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The First Play Date
If you’ve followed my advice in Part 1, then you’ve already experimented a little. Perhaps you and your wife enjoyed some fun experimental flirting, kissing, and petting without either of you having an anxiety attack or major jealousy issues. At this point you may feel comfortable enough to arrange your first sex date with another man. I’ll describe our first such foray and try to impart what we learned, for whatever that’s worth. Hopefully we can at least give you both some thoughts about how to go about it.
When we decided to arrange our first real play date, my wife and I had already had a successful and fun evening with the other man. We got a chance to get to know him and feel comfortable with him. We continued to text each other, using group chat so that we were all in the conversation. I can’t emphasize this enough. My wife likes the texts because it’s basically foreplay. Some of the texts were hot and erotic, yet others were just to get to know each other. In parallel, I also sent an email to the other guy explaining a handful of key ground rules. This is kind of a buzzkill, but it’s necessary to go over the basics. For example, if your wife doesn’t like being called dirty names during sex then you should mention that. Conversely, if she likes name calling (mine does!) then mention that as well. If your wife has any physical issues (e.g., like a sore left wrist or previous neck surgery or anything along those lines) then you should mention it. If your wife has any limitations or strong dislikes (e.g., hair pulling, anal, knock-knock jokes during sex) then list them out. Face it, we all know our wives like the back of our hands. The other guy doesn’t. If you want the evening to go smoothly, make sure he knows what he needs to know.
You need to cover the raw basics, like tell him to bring his own condoms. That said, we always bring extra condoms just in case the other guy has a brain fart moment and forgets his own. If you want to bring sex toys, bring them. Also, you would be shocked at how many guys have trouble performing in this situation. Every guy is a porn star in front of his computer screen. Show up to a hotel room with a smoking hot wife in lingerie and all of the sudden shit gets real. For that reason, I recommend that the guy takes a little blue pill prior to the date. You can get a free sample from your doctor. If a guy is too timid to ask his doctor for a free Viagra sample, then that’s probably not the type of guy we’d ask to jump headlong into a hotwife threesome with us.
I provided a very basic script for how it should start. We didn’t want to over-plan the night, but we wanted to loosely script the first “set of plays” to alleviate any potential awkwardness or hesitancy in getting started. For example, you could suggest that she start off with sucking him off, then have him take her missionary style on the bed. For our first play date, my wife and I decided that I would simply watch (at least for the first round) rather than start off with a threesome. It sounds weird, but this somehow felt like an easier first step. I also told the other guy in the email him that we would be ready to go immediately upon his arrival, and that she would be in lingerie when he got to the room. We chose to dispense with any small talk and go straight to the fun. Believe it or not, that actually makes it easier for us to get over our nerves. It’s kind of like jumping straight into a chilly pool rather than trying to ease in gradually. Banzai!
I will say that for subsequent dates we tried meeting in the hotel room bar prior before adjourning to the room. Good grief. Having a pre-threesome conversation in a place like that is like opening a bag of chips at a funeral. The bartender is like two feet away from you at all times. Certain phrases seem to travel farther in an open room. Like, for instance, “double penetration.” And never mind the fact that it’s two men and one woman huddling over a table…in a hotel bar. And then walk to the elevator together. I don’t recommend it if you’re the least bit self-conscious about it. One final side-note on this, though. We recently went out on a date where we did exactly that in public, intentionally. We even held hands, her holding both of our hands as we walked through a lively nighttime crowd. At one point we each had a hand in the back pockets of her jeans. We garnered many stares, I will say that. Fucking hot. More on that later, but back to the first date.
I arranged the hotel room for our play date. We always prefer to get the hotel room ourselves so that we have control over the location and type of room, and so that we can check in first and be ready when for when the guy arrives. That also means that it’s easier to set up a video camera, if you choose to record your fun for your future enjoyment. For our first date, we chose not to take any video or pictures. That made it a lot more comfortable for all of us, but I kind of regret not having a video of that night. We both like getting off to pictures and videos of our escapades.
My wife and I again agreed that we could call the whole thing off at any point up until the moment he arrived. At that point, we agreed to a “point of no return.” Unless one of us was having a panic attack, we were going to go through with it. Honestly, I didn’t know if I was going to be sick to my stomach and hate the whole thing. I’m pretty sure I was more nervous than she was. We brought a couple large bottles of white wine to the room so that we could have a few calming glasses of liquid courage before he arrived. We also wanted to be able to share a few glasses during any “intermission.” I think I finished most of the first bottle myself while we were waiting. But we wanted to have a designated point of no return so that there was no awkward hesitancy during the sex. We also agreed that if the experience sucked, then we’d simply treat it as a shared adventure that we tried and wouldn’t do again. I confessed to my wife that I wasn’t 100% certain that I wouldn’t regret what we were doing, but that I wouldn’t stop anything after the action began. We had agreed on a code if either of us really needed to stop the whole thing, but I was emphatic that I didn’t plan to use it. I wanted her to know that she could end it at any time, but I didn’t want her to worry about me or have to spend the night second-guessing what was going through my mind. I was all in.
More than anything, we assured each other that this was about US. He was a prop, and nothing more.
That evening he had been texting us as he was on his way. When he got arrived at the hotel, I texted him our room number and told him to came straight up to the room. We turned all of the lights off, leaving one light in the little kitchenette on for ambient lighting. I gave my wife one last kiss and we both assured each other than we loved each other madly and that nothing that happened that night, or ever, would change that. Then…the knock on the door. I let him in, quickly greeted him, and closed the door behind him. He walked directly over to my wife, who was nervously standing in the middle of the dimly lit room in a lovely pair of matching lace bra and panties. They exchanged some quick “hellos” and he told her how beautiful she looked. They kissed. At first gently. In a moment they were making out, her mouth open for him. They were pressed against each other for several minutes, grinding, hands exploring each other. That was the point of no return.
They moved into the completely darkened bedroom area of the suite, the glass french doors open to the sitting area. I settled in on the couch with another glass of wine and watched as she dropped to her knees next to be bed, unzipped his jeans, and took his already-hard cock in her mouth. He stood over her, his hands resting on the back of my wife’s head as she started bobbing slowly up and down.
In my mind, I was nervously anticipating my own “freak out” moment and was doing my best to reassure myself. It’s kind of like getting on a roller coaster, and as it starts to move you wait for that second when you think, “Oh shit! I really wish I hadn’t done this.” But that moment never came. I admit, watching my wife suck another man’s dick was surreal. Fucking surreal. I honestly kept thinking that I couldn’t believe this was happening. But the thing it, it was really fucking hot! I mean, I was seeing my wife’s face a few feet away with another man’s (rather large) cock in her mouth. It was really hot and I was filled with a weird sense intense relief, believe it or not.
Her eyes darted over to me as she knelt there on the hotel room floor. I’m not sure if she saw the look of reassurance on my face, given the darkness of the room. But she definitely got the point, as my own pants were around my ankles and I was slowly jerking off. That did more to comfort her than any subtle wink or smile I could muster. I told her how fucking hot she looked to let her know that I was having a good time. Hearing my words of encouragement definitely put her mind at ease. I could tell she was getting into the moment and leaving her earlier nervousness behind. When she laid back on the bed and he buried his face between her legs, she was thinking about nothing beyond his tongue on her labia and lit.
By the time he opened a condom wrapper I was over my anxiety and acclimated to what was happening, yet it was still kind of a blur. To be honest, the actual moment of penetration was moderately anti-climatic. The room was too dark to see much of anything except that he was on top of her. I know a lot of hotwife fantasies focus on that very first instant of penetration, but it was over before I could grasp it. I got up to get a closer look, by now completely naked myself, and walked over near the bed for a better view. By the time I got close enough to see, he was already slowly pumping away inside my wife. I stared at her, hoping for eye contact, but she didn’t look back. They were in their own world. She looked entranced.
That was my second surreal moment of the evening. I had abandoned my jitters and was taking the whole thing in, genuinely enjoying the scene. But at that moment I had a complete realization that my wife was having sex with another man. My wife. It was almost overwhelming. I was standing in the doorway of the bedroom, looking down at both of them from the foot of the bed. My wife was on her back, legs spread and knees slightly bent. He was naked and between her legs. Her hands were caressing his back and neck, staring up at him, her eyes locked on his. His ass clenched as he pushed himself deep inside my wife. My wife. She had stopped looking over at me and was completely one with him. Surreal.
I retreated back to the sitting area and took another drink of wine. He was fucking her doggy style. It wasn’t a great view from the couch, as she was facing away from me. It was obvious that neither of them was thinking about putting on a show for me; they were simply fucking each other. He was thrusting harder, causing the headboard to slam against the wall. She was moaning, then crying out, then gasping, then moaning again. It was odd to hear my wife’s familiar voice in that context, calling out his name. Telling him how incredible it felt and how big he was. He was grunting as he thrusted away. This will sound ridiculous, but I actually felt uncomfortable about the noise, worried that people next door might call to complain and maybe send someone up to our room. He was fucking the shit out of my wife, and it was REALLY loud.
They fucked for over an hour. He changed positions frequently. Probably too frequently for her taste, as she didn’t really get to orgasm. First missionary, then doggy, then her legs on her shoulders, then her standing and bent over the bed, and so on. A lot of guys think that, as the third wheel, that they need to go into full-on porn star mode and do every position in the book. And fucking a hotwife is like having a new (fuck)toy anyway. Guys can’t wait to fulfill all of their sexual fantasies. This guy was clearly having the time of his life and making the most of it.
I kept drinking wine. Too much at this point. By the time he said he was getting close, I was half in the bag. I had moved to the bed, sitting on the edge and occasionally holding her hand as she fucked away. She was on top of him, riding him. He was pulling hard on both her tits and tugging at her nipples. Her hands were behind her head pulling her hair back, offering her breasts to him freely. I was caressing her hair and rubbing her her back as he finally came.
She collapsed on top of him and they stayed there like that for several minutes, sweaty and breathing hard. He left to go into the washroom. By the time he came back to the bed I was drunkenly fucking my wife. He stood in the doorway and watched as I enjoyed sloppy seconds with my wife. I came in probably about five minutes. It wasn’t my finest performance, but I had been stroking my own cock off and on for over an hour. And I was drunk. The date ended shortly thereafter, and that was it.
This definitely wasn’t the best date night we’ve had, but it was the first. Like all firsts, it does have a special place for us despite the anxiety and initial awkwardness. The sex with him was good, but not earth-shattering. It was the scene itself, with me watching her fuck, that was the real thrill. On the drive home we were rapidly chatting about how much fun we had. We were both more relieved than anything that neither of us had a panic attack. Also, we both concluded that sex is just sex. If you can get over the taboo of another man sliding his cock inside your wife, it’s just fucking. After it was all said and done, it wasn’t as big of a deal as we had thought it was going to be. She got laid, I watched and jerked off, and we both enjoyed the experience immensely. And we’re both still madly, crazily in love with each other.
Since then we’ve had some awesome experiences. We’ve also had a few duds. We still love threesomes and are planning a gangbang with some of our friends in the very near future. She’s fucked other men while I’ve waited at home. She had a longer-term mildly romantic “affair” with a man who thought she was cheating on me (her boyfriend didn’t know that I knew, if you can follow that). She’s fucked a couple of guys when I didn’t even know she was playing. And she’s recently fucked one of our friends in our marital bed while I was at work. More on that in later posts.
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