Transsexual

a new Mistress 5

/ Categories: Anal, Blowjob, Cum Swallowing, Domination/submission, Fiction, Transsexual, Water Sports/Pissing / Anal, Blowjob, Cum Swallowing, Domination/submission, Fiction, Transsexual, Water Sports/Pissing / By

The 5th Thursday finally arrived. I had to make myself drive the speed limit. I was a mess. I was consumed by Natasha. I felt bad about cheating on my wife but obviously not bad enough to stop. I was as good to her as always; maybe even better because of guilt. Always had sex with her when she wanted and always waited for her to “tell” me to cum. I just could not stop think about Natasha. If I could find a way to become her bitch permanently without hurting my wife…. I was still very much in love with my wife…I was just consumed by Mistress Natasha. I forced myself to calm down and entered her foyer and stripped, as usual, folded my clothes and went into her living room. She sat naked, …

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Rebecca Chapter 01

/ Categories: Cum Swallowing, Fiction, Transgendered, Transsexual, Transvestite / Cum Swallowing, Fiction, Transgendered, Transsexual, Transvestite / By

My wife Jasmine knew that I was a trannie. She was OK with it when I first told her and even helped me with make-up, clothes, deportment etc. However, as with all these things, I became obsessed with dressing all the time. I even toyed with the idea of changing sex. I guess this all became a bit too much for her and she gradually lost interest in helping me. Our sex life deteriorated to nothing; my fault again as I always wore lingerie to bed and she really wasn’t too keen on touching me, although we were still the best of friends. I began to notice though that she was wearing sexier underwear, not that I minded as I always got a thrill from wearing her used panties, usually with the thought in my …

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trannie 3 some

/ Categories: Bi-sexual, Transsexual, True Story / Bi-sexual, Transsexual, True Story / By

I met Chrissy about a year ago at a bar. We really hit it off. She was about 5’5″ 120 with a nice, athletic body. She was Filipino. Her face, well, unless you knew, you would never know. She was different than the rest of the girls at the bar. While she was there to make a living, she was also there to have fun, with the right guy. Fortunately for me, I was the “right” guy. We went out a handful of times and always had a great time. Then, for whatever reason, we did not see each other for a while. One night I was planning on going into NYC, so I gave Crissy a call to see if she wanted to hang out and have drink or whatever. She was pleased to …

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Frank’s Inner Woman

/ Categories: Anal, Blowjob, Fiction, Transgendered, Transsexual, Transvestite / Anal, Blowjob, Fiction, Transgendered, Transsexual, Transvestite / By

Frank’s nuts ached; he had been in and out of at least ten porn parlors around Times Square and had spent upward of $40 on the video peeps. Now he was sitting in a nice cool bar with a martini in front of him deciding if he wanted to do it or not. ‘What the hell.’ He thought and turned the copy of the underground newspaper he had bought to the Transexual/Shemale section and began to read the ads, trying to decide which one to call first. Frank had taken the opportunity of his wife being out of town to visit Manhattan and the porno parlors, telling himself that he wouldn’t visit a shemale prostitute again. But the fever was in him and the martini was lowering his resistance. ‘Of course I was going to …

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My transistion part 3

/ Categories: Consensual Sex, Cruelty, Fiction, Lesbian, Transgendered, Transsexual / Consensual Sex, Cruelty, Fiction, Lesbian, Transgendered, Transsexual / By

Part 3… Jill meets a guy and Lisa teaches Jill a lesson. As always I look forward to your comments or requests. Jill has been working for almost four months now. It’s been very busy and getting busier every week. Now that we got the contract to fix and setup all the computers in the public schools in the area. Jill was looking forward to getting some overtime. Ted hasn’t been seen once by Jill. Then one day Jill is called to Ted’s office. I wonder what he wants Jill mumbles to herself as she leaves her work area and heads up stairs. Jim’s secretary looks up at me and says, he’s waiting for you. Please go right in. Jim’s secretary is a hot little number. About 21 or 22 years old 5’8″ 125 lbs …

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a new Mistress 3

/ Categories: Blowjob, Bondage and restriction, Cum Swallowing, Domination/submission, Fiction, Foot or shoe fetish, Transsexual / Blowjob, Bondage and restriction, Cum Swallowing, Domination/submission, Fiction, Foot or shoe fetish, Transsexual / By

I had become obsessed. Natasha was all i could think of. I had to concentrate to keep my mind on work or listen to my wife when we were togehter. Sex with my wife was still good, but I found myself tinking of Natasha to maintain an erection. I arrived at Natasha’s house, on time, the following Thursday night. I performed my usual strip in the foyer. Again, she called out to me, “In the bedroom, pet.” I ran down the hall and dropped to my hands and knees at the threshold and crawled into the bedroom. I glanced up for a second and saw her naked and smiling. She walked to the edge of the bed, sat down, scooched back so her feet could dangle, and beckoned me, “Come and greet your Goddess, pet.” …

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2 she males 1 lucky male

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

They didn’t waste anytime. As soon as the 3 of us were through the door they went to work. They were eager. One in front of me and the other behind. This is how it would be all night, me the filling to their sandwich. The one in front had her hands caressing my lower back and butt cheeks. The one behind had her arms around me and her hands over my lower abdomen. Her palms brushed over my abbs and her finger tips gently pressing into my navel. She kissed my neck and jaw line from behind. I loved that. The one in front was kissing me hard. We were mashing our lips and tongues together. The one behind was pulling my mid section back into her. She pushed her crotch into me. I …

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Fantasy date (part 2)

/ Categories: Anal, Blowjob, Consensual Sex, Cum Swallowing, Fiction, Transsexual / Anal, Blowjob, Consensual Sex, Cum Swallowing, Fiction, Transsexual / By

I called Kim later that morning, and we agreed to meet at her house that night. When I got there later that evening, she greeted me at the door wearing a long robe. I couldn’t tell what was underneath. She invited me in and poured us a drick. We sat on the couch and kissed and made small talk, and she suggested we retreat to the bedroom, that she had something special planned for me. I lay down on the bed and she went into the bathroom to freshen up. When she came out, she was wearing a silky red teddy. Her long dark blond hair was pulled up sexily, her eyes sparkled. She came over to the bed and kissed me gently on the lips, and started unbuttoning my shirt, kissing my flesh as …

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Crossed Lines

/ Categories: Anal, Coercion, Domination/submission, Fiction, Non-consensual sex, Rape, Transgendered, Transsexual, Written by women / Anal, Coercion, Domination/submission, Fiction, Non-consensual sex, Rape, Transgendered, Transsexual, Written by women / By

Leo took a slow refreshing drink from a cup of now warm water, sitting at the edge of an intricately designed diagram drawn out with fine red chalk, his eyes scanning studiously over his magnum opus, checking it for errors or faults, knowing even a single smudged line could result in his downfall. Everything was perfect and exactly as the book had detailed, the chalked lines the definition of precision on the designated aspen wood floor, stones and gems of varying origin expertly carved with runes long extinct from the world placed around the central circle, candles dotting each of many points, the wax of the candles infused with his own blood, the fire burning with a slightly greenish tinge, a sign things were as they should be. Now all he had to do to …

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The Dream_(0)

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

She slipped into my room so quietly I thought she was a dream. Her daphenous gown billowing in a subtle breeze like some scene from a movie. She smiled as she crossed the room with her coy little shy girl smile and I was hard immediately. I must be dreaming, this was too good to be true. As she neared my bed she stopped and let me take in the full glory of her. The gown clung to her gorgeous breasts and hard nipples so while I couldn’t see them, I could see their full shape hinted at. The light made the gown transparent at her waist so I could see perfectly the outline of her long luscious legs and the sway of her hips. I knew I had to be dreaming but I didn’t …

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My little secret 2

/ Categories: Anal, Bi-sexual, Enema, Fantasy, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Enema, Fantasy, Transgendered, Transsexual, Transvestite / By

Katelin and I broke our kiss and looked over towards Jim. He was sitting in one of the kitchen table chairs, boxers down to his ankles stroking his cock. “Don’t my girls want their morning milk??” he said again. Katelin led the way as I followed, getting down on our knees we started to pleasure our daddy. Katelin started licking his cock, getting it nice and wet. Taking it in her mouth, and going down about halfway. I started licking and sucking on his balls and ball sack. From time to time I would lick under his ballsack, giving him a quick fluster. “Hey Ashley, come here and kiss me” Katelin said. As I moved my head up she kept his cock inbetween us. We wrapped our lips around the sides of his cock, trying …

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Cecil Part II

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

CECIL PART 2 The bar was packed, not because it was entertaining or a nice place for conversation, it was packed because the Buffalo Pussy Posse was out in force tonight. The bar was three deep in streetwalkers, hookers, pimps and huggermuggers. Ruby and Cici (nee Cecil), had seats on the end of the curved bar in the back. The city was doing its once every six months attempt to keep the Chippewa Strip free of ladies of the evening and all that was associated with them. “Must be a convention in town.” Stated Ruby in a matter of fact manner. “Must be.” Answered Cici. Cici had recovered from her facial surgery in Baltimore the month before, and was in full make up. Her hair now extended down to the middle of her back and …

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t-girl girlfriend

/ Categories: Bi-sexual, Transgendered, Transsexual, Transvestite, True Story / Bi-sexual, Transgendered, Transsexual, Transvestite, True Story / By

I have stated in the past that I am disabled and unable to dress up anymore because I cant get out and buy new outfits after my ex destroyed everything. well i was able to sneak out and finally after 5 years buy a pair of panties. I was working a temp job at the local mall and wore them to work when i bought them. there was a store close to where my store was that let us use the restroom and i headed over there. I didnt notice they had a new girl working the counter til i got there. asked if i could bathroom and went to the back room. finished and it was time to close up my store. I rushed through closing so I could go talk to the new …

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Alan Gets A Tranny

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

Cheryl was friends with Jack’s wife, but she was single. She needed manly advice from time to time. So she caught her son, Alan, jacking off and asked me to talk to him about it. He was 15 and always horny. Of course, she had no idea I was bisexual. I took her up on the idea to talk to him. What started as me innocently talking to her teen son about masturbation descended into a twisted tale. ————————————————————————– I went to Alan’s house after work one day to talk to him. His mom was single and she need a male figure to discuss masturbation since she had caught him doing it. I rang the bell. I heard footsteps on the stairs and then the door opened. “Hi Alan.” “Oh, hi Mr. Jones.” “Can i …

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Camming Down the Rabbit Hole Ch10

/ Categories: Cum Swallowing, Exhibitionism, Fiction, Masturbation, Pegging, Transgendered, Transsexual, Transvestite / Cum Swallowing, Exhibitionism, Fiction, Masturbation, Pegging, Transgendered, Transsexual, Transvestite / By

As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous night, which only heightened my state of arousal. One thing which did differ from the previous mornings was my sore throat. No doubt a result of my getting a little carried away although its scratching as I swallowed some fresh water easing slightly, I smiled and remembered with pride what I had achieved and the results of my dedication. Coughing a little I could clearly hear my voice was a little horse, maybe not croaky …

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Sissy Story Chapter 03

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

The Adult Sissy I’d kept in touch with Tommy while I was away, but he didn’t text me much, so I was not really expecting him to see him after my appointment that Wednesday. I had texted him and told him my appointment would be a little longer, might last for a couple of hours. He was pretty noncommittal. I didn’t tell him I was dumping the curls and going with a more adult style, shorter and, I thought, more sophisticated, straight, like European girls wore. And I didn’t tell him about my new boobs. I decided to keep the platinum blonde color. I wore a t-shirt without a bra, so he and everybody else could see my new tits. Blue shorts and sandals and a huge white leather purse completed my outfit. I guess …

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Summer vacation changed whole life pt2

/ Categories: Anal, Bi-sexual, Body modification, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / Anal, Bi-sexual, Body modification, Cum Swallowing, Transgendered, Transsexual, Transvestite, True Story / By

From that day I felt differently I wanted to be dressed like a girl I dreamt sucking cock and being fucked . It has been a week and I could not resist any more by luck sis has gone out with friends for a week and aunt have gone out to buy some thing in the evening. I dressed up as a girl and hid some of my clothes in the front garden to change when I return home late night, I messaged my aunt that I was going out and will be back late night so do not wait for me and went to pub near by to have some sex. An elder guy offered me drink and asked me for some fun and he took me to a hotel . he locked the …

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Gap Year

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

With a low sigh, Charlie ran the back of his hand across his forehead, collecting the beads of sweat that the Brazillian heat had gifted to him before wiping his hand on his already quite sodden T-shirt, looking down at his open luggage on the rather meagre single bed with a serious lack of motivation. He should unpack, find his toiletries and find the shower, but to do so he’d have to search through his stacks of clothes and he knew, in doing that, would have to spend the time meticulously folding them all neatly away. Charlie didn’t consider himself to have OCD or anything like that, but he was a guest in this house, albeit courtesy of Air BnB, and the second he had caught sight of the owner, he had known he wouldn’t …

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Working the holiday Monday

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

So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dark chestnut hair that is short at the back but gets long at the front. It matches her deep espresso eyes. She dressed very professionally at work ankle length skirts, blouses and blazers that type of thing. She has perky c cup breasts that when she trots or runs through the office they have a nice firm bounce. She looked to me to be about thirty five. She has no rings on her fingers so she is …

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My little secret 4

/ Categories: Anal, Bi-sexual, Body modification, Fantasy, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Body modification, Fantasy, Transgendered, Transsexual, Transvestite / By

I woke up very groggy and laying in a hospital bed. Bandages wrapped around my chest and a pain like I had never felt. Jim came over to my side and looked at me. “How do you feel” he asked. “Hurting alot” I answered as I tried to look around the room. Jim grabbed my left hand and put it between my legs. I felt bandages and gause in a hefty amount. I started to get excited, Jim tried to calm me down but it was no use. I started trying to get out of bed when my meds kicked in, I was knocked out cold and lying back on my back. When I woke up Jim was still there. I looked up at him with concerned eyes, not knowing what to think of him. …

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