Stuck at a Stranger's House

"That's it?"

"Well yeah."

"Why were you embarrassed about that?"

"Do you mean: why was I embarrassed to tell you that I have the compulsion to put on makeup and a wig so that I look more like a girl?"

"I guess when you say it like that it does sound a little bit different."

"It's so embarrassing."

"I'll tell you what. Why don't you go upstairs, do whatever you need to do, and then come back down here. I won't even say anything about it."

"Seriously?"

"Seriously."

"Well, alright then."

I got up from the table and made the quick walk upstairs. As I entered the room, which I guess at the moment was mine, I quickly made my way over to the vanity and sat down. I did a quick inventory of everything — half of which I had never seen before — and was lucky enough to find a book in one of the drawers that was attached to the vanity. The book was a picture book that showed how to put on makeup; how lucky!

I poured through the book quickly and decided to start where the book did: foundation. I picked up the foundation, which just so happened to be near my skin tone, and applied it to my face just as the book instructed. This was followed by a layer of pressed powder.

I then moved onto my eyes. Rather than following the book's instructions, I opted to go for a pretty casual eye makeup, and only apply eyeliner. That seemed to be the style among women today; they tend to not go too heavy with eyeshadow but they did a pretty good job with the eyeliner. The book instructed me on how to do a cateye — and after a couple of tries — I was able to be confident that my eyeliner looked pretty good.

The book then instructed me to add a little bit of blush to my cheekbones so I followed suit.

The final instruction was for lipstick. I had always had an affinity for red lipstick, so I opted for that.

I looked in the mirror on the vanity, with my makeup complete. Not bad, I thought. But I was still missing something.

The blonde wig that was on the vanity earlier was still there and I quickly realized that of course I was missing something.

I picked up the wig and placed it on my head. I used the mirror to position it on my head and fix it so that it looked fairly natural. After doing so, I was shocked.

I looked pretty good, I thought to myself.

I went into the closet to look in the full length mirror and was still shocked at how I looked. I actually look a little bit like a girl.

As I was examining myself in the mirror, I noticed that I had spilled something on the dress at some point though. I have no clue what it was but I knew I couldn't wear this anymore. I pulled the dress over my head and the sensation of the hair from the wig was a new one. Then I was stuck there in the thong and bra that I had picked out the day before, looking for a new outfit.

I looked at the tons of clothes at my disposal and decided to try out a skirt this time. But first, a green tank top had caught my eye, so I pulled that over my head. There were a number of skirts that were in the closet and I liked the look of a lot of them, but I wanted something a little looser than the dress that I had worn — if I was gonna be forced to wear women's clothes, I might as well experiment a little. I chose a short, white, flowy skirt that came down to about mid-thigh. I stepped into it and decided to keep the tank top tucked into the skirt.

I was about to step out of the closet when I noticed the multiple pairs of shoes in the closet. Fuck, I thought to myself.

I picked out a pair of modest wedge sandals and put them on.

----

"Holy shit," Bryan said.

"You said you wouldn't say anything."

"That's cause I thought you would look stupid, but you're actually quite good-looking."

"You really think so?"

"Yeah, I mean if I hadn't seen you earlier, I would probably think you are actually a girl."

"I thought I looked good too, I just wasn't really sure."

"Well turns out you make a pretty good looking girl."

"I'm not sure whether that's a good thing or not."

"Yeah that's a tricky one. Does it feel weird though?"

"Well it's certainly weird to not be wearing pants. All of these women's clothes are a lot more soft, I feel like all other clothes are kind of rough and hard."

"Interesting."

"I feel like I put a lot more into looking like this then I normally would though."

"It certainly shows."

I giggled at this for some reason.

"So what should we do for the rest of the day?" Bryan asked.

"Hmm, I'm not sure. I'm just looking to pass the time as fast as possible."

"We could play like a board game or something."

"No that's boring."

"We could get drunk off our asses."

"That actually seems like a good idea."

"Seriously? I was just kidding."

"Well what else would pass the time as well as getting drunk?"

"I can't really argue with that."

Bryan got up and got us two glasses and a bottle of vodka from his alcohol cabinet at 11:30 a.m. in the morning, and we both drank.

It didn't take very long at all, until we were both pretty well sauced — probably only a couple of hours.

"Well, if I don't stop drinking now, I'm gonna pass out," Bryan said.

"What a pansy."

"Oh really? I'm a pansy? You sitting there in a skirt and heels and makeup, and you're gonna call me a pansy?"

I giggled before responding.

"That's right, you're a pansy!" I said as I took another sip of vodka.

"Well fuck you, this pansy needs a nap."

Once again I giggled — alcohol seemed to make me giggle.

Bryan got up and went to his room and I was left at the table with the bottle of vodka, but when Bryan stood up I noticed something. There was a noticeable bulge in his pants. Weird. Why was excited? More importantly why did I notice or care? I quickly shook these thoughts.

Drinking alone was not fun, I thought to myself, so I decided to ditch the idea and go exploring in the house. I was bored and drunk so why not?

I stood up and then realized that I was still wearing the heels. I took one step and realized that this was a bad idea, so I took them off and carried them in my hand, just like I had seen women do on the 'walk of shame.'

My exploring led me, at first, to all of the downstairs rooms. Nothing too eventful in any of them. There was one room with a bunch of exercise equipment — that would explain why Bryan was in good shape. Another room was an office, where I suppose Bryan did some work. There happened to be a computer in the office — not really a surprise — and I decided to do a little searching, so I put down my heels on the desk and sat at the chair.

Keeping in mind that I was pretty drunk, I was a little curious about my situation. Surely there must be other guys that had worn women's clothing — I had seen it in movies after all — so I typed into the search bar, "man wearing. . . " but before I could finish, a suggestion popped up saying, "man wearing women's clothing." That's weird I thought, was Bryan doing the same thing I was doing? He must have been. I wonder what else he was looking at? This gave me the idea to look at his search history — a nightmare for almost everyone.

I clicked a couple of the links, and they took me to regular pictures of men in women's clothing — or crossdressers as I came to find out. As I went down the list though, the images began to get more explicit, it didn't take long until the pictures featured a crossdresser with a penis in her mouth or her ass. Wow, I thought to myself. I even began to get a little bit aroused.

I continued going down the links and eventually got to see a few videos. I was transfixed and the state of my arousal was growing. I spread my legs in the chair and lifted my skirt, as I began to gently rub my penis through the thong I was wearing.

I was getting lost in the videos, and lost in myself, as I continued to gently massage and caress myself through the panties. So much so, that I didn't even hear Bryan enter the room. I never heard him, I only felt him. He had come up behind me and started to massage my shoulders.

I was so lost and drunk, that I didn't even think anything of it, and continued masturbating. Bryan moved my hair, so that it was all covering my left shoulder, and started to kiss me on my cheek. All of it felt so good, tiny moans began escaping my mouth.

Bryan continued kissing my cheek until he started moving closer and closer to my mouth, but before he got there, I turned my head so that our lips would meet — and they did. They met for the first time and I could feel his stubble scratching me a little bit, but I didn't care. Our lips moved together, our tongues wrestling one another. Occasionally, Bryan would stop and would bite my lip just a little bit, which felt amazing.

We continued kissing for quite a while until Bryan stopped. I opened my eyes to see Bryan standing over top of me. He grabbed my hand and led me to his bedroom.

We entered the room and he sat me down on the edge of his bed, and then just stood in front of me for a moment. Then, he started unbuckling his pants, ready to show me his penis. I responded by instinctively pulling my tank top, up and over my head. By the time I finished doing so, he had succeeded in pulling down his pants and I was greeted with my first living penis — other than my own of course. It was definitely bigger than mine, his being about 7.5 inches (mine was only about 5 inches).

Bryan moved closer to me and when he was within reach of my grasp, I reached out and touched it. I took his penis in my hand for the first time ever and it was a little weird, but I didn't stop to dwell on it. I merely began moving my hand up and down as I started to stroke it.

It had moved closer to me, and I was now only inches away from it. I knew what to do next. I slowly began licking around the head of the penis. I did this a couple times, just to get used to it, but then I took the head into my mouth.

It was a bit foreign, but it was really no different than putting anything else into my mouth — well other than the fact that it was a penis.

I was familiar with the general idea of giving a blowjob — having received a couple myself — and applied my existing knowledge. I knew to bob up and down while simultaneously moving my hand up and down his shaft. Due to my inexperience I was unable to get to far down his penis, and the hand was more than helpful.

I focused very hard on moving my mouth up and down on his penis. At this moment, everything else had escaped my mind and the only thing I wanted to do was pleasure this man.

I must have been doing a very good job because out of nowhere, I heard a slight moan from Bryan.

"I'm cumming," he moaned.

I didn't even register what he said and before I knew it, his penis was erupting in my mouth. I stopped moving my head up and down, because I was caught off guard and didn't want to choke myself.

I caught all of his semen in my mouth and when he finished, I swallowed it all — I didn't even bat an eye, I just did it.

After Bryan finished, he pulled his penis out of my mouth and it was still half erect. He walked into the bathroom, leaving me still sitting on the bed. I crawled up onto the bed and laid down on my back, exhausted and drunk, with the taste of semen still in my mouth.

I passed out right there on the bed.