How Was Your First Time With A Prostitute?

Over-reaching

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Pussy is NEVER free. Most guys spend far more for pussy over a lifetime in a marriage than they would if they just paid for it when they desired sex.
Not to mention the time and energy we men expend on getting pussy. Well worth it, but it's not by any means negligible.

Some guys I knew used to calculate the cpf factor – cost per fuck. It only took into account money expended, but it could be adapted to include other measures – the adapted cost per fuck factor (a-cpf).
 

Haggard_Wisdom

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I've always had a fairly high sex drive, and it hasn't always been fun. In Australia sex work has been legal for a while and when I was a single bloke I would go to one of several legal brothels. The sex workers are protected by the venue and in principle the money that they earn is theirs less the fee the brothel charges the worker. 'Pimping' is illegal, as it should be.

I remember my first time with a sex worker, she must have been up on her kegel exercises because when I pulled out she sucked the condom right off my cock! I had to dig it out of her and it wasn't easy either. It was like trying to catch a small rubbery fish and conditions down there were very moist by the time I managed to 'land' the little fucker.

We actually became sort-of friends after that!
 

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My first sexual experience of any kind was with a prostitute. I had just graduated college, finally had my own car, and decided to check out one of the areas in San Diego known to have street walkers. I picked her up and found a dark, quiet place to park. I was incredibly nervous. She sucked me off...I know I came fast. I don't think she was expecting it, but she took my load in her mouth, then spit it outside the door.
 
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My first sexual experience of any kind was with a prostitute. I had just graduated college, finally had my own car, and decided to check out one of the areas in San Diego known to have street walkers. I picked her up and found a dark, quiet place to park. I was incredibly nervous. She sucked me off...I know I came fast. I don't think she was expecting it, but she took my load in her mouth, then spit it outside the door.

Nothing like the first time. That’d be quite a rush.
 
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jakeytollboy

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My first sexual experience of any kind was with a prostitute. I had just graduated college, finally had my own car, and decided to check out one of the areas in San Diego known to have street walkers. I picked her up and found a dark, quiet place to park. I was incredibly nervous. She sucked me off...I know I came fast. I don't think she was expecting it, but she took my load in her mouth, then spit it outside the door.
You still in san diego :)
 
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8896851

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So I was 24 at the time. Friend told me he visited a whorehouse and that the girls are like any other only sluttier. I said wtf I’ll five it a go. Was single at the time doing amateur bodybuilding so constantly jacked up on all sorts of sups that gave me constant hardons and balls full of cum. If I didn’t jerk off at least 2x day I’d feel like I’m gonna burst out of my skin.

So one day I got back from work it was a Friday and was horny af. Took out my fav porn magazines ( was the year 2000 and computers were expensive). I jerked off and cummed 5x in the space of about one hour. Was still horny so I said this is it I’m gonna go and visit a nearby brothel.

It was in Canberra a place called ‘a touch of class’, it’s still around today. It took be some courage and a few beers to go inside. They had Aussie girls only at the time and mamasan the lady of the house was extremely polite and friendly when I told her it’s my first time. She introduced me to about 4 girls of which 3 were not my type. Then a tall fit long legged blonde came in and my balls began to twitch. She introduced herself as Talli, said she was also a stripper and had her own website. I stared like a pervert at her long toned legs and feet as she pivoted in very high glistering platform heels.

Mamasan said to take her so I paid $95 for half an hour while trying to hide my hardon that left like it was about to burst through my jeans.

Tali took me by my hand and led me inside a large clean and decorated room and asked me to shower. After my shower Tali brought me a glass of champagne which I began to sip while watching her undress.

Her body was spectacular, to date one of the best I’ve fucked. Toned and lightly tanned all over with flawless right skin. She was probably in her later 20’s, I was too shy to ask. She set the rules -: not kissing on the lips or going down on her, but that everything else is ok.

She complemented me on my body and was fascinated with my huge shredded quads while I started to kiss her all over her body paying attention to her legs, knees, calves and thighs while my cock grew to it’d maximum. Tali took control and stretched the dom on then pushed me on my back and sat on top in cowgirl pushing my cock into her rather tight cunt.

Having just blown 5 loads I wasn’t particularly sensitive so I began pounding her hard and deep. While she initially let out a few fake moans, her moaning soon got real.

Switched positions to miss then doggy then back to reverse cowgirl. She loved to ride me with little support working out her thighs when I heard the bell ring. I paid another 95 for a further half hour as there was no way I was gonna leave without Tali draining the last drop from my balls.

Another glass of champagne and it was on again, this time Tali got kinky and asked if she can trample my quads in her high heels. I said fuck yeah do it and she stood on the bed placing her leg on my thigh, first the one and then the other before standing on me with her full weight. Even though she was light I felt the points of her heels dig into me as she tip toed and walked on my flexed quads.

Pretty soon I had enough of this masochism and pushed her over grabbed both her legs by the ankles and thrust my cock into her fucking her cunt hard while holding both her legs. I knew I was gonna cum like this and Tali knew it too so she clenched her cunt as I violently pumped her. I pulled out just in time to rip the dom off and douse her legs in my sixth load of cum for the day.

Satisfied I went home to sleep, it must have been like 3am by then. When I woke up first thing I thought of is Tali and I looked at my quads which had square red marks from her high heels.

I never saw her again but often thought about her. She was my first hooker I’ve banged and left me hooked on hookers for life.
This sounds incredibly hot and manly. Ignore the haters.
 

hardonistic

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wow this thread took me a while to realise when my first time was.

Was back in my early 20s, and a bunch of army mates took me across the border to go have some fun for the weekend (we're in south east asia). They were all pretty experienced and I was a virgin so they figured they'd help a brother out.

At first we went to a pretty nice massage parlour where I didn't expect the young cute masseuse to wank me off then wash me up in a bathtub. Massage room was done up like a private Bali villa and it was pretty hot I was just quite the virgin and really shy, even tho she kept commenting on my army bod.

We later had drinks and on the way out of the bar at 3am an army bud makes friends with an older tourist who frequents the brothels and somehow we all end up in a fish tank picking out whoever is left at the end of the night. I like my girls smaller cause I'm not as tall, and this lady had amazing tits.

Fast forward I end up back in my hotel room with my buddy and we both got a chick riding us and its hot as fuck but she was also taking my virginity and I didn't know how to tell her that but I think she could tell from what she told me in her broken english - "big dick, bad moving".

Eventually I shot my first load pretty quick with her riding me, then we took a rest and I was talking to my mate about how tight she was so we ended up swapping side by side with both of them doggy at the edge of the bed.

Sounds fun but I think I was too drunk to function and the two girls left after 2 rounds even tho we arranged for a whole night, and my bud and I ended up wanking out a third round watching some porn on the telly cause we were so worked up before washing up and catching our morning flight back

Needless to say the flight was filled with details from the other dudes in their rooms too hehe can't wait for covid to reopen to clock in more stories
 
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1069369

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wow this thread took me a while to realise when my first time was.

Was back in my early 20s, and a bunch of army mates took me across the border to go have some fun for the weekend (we're in south east asia). They were all pretty experienced and I was a virgin so they figured they'd help a brother out.

At first we went to a pretty nice massage parlour where I didn't expect the young cute masseuse to wank me off then wash me up in a bathtub. Massage room was done up like a private Bali villa and it was pretty hot I was just quite the virgin and really shy, even tho she kept commenting on my army bod.

We later had drinks and on the way out of the bar at 3am an army bud makes friends with an older tourist who frequents the brothels and somehow we all end up in a fish tank picking out whoever is left at the end of the night. I like my girls smaller cause I'm not as tall, and this lady had amazing tits.

Fast forward I end up back in my hotel room with my buddy and we both got a chick riding us and its hot as fuck but she was also taking my virginity and I didn't know how to tell her that but I think she could tell from what she told me in her broken english - "big dick, bad moving".

Eventually I shot my first load pretty quick with her riding me, then we took a rest and I was talking to my mate about how tight she was so we ended up swapping side by side with both of them doggy at the edge of the bed.

Sounds fun but I think I was too drunk to function and the two girls left after 2 rounds even tho we arranged for a whole night, and my bud and I ended up wanking out a third round watching some porn on the telly cause we were so worked up before washing up and catching our morning flight back

Needless to say the flight was filled with details from the other dudes in their rooms too hehe can't wait for covid to reopen to clock in more stories
Brah, hot as fuck. Nothing beats fucking in exotic Asian countries. I fucken love it!
 

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Joined the army in 79 and was sent to Ft Bliss Tx. The guys in the barracks were always joking about the hookers across the border in Jaurez MX, that you could get laid for $20. As a private in the army I wasn't even clearing $400 a month. The bars and clubs around base were about 100 guys to every gal and I was shy so my odds of getting laid were about zero. One night I decided to head to Jaurez, the booze was cheaper and who knows. Went to couple bars and on the way to the next one a cab drivers says "hey do want to meet some women?" Hell yes, he says come with me. I jump in the cab off we go, pull up to a bar and go inside. I sat at the bar and ordered a beer and the driver was talking to a woman behind the bar, he comes back and tells me it will be $5 for the ride and he will wait for my and give a ride back. Soon a good looking woman comes over to me and says come with me and we go to a room with a bed. We sit on the bed and she tells me it's $20, I never thought to ask for what. So I give her the $20 and she tells me to get undressed, I do and lay on the bed. I'm hard as a rock since it's been months since I'm gotten off and at 19 years old a slight breeze can get me hard. She's still dressed and starts playing with my cock and starts sucking my cock, or so I thought. To this day I'm not sure if it was lube or she was sucking my cock. But to couldn't have been 2 minutes in and I'm trying to pull away because I'm going to cum and and she's not letting go and bang it was over. She starts walk out and I'm trying to tell her wait I'm not done, I'll pay again. Hell, she didn't even have to undress and it was over. I get dressed come out of the room, get my cabby and head back. The whole thing was less than a half hour.
 

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So I was 24 at the time. Friend told me he visited a whorehouse and that the girls are like any other only sluttier. I said wtf I’ll five it a go. Was single at the time doing amateur bodybuilding so constantly jacked up on all sorts of sups that gave me constant hardons and balls full of cum. If I didn’t jerk off at least 2x day I’d feel like I’m gonna burst out of my skin.

So one day I got back from work it was a Friday and was horny af. Took out my fav porn magazines ( was the year 2000 and computers were expensive). I jerked off and cummed 5x in the space of about one hour. Was still horny so I said this is it I’m gonna go and visit a nearby brothel.

It was in Canberra a place called ‘a touch of class’, it’s still around today. It took be some courage and a few beers to go inside. They had Aussie girls only at the time and mamasan the lady of the house was extremely polite and friendly when I told her it’s my first time. She introduced me to about 4 girls of which 3 were not my type. Then a tall fit long legged blonde came in and my balls began to twitch. She introduced herself as Talli, said she was also a stripper and had her own website. I stared like a pervert at her long toned legs and feet as she pivoted in very high glistering platform heels.

Mamasan said to take her so I paid $95 for half an hour while trying to hide my hardon that left like it was about to burst through my jeans.

Tali took me by my hand and led me inside a large clean and decorated room and asked me to shower. After my shower Tali brought me a glass of champagne which I began to sip while watching her undress.

Her body was spectacular, to date one of the best I’ve fucked. Toned and lightly tanned all over with flawless right skin. She was probably in her later 20’s, I was too shy to ask. She set the rules -: not kissing on the lips or going down on her, but that everything else is ok.

She complemented me on my body and was fascinated with my huge shredded quads while I started to kiss her all over her body paying attention to her legs, knees, calves and thighs while my cock grew to it’d maximum. Tali took control and stretched the dom on then pushed me on my back and sat on top in cowgirl pushing my cock into her rather tight cunt.

Having just blown 5 loads I wasn’t particularly sensitive so I began pounding her hard and deep. While she initially let out a few fake moans, her moaning soon got real.

Switched positions to miss then doggy then back to reverse cowgirl. She loved to ride me with little support working out her thighs when I heard the bell ring. I paid another 95 for a further half hour as there was no way I was gonna leave without Tali draining the last drop from my balls.

Another glass of champagne and it was on again, this time Tali got kinky and asked if she can trample my quads in her high heels. I said fuck yeah do it and she stood on the bed placing her leg on my thigh, first the one and then the other before standing on me with her full weight. Even though she was light I felt the points of her heels dig into me as she tip toed and walked on my flexed quads.

Pretty soon I had enough of this masochism and pushed her over grabbed both her legs by the ankles and thrust my cock into her fucking her cunt hard while holding both her legs. I knew I was gonna cum like this and Tali knew it too so she clenched her cunt as I violently pumped her. I pulled out just in time to rip the dom off and douse her legs in my sixth load of cum for the day.

Satisfied I went home to sleep, it must have been like 3am by then. When I woke up first thing I thought of is Tali and I looked at my quads which had square red marks from her high heels.

I never saw her again but often thought about her. She was my first hooker I’ve banged and left me hooked on hookers for life.
Hot story unfortunately in most states in US it is illegal to have those
 
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uncuttexasdad

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Picked up a hooker once for a BJ in the car. She said “you a cop?” Nope are you? She bared her tits. She sucked away. It was my first BJ. Being uncut I wasn’t used to bare head action. It was incredible. I reached in the back of her pants and felt her asshole. She pulled off said nuh uh I don’t do greek. She let me finger her a little them went deep on me. Put me over the edge. She took my whole load. Then opened the door had a massive hack a lugie, wiped her chin and left.
 

uncuttexasdad

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My next one was a massage parlor. Asian lady about 35 said take a shower. There was no hot water i told her. She said ok get on the table. I was nervous shaking plus the cold shower. She said I warm you up. Leg rub 30 seconds and straight to the cock. “ Ooooo you so big!” Ya ok. She oiled my cock. Again being uncut I wasn’t used to lube. Wayyyyyy more intense! Then she used the palm of her hand flat on tip of my knob. She was a pro and knew what that would do. Ohhh you so hard. That tip massage was unlike any stroking feeling. That did it i exploded.
 

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I was 25 and my first time having sex, so yes, I lost my virginity to a hooker, and I don't care because she was wild and hot as fuck. We met at her apartment and she took me to her room, making small talk etc. We had got naked and she shoved me onto the bed, and took my cock in her mouth and sucked madly, suprisngly I didn't cum. Then he got on top and rode my cock like a horse, felt like she was gonna break it. A half hour later of fucking and changing positions I told her I was gonna cum, she said I could either cum in her pussy or her mouth, not risking impregnating her I pulled out and came all over her face. She was coated in cum and said it was the biggest load she'd ever had. Never saw her again.
 
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deleted817718

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I dated a woman who had been a prostitute before we met, and still occasionally did it part time to earn extra money when she was short on cash. The sex between us was honestly not great. She has little interest in it and was pretty honest about not really getting much out of sex, but rather preferred the closeness of a relationship. The image of having a wild and crazy sex life with a professional sex worker was absolutely not the reality, and she was more restrictive with sex than any woman I had been with at this point.
 

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I was actually unaware that it was my first time with a hooker.

I met a girl during the Occupy movement that was living in the tent with other protestors downtown and we struck up a social media relationship. As that wound down she reached out to me looking for a place to stay. My daughters had moved out so, I had room and I offered to let her come until she had a more permanent place.

She ended up staying a couple of months, first in another room and pretty quickly in mine. The fact that she wasn't much older than my daughters was kind of a novelty to me. She was a tiny little thing and, honestly, one of the best pieces of ass I ever had. She is one of the few exes I kept pictures of, because she had the most perfect, heart shaped ass and right on 5 feet tall.

She did not tell me until a couple of weeks into it that she had been sleeping with men for money for a few years. What immediately clicked when she told me that was one of the things she oddly brought up during foreplay was if she had a cock, she'd want one like mine. I immediately realized she had seen more of them that a woman that age might have normally experienced.

She was also really sassy in public, as we went out a lot of places where we were complete strangers. A couple of the short road trips really would make good adult oriented storylines.

She finally moved out and I lost track of her almost right away. A couple of years ago she reached out and we got together for an evening. Still beautiful. It turns out that when she was living with me she was already pregnant with the baby of one of her last clients - a 55 year old neurosurgeon. She and her kid were set based on court orders and the fact that she figured out investing. Funny for a little waif I found living in a tent in an anti-capitalist protest.
 
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1069369

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Picked up a hooker once for a BJ in the car. She said “you a cop?” Nope are you? She bared her tits. She sucked away. It was my first BJ. Being uncut I wasn’t used to bare head action. It was incredible. I reached in the back of her pants and felt her asshole. She pulled off said nuh uh I don’t do greek. She let me finger her a little them went deep on me. Put me over the edge. She took my whole load. Then opened the door had a massive hack a lugie, wiped her chin and left.
Outstanding brah. I bet that protein load did her good too.