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.
Good afternoon Kyle, hope y’all are getting along well over there in whereever you are. Like we talked about earlier I’ll start with some things I really enjoyed from other couples I’ve played with over the years and progress to ideas for us when you get back.
I’ve found that every couple is totally different with their own kinks and personality and quite of lot of what makes a particular scenario fun with one wife or couple wouldn’t work at all with you and Emily. However, I’ve also found some kinks that I never, ever would have guessed would be fun ended up being incredibly hot with the right partners. So while I wouldn’t suggest we should actually play some of these out with Emily it might get some ideas brewing in the back of your mind that you can tell her about while you’re laying in bed together. You might surprise each other and we’ll have something new to try. Or she’ll look at you like you’re a complete fucking moron and sexy time will most definitely be cancelled for the night. You never just know.
Mary and Ben were the first couple I played with several years ago and my relationship with Mary was a rollercoaster of a ride from the very beginning. Some things happened early-ish in our friendship that allowed a strong emotional connection to develop. It was complicated and nuanced and wildly ill-advised and will take a LOT of time for me to write out. Through it all we had some ridiculously fun sexual adventures together so I’ll definitely get back to her later but for this letter I’m going to write about Betty and Tony, the second couple I played with regularly. My relationship with them was straightforward and quite vanilla as threesomes go so it’ll be a good warmup for me to figure out the form these letters will take.
I met them much the same way I met you. Tony posted to reddit and we chatted a bit as strangers with a mutual interest will do. The big difference is that unlike your wife, Betty was very directly involved almost from the beginning. After I got past the initial screening with Tony it was almost exclusively Betty that I communicated with while Tony just observed. Through some weeks of messaging I figured out they were both 10-15 years older than me but far less experienced with the wifesharing thing. They’d talked about it off and on for years but had just recently built up the courage to actually move past bedroom dirty talk and go find a real cock to fuck her. That was the basis of Tonys fantasy; I have no idea what Bettys impetus was. He basically wanted to be there to watch, take pictures, and join in when he wanted, but more than anything he wanted to sit back and watch his wife being pleasured by another man.
It took time, maybe a month or two, but when everyone was comfortable enough to meet in person they invited me over for “dinner” on their patio. They lived in town, so there were neighbors on both sides, but the back of their property was solid trees and there was no line of sight from the patio furniture we were sitting on to either of the neighbors. In other words, there were no snooping eyes to worry about when Betty left her husband’s side and came to sit with me on the big sofa.
It started slowly. Her hand on my knee. My arm around her shoulders. A small groan when I rubbed the back of her neck and trailed my fingertips down between her shoulder blades. She hated being the center of attention so Tony and I were doing our best to ignore her, chatting away about a steady stream of topics while she adjusted to a strangers hands on her body. As far as I knew Tony was the only man she’d ever been with so it took some getting used to for her. But by the time the sun was setting she’d nudged me down to the far end of the sofa so she could stretch out on her back with her head laying in my lap.
She had on a light summer dress and was clearly not wearing a bra or panties. The thin material was snug across her breasts, making the slight outline of her nipples visible when she stretched her arms over her head and tucked her hand under the back of my thigh. As Tony and I chatted I idly ran my fingers through her hair and rubbed her temples for awhile, moving on to her bare shoulders and arms when I felt her relaxing into me.
Tony had started losing track of the conversation by this point. Less conversation and more silent nodding with an occasional grunt of agreement. He was pretending to listen but the majority full attention was watching my hands exploring his wifes body. He watched me lightly run a finger down her neck to her chest. He saw her nipples harden when my hand slid low enough on her belly to feel her pubic hair and lightly trace the crease between her thigh and her vulva. When she shifted her hips to put one foot on the ground I saw him take a good long look between her parted thighs, thoroughly enjoying the view judging by the growing bulge in the front of his shorts.
I slid my hand under the cups of her dress and trapped her nipple between my fingers, gently squeezing it and pulling a deep, lusty moan from her. That was the tipping point for all of us where the pretense of dinner ceased to matter. She slipped the straps off her shoulders to fully expose her breasts to us, then hiked her skirt up past her hips so she could give her husband an even better show of her arousal. He watched her work her pussy for a moment or two, spreading lips wide so he could see the evidence of her excitement leaking onto the cushions under her. He looked at me briefly and not seeing any opposition he pulled his fully erect cock out of his shorts and started slowly jerking off to his wife masturbating in the arms of another man.
Despite her reservations about being the center of attention she was LOVING having Tony watch her. She spread her legs wider so he could see her dip her fingers into her soaking wet pussy and rub circles around her erect clit. She would alternate between watching Tony stroke himself and closing her eyes to focus on feeling my hands all over her, arching her back when I cupped her breasts in my palm or lightly pulling and twisting her nipples.
She was getting so close to cumming for us. Forget line of sight, if her neighbors were outside they would easily have heard her panting and moaning while she fingered herself. Tony wasn’t being quiet either. He was egging her on, telling her how hot she looked spreading her legs for me and saying how he couldn’t wait to see me bend her over and fuck a load of my cum into her married pussy.
That was all it took to push her over the edge. She squeezed her eyes shut and clamped her hand over her mouth to hold in the gutteral grunts and groans when it hit her, bucking her hips and frantically finger fucking herself through the waves of her orgasm as Tony and I watched her. He was jerking his cock every bit as aggressively as she was fucking herself, quickly approaching his own release.
She took her time coming down from it, slowing the pace down until she was lazily rubbing her pussy as she basked in the post-orgasm high. She took a deep contented breath, stretched, and opened her eyes. She pulled my hand to her mouth and gave it a light kiss then turned her attention to Tony with a playful smile. He hadn’t cum yet and he was still stroking his hard cock, albeit without the intensity he had when she was cumming.
Without a word passing between them he got up, walked over to us on the sofa, half kneeled/half stood next to her, and offer her his cock, which she happily accepted. That was one of the best parts of Betty and Tony; their ability to read each other and adapt to it. She knew he had all that pent up excitement in desparate need of release and he knew she was practically swimming in dopamine after a hard orgasm like that. They met in the middle with a slow, sensual blowjob.
She laid her arm over her head again to find my hand and hold it tight, reaching up with her other hand to guide Tonys cock to her mouth. She kissed it softly, slowly. She flicked her tongue over his balls and licked her way up his shaft before taking him into her mouth and gently sucking his head. She cupped his balls in her hand and tugged him toward her, signaling him to fuck her mouth.
He slid in and out of her in long, smooth strokes, sometimes pulling out completely so she could suck on his balls and stroke his cock for a couple seconds before pushing himself back into her mouth. While he was busy using her to get himself off I was caressing her body with my free hand, from the middle of her chest over her breasts and down her belly to brush across her clit, then back up her side. She never let go of my other hand and she’d occasionally give it an appreciative squeeze when I gave her nipples or pussy some extra attention.
Between Tonys cock in her mouth and the ever increasing attention I was giving to her clit Betty was gradually working herself up to another orgasm, which Tony finally noticed when she started squirming in my lap and moaned a little around his cock. I was full on masturbating her by this point, her pussy rhythmically squeezing the three fingers I had buried inside her. Tony was looking from my cream covered fingers penetrating his wifes pussy to his cock disappearing between her lips. He was definitely enjoying the scene because his thrusts started getting more and more aggressive as he got closer to emptying his balls onto her. When he reached down to grab a fistful of her hair and give her a proper face fucking she gave up playing with his balls and moved her hand between her own legs. She hiked her leg up over the back of the sofa to give us both room between her thighs, her frantically rubbing her clit and me fucking her with damned near my whole hand.
He finished first, pulling out of her mouth at the last second to shoot a huge load of cum across her chest with a groan. His cock hadn’t finished pulsing when she announced her second orgasm to the whole fucking neighborhood. This time she made no attempt to cover the stream of profanity that ended in a “ahhhhhhh fuck fuckfuckfuckFUUUUUUUUUCK” when she came for us.
Tony had no trouble staying fully erect after watching that display so I think he could have gone another round but she was down for the count after that. She was covered in sweat and cum with a sore throat, a sore pussy, and a very, very satisfied smile on her face. Tony tucked his erection back into his shorts and sat down in the chair across from us again. We sat around chatting, drinking, and recouperating with his half naked wife laying in my lap like that for probably another hour before I excused myself to head on home.
Tony, Betty and I had lots of other visits over the course of our relationship but I chose to share this one with you for a couple reasons. First, it’s the only sex we had outside their spare bedroom. I love outdoor sex. On a picnic blanket, beside a campfire, on a beach at night. I can’t put words around why I like it, I just do.
Letting Tony watch me coax his wife into arousal was unexpectedly fun for me. I mean, I’ve known I have a minor exhibitionist streak for years so I’m sure that was part of it. I had an experience awhile ago that involved me and some woman I didn’t even have a name for watching each other masturbate that I’d rate as one of my top 10 experiences. This was something different though. This was…hmmm. This was something. I don’t know what this was. The cynic in me says it was simply an ego boost; demonstrating my sexual prowess to an attractive womans husband or some other alpha male bullshit. I don’t think that’s exactly it though. Maybe sometime you and I can talk about why you like seeing me with Emily and why I like being with you and Emily together and we can figure this one out. Until then it’s just one of lifes little mysteries I guess.
I also have a particular liking for the casual way we progressed through the evening. For some couples I’m there for exactly one reason; they want me to show up, scratch whatever itch they have, and I’m on my way. That’s fine and all but given the choice I like a slower buildup. I like the teasing and playfullness of it all. Dirty sexy playtime is obviously the end goal but there’s fun to be had by not being laser focused on the goal itself and just letting it happen however it happens. Taking the scenic route is sometimes better than actually arriving at the destination.
Lastly, watching Betty give Tony what could possibly be the sexiest blowjob in history is what made me consider bisexual play. I wasn’t ever against it as such, it just hadn’t ever crossed my mind as a possibility. Bisexual porn didn’t do anything special for me. Pictures and videos of objectively attractive men never did anything for me either, other than I’d be like yep, that’s an attractive man. But in a moment that legitimately could have ended with me sexually pleasuring another man it seemed like a fun thing to try, and beyond the social stigma of it there wasn’t a compelling reason not to. If Betty or Tony had shown interest in me helping her get him to cum I absolutely would have. I would have held his cock for her while she sucked on him. I’d have jerked him off onto her breasts while she was fingering herself. I probably have even given him a blowjob myself while she watched if that’s what she had wanted. Lol…I might have been better practiced for when Emily and I shared your cock if that first experience with Betty and Tony had gone just a little different. Your loss I suppose. Maybe next time Emily can stick to coaching from the sidelines and I’ll pick up a couple tips and tricks.