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Claire M

Author: 

  • Claire M

Organizational: 

  • Author Page

Audience Rating: 

  • General Audience (pg)
BigCloset TopShelf Featured Author
Claire M

How Halloween Became My Favorite Holiday!

Author: 

  • Claire M

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Elements: 

  • Costumes and Masks

Permission: 

  • Posted by author(s)
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When Joyce told me all the husbands were dressing up for the Halloween ball, I said okay. I wasn't too keen on a costume. Costumes were for kids. But she was so impressed with her new Bridge Club. And when she told me about the good things they did for the community, I didn't want to say no.

I asked her what she had in mind for a costume.

She told me to just wait until I saw it. She pulled out a ball gown from a fancy box. It was a dark purple, low cut, very shiny, and quite attractive.

I thought it was beautiful and knew that my wife would look great. "Wow, I can't wait to see you in that."

Joyce laughed. "Me? Oh, no, Arthur, this is what you're going to wear."

I shook my head. "You've got to be kidding. I don't dress up like that. I especially won't do that in front of strangers."

I learned never to say never to a strong-willed woman.

Two weeks later, I sat in her salon and watched as one operator attached extensions to my hair and another carefully glued acrylic nails over my own.

After the lengthy process of tinting the extensions to match my own color, I watched as my new long hair was cut and shaped. It was fascinating. It was also a struggle for me not to complain.

After all, I created this problem. I had told my wife that I wasn't about to do this because I wouldn't make a fool of myself. I wouldn't be laughed at looking like some foolish clown who dressed up in women's clothing. And I knew she couldn't make me look like a real woman.

My lovely wife agreed that making a fool of myself wasn't in the plans. "If we can't do this right, I agree not to do it at all."

Then, why was I sitting here being fussed over for hours on a Friday afternoon instead of being out on the golf course? Well, my wife promised me that the disguise was going to be a great one and if it wasn't then I could have anything I wanted from her until Christmas.

So I gave it a try. I had nothing to lose. After all, to be king of my domain until Christmas, having my wife at my beck and call, doing anything and all I desired? Who could say no?

I watched as the operator set my hair. Then she turned to me and said, "we're going to start on your face next."

I watched as she rubbed something over my lips. It was some sort of cream, and then my lips went numb. She rubbed more of the cream on my chin and then under my eyes around my cheeks.

Before long, my face was stone, cold and I couldn't feel a thing. The last touch she did was to rub the last of the cream on my earlobes.

I don't know where the needles came from. Maybe it was the two glasses of wine or the pills my wife had given me, but I sat there and watched as the operator injected something directly into my lips.

"Collagen, perfectly harmless and the effects will be gone before you know it." She smiled and continued to push more needles into my face.

Fascinating, I thought. I didn't feel anything. I think I must have dozed off because when I came around, there was a different face staring at me.

"We went ahead and started on your makeup, Mr. Franklin. This is just what your wife wanted us to do."

I had never seen makeup applied like this. They were using an air gun that sprayed on thin coats of color all over my face. I tried to talk and found that my lips were swollen and it was hard to speak. My voice surprised me. It was higher and came out like a squeak.

"What's happened to me? What have you done?"

The operator smiled. "We've injected some collagen and tightened your vocal cords with a little nitrogen. Nothing permanent, just temporary, but you will sound as cute as you look."

I tried to talk, and she assured me that my voice would stabilize in a few hours and that I'd get used to my lips and talking long before that. She was right. I was able to talk eventually without lisping.

After they put the finishing touches on my face, they sprayed a sealer on. "It's all organic. It helps the vegetable dyes sink deep into your skin under the pores, almost like a tattoo but nowhere near as deep or permanent. You'll be able to wash your face in an hour and not disturb any of our work."

I was amazed. Joyce was right. With my large pouty lips and more pronounced chin and cheeks, I did look a lot less like me and a lot more like a woman.

I stumbled when they helped me from the chair. Someone handed me another glass of wine, and I had trouble holding it. Those long fingernails would take some getting used to.

I was led down a hall where a beautiful woman helped me take my clothes off. It was strange just how relaxed I was standing naked in front of a stranger.

I lay down on a table while a machine was pulled out and aimed at my body. Slowly, the hum of the machine and the warmth of the room sent me back into a slumber.

When I awoke, I felt someone pushing on my skin. I was turned over and felt something wet and warm against my cheeks. I opened my eyes and tried to move. I heard a voice telling me to hold still for one more minute until the glue had dried.

"Glue?"

"Sure, Mr. Franklin We can't attach the pads without glue, and it won't work if you move."

I did my best to lie still. I was told that I could sit up and when I did, I got a surprise.

I had breasts! I looked down and was surprised to see that they formed a seamless seal on my chest, which was now completely hairless. "How'd you do that?" I was pointing at the two melons pointing outwards from my body.

"These are silicone, and the adhesive melts very nicely to your skin. We used a laser and a mild defoliant to remove your body hair. Don't worry; it's all very safe. Nothing will affect your vital stuff."

I was shocked to feel her reach between my legs and fondle my cock. I had no trouble getting hard, almost too hard and way too quickly.

I moaned and felt myself having an orgasm. I sprayed all over her hand and arm. I was breathing hard. "Oh, I am sorry! I've never responded like that before!"

She laughed and told me it was perfectly all right. "We see that sometimes with the adhesive we use to tack on your new body parts. It causes certain physical responses that lessen eventually. We suggest you wait to have sex. You'll find yourself to be too responsive in the bedroom."

I wiped myself off. It felt like I was sitting on a cushion and when I looked, I realized that the woman had also attached pads to my hips and my rear end. "I can't feel my bottom."

"One more treatment and you will. The adhesive has to dry first."

I kept looking down at my chest. My new fake breasts were big and round, and the nipples were thick and pink. It was surreal.

I was helped up and propped against the wall. Then the same woman appeared with a sponge and started to cover me with a blue fluid from head to toe.

"It won't be too uncomfortable for long. As soon as I finish, we will get you in the lights, and you'll be amazed at what will happen."

I was covered from the neck down with this blue sticky stuff that felt like honey. I marveled as it soaked into the pads covering my chest and my rear.

Then, Denise led me to a room used for tanning. She handed me two tiny eye covers. I placed them on my eyes. "Stand here and close your eyes. It only takes a few minutes."

I felt the lights get bright and the honey like stuff started to warm on my skin. After a few minutes, it felt like I was tingly all over, almost itchy.

"Done, Mr. Franklin You can open your eyes."

I looked down and touched the pads on my chest. The glue seams were gone, and I could feel sensations through the pads and into my own skin. It was strange. I rubbed my hand across my bottom, and it almost felt like I was touching skin.

"You will get more and more sensation as we go along. The silicone is warming to your touch, and the contact jelly is helping create hypersensitive nerve endings through the silicone and into your body. It's all perfectly harmless, but a great technology breakthrough."

"How much is this costing my wife?"

She grinned. "Nothing. The bridge club annual costume ball and auction not only pay for all of this but sends a great deal of money to a number of charities."

"Wow. I'm impressed."

So I stood there naked and looked myself over. My mother wouldn't have recognized me. I had a generous, lush figure attached to my 5'9" frame. I had high, round breasts with incredible nipples. My rear was round, and my hips were wide enough to make my waist look small and nipped.

And my face was incredible. My lips weren't numb anymore, and I could talk. My voice was higher but sounded perfectly natural for a woman. I looked in the mirror and was amazed at my makeup and hair. My tresses fell below my shoulders in thick curls. It was the same light sandy color of my own hair but seemed to have highlights of gold and blonde.

"Amazing," I squeaked. I can't believe this is happening. "How many other guys are you doing this to?"

"All the new women in the Bridge Club volunteer their husbands for our auction every year. Its part of the fun of the Grand Ball and that's how the group raises most of their money."

An auction, I thought? What is she talking about? This wasn't the time or place to ask, and I figured my wife would know the answers when I got home.

Then it dawned on me. How was I to get home? I couldn't wear my own clothes! And standing there naked, it was apparent that I'd be hiding from the neighbors until this was all over tomorrow night.

I looked at the hairdresser. "Am I coming back here on Sunday to get all this off?"

Denise looked at me strangely. "We aren't open on Sunday."

I figured that I had better call the office and tell them I'd need a vacation day on Monday. I needed to have all this removed before anyone saw me at work. My credibility would go right down the tubes. Guys in drag don't sell commercial construction equipment.

"How am I going to get home? What am I going to wear?"

Denise smiled and led me down the hall. I was hard again. It was embarrassing, and I was glad no one saw me. What would they think if they saw some woman with a hard-on and C cup breasts strolling naked in a salon!

Denise took me into a dressing room and began opening packages. She showed me how to slide stockings up my smooth legs and how to fasten a garter belt. She laughed when I tried to get my erection inside a pair of panties and with a few expert twists of her wrist, I had an orgasm. I was able to put on panties when I was soft again.

She helped with a cotton bra and then a yellow tee shirt. Even with the top on, I felt half undressed. Woman's clothing is so much softer and thinner than men's clothing.

Then she showed me how to fasten a wrap-around skirt, and I was amazed. No more signs of my male self at all. I was a different person.

I was getting worried. The pads seemed to be growing more and more sensitive. I could feel the underwire of the bra cups touching my skin and my new breasts. I wondered when it would stop.

The hardest part was wearing a pair of slides. Slides are shoes with no backs and some heel, and it took some careful steps to get out to the entrance of the salon.

My wife was waiting. She smiled and gave me a peck on the cheek. "Beautiful. I was right. No one will recognize you."

I had to agree. I was using my full concentration to walk to the car and was happy to be driven. I had no desire to get stopped by the cops and try to explain what was going on.

Then a thought struck me right between the eyes. What was going on? Why was anyone going so far as to create such an elaborate costume using all this technology?

I started to question my wife. She giggled.

"I love your voice, and those lips of yours are great."

I pulled down the visor. My lips were big but pretty. I touched them and was surprised when the pink, glossy lipstick didn't come off on my finger.

"Don't worry, sweetie. We are going to have a ball tomorrow practicing for your ‘coming out'. You are going to be a real hit. I am so happy you are going to be a success."

I must have dozed off because the next thing I knew, Joyce was helping me into the house.

She sat me down in the living room and turned on the television. "You need to watch this tape."

It was a professionally done sales production. The narrator mentioned that the Bridge Club of Washington, D.C was the largest contributor to the Girl's Clubs of the United States. The funds were all raised through their annual Halloween auction.

I watched as men bid on beautiful women. Thousands of dollars were raised to help underprivileged girls across the US through this annual event being held in many cities across the country.

The tape went off, and I turned to my wife. "What's that got to do with me?"

She giggled. "You were so busy asking me what would happen if you won the bet, you never asked me what would happen if you lost."

She was right. I was so intent on planning to be the lord of the household that I never even thought I would lose. But looking at me, I realized that I had lost the bet.

"What do I have to do?"

Joyce smiled. "You simply have to cooperate."

"By doing what?"

"You're being auctioned off for charity."

"Charity?"

"Uh-huh. We are going to dress you up and then you are going to be auctioned off for fun to some guy who wins you as his date."

"I have to go out on a date?"

"For fun."

"Who's going to have fun?"

"Silly, it's for a good cause. All the women's husbands have done it and you will, too. I've heard that some guys understand it's for a good cause and sign up for it annually."

"But, I don't know how to act! I'll make so many mistakes trying to act like a woman. I don't want to be laughed at. I hated being laughed at like I'm a fool.

So, on Saturday, we practiced. I learned to walk and sit. I learned to gesture with my hands. I reviewed everything I needed to do to be a date. I was determined to get it right.

That night, the worst thing was discovering that everything was securely glued on. My makeup was there under my skin and didn't need to be reapplied. It wouldn't smear or run. It was strange looking at myself with glossy pink shiny lips and dark mascara and liner and blush. Looking in the mirror was awkward.

The pads that were glued to my body kept growing more comfortable every hour. By the time I went to bed, it was hard to tell where the pads stopped and I started.

The most amazing part was how quickly I was aroused. Those nipples were sensitive to touch, and all my skin felt like I was on fire. I loved contact.

Joyce laughed at how hard I got and was amazed at how fast I recovered. I was getting better controlling my premature ejaculation, and we were both exhausted after an hour of lovemaking.

After much rehearsal and practice, I was ready to go to the party.

My ball gown was deep purple and showed off my lush cleavage and seemed to accent my curves very nicely.

I still was a little shaky in heels and had to be careful with each step. I was used to hearing my voice, and while it still sounded strange to my ear, my wife assured me that it was lovely.

After brushing my hair and pinning it up, I was ready.

I was surprised when all my wife was wearing was a woman's tuxedo. She looked pretty in it. Without a shirt, her own cleavage showed through her lacy bra, and well, you couldn't make a mistake that she was all woman even in what looked like a man's outfit. It was cut differently accenting her slim waist, round bottom, and generous hips.

We took a cab to the convention center. My wife helped me up the steps, and we entered the lobby. There, my wife kissed me goodbye, and a woman appeared. She smiled and said to follow her. I was led off to the back of the stage. I wasn't surprised to see a lot of lovely women standing around talking, but I was amazed when I realized that they were all men.

Some of them were obviously old hands at this and were laughing and talking and having a great time. I was shy and didn't want to say anything to give away that I really was new and very nervous. The last thing I needed was for someone to realize who I really was.

It was odd. Each of these men had undergone the same treatment I endured. All the conversations sounded just like women having a grand time. They were all beautiful with long flowing tresses, elaborate makeup, and gorgeous ball gowns.

I was given a sash with a number on it, and someone placed a tiara on my head. Then, when it was my turn, I was ushered out into the spotlight and walked around and turned and then the bidding began.

I was amazed at the bids. I swore that my own wife was bidding, too. I could hear both men and women, and finally, the bidding seemed to stop at ten thousand dollars! Yeah, someone was bidding ten thousand dollars for a date with me!

I was led to the back, and then two ushers took me to my seat. I was introduced to the man who had bid on me, and I smiled. Then when I saw who it was, I was shocked! Charlie Brooks was one of the owners of the company where I worked. I had known this guy for years. I smiled and told him how nice it was to meet him.

He looked at me and laughed. "Don't clown around, Franklin I've met you on so many occasions that it's not funny. What would you like to drink?"

Oh my God! I wanted a drink so badly that I would have drunk anything. My head was spinning. What was going on if my boss was in on this and had given ten thousand dollars to charity to go out with me?

I drank a glass of wine and after the second one was shocked when Charlie Brookes put his hand on my leg. He slid it up my dress and was touching the top of my stocking where it touched my garter.

"Nice legs, Arthur. Never realized until tonight that you'd make such a cute broad."

I was frozen in space. I was afraid to make a scene, and well, this was my boss! Maybe he had too much to drink, and perhaps he was joking! And who was I to upset the apple cart?

When his hand reached my silk and lace panties, I held his arm. "Uh, Mr. Brookes…"

"Call me Charlie."

Suddenly his hand had a firm grip on my unit, which was standing at attention. I was ready to launch thanks to my body's reaction to the glue they used to hold my pads in place. "Uh, Charlie, are you sure you want to be doing that?"

He kissed me hard on the lips. I couldn't pull away because one of his hands was squeezing my member and the other hand was holding my neck firmly. I didn't realize how strong he was.

I let him kiss me. I guess it was the wine or maybe all the stuff glued to me, but his lips felt good on mine. Geez, what was I saying?

I was straining in my panties, and his hand was massaging me, and it was all I could do was to spread my legs to give it some room.

Charlie continued massaging me and kissing me and the next thing I know, I was having a small, very intense orgasm into his hand.

I was quivering and leaned against him. It was pretty shocking how intense it was. I realized that I was leaning my breasts against his arm and he was cupping them as he started stroking again.

My panties were sticky and wet, and I was dripping down my stockinged leg. As embarrassed as I was, my body was deserting me. I was ready again.

I tried to stand, and Charlie helped me up. I told him I needed to find a bathroom and he was suddenly a gentleman as he helped me up and out of the room.

I searched the place for my wife, and she was nowhere to be found.

Charlie held the door open for me, and I was surprised when he followed me into the bathroom locking the door behind us.

I was surprised how hard he kissed me on the lips, pushing me back against the tile wall. His hands roamed my body, and I moaned, as the pads seemed to radiate feeling and heat. I spread my legs for balance.

He lifted my skirts, and his hand found me again. I made a groaning noise as I started to erupt again.

This time, he levered me back between my legs, and I sprayed all over my own backside. He still cupped my unit and was rubbing my fluids against my hole.

I was helpless and held my arms tight around his neck. His fingers probed my hole and grabbed my bottom.

Suddenly I was lifted up in the air, and I instinctively spread my legs around his waist. I kissed him and begged him to stop.

Charlie laughed and kissed me back. He reached down and dropped his pants and pushed me back against the wall.

I felt his hardness probe my rear, and suddenly he slipped into me. I shuddered with the overwhelming feeling of my body being entered. I trembled. But, it felt good. I grabbed his neck and sucked hard.

I held him tight as he impaled me and began to pump. It wasn't my voice that was demanding to be taken but some woman's moaning, cursing voice that was begging for more.

After he came, I found myself on my knees worshiping his magnificence. I demanded that he use me doggy style and take me right there at the sink.

I watched in the large glass mirror as the woman in the satin gown was being fucked in the rear standing up at the sink. She seemed like she was having fun.

We did it three more times before we were exhausted. My legs were shaky as we kissed and shared a cigarette.

My wife never mentioned the chemicals wouldn't dissolve right away. The pads and the makeup and the hair and nails were with me well through the holiday season.

I went to work in a dress and was surprised that contractors still took orders from a beautiful woman. Charlie and I enjoyed our romance and stole some time each day to ripe off a couple of quickies.

By January, I was able to get out of the costume and resume being myself. It was a strange sensation to wear my old clothes again.

Joyce and I were much better off for my change in attitude and sexual orientation. Nothing wrong seemed to come of it. I earned a great bonus at Christmas, and my job was indeed secure.

And I was looking forward to celebrating Halloween again in the fall. I had learned that costumes weren't just for children.
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Dear Reader:

Thanks for reading. Just to mention I have two books out on Amazon. One is called “Living My Fantasy.”
an erotic transgender story.”

It tells the story of a guy who loves reading transgender erotica so much that his wife helps to change him into a transgender woman who gets to live out the fantasies he loves so much.

The story takes him through the drama of the confrontation with his wife about his favorite stories; his complete transformation; and finally all the imaginable erotic fantasies that one person can have are all in there.

The second book is called, “Turned Into His Girlfriend, first-time transformation.”

This one tells the story of a nineteen-year-old guy who becomes an older man’s sissy girlfriend. It’s a fun walk on the wild side. It’s full of fun, sex, smiles, more sex, and lots of fun.

Both books have lots of free chapters to look through.

Thanks.

Rooster

Author: 

  • Claire M

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

Rooster
lingerie 1.jpg


By Claire M

TG Themes: 

  • Romantic

Rooster Ch1

Author: 

  • New Author
  • Claire M

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Romantic

Permission: 

  • Posted by author(s)

It was a contentious meeting.

General Food Products was trying to acquire Matilda's, a leading name in the custom lingerie industry. The lawyers were negotiating while the principals sat there patiently trying to stay awake.

Finally, after a one-hour impasse, Matilda Davenport pushed back her chair and stood up. She surveyed both sides of the table. She looked at her team of lawyers and then looked at the General Foods team of lawyers. Right in the middle of the group was the CEO, Adelajda Novak.

Matilda Davenport leaned in making sure she had eye contact with everyone. She rested both her palms flat on the table. And shook her head in distaste. ”That's it. I'm leaving. As my daddy used to say, ‘There's only room for one rooster in the hen house.' I've been sitting here listening patiently for sixty minutes while you two attorneys crow at each other.” She waved at both sets of lawyers disdainfully.

She straightened up and looked across the table. "I'm going to lunch, and I'm taking your number cruncher with me. Come with me, Mr. Rollins, you're going to buy me lunch. And then, the two of us will negotiate a contract while these useless, high paid solicitors waste our money."

Matilda headed for the conference room door, her shapely rear swaying as her three-inch stilettos emphasized her determination and femininity. She was not looking back as she spoke. "Now, Mr. Rollins."

Lester Rollins panicked and looked over to his boss. He saw the look of exasperation and frustration on Adelajda Novak’s face as he gestured for Lester to get up and get going. This deal was essential to General Foods Products. They needed this legitimate quality name brand to front their plan for a national division of mall stores where they'd flood the market with their factory made inexpensive goods. Matilda's name recognition meant excellence as a recognized leader in undergarment fashion. They needed her name to sell their low-cost products.

For the past ten years, Matilda's produced a lingerie catalog like no other. Their Christmas catalog was released every September. It was considered a high art form. Inside the glossy production were forty pages of the most beautiful undergarments ever seen modeled by the most famous women on Earth. The catalog elevated lingerie to a level where women jokingly discussed wearing just Matilda and nothing else out for that special evening.

The catalog was the company's bread and butter. Their mail order business sold all those items displayed. Men and women both eagerly perused the pages looking for that something special to buy for themselves or their favorite person.

As they rode the elevator up to the restaurant at the top of the building, Matilda had a chance to evaluate Lester Rollins fully. Discreetly looking in the reflections from the four glass walls as they rode to the top together, she sized him up. After studying his bone structure, features, and coloration, she thought he would do just fine as a candidate for a project.

After all, when she got done liquidating Matilda’s today, she'd need a new project, something different to amuse herself with.

They sat together at a table in the back of the dining room where it was discreet and quiet. As Lester gazed out at the New York skyline, Matilda studied his profile. ‘He's perfect,’ she thought. "Are you married, Mr. Rollins?"

Lester was shocked from his reverie. He turned to look at the beautiful woman staring at him. His eyes nervously looked down at the table where his hand was running across the tablecloth's quality cotton-linen blend. Whenever he was anxious, he became quite tactile. "No. I'm not married." He did his best to look this powerful woman in the eyes.

"Dating?"

Lester shook his head no.

Matilda took a deep breath. She smiled and looked Lester directly in the eyes. She noticed that his eyes were a beautiful deep blue. “Okay, Lester Rollins. It’s time to do some business. Are you ready to listen?”

When Lester nodded yes, Matilda began to tick off her points one by one. “Here we go, Mr. Rollins. I want one hundred million dollars of your company's stock. I sign a five-year non-competitive binder. I agree to a one-year consultant contract for two hundred fifty thousand dollars which will include six positive press conferences and a dozen public appearances with the company paying all my expenses. General Foods will be buying all our logos, and my face is part of the package. That package is ten million dollars. If you chose to make a catalog, I would help supervise it. We start that on January 5th of each year. Your company, General Food Products, will own everything Matilda."

Lester Rollins smiled. Now he was on familiar ground. He nodded and picked up his phone. He dialed the CEO he'd left sitting at the table. He leaned over and whispered into the phone. ”Boss, we've got our deal." He listened. "Yes, everything, just like we talked about before the meeting."

Lester leaned across the table and offered to pass the phone to Matilda Davenport.

As she reached for the phone, Matilda took Lester’s hand in hers. As she talked, she held his hand gently. He had soft, delicate hands. She was pleased to see he took care of his nails. She looked him in the eyes while she confirmed her offer again to Adelajda Novak, the chairman of the international conglomerate.

She returned the phone to Lester. "My lawyers already have my offer in their hands. I’ve signed my offer, and it’s been notarized. My team is presenting our contract to your boss to be signed."

Matilda let out a deep breath and smiled directly into Lester’s eyes. “We've finished all the business. Now it’s time to order lunch." She signaled to a waiter.

When he arrived, she ordered for the both of them. "Two petite filets, medium. Two tossed salads, dressing in the side. And we'll have a bottle of Peter Michael Cabernet Sauvignon, 2012. Open that now for us, please.

Lester remembered the last words his boss had said to him before he hung up. "Whatever you do, Lester. Don't blow this deal. You've charmed her because she gave us everything we wanted. It's a great deal. Remember, Lester, don't fuck this up. You need to be charming and agree with whatever she wants. She has to stay happy until at least three days have passed.”

Lester knew precisely what his boss meant. The contract was only binding after a three-day moratorium had passed. Before that, Matilda could change her mind and tear it all up. Adelajda Novak wanted the signed deal, and Lester Rollins was the difference between success and failure.

When lunch was over, Matilda stood and asked Lester to take a walk with her. "I overate, honey. I need to get some fresher air. Why don't you join me?"

Lester just nodded and shuffled along. He was feeling stressed after the lecture his boss had given him. He certainly didn't want to report to work tomorrow to find out Matilda had rescinded her agreement. Lester knew by law that Matilda had three days to change her mind and cancel. He also knew that his career with General Food Products depended on it.

That meant he had to do his best to keep the charm flowing for at least the three days. He smiled as they walked along the East River.

Matilda reached over and grabbed his arm, inserted her arm into his. She was steering him along, setting the pace. She leaned down and whispered in his ear. “You're a lot of fun, Lester. I like the way you can relax and go with the flow. I appreciate that in a man. That's nice."

Lester smiled. He felt relieved that he was scoring points. He thought that keeping his mouth shut and just nodding was his best move. Lester figured that the less he said, the better.

Matilda steered them to a bench set back from the walking path. She sat them both down. Matilda and Lester both stared at the water and the occasional jogger running by.

Matilda moved closer to Lester until their thighs touched. “I like you, Lester. I like the way you don't feel the need to take charge. That's the sign of a confident man who can sit back and enjoy life. I'm impressed. I can't believe you don't have a girlfriend or aren't married. So, now tell me the truth.” She looked directly at him and smiled.

Lester smiled back. “No, Matilda, I'm not gay. I love women.”

Matilda laughed. "What's the catch then, Lester? How come you haven't been swept up by some lucky woman? How old are you?"

Lester smiled. "I'm twenty-seven. I've had a lot of dates and have met some women who are fun. But, I've never met the woman who would fulfill me. I guess I must be too picky. But, how about you?"

Matilda laughed. "I'm thirty-nine, Lester. I have a son from my first marriage. He's nineteen years old."

Lester did the math quickly. “Miss Davenport, why didn’t you remarry?"

“Well, Lester. First, you have to call me Matilda. After my divorce, my business took off. I was busy raising Charli, and I guess that my business became my second husband. Raising a child takes a lot of energy, too. Charli is very special to me. I guess you could say that he's that he’s that special person in my life."

Lester tired to smiled. He was uncomfortable. This whole afternoon all seemed like a really oddball interview. Lester felt like he was auditioning for a part in this woman's life. Lester wasn’t big on relationships. Lester was afraid of any commitment and wasn't ready for failure. After leaving home and moving out from his mom's house, every relationship he'd set his hopes on had ended poorly.

Matilda stood up and looked down at him. "C'mon, Lester. That wine with lunch made me sleepy. I think I want a nap. Will you escort me back to my room?"

Lester nodded, and Matilda gave him a hand as he stood. He had been raised properly to be a gentleman, but this was odd. He'd never had a woman offer him a hand.

As they walked back, Matilda grew quiet. They were soon nearing her hotel. When they entered the lobby, Matilda still had hold of Lester's arm as she steered him to the elevator.

"I would like you to escort this lady to her room, Lester." She smiled as if it was understood.

When they got off the elevator, Matilda led him down the elegant hall to her accommodations. "You have to see my room, Lester. Your company paid for a wonderful suite for the next three days. I guess they wanted me to hang around until I couldn't withdraw from the contract. C'mon, honey. Come on in." She laughed and gestured.

Lester knew that saying no to Matilda was a tactical error. Once they were inside, he hoped they'd sit and talk. Two glasses of wine had also affected his judgment. He expected that maybe Matilda would relax and close her eyes. Then he'd get to slip out once she was snoring.

As soon as they walked into the living room, Matilda smiled. She turned and started to walk away. "Enjoy the view, Lester while I slip into something more comfortable." She stopped and backed up grabbing his hand. “Oops, you'd better unzip me, sweetheart. Now, don't you disappear."

After Lester unzipped the top of her dress, she turned and placed both hands on his shoulders. She kissed him gently on his lips. She held the kiss for a second longer. She was sending a message. “I’ll be back, sugar."

He watched as she walked across the hardwood floors, her heels making that beautiful sound a stiletto makes. He admired her shapely figure as she went into the bedroom.

Lester shook his head. He knew things were not going to go well from here. He knew what Matilda wanted to happen and was afraid he wasn't the man for the job.

Lester contemplated his two choices.

He could flee right now. Take the elevator to the ground floor, and then he’d lose his job, He knew he’d be blackballed and any hope of ever working in the accounting field again.

Or, Lester would stick it out and inevitably fail here. Once he proved to be less of a man, he’d lose his dignity and self-respect.

Before he could decide, Matilda returned. It seemed that she had slipped off her dress and freshened her makeup. She wore a sheer, diaphanous gown revealing her perfectly sculpted body wrapped in her own product.

Lester lost his breath and gasped for air. “Its model three oh two," is all he could croak.

Matilda smiled and kissed him again a bit harder on the lips. She whispered intimately. "You know my catalog! How wonderful! What a lovely thing to find out.” She spun around showing off the beautiful detail of the Merry Widow and the matching thong. Her pale flesh only accentuated the contrasted the deep black of the satin material.

Lester was mesmerized. "That's an original three-oh-two; it was shown for the first time seven years ago! This bustier was one of the most popular from the Matilda line ever. It appeared in four runway shows in Paris and New York. It was made from satin, Lycra, chiffon, and lace.”

Matilda came back over to him. He was sitting in a fabric covered armchair. She leaned over showing off her soft, creamy bosom and kissed him firmly on the lips.

Matilda winked. "Do you like what you see?" She placed both his hands on her hips.

Lester nodded. His hands reached up and touched the fabric where the bustier touched the top of the hip. He was hypnotized by the beauty of the stitching and the material where it met her flesh. He moved out of the chair and fell to his knees. Lester moved his head closer to her body. He lined up with the top of the satin thong. He moved his head close and kissed the flesh between the top of the thong and her exposed navel. Maybe it was the wine, her perfume, or her beauty, but Lester felt that he was losing his mind over Matilda. He had no self-control. He was mesmerized by this powerful woman.

She opened her mouth and gasped. His touch was so delicate and gentle. His lips caressed her skin softly the way she loved it. And his lips were so pillowy tender on her flesh. It had been a long time since she had a worshiper. That is what she adored in her man.

Matilda gushed. "Oh, Lester. We are going to have so much fun this afternoon. I am going to take you places you’ve never been before. Are you ready to pledge your heart and soul to your mistress?

Lester looked up. He felt safe and secure with such a powerful woman. He wanted to feel love again the way his mother had loved him as a child. He wanted to adore the woman who would tell him what she wanted. No mysteries, no games. Just unconditional love.

Lester nodded. He was so excited he was having trouble catching his breath. "Yes. I am ready. But you need to understand. I am inadequate. I am unable to give you what a man can give a woman." He stood and started to get undressed.

Matilda helped him take all his clothes off until all that was left were his boxers. Her heart was beating faster as she examined his body.

Lester's body was slight and pale. He was without any musculature on his small frame. His upper body and arms were not defined but soft. His chest was flat and nearly sunken. He had no hair on his upper body.

Lester looked at his queen briefly, and then his eyes dropped out of respect. "All my life I've suffered from low testosterone. I've grown up without any of the boosts that the hormone would have brought to my body. I'm unable to function as a man. I'm afraid I will be unable to please you or satisfy your cravings."

With that, Lester dropped his boxers to the ground and delicately stepped out of them. He revealed his manhood. The fact that he had no hair between his legs only emphasized how small his genitals were. It looked like his growth had stopped in middle school leaving him a tiny penis and testicles. They were perfectly formed and pink.

Matilda was caught up in emotion. "Oh, Lester. You make me so happy. The last thing in the world we needed to come between us was a large erection that demanded our attention. I love you and your body and will be happy to show you many ways we will be able to satisfy each other. You will be pleased to know that when I find satisfaction, so will you." With that, she pulled him up from his knees gently, the way you would treat a lovely wife. She took him in her arms and held him tight. She leaned down and kissed him.

Lester was not tall. And the fact that Matilda was wearing her three-inch stilettos made her loom over her new conquest. She took him in her arms and heard him sigh with contentment. Lester felt elated. ‘This was the way it was supposed to be,’ he thought.

Lester closed his eyes. He had told his worst truths and instead of being cast off was drawn closer. He was happier than he had ever been.

.

to the reader,

Please take a look at my new novel on Amazon under my name, Claire M Drake called

Living My Fantasy, an erotic transgender story

there are a number of free chapters to look over

Rooster Ch2

Author: 

  • Claire M

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

Permission: 

  • Posted by author(s)
Lester In Lavender.jpg

Chapter Two

Lester In Lavender

Lester closed his eyes. He had told his worst truths and instead of being cast off was drawn closer. He was happier than he had ever been.

But, Lester knew happiness was like a struck match. A quick, bright flame burns hot and bright but extinguishes quickly. Experiencing joy or pleasure in brief, fleeting moments only to vanish altogether, crushed under the dreariness of his mundane existence.

Today, Lester sensed that something different might have transpired. Instead of humiliation and rejection, Lester stood in the doorway of something new. He felt the breeze from an open window.; the sun shined on his face and into his heart; Lester had met someone who embraced him knowing his shortcomings.

He had stripped himself naked both figuratively and literally. In baring his soul, a goddess had embraced him. She had gathered him in her arms and expressed pleasure in discovering Lester. He had not felt so happy since he was young.

Lester learned early how different he was from others. He observed that differences are disliked in society. As he progressed through those formative years, he understood that the hive mentality rejects challenges to the status quo. Conformity was embraced and anyone who didn’t walk in lock step was viewed as a threat. Threatening people had to be driven out and destroyed.

It wasn’t his fault that he was odd. Lester was slow to develop physically. His mind grew quickly and knew all the academic answers. But, being too smart was also a threat to the system. Lester learned the hard way through mockery and ridicule to tamp down his eagerness to please the teacher. By appearing to be less, he briefly gained acceptance. But it was short lived.

Lester didn’t develop at a reasonable rate. While his peers were going through puberty, he seemed to have frozen in place. The gym class locker room became a nightmare. Classmates were eager to show off their changing genitalia and flaunt sprouting pubic hair. And Lester was teased about his undeveloped body. Lester waited for his turn. His pediatrician called him a late bloomer. But the blooming never happened.

He watched as the boys in his class grew into men and were gifted with muscles and height. The giggling, little girls grew ripe and lush with feminine beauty. Lester was not a late bloomer, he was a non-bloomer.

He learned to hide those differences with thicker soles on his shoes for added height and heavier clothing to bulk him out. He tried to camouflage his differences by wearing drab colors. He was so self-conscious, he wanted to disappear. Lester was learning to hate the world he was stuck in.

If it wasn’t for his daily escape, Lester knew he’d explode.

Every afternoon, he’d endure the school bus ride home to an empty house where a crock pot was the only sign of life. The comforting smells would envelop him as he walked through the front door and down the basement to the laundry room. Since everybody else worked until late, It seemed fitting that he should perform a share of household chores.

Lester was responsible for all the family’s laundry. He sorted, ran the washer and dryer, hung clothes up, then ironed and folded. He learned quickly how to separate by colors and fabrics. He learned which clothes needed different washing temperatures and treatment. This became his world.

He did well, filling drawers and closets with fresh smelling, clean clothes. He was praised for his efforts. He was rewarded. He was accepted and appreciated.

In all the other worlds, he was still considered a freak. He was only five foot six inches tall and slight. He was used to being bullied and treated badly in school.

His home was safe. Lester never grew much taller and didn’t develop like his peers. He was stuck and sadly even his older sisters and mother looked down on him in their high heels.

His world was their basement. He had developed a routine that provided comfort. Each day, he’d walk down the steps into the cinder block walls and concrete floors, where the light shined in from high casement windows. His drying racks and clotheslines waited. Lester would strip off all his clothes and carefully fold and hang up them up. Then he would begin his routine.

No one arrived home to this working household before six o’clock. Until then, he was alone in his own world. Lester would start with undergarments. He had a world to choose from. Both his mother’s and sister’s lightly soiled bras and panties waited to be washed. And to his joy and comfort, he had colors and styles to mix and match. Each day was filled with a multitude of delightful choices.

Before he would start to sort the dirty laundry into his different baskets, Lester would choose his outfit of the day. His hands rapidly combed through the piles of yesterday’s clothing as he searched out the right outfit to wear.

He’d find a piece of clothing and search for its mate. Once he was successful, he would hold them up for his inspection. He’d caress the fabric against his cheek inhaling the scent. And then he’d start to get dressed in his choice of lingerie.

He took his time dressing, sliding fabrics up over his smooth and hairless skin. Once he had his lingerie on, he got out his true prize. His oldest sister had gone to many weddings as a bride’s maid. She had a collection of dyed to match the dress pumps that she swore she’d never wear again.

One day, she cleaned out her closets and threw them all in a box for the trash. These were Lester’s salvaged prize, four-inch stilettos in red, black, navy, lavender, and pink.

Today, Lester was in lavender. He wore his sister’s panties, a matching lace cup underwire, softly padded B-cup bra, and his prized high heels. He stood tall and proud as he modeled in front of the full-length mirror he had installed himself on the back of the powder room door.

He inhaled deeply catching whiffs of his sister’s perfume, lotion, moisturizer, and deodorant. He proudly turned, admiring his long legs and slender body. He relaxed and began to work. For the next two hours, he washed, dried, ironed, and folded. He did his homework and read in the warmth of his inner sanctum.

Lester found comfort in lingerie. He felt peace and contentment. There were few sexual stirrings. There were rare moments of masturbation or release. Lester valued his solitude by imagining this was his life, his role.

At five thirty each day, Lester would disrobe and add the beautiful underwear to tomorrow’s basket to hand wash and air dry. He would return into his school clothes and tote the clean laundry upstairs to put away in closets and drawers.

At that moment, his phone rang interrupting an interlude where time had stopped. He had been hypnotized by Matilda’s finery. He found himself on his knees worshipping a beautiful living goddess come down to earth. But, now, the insistent squeal of the company phone interrupted his reminder of the celebrated part of his youth. He guessed who it was. He looked at Matilda for permission, and she nodded her tacit acceptance.

He scrambled over and located the offending device. He extracted it from where all his clothes remained scattered on the floor. He had undressed right in front of Matilda, the matriarch of custom lingerie, when she strolled out from her bedroom in seamed stockings, three-inch stilettos, a garter belt, the breathtakingly gorgeous Merry Widow and the matching thong.

Now he stood naked, pulling his phone from his pants pocket. He held the phone in his hand. It was his boss, the CEO of General Foods Products, Adelajda Novak. Lester had a confused moment. He wanted to run away and hide in the basement where no one could find him. He wanted to feel safe and free.

Instead, he bravely answered. “Yes, sir.”

“Rollins, Adelajda Novak here. I need to talk to you. Are you there with the woman or can you talk?”

“Give me a moment, sir.” Lester looked up into the eyes of Matilda.

Matilda smiled. She nodded and pointed to another door in the suite located directly across from her bedroom. Lester walked quickly through that door assuming it would be a bathroom, but instead it was another bedroom. He realized he was still naked as he glanced in the large mirror by the doorway and the en suite bath. He ducked into the smaller room, lifted the lid, and sat.

Lester had always seen his mother and sister sit on the toilet and grew up thinking that was the way. His father was a cipher. Until he was in school and walked into a boys room, he never knew he had an alternative. It was a cultural shock when he saw others pulling out their members and urinating in a porcelain fixture that seemed to be designed for that purpose. Imbued with this new cultural knowledge, he still chose to open a stall door and sit on the toilet.

He made himself comfortable and took advantage of the toilet to release a stream into the bowl water. “Yes sir, I can talk openly, sir.”

“What’s her mood, Rollins. Are we going to have a deal?”

Lester smiled. It was the first time he’d ever had a conversation with Adelajda Novak while using the toilet. It was also the first time he’d had a conversation with him naked. “Yes, sir, we will.”

“How sure are you, Rollins?”

Lester Rollins knew there was no going back. He had become the samurai ronin. Lester now had no master. He bravely spoke. “I’m betting my job on it, aren’t I?”

Adelajda Novak didn’t even hesitate. “Damn fuckin’ right, Rollins. Your job hangs by a thread. You succeed or don’t return.

“But, I can’t believe that I need you here, too. I depend on you, Rollins and unfortunately I can’t clone you. Who’s here in your department to give me financial advice? Who is handy Who can I use while you are on this assignment?”

Lester was done using the toilet and reached for a tissue. He dried the head of his penis carefully. He stood up, but waited to flush.“I have two great assistants who do a fine job, sir. Either of them could step into my position tomorrow.”

“But, your assistants are women, Rollins. Am I right?”

“Yes, sir.”

“I don’t take advice from a woman, Rollins. I’m old school. I’m not some liberal pansy who thinks women are his equal. I need to talk to someone with balls. When you get back here, you find me a guy to talk to, right?”

“Yes, Sir” Lester heard the phone disconnect. He flushed the toilet and washed his hands carefully. He walked back into the living room.

Matilda had sat down on the couch. She smiled and crossed her legs. “Was that our new friend, Adelajda Novak?”

“Yes.”

“Was he concerned that I would back out of the contract?”

Lester nodded, “Yes, very concerned. He wants Matilda’s cachet. He’s banking on it.”

Matilda sighed. “Yes, I know. He wants to open one hundred mall stores and call them Matilda’s. He wants to sell his vastly cheaper, shoddy material under my name.”

Lester looked up and into her eyes. “Yes, that’s correct. How long have you known?”

“I knew the day he called you into his office and told you he wanted a month’s worth of research done on my company. I knew the day he told you he wanted to buy me out.”

Lester looked at Matilda with more respect. He wondered who told her. “And you didn’t try to stop him?”

He looked her in the eyes as his mind examined the possibilities. “Did you want to liquidate?”

Matilda smiled. “Oh, yes. I get offers frequently to buy out my business. But most bidders want my help running the company. They want to continue the traditions I worked hard to establish. But, your boss was just buying the name. Imagine, he just paid one hundred million dollars for my name. And now he doesn’t even want the catalogs.”

Matilda realized Lester was still standing there in front of her, naked yet smiling. “Come here, Lester. Sit on my lap, and I will tell my plans for the future.”

Lester obediently went and sat on Matilda’s lap. He really sat on the couch right next to her with one leg straddling her. He was too much of a gentleman to plop down and crush her.

Matilda surprised him when she reached around his waist and lifted him into her arms and seated him sideways on her lap so that he was looking into her eyes. She pulled him in close so that he was crushed into her lingerie covered breasts. She smiled and took his chin in her hand. She held it with her thumb and forefinger. She kissed him on the lips.

Lester put his arms around her neck and kissed her back. As he did, her tongue pushed his mouth open and probed. Lester accepted her aggression and eagerly kissed her. His arms squeezed her neck and shoulders. He loved the way his skin felt as he touched the beautiful bustier and warm flesh.

Lester felt her hand reach down between his legs and grasp his member. She used her thumb and forefinger to pet the head. Shivers ran up from his groin to everywhere in his body, and he pushed himself closer to her. He felt Matilda’s free arm wrap around his waist and snuggle him in tightly. Lester was in heaven.

Matilda was using her tongue to stimulate him. She paused. “If I tell you my plans, you become my co-conspirator. You will have to honor all of my wishes and keep everything I say in confidence.

“I am starting up another business. It will have a different name, and we will have a much more diverse catalog to offer. We are going to feature men’s and women’s’ lingerie. I already have this year’s inventory ready. All the lingerie is completed and sitting in warehouses.

But, I am only an advisor to this new company. My son, Charli, is going to run the business. We just received a one hundred million dollar investment from your company to get us off the ground.

Matilda continued to kiss and pet Lester for a reasonable time before she lifted him off of her lap and took him by the hand. “We need to make ourselves more comfortable, Lester. It’s time that your mistress shows you how to please her.”

Lester held her hand and followed her into the bedroom. He was already feeling lightheaded with excitement...

.

to the reader,

Please take a look at my new novel on Amazon under my name, Claire M Drake called

Living My Fantasy, an erotic transgender story

there are a number of free chapters to look over

Rooster Ch3

Author: 

  • Claire M

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • College / Twenties

Permission: 

  • Posted by author(s)
Charli 2.jpg

Chapter Three

Charli

When I woke up this morning, I stood up and staggered slightly on my way to the bathroom. My family doctor had warned me long ago. Because of low blood pressure, I need to take my time getting out of bed. I have to be careful standing up too quickly.

But, in my case, I was only interested in sitting down. I reached under my nightgown and pulled on my underpants taking them down to my ankles. As I reached in to direct my flow, I closed my eyes and sighed. I regularly consume too much liquid for the size of my bladder.

You see, my best friend Joy told me, "Charli, when you drink wine you need to drink water, too!"

Last night, I drank a lot of wine. We were also doing tequila shots. I like tequila. So, this morning, I was full of water.

Once I was done going, I gave it a shake and used a bit of toilet paper to dry little Dizzy off. I stood up carefully, held onto the counter, and looked in the mirror. I was a mess, but I was secretly pleased with my reflection. Even first thing in the morning, without any makeup and my hair looking a mess, I am pretty. I’m happy about that.

I carefully reached for my pills. I counted out my hormones. I like the colors. Estradiol’s lavender, oval tablet and the funny look of the spray-painted blue finish of my Premarin. But, the real party color was my antibiotic Cefalexin. I finished up my last one this morning. They were gorgeous enormous bright shiny red capsules.

Three days ago, when I first got my prescription from the pharmacy and shook one out into my hand, I immediately had to show it to my BFF, Joy.

She was funny. "Charli, I think it's the color of lipstick."

I said, "Stilettos!"

We both starting associating the color with an incredible cocktail dress. I riffed and pictured an adorable cap sleeved, body-hugging, pleated mini. These were huge pills and incredibly red and shiny. The prettiest red ever. I wanted a pair of heels in that color.

When I got dropped off at my house, we did our air kisses and promised to talk tonight. I thanked her for the afternoon and taking care of me.

I turned and faced my house. Matilda and I own a three-story Victorian three blocks from campus. Sure, she's my mom and I love her more than anything else in the world. But she's the one that said, "Charli, you're old enough to call me Matilda and stop making me feel ancient!"

I was achy and feeling the local anesthesia wearing off. A ninety-minute ride back to The Art Institute from over near Sea-Tac with six stitches in your crotch ache. But, for some reason, I was pumped. These were the coolest pills ever, they were awesome.

I showed them to my three roommates and their friends who were crowded into the living room. They all gave it a quick look, and the consensus was ‘candy, Mike & Ikes.’ They went back to playing video games on a huge TV and ignored me. I guess I was used to being ignored. I live with three guys. But, It’s a tough thing for an only child to be ignored.

For eighteen years, I grew up as the most important thing in the house. I talked, and my mom would stop and listen. Mom used to always say that she didn't have time to run a lingerie company, raise me, and be married. She said I was the sun that everything revolved around. Until the world hit me square in the face and I wasn’t a god anymore. I graduated and went to college. Life as I knew it had come to an end. It was all over.

Now I was just some skinny thing who was way too excited about the color of some pill. I was ignorable. Sometimes when that happens, I fell like lifting my shirt and flashing them, especially when I wasn’t wearing a bra.

As I was walking away, I knew a few of their new friends, yeah I noticed them, were staring at my butt. Even though everyone knows I’m trans, I am still a curiosity to guys.

They were staring at me, thinking about my gender and what was between my legs. My roommates all knew me well. We had gone to school together forever. But their new friends had trouble adjusting to the fact that I’m in transition. I confuse them, seriously, I do.

I can tell you stories, well, and I will, that’s the purpose of this whole writing effort. You see, my counselor wanted me to take notes about my day and how I react to stimuli. So I was doing my best to jot down notes when I could and flesh them out later.

What can I say? Yes, I like guys. Yes, I was born in the wrong body. And yes, I’m spending a lot of time and energy correcting that.

Back to my antibiotics, right. I think lipstick, stilettos. They guess candy, Mike & Ikes. Life has definitely made me hold back on speaking my thoughts aloud. If I gushed about how I thought they were a beautiful color for lipstick or four-inch stilettos, they’d just look at me weirdly.

Communicating with these guys was tough. It’s simple to understand. I’m not like them. Sure, I might have been born in a male body, but my brain isn’t wired like their brains. I wish it were. Things would be a lot simpler. But, at this point, that ship sailed, and I’m on my way to Girl Land.

As I thought about our Mike & Ike conversation, I wondered what my roommates would say if they knew about my most recent surgery. I never told them that Joy and I were going over near Sea-Tac to see a doctor. If they knew, they'd cringe.

But, in all honesty, I have no idea what they honestly think of me or how they describe me to their friends.

I imagine this dialogue if one of my roommates was standing with his friend and saw me walking by. I see them, and I wave hi.

A friend of roommate would say, ”Hey, who's that chick?"

Roommate would look at his shoes. When he looked up, he’d have this strange smirk on his face. “Uh, well, that's our roommate, Charli."

A friend of roommate would respond. ”Oh wow, dude. She’s cute. You’re one lucky guy having her around. Wow."

Roommate would look sheepish. ”Uh, dude. She's a tranny. She's a guy."

The confused look would appear on the friend's face as he wonders what the fuck a tranny is or salivates because he enjoys porn, and knows chicks with dicks are hot.

Okay, so it’s not easy being an alien among earthlings. I have to watch where I tread. You don't want to step on toes, especially some that would kick you when you are down. And honestly, I do get feeling down. I have a hard time railing against injustice, especially when its pointed towards me. But, I bite my tongue cause you just don’t want to upset the old apple cart.

Apple carts? You have to go back to old black and white movies to see apple carts being upset. Of course, that's easy for me to dig as a film buff. I've spent many a hot, humid afternoon watching old black and white movies on cable. I love to escape to old b&w movies. Dreaming of a PG world that where the bad guys are dark haired and wild-eyed, and the good guys have dimples, strong jaws always get the girl with their smile.

No one knows what's going on in your head when you watch a movie. Growing up, I always stared at the women and what they were wearing. Because of mom, I was always hip to lingerie. I mean, when your mom designs the stuff and it at the top of her class, you have to get into it. But, I was into other things. I mean I got gooey over the handsome guys. Back when you were in middle school and getting all misty over a Jimmy Stewart flick , no one could see inside your head about how you wished to be held by that right guy. How you wanted to be cute and demure and pretty and attractive and desired by the handsome, hunky man.

So, you go over near Sea Tac. I mean. You and Joy quietly slip away with your medical procedure prescription in hand and drive to all the way over to Burien to spend an afternoon in an outpatient clinic having an orchiectomy. Of course, if I were to say Burien to anyone who is not from Seattle, they’d look at me funny. Everyone knows what Sea-Tac is. Note to others considering the procedure. One pound bags of frozen peas make a much better ice pack than an ice pack. And when it’s all over, you can eat the peas, too. And when the pain goes away, which it does. And, yes, you have peas. No regrets, no loss. No deep pain in my heart. Dude, I was gleefully happy. Those parts of my body were never placed on a pedestal, they were not sacred or worshiped.

But, did I hear it. Wah. Wah. “Aw, gee, Charli. You made more peas? C’mon. How many peas can a guy eat?"

I smiled and pointed the wooden spoon at him. “Hey, I told you, they were on sale. Don't eat them if you object. You didn't buy them.”

Roommate Two says, “Peas like this, they’re great in a beef stew with those little white onions. Hey, Dizzy. Would you make that?” A quick aside. I’ve had the nickname Dizzy for most of my life. It’s that blood pressure thing. I move to fast, I get Dizzy.

Roommate One and Two are standing there in my kitchen coming inside from running around outside in the heat. It’s October. They are both hot and sweaty from playing with a football with other hot and sweaty guys. I stand there and smell the testosterone and look at the damp hair and flushed faces. Apparently, my thoughts are not in line with theirs.

I turn to Roommate Two. “Sure. I'll give you a grocery list of what to buy. You get all the ingredients, and I'll make it for you on Sunday."

Roommate Two gives me a big grin that melts my heart. I've known Ronny since middle school, and I would climb in bed with him in a New York minute if he showered first or maybe not, depending upon my mood.

By the way, filing this under too much information. My moods are all in my head. All this medication has made my sex drive live in my head and not in my groin. Nothing is happening between my legs.

I want to be a girlfriend. I want to be somebody’s girlfriend. I want to be the one to make him hot and sweaty. I want to be cute, demure, pretty, attractive and desired by the handsome, hunky guy in my old B&W movies.

Standing there in the kitchen spooning out another pound of cooked peas with butter on the top, I feel like bursting into tears. Fuck, I can’t believe I’m getting emotional over peas and the fact that I’m not pleasing these guys. Green vegetable rejection. Instead of crying in front of sweaty, hunky guys, I turn away and say, "eat them, don't eat them." I toss the wooden spoon in the sink. I head to my room on the third floor. I feel my hips shift and my butt sway as I walk across the room and up the steps.

The whole way walking up the steps the tears rain down my cheeks. I know it’s because my hormones are out of sync and I know it’s going to settle down soon enough, but right now all I want to do is lay on my bed and cry into my pillow.

Of course, most of that is in my mind. I've only been on Premarin and Estrace since last February, eight months and counting. My only salvation early on was the neutering implants I received when I turned fifteen. The anti-androgen kept my puberty in check, so I'm not like the rest of my roommates, all hairy and huge. I am slim and well, neutered. I look like a girl because we blocked all that testosterone before it had a chance to damage my delicate little body.

So, knowing that those implants were running out of steam, I saw my doctor and got this prescription to drive down to the doctor to eliminate this problem. This is what I surgically had taken care of three days ago.

My anti-androgen implants lasted for three years. Now, I don't have to sweat the details. Plus it made for some bonding time with my BFF, Joy.

Joy drove us to Burien. It was a sweet girl's road trip. We stopped for diet cokes on the turnpike. We chatted the whole way down all merry and gay. On the way back, I reclined my front seat and stretched out on two pounds of peas as the local anesthesia wore off and the incision started to throb. I wasn't quite as merry and gay. Just gay.

I'd moan, and Joy would laugh. I'd tell her to go fuck herself, and she'd reply, you wish. I'd look over at her 34 C's and contemplate rolling around with her. She's twenty-two and totally post-op. She's one of those remarkable children who knew she was trans at birth and her body got the message from her brain. So cute, so cuddly, and so totally a woman. All her men are big hunks, and she's barely five foot six inches. So even when she wears big heels, she still looks beautiful and demure.

Me, I'm the freak. I'm five eight and skinny. I'm that underfed and way too thin looking scarecrow. I'm still waiting for the estrogen to give me a girly body. I’m counting on it. Praying for it. But, it’s starting. I'm thickening up in my thighs and butt. My waist is looking better, and I've got a serious A-cup bust with amazingly sensitive nipples.

And let’s not forget, I have a great face thanks to my mom.

Mom. What can I say? I love her. She’s been my savior throughout my discovery process. She's Matilda. Maybe the most famous lingerie designer in the world. And she ran a business and raised me by herself. We thought I was gay until realizing that I was trans at ten.

She was a champ. She made sure I saw the best people and everyone agreed that I was trans. And everyone told me just how fucked up my life would be. I was trans which meant I should get used to prejudice, hate, ridicule, and discrimination early in life. But, God bless my mother. My mom takes no shit. I said she’s an entrepreneur. Let me tell you. She had a vision. She pictured a catalog where anyone in the world could order the most beautiful hand-made lingerie in the world. No one believed in her until she proved them all wrong. She takes no prisoners. She’s an ass kicker.

So, her little fairy son grew out his hair and wore precious outfits and was a princess even though his body didn't fall in line. Mom was my champion, and I grew up healthy and felt loved.

And sure I felt rejection and ridicule. Jeers from lesser souls who thought by putting me down it made them taller. Stupid comments from anonymous voices saying mean words when you’d walk by in-between classes. Shit heads who would actually get up and move if you sat close to them in class. Treating me like I had Ebola.

And I endured. I lived by the rule, what doesn’t kill you makes you stronger. Which is total bullshit. It should read, what rips your heart out through rejection and pain, just helps you get used to future rejection and pain.

But. I have a great face. Thanks to my mom. When I turned eighteen in January of my senior year, My mom's gift to me was facial feminization surgery. I was homeschooled after the new year and had my operation in early February. I was healed by June when I walked with my class. My nose was still a little puffy, but everything else looked good.

I wore a red satin robe like all the other girls. I wore a little makeup, and under the gown, I wore a pretty dress and three-inch stilettos. My nails were done, and I felt that all was right with my world. All the girls standing near me were complimentary saying how pretty I looked. I'd been out since I was in middle school, so it wasn't a big shocker, but now my face looked feminine, and I felt like I fit in as a woman.

I felt like smiling.

Oh yeah, so they ate all the peas and even remembered to put their dishes in the dishwasher after rinsing them off. Good boys, good.

I sat in my room contemplating my options. I needed a shower and a change of clothes. The only class I had on Tuesday was an eight o’clock at night. I’m guessing I’ll meet some commuting night school students tonight. It’s a general lecture course, a pre-requisite for my major, Film. I capitalized it because this is costing me thirty grand a year to get a BS in marketing and fashion. When I graduate, I am going to run Matilda’s for mom.

I settled on a shower, my first in three days. The doctor said I needed to leave the bandages on and keep the area dry until I stopped the antibiotic. I started to undress and check out the dressing. The big reveal.

The sweetest thing about this house was that my apartment was private. My apartment was the entire third floor, and I had a locked door to a sitting room, a bathroom, and a decent sized bedroom. Mom bought the old Victorian, and the deal was that I covered the mortgage and the utilities on my own. That’s why I had three roommates. They all paid me a fixed amount each month.

I went into the bathroom and stripped down. Usually, I wore a softly padded bra and panties. Oh yeah, and a gaff which is merely a tight little bikini that kept my genitals compressed and out of sight. Since I’d officially been a girl since I turned eighteen with a license, ID, and adjusted birth certificate, the gaff helps because most girls don’t have a penis and scrotum between their legs.

I pulled down my underwear and used a mirror to look at the damage. I started to remove the tape and gauze until I was staring at my empty scrotum sack. There was a tiny cut with six stitches in it. I had to sit down.

Everything was covered in this reddish tan solution. My body looked fine, no crazy swelling or redness. I gently touched myself, and it was a bit tender around the incision, but otherwise, I was okay.

I stood up slowly and turned on the shower. It takes a while for the hot water to get up to the third floor. When I walked across the room and turned on the shower, I got a shock. It was all different down there, and every step made it obvious. I had a lot less, and weight between my legs was very different. It was very freeing. I was reminded that less is more.

After my shower and moisturizer routine, I brushed my hair and wrapped it in a towel. I picked out new underwear. Sometimes I think about buying different sized bras and padding myself up a cup. A B-cup would be sweet. Every night, I say my prayers. “Dear God, Help fill me out. Add ten pounds of womanly curves to my body and let’s have peace throughout the world.”

I pulled on a striped long sleeve tee. Then I reached for a pair of black leggings. I knew I’d be wearing them all fall and winter and common sense said, ‘Its nice out, wear a dress or skirt.’

I felt like saying back, ‘dude, you don’t wear a skirt to a large class unless you want to look like a pioneer and add a hoop at the bottom.’ I decided not to take the buckboard. My shirt was black and white stripes, and my leggings were black. An easy way to layer. I wore a red dress on top. It had spaghetti straps and a mini skirt. I thought I looked sexy and I thought it gave me some shape and emphasized my legs and booty. I slipped on flats. After all, I’m tall.

I stood in front of the mirror while I brushed out my hair. It was dark and to my shoulder. It fell in waves past my shoulders. Then I pulled it back in a high ponytail. I put in some hoops, matching silver bracelets, a touch of perfume, and did my makeup.

I did the college girl look. I brushed on some powder, did my eyes, and blotted my lips after applying matching red lipstick.

I stared at myself. I did one of those tear downs. ‘She’s dressed like the Wakanda national flag. (a reference to Black Panther).’ ‘She’s matched her Garanimals perfectly, now she wants to go out and play.’ ‘A lovely combination if your boyfriend is wearing a leather jumpsuit.’

I fell short on the last one. I took a deep breath and picked up my book bag. I had the books, I’d checked my supplies. I was ready.

And then I got the call. It was my mom.

“I’ve sold the business, but the new owners don’t want next year’s product that’s already been paid for. How would you like to start your business career earlier than planned? We have a year’s worth of lingerie we can sell.”

“Hi, mom. How are you?”

“Come on, Charli. Here’s a great opportunity to bankroll your catalog now.”

“What happened to me taking over Matilda’s?”

“I sold the name and all its rights for one hundred million dollars of General Foods Products stock.”

“Oh.”

“So, you start your own catalog.”

“Can I call it Charli?”

“Of course.”

“Can we sell men’s and women’s lingerie?”

I heard my mom hesitate. “What a great idea! All that free publicity you will get. Of course, if you put your name on it, everyone is going to want to know all about you.”

“Yep. I’m the face of the company.”

“Can you handle it?”

“I’ll have to let you know next year when we start catalog number two.”

“Okay. So grab a pencil. You’re going to need to go to Sea-Tac and receive some cargo in a week. You’ll need a moving van and a large crew. Well, never mind. It’s too big a list. I’ll write it all down and text it to you.”

“I’m going to class now. Bye, mom.

.

to the reader,

Please take a look at my new novel on Amazon under my name, Claire M Drake called

Living My Fantasy, an erotic transgender story

there are a number of free chapters to look over

Sold, Chapter 1

Author: 

  • Claire M

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • Novel Chapter

Genre: 

  • Erotica

Character Age: 

  • Teenage or High School

TG Elements: 

  • Gay Males

Permission: 

  • Posted by author(s)

I’ve had this story floating around in my head for a while now. This could be chapter one or simply a little taste. Y’all will just have to let me know.
-Claire

Sold

“Yes, mom. I’ve heard the story before, maybe a hundred times. I remember that both of you emigrated from Poland twenty years ago hoping to find a new life in America.”

“I know that you worked as a chef and dad was a mechanic. Yes, I remember you telling me that the Greenfield family offered to sponsor the two of you and paid all your expenses. I know you had been offered jobs working for the family as servants. And yes, I remember how excited you both were.”

Mom still had a pretty look about her. She was in her early forties and dad was a few years older. Mom looked like a movie star from the sixties and dad had that distinguished look men get when they gray up a little. They made a handsome couple.

They were given a small cottage on the grounds and worked for the family for five years before I was born. The pair of them enjoyed hard work and were happy living in America. Naturally, they hoped their son would prosper in this new land of opportunity.

“Yes, mom, I get it. I understand how grateful you were and how important I am to you. Yes, mother, I am your future. I know. But, it’s really hard for me to get excited over some of the decisions the two of you have made for me without asking for my opinion.”

This isn’t a history lesson. I’m eighteen as I write this memoir. It’s going to be a short story because my life really didn’t get interesting until three years ago. Life would have continued to be pretty normal except for the Greenfield family’s son William. His interjection into my life changed me forever.

You see, the Greenfield family, technically Abigail and Arthur purchased me from my parents for an arranged marriage with their son, William. Crazy, huh? I know. I thought so too.

So when I say my intersection with William changed my life forever, I wasn’t kidding. While I don’t think this could happen in America or under any circumstances, right? I mean, can you really buy a human here? Is there still really a sex slave trade?

Well, the answer is yes, seriously yes. But, this was a private transaction between a family from the old world and an extremely rich couple that was looking to keep their really weird son under control.

Okay, so until I was fifteen, I really was pretty innocent. I mean, we had make-out parties after school in junior high, and I touched a few breasts here and there. But, that was the extent of my sexual awareness and exploration.

I’ll give you an example. My friend Suzie and I were out for a movie, and she had her mom’s car. Straight A students in New Mexico can have their license when they are fifteen. So after the movie, we were out parking, and I was sucking on her neck and feeling her boobs under her sweater and through her bra when she had an orgasm.

I was completely freaked out. I mean I thought I’d done something wrong and was asking her if she was all right. I mean, I was really concerned. I really had no clue. I mean I knew what an orgasm was and I mean any fifteen-year guy has had plenty of them. I mean my right hand was my best friend. But I really fucked things up. I totally embarrassed her, and she didn’t talk to me for days.

I’m sharing this story just to demonstrate how innocent I was.

So, my story starts when I was in the big house using one of the many Greenfield computers. I was in their kitchen while mom was making the family their dinner.

And here comes William. Mom didn’t like him. She said some strange things in Polish about him. She’d mumble them so really she was saying them to herself. I’d find out later those words were child molester and pedophile.

I was standing in front of the computer and researching some stuff for school. So William comes up and stands right behind me so he can see the computer, too.

He puts one hand on my shoulder and gently rubs my neck with his other hand. “Hey, what’cha doing, fella?”

He was so close I could smell the mints on his breath and feel his leg touching the curve of my bottom. “Uh. I’m trying to research some stuff for school. I have a report due, but it’s going to be tough without a printer.”

William squeezed gently on my shoulder and leaned in even closer. “Hey, guy. I’ve gotten a laser printer up in my room. You’re welcome to use my machine.”

His hand on my shoulder was massaging my muscles. His other hand had left my neck and was on my other shoulder. It was kinda like he was giving me a back rub.

I went to turn around, and instead, he pulled me in close, so I was being spooned by his much larger frame. He was talking into my neck and shoulder. I had never been this close to another guy before. His body was really warm.

I was ignoring my mom. She had left her stove and was giving me the third degree about going into the Greenfield house.

“No. Your father will drive you down to the public library, and you can print out your report there. Just tell your father, and he will drive you down into the village. You have no place in the Greenfield home.”

William hadn’t let me go but was addressing my mother. “It’s all right Freida. Paul doesn’t have to go into the house. I have my own entrance through the garage. He can just come up to my room that way.”

My mom was respectful but very firm. “Mr. William, I do not think my son should go up into your quarters. Paul is only fifteen years old. He is a child.”

I got mad. “Mom, I’m not a baby. I’m okay. I can take care of myself.” I was getting embarrassed over this whole conversation. I mean, what was the big deal?

In the meantime, William had turned me around and still holding my shoulder was steering me out the kitchen door and around to the garages. William’s suite was above the garage. I’d never been in there before.

As we walked up the steps, William kept his hand on my shoulder. When we got up to his room, he put his arm around my waist and pulled me close. He was still standing behind me and hadn’t let me go. He spoke into my ear. “So what do you think?”

As I turned to look around at his room, his face was very close to mine. Things seemed to slow down and almost come to a stop. He smiled and kissed me gently on my lips.

I found myself in his arms. He was much bigger than I was and I found myself enveloped in his arms and pulled in close to his body.

It was all very warm and comfortable. It was strange. I’d never been kissed by a man or held by a man or felt another guy’s erection pushing into my stomach. I guess I should have been really upset, but I wasn’t. It was dreamy.

I kissed him back, maybe a little too eagerly. I liked being held and pulled in close like that. It was very strange to be standing there kissing another guy.

I looked him in the eyes. “This is strange. I mean, not the kissing part but being kissed by you.”

William smiled. “I like kissing you. I’ve watched you for a while and really wanted to touch you and kiss you and lots of things.”

I grinned and kissed him softly. “What’s lots of things?”

William dropped to his knees and unbuttoned my pants. He pulled down my pants to my ankles and reached inside my underwear. William knew what he wanted and what to do.

When it was over, I needed to sit down. I pulled up my pants and sat on his bed. I was dazed. That was a crazy moment. I guess I must have put my head down while my brain was trying to take in what had just happened.

Willam came over and stood directly in front of me. He put his hands on my shoulders. I looked up, and he was grinning. He bent down and kissed me on my lips. His tongue pushed out between my lips and swirled inside my mouth. His tongue tasted strange and salty. I realized what he still had on his tongue and in his mouth.

I don’t know. It wasn’t like gagging or anything. I mean, it was pretty easy and kissing him was nice. I guess I liked it.

Then he straightened up, and I was staring at his belt and his pants. It was pretty easy to see what was poking through his pants. It was big and well, really big. I took a deep breath. I knew what I wanted to do.

“Uh, William. Can I?”

He looked down and smiled. “If you do, then you have to marry me.” He grinned.

I shrugged and went for it.

When we were both lying on his bed together, I still had him in my hand. He was still wet from where I cleaned him off. It was pretty neat.

He kissed me and grinned. “You’re going to be my bride.”

I laughed. “But, I’m a guy,”

He smiled again. “For now.”

I didn’t know what he meant. Rather than ask about that, I smiled. “Uh, I still need to use your computer.”

“Of course, honey. You can have anything you want.”

——————————————

Just want to mention that I have two stories available on Kindle. “Living My Fantasy: an erotic transgender story” and “Turned into His Girlfriend: first-time transformation”. Both books have lots of free chapters to look through.

Thanks, Claire.

https://www.amazon.com/s/ref=dp_byline_sr_ebooks_1?ie=UTF8&t...


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