Exceeding Expectations

by Pinch of Something

What’s your gender? Man
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Portugal
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Gainfully Employed
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
Any other term(s) that describe your sexuality or sexual identity? Adventurous and Intense
How many sexual partners have you had in your life (including oral sex)? 15+
How many hookup stories have you here posted before? 0

Exceeding Expectations

How long ago did this hookup happen? Summer of 2008

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 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? Lynne (not her real name) was a girl that I met through a mutual friend. He brought her to a house party I had organized. They were together at the time, but I was instantly and insanely attracted to her. She was Asian, had long wavy black hair, was about five foot six with amazing curves and the cheekiest smile I had ever seen. I spent about 90% of the party talking to my friend, just so I could be close to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My friend was a bit of a player and I found out that he and Lynne had ended their fling about a week after the house party. I waited maybe a day after finding out before I invited her to hang out at the beach. When I turned up at the beach Lynne was already there, but without a towel. She assumed we were simply having coffee at one of the cafés at the beach-side. I suggested we simply share my towel, to which she agreed. We laid next to each other for a couple of hours just talking before I decided to make a move and kiss her. We spent the rest of the afternoon just making out on the beach, and it is one of my fondest memories. We ended up going to our respective homes that day, as we both had commitments we couldn’t back out of.

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 that day at the beach we began talking constantly either through MSN Messenger or simply texting, getting to know each other better, sharing likes and dislikes, and with the occasional light sexting. The next time we met was at my place. I told her I would love to give her a full body massage and she readily agreed. She had told me she loved sangria so I prepared some just before she arrived so we could have something to loosen up. She arrived wearing a short summer blouse and skin tight jeans that showcased her sexy legs, and I had to control myself. It was hard not to grab her and take her on the couch. She loved the sangria and complimented my skills, which I used as an opening to move onto the massage. I took her to my room and asked her to undress and lie on the bed while I fetched the oil I’d forgot in the bathroom. I got back up expecting to find her with her bra and jeans on, and was dumbstruck at the sight of her. She was laying naked on my bed with nothing on but a black thong. I started with her upper back and made my way slowly to her was, taking my time to knead her buttocks before moving onto her upper thighs and the down to her feet. I then spent about ten minutes gliding my hands all the way up her legs, using both of my thumbs to lightly brush her mound just before gliding back down again. It didn’t take long before she began thrusting her hips back each time in anticipation. I pressed my thumbs a bit deeper on the last go and asked her to turn around, at which point her eyes locked with mine and begged me to take her. I had dressed down to my boxers by this time and there was no hiding my erection. I chose to prolong the tease a bit further and finish the massage. I decided to spice things up however, and knelt on the mattress in between her legs, with each of her thighs resting on mine. I told her she was not allowed to move her arms or legs, no matter what happened, and began gliding my hands from her knees up her body, leaning my body forward and grinding my dick against her mound. My hands reached and squeezed her breasts. I held myself in that position for a few seconds, never breaking eye contact, and brought my lips half an inch from hers and pulled back before she could kiss me. I did this a few times before I finally gave in and kissed her, letting my body fall onto hers. Her arms and legs wrapped around me and we kissed and humped each other for a few minutes. She was so wet by this stage that her thong had soaked through and wet my boxers too. Before we could take things any further, her phone began to ring, and she had to take the call. When she came back into the room, she sat on the edge of the bed and started stroking me through my boxers, saying she had loved the massage and wanted to know if I’d like to have one too. I said I’d be very happy if she could give me an upper body massage, since my chest and arms were sore from all the work earlier. She agreed but as she got up to fetch the oil, I grabbed her waist and pulled her toward me until she was straddling me. I pulled her body onto mine and told her she had enough oil for both of us. She smiled and began rubbing her breasts against my chest and her panty-covered mound against my dick. At this point I decided I’d had enough foreplay and pulled my boxers down as much as I could in that position. She stopped as soon as she felt my penis against her navel, lifted her chest off mine and reached for my dick with one of her hands. As it closed around me she bit her lip and said “I promised myself we wouldn’t have sex today…”. I didn’t say anything and felt her rub my head against her clit. She then said “…but after everything today, there’s no way I can’t!” and pushed her thong to the side slid me into her. It was the second time I’d been inside a girl without a condom and it felt like heaven. She rode me very slow at first, accommodating herself to my size, and I eventually told her we had to get a condom on, because she wasn’t on the pill. We got off the bed, took our underwear off, put a condom on and got back onto the bed all in less
than a minute. We started with missionary and I didn’t last long, possibly on account of all the teasing, but after a ten minute break we were back at it. We spent whole afternoon fucking each other senseless and I can honestly say it was the best sex I had had up to that point in my life. She couldn’t spend the night, so toward the end of the afternoon we had one last go in my apartment’s walk-in shower. It became a favorite of ours and we used it every time she came over after that.

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? We became friends with benefits and had an incredibly intense summer together. Unfortunately I traveled to study abroad in the Fall and we lost touch after that.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection

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? My best friend, he was happy for me.

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

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The intimacy, the fun and learning and exploring about sexuality with some I truly liked

What was the WORST thing about this hookup? Ending It. Had I not traveled to study abroad we may have made it into a serious relationship – I think we both wanted that but knew it wouldn’t be possible at long distance.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general?  It did, made me aware of how much fun and intimacy can be had with the right partner, and definitely made me a better lover.

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? I believe it’s a necessary experience everyone should have. It’s liberating and teaches you a lot about yourself that you might otherwise not learn about.

What do you think about the Casual Sex Project? It’s awesome, keep it up!

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