Transsexual

Sissy Story Chapter 02

/ Categories: Authoritarian, Fiction, Transsexual / Authoritarian, Fiction, Transsexual / By

Mother and Sissy Mom and I had obviously taken things to a different level. Just like when I had first worn pigtails and hair ribbons, our relationship, and understanding of that relationship became even more intense and our connection became even deeper. I was happy and Mom was obviously pleased coming out of the mall, me wearing clothes bought that day; a light t-shirt, some shorts, sandals that showed my toenails polished, panties and a training bra. She pushed a cart full of things for my new wardrobe. She chatted constantly about her Sissy and the things we could do and how much she was enjoying life. On the way to the kiosk to get my ears she had leaned over and kissed me on the head and emphasized how proud of me she was. …

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The Landlord’s Submission

/ Categories: Anal, Black, Consensual Sex, Domination/submission, Fiction, Transgendered, Transsexual / Anal, Black, Consensual Sex, Domination/submission, Fiction, Transgendered, Transsexual / By

I finally did it! I bought my first house. I’m not a real estate investor… Haha, that’s a bit of stretch, but once I get some renters, I’ll start earning some passive income. Although, it kind of sucks that I’ll have to live in the house with the renters for now. But, once I get enough money saved, I’m going to buy another house and rent it out as well. Eventually, I’ll be able to afford my own house. It’s only a matter of time before I’ll be able to afford to buy an apartment complex. I just have to be patient. It wasn’t long after I put the ad out, that I heard back from someone. I got a call from a woman looking to rent. Her name was Kendyll Terrell. I invited her …

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A Shemale Fantasy and my wife (Part 4)

/ Categories: Anal, Fantasy, Transsexual, Wife / Anal, Fantasy, Transsexual, Wife / By

Basking in the glow of what just happened, I put my head back and just passed out from total bliss. I didn’t know what else Carol had in store, but I knew I wanted to be well rested. A few hours later I was woken up by Carol. “Wake up baby this day is just getting started” she said. My eyes opened and I was like a kid on Christmas morning. I couldn’t wait to see and “feel” what she had in store for me next. Carol instructed me to shower get dressed and leave the house for a few hours. My next surprise needed some set up. I did ask she told me. Before I left Carol came up to me grabbed my dick, kissed me and said “get ready for some fun”. Having …

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Your tansgender girlfriend

/ Categories: Transgendered, Transsexual, Transvestite, True Story / Transgendered, Transsexual, Transvestite, True Story / By

There are times in a young man’s life when it is so full of fun and sex that it’s a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it’s self. Yea, it was the late 80’s and the me decade was in full swing. I can’t say that I immersed myself in the culture of the times, but just like walking across a muddy field you can’t help but get some on you. I was in and out of several relationships with girls of many different types but couldn’t seem to find that one woman who rocked my world. Well, at least not …

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A sexual journey – Chapter 1

/ Categories: Bondage and restriction, Cuckold, Domination/submission, Fiction, Transsexual / Bondage and restriction, Cuckold, Domination/submission, Fiction, Transsexual / By

My husband, Reg, and I (Peggy) had been married for 6 years. We both enjoyed sex very much and was always finding ways to make it better, more exciting and pleasurable. Our research extended to porn to find new ideas. Most of it was pretty mundane with the usual straight sex, bisexual games and such like. We found some of the more, shall we say, weird stuff more appealing. Things like bondage and submission were quite exciting. Of course the problem was finding the equipment to partake in such things. Getting on the internet we found what was called an Adult Bookshop. In reality it was a sex shop with all kinds of weird and wonderful things. I already had a 6” vibrator that I had bought on-line. But in their catalogue there was pages …

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One Summer Day

/ Categories: Anal, Consensual Sex, Fiction, Transgendered, Transsexual, Transvestite / Anal, Consensual Sex, Fiction, Transgendered, Transsexual, Transvestite / By

I always found my sister-in-law, Cara, kind of attractive, even as my girlfriend and I were dating at the time. She was already married when I started dating, but I was already mesmerized by her beauty. At my wedding, Cara wore a beautiful strapless turquoise dress that rivals my wife’s white wedding dress. I would have been fine if they had switch places that night. However, my wife never truly got along with her sister. Cara was…careful with their money with her own family, but freely spend it with friends and her husband’s family. She would also spend time with her friends weekly, but only went to her parent’s house once or twice a month for dinner. My wife has always taken care of her parents better than Cara did. The animosity between them was …

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Suzy Unleashed Chapter 11

/ Categories: Bi-sexual, Diary, Transsexual, Transvestite / Bi-sexual, Diary, Transsexual, Transvestite / By

Whether it was exhaustion or the fact that I was beginning to accept my new life, I slept really well on Thursday night and woke up refreshed and ready to go. As usual, while I showered, Kathy laid out my outfit for the day, ***********ing one of the dresses she had bought the day before to help fill out my closet. The tight red dress barely stretched over my enhanced chest and the hemline was only inches below my ass. I knew that as tight as it was, bending over the coffee table at work was going to be an adventure, and when I tested it by bending over in front of the mirror, my suspicions were confirmed: the matching red panties Kathy had laid out were clearly visible. Surprisingly, I found myself smiling at …

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A Shemale Fantasy and my wife (Part 3)

/ Categories: Anal, Fantasy, Transsexual, Wife / Anal, Fantasy, Transsexual, Wife / By

After our night of raw sexuality, I started to look at Carol in a all new way. She wasn’t just my wife, now she was so much more. Their was so many areas I wanted to explore with her. I felt like a teenager again. I couldn’t stop thinking about how naughty Carol was being. It was Sunday, and my only day off so I decided I would do something nice and bring Carol breakfast in bed. I went to our kitchen and made our favorite breakfast, bacon and eggs. As I began to walk up the stairs I could hear moans coming from our bedroom. They weren’t Carols. I walked into the room to see Carol totally nude, with her legs spread. She was playing with herself and on the TV was porn. I …

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Work Diaries

/ Categories: Anal, Black, Blowjob, Fiction, Interracial, Oral Sex, Romance, Transgendered, Transsexual, Written by women / Anal, Black, Blowjob, Fiction, Interracial, Oral Sex, Romance, Transgendered, Transsexual, Written by women / By

***** Diary Excerpt One: “Following the threat of a sexual harassment lawsuit, the second such threat levied against me by two separate Personal Assistants the suits in HR, in light of my skills and results, decided to give me one last chance before they would be forced to take additional disciplinary actions. In an effort to reduce the likelihood of a repeat scenario they decided to assign me a PA that they assumed, correctly, would not be to my tastes. However, they did not take into account how much to his tastes I would be.” ***** Ayesha drummed her fingers irritably against the corner of her desk as the representative from HR vacated her office, like a zebra fleeing from a lion it’d just asked politely to stop eating its herd, leaving her with a …

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A Shemale Fantasy and my Wife (Part 2)

/ Categories: Anal, Fantasy, Transsexual, Wife / Anal, Fantasy, Transsexual, Wife / By

I arrived at work, walked into my office and settled in for the day. Just as I was checking emails on my computer my phone vibrated. I took a look. It was a text from Carol. In closed was a picture of her laying in bed totally nude with her legs spread. The text read, “my tight wet pussy is waiting for you. I instantly got horny. I would never dreamed Carol would send me a picture like that. I texted back “I can’t wait to stick my dick in it when I get home”. After a minute to compose myself I got to my work for the day. About an hour later my phone vibrated once again. It was from Carol. This time she had send me a picture of a shemale. The text …

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A Shemale Fantasy and my Wife (Part 1)

/ Categories: Bi-sexual, Fantasm, Transsexual, Wife / Bi-sexual, Fantasm, Transsexual, Wife / By

I was always a sexually open individual. But in my world sexual expression wasn’t really part of my routine. I’m a 35 year old married man. My wife and I met back in high school and have been together ever since. Our relationship has always been good. We love each other, and the life we have built. But lately our sex life and our life in general has become some what stagnant. We get up go to work, come home have dinner, then go to bed. It’s the same thing you’ve heard from couples who have been married for ten years. The excitement level no longer exceeds sexual intercourse more then once a week. It becomes frustrating at times because I’ve always been the type who wants to try new things sexually. My wife is …

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Suzy Unleashed Chapter 2

/ Categories: Fiction, Slavery, Transgendered, Transsexual, Transvestite / Fiction, Slavery, Transgendered, Transsexual, Transvestite / By

I tossed and turned most of the night trying to think of a way out of the trap Kathy had put me in. At times I told myself that she’d never follow through on her threat and that I should refuse to go along with her desires. Of course, I also wouldn’t have believed the things I’d already found out—that she was fucking Ron and that she was more than willing to force me to blow him. If she was willing to do those things, how could I be sure she wouldn’t distribute those damn videos? I woke up about 6:00 with my bladder ready to burst. Quietly I climbed out of bed and went to the bathroom. When I finished, I walked back into the bedroom, still not sure what I was going to …

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Transformation_(0)

/ Categories: Bi-sexual, Fiction, Transsexual / Bi-sexual, Fiction, Transsexual / By

The story is clearly of a shemale/transexual nature please don’t read on if your into that. Chapter 1 Jazz stood naked in the middle of her bedroom floor, the thick grey carpet feeling lush beneath her feet. Looking back over her slim shoulder, she admired herself in the mirrored wall that, like the mirrored ceiling, was a feature of the room. Jazz took in her body and her eyes scanned herself critically. Starting at her feet she examined her smooth shapely legs. She thought her calves were a little muscular and made a mental note to try and do something about it. Her eye’s moved to her pert little bottom and she pushed it up and out, arching her back as she did so. “Hmn” she murmured thoughtfully as she swivelled her hips, checking herself …

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Kylee’s Sauna Fantasies

/ Categories: Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Fantasm, Toys, Transgendered, Transsexual, Transvestite, Young / Anal, Bi-sexual, Blowjob, Cum Swallowing, Drug, Fantasm, Toys, Transgendered, Transsexual, Transvestite, Young / By

Last Saturday I went over to a friend’s house to eat and he had his sister, Kylee, over for dinner. For some reason it seemed like they didn’t like each other very much. As the food was set out to eat they argued over who was going to sit where; she wanted to sit next to me, but my friend was the man of the house and he won the debate. Rosa sat across from me. She sat down slow and winked at me while doing so. We were having a roast with broccoli and baby carrots. That night Kylee was wearing a thin blue silk dress that rode up half her thigh when she sat down. Constantly I was in an internal conflict; trying to get a peek under that flimsy dress and trying …

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Life on the Ranch Ch 2 – Later that Night

/ Categories: Anal, Authoritarian, BDSM, Cruelty, Cum Swallowing, Discipline, Domination/submission, Erotica, Female Domination, Hardcore, Humiliation, Non-consensual sex, Oral Sex, Rape, Reluctance, Science-Fiction, Spanking, Teen, Transgendered, Transsexual / Anal, Authoritarian, BDSM, Cruelty, Cum Swallowing, Discipline, Domination/submission, Erotica, Female Domination, Hardcore, Humiliation, Non-consensual sex, Oral Sex, Rape, Reluctance, Science-Fiction, Spanking, Teen, Transgendered, Transsexual / By

“You’re not going to tell her about what we just did, right?” She said as she lifted an eyebrow. All I could do is nod. “That’s a good boy, now hurry up n’ get your things and sneak out the back. I’ll distract Steph,” she commanded. I nodded as I rushed to grab my things I looked up at her. “Please don’t say anything to Steph about what happened with the others.” “Don’t worry about that, now get going!” I ran off to the back entrance and snuck around the stables. I waited as I heard Amanda approach Steph. “I finished my chores so I decided to start sweeping out the stables.” “Now that’s what I call dedication, I wish I had three more just like you instead of those other morons. Speaking of the …

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THE PRIMA DONNA

/ Categories: Ass to mouth, Authoritarian, Bi-sexual, Blowjob, Body modification, Consensual Sex, Cosplay, Cuckold, Cum Swallowing, Erotica, Exhibitionism, Female exhibitionist, Group Sex, Hardcore, Male / Older Female, Older Female / Males, Oral Sex, Prostitution, Threesome, Transsexual, True Story, Voyeurism / Ass to mouth, Authoritarian, Bi-sexual, Blowjob, Body modification, Consensual Sex, Cosplay, Cuckold, Cum Swallowing, Erotica, Exhibitionism, Female exhibitionist, Group Sex, Hardcore, Male / Older Female, Older Female / Males, Oral Sex, Prostitution, Threesome, Transsexual, True Story, Voyeurism / By

Her PA has asked me if I can organise a suitable man for her pleasure. He told me she expects a younger man, ten or fifteen years younger, good looking, a taut masculine body. And he stressed the man must be well hung with no inhibitions or hang ups.” “Does Friday afternoon in the Hyatt penthouse work for you? Her agent offered ten-percent over our normal fee, plus a performance bonus.” “How can I earn the performance bonus, what do they expect for them to pay it?” “Roger, for a very experienced gigolo, or male prostitute, you can be very naive at times.” “You mean ..?” “Yes, I think so.” I was reminded of a few prima donnas I had encountered in my work as a gigolo, often they had grand off-stage personalities and were …

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Massage therapy

/ Categories: Anal, Fantasy, Transsexual / Anal, Fantasy, Transsexual / By

Every Friday evening I used to go to my local Asian massage parlor. It was nothing derogatory just relaxation and a good rub down after a weeks work. One particular Friday that all changed. When I arrived at the parlor I was greeted by the female owner, a sweet old lady with a kind smile. She explained that I had been double booked and apologized profusely. I told it was OK and not to worry about it. I was being polite, I really wanted a rub down as my back was full of knots. The old lady must have sensed my disappointment as she told me to wait and disappeared in the back. Moments later she returned all smiles. She told me of another parlor, she had rang ahead for me and given my name …

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Suzy Unleashed Chapter 7

/ Categories: Blowjob, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / Blowjob, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / By

I woke up on Monday morning to the feel of Kathy stroking my erection through my sheer panties. “Mmmmmm,” I purred, “that feels nice. You haven’t done that to me in a long time.” “I know,” she smiled. She kissed me softly on my lips and explained, “I woke up so excited, and when I saw your cute little hardon, I just couldn’t resist. Do you like it?” “Oh, yeah,” I sighed. “Does it make you want to fuck?” “Oh, God, yes,” I groaned. She kissed me again. “Do you want to fuck until you cum? Would you like that?” “I’d love that!” I answered excitedly. Again her lips found mine, and this time her tongue slid into my mouth. I moaned softly and she said, “Oh, my, you really are horny, aren’t you?” “God, …

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Suzy Unleashed Chapter 6

/ Categories: Blowjob, Domination/submission, Fiction, Transsexual, Transvestite / Blowjob, Domination/submission, Fiction, Transsexual, Transvestite / By

I woke up on Sunday with Kathy’s words from the night before echoing endlessly in my head. It was now beginning to sink in that I was actually going to spend an entire week as a slut, sucking whatever cocks Kathy and Ron told me to. As I thought about my situation, it dawned on me that I wasn’t sure which part was the most disturbing—that they were going to use me that way or that I wasn’t repulsed by the idea. “How can I be letting them do this to me?” I wondered. “How can I be willing to go down on whoever they say? It’s so humiliating and disgusting!” I closed my eyes and pictured what I knew was going to happen to me, with cock after cock spewing into my mouth. As …

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The Retirees Club (12)

/ Categories: Anal, Fantasm, Transsexual / Anal, Fantasm, Transsexual / By

Andie stood up and we wrapped our arms around each other. “Let’s go to bed,” I whispered. Her reply was a soft moan and we both turned to go, with her grabbing her purse. When we arrived, I asked her, “I would love to please you, my darling. I gently pushed her back on the bed, then began to run my hands up and down her legs. Reaching for her pants buckle and zipper, I opened them and reached for the waist of her pants. I didn’t know what to expect, since she said she hadn’t had any surgical changes. Whatever she had, I was determined to make her feel like the sexy feminine creature that she was. She lifted her hips so I could pull her pants down. Making sure I had pants and …

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