A Nice Midnight Surprise

by KV

Gender: male
Age: 27
Race/ethnicity: Caucasian
Location: New York, NY
Highest education received: Some college (not currently in college)
Occupation: Illustrator
Religious affiliation: No religious affiliation
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before? This is the first

gay-boss-wants-a-blowjob-t-1A Nice Midnight Surprise

How long ago did this hookup happen? 8 years ago

How would you best classify this hookup? First oral experience

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? This person, we’ll call him B, was about average height and had an athletic build. He had jet black hair cropped on the sides and stylishly wavy on top, with very pale skin. Like a sexy vampire, with devilish grey eyes. He dressed in fitted black and grey clothes, he was studying fashion after all.

I only knew B for about 1 week. We were in the same university orientation group and had exchanged flirtatious looks throughout the week. At the end of orientation, my group decided to go out and see what bars we could get into without IDs because we were all under age.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had never shared a sexual experience with another man before but knew that I was always curious, so being a new college student far away from home and having just enough alcohol to shed some inhibitions; I felt like a different version of myself. And I enjoyed it.

B and I were quick to flirt while out, he initiated most of it because he was already out and very comfortable with his homosexuality. I was a newbie, but easily seduced. We danced and kissed throughout the night until it was time for the group to head home.

As we got into a cab, B and I cuddled up in the back and promptly started stroking each others penises. This continued until we arrived at our mutual friend’s apartment, where I promptly fell asleep on the couch while B and our friend talked in the bed room.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I am still not sure how long I had been asleep, but I awoke to the caressing touch of someones hands on my body. I was already hard when awoke, and this person started unbuckling my pants. There were no words exchanged. After my pants were pulled down, this person pulled my penis from my underwear and started sucking me off. I had never had a blow job before, so this was an entirely new and astonishing sensation. This person continued, and I reached down to touch their face. Only to realize this was a man’s face, the stubble on their cheeks gave it away. I knew immediately that it was B, and I thoroughly enjoyed it. B continued to use his mouth and hands on me until I came, he moaned with approval when my cum hit his throat. Taking everything that I could give him he slowed down his pace.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not really discuss our past sexual history at all, let alone STIs. I was also still very new to sex and had not put myself in any situations that could have resulted in infection or detrimental outcomes.

What were your REASONS for having this hookup? I was so taken by this brand new life of mine. A new city, new people, new social possibilities. I was also very comfortable with my sexuality and the desires associated with it.

Were alcohol or drugs involved? If so, how much? Yes. We had both drank a fair amount of hard alcohol that night. But no drugs were involved.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I felt happy and safe, both during and after the hook up. When the experience was over, B had no expectations of reciprocation that night or any others. In fact that was the only experience that I shared with B. We became fast friends and hung out in the same social circles throughout our time at university.

To whom did you talk about the hookup? How did they react? I didn’t really tell anyone, because I was still getting to know people. So I didn’t really have any close confidants to share with.

Was this a consensual and/or wanted experience for you? For your partner? Absolutely it was.

Do you regret this hookup? If so, why? Not at all or ever.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best part was the newness of it. There wasn’t anything bad, except maybe that I never found the chance to play more with B.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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