by Michael

Gender: Male
Age: 48
Race/ethnicity: British Indian
Current location: UK
Highest education received: College degree (eg., BA, BS)
Occupation: Office
Relationship status: Partner
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 46
How many hookup stories have you here posted before? 0

Office Sex

How long ago did this hookup happen? 10 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? one-night stand (well during the day!)

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 met this 28 year old woman through a British dating site. We chatted on the phone for an hour or more on each occasion, before we met.  Our last conversation did turn to sex and she explained to me what she liked. Helen described herself as attractive, 5’7″, nice figure, liked to wear tight corsets and that she had very large breasts.  I recall also that she was a theater set design artist, and that she also sold paintings.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Helen was in London to window shop for the day with a friend, and we decided to meet for two hours whilst her friend did some shopping.  We met in a busy old fashioned pub in Central London and had one glass of wine each.  After about an hour of conversation in a cubicle in the pub, and given that time was short, I asked Helen if she found me attractive, she said “Yes!” and we kissed, and we do so very passionately.  I love it when she pushed her tongue into my mouth, and I recipricated by pushing mine into hers and sucking gently on her tongue.  Mischievously I suggested that she came back to my office where we could continue matters.  She very briefly hesitated but said “yes”, and given that she had to meet her friend in an hour, we then hurried out of the pub and headed to my office, that isn’t far from the royal palace.  It was a Saturday afternoon and after signing in Helen at the security gate of my office, we took the elevator up to the 14th floor of my office building.  Helen to my delight was quite forward and groped my crotch as the elevator ascended.  We kissed and I cheekily reached under her skirt in the elevator and stroked her knickers, and I could feel that her pussy was wonderfully damp.  When we arrived we headed straight to my office.

Will tell you shortly what happened.

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 went to my office.  I locked the door and we started to kiss and strip off our clothes.

Although Helen had told me that she had large breasts, I wasn’t prepared for our large they round as she didn’t show it in the dress she wore.  And underneath was a tight corset with her breasts spilling out above.  She removed all her clothes, but for the corset.  I was completely naked.

Sitting on a desk, Helen sucked my cock whilst I fingered her very wet and dripping pussy.  I asked Helen to suck my balls whilst I masturbated the shaft of my cock.  After about five minutes I asked Helen to open her mouth and watched my sperm shoot hard into her mouth.  The sperm sat on Helen’s tongue and then she swallowed the lot.

I wasn’t sure whether Helen was on the pill, and think I asked her, but by this time her mutterings were not articulate.  I fucked Helen against the desk.  I wanted badly to cum in her pussy but didn’t want any consequences so when I was ready to cum she asked me to spurt all my cum on her face.   She grabbed a tissue from her bag and wiped it up.

I am very lucky in that when turned on, and if I haven’t come for more than a day, I can cum a lot – up to six or seven times in a few hours.  I asked Helen if I could have her anally and she quickly agreed.  She layed her body on the floor and I got on top of her from behind and fingered her bum, and also using some of my saliva I frigged her for a few minutes and tried to also with the other hand and finger touch her clit.   Then using more of my saliva I lubed my cock with spit and entered Helen without difficulty.  I have a long about 7 inch cock that isn’t very thick, so I slid into her arse quite easily.  After a few strokes and with her head turned to the side she stuck her long tongue out and I was able to kiss and suck her tongue whilst fucking her beautiful peachy arse. I asked twice if i could cum inside her velvety arse, and both times she responded yes, so i did.  When I did come I moved her body onto the side and before long we managed to have anal with me on top and facing her.  I then came again in her arse.  Helen looked at her watch and realised that she was late, so I quickly got up and we both then dressed.  I went to the gents toilet to clean my cock.  We then left the office and the building and headed to where she was going to meet her friend.  I kissed Helen passionately and we said goodbye.

Did you have an orgasm? Did your partner(s)? I came twice in her mouth and as I wasn’t sure whether she was on the pill, I then came twice in her bottom – anally.  I played with her twice and believe that she came once.  I didn’t get the chance to lick her and thought that this was something we might possibly do in future if we ever met again.  But we never did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None.  We used the withdrawal method.  We discussed before we met on the phone about STIs and we both said that we had recently been checked.

What were your REASONS for having this hookup? Was single and actually looking for a potential relationship through a dating website.  But met this woman and this turned out to be a one-off hookup.

Were alcohol or drugs involved? If so, how much? I had one large glass of wine, and the woman had one small.  Neither of us were noticeably drunk.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? The woman did text me to tell me that she had carpet burns on her knees the following week, but stupidly i didn’t respond at the time to arrange another meeting.  I regretted this as she was actually a nice and decent person, regardless of the fact that we had sex on our first date.  Some months later I did text this woman twice, but received no response.  I recorded in my notebook the experience and I am now relaying it as part of this project.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? Yes, both of us consented.

Do you regret this hookup? If so, why? Definitely not!  If i did, I wouldn’t have spent the time to write about it and share with everyone.  I try to leave regrets in the past as best as I can.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The sex was mindblowing within a short space of time.  Regret not meeting this woman again for dinner and further dates, and yes, lots more sex!

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? If the woman every recognises this post, please get in touch! lol    Me Indian guy, 6ft, slim to medium build and toned.

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!