Work Meeting Room With My Boss



What’s your gender? Woman
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: High school diploma
What’s your occupation? Office worker
What’s your current relationship status? Engaged/Married (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)? 15
How many hookup stories have you here posted before? 0

Work Meeting Room With My Boss

How long ago did this hookup happen? 2 months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For more than 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? My boss, with whom I have worked in the same place for 10 years. He has been my manager for the last 18 months but I have known him all 10 years.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We have occasionally kissed on drunken nights out, maybe 6-7 times. Each time I have regretted it because although I fancy him like crazy, I am married and tried to shut it down afterward. A couple of days after the last time he called me into a meeting room just before lunch time. The meeting rooms at work can be locked from the inside, and they have heavy soundproofing with lead lined doors as we discuss inside information on calls.

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? As soon as we got into the room, he shut the door, locked it and slid the shutter across the peephole. He pushed me up against the door hard, and just said he had to have me. Within a few seconds, I found myself pressed face first against the door with my dress hiked up around my waist and pulled down off my shoulders, my breasts exposed with my knickers around my knees and the head of his cock rubbing up against my pussy. He was manhandling me roughly and it got me wet pretty quickly, then he barged his dick into me forcefully. His size shocked me, I didn’t see it before he entered me but it felt thicker than anything I had known before. He got so deep inside me, I have never felt as full, it was so thick it hurt, but it felt good.

He pounded me hard, it was just straight up roughness, it felt like he was unleashing frustration on me. I felt an orgasm start to build up which is unusual for me as I can’t usually come from penetration alone, but he came hard inside me before it hit.

I felt him start to soften inside me, and we just stood there tying to get our breath back. Then he started working my tits, he was still rough, groping me hard, digging his fingers in and pulling roughly on my nipples and twisting them. It hurt me and I wouldn’t normally allow it but something about it was really turning me on. As he continued this I felt him start to get hard again, soon he was rock hard and once again ramming me hard into the door, this time roughing my tits up constantly as he fucked me. I had a huge orgasm and as it started he gripped my nipples hard and then pulled them down really really hard, which hurt like hell but it did intensify the orgasm. He came again deep in my pussy.

When we got our breath back he suddenly grabbed me by the hair and dragged me over to the table and pushed me down onto it. He held my hands behind my back and then just laid into me, spanking my butt. It was pretty intense, I had never been spanked before, not as an adult anyway. I squirmed and struggled but he was far stronger than me. He must have hit my ass over 100 times, I was blubbering and squealing at him begging him to give me a break. Eventually, he was hard again. He rubbed my clit a little after the spanking and I came again.

Then he started playing with my asshole. I was pretty shocked by this, I had had anal sex a couple of times but not since I was a teenager. But I didn’t say anything. I just let him do it. He started rubbing saliva into it and wiping his cock head again my pussy. I was nervous and tense. He actually made me finger my own asshole a bit. Then he pushed one of his fingers in as well. It was tough taking two fingers, it hurt, but I kept doing it. Then he spat on his cock again and I felt him press himself against my asshole. He wasn’t as rough as he was with my pussy but he was still forceful and he pushed it in. The pain was awful because he was so thick but I still did nothing to stop him, I just took it. He started to build up the pace and it became really rough, he was spanking me hard as he fucked me. He lasted a long time having already come twice. After a while he stopped and pulled me upright then played with my pussy and clit, I had another big orgasm despite the pain I was in from his cock being buried to the hilt in my ass. He got me to talk dirty to him in his ear, telling him how hot his rough treatment of me was making me and that I loved taking it in the ass. He pushed me back down onto the table face first and pounded my ass until he came deep inside me again.

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? I was bruised all over my boobs and ass and my pussy and asshole were sore to the core. I don’t know how I managed to hide that from my husband. A couple of weeks later my husband was away for the weekend and I spent most of that weekend being dominated again by my boss.

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

What were your motives for this hookup? Attraction to partner(s), Submission / Relinquishing power, Just happened, I don’t know why, just went along with it

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? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? A little bit

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? Very much

Why do you regret this hookup? Because I am married.

What was the BEST thing about this hookup? The orgasms I had were very powerful, much more than normal. I don’t know if was the risk, his dominance/roughness or something else.

What was the WORST thing about this hookup? The guilt. The bruises and being sore for a week.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes

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

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

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