tagTranssexuals & CrossdressersLaying Down Some Tracks

Laying Down Some Tracks


I never expected what was to come of me, and even now, I'm still shocked by what I did.

My name is Shawn, and I was just out of college and had a really hard time finding a job. I spent four years studying to be a teacher, yet I only ended up working at a fast food place and playing guitar for a band.

The story takes place in early November, but it really started on Halloween. My band, "Pedestrian Wolves," was doing a show at a local venue that housed small local bands. We played a mix of new wave and metal. We usually wore suits, but all our hair was long and black, our fingernails black, and we wore make-up that was a throwback to the gothic-industrial music of the late 90s, early 2000s.

But being Halloween, we all went in costumes, but kept them matching. We we're the humunculi from an anime we were all fans of. Our singer/keyboardist, Vanessa, went as Lust, with her luscious black hair made wavy, and a dress that went past her legs, but exposed her breasts, and let me say that they were glorious!

Our drummer, Kent went as Gluttony, since he was overweight, he wore a bald cap, and tights that were just embarrassing. Jimmy, our bassist, the ladies man of the group went as Greed, and looked all sleek. And I went as Envy, the shape shifter. In the show he was a guy, but could change his shape and looked pretty androgynous with a belly shirt and skirt.

We played our gig, and some anime nerds really dug our outfits, but those unfamiliar with the show kept mistaking me as a woman the entire time. I was embarrassed and got pretty frustrated at first. I was short, only about 5'5'' and I was thin, I was never able to gain weight, no matter what I ate. Even worse, I was never able to really build up any muscles. But, after a few drinks, I started to get accustomed to the cat calls and whistles. I decided to play it off, best I could. There was a part of me that enjoyed it, after the alcohol worked its way, but nothing I would pursue... or so I thought.

The next day, someone through our Facebook page contacted me and asked if I could lay down some guitar parts for some of his songs.

I didn't really think too much of it, as I've been asked before, usually by young kids with shitty emo lyrics, but this guy, Pete, was a bit older, in his early thirties, and judging by his facebook page, his taste in music was up my alley. He was big into Pink Floyd and Radiohead, two of my favorite bands.

I messaged him back, asking about what he was looking for, and some samples. He messaged me back that he mostly worked with drums, synths, and piano and played a few small gigs at some bars, but he wanted to record an EP to sell at those shows. He even offered to pay me a hundred bucks.

Let me tell you something, when you're 23 years old, working at a burger joint, flipping burgers, with a college degree under your belt, making maybe 200 dollars a week, a hundred bucks sounds mouth watering.

I asked him what brought me to his attention, and he had replied that he took his younger brother to the Halloween show and I caught his eye. There was a hint of "what-the-fuck" in the back of my head, but my wallet snuffed it before I could give it a passing thought. I agreed to meet Pete the next day and we bid farewell there.

The next day came and I woke up to a shower and coffee before packing up my acoustic guitar and headed off to meet Pete. He lived not too far away, a town over. I had no problem finding the place as we went there often. There were some nice bars near by that my band mates and I had frequented.

His house was small, but the lawn was kept and the front porch looked clean, despite an old welcome mat that had definitely done it's job over the years. I rung the bell and shuffled my feet with my guitar slung over my back.

The door opened, and Pete stood there. He was tall, bigger than six feet. His shirt was tight against his arms, it was apparent he didn't have a problem putting on muscle mass. He greeted me with a smile, "Shawn, I'm glad you wanted to do this."

"Hi, it's nice to meet you, I was just glad you weren't some snotty teenager crying about some freshmen he dated for three weeks."

He chuckled, "Well, I do this for fun, but I saw you the other night and I was awe-struck."

I was flattered, I never really got that big of a compliment on my music. "Thanks, I do my best."

"I noticed, would you like to come in." His smile was accentuated by his eyes that seem to just pierce me.

"Do you live alone?"

He lead me to a room in his house that had a computer desk, a piano, and a drum set. "I do, no girlfriend or roommate here. Just me."

"That's got to be nice, I'm back living with my parents. I don't make enough to afford my own place."

"Well, there's always opportunities out there, I'm sure one will find you." He gave me that piercing smile, and it looked like he was eyeing me up.

"Thanks, I hope soon." I felt a little uncomfortable, but do I need to repeat that there was a hundred bucks on this?

He then moved over to the door to the room, "do you want a drink or anything?"

I put my guitar down and replied, "Sure, I'll take whatever."

He walked out of the room as I tuned my guitar. I strummed a few chords playing a random progression when he re-entered with two glasses.

I took the cup and sipped from it. I was surprised that it was a rum and coke.

"I hope you don't mind, I find a little liquor loosens me up."

"It happens to us all." I wasn't opposed to a drink, and I took another sip.

We talked and bullshitted for awhile, about what he was looking for, the drinks dwindled and he returned with another and as I took another sip, he pulled something from his pocket.

"I hope you aren't offended by weed."

I was definitely on good terms with the herb, "Not at all, as long as you share." I felt the alcohol in my system now, as I reached for the pipe. I did not realize how strong his drinks were.

"Excellent, you know some think it's weird for a guy my age to do this."

I chuckled, "Oh you're not that old."

"I'm ten years older than you!"

"So?" I muttered before inhaling the smoke into my lungs. I passed the pipe back to him before exhaling.

We passed it around a few more times before it was spent. I was feeling very loose at this point, not my favorite way to play, but I had no problem performing.

"So, don't take this the wrong way," he began. I sobered up slightly when he said this and looked at him, he chuckled before commenting, "But I really liked your Halloween costume. You pulled it off very well."

I laughed, "Oh, are you a fan of Fullmetal Alchemist?"

"My younger brother is, but I'm familiar enough."

"Thanks, I wasn't sure, the character is very androgynous."

"Yeah, but you pulled it off, I bet you could even pull off looking like a girl, that is if you wanted too."

I was a bit taken back, "Excuse me?"

"You know, like with a skirt and cute shirt, you could do it!"

I was thinking it was just the pot and booze talking, I should of left at this point and I wanted too, but a hundred bucks was hard to turn your back on. I decided to put up with it. "I don't think I could, I really couldn't."

"Yeah, you've got that long hair, you could put it in pig tales, and shave your legs and wear a skirt."

In my head I was picturing it, and I really could, but that's not something I would want to do, "No, I don't think I could."

"Prove me wrong!" He cried, "My ex left some things behind, she was about your size!"

I was starting to blush, "I couldn't!"

"You're blushing! You're going to do it!"

"No, no, I couldn't!"

He then replied, "Try it, I'll double the money."

I finished the glass of rum and coke with one gulp, toying with the idea. Another hundred bucks? I couldn't turn it down, and I just had to put on some girls clothes. Looking back, I probably shouldn't have finished the drink, as it really messed up my reasoning. "Okay, but I just have to put it on, right?"

"And let me see, of course. So I can judge." He gave me that smile again.

"Show me the clothes."

He took me up to his bedroom and opened up his closet, inside was a box with "Margot" written on it. He pulled it out and opened it up. "I get to pick what you wear!"


"Well, I'll make it easy for you, something slutty."

I was ready to stop there, "What?"

"Well, if I give you something more conservative, it'd be easier to pull it off, but I give you something slutty, then I'll be more likely to tell you're a boy."

"Yeah, that makes sense." I was drunk.

"Okay, then go and shave all the hair on your body, you have to try to pull it off too. There's some make up in the box too." He handed me a small bag from there.

I peeked inside and saw eyeliner, lipstick, and blush. I knew how to put all this stuff on, as the band regalia required it. "What am I to wear?"

He dug through the box until he found what he was looking for, he was definitely familiar with what was in there. I wondered how many times he had gone through it since his break up. He pulled out a pleated micro skirt, dark red and black. He then pulled out a black tank top, a black bra, and a pair of black, lacy panties. He handed them to me, and then put a pair of black leather boots with 3 inch heels on the pile. "This."

I looked at them, and I admitted to myself that I would of dug any girl wearing this. "Okay, but only for a few minutes."

He chuckled, "I promise, as long as your comfortable." He pointed me to a bathroom off the bedroom, and before I closed the door, "Don't forget the pig tails!"

I closed the bathroom door and began to lather up my legs. I had shaved them for the Envy outfit, so the leg hair wasn't hard to shave, same with my chest and armpits. I went over my face once more, just to be safe. I then looked through the lipstick and found a deep dark crimson, and applied it to my lips, I traced the eyeliner around my eyes, and applied a little blush. I looked in the mirror at the person staring back at me. There was almost the perfect naked chick looking back at me, except for the dangling cock laying half erect. Why am I getting turned on by this? I thought, but figured it was from the nerves and booze. I slipped on the panties, tucking my penis as best as possible, I applied the bra and found that it had gel pads in it to add two sizes. His ex must have been pretty flat. I slipped the skirt on, threw on the tank top and adjusted it. I then sat down on the toilet and pulled on the leather boots. I stood up and found it a bit difficult to walk in the heels in my drunken state, but I got the hang of it. I was about to walk out when I remembered the pigtails. "Why did he tell me to put on pigtails?"

I thought about it, but still put my hair up into two pig tails, letting a few strands hang down the side of my face in front of them. I turned back and looked in the full length mirror. Damn.

That's all I could say, I pulled it off, and he was right. Then I thought about the position I'm in. I'm in a guy's house, who only saw me dressed as an androgynous shape shifter, he got me drunk and high, and put me in ladies clothes.

What. The. Fuck.

Seriously, what the fuck was I doing here? How did I let him talk me into this.

There was a knock on the door.

"Uhm, I'll be out soon."

"Okay, I was just hoping you weren't going back on the deal. Two hundred bucks is a lot of money."

Damn he was right. I said to myself: "Okay Shawn, he can't make you do anything you don't want to."

I took a deep breathe and opened the door and went into the bedroom.

"Oh wow, Shawn, or should I say Shannon? I think you lost this bet."

I looked up at him sheepishly. Even with the extra three inches from the heels, he towered over me.

"I'm not Shannon."

"You're dressed as one!" He laughed. "Now come closer, I want a better look."

I took a few steps forward, but lost my balance and fell forward towards him. He held out his big arms and caught me, pushing me up against his chest. There I was, dressed as a slutty girl, up against the chest of a toned guy, his arms wrapped around me.

"Why hello there." He cooed

"Uhm, yeah. Sorry." I apologized, looking up into his face. He had a very masculine smell and it filled my lungs. He let me go and I stood up, catching my balance, then I heard a click. I looked back at him and he took a picture with his phone.

"Did you just take my photo?" I asked, sternly.

"Two hundred more dollars, if I can get a few pictures."

Damn, that was a lot of money. "No!"

"Please, baby? You look so sexy, Shannon!"

"I'm not Shannon!"

"Okay, it's just you look so good."

I did look good, I wasn't going to deny it, but I couldn't just let him take pictures of me, I couldn't be some object he was just going to jerk off to later. "I can't."

"Why not, it's not like anyone could recognize you. I'll make it three hundred, plus the other two. That's five hundred dollars. What's what, like a months pay?"

"Yeah, but... I don't know."

"How about this, you let me take one picture, if you don't think it's sexy, then you can have my phone and delete all the photos."

"And if I do?"

"You let me take a few pictures, of whatever pose I want, and you leave with five hundred big ones." He then pulled out his wallet and pulled out the five one hundred dollar bills. "Take this one, and check, you'll see they're real."

I held it up to the light. I was literally holding more money than I've seen in so long. "One picture."

He smiled. He was enjoying this. "Okay, get on all fours on the bed and look at me."

I reluctantly did.

"Now come on, get into it!"

I sighed, I arched my back a little and looked up at him. "Good enough?"

"Almost there, baby. Give me a sexy look, use your face to tell me you want my big cock in your mouth."

"WHAT?!?" I shouted.

"Come on, I said get into it. You're a slutty woman looking for a big cock. Just play along. You got to try to make it convincing!"

I tried to give my best cocksucker face, but I just wasn't that type of guy. I never wanted to do anything with a guy, I never gave them a second look.

"Almost there, babe, say "I want your cock."

"I'm not saying that."

"You want this to be fair?"

In a bored tone, "I want your cock."

"Come on, get into it!"

"I want your cock," I said it with more feeling.

"Tell me how bad you want it."

"I want your cock real bad, baby." Did I just say that? It must have been the booze.

"One more time, beg for it!"

And I did: "Oh Pete, just let me have that big cock of yours!" I don't know what happened to me there, I just gave in to it. Pete was so dominant now.

I heard him click the picture, and then he turned the phone towards me. "Well?"

It looked sexy. I didn't even say anything.

"Now come on, Shannon, get up and bend over my dresser, showing me that cute butt of yours."

I kept telling myself, "Five hundred dollars." but as I bent over and looked into the mirror over the dresser, I couldn't deny it looked sexy, I felt my cock begin to stiffen. What was happening to me?

"Stick that butt out a little more."

I couldn't help it, I did what he said. I heard another click, then I felt his hand run up my butt cheek, followed by a slap. I jumped forward and moaned. Wait, did I just moan? My cock was hard now.

"Sit up on the dresser now, and spread those sexy legs of yours."

I got up on the dresser and spread my legs. I can't tell you why, but I even gave him my best "fuck me" face.

"I see you're getting into this baby, look at your little cock standing straight up. You like being naughty."

"Yeah, I do, baby." Did those words just come out of my mouth?

He had me bend over again, followed by another slap on my bottom. Then he had me pushing my "breasts" together, and a close up of my face licking my lips.

I felt so loose now, it was starting to be fun. And I was getting horny. Why was I getting horny?

"There's one more picture I want to get, baby." He said as he got closer to me.

"What?" I could tell he was unsure of it, and it started to bring me out of it.

"Well," he said moving closer to me, "I want one of you kneeling down."

"Okay, I can do that."

"With my cock in your cute little mouth."

I stopped. "No, I couldn't do that. I'm not gay."

"Oh, stop it Shannon, you're such a sexy girl." He was right up against me, he placed his arms on my hips. "And you're so sexy. I just think you'd look so sexy letting that little slut in you out to play."

"Listen, dude, I don't swing that way."

"Sure you don't. You've been enjoying this."

"I'm drunk and high."

"And doesn't being stone make every ounce of you skin feel so good." He whispered into my ear.

I felt his breathing on the side of my face, his hands began to run down my hips and around to my butt. He grabbed my cheeks, and I just let him. He was right, his hands felt so good. He rubbed them up my back, and back down, massaging my ass cheeks. I felt my cock harden again, it was stiff now. He was so close to me now, I could feel the bulge in his pants rubbing against me.

I looked into his dark eyes, "I really can't." He began to rub his crotch against me. "Sure you can."

I couldn't take my eyes off his as he moved in closer, I felt his mouth breathing close to mine before he put his lips against mine and began to kiss me.

His one hand was on my butt cheek, while his other was rubbing up and down my spine. I couldn't deny how turned on I was. I began to kiss back. I never kissed a man before, but as his tongue twirled with mine, I found myself enjoying this greatly. I was his babe right now, and I wrapped my arms around his neck and kissed him some more.

He then pulled back, I didn't want him to stop, "Come on, one more picture."

"I-I" I felt his hand take mine and place it against his warm crotch. I could feel his cock through his jeans, and I began to rub it.

We kissed again as I rubbed it, maybe I could just get him off now before this goes further? Once he released, he won't want to do this anymore, and I could just go home. "I am in control here," I told myself. I have control over his cock, I can make him cum. I felt so empowered by these thoughts.

"Oooh, girl, that feels so good. Oh baby."

I felt more in control, and more turned on. I kissed him harder now, rubbing faster.

"That's it baby." he whispered into my ears. "Now come on, I want to see your sexy body kneeling down."

And then, I don't know why, but I pictured myself down in front him.

"You just have to put it in your mouth for one picture. That's it."

I giggled, "Okay, cutie," did I just call him cutie? "One picture."

I knelt down in front of him, and found myself looking straight into the crotch of his jeans. I could see it bulging, just asking to be let out. I unbuttoned his jeans, and pulled the the pants off. I reached inside his boxers and found his dick. I never felt another man's before, it was soft on the outside, but I could feel the stiffness of his erection begging for release. I could smell the musty odor wafting out as I pulled the erection out from the boxers.

There it was, in front of my face, a giant veiny cock. Swollen and pulsing begging for my mouth. I swallowed my pride, telling myself, "five hundred dollars." I grabbed it with my hand and wrapped my lips around the end of it. It was a little salty from the sweat, but there was something about this position. Something that stirred my own cock. Here I was, kneeling down with this guys dick in my mouth.

"Look up, sweetie!" I heard him say.

I peered upwards with his dick in my mouth, and he snapped a picture with his one hand, but before I could pull off, I felt his other hand against the back of my head. He wasn't going to let me off.

"Now, doesn't it feel good in there?" He said as he began to thrust lightly. I felt it move back and forth over my tongue.

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