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What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Sales
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Very interested
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? 0

Facebook Reconnection I Never Expected

How long ago did this hookup happen? 4 years

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For 1 to 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? I knew Holly (not her real name) from when we were both shy awkward teenages involved in youth groups together. I barely paid any attention to her back then, and knew honestly nothing more than her name, and that she was a few years younger than me. About 4 – 5 years after we had last seen each other we reconnected on Facebook. I of course knew who she was by the name and the mutual friends that we had, but not really from her photos. While this wasn’t necessarily a case of the ugly duckling turned stunning princess, she had definitely matured into an attractive woman with shoulder length blonde hair, a gorgeous set of eyes covered by a nerdy, but adorably sexy pair of glasses. She was about 40 cm shorter than me, and had a tight dancer’s body, with smooth pale skin. After reconnecting, I didn’t really think anything of it, as many young adults could attest merely being Facebook friends doesn’t imply anything further.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? But after seeing that she had turned into a very cute pretty young woman, I decided I wasn’t going to let the opportunity pass.  I was going to write her, and who knows – see what could happen. I didn’t even have to: by the time I had let a few days pass she had already written me, with a subtly worded, “Remember Me?”  Five days later we were arranging to catch up for drinks…. and more. Meeting out at a cocktail bar in the city, we wasted no time getting reacquainted, and I had a really nice time hearing about what she had been up to, her hopes and goals, her university, etc.  She also seemed genuinely interested in my life. She was looking gorgeous in a tight fitted pair of light blue jeans and a loose, flowing singlet top. Gradually we started flirting, and after only a couple of cocktails were making out intensely in the bar. She told me with a whisper that it was time to go, and we walked out to my car. On the ride home, we were laughing a lot, touching each other when we could and hooking up at every set of red lights – until we broached the subject of politics, with the knowledge that both of us were interested in this topic.  We were speaking on one specific issue that she seemed to take offense at my opinion of, and this led to a rising intensity in conversation.  During this time I slipped my finger down the front of her jeans and started to rub her already wet pussy while she insisted that her opinion was right, and mine wasn’t.

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? After we got back to my place, I led her into my room, asked her if she wanted a glass of water or another drink, and proceeded into the kitchen to bring us two gin and tonics with a couple of glasses of water, thinking that maybe after the discussion in the car I’d need to warm her up to it again. Walking back in the room, I saw that she was naked except for a matching bright pink G-string and bra set; she took the drinks from me, took a big gulp from hers, turned around and sprang onto me, where I caught her she wrapped her legs around me, and started kissing me deeply.
After holding her for as long as possible, I put her back on the ground and she started to strip my clothes off me.  When she got to my cock, she gobbled it straight down as soon as it popped out of my briefs. Here I was with this girl I had known since she was a shy teenager, on her knees sucking my cock while she stared up into my eyes. After I had enough of that I put her on the bed and dragged her G-string slowly down, exposing her beautifully pink, glistening, trimmed pussy. Licking up the inside of her legs I dove down into her delicious pussy and spent a good ten minutes licking away while she ran her hands through my hair and repeatedly said how she could’t believe I was licking her pussy after all these years.
After this, she pulls my head away and says she wants me inside her; without thinking or caring about protection at that stage, I put her on the edge of the bed so I could bring the head of my cock to her lips and pull her towards me. I slipped in, with nothing but warm wetness engulfing my cock, and proceeded to slowly fuck her – this was not what she wanted though as she started encouraging me to fuck her harder.
After five minutes of this, I turn her around and maneuver her into doggystyle, as from our conversations she had told me this was a sure fire way to get her to cum – and it didn’t take long, as I pushed her head down into the bed while fucking her, hard but slowly, gradually building up speed. I pulled her hair and moved her body up close to mine so I could bite and suck her neck while she got closer, until she had her loud and wondrous orgasm.
Needing a few minutes break we grabbed a drink, and decided to move the blankets and doonas to the floor. After a few minutes she moves down and starts to lick her juices off of my cock, taking me whole into her mouth. I tell her I want to take her to another orgasm in doggy and then cum all over her, so I get her into place again – just as I am about to enter, she asks about the sex toy, (another thing we had talked about, a nice sized vibrator that I have stashed away).  I go and retrieve it, and she asks me if I want to fuck her in the arse with it. This gets my cock almost as hard as it has ever been, and I proceed to fetch the lube also, and lube up my finger to play with her asshole before getting the sex toy.  It slides in easily, and I maneuver it so that its on my pubic bone and going in with every stroke of mine in her pussy. This sight has me instantly going crazy, and I manage to last a few minutes all the while she is moaning about how good it feels to be filled up in both her holes, and how I am her new fuck-buddy she will fuck whenever she or I wants it. At this, I decide to get her more into it, and I turn the vibrator on full blast.  I can feel it on my dick and in her pussy, and she starts going over the edge with a wail in an almost instant orgasm – and I follow, cumming deep inside her.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? After this, we laid around and talked a bit more, no more politics this time.  We started to organize the next month of sex dates that were going to work for both of us. She stayed the night and I drove her home in the morning, and we started a maybe month long affair of incredibly hot steamy sex. I slowly stopped contacting her, as I had a couple of other fires burning, and we had grown to become even more devisive on our various and very difficult political ideas. This led in the end to her coming over for sex, with virtually no conversation as we just satisfied each others carnal desires. We met up once a few months after the hot and heavy first month, and that was also nice, and I though that we may actually slip back into what we had previously.  However, in typical male style, I was chasing a couple of others then, and was craving the new and untried. A big mistake in the end, after finding that there weren’t too many out there like her….

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), It was easy / convenient

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? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? A few friends.

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? Turning the vibrator on inside her arse and watching her go over the edge.

What was the WORST thing about this hookup? Never actually fucking her in the arse, despite several invitations.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, I have always been of the opinion that it’s up to two consenting adults and they can do what they please.

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? I love reading the stories, and I am excited to read my own and have other people read it.

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

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