Not So Hard

by MrSqueak

Gender: male
Age: 33
Race/ethnicity: European
Current location: Munich (Germany)
Highest education received: College degree (eg., BA, BS)
Occupation: Informatics
Relationship status: Single
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 1 2

Not So Hard

How long ago did this hookup happen? 2 months

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…)? ONS

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? She was a very attractive 40-year-old. I met her on a Casual Dating Site,, that I got an account on after my previous hook-ups (see Weird Metro Girl and After The Big Game) left me wanting more casual sex, badly. The fact that we actually met already made me feel pretty excited, as it seems to be incredibly hard to get any of the women there to even answer to your messages, let alone meet with you. There seems to be a huge difference to the numbers of male/female users on these sites, and the experience had been quite frustrating to that point. Had two dates with other women prior to this, and they were going nowhere, either.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We chatted for a bit on the site, and she had written in her profile that she like to exchange sexy stories and phantasies, so I asked her if I should write her something. It quickly became clear that she enjoyed my writing, and the build-up was actually quite exciting for the both of us. We exchanged about four stories, or actually one story that just went on and on, and decided to meet at a café in Munich’s Glockenbach area. Funnily, she actually got the name of the place wrong and we both thought for half an hour that the other had bailed. Thankfully smartphones exist, as we did not have each others’ numbers!
After having dinner together and some normal conversation we moved from the Thai restaurant that she mistakenly had sent me to to the café we originally had planned to go to 🙂
We got a nice seat overlooking the street and I sat down close enough to her to be able to innocently touch her now and again. After some time with wine and beer we got really comfortable, she mentioned how stressed out her job makes her sometimes, which I decided to interpret as a reason to give her a neck massage. Obviously I was quite good at it as she nearly started to purr, and lo and behold, a couple of seconds later our tongues were intertwined, our hands were everywhere, and there we were, a 33 and 40 year old making out in a café like teenagers! 🙂 She said I had to go slow, as she was already on the brink of going insane from all the sexual tension. She is going through a divorce right now, her husband still living in their house, so there was a lot of horniness on her side and a lot of not-possible-to-go-to-her-place-ness as well. I stupidly had not cleaned up my room that day, so I suggested we go to a hotel, which she found intriguing. She said yes, obviously 😉

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 made out on the way to the hotel I instantly booked (again, smartphones are great 😉 ), and also in the hotel lobby. Then we quickly got to the room and decided that clothes were not a real necessity anymore. I undressed her pressing her against the wall, enjoyed every part of her great body (nice tits, ass, and slim figure; not terribly important for me, but nice nonetheless), then proceeded to lick her gorgeous pussy. She got me out of my clothes as well, gave me a blow job. I caressed her just like I knew she wanted to be caressed from our story-exchange; I could tell how badly she wanted me, but I took it slow, made sure she enjoyed every second. She lauded my caressing and oral skills, came for the first time through foreplay if I remember correctly. She also wanted me to finger her, and to my surprise she was incredibly flexible, taking in four fingers without much preparation (she said she had been wider ever since the birth of her daughter). Intense fingering was new for me (she was only my fifth sex partner, and the others weren’t so much into it), and I enjoyed the feeling of her contracting pussy against my hand…

Then she wanted me to fuck her really hard, and that’s where the trouble with the night became apparent: As I mentioned in my last story here, due to some medication I take (which I found out later) I have erectile problems. So I could not get properly hard, even though I was incredibly horny and wanted to fuck the living daylights out of her. We tried anyway, but my dick was too soft for her eventually, and I did not come either. I could tell that she was frustrated about it, and for me it was pretty shameful, and the stress after a few minutes did not make it better. We gave up eventually.
I pleased her orally again for a while, which she still enjoyed veeeery much, but she told me the next day that it was a bit disappointing for her that we could not fuck properly.
After a last orgasm for her, we cuddled and went to sleep in each others arms.

Did you have an orgasm? Did your partner(s)? She had several.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms. No discussion. I have since been tested.

What were your REASONS for having this hookup? I enjoy sex very much, and the chat on the site made us both horny beyond belief.

Were alcohol or drugs involved? If so, how much? A bit of beer for me and wine for her.

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? We parted ways in a friendly manner. I had written her a couple of messages, complimenting her on her skills, body, and how generally pleasant an experience it had been with her; also, I explained my medical condition after I found out. Generally I’d like to hook up with her again, but don’t know if it will ever come to it. She is on an extended holiday trip with her daughter right now, dunno if I will ever hear from her again.

To whom did you talk about the hookup? How did they react? My usual friends. They are always very positive about stuff like that 😉

Was this a consensual and/or wanted experience for you? For your partner? Absolutely.

Do you regret this hookup? If so, why? Not at all.

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 best was the horniness and passion of it all. Also, she had a great body, character, pussy, ass, everything. The whole experience was also good for my self-confidence. And it made me want sex even more 🙂
The worst was the erectile dysfunction. Luckily it made me see a doctor, and now I have pills at my disposal that made the problem go away for good. 🙂

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

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