My First Bisexual Experience



What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: High school diploma
What’s your occupation? Other
What’s your current relationship status?
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Cross dresser
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? None

My First Bisexual Experience

How long ago did this hookup happen? 19 years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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? My partner was a handsome man and we hit it off right away. I liked him and I knew he was the one I wanted to fulfill this long-awaited fantasy with.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It happened in a gay bar and we just made eye contact and we both were physically attracted to each other.

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 started seeing him on a regular basis and he didn’t know I was into cross-dressing. I decided to tell him one day when we were in bed and I shared my cross-dressing fantasy with him. He took it really well and encouraged me to live out my fantasy. So I wore a shoulder length brunette wig in a wild 80’s style big hairdo. I shaved my legs and body hair off and I put on my make up. I looked very feminine as I finished my make up. Then I put on a silky satin halter top in a lavender color with matching silk thong panties. Then I slid into a pair of pink vinyl booty shorts and pulled them up high up in my ass. I got my pink high heels and put them on. I looked at myself in the mirror and I felt so excited that my fantasy was finally coming true and the things I wanted to do sexually dressed as a hot slutty girl. I then went into the room where my boyfriend was and he told me how pretty I looked. So I got into the role of being his woman and I sat on his lap and let him touch me all over. It felt so amazing and I was all into the moment. Then we kissed and rubbed and touched each other all over. I got up off the couch and I gave my first blow job ever. I licked the tip of his hard dick then put my red glossy lips on it and wrapped my lips around his big hard juicy cock. I never felt so turned on in all my life when I finally fulfilled one of my fantasies as a cross-dresser. Then I went up to him and asked him to take me to the bedroom and fuck me. He had his hands on my waist as I walked in front of him. He had me wait for him on the bed bent over waiting for him to give me my first anal fuck as his slut. He lubed himself up and slid some lube up in my ass. We had lots of mirrors in the bedroom so I was able to watch e everything he did to me which made me more excited. Then he slid this big hard cock inside me and it hurt at first until he gradually started fucking me. Then it felt so damn good going in and out as he pumped me with his big hard dick. I loved riding it and taking it in all the way. He started fucking me faster and faster and I loved every minute of it as I watched him pound me from behind. His balls smacked against my ass as I wore my pink vinyl shorts for him. I looked at myself and felt so euphoric as my fantasy finally came true. He shot his cum inside me and he smeared it all over my ass after he was finished with me. Later on that night I had him shoot cum on my lips as I sucked his dick. I had all over me. It was the best time of my life ever sexually.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? I felt very comfortable dressing up for him and being his slut. I continued dressing up in hot slutty outfits but eventually, he wanted a more manly looking man. We broke up eventually and went separate ways.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Submission / Relinquishing power

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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 cross dressers after him. They were turned in by my experience.

How would you best summarize people’s reactions to 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? The acting out of my long awaited secret fantasy.

What was the WORST thing about this hookup? It was a brief experience.

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

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I’m glad I did it and I am very happy about it.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I think it is something we all want at some point in our lives. I just wish people would’ve more open-minded and explore their wild and kinky side.

What do you think about the Casual Sex Project? I liked the project.

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