Free Erotic Stories

Round 1 with Crossdressing Hubby and their Hotwife

I met this couple on another site a decade ago. Mary, the hotwife, was mid 40s, taller than average, and super curvy / with a beautiful face. Her pictures indicated that she liked to wear fancy dresses, stockings, and heels. The playful nature of her eyes in the pictures had me hooked from the start. Michelle, the crossdressing husband, also liked to wear dresses, stockings, and heels, and bore this striking resemblance to the comedian Tina Fey. To say that Michelle was passable would be a massive understatement.

Their ad said that they were looking for a (top) bi guy and that everyone would participate. Michelle wanted to see a bi male giving pleasure to Mary, Mary wanted to see a bi male giving pleasure to Michelle, and there would be oral all around. Ultimately, both of them wanted to be treated like ladies. Perfect! They laid out what they were looking for, physically, from the bi guy, and I fit the bill, in my opinion, for the most part. But I lived hundreds of miles away, so I wasn't sure if that would be a blocker, even though I visited their city at least quarterly. Regardless, I wrote them a message, and sent it along -- with the type of pictures that they had requested.

To my surprise, they got back to me a few days later. We ended up having a great correspondence through email, and talked on the phone a few times. Still, our calendars didn't quite sync up. They had kids at home. I was only there quarterly. We still kept in touch here and there, and I kind of wrote the whole thing off at that point, but suddenly the stars seemed to align. I would be in their city at the same time that they had some room to breathe for their "special" playtime, as they called it. They invited me to have a drink with them, stressing that maybe no play would happen on the first date, and also insisted that I bring my "test" results along with me. They would also bring their test results along.

My flight to their city could not be longer if it tried. The workdays leading up to our date dragged by. But finally Friday night hit, I'd be in their city for another week, so I returned to my hotel, showered and shaved (everything), and put on a fresh suit. They both told me that they like a man in a suit. Then I got a cab and headed out to the bar.

Honestly, tho? I wasn't sure. I had been dreaming about this type of scenario for ages. But maybe I wasn't fit enough, tall enough, they didn't like the fact that I was hairless. This bizarre imagery kept going through my head as I sat quietly in the cab. It had taken so long to get to this point, and I had come such a long way to meet them, so I was hoping that we all felt that it was worth it.

They were already at the bar when I got there, and I was surprised, because I was actually 15 minutes early. As the cliche goes, they both looked even better than their photos. Mary was a major cutie, and was wearing a navy dress, mid thigh with a slit, black stockings (I could briefly make out her stocking tops, while trying not to stare, as she sat down), and black stiletto heels. Michelle was Tina Fey all the way, wearing a pearl necklace with a "little black dress" and black stiletto heels as well. They recognized me right away, of course telling me that I looked amazing, and a lot better than my photos (maybe we should all take better photos?) and that they loved my suit. We all exchanged hugs, and they both gave me a peck on the cheek, so I returned the favor. Plus, they both smelled amazing.

It was almost like we'd known one another for an eternity. The conversation flowed, we had several drinks, and everyone was laughing. Thing is? I was totally into having a sexual encounter with them, but it seemed more like a friendly date than anything. About a couple of hours into it at the bar, I had to pee. So I excused myself for 10 minutes or so. I was hoping that I would get some kind of information or feedback once I returned to the table.

I could feel their eyes on me as I walked back to the table. What was happening here?

They prompted me to sit down. To my surprise, Mary was the one who did the talking.

"It's been so great to finally meet you. You're such a nice guy, and we've both been having a great time. But, two things," she said. "First, did you bring your 'test' results with you?"

I reached into my suit coat and pulled out the results and handed it to them. They did the same for me. They both nodded, as did I.

"So, this is really good," Mary said, in reference to the test results. "But the second thing is that while we would like you to join us for the evening, there are some ground rules, if you'd like to hear them."

I nodded in agreement. You have no idea how excited I was at the prospect of being with a sexy couple like this. I guess we should've discussed ground rules months ago, but hey, they were clear early on that they were going to take the lead with this, and that I was a guest in their relationship, so I suppose that their approach made sense.

"With this in mind, the first rule is 'no means no'."

I nodded.

"Good. The second rule is that even though Michelle is my cuck, there will be no insults or degrading of her."

I nodded again.

"We will both be present for the entirety of the evening/night, and will both participate. This includes everyone kissing, touching, fondling, asking for permission as necessary, topping me, DP, mutual oral, and if it goes in that direction... topping Michelle."

I nodded and smiled. Mary was stunning, but I was really, really curious about what it would feel like to "make love to" Michelle.

"Finally, if you are comfortable with it, and since we all have shared our tests, we like to go raw. Sharing Mary like that is very special to Michelle. Is that OK with you?"

"Definitely," I responded. "For regular intercourse, but I use a condom for anal. Is that OK with you?"

They said that it was fine, then Mary said that they had gotten a room for us nearby, and that they would drive us all there.

The building was non-descript, but it certainly wasn't a hotel or a motel. Mary briefly talked to the guy at the front counter, then we started walking towards the back of the building. There a bar on the side. Loud music was playing. There was a stripper to the left. People were having sex everywhere, and in public. Holy shit! It was a sex club. I had never been to a sex club before! I only wondered what their plans were. I mean, it wasn't that bad of a place, pretty clean, lots of leather couches and brass rails, my feet weren't sticking to the floor, etc. We stopped at a door at the end of a very long hallway.

Mary put a key in the lock, and ushered us into the room. She locked the door behind us. My eyes were still adjusting to the light. It was actually a pretty nice room, and somewhat private. You could hear the sounds of moaning somewhat above the pounding bass from the speakers. I actually kind of liked the idea that we were going to have some kind of encounter behind closed doors, and that people might be in the next room, or outside of the door listening.

Even though it was small, the room had a double bed, a dresser, with a tv/DVD player on it, a small couch, and a rug. It was slightly dim in the room, but I felt it was intimate. The next thing on my mind was who was going to get us started.

It was Mary of course. She motioned us in towards her, and we all embraced. They both told me how excited they were to be with me, and I thanked them for inviting me. Then Mary initiated a kiss, which was absolutely mind blowing: the gentle tongue slipping into my mouth, biting my lip a bit. We broke the kiss after a few seconds, then I turned my head and returned the favor to Michelle. Mary offered encouragement, and told us how beautiful it was to watch the two of us together. I started kissing Mary again, while Michelle ran her hands down each of our bodies, periodically stopping to either join in a three-way kiss or to kiss us on the necks and/or breathe in our ears.

Michelle started to undress me as I paid a lot of attention to Mary. When she started to undress Mary, I asked if I could have the honors to do it. they both said that they would love for me to do that. As Michelle worked on stripping me, down to my obscenely tiny male thong, I got Mary down to her thigh high stockings and heels. I asked if she would leave them on for me, and she told me that she wouldn't have it any other way, and how fucking her lovers wearing nothing but thigh highs and heels made her feel so hot and sexy.

In the background, Michelle started disrobing. To my surprise, she wore absolutely nothing but her heels -- and that she had breast implants! They were so cute and perky, and her dark and erect nipples demanded some good tonguing and sucking. I broke my kiss and fondling with Mary and asked if Michelle would mind if I would kiss and suck her nipples. She agreed, and once again, Mary told us how hot this all way, but she suggested that Michelle and I get on the bed for a "69" before moving on to the next event, whatever that would be...

I'm actually surprised that Michelle got so much play. This is not what I understood cuckolding to be, but whatever. We all seemed to be sexually compatible, and this was all so hot, so who cares?

Michelle was delicious. I've always been able to produce a ton of salty pre cum, but Michelle was maybe even able to produce more than me. We sucked for at least 15 minutes, a guess, before Mary, who was pleasuring herself with a tiny vibrator, had a very loud orgasm and squirted everywhere. She didn't even come down from her orgasm when she got up from her place on the bed, and asked me if she could try something that I would really like. I said that she could, and next thing you know, her tongue was snaking around my asshole as her fingers massaged and squeezed my balls. I didn't last long after that, but gave warning. Michelle drank every drop, and once I finished, Michelle kissed Mary. Mary then kissed me, and I tasted myself for the first time that evening.

We all kind of cuddled, chatted, and laughed while laying in the bed before Mary asked if I was able and/or willing to go another round. Just with the hotness of it all, I was already semi hard. I asked if Michelle could do me a favor (to speed me up so that I could go another round), and Mary asked what it was. Now, they had told me early on that they weren't into topping other guys, but Mary had just tongued my asshole, so I wondered if Michelle would play with and finger my asshole a bit, and slowly jerk me off until I was fully hard again. Mary said that she didn't see why not, and I told them that I had a tube of Astroglide in the suit pocket of my jacket. Michelle did an excellent job of getting me to where I needed to be, all the while telling me how much she couldn't wait for me to properly consummate my relationship with Mary. So hot. So very, very hot. I kept looking at Mary who was playing with herself.

I said that I was ready, and Mary said that for our first time, missionary was exactly what she wanted: nice, slow, passionate, and tender, basically in those words. I asked if Michelle would put me in her, and Mary said yes. Mary and I kissed tenderly as I took long and slow strokes, as our bodies would slap together when I bottomed out. Michelle told us how beautiful we looked together, and that it was also so thrilling to watch a special "boy" consummate things on the first date with Mary. I went a lot longer than expected, and for my end of things I kept whispering "secrets" into Mary's ear like how hot she was, and how this is the way every relationship should be consummated, perhaps I'd put a baby in her, and so on. This got Mary revved up, and she came hard enough that she pushed me out of her. I managed to force my way back in, announced my intentions, and pounded whatever I had in me -- deep inside of her. We cuddled and kissed a little bit then I pulled out of her.

We all relaxed in the bed for a bit longer when Mary looked at her watch. It was 1am, and the place closed at 2am. She asked if I was able to go another round. At first, I wasn't sure. It had been so hot, and there had been so much sensory overload that I was pretty pooped. Usually I can go 3-4 times per setting, but I was trying to get my body back in order.

And that's when Michelle stepped in, likely adding her $0.02 when Mary didn't want her to. Mary looked legitimately shocked at first. But then Michelle continued, "well, if you can go again, this is where we all share this consummation together. Is this something that you think you can do for us?"

At first I thought that Michelle wanted me to top her, and my little guy started waking up again. But no, that wasn't it. Mary fingered at her cunt and scooped up some of my cum. She used it to lube Michelle's cock. Then she did it again, and lubed mine with my cum, while jerking us both off. Mary told us that she wanted DVP to complete the proper consummation.

Michelle laid on the bed, and Mary got on top of her. I got behind Mary, and surprisingly it was really a perfect fit. I didn't know if I'd be able to cum until... the dirty talk started again. Well, maybe it wasn't so dirty, but it got me going. Mary asked how much I loved this. I told her that I loved it all and that it was amazing. Mary asked Michelle the same thing and she agreed. Then Mary surprised me if I enjoyed making love to her. I said that I did and told her how both erotic and passionate it was. She asked me if I loved her, because of the way that I made love to her, and I said that I did. And that's when I felt it for the first time. Michelle started bucking her hips, and I felt the warmth around my cock head. And then I lost it too, and kept yelling out how much I loved the both of them. Phew!

By the time we were finished, they were practically closing the place. The dropped me at my hotel, and off they went. They ended up contacting me on Sunday, but that's a story for another time.

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