Trans

I (15) have fucked up thoughts about my trans online friend (17)

/ Categories: BDSM, Teen, Threesomes, Trans / BDSM, Teen, Threesomes, Trans / By

I have an online friend who is a transgender girl, and I have been having some very fucked up thoughts involving her and wish they’d come true. I am 15 and I have been friends with a 17 year old trans-girl who I met online a year ago. We are reasonably close and talk a lot (although I an very clingy). Despite my clinginess and weirdness she still treats me with respect and she’s always so kind to me. I had developed feelings for her since we had met and they never went away, sadly she never showed any liking (in that way) back to me as she has a boyfriend. As we continued speaking and I fell for her more, I began getting more and more jealous and falling into a dark rabbit hole …

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Jenny

/ Categories: Exhibitionist, Mature, Trans / Exhibitionist, Mature, Trans / By

“I could get arrested if somebody sees me with my penis hanging out of my pants.” I replied to her. I had been dating Jenny for 2 months. We hadn’t been intimate yet as we were still in that, getting to know you stage. I wasn’t sure about her, but I was in love. She was definitely one of the prettiest girls I’ve ever dated. She had small A cup breasts, which I love little titties, and a perfect hourglass body, with what you would call an onion ass. If you’ve never heard of that expression before, an onion ass is an ass so perfect, it makes you cry just to look at it. When we made out, I would get hard. As we made out, I would flex my penis which made precum leak …

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Teen crossdresser and jake

/ Categories: Gay, Trans, Zoophilia / Gay, Trans, Zoophilia / By

I have always dressed as a girl. Mom basically raised me as her daughter and I loved wearing makeup and lipstick and mini dress and corset and stockings and heels and etc. Well I was 15 at the time mom just got home from getting or nail done and hair done I very long hair and shopping. We weren’t home half hour and mom got a call. She kinda of arguing and then she said that she would. She said that she had to go to work for a couple days out of town. I said ok. I helped her pack she said I should be ok . She said yes since our great dane Jake was very protective. Well she finished packing and left. I changed into mini skirt and crop top. We lived …

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Crossdresser husband adult book store

/ Categories: Gay, Trans / Gay, Trans / By

I got up early one day and took a hot bubble bath then I got dressed in purple corset seamed suntan thigh stockings and hooked them to the garter straps on the corset. Glued on my silcone breast. Did my long lasting smudge-proof non-transferable makeup and lipstick. Putting in my heavy long dangling earrings. Well I picked out black micro mini dress skin tight and really didn’t cover my ass. Well I put on my 5 inch strapping stilettos heels. When my wife came in. She said dam you are dressed very hot and slutty. I said yes I am she asked me if I was going somewhere so early to meet someone. I told her no that I was extremely horny and wanting and needing cock. I told her that I was actually going …

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Crossdresser husband

/ Categories: Cheating, Gay, Trans / Cheating, Gay, Trans / By

Ron and I had affair over 5 years till his job transfered him and our wives new about it. Well my wife and I were talking an she told me that since Ron and his wife moved away not only did I lose my lover that she lost here partner in crime going out together finding fuck dates. I said yes true. I was surprised when she said you know that you have been with Ron for 5 years and Paula full time 24/7 an since they moved away that I not going to stop seeing an fucking other men. I said I know that. She also said that she had gotten rid of all my male clothes so I was going to stay as Paula. Well it had been a couple of weeks since …

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I am fantasizing about being a woman

/ Categories: Gay, Trans / Gay, Trans / By

I often wonder what it’s like to be a woman. I fantasize about it a lot. This isn’t so much a story rather than my own fantasy. Unlike the other stuff I’ve posted here, this is actually true. A little dive into my mind I guess. I was an only child raised by a single mother. I was always a loner and didn’t have many friends and my mom and I were kind of close. I didn’t so much fantasize about having sex with her but I was curious about seeing her naked. I would spy on her in her room as she dressed or when she’d shower. I would try to sneak peaks at her as she slept. The few times my dad was in the picture I would spy on them while they …

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My aunts friends carry on my journey…

/ Categories: Incest, Lesbian, PreTeen, Trans / Incest, Lesbian, PreTeen, Trans / By

Anal, Young, oral, lesbian, forced….. Trans Iydia was still on the sofa, marylin my aunt had actually passed out from her ass fucking by me… I was still laid over my aunt.. My ass still being probed by two fingers now and a hot tongue.. My cock even though I had cum was still inside my aunts tight ass… The tongue in side my own ass… The sensation was unlike anything… Lydia was complaining she hadn’t had time to cum… Maria… Went around to her on her knees she moved so her legs wrapped around Maria’s head… As soon as she started to lap her pussy Lydia groaned and said your the best mummy… Lick your babies cunt… My cock was starting to get hard again while I was watching and listening to this her …

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Attention Campers ;)

/ Categories: Incest, PreTeen, Threesomes, Trans / Incest, PreTeen, Threesomes, Trans / By

How working at a huge summer camp for kids made me the perv’ I am today. As the kids walked thru the door, there little friend in tow, I could tell tell the girl probably had a broken arm. She was about 11ish, curly brunette hair, the kind not often seen on little girls today. She was a real cutie. I could see she was in pain. I lead her to an exam room where I’d take a X-ray and set her bone, then after a pain pill or two, Id show her my bone. I’m Tim, I’m 23 and have a degree in sports medicine, along with being a certified EMT, I’m on the medical staff at a huge kids summer camp in the Mount Diablo Mountain range near San Francisco. I got this …

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Crossdresser and best friend part 4…

/ Categories: Gay, Group, Teen, Trans / Gay, Group, Teen, Trans / By

Mike had been gone 2 weeks and I heard nothing from him. I was so horny by now and keep think about how I was used by that oldman. Well my mom had been staying out late and not coming home. I was dressing more slutty and hot and naughty. Finally I got mom to fill my nails an eyebrows. Well she told me that she was going to be gone for a few days and I said what for she said business. I said ok. Well I was 15 now so it was fine. So the morning after she left. I got dressed very slutty and hot. I decided that I was going to go up to the old house. Well like I said I had to worlds most horny teenage full-time crossdresser. Well …

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My Tranny GF

/ Categories: Bisexual, Trans / Bisexual, Trans / By

I found out real soon that this transsexual was the right person for me. I had been dating Krystaline, a transsexual, for a couple of months now and things were as they usually are in the first few months of a relationship: really good! We hit it off really well at the bar and ended up having sex the night we met but once we realized we liked each other more than just a fuck we met at a bar, we had decided to slow our roll a bit and get to know each other better. I had come home from a date with Krystaline and this time just a bit disappointed that nothing happened between us. I knew that if I really needed it, I could get Mom to take care of me but …

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Crossdresser and best friend part 3 the twist of fun

/ Categories: Gay, Rape, Trans / Gay, Rape, Trans / By

Well Mike and were having sex every day for a few months. So one morning I called him to see if he wanted to go to our special place I was extremely horny and wanting it. He said that he wished he could but had to go visit his grandparents on his dad side. I said ok. So I decided since I was dressed very hot and slutty I would go to our place and do some stuff there. Well I got some clean sheets and stuff an put them in a pack pack and rode my bike there. I got there and went upstairs and was doing stuff when I heard something like someone coming upstairs. I just figured I was hearing stuff till someone grabbed me from behind. I turned around seeing it …

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Crossdresser and Best friend part 2

/ Categories: Gay, Teen, Trans / Gay, Teen, Trans / By

Well the rest of the day we kissed an made out. I sucked him and he licked my glued down boi virgia and gurly boi pussi hole. So this went on for a few days. We even got up the nerve to give each other hickeys on our necks. So about a week or so had gone by . Not once did I even think or want to be anybody but Paula . Well I came downstairs one morning Mike’s mom Becky and my mom were having coffee at the kitchen table. When said sit down we have to talk about stuff. Well my mom asked me if I was going to be Paula full time 24/7. I said yes. She an Becky said ok then basically had a heart to girl talk to me. …

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Crossdresser an best friend

/ Categories: Gay, Teen, Trans / Gay, Teen, Trans / By

I lived in a rural area with my single mother school was mostly home schooling. Well form the time I can remember I was always feminine as long as I can remember I had my ears pierced and was basically completely hairless except for my eyebrows eyelashes and long hair on my head. I remember mom teaching me how to do makeup and lipstick and girl stuff and letting me get dressed as a girl. Well I had one friend who was very open minded and never judge me for anything. We were both 14 and out riding bikes. We had stopped by the creek he was bigger than me. I sat down and he came up behind me and pushed me backwards onto my back and started to tickle me this went on for …

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Teen boi and oldman 2

/ Categories: Bisexual, Gay, Incest, Teen, Trans / Bisexual, Gay, Incest, Teen, Trans / By

The next morning he woke me up with a passionate kiss. I asked how long he was awake. He said long enough to admire you for a while and how sexy and beautiful you are. Well he said so do you regret anything that happened..I said nothing at all. He said great. Well for the next couple of weeks we made love every single day at least 3 times a day if not more. Then one day we were watching tv and I guess my parents were not happy I was gone. So they said that if anyone seen me contact a number. Well I said that I didn’t an won’t go back. I was going to stay with him. Well he kissed me and said let him figure this out. Well a couple of …

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My First Time Getting Fucked

/ Categories: Gay, Teen, Trans / Gay, Teen, Trans / By

I had fucked girls and even fucked my best friend in the ass but now it was my turn to get fucked. As a kid and into my teen years I had a kind of boyfriend. His name was Jayson and we would masturbate together and then it progressed to giving each other blow jobs and ultimately it lead to anal sex. All of that took 7 years to progress to. Jayson and I would continue this secret sexual relationship well into our 20’s and I always was the top and he always the bottom. There was a kid in my neighborhood that I also fooled around with when we were in high school. He was 2 years younger than me and we would just watch porn together and Jack off. His name was Jo. …

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Getting doubled up on

/ Categories: Gay, Threesome, Trans / Gay, Threesome, Trans / By

This is a quick story about how my other side, I call her Stephanie got fucked by two guys. If you’ve read my stuff, you know that I have two very different sides to my sexual identity. My bisexual side that is full of testosterone and manhood and Stephanie. My cross dressing, cum swallowing whore that just wants to be a lady. When I was 18 I was fairly open about my cross dressing. I had a couple straight friends that knew and didn’t care but that was because they didn’t know the whole of it. I had also made friends with a couple of gay guys that knew about it as well. One particular night I was having a party at my apartment and Jeff, one of the gay men I knew and I …

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Figuring myself out

/ Categories: Bisexual, Gay, Teen, Trans / Bisexual, Gay, Teen, Trans / By

I’ve been doing a lot of soul searching lately as to why I am the way I am. Here’s what I got so far. I found out about sex at a very early age. The first time I remember being attracted to a girl was in 2nd grade. A friend of mine and I started fooling around with each other’s dicks when we were 9. We’d masturbate in front of each other. That progressed to masturbating each other. Which lead to blowing each other, then getting completely naked and humping each other and eventually when we were in our late teens, we began penetrating each other. I never saw myself as gay while I was doing those things. When he’d suck my cock, I’d pretend he was a girl and when I’d fuck his ass, …

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Crossdressing truck driver

/ Categories: Gay, Trans / Gay, Trans / By

I am crossdressing truck dressed as a woman 99% of the time. I do most of my driving at night due to less traffic and headaches. I had taken a shower and since I had all of my body hair and face hair completely removed permanently I don’t have to worry about shaving. I glued on my silicone breast and put on my red bra then halo corset and red garter belt and thigh suntan stockings with red lace matching thong. I did my makeup and lipstick and long hair. I didn’t have to worry about my finger nails since I had a full set of square tip gel nails done and painted a few days ago and toes painted the same color red metallic. I put my ears in and jewelry on an red …

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Kari’s Sissy 3

/ Categories: Bisexual, Cuckold, Pregnancy, Trans / Bisexual, Cuckold, Pregnancy, Trans / By

After my first taste of cock as a sissy, Kari moves me further down the path of becoming a girl When we got in the bedroom, Kari jumped on the bed with her legs spread. God, Alex, I am so horny watching my sissy faggot husband take your cum. Fuck me. Fuck me with that big black cock. Breed my white cunt. Fill ne with baby juice. I should have been jealous. I should have been shocked. Instead I was turned on. Oh Kari baby. You’re going to love that big black cock. I can’t wait until he breeds you, I heard myself saying. I was stroking my cock, or more appropriately given my current state of wearing a teddy, makeup, nail polish, etc, my clitty. I was so turned on watching Alex slide into …

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My first cock in a while! Pt. 2

/ Categories: Gay, Mature, Trans / Gay, Mature, Trans / By

I had sex with a man for the first time in a long time and I wanted more! My phone rang early this morning and woke me up. Immediately I was annoyed since I was on vacation from work this week but when I looked at the number, I noticed it was Paul. Paul was an older man, in his early 50’s I had hooked up with a few nights ago. When I met him at the bar, I was fully intended to be a one night thing. I’m in my late 20’s, a man of his age is not what I’m looking. The night was so incredible though and he treated me exactly how I wanted to be treated that I decided to see where this went. Plus, for a 51 year old man, …

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