For as long as I can remember I've been a boob guy. The bigger the better, always. I would wank myself to whatever pair of boobs I found on the internet or in magazines when I was a teenager. I lost my virginity at 18 to a girl called Katie who had lovely D cups with large pale areolas. The sex was fantastic at the time. In hindsight, not so great. For years afterwards I would picture those marvellous breasts swinging in my face as she bounced on top of me. It was around 5 years until I got a feel of anything bigger than a C cup and it came courtesy of a hooker.
I'd had a couple of girlfriends in the years after Katie, and a couple of one-night stands. They were all smaller in the chest department unfortunately, but I would take whatever I could at that age. By 22 it was really starting to bug me. My mates didn't know I was a tit lover because I didn't want them to think I was staring at every girls chest. I kept my desires to myself.
I moved to London and it was there that I started thinking about seeing an escort. There would be little cards stuck up in phone boxes all over central London that I would ring but then chicken out of going to. Then, one night, I lost my hooker cherry.
Drinking with friends in Soho all night had left me drunk and, coincidentally, alone after we all went our separate ways. I walked towards Piccadilly to get the night bus and wandered past the famous Soho 'model' doorways. I paused and thought about it. Fuck it. I headed into the brightly lit corridor and to the rickety staircase at the back. My steps echoed through the building as I made my way to the first floor. There was an A3 poster on the door saying 'Exotic model. Very friendly'. Before I reached the last step the door opened and a tall black lady in lingerie smiled at me and invited me inside. I spied another sign pointing to the second floor and decided to try that one instead. At the next door the poster said 'Busty blonde, Very sexy'. Yes! I was going to do it.
I knocked and an old woman of about 50 answered, cigarette in her hand and very grumpy looking. 'She's busy, only 5 minutes. Come inside'. I was ushered into a pokey sitting room where the old woman was watching television. I was so uncomfortable. I saw a price list on the wall opposite. Services ranging from £15 – £80 pounds. Before I could digest all of the services I heard the front door open and close. Then, the sitting room door opened and a blonde lady of about 30 walked in wearing only a bra and knickers. She was a touch shorter than me, slightly curvy and with nice, full breasts, maybe a DD. Her accent was eastern European, her English broken. She asked if I wanted to move through to the bedroom and I just nodded. She led the way as I stared at her arse as she walked.
Once inside the bedroom she told me to sit on the bed. It was quite small and very firm. She asked what service I wanted. 'Sex and blowjob', i said meekly. I handed over £40 and she asked for a tip. I dug around my pockets and produced a fiver. She stood up and told me to undress whilst she popped out. I stripped to my boxers and sat back down. 2 minutes later she walked back in and said 'and your pants'. I stood and dropped my boxers, now totally naked. She reached behind her and unhooked her bra, her face was bored and uncaring. Once she had uncovered her tits I stared at them for a moment. They were clearly enhanced, and not a good job. The scars were still prominent and they looked red around the nipples. She walked towards me and told me to lay back. She produced a condom and unwrapped it swiftly before sliding it on my soft cock. She didn't say anything but just leant over and put her mouth around my dick.
It was an odd sensation. I wasn't turned on but she was sucking my dick. To be honest, it was a terrible blowjob but it did get me hard after a couple of minutes. Once fully erect she stopped and told me to get on top. She rolled over and spread her legs. I looked at her pussy and saw her applying some lube to it. Then she pulled me towards her and I entered her warm cunt. She held her hand about 2/3 of the way down my shaft so I wouldn't go into her very far. I've only got a 6.5inch dick so assumed this was because she was being fucked all day every day. Immediately she asked me to fuck her harder so I did. I started to cum after 3 minutes or so and unloaded into the condom whilst inside her. I pulled out and rolled over, spent. She grabbed a tissue and removed the condom and wiped my dick. She passed me another tissue and I cleaned the rest.
She was dressed within 30 seconds of me cumming, so I quickly put on my jeans and shirt too. She led me to the exit which was a different door to the one I came on. She opened the door to the blinding lights of the stairwell and said thanks. I thanked her too, still sounding nervous and I left. I was both pleased and disappointed in what had just happened, but most of all I had wanted to play with some big tits yet I didn't even touch hers.
Source: reddit.com/r/gonewildstories/comments/3w75mo/first_time_visiting_a_hooker