One night with Katherina – Part 6 [M+F][prostitution][fingering]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), who is competent and experienced in the anal arts, but touches on some other kinks along the way.*

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***Mathis:***

As my cock springs free of her mouth and she gives me her dazzling smile I can´t help but return it.

“I like to think so.” I reply to her compliment.

I look up at her and her amazing boobs. I could get used to the view, but I have something better in mind as I grab a hold of her hand and pull her towards me. I place both of my hands on her hips before starting to direct her into my lap again, wordlessly giving her to understand that I would like her to sit down with her legs spread around me.

When she sits down, I grab both of her tits, squeezing them repeatedly before guiding her left boob towards my mouth. My tongue darts out giving her hard nipple a flick before I let it circle it, covering her areola with my spit. Finally I suck on the nipple and bite down on it lightly. Then I repeat the process on its twin all the while kneading them with strong hands. Read more »

That masseuse [F] I [M] have been coaxing came by Sunday

One part of my lifestyle that I love is the massage with happy ending situation. For a very long time I have been into massages, even to the point of going to college, two different ones in fact and actually working part time as a masseur myself. A few times I had as many as 3 clients a week, and ended up in quite a few sexy situations.

All of the latter is a bunch of other stories, this one is about last Sunday. I found this local lady working free lance online, managed to get an appointment for here at home. Craigslist used to be a good source, but with that gone now, it’s more difficult. This one, believe it or not, I found on Facebook. First find one local, send a friend request, move to messenger. Not easy, but the ad sites are full of hookers.

Now my wife knows all about this fetish of mine, she gets a kick out of it and often we both get rubdowns. My wife is a Doctor, and she has a totally different outlook on life, sexuality, than any female I have ever known in my entire life. No jealousy at all, she will often elbow me and point out some nice looking lady we might see out in public to make sure I don’t miss out. Or she will want me to describe how my own recent massage went while working to get me going herself. Read more »

Sharing My Wife with an Old Pal [MFM]

Years ago, my wife and I discussed having a threesome with another guy. I’m not bi, so I wasn’t interested in anything like that, and I’m not into cuckolding, but it was something I was into, in terms of fucking my wife with another guy. We found a guy, he came over, and it was fun, but my wife thought he was a bit of a dud in the sack, so that was kind of that.

More recently, we’ve been discussing the idea again. My wife is an extremely shy person, but she even went as far to text her high school ex about the possibility. He was very keen, considering they had never done more than oral back then. He seemed a bit flighty though, and was wishy washy throughout a couple of months of infrequent texts about the idea.

I had a friend of mine in mind though, a guy I had worked with once, who I hadn’t seen in a while. Honestly, the perfect kind of friend. We wanted someone we were familiar and comfortable with, or at least I was, but who wasn’t in our life, per se. Read more »

I’m a cuck. My wife is on vacation with her boyfriend and often sends me pics of them doing dirty things to each other. [FM]

My wife and her boyfriend are in love. They spend a lot of time together. Sometimes they make out in the couch while I’m right there kneeling next to them. They almost always fuck in front of me .

I enjoy the humiliation. I love being dominated by my gorgeous wife and her lover who is superior to me in every way imaginable.

Right now they’re on vacation together and several times a day, I get pics of my wife getting fucked by her man. They’re pics of her with his cock in her mouth, of his cum on her tits, of his huge cock snuggled between her tits, his cock deep in her wet pussy etc.

I can’t stop jerkinv off to them. I can’t wait for them to get back so I can like the alpha male’s cock clean after he’s done fucking my wife.

I love being a cuck.

One night with Katherina – Part 5 [M+F][prostitution][teasing][oral]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (*u/lmczpn*) in first person ordering and enjoying a prostitute, Katherina (*u/aurora_w*), who is competent and experienced in the anal arts, but touches on some other kinks along the way.*

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***Katherina:***

As you spur Katherina on, she gets off her left knee and puts her leg under herself in a semi kneeling-crouching position. This raises her head a little higher and gives her a better angle when going down on you and allows her to get your dick a little bit deeper.

She steadies herself on your hip with her left hand. The movement is still methodical and both mouth and hand are in sync. As her head moves down she pulls on your cock with her right hand and it looks like she is trying to stuff her mouth with it. It looks really hot. The strokes from her hand get longer, so long that at some point her lips and hand begin to meet.

You let out a groan and again you see the corners of her mouth turn up in a slight grin. Read more »

One night with Katherina – Part 4 [M+F][prostitution][teasing][oral]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), who is competent and experienced in the anal arts, but touches on some other kinks along the way.*

***Katherina:***

Happily Katherina turns around and crawls towards you, getting rid of the denims around her knees in the process. She stops kneeling sitting in her lower calves before you. Her eyes are fixed on what you have to offer and she moves her arms up and her hands glide all the way from your knees (she pushes them slightly apart to make room for her) to your hips and further up your to your navel, then just like a wave on the beach her hands retreat again on the side of your hips but in the process hooking her fingers on the rubber band of your shorts, pulling them down and out from underneath you. Her pull was strong as the movement comes from her upper body pulling back. Your cock springs free. Read more »

One night with Katherina – Part 3 [M+F][prostitution][teasing]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (*u/lmczpn*) in first person ordering and enjoying a prostitute, Katherina (*u/aurora_w*), which is competent and experienced in the anal arts, but touches on some other kinks along the way.*

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***Mathis:***

I lift my glass reciprocating the toast and taking another small sip.

“Cheers Katherina. Charlotte actually recommended you to me. She told me if I wanted the best piece of ass they had to offer, that would be Katherina. She is into all kinds of backdoor stuff. I hope that is an apt description.” I reply with a teasing grin. I open my pants a little, readjusting my cock since my full on boner is actually pressing painfully against them. Then I decide to just get rid of them entirely. she seems to want to see what I have to offer anyway, so why not give her a small glimpse. She could take off my boxers later on on her own. Read more »

One night with Katherina – Part 2 [M+F][prostitution]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), which is competent and experienced in the anal arts, but touches on some other kinks along the way.*

​

***Mathis:***

I smile down at her in greeting as she is actually quite a bit smaller than myself with a height of 6’2″, but it made her all the more enticing.

“Hi Katharina, I´m Mathis and the pleasure is all mine.” I say with emphasize on the word pleasure as I turn on the vibrator through the love sense app. I was excited and a little nervous as it was the first time I ordered an escort.

“Come on in. You look even better than on your photos.” I compliment. I was sure that´s what every customer said to her, but I didn´t much care. It was in fact true.

I stand to the side, holding the door open and gesturing with my hand towards my apartment. In view of the door was a large couch, that could be converted to double as a bed. Read more »

The time I[M] tried sucking another guys[M] cock only to realise it wasnt for me

So last night I [M25] was spanking the monkey and got a strange urge to suck a cock. I’ve gotten off to Gay Porn before and been attracted to a few of my friends as well but never acted on it.

Last night i downloaded Grindr and was having a lot of fun sending and receiving texts and pictures.

Roll on to this morning when i started chatting to this guy [M20] on the app. He was super cool and we started teasing back and forth. Talking about sucking and fucking and what not.

I work in a third level institution (not a lecturer) in which he is a student. I took my lunch break at one o’ clock and learnt that he was at home, 5 minutes down the road, he sent me a picture of his rock hard cock and asked me to come over.

So i went over to his place, he was a lot smaller than me (twink) but a lot more hairy which surprised me. Read more »

One Night with Katherina – Part 1 [M+F][prostitution]

*This story is the result of a long term roleplay exchange through* r/dirtypenpals

*It features Mathis (u/lmczpn) in first person ordering and enjoying a prostitute, Katherina (u/aurora_w), which is competent and experienced in the anal arts, but touches on some other kinks along the way.*

​

***Katherina:***

When you called the agency and were asked what you were looking for in your girl of choice you were looking for a nice piece of ass that enjoys anal. The woman on the phone – you could hear her smile through the phone – told you that if you wanted the best piece of ass they had to offer, that would be Katherina, a part Estonian part Norwegian girl that was heavy into all stuff back door. The operator directs you to a website with Katherine’s profile:

She is 24 years old 5 ft 3, has long blonde hair, green eyes and a very fit body

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***Mathis:***

I was immediately smitten by the girl the agency proposed to me. She was beautiful, just like you would expect from an Estonian/Norwegian girl, but what was more important to me, she had an amazing bubble butt I was already daydreaming about. I was envisioning her butt jiggling with every thrust of my cock. My balls slapping against her clit. Read more »