HER: I was deep into post-holiday work mode when a couple of texts lit up my phone.
Happy holidays gorgeous. Hope you are keeping well and had a lovely Christmas.
Thinking of you both. All the best for the new year as well. 😚 Would love to cross paths some time.
I got messages like this every few months from Justin, a friend we met four years ago. He was the first single male we ever met online and deemed worthy of a date. He’s still the only man I’ve met through a web site that I’ve ever had sex with. We’ve been on the once-a-year plan ever since, but we had somehow missed the most recent year. And this is one guy that I did not want to let slip through the cracks!
HIM: Single males often get a bad rap in the lifestyle, but the truth is that they play an indispensable role in the swinging ecosystem. Of course, they are absolutely essential to every hotwife, cuckold and two-guys-and-a-girl scenario, but even when there is no sex involved, the best of them can boost the energy level of any social setting. So I was thrilled to hear you had arranged for us to meet Justin for dinner at our favourite oyster place. The conversation was great, as it always is with him. He started by updating us on his parents’ health challenges (he’s a compassionate and dutiful son) as well as his recent business successes (he’s a creative, hard-working achiever).
HER: Not to mention extremely good looking! He’s tall, athletically built and has a great smile. But in the end, it’s always about personality and intellect for me. He’s witty, charming, genuine, and very free with his compliments.
HIM: The platonic ideal of the single male.
HER: Sure. As the evening progressed, our party of three spilled over to the couple at the table beside us. I recognized earlier in the evening that I had gone to school with the man years ago, and we discovered that the woman had a business a few doors down the street from Justin’s new office. We carried on laughing and joking until just past 10. I guess we weren’t too disruptive, because the owner of the restaurant comped our meals!
HIM: By that time, I assumed it was too late for sex, given that you had to work in the morning. But just as I was explaining this to Justin on the sidewalk outside, trying to provide you with an easy out, you interrupted me to say no, it wasn’t too late at all. Justin replied that he was ok as long as you were, so we asked him to follow us back to our place. In the car, I told you how surprised I was. Just a few hours before you had actually said that you hoped he would cancel. You had been extremely busy at work the last few weeks and would have appreciated a quiet evening at home. Yet now, as I stepped in to get you gracefully off the hook, you were full of enthusiasm.
HER: This happens to me a lot. Sometimes the potential of a sexy get-together is just too abstract to motivate me. Remember, after a tough day at work I had just spent an hour with my sweetly sadistic personal trainer at the gym. Throwing on some comfy clothes and settling into the couch would require no effort, while going out would require energy I just didn’t have. But once I made it to the restaurant, the sexual chemistry between me and Justin took over. There was no way I wanted the evening to end with a chaste kiss on the sidewalk.
HIM: When we got to our house, I explained that I wanted to try an experiment. This time I would leave the two of you alone in our bedroom while I was downstairs in the family room. In the past, I had been present in the room with you and Justin, just to watch. But I was curious about the effect my absence would have on me both during your time alone with him and when we reconnected after. I also thought it might be freeing for you not to be distracted by me, looking for signs as to how I was reacting as things progressed. Kind of like a same-building hotwife experience. Justin seemed happily surprised by my idea, like he couldn’t believe his luck. So I settled into the family room downstairs to do a little reading.
HER: We started with him stripping to his underwear and putting on his playlist while I lit the candles. He then took my clothes off, admiring the leather and zippers of the lingerie set I had on underneath. Those came off quickly, and he went down on me for a short time (he reads this blog, so he might have remembered oral isn’t a top priority for me). Instead, he fingered me until I squirted. I sucked his cock, and he guided my hand to cup his balls. He also seemed to enjoy a gentle finger stroking his asshole while I sucked (who doesn’t?).
Then he asked if he could fuck me. It was the gentlemanly thing to do, but I just laughed and grabbed a condom. Silly man! We had sex for the next hour or so.
HIM: It was more than an hour. You carried on for a long, long time, probably more like an hour and 45 minutes. I wasn’t feeling turned on, but interestingly, I was occasionally shaking. It was like I was having a panic attack without the anxiety, so I knew something powerful was going on inside me. It didn’t register as arousal, though. I felt torn in two directions. The scientific side of me wanted to preserve the purity of the experiment, to find out what it would feel like to be completely disconnected from your involvement with another man. But the other side of me was insanely curious about every little detail. That side won. At times I stood by the family room entrance, straining to hear you over the music. A couple of times I even snuck quietly up the stairs to catch a glimpse without being noticed. I guess I was afraid you would do exactly what you just did: tell me that you fucked for an hour or so, when what I wanted was a minute-by-minute breakdown of every little thing that happened.
HER: Unfortunately, I’m not great with that kind of detail. Things all blur together for me. Let me see: I know we did cowgirl, reverse cowgirl, and doggy-style. He did me from behind with me hanging my head over the edge of the bed, we spooned for a while, then we positioned ourselves at the end of the bed so we could both watch him enter me missionary style, legs up over his shoulders, in the mirrored headboard. We both loved that: the contrast of his black skin against my pale, winter white. At one point I asked Justin if he wanted to put it in my ass. He said “Really?” and I immediately thought What am I saying? This man has a massive cock! So I said maybe next time, and he didn’t bring it up again.
The whole thing was fluid, comfortable, and very sensual. There was lots of kissing and holding each other close. You know the feeling when you’re riding someone with your hands dug into their hair?
HIM: No, but I watch a lot of movies.
HER: “Passionate” was the word he used in his thank-you text the next day. Towards the end, I went down on him again. When he let me know he was going to come, I said that was great and kept sucking. He asked “Are you sure?” and I told him I was. He came in my mouth and seemed very appreciative. After a little washing up, I went down to find you.
HIM: When I heard your steps on the stairs I rushed back to the sofa from my listening post by the family room entrance. Moments later you walked into the family room naked, straddled me on the sofa, and whispered that Justin had just come in your mouth. Then you kissed me passionately so I could taste it. I was on fire. I can’t remember the last time I got that hard that fast. It’s interesting: I have licked your pussy before, right after another man has come in you, and it is frankly the worst thing I have ever tasted. Kind of like spoiled cream mixed with battery acid, except much worse.
HER: That’s often the case. But Justin actually had a very neutral taste. No problem.
HIM: Well, it definitely added something. I’ve kissed you thousands of times and this was different. With just a trace of his semen in your mouth after you had swallowed, the psychological and sensual combination had me reeling.
Justin soon came down the stairs after getting dressed and collecting his things. You and I jumped off the sofa and went to the front door to wish him goodnight. After he left, I asked you if you were still good for sex, even though It was now past midnight. “Yes,” you said, “I haven’t even come yet.”
HER: That’s pretty common for me. I had a fantastic time with Justin. He was as good as a man can be in bed. But he’s not you. Having an orgasm is complicated for me, and I guess I need an experienced accomplice to get the job done right.
HIM: You started by lying face down on the bed with your legs spread, using the vibrator. I paused to enjoy the sight of you by candle light. When you raised your hips up in the air, my cock went from ‘hard as wood’ (pine, not oak) to ‘hard as rock’ (granite, not soapstone). How do I say this delicately? The sight of your asshole made my knees buckle. I can’t explain it. After a little more staring, I decided it was time to get to work. I told you to get into your coming position — face down, with your head hanging over the side of the bed. I started to fuck you the way you like it, slow and forceful, with the vibrator still on your clit. You came really quickly. Then I grabbed a handful of your hair and pulled it while fucking you in a more upright position (like holding the reins while riding a horse) until you came twice more.
HER: They were pretty great orgasms, which shouldn’t be surprising considering the yeoman effort Justin had invested in taking me to the edge of ecstacy. Finally, it was your turn. I asked you what you wanted and you asked me to get the realistic cock vibrator. You seem to love that thing!
HIM: I do. It all started one day on the massage table when you used your egg shaped vibrator on my ass. In my mind, I imagined that you were using a penis-shaped device and, unexpectedly, the idea really turned me on. That’s how low-key bisexual I am: I am not interested in having a real cock in my ass (yet), but the thought of a real-looking toy tickling that area almost made me explode. So we went out to our local sex shop and bought one the next night. The exhibitionist in me enjoyed the process of being served by a young woman who knew that the product was for me. She even had me grip the various models to see which one felt best.
HER: Well, imagining a cock playing with your ass also really works for me. I started by using it on your balls and rimming your ass while I sucked your cock. You were so excited, I thought I was going to swallow my second load of cum in less than an hour. But then you got up on your hands and knees and I focused on your ass until you asked me to slide it in. So I lubed you up and went very slowly. We both loved it. (Note: this isn’t over – we have got to go out and buy a strap-on.)
HIM: It was awesome (and yes to the strap-on!). You had been stroking my cock the whole time the vibrator was in me and I was desperate to come. So I asked you to ease it out and we changed positions so I could fuck you. It felt fantastic after everything that had built up in me, and my orgasm was explosive. It was an amazing end to an unbelievable evening (sorry for the double-superlatives).
HER: Regular readers of our blog will know that not every adventure we undertake is a total success. We are committed to sharing things exactly the way they happen, so let me assure our readers: those double superlatives are not out of line! The fantastic sex we had together after Justin left was definitely connected to all the things Justin did before he left. And for reasons we no doubt do not fully understand. That’s the mystery of the ‘single male experience’ at its best.