tagTranssexuals & CrossdressersCD Second Time with a Man

CD Second Time with a Man


It had been about two months since I gave it up the first time and had my ass virginity taken by a rather handsome man. I had been thinking about how unbelievable it was having a man's cock work my pussy over.

I signed into my email one night and found an email message from the guy. Thinking he wanted some more of my body, I was quite surprised to see what he wrote. He told me that he has a friend who had never been with a cross dresser and wanted to know if I would consider him. I was told that he is a decent guy and that he plays safe.

I thought about it and replied back and got the guys email. I asked what he was looking for and he told me that he wanted to fuck a school girl who will let him fuck them hard. That made me nervous as I don't like it rough but I asked for a photograph anyways. He sent a photo and he didn't have a lot of body hair. I asked for a photo of his cock and he told me that he has to save something for when we meet. I emailed back asking if he would rent the room and he told me that it would be at his house or nothing.

A little mad at the ultimatum I didn't answer for a few days. My sexual desire to be taken by a man burned deep pushing me to send a message telling him that it would be fine but I needed about fifteen minutes to get dressed when I would get there. He told me if I wanted to be like a woman than I need to arrive like one. I waited another day before telling him that would be fine and I set up the date and time.

I so full of anticipation waiting for the day to arrive wondering what this would be like. I imagined it so many different ways as I jacked myself to orgasm almost every night. I laid awake the night before realizing that in twenty-four hours I would be riding his cock.

I took my time shaving my body to ensure I would be shaved for my man tonight. I have gotten a lot better in putting on my makeup. I put on my satin white panties and white bra. I placed some water balloons inside my bra to give me the bounce that boobs would and it filled the bra nicely. I slide on my black and white plaid skirt and buttoned up my white dress shirt. I used white and pink ribbons to tie my hair up in pigtails. I next put on my white lacy socks and put my saddle shoes on. I checked myself in the mirror to make sure everything was alright when my phone rang.

"Hello?" I said.

"Where are you honey?" he said.

"I'm running behind, sorry." I replied.

"I'm gonna fuck that behind, hurry up. The longer you take the harder I am going to fuck you." He told me.

I headed for the door and I was nervous as hell as I haven't been out in public dressed as a woman much less a school girl. I couldn't wait to get there as I didn't want to be discovered.

I arrived at the house and I walked toward the door doing my best to act like a woman. After knocking he opened the door completely naked and he invited me in. I looked down to see what would be working my pussy and I about fainted, his dick was huge. It had to be eight or nine inches long and about five or six inches around. "Oh, my God, you could hurt someone with that." I told him.

He asked me if I kiss and I told him that I didn't. I asked him if he had ever had sex with a man and he told me that he hasn't. His girlfriend has turned him down numerous times for anal sex so this would be a great way to get to have anal sex. After seeing how big he was it was no wonder why his girlfriend didn't want him in her tight ass.

He grasped my hand and walked me back to his bedroom which was on the second floor.

"Do you have a name?" I asked him.

"Just call me mister." He replied.

"What name do you use?" he asked.

"Call me Stephanie. The more you use it, the more turned on I get, the more I'll let you do." I said with a smile.

We arrived at his room and I sat down on his bed which wasn't made and smelled like he had sex with his girlfriend earlier. I placed a box of condoms down on the night stand along with the lube as he moved over to me and asked me to give him a blow job as he held his half erect cock in front of my face. I have only sucked one cock and it had a flavored condom on it making it easy to suck. I reached for the condoms and he told me no.

I took a deep breath and I ran my tongue down his shaft to his balls tasting how he was salty. I licked around the ridge of the head of his penis tasting what seemed to be dried cum and pussy. I looked up and asked him if he had sex today and he told me about an hour ago with his girlfriend.

I opened wide as he shoved his mammoth dick deep into my mouth making me taste his girlfriends pussy juices mixed with his semen that still coated his dick. He moaned out loud as he ran his hands around the back of my neck pushing his dick in my mouth so deep that it made me gag. I put my hands up to stop his thrusting hips telling him to be gentle.

He said "Shut up and just suck it you bitch." As he pushed it back into my mouth deep bouncing the head of his mammoth dick off the back of my throat. I put my hands up keeping him from pushing so deep and hard.

He slid out of my mouth which caused me to drool down my chin from taking him so deep. He pushed me back onto the bed as I put my saddle shoes onto the edge of the bed. He went down between my legs running his moist wet tongue down my thighs to the edge of my panties. Sliding my panties aside I felt his hot warm tongue start to lick my pussy. Despite my best efforts of trying to be quiet I let out a moan. I have never had anyone lick me down there and I never realized how wonderful it felt. It made me feel like a woman getting her real pussy eaten out. I could feel his tongue darting in and out of my hole lubing it up to help his member fit in.

He stood up asking "Stephanie, where did you put the condoms and lube?" as he pressed his bare cock against my hole.

I told him that they were on the night stand as I reached over to get them. As I went to do this I felt the head of his huge cock start to penetrate me without a condom on.

"Stop mister, please stop, you're not lubed and I need you to be a condom on. It's hurting." As I felt the head make its way past the first layer of my pussy muscles as I tried to move my hips away from him. He pulled out and pushed a little harder making me let out a little scream from the sure size of his dry cock in my pussy. He pulled back out so I could put the condom on him and I lubricated him really well.

He then lubed his fingers and began finger fucking my pussy using two fingers. He was pushing them in and out of me like a virgin fucking his first pussy. He then stuck his other two fingers in from his other hand and he pulled my pussy apart. He did this in every direction to loosen my tight muscles.

He slowly looked up at me saying "Stephanie, I'm going to treat you like a woman, which means I fuck you the way I want and how long I want."

"Yes mister, my body was meant to please you."

I grunted loudly as he shoved his huge cock in with one deep push. I tried to sit up from the pain but he held me down by pressing my shoulders into the bed.

"Oh, my God Mister!!!" I squealed as he pulled out and slide back deep inside of me. "Not so fucking hard!" I yelled.

He only smiled as he continued to slide it in and out of my now torn apart pussy. All I could do was to pull my thighs up into my chest opening myself up wider as his body worked his cock deep inside of me.

"Stephanie your pussy feels good, do you like it?"

All I good do was mutter "Um-Hum."

I was thinking was what did I get myself into as he continued to press himself into me at a good rhythm with his thick member. He was doing me so hard that I was bouncing me off his dirty sheets. I was now getting used to his size so I laid my head back onto the bed now starting to enjoy the depth at which he was pushing into me feeling how primitive this was.

Suddenly he shoved every inch into me hard causing a deep pain.

I yelled "oh, fuck that hurt."

He looked at me and said "kiss me."

"No!" I said. He pulled out driving it home harder than the last time making it hurt more saying "kiss me."

"Absolutely not!" I yelled as he kept driving it in as hard as he could and with each thrust demanded that I kiss him if I wanted to be like a real girl.

After the seventh time I yelled louder "Please stop that mister."

He buried it in deep and he didn't pull out this time demanding to be kissed or he would pull the condom off and come deep inside my belly.

"Okay, okay." I leaned up and kissed him deep on the mouth. His tongue quickly parted my lips exploring the inside of my mouth making my stomach jump like the first time I kissed a girl. He kissed me passionately with him still pressed deep inside of me as the sweat of our bodies began to mingle together.

Turning my head I said "I let you kiss me, please back out of me mister." He smiled and slid out and told me to get on my hands and knees.

I rolled over onto my stomach and he said "Not on your stomach you dumb bitch, hands and knees you stupid cunt."

I got up on my hands and knees as he pulled my panties off sticking them in my mouth as he pushed my skirt up over my hips. I glanced back to make sure he still had the condom on as he lubed his fat cock so that he could start having sex with my body again. I felt him spread my ass cheeks a part and his dick just slide in.

He then spanked my ass hard as he said "that's a good girl Stephanie, take it all!" I felt so naked with my cock half erect which began bouncing into my stomach with each of his thrusts into my pussy.

He began fucking me harder and harder causing me to grab a hold of the sheets while moaning loudly. He would edge himself and pull out of me to keep from cumming.

After doing this for what seemed like a half hour, my knees where getting weak causing me to collapse on the bed.

He then rolled me onto my side as he put himself back inside my poor little beat up pussy. He lifted my leg up in the air and then placed his other leg over mine and pulled my legs apart spreading me wider for him. I couldn't help but reach down as I closed my eyes and I began to stroke my now very hard cock. He then slapped my hand and told me that I'm not allowed to do that. He was relentless with how hard he was fucking me as I looked down watching him slide in and out of me. I then began to ache for him to blow his baby makers so I could feel his throbbing cock. I felt him beginning to get thicker and his cock started to jump around inside of me.

"Stephanie can I take my condom off and come inside of you?"

"No mister."

"Can I cum on your cock and stomach if I promise to not stick it inside of you?" he replied.

"Yes." I replied.

I felt his cock start the verge of spasming when he pulled out and he moaned "Oh, shit Stephanie I'm cumming!"

I felt his hot sticky semen spraying all over my penis and stomach. His cum started to run down my body and onto the sheets. He reached up and rubbed his thick gooey sticky cum into my cock and thighs.

I used every muscle I had so I could sit up on the bed so I could put my panties back on. Without saying another word I walked for the door. He followed me giggling and he stopped me short of the door pressing me against the wall as he kissed me hard on the mouth. "You would've made a good woman Stephanie."

All I could do was smile as he wouldn't let me go as he looked me deep in the eyes.

He then placed his hand under my thigh bringing it up to my chest keeping me off balance as he pressed me into the wall with his warm sweaty body. I then felt his warm sticky cock slide through the lube and his semen right toward my pussy. He managed to get it inside of me without a problem and he began fucking me again.

"Are you fucking kidding? Didn't you have enough?" I said through my moans of having a bare cock fucking my gaping ass. He slapped me and said "shut up you little slut and take it."

I couldn't help but realize that it felt so much better bare back than it did with a condom on. I kept moaning louder as he slid his other arm under my thigh so my feet were completely off the ground with my back to him.

I looked at the shoe laces on my saddle shoes bounce with each violent thrust of his hips into mine as he impaled me on his massive tree of a cock. He let out a deep moan as he just dropped me on his thick pole making me shriek loudly. I then felt his cock begin to spasm inside of my body. With each spasm I felt his warm man seed bounce off of my insides as I muttered "oh my god, your cumming inside of me." I then felt it start to leak out of me as he started thrusting his fat dick in and out of me until he became soft.

"Now I am done with you Stephanie." as he set me on the ground.

My legs were so weak I dropped to the floor. He told me to get out of his house and began pushing me out of the door while I was on my hands and knees. His last push made me fall down again just outside of his door. He spit in my face and then slammed the door shut.

I just slowly got onto my feet and walked to my car to drive home. I was spent after two hours of his cock pounding my now sore pussy. I ended up masturbating into my panties on the way home to relieve my own pressure letting my cum spray on me which just mixed in with his semen.

I found myself thinking that I can get used to being used by a man despite how he treated me.

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