Transvestite

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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Growing Up Chapter 11

/ Categories: Anal, BDSM, Bi-sexual, Diary, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite / Anal, BDSM, Bi-sexual, Diary, First Time, Male / Female Teens, Teen Male / Female, Threesome, Transvestite / By

Sophomore year. I move back into a shared room with the same roomate. His regular absence on weekends is convenient. Alexa stays in the apartment with Chelsea and another girl but Shelby comes back to campus and the dorms… and the trysting room. I am Cool Joe Sophomore on campus. I get lots of hugs and attention from the sorority sisters. People look at me like I’m some kind of stud! I’m updated on what everyone did over the summer. . . . . . Shannon sees me. “well hello beautiful boy. Did you have a good summer?” “I surely did. Are you still a virgin?” “Of course sir! And I’m engaged!” She shows me a huge ring. “Wedding is in June, you’ll get a save the date notice.” “You think that’s appropriate? Inviting me?” …

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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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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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Sometimes short for Samuel pt. 1

/ Categories: Anal, Bi-sexual, Blowjob, Fiction, School, Teen Male / Teen Male, Transvestite / Anal, Bi-sexual, Blowjob, Fiction, School, Teen Male / Teen Male, Transvestite / By

Sometimes that’s short for Samuel I’m Sam. Sometimes that’s short for Samuel, A slight young man, trim and clean, round soft features and full lips framed with shoulder length brown hair and bright green eyes. I’m a short 5’9” and a bit of a slouch, so I come across as very short. I was never very athletic so I didn’t have much muscle tone, but I keep fit skating and playing hacky sack with my small group of oddball friends. I keep to the skater look mostly, layers of t-shirts and skate gloves, torn up black jeans or tactical cargos, and either skate shoes (I LOVE my Vans but I’m usually rocking DCs or Etnies these days) or combat boots. Punky bracelets, some chains and a bit of eye liner complete something of a look. …

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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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Realising Our Fantasies Together part 2

/ Categories: Anal, Authoritarian, Discipline, Domination/submission, Fiction, Transvestite, Wife / Anal, Authoritarian, Discipline, Domination/submission, Fiction, Transvestite, Wife / By

“Steve, come in here now!” Two weeks had passed since my first strap-on session with Maria, and since she had fucked me with it a few times, but she had never let me take off the cock-cage in those two weeks. She was gradually taking her dom role more and more seriously, to the point where she had ordered a black vinyl outfit just to push the point home for me, and it was that same outfit I was looking at as I entered the bedroom. She was standing there, her legs akimbo, letting me see her lips hanging down softly, slightly moist. Her tits were spilling out of the top of the outfit, and she had her hair tied into a tight ponytail, a sliver of it hanging loose on her right temple. My …

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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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Auntie’s home tuition (pt3)

/ Categories: Anal, Cum Swallowing, Fiction, Interracial, Males / Females, Transvestite, Water Sports/Pissing / Anal, Cum Swallowing, Fiction, Interracial, Males / Females, Transvestite, Water Sports/Pissing / By

Continued from Auntie’s home tuition (pt2) Because uncle Robert went out and Silvia was tucked up in hospital due to her allergic reaction to her insect bite l had a bath and went to bed, but was woken by a hand around my cock, instinctively l thought it was Silvia and pushed myself backwards to feel a hard cock pressing against my bum, a male voice said l had a lovely cock with a peach of a bum, my eyes sprang open and l half sat up bemused at what was going on. Stood beside the bed was uncle Robert with an Indian man who he introduced as Amyl then told me the man in bed with me was called Rasheed who asked me to lay down, l did as Rasheed asked, he began kissing …

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Becoming Kim

/ Categories: Bi-sexual, Consensual Sex, Cum Swallowing, Transvestite, True Story / Bi-sexual, Consensual Sex, Cum Swallowing, Transvestite, True Story / By

Little backstory first. I was blackmailed into coming out to a family member from an ex friend. I had quit dressing for 5 years cause of my living situation. When I told that family member they said just don’t run around in bra and panties in the living room. So I started buying panties and teddies again. I started wearing them every day. I only wore them in my room I wouldn’t even wear them in the common areas because I was nervous one roommate who was big time anti-any alt life style would see them under my shorts. Finally one day I got the courage to wear a pair while cooking. Then outside. Then every day. I ordered a few teddies from Lane Bryant and had them shipped to the store. I went to …

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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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pre surgery fun

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

So. I had back surgery the 2nd of May, was supposed to be there that day but my dr called me and had me come in the night before. I forgot i was wearing my black baby doll under my clothes, what follows is my last sexual encounter in over a month now. i got to the hospital and they took me into the surgery prep area to start with, and it was then and there i remembered i had my black baby doll on, and nowhere to hide it so i just went with it. and by that i mean i stripped down to it right in front of the sexy little nurse who looked at me kinda funny then said that’s cute. She said here is a robe, since you are not shy …

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Fun In Twickenham

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

Fun In Twickenham (The adventures of Chris and Linda) Bisexual, Crossdressing After my bath I stood naked in front of the mirror. At nineteen years old, I knew I was less than masculine. I had long ago given up any pretence of being manly. My body was slender, with no muscles to speak of, hairless except for a small patch on my pubes. My hair was long, dark brown and slightly wavy, down past my nipples now. My face – well, nice looking in a girlish sort of way. The whole effect was rather feminine. I was looking forward to seeing my girlfriend, Linda. She was twenty-four, blonde, and very pretty, with gorgeous green eyes. She was also rather kinky, which I loved, and liked my long hair and my feminine looks. I decided to …

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My little secret

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

My crossdressing started in Jr. High. When I started to get curious about girls, and also about other boys. I started crossdressing with my moms things, and slowly started to collect my own. By the way, I’m Mat… or Ashley as i’m known. I’m 17 and I guess you could call me Bi-Curious. Although after this story you could call me purely Bi-sexual. I have a friend, Katelin is his girl name but everyone knows him as Jake. He’s the same age, and we’ve been good friends for quite a while. We found out about each other last summer. When a pair of panties I thought I had hidden, suddenly came out into the open. Before I could react, he grabbed them and started asking me all kinds of questions. “Whos are these, what are …

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Dressed to Thrill (Part 1)

/ Categories: Bi-sexual, Domination/submission, Fantasy, Female Domination, Masturbation, Transvestite, Wife / Bi-sexual, Domination/submission, Fantasy, Female Domination, Masturbation, Transvestite, Wife / By

Dressed To Thrill – Part 1 It was only a matter of time before my wife discovered what I am, and I discovered her need to dominate and control me.   We worked different hours and I was often in the house alone which only encouraged my kinky tendencies. When she was away or had meetings she would get up and go to work early and I would stay home until it was time to go out later. It began innocently enough I suppose with looking at things on the internet and whilst my wife is an incredibly sexy and curvaceous woman I knew I needed more. I began to look through her drawers and her wardrobe to find the sexy and sluttish outfits to wear after she had left the house. I would get …

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Bitch in Heat_(3)

/ Categories: Anal, Authoritarian, Cum Swallowing, Gay, Spanking, Transvestite, True Story / Anal, Authoritarian, Cum Swallowing, Gay, Spanking, Transvestite, True Story / By

Bitch in heat Sitting at home, late at night, surfing the AOL chat rooms way back when could bring about some interesting opportunities. This is one such story. I had put away a considerable amount of work one day and was relaxing by searching through some AOL chat rooms… back in the day when it was the thing to do. Titles of chatrooms was one thing, but screen names were another… and searching for one of interest was always a bit of a chore. I had been hopping around different rooms for a while until I came across “Red Bottoms” which only had one member… “Master.” It didn’t take long for him to pipe up when I stayed in the chat room and offered a “Hello.” “Tell me about yourself” was what I got. “NOW”. …

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My little secret 3

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

Sunday started with the sun in my eyes to wake me up. As I sat up in bed I heard moans and screaming of pleasure. Putting a Bra and panties on, I slipped on my robe and went to investigate. Jim and Tom were downstairs, pounding Katelin and she was enjoying it. Moans escaped Katelins lips as she sucked Toms cock, Jim was behind her thrusting in and out very violently. As I watched my own boy thing started to get excited, while it wasn’t fully hard it was still ready to go. “Get on the floor Tom” Jim said panting and breathing heavily. Tom laid down on the floor as Jim moved Katelin on all fours. “You go in first” Jim said pulling out of Katelin. Tom put his hard cock to Katelins hole …

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More than before.. part 1

/ Categories: Blowjob, Cum Swallowing, Fantasy, Humiliation, Transgendered, Transsexual, Transvestite / Blowjob, Cum Swallowing, Fantasy, Humiliation, Transgendered, Transsexual, Transvestite / By

for more of this story dm me ! enjoy! It had been a week since everything changed. A week since Lina’s body had started transforming and a week since they first crossed the line from curiosity into something deeper, something neither of them had words for yet. At first, she was shy about it. The way she tugged the hem of her hoodie down over her hips, the way she avoided his eyes when he touched her… Jason remembered every detail. But it hadn’t taken long for something new to wake up inside her, something bold. Something hungry. Now, it was Lina who led the way. Jason lay back on the bed, heart racing, as he watched her move with effortless confidence. She was small, barely reaching his shoulder, with a frame that still managed …

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What If I Told Him I Wanted To Give Him A Blow Job?

/ Categories: Bi-sexual, Blowjob, Fantasy, Oral Sex, Transvestite / Bi-sexual, Blowjob, Fantasy, Oral Sex, Transvestite / By

Tom called the other day and invited me to come spend the night at the cabin. He said his wife was out of town and suggested we could do some fishing and drinking. It sounded like fun so I told my wife I was going. (Actually, I asked if I could go and she said yes). Tom met me at the cabin with a beer in each hand and offered me one as we went inside. We got the boat out and spent the day fishing on the river. We didn’t have much luck but had a good time, downed quite a few beers and were feeling pretty good by the time we got back to the cabin. Tom’s a good cook and he fixed up a great pasta dinner. We drank beers, swapped lies …

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Sometimes Short for Samuel pt. 2

/ Categories: Anal, Blowjob, Fiction, Masturbation, School, Transsexual, Transvestite / Anal, Blowjob, Fiction, Masturbation, School, Transsexual, Transvestite / By

Sometimes Short for Samuel pt. 2 The first week in the dorm had flown past, I was falling into a routine. My nightly rendezvous with Matt was earning me some freedoms that I enjoyed. Jacob was so far unaware I think but growing suspicious of why I was getting up to use the bathroom every night at 2 AM. Jacob hadn’t mentioned the hand job I gave him on our first night together and I hadn’t brought it up. I imagined he was struggling with the idea that he had allowed a boy to handle his cock. I let it alone, figuring he would talk about it if he wanted, or maybe if he wanted another hand job. He was however not any stealthier about jerking it which was happening with what seemed like increased …

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