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-Jun-21
Hey Kyle, so I got to thinking the other day about a conversation you and I had awhile ago about the difference between a bisexual play date with all three of us vs you and I playing without Emily. Looking back, you and I could easily have gotten each other warmed up that time we sat around talking in the hotel room while we were waiting for her to get off work and I wouldn’t have had any problem with that at all. Specifically scheduling a time for us without her feels different though. Can’t say why, it just does. So that led me down the path of imaging what it would look like were that to happen, why I perceive that as less exciting, and put some logic to the whole topic.
Some days when I’m at work I just can’t focus on anything. Might as well not even be there, really. It’s better for both me and my employer if I just cut our losses and split for the day, which I sometimes do. Leave around noon and just never go back. Shoot, sometimes I even take a coworker or two with me. Go wander around the zoo or catch an afternoon baseball game or something…anything’s better than sitting under fluorescent lighting when it’s a gorgeous day out.
That only works if it’s nice out. When it’s rainy or cold out, I think that’s when I’d possibly shoot you a message and see what you’re up to. If you’re sitting at home doing not much of anything I might suggest you get your ass out of bed, go jump in the shower, and I’ll be there in an hour.
Now, see, right there. That’s where I get conflicted again. My initial reaction would be that telling you to wait until I’m there and I’ll join you in the shower isn’t appealing at all. I mean, I don’t find the overall premise offensive at all, it’s just not particularly exciting. But when I flip it around and think through what would happen if you said the door will be unlocked and you’ll be waiting for me in the shower, some of what that might entail sounds fun.
I can easily imagine how your body would feel. I can imagine sliding into the shower behind you and reaching down between your legs to cup your balls with one hand while my other hand is exploring your chest. I can feel your half hard cock twitching with anticipation in my hand when I wrap my fist around it. I can hear you groan as I stroke you and pinch your nipples. I’m sure my own cock would be rock hard as well; you and Emily seem to have that effect on me.
Can you imagine yourself there in the shower? Head down, getting a slow, steady hand job with my hard-on pressed against you, sliding up and down against your ass as I grind against you. I’m almost certain I could get you off like that, and I find the image of you cumming with your cock in my hand very exciting, not to mention that I’m practically fucking your ass while you do it. And maybe that’s all that happens. I get you to cum in the shower to start your day off right, we get out and have lunch, I have fun messaging Emily and bragging that I did a better job than her today, and I’m on my way.
Ignoring the possibility of shower handjobs, how would it work otherwise? If you were already through the shower when I got there I’m guessing I’d find you in a loose t-shirt and baggy shorts. You’ll know why I suggested going over there; do we pretend it’s a social visit or jump right in? I’ve had mutual masturbation meet-ups with women before and there’s always this awkward transition period from casual conversation to sexy time. With you, since I’m already comfortable with you, I think it would be simpler to jump right into it.
I’d kick off my shoes, lose my jeans, and take a seat next to you on the couch. At first I think I’d just like to jerk off together. See you rub yourself through your shorts for awhile before you pull your cock out. Maybe we’d put some porn on to watch, or maybe we’d talk about things we’d like to try sometime. Or I could give you all the details about past play dates I’ve had that didn’t make it into these letters, complete with pictures and videos for the ones I have permission to share. I’d also love to hear some of your adventures. Whatever path it takes I would definitely be interested in watching you.
Depending on how we’re feeling about it I might even be interested in stroking you myself. Let you sit there on the couch with your head back and your eyes closed while I work your cock for you. A word of warning: It’s a lazy Tuesday afternoon so I wouldn’t be in a hurry to get you off. That’d be a terrible waste; what would I do with the rest of my afternoon off work then? No, I’m going to enjoy giving you a handjob as much as you’re going to enjoy receiving it, so you’re going to have to wait until I’m done having my fun before you cum.
And sitting beside you would be uncomfortable. I’d relocate to the floor between your legs if it looks like things are going to escalate. And you’d need to ditch those shorts. I’m not exactly an expert at this so I need easy access, room to work, and all the advantages I can get.
I’d start by running my fingertips up and down your thighs after you’ve settled into place. You might as well just lean back into the cushions and put your hands behind your head because I’m not going to let you rush this along by doing it yourself. Nope, this is my time to practice and explore. I learned what I could from watching Emily last time we played; if I’m not doing it right this time you’d better tell me ‘cuz I skipped out on my whole workday and I have like the next 5 hours free. You can have a fucking awesome time and I can drain your balls in under an hour or you can go to work horny and frustrated later. The difference between those two is you being open about what you like and how I’m doing on the delivery.
I’m going to run my hands over your body for a bit before I get back to your cock. Up your thighs and hips, across your chest…maybe let my wrist rub across your shaft occasionally or lightly brush your balls with my fingers on my way up your thigh. Just enough stimulation to keep you decently hard and to make you squirm a little. When I’m teasing a woman that’s my favorite part, those subtle little signs of arousal and an appreciative moan now and then. I’d have to guess seeing you respond to my touch would be no different.
When I finally get to your cock I’m going to barely touch you at first, just my fingertips tracing your ridges and contours, watching your abs tense up and your shaft flex in anticipation, working my way from the tip of your cock down until I can cup your balls and feel their weight in my hand. I wouldn’t be working you to orgasm yet, still just playing and letting you relax and feel my hands all over you. Chest…arms…legs…and a steadily increasing amount of attention to your cock, eventually circling my thumb and index finger around you and giving you a couple teasing little tugs, then using both hands to squeeze your whole cock and stroke you.
Your balls need some attention too. I’d cup them in my hand and roll them back and forth with my fingertips while I’m stroking you. You’d be in heaven with all that attention, leaning back with your eyes closed while I build up to making you cum. That’s exactly what I like to see from my partners, totally disconnected from everything but the feeling of the moment. If I’m doing it right you’d be so preoccupied by what I’m doing to you that you wouldn’t even notice that Emily came home.
I’d message her while I was driving over so she’d know I was there, just in case she was bored at work too and wanted a show, and since she saw my car in the driveway she’d know to be extra quiet so she can sneak in without interrupting us. I’d hold her gaze for a moment or two when I see her peeking around the corner to acknowledge her presence, then swallow as much of your cock as I can. After teasing buildup I’ve given you the unexpected sensation of my hot, wet mouth sliding down your cock makes you groan loudly and thrust your hips a little, eager to find your release. If she came home for a show that’s what I’m going to give her.
Not just a show of me sucking your cock, that she’s seen before. I want her to have the chance to be a spectator, completely separate from what’s going on if she wants. She could certainly come around the couch and join me if she wants. Kissing Emily with your cock between us is near the top of the sexiest things I’ve done with you, top 5 at least, so that’s always an option for her, but she could also decide to snuggle up to you on the couch, alternating between watching me and kissing you. I can easily see her plopping down beside you with her head on your shoulder and an arm around you to just hold you, to feel your body responding to me, and to watch you completely focused on enjoying yourself without worrying about her having fun. Depending on her mood she might want to have just a little bit of fun with you, possibly holding your cock up for me and whispering some delightfully dirty things into your ear while I’m sucking you off.
Forget about what Emily wants to see, that’d make a pretty ok scene that I’d like to see! Think about what that would look like from a third person point of view. This cute little wife comes home to find her husband half naked on the couch with his cock down another mans throat, completely engrossed in the blowjob he’s getting, then she decides to join in by curling up in his arms, talking dirty to him, and nudging him closer and closer to his orgasm with soft touches and little kisses until he shoots his load…dirty and sexy and intimate all in one. Checks all my boxes, plus I get to have your cock in my mouth.
Of course, those paths all mean she’s involved in the play. I’ve noticed she sometimes likes to be more of a behind-the-scenes kind of girl so she may well decide to stay completely out of your sight. She may opt to watch you empty your balls into my mouth without you ever even knowing she was there, waiting until we’re done before she snuggles up to you on the couch for some post-sex cuddles.
Being an invisible spectator can be fun but she may also decide to take a seat in the chair across the room, kinda halfway between invisible and involved. And you know what? Since I’m the one writing this letter I say she just happened to be wearing a sundress that day, or at the very least I say she ditched her pants on the way into the living room and was wearing just a t-shirt and panties so she has easy access to touch herself while she’s watching us. Being watched is one of my kinks so in some ways that’s sexier than her helping me make you cum. If she helps that’s her showing acceptance and sharing in your pleasure; if she masturbates from across the room that’s her being aroused by your pleasure. Or being aroused by you being pleasured by another man. Either way, that’s an intensely erotic scene for me.
I’d have to up the ante if she does that. Maybe I’d have to let you take over stroking your cock so I can focus on tonguing and sucking your balls for you. And since you’re fresh out of the shower I probably wouldn’t stop at your balls. I’d have you scoot down even further on the couch so I can let the tip of my tongue flick across your asshole in-between licking your balls. I’ve never had anyone do that for me but I bet it’d feel absolutely amazing, and I’m sure Emily would love the moans and groans I get from you every time I did it.
It wouldn’t take but a couple minutes worth of stimulation from your hand and my mouth for you to be covering your stomach in ropes of cum, especially if she’s watching you with her panties to the side and her shirt pulled up. I’d put money on it…not even 5 minutes after we got to that point and you’d be unloading all over yourself. If she wants to push the scene even further she’d better go grab the lube from the bedroom before you cum.
I know she wouldn’t tell me directly but if she sets the bottle of lube on the floor beside me I’d figure out what she wants to see. Like I said, that whole scene would be ridiculously hot for me so I’d definitely be stroking my own erection the whole time I’m sucking yours, and if she wants to see me fucking your asshole instead of teasing it I’d be more than ready to show her by that point.
I’d have you reposition yourself on the couch, laying on your back, and spread your legs for me so I can fuck you without blocking Emily. I want you two to be able to see each other the whole time. I want her to see you watching me lube up my cock and the pleasure on your face when I use my thumb to get you ready for me. I want her to see you close your eyes and focus on the sensation of my cock pressed firmly against your hole, coaxing you open, slowly penetrating you until she hears your breath catch in your chest when my head finally slips inside you. I want her to hear the groan deep in your chest when I reach down to fondle your balls and stroke you, my hand still covered in lube from coating my own cock, while I let you adjust to me. And when you give me permission to keep going I want her to be able to see how hard her husbands cock gets when he’s on his back, legs spread, and a cock balls deep in his ass.
This time, that’s where that scene would end up. What started as you and I jerking off together to fill a boring, restless afternoon escalated into your wife watching me fuck you in the living room. It could have gone a thousand different ways but that’s where my imagination took me this time. If I wrote this yesterday instead of today it probably would have been different. It definitely would have been different if you or Emily had been here to tap me on the shoulder and say ‘yeah, no, it’s never going to happen like that”.
So back to what prompted this letter: you and I playing without Emily. I still don’t know what I think about that. I think where I am is that I wouldn’t turn down the opportunity to try it. In fact, I think I can go so far as to say that I want to try it. That’s one of the really great things about you two. I know if we put it on the calendar and it just doesn’t feel right for me as we’re getting into it it’s no big deal for me to just say that. We stop and add that type of play to the Nope column and there’s no harm done.
I don’t have specific hangups about playing with you alone, same as I don’t have any specific hangups about sexy time with just Emily. If that’s how things work out and there’s full knowledge and consent for all then yeah, why not? But having both of you is soooo much better. I think that’s the difference for me. When I play with both of you I get to watch you two fuck, which is incredibly hot. I get to suck your cock with her and fuck her pussy with you. I get to hear her giggles and your groans. Everything’s better with both of you so if I had the option I’d go for the threesome every time. I doubt I’d ever get bored doing that. In second place then would be seeing Emily without you. I mean, it’s not really a competition if I’m being honest. That woman’s adorable and you’re, well, just a dude. Dudes are going to lose against a pleasant smile and a pretty face every day of the week, plus twice on Mondays.
That’s not to say that you coming in third place is unappealing or that because there are two options I like better I would not want the third option once in awhile. I just wrote a shit tons of words about how I could have a lot of fun with that. That’s just me trying to articulate my feelings, to you as well as myself. This one’s a bit elusive and I’m sure this won’t be the final word on the matter.
Source: reddit.com/r/sexystories/comments/ny9pnh/open_letter_6_some_days_arent_meant_for_workingbi