Sex with a Man 39 Years Older Than Me



What’s your gender? Woman
How old are you? 18
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Surrey, England
Highest education received: Some college (not currently in college)
What’s your occupation? Working holiday
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Inexperienced
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? None

Sex with a Man 39 Years Older Than Me

How long ago did this hookup happen? Last week

What was your relationship status at the time? Same as current status

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? My mother’s 57-year-old ex-boyfriend from before she met my father. I had never met him before the hookup.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Bob took me and a friend out for dinner to celebrate my 18th birthday. Sex was in his bedroom with my friend in the living room.

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?

I finished high school last year and like many Australian’s decision to take a gap year before starting university. As my grandmother was coming to Australia for a year I had the use of her apartment in England so my friend Nairy and I decided we would live there while we worked to save money before backpacking around Europe.
I was young for my year so didn’t turn 18 until last week. A few weeks ago I was talking to my mum and told her I was disappointed that my birthday celebration would be a few drinks at the local pub as I had no money. That was when she suggested I contact Bob. He was her boyfriend before she met my dad. Mum had always told me what a great lover Bib was and I often suspected she occasionally got together with him even after she and dad got married.

My mum is convinced I’m a complete prude, perhaps I am, but she is always going on about how I should act sexier and dress to show off my beauty. I’m five feet five, slim, pretty and have 34c breasts but never wear anything revealing. I also only had my first boyfriend last year and mum thought I was still a virgin.
Anyway, I called Bob and he told me that my mother had already called and he would be delighted to take Nairy and me out for a nice dinner. The date was set for two days after I turned 18. When I put down the phone I thought, “Imagine if I had sex with Bob and he told my mum I was great in bed! That would shock her… and me!” Over the next few days I occasionally thought about it again but really thought the idea of sex with a man who was nearly sixty and my mum’s ex-boyfriend was pretty disgusting. I did, however, decide I would flirt with Bob and make him think I was up for it.
The day before our dinner I planned a sexy outfit, skirt half way to my knees, heels, pushup bra, buttons were undone on my shirt and “slutty” makeup. I even waxed my bikini line and “accidentally” spilled some wax resulting in a complete Brazilian, which I’d never done before.
That night I was lying in bed and the smooth feeling of my pussy got me extra aroused. I got out my vibrator and was really going for it. At one stage I stuck my vibrator up my bum, which I often did, and started fantasizing about fucking Bob! With the vibrator up my bum and fingers on my g spot, I had a huge orgasm imagining Bob watching me and cumming in his pants moaning “you are the sexiest girl I’ve ever met”. I knew it would never happen but it did get me all the more determined to wind Bob up so to speak.

When I dressed for the evening I decided I might give Bob a little flash so didn’t wear knickers!
We arrived at Bob’s apartment and met his friend Marty and had a gin and tonic before leaving for the restaurant. I could tell Bob was interested and he kept looking at my somewhat exposed breasts and I was certainly playing up to him.
We were seated in a booth with Bob next to me and after a few champagne cocktails I was really playing up. Then I felt Bob put his hand on my thigh. My plan was definitely working and he started to move his hand up my leg when I remembered I wasn’t wearing knickers and pushed it away. Damn, I thought now he would think I was just teasing, so I went to the bathroom and when I came back I had undone another button on my blouse.
After dinner, we went back to Bob’s for a nightcap by which time I was really quite tipsy. So when Bob asked if I would like to see the view from the other side of his apartment I quickly, and naively said yes. As we walked down the hallway I realized this was code for “would you like to fuck me?” My head started racing, “how would I get out of this without looking like a stupid schoolgirl?” I decided when he asked I would simply say he was too old for me.
We got to his bedroom and he showed me what was a magnificent view of London. Conveniently, although it didn’t occur to me at the time, the view was best seen by leaning on a ledge so that I was bent over ready to be fucked.

When Bob asked if I would like a shower I really freaked out but managed a calm “no thanks”. He said he would and suggested I enjoy the view while he did. There I was, alone in his bedroom, my head spinning, wondering if in this position my skirt fully covered my pussy and frantically thinking how was I going to get out of this and maintain my dignity.
When I heard the bathroom door open my heart rate doubled, I peeked back to see Bob in nothing but a bathrobe. Stunned I concentrated on the view. I figured Bob would invite me to the bed and then I would say no but he gave me no chance. He simply came up from behind, lifting my skirt and started to put his cock in my pussy and instinctively I pushed back and then sort of blacked out. I was not sure how long I was out for, perhaps a minute or two, but when I came too Bob was pumping away and moaning how beautiful I was. My head was still spinning and I thought I had to take control. I wanted Bob to think this was my idea and that I was a sexy and sexually experienced woman. I reached between my legs and massaged his balls. His sped and moaning increased and I thought he was about to cum when he pulled out.

Bob then asked me to turn around and took off my blouse and skirt. There I was in nothing but a bra and heels with my bald pussy completely on show. Then Bob stepped closer and put his hands on my shoulders and I knew what he wanted and squatted down. This was my chance I thought. My boyfriend told me I gave the best blowjobs. I could control my gag reflex so was able to deep throat with ease. I decide Bob was about to get the best blowjob he had ever had. Slowly I licked his shaft then gradually devoured his cock all the way to my lips which were touching his balls. Bob wasn’t that big so it was very easy. I was sucking away and pumping his cock when Bob asked me to look at him. I did so and smiled when I saw the expression on his face, he was having the time of his life and looked like an excited puppy dog. I sucked his balls then went back to his cock and he started pumping deep down my throat. Again I thought he was about to cum and not wanting sperm on my bra so I took it off. I was actually getting turned on and reached down to my pussy. I was dripping wet! Then Bob pulled out and asked me to sit on the edge of the bed.

He asked me to part my knees and then to lie back on the conveniently placed cushions which I did. Then he asked me to put my hands behind my knees and bring them back to my shoulders. There I was with my pussy wide open while this old man masturbated repeating “oh you are beautiful.” I had mixed feelings of fear, disgust, and embarrassment but was also extremely turned on. The look on his face was one of sheer pleasure. I was enjoying the fact that I had so much ability to turn him on and that I was acting like a complete slut. What would my mother think?
I started to rub my clit and Bob put his cock back inside me. He would put his cock in and pull it out and moan “you are beautiful, you are stunning, you are so sexy.” I was feeling the horniest I had ever been but still wanted to make sure this was MY plan in case he told my mum about it.
I asked Bob to give me a moment, then I stuck a finger in my pussy and then starting massaging my arse. I lived it up well then grabbed my cheeks and said: “be gentle”. You should have seen the look on his face! I AM A COMPLETE SLUT I thought and imagined my mum hearing about this. Bob slowly entered my butt and even though I was used to my vibrator being in there it did hurt at first. Then I started moaning while Bob pumped deep inside. I stretched my neck to get a good view of his going in and out of my arse and came again. I could sense Bib was about to cum and thought a good slut would let him cum in her arse but didn’t want cum dripping out of me all the way home so I told him I wanted him to cum in my mouth and got down on my knees. He came in seconds and I kept thinking, “Liza the slut, how about that mum!”

While I was getting dressed Bob told me that lots of his friends would pay good money to have sex with such a beautiful girl. I was shocked but asked, how much? When he said for anal they would pay 3,000 pounds or more I told him I would let him know.
It was a bit embarrassing going back into the living room where Nairy and Marty were sitting so we left straight away. I told Nairy I only gave Bob a blowjob (only to shock my mother) but wanted to tell her everything.
I can’t stop thinking about sex with his friends and the look of pleasure they would have to fuck my 18-year-old body really turns me on. I think I will call Bob after I finish this and arrange a date. That’s another story

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? As I said, I’m planning on going back for more with a different old man.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? To prove to my mother I was sexually liberated

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A 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? A little bit

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

Do you regret this hookup? A little bit

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