Losing my virginity to my best mate

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Losing my virginity to my best mateWell, last time I left you with how I basically got ****d by a black teacher at school when he discovered I was a crossdresser. There’s a lot more involving him as I spent two years of my life being his personal fuck toy, including him giving me my first taste of pussy. But that’s for another time. Today, I’ll tell you how I got my first taste of cock, from my best friend.It’s 1994, and PCs are still rich peoples toys. The internet is still for geeks and online porn doesn’t really exist. As a teenage crossdresser with a huge nylon and school uniform fetish, the world is a very different place to how it is now. I’m a slightly chubby boy, and my best mate is a lanky k** called Mark. We’re a few months apart in age, and we’re inseparable. Like all k**s our age, we spend our free time hanging around and riding our bikes together. Mark comes from a way richer family than mine. They have cable and a big TV, and a PC. I was hanging out at his one weekday during a school closure; both of his parents worked full time and his sister was out at her friends. We’d been out on our bikes and watched the dreadful TV movie Airborne (Hockey Nintendo! – this movie will stay with me forever) and we were bored. He’d tried to show me the internet, but his dad had locked the PC down. I randomly said “shame you don’t have any porn!” to which his eyes lit up.”I’ve got porn!” he says. He races out of the room, and comes back with a carrier bag stuffed with newspaper. It’s a Sunday Mail sexual health supplement. I couldn’t be any less turned on if I tried. I just wanted to be back home, wearing black opaque tights and the rest of my newly acquired school uniform. I’d finally found a lower school grey pleated skirt in my size, and I literally didn’t want to take the thing off. I try to hide my disappointment and begin reading the “Dear Miriam” type letters desperately hoping I can get the horn.I read out one of the letters jokingly; “Hey mate! Listen to this! ‘Dear Miriam – I like to crossdress in my spare time as a form of stress relief. Is this normal?'”He’s sat on the edge of the computer desk, flicking through a lingerie catalogue. He looks up at me, possibly misunderstanding what I’ve said and utters “I like to crossdress…” Taken aback, I quietly say “Really? I… like… to… crossdress… too…” His eyes were like saucers. He gleefully says “Let’s start a crossdressing part!” as he slips off the güvenilir canlı bahis siteleri desk and darts out of the room.I’m left slightly shocked by this, and he comes back in 5 minutes later completely taking me aback. He’s changed, into a pair of thick black tights, a tiny little red wrap around skirt and a white strappy tank top. He’s also wearing a pair of silver strappy wedding style shoes at least two sizes too small, but they have a heel and I’m jealous.He hops back up onto the edge of the desk, crossing his legs. He sits there, stroking his thighs, and begins to cross and uncross them like Sharon Stone from Basic Instinct. I get up, and before I know what I’m doing, I’m stood in front of him, his knees together, and I begin to run my hands along his legs, feeling the soft nylon on my palms. The tights, obviously belong to his younger sister, as they don’t fit him fully. At this point, my eyes almost bulge out of my sockets. He’s wearing a tiny pair of bikini knickers, that do not contain his massive erection. It’s sticking bolt upright out of the top, peeking out of the waistband of his tights, and is easily three times the size of mine.I sit back down nervously, and he begins to lean back on the desk and groans “taaaake meeee!” in a husky voice before sitting up laughing. I stand up, walk back over to him, and he parts his legs and places them on a chair behind me. I run my hands all the way up his thighs to the very top of his hips. He spreads his legs wide, causing the tights to pull down slightly exposing even more of his rock hard cock. I just utter “Huh! Log!” as his eyes make contact with mine and he asks “Want to touch it?” as he grabs my hand and places it on the bare skin of his shaft, giving me my answer for me. I wrap my hand round it, grasping it firmly as he slowly wanks himself with my hand. He groans deeply, before hopping off the desk once more, grabbing my by the wrist and dragging me to his parents bedroom.He hops up on the bed before I have time to admire his long shapely legs, and lies flat on his back. His skirt is now up round his waist and his tights have slipped down to his thighs as he ushers me up on to the bed. I kneel over him, and once more take his cock in my hand.I slowly begin to jerk him off. His eyes, closed, as he slowly thrusts his hips into me hand. He opens his eyes, sits bolt upright and says “wait!” before jumping off the bed. He kicks his heels güvenilir illegal bahis siteleri off, before dashing out of the room. He comes back a minute later. My head is swimming. He holds out his hand, and offers me a bundle of clothes and tells me to go get changed. In his hand is a pair of black tights, a blue school skirt like we’d wear at our school, and a white shirt. I go out of the room and get changed on the landing, sitting on the stairs to put the tights on. I struggle with the clasp on the skirt before getting up and going back into the room. He’s changed too. He’s wearing his sisters school uniform. A tiny grey pleated skirt, with his massive erection sticking out the front. He’s also wearing a black lace bra, with a white shirt tied over it Britney style, and a pair of fishnet stockings and suspenders that obviously belong to his mum.He lies back on the bad, his legs spread and he begins gently wanking himself off. He ushers me on to the bed next to him. Nervously, I climb up on it, and before I know what I’m doing, I have my hand wrapped around his dick and am slowly tossing him off. His cock is absolutely oozing precum, and he’s moaning deeply. I open my mouth and lick my lips, wondering what it would taste like. Somehow, as if he’s reading my mind, his hand is on the back of my head pushing me down onto it. I resist slightly, but give in before that giant helmet pushes past my lips and fills my mouth. He starts grunting deeply, thrusting his hips into my face, gagging me as I choke and cough on his battering ram of a prick. I have no clue what to do, other than try to do to him what I like the feeling of. It seems to work, as before I know it, I’m sucking on his helmet like a straw, wanking his thick shaft into my mouth before he grabs my hair ond hold my head in place before flooding my mouth with more thick creamy spunk than I ever thought possible one person to make. I’m choking and gagging as it rolls round my mouth before I realise he’s telling me to swallow it. It tastes horrible. It doesn’t taste salty, just; sour. I swallow every last drop but it’s running down my chin and the taste is in my mouth still. He lies back, spent, his cock soaking wet with a mix of his cum and my saliva. Something snaps inside my head, and as he lies there panting, I lower my head to him and slowly lick the entire length of his dick, making him gasp and open his eyes. He’s still rock güvenilir bahis şirketleri hard, unlike me that goes soft every time I cum. He springs up, skirt failing to cover his still engorged tool, as he dives into his parents bedside drawer. He pulled out a pack of condoms, holding them up counting them. 5. I still remember it to this day. He exclaims “They’ll miss one, they never fuck” before putting them back. He pulls out a tube of KY Jelly, before opening it and smearing it all over the end of his bare manhood. He then grabs me by the hips, bend me over on the bed, and tells me to grit my teeth. All I can mutter is “NO!” but it’s no use. He’s taller and stronger then me. I fell him flipping my skirt up, yanking down the back of my tights, and instantly freeze at the sensation of the cold lube on my ring. I whimper gently as I feel him finger me gently, working more of the lube up my arse, before he lines up. Before I know it, in one fell move, he forces his way inside, as he pushes my head down into the pillow to stifle my screams of pain. He must have a 6-7″ cock, and my tiny little ring has never been touched before. I’m bucking and struggling for all I’m worth, but he’s holding my wrists behind my back like reins. Eventually, the pain subsides and he loosens his grip. My insides feel like they’re on fire. He places his hands under my arms and pulls me back up into him. He begins kissing my neck and riding me slowly, before snaking his way into my tights and pants to grab my semi erect cock to wank me into life. I reach back behind my head, pulling his head forward into my neck from behind. He’s panting and groaning as his giant dick batters my virgin hole. Every thrust I can feel him pushing deeper under I eventually feel his balls slapping my arse.He lets go of my shoulders and pushes me down into the bed again between the shoulders. He picks up his pace, using me to get himself off. I’m grunting and screaming for all I’m worth. All I can do is mutter “Fuck! Ugh! Shit!” Before I know it, he bellows deeply and unleashes a second torrent of cum straight into my arse. He collapses on top of me whilst he catches his breath, before slowly pulling out of me with a loud “plop!”. A slimy mixture of cum and lube slips out of my red raw arse, soaking my tights and making me shiver at the sensation. I get up onto my knees, as he offers me a tissue. Tears are streaming down my face, and the only thing I can think to do is reach down and try to suck him hard again wanting round three. Alas, he’s spent, and we must go our separate ways. he tells me I can keep the cum splattered skirt and tights which I will come to treasure for many years to come. Little did I know, what was going to unfold for me in the months ahead…

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