A Guy I Liked At Work

by Tippy

What’s your gender? Woman
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Atheist
What’s your sexual orientation? Pansexual
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 6

A Guy I Liked At Work

How long ago did this hookup happen? 10 years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a year

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?
I worked in a department store when I first met Seth. He was about 5’8”, stocky and broad, with black hair, and he was about my age (19). He had dark blue eyes and seemed quiet, he was really interesting to talk to and was a genuinely warm and funny guy. He was a naturally flirtatious person and we often made each other laugh sharing in-jokes or coming up with ways to make work more interesting.

Initially, he started as a temp, but then got a permanent job. Our shifts didn’t always line up, but it was always fun when they did or we got sent to each other’s department. I was in a monogamous relationship and had never cheated before, but it was becoming increasingly toxic at home, and having some flirty attention and feeling sexy wasn’t something I was used to. We both went full time and saw each other regularly. I started making a bit more of an effort (for me that’s actually putting make up on) and we started to spend break times together. He was leaving work to go to uni (a long way away) around the time I’d known him close to a year. I had fantasised about him a lot and we’d playfully joked about sneaking off together at work. On the day he left, I awkwardly asked for his number, wondering if I could escalate things as it was now or never. I had always kept behind that ‘work’ line before.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?
Seth gave me it and his AOL info and it didn’t take long for us to start chatting and being suggestive. I was quite direct in what I wanted and he was on the same page. I’ve always been very confident online, but in real life I was bricking it. I’d never had casual sex before. We agreed he’d pick me up and we’d go to his when his parents were out of the house.

I got in his car on our agreed time. I was incredibly sober and nervous. We joked and chatted in the car as normal, but I was so turned on knowing he’d picked me up for sex. When we got to his home, he invited me upstairs. We sat beside each other on his bed and talked a little, and he said he had a bit of a headache.

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 can’t remember who initiated our kiss, but I remember his mouth feeling small with little pecks and nibbles. It was pleasant, but not terribly passionate. We felt each other up and I took our bottoms off.

I felt his dick, but it felt small. I didn’t think he was aroused. When his boxers came off, however, it was clear he was hard, but his dick was very small, maybe 3 inches, and it was not girthy either. I laid on his bed, we still had our tops on, and he rolled a condom into his dick. I honestly think I wondered at the time how much of the condom he actually had to unroll. He started penetrating me and I could barely feel anything, but tried to at least act a bit so as not to hurt his feelings – I really liked him as a friend. He fucked me for a bit and came. I was kinda confused, as I’d gotten horny and wet, but had virtually no stimulation, the situation was a turn on but not much else was.

He apologised and said his headache was really bad. He hadn’t been himself and I do wonder if he’d had an awful migraine but just tried to follow through to get laid as it was our only opportunity before he left town. We watched a bit of ‘Horton Hears a Who’ on his tv and he made me a cup of tea. We chatted a bit and eventually he drove me home.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

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 felt awful for cheating and not even having a good time. My emotions felt funny and I briefly tried to get together with Seth again then changed my mind and we left it. I never saw him again, but if I ran into him I’d give him a big hug. He’s a good guy and I feel bad he has such a small penis.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

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, To feel better about myself, To feel more desirable, To feel more confident, I was feeling lonely, Boredom, It was easy / convenient

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 feel bad but when friends share bad sexual experiences I do usually tell this story. I hope he’s learnt other ways to satisfy women now.

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

Did you get emotionally hurt as a result of this hookup? Very

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? The sex was awful and it was such a disappointment after all the build up and flirting. I left awful for betraying my partner even though he really didn’t do anything to deserve me.

What was the BEST thing about this hookup? Learning about myself, having casual sex, and fulfilling a fantasy.

What was the WORST thing about this hookup? His tiny dick and him not feeling great.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I think I was really glad I knew I could enjoy sex outside of a relationship and walk away without it getting messy.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Fairly negative

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