Losing My Virginity To A BBW

by Richie

What’s your gender? Man
How old are you? 34
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Businessman
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50 ish
How many hookup stories have you here posted before? 0

Losing My Virginity To A BBW

How long ago did this hookup happen? 14 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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

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? Her name was Sara. 27 years old, was perhaps 5’6, 180 pounds, red hair and a pretty face and a bubbly personality. We met at a park where she was trying to get in shape and our discussion was mostly about fitness. I didn’t even think about sec with her prior to the hookup.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She invited me to go running with her starting at her house. We did 5 km and she invited me into her townhouse. She said she needed to take a shower and invited me to join her.

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? I was a virgin and felt uncomfortable getting undressed even though I had and still have a nice fit body. She was waiting for me in the shower completely naked. We made out for a bit, playfully splashing water on one another. She put some body wash on her hands and stroked my massive hard cock, cleaning it. Then she got down on her knees and wrapped her mouth around my cock. Part of me was hoping to cum then and there as I didn’t have a condom and was still only in my 2nd year of university. She asked me if I liked it. She told me not to cum. So I held back. She sucked me more and more. She was skilled at not letting me cum though. She then shut off the water and got out, telling me to follow her to the bedroom. Nervously I followed her. “I have an IUD” she told me, calming my nerves. We went to the bed, her legs were spread. I climbed on the bed and she grasped my cock and guided it into her pussy. Now I was a man. She told me she likes to be banged. So I thrusted hard, arching my back and sliding all the way in and pulling out until only about an inch of my cock was still in her. I lasted a surprisingly long time inside her wet pussy then she said the magic words: cum inside me. I thrusted a few more times until my body couldn’t take it anymore and I released all my seed up into her pussy. We kissed. Then decided go call it a night.

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 remember looking at myself in the mirror and thinking that I was a man. Proud of myself.

We hooked up twice more. Thats for another story.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? My best friend. He congratulated me, we were 20.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I lost my virginity, it was spontaneous and cumming inside her felt A++.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I always kind of envisioned it happening unplanned

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? It was great!

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? I wish people were more expressive of their sexuality outside of the bedroom

What do you think about the Casual Sex Project? Its great

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