The Woman from Craigslist

by Derren

What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Brighton
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Self Employed
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Unsure / Questioning
Any other term(s) that describe your sexuality or sexual identity? Heteroflexible
How many sexual partners have you had in your life (including oral sex)? 27
How many hookup stories have you here posted before? 0

The woman from Craigslist

How long ago did this hookup happen? 2 days

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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 38 year old Asian oriental female. We met after she responded to an ad I posted on Craigslist m4w casual encounters. I did not know them at all before meeting and so did not have any feelings about them before the hookup. She told me that she has two children and is still in a relationship with their father but only for the sake of the children. Her partner I believe was in another country and so were her children. She had used craigslist many times before for hookups and once developed a relationship with a married man she had met through the site but his wife had recently found out so she and the other man split up. She was upset about this as she had begun to develop feelings for him but decided to go back on Craigslist. I believe I was her first hookup since the demise of her affair-relationship.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was visiting a town I had previously lived in and knew that I would have a flat to myself for the weekend so I posted an ad on the local Craigslist m4w casual encounters board. I received a response that just said ‘hiya’ so I replied and asked for more info. I got a reply to say that she was Asian, slim, and attractive with a phone number to call. After some deliberation I called the number and we arranged to meet at a bar in town. The advert I posted was very clear that I wanted sex.

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 visiting two bars and paying for a lot of drinks we went back to the place I was staying. We listened to music and I stripped for her, then I started to undress her and she finished it off. I sucked and played with her breasts and kissed her torso and neck. I rubbed her clitoris and inserted fingers into her vagina to stimulate the clitoris and g-spot simultaneously and she achieved orgasm. I then gave her oral cunnilingus for a few minutes. I then put a condom on and penetrated her vagina while holding her legs down so that she was bent in two underneath me. We then carried on with missionary position and she asked if I wanted to cum now. I said I could but let’s change position first so she suggested doggy style. So I was fucking her from behind and then came. She pretty much went and got a shower straight afterwards and asked me to book her a cab which I did. It felt a bit like I imagine using a sex worker to feel like, but not quite. She was funny and we had a good time talking but the sex lacked real intimacy and didn’t last long. After she had cum she wasn’t very interested in doing much more. I asked if everything was ok and she said yes, that once she’d come she was basically done, that ‘I knew what I was doing’ and that I could call her again when I’m next in town. She had a slightly dominant personality whilst we talked at the bars and we discussed kink, she said she can also be submissive and I suggested we explore this one day which she was open to.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, 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? I felt that my confidence had improved. I have recently come out of a long term relationship and although it was open and I had played around with other women recently this is the first time I’d had full penetrative sex with a woman other than my (now ex) partner for about 3 years. I had also been rejected recently by women I liked so my self esteem was not great. This hookup coupled with spending a lot of time with good friends over the weekend made me feel better about myself. I don’t have any hopes or expectations for this person. I may contact them again to see if they want to come over for sex but I do not wish to pay for expensive alcohol next time. I don’t really believe in the man paying for everything – in this context it just felt like I was paying for sex and if I wanted to do that I’d rather pay an actual professional for a better ‘service’ – but for hookups I’d prefer the enjoyment was more mutual.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, Making new friends, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? A few female friends and one male friend. They enjoyed the story. They know I have a very high sex drive and sometimes partake in casual sex so were not especially surprised. Some were curious about the wording of the Craigslist ad I posted so I let them have a link to the ad. I told my ex from 8 years ago about it over facebook and this developed into quite a sexual conversation between us.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? She was very attractive I liked her body type (slim). She had a tight vagina. She was kinda fun to be around although not someone I’d usually be friends with.

What was the WORST thing about this hookup? It was a little bit mechanical, I’d have liked a little more of a genuine connection, more kissing, more sex, her to give me oral and so on.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really I suppose it might be that I now have more confidence in instigating and following through on casual encounters like this one.

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

All things considered, how NEGATIVE was this experience? Not at all 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? I’m not sure how I feel about totally casual sex. I have absolutely no moral issue with it but I have rarely just engaged in sexual acts without at least spending some time chatting too and flirting with the partner. IT could even just be half an hour over a beer but I like to find the chemistry and vibrations between us ideally before jumping into bed. I also like if possible to openly discuss with the other person what we enjoy or don’t. I have had a few very casual hookups with men, but I much prefer women and much prefer to flirt and find a chemistry with them before going to bed but I have also had quite casual encounters with women – but they are never as satisfying as when some sort of connection, however fleeting is established. I have always been very sexual with a high sex drive and don’t judge anyone on their (consensual) sexual decisions. I don’t like how sex negative society is and think that it damages so many people. I have recently read ‘the Ethical Slut’ which made me realise how sex negative society is and how sex negative my upbringing was. I think people are sometimes taught to place too much problematic significance on sex, I mean I believe it is profound but it doesn’t have to be exclusive or rare to be profound, but then I find it easy to love and connect with people in general. I have lived in communal housing where there were overlapping polyamorous relationships and have seen how this can work and dislike the judgements people make about for example swingers and poly people. I don’t think heteronormative monogamous relations ships between people of binary genders should be the default setting but one of many ways of doing relationships based on individual preferences and needs.

What do you think about the Casual Sex Project? I think it’s great. I suppose it’s open to abuse or lies but I think it’s usually clear when a story is genuine and when it is fantasy. It’s good to have this stuff that is often not talked about openly in the public domain, to inform a more honest discussion about casual sex and it’s role in people’s lives and wider society

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