Straight Female / 20
When I say I had sex with an older man, I mean much older. Bob was an old boyfriend of my mother's he was 57, I had just turned 18! My name is Liza, I'm 20 years old, in good shape and did some modeling when I was 17. This all happened whilst I was living in England. It was my gap year and my friend Nairy and I were staying in my grandmothers flat in Surrey while she stayed in Australia with my mum. We both had jobs and were saving to backpack around Europe for a few months.
I was young for my year and didn't turn 18 until May of the year after my HSC. That was six weeks after we arrived in England and were frantically saving for travel. That meant a couple of drinks with Nairy at a nearby pub to celebrate my 18th. Or I could call Bob.
My Mother dated Bob when she was 19. He had never married, lived in London and was loaded. She still kept in contact with him and suggested if I rang Bob, he would take Nairy and I somewhere special to celebrate. I did as Mum suggested and Bob was very happy to hear from me, we arranged to meet at his place before he would take us out for dinner. It would be two days after my 18th birthday.
My mother had often talked about Bob, mostly telling me what a great lover he was! Which I found kind of weird that she would tell me. But my mother was always encouraging me to enjoy sex and act sexy, as she called it. She thought I was a prude and thought there might be something wrong with me as I waited until I was 17 to lose my virginity. She took me to the doctor to get the pill when I was 15! All of that is to say that I often wished I could prove to my mother I was good in bed and enjoyed sex, it's just that I didn't talk about it all the time.
That night I dreamt of fucking Bob, not being fucked by Bob. I was in charge, I was the aggressor so to speak. Throughout the dream Bob kept moaning how; beautiful I was, how sexy I was and that I was the best fuck he had ever had! Having a weird dream doesn't mean much but what happened next did. I woke up and masturbated til I came, all the while imagining Bob moaning "you're the best, you're the best".
When I woke in the morning I struggled to understand how thinking about fucking a guy three times my age could turn me on? Yuk! I thought. But the idea of Bob somehow telling my mother I was the best fuck he had ever had did turn me on. I decided I could have almost as much fun if I didn't fuck Bob but made him think he was going to. I was going to be an absolute flirt, maybe even a flash some boob or? I planned to act like a slut to such an extent that Bob would actually proposition me. Then I would let him down by explaining that "whilst I would like to, I would feel like I was cheating on my mother". I began to get nervous that I could in fact, do it. "What if he just thinks I'm a silly little girl"? I decided I could make a judgement on the night. If he seemed interested, play up. If he doesn't seem interested tone it down.
It just so happened that Nairy and I were getting free makeovers from students at a nearby Beauty School on the morning of the day we were due to have dinner with Bob. Hair, make-up (I told the girl I wanted a bit of a slutty look!), nails, a spray tan, and I had my first brazilian! Not completely, I left a little strip of my blonde pubic hair at the top. We wore loose dresses home so the tan didn't smudge and I didn't wear any knickers. The cool breeze on my bald pussy gave me tingles, I loved being bald.
I wanted to look like I was "up for it" so to speak, but I didn't want Bob to think I was easy. I wore a summer dress that went to mid thigh length, heels and a jacket. Oh, I also wore a push up demi-bra and...no knickers! I did think I looked hot and the idea of Bob trying to get into my pants made me even hotter.
We had a Gin & Tonic at Bob's where we also met Marty. Bob was as expected, charming, quite good looking, although a little overweight, and ogled me from the moment we met. He was definitely interested.
At the restaurant I had 5 Brandy cocktails, yes 5! I was getting quite tipsy but felt I was in control. When Nairy and I went to the bathroom she asked me if "I was planning on fucking Bob?" "Because it sure looks like it" she added jokingly. When I responded "I'm not planning to have sex with Bob, but I am hoping he thinks he's a chance"! Her jaw dropped and she said "I hope you know what you are doing?" When we got back to the table I toned it down a bit.
But that wasn't stopping Bob. After a while I felt his hand on my knee. "Don't freak out" I thought, "let him think he is a real chance". Then his hand started moving slowly up my thigh. I froze and then, just in time, pushed his hand back down. "Phew" I remembered I wasn't wearing anything under the dress, I didn't want him to think I was that easy!
I ordered another drink to calm my nerves. We finished at the restaurant and went back to Bob's for another drink. I didn't intend on drinking mine, I'd had enough to drink. I was disappointed I had pushed Bob's hand away, "now he will think I'm all flirt and no action". I wanted him to ask for sex so I could pretend it was cause of my Mum, not cause I'm inexperienced or frigid. I was trying to sit in such a way that he could get a look at me pussy when Bob suggested he take me to the other side of the apartment to see the view. I knew that was code and thought "great, now I can let him down". As we walked down th hall I reassured my self that I was in control. Was I? I wasn't sure I could pull off the let down in a way that made him feel I was up for sex, but not with him.
And yes we were in Bob's bedroom! The view of London was magnificent, but the window was a little low so I rested my arms on the shelf and just stared at the view. Then Bob asked "if I would like a shower". Oh my god, it was happening! "No I'm fine" I said. Bob then told me he was having a shower I should just enjoy the view. There I was bent over, my dress only just covered my pussy, staring at the view with a million thoughts racing through my mind. Mostly about how was I going to get out of this? Act cool I told my self and say "Oh Bob I'm flattered that you are interested but I couldn't do that to my mum". Over and over it was going through my mind when I heard the bathroom door open. I glanced back without turning around and it looked like Bob was wearing a bathrobe without the belt. Oh shit! I am freaking out! I was just about to turn around and blurt something out when it just happened. In one quick movement, Bob lifted up my dress and shoved his cock in my pussy. Instinctively I pushed back, did I really want this after all? Then my head started to spin, Oh my god, what have I done. Then I sort of blacked out for a few minutes. When I "woke up" so to speak, my first thought was "be experienced" whatever that meant, and then the reality that I was being fucked by a 57 year old man while my friend was in the next room hit me. "Can't stop now", I told myself. I wanted Bob to think I was experienced, so I reached between my legs and started stroking, then squeezing, his balls. Bob moaned a little louder.
After a few more minutes Bob pulled out and asked me to turn around. He then asked me to let my dress fall to the floor. I was completely embarrassed as I wiggled out of my dress, I hoped it didn't show. My dress fell to the floor and I stepped out of it. I was standing in nothing but heels and a bra and Bob staring at my bald pussy saying how beautiful I was. Then he stepped closer and put his arms on my shoulders. I knew what he wanted.
"This was my chance" I thought. I give great blowjobs! I can control my gag reflex so I can deep throat easily. I was going to show Bob I was a woman of the world!
I knelt down and started licking his shaft, then slowly I engulfed his entire cock and my lips were pushing against his body. I pumped up and down his cock and would stick out my tongue to lick his balls. Bob then asked me to look up at him while I sucked his cock. I looked up and he just kept moaning "you are so beautiful" over and over. I did like the look of sheer ecstasy on his face but went back to focus on a great blow job and then licked and sucked his balls. Bob grabbed his balls and moved as if he wanted me to lick his arse. Something I've never done but I thought "you've come this far, make it a night he will remember". I licked his arse and then went back to deep throating him, only this time he was pumping me.
Bob pulled out of my mouth quickly and held his cock. I think he was about to cum. Then he asked me to sit on the edge of the bed with my legs apart. This was definitely not me, I was freaking out again, but desperately trying not to show it. I did as he asked and he just stood there rubbing his cock moaning how beautiful I was. Then he asked me to lie back and bring my knees to my shoulders. I don't know how I was doing it but I was. And then he asked me to masturbate. Strangely I didn't freak at that. I figured I could hide my pussy with my hands and that would reduce my embarrassment of being in a pornographic pose in front of my mother's old boyfriend!
I started to masturbate and it actually felt good, my pussy was wet and tingly. I decided the only way I was going to get something out of this was to bring myself off. I really started going for it, rubbing my clit and stickking two then tree fingers in my pussy. Bob kept rubbing his cock and moaning and I was about to come when I felt his cock nudging my pussy. His cock wasn't very big so it was a let down after my fingers. I rubbed my clit while Bob watched his cock sliding slowly in and out of my bald 18 year old pussy. He was in heaven, and strangely so was I!
I just blurted it out. I was embarrassed the second I said it but while he was fucking me I asked Bob if I was better than my mum! He paused and started to say well...I quickly stopped him and said why not? He responded with "she likes anal". Oh my god, I'd never been fucked in the arse, but I didn't want Bob to know that. I instantly wished I hadn't said it but I simply said "who said I don't?" I could feel myself shaking, not because I didn't think I could handle it. I hadn't been fucked there but I did like to stick my vibrator up my but and it was bigger than Bob's cock.
I slipped my fingers in my pussy and use the lube on my arse. Then with my knees up near my shoulders and Bob staring at my pussy while he jerked off, I stuck one then two fingers up my butt. Bob then moved in and slowly slid his cock in my arse. I closed my eyes and tried not to think how I was getting butt-fucked by a 57 year old man that used to be my mothers boyfriend. Bob soon came, in his hand, and it was over, or so I thought. As I was getting dressed he said he had an idea for how I could make a lot more money than working in an office.
Quite casually he said he had many friend who would pay a lot of money to have a few hours with me. I asked him what a lot was and he said 1000 pounds and hour!
Over the next six weeks I had sex with about thirty guys, all over 50. I had 2 & 3 guys at once on a couple of occasions and earned over 60,000 pounds.
That was 18 months ago and I've since returned to Australia, but I'm heading back to London next week. Imagine how much money I can make in a year!
I was young for my year and didn't turn 18 until May of the year after my HSC. That was six weeks after we arrived in England and were frantically saving for travel. That meant a couple of drinks with Nairy at a nearby pub to celebrate my 18th. Or I could call Bob.
My Mother dated Bob when she was 19. He had never married, lived in London and was loaded. She still kept in contact with him and suggested if I rang Bob, he would take Nairy and I somewhere special to celebrate. I did as Mum suggested and Bob was very happy to hear from me, we arranged to meet at his place before he would take us out for dinner. It would be two days after my 18th birthday.
My mother had often talked about Bob, mostly telling me what a great lover he was! Which I found kind of weird that she would tell me. But my mother was always encouraging me to enjoy sex and act sexy, as she called it. She thought I was a prude and thought there might be something wrong with me as I waited until I was 17 to lose my virginity. She took me to the doctor to get the pill when I was 15! All of that is to say that I often wished I could prove to my mother I was good in bed and enjoyed sex, it's just that I didn't talk about it all the time.
That night I dreamt of fucking Bob, not being fucked by Bob. I was in charge, I was the aggressor so to speak. Throughout the dream Bob kept moaning how; beautiful I was, how sexy I was and that I was the best fuck he had ever had! Having a weird dream doesn't mean much but what happened next did. I woke up and masturbated til I came, all the while imagining Bob moaning "you're the best, you're the best".
When I woke in the morning I struggled to understand how thinking about fucking a guy three times my age could turn me on? Yuk! I thought. But the idea of Bob somehow telling my mother I was the best fuck he had ever had did turn me on. I decided I could have almost as much fun if I didn't fuck Bob but made him think he was going to. I was going to be an absolute flirt, maybe even a flash some boob or? I planned to act like a slut to such an extent that Bob would actually proposition me. Then I would let him down by explaining that "whilst I would like to, I would feel like I was cheating on my mother". I began to get nervous that I could in fact, do it. "What if he just thinks I'm a silly little girl"? I decided I could make a judgement on the night. If he seemed interested, play up. If he doesn't seem interested tone it down.
It just so happened that Nairy and I were getting free makeovers from students at a nearby Beauty School on the morning of the day we were due to have dinner with Bob. Hair, make-up (I told the girl I wanted a bit of a slutty look!), nails, a spray tan, and I had my first brazilian! Not completely, I left a little strip of my blonde pubic hair at the top. We wore loose dresses home so the tan didn't smudge and I didn't wear any knickers. The cool breeze on my bald pussy gave me tingles, I loved being bald.
I wanted to look like I was "up for it" so to speak, but I didn't want Bob to think I was easy. I wore a summer dress that went to mid thigh length, heels and a jacket. Oh, I also wore a push up demi-bra and...no knickers! I did think I looked hot and the idea of Bob trying to get into my pants made me even hotter.
We had a Gin & Tonic at Bob's where we also met Marty. Bob was as expected, charming, quite good looking, although a little overweight, and ogled me from the moment we met. He was definitely interested.
At the restaurant I had 5 Brandy cocktails, yes 5! I was getting quite tipsy but felt I was in control. When Nairy and I went to the bathroom she asked me if "I was planning on fucking Bob?" "Because it sure looks like it" she added jokingly. When I responded "I'm not planning to have sex with Bob, but I am hoping he thinks he's a chance"! Her jaw dropped and she said "I hope you know what you are doing?" When we got back to the table I toned it down a bit.
But that wasn't stopping Bob. After a while I felt his hand on my knee. "Don't freak out" I thought, "let him think he is a real chance". Then his hand started moving slowly up my thigh. I froze and then, just in time, pushed his hand back down. "Phew" I remembered I wasn't wearing anything under the dress, I didn't want him to think I was that easy!
I ordered another drink to calm my nerves. We finished at the restaurant and went back to Bob's for another drink. I didn't intend on drinking mine, I'd had enough to drink. I was disappointed I had pushed Bob's hand away, "now he will think I'm all flirt and no action". I wanted him to ask for sex so I could pretend it was cause of my Mum, not cause I'm inexperienced or frigid. I was trying to sit in such a way that he could get a look at me pussy when Bob suggested he take me to the other side of the apartment to see the view. I knew that was code and thought "great, now I can let him down". As we walked down th hall I reassured my self that I was in control. Was I? I wasn't sure I could pull off the let down in a way that made him feel I was up for sex, but not with him.
And yes we were in Bob's bedroom! The view of London was magnificent, but the window was a little low so I rested my arms on the shelf and just stared at the view. Then Bob asked "if I would like a shower". Oh my god, it was happening! "No I'm fine" I said. Bob then told me he was having a shower I should just enjoy the view. There I was bent over, my dress only just covered my pussy, staring at the view with a million thoughts racing through my mind. Mostly about how was I going to get out of this? Act cool I told my self and say "Oh Bob I'm flattered that you are interested but I couldn't do that to my mum". Over and over it was going through my mind when I heard the bathroom door open. I glanced back without turning around and it looked like Bob was wearing a bathrobe without the belt. Oh shit! I am freaking out! I was just about to turn around and blurt something out when it just happened. In one quick movement, Bob lifted up my dress and shoved his cock in my pussy. Instinctively I pushed back, did I really want this after all? Then my head started to spin, Oh my god, what have I done. Then I sort of blacked out for a few minutes. When I "woke up" so to speak, my first thought was "be experienced" whatever that meant, and then the reality that I was being fucked by a 57 year old man while my friend was in the next room hit me. "Can't stop now", I told myself. I wanted Bob to think I was experienced, so I reached between my legs and started stroking, then squeezing, his balls. Bob moaned a little louder.
After a few more minutes Bob pulled out and asked me to turn around. He then asked me to let my dress fall to the floor. I was completely embarrassed as I wiggled out of my dress, I hoped it didn't show. My dress fell to the floor and I stepped out of it. I was standing in nothing but heels and a bra and Bob staring at my bald pussy saying how beautiful I was. Then he stepped closer and put his arms on my shoulders. I knew what he wanted.
"This was my chance" I thought. I give great blowjobs! I can control my gag reflex so I can deep throat easily. I was going to show Bob I was a woman of the world!
I knelt down and started licking his shaft, then slowly I engulfed his entire cock and my lips were pushing against his body. I pumped up and down his cock and would stick out my tongue to lick his balls. Bob then asked me to look up at him while I sucked his cock. I looked up and he just kept moaning "you are so beautiful" over and over. I did like the look of sheer ecstasy on his face but went back to focus on a great blow job and then licked and sucked his balls. Bob grabbed his balls and moved as if he wanted me to lick his arse. Something I've never done but I thought "you've come this far, make it a night he will remember". I licked his arse and then went back to deep throating him, only this time he was pumping me.
Bob pulled out of my mouth quickly and held his cock. I think he was about to cum. Then he asked me to sit on the edge of the bed with my legs apart. This was definitely not me, I was freaking out again, but desperately trying not to show it. I did as he asked and he just stood there rubbing his cock moaning how beautiful I was. Then he asked me to lie back and bring my knees to my shoulders. I don't know how I was doing it but I was. And then he asked me to masturbate. Strangely I didn't freak at that. I figured I could hide my pussy with my hands and that would reduce my embarrassment of being in a pornographic pose in front of my mother's old boyfriend!
I started to masturbate and it actually felt good, my pussy was wet and tingly. I decided the only way I was going to get something out of this was to bring myself off. I really started going for it, rubbing my clit and stickking two then tree fingers in my pussy. Bob kept rubbing his cock and moaning and I was about to come when I felt his cock nudging my pussy. His cock wasn't very big so it was a let down after my fingers. I rubbed my clit while Bob watched his cock sliding slowly in and out of my bald 18 year old pussy. He was in heaven, and strangely so was I!
I just blurted it out. I was embarrassed the second I said it but while he was fucking me I asked Bob if I was better than my mum! He paused and started to say well...I quickly stopped him and said why not? He responded with "she likes anal". Oh my god, I'd never been fucked in the arse, but I didn't want Bob to know that. I instantly wished I hadn't said it but I simply said "who said I don't?" I could feel myself shaking, not because I didn't think I could handle it. I hadn't been fucked there but I did like to stick my vibrator up my but and it was bigger than Bob's cock.
I slipped my fingers in my pussy and use the lube on my arse. Then with my knees up near my shoulders and Bob staring at my pussy while he jerked off, I stuck one then two fingers up my butt. Bob then moved in and slowly slid his cock in my arse. I closed my eyes and tried not to think how I was getting butt-fucked by a 57 year old man that used to be my mothers boyfriend. Bob soon came, in his hand, and it was over, or so I thought. As I was getting dressed he said he had an idea for how I could make a lot more money than working in an office.
Quite casually he said he had many friend who would pay a lot of money to have a few hours with me. I asked him what a lot was and he said 1000 pounds and hour!
Over the next six weeks I had sex with about thirty guys, all over 50. I had 2 & 3 guys at once on a couple of occasions and earned over 60,000 pounds.
That was 18 months ago and I've since returned to Australia, but I'm heading back to London next week. Imagine how much money I can make in a year!
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