Unexpectedly Three in a Row



What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? London, England
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Senior Manager
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
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)? 21
How many hookup stories have you here posted before? 0

Unexpectedly Three in a Row

How long ago did this hookup happen? Yesterday

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Paid sex

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? The first was a Polish escort I’ve been seeing once or twice a month for about eighteen months. We have become more friends than it’s maybe wise to be, but the sex is still good. The second was a Rumanian escort I hadn’t seen for a couple of years until yesterday. I had been having a difficult time at work and home and somehow this was part of why I contacted the first escort for a lunchtime meetup who didn’t reply that quickly – when this happens she is usually back in Poland – so I texted the Rumanian escort for a meetup at the end of the day, as I was going to be nearer her part of town for work then. The third was my partner who I’ve been with for just over three years. She travels a lot and we often have sex just beforehand as a farewell bonding, though we hadn’t been getting on that well and I wasn’t hoping or expecting it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began at about ten in the morning when I texted my Polish friend/escort and didn’t hear back. I texted the Rumanian then, and arranged an early evening meet up. Only much later, about quarter to one in the afternoon did Ms Polish text me to say come over, which I did straightaway. It felt wrong to cancel the Rumanian in itself, but I also hadn’t seen her for ages and wanted to know how she was. Finally at about half ten at night, both of us getting an early night in separate rooms, my partner came into the room I was in with lube, a condom and a happy face. “It’s got to be quick,” she said, smiling.

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? Ms Polish is down on her luck at the moment, suffering from a hormone imbalance which gives her severe headaches. She’s being treated but is tired and spaced out. She was glad to see me – we talk mostly about her problems, including family ones back home, and then we transition to tender sex. Recently I’ve asked her to wear underwear, just standard underwear, when I arrive, as before it was just a negligee and bare beneath – which I don’t find exciting. She gives me a gorgeous blowjob without a condom, I kiss a lot, a kind of boyfriend experience, lick her tits and give her as much oral as she wants. She then pops a condom on and we usually do missionary which she says she prefers in her real life. She came before I came this time; she doesn’t always come, but fairly often. We talk a little afterward, again usually about her illness and I try to give her optimism. I feel sadder and sadder with Ms Polish and also less excited by her (and guilty than I feel less excited).

With Ms Rumanian, again we are nearly at a kind of friendly level, though clearly not possible in an escort situation, and we talked about her teenage daughter back home, being looked after by her sister; the daughter has recently had difficult heart surgery, successfully. Ms Rumanian is going to go home permanently probably this year, so I was very glad to catch her before. She says so where you’ve been sticking that dick of yours, but she’s laughing (maybe a bit hurt, too?), and I just smile and shrug it off, “here and there, but not too much.” Unlike Ms Polish, who used to be a medical doctor and has low-key style (no make-up, conservative style), Ms Rumanian wears red lipstick and sexy underwear. She always asks about me and my family and we’ve both got problems that we can relate to. After talking, she invites me to shower, I take my trousers off, but then she’s got her hands in my boxers and my cock hardens and peeps out, she’s joking about how I mustn’t wear shorts in summer, and then I’m wholly undressed, she’s tit-fucking me a bit, then a condom on before she blows me for a bit. She touches my balls and my perineum and I lift up my arse hoping she’ll put her fingers in, but she doesn’t. She is exciting in a way that Ms Polish isn’t, I like her long straight dark hair touching my skin, and then I’m licking her pretty big tits, moving my tongue gently around the nipples like I like to do, and then moving down. Unlike Ms Polish she is not completely shaven down there, has a little hairy ‘landing strip’, something I like, and now I’m licking her clit, and I’m saying I missed your cunt (I love that word, cunt, but I hate it used violently), and then she’s on her back and it’s missionary again. I’m surprised I feel big and hard, as I’m 50 and not what I used to be in that department, but all is good, I love fucking you I say, and we fuck and I come (she doesn’t come, though she has in the past). She notices there’s hardly any sperm in the condom and asks when I last had sex, but I just laugh and say nothing. She’s a clever one, and I like that. We leave on really good terms, and I’m sure I’ll be back before she leaves. She tells me, ‘maybe we do some prostate massage next’, but I’m all coy and non-committal and then I do say, “I might like that.”

I go to my work thing, get back home. Our child is still awake and I read him a story before I even see Significant Other, though I say hello (I can see she’s napping on the sofa) and he takes a long time to get to sleep, then I join S. Other, we watch some tv and decide we’ll go to bed earlyish as hard day for both tomorrow. I’m reading in bed and she comes in with lube and a condom, laughing, telling me to let’s be quick. She just takes her pajama bottoms off, she has a gorgeous arse, and for a few minutes, we get each other going. She is very wet, the wettest I’ve known her for a couple of years, and we don’t need the lube at all. I am really turned on by that, and, though I was nervous I wouldn’t be able to get it up after a day like today, there’s no problem and again I am bigger and harder than I’ve been before today for a while. She crouches right down, on the bed, across its breadth. Do it this way, she tells me, meaning I’m to be standing up as we fuck, I mean me off the bed, next to the bed, doing it doggy, but she’s not on all fours, she’s sort of bent her body in more than that. I put the condom on and enter her, she’s wet but very tight (I always think her having a Caesarian means her vagina stayed that way). In the recent past, I’ve been afraid of coming too soon as she has been furious if I come and she hasn’t come yet, but tonight I just fuck her relatively, but not painfully, hard and she is happy. I think she does come, but she doesn’t like talking about that kind of thing afterward, all I know is she’s happy and we go to bed in our separate rooms, no talking after that. I feel very good, an amazing day, full of a kind of love, or a lot of different kinds.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? Today is the next day and I feel great – such amazing luck.I also feel relieved I haven’t been caught by my Significant Other – I wish I could feel guilty for liking casual sex, but I don’t. But I do feel the high risk of being caught and the damage to the family in the fallout.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Noone.

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? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best thing was the fantastic sex with Ms Rumanian and then with my longterm partner. It was brilliant in itself, but also reassured me that I can still have great sex (Iif I am right in thinking that Ms Rumanian and my partner also enjoyed it a lot, but that is perhaps to assume to much). There is something braggish about having three different partners – almost by accident, so it wasn’t a macho thing – that is just a glorious wonder.

What was the WORST thing about this hookup? I worry about my escort hookups, they have such tough lives, and I still don’t know if I am unequivocally just making things worse by being their customer. It also reminded me that things are not great emotionally between me and my partner and I can’t see them being fixed or me breaking things up either – a kind of strange disagreeable limbo at times.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, it’s just confirmed what I already know – I like different kinds of sex, casual sense alongside apparently monogomous sex, incompatible with what society publicly owns up to.

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

All things considered, how NEGATIVE was this experience? A little negative

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? Casual sex is now very important in my life. I only met my current partner after having casual sex with her, while I was in a longterm relationship that had changed drastically when that partner became permanently and severely disabled it. I over-reacted and rushed into another longterm relationship after that, not understanding that I could have casual sex without that. Since that disability accident I slept with over a dozen people in just a few years – before it, I had only had two, monogamous, relationships with no casual sex at all.

What do you think about the Casual Sex Project? I think it’s brilliant and may even be important.

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