tagTranssexuals & CrossdressersMy First Time Dressing Ch. 02

My First Time Dressing Ch. 02

byChrissyCD©

This is a continuation from my first story where I bought and completely dressed in women's clothes and started my transformation into a crossdressing slut.

Chrissy's First Real Cock

After my first night dressed up like a girl I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the sexy feeling of the panties on my cock and the nylons on my legs.

By now I had purchased quite a few women's clothes. I had all different colors of matching bras and thongs, I loved the way the thongs felt between my ass cheeks. I had 4 or 5 dresses, mini dresses of course. I bought 3 different mini skirts, 1 denim that was in style then, a black mini, and a red spandex mini with a nice slit up the side. I had 7 or 8 different tops from satin blouses, stretchy tanks, to slutty sheer see through tops.

I would dress almost everyday watching porn and jacking myself off to incredible orgasms. I had even bought a few short night gowns and baby dolls to sleep in. I bought some satin sheets and they felt like heaven when I would run them across my stocking clad legs. Besides they made me feel sexy and feminine when I laid on them while dressed.

I would make regular trips to Houston browsing my favorite lingerie store & boutique and got to be pretty good friends with the lady that worked there. She had soon figured out who the stuff I was buying was for and became very helpful in getting me the correct sizes and right fit.

After the first semester of college was over my roommate decided not to return so I moved into a one bedroom alone. It was fantastic because I could dress whenever I wanted to now. I became fairly good at applying my make-up and doing my hair. I had let it keep growing to about 6 inches past my shoulders. My parents hated it, they told me I looked like a damn hippy. If they knew what I was doing I think my mom would have accepted it. My dad on the other hand, the ex Marine and Vietnam vet would have disowned me.

I still only dressed in the privacy of my own place. I hadn't gotten the courage to venture out yet.

On one occasion I decided to go to Houston for the weekend and check out one of the adult video stores to buy some new porn. I of course had on my panties and thigh highs under my pants and a nice little satin tank under my sweat shirt.

I got there around 9:00pm and was browsing around the store when I noticed that guys kept going in the back through a door. I ask the clerk what was back there and he told me an arcade. I bought the required amount of tokens and journeyed through the door. It was very dark and lots of guys walking around and standing in doorways. I walked through and noticed that there were little rooms with a TV playing pornos.

I went into one of the rooms and locked the door. I pumped in a few dollars of tokens and the movie started playing. I sat down on the bench and started watching the flick. Of course I started getting hard and decided that since I was alone in a room I could do a little stroking. I pulled my pants down to my knees and took my shirt off.

I started stroking my cock through my panties when I thought I saw something on the wall about waist high. I stopped and focused on the wall, and I saw it. It was fingers poking through a large hole. I was totally shocked. Here I was wearing panties, thigh highs and a satin tank top with someone watching me. I went to the wall and bent down and the guy told me he liked my panties and stockings. I told him thanks. He then hit me with a question that sort of surprised me. He ask if I wanted my dick sucked. I said I guess, and he told me to put it through the hole. I put my cock through the hole and he sucked me into his mouth.

I had my fair share of cock suckings, but this guys mouth was amazing. He sucked me for about 3 or 4 minutes before he pulled away. I leaned down to see what happened and then his cock came through the hole. I stared at it for a few seconds then I slowly started licking the head and took it in my mouth. It was a nice cock about 7 inches or so, thick and cut. I sucked for about 4 or 5 minutes when he pulled his cock out of my mouth. He leaned down and our faces met at the hole. He ask me if I wanted to go to his place which was right around the corner. I said sure.

We met in the parking lot and introduced ourselves. His name was Todd. I was 19 and he was about 25 clean cut preppy type. I got in my car and followed him to his place. We went in and he offered me a drink, which I accepted and told him to make it strong. We made small talk and finished our drinks. I told him that was the first time I had ever touched another mans cock, let alone putting it in my mouth. He sort of laughed and ask if I liked it? I said yea I did. We went to his bedroom and started to undress. I got my pants and shirt off and started to remove my panties, stockings and little chemise top. He stopped me and told me to leave it on.

He stepped close to me and took me in his arms and started kissing my neck and running his fingers through my hair. I started following his lead, doing to him what he was doing to me. He looked into my eyes and then he kissed me. I wasn't sure what to do. My emotions were running wild as I had never touched another man like this. I started kissing him back and pulling him closer to me. Our cocks were rubbing while we made out making me so horny I could barely stand it.

He pushed me back on the bed and laid on top of me. I spread my legs open so he had one leg between mine as he caressed my leg running his fingers on my stockings. I laid there and let him take control. He ran his hand up my top and started pinching my nipples while we kissed. He slowly slid his body up so his cock was in my face. I took him in my mouth and was doing my best at sucking him off. I believe I was doing ok because he was moaning and rocking his hips fucking my mouth.

He pulled his cock from my mouth and came down and started kissing me again. He got between my legs and I spread them wide for him so out cocks were rubbing one another. He pulled my legs up and started dry humping me rubbing our cocks together hard. He was running his hands up and down my nylon covered legs. He started kissing me hard and humping me faster. I wrapped my legs around his waist and pulled him to me. I did this knowing how much I liked it when girls wrapped their legs around me when I was fucking them.

He reached down and pulled my panties to one side and started rubbing his cock on my ass. I had finger fucked myself plenty of times to know that I loved the feeling of something inside me. I had never imagined that one day I would have a real cock inside me.

I grabbed his ass and pulled him tight against me, and I whispered in his ear that I wanted him to fuck me.

He ask if I was sure, and I told him yes.

He got up and went a got a bottle of lube and had a small brown bottle of something else.

I ask him what was in the brown bottle?

He told me it was a popper and he took the top off and inhaled deeply in one nostril, and then again in the other and held his breath. He handed me the bottle and I did the same.

When I let my breath go I was so dizzy and light headed I thought I was going to faint. Then as the immediate rush passed I felt so relaxed and uninhibited.

He pulled my panties down and licked my cock a few times while he was down there and then told me to get on all fours on the bed. I got on the bed in the doggy style position and he rubbed lube all around my ass and pushed a finger inside me. I eased forward a bit as he pushed and he grabbed my hips and pulled me back and said to hit the popper again and relax.

I hit the popper again as he pushed a second finger inside me slowly pumping them in and out of my ass. It felt absolutely wonderful. I could feel my ass relaxing and giving less resistance to his fingers.

I felt him remove his fingers and grab my hips pulling me to him. He rubbed his cock up and down the crack of my ass spreading the lube all over his cock. He took one hand off my hip and I felt him pressing his cock against my hole. It was much bigger than his fingers and I could feel it start to push inside me. I leaned away because it started to hurt a bit but he pulled me back and said to hit the popper again.

I took 2 or 3 good sniffs in each nostril this time making my head spin, when I let my breath go I was so high I almost collapsed on the bed. I felt him push his cock against my ass harder. Then I felt the head pop right in. I let out a loud moan and he just told me to relax as he held still.

He held his cock there for about 15 to 20 seconds. I said I was ok and he started to push his cock in slowly. He would push in a bit and then slide it out to where just the head was in. He did this quite a few times until I could feel his pelvis against my ass. I couldn't believe he had his entire cock buried deep inside me.

He slowly started fucking in and out of my ass. I couldn't believe how great it felt to have his cock pumping in and out of me. He fucked me like this for about 10 minutes and he let his cock slip from my ass. I felt so empty when it came out.

We changed positions because his legs were getting tired. He got on the bed and laid on his back and told me to climb on him. I straddled his body and we both took a big hit off the popper. He held his cock up while I slowly lowered my ass down on to it. It felt amazing when it penetrated my ass, it just slipped right in this time. I slid all the way down on his hard cock while I had my hands on his chest and was slowly rocking back and forth.

I was enjoying having this hard cock buried inside me so much that I didn't even realize that he had a wall of mirrors beside the bed. When I noticed this I couldn't help but watch as I was having his cock slide in and out of me. He started talking dirty to me as I rode his cock, telling me what a slut I was and how he loved being the one to pop my cherry and fuck my tight virgin ass.

As I started fucking faster on his cock he told me he was going to cum soon. I got off his cock leaving me feeling empty again. He rolled me on my back and pushed my legs back against my chest. He pushed his cock in hard this time making me yelp at the pain. He handed me the popper again and we both took nice big hits of it. He started driving his cock in and out of me as deep as he could. I could feel his balls slapping my ass he was fucking me so hard.

I kept looking at the mirror next to the bed. My legs up in the air covered in black sheer stockings with a man between my legs fucking me. I couldn't believe it as I watched his ass rise and fall on top of me with each deep thrust. I finally got to wrap my legs around him to hold on. He was driving into me with such force that I could hear his balls slapping my ass. The bed was bouncing and I was moaning in total ecstasy.

He told me he was going to cum and all I could say was yes, cum for me, give me that load. He pumped me real hard 3 or 4 more times and pulled his cock out and shot his hot seed all over my chest, stomach, and my cock. As soon as he finished shooting his load on me he rammed his cock back in my ass. It hurt, but it was a good hurt as he buried it all the way in. He continued fucking me until I could feel his cock getting soft inside me. He held it there and started rubbing his cum all over my cock. He stroked me fast and hard until I couldn't take it anymore and shot my load all over myself.

He started rubbing our cum all over my stomach and licked his fingers and then he offered his fingers to me. I greedily sucked his fingers into my mouth and licked them clean. He scooped all he could up and brought his hand to my face and wiped it all over my mouth and chin. I was starting to lick it off when he leaned down and kissed me deeply. We kissed for what seemed like forever rubbing cum all over our faces.

We laid together for a while until he went to sleep. I went his bathroom and cleaned myself up and got dressed. I left my number on a pad by his phone and quietly left.

I drove all the way home in a sort of daze about what I had just done. I knew one thing though, this would not be my last time getting fucked.

Too be continued...

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