Please see the note at the bottom of my post for details to clarify authenticity. Enjoy!
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I regularly booked escorts when I wasn’t in a relationship. There is only so long you can pleasure yourself before you start craving the real thing. The booking I had with ‘Shelly’ was nothing special until a second booking with her working as ‘Jen’ (and her appearance in the news) that totally changed how I felt about it.
‘Shelly’ was mid/late 20s. When you imagine escorts you might imagine great beauties but that’s not often the case. She was pretty plain: dark hair in a fringe, well tanned skin. Her body was the real killer though. That’s what I’d seen on the profile. Tight and toned, just the way I sometimes liked it. After opening the door to her serviced apartment she took the cash and led me in. I wasn’t disappointed in person – great body and a friendly, flirty demeanour. Her services were limited: pecking kisses, all actions a little bit rushed etc. but what really stuck in my mind was the blowjob. She had my full bottoms off early and took me in her mouth while I was still soft. She suckled hungrily on my still small cock with her eyes closed and would have felt it grow quickly in her mouth. Once I was fully hard, her eyes opened and she locked them with mine, giving deep eye contact as she worked the full length of my dick with her lips. At one point I remember her grabbing the shaft with one hand and holding it up and flat to my stomach while she licked my balls, still keeping regular eye contact. She was savouring sucking my dick and the way it made me feel, small moans escaping from her as she worshipped it.
Some escorts like to be touched and be made wet. Honestly, that was one of my favourite parts. I loved pleasuring women I’d paid to open themselves up to me. Shelly was not one of these escorts. She quickly moved so her back was on the bed, slapped an industrial amount of lube onto her hands and lathered her pussy with it. She chucked me a condom and simple said “Fuck me”.
I fucked her hard, mostly in missionary and recall finishing on top of her, my hands under her shoulders gripping onto them as she groaned loudly into my ear. She guided my softening cock out of her and she giggled as it caused her pussy to squelch. A good time was had by both.
Imagine my shock a couple of years later when I saw her on the news. Local WPC arrested and charged after working as an escort and helping the owner of the agency she worked for (her pimp) with details of rivals’ activities. She was eventually sentenced to over a year in prison. She looked rough in her police photo and in media pictures of her outside court before the trial.
However, it made the meeting with her seem even hornier when I’d think back. I’d fantasise about her in uniform, handcuffing her, spanking her as ‘punishment’. It must have made her so horny doing what she was doing on the side. Copper by day, hooker by night. I admit I also thought about her in prison. It couldn’t have been easy as a former policewoman. I wondered if she’d needed, wanted or maybe been encouraged to lick another inmates pussy or pleasure them in some way. She was a ‘take no shit’ type of person so I couldn’t see anyone forcing her to do something she didn’t want: more likely she would be the one in charge. I shot so many big loads to that thought over the years.
My second meeting with her, around 7 years after the first, was when she worked as ‘Jen’. I only recognised her when she opened the door. Agency workers in my area tend not to show face pictures so it’s always a surprise when you get there. She definitely looked a lot older. Her expression was quite surly. Her skin was a lot more leathery than it had been last time. Her body was still otherwise perfect. She was in great shape. She didn’t recognise me at all but I recognised her. She was working out of a very cheap hotel close to me that was regularly used by agency escorts – you would sometimes see them smoking or chatting out back or buying condoms from the local shop. Her services were worse than the first time. The blowjob she gave me was terrible. I was allowed to touch and finger her this time but there was no enthusiasm. Again, though a little wet, she slapped on the lube and asked “Can we fuck now?”
I’d had so many fantasies about her but this fuck was different to anything I imagined. I knew I wouldn’t be returning and I knew she wasn’t going to indulge handcuffs or even any mention of her past life so I just fucked her doggy style as hard as I could for as long as I could. She had the TV on loud in this small room so other hotel guests couldn’t hear too much but I was determined to test that. She was on all fours on the bed, in front of the mirror in the room. My hands were constantly either firmly gripping her ass or her small hips as my cock smacked in and out of her lubricated cunt, loud smacking noises as my balls or skin made contact with her every single thrust, with every single cm of my cock finding its way quickly inside her. Looking at her hard face in the mirror her mouth was open in an ‘O’ and she groaned in an animalistic way, her cheeks and chest flushing red. All I did was pound her mercilessly and keep eye contact in the mirror, while I thought about all the kinky stuff I’d wanted to do to her in my fantasies. The amount of lube she’d used made it easy to do this and it mixed with her cum to dribble down both our crotches. Eventually, I pushed her upper back down to put her face to the mattress and filled her up. I can promise the TV wasn’t loud enough to mask the volume of my groans as I came hard inside her.
After leaving I never saw her in person again. I heard she was working at a gym as a personal instructor for a while but then left to live in Spain. I do wonder what she’s up to sometimes and stroke my dick thinking about the contrasting meetings I had with her.
***
I am currently writing up a number of the real-life encounters I’ve had over the past few years. This is a 100% true story: she was given a little over a year in prison and removed from the police force. It was a big story locally at that time. There’s some weird and wonderful stuff happens when fucking escorts. I’ve got a lot more to come…
Source: reddit.com/r/gonewildstories/comments/v9xp76/fucked_a_police_officer_who_was_moonlighting_as