How I got it in a hotel room

This is a story about my Cross dressing ways and meeting up with a friend i had made online.

I'm a 28 year old guy, named Michael I'm married with 2 kids and i have a tendency to wear my wife underwear and mini skirts, when she's not around. I'm average height, average build with a 6 inch un-cut cock. A little about my friend Dave, that i made online a few years back.. he's about 6 foot, wears glasses, average build with a 6 inch thick & cut cock.

We met online a few years ago at a gay chat website and we'd caught up a few times at my place when i was with my girlfriend (now wife) and had some fun, but we'd lost contact. And i assumed he wasn't interested anymore.

I had saved his number in an old phone so it never got found and I had been feeling really horny recently and decided i would text him and see if he remembered me. So i grabbed my old phone, got the number and sent him a text message. It said something along the lines of "hi its Michael, do you remember me?" and eventually I got a text message back saying he did remember and we caught up via text message.

I would text message from time to time and we would talk about the times that we had caught up and how we would like to do it again some time. Except now my circumstances had changed a little... i was married.. he was married & I had two kids and I lived just a little further away than i used to, so it was hard trying to catch up at my place or his place. This was the main reason we hadn't caught up since we'd been texting again. I decided enough was enough, I organized the day off work (even though my wife thought i was at work) and we organized a hotel room in the city - We split the costs and we organized to meet up during the day.

On the day, I told my wife that i was going to be starting and finishing work late. I did this because the hotel room wouldn't let me check in until 2pm. I organized the day before to get my wife hottest G string and her little layered mini skirt and a top to wear for Dave. He loved it when i dressed up like a little slut for him. I got to the hotel at the earliest time i could check in, i got myself ready and was wearing my slutty little skirt. He got a hotel room key and let himself in via reception. He had organized a bottle of champagne for us to have a drink. We caught up a little more over a drink, until i decided i would go into the bedroom.

I lay down on the bed and he came over to me, and started touching my thigh with his hand, and had a little peak up my skirt. He could see my buldged cock in a tiny G string. He asked me to roll over so he could check out my ass, and i obliged. I had my feet on the floor and bent over the bed, he was feeling my ass and massaging my hole over the G string.

He asked me to get on my back and he released my cock from my G-string and it was standing to attention! he started to give me a head job and got me a little worked up. Then he stopped and got himself naked and told me to wait right there and that he'd be back with a surprise.

He returned with a vibrating butt Plug, it was about 7 inches long and it had a hand pump attached to it. Without being pumped up it was about the girth of a cucumber. He asked me to put my feet up on the bed with my legs spread a part and he lubed up his fingers. He started to finger my ass and my god it felt amazing! it had been a few years since i had anyone in me. He masturbated my cock with his hand a bit while he continued fingering my ass. Then he asked if i was ready to have the toy in me. I once again like a good little slut, obliged and say "yes please!" he turned the vibrating function on and started to work it into my ass, first the tip then he started to fuck me with it. I was in ecstasy.. moaning louder and louder, eventually he got it all the way in and over the end of the plug.

He then asked me to get on my hands and knees... and i did... when i did this the plug slipped out. He quickly grabbed it and pushed it all the way back in. "oh my god, that feels great" i said. Then it popped out again.. so he pushed it all the way back in and this time used the hand pump to inflate it so it wouldn't come out again. I don't know how wide he ended up getting it, but fuck it felt amazing and i felt full! All this While it was vibrating away. He asked me to stand up and come into the lounge room for another champagne, so i went in there like I was told to and we had a drink while my ass was full of this massive black butt plug vibrating away! I couldn't take it for very long... I had to go back into the bedroom and lay down. He followed me and asked me if I was "ready to be fucked?" I said "Hell yes!" so I got on my hands and knees on the edge of the bed.

He pulled out the vibrator and then he pushed his thick hard cock straight into my ass bare back. He didn't give my ass time to tighten back up and he fucked me as hard as he could. I was moaning and asking to be fucked harder and harder. He reached around and started playing with my cock. At this point i was ready to blow my load, and i did onto the hotel room sheets. Because I hadn't given him head or anything he was good to keep going and did he ever. He had some staying power! He kept fucking my ass for a good five minutes and i loved every second of it. He was getting faster and faster and eventually tensed up and let his load of cum go into my ass.

We flopped onto the bed in a bit of a heap and then moved to the couch in the lounge room. We talked a bit and had the rest of the bottle of champagne. We finished up with a shower and then went our separate ways.. I caught the bus home that night and i could feel the cum dripping into my jocks.

We're organizing now to catch up again in a couple of weeks... I'm sure there will be another story about that one.