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What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Charleston, NC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Banking
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Finding Myself

How long ago did this hookup happen? 2 weeks

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

How would you best classify this hookup? Short fling

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

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 found him on an online ad for a gay erotic massage. I had seen him twice before and enjoyed a nice massage with a happy ending in my hotel room. He was slim, with a tight butt, muscular legs, cut abs, and a nice beard. While traveling on business, I arranged for him to meet me at my hotel. I am a guy who did not explore my attraction to men until about five years ago and found I like it much more than I thought I would. I had many gay massages before, but I felt a connection with J and always fantasized about more with him but didn’t expect it. Also, I had never experienced anal as a top or bottom.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been overweight (325 pounds) but had lost over 150 lbs since I had last seen J. When he saw me, he couldn’t believe I was the same person. We walked into my room and he continued to gush over my new physique, which I didn’t mind! I undressed and lay down on my stomach on the bed ready for my massage.

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? J proceeded to massage me well, as usual. When he had me turn over, I was hard as a rock from all of the sensual touching. He massaged my shoulders and chest some and then gently started stroking my cock. Suddenly he stopped and said, “how about we end the massage now?” With a raging hard on my reply was, “now??” He said, “yes, if you want the off the clock treatment”. With that, he climbed on top of me and kissed me deeply. Then, he moved down my body and took my cock in his mouth and started slowly taking it all in while stroking my balls. Then, he moved his huge dick above my head and lowered it to my lips. I was so hungry for him I took in more than I expected. I loved this position as I could alternate between sucking and rimming him. I felt the climax building in me and told him I was close and he sucked me harder until I came and he swallowed every drop. He started thrusting down my throat and I felt his cock start to pulse and fill my mouth with his sweet salty come. It was amazing. We lay there touching and recovering when he said, “I want to be inside of you”. I had never done this before but I wanted him to be my first. I told him I was an anal virgin and he promised to be gentle. He had me lay on the edge of the bed and he pulled my legs back before he started rimming me. Then, he gently inserted a finger into me until I relaxed and then two and finally three. I couldn’t believe how amazing it felt. He got lube out of his bag and a condom. I was so crazed with lust for him at this point that I told him I didn’t want the condom, he assured me he was clean. He lubed himself and my hole and slowly pushed his cock in me. It hurt for a moment but then he slowly but firmly pushed all the way in and stayed there until I was ready. I practically growled for him to fuck me. He started slowly and we stared into each other’s eyes while he brought this wave of pleasure over me. This is what lovemaking is, I thought. After a while, he had me flip over and did me doggy. We finished in missionary, me shooting all over his stomach and him filling me with his load. We ordered room service and had some dinner, then he fucked me in the shower, on the desk, and standing in the window looking out at the city. Never have I had such amazing sex before.

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? I hoped to see him again the next time I was in his town, about 6 months later, but when I tried to contact him his ad was gone and number disconnected. I wish I could find him again.

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, Emotional intimacy, closeness, connection

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

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

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Opened me up to a part of my sexuality that I had not experienced before

What was the WORST thing about this hookup? Made me want him again

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

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