Hello all. Firstly this is a work of entire fiction none of this took place as described! Secondly this story involves the sexual activity of a sexually dominant teenage crossdressing boy and a submissive gentleman. They are both willing participants!
Please If this offends you then please read no further! I do not wish to offend anyone! I in no way encourage the activities I write about. This is merely a fantasy I had while I was a teenage boy! So if you haven't been put off by this warning please enjoy the story! And drop me a mail to tell me what you think of it. Thanks!
Shop!
Every day I had passed the shop, and longingly looked in the window! Once or twice I had plucked up the courage to venture in and touch the beautiful pretty things! This was to be one of these times.
I was still at school, and this shop was in a little shopping quad that I had to out of my way to get to. Quite a bit out of my way.
But here I was again, the door bell chimed as I pushed it open; I timed it so there was a woman going in at the same time as. My theory was that she looked like she was with me perhaps my mother.
I walked passed the lovely skirts and dresses. I touched one or two of them as I passed. There as something about the feeling of them that I craved if I saw something I liked I wasn't satisfied until I had thoroughly touched. Mesmerised by the feel. I went through the sexy lingerie section I adored the bras and garter belts, the knickers looked so conformable, not like Mrs Peterson our next door neighbour who panties I had raided off her washing line. They were big and bland, these were dainty and sexy!
I got to my favourite section, women's shoes! For a local shop in a small town I never realised how varied their ranges were. There where flats and courts for the older women. And slippers for the grannies. There where stilettos for the working ladies of the town. Then there where massive black or white or red fuck me boots for the 14 year old tranny! I lifted the black ones off the shelf and held them in my trembling hands. The cashier could probably hear my heart pounding, on the other side of the shop.
I held them up to my nose and took a massive breath I inhaled the beautiful leather smell. The leather was so soft. And the massive 4 inch spike heel was so hard.
I have been having wet dreams about these boots. They where the holy grail of a young sissy rugby player. In one hand I could count the number of times I had pleasured myself while not thinking about these beauties! And I would need the most powerful computer to calculate how many wanks had been because of these boots. The stuff dreams where made of.
I have no idea where this fascination has arrived from. Many times I have tried to place it, wondering if I wasn't given enough attention from my mother or father? I grew up in a normal house my mum and dad where a normal couple they had there moments, I have a twin sister. She is a normal 14 year old. I go to a normal school, where I neither bully nor am bullied. I'm quite popular with the entire school fraternity; I get a lot of attention from girls. I play rugby for my school and my county. I'm still growing about 5 ft 5. About 8 stone in weight and most importantly a size 5 shoe! I sometimes hate myself for my adoration for women's cloths. I find my self in tears post ejaculation in my sister's panties ashamed at what I'm doing! I to this day have no explanation for it.
I'm in the middle of a nearly wet daydream about these boots when I felt a hand on my shoulder.
"Are you ok there son?" the old shop keeper asked I was burning my face was so red I'm sure air traffic control had problems with landing planes! "err err ea." I stammered getting hotter and hotter. "It's ok Mr Daniel's, I'm sorting him out! Good night now sir" said a younger sales man.
"Right you be then, have a nice evening then Craig. Good night" I was stuck I didn't know what to do should I run, should I stay I was totally frozen. My face was burning up. I heard the door bell chime as Mr Daniel's left for home. "I will be with you in a second son!" Craig shouted over to me. I flashed my mind screamed "Get out of here quick" I turned and ran. I got to the door but I was locked. Panicking now I realised that I was still holding the boot. Would he think I was shoplifting? He calmly walked over to me and gently said "Don't panic love I want to be your friend" he took the boot out of my hand and reached passed me to pull the blinds on the door. "Come with me sweetie!" he swaggered off towards the shoe section again. I hesitantly followed him. We got there and he said "Now sweetie plop your wee arse down there and we can measure you tootsies." I sat down my head was whirring. What in the world was happening? He kneeled in front of me and took off my shoe and tutted when he saw my dirty sweaty white sport socks. This won't do he said pealing them off my feet, and causally tossing them toward a nearby bin. He placed a foot measuring board to my feet and said "Ah good a size 5, we can work with that!" my heart was beating double quick time. He got up and disappeared. I was too stunned to move. He came back several minutes latter my eyes could not focus on what he had brought with him. He said stand up love, and we can get you ready! I did as he asked, he first told me to take off my blazer, shirt and tie. Which I did the he asked me to remove my trousers, he gasped when I had done this. I was standing naked except my black cotton boxer shorts, and the hardest erection I've ever had in my life. He said "Shorts too" I put my thumb within the waist band and eased them down my legs, stepping out of them. He tutted at my boner and said "Now give me a twirl" I began to turn round totally dazed and confused when I faced him again he brought his hand hard onto my penis. With a spanking action. It was soft in no time I was in agony. After I had recovered he handed me a pair of skin coloured nylon stockings with lace tops. He gasped as I tried for the first time to put them on. I thought it was like putting on a pair of socks. He knelt in front f me and said "Here like this!" rolling them up my smooth legs. He then stood me up and clipped on a black Basque, clipping the stockings on to the 6 dangling straps I was amazed. He handed me a pair of knickers that matched the Basque and while I slipped them on he put some jelly like things into the cups of the Basque.
He gave me a skirt it was like the skirts the 6th form wore at my school about knee high and skin tight. I always thought that they where too sexy for schools but I considered my self lucky. With it he gave me a white blouse and handed me back my school tie. When I was standing in my school uniform he passed me the black knee high boots. "Not quite school uniform but it looks great!" Was amazed and couldn't believe my luck.
I sat down my hands trembling and unzipped the left boot and began to put my right foot into it. I realised and corrected myself. H Then I slowly zipped it up to my knee. Wow what a noise, what a feeling! I felt empowered somehow. Then I put on the right foot. And zipped it up. I felt like nothing could bring off this cloud. They felt like they where made for my feet. I stood up. And a little gingerly I took my first step as a woman.
I wobbled around a bit but soon I got the hang of it. I stood in front of the full length mirror and gasped. Although I had no make up on at all I looked like a girl with short hair. I began giggling with excitement. "Oh thank you so much!" I managed to squeak out. I reached over and touched his hand in a grateful gesture. He smiled. "Now it is time to thank me." I didn't know what he meant but I didn't care. This was the most alive I had felt all my life. I for the first time was who I was supposed to be! "Twirl for me again!" he asked I gleefully spun around. When I came to face him again he was closer to me and his hand reached out and touched my bottom. I swatted it away and tried to ignore it but he stepped even closer to me and placed both hands on my face. He pulled me closer and planted his lips on mine! I stood in shock, for a second or two. His hand slipped to my ass again, and then I kissed back. Sparks of electricity shot up and down my body. I unconsciously raised my left leg, and pointed my toes out. The kiss got more passionate his tongue forced into my mouth and began to explore me. I slipped my tongue into his mouth. He pulled me even closer and began to grind his crotch into my own. I could feel his hardness begin to grow. I broke the kiss and stepped away my breath lost I was in a slight daze. As I backed away I tripped over the chair I had been sitting on I fell backwards into it and blinked. As my eyes opened there was his cock inches away closing in on me? Instinct took over I open my mouth and swallowed. Within seconds his balls rested on my chin. I reached up and massaged his ass. His bottom shaven and smooth. He began to withdraw his cock from me. I followed it out a bit. He stood there kneeing in front of my face his manhood bobbing in time with his breath. My eyes focused on it. He took hold of his meat and placed it on my lips. Then as I tried to open up for him he began to smack my face with his penis. Then he slammed it into me. He began to work my mouth like a pussy. Slam fucking my face pulling it almost all the way out only to force it all the way in. I loved it. Why did my girlfriends hate this so much? I was moaning like a crazed whore around his lovely cock. It must have sounded like a porn movie, for I was truly in character.
He pulled out of me and winked. He stood up and took hold of my hair lifting me out of my seat. I stood facing him and he turned me round and pushed me forward onto the chair face first. I was on my knees my head dangling over the top of it. He lifted my skirt and I heard my knickers rip. I felt his hot breath on my ass and soon he parted my cheeks and was tongue fucking my little hole. This blew my mind.
That's why they prefer to be ate out than to blow. I thought thinking of my past girlfriends. His tongue darted out of my little hot hole. I was moaning again. This was the greatest pleasure I have ever experienced. "Oh my god yes!" "ohhhhhhhh don't stop!" "mmmmmmmmmmm fuck yea!" Then he pulled away. And his fingers replaced his tongue getting deeper. He slide them in and out a second then third followed. They seemed to be slipping into and out of my little hole; he must of lubbed them with something! Then he said: "you're ready now!" I was nearly passed out draped over the chair. Trying desperately to catch my breath. And to figure out what exactly was happening to me. I knew I was about to get fucked and I couldn't wait to be penetrated! He stepped closer to me I felt his tip brush against my thigh getting caught on my stocking strap. I reached round out of sheer desperation and took hold of his cock. And aimed it at where my pussy was. Then he was at the door! I felt just the tip enter. The feeling was out of this world!! He stood the with less than an inch of his dick embedded in my little boy pussy. I lunged backwards to get more of him in me. I heard him grunt as half of him slipped passed my tight sphincter muscle. The pain was in the back of my mind, somewhere but this unbelievable feeling of lust had taken over me. I looked over my shoulder (what a sight that must of been, a 14 year old boy dressed in a girls school uniform complete with stockings, Basque, ripped panties and knee high kinky boots, and skirt hooked over his waist. with a 40 something grey haired man in a tweed suit trouser round his ankles holding up his shirt and tie with his cock sticking through his grey y-fronts into the boy-girl's little ass pussy!) "Fuck me you Faggot" I screamed at him! he gasped and then began to thrust into me. Slowly at first but with some encouragement he got the idea. "stop making love and fuck me" "get it into me harder" "fuck me" "for fuck sake fuck me!" In no time he had taken hold of my hips and was giving me the fucking I so desperately needed. I'm not sure how long had passed but he slowed down again and his breathing grew very heavy. I sensed he was getting tired this would not do. I pulled off him and stood up. He was still bucking my side like a little puppy dog. I turned him round and sat him down. He sat there looking up at me and his puppy dog resemblance continued. I squatted down on his cock, and he slid in quite easily. I looked into his eyes he seemed grateful. I began to raise myself on my knees the full length of his cock. Then slammed my self down again. The feeling of his hardness inside me was divine.
My hands began to explore has chest through the buttons of his shirt. But it was fidgety, so on a down ward stroke I ripped open his shirt. He looked a little panicked. But he was buried to the hilt in my fanny. As I rode him my own cock rubbed up against his hairy chest. I began to grind my hips forwards and backwards along with upwards and downwards with my strokes to provide me with that extra wow factor! After a while of this my knees grew tired, I wasn't going to let this faggot beat me, so I turned away from him and lowered my boy-fanny on to him again. I sat on his cock my back to him and he exploded into life again! The two of us began to fuck in complete unison. I was truly bouncing on his dick my own cock hard and horny flopped about in time with my movements.
I would grow to love the symphony of fucking. The slapping of flesh on flesh provided the percussion section. The squeegee of the lubed cock and ass provided the wind and brass sections and the sheer passion of the grunting and groaning provided the rest. We where truly fucking as one his forward thrusts into my pussy where met with my reverse thrusts into his cock. With a smack when me met. He began to stand up mid stroke and I did like wise. We ended up in a standing doggy fashion. I noticed the full length mirror and the sight was truly amazing. I lost my rhythm now. I was totally flabbergasted that the little slut getting a hard fuck was in fact me. Add to that I was the same height as him and now my boots made it slightly challenging for him. But he kept hold of my hips and pounded away! Thrusting deep and hard into me.
I was soon so over come with the raw lust and I was hyperventilating. I collapsed onto a sort of dressing table. I lay there for a second. My little hole stayed open as I laid there. For an eternity I lay there. Both our breathing hard and deep. I slowly rolled over and on my back I looked up at his little cock poking through his grey y-fronts. I smiled
"I was lusting after a man who was too dull to be a history teacher"! He approached again and stood between my stocking clad legs he lifted them forcefully holding on to my thighs. His cock seemed to guide itself to me and in no time at all he was buried deep inside my fanny. This was deep but I wanted more. Much more. He sensed my frustration and raised my legs taking hold my heels he used this leverage to really give it to me. Now he didn't last seconds it was such a pity cause I felt my own orgasm building but he screamed "I'm cumming darling" He collapsed on top of me. We rested for what seemed like seconds, him lying on top of me my legs locked around him. The stiletto heels must have been digging into him. I felt the sudden softening of his cock. It slipped out of my pussy gently then the steady trickle of his seed followed. But we must have been longer for when I finally stood up and glanced at a clock it quarter to eight. Three hours had passed. My ass was sore. I was getting cramps in my legs. And I was completely unable to control my wind. My hole felt a foot wide! I fixed myself and ran to the door. I had it unlocked and was in the street about a hundred yards down the road when I noticed that the heels made the cutest noise on the path. It was only then that I realised that I was still wearing the sexy girls school uniform, underwear and those lovely boots he had gave me. I calmly walked back towards the shop trying desperately not to draw attention to myself. Difficult given that I was dressed as I was!
For some reason the door bell didn't chime as I entered. There sitting where I had left him was my "lover" he was sitting fingering his ass, and wanking and had my discarded boxer shorts over his head and had the crotch of the deep in his mouth. I stepped silently toward him. For some reason I was furious "Was I not enough for this little fag?"
He was sat with his trousers off and his y-fronts round one ankle, his skinny, bony legs akimbo cock in one hand and the fingers of the other hand were playing gently with his little hole. I placed the pointed toe of my newly acquired boots to his mouth! He sucked at it excitedly. "I don't remember giving my little faggot permission to pleasure himself!" I screamed at him. He tried to speak, but my toes in his mouth prevented him. I forced some more of my shoe into his mouth. I'm pretty sure he was deep throating my sexy boot! "For that you owe me bitch!" I shouted again. "What does my little slut servant have to say to that?" he tried to speak but nothing but a muffled gag came out. For some reason I was incredibly turned on! I leaned on his mouth forcing this dull man to the ground he sat there sucking on the toe of my boot. I removed my toe from his mouth and stepped closer. "Continue!" I could tell trough the white cotton material of my boxer shorts that he was confused, so I forced the matter my leaning forward and whispering "Don't make me repeat myself!" he began masturbating his pitiful dick. I was partly impressed at this as he had already shot a load in me. But he would never know this! "Tell me, what are you thinking of while you disgust me?" "I'm thinking about you!" he gasped "What about me?" I said checking my nails! "I'm thinking about fucking your sweet little pussy!" as he gasped this I could sense that he was close to climax, that wouldn't do. I stepped forward and placed the heel of my right boot onto his scrotum. He squealed in pain. And like an idiot he tried to stand up, pulling his sac even more causing him more pain! "You will cum when I tell you to cum! Understand!?" it didn't seem like he did so I twisted my right boot round a little forcing him to nod in agreement. I released his balls and allowed him to stand. As he stretched to his full height he began to protest. He was all winney and it was such a turn off. I was horny and I needed to be satisfied! This was going to be fun!!
I slapped him across the face and he recoiled in horror! I looked him in the eye and said "when your spoken to!" he was not sure what to make of the situation. I leaned forward and said "I'm 14 years old. You are considerably older! I have a photo of you on my mobile undressing me and if I wanted you could go to jail for a long time. Child molester!" he shook his head and began to say "n..." I stopped him by grabbing hold of his balls and yanking them. He screamed in pain. "you are now my little slut. You will give me a part time job here, and whatever else I want!" I still had hold of his little balls "I am blackmailing you but you love it!" I giggled at him. He looked like he was about to cry, I slapped him again and he turned his back to me. I forced him over the back of the chair I raised my skirt and began to find his little brown hole. Remember this was my first time in there so it took quite a lot of fumbling and he was trying to fight me off. So it too a while. "this would be better for you if you help me!" I said gently. "we both know you want it. And if your nice to me you can have all the used panties to suck on that you wish!" I urged. That did the trick he reached round and parted his saggy ass cheeks. "please be gentle. I am a virgin, I don't want to blee..." I cut him off as my cock entered him. I hovered there for a few seconds, waiting for him to stop moaning. God I thought queers would be tougher than this fruit. When I felt that he was ready (ok just before I thought he would be ready!) I slammed into him I began to ride him! Like he was a cheap whore. Not that I knew what that would be like!
"take this you little fag" I screamed as I forcefully fucked him. He whimpered a little as I began to fuck his ass. I fucked him hard, as hard as I could. For some reason I as really angry with him. "No please stop!" he was crying his cries muffled by the top of the sofa. "Oh please no!" His ass was so sweet I just pounded my little 14 year old cock as deep as I could into him. My grip tightened as my orgasm built up. It was an amazing feeling being dressed as I was. And fucking the brains out of a little pussy like this. My balls began to swell and I was done. "fuck" I screamed as my load shot out of my cock into his little brown hole. To my surprise he spun round and engulfed my dick in his mouth. Taking me deep down his throat. Lapping up my cum and his ass juices!
Minutes later that post orgasmic regret that teenage boys suffer from, kicked in. I realised that I was standing in a shop dressed in a sexy girls school uniform. An old man was licking my cock and balls. I pushed hum away and hurriedly began to strip off. He began begging me to stay. There was no way I was staying like this. I quickly got dressed, and ran out the door.
It was nearly 10 by the time I got home. My dad was furious until I told him that I was working in my new after school job. He seemed quite pleased that his son was learning the value of money.
The next day walking home from school I stopped by my shop.we talked a little about what had happened, he confessed that he had enjoyed being my little bitch! And that he spent the night sucking on my boxers! We agreed that I would begin to work there after hours he would pay me what I asked for, and I could have my pick of the cloths. I would also help him pick the new ranges from the catalogues.
He was to refer to me as Mistress or Madam Stephanie from then on in. He would do my laundry cause I couldn't get my mother to wash my panties! I was a 14 year dominatrix! And now owned my own cloths shop!
This is the start of a rather long story. I'm not sure whether I should document it but if you liked it let me know and I will try and continue it. It is my first adventure into this world of domination so if this is your cup of tea let me know how it rated? Or even give me tips on how to improve it!
Many thanks
Stephanie Magowan