My First

by H

What’s your gender? Man
How old are you? 25
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
What’s your sexual orientation? Mostly heterosexual

My First

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Sex with an ex

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? Shannon had been my first kiss and later the person I had most of my firsts with, all of them after we broke up. Shannon was petite, with toned legs and milky pale skin. Aside for some experiments with hair die, she was a brunette with shoulder length hair. Her chest was modest, but perky with great tits.

I’d started another relationship, as had Shannon since we’d broken up. She’d lost her virginity to an older guy, whereas I was dating someone who wanted to wait. It didn’t bother me at the start, but I’d had just a taste of the things two people could do together and I wanted more.

Shannon still liked me and we’d been finding ways to pleasure each other, taking in turns to give each other head. Shannon’s boyfriend has encouraged her to shave and I enjoyed the result.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was between Shannon’s legs, putting my new skills with my tongue to work. For the first time, I used my fingers at the same time, pushing her over the edge to orgasm.

As I sat there with Shannon’s pussy in my face, I knew I wanted her and hoped the feeling was mutual. Almost on cue, Shannon asked me why I was still a virgin. I told her my girlfriend wanted to wait. Shannon asked why I was waiting, looking me in the eye and with a small voice told me I didn’t have to wait, if I didn’t want to.

Shannon stood up, and I thought she was going to leave. Instead she walked to her bag and pulled out a condom. She walked over to me and undid my pants, stroked my cock, and then dropped to her knees, taking me in her mouth. To my disappointment she stopped. Then opened the condom, unrolling it down my cock. I’d been having second thoughts.. I was dating someone else!

My eagerness to lose my virginity overcame any doubts. Shannon asked me what position I wanted, I said I wanted to be on top. She sat down and lay back on a table and I awkwardly climbed on top.

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? With more than a little help from Shannon, I lined myself up and entered her. I remember being surprised that there wasn’t much sensation.. and then she wrapped her legs around me, pulling me deeper and we began to fuck in earnest.

How sexually satisfying was this hookup? A little

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? Things were awkward for a while, and it was years before we got close again

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Learning new things, experimenting, Everyone else was/is doing it, Peer pressure, Just happened, I don’t know why, just went along with it

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? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Very

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

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? A little bit

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

All things considered, how NEGATIVE was this experience? A little negative

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