by

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Seattle
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Photographer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 4

Helping Out A Friend In Need

How long ago did this hookup happen? 11 years ago

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? My best friend from college: a thin, medium-short, petite woman with short brown hair and freckles. Her style was the hybrid of nerd and punk that so many of us were at that age: glasses with thick black rims, leather jacket with patches from favorite punk bands, skinny jeans with a Nintendo-controller belt buckle, Chucks. She was cute, and had a nice figure, but I didn’t think too much about that, since she was my best friend: I knew nothing was going to happen between us, and I didn’t want anything to, since I was totally content with the friendship and didn’t want to risk messing it up. Besides, I knew from past experience that getting sexually involved with a friend can lead to pretty awful drama. But all the same, I had noticed her cuteness, and I harbored the guilty secret that there were a few times when I had thought about her while masturbating (if more out of curiosity about what it would be like than actually wanting to be more than friends). I did honestly feel guilty for having done so: she was my best friend, and I generally didn’t think of her in a sexual way at all, to the point that I was even a bit surprised on those occasions when I was jerking off and thoughts of her crept into my head. Our friendship was quite strictly platonic: we’d talk to each other about our dating and sexual adventures with other people, both when we wanted to share something really exciting that had happened, and when we needed to vent when things weren’t going well. But during one part of Junior year, we both had a serious dry spell in the sex department. We were both pretty frustrated, and as we did with everything else, we talked to each other about it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were sitting in her apartment one night, playing Playstation and eating pizza and drinking beer as we so often did, and as so often happened, the topic of our frustrated love lives came up. We had both recently asked other people out, and in both our cases it hadn’t panned out. She mentioned how it wasn’t even the having a boyfriend that she missed, but she was getting crazy sexually frustrated since it had been so long since she’d gotten laid. I know the feeling, I told her – it had been quite some time for me too. She semi-sarcastically made a crack about how much she’d been masturbating lately. Again, I told her me too: “haha, if I’m honest, I definitely jacked off before I came over here tonight.” She laughed: “so did I! Ugh, it definitely didn’t scratch the itch, tho. I just need a guy to fucking eat me.”

To the casual observer, this may sound like a come-on, but it wasn’t; we were just totally comfortable around each other, and we both knew we could talk bluntly like this and it was safe. But maybe it was that we’d just had a couple beers and it loosened us up, or maybe it was just because we really needed a helping hand and it made us wonder about the possibilities, but tonight was a bit different. “Fuck this is frustrating,” she said. There was a moment of semi-awkward silence as she took a swig of her beer. Then she kinda timidly said, “Hey, so, this may be a super awkward question, but… we’re both really comfortable with each other, yeah? And we’re both clearly pretty horny… do you think it would awkward if we… maybe tried to help each other out with that? I mean, would you want to? Or would that be weird?” I had not expected such a proposition to come from her, and for a moment I was just silent as I looked at her and tried to gauge if she was serious. “You’d want to?” I asked. She responded: “Sure… I mean, to be clear, I don’t think of you romantically – I definitely just want to stay friends… but physically you’re definitely good-looking enough that I think I could fool around with you, and I definitely trust you.” That was a pretty nice compliment to hear, in an unusual way “I think I feel the same way… you don’t think it would be awkward, though, or strain the friendship? I definitely don’t want to mess this up…” She said, “I think I could do it without it getting awkward… let’s just be on the same page – no romantic feelings, just friends helping each other out, and we keep talking about how we feel about it, and where we want to draw boundaries?” I told her it was a deal. “Good,” she said, “because I really need something that isn’t battery operated for a change!”

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? Things started a little awkwardly from there: I think neither of us was sure how we should get things started, sparking a friendly hookup without romantic feelings involved. I asked her how she thought it should work – does making out cross the boundary of just-friends that we had just agreed to? She laughed: “I don’t know, maybe this won’t work… let’s just try it and see what feels good.” We both tentatively leaned in for a kiss, and at first, it felt a bit awkward since we’d been strictly platonic friends for so long. But pretty soon we got into a good rhythm and started deeply kissing in a way that felt really good. We put our arms around each other and pulled each other close on the couch. Then I started massaging her body, which inspired a happy “oooooh” from her – “Yeah, I think this is going to work after all,” she said. “I definitely think so!” I told her in return, and moved my hands towards her breasts, over her shirt. She let out a small moan when I started massaging them – and wow, they felt really good in my hands, small but very soft and nice. She reaches down and takes hold of my penis through my pants – I’m getting pretty hard. “Wow, it’s been way too long since I got one of those into my hands,” she says, “kinda makes me wish I’d suggested this sooner!” “Me too!” I say, and I let one of my hands slide down the front of her body in a similar fashion, and rub her crotch through her jeans. “ooooh,” she says, and arches her crotch forward to rub it there. “Shall we take it to the bedroom?” she asks.

We’re still both trying to figure out exactly how this works: we’d both had casual sex with people we’d just met and been attracted to, and my other (former) good friend whom I’d slept with I had actually fallen a bit in love with first, and the sex followed. Deciding to have some friendly, just-for-the-hell-of-it sex with a hitherto-platonic friend, based more on need and horniness than significant attraction per se, was new, and we were still feeling out what worked or was awkward. As we stood in her room, I asked her what she wanted us to do, and what would feel good without being awkward. “Well, like I said before, I really do need my pussy eaten!” “I would love to eat your pussy,” I tell her. She smiled and started undoing her belt and pants. She dropped them to the floor, and all of a sudden I was looking at my best friend’s vagina: trimmed, but fuzzy with her brunette bush. I had never looked at her in this way before, but damn her legs and bush and vulva were beautiful – and I loved the idea that she had invited me to put my mouth on them. She started idly, and kind of nervously, rubbing her clit, still standing in front of her bed. “You’re sure you’re alright with this, and it’s not awkward?” “I am more than alright with this,” I answered, gesturing to the decidedly obvious boner in my pants, “I don’t feel too awkward, do you?” “No,” she said with a smile, “a little nervous, but really happy to have some help with this!” I thought that I should tell her something that I’d been hitherto keeping secret: “I’ve gotta admit… there have been a few times when I’ve wondered what this would be like.” She smiled, “me too, honestly.”

We quickly remove the rest of our clothes and get onto her bed. She looks great nude. She reaches out and strokes my dick once it’s out of my pants. “Ooooooh, nice – definitely a welcome change from my vibrator.” We kiss again – it definitely isn’t awkward anymore. As we kiss, she’s rubbing my dick, and I’m stroking her labia and clit. She’s getting pretty wet. Then I do as she asked, and start kissing down her body towards her crotch, showing her breasts quite a bit of attention along the way. “Please tell me exactly what you like, or what I should do differently,” I told her, “I still want us to be able to talk about anything – just like always.” She smiles, relieved that our agreement seems to be working great. “Ok! Get down there and I’ll tell you how I like it.” And with that, I I lower myself down and start pleasuring my best friend. Her bush feels great against my face, and she tastes and smells delicious. I really love giving cunnilingus (or oral sex period, for that matter), and since I haven’t in so long, I really savor the moment and try to make it extra great for her, showing her clit, labia, and the opening of her vagina plenty of attention. She occasionally gives me some directions on what feels the best – primarily telling me when to move back and forth between licking her clit and tonguing the opening of her vagina. “Ooooh, yeah, this is exactly what I needed,” she tells me. She reaches down with both hands and puts them on the back of my head, holding my face close to her crotch as I lick and kiss her clit. “Use your fingers too!” She tells me. I start fingering her as I continue to lick. Her vagina is tight, and the muscles are twitching with pleasure. “You’re gonna make me come!” She says – “go faster!” I lick faster, and speed up the pace of my fingers. Her grip on the back of my head tightens. “Fuck!” I feel her start to come around my fingers – a hard, long orgasm that definitely feels like the feeling of relief after not getting laid for way too long.

Her orgasm done, she relaxed onto the bed, “fuck this was a good idea,” she said. But she soon made it clear that she wasn’t done yet. I got up next to her, and she rolled over to face me. We kissed, deeply, and our hands were all over each other once again. Her hand went to my still-hard penis. “Do you want to?” She said, “because I really want to.” “Absolutely!” was my response. With that, she got up and went to her dresser to get a condom. She comes back with one, kneels on the bed above me, strokes me a little to make sure I’m fully hard, and rolls it on. “I like being on top, especially the first time with a new partner – is that ok?” she says. Of course it is! She straddles me, takes my dick in her hand, and slides herself down around me. She had mentioned a couple times in her boastings about her sexual adventures that she had a really tight vagina, but now feeling it for myself… holy crap, she wasn’t kidding. It feels so good: on those occasions when I had imagined what this might be like, I hadn’t imagined it this good. “Oh fuck, you’re a good friend!” I tell her. She laughs – “same to you!” She leans down and kisses me, then arches her back up so I can kiss her breasts. She is totally in charge – setting the pace, controlling the movement, making very sure she’s getting what she needs – which is exactly what I need too. Eventually, she reaches her hand down and starts rubbing her clit. “I’m getting really close!” she tells me. “Are you?” “Oh yeah…” I tell her. “I’m definitely going to come when you do!” With this, she picks up the pace, and it doesn’t take long before she rubs out an orgasm, and screams with pleasure as she starts to come. As I feel her muscles clench against me with her orgasm, I come too, filling the condom inside her with the most intense orgasm I’ve had in months. Once our orgasms are spent, she collapses on top of me. She smiles – “thanks for helping out a friend in need!” We both laugh, and kiss.

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 laid in bed and talked – about how it was, what we might do differently next time, and above all, how we felt about it, and our friendship. We both remained firm on the point that we didn’t want the sex to screw up our friendship, and the communication and honesty about what we both wanted and needed definitely helped with that. After a while, as we started to get tired, we agreed that I should go home – spending the night seemed a little too much like a relationship thing.

Ultimately, it worked – our good communication about everything allowed us to stay best friends without it hurting our friendship or creating any awkwardness, while still having some friendly sex every week or two. It’s somewhat ironic that both of the times I actively tried to have a friends-with-benefits arrangement, it went quite badly, and drama and unreciprocated feelings ensued, but this time when sex just kind of happened into an already solid friendship, it actually worked out very well. Eventually, when one of us got into a relationship, we went back to being platonic friends, but for much of those last two years of college, being able to sleep together when we wanted/needed to really helped each other out, and lead to some amazing sex as well.

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, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? No one – we kept it a secret just between the two of us.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Fun, friendly, really good sex with my best friend, which wound up being a situation we both really needed!

What was the WORST thing about this hookup? That we didn’t think to do it sooner!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? After a couple bad experiences with past partners, trying to do the whole FWB-thing and having it backfire when I got romantically invested and then got hurt, this was the first time that an arrangement like this really worked – I think because it kind of just happened organically. It only worked because she and I had an open, strongly-communicating friendship that allowed it to work, though, so I know it wouldn’t work for everyone, but I’m glad I finally got an experience that proved to me that it definitely can work with no ill effects to the friendship.

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

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

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 think in the right circumstances – with the right partner with whom good communication, trust, and a lack of jealousy are all present – it can be a great thing, and certainly something people should be free to explore without judgment.

What do you think about the Casual Sex Project? I love it – it is a wonderful place to share these experiences that I wouldn’t feel comfortable sharing in a non-anonymous setting, for the privacy of all involved, and it’s also great to read about other people’s experiences. It’s a great way to expand our understanding of casual sex experiences, and have some fun in the process!

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

Comments