Finally With My Roommate



What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: High school diploma
What’s your occupation? Writer
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? Insatiable
How many sexual partners have you had in your life (including oral sex)? 35
How many hookup stories have you here posted before? Several

Finally With My Roommate

How long ago did this hookup happen? 2003/4

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? She was a female roommate of mine. We’d known each other for several years before moving in together. She had blonde hair, a slightly larger build, or “thick” would be a good descriptor. I’d caught hell from some co-workers that said it was only a matter of time until we hooked up. While I agreed with the sentiment of inevitability, I wasn’t trying to make anything happen.

She was a late sexual bloomer, several years older but a few years behind me in many ways.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had come home earlier that day absolutely aglow. This guy she had been seeing finally took her virginity, and she saw the world through new eyes. She didn’t go into much detail, and I didn’t pry except to make sure she was ok with things, and it was a safe experience. But, chatting with my female roommate about her getting laid definitely had me with sex on the mind for the rest of the day.

That night, I went out drinking with some friends, and my roomie stayed home. One of our mutual friends kept trying to set me up with this girl I was super into, but I struck out. With a belly full of alcohol, I found my way home, expecting to be the only one awake. Nope, I had late night company! I had a story to tell about my attempts and failures of the night, but she wanted to go to bed. “Hey,” I suggested, “why don’t you just come lay down in my bed, and we’ll talk for a while?” This had happened before, no big deal, so she made her way to mine.

So I’m regaling her with my tale of horniness and tragedy, and she makes mention about how she misses just being cuddled. This was new territory, mind you. We’d hugged before, no big deal, but cuddling? Eh, what the hell. So, she rolled over, and we started to settle into a spooning position. Well, my wrist grazed her breast, and I was surprised by the sudden appearance of a rock-hard nipple. I didn’t react, but she gasped slightly, causing my loins to stir.

Her hair smelled nice, and the skin of her neck was so soft, and I kept thinking about that nipple and my swelling penis. I adjusted myself behind her slightly, and accidentally brushed her breast with my arm again. This got a slight moan, and she started to softly grind her ass against my hardening penis.

Finally, I just went for it and took both of her breasts in my hands. She abruptly thrust back into me. “Is this okay,” I asked, and she gave an exhaled “yessssss.”

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? So I’m in my boxers, with a hard dick straining against the fabric and a river of pre-cum soaking through. With a mind of its own, and aided by her body movements, it freed itself from the fly of my boxers and began worming its way between her legs.

Before we knew it, she had my tip inside her. We both froze. Slowly, as if she was about to change her mind if I went too fast, I started to push into her, and she started to push back. Slowly, inch by inch, I sank into her wetness until my balls rested against her ass and I bottomed out inside of her.

Again, we froze for a moment, and then she spoke up. “I want you to fuck me,” she said. Hearing those words, my dick wanted to spray her insides with all the cum I could muster. I don’t need to get my roommate pregnant, though.

“We’ll need a condom then, yeah?” We uncoupled; she rolled onto her back, as I quickly found a condom in the bedside table and rolled it on. I easily slid into her in missionary, and she reached down to feel me going into her soaked vagina.

I started slow, wanting to make this experience last. Next thing I know, we’re fucking, and not being coy about it. She was a little loose, and incredibly wet, so I kept giving her my entire length with each thrust while I paw at her nipples. She pulls me down, and we start kissing for the first time, and it’s super aggressive. This is enough to put me close to the edge.

“I’m about to cum,” I announce.

“Yes, yes, yes,” she says with every thrust. Finally, I go in as deep as I can and fill the condom up while we kiss. I carefully remove myself from her and go into the bathroom to tidy up.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? This was the first time, but not the last time we fucked. Experiences usually started the same, innocent drunken cuddling turning into more. We honed our oral skills on each other some nights. It was just so damn convenient: if we went out on dates, but things didn’t work out, and we’re still all hot and bothered? Let’s bang it out real quick!

It all wrapped up when each of us got serious about people we were seeing.

Best part? None of our friends ever knew! She was a bridesmaid in my wedding several years later, but not even my wife knew we used to fuck.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

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

How intoxicated were you? A little tipsy/high

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? Just 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? The sheer electricity of feeling that nipple harden.

What was the WORST thing about this hookup? Nothing, really.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I had thought the roommate boundary was set in stone. When that fell, it made me look at other similar situations in my life, and suddenly the world was open to me.

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? As long as two adults communicate their needs, I’m good with it.

What do you think about the Casual Sex Project? Big fan for some time!

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