The first time I was exposed to feminization and with it sex with another person was around the time I was 14.
I had lost my role-model and close friend a couple of years before that and was from a rather broken home that never really communicated.
I stayed to myself and in addition my father really didn't pay much attention to me either. A few months before summer vacation started an old family friend stopped by and started taking me out to hang out every Saturday. I enjoyed my time with him as I finally had someone paying attention to me.
After a few weekends like that he asked if I could stay the night since it was getting later and later each time. I saw no problem so I agreed with him. A couple of weeks later it was raining pretty hard and cold and by the time we got to his apartment I was soaked to the bone. He offered that I take a hot shower so I wouldn't catch a cold.
Thinking nothing of it I agreed and readily went to the bathroom to get into the shower. As I finished and stepped out, drying myself off I noticed that my clothes were not hanging up as I had them before getting in the shower. I stepped out looking down the hallway towards the living room and saw him sitting on the couch staring at the TV intently.
I called out to him asking where my clothes were and without even looking in my direction he explained that they were in the dryer and wouldn't be done for a while but that he had set out some clothes on the bed in his room. I quickly made my way across the hall to the bedroom and stopped short with what I saw.
On the bed was definately a set of clothes but rather they were girls clothes.right down to the undergarments. Confused I shouted out to him asking if this was a joke and he replied that it wasn't but those were the only clothes he had that would fit me.
After a couple of minutes of standing in nothing but a towel I decided to say to hell with it and amuse him. I quickly dropped my towel thinking to myself how much of a laugh we would have once this was all done and over. I put on the bra and panties first, followed by the stockings and blouse/skirt. Looking around I saw a pair of platform heels set out and laughing decided to put them on too.
Standing up I noticed that the bra and blouse of the dress rather sagged in the front and yelled that the outfit didn't fit and without so much as hesitation he yelled for me to check the top drawer of the nightstand. Not knowing what I would find, I slowly opened the drawer and sitting right there was a set of C cup fake tits and a blond wig.
Having already done so much I figured it wouldn't hurt and put the fake tits into the bra which slid in almost perfectly. Then I took out the wig and deciding that I might as well complete the ensamble and fitted it on top of my head. Taking a chance to look at the full length mirror I noticed how much I did in fact fit in that outfit and if I didn't know better I would have said that the girl looking back at me was someone else.
As I exited the bedroom into the hallway I could feel my cheeks blush as I heard a shrill whistle. I smiled at him and made my way down the hall to the living room I turned my head and saw that whatever was on the TV was paused.
I made my way to the couch and as I sat down I felt his hand grab my hip pulling me almost on top of him.
I gasped and looked at him but his stare was fixated on the TV as he resumed the program and turned up the volume. I turned and looked and noticed that it was a man and a woman talking seductively right before they both started groping and feeling each other. Something odd clicked in my head and it dawned on me that I was wearing the exact same outfit as the woman on the TV.
Suddenly the woman dropped to her knees and pulled out the mans rock hard cock, licking, stroking and finally engulfing it, slurping as her head bobbed up and down. It was then that I noticed that my hand had somehow landed over his crotch and I suddenly felt his manhood jump and begin to harden.
He then suggested that since I did in fact look like a girl, and more specifically the girl in the movie, that maybe I should act out the scene.
My mind was racing with all the things going on so swiftly and before I knew what was going on his hard cock was out of his pants and in my hand, which was slowly stroking it up and down as if it was natural. I looked between his cock and the TV screen and without so much as a second thought I figured what the hell and slowly descended my mouth to his cock. Parting my lips slowly, I gently lowered my head allowing his hard cock to enter.
There was a slight salty taste but I ignored it as I started to bob my head up and down like the woman on the TV. Slowly I bobbed my head up and down, feeling more and more of his hard cock filling my mouth.
I felt his hands, one on the back of my head and the other all over my body until finally pulling up my skirt and sliding it into my panties. I gasped as I felt his finger start to circle my hole and suddenly slid in.
I relaxed as he told me to and felt his finger going deeper and deeper.then two fingers. I moaned and could feel his cock pushing down my throat his vein pulsing against my tongue. Before I knew what was going on I felt his fingers pull out and felt his hands pull my head up off his cock. Looking at him he motioned to the TV. Somehow I had ended up on the floor on my knees in front of him and as I turned to look at the screen I saw the woman on hands and knees, the man pounding his cock into her from behind.
I instantly knew what he wanted and in my hazy state readily complied.
I turned around facing the TV crawling a little forward on my hands and knees. I felt his hands on my hips pushing the skirt up over my ass.
I felt my panties being pulled down from the back exposing my virgin ass.
I jumped slightly as I felt the head of his still hard cock press against my virgin hole. His soothing words relaxed me and I felt him pushing forward opening my hole for the first time. I did what he said without question or hesitation and before long I could feel his hips pushing against mine, his rock hard cock buried in my ass.
He started pumping.slow at first and then faster and harder. I couldn't contain myself, my mind reeling from the progressing events.
I started to moan, softly and the harder he thrust the louder I got. I was lost in the moment and lost in lust. I even started pushing back against him the feeling was overwhelming. Slightly coming to my senses I looked up at the TV to see if anything had changed and I noticed something was different. Then it hit me, the woman on the TV WAS different as was the man. The man on the TV was the same one that was inside me and the woman on the screen moved the same way I did.
The woman's face was twisted with ectasy and she and I smiled. Then I felt him tense, thrusting his cock in hard as far as it would go, his hot cum filling me up and at the same time I felt myself twitch and let loose my own cum into the soft satin panties still covering it. He sat there for a few more moments, making sure that every last drop he could pump was inside me.
As he pulled out slowly I squeezed, trying to suck out every drop from his softening cock. He got up and moved back to the couch, pulling my panties up over my used ass, and sat back on the couch.
He motioned for me to come nearer and as I scooted on my knees closer to him I could feel his thick cum running into my panties, mixing with m own. I got to him, sitting there on my knees smiling up at him, my head still swooning.
I felt his hand running along the side of my face and felt myself nuzzling against it. Suddenly I felt his hand on the back of my head, forcing it down. I opened my mouth to gasp but instead I gagged as he shoved his cock into my mouth.
I struggled slightly, gagging because his cock had hit the back of my throat so quickly but also because of the strange pungent taste that invaded my tongue.
I realized, as I started to relax my throat and suck his cock clean, that the taste in my mouth was in fact.me. That thought sent me for another loop and I proceeded to suck his cock hard and long enough for him to become hard again and he was barely able to get it from my mouth before spraying my face with his hot sticky cum.
We had sex a couple of more times that night and every weekend after that was more and more exciting.especially when summer vacation came. But that is another story.