Sleeping Giant

by Tom

What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? England
Highest education received: College degree (eg., BA, BS)
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? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 28
How many hookup stories have you here posted before? 0

Sleeping Giant

How long ago did this hookup happen? 4 years

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

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? She was my girlfriend’s roomate. A trainee doctor, 24 years old, with thick, long black hair, a pretty face, she was thin but with big tits. We got on well and I always fancied her and fantasised about what it would be like to be with her. Her room was next to my girlfriend’s and I occasionally heard her having sex, which turned me on so much.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My girlfriend is a keen gym goer and she used to get up early before work and go. I had a plan to leave our bedroom door open slightly, with the covers off me while I ‘slept’ naked after my girlfriend had left. The floor in the hallway was wood and fairly noisy so I could hear (I’ll call the roommate J) slow down and sometimes stop to look at me as I ‘slept’. Things started to change between us. She was being much more flirty with me I used to catch her looking at me. One night when there were a few of us out for drinks, she mentioned to me how she’d seen me naked while I slept. I pretended to act shocked and embarrassed, but I loved the compliments she was giving me.

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? One of these mornings when my girlfriend was at the gym, I heard ‘J’ come into our room and before I knew it her mouth was around my cock. At this point I was past pretending to be shocked. We both knew we wanted it, so I let it happen. She gave such good head and it felt so naughty to cheat, which is something I’ve never done before. She kept complimenting me about the size of my cock, saying she’d never had one that big then she stripped naked and sat on my face so I could lick her. She looked better naked than I even imagined. She had perfect, big natural tits and a deceptively good arse. Her pussy was also a thing of beauty. She tasted and smelt so good. She knew what she liked and she wasn’t afraid to do it, which I loved. She ground on my face while I reached up to play with her unbelievable tits. I couldn’t take it anymore and I bent her over and fucked her. She came after about 1 minute. I carried on fucking her, whilst I fingered her arse. She came again & I didn’t last much longer because she felt so good! After a few minutes, she was back sucking me off and we were ready for round 2.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? There was no awkwardness between us, and we carried on hooking up even after she got a boyfriend. Eventually she moved out and that’s when it stopped. She’s married with a child now.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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 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? I never told anyone.

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

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? A little bit

Why do you regret this hookup? I felt guilty about cheating.

What was the BEST thing about this hookup? The sex was incredible! I’ve never experienced sex with such a perfect woman before.

What was the WORST thing about this hookup? The guilt.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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? We’re all animals and we’re not meant to be monogamous. If life presents you with opportunities you should take them.

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