My First Time in a Dress
How I Became a Crossdresser
When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age.
Dan and I used to go mess around everyday. His parents worked from early in the morning to around six to seven in the evening. One day we were out messing around way out in a pasture and came across a pond that had a small dock on it. It was hot so we decided to take a swim. Dan started to get undressed down to his underwear and I followed suit. We jumped in and swam around a while before we got out. When we got out our tighty-whitees were see through. I was looking at Dan's cock and realised how large it was. I looked up and he was looking at me and pulled his cock out and shook it and laughed, I did the same. We started laughing as we shook our cocks at each other. His started to get hard and I commented on how big it was. He said "yea it's a big ole dick huh?" I said "hell yea and you got hair too!"
Dan started to stroke his cock and he looked at me and said, "you want to touch it?" "No", I said. "Come on, feel how soft the hair is". I reached over and felt the soft hair then he slapped his cock against my hand making me jump a bit. His cock was completely hard probably 6" or a little bigger. He looked at me and said, "go ahead, touch it". I reached over and touched the head, it was soft but yet firm. I slowly wrapped my hand around it and stroked it a couple times when he reached over and grabbed my cock and started to stroke it as well.
Dan looked at me and said "I'll suck yours if you suck mine". I wasn't sure what to say or do about this. Dan leaned close to me and licked the head of my small cock and sucked in and out of his mouth a couple times.
"Feels good doesn't it?" he said.
"Yea it does" I told him.
"You go ahead and suck mine for a while then I'll suck yours" he told me.
"Ok", so I leaned over as he laid back and pulled his underwear off. I slowly started licking the head and sucking his cock. It really felt strange to be doing this, but also sort of exciting. I sucked his cock for probably 10 minutes or so when I felt his body start to wiggle and his breathing was short.
"Do you want me to stop?" I asked him.
"Oh no keep going, it feels really good" he said to me.
"Ok, just tell me when your going to cum" I told him.
"Ok, I will" he said to me.
I slid his hard cock back inn my mouth and started sucking him again. This time he kept pushing my head down until I would gag bit. I would come up, take a few big breaths and slide his cock back in my mouth. I started sucking faster and stroking his cock taking as much as I could in my mouth without gagging. All of a sudden Dan grabbed the back of my head and held it down as his hips bucked up. I felt the hot shot of his cum hitting the back of my throat and then flooding my mouth. I started to gag but he held my head down until I started to swallow what I could. He finally let go of my head and I pulled back with long strand of cum trailing from my mouth to his cock.
I looked at him and said "you were supposed to tell me before you came."
"I know, but it felt so good I didn't want you to stop" Dan said to me.
Dan got up and started getting dressed. I looked up at him and said "what about me? You told me if I sucked yours you would suck mine."
He looked down at me and said "I will tomorrow, but we have to go now, hurry up and get dressed so we can go."
The next day around ten in the morning I went down to Dan's house to see what was going on. When I got there he was sitting on the sofa watching a porno flick rubbing his cock. We sat there and watched it for a few minutes and then he asked me if I wanted a beer. I gladly accepted and before I knew it we had drank 2 beers each down.
We sat there watching the porno stroking our cocks when Dan reached over and grabbed my hand and put it on his cock. I slowly started jacking it up and down feeling the firmness of his meat in my hand.
I looked over at him and he smiled at me and said, "come on, suck it, you know you want to".
"No, you lied to me yesterday and never sucked mine" I told him.
"I promise I'll suck yours today but lets have another beer first then I have an idea" he said to me.
We got another beer and we sat on the sofa and drank it. I was slowly stroking his cock and he would stroke mine a few times them stop just to keep me interested. I leaned over and slid his cock in my mouth and started sucking his wonderful meat for about 5 minutes when he stopped me. We finished our beers and when I got up to go use the bathroom I almost fell from the buzz I had.
When I came out Dan was standing inside his parents room which was usually locked. I went in with him and he started showing me all sorts of stuff. Sexy looking bras, panties, teddies, thigh high stockings, dildos and all sorts of other sexy stuff. Apparently his parents were a little on the wild side when it came to sex. I couldn't believe my eyes, I had never seen such stuff except in porn mags.
He threw a pair of red satin panties at me, a red bra, pair of sheer black pantyhose and a black satin nighty that was very short.
I looked at him and ask "what the fuck do you want me to do with these?"
He looked at me with a wicked grin and said "your gonna fucking put it on and suck my cock some more".
"You lost your damn mind if you think I'm wearing that shit" I spouted back.
He started to laugh and said "You'll wear it and do what I tell you or I'll tell everyone on this street your a cockscuking faggot".
I couldn't believe my ears, he was going to black mail me into dressing in girls clothes and sucking his cock. All I could do was stare at the ground.
He looked at me and said "that's what I thought, now go get dressed in Pam's room and come out when your done, I'll be waiting."
I walked into Pam's room and shut the door and sat on the bed looking at the clothes he wanted me too wear. I couldn't believe what was happening. I mean I had snuck into my mom and dads room when I was real young and put on pantyhose like my mom had done and just a year or so ago I took a pair of hose and jacked off in them. The feeling of the nylons on my bare cock was electrifying!
I got undressed and rolled up one leg of the hose and slid my foot in. As I pulled it up to my knee the feeling of the nylons gave me goose bumps. I slid my other foot in the hose and pulled them all the way up. When the nylons touched my cock the feeling was so sensual. I ran my hand up my legs getting the hose tight against my legs and snug on my ass and cock. I picked up the string bikini panties and stepped into them sliding the up and on. I put the bra on how I had seen my mom do it by putting it on backwards then spinning it around then sliding my arms through the straps. It was of course to big since I had no tits so I rummaged around and found some socks to stuff in the cups. I slid the nighty over my head and adjusted it so the bra fit into place under where my tits should be.
I looked into the mirror and couldn't believe my eyes, here I was standing there dressed in womans clothes. I was so nervous I must have lost track of time because I heard Dan say "what's taking you?", "nothing, I'll be right out" I said back. I looked in the mirror and did a spin making the nighty flare out, damn that was sexy I thought to myself. I opened the door and walked out.
When I walked out I didn't see Dan anywhere, I called out , "Dan, where are you?"
"I'm in here in the kitchen" he said.
I walked to the kitchen and he was standing there with a couple of shot glasses filled with booze and smoking a cigarette.
"Damn!, you look pretty good dressed like a girl, here take this shot of whiskey, it will make you relax." he said
"I've never had whiskey before." I said to him.
"Try it you'll like it" he said to me.
"Ok, I'll try one but I already have a buzz and I don't want to get sick or anything" I told him.
He handed me the glass and took his in his hand and raised it like a toast.
"Here's to you, and your sweet mouth" he said with a grin.
We touched glasses and I drank the shot down. It burned as it went down and he handed me a glass of water to chase it with. I drank a few good gulps of water to soothe my throat.
"Wow that burned a little but it was ok" I said to Dan.
He grabbed another beer from the fridge, I told him I didn't want one.
"That's fine we'll share this one while we smoke a cigarette" he told me.
"I've never smoked before" I said to Dan.
He looked at me, smiled and said "today is going to be a day of firsts for you, let's go to the den and watch some porn and you can suck my cock some more."
I turned to walk out and stumbled a bit. I was buzzing real good from the beer and whiskey shot. As I walked away he slapped my ass and gave a cat call whistle.
We sat down on the sofa and he handed me a cigarette. I put it in my mouth and he lit it for me. I inhaled and started coughing. He started laughing at me and said "it will get better don't inhale so deep." By the time I finished the cigarette and the beer was gone my head was spinning, I was really buzzed. Dan was sitting right next to me and he reached over and pulled my legs across his and started running his hands up and down my legs.
It felt so good with the nylons on my legs it was giving me goose bumps. He was slowly running his hands up higher until they went under my skirt and he was caressing my ass too. He pushed my legs off him and laid back on the couch and started shaking his cock at me.
"Here you go, come suck this dick my little girly" he said to me
I leaned forward on my knees and got between his legs and started licking his cock. I licked from the base to the tip and all around his balls and sack. I slowly sucked his cock in my mouth while cupping his balls like the women did in the porno. I sucked his cock for 10 minutes or so while he was caressing my head and pushing my mouth down on his cock until I would gag. I don't know if it was the alcohol or what but I was really enjoying his cock being in my mouth.
He leaned up and told me to lay down on my back. I did as I was told and he put one leg across my chest and aimed his cock at my mouth. I greedily took him in and he started to rock back and forth slowly fucking his cock in and out of my mouth. He fucked my mouth for around 5 minutes and he pulled out. He slid down on top of me and spread my legs so our cocks were touching. He started to slowly dry hump up and down on me.
He pulled my legs up and around him so he was completely between my legs. He started kissing my neck and shoulders and squeezing at the bra like they were real tits. This was a little strange to me but I was getting very turned on. He reached his hands down under my ass and was pulling me hard into his thrust.
He whispered in my ear "I want you so bad."
He slowly slid his hands under my skirt and grabbed my panties and pulled them off. He pulled me down on the floor beside the sofa and was laying half on my with one leg between mine and was rubbing my cock through the pantyhose as I stroked his cock. He reached down and started rubbing my ass and trying to finger my hole. I was enjoying his touch and I slowly spread my legs to give him better access. He got back on top of me and spread my legs wide while he kneeled between my legs. He started rubbing his cock head on my ass and trying to push it through the pantyhose.
He finally got discouraged and leaned back off of me and ripped a hole in the crotch of the pantyhose. He laid back down and I could feel his cock head between the cheeks of my ass, rubbing and trying to push it's way in.
I didn't know what to do so I told him "please stop, I don't think we should do this."
"Shhhhh, it will be ok, just relax he whispered in my ear.
"No, I've never even had sex with a girl much less a guy screwing me, it's gonna hurt" I said back to him.
"I'll be very gentle it will be ok, you'll like it, it will feel good" he said back.
"No, I really don't want to, we should stop, I'll suck your dick, but I don't want you to fuck me" I said back to him.
"Look, your going to do what I say or I'll tell everyone, remember that" he spat back at me.
"Ok, maybe just a little, but you have to be careful and go slow, ok?" I said back.
"He smiled at me "hang on, I'll get something that will make it go in easier."
He got up and went to his parent room and came back with a bottle of clear liquid. He squirted a big glob in his hand and rubbed it all over his cock then told me to get on all fours in the doggy position. He squirted some on my asshole and rubbed it around slowly pushing a finger inside me.
"Ow, that hurts" I told him.
"Just relax, this will help you loosen up" he said to me.
He slowly started to pump his finger in and out of me, he was right it didn't hurt anymore. I felt him slide another finger in me, it hurt a little at first but went right in. He was slowly fucking his fingers in and out of me. It was starting to feel pretty good and I started to push back to meet his thrust. I felt his fingers slide from my ass as he pulled them out.
"Are you ready for me to fuck you?" he asked.
"I guess I am" I said back.
He got behind me and I could feel the head of his cock pushing at my hole. I could tell it was going to hurt a bit. He pushed a little harder and I could feel the head slowly pushing it's way inside my virgin hole. He pushed a little hard and I felt the head slide in and a sharp pain followed.
"Ow, stop, that hurts, please stop!" I said to him
"Just relax, it will get better in a second, tell me when it quits hurting ok" he said to me
"Ok, but don't push anymore until I tell you" I said.
He held still for a little bit and the pain went away as I relaxed, "ok, I'm ready". I felt him put his hands on my hips and slowly start to push his hard cock inside me. He would go in a little then back out. A little farther the next time, then out. He gently pushed his cock in and out of me until I could feel him slowly start fucking me. It hurt a little but yet it felt so good.
" How much do you have inside me?" I asked Dan
"Almost all of it, maybe an inch or so left, you want to go all the way?" he asked
"Yes, it kind of feels good go ahead and put the rest of your cock in me" I told him.
He slowly pushed his cock the rest of the way inside me until I felt his stomach on my ass. The feeling was strangely erotic. (I couldn't believe I was dressed like a girl and getting fucked by a guy.) He slowly started pumping his cock in and out of me, fucking my ass. With each thrust he seemed to be pumping harder and faster until he was literally, fucking me like crazy. He pulled back once too far and his cock slipped out, I felt so empty. He rolled me on my back and got between my legs and told me to hold them back. He aimed his cock at my ass and pushed it back inside me. It hurt at first but the pain went away quickly.
He was kneeling between my legs while I held them back pumping his cock in and out of me. I was really starting to like the feeling of his cock being inside me, fucking me, like a girl. He laid down on top of me and put his elbows above my shoulders and started driving his cock hard and deep inside me.
"Oh God stop, your doing it too hard" I said him.
"Shut up slut, I'm almost done" he spat back at me
I wrapped my legs around his back and my arms around his body trying to slow his animalistic fucking. It didn't help, he just kept pumping harder and faster into me.
"Don't shoot your cum in me ok, please" I told him.
"Shut your fucking mouth cunt, don't fuck it up for me" he spouted back.
I was hanging on as tight as I could while he was jack hammering his cock in and out of my virgin ass. I felt him slam his cock into me as hard as he could 2-3 times and he let out a loud groan as he drove it as far as he could inside me. I felt his first shot of hot cum squirt inside me and then the feeling of the rest of his load filling me up. He pumped his cock inside me 4-5 more times real hard and then collapsed on top of me. He was breathing so heavy as we laid there, my legs still wrapped around him holding him tight inside me.
I felt his spent cock soften and slide out of me. I felt his warm cum ooze from my fresh fucked virgin ass and down my cheeks. He raised up between my legs and smiled down at me.
"We're going to have some real fun this summer, now get that off and get cleaned up, my folks will be home soon" he said to me.
I got up and went to the bathroom and cleaned up and got dressed. He grabbed the bra, panties and nighty from me and threw them back in his parents room and told me to get rid of those torn up pantyhose and he would call or come over tomorrow when he was ready. I left his house and walked down the street to my grandmas house.
She was cooking dinner and ask what Dan and I did today, I looked ate her and just said "Oh we screwed around a bit."