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What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Las Vegas
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Something
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? I’m a bi crossdresser.
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

Fucked While Crossdressed

How long ago did this hookup happen? 1 year

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

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 didn’t know him at all. He was very tall and muscular. I met him on Craigslist; I had posted as a crossdresser looking for a man for sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began just inside the door of his apartment.

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 knocked, and he opened the door and told me to come in. He was in his underwear. I told him I was very nervous, and he said, “This will help,” and proceeded to put my hand on his bulge. I played with it for about 20 seconds, and I was getting really horny. He then said, “Why don’t you go get dressed up for me?” I went into the bathroom and put on my panties, thong, heels, bra, dress, and wig. I went to the living room very nervously. He came up to me and sat down on the couch. He guided me in front of him. His cock was a really nice size, maybe 8 inches and uncut. I sucked it for a while, and eventually, I started trying to deep throat it. When I did, he grabbed the back of my head and held it in my throat for a while. I love that he was starting to control it. After about 20 minutes, he had me get up on the couch on my knees and pull down my panties and pantyhose. He got a condom and lubed himself up. He shoved it in me from behind, and it was very intense. I was so horny that I was in a fog. He fucked me hard. I remember my head being pushed into the wall with his hard thrusts. After about 10 minutes, he had me move to the other couch standing up but bending over the back of it. It felt so slutty to be fucked while standing. He fucked me for another 10 minutes or so and then we moved to the bedroom. I felt so hot and slutty walking down the hall while he watched my freshly fucked ass moving back and forth. We laid on the bed, and he started to suck me. I came very fast.
Once I came, I lost all my desire and told him I needed to leave. He clearly did not want me to but I lose my desire after I cum. I went to the bathroom and got dressed back to my normal clothes and then left. Looking back, I wish he would have been a little more forceful in making me stay. I would have gotten horny again real fast. He had not cum yet, and I think he was saving it for round 2 since he said he had only 1 condom. I think he wanted to cum in me, and I kind of wish I would have stayed and let it happen.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? Immediately after the hookup, I regretted it. But, the next day thinking about it would make me extremely horny.

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, Submission / Relinquishing power, Boredom

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

Did your partner(s) consent to this hookup? They gave enthusiastic consent

What was the BEST thing about this hookup? I felt like a woman being fucked.

What was the WORST thing about this hookup? It ended too fast.

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

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

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