Online to Real Time

We first met on line in a chat room called crossdressers for males. I first met and was chatting with Bob, one half of Bob and Ann. We chatted about anything and everything under the sun. We talked about everything from life’s experiences to politics. That first day we chatted for at least five hours. But what we were really getting at the whole time was, what we were sexually interested in.

I am not only a crossdresser, I am also bisexual. Bob was interested in both. He was also bisexual, and liked the fact that I am a crossdresser. But the best was yet to come. He then informed me that the catch was, his wife Ann. It seemed that she liked to watch and almost direct the action of her husband being with another man. And she really liked the fact that I’d be dressed as a woman.

The chatting went on for about two weeks. All marathon chats, at least 5 hours each time. It was then time for me to meet with Ann. So one day we planned to all meet on the phone. Now if you’ve ever been in the situation, you can relate to how uncomfortable this can be. But, it could have not gone better. It was so comfortable talking to both of them on the phone. It was there and then that I knew I had to meet them. So we made a plan to meet the next night at a bar somewhere between where we both live.

The anticipation was a killer. How would we all get along, would I like their looks, would they like mine? What to wear? I assure you this was not easy. I decided since this was our first meeting, and it being in public, I’d go in male attire with something more feminine on underneath. I chose pink tights ( I just luv pink ) with a very pretty pink matching bralett and tap pant set. It was hot I have to admit.

I got there first, and found a table toward the back in the corner, a perfect little spot. I wasn’t there for more than five minutes when they arrived. Bob is a big cuddle bear type, and Ann was just simply hot! Long pretty hair, a beautiful face with piercing sexy eyes, and a great body. We introduced ourselves and ordered drinks. The conversation flowed really well, no uncomfortable moments at all. We started with light conversation, but after a few drinks, it got serious. We talked about our sex lives, past and present and our preferences. It turned out that everyone was bisexual. By the way, Bob has voyeuristic tendencies to the extent that he likes to show off Ann in public, and he should be proud to! Ann was wearing a dark pretty low cut top, and a very short skirt with garters and stockings. Oh by the way, she wore no panties at all. So during the whole time we sat there and talked, I was getting the flashing of my life. She has one of the prettiest pussies I have ever seen. Very neat lips and a very nicely trimmed bush. Needless to say, I could have not been happier.

By this time we were all horny. It was getting late, and there were no rooms to be had, so we decided on the car. They had a large SUV, which was the best we could do at the moment , and we all needed to be somewhere private now. So out we went. Ann sat in the back, Bob in the drivers seat, and me in the passengers seat. Ann got good and ready to watch the show she was about to see, she hiked up her skirt, her pussy completely exposed and she went right to work on herself. I reached out and caressed Bob’s crotch through his pants. He was already hard as a rock and informed me that his pre-cum was flowing. Not wanting him to mess up his pants, I assisted him in getting his cock out.

Wow, was what first came to my mind. He has a big cock. A good seven inches and thick as my wrist. He was not lying, because his per-cum was sure flowing, and I had to have a taste. I brought my mouth to his cock, stuck out my tongue and licked it all up. I have to admit it was tasty. Ann just has an ear to ear grin on and was viciously working her fingers in and around her pussy. Then I opened wide and began to take that monster cock into my little mouth. I started by swirling my tongue around the head, then licking the length up and down. He was so hard and I couldn’t take it any more, so I took it into my mouth. Using as much suction as I could while swirling my tongue around the head of his cock the whole time. Up and down, up and down. Taking as much as I could into my mouth without gagging.

My arm was kind of behind the seat I was in and I felt Ann grabbing at my hand. She Extended my fingers and inserted first one then two fingers into her steaming hot wet pussy. So now, I have this big cock in my mouth, and my fingers in her hot pussy. I continued to finger fuck Ann while she worked her clit. I think she was cumming constantly at this point. Seeing this brought Bob right to the point of no return, which he informed me of. I responded by trying to get more of that big cock into my mouth.

He came like a volcano. I could feel stream after stream hitting the back of my throat. The taste was great, salty like most, but something also undeniably pleasant about the taste of this particular guy’s cum. Ann meanwhile was freaking out riding my fingers and playing with her swollen clit. I kept some of the cum in my mouth and managed to ask her if she wanted some. She did, and reached up and we kissed. I was sharing this man’s cum with his wife….what a turn on!

We kept kissing for a while and I began to play with her tits. They were perfect. Not too big, not to small, and the best nipples I’ve ever seen. She offered me one than the other. I sucked, licked and needed them for some time, all the while, she was still playing with her wet pussy. I then thought turnabout is fair play. Since I tasted him I should taste her. She moved up into a position where I could get at her pussy. It was like heaven, she tasted great too. I licked all around the outside of her swollen lips, Then up and down her dripping slit till I (with not much difficulty at all) found her swollen clit. She moaned quite loud as I got two fingers into her hole and began cumming right away.

The sight of all this got Bob hard again and out of the corner of my eye I could see him stroking his once again hard cock. Hmm I thought to my self. This is like a playground. What should I have in my mouth. Her pussy or his cock? I stayed with her pussy till he was about to cum again. I then diverted my attentions back to that big cock, which I immediately took back into my mouth. It didn’t take him too long to shoot another load down my throat. I savored and kept this load all to myself.

We all sat basking in the glow for a while. Then both Ann and Bob turned their attentions to me. I took my cock out, and they both began licking my shaft up and down. They were licking and stroking at the same time. I have to admit, I’ve never had two people working on my cock at the same time. What a wonderful feeling! With the combination of earlier conversation and the heightened feelings, it didn’t take me long to cum. I erupted all over the place. We scoped most of it up and all had a little taste.

By this time we were all really tired and spent. So we got ourselves dressed and back together again. We said our goodnights. A nice long deep kiss from Ann, and a great big hug from Bob. We agreed that we must do this again, but in a more comfortable place. I know Ann really wants to see Bob fuck my tight little ass. With that in mind. I Really can’t wait to see them again.

To Be Continued...