This is a continuation of my first story "MY First Time in a Dress". I love reading your comments, enjoy!
I avoided Dan for the next few days by playing sick. I was not ready to go over to his house again yet. My ass was so sore the next day I had to have some relief. I was still having a hard time comprehending what really happened.
I finally went to his house three days later. Dan was a kind of pissed. "where the fuck have you been" he asked. "I was sore so I didn't want come over".
"Well were going to have some fun now, my folks have to work late and Pam's gone all night too". He said as we walked to the kitchen. He opened the fridge and got us each a beer. "I have some real fun planned for us today, I found some real slutty stuff for you to wear" he said.
"Man, I don't want to do that again, it ain't right and it hurts my ass" I told him.
"Well that's too bad, I guess I'll let everyone know that your sissy and wear girls clothes and like sucking dicks" he spewed at me as he took a long swig of beer and smiled at me.
"I guess were gonna have some fun then, where is the shit you want me to wear" I said as I finished my beer and threw the can in the trash.
"That's what I thought, now let's go and get you dolled up" as he lead me to his parents room.
"I thought your folks keep this door locked?" I asked.
"They do, but I found an extra key they had hidden, so I can get in anytime I want without them knowing" he laughed.
We entered his folks room and he went straight to the closet. I was standing there nervously awaiting him to hand me some clothes. He handed me a purple lace bra that was lightly padded and a pair of very skimpy purple lace bikini panties that matched. I held them up and looked at them, they were pretty sexy I have to admit.
"Your going to look real good taday, I'm gonna dress you up like a real slut" he said with a laugh.
He dug around some more and handed me a pair pink thigh high stockings with a lace band around the top. I rubbed them against my skin and they felt so silky & smooth. Then he handed me a little mini skirt that was pleated like a cheerleaders skirt, it was also purple and then a completely sheer pink blouse that was low cut and buttoned in the front.
I couldn't believe this was happening again, but as he handed me the sexy clothes my cock started to twitch with excitement.
"When you get dressed let me know, we're gonna get you fixed up nice today" he said with a laugh. "And when you get dressed you look in the closet here and see if you can find a pair of shoes to wear too" he said as he smiled and walked away.
I went and sat on the bed and started getting undressed. I put the bra on and had to adjust the straps a bit and then stepped into the panties and pulled them up. My cock was hard as a rock. They were skimpy bikini panties with string sides and barely covered my cock and balls. I sat down and slid one stocking up my leg, then the other. These looked really hot! I loved the sexy lace tops and the pink looked great against my tan skin. I stood up and pulled them up and smoothed them out against my legs. I stepped in the skirt and wiggled my hips as I pulled it up and into place. It was pretty damn short and just barely covered my ass. I put the blouse on and buttoned it up and looked in the mirror. I turned side to side looking at myself and then did a spin and made the skirt flare out as I spun around. Wow! I thought, from the neck down I really did look like a girl.
I looked around in the closet for some shoes. There were all sorts of high heels, pumps, sandals and other sexy shoes. I tried a few of them on but they were a little too big and slipped off. I looked some more and in the back of the closet I found a pair of silver strappy sandals with probably a 3-4 inch heel. I slipped my foot in them and pulled the strap as tight as it would go. Bingo! They fit perfect! I put the second one on and stood up. I wobbled a bit and took a couple small steps. I almost fell over but caught myself and took a few more steps. In a matter of minutes I could walk pretty good in them. I walked around the room a few times until I felt somewhat comfortable.
I looked at myself in the mirror on the door. I was amazed at how sexy my legs looked. The stockings and heels were so hot! And the skirt and blouse were pretty damn sexy too. If I just had long hair and make up It would be great I thought.
I called out to Dan and said I was ready. "Hang on, I'll be right there, I need to help you with something else while your in there". he said.
I sat on the bed and crossed my legs like a girl trying to look sexy. As I waited for him I felt the bra and squeezed. It pretty much just collapsed because I had no tits. I looked through the closet and found some socks. I stuffed a few pair in the bra until I had some nice size tits, probably a nice B or a small C cup. Just as I finished feeling the full bra Dan walked in.
"Fuckin' A, you look pretty hot for a sissy boy, I'm gonna love fucking you dressed like that, but we ain't done yet". He said as he lead me to the bathroom.
"Here sit down, were gonna make those lips and face pretty too" he said with a smile
"No, make up man, that shit may not come off" I said to him.
"Listen here, you better quit fucking around and get used to this cuase this is the way it's going to be until you leave, got it?" he spouted.
"Whatever, let's just get this shit over with" I said back to him.
"That's a good girl, now put some of this make up on and look pretty the best you can and put some of this bright red lipstick on heavy, I wanna see it on my cock after I fuck your mouth" He said as he walked out.
I sat there at the vanity with tons of make up in front of me. I had seen my mom put make up on before and had some idea of how to do it. I grabbed a compact and opened it up. I took the pad and rubbed it pretty good on the make up inside. I started brushing it on my face starting on my forehead and working my way down and under my chin until my entire face was covered. Putting this on was pretty easy, I didn't have to do much but apply it all over. I was looking around for some blush for my cheeks when Dan came in.
"Hey, looking good there, drink this" he said as he handed me a tall glass of what looked like coke.
I took a pretty good drink because my mouth was so dry. I almost choked. "What the hell is that?" I ask.
"It's whiskey and coke, just drink it and hurry up, my dicks hard already" he said as he grabbed his crotch and walked away.
I took a couple more drinks from the glass and could feel the alchohol taking affect. I found some blush and a brush. I rubbed the brush in the powder and applied it to my cheeks using a sweeping motion from my cheeks back and up towards my ears. It took a few strokes but I finally got in on where you could see it but not to heavy. I found a compact with about 10 different eye shadows in it. I decided on a glittery light blue. I took the applicator and ran it across the eye shadown and then brushed it on my eye lids from the inside out until I had both eyes made up like a cheap hooker. I sat back and looked at myself in the mirror. I was pleasantly surprised at what I saw, I was actually pretty cute. I grabbed the glass and in a couple big gulps I drank it all down. I grabbed the tube of lipstick he showed and twisted the bottom until the bright red creamy stick came out the top. I leaned close to the mirror and slowly started tracing my lips with the creamy stick. I put it on real heavy and kissed at the mirror a few times to spread it evenly and then took some tissue and blotted the excess off. I stood up and almost fell from the heels and the booze. I stood and looked at myself in the mirror, not bad, not bad at all I told myself. I grabbed a hair brush and brusjhed my hair a few times, there, now I'm ready. (I guess it had paid off watching my mom getting dressed and applying make up quite a bit)
"Dan, I'm ready, do you want me to come out?" I said loudly as I walked toward the door.
"Yea, come on out, I'm in the kitchen" he yelled out.
I took a deep breath and walked out the door and towards the kitchen. When I got to the kitchen Dan had his back to me. As soon as I stepped on the tile floor I heard my heels click. As I walked toward him that distinctive sound of high heels clicking was sounding off. Dan turned around and had a cigarette in his mouth and a shot in each hand.
"Holy shit! You look pretty damn hot, turn around and let me look at you" he said.
I spun around making my skirt flair out and flashing him my panties. He handed me a shot glass and a cigarette.
"I really don't care much for the cigarette" I told him.
"Just smoke it, it makes you look sexy" he said with a smile.
He raised the shot glass in the air for a toast, I raised mine to his.
"Here's to good booze and good sex, and were having both today" he said as we touched glasses and drank the shot down. He lit a lighter and held it up for me to light my smoke. I puffed it a couple times and of course choked a bit. As I took the cig from my mouth I noticed the lip print that I left on the filter and thought how sexy it looked.
Dan was looking at me with hunger in his eyes. I could see the animal lust as he looked me up and down as he smoked and drank his beer.
"Damn, your making me fucking horny as hell, walk around in here so I can see your ass wiggle in that skirt" he said with desire in his voice.
I walked around the kitchen clicking my heels on the floor and stumbling a few times. I was really starting to feel buzzed from the booze. I walked close to Dan and brushed my hand across his thigh close to his cock. He twitched a bit and then reached over and lifted the back of my skirt revealing my panty covered ass.
"Damn, that sure is a fine ass you got there girly" he said as he slapped my ass and I walked away.
"Well I like wearing little skirts to show of my ass and legs to the boys" I said to him as I wiggled my ass. I don't know where it came from but I said it, it even surprised me a bit.
"Well baby, I may just make a woman out of you yet" he said to me.
I laughed and stubbed out my smoke and walked over between his legs ( he was sitting on a bar stool) and ran my hands up his thighs to his crotch and felt his hard cock bulging in his shorts. He reached out and grabbed my hips and pulled me close to him.
"Your sure look better than I thought you would, too bad you don't have long hair cause you really would look like a girl" he said staring into my eyes.
I didn't know what to think. My head was spinning from the booze, I was more than buzzed, I think I was drunk.
"Come on, let's go watch a movie" he said as he grabbed a couple more beers and led me to the den.
We sat down on the sofa and the movie started to play. I sat with my legs crossed like a girl looking down at my stocking clad legs and my feet in these heels admiring myself. The touch of my legs together with the nylons between them was almost electric. I could feel my hard cock throbbing in my panties. I looked over and Dan had his cock out and was stroking it. He put his arm around me and pulled me close beside him. I watched him stroke his cock, the skin sliding up and down his shaft, pre cum glistening from the tip of the head.
We sat and watched the porno for a few minutes while I uncrossed my legs and started rubbing my cock through my panties, I was so hard and horny. Dan noticed this and reached over and took my hand and placed it on his cock. I slowly wrapped my fingers around it and started stroking his hard shaft. He reached over and grabbed my leg and pulled it across his so I was almost facing him. We were staring into each others eyes when I felt him pull my head towards his. I felt his lips touch mine as I closed my eyes as he slid his tongue in my mouth. I started kissing him back while pumping his hard dick.
He laid me back on the sofa as I spread my legs for him, still stroking his cock we kept kissing. I couldn't believe I was kissing another guy, and actually likeing it. I had kissed plenty of girls, but I guess with my eyes being closed it pretty much felt the same. He was running his hands up and down my legs sending shivers through my body. We kissed and made out with him kissing up and down my neck for what seemed like an hour, but was only about 10 minutes or so.
We finally broke our mouths apart and he leaned up while I still stroked his cock. It was hard as steel, and I was so horny I wanted him. He looked down on me and smiled, I smiled back.
"You ready to suck my dick baby" he said to me.
Still stroking his hard cock "yes, I'm ready to suck your dick".
He slid from between my legs and took his shorts and shirt off and leaned back. I slowly slid down between his legs and started licking his hard dick. I licked from tip, tasting his precum all the way down to his balls. I slowly slid his hard dick into my mouth while I stroked it and rubbed his balls. Dan was moaning and pushing my head down until I would gag then hold it there a few seconds and release me. I sucked and licked his wonderful cock for about 10 minutes before he pulled it from my mouth leaving a long string of spit from the tip to my lips.
"Let's go to the bedroom, I want some of that ass now girly" he said to me as he stood up, grabbed my hand and led me to his bedroom. I laid back on the bed and he leaned over and we started kissing again. He slowly unbuttoned my blouse while kissing down my neck and chest while playing with my fake tits. I reached out and took his cock in my hand and started stroking it. He slowly slid my skirt off and the head of my hard cock was poking out the top of my panties. He kissed his way back up my legs until he reached my panties and grabbed them at the sides and slid them off as well.
He laid down on top of me and I spread my legs to welcome him to me. He leaned down and we started kissing again while our cocks rubbed together. He was humping up and down on me as I pulled my legs up to give him access to my waiting ass. He slowly rubbed his cock head on my bud sending shivers of excitement through my whole body.
"Fuck bitch, you got me so hard and horny, I want to tear that ass up today" he said as he pushed his cock head harder against my ass.
He reached over on the night stand and grabbed the bottle of lube and squited it on my ass and on his cock. He stroked his cock until it was coated with the slippery gel and then slowly pushed a finger inside me. I jumped a little as his finger plunged inside me. He fingered me until he had 2 fingers all the way inside me.
"Tell me what you want" as he slid his fingers out.
"I want you" I said as I looked him in the eyes.
"No, tell me that you want me to fuck you with my big hard dick slut" he said as he rubbed the head of his cock on my hot hole.
"I want you to fuck me with your big hard dick" I said back to him.
He pushed my legs back and started pushing the head of his dick on my waiting hole. I could feel it slowly start to stretch my hole. Then I felt a sharp pain as his head broke through and he slowly started sliding his cock in me.
"Wait a second, it hurts a bit" I told him.
"I'll wait until you tell me your ready" he said smiling down at me.
After a few seconds I told him it was ok to go on. He leaned back a bit and slowly started pushing again. I could feel him slipping deeper inside me.
"How much do you have in I ask?" I ask.
"About half, you ready for more?" he asked me
"Yes but go slow so it doesn't hurt" I told him.
He grabbed my hips and leaned down as I rose to meet his mouth and we kissed again. Our tongues dancing and darting from one anothers mouth. All of a sudden I felt him squeeze my hips and slam the rest of his cock deep inside me. I tried to scream or yell out but he kept kissing me. I relaxed after a few moments and the pain subsided.
"You like that big dick inside you don't you, you fucking slut" he said to me as I felt him start pumping his cock in and out of me.
"Yes I love you cock inside me" I said to him as I wrapped my legs around him.
He pulled my legs from around him and pushed them back and put them on his shoulders. He started driving his dick hard and deep inside me. I could feel his swollen balls slapping my ass with each thrust, god it felt good having him buried inside me. He fucked me like this close to 10-15 minutes before he got off and told me to stand beside the bed and bend over. I stood up and leaned over the bed. I could feel him pushing his cock back in my ass.
"Reach around and spread your ass you dirty bitch" he told me.
I leaned down so my chest was on the bed and spread both my cheeks. I felt the tip of his hard dick touching my hot hole. I felt his hands on my hips again and I knew what was coming next. In one fluid motion he drove his cock all the way inside me. All I could do was groan and moan, oh GOD! He never gave me a chance to relax, he immediately started pounding away. He had a hold of my hips pulling me back to meet his hard thrust. With every thrust his pelvic area would slap my ass he was driving so hard and deep.
"Come on bitch, talk to me while I fuck you, tell me how much you want it, how much you like it, talk dirty to me" he spewed.
"Come baby, fuck me, fuck me hard, I want your big dick ramming my hot ass" I told him.
This must have got him really hot because he started slapping my ass hard and fucking me like a wild animal. He was fucking me so hard I fell over on the bed and he fell on top of me and kept driving hard and fast.
"Come on bitch talk dirty, I'm gonna cum soon and I want it to be good" he said to me breathing heavily.
"Come on mother fucker, fuck me you son a of a bitch, fuck me with that hard dick" I spewed back at him.
All of a sudden he pulled out and rolled me over on my back, pinned my legs up by my shoulder and drove his hard dick all the way to the hilt inside me. I could feel his balls on my ass as he started pumpimg me furiously.
"Come on keep talking, I'm almost there" he said to me.
"Come on baby, fuck me, fuck me hard deep, I want you hot cum deep inside my slutty ass!" I said back to him.
"Oh yea, here it comes" he yelled.
He leaned over and kissed me hard and deep as he kept plowing my ass. I felt him grab my hips and pump 3-4 times real hard and then stop. He moaned loudly as I felt the first shot of his hot seed filling my battered ass. He kept kissing me as he pumped 5-6 more times until he was spent. He fell on top of me and I let my legs fall to my sides and I felt his softening cock slide from my ass. He pushed himself up and looked down on me.
"We need to get cleaned up, I have to go somewhere, go wash that shit off your face and bring me those clothes, i'll keep them for next time" he said as he walked out the bedroom door.
I got up and took the bra, shoes, and stockings off. I gathered up the other stuff and laid it on his bed. I went and washed all the make up from my face, got dressed. He walked me to the door.
"You be here around 10:00 tomorrow morning or I'm coming looking for you, understand" he said
"Yea, I'll be here" I said as I walked out and went home.
