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What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? Idaho
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Artist/musician
What’s your current relationship status? Single
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 0

I Was a Younger Co-Worker’s Side Fling

How long ago did this hookup happen? 10

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 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 short. Latina with short hair. Wore glasses which I really like. A nose piercing and small gauges in her ears. A bit of a mid west hipster girl next door type. Small perky breasts. Very shapely legs and a nice firm butt. She was 18 the first time we hooked up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We worked together. I was a department manager and she was a sales associate. I was one of the three guys that worked there out of about 35 women. I was one of the younger mangers and probably the more easygoing managers that worked there due to my age and my fun attitude toward things. We recently found out we lived three doors down from each other which led to a friendship and small playful flirting. I didn’t think much of it because I’m a natural flirt. We would text often and she would come to me about her boyfriend problems. At this point never thought anything would happen because I was her boss and I was older then her. The hookup started one late night around midnight. I got a text from here complaining about how her boyfriend passed out drunk on her floor. I did my usual consoling and gave some safe advice. I really tried to stay out their high school drama. My roommates were sleeping and I was watching movies so I invited her over to chill, not really thinking that she would take me up on the offer.

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? 15 minutes later, she came over. Things were pretty low key. She thanked me for letting her come over and giving her an excuse to leave her house. She was wearing a little red summer dress and black flats. I always thought she was cute but there was some extra special that night because as soon as she walked through the door I got a little extra excited. I chalked it up to the late hour because I usually feel a little extra horny when I’m winding down for the night. We went to my room because I didn’t want to disturb my roommates while we talked and watched movies. I have a big Lazy boy chair in my room which I plopped down in and she sat on my bed.  We sat there for about 20 minutes talking but I couldn’t take my eyes of her legs. I think she noticed because every time I tried to sneak a peak her skirt was just a lil higher. Instead of movies we decided on listening to records. My record player was by my bed so I had to sit on the edge to play the records. As we listen to the first couple she sat close to me to look at the sleeves and album covers. As she sat close I started to become obsessed with the idea of kissing her. Without another though I reached over, lightly grabbed her face, and kissed her. It was a very deep and passionate kiss, the kind you see in movies and what not. Within a matter of minutes she was sitting on my lap and we were going at. She told me she never been kissed like that before, which made me chuckle. I picked her up and laid her on my bed.  She soon began to grind against me. I picked myself off her and slowly began to slide her skirt up to see a pair of lace panties. She then lifted her self and told me to take off her panties so I did. Back then I wasn’t too into going down on girls but I just had to taste her. I spent about 40 minutes tasting her as she wrapped her legs around my head and fucked my face as she orgasmed. which really got me hard. I stood up and took off my clothes. I could see the hunger in her eyes as I stood there with a raging hard on. I laid back on my bed and without missing a step, she slid on top of me. She slid off her dress as she sat on my rock-hard cock and I swear I almost came when she moaned as I entered her. Within a minute, she was riding me and rocking back and forth like no woman I ever had. It was still to this day the best I ever had. After riding me for a while she came once again then fell of me. We started to spoon for a bit but the passion soon got me hard again. I spread her legs again and took her from behind. The time I was a bit more gentle and soft but still very intense. After we were done she wanted to smoke a cig so we went to my back porch. We sat there with two huge smiles on our faces. I told her in all seriousness that I didn’t plan that and wasn’t expecting that to happen. She then told me she wasn’t expecting it either but was glad it did happen. She also said she was surprised she didn’t feel guilty for cheating on her boyfriend, and she was happy that I was her first older guy. I as still in shock that it all went down and from how good it was. I told her I was glad also. She hung out for about 5 more minutes and we said goodbye.

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? When we saw each other again I thought it might be weird but it really wasn’t. Over the next few months we got even closer and even started to develop feelings for her.  I hinted at another go but she said cheating on her boyfriend was a one time experience and wasn’t ready to call it quits with him yet. So we just continued to build our strong friendship. She ended up leaving the job and I moved so we slowly fell apart. I ran into her a few years down line and ended up dating for a while. I wanted more and she wasn’t ready for the kind of deep intense relationship we would have ended up having, so we decided to split ways. We lost touch over this last year but I still think of her often.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel more confident

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Marijuana, hashish

How wanted was this hookup for you at the time? Somewhat

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 told a couple friends years later about who were also the roommates that were living with me at the time. They were shocked because they never saw me really bring women home when they were around. I then got the nickname CIA because I was so secretive with my hook ups.

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

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? It was the best dick ride I ever had. Also my one and only experience with a girl that much younger then me. It gave me a lot of confidence that I was lacking at that time in my life.

What was the WORST thing about this hookup? Her boyfriend found out about it a year later and even to this day there is tension between me and this guy. Tried to cause a lot of drama between me and her while we were dating.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, I’ve always been very open to casual sex and it just proved even more I can be friends with a girl and still have sex with them without messing anything up.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? Casual sex partners do not work sometimes, but when they do it’s amazing!

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 enjoy casual sex. I have had more casual sex partners then I ever had relationships, which has lead to problems being in a deep relationship now that I want more out of my relationships with women.

What do you think about the Casual Sex Project? I think this is great thing and have been telling people about it!

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