Earlier this week, I invited my play partner over for the evening. We had met here on Reddit and she had visited me a few times before this story. I’m 42M, Dom, divorced, poly, just under six feet tall, a couple extra pounds, blonde hair, blue eyes, and a beard with a bit of gray in it. She is 21F, submissive, pretty, and short, with a lithe little body, long brown hair, beautiful eyes and a smile to melt your heart.
She had hinted before that she’d found a dress and bought it to look cute for me, and she showed up to my apartment wearing it. “Cute” turned out to be an understatement. It was a short black dress with a rose pattern sewn into it, a little transparent at the bottom to show a hint more of her thighs, a low neckline to show a generous view of her chest. I gave her a hug and told her how pretty and sexy it looked on her, and we sat down and cuddled on the couch and made out for a bit. Then I had her stand up in the middle of the room and model the dress for me. I started stroking my cock as she showed off, posing and turning, shifting her weight from hip to hip, slowly lifting up the hem of the dress to show her panties, lowering the straps to expose her breasts. Turning around again, reaching down to her touch her toes to reveal her ass as the dress rode up.
After a bit I called her back over to the couch and kissed her, drawing her hand to my cock and letting her take over the stroking. “It’s a really pretty dress you got for me,” I said. “It would be a shame not to fuck you in it, don’t you think?” She agreed eagerly and I told her to take her panties off and to give me a condom from a small pile I’d left nearby. She pulled off her thong and I pulled her over my legs, straddling me as I lowered her onto my erection. She rode me for a while, arms around my neck, while I kissed her face, and neck, and breasts, gripping her ass and back. After a few minutes, her body shuddered against mine as she orgasmed. She made the cutest little squeals and whimpers as she came, and I held her close, and thrust my hips slowly into her from below, kissing her and telling her what a good girl she was for cumming on my dick.
We made out a little more with me inside of her like that, letting her catch a breath, and finally I lifted her gently off of my cock. “Let’s go to the bedroom,” I said. We stood up, and I took the dress the rest of the way off of her (it was dangling anyway at this point) and led her down the hallway to my room.
Earlier in the day, I had made a little extra space in my bedroom and moved my coffee table from the living room to the bedroom. I put a body pillow on the top and tied a rope in a capital I-shape between the legs underneath. That had conveniently also made space in the living room for her to model the dress. But now I had her lie down naked on her stomach on the body pillow, positioned with her crotch at the edge of the table, legs spread and feet on the floor, arms stretching toward the other end of the table. As a makeshift spanking bench, it worked rather well! I cuffed her arms to the rope on the one side and tied each of her legs in place to the rope around the table legs on the other. I put a sleep mask over her eyes for a blindfold.
Her legs spread, she was exposed perfectly to tease her cunt and ass, and so I crouched behind her and touched her very gently on her inner thighs, her labia, and the bit of flesh between her pussy and anus. She started moaning, and I slipped a fingertip just barely between her pussy lips…then slowly down across her clit. She shivered and I continued slowly rubbing her clit, until soon enough she came again.
Then I slowly circled a fingertip around her asshole, before pushing it inside, eliciting a squeal from her. I started working my finger in and out of her ass, as she whimpered and moved against the restraints. They held, and when I decided she was ready for it I took my finger out and slowly pushed a plug into her hole.
Plug securely inside, I checked with her to make sure the ropes were comfy and then I took out a small flogger to warm up her cheeks. She was very vocal about the flogger, so once she was turning a bit pink with that I moved through the next few implements, taking my time with each. First, a riding crop for some precision strikes, moving to a wooden spoon which left circular marks that turned pink and then red on her ass, then a long wooden paddle that could reach across both ass cheeks at once. Finally, a wicked little DIY flogger made from a folded USB cable that left looping stripes. She called Yellow after a couple strokes with that, and we stopped the impact play immediately and I checked in with her, kissing her and stroking her back for a little while, until she assured me she was really good to keep going, but would prefer no more impact on her bottom, please.
Deciding it was time for a little more pleasure, I plugged in the Hitachi wand. Starting on the lowest setting, and teased out another orgasm from her pussy. Then I increased the setting and quickly got another orgasm; she was practically howling. I turned it up to high and kept it pressed tight against her clit through another couple orgasms. One of her legs and both of her hands were shaking by the end of it. Eventually I turned off the wand and gently touched her thighs and pussy as she came back down to earth; she was extra sensitive at this point from the sound of things and the little wriggles she was making. I pressed two fingers into her pussy and fingered her for a while, to several more wriggles and squeaks. She was so wet and tight and her pussy clenched over and over on my fingers, and very quickly I decided I absolutely had to have my cock inside of her.
Unfortunately the coffee table is a little too low, and apparently it makes for a better spanking bench than a breeding table, and after trying out angles and trying to prop her up a bit…I came to the conclusion that I would need to be more of a professional baseball catcher to crouch in the proper way for long enough to use her cunt properly. Fortunately, though, she had another hole available with easier access. I slowly took out the plug and told her I was going to use her ass to please my cock. She nodded and whimpered out a Yes Sir.
I pressed the head of my member against her back hole and slowly entered her. The plug had done some good preparatory work, and lots of lube made it easy to slide myself in bit by bit. She pleaded with me to go slow, and I did, and it felt amazing, so tight and warm and just the slightest movement sending spasms through her body that I could feel on my cock. She moaned something about how I big I am. One never minds hearing that. I told her to do the moving for us, and she managed little movements accompanied by more of her cooing and squeaking.
I began to make gentle thrusts against her movements, bent over her on the table, practically lying on top of her but propping myself up a little so as not to crush her. She moaned me that she was going to cum again. I told her if she came it would make me cum, deep inside her ass. This proved to be a self-fulfilling prophecy, because my saying that sent her over the edge, and feeling her orgasm from inside her ass was more than enough to have me unloading into her. I moaned and growled in her ear and told her what a delicious little anal slut she was and how good it felt to cum inside her ass.
We stayed like that for a couple minutes and enjoyed the feeling and then I carefully pulled out of her and untied her from the table and we moved to the bed. We cuddled and kissed a dozed off for a while and then I cleaned up a little and we cuddled more and talked about hot it had been and how good it had felt.
Eventually my hands started to wander over her body again, over her breasts and stomach and legs, until inevitably they found her pussy. She buried her face in my chest and I teased her clit and held her close and gently rubbed her to another soft orgasm. We dozed a little again, after she woke up again I kissed my way down her body and used my tongue and fingers for a good long while. I think I lost a little bit of time there; I don’t really know how long she was moaning and trembling with my head between her thighs. By the end of it, however, my erection had come back and so I put on another condom, turned her over onto her stomach and pulled her onto my cock again. Afterwards we both collapsed, exhausted, and we held each other and kissed for a little longer, talking about other things, until sometime long after midnight.