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What’s your gender? Genderqueer / Nonbinary
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
Highest education received: High school diploma
What’s your current relationship status? Dating casually
What’s your sexual orientation? Bisexual

Boy Becoming A Gurl

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I have a thing for tall guys, so I made sure that I found somebody over 6 feet tall. My personal ad stipulated that my lover must be big in other places as well. Even though I had made it clear this was my first experience with a guy, I have been masturbating with large dildos and cucumbers for a while, so I new what I could handle. I wanted a man who could pic me up off the ground and make me feel like a girl, a slut…a slutty little bitch. My personal ads drew quite a lot of attention (like 60 reply’s, tell you why soon) so I was able to be fairly selective. I chose a well built guy in his late 30s, based on some hot pics and some chatting I was soon on my way to his house to give my body to him and lose my virginity for the second time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Ok so I was completely straight up until I was 19. In fact, I still like girls and am fascinated with femininity and the female form, which makes up a lot of my desire to use my own body in such ways. My body just wasn’t filling out like other boys, plus I’m pretty short and have always had long hair on my head (none on my body), and then i discovered my butt. Just drying my hair facing away from a mirror one morning, I caught a glance of something i had never realized before… I had a booty! I was a 19 year old guy with a thin female frame and a fucking bubble butt. This kind of annoyed me at first, however it suddenly turned me on more than I ever could have expected. I started to turn around in front of the mirror, inspecting my ass from different angles. As I worked my hands up and down my slender legs, staring at my slim waist and broad hips in the mirror, I think it was right there and then that I decided I wanted to see myself wearing girls clothing. From X-dressing (in private) to anal masturbation it was about a year until I started chatting to boys online and sending them pics of me in sexy girly outfits that I would secretly purchase. A lot of fun, but I was ready to take the next step. To use my body like a woman and to use my ass like a vagina.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I’m sitting out the front of his house in my car. Dressed, shaved and prepped like a porn star under my tracksuit, wondering what the fuck I was doing. I hadn’t sent a face pic so I was a bit worried he may not even like me! The house door opened and a good looking guy invited me in. OMG he’s already completely naked and smiling like it was the normal thing to do. We hug and I’m trying to keep my cool but kind of panicking a bit inside. I’m about to have gay sex for the first time I just realized. I ask myself, ‘Should I just bail out now before it’s too late? Sitting on the couch with him, I decide to be honest and tell him how I’m feeling. He was really cool and didn’t push me at all. I think he knew exactly what to say in these circumstances and chilled me out pretty quickly. The whole time he sat there naked and gently stroked his cock making it harder and bigger. I kept looking down at it, feeling more relaxed I said, ”fuck it, I’m here to have fun.” While he made conversation, I got up and took off my tracksuit and bent over in front of him on the carpet. Poking my ass in the air for him to see for the first time in the flesh, needless to say he stopped talking. My new lover wasn’t really into my crossdressing side so I just kept it simple for him. Little white top with tiny shorts and some thigh high socks. I was however shaved and cleaned to perfection. Ready and willing to act out some of my favourite porn scenes with this gorgeous man and his sexy penis, starring me as the girl! I’ve fucked this guy at least 20 times now and I love his cock! It’s got to be 8 inches I think but it’s big and heavy. Never will I forget this first time I was in front of it. After stripping down to just my thong and doing different poses for him on the soft thick carpet, I realised I had made him really hard. ”Well bitch, this is what you wanted, wasn’t it?” I remember telling myself. I crawled to him and he spread his legs out to let me get in between.

I’ve touched my own cock daily of course all my life but the feeling of another persons penis in your hands is a completely different sensation. Addictive in itself! That’s when I totally left my normal self behind for the night. I’m not going to lie and say I was great at it, but I gave him the best and horniest head I could imagine. Yes, I licked his balls and the shaft and basically choked myself on him, leaving his dick dripping. I had to be warned about hitting him with my teeth a bit so I knew I needed practice to make a guy actually cum. ”Lets go to the bedroom,” he says. So he picks me up and walks me into a room and throws me on a bed in front of large full length cabinet mirrors. YES that’s how i wanted it. I actually wanted him in me really bad so I spread my self for him and snap off my undies. At this point, I am a girl and I wanted to be treated as such, so I bounce back up on my knees and start sucking him off again. That’s when I developed my love for sucking cock, right then! He pushes me back on the bed and lays behind me, I spread and start saying stuff like, ”You like this little ass?” I know he does because his dick is ROCK hard. I’ve never seen anything like it and laying on my back with one leg being held up is how I first took it inside of me….WOW. Ok so this wasn’t like a dildo or a cucumber and I wasn’t in control now. This was big hard cock and it was almost too much at first. Reality alert, after some bathroom checks and more lube I actually relaxed and loosened up, then I started to enjoy it. His cock had opened up my new little sex hole completely now. I had at least 4-5 anal orgasms that night. Some making me cum with my cock and some not, but all made my body shake uncontrollably. We did it in every position we could think of and fucked in the shower twice. I found out my talent in bed is riding and taking it deep and fast on top. Watching myself riding with my hands behind my head is my fave..tbh i look better than a lot of girls doing this and I fuck better too, boys have told me. Even though we used protection it was still maybe the best sex I’ve ever had. I let him cum on my belly once and inside me with a condom on. Next time… I would end up with it up in my tummy and on my face…next time xx

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? At first a bit of regret…but that didn’t last long. Too much fun!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, To feel better about myself, To feel more desirable, To feel more confident, Boredom, Just happened, I don’t know why, just went along with it

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

To whom did you talk about the hookup? How did they react? other men

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I’m an anal sex addict now.

What was the WORST thing about this hookup? I’m an anal sex addict now

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? probably

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? A little negative

What do you think about the Casual Sex Project? It’s great

You have a hookup story to share? Submit it here!