I have a friend that I shall call Scout. And when I say “friend,” I mean that Scout is a colleague that I’ve had a bit of a romance going on with for over a year now. He’s tall and muscular with salt and pepper hair (he’s in his late 40s) and a boyishly handsome, clean-cut face. He treats me well and we have off-the-charts sexual chemistry. He’s pretty much perfection. Only, he’s married. I know, I know…bad girl. But I will say that this is not by any means any kind of deep, emotional affair. We get along well and text pretty much daily while we’re both at work during the day (not so much nights and weekends, when he’s home), and I’d even classify us as good friends, but this is not exactly a lovey-dovey type of thing. We’ve never broached the subject of feelings or love or expectations or anything of that nature. While I do sometimes miss him or feel the urge to talk to him when he’s unavailable, and I do really care about him because I think he’s a good guy and we have fun together, it’s not like I love him or anything. At least, I don’t think I do. Who knows?
In any case, this is not a thing where we’re making plans to ride off into the sunset together. I’ve never asked him the whys of his infidelity (well…once when I was drunk but I don’t remember the answer) nor has he ever offered any reasons. He doesn’t bitch about his wife or try to cry on my shoulder or anything like that. If I had to guess, as he’s just shy of 50 and I’m assuming his wife is somewhere around the same age as him, I’d just assume that, like most marriages that have been in effect that long, it has lost its spark. They’re probably not having sex regularly, or even at all at this point, and so he has to take care of his physical needs elsewhere. Otherwise, I assume he’s comfortable with his home life and I’m perfectly okay with that. I don’t have any intentions of trying to disrupt that for him. Not my thing.
Scout and I get together maybe about once a month on average. Every so often he will manage to get out of the house, usually on a Friday night, under the guise of going out to drink, and he may or may not actually do that to some extent, but then he sneaks over to my house for the rest of the night and the fun commences. Despite the fact that it’s not an emotional affair on the surface, it’s also not a wham-bam-thank-you-ma’am sort of thing either. He comes over and we may or may not have a drink or two together and hang out and talk some first, or sometimes we might just get right down to it. Whatever the case, he always sticks around for a while after and we cuddle and talk. It’s nice, for what it is.
So, we’re both pretty sexually adventurous people, and at certain points in the past we had discussed the possibility of having a threesome with another woman. It was something neither of us had ever done and we both agreed that it’d be something to consider if the opportunity ever arose.
As it happens, in early to mid-January, I got a text from another work colleague – Tyra. I’ve known Tyra for a few years and we’ve hung out several times years past, but I hadn’t really seen or talked to her in a while. She was hitting me up to tell me about another mutual friend she had heard from out of the blue, and we did some catching up from there in ensuing conversations. And they were perfectly normal conversations, until the point where she started making mentions of a guy she was seeing and how good in bed he was. And proceeded to share with me an x-rated picture of him. Standard (or slightly borderline) girl-talk fare I guess, but things seemed to be starting to take another turn when she suggested that we all hang out together.
See, Tyra and I are cool and she’s never overtly flirted with me or made a move on me or anything like that, but even from years ago when we hung out more, there were some subtle vibes I used to catch from her sometimes that kind of seemed to be on the sexually suggestive tip. Super subtle, but I’m a very intuitive person.
In any case, given that history and the fact that she suggested that me, her, and her boy-toy “hang out,” I started picking up on some of these very subtle vibes again. It was clear to me that she was trying to gauge my interest in joining her and one of her guys in bed.
But while her guys sounded great and the one face picture I saw was of a decent looking gentleman, I wasn’t interested in sleeping with them. What I WAS possibly interested in was getting her to join me and Scout if I could finagle it that way. Of course when I mentioned it to Scout that I was getting that vibe from her, he was all for me trying to work the angle. So I did.
I reversed her technique back on her. I told her about Scout and how hot and good in bed he is. She didn’t know who he was at first, but once I gave her more details about him it turned out that she knew of him from in passing. Even better, her exact words upon realizing who he was: “OMG…I LOVE HIM.” Even better, it turned out that she had a little bit of a thing for him. So I suggested that WE could all hang out, and she was with it.
Of course, Scout was absolutely elated once I let on to him that Tyra thinks he’s hot and said she wanted to hang out with us. While there was never anything overtly said about threesomes or sex, it was quite obvious what the underlying agenda was…an implicit understanding among all parties.
So now we had this threesome event progressing from an abstract idea into what looked like a tentative thing with an actual viable candidate, and I started having my reservations.
Firstly, I always envisioned something like this with someone who was NOT actually a friend, so as to avoid any possible awkwardness or complications in the future. Like, me and Scout just happened to be out and to run across a candidate and one thing led to another and it was more of a one-night stand thing with someone we didn’t ever have to cross paths with again if we didn’t want to. But not only is Tyra a friend of mine, she’s also a colleague of ours. I’m always careful with workplace relations because I’m a discreet person and don’t like everybody knowing my business. Scout is married and so he has even more interest in keeping our thing low key than I do, so I trust him, but Tyra was kind of a wild card in that there’s now a third person in the equation that could possibly run her mouth at some point. I had no reason to think she would do that, but it was something in the back of my mind.
So there was that. And then there was the fact that Tyra is very pretty. Great body, great face. Beautiful girl. Maybe too beautiful. From a female competition standpoint, I was a little intimidated by the prospect of being overshadowed. What if he liked her better than me?
Be that as it may, since there was nothing set in stone yet and thus no reason to think that this would happen anytime soon – or even at all – I played along with his fantasies. No harm, no foul.
Well, that changed when Scout and Tyra ended up crossing paths at work one day. He texted me to tell me he had just seen her and had tried to catch up to her to speak more but he kept getting pulled up by people and then she was gone. On her end, she said she “wanted to squeeze him,” and then shortly thereafter asked when we were all going to hang out. So I took that as a sign that she was still pleased with him in person and was definitely on board for the thing-that-no-one-would-mention.
Scout and I had already planned for he and I to hang out on Friday, Feb 12. I asked her if that night was okay with her, and she said it was. So now we’d moved on from abstract to tentative to a definite plan. On Scout and I’s end, the plan was for us to meet up that night for drinks and see what happens from there. But my emotions started getting the better of me once there was actually a firm plan in place. Jealousy started rearing its ugly head a bit more.
I was a little jealous at his obvious interest in someone else. Jealous at the thought that he might want her more than he wants me, since she’s the shiny new toy and I’m the oldie, but goodie. Then, I just wasn’t sure how things were going to go and how I would feel in the moment and what would happen. I was still harboring my aforementioned misgivings and so I wasn’t really sure I wanted to go through with it. I started having more poignant thoughts in my head that he really would prefer her more than me and end up ditching me for her at some point – like, they’d start doing their own thing behind my back or something on their own eventually.
I talked about some of my reservations with Scout in the days beforehand. I called myself testing him by telling him that while it might turn out that I don’t want to proceed with the threesome, I also don’t want to be a cockblock, so even if I back out, if he and Tyra want to do their own thing together at some point, I’d understand. Was he really supposed to take me up on the offer? NO. Did he? YES. He asked if I would really be okay with that. And at first I said yes, because how can I really tell a grown man, who I’m having an affair with to begin with, who he can and can’t have sex with? Ugh.
The next day I asked him if he wanted me to see if Tyra would pass along her number to him. But he had wised up by that point and told me no – that it will just be me and him hanging out the next night. So then I felt bad because I was kind of playing mind games and being the buzz kill to this whole possible experience that I worked into being in the first place. I decided that it wasn’t fair to be selfish and let my own reservations ruin the possibilities, and I felt bad thinking of him being disappointed, so I got myself together and told him I’m down with all of us hanging out and seeing what happens. So it was decided once again that we’d at least go out and meet with Tyra for drinks and feel out the situation. No promises or expectations.
The agreed upon time was around 9:30 p.m. Earlier that day, Tyra texted me and told me she had a party she had to go to around 8 p.m. but would try to make it out afterwards. That story sounded fishy to me, as if it was her way of setting up a convenient excuse to use to back out. Why would you just be remembering a party you’re supposed to attend when we’ve been talking about this for days now and you were allegedly good to go? Nevertheless, I found I didn’t really care one way or another. If she didn’t show, it’d be letting me off the hook. So whatever. I let Scout know what her deal was, that she might flake out, and even if he was truly disappointed on the inside (which I suspect he was), he did right and acted nonchalant about it: he and I were going out for drinks…if she showed, she showed. If she didn’t she didn’t. Good boy.
I left work and went home to chill out for a few hours and contemplate what the night may or may not bring before doing myself up for our big outing. He texted me a little after 9 p.m. that he was at his usual bar and would head down my way shortly. Coincidentally, I got a text from Tyra shortly thereafter that she would be leaving her party soon and would be heading down too. I guess it was fate, after all. I shot her back the address of the place we were going – a chill spot not far from my house. Scout arrived about 30 minutes later to get me and we headed out. I told him that it looks like Tyra was going to make it, which I’m sure was music to his ears.
We walked into the bar 15 minutes later. There were two distinct sections – the actual bar side with a crowd and music and pool tables, and the dining part with normal tables which wasn’t as active. We opted for the quieter section so we could talk easier. As luck would have it, as Scout and I were sitting down, Tyra walked in. It turned out that we had all arrived simultaneously and she had actually watched us walk in. We waved her over and Scout and I took seats beside each other while she sat across from us. Like a job interview…go figure.
I was pretty comfortable immediately. There was no weirdness or awkwardness or any kind of negative vibes…we were just all 3 friends, drinking and talking together. I had a couple of shots and a couple of beers (trying to develop some liquid courage), Scout had several beers, and Tyra kept it simple with just a martini. We later all did a lemon drop shot together. We’d probably been there for close to an hour and a half when our waitress informed us that her shift was about over and after that we’d have to fetch our own drinks from the bar side. It was at that time that I suggested that we all retire to my place to drink, which Tyra took me up on.
We piled back into our respective vehicles for the ride to my house. On the way, Scout and I concluded that SOMETHING was definitely going to happen here…she wouldn’t have agreed to come back with us if not. We got to my house and settled onto the couch. At this point, I had to start providing a bit of guidance. For instance, the couch in my living room is one of those L-shaped sectionals. Tyra sat on the short section and Scout had settled in on the long section at first. I slid in beside him and suggested that he move over to Tyra’s side, which he did, with me following behind. So we then all ended up on the short section with she and I on the ends and Scout in the middle. And we were CLOSE…basically all snuggled together. Tyra was on his right side with her knees and feet propped up on the couch, kind of leaning into him. And I was on his other side leaning into him. Tyra declined any further drinks, but Scout retrieved a beer for himself and made me a mixed drink. Then we settled in together and watched TV for a bit. I was pretty tipsy at this point so I was feeling especially emboldened.
Eventually I suggested that Tyra might be more comfortable stretching her feet out over Scout’s lap instead of leaving them constricted against his thighs. She agreed, and stretched them out. Another good sign. He took full advantage by placing a furtive hand on one of her thighs as we continued talking and watching TV. At some point she went to go use the restroom and he and I kissed and may or may not have actually commented on where things looked to be headed, but I don’t remember because I was a little drunk at this point. In any case, not long after Tyra came back from the bathroom and was back snuggled against Scout, we decided to get the party started by kissing in front of her, and then I nudged him on over toward her and they started kissing.
We headed upstairs to my bedroom and all started to simultaneously disrobe. Scout and I made out some and then he made out with Tyra some more. I watched them from across the room for a little bit and then I sauntered over and she and I started kissing.
Now, just to clarify: I am in fact a heterosexual female. Be that as it may, I can appreciate and am drawn to beauty in all forms, including that of other females. As such, I’ve always been pretty open to the possibility of a scenario such as this and the inclusion of light to moderate sexual contact with another woman. Nonetheless, I don’t (at least not at this point) really have an interest in any kind of hardcore lesbian play. And I really didn’t get the vibe that Tyra was either. So while we did kiss and fondle here and there throughout the rendezvous, that was pretty much the extent of it as far as contact between she and I went. I mean, I wouldn’t see the point of having a threesome without that aspect of it, because it was partly that sensuality with another female that attracted me to the idea, but we didn’t take it any further than kissing and light petting. In the end, my primary objective was pleasing Scout, and there are not many hot-blooded straight men who DON’T want to see two hot girls make out. So make out we did.
From there, Scout really outdid himself, I must say. I was wondering if he might get so excited and overwhelmed that he would have trouble performing, but he really rose up to the occasion, so to speak. He did us both, twice.
Afterward, he lied in the middle of us for a while, silently reveling in his newfound glory (I could tell – who wouldn’t be at that point?), before eventually having to drag himself out from between the naked bodies of two beautiful women to get dressed and head home. Sucks for him! Tyra left shortly thereafter. I showed her out and then went back to bed and fell quickly into a peaceful slumber, in mild disbelief that what had just happened had really occurred. But feeling a bit accomplished myself.
Even the next day, I couldn’t really believe that the plan had actually come to fruition. But having the chance to really reflect on how I felt about it, I decided that I actually liked it. I was especially surprised at the fact that, despite all my initial hesitations and jealousies, I never felt jealous or territorial in the moment. Nothing of the sort.
Scout and I have had our thing going for a while and I really do care about him. While he is not mine, per se, and never will be, and despite the fact that he is not fully available to me physically or emotionally, he has actually turned out to have been the most steady man in my life for a long while. Weird. That being said, I was hesitant about this whole thing from the jump just because I didn’t know how it’d make me feel to see him lusting after and partaking in the pleasures of another woman right in front of my face. So it surprised me that I actually enjoyed it. Seeing him with her even kind of turned me on. Because at the end of the day, it was something we planned and executed together. Like some dysfunctional team-building exercise. It wasn’t just him seducing another girl, it was US seducing a woman together.
This was all a while ago at this point, obviously. I actually started this entry not too long after, but life got in the way of its completion. I talked to Tyra some in the ensuing days after. Scout was kind of pressed for me to ascertain from Tyra whether she enjoyed it or not, and for me to keep the lines of communication open. I think he was hoping that she would signify in some way that she was interested in a repeat at some point. She said she enjoyed herself and that it was her first threesome, but I didn’t get any vibes that she was interested in another rendezvous at this time, nor was I particularly pressed for one myself. Since then I’ve seen her around work here and there and we hug and speak just like old times. No awkward vibes or anything. Perfect.
So I think at this point, Scout has resigned himself to the fact that another threesome with Tyra is not in his immediate future, and has made peace with that. I show him pictures of her from Facebook from time to time, and he expresses tactful delight in seeing her, but it’s pretty much me being the one who brings her up. He and I have been together a few times since then and all has been well. Back to normal.
All in all, it was a positive experience overall and definitely something I’d partake in again with a lover.