My Roommate’s Boyfriend

by Audrey

What’s your gender? Woman
How old are you? 27
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? Plenty
How many hookup stories have you here posted before? 3

My Roommate’s Boyfriend

How long ago did this hookup happen? 8 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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 freshman roommate Claire was a sexy curvy blonde with fair skin and blue eyes. Her ass and breasts were amazing. I secretly wanted her so badly. Her boyfriend Kevin was on the football team and was solid muscle and very sexy and hung. He had sandy blonde hair and blue eyes. I’m a petite lean brunette with a dancers body. My legs are long and toned and my ass is cute and my breasts are very small but very perky.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It wasn’t uncommon for them to fuck when I was asleep or when they thought I was asleep. Often I peeked from under my comforter, watching two gorgeous people make love. I would have done anything to join them but was shy. Sometimes I would softly rub my clit as they fucked. The night it happened seemed normal enough. I woke up to them giggling and kissing. I closed my eyes and tried to go back to sleep but was intrigued. I rolled over pretending to still be asleep and peeked to see him on his back and she was hungrily sucking his large cock. After a few minutes, they switched and he began licking her. She loved it as his tongue probed her. I was so turned on that I began to slowly finger myself. Her pale curvy body looked amazing in the moonlight and I could see the soft fluffy tuft of blond pussy hair as his head was buried between her luscious thighs. She then climbed up and slid his cock into her. He looked to be a thick eight inches and she clearly loved it covering her mouth as she moaned. They switched positions and she was riding him. I slid my panties to my knees and had two fingers in me and began to cum I stayed as still as I could and my orgasm kicked. Soon they were cumming together. She collapsed on top of him and I fell asleep as they kissed. I awoke a short time later to them talking. He was asking to go again but she made it clear she just wanted to sleep. He begged but she had none of it and I drifted back to sleep…

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? I don’t know how long I was out for but I awoke to something pressing against my pussy. I had never pulled my panties back up, making it easier to be entered. Kevin was on top of me and pushing his big dick into me. I didn’t know what to say or do. I knew what was happening was wrong on so many levels but I knew I wasn’t strong enough to push him off and I knew he wouldn’t take no for an answer and I also knew I wanted him so badly. “What are you doing?” I whispered.
“I know you want this Audrey.” He said. Knowing I did. “I know you saw me and Claire.”
He was having a hard time entering my tiny pussy so I reluctantly spread my legs and he was able to slide into my tight hole. He traced his finger down my thin landing strip until he was gently rubbing my clit as his big cock slowly fucked me. I looked over at Claire, she was sound asleep facing away from us. Kevin’s cock felt so good as he picked up the pace a little. Then he began kissing me and I could taste Claire’s sweet pussy on his lips. Soon I began to cum, it was so intense. Then he rolled me over and I lay on my belly as he fucked me from behind. He pushed his thumb into my ass prompting my second orgasm. We went back to missionary and when he was ready to cum I wrapped my legs around him and we came together. He spilled his seed into me, gave me a soft kiss and climbed back into bed with Claire. I was asleep within minutes.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? It never happened again and Claire never knew. I witnessed the two of them a few more times and I think Kevin knew I was watching. I would have loved to have a threesome but it never happened. Nothing was awkward and I soon started dating a guy.

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), Submission / Relinquishing power

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? Very

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? No one

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? I loved watching a beautiful couple have sex and then for him to just take me was so sexy. I was a little reluctant but I wanted it too. His cock was so good.

What was the WORST thing about this hookup? I wanted Claire too but never got to be with her.

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 love sex, plain and simple.

What do you think about the Casual Sex Project? I love it I can’t wait to write more. There should be comments I would love to know what people think.

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