A Night Of Firsts



What’s your gender? Man
How old are you? 55
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? Los Angeles
Highest education received: Some college (not currently in college)
What’s your occupation? Electrical Utility Worker
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Curious
How many sexual partners have you had in your life (including oral sex)? 100
How many hookup stories have you here posted before? 0

A Night Of Firsts

How long ago did this hookup happen? 20 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Paid sex

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? She was a trans hooker, about 5’ 10”, with shoulder length black hair, small tits, and a small waist! She was pretty with a sexy smile. I met her that evening in downtown LA.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was out drinking after work on a Friday night hitting up some bars trying to get laid but having no luck with the ladies. After the bars let out, I was drunk, frustrated, and way too horny, so I went cruising for some pussy or ass whatever I could find. I ended up finding this Latina wearing a mini skirt, with long legs, and a nice tight ass! I pulled up and we start the negotiations. She tells me she’s transsexual and has a place up the street. I figured she was trans, but that was no big deal for me since I’d had my fair share of trannies, especially when drunk and horny!

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? We go up to her room in a flop house with mostly trans tenants. Her room is just a bed with nightstand and tv. It looks pretty squalid, but fuck it, it’s not like I’m moving in! I had told her “queiro cojer” (I want to fuck), and I paid her 50 bucks I think. We start making out, and I’m sticking my tongue down her throat and she’s stroking my rising cock through my work pants. I’m 6’3” and like I said before, I had gone out straight after work. I was an apprentice lineman at the time, climbing poles and doing an extremely physical job! So I’m sure I wasn’t the freshest daisy, but I didn’t give a shit…that’s probably why I wasn’t getting any play from the ladies!

So I’ve got my tongue down her throat and I’m feeling up her ass and getting hard as a rock! She pulls away and asks if I want to smoke? Fuck yeah! She gets a glass pipe, and pulls out what looks like crack! Hmm, I was expecting some pot, but then she says it’s crystal meth! We take some hits and I can feel my buzz going into overdrive! She drops to her knees and pulls out my cock. I’m 7 inches and average girth. She starts circling her tongue around the head and stroking her own cock! She takes me in her mouth and is licking up and down while continually stroking her own 8 inch cock! After about 10 minutes of expert bj technique, she tells me to lay down on the bed. I strip off my climbing boots and get naked, as does she, but she leaves her high heels on.

I’m laying on the bed with my hands behind my back and she’s is rubbing her naked body all over mine. I can feel her hard dick rubbing all over me. She’s kissing me everywhere as she makes her way back to my cock and starts licking all over my cock and balls. She lifts my legs up and starts licking my taint. Then, her tongue starts licking my asshole. My cock is hard as fuck as she strokes it I feel her tongue start penetrating my asshole. My head is spinning and then I feel her starting to finger me! I still haven’t come and she says how about another hit? She takes a hit and passes it to me. While I’m hitting it, she’s fingering my asshole and stroking her cock! It looks sexy as all get out! She stands up to get the pipe and I’m sitting on the bed. She’s hitting it again and her cock is in front of my face! She puts the pipe down and is stroking her dick at my eye level! She then asks me to suck it!! Now, I’ve been with a lot of trannies, but I’ve never sucked any cock. I’m attracted to transsexual women because they are women! I’ve never been attracted to men and always considered myself straight, but I was high and horny and that cock looked good, so I told her to put on a condom! She reached into her nightstand and I saw it was full of rubbers!! She wraps her cock and I start sucking like a madman! I’m sure my skills weren’t that good, but she wasn’t complaining!

I moved myself so she can reach my dick and she’s stroking it as i’m sucking her. She starts fingering me and I feel my cock ready to explode. After about 15 minutes of me sucking and her loosening my asshole, she asks if she can fuck me!! Now, an hour earlier, I had never sucked a cock, but now I was ready to get fucked in the ass!! I maneuver myself on all fours and stick my ass in the air. She pulled me onto the edge of the bed and slowly inserted the head. I felt my sphincter open to take her in. I was surprised how easy it went in. I guess the combination of her fingers and the meth had made me ready to take all of her long cock inside me!! After a minute or two, she was all the way inside me and I was pushing back onto her cock with her every thrust. I pushed my head down on the pillow to muffle my screams! After a bit, I could feel her start to speed up and she tells me she’s about to come! She’s pounding my ass and I’m ready to explode! I feel her coming in me and I can’t hold it anymore and I came then also, just from her fucking me!!

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 kept hitting the pipe and sucking and fucking each other! Her friend, another tranny, came in and started partying with us. I laid there naked and she was showing me off to her friend! My girl got a call and said she had to see a friend! A big black guy came to her door and I guess he was there to fuck her! Her friend offered to take me upstairs to her room and since I was still horny and high I went. We partied some more and I fucked her. She wasn’t as attractive as the first girl though, so I didn’t suck her dick or let her fuck me even though she tried!

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, Attraction to partner(s), Learning new things, experimenting, Intoxication, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol, Marijuana, hashish, Meth

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Meth

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

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

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Smoking meth for the first time! Sucking cock for the first time!! Getting fucked in the ass for the first time!!! A night of firsts!

What was the WORST thing about this hookup? I haven’t repeated it since.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve always been open to straight sex with any feminine partner, paid or otherwise. This made me realize that under the right circumstances I can open myself up to much more sexually!

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? Now that I’m married, I no longer indulge in these types of experiences, but writing this makes me think I need to try this again without the meth!!

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 my personality is geared to these types of casual hookups! I tend to bore easily and I need these sexacapades to keep me stimulated! If you’re being honest with yourself you may feel the same!

What do you think about the Casual Sex Project? I love reading these stories and they’ve made me want to find some strangers!

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