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 just about everyone there, including my soon to be roommate Ben. Jen had made me up so well that no one recognized me. They thought I was one of her friends, dressed up in a slutty outfit girls like to wear on Halloween.

I had a soft voice and Jen thought it was hilarious for a guy to hit on me and then reveal my real identity. I didn’t mind it, because it meant I could spend more time with her during the party. We were drinking and having fun, and I was hoping something would happen afterwards.

My hopes were dashed when a new guy started to hit on me and out of the corner of my eye I saw Jen making out with another guy. I was so distraught that I excused myself to go to the bathroom. I took some time to compose myself and then I heard Jen knock on the door.

“You ok in there?” She asked.

“Yeah, be out in a sec,” I said.

I opened the door to see her waiting for me.

“Hey, I just met this cute guy and he’s gonna take me home,” she said, “Are you ok to drive yourself home?”

“Yeah, I’m good,” I said.

“Perfect,” she said and kissed me on the cheek. “Oh, I left a bag in your trunk with some surprises inside in case you’re interested in having some more fun.”

I wasn’t exactly sure what she meant and just said, “Thanks.”

Since my hopes of hooking up with Jen were gone, I said my goodbyes and drove home.

The bag inside the trunk was pretty big and I brought it inside. I was a still a little buzzed and exhausted. It took me a minute to get my dress off and started to remove my lingerie. I took the bra and stockings off and decided to sleep in the panties. That was the beginning and I’ve slept in panties ever since.

The surprise bag contained exactly what you thought it would. There were several bras, panties, and a red dress that matched the black one I had worn the night before. Lastly there were some cosmetics and a dildo. On top there was a note:

“Babe, I knew you would look so hot dressed up that I figured you’d want some things of your own. If I’m totally wrong, just donate them and get a tax write off. I’m pretty sure I’m right though! XOXO Jen.”

I was totally surprised. Why would she think I would want to play around with women’s underwear? I’ve been trying to hook up with this girl and she was buying me lingerie instead. I was very confused. Then I looked down to realize I was still wearing her thong from last night and it was barely containing my hardon. Maybe I did like this stuff.

Just in case, I buried everything in the back of my dresser drawers and hung the dresses in the corner of my closet and hid them as best I could. I certainly had no intentions of using the dildo, but I kept it anyway. I lived alone at this point, but I was still being cautious.

It took me a week of twisting and turning in bed before I tried sleeping in panties again. She had given me 5 pairs, which of course wasn’t enough. I went on Amazon and before I knew it, I had 30 pairs, one for each day of the month. I only wore them to bed and pretty much disregarded everything else.

Time went by and Jen got engaged to the dude from the party. Our friendship had basically faded at that point. She never mentioned the bag she left for me and of course I didn’t volunteer anything. I dated a few girls, but was always afraid to bring them back to my place, because I was embarrassed to tell them I slept in panties.

I was doing well at work, but I had this extra bedroom just sitting there unused. I heard though the grapevine that Ben was looking for a place and asked him to move in. I might as well have someone help with the rent and it was nice to have a friend to hang out with.

That brings us to today. I had been wearing panties to bed for over a year and until now my secret had been safe. Who knew it would be a January snowstorm that would change my life?

I got up and put on a pair of boxers. I walked to the front window and saw Ben shoveling the driveway. I figured he would go to work and I would have all day to come up with an explanation. I went into the bathroom and took a long hot shower.

As I usually did, I wrapped a towel around my waist and walked back to my bedroom. I was surprised to see my door was closed and locked. I fiddled with the doorknob, but that was no use.

Ben was inside and when he heard me he said, “Good Morning, Sweetcheeks!”

“Dude, what the fuck!” I screamed, ignoring the pet name he used. “Why are you in my room? Why aren’t you at work?”

“Well Pantyboy, after the show you gave me I called in sick,” he said.

My cheeks turned bright red. I couldn’t believe he was calling me these things.

“That’s great,” I said sarcastically. “But I do have to logon to work from home, so let me in so I can get dressed.”

“Don’t worry about it, I already texted your boss that you weren’t feeling well. He said no problem and to feel better. You really should have a lock on your phone,” he said.

“Ok, you’ve had your fun. Open the door and let me get dressed. I’ll tell you whatever you want to know,” I said, sounding defeated.

“Actually your outfit is on my bed. Go into my room and get dressed, then I’ll come out,” he said.

“Dude, enough already,” I said, “And what do you mean by MY outfit?”

“I think you know exactly what I mean,” he said, “you looked so hot on that Halloween!”

I didn’t respond and walked into his bedroom. On his bed was pretty much what I expected. A black bra, thong, garter belt, and stockings. Draped across the bed was the red dress that I had never worn. Then there was the blonde wig and a tube of lipstick and eye shadow. At the foot of the bed were the 3” heels I had only worn the one time on Halloween. It had been over a year since I wore anything like this, and I was actually a little excited about it.

The memory of how to put everything on came back to me. I didn’t do a bad job with the limited makeup either. I had no idea what Ben had planned for me, but when I picked up the dress, I saw the dildo underneath it. I started to get nervous. We were both straight guys and I just liked the way panties felt in my bed. Now I was fully dressed again and didn’t know what I was walking into.

I put my heels on and walked in them easily enough. He must have heard them clicking on the wood floor and he finally came out of my room. I peeked in the doorway to see all of my panties scattered across my bed along with the bras Jen had bought me.

“Dude was all of this necessary?” I asked.

“Yes it was Sweetheart,” he said, “And may I say, you look as hot as I remember.”

“Gee thanks,” I said.

He led me to the couch and we both sat down.

“So why didn’t you tell me you liked to cross dress?” He asked.

“Because I don’t,” I said.

“The thong riding up your ass crack that I saw this morning says otherwise,” He said.

I took a deep breath and said, “It’s just panties, I like to sleep in them. They’re...um…really comfortable.”

“What about the other stuff you have?” He asked.

“Jen left it for me after Halloween. I kept it all because…well, I’m not exactly sure,” I said.

“Like I said, you look hot all dolled up. I wish you told me. I’ve always had a thing for girls with a little extra,” he said.

“And I like girls, girls. Like I said, I just like to wear the panties to bed,” I replied, trying to convince him.

As soon as I finished speaking, I felt a twitch in my dick. I tried to think about anything else, because I didn’t want to get an erection. Just then there was a loud pop and the power went out. It was still day time, but since the snow was covering the windows and there was no sunlight, it was pretty dark. Ben got up to get some candles to brighten the room. I had no luck in calming my erection and a put a pillow on my lap as my only hope of concealing it.

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

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 said again.

“Listen, we’re snowed in with no power. I can’t think of a better time to do a little experimenting. Can you?” He asked.

“Dude, I don’t know…” I replied.

“You can’t tell me you haven’t thought about it,” He said, “How long have you been wearing panties to bed?”

“Over a year,” I said, reluctantly.

“And how many times have you played with your dildo?” He asked.

“What?” I said, surprised, “Never!”

“Then why do you have it?” He asked.

“Jen got it for me, but it’s been in the back of my drawer until you took it out today,” I said.

“Sure,” he said.

“I’m serious,” I said.

“Ok, I’ll take your word for it. Seriously though, you’ve never thought about hooking up with a guy while you were wearing your panties? I’ve never seen you bring a girl around,” He said.

“Honestly no, I’ve never thought about it,” I said.

He reached over and began to rub my dick through my dress. I moaned. It had been so long since anyone had touched me.

“Well your hard cock says otherwise!” He said.

He kept rubbing.

“It’s just…the clothes…the candlelight…it’s been so long...ahhhhh,” I moaned as I had a massive orgasm, blowing a huge load in my panties.

“Feeling good Baby?” He asked.

“Yesssss,” I hissed, totally disregarding that he called me Baby.

“So what do you think? You want to fool around? It’s not like there’s anything else to do,” He said.

“Ben, I just don’t kn….” I started to say.

Before I could finish my sentence he kissed me on the lips. I kissed him back and soon his tongue was pressing on my lips. I opened my mouth to accept his tongue and we made out. It had been so long since I had kissed anyone like this and it felt awesome! We continued sucking on each other’s tongues until we finally came up for air.

“I guess that’s a yes?” He asked.

“I guess so, but…” I said, reluctantly.

“Don’t worry, you don’t have to do anything you don’t want to do, but I want to make one thing clear,” he said.

“Yeah?” I asked, curiously.

“I was ok with using my hand to get you off, but from this point forward, I’m the guy and you’re the girl, is that ok with you?” He asked.

“I think we can make that work,” I said.

“Believe me, I’ll make you feel so good, you won’t even think about acting like a guy,” he said.

“In that case I have a confession,” I said.

“Okay?” He asked.

“I lied before when I said I never used the dildo. One night I was out with a girl and came home with blue balls. I was a little drunk and instead of just putting on my panties I put on a bra too. I put the dildo in my mouth and sucked on it while I jerked off. Since then I had always been curious what it would be like to suck I real cock,” I said.

“I definitely think we can make that work,” He said, repeating my earlier comment.

“So how do you want to do this?” I asked, nervously.

He pointed to his shorts and I could see he was hard.

“You’ve inspired me!” He said.

“Do you mind if I take this dress off? You must have the heat turned all the way up. I’m really hot!” I said.

“Yeah you are!” He said, twisting my words a bit.

“I’m serious,” I said.

“Of course Baby, I’d love to see you in your sexy lingerie!” He said.

I stepped out of my dress and slung it over the back of the couch. He looked me up and down.

“Damn girl! You really need to wear things like this more often!” He said.

“Baby steps,” I said.

He stood up and dropped his shorts, exposing his huge dick.

“Holy shit!” I said.

“Nice, right?” He said with a smirk.

“Yeah, but how do you expect me to get that in my mouth? Remember I’ve never done this before,” I said, nervously.

“Just go slow and take your time. You have gotten head before, right?” He asked.

“Of course,” I said.

“Pretend you’re one of those girls and try to copy what they did,” he said.

I took a deep breath and said, “Ok, but don’t blame me if it sucks.”

“As long as you suck I’m sure it will be wonderful!” He said.

“Ha,” I said as I dropped to my knees.

Up close his dick was even more massive. I couldn’t believe I was really going to do this. I mean I’ve come this far. I’m wearing lingerie and on my knees in front of my roommate. It guess can’t hurt to suck a little cock. Maybe he’ll be happy with one blowjob and we can go back to being buddies again.

I kissed the head of his dick and he let out a moan. A drop of precum leaked out and instinctively I licked it off. I was surprised I didn’t mind the way it tasted. I licked again, this time swirling my tongue around the tip.

“Oh yeah! Bathe my cock!” He screamed.

I was happy I was making him feel good and I was getting excited myself. I felt my dick get hard in my panties as I gave my first blowjob.

After a while of licking his huge member it was time to put it in my mouth. I tried to think about the girls that had blown me like he suggested, but all I could think about was his dick. I had been curious about sucking a dick, but I never thought I’d actually do it. Now it’s the only thing on my mind! I want to blow my roommate and I want it to be the best he’s ever had!

I opened my mouth and quickly closed it around the tip. I waited for a second to get used to his girth. The biggest thing that had been in my mouth up to this point was the dildo and this was completely different. The dildo had been cold and rubbery while his dick was hot! I used some more tongue swirls, and then I felt his hand on the back of my head.

Ben was getting impatient, and I can’t say I blamed him. I was certainly taking my time. I tried to speak to tell him to relax, but with his dick inside my mouth it just came out as an “Mppphh.” Somehow that did the trick and he removed his hand.

I moved my head slowly, taking him deeper and deeper. When I didn’t think I could take anymore I stopped. I lifted my eyes up and saw the happiest look I had ever seen on Ben’s face. That inspired me even more!

I started to pull my head back and moving my tongue in circles. He was moaning and panting and I knew I was doing a good job. His dick was so big there was no way I could take it all. I put my hand around the exposed shaft and stroked him while I sucked. I remembered that I liked my balls rubbed while I was getting head. I moved my hand down and cradled his balls while I continued to blow him.

“Oh My God!” He yelled. “So Good! Suck on my balls!”

Challenge accepted I thought to myself! I pulled my head back and as soon as his dick popped out I gobbled on his balls. I continued to stroke him as I sucked on his balls. I was concentrating so much on giving him pleasure, I couldn’t make out what he was saying. It just sounded like gibberish. Finally I was able to hear him.

“I’m…gonna…cum!” He yelled.

As soon as I heard that I stopped sucking his balls and stroking his cock. There was only one way my first and possibly only blowjob was going to end, with him shooting his load into my belly!

He groaned in disappointment when I stopped, but that was short lived when I took his dick back in my mouth. As he slid back inside me, I saw my lipstick marks for the first time. I smiled, well as much as I could with a dick in my mouth!

I was determined to make him cum and I was moving my head back and forth as fast as I could. I was basically jerking him off with my mouth. I felt his dick grow even bigger and I knew what was coming. I took him as deep as I could and he exploded.

“Holy Shit!” He screamed.

His first spurt caught me by surprise, because the second his cum hit the back of my throat there was a huge popping sound and the power came back on. It was like his orgasm was in charge of the power grid! I swallowed and then moved back so his next shot hit my tongue. Just like the precum, I didn’t mind the taste. Maybe I just liked sucking cock? I continued to bob my head and he continued to fill my mouth. I did my best to swallow, but he was cumming so much that some leaked out onto my lips and cheeks. When he was done cumming he slipped out of my mouth and I stood up.

“Damn Sweetheart that was a world class blowjob. Are you sure you haven’t done that before?” He asked.

“First and maybe last,” I said.

“No way! We’re definitely doing that again,” he said.

“I’ll think about it,” I said and winked.

He pointed to my cheek and giggled. He said, “Looks like you have a little spillage.”

I knew some had spilled out, but I didn’t expect him to embarrass me like that, especially after I swallowed so much of his cum. I didn’t say anything and walked quickly to the bathroom. With the lights back on I got a good look at myself in the mirror and I was a mess. My wig was all tussled and my makeup was smudged. I thought about changing back into my guy clothes, but then I remembered he promised to make me feel good and I was curious about what that meant.