Fun With A TS

by Steve

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? always looking
How many sexual partners have you had in your life (including oral sex)? about 60
How many hookup stories have you here posted before? over 10

Fun With A TS

How long ago did this hookup happen? yesterday

What was your relationship status at the time? Same as current status

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

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

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 was cruising some of my favorite hook up sites when I got a message from Danny. I checked his profile and found that he was a pre-op TS looking to give blow jobs. I am always looking for a hole to put my dick in so I responded to him.
He sent me some links to his pornhub profile that showed him in his car apparently out in the desert fucking his ass with a flashlight and in another he was giving some guy a blow job. We couldn’t seem to find a place to hook up at first but yesterday things fell into place

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He contacted me yesterday and asked if I could meet him, I was free so I said yes. He gave me directions and 30 minutes later I was at his place

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 rang the door bell and Danny met me in a short floral dress with a v neck showing some nice cleavage. He invited me in and led me back to the bedroom. Our conversations had always been about him giving me a blow job and “we’ll see how things go.” He lit up a bowl and we smoked a little while we talked.
He dropped to his knees, unbuckeled my pants, pulled my cock out and proceeded to suck my cock, deep throat, massaging my balls, sucking my balls, sliding a finger in my ass and massaging my prostate. It didn’t take long and I was filling his mouth and throat with cum. He continued to soak and caress my cock until I was limp.
He asked if I wanted more and I agreed. He undressed me and laid me on the bed and slowly began caressing my cock and balls. Kissing, sucking, truly acting like he was worshiping my cock and balls. It did not take long and I was hard. He asked if I wanted to fuck him and I told him I did. He got out a condom, put it on me, lubed his ass up and squatted over my throbbing cock and sank down on it in one motion. nice, not too tight but definitely nice. He rode me for several minutesand then asked that I take him missionary. I rolled him on his back, put his legs over my shoulders and slid into him and pounded his ass. The room was a little warm and before too long I was dripping sweat all over his dress. I pulled his dress top down and exposed his breasts, started sucking his nipples as my cock continued to stroke his ass. Another 5 minutes or so and he said he wanted doggie. I had him get on his knees and slid in again. I could feel myself getting closer, I reached around him and began to stroke his cock as I stroked his ass. His cock was probably close to 8 inches but not very thick… just the size I like if I’m going to be fucked by a guy/girl. I finally unloaded into the condom. He turned around, slid the condom off and began sucking my cock again and cleaned all the residual cum up.
I asked if he would like to fuck me. He said ok. I got down on my knees and sucked his skinny cock until he was good and hard, put a condom on him and lubed up. He positioned himself behind me and slowly slid in, allowing me to adjust to him. He was the perfect size and felt good going in. After a little bit he got into a rhythm, stroking me, hitting my prostate with each thrust, it felt so good. He fucked me for probably 15 minutes, I finally had a big orgasm and I guess that set him off because I could feel him getting bigger, throbbing in my ass. I swung around and pulled the condom off and sucked him dry.
He sucked me off once more and I fucked his ass once more before I left

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 agreed that we would do this again, a very fine cocksucker and bottom

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, Hoping or expecting it would lead to something more, Power / Dominance, Making new friends, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Marijuana, hashish

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

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? great cocksucker

What was the WORST thing about this hookup? nothing

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 prefer pussy, but any hole in a storm

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