What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Albany, NY
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Software Support Specialist
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Heteroflexible
How many sexual partners have you had in your life (including oral sex)? 45
How many hookup stories have you here posted before? 0
Working Hard, or HARD at Work?
How long ago did this hookup happen? 7 years
What was your relationship status at the time? Dating casually
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? Nikki was coworker of mine, 20 years old, about 5’5″ athletic muscular legs and a slim waist. She had gorgeous reddish brown natural curly hair, but not frizzy curly hair, the kind of curly hair girls with straight hair all want but curlers just can’t quite match.
She had started working in the same office probably about 2 years prior, but in a different department. She had caught my attention a little, but I didn’t even know her name and we never really had any reason to talk. After about 6 months I noticed she was no longer at her desk when I had to pass by her cubicle, and I assumed she had moved on. A few months later I got a system request to configure some changes on her computer (I’m in Software Support), apparently she had moved to second shift for a raise, but was taking a promotion and moving back to first shift, and her new cubicle was just 10 feet or so from me.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I knew her name now, and although I had to this point avoided dating in the office, I thought she was cute and figured it couldn’t hurt to be a little flirty. I saw her pretty often now since our two divisions shared a kitchenette area, and said hey and flashed a smile a few times. I didn’t want to be too vocal about my flirting, our office was mostly women and I didn’t want to start any rumors, so I decided to send her an email just to strike up some conversation. We talked a bit, I learned that she had a young daughter, not quite 2 years old, and she had a boyfriend she had been with since high school. It was nice to have a friend in the office, although it wasn’t headed the direction I was hoping it might.
It was a beautiful day out one morning and we decided to go for a walk during early break. We talked about, and walked around the neighborhood surrounding the office, she confessed to me that she was very unhappy with her boyfriend, but was staying with him because of their child. I genuinely felt bad for her, I told her she was too young and beautiful to concede her life to a relationship that made her so unhappy. We continued to talk and eventually changed the subject and headed back to the office.
We couldn’t have been back at our desks for more than a few minutes before I got an email that said “Do you really think I’m beautiful?” I explained all of the reasons why I thought so, she loved the compliments. We chatted back and forth furiously, ignoring our work for hours. She told me since she had been with her boyfriend since she was 15, she had only been with 2 guys, and one was a mistake she made at 16 during a brief time when they had fought and broken up. The poor girl had no self esteem, and no idea how beautiful she really was, her boyfriend was a selfish lover who never cared about her enjoyment. She confided that she had never had an orgasm not even from masturbation, and didn’t believe that she could.
Our conversation turned sexual from there, I definitely instigated, but I honestly believed that this poor girl needed someone to show her the things that she was missing. We talked about passion, and sex and how orgasms felt. I’m no Casanova, but I know what I’m doing, and I knew she was very attracted to me. We decided to take our afternoon break together and walk again.
She had a flowing pink and tan sun dress on, that went up to about mid thigh, and some strappy flat sandals. Her beautiful curly hair was blowing in the wind, she had a cute little nose ring and full lips and her cheeks were a little rosy from all of the dirty emails we had been sending back and forth all afternoon. We were considerably more reserved face to face, and our talk was back to normal subjects until we got to an area of our walk where we had to cross a private little foot bridge. I stopped her and turned her toward me and gave her a long, sensual kiss. When we finally broke I pulled back a few inches to look at her, she just kept her eyes closed, savoring the moment. I think she thought I might kiss her again, but instead I slipped a hand under her dress and brought it right to her pussy. To my shock she wasn’t wearing underwear! She was soaked, the entire inside of her thighs were dripping, and she was so swollen. She finally opened her eyes, and looked at me with a big smile. She told me she soaked through them while we were talking and it was uncomfortable so she took them off. I pressed my middle finger into her swollen lips and began to rub circles her clit as we kissed passionately again. Unfortunately before too long we heard a few people coming along the path and we had to retreat back to work before break ended.
There was no going back from here, we both knew we needed each other. That day was out, but we made plans to go for a longer walk on lunch the next day.
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? We left the office a couple minutes apart to avoid gossip, and met nearby and giddily skipped out toward the park. There was a wooded trail there that was very private and we figured we could find a quiet spot. Once we got there we started kissing passionately again, and I reached my hand under her dress again. This one was white with a purple design, she knew I loved it that she had ditched her panties the day before, so I was pleasantly greeted again with soft bare skin. She reached down and unzipped my pants and pulled my rock hard dick out. We stood face to face, kissing as we had done yesterday as I rubbed her clit, I used every motion and speed I could think of. She was so wet and ready, I could hear her breath shortening and her body was tense, but despite being right on the edge I wasn’t able to push her over. After a while I could sense she was frustrated and she broke our kiss and squatted down to take my cock in her mouth. She looked so hot squatting down, knees opened wide so I could see her exposed glistening pussy. She slowly licked and bobbed up and down on the head of my cock, just loving it and taking it all in. At one point a jogger ran by us on the trail, she never stopped and I just kept my eyes locked on her mouth around my cock. The jogger never even slowed. Soon after I told her I was going to cum and she just shifted her gaze from my shaft to look me in the eyes as I filled her mouth. At this point I was feeling euphoric, but was pretty disappointed I hadn’t been able to make her cum as well. My cock never even skipped a beat and I wanted to fuck so bad. I called back to the office and told my supervisor I was meeting a client for lunch and wouldn’t be back in the office until later that afternoon. She walked back to work by herself, and told her boss she wasn’t feeling well and needed to go home sick. She met me in the parking lot and followed me to my apartment.
Once we got to my apartment it took second to pull her dress up over her head and for me to lose my pants. I finally got a good look at her body nude. She had great soft olive colored skin, cute perky tits, probably Cs. Her body was firm and her ass and legs were astonishingly athletic. She had a C-section scar, just above her small curly landing strip of pubic hair. I guided her into my living room kissing her neck and chest and pushed her on the couch. I kissed my way down her torso to her hips, going around her wet slit to her thighs as I slid back off her onto the floor. I then worked my way up the inside of her thighs until I was at her pussy and she had her knees over my shoulders. I went down on her for about 20 minutes, she moaned and writhed and tensed in pleasure, but she still couldn’t quite pull the trigger.
Eventually she reached down and lifted my shirt over my head, then wrapped it around me like a lasso and pulled me up onto her. I hovered over her in a plank, using my hips to guide my cock over her shaved box. Then slowly I pushed in the head, pulling it all the way out and teasing again. I continued to tease her like this, each time deepening my stroke a half an inch or so until I sank my cock all the way in and left it there filler her up while we kissed.
We fucked passionately in missionary like this for about 20 minutes, tasting each-other’s lips and necks. Eventually the passion turned visceral and we switched to doggystyle where I pounded her hard from behind, and then I flipped her back over and put her feet on my chest, bringing her keens to her chest. I was able to look down as my cock went in and out of her, and the sight pushed me to the edge. I told her I was going to cum again and she reached around and grabbed my ass holding me inside her. I groaned and convulsed and filler her with cum.
We moved to the bedroom to cuddle in my bed for a bit and talk some more. Talk was somewhat innocent at first, but I was still disappointed I wasn’t able to make her cum. I’m not the most selfless lover always, but knowing this girl had never had an orgasm and wasn’t going to get one at home had made me so determined. I was exhausted and part of me was content to cuddle, but I couldn’t just let it go. I stopped talking and slid my body down the bed, opened her legs and flicked my tongue over her clit again. I was really going to take my time this time, and make it clear that this was only for her, and not foreplay. To my surprise she was reacting really well to very very light soft teasing licks. I kept this consistent, barely there light licks up for a few minutes and then boom, like a bear trap her thighs closed around my ears and her back arched so high hips bent my head back. Her breathing stopped completely and the room was silent for about 15 seconds as I continued to flick my tongue over her, a little slower now with more deliberate pressure. Eventually she gasped for a deep breath and her body collapsed as she pushed my head away.
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? I moved back up the bed and we spooned for a bit. She was in disbelief. She had truly believed that she was “broken” and I was wasting my time. We now knew that she was extremely sensitive and all previous contact had just been too intense. We didn’t talk much, and eventually I realized I had better go back to work. I let her stay in my apartment to shower and watch TV until it was time for her to go home.
Our dirty emails and walks continued on and off for years. We became good friends in the office, and there were some rumors we dated, but mostly people assumed we were just friends. Nikki was sort of empowered about her body after realizing that sex was something she really could enjoy. She would often stop in my cubicle and we would talk – we were surrounded in other cubicles by 15 or so people (most cubicles were quads), but she would sit with her back to my cubicle opening and spread her legs and slip a finger in if she was in a dress, occasionally she would pull a chair up by my desk and we would sit face to face, she would slip her shoe off and rub my cock with her foot.
She was really curious about fooling around with another girl. She really wanted to have a threesome with me, but we had trouble finding someone that we could trust to keep it to themselves. About a year later she told me she had seduced a female friend of hers, I was a little jealous I couldn’t have been a part of it, but happy that she was no longer missing out on enjoying life. At one point I had a far more public fling with another girl from the office named Shannon. Nikki knew about Shannon, but Shannon like everyone else thought Nikki and I were just friends. I wasn’t exclusive with either of them and continued to hook up with them both. Eventually the thing with Shannon ended, and I continued with Nikki.
We ran out of the office for fuck lunches on a fairly regular basis for a few years. She wanted to leave her man for me. I always told her if she wanted to leave her boyfriend, we could see where things would go, but I wouldn’t promise her anything. I wanted her to make the decision to leave him for her own happiness, not to leave him to run to me. During the years we hooked up she never did leave him.
Eventually I met the woman who would become my wife, and I decided to put an end to our years long fling. It would have been very difficult for me to hold myself to that decision honestly, but not long after Nikki left the company for a much better career opportunity. She has tried to make contact with me once or twice in the years since then, but my wife knows about my history with her and I don’t want to rock the boat. I do know she eventually did leave the jerk she had been dating, and she has met someone else.
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), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have
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 later told another female coworker about it. It actually really turned her on and we ended up an amazing fling of our own (another story for another time!)
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 was able to help her open up about her sexuality, and on the side we had consistent great sex.
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? I think casual sex is important. It may not be something for everyone, but you learn so much about yourself through casual sex.
What do you think about the Casual Sex Project? Its great! I love that there are some stories that are just erotic reading, some that are about lessons learned, and others about people experiencing empowerment.
Unfortunately some of the stories on here seem completely made up, but I suppose that is to be expected.
You have a hookup story to share? Submit it here!