Fun Times With Co-Resident

by ifonly09

What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? Middle Eastern
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Dentist
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? None

Fun Times With Co-Resident

How long ago did this hookup happen? 4 years ago

What was your relationship status at the time? Single

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? D was 26 year old, middle-eastern, short brunette with curly black hair, a firm round ass and firm C cup breasts. I met her as part of a post-graduate medical training program as we were assigned to the same site during the year, but she had spent the first 3 months on rotation and so I did not see her much initially.
I had just moved to the city and broken up with a girlfriend of 4 years who I genuinely thought I would marry, so I was dating a lot of girls and hooking up occasionally, trying to feel better about myself.
When D finally made it to our common site, I was immediately drawn to her as we were both from the same ethnic background. She was always fun to be around and was smart and witty as we would engage in endless rounds of sarcastic banter, but I never thought much of it aside from the fact that this was pretty entertaining, especially because she was in a relationship with a boyfriend of 4 years and knew I was messing around with a lot of women.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I knew D loved her boyfriend, but she was by no means passionate about him (nor do I think she ever was or has become). She just thought he was a good person and felt like he truly cared for her and would do his best to make her happy, and she was not sure that she could find someone who would be as good to her as he was. D and I had become very friendly as time went by, and I could feel that her interest in me was a little more than platonic. I enjoyed our sarcastic bickering and would often initiate, and at times it became more intimate and sexual. One day after clinic, I had a date in the city but decided to drop by D’s place for a small drink before I met up with my tinderella. I sat next to her on the couch as she was sipping red wine from a tall glass and giggling at my horrible jokes. We would often talk about what it would be like if we hooked up but never acted on it, so that conversation came up again and in the middle of it, I attempted to kiss her. She initially resisted, feeling bad about cheating, but she finally succumbed. I flipped her over and made her sit on me, legs spread around my waist, as I moved my hands underneath her shirt, up her perky breast and unhooked her bra. She began to shake and hyperventilate but I could tell that she just wanted more, so we kept kissing for a few minutes as I was caressing her breasts and her back, but it did not go further right away as I was getting late for my date. I left her apartment with the mindset that I would return once I was done.

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? During the 2 or so hours that I spent away from her, D kept texting me trying to convince me not to return as she felt bad enough about what had happened already. But I was determined to come finish what I started and I knew she wanted it just as badly as I did. Once my date was finished, I returned to her place. She played a Neyo song on her radio as we laid on her bed and started getting undressed. I should mention that D was a virgin and wanted to stay that way until marriage. I got her completely naked and rubbed her inner thighs as I worked my way up to her clit. She was already extremely wet and came within minutes of me touching her. She gripped my dick and went down on me for a few minutes, taking it in as best she could. I did not cum, however, as it is pretty difficult for me to orgasm without penetration. I flipped her on her back and started kissing her breasts, stomach and worked my way down to her inviting wet lips. She moaned and caressed my hair as I licked and sucked her clit. She came 4 times that night, getting louder and shaking more every time. I could still hear her to this day. It was one of the most satisfying orgasms I had ever given up to that point. After we were done, we laid in bed for a few minutes and I caressed her breasts as she was on the phone talking to a friend of hers. I finally got up, got dressed, we kissed and I went home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? D and I hooked up again a second time a few days later. She came over to my place and spent the night. We still didn’t have penetrative sex but it was still awesome. D was very happy we got to be intimate together and did not regret it, but she felt terrible about cheating on her boyfriend. I have to say I did not feel great about it either, but rationalized it by thinking that the relationship was not going great anyway and I was probably doing her a favour by making her realize she should not be with him. She ended up telling him about our encounters, and he agreed to forgive her and try to work on their relationship. To be honest I did not think about being with D longterm, but I do wonder to this day what would have happened if we had tried. I ended up meeting a great girl and we’ve been dating for 3 years and are getting engaged next month. D and her boyfriend worked out their differences and got married a year after our escapade. She still texts me to this day from time to time to see how I am doing and get my news. Our conversations have turned sexual on a couple occasions and I do feel that if it weren’t for the immorality of adultery, that she would be interested in hooking up again. I feel the same way but we both would never want to ruin our current relationships, so we agreed to keep the conversations PG rated. She did however mention playfully that had I suggested we try anal, she would have been up for it, and I kicked myself in the head (and still do) for not doing so. You know those times when you think to yourself “If only”… Yeah, that was one of them…

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? I initially kept it to myself as I did not want to tarnish her reputation within the training program, but I told my now girlfriend (who met D a few months after we had hooked up) as well as another male co-resident of ours. My girlfriend actually liked D and did not mind hearing this story since she was not in the picture when all of this happened, but was very disappointed in me for having jeopardized D’s relationship.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The build up, the naughty texting and sarcastic banter. She had a great body underneath her clothes and she was short enough that I could flip her in every which way I pleased and she loved it.

What was the WORST thing about this hookup? The guilt from being the cause of a potential break up and making her cheat on her boyfriend.
The disappointment of knowing we could have had anal sex but didn’t because I was stupid not to suggest it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. I believe casual sex is ok as long as both parties understand and know that it is meant to be casual. It stops being ok if one person is aiming for the long haul and the other just wants a quickie.

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

All things considered, how NEGATIVE was this experience? A little 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? It taught me what I like and don’t like and made me appreciate sex with someone I cared about deeply. Not to be corny or anything, but to me sex feels a lot better and more satisfying when done with someone I have feelings for rather than a random hookup.
I was not in love with D (and neither was she) but having known her for a while made it a lot more satisfying.

What do you think about the Casual Sex Project? It’s a great way of sharing stories, although having read a lot of them, I do feel that many are made up/too porn-like, or even people’s repressed fantasies. I am however shocked at the number of adulterers who do not feel any shame or regret for having erred on the wrong side of the highway.

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