Fucked my former pupil who was working as an escort [MF]

As I said on my last post, I’ve used escorts quite extensively in the past, often with the aim of fulfilling a specific fantasy. This one is different in that it inadvertently led me to fulfilling a fantasy I never thought was possible. This post is just about our initial meeting but she became a regular of mine and we grew close. It was never a relationship other than client/user but it did get a lot more intimate/dirty over time.

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I felt horny and contacted a local agency. The girl I wanted wasn’t available so they mentioned a girl called ‘Sassy’. A quick look on their website and she looked OK. Rail thin. Blonde. Amazing legs. Tits were almost non existent but she at least had something of an ass. There are rarely face pics on agency sites. There was no-one else on offer so I booked her. £120 for me to go to her place for an hour of fun.

A lot of girls in my area work out of anonymous looking apartment buildings. Lots of short-term renters. She buzzes me up without a word and I get the lift up and knock on the door. 304. Usual routine is they hide behind the door as they open it. This happens and I go in. I look at the girl and my heart skips a beat.

I know her.

You think for most guys who use hookers this would be a major fantasy but it’s actually something many dread: the fear of being outed for your hobby.

I knew for a fact she’d recognise me: she was a former pupil of mine!

I could tell she was as shocked as me. She stammered a greeting, calling me by my ‘professional’ name. “Oh! Mr XXX…”. She didn’t know where to look but, luckily for me, closed the door behind me, not wanting any of the neighbours to witness this awkward encounter.

My heart was racing but I composed myself and asked her if we should go through to the other room. There was a living room but she took me to the bedroom next door. My dick began to twitch.

Long story short we had a discussion that started off as frosty but started to heat up. I’d known her 8 years ago when I was training, worked with her as a pupil five times a week for a year, and here she was 8 years later ‘all grown up’. She grew in confidence as we talked and became more professional, treating me like a normal client. How long she’d been an escort (not long), how she wound up doing it (though her cousin) and how often she worked (trying to go full time). I tentatively asked if she still wanted to go ahead with the booking and I’d understand if not and…

“Of course.”

My dick got hard quickly and I fished in my pockets for the bundle of notes.

That first time the sex was pretty standard. Full kissing (with tongues) while I ran my hands over her flat body. Her tits were almost completely flat, apart from her hard chunky nipples. I traced my fingers along her slit and could feel her getting a little wet. I moved my hand up to brush her hair back and kiss her deeply. She moaned lightly in pleasure as our tongues danced and I knew she was genuinely into it. I planned to go back to fingering her pussy but she moved straight to her knees to unzip my fly and pull my dick out. She went straight to work on the head for a minute then moved back to let me stand, take everything off and watch this girl I’d last seen nearly a decade ago suck the full length of my dick.

After a few minutes I got her on the bed and started to lick her. She was soaking. Her juices were tangy and quite pleasant. She got a condom out of its packet, slipped it over me and I wordlessly climbed on top of her and started to fuck her in missionary. Her moans were getting louder and louder and I could feel the juices flowing down the top of her thighs as they made my own wet. We came together when I gathered a bunch of her hair and yanked her head back while pumping into her. I was almost as loud as she was and didn’t stop groaning until the last of my cum had shot into the condom. When I took it off, we both laughed at how much cum there was inside. Understandable though, right? All the tension gone, she smiled and asked me if I’d enjoyed myself. You can imagine my answer.

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There is at least one more part to this story for another time. I saw her once more with the agency then saw her several more times when she went independent. She got progressively sluttier and lost more of her inhibitions, let me give her anal and take pics of her. No idea if she did that for all her clients or if it was just me. All I know is that day went from being potentially one of the worst to one of the best of my life.

Will do a follow up if there’s interest. Aiming to write more about other exploits from my single days in future too so let me know if you like it!

Source: reddit.com/r/gonewildstories/comments/v5cdp6/fucked_my_former_pupil_who_was_working_as_an