by Coffeelover

Gender: Male
Age: 29
Race/ethnicity: White
Current location: Oregon
Highest education received: College degree (eg., BA, BS)
Occupation: Banker
Relationship status: Engaged
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? None

The 27 Year Old Virgin

How long ago did this hookup happen? Almost 3 Years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? First Time/One Night Stand

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? Julie was a heavy set woman, curvy with big breasts and a little taller than me and I remember she had long brown hair.  We met online, I will go more into that below.  I felt an instant attraction to her.  She was also the first person I ever had sex with.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Now I was a much later in life virgin, out of all my friends I had sex for the first time last.  By the time they were all my age, most had multiple partners and two of them even had divorces under their belts.  My lack of sexual activity was hardly from a lack of interest, just opportunity but I always felt like I was missing something.  In High School girls always made me nervous and they showed me no interest.  In College I dated some, made out with and felt up a few girls and once had a girl’s shirt off but was interrupted.  I also dated a girl for a year who was waiting until the wedding night to have sex.
After college I dated some, but still things just never fell together.  Without realizing it I was 27 and never had sex.  I was at a training event a few hours from where I lived in a much bigger city.  I put a post on craigslist saying basically I was a virgin looking for his first time not really expecting much to come of it.
Julie responded and we emailed back and forth a bit and she sent me a few pictures including nudes.  We agreed to meet and decided on an Arby’s next to the hotel I was staying at.
I was very nervous, as I said I had never done this before. Julie met me, was dressed conservatively and we ordered something to eat.  We actually talked for about an hour about all kinds of things to calm me down.  Julie was quite patient with me with some light touching and flirting.  We finally went back to the hotel.
We sat on the bed and talked for a bit and finally Julie got close to me and we started kissing.  I felt her a bit and grabbed her boobs a little and that moment finally came.  Julie was patient but quickly figured out she was going to have to make the first move.

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? We took our clothes off and looked at each other, she had a tattoo on her breast and I was staring at them.  I had seen boobs before, as I said I had a girl’s shirt off once and I had been to strip clubs a few times.  Still I laid her down on the bed and buried my face in them and licked her breasts and sucked on her nipples.  Julie offered to suck on me, first I was a bit confused but she told me to lay back and began to suck on my cock.  I moaned a bit and Julie sucked me until I was very hard and then laid back and told me it was time.  I mounted her and penetrated her and it did not take me long to finish.  I had to lay there for a while after.
Julie and I cuddled for a bit and I kept thanking her and she laughed.  We talked for a long time about all kinds of things and she used the bathroom before we went again.  Julie mounted me this time, in what I have since learned is called cowgirl and what is now my favorite position.  She would bounce on my cock a bit, lean forward after a while and kiss me and then let her breasts rest on my chest and I really liked that.  It took me about fifteen minutes but I came again and afterwards we fell asleep quite quickly as it was now quite late and we were tired.
We went one more time in the morning, Julie sucked me until I was quite hard and then I penetrated her again and finished.  We took a shower together with a lot of touching and kissing but no sex, I ordered room service and we ate breakfast and then I had to get to work so Julie and I kissed and went our separate ways.  I had quite enjoyed myself.

Did you have an orgasm? Did your partner(s)? All three times, I don’t think Julie ever did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Since I had no sexual history STIs never came up but we did use condoms all three times, I wanted to be safe.

What were your REASONS for having this hookup? I was horny and wanted to and Julie was willing, but mostly because I wanted to have sex for the first time

Were alcohol or drugs involved? If so, how much? Nope

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 texted Julie to thank her later that day and she said she had quite enjoyed herself too.  This opened me up to the world of sex and I would go on to have my first one night stand two months later and not long after that have the nerve to ask the woman who would become my fiancée not long after.  I tried getting in touch with Julie via email and text the next time I was in town about three months later since I was single at the time but she didn’t respond to my texts or emails and I have not heard a word from her since that night.  I am quite grateful to her for being my first and will always remember her.

To whom did you talk about the hookup? How did they react? Told a few friends who were impressed with me for finally popping my cherry.

Was this a consensual and/or wanted experience for you? For your partner? Yes for us both

Do you regret this hookup? If so, why? Not one bit

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? I would say the best part was having sex for the first time, I feel this was a very formative experience in my life.  The worst part was she didn’t get back to me when I wanted to get in contact with her again.  As I said I am quite grateful to Julie for being willing to be my first, I brought another girl home not long before this who was quite weirded out when I told her I was a virgin and left.  This opened me up to casual sex and sexuality, without this hookup I would probably have not been wiling to have that one night stand or been willing to sleep with my fiancée when we started dating.  I felt really good about myself and have been a lot more self confident since then.

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 or anything else? I did want to add this in, when I started sleeping with my fiancée we had an awkward conversation when we realized she had a much larger and more extensive sexual history.

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