Early Discoveries

Amateur

I’ve always been confused about my sexuality. For as long as I could remember I found women sexy and irresistible, I know for most guys this was normal. For me it was normal as well, until I found a pair of my sisters panties mixed up in my washing and tried them on. To this day I can’t remember having a larger erection or being more turned out.

That started my fascination with cross dressing and transvestites but for the most part I controlled my desires and stayed at least semi normal. But after I graduated and moved out of home, gaining more freedom, my urges resurfaced with more intensity than ever before. Thank god the internet exists otherwise I wouldn’t have been able to buy half the crap I wanted, being too timid to actually go into stores and by them IRL.

Before I go on I should probably describe myself. My name is Matt, I’m about 5″12′ slim build and pretty lanky, I’m more leg than torso and unfortunately for my high school life I look extremely effeminate. I work as an IT consultant for a pretty big law firm, it might sound complicated but it wasn’t it was ridiculously easy. Most of the problems were simple fixes and anything more complicated I literally just Googled how to fix it.

But it was a well-paying job and it gave me loads of spare time to explore my sexual urges. You see I didn’t start work until 11 and I finished at 2 so my day was pretty short even though I was getting paid full time. Don’t ask me how I was able to score these hours but it basically boils down to an unfortunate choice of sweater and skinny jeans on my part and an inability for one of the major partners to check if I was a chick. Sexual harassment avoided and easy work day for me. In his defence I do wear my hair pretty long (down to my shoulders).

My cross dressing was my biggest source of confusion as you could probably understand. On one hand I loved chicks; I loved how they moved and their sexy bodies. I wanted to fuck them and when I went home I would dress up as a hottie I saw that day and jack off looking at myself. I got very good at makeup and hair styles, because of my body type I could make myself into a very convincing girl. The only issue I had with the entire process is as I looked in the mirror at my hot girl form I couldn’t decide whether or not I wanted to fuck this chick or be fucked.

I would watch porn, looking at the actresses wondering how I would do their hair and makeup so I could recreate it later. But then I would start to wonder what it would be like to be them and suck cock and get fucked. It majorly messed me up, I was sure I wasn’t gay and I definitely wanted to keep my dick but I still wanted to be hot. To be desired. To be lusted after. How naïve I was, I didn’t have the first idea what it would be like to be a woman.

This went on for months. Every day after work I would go home and immediately doll myself up. I had loads of cute outfits (hidden away of course), I had nightclubbing clothes, work clothes, exercise clothes. I had brunette, blonde, red head wigs and extensions. I had washable dye kits so I could temporarily dye my hair. My eyebrows were sculpted but my hair was long enough so I could hide it at work. I had several cup sizes in fake glue on tits. I had C’s, DD’s, B’s, but my favourites were just the straight D’s. They were big, but I always loved big tits, but they weren’t so huge that they sat weirdly.

They were the perfect size for all my outfits. At first just dressing up was enough to get me horny and cum. But it started to get more difficult. My body yearned for more but I just didn’t know what yet. I started posting pictures of myself in chick form in skanky clothes and my fake tits out. With makeup and some glue (to hide my junk) no one on these anonymous sites even knew. I would get comments of guys saying they were wanking to me and telling me how hot I was.

This was enough for a while and I made several different profiles because even then I was still scared someone would find out about me. I would look at myself in the mirror, so sexy and fuckable but I knew that I was too chicken to ever do anything. kocaeli escort It was always going to be my secret, and while that made me sad I was also slightly relieved.

I woke up one morning way too early. It was eight o’clock and while most people were getting ready and heading off to work, I usually didn’t get up till nine. I rolled out of bed and quickly went for a shower. Because I started work so late I usually went for a jog around nine thirty before coming home for a shower than going to work. Today instead I just went onto my laptop to watch some Youtube videos while lying in bed. I got bored of that pretty quickly so I decided to go have a wank at some of the comments to a picture I had just posted.

It was with a profile that I was getting ready to retire because I felt it had too many viewers but I was holding on a little longer because the perverts were getting really excited. I logged in and scrolled through the comments on my last post. It was a high shot of me looking up at the camera in two high pig tails with my tits out on my knees. Predictably it had a lot of graphic comments of what guys wanted to do with that hot body. I was stroking my cock reading the comments but before I could even get close to cumming I reached the bottom of the page.

I sighed pulling my pants back up my cock still screaming for release. I decided to go for a shower to try and calm myself down. I hopped into the shower and turned the shower a bit colder and soon my erection subsided. I finished showering and as I was drying off I realised even though my dick was soft I was still horny as. I glanced at the time and saw I still had over two hours until work and decided to dress myself up. I went into my closet pushing on the false door (I didn’t put the door in, I discovered it months after I’d been renting) and grabbed my box of clothes and wigs. I went to my bathroom standing in front of the mirror and got to work.

I wondered what these hot girls would be doing right now as I was applying my blush and very pale pink lipstick. Probably going for a run I guessed. I went into my box and grabbed tight black yoga pants and a green tank top. I took my shirt off and glued on my D cup breast forms, I used my makeup kit to blend them into my chest. By the time I was done they looked like real breasts. I played with them a little and being slightly masochistic the pain started to get me horny. I decided to go all out and I glued my junk down so I could put on the g string then yoga pants without my cock ruining the image.

I put on my sports bra, slid my green tight tank top over it making my tits look understated but still with a full cleavage. I made sure my cock was securely glued on (don’t worry I had anti-agents which would dissolve the glue) and slid my g-string over the top. I probably don’t have to say this but I shall add it in anyways my body is completely hairless, apart from my head. I slid the yoga pants on then touched up my makeup, clipped on my brunette hair then tying it into a high ponytail. I surveyed myself in the mirror, the timid shy boy was gone to be replaced by a drop dead gorgeous woman. I tilted my head looking at myself in the mirror checking myself out. My green eyes made emerald by my touches of makeup. I started to get slightly hard which was a problem, because of the glue my cock would cause me pain if I started to get hard. Meaning the only way I could cum would be to finger myself. Unfortunately like most erotic things in my life that wasn’t helping lately either.

I looked at the time and saw I still had an hour before I would even need to get ready for work. I decided, even though I’d already been for a shower, that I would go for a run on my favourite route. I had to keep my body looking hot as hell of course. I reached up to my hair to take the wig off then stopped myself. It was pretty late so most people would be at work. Plus I’d only ever seen two people on my morning run in the ten months I had been living in this place. I could just go out dressed as I was.

It would be kocaeli escort bayan exciting and would probably give me something to jerk over. I looked at my girl again and thought for a moment.

“Tara.” I said in my girly voice I had been practicing.

“Hey I’m Tara pleased to meet you!” I did a twirl watching my pig tail swing back and forth. I grinned at myself. I would be Tara today.

I left my hours nervously and quickly got into my car, I drove five minutes down the road to the edge of a forest that had an awesome running path up to a bench and an amazing view of my city. I got out of my car, stretched for a bit and started jogging. I breathed deeply filing my lungs and smiling as I started jogging up the hill. I didn’t realise the man was following me until I’d gotten three quarters up the hill. My heart raced when I noticed him, panic gripped me. He was out exercising like me but I had never seen him before.

I continued my way up the hill trying to figure out a plan as to how I could get out of this situation. I was still naïve, this being my first time being a girl in public. I got to the top of the hill and decided to walk off the track to go over to the benches. As always apart from this mysterious man and me the place was deserted. I stretched slightly waiting for him to go past but instead he crouched down to tie his shoelace. I felt like my heart was going to explode from my chest.

“Beautiful day eh!” The man called out to me. I froze and turned slightly toward him.

“Um, yeah it is…” I nervously went back to stretching just wishing he would leave.

“I’m new to town but I’m glad I found this run, do you do it often?” He started walking closer to me. I turned to him, he was tanned and muscular. He had broad shoulders and was over 6″ tall. Taller than me easily.

“Uh, yeah it’s really nice,” I stammered, blushing slightly now. He walked toward me looking me up and down.

“You must exercise all the time with a body like that,” He smiled at me but his eyes were lustful and hungry. I stepped back into the bench looking around quickly, but we were still alone.

“Not really, I might see you around,” I turned to leave but he closed the gap between us in an instant.

“Where are you going, what’s your name?” He grabbed my waist tightly pulling me closer.

“It’s uh…Tara..” I was scared now, but also ashamed at how aroused I had become. I could smell him and feel his strength and I felt weak and helpless in his arms.

He smiled again “I’m Jack.”

“Well it was nice to meet you but I should be going” I moved to push him away but he pushed me back into the bench. He kissed me full on the mouth and I struggled surprised. I managed to push him away slightly; his tongue was rough and forceful.

“What are you doing!?!” I exclaimed. He just laughed and pushed more onto me, starting to cause me pain.

“What are you talking about? Dressed like you are, I’m doing exactly what you want me to do!” He grabbed one of my breasts and squeezed and pulled at it, the pain making me even more aroused and excited. I slapped him and tried to run away but I realised quickly that was a mistake. He backhanded me and I saw stars going limp in his arms. Jack quickly turned me around bending me over the bench feeling up my ass. For the first time I could feel his hard cock and realised it was much larger than mine.

“Stop! I’ll scream!” I struggled to get away but he was too strong.

“Scream all you want bitch no one will here you, besides once you have my cock in your ass you’re going to love it,” He ripped my yoga pants down tearing them apart. He laughed when he saw my g string and quickly pulled it aside sliding a finger inside my hole. I screamed but he pushed my face into the bench and my pleas for help were quickly muffled. Tears streamed down my face as he fingered me faster and faster.

“You ready slut?” I could barely comprehend his words before I felt the tip of his cock start to push against my pink hole. I truly panicked then, my virgin arse escort kocaeli was not ready for his massive cock.

“No, no, no , no , no, please I’ll suck you I’ll do anything just don’t fuck my ass,” I begged him stopping my screaming. He petted my hair softly and kissed my neck showing a gentleness I hadn’t seen from him so far. I began to relax.

“You’ll love getting fucked in the ass by the time I’m done with you Tara,” My eyes widened as he leaned back up grabbing my ponytail and started pushing his cock inside me. The pain was unbearable, I felt like he was tearing my ass apart. All I could do was close my eyes gripping the table my fingers going white. He eventually slid the entire way in, it felt like his cock was pushing my stomach up into my throat. He pulled out slightly and thrusted back into me. He repeated this over and over gaining more speed and slamming my ass harder and harder. It took me a while to realise what was happening. I was being fucked.

This man was fucking me, technically he was raping me but I was in such shock about the entire situation I hadn’t fully comprehended my circumstances. He continued to thrust inside me as I gripped the bench harder closing my eyes tight. I had long since lost the urge to scream and I no longer held any hope that someone would come to my aid. I had stopped crying but tears still coated my face making my makeup run. I started to lose all sense of time and for the life of me I couldn’t say how long he violated me. The worst part was a turning point when the pain subsided and my ass adjusted to the feel of his cock. I felt myself fighting back moans of pleasure my own cock growing close to climax as Jack got into a steady rhythm.

I was getting closer and closer to orgasming when suddenly without warning Jack pulled his cock out of my ass. I was in complete shock, my asshole felt empty and cold without his strong member inside me. His hands grabbed me upright and he spun me around lifting me back onto the bench, this time I was facing him. I held him weakly as he hoisted me onto the bench and kissed me again. He grabbed my throat lightly looking at me a viscous grin on his face.

“Yeah you whore you love my cock now don’t you,” I was silent not fighting any more, hoping it was over but deep inside hoping it wasn’t. He grabbed my legs and pulled me towards him, my yoga pants only pulled down past my ass so my dick was fortunately still hidden from him. I hated to think what he’d do to me if he knew he’d been fucking a guy. He pulled my top further down exposing my tits, he raised my legs and positioned his cock against my ass again.

“I wanna see those beautiful titties bounce as I fuck you Tara,” He pushed his cock into my ass again. The pain returned but nowhere near as intense as last time. It was like a burn and it was quickly replaced by feelings of pleasure and my own cock straining to cum. I was ashamed of myself as I moaned softly bucking my ass back into the cock of the man who was raping me. I hoped he wouldn’t notice I had become a willing participant of his sexual assault but I had.

“Fuck slut! Your ass is clenching my cock hard! Bitch you love my dick in you,” Jack laughed harshly grabbing my hips and slamming into me. I moaned uncontrollably now lost in ecstasy my cock cumming into my g-string. He moaned gripping me roughly pulling at my tits with one hand while also shoving his cock into me.

“Damn girl, I’m gonna give you what I know you want!” He thrusted faster and faster into me, moaning louder getting close to cumming. He moaned loudly before pulling out of me. I had been close to cumming for a second time so I looked up at him. He grabbed my hair holding his cock firmly in his other hand before pulling me off the bench onto my knees roughly. I looked up at him as he jacked him cock once and came onto my face and tits. I closed my mouth stopping any getting inside as his hot load covered my face.

“Haha shit Tara, you should walk around with my cum on your face all day!” He laughed again rubbing his dick on my face pushing his cum out. He pushed the tip of his cock into my mouth, but my lips stayed closed. He just laughed louder.

“Haha baby you don’t wanna clean me off? We’ll change that don’t worry. I’ll see you tomorrow,” Jack rubbed my lip before putting his cock away and jogging off. I stayed there on my knees covered in his cum, confused more now than ever before.

To be continued….

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