A nearly true story with embelishments to make it a little more interesting. I hope you enjoy it. Feel free to contact me at MartinFail1993@yahoo.co.uk
It all started with a little innocent dressing up. I was a 13 year old blond boy whose older sister had just moved away to university. Home alone one summer day I'd gone into her room looking for whatever I could find... some fags, alcohol or incriminating evidence I could use against her for personal gain. I was just your typical annoying younger brother.
Whilst rifling through her drawers I found her lingerie collection. She had a lot of lingerie, and something compelled me to take some out and feel it. I thought I was doing it just to get to know what it felt like for when I got a girlfriend. But the bra and panty set I'd got out was silky smooth and I loved the feeling of it. So soft and unlike any clothing I owned. I felt an urge, an awful urge, to try them on. I quickly put them back and left the room.
A few days passed and I hadn't been able to stop thinking about the feel of those panties and how they might feel if I were to wear them. Home alone one afternoon I thought "What the Hell? It won't harm anyone!" and gave in. I grabbed the bra and panties and went to my room.
I stripped off my boy clothes and picked up the panties. The silky, soft material felt great as I stepped into them and pulled them up. My sister's size fit me well except for the small bump of my cock. They felt fantastic against my body, and I couldn't help feeling how tight they were on my bum. My little cock got hard within seconds. I put the bra on too, feeling tremendously naughty, then wandered back to my sister's room to use her full length mirror.
I was pretty cute! I was shocked to see how, even with only medium length hair, my slim body and boyish looks were transformed by just some underwear into looking like a girl's! I stuck my hips off to one side and thought I even looked a little sexy. I stuffed some stockings into the bra and created a pretty good attempt at tits. I looked like an 18 year old girl. I was amazed.
And I was bloody turned on.
Over the next few weeks, whenever my Mum and step-dad were out, I spent most of my summer holidays playing "dress up". First various panties and bras. Then dresses, tops, skirts and heels. By the end of the summer I was watching Youtube videos on how to apply make-up and my blond hair was nearly at my shoulders.
And during that period, my sexual fantasies changed. Like any typical boy I'd been starting to think about girls from school. But as I messed around with girl's clothes and make-up I started imagining myself as a girl meeting a boy. Sometimes a boy from school or someone famous. But they were always kissing me, dominating me, spreading my legs. I'd stopped thinking of girls completely.
The final Friday before school restarted I got a bit bold. My Mum headed out to work and my stepdad went off to visit his family in London. I decided to go out as my feminine self. I'd taken to calling her "Jasmine" and I wanted to see how people would react to her. I got dressed up in a lovely summer dress, rather short, with some high heels and decent make-up. With my long blond hair put into a pony-tail I looked like a 16/17 year old girl. And, if I say so myself, a very pretty one.
I headed out nervously, but my street was empty on a warm summer's day. I'd been practicing with heels for a month and was very proud of the confident way I walked in them as I turned at the bottom of my road into an alleyway that took my on to the main road into town. There were three boys from school, one from my class and the other two in my year, loitering in the alleyway.
I was terrified at the prospect they might recognise me but they'd already seen me and I knew turning and walking back might draw even more attention. I put on an aloof look and walked up to where they stood.
"Oi oi boys, what do we have 'ere?" said the tallest of the three who was a 14 year old called Mitch.
"Fucking stunner by looks of things" whistled a smaller, but way stockier, Dave who was in my class at school.
"Babe, want a ride?" Mitch said, thrusting out his hips provactavily.
I was stumped as to what to do. I decided to just fuck it and go for gold. As I reached them I ignored Mitch and Dave and went to the slightly shy looking guy I thought I remembered might be named Nick. I rubbed my body against his and kissed him gently on the lips before turning to the other two, sticking my tongue out in a not unkind way and walking off, swaying my hips as I went.
"Fuck!" I heard Mitch shout as he slapped a dazed Nick on the back. I walked off, feeling on top of the world. I had my first taste of the power of flirting and how much boys and men were influenced by what they saw. Attention from men in the street was intoxicating. Boys whistling at me, married men drooling over me as discreetly as they could whilst their wives dragged them around shops and girls giving me evil looks as I walked passed. I loved it.
I got home around 2pm, and thought I'd made it home in good time. But as I walked up the driveway I heard a sound that brought my soaring daydreams crashing around my head. The metallic clashing sound of my step-dad, Mark, working out in our garage which he'd turned into a pretty impressive gym.
And then a second issue presented itself. Not having a handbag, I'd nowhere to put my keys so I'd left the back door unlocked so I could get in by going around the side of the house. Unfortunately the back door was directly across a tiny utility room from the door to Mark's gym. My chances of sneaking in without being seen were low but better than they would be when Mum got home. I cursed myself for not leaving out some male clothes so I could avoid this.
I realised I needed to see if Mark was facing the door or not. If not I could sneak in and rush past before he'd see me and then shout a hello once I was out of sight and on my way to my room. If he was facing the door I'd need to think again.
I wandered round the back of the house and peered through the back door window as discreetly as possible. I could see him sat on a bench doing some dumbbell lifts... with his muscular back to the door.
Thanking whatever God there might be, and praying they'd see me through this I slid open the door and was about to burst into a run when I realised I'd still got my heels on. The momentary hesitation to move as I reconsidered my balance was enough for Mark to turn round and see me.
Mark was a 6'4" black guy who thought body building was the key to a happy life. He was topless and wearing just a pair of grey sweat pants, his large pecs and arms were clearly visible and his body ran with sweat. He had a shaved head, and a face that was permanently angry looking, though he was actually an alright guy.
"Well hello there" he said, his grumpy face breaking out into a shit-eating smile I'd rarely seen as he stood up and walked through the gym towards the utility room. "Ya won't find him about, guess he's out"
"Who?" I asked with genuine curiousity despite the horrific fear currently threatening to cause me to scream.
"Justin, silly." he said as he grabbed a towel and started wiping down his massive chest. I couldn't help gawping like a... well a teenaged girl. "You popping by for a bit of fun, huh?" he gave me a wink.
"Erm.. yeah.." I was struggling to get my brain to plan an escape as my eyes moved down to the large bump in his sweat pants. I foolishly misused my new powers and gave him a naughty little smile before muttering "Guess... I'll be going". I turned to get back out the back door but by then Mark was towering over me, and I froze. The smell of his body was intoxicating and turned me on more than anything ever had. It was musky, stronger because he'd been sweating, and really exciting.
"Oh there's no rush" Mark purred, like a cat that'd got the cream "Just because Justin ain't here don't mean you can't have a little fun".
"I really think..." I started as he got a hand on my back and propelled me through the kitchen towards the front room
"Girl, I seen the way you looked at my package, don't fight it babe" he growled as he pushed me on to the sofa and fell upon me, his hands on my body and his mouth on mine.
I was so scared he'd realise I wasn't what he thought I was. But at the same time, I wanted him so badly. He was a fantastic kisser and when his tongue forced its way into my mouth I started sucking on it like I imagined a girl was meant to. His heavy body pinned me down as he ground his hard on against me through his sweats. I knew I had to do something to stop him getting me undressed whilst keeping him happy. I was feeling dizzy from the mixture of stress, excitement and confusion. I had to get control of the situation somehow.
I pushed him up, disconnecting our kiss with a twinge of disappointment. He went willingly, looking quizical as I slid out from under him and silently repositioned him to sitting position. I fell to my knees on the floor before him and pulled his sweats down. Out bounced a large uncut hard cock. I'd find out later it was 9 inches long and 5 inches in circumference. As I pulled his sweats down to his knees I revealed his huge balls. I was so horny and so turned on, this felt so right yet I knew I needed to get out of here as quickly as possible. The only way out was through, I decided.
"Girl, you are such a fucking slut. I love it" Mark groaned as I reached out and started stroking his big cock, my hand not yet able to get round it all. I loved the way his foreskin looked as I pumped his cock and actually felt myself salivating. I couldn't understand what was happening to me. He reached over and grabbed me by my pony tail and forced my face down to his cock. "Suck it bitch"
I started licking the head but he didn't let that go on for long. "SUCK IT!" he shouted as he slapped my face with his free hand. I opened my mouth to protest at which point I found his cock thrust three inches into it. My little mouth only just stretched around his cock as I struggled to keep my teeth clear. "Mmm.. yeah... that's it" he said as he roughly held my head and began to feed me more of his cock. My mouth was tight around his big cock, which got thicker the closer to the root it went. However even at that age I managed to get 7 inches down, the last two inches just too thick to fit. I could do nothing, as my mouth was used to pleasure him, other than enjoy the salty taste of his cock and nurse on the precum I felt in my mouth.
He face fucked me for five full minutes, during which I moved my hand to his balls and massaged them. He called me names and told me I was just a white slag good only for fucking. I was so overwealmed with conflicting feelings of lust, fear, pain and pleasure that I didn't realise what the tensing up of his legs beneath me meant until the first blast of cum flew down my throat. He pumped my mouth full, most of it straight down my throat, and he held my head in place until I'd sucked every last drop clear of his massive dick.
"Oh babe, your mouth is better than any cunt I've ever fucked" he groaned as he pushed me off like a piece of used meat. "Bet Justin doesn't cum half as much as I do" he laughed as he laid back in the afterglow. I mumbled something I can't even remember now, and struggled to my feet. I felt weak with fear as I stumbled out the room, grabbing my keys from a side table as I did. I ran out the front door and hid round the side of the house panting and finally tasting the cum he'd mainly forced to bypass my tongue. It tasted good. I'd enjoyed it all. But Jesus, what a risk.
It took an hour for me to risk going in the front door, knowing I had a better chance of getting past him that way even if he was still in the front room.
I quietly undid the door, and stepped into the house (this time heels in hand) and listened to see if I could hear where he was. The tell-tale sound of snoring from the living room sent a sign of relief through me and I tip-toed over to the front room door. He was sat as I'd left him, his immense cock now soft and lying on one leg as he slept. I ran then, up the stairs into my room. I grabbed some clothes and ran into the bathroom to clean off my make up before Mark woke up. I changed, ran back down stairs and then dramatically opened and closed the front door in the hopes of waking Mark. As I approached the door this time I heard him moving about. I got to the door just as he stood up and finished putting his sweatpants back into place.
"Hey Mark!" I said with feigned enthusiasm
"Hey Justin" he said with a raised acknowledging hand. "Just about to work out, wanna join me?"
It was a running joke, his disdain for my slim body was real but he never meant much harm.
"No thanks Mark," I managed a laugh "I've been out with mates and need a rest"
And with that I headed to my room to contemplate what had happened.
Weeks later it all came to a head. I hadn't played as Jasmine since, though I'd spent nearly every minute since the last time I had at school and in bed fantasising about Mark, his body and what I wanted him to do to me.
I was lying on my bed in just my boxers one morning before school when Mark strode in looking angry.
"You been fucking wearing my socks again?" he shouted
"No!" I shouted back, honestly. He was obsessed with the idea I might be stealing his socks but given he was a size 14 and I was a size 8 it was just not feasible. What happened to his socks I'd never know.
"You fucking little liar!" he screamed as he strode over to my bedroom cabinet. I had mere moments to contemplate the fact that my underwear drawer also contained my prodigious panties and bra collection before he'd reached out a hand and flung the drawer out of the cabinet and on to the floor. The false bottom I'd rather cleverly put in to stop Mum finding my little collection flew out with it and boxers, briefs, socks, panties and bras flew out all over my bedroom floor.
As Mark turned to look for his socks among the mess, he saw the lacey, silky numbers I favoured lying around.
"What the fuck?" he screamed, thankfully to no effect as Mum was already out at work "Your little slut been round here more than I thought huh?"
He pulled out the drawer below and again my false bottom trick turned out not to be that clever. T-shirts, girly tops and dresses flew out as he upended it.
Including the dress Jasmine had been wearing that day. That day he'd forced his big cock down my throat.
Now his eyes went wide as his brain began to process the information and create a new picture.
"You...." he stammered "Ah, shit"
He was angry. I can almost forgive him for what he did. He picked me up off the bed and slapped me so hard I hurt for the rest of the day. But he pulled back before he did anything worse, holding me effortlessly up against the wall, arm muscles bulging.
He lowered me slowly to the ground and I tried to catch a breath as he removed his hand from my neck.
"I want your little bitch friend downstairs, in that dress again, in 10 minutes." he said with a deep and angry growl.
"What?" I struggled to ask.
"You heard me." he said with a truly menacing look in his eyes "10 minutes." With that he left the room.
I realised I had no choice, forgetting about school or even about feigning ignorance. I knew he'd hurt me if I didn't do as he said. I quickly did my hair, my make-up and got dressed. I was downstairs, in heels, just in time.
I found him in the front room. He was wearing just some boxers which were already tenting out a fair bit. He smiled, surprisingly sweetly, when he saw me.
"Hi babe, back again huh?" he said as I walked through the door "Couldn't get enough last time?" he sneered now, his sweet smile turning a little malevolent as he grabbed me and pulled my body up against his. He leaned down and kissed me, his hands working down my back as I relaxed against him and let him have his way.
He pulled away. "You helped get me off last time but left before I could return the favour. I bet your pussy is begging for a big cock." He smirked as he began to pull my panties down. "Don't worry though, I'm gonna make sure it's your turn to get off".
With my panties round my knees I couldn't put up any resistance as he pushed me down by the sofa on to my knees and over the sofa arm. Without any lube he slid a big fat finger into my virgin hole and made me scream. Feeling my tight hole spreading the way it was made me shudder with fear at what was to come.
"Mmm... baby girl that's one tight pussy!" he laughed as slid his finger all the way in and out. "Gonna hurt the first time with my fat cock but don't worry, you'll soon be begging for more". He continued to laugh as he used one hand to hold my squirming body down on the arm of the sofa and his other to viciously finger my hole. I was moaning in pain as he put another finger in and then another, barely able to think as the sensations overwealmed me. As his fingers got as far into my hole as they'd go I started to feel bursts of pleasure that made me moan even more. Quickly it turn from me struggling to get away to me pushing back on his fingers.
"Mmm yeah cutie ya like it don't ya? Now you need a big fat cock in that pussy, bitch" He pulled out his fingers and gave my arse a hard slap that made me moan pathetically. I heard him unzip and felt him spit on my now sore hole. He used his cock to rub his saliva around my hole and I won't pretend it didn't feel good. I groaned again like a bitch in heat and couldn't stop myself pushing back against it again.
"Fucking slut for cock, huh? Don't worry babe, you're getting it all" and with that he pushed the head harder against my boy-pussy and I felt it first spread my hole and then once it had spread it enough slide deep into me in one hard and painful thrust.
I screamed again as Mark grabbed a hold of my waist with both hands and began to deeply plough me. The pain was intense, his cock going all the way to the very thick hilt. He started to thrust in deep and then take it nearly all the way out before pushing it all back in again. Soon enough, inevitably for a slut like me, the pain started to become a secondary concern as the pleasure ramped up. The sensation of his big fat cock spreading my hole and rubbing my prostate had me making the most girly squeals of delight. This seemed to excite him.
"Bitch, take my cock, you love cock, you're gonna take my cock all the time, oh you slut, you whore, nasty like ya Momma" he said as he moved one hand from my waist up to my hair which he grabbed and pulled on as he sped up even faster. His heavy breathing got faster and faster too as I realised he was getting close to cumming, my own little cock was leaking pre-cum all over the arm of the sofa now.
"Take my load" he moaned as he collapsed on my back and I felt his thick cock pumping inside me and felt the warmth of his spunk filling my now hungry hole. After 30 seconds of that he whispered in my ear "Fucking tight little pussy babe, sweet fuck, now I know what you are for". He kissed my cheek then withdrew and walked out the room. I was left lying on the sofa, arse in the air, feeling a little bit of cum leaking down my leg.
"Tell Justin he better not be late for school" I heard Mark shout. I looked at the clock and realised I had about 5 minutes to get changed and out the door. I rushed through it, no time for a shower and barely time to remove my make-up. I sat through my first two lessons full of cum and still wearing lipstick. And when I rushed to the loo straight after to sort that out I found a text from Mark on my phone.
"Hey slut, thanks for this morning. Be in Justin's room tonight after his Mum's gone to bed so we can play again. Fuck you later, M"
Aw... shit, I thought.