There is a backstory for this series of posts in my profile. The format will make more sense if you at least scan through that first.
10-May-21
So Kyle, I may have told a bit of a lie earlier. I don’t think I’ll be writing as many of these about previous couples as I said I would. Maybe one more after this one, tops. I’d rather spend my time telling you all the dirty things I want to do with you and Emily. Or have you and Emily do to me. Or Emily and I do to you. Or maybe all of them. Hopefully all of them.
Speaking of Emily, did she tell you we’re going to see each other this weekend? So far we have breakfast and bookstores on the agenda, beyond that we’ll see where the wind blows us. If the weather is nice maybe we’ll end up using one of those walking paths the state maintains. Gotta beat the skeeters out there otherwise it’ll be miserable.
Anyway, back the real topic, Riley and Kurt. My relationship with them was probably best described as a bull and cuckold dynamic, though I absolutely hate that phrase. Sooooo much douchery from ‘bulls’ here on Reddit. It’s an absolute cringefest. However, that’s generally what Riley and Kurt wanted. More specifically that’s what Kurt wanted. Riley was playing the good wife and indulging his fantasy at least to begin with. The big difference between what they wanted and what is typically advertised as a bull was that the aggression and domination would all come from Riley, not from me. “You don’t worry about my husband” she told me. “You’re here to take care of me. I’ll take care of him”. The really wild part was watching them figure out how to really do that though. They mostly stuck to their fantassy roles but they did flip-flop on me a couple times, mostly because Riley needed some reassurance from Kurt the first couple visits.
Kurt was very much in charge of, well, everything so far as I could tell. When we first started chatting he would very aggressively intervene if he thought I was testing the boundaries, being disrespectful, or when the conversation strayed into personal topics. Very aggressively, borderline dickishly and generally unnecessarily. Overly protective of Riley is how it felt. But once he laid out the rules and we figured out how to interact with each other it smoothed out nicely with Riley and I flirting, teasing, and sexting right up until we scheduled our first meeting.
They’d had several guys bail when things got serious about meeting in person, which was a huge letdown for Riley and a major blow to her self-esteem. I think right up until she opened the door to her hotel room and saw it was me she had convinced herself I wasn’t going to show. When she recognized me her face lit up with this beautiful smile and she opened the door to invite me in.
From our chatting she knew I have a weakness for a woman in nothing but an oversized button down shirt and panties and she dressed to take full advantage of that; a white cotton top that hung down just past the tops of her thighs and a pair of dark burgundy panties. Seeing Riley standing in the doorway, clearly ecstatic to see me and holding her hand out to me, is one of my favorite memories…second only to your own wife that time she had the dark blue-grey dress on.
The room they had was one of those big suites with the open kitchenette and living room with a separate bedroom off to the side. Kurt was sitting at the peninsula on the kitchen side, which faced the big L-shaped couch in the living room. Riley took me over to the couch and put me squarely on the enter cushion then took a seat reclining to my right, one leg folded under herself and the other stretched out across the long section of the couch. I’m pretty sure she chose that arrangement carefully as it meant Kurt was to my left and completely out of my view when I was looking at her but she could see both of us at all times.
We had been chatting for maybe 10 minutes or so when I saw her eyes look past me and focus on Kurt for a moment. When she looked back at me she smiled a bit and said “I think I’d like to kiss you”. I wasn’t expecting the abrupt change in the mood so I kinda just nodded my head in agreement and said “I think you should then”.
She scooted up onto her knees so she was kneeling on the couch next to me and gave me a long, wet, sexy kiss. She had been fantasizing about this exact moment for years and she was not in any mood to rush through it. I felt her shiver with excitement and moan into my mouth when I reach up to caress her cheek while we kissed. We stayed like that for several minutes, letting her soak in the sexual tension.
Without breaking our little makeout session she swung one leg across my lap and straddled me, resting both her arms on my shoulders for support. My hands were busy exploring her body while we kissed; her shoulders, the curve of her back, the soft, smooth muscles of her exposed thighs, and the deliciously soft swells of her breasts. When I got to the hardened nipples pressed against the fabric of her shirt she broke off our kiss and laid her head on my shoulder. As I palmed her breasts and tweaked her nipples she started rolling her hips back and forth, grinding her crotch against the bulge in my pants.
I started to unbutton her shirt but after three buttons she put her hand on mine to stop me. “I bought this shirt for you to fuck me in” she whispered in my ear. “Whenever I wear it I want Kurt to remember the night I made him sit in the corner and watch another man fuck a load of cum into me”. With that she stood up in front of me, slide her panties to the floor with a sexy little shimmy, and told both of us she was ready to find out what she had been missing by only letting Kurt fuck her for so many years.
I took her to the bedroom and she stopped in the doorway to address Kurt, still sitting in the kitchen. “You heard what I said. Come in here and go sit in the corner. And take your pants off. I want to see your cock get hard watching him fuck me”.
She didn’t wait for Kurt to take his place. Just inside the door she pulled my shirt over my head, then quickly stripped off my pants and underwear. When I was fully naked she gave me another kiss and reached down to give my balls a light squeeze. “I hope these are nice and full for me.” she said between kisses. “I want it to be dripping out of me when you’re done”.
She climbed onto the bed on all fours, giving her hips an extra wiggle so I got a good look at her ass up in the air and her pussy peeking out between her thighs. She arranged a couple pillows against the headboard and rolled onto her back. She was leaning against the pillows so she could see Kurt, who was now sitting in the armchair in the corner of the bedroom, naked from the waist down and sporting a solid erection.
Satisfied with Kurt she turned her attention to me, locking her eyes with mine and spreading her legs wide for me. I know an invitation when I see one so I climbed on the bed and kissed my way from the soles of her feet up to her very aroused pussy. I worked my way up her legs and was planting little kisses up and down her slit when she put her hand on my head to urge my tongue deeper into her. With her free hand she pulled her shirt to the side to expose her nipple, lazily pulling and twisting it while she watched Kurt and let me lick her swollen clit.
She was putting on a heck of a show for him, moaning and bucking her hips while I tongued her clit, but oral sex was only a warmup for her and not what she was really after, so she pushed me away after awhile and got back on her hands and knees in the middle of the bed. She looked over her shoulder at me and pulled the tail of her shirt up over her hips, letting me know she was ready for me.
I entered her slowly that first time. That’s always the best part, sinking into a woman, the feeling of her pussy swallowing my cock, and the delicious steady squeezing around my shaft when I’m buried up to my balls inside her. When I bottomed out in her I stayed still, just my hands holding her hips and my cock pulsing insider her. From our chatting I knew she had a very specific fantasy for our first time together but she would never give me any details. Rather than mess it all up I just let her control the scene.
She start fucking me slowly at first, leaning forward until I could see her pussy lips beginning to part around my head, then back down my shaft until her ass was seated firmly against my hips again. Back and forth in a steady rhythm, rubbing her clit and never breaking eye contact with Kurt.
I don’t know what gave her more pleasure, my cock sliding in and out of her or staring into Kurts eyes as she used me to get herself off. Her pace never changed, the only sign she was getting close was the gradually increasing urgency in her grunts and groans. She pressed her ass against me hard and held it there when she came. Her orgasm was nearly silent, only a few quiet moans, but I could feel her dripping down my balls as her pussy clenched around me. She wasn’t a squirter by any means but her body wasn’t stingy with the lubrication when she was excited, doubly so any time she orgasmed, and every time we fucked she left me covered in her cream from my balls to the tip.
She didn’t pull off of me like I expected her to when she was done. Instead, she switched to grinding her ass against me with these short but firm strokes and beckoned Kurt to the bed with her finger. “Lick us clean” she ordered. “And you”, she said as she tapped one of my hands holding her hips, “give me that cum you promised.”
When Kurt stood up his cock was painfully hard, which I’m sure Riley was quite happy with. He laid on his back and scooted underneath her until he was staring straight at her lips stretched around me. She was still fucking me with agonizingly short strokes but had moved so only the very tip was insider her. Feeling her pussy working my head was heaven…then I felt Kurt start to clean her juices off my balls. That was a sensation like no other, the whole scene. Watching Rileys ass up in the air, the end of my cock disappearing inside her. Looking between us to see Kurt licking my balls and the base of my cock clean. Feeling her squeeze tight around me and slide the full length of my shaft into her when he moved from cleaning my cock to lapping at her pussy. Seeing her hand wrapped around his cock when she laid her upper body against him and rested her head on his thigh. Every bit of it was dirty, sexy, and fucking awesome.
I knew I wouldn’t last long when she laid against Kurt like that, essentially relinquishing control of our fucking to me. I put one hand on her lower back to hold her in place while I fucked her for just a couple more minutes, then gave up fighting it and unloaded into her, filling her pussy with the cum she very much deserved.
Almost as soon as I was done pumping into her she slid off my cock and started grinding herself against Kurts mouth. I watched him eagerly tonguing her clit and lapping up the combined cum that was streaming our of her pussy for a couple minutes, then crawled around her so I could see her face. She flashed a wickedly devious smile at me and said it felt like I had really enjoyed myself back there.
We had a laugh about that, I kissed her forehead, then we had the most surreal conversation ever. She thanked me for stopping by, said it was everything she had wanted, and that she hoped we could do it again sometime. Just an everyday conversation like we’d just finished a round of mini-golf or something, totally ignoring the fact that she was still on her hands and knees with her tits hanging out of her top and her husbands erect penis leaking a steady flow of pre-cum against her cheek while she humped his face and made him eat the creampie that I just deposited into her a couple minutes ago. Surreal and actually kinda hot. She told me to get dressed, grab a bottle of water out of the fridge, and see my way out.
This letter ended up waaaaaaaay longer than I had expected but, in the interest of sharing things I’ve done with other couples that I liked, this one is important to me. Riley and Kurt were the first couple to actually show me how to incorporate this idea of domination and control in a respectful and mutually satisfying way. I went into it with a lot of reservations about the types of play Riley had written to me about, and honestly I think she was also worried as this was 100% Kurts idea. We ended up having a lot of fun with the whole femdom/cuckold/whatever-that-was dynamic though. Their bedroom kink was the exact opposite of their ‘normal’ personality. The last couple I’m planning to write to you about next week is Jamie and Gary; those two took submission to an extreme. Well, Jamie did anyway. I’ll try to keep that letter a bit less wordy. ;)
Source: reddit.com/r/sexystories/comments/nbv6z4/open_letter_2_past_partners_riley_and_kurt_mfm