This is a print version of story 3 Teen Cross Dressers Misadventure - Part 1 by ClaireCD from

3 Teen Cross Dressers Misadventure - Part 1

Two friends and I decided to take a trip to upstate New York for a weekend of skiing and some messing around. We were friends since elementary school and have been dressing in our s****rs and mothers clothes for over a year and then play around with each other. All of us were young and dumb; 18 and quite petite,under 5'7 and lean. With our bags packed full of our dress wear,skiing gear and lots of liquor we were on our way.

We were about 4 hours into our 6 hour drive in the pouring rain when we realized we had no clue where we were. We all figured it would be best to just find the closest hotel, crash and get an early start the next morning. Not more than 20 miles or so we found a small motel; not terribly nasty but not exactly the lap of luxury either. So we settle in and decide we will have some drinks and play a bit of cards before bed. Some drinks turned to more drinks until we were getting a bit smashed. Brett in particular was trashed and even though he was the most shy out of us three, he decided he wanted to roam area some.

This did not sound as enticing to myself or my other friend Sean. There was nothing around except a small lodge and a gas station anyway. But entertaining Brett, we went along with it and led us into the start of a night we wouldn't soon forget.

All lightweights and on our 6th drink or so we headed out, first to grab some snacks at the gas station across the street. We must have been in there for sometime, noticeably buzzed and fumbling with some items because a few customers seemed to be staring at us. In particular 4 men in their late 20's or early 30's that were in there probably as long as we were. We didn't pay any attention to them and instead thought some beer might go well with our snacks.

Although none of us were even close to 21, we opened the cooler and browsed a bit. While Brett was bending over Sean saw all 4 of the men staring at him. Now, we were dressed as regular teenage boys but regularly wore thongs and stockings under our clothes as we did that night. This must have caught their eye although we were unaware that was the case. 2 of them came over and said something to the effect that we didn't look old enough to be looking to buy beer. Not sure exactly but we made some kind of joke and we all had a little laugh. At this time the store clerk was getting a bit annoyed and told us if we were looking to buy alcohol he would card us all. With that plan squashed we just bought our snacks and went outside.

Sure enough before we were more than a few steps out the door the men from inside said they would buy us the beer. We gave them about $25 and told them to grab anything, we didn't care. They came outside with the beer but told us that he didn't want to hand it to us in public; then when we mentioned that we were staying at the motel right across the street they offered to give us a lift and drop it in our room. This seemed like a good deal. They bought us beer, offered us a ride, and would bring it to our room which was good because it was 4 cases of beer with no bag and we don't look near 21. Not such a good idea in hindsight.

Everything started out fine, we got to our room and thanked them for their help. One of the men said, "how about a beer before we take off?" We said sure and Sean offered the others. We casually sat around and told them about our trip and where we were from, you know small talk. Craig, the only guys name we actually heard, helped himself to another beer and said, "I like those panties your wearing slim" motioning to Brett. All three of us looked at each other dumbfounded and they looked at each other with mischievous little smirks.

Story URL: