Seduced By An Older Woman



What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Turkey
Highest education received: College degree (eg., BA, BS)
What’s your occupation? self-employed
What’s your current relationship status? Single
Religious affiliation: Muslim
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? none
How many sexual partners have you had in your life (including oral sex)? 100
How many hookup stories have you here posted before? 0

Seduced By An Older Woman

How long ago did this hookup happen? 25 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For more than 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? She was a very good friend of my mum who I had known since I was a child. She was married and had one small child but, her husband used to drink a lot. I had witnessed quite a few arguments between them when they came around to visit my parents or we went to theirs. She was Mediterranean looking with dark hair and light skin. Her best feature was her backside, which was round and big, but still looked great on her body, which was just a little bigger than I would classify as slim.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I must have been around 18 when she started flirting with me. I think she must have realized that I couldn’t keep my eyes off her, and particularly her bum, whenever I got the chance. It got a little weird for me because I think her husband realized too, but it felt like he was encouraging me. On one occasion she actually revealed the tops of her legs and panties, when her son was sitting on her lap, blaming him for being restless. She would also touch my arm and even leg whenever she got the chance. There were a lot of signs, but I was scared of the consequences and felt weird about her husband seemingly encouraging me. Then I went traveling one summer, during university and we ended up in the same place. They were moving on to a resort and asked me if I wanted to come. That’s where we finally hooked up.

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? The actual hook up was more than 25 years ago, but it had such an effect on me that I remember it as if it was just yesterday. The first night we were at the resort her husband got drunk a lot and went to bed early. She was going to put her son to bed but, she said she wanted to stay up a bit more and asked me if I would go to the hotel disco with her. We danced, including a couple of slow dances. I had also had some drinks, so was feeling a little braver, and actually made sure our legs were fully touching throughout the slow dances. Even if she had been touchy in the past, I never got so close to her before. We then went for a walk and sat down in a quiet area on the beach. She was questioning me about the girls at university. She asked me what I liked (physically) in women. I said legs and bum, to which she replied that she had guessed. I had a little trick, which I had used on her son, and she had seen which basically entails tickling the knee area. She said she was curious as to how it felt, as her son had got into fits of laughter when I did it to him. So she asked me to show her. When I did, she started laughing too, but grabbed my hand and held it in place on top of her knee. She then came out and asked me if I thought her legs were nice. I felt the air getting very heated, and the way she was looking into my eyes and the way she had asked me had me getting hard. I felt nervous and mumbled a yes, but as she relaxed her grip on my hand, I had the courage to keep it there. She put her hand on my leg and started stroking. As she was gradually moving her hand up my leg, I felt that I had been given the green light to go further up her leg too. Eventually, she was stroking halfway up the inside of my thigh, through my trousers, and I was doing the same to her naked thigh, under her skirt. There was a wooded area nearby and she said we should go there. She was sensually stroking my back, through my shirt, and that was making me even more aroused. I was actually worried that she would notice. I soon found out that she was well aware of it. A little after we got to the wooded area, she suddenly stopped, turned towards me, and hugged me and kissed me on the cheek. But it wasn’t just a peck. It was a very sensual and very lingering kiss. I kissed her too. Then I suddenly felt her legs and thighs rubbing against mine, and my cock rubbing against the top of her thighs. She looked into my eyes, said, “our secret” and kissed me on the lips while moving her hand down to unzip my trousers. What followed was her kneeling down to suck me off. I was already very excited, so didn’t last long. I think I must have come quite a lot because she swallowed some, but couldn’t deal with it all and spat some out. I was ecstatic. She took the lead again, saying we should go to my room and clean up. I thought that was it, so I felt a bit dejected. I really wanted to fuck her. I think she saw the look in my face, and then said, we could continue in my room. When we got to the hotel building, we were alone in the elevator, and I couldn’t keep my hands off and groped her bum. She turned around and ground her bum against my cock, which I could feel starting to stir again. In the room, we started kissing passionately and touching each other as soon as the door was shut. It never even occurred to me that I had just come in her mouth and was now kissing her. I probably wouldn’t have cared even if it had, anyway. The clothes came off, going all over the room. I finally got to get my hands on her naked arse. We stumbled onto the bed and she just took hold of my cock and guided me inside her very wet vagina. After a little while, she said, “You like my arse, don’t you? Do me from behind.” She turned over into doggy position, and then, once I had entered again, she actually lay down flat on the bed, with her arse just naturally sticking out. I finished inside her.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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 was ecstatic. I had been fantasizing about her for about three years. But I was also worried that I could give something away with my behavior when I saw her husband the next day. Luckily, he started drinking again from mid-morning and was worse for wear quite early in the day, thanks also to the heat, throughout the whole holiday. Other than that, I did feel bad about sleeping with someone else’s wife, especially since I liked her husband and thought he was a good bloke too. But that didn’t stop me from hooking up with her again, both during the holiday, and again several times over the next few years. Eventually, also let me do anal, which she said was a first for her. I learned a lot from her, including how to eat pussy (which is something I really love doing now).

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, 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), Emotional intimacy, closeness, connection, Intoxication

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? No one. I didn’t feel anyone would understand, and it needed to remain a secret.

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? 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? Finally getting what I had been fantasizing about for a long time. And the reality turned out to be just as good as the fantasy.

What was the WORST thing about this hookup? Feeling bad because her husband was a good bloke. However, there was a brief period a couple of years after the first hook up when I felt very different because just after my parents split up, around that time, he said some nasty things about my dad, and that upset me. In fact, the next time I was with his wife, I was a little more aggressive and felt more of an urgency. That probably reignited our affair, which had started to feel less and less exciting over time.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? She was my first “older woman” fantasy. I actually fantasized about other older and married women as well, both before and after we hooked up. I actually became so into this that I ended up going to swinging events, just to hook up with other older women.

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

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

Anything else you want to add about this hookup? Maybe the one thing that was a little negative was that for a few years I actually avoided relationships with women my own age, preferring older women.

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 have no problems with it. I am quite a pro at open relationships. It is difficult for me to understand how a person, of either sex, can have a fulfilling sex life, with just one partner, for the whole of their lives. I think the internet and online dating apps in various forms have made casual sex more freely accessible. Still feel a little guilty if the person I hook up with is going behind her partner’s back. But it does sort of give me a strange enjoyment to know that we are doing something forbidden!

What do you think about the Casual Sex Project? I like it. I am happy that I found it. Would quite like it if the categories were a little more specialized (for instance a separate heading for older women, older men, cheating, etc.), so it is easier to find the stories everyone is more interested in.

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