Crossdresser Fun



What’s your gender? Man
How old are you? 40
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? Manager
What’s your current relationship status? Single
Religious affiliation:
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Bi open minded
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 1

Crossdresser Fun

How long ago did this hookup happen? 3 days ago

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For more than 3 years

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 knew Ken for 6 years. He is my neighbor. He’s married and retired in his 60s. We would hang out from time to time and have a beer. One day at his house, I noticed some porn laying around about transgender and gay people. I didn’t know he was bi, so I asked what he thought about men who dress in women’s clothes. I saw he was rather openly excited to talk about it, how he would love to find a friend who would dress for him so he could explore his bi needs. I started thinking I should dress for him…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The morning came. I got all cleaned up, watched for his wife to drive off, and got dressed in a nice tight skirt, nylons, and a garter wig. I also put on makeup. I was nervous but excited. I called Ken. I asked him if he knew anything about wall repair because I had accidentally made a hole in my wall. He said he could come over and check it out for me in 30 minutes. I sat and waited for him, nervous and excited.

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 opened the door for him. He didn’t recognize me and asked who I was. I smiled and said he could come to explore with me. He quickly came in and began to follow me, his hands quick to grab my ass and peek up my skirt. He asked if he could do anything to me and I said yes. He stopped me in the hall and removed his clothes. He pulled me close and began to kiss me. His erect cock was throbbing against my inner thigh. I fell down and took it in my mouth. I sucked him good, licking and sucking it deep. He pulled me up and walked me to my bed. He pulled my skirt up and began to eat my ass until he was ready to fuck. I got on all fours. He fucked my ass until he came and filled my ass with a hot warm load.

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? We meet as much as possible for sex.

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

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? Somewhat

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

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? No one

What was the BEST thing about this hookup? All of the cum in my ass

What was the WORST thing about this hookup? We live next to each other

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? None

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 am a cum addict

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