradually showed up before lunch was over. In case anyone asks ‘what did Lindsey look like’ you can tell them she was wearing a khaki blouse with matching pants, moccasin style flats, a camisole, pettipants, pantyhose, a gold anklet, matching lipstick and nail polish, tasteful eye makeup, beautiful gold hoop earrings, a stunning diamond ring and a very broad smile. And be sure to mention my hair too.”

Lindsey’s comment resulted in a good laugh for all.

Lindsey held up her shot glass of tequila and pronounced, “Thank you all and happy birthday to Lindsey! Thank you for accepting me. Please tell everyone thank you for the gifts. Megan would have been pleased.” Jack and Bill echoed her sentiments and they all downed their shot.

They hugged. They even kissed and they left.

The mild story ends here unless you want to know what Lindsey and Jackie didn’t want Bill to hear.

The ADULT TALK that Bill never heard. The conversation gets graphic. The story continues.

As Bill disappeared down the hallway and out of hearing range Jack and Lindsey began a serious and X-rated conversation.

Lindsey: “So… Jackie, what’s new with you? After high school I went to college and came home with a degree. You enlisted in the Navy and came back with a boyfriend.” Lindsey’s tone seemed a bit bitchy.

Jackie: “Scott wasn’t my boyfriend; he was my on board girlfriend. Heck he had his own panties, for god’s sake AND he ironed my shirts and pants. He made lonely nights on the ship not so lonely. I couldn’t turn that opportunity down. After being discharged we shared an apartment and a bed while I was getting my hair stylist and cosmetologist licenses using my GI Bill. Scott got married.”

Lindsey tapped her painted nails on her glass, took a sip and began.

“What I didn’t tell Bill is that Megan has given me another gift. A gift I’m scheduled to receive in two weeks.”

Jackie was taken aback and looked alarmed. “You’re having gender reassignment surgery!?”

Lindsey laughed softly. “I think I’m headed in that direction but not right now. Before Megan became sick we were discussing a unique business opportunity that matched our lifestyles and my retirement. She suggested, and I agreed, that I would get modest B cup breast enhancements; a size that matches my frame, her needs and our business goals. It’s been scheduled for a month. The healing takes about eight weeks.”

Jackie looked shocked. “Have you looked in the mirror lately, Missy? There is not a lot of Lyle to be seen. In fact all I see is Lindsey. Why on earth would you do that?”

“There are several reasons to get boobs. One is because I’m going to start living full time as Lindsey. Also Megan wanted me to have breasts and I promised her that I would do it. Additionally breasts will improve the way Lindsey’s clothes fit and I’m sure boobs would help with the business venture I’m considering.”

“Business venture?” asked Jackie.

“Yes. This is another thing that Bill and our friends don’t need to know about. Based on our experience with Princess I’m considering opening a ‘Sissy Salon & Panty Parlor’ that caters to people with special needs, fetishes and desires. People are curious and may want to discreetly experience something new in private and secure setting. The concept is not unreasonable. I already have Megan’s salon room that is a fully functional hair salon. And I have two spare bedrooms.”

“Besides the obvious income from being a specialty salon there’s income to be had from many sources. I can sell larger size women’s clothes, shoes, lingerie, wigs, makeovers, photography services, etc.: all from the comfort of home. There’s income to be had for referral kick-backs for special services that we won’t do; like piercings, tattoos, hormones, hard core sex, etc.”

“Schedule work for two or three days a week. What working girl wouldn’t want a three day work week? I’ll get all employees certified as ‘sex surrogate-counselors’ or ‘sexual health therapists’ or ‘gender exploration therapists’ to make our ‘personal services’ legal. I’d also have a medical clinic on retainer for free routine testing and care of staff.”

“I need to find a versatile licensed hairstylist that understands and appreciates my type of clients. I envision a man that, like them, can dress and present like a woman; a stylist they can relate to; someone non-threatening; someone that could gently guide them down the road to their femininity like you did to me. I need someone who would take the situation in hand… or mouth when needed. In fact I need someone like you.”

Jackie alerted and his eyes became wide. Was he about to receive a job offer?

“So looking and acting femme are part of the job description? Is that all?” asked Jackie.

“No. In addition to the sex element another job requirement is that all my personnel must be willing and able to work their entire shift wearing 3 inch or taller high heel pumps. We are selling image and illusion to our clients and we need to give it to them. Let them see, and if need be, let them feel a shapely stocking encased leg. Let them see and feel the erotic snugness of a garter belt. Indulge their fantasies. Don’t spoil their illusions.”

Jackie was about to say something when Lindsey waived him off.

Lindsey: “I figured that I would manage the business, like a mommy runs a household. My business ‘family’ would service the customers. I’d run the Boudoir photography business; web sales, service referrals, etc. and have total control over the business. I would fill in where and when needed.”

“I was thinking that Princess could take care of Client Care which includes scheduling, clothes fitting, special requests and fulfilling carnal needs.”

“My ‘Sissy Salon & Panty Parlor’ personnel would need to be switch hitters when needed; willing and able to provide a variety of sexual ‘therapy’ services when business required it. The willingness to present as female, while on duty, and to be able to function sexually as a top, a bottom or as a big sister confidant is essential.”

Jackie was intrigued. What Lindsey had said was exciting. If he was to be part of this adventure he had better make his willingness known.

Taking Lindsey’s hand Jackie leaned over and gave Lindsey’s lightly perfumed hair a prolonged sniff. “Lindsey, you know I’m an open minded person. I can help you and the salon in many ways. I’m a licensed stylist in need of a gig. I can paint nails, shape eyebrows and do cosmetics. Not only can I fulfill the client’s physical needs I can fulfill your needs, remember? And as you know I can function as a giver or a receiver.”

“I femme up nicely and I can subtlety bring out the inner girl in men and boys as I did for you. We have history; it was me that found us the ‘How to Tuck and Tape’ video. We watched it together and we practiced together. I have the exact experience that the ‘Sissy Salon and Panty Parlor’ needs.”

“I can be on the job as soon as you need me. I have no commitments. And we have history that no one knows about but us. Why don’t you make me an offer?”

Lindsey responds

“Jack, you were the first man to paint my nails. I was 13 and you were 14 or 15. It’s been years. On any given weekday when our folks were at work we would experiment with our sister’s clothes, makeup and nail polish. You would paint my nails and then I’d paint yours. It always seemed to be a labor of love for you” Lindsey commented. Jack quickly responded, “Yes but only my toe nails!”

Lindsey smiled, shook her head and softly said, “We also explored and experimented with each other’s body. You liked it. So did I. You gave me so many new pleasures and taught me things I never would have discovered without you.” Jack nodded his head in agreement. “We were so young and inexperienced.”

Lindsey took another sip of her drink before she continued, “Jackie, you were the one who taught me how to put on panties with a garter belt and nylons. In fact you didn’t just tell me how to put them you showed me how by putting on your own stockings and panties first. Once you got yours on ‘just right’ you began to dress me. ”

”I still reminisce about you hooking me into my first garter belt and stockings. ‘Roll the stocking up like a donut, stick your foot into the donut hole and then easily roll the stocking up your leg smoothing them as you go.’ you said. ‘Panties always go on last over your garters’ is what you taught me, right? You were on your knees and rolled each stocking carefully up my legs making sure they were perfectly smooth; you caressed my stocking covered legs much longer than what was needed. You showed me how to fasten my garter tabs to my stockings. Your touches gave me the hardest and most urgent boner of my life.”

”You held pretty red satin panties open for me to step into. You were concerned about the large bulge that you had given me… you said it wasn’t ladylike… that it ruined the illusion… that you could do something to make my boy-bulge go away. Remember? ”

Jack nodded and said “Yes, I remember. I didn’t think I could get the panties over your hard on! I kept smoothing your stockings and thighs to buy me time as I wondered if I should do to you and your erection what I had been fantasizing about doing. I was young, inexperienced, scared and very, very, horny.”

Lindsey:”My panties were only up to my knees and my erection was framed by my garter belt; it was waving in your face. Remember? You gently took hold of my penis and stroked it a few times before pulling me closer to your face. You kissed and tongued the tip of my penis and began to slowly suck my shaft into your mouth. It was marvelous.”

“You fondled my balls with your free hand for awhile and then began probing my rosebud. You wet your finger with the pre-cum drooling from your penis, smeared your finger and slid it into me; I remember that I gasped. That was another marvelous sensation. You began bobbing your head up and down on my penis in coordination with your finger fucking. You finger fucked and sucked me to my first orgasm. I was in virgin heaven.”

Jack: “Yes you gasped and ejaculated in my mouth. Your anal muscle clenched my finger so tightly that I thought you would sprain it.”

Lindsey: “As I recall you swallowed what I had to offer but only after slipping some to me in a post orgasmic kiss afterwards. I had never tasted sperm before.”

“We shared many firsts, Lindsey.” Jackie paused, took a sip from his drink and continued. He had a wistful tone as he spoke. “You were the first person I went down on. I was horny and scared. I didn’t know how you would react; I knew I had to do it. I didn’t know what I was doing and you didn’t seem to mind. You were so cute and willing. Afterwards you wanted to try it on me; you were begging to blow me! I made you wait a few days before I let you and you didn’t disappoint.”

Lindsey: “Yes, we shared many firsts. You were the first man I ever saw dressed in lingerie and makeup; that’s when I started calling you Jackie, remember? You were the first man to see me wearing lingerie and women’s clothes. You were the first person to sexually pleasure me. You did things with your mouth and middle finger that I still dream about. You were the first man I sucked off. And maybe that’s why you wouldn’t be the best roommate for me. I need to think with my big head and not the other.”

After a few moments of thought Lindsey continued with the conversation she didn’t want Bill to hear.

“Yes, it was a memorable summer. I willingly went down a road I wanted to explore and I willingly went down on you. You literally took my hand and pointed the way. You also physically took my hand and placed it on your penis. I’d never seen another person’s erection before let alone touch one. It was warm, firm and… pretty. I kissed the head and was tickling it with my tongue tip. You made me stop and wouldn’t let me suck you until I put on slutty bright red lipstick; you wanted red love rings on your shaft and I gave them to you. The force and the amount of your ejaculation took me by surprise.” Lindsey involuntarily ran her tongue slowly around her lips.

Jackie: “I may have started you down a path but you turned that path into a major freeway and a way of life; total immersion you could say. Unlike you I only dabble in my fetish; I don’t live it.”

Lindsey: “Because of you I always wear lipstick when I blow somebody. You started a tradition.”

Jackie: “You were and are so damn cute. I knew you were special then and I was desperate to suck you to orgasm; I needed to taste you. You weren’t very reluctant.”

Lindsey: “Megan thought I was special too. Not only did she see the ‘girl’ in me she encouraged me to embrace my femme side. Some of our best sex was while I was wearing lingerie and makeup. There was a particular sundress and a satin turquoise chemise nightie she liked me to wear; and always a garter belt and stockings. She said I was destined to be the perfect bottom.”

Jackie: “She preferred to be on top; to be the assertive one?”

Lindsey: “Yes. She’d wrestle me in bed, pin me down and have her way with me. She liked burrowing under my dresses and panties to get to me. I liked feeling vulnerable and we both loved the sensation of our lingerie and stockings rubbing together.”

Jackie: “I love those sensations too. I love the feel of my nylons rubbing against another person’s stockings and panties. Like you I love wearing stockings and panties. It’s been awhile for me.”

Lindsey: “Megan had two custom silicone dildos made of my penis. One was a strap-on. She said the strap-on made her feel like she was raping me. I’ve been on my back with my legs over her shoulders many times. In a way I was fucking myself and we all know how erotic that is.”

Jackie: “Jesus, Lindsey…”

Lindsey: “Although we never spoke about it much Megan had some serious lesbian feelings. As long as I was her sex girlfriend she didn’t need to succumb to her lesbian tendencies. A relationship between a crossdresser and a lesbian is a perfect union. It’s symbiotic.”

Jackie: “Why did you have two dildos made?”

Lindsey: “Sometimes, but not always, while she was pegging me I would suck on the spare dildo. Seeing me blowing the silicon cock excited Megan a lot. She always asked me to moan. Mentally I was blowing myself which turned me on. I liked leaving lipstick rings on the shaft just like in my bachelor days. Sucking the silicon kept me monogamous and out of gay bars through most of our marriage.”

Jackie: “Through MOST of your marriage?”

Lindsey: “Megan had her fantasies and I had my own. She had a source for medically prescreened lovers. Four or five times during our marriage Megan would bring home a handsome bisexual young man for us to share. I would dress up as pretty and feminine as I could; always with matching lingerie, garter belt and perfect makeup. She loved to see me sucking cock. It excited her. But seeing me being properly fucked was the ultimate for her; she got off on seeing me take a dick up my ass bareback. She would even lube the guy’s penis and help push it in my boy pussy.”

”While I was being bred, as she called it, she would use the dildo on herself or sodomize my lover. It was always good for a more powerful ejaculation for all of us; I enjoyed feeling the more forceful warm squirts. In fact I’ve learned how to milk a penis using my butt muscles. You’d love it.”

Lindsey and Jackie took a break from their conversation and drank more of their cocktails. They were both getting aroused. It must have been the effects of the booze.

Jackie: “Bareback? No condom right?”

Lindsey: “Right. Seeing a semen crème pie leaking from my anus was another turn on for Megan; she said it made me more ‘girly’. It also gave her an excuse to indulge in another fetish. She liked to insert a tampon in my anus to avoid me leaking on the furniture. Seeing a white “mouse tail” tampon string dangling from me aroused her and proved my femininity.”

”One ‘John’ paid $25 to tampon me and another $25 for Megan to plug him. Technically it could be said Megan and I were ‘working girls’. Our guests would usually spend the night.”

Jackie: “Whew! You could write a book. There are websites that specialize in such stories.”

Lindsey: “One year Megan brought home a young post graduate college student. He was a confused cross-dresser that would only participate if we femmed him up a bit; makeup, panties, pantyhose and a bra. We thought he had sissy tendencies and so to his delight we called him Princess.”

Jackie: “That doesn’t sound so kinky.”

Lindsey: “Oh, yeah? He knew I was a male but only I could apply lipstick on him. I held his chin and told him ‘Mommy wants you to wear lipstick and pretty panties’ as I slowly coated his lips. Then I pulled down my panties and ‘made him’ hold my dick. He was so eager. I told him that he could blow me but only if he asked. He did more than ask; he begged to suck me. I made him leave lipstick prints on my shaft like you had me do to you. I ejaculated a mouthful of cum but I wouldn’t allow him to swallow until I came.”

Jackie: “So?”

Lindsey: “He was randy as hell and needed to be fucked. Before I pulled out of his mouth I had him lube my penis with my cum. He had such an eager and talented tongue. I told him he could not swallow my load until I came in his ass. I made him hold and savor my sperm until he felt me squirt in his rectum! He held it for more than 10 minutes.”

“Princess had a thing about being inseminated… of being bred, receiving sperm; he didn’t seem to care which orifice received it. He’s a committed bottom but he can give as well as receive. I was only helping a person out.”

Lindsey: “I pulled down Princess’s panties and pantyhose and had him bend over the side of the bed. I had him reach back and grab my cum coated penis and position it at his anus. He rubbed my slippery cock head in circles around and around his rosebud. He wanted it so bad that he began pressing backwards onto my penis like a cat in heat. He got the first two inches in all by himself. It took Princess a few times of sliding partially in and out before he could get my shaft buried deep enough for him. I just stood there. Princess controlled how deep he wanted it. He eventually got a nice rhythm going. I must have hit his prostate just right because Princess gripped my penis with his butt muscles and spewed! He milked me like a pro and I shot my load deep. Princess swallowed and ejaculated at the same time! It was a beautiful thing.”

“As I tried to pull out Princess kept butt gripping my penis; he didn’t want me to withdraw. It was only after I was totally flaccid that he pulled himself off of me. Then he began crying. ‘Thank you Mommy,’ he said! I hugged him and kissed him tenderly. I told him, “It’s OK my sweet Princess now you know what you need’. I felt so maternal.”

Jackie: “Very heartwarming Lindsey. He calls you Mommy? Does this twink have a name?”

Lindsey: “Yes, I’m Mommy and he likes when I address him as Sissy or Princess.”

Lindsey: “His main goal was to get pegged and inseminated. I must have done it right because a few hours later he begged, ‘Please fuck me again Mommy’. Princess told me he wanted to be on his back with his legs over my shoulders this time! I did as he begged. I had Megan plug him afterwards. He loved it! His dangling tampon string was like a merit badge to him.”

”Before we let Princess leave I had him paint his toe nails a bright red. Megan let him apply mascara and eyeliner but didn’t tell him that it was long lasting and water proof. Princess was also wearing panties and nylons under his skinny jeans when he left. He actually asked for a few ‘tampons-to-go’. Princess has goals. I think he has a bright business future. He gave me $200 and a note when he left. It was a beautiful thing. I could have had a thriving cottage industry with Princess as my sole client.”

Our experience with Princess and the idea of having a cottage industry of cross-dressers and panty lovers planted a business idea in our mind.”

“About nine months after Megan passed I called Princess. I needed carnal release and apparently Princess did too. She called me two weeks later. When we met again she had her ears pierced; two holes in each ear…very cute. She’s the most feminine man I know when she wants to be.”

“Princess had completed his MBA and was looking for a job and a living arrangement. It seems her folks were as not thrilled about their son’s femininity as I was. She needs a place to live and she needs a job.”

Jackie: “I could use a good job and a nice place to live as much as this newly found Princess person. Remember that you and I are sexually compatible. Being around you is as stimulating as when we first met. Let’s give living together a try before you launch the ‘Sissy Salon & Panty Parlor’ business. It would be fun.”

Lindsey’s heart raced as she processed all of what her friend had said. Had she just been propositioned? Was she and Jackie destined to be a couple again? Would Princess be a better roommate? Or would Jackie? Who would be the better employee? Could they work together?

Not knowing what to say or how to respond Lindsey was spared having to say or do anything by the return of Bill. Thankfully Bill had been spared the intimate personal conversation that had just ended. He pulled out his chair and sat down.

Bill returns and the conversation topics change

“Heck, I’m gone for a few minutes and I come back and find you two holding hands. I’d tell you to knock it off and get a room but I think you would!” Bill joked.

Lindsey: “Thanks for the alone time. Jackie and I were talking about how we came to know each other and how Lindsey has evolved from when we would dress up in our sister’s clothes and makeup. In fact I’ve inspired her so much that she’s getting her ears pierced. Right, Jackie?”

Taken aback by Lindsey’s admissions and her use of feminine pronouns in reference to him Jack blushed deeply. “Lindsey has always had an interesting effect on me; care to get your ears done when I have mine done Bill? I bet we can get a discount.”

Bill thought about what Lindsey and Jackie had just revealed before speaking. This new knowledge filled in several points of wonder that Bill and Amy had always had about Jack and why he had never married. “I will pass on that opportunity girls; but thanks for asking.”

Their extended lunch was winding down

Glancing around the table Lindsey made sure everyone had their tequila shot at the ready for a last toast. Standing, Lindsey said, “I know that meeting Lindsey has been of great interest to you all. I hope your curiosity has been satisfied and that you are not disappointed.”

Lindsey held up her drink and pronounced, “Thank you all and happy birthday to Lindsey! Thank you for accepting me. Please tell everyone thank you for the gifts. Megan would have been pleased.” Jack and Bill echoed her sentiments and they all downed their shot.

They hugged. They even kissed and they left.

The next day

Lindsey awoke, showered and set about becoming her feminine self.

Fully dressed from the skin out in women’s clothing, and tastefully made up, she blended herself a banana fruit smoothie and prepared a simple breakfast of toast, one egg and coffee. She sat back in a reclining lounge chair in her living room. Placing her coffee and her new nail polish on a side table Lindsey popped out the foot rest and sat back to finish painting her nails and to ponder how to launch her Sissy Salon & Panty Parlor. She needed a couple of very special employees. Could Jackie and Princess get along?

Readers Poll

If Lindsey decides to have a roommate who should she choose? Jackie? Princess? Why?
Would Jackie and Princess make good employees? Could they all work in harmony?

Back story: Lyle’s character was introduced in my PG rated story called “Rosebud” as part of the Big Closet July 2018 ‘Staycation’ story contest. Lyle was a likable person and I wondered if she had more of a story to tell. She did.