First Time (Male)

by Tom

What’s your gender? Man
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Miami
Highest education received: Some college (not currently in college)
What’s your occupation? Route Manager at a Window Washing Company
What’s your current relationship status? Single
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? No. Just VERY straight.
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

First Time (Male)

How long ago did this hookup happen? Two weeks ago

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

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than 6 months

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? So I used to work at a small, not-so-busy (relatively speaking) Dunkin Donuts just outside the city limits. I worked afternoon-to evening shifts so I worked it with people who often had something to do after hours. One of the people I worked with was a beautiful (and I mean beautiful in the sense that she probably shouldn’t be working at DD) blonde haired lady with blue eyes. She was a little older than me (about 3 years) but she looked younger (I would have guess 18 or 19 instead of 23). We got along pretty well and we often chatted about our personal lives. About five months into our professional relationship, she asked me how many girlfriends I had in highschool. I told her the truth and said that I had never had a girlfriend before. She seemed very surprised. “Like, never ever?” she asked me. I explained to her that until highschool I had been homeschooled and in highschool I just didn’t find the dating scene appealing. I then turned the question around on her and asked her how many boyfriends she’s had. She told me 3. One was serious and two were just for fun. We went back to work after that (because a new order came in) and didn’t talk much after that until we were done with work.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After work that day, Kristy (that’s the girl’s abbreviated name) invited me to go for a drink. I don’t usually drink (not even socially) but I thought it couldn’t hurt. It also helped Kristy was absolutely beautiful.

So we went to a local club (it was my first time at a club) and talked for a few hours. We didn’t do any dancing, tough, which I think is kinda funny looking back. Anyway, Kristy has a few margaritas and asked me to take her home around 10 o clock that night. I agreed and drove her home in her Chevy Cruz (we had carpooled to the club) and walked her to her door. I was about to tell her good night (I was getting nervous) but she invited me inside to have glass of wine. I agreed, and before I knew it, I was sitting on Kristy’s couch drinking a bottle of Zinfandel.

I don’t exactly remember how it happened, but a few minutes into our conversation, Kristy interrupted me, saying, “So like, you’ve never had sex before?” I was very taken back by the question and became really awkward. I hadn’t been expecting a topic change like that at all. Obviously I didn’t know how to respond, so I just said yes. Kristy appeared genuinely surprised at my answer. She then proceeded to ask me a number of much deeper and more intimate questions about my sex life, such as if I watched porn or masturbated. I (very nervously) admitted that I did both but only occasionally (once or a twice a month) when I was aroused by suggestive content on social media. She then asked me why my favorite kind of porn so I replied softcore because I found the more hardcore stuff (such as anal sex) revolting. She then asked another question that once again surprised me. “So you’ve never had a girl give you head before?” I said no. She then put down her glass of wine and began to undo the belt on my pants. “Let’s fix that right now.” She said, or something to that effect. At those point I completely froze.

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? Kristy reaches into my pants when the belt was undone and began to stroke my penis with her soft hands. I didn’t know what to do or say, but the feeling of having someone else’s hand on my shaft was incredible.

Kitty then leaned over from her sitting position next to me on the couch and began to suck my now-erected penis. Her mouth was pleasant and warm and it only took me a about two minutes before I was ready to cum. I began to tense up in anticipation but Kristy stopped sucking for a minute and looked up at me with those beautiful blue eyes. “Does that feeling good?” She asked me.

“Yeah,” I replied.

She smiled sweetly and leaned forward to whisper into my ear. “Would you like to put it inside of me?” She asked. I really wanted to, but I told her I was really nervous because it was my first time.

She said it was okay and took off her clothes in front of me. Her body was incredible. About that, I have nothing more to say. She then climbed on top of me and guided my penis into her vagina. I groaned with pleasure while she gasped. My penis is not very large (it’s just over 5 and a half inches), but because she was sitting on top of me, I felt like it went very deep inside of her. She grasped my face gently and began to ride me very slowly. I wrapped my arms around her back and grabbed her butt. We locked eyes and stared at each other for the rest of the experience. About five minutes in she asked me if I wanted to try doggy style. I said no and so we stayed like that until I came inside of her a minute or two later. I apologized that I came so quickly, but said that it was fine and that I did really well for my first time. She asked me if I would like to do it again and I said definitely. From then on I’ve been intoxicated by her and looking forward to seeing her everyday. We probably had sex three or four times after that but I got a new job shortly after. We remain friends until this day but it’s been a month or so since we last had sex. I’m inviting her over this weekended so hopefully we will do it again again.

How sexually satisfying was this hookup? Very

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? The next day I felt really guilty for losing my virginity, but I had sex with her again a few days later. This time we tried doggystyle and I lasted about 10 minutes.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

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

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

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? I don’t know / I’m not sure

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, which is why I am posting here.

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I lost my virginity to someone that I like a lot, but am not sure if she sees me as anything more than a casual fling.

What was the BEST thing about this hookup? She was very accommodating and didn’t ask for me to do anything I wasn’t ready to try.

What was the WORST thing about this hookup? I lost my virginity. Duh.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, I still think sex is better in a committed relationship.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Nah.

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? More commitment would be nice.

What do you think about the Casual Sex Project? It’s cool. I dig the idea of being able to talk about this stuff.

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