What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? Australia
What country and/or city do you live in? Sydney
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Business owner
What’s your current relationship status? Engaged/Married (monogamous)
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)? 25 approx
How many hookup stories have you here posted before? 0
Spontaneous Office Romance With Older Woman
How long ago did this hookup happen? 9-10 years
What was your relationship status at the time? Single
How would you best classify this hookup? Short fling
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? Let’s call her B. This happened around 10 years ago when I was working as her assistant on a freelance basis. We’d go from project to project, and we’d work together a few times a year. She never did say how old she was, but I’d assume she was around 15 years older than me. I’d always had an attraction to older women since high school, so sleeping with an older woman was a fantasy of mine.
I found B attractive, but I was professional and never let on that I was interested as I valued our working and personal relationship. She was a brunette, slim, and had a big smile and easygoing manner. She had a slight bohemian vibe and was very confident and funny, which I found sexy. I’d occasionally think of her while masturbating and leave it at that!
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had worked late one day and were the last left in the office. It was the end of the week on a busy project, so she suggested we finish one of the bottles of wine that was opened earlier. I poured us both glasses, and we finished up our work while chatting and joking as we usually did.
Towards the end of our second glass each, she noticed one of the songs that we played during the day and asked me to turn it up, saying she loved that song. She said it was a great one to dance to, and I joked that I’m a terrible dancer. She was leaning on a table near me and things had been getting a little flirty. She was wearing a long flowery dress and a long headband, which she was twirling between her fingers. I took this as a bit of a sign. She said something along the lines that I’m being modest and she’s sure I’d be a good dancer. I was protesting, and she reached over and took my hand and pulled me in. No words were said, just lots of eye contact and smiling. She leaned in close, and we swayed together. Her slim body was pressed against me, and she took my hand. She held it and slung it around her back as I pulled in close.
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? After a bit more close dancing and eye contact, we began to kiss. I was getting hard by this point, and she was using her free hand to rub my cock through my pants. The kissing and fondling were becoming more urgent by this point, and I was starting to unbutton the front of her dress and kiss her breasts through her lacy bra. I had checked earlier that we were alone in the office when I poured the wine, but she said that we should lock the door so there is a bit of notice in case anyone walked in. I quickly did that, and when I got back to the desk, she was finishing her wine and motioning me to come closer.
We resumed kissing, and she started unbuttoning my shirt and belt. She placed down her glass and I used that cue to push her down onto the desk and with my two hands, I hiked up her dress and removed her underwear. She had beautiful long legs and a lovely trimmed pussy. I kissed and licked her on both legs from the feet to her pussy and lightly blew on her clit, which she loved. I teased her for a bit, kissing around her pussy and ass but only licking her clit now and then, which was fun. Eventually, she grabbed me by the hair and pushed my head into her, and I started going down on her. She tasted amazing and was really enjoying it. Things were heating up, and I escalated proceedings by entering two fingers as well. She was moaning and writhing a lot by this point, and she pushed me off and said it was my turn.
She pulled down my pants and started nibbling my cock through my boxers. She was running her arms up and down my chest. The best part was her beautiful eyes as she looked up at me with my cock in her mouth. After a minute, she pulled down the boxers and took me in her mouth. She pulled her dress down off her shoulders and was playing with her pussy while sucking me off. The next part is a blur, but after a while, I pulled her back up, and she stepped out of her dress and removed her bra. I didn’t want to come early, so we stood kissing for a bit while I played with her pussy. I laid her back on the desk, and she guided me in to her wet pussy. I started slowly thrusting while playing with her clit. She was massaging one breast with one hand and covering her mouth with the other, groaning. My thrusting became more urgent, and I could feel an orgasm coming on. I pulled out, went down on her again (which annoyed her a bit, playfully), and then, I reentered her. I pounded away, and since she was very wet by this point, things were very noisy.
I came quickly after that, so I went back down and began eating her out again. She was rubbing my cum all over her stomach and the smell was quite strong, which I remember well. I ate her pussy until she jerked and arched her back and I could taste her salty cum. At this point, we laughed and said, “Wow, how did this happen?” She pointed out that I was still hard, and I said that I wasn’t done fucking her. She said she liked the sound of that, and we started kissing while she took some tissues and wiped her stomach.
She then led me to the couch where she went back down on me, and we fucked in a few positions, mostly cowgirl, until we had at least one more orgasm each. Remember the long handband/scarf I said she was wearing – at one point, I pulled that off and tied her hands together while I fucked her from behind.
After we finished, we laid on the couch kissing, and I said that I owed her a date. She said she’d love that except she’s married (which I knew) and laughed. Eventually, we put our clothes back on and went for a quick dinner. Things weren’t awkward, and I dropped her to a taxi.
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? The next day we spoke on the phone and it wasn’t awkward. Her husband was away, and I went over to her place on the Sunday for lunch, which led to some nice afternoon sex. At work the following week, things were flirty, but we kept it together. We mostly kept it to looks and a quick kiss when we knew there was no-one around.
On the second last day of the project, we hooked up again at the office. In the late afternoon, she came past my desk and said she had something for me. She said to close my eyes and open my hand. I did as she asked, and I felt her place some soft fabric on my palm. I opened my eyes to see her smirking and walking away. In my hand was her red satin g-string. My cock immediately went hard, and since everyone was still in the office, I was genuinely worried I wouldn’t be able to last the rest of the day without jerking off! She texted me at her desk to instruct me to wrap her g-string around my cock and that she’ll pull it off me later. This made me even hornier, but I did as she asked.
I managed to distract myself for the last few hours by surrounding myself with other people, and when the office finally cleared out, I pushed her up against a wall, and we were urgently kissing as she was undressing me. She said she was already wet thinking about her panties wrapped around my cock. I took her to the sofa and bent her over the back of it where she lifted up her skirt and I went in without going down on her. As expected, neither of us didn’t last long, but we both came. And yes her panties stayed wrapped around the base of my cock, so by the end of it, they were quite wet!
We played around a bit more and went back to my place where we had more sex, and she spent the night.
After this project, we spoke again and things were fine. I started seeing someone, and since we went onto other projects, things fizzled out. But, I’ve since run into her on occasion over the years, and we maybe exchange a knowing glance. But now, we each have partners and don’t speak about those fun weeks.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Intoxication
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
What substances did your partner(s) consume? Alcohol
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 haven’t told anyone.
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? 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 most spontaneous, best sex I’ve had. I also gained a lot of confidence from the encounter and was less shy about approaching women after that.
What was the WORST thing about this hookup? She did feel bad she was cheating on her husband, and I, in turn, felt bad about that as well. I don’t think their marriage was going so well, and she had remarried last I heard.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? As mentioned, the confidence boost was great. It was also a good affirmation that women can be just as forward and well, horny as men and that they can instigate it.
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? I’m married now but still very much fantasize about the older woman. I haven’t acted on it though.
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’m all for casual sex, as long as it is done safely and with respect (admittedly our encounter had a third party involved which isn’t ideal). It allows people to get to know themselves and their partners.
What do you think about the Casual Sex Project? It’s a fantastic resource and great place of shared experiences. It’s very human as well, and I love reading the various ways people make connections.
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