Snowed In Roommates - Sex Stories

Snowed In Roommates

My roommate Ben had just put two candles on the coffee table and sat down on the sofa next to me. I had a throw pillow in my lap in an attempt to cover my budding erection. The problem is that I am a totally straight guy. Well at least I think I am…

If I was with a girl this would be romantic, but currently I was dressed like one. I was wearing a short red dress with sexy black lingerie underneath that Ben chose for me. My knees were clad in black stockings and I was doing my best to hold them together. I had a blonde wig on and made my best attempt at makeup. My roommate was dressed casually in a t-shirt and shorts.

With only the candle light in the relatively dark room, I felt Ben inch closer to me. His hips touched mine.

He asked, “What’s with the pillow? Are you cold or something?”

Totally embarrassed by my now completely hard dick, I could only get out, “Ummmm.”

Not satisfied with my answer, he grabbed the pillow and threw it on the floor. Through the light of the candles he could see the tent sticking up through the fabric of my dress.

“I knew you’d be into this too!” He said.

“Ummmm,” I stuttered.

EARLIER THAT MORNING

The weatherman on the news had predicted the blizzard of the century. My office had already texted last night that I should work from home. Since I didn’t have to get up early to get ready for work, I slept later than usual. My roommate Ben wasn’t as lucky, because his office told him he needed to come in.

I was sound asleep ...

... enjoying the warmth of my bed when I heard my door begin to open. I typically kept it locked due to my choice of sleepwear. The sheet must have slipped off me during the night and my thong clad ass was pointing right into the doorway.

“Dude, can you help me shovel so I can go to…What the fuck?!” He shouted.

I realized my predicament and covered myself quickly. It was already too late. Ben started giggling and I was too embarrassed to roll over and look at him.

He finally said, “Don’t worry about it, I’ll do it myself.”

My door closed and my mind started to spin. I felt my dick twitch and I reached down to feel it. I was hard which was nothing new since I had just woken up. What was different was that it had slipped out of my panties and was leaking precum. Was I excited about getting caught?

I’ve always been curious about lingerie, but had been scared to try some. That changed two Halloween’s ago when a friend convinced me to go to a party in drag. I had a crush on her and would do anything she said to be with her. When I finally got into her panties, it was because I was actually wearing them.

Jen had me shave my entire body, before putting me into one of her bras and thong. She completed the outfit with a garter belt, stockings, and a blonde wig. My makeup was done so convincingly that even I didn’t recognize myself. I stepped into a short black dress and 3” heels and we were off to a party.

The party was at one of our mutual friend’s houses and I knew ...