How Was Your First Time With A Prostitute?

[1069369]

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.

 

[cherryboom66]

That was the most hideous thing I think I’ve ever read.

 

[HorsemanUK]

Pretty positive experience all around.

Was in a bit of a dry spell and was getting a little fustrated with the dating scene, had gone through a string of dates where i'd been turned down at the 'final hurdle' for being too large.

So i decided I'd look into the local indepedant escort scene, give it a try. Found a one not too far from me, curvy nice body (phat ass, big boobs) around the same age as me, gave her the heads up first that id had a few knock backs lately for being very large. She said it was ok, she'd take the booking and was looking forward to seeing it.

It felt a little odd, the process and meeting for the first time but after the formalties, she seemed eager and excitable. She was shocked and very complimentary when I pulled down my trousers, even asked if she could take a picture to show her friend. Cutting to the chase she handled it very well and I saw her a few more times over the next few months.

On my last booking with her she told me she was leaving the 'business' but I was her favourite client and the sex was actually mindblowing for her. She wanted to stay in touch and we became FWBs, still are.

 

[H.ricky]

She wasn’t necessarily a prostitute or at least I don’t think so. It was at a massage parlor and I really didn’t have any sexual intention - I was just going to get a massage. it was all going well and once im on my back and she’s finishes up she asked if I wanted a happy ending. Of course I didn’t pass it up. She actually did a good job and about maybe 10-12 mins later I nut. My load is a lot so from her reaction I know it caught her off guard. Some of it got on her, her shirt, on the floor and table. It was a mess. Now that’s important because it took a second to grasp it all and she kept commenting about it. now I’m thinking it’s done because she’s wiping up and im about to get dressed but I’m still kinda coming back down to earth. So im sitting up to prepare to put my clothes back on but my high was still present.

So I’m still hard and as she’s getting things back in order she asked if I needed more help because of that. I thought another handjob or MAYBE a bj. I was surprised when she pulled a condom out. And of course I agree. The condom was way too tight but hey I put it on and we had sex. It was about 20mins. Nothing too crazy. She was extremely tight but could handle it. So I enjoyed myself. After we were done .. I got dressed and left a great tip.

I can tell other staff knew what happened based on the vibes. Lmao

 

[hardonistic]

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

 

[BubbleButtHungBoy]

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.

 

[Nemorex]

I just turned 18 and was still a virgin, and never had a girlfriend at this point, I went to an Asian massage parlor. She was like in her 40’s with big fake tits. She gave me a back rub, and the she let me rub her big tits. the she gave me a blowjob. Then I fucked her doggy for a little bit. But then I fucked her missionary and just loved having her big fake tits rub up against me while I was fucking her. At Some point she must of thought I was taking too long so she pulled the condom of Pfizer me and we did keep doing it without the condemn and I cummed inside her a few minutes later.

 

[jdoe86]

I used prostitutes in the past when I was between girlfriends or didn't feel like going out to the bars to spend $$$ on drinks with blue balls at the end of the night. A few different ones in Nevada, numerous ones in Germany and assorted massage parlous around where I lived. Nothing really wild and crazy. You get what you pay for.

I had a few working girls take a liking to me and would go out on dates with me (no charge) and the sex was more boyfriend/girlfriend than kinky.

One time in Nevada, I hit a major jackpot and treated myself to 3 girls. Two did anal and it was included in the tip. The 3rd said her ass was off limits, but she would do other things like spanking and bondage.

 

[HorseHung40's]

I was the prostitute; it was lucrative!

 

[longstroke7]

I've never paid for sex. Well unless you count dinner and a movie? Never had sex with a hooker. Never could wrap my head around paying for pussy when there are plenty of women giving it away free.

Pussy is never free, that's why it's a commodity. It costs something, either it be money or time, to obtain.

If a guy wants no strings attached sex without having to deal with courtship, hiring a sex worker is perfectly sensible. Having paid for sex before, I enjoyed it. Sex with someone new, no feelings involved, just a hot fuck and life goes on.

I am an advocate of legalizing and regulating prostitution in the United States. Make it safe and profitable for all involved, and tax proceeds are a benefit to the country. I think it's a legitimate profession and service that is well overdue for legalization. Some men may not even want sex, they may just want some company for awhile with women that they may not get to have any other time due to life circumstances.

 

[stretch8888]

One an only time, i was 28 she was 19. I always used to browse the craiglist ads but never actually used them. Then one night i came across one with a few pictures, no face but i immediately recognized a couple of her tattoos. It was my exes best friends younger sister, she was a little over 5ft, 100lbs or so, long brunette hair, stunning brown eyes, pretty smile, dimples, very tight body, decent sized pierced tits and a great little ass, she was a solid 10+ just unbelievably hot and well manicured, eyebrows, lashes, nails, tanned nothing out of place. I'd known her a few years and she was always a slutty little tease so i can't say i was overly surprised. I sent her a message and she responded with her rates, dos and donts and so on, $250 got me 2hrs in a hotel room, i was hesitant but figured fuck it why not, she sent me a room number and instructions.

I arrived at the hotel went up to the room and knocked, she answered the door in a lacy black bra and thong and high heels, and her jaw dropped as she blurted out "what the fuck?" and she grabbed a jacket to cover herself and asked what i was doing there, i said i was the guy and she just stared almost speechless then said she'd never done this with someone she knew, usually just horny old guys, i said we didn't have to if she didn't want to and that i wouldn't say anything, she thought about it for a minute while looking me up and down then said she'd heard things from my ex and her sister, things she'd like to see for herself then stepped back and let me in. She took the money then sat me down in a chair, got on her knees and removed my pants, i was already half way as she began sucking and fuck it felt good, she had me hard in seconds, then sat back almost admiring it and says "No wonder she missed you, this is a nice cock" then went back to sucking for a few minutes before asking if i wanted to get straight to the sex or if i wanted her to get the first one out of the way, i opted to have her suck me off first and let her do her thing as i sat back and enjoyed myself, on her list of dos and donts was warn her when i'm about to cum and don't cum in her mouth, well i felt it building and warned her i was getting there, she just kept sucking, i warned her again and again she just kept sucking, i was trying my hardest to not cum but i could only hold out so long before blowing my load and fuck me when i did it felt like a gallon of cum drained from my balls as she sucked and jerked until i collapsed in the chair, as i sat there coming down from the orgasm i apologized as she gulped it back and she just laughed and said "No need to apologize honey, i figure we go back so i'd swallow for you" . She went, grabbed a drink of water and returned and says i still have an hour and half to fuck her and asked if i needed a minute or wanted to get to it, i told her we could go as soon as she got me hard so she told me to get on the bed, did a little strip and began sucking my cock again, she got me good and hard then grabbed two packages from her bag and handed them to me, a condom and a rubber cock ring, she says "you don't have to wear the ring but it'll make your dick harder and feel even better when you cum" I slipped both on and i'd worn cock rings before but this one was certainly tighter, she grabbed my cock and ease herself onto it, we proceeded go at it for a while, thanks to the blowjob i was able to hold out, i expected a lot more overly dramatic moaning and such but it was just some hot sweaty fucking, we talked for the last 20 minutes or so and as i was about to get dressed to leave she asked if i wanted to go again, i said i couldn't afford anymore to which she said no charge she just wanted to fuck again.

Few weeks later she called me up for a hookup and we ended up being fuck buddies for almost a year until she got a boyfriend

 

[Reg]

I was about 45. I was in Chicago on business and was walking back to my hotel when I was approached by a petite young black woman. She asked me if I was interested in some company and it took me a minute to realize I was being approached by a prostitute. I thought about it for just a minute and said sure. We walked the short distance to the hotel and up to my room. There was really no conversation and no real foreplay. She got naked and helped me get out of my suit. She blew me for a minute then laid back and spread her legs. I put on a condom and slide right in balls deep. She worked her ass as I fucked her and she made me cum fairly quickly. After I pulled out she took the condom off me then got a warm wash rag and cleaned me up. It was now around 2 am and she asked if she could spend the night as it had started to snow. I said sure. In the AM she reached down and got me hard again and then rode me cowgirl until I came again. She got off me and went to take a shower. I laid there as she showered and when she was through I asked her if she was free again tonight.

We spent another night together.

Cost for those two days was $350.00.

 

[Over-reaching]

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).

 

[hlariv]

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.

 

[1373263]

My first and only time with a working girl was one of my ex's friends who started paying her way through university by escorting and became hooked on the easy money and attention. I met her a couple of years after I broke up with my ex, and she allowed me to "sample the merchandise" as she put it, as long as I could make her squirt like my ex had told her about. It took a couple of goes to get her there; she agreed we had made a fair deal.

 

[opinionman]

Eww, no protection? And behind a bus stop??

Who needs protection from a bus??

 

[Haggard_Wisdom]

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!

 

[uncuttexasdad]

I got first handjob from asian massage lady. She said take shower first. Didn’t have warm water so I shrunk. But once she started on me gave me the old “oh you so big! She oiled me up, something I never did because of just using foreskin. She pulled on my balls. Then she grabbed my shaft, and put the palm on my tip and rubbed circles. Omg again something I’d never done. I blasted a huge load. She knew how to make a guy cum quick with that polishing motion.

 

[hardonistic]

Any kids come knocking at your door later on? lol

Did you get tested for everything? Hope it all came back negative.

hahhaha I had a drunk friend who once spent the whole night with a hooker without using protection at all, he was scared as fuck for a week after going to the doctors

 

[Aezon]

To be honest, I don't remember what it was like. It was my first time and I had absolutely no experience in sex. In order not to embarrass myself in front of my future partner, I decided to turn to an escort for help. Thanks to my friend, I found a London escort service where I was able to view photos of all the girls who are there and choose exactly the one that would fit me perfectly. I warned her in advance that this is my first time and she took the initiative in "her own hands". We did this for almost eight hours, although for me the time passed sooo quickly. I am still grateful to that girl for the invaluable experience she gave me.

( Moderator edit removed the link to the escort service )