One night with Katherina – Part 8 [M+F][prostitution][rimming][toys]

*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:***

She moans surprised as you enter her, but then falls into a synchronous rhythm of slightly pushing back and sighing every time you force your tongue inside her.

At first the hole is repeatedly clenching up in surprise to your contact but after several strokes it remains still and open. Perhaps she is willing herself to relax. Her eyes are still closed.

As you continue Katherina lowers her front to her elbows and placed her brow on her arms on the floor.

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***Mathis:***

I continue for some time lost in the rhythm of tongue fucking her ass. Pushing my tongue inside, holding it there a little, trying to swirl it around before pulling out and repeating the process. After a while I stop and get up. “Stay right there.” I request as I walk over to the suitcases and open them. I look through the gigantic assortment of toys the agency has provided us. Finally I find what I had been looking for. Some anal beads and a decent sized dildo.

I return to Katherina still in her initial position with toys in hand. I get down on my knees again, placing the dildo on the floor while I start to work the first bead into her ass which isn´t to hard. The lube and my tongue have done their job to prepare her tight hole.

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***Katherina:***

One of them has the various toys, plugs, beads, dildos, vibrators, a ball gag, a choker with a metal ring and a thin metal chain, different sorts of lube, condoms, a second lovesense and probably a lot more

The second Pelicase includes a sybian with several different possible attachments. But in addition there are several clear zip bags with what looks to be lingerie. It’s difficult to make out in this folded state bit there are differently colored sets of nylons, you can see a metal clip probably belonging to a garter belt, there is one bag perhaps containing a black lace body suit.

As you continue with Katherina she lowers her front to her elbows and places her brow on her arms on the floor.

She remains in her relaxed position, head on her forearms on the ground, while you put in the beads. Putting your hand on her pussy provokes a gasp. The love sense is still vibrating inside her and you can see liquid between her folds and on the antenna. Her pussy is fully shaven and silky smooth as is the rest of what you can see of her.

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***Mathis:***

Seeing as there are no problems for her so far I decide to speed up the process of inserting the beads. There are nine in total in increasing size. To help a little I pull the left hand away from her pussy after letting in slide between her inner and outer lips. Then I use her own wetness to lube the following beads up a little before pushing more in. The fourth, fifth, sixth and seventh follow without a hitch. I return my hand to her pussy. “Want another one Katherina?” I ask expectantly, pressing a kiss to her ass.

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***Katherina:***

With you putting in more and more beads in Katherina’s gasps become more intense. With the sixth her head comes up from her resting position looking forward.. Her mouth opens and the metal plug drops to the floor. She slowly moves her torso a bit trying to accommodate the chain inside her. You wait a few seconds after her movement stops, which you interpret as green light to continue and push in the seventh.

This one is already at about 1,5″

“How many are there already?” she asks. “Seven” you answer.

Answering your question whether you she wants another one, she says “yes, but could you get some more lube from the case, please. Be generous with it. There should be different flavors… ”

Next beads increase faster in size than the ones earlier. It’s difficult to be certain, but the 8th could perhaps be 1,75″ and the last on, the 9th, 2″, maybe even a bit more. The entire chain finishes of with a large ring, bigger in diameter, than the last bead.

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***Mathis:***

I nod in acknowledgement as I leave her with seven beads already inside of her, the rest of the chain sticking out prominently. I get up from my kneeling position and walk over to the cases, thinking about what kind of lube I should get. Since she already has some mint oil applied to her butt I don´t want to pick something that will create something unpleasant. Not willing to take a risk, I just choose a flavorless one and walk back to her.

I take my old position and liberally squeeze some lube on her tight hole before using my finger to spread it around. Then I squirt some more in my hand and apply it to the beads itself. When I´m satisfied I look to her for approval. After she consents, I begin to push again, the eighth bead going in a lot smoother than before. With my finger hooked into the ring at the end I prepare to make the last one vanish in her butt.

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***atherina:***

“Thanks for not arguing about the lube.” she smiles as you follow her wish. “Some guys can be really dicks about that. They think spit is enough or whatever.”

As you apply the lube and look at her, she nods and while you push in the 8th bead you can hear her sob:”Oh my God! Fuck. Me!”

The bead vanishes and she is panting hard. Her head falls down to her arms, then up again and also her ass moves around as she squirms, tying to deal with the stretching. She notices you preparing the 9th bead.

“Wait!” She exhales more than actually says the word.

“Gimme a minute, please” her ass is still moving.

You can see it clench slightly, followed by an abrupt “Ah!” exclamation that sounded more like pain than pleasure. You wait expectantly, while her face is buried in her forearms on the floor.

“Try pulling this one out again, but gently.”

You take the ring and while massaging the inside of her cheeks with the other, you slowly pull on the string. It is stuck pretty firm and at first you pull her butt towards you but then millimeter by millimeter the ball begins to appear as her hole opens back up. You make sure to go slow about it, as the muscle begins to close again behind the large bead.

Katherina is panting and you can see her toes curling up now and then.

“Hah,… Yes.. Thank you.” Ok, well that one was pretty huge already. She took 8, that is amazing. There must already be more than 25 cm in her. You think about the string of beads and how they must follow the path of her guts. You are thinking about how you are going to put your dick into that.

“Now put it back in”, she surprises you. “But slowly. ” You don’t wait for her to ask twice but just in case you put some more lube on the ball and her opening and then you start to push it back in real slowly. “Just. Don’t. Turn. It.” she gets out one word after the other between gasps. She still looks straight ahead, though maybe her eyes are closed, you’re not sure. But her mouth is wide open.

“Oh yes.. Oh yes.. Fuck” she comments as the bead disappears again fully. Her head falls back down to its resting position. Small twitches shake her body. She is breathing heavily, trying to suck air in, just like a diver before going under.

“OK.. Go ahead..But real slowly…Real slowly.”

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***Mathis:***

I grow a little worried at her exclamations of pain, after all I don´t want her to call off our meeting because she is in pain.

“Don´t mention it, if you need more lube or more time I´m happy to comply.” I assure her. I get increasingly horny as I see the beads vanishing in her ass and I can feel a little precum forming on the tip of my cock as I watch her muscle stretch around they toy as I pull it out slightly.

I´m pleased when I hear her wanting to take the ninth bead. To ease her into it a little and take her mind off of the possible pain, I start rubbing her clit a little more, sinking my middle finger into her pussy besides the vibrating lovesense. I use a little more lube on the last bead and once again spread it around her sphincter. Then I start applying pressure with the ring at the end of the toy. Just as she asked I go very slowly, watching for any reaction of discomfort from Katharina.

“You look so sexy with the beads going into your ass I can´t wait to fuck it.” I say voicing my thoughts out loud. Probably not the best thing to say in a situation like that, but I couldn´t contain myself, seeing her take the beads like that made me just too horny.

Source: reddit.com/r/sexystories/comments/d4329t/one_night_with_katherina_part_8