Current location: New Zealand
Highest education received: College degree (eg., BA, BS)
Occupation: Company director
Relationship status: Single (separated)
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)? 32
How many hookup stories have you here posted before? 10
Third Hookup With My New Fuck Buddy
How long ago did this hookup happen? Yesterday
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…)? Fuck-buddies
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? He is a 6’2” handsome guy, my own age, brown hair, blue eyes, nice, normal physique. I met him on Tinder and I liked his profile because it was very straightforward in that he stated he was relatively newly separated and was looking for an exclusive friend with benefits situation, i.e. he was looking for someone who he had some chemistry with, who he could meet regularly for sex, without getting into a relationship as it was too soon for him. He described himself as well-dressed, smelling nice and being a good lover, none of which was false advertising. I am looking for the same, I have been separated longer than him, but have a really really busy life with my kids and my business and my wonderful friends and I don’t really want much more than the physical company of a man from time to time, but like him, I want it to be someone who I am attracted to and whose company I also enjoy.
We chatted a bit and I had some free time on the weekend to meet up, but both of of us had some other matches on Tinder we were juggling. We decided to squeeze in an afternoon meeting in a pub just to meet each other in person so we could decide if we wanted to meet up again. We had a couple of drinks in a deserted pub and I liked him and found him attractive. He thought the same. Before we left he kissed me and I knew then that we would be in a good match sexually because he was a superb kisser and I felt very aroused just kissing him and didn’t want to stop. We met up the following weekend for our first hook-up which was pretty spectacular, then he visited me during the week in the early hours of the morning while my kids were asleep for a quick and quiet fuck, then we arranged our third hook-up for the next Saturday night, at my house which was empty with my kids having gone to their Dad’s.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was a lot of anticipation leading up to our third hook up when we knew we would have lots of time and were now comfortable enough to be very upfront about what we wanted to do together. Our messaging was a form of foreplay and we were both pretty excited. I also went to meet him for a coffee one day and we went for a walk and kissed in some gardens and that helped the anticipation to continue to build. Also I knew from my first encounter with him that he has an amazing ability to bounce back after coming and get another erection. He can easily do 4 or 5 times in a night.
We had done anal during our first hook up, my first time in over 20 years and it had gone OK but we were excited to spend a bit of time working on that, and he asked me in advance if I would be interested in some toys. I said yes, so he went for a visit to a sex shop and bought a few things to bring over, which he kept as a surprise so that was exciting.
He also told me during our messaging that white lingerie really turned him on and he would love to fuck me from behind with me wearing white lingerie, stockings and heels. I have a gorgeous white basque and all the trimmings so told him I would dress up for him. Knowing he would arrive at 6.00, I got all dressed up in my lingerie and this made me even more excited.
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? When he arrived I answered the door in my lingerie and heels and he was super super excited, he dropped all his things and just grabbed me telling me how sexy I was and how much he wanted me. I thought he would end up fucking me pretty quickly but he actually managed to not do that. We kissed for about 15 minutes and I love kissing him he is fantastic at it, while he caressed my body. Then he went down on me for ages and made me come three times. Each time I came he just kept going and it was pretty intense and totally amazing. Then I sucked his cock for a while and when I thought he was close he stopped me, and then we fucked with me on my back and my legs over his shoulders. That part was hard and fast and pretty fantastic and he came.
This was on my couch and after a short rest, he grabbed me again and we went to my bedroom for a long and gorgeous 69. After that, he did fuck me from behind as he had wanted to do and we both came. I took my heels off at this point!
After that we had a break and had a glass of wine and chatted while I prepared some dinner. While dinner was in the oven, we lay on the couch kissing and he sucked my nipples and we both played with each other manually, building up again. Some more 69 which made me come again. Then he fucked me again from behind, this time he rubbed himself against my ass for a bit which really turns him on before entering me again to come.
Then we had dinner and a bit of a longer break. After dinner we had some chocolate and a cup of tea and did the dishes. Told each other some stories.
Then we went to bed for the night, I got him to undo my basque which has a lot of hooks and eyes and took the stockings off etc. Then he showed me the anal stimulation toy he had bought and said it was time to try that out. We got back into 69 position but this time, while he was licking my clit, he was also gently probing my ass with this toy which was well-designed and he got it in there pretty easily. It vibrated and once it was in there vibrating, he continued to lick me while fingering me and the combination of all 3 gave me probably the most fantastic orgasm I can remember having. It was mind blowing and I was moaning and shaking. Absolutely fantastic stuff. After that, he got me back on my hands and knees and we had anal sex which is his favourite. It was much easier than last week and felt great, he had another orgasm and seemed very happy. After that we went to sleep, pretty exhausted.
I woke up in the morning to feel him stroking my clit very very lightly and gently and I could feel his hard cock pressing against my side. After a long time kissing we had very nice missionary position sex.
Then I went for a run, then we both had a shower and I cooked some breakfast. More chatting and he is very easy to talk to. After breakfast we fucked one more time before he left. My kids were coming back soon.
Did you have an orgasm? Did your partner(s)? Yes, many many orgasms. Him, 6 times. Me, countless.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? He is sterile due to a medical condition. Our first time together we used condoms. After that, when we decided to pursue an exclusive fuck-buddy situation, we discussed STI history and are both clean. We are no longer using condoms.
What were your REASONS for having this hookup? Having good sex makes me happy and it is the only thing missing from my life. I met someone who also wants to have regular sex and who I’m very sexually compatible with.
Were alcohol or drugs involved? If so, how much? We had a couple of glasses of wine throughout the night. Neither of us were 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? I feel absolutely fantastic and can’t think of a better way to spend my precious time off. I feel satisfied and relaxed and fulfilled.
My expectation is that we will continue this arrangement for as long as it works. I like him and I hope we can manage it for a good while.
I think that long-term it will not be able to continue. It will end because:
a. Either one of us will meet someone we want to have a serious relationship with; or
b. one of us will get more attached than the other making it untenable (probably him as from his history he strikes me as being a bit of a romantic which I am definitely not); or
c. I will not have enough time to see him to keep him happy and satisfied and he will start to look elsewhere.
At the moment I feel very fond of him and very excited about seeing him next time.
To whom did you talk about the hookup? How did they react? I have one close girlfriend who knows that I’m hooking up with him. She doesn’t know anything about what we actually do though, and she probably won’t ask.
I also have 2 online friends who are both married men (who I don’t and won’t see in person because they are married and I don’t do that) and they know I’m hooking up with someone new and will both want to know details. I’m not sure if I’ll tell them or not though.
Was this a consensual and/or wanted experience for you? For your partner? Absolutely yes.
Do you regret this hookup? If so, why? Absolutely not.
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 thing was finding someone who I’m very sexually compatible with who is just a really great lover, so I am getting immense satisfaction from being with him. I also like that he has a really similar attitude to sex to me, that it is just a really fun, happy and natural thing to do so there are no hang-ups or feeling that it’s dirty or taboo to do certain things, so we can be really really open with each other about what we like and what we want to do. I’m sure we’ll experiment further and it will be in a nice atmosphere of fun and mutual acceptance.
I already knew sex could be like this so it hasn’t changed the way I think about casual sex or sexuality. Just pleased to have made a good connection.
With regards to myself, I am feeling sexier since this hookup. It is really nice to hear someone say how hot and sexy you are and how much you turn them on. He told me I’m every man’s dream woman and the best he’s ever had and that’s a big confidence boost and with that confidence I do feel that I would be more likely to share my more secret fantasies with him. I feel appreciated for that part of myself. (He also said that I’m awesome because I’m smart and funny so I feel appreciated all round really!)
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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