First Date Turns Into First Casual Sex



What’s your gender? Man
How old are you? 30
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: Some college (not currently in college)
What’s your current relationship status? Single
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)? 20
How many hookup stories have you here posted before? 1

First Date Turns Into First Casual Sex

How long ago did this hookup happen? 11yrs

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 a month

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? She was 18, short and very petite body, small perky tits, a nice ass and legs, short dyed black hair, blue eyes, dimples and a very cute deceivingly innocent looking face. She was a year younger and I’d met her through friends and despite her innocent looks I’d heard some rumors but she was still fun and flirty and i had a bit of a thing for her so we started hanging out more. I was definitely into her but at that point in time, I’d never done the casual sex thing so  I pursued her as a girlfriend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We’d gone on a few group dates with friends and I figured I’d ask her out on an actual one on one date, so I did and she happily accepted, however, she was going to stay at her dad’s for the weekend and he was kind of overprotective and against her going on dates, but she suggested I could take her out during the day and she’d just say I was a friend and we were going swimming and her dad lived out in the country and it would only be a short drive into the mountains with plenty of lakes to choose from.

Saturday rolled around and as we planned I drove out to her dads place to pick her up, when I got there it was hard for me not to drool, she had on the tiniest cut off jeans I’d ever seen, you couldn’t really call them shorts, and a little tank top that left her mid section exposed and a bikini top under that, we loaded up some stuff as her dad gave me a mini interrogation, but she brushed him off and we left and headed for the mountains, the first couple lakes we stopped at had people at them and she insisted we move on to one with fewer people, the third lake we came to was a little more secluded and there wasn’t another person to be found, we pulled up to the beach unloaded, got a fire going laid out some towels then went for a swim, we spent a while in the water messing around then she got out and laid out on one of the beach towels, I went and laid next to her and we chatted a bit, then I started to poke and tickle her and a little horseplay ensued she got on top of me as if she was pinning me down and that’s when she leaned in and gave me a kiss, she sat up and giggled with that cute innocent smile on her face, then as we’re staring at each other she reaches down and starts rubbing my crotch, I took a surprised breath and blurted out “wow, uhh what are you doing?” she giggled again and asks “What does it look like I’m doing silly? I’m getting your dick hard ” I was speechless as she continued to rub my rapidly swelling cock then she says “Why do you think I wanted a beach all to ourselves? couldn’t exactly fuck you with an audience” I was at a complete loss for words and all I could focus on was her hand rubbing my cock through my shorts, she leaned in and gave me another kiss then asked “well you going to fuck me or what?” the only response I could muster up was “I don’t think I’ve any condoms” she just smiled and said “That fine, I’m on the pill” I was still blown away by the whole situation and just unable to come up with words, she was obviously horny as fuck and getting antsy so she says “Well I’m gonna give you a blowjob while you think about it”

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? She slid down towards my feet and gave my shorts a tug, as she did my erection sprung out and suddenly that giggly look on her face turned to complete shock followed by excitement and she blurts out “Oh. My. God. That’s the biggest dick I’ve seen in person”, now I’d heard that before but it was usually followed by concern, but this chick was like a kid at Christmas, she gave it a feel, grasped it in her hand and giggled as she said “Holy shit, i can’t even get my hand around it” , Then she leaned forward and started sucking, I’d never felt something so amazing as she struggled to take more, her head bobbed up and down as she slurped and drooled all over it, she kept at it for almost 10 minutes without coming up for air, when I felt it building I warned her I was close but she ignored me and just kept at it, her hand stroked in sync with her bobbing head, I frantically warned her again but it was too late, I erupted in her mouth so hard my hips thrust upward but she didn’t miss a beat as my toes curled, I grunted and groaned and convulsed uncontrollably as she sucked the cum out of me, I finally settled and she came up with an obvious mouthful but without hesitation she took a big gulp and it was gone. She smiles at me and I couldn’t believe this cute innocent looking chick had just given me the most mind-blowing blowjob of my life, she bites her lip and says “So you wanna fuck me?” , I gave her a big smile and a nod as she jumped up with excitement, pulled the string on her bikini top then spun around and peeled her wet jean shorts off in a very sexy little striptease, she straddled me and gave my rapidly recovering erection a few tugs, leaned forward then sat back as I felt my tip spread her wet lips, then with a little pressure I slipped in, she was incredibly tight, wet and hot, we both let out moans of pleasure as I stretched her out and filled her, all I could think was thank god she gave me a blowjob first cause her pussy felt like the best thing ever and I would have blown my load in seconds otherwise. She rode me cowgirl for a while and had now issues getting herself off, her cum was dripping down my balls and she had a permanent smile across her face, the only problem was every time I’d start to get close she’d have an orgasm and have to stop and catch her breath, i finally told her to hop off cause i wanted to fuck her doggy style, she happily assumed the position and i took her from behind, i began fucking her and she quickly matched my thrusts, she was taking it hard and deep and loved every inch, finally i was getting close and I’d be able to finish, the closer i got the faster and harder i went until she couldn’t keep pace any more and put her head down and just took it, she was getting wetter and more tense i knew she was close but i was gonna finish this time, then it hit like a freight train, i hammered a few more deep hard thrusts into her and let out a long deep groan and began to unload inside her as her orgasm hit, it was the hottest most animalistic thing I’d ever felt, I’d never cum inside a woman before and it felt amazing, after a few minute i pulled out and my thick gooey white cum spilled out of her tight little pink pussy and down her thighs, we laid there naked for a while catching our breathe before packing up and driving her back to her dads place.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? I was ecstatic but at the same time unsure what to think, it was my first casual sex experience and I knew it was risky without the condom but it was incredibly hot. We met up later that week and she said she wasn’t really looking for a boyfriend but if I was interested she definitely wanted to continue fucking, I was ok with that and we kept at it for a while until she got a boyfriend, she eventually started cheating on him with me but we eventually parted ways after I ran into her at a party we hooked up then I found out after I left she fucked four more guys and when I asked she lied about it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), 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? 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? 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? a few buddies

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? A little bit

Why do you regret this hookup? unprotected sex, despite her deceivingly innocent appearance she’d fucked a lot of guys.

What was the BEST thing about this hookup? first casual sex, first creampie, wild sex

What was the WORST thing about this hookup? unprotected sex and I wasn’t the only one fucking her, luckily I never caught anything.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? opened my eyes to casual sex and the fact sex doesn’t have to be tied to a relationship

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!