by Jacrou

Gender: Female
Age: 45
Race/ethnicity: Caucasian
Current location: New Zealand
Highest education received: College degree (eg., BA, BS)
Occupation: Company Director
Relationship status: Single
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)? 31
How many hookup stories have you here posted before? 0


How long ago did this hookup happen? 2 weeks

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…)? casual lover

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 man via an online dating/hook-up app. We sent messages to each other for a couple of weeks before meeting up as we don’t live in the same city. He is a slightly older German man, he is good-looking in that typical German fair and chiselled way. Quite tanned, reasonably good shape. Whilst I had never met him before, we had chatted a fair bit so I knew his full name, where he lives, what work he does. I had seen his Facebook page plus his business website. I was excited to meet him and felt like he was going to be an interesting person to meet. He was extremely direct and upfront about what he was looking for, which was the same as me. Not a relationship. In my case I am a busy solo parent and business owner and don’t really have the time at the moment to put  any effort into a serious relationship. So I was interested in meeting potential lovers. He is also a very busy person who travels for work a lot, also divorced.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He asked me pretty directly what I was interested in, and because his own approach was so unashamedly upfront, I felt able to tell him. We were able to establish this fairly easily, and we then worked out a date on which we would be able to meet up. He suggested we meet for dinner, with a view that if we passed mutual inspection we would go to his hotel room for sex. Planning was definitely involved. We discussed sexual preferences, contraception, expectations, etc beforehand, plus made it very clear to each other that there were zero expectations that anything would definitely happen, just that we were both open to it should we want to on the night. He sent me a photograph of himself naked. It sounds very clinical but I really appreciated him being so blunt and open about it. It made it much less stressful and suited my own approach. There was also warmth in our pre-hook-up chat, some jokes, flirting, and a bit of online foreplay/warming up by talking about what we might want to do together. The dinner itself was tremendous fun. We had some business interests in common and had a very lively and interesting conversation, including striking up conversation with another diner near us, plus talking to the restaurant staff. We had a very frank discussion about prior experiences of sex and our feelings about sex. I found him to be extremely open-minded and non-judgmental which allowed me to open up completely about my thoughts and experiences. After dinner was concluded he took my hand and told me he thought I was beautiful and smart and he would very much like to have sex with me, and asked if I would like to? When I said yes I would like to, we left the restaurant and went to his hotel room which was just across the road.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We started kissing in the lift and then kissed some more in the hotel room. Then he got up and took all his clothes off and suggested I do the same. Again, it sounds clinical but it was actually great as it diffused any tension about getting naked. He was not perfect as most men in their 50s would not be, but he didn’t care one bit about that, walking around naked as he put some music on and got me a glass of champagne. It made me feel more confident to strip off as well. I’m in reasonably good shape but have imperfections I am self conscious about, as a middle aged woman who has given birth a number of times. But I didn’t really care in this situation. He quite casually told me my body was beautiful and he hoped I knew that. 

We started having sex quite quickly, with me on top, allowing me to set the pace and control things. He was quite big and felt absolutely wonderful. I orgasmed reasonably quickly. He then asked me if I was averse to using a toy and I said no, and he went into the bathroom and came back with a We-Vibe which I hadn’t encountered before. We then had sex again, missionary position, using the We-Vibe. While doing this, he was murmuring dirty talk in my ear, I can’t remember exactly what he was saying as I was losing my mind a bit, it was spectacular for me, I had another orgasm. 

He had talked previously about wanting to perform oral on me, but at this stage we discovered that I was bleeding slightly. I had had my period the week leading up to this encounter and thought that it was over, but it had started up again, albeit only a little bit. But he understandably did not want to perform oral then- he said next time. He was quite matter of fact and unperturbed about the bleeding, he got me a towel from the bathroom, and then he proceeded to use his fingers, very expertly to make me come again. 

We then had a rest while I recovered and chatted about fantasies. He asked me what I fantasised about and it was easy to talk to him about that. He suggested he might be able to help me make some of these happen for real if I wanted to, with no pressure. We worked out that I am a bit of an exhibitionist at heart, albeit with limited experience in that area and we discussed the possibility of hooking up again in the future with another couple. 

After that I performed oral on him which was enjoyable for both of us, but he still hadn’t come at this point. He asked me if I wanted him to take some photographs of me doing that, on my phone, for my own personal use but potentially also to show other people we might want to meet up with in the future. He took some photos on my phone of me performing oral sex on him, with my face obscured. Finally he turned me over and entered me from behind, at which point he did orgasm. 

We lay talking for a while about various things and he asked if I wanted to stay over or not. I had a babysitter so needed to return home. He offered to drive me home, but I said I would take a taxi. He walked me to the street and kissed me again, and said he hoped that we could do this many more times, which I was enthusiastic about. We discussed me visiting him for a night at his house in a different town, and also discussed me travelling with him for a few days if he is going somewhere interesting for business. We both reinforced that we did not want to have any kind of a conventional relationship together. 

He was a very good lover, very considerate, dedicated and focused on my pleasure. He tried very hard to make sure I was at ease and was enjoying myself throughout. I told him that he was a very good lover and he said he thought the same of me, in fact he said I was talented and spectacular which made me feel very good.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We discussed this during our chatting before meeting. He told me that he had had a vasectomy and that he was clean and healthy. I am still fertile and am not on contraception so was pleased to know this. I do not have any STIs and told him this. On the basis we both believed ourselves to not have diseases and that pregnancy was not a risk, we had unprotected sex. I am quite aware of the problem with believing him when he told me this. If he goes around having unprotected sex with people then he can’t really be certain he doesn’t have anything, and neither can I. I chose to take the risk, perhaps stupidly, because I don’t enjoy sex with condoms as much. I know it is risky behaviour but did it anyway.

What were your REASONS for having this hookup? Because I am a healthy woman with a strong sex drive who is single. I’m not in the right space to look for a serious partner, too busy, too hard with my kids at the age they are, but I want to have sex and experience sexual pleasure with a man.

Were alcohol or drugs involved? If so, how much? We had drunk wine with dinner, and I felt a little tipsy but not too much at the time we started having sex. He was less affected. By the time I went home I was a little more drunk as he had champagne which was lovely and I had a few glasses.

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? After the hookup I went home and back to my regular life, but I felt wonderful. It had been an immensely pleasurable experience for me and I felt very happy that I had been able to enjoy the sexual side of myself with another like-minded person. It is only a few weeks since the hookup. We have stayed in touch, sending each other the odd message, perhaps every second day or so. It is about equal between us as to who sends the first message. We talk partly about what we are doing, partly about what we might like to do with each other when we next meet up. We haven’t yet arranged a time to do that as he has been in a different country for most of the time, but I have no doubt it will happen. I am optimistic that he is someone who understands the parameters of what I want and is happy with that.

To whom did you talk about the hookup? How did they react? I told my best friend and no-one else, although I told her only that it had happened, with none of the details. She was kind of happy for me that I had had a good time, although she doesn’t really understand it.  She isn’t judgmental but she is someone who is open about the fact she can’t understand the attraction of casual sex. She can’t even really understand that I don’t want or need a partner at the moment. She also expressed some wariness/confusion about what kind of man doesn’t want a relationship.

Was this a consensual and/or wanted experience for you? For your partner? Yes and 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 about this hookup was connecting with someone who seemed to have the exact same feelings about casual sex as me, namely that it is healthy, natural and a whole lot of fun, for people who enjoy sex and who aren’t in relationships. I can’t think of anything bad. 

It hasn’t really changed the way I think about casual sex, but one thing it has added I think, is that I am more optimistic about there being potential casual sex partners out there with the right mindset. What I mean by that, is that with some of my previous casual sexual encounters, I have come across disappointing attitudes from some men, who are happy to have casual sex but harbour feelings (often hidden, but discernible) that women who want to have casual sex are sluts, are damaged in some way or are lying when they say they enjoy it and have hidden agendas. The other kind of casual sex that I don’t enjoy as much is when the man is conflicted and wants to have sex but also thinks that it is dirty or wrong in some way, and brings some guilt along for the ride. This experience was exactly as I like it to be, open, honest, fun, respectful, appreciative and equal.

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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