Gary’s Dressup Sissy

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Gary’s Dressup SissyWhen I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games. One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One movie was all transvestite scenes. This shocked Gary but I found it a massive turn on. I’d been experimenting in wearing my sister’s clothes for a while. Gary could obviously see this, so suggested I dressup. We went up to his sister’s room and looked in her wardrobe. Gary immediately picked out her school uniform. She was a little younger than me, so when I slid into her grey pleated school skirt it was way above the knee. “Too short for school” Gary had commented.This went on for a few days. I would go over when Gary was alone. He’d have me dress up in the schoolgirl outfit, skirt blouse, panties and ankle socks, and we’d either play games or watch movies.Gary would tease me a little. But I could tell he liked me to dress up. Maybe he missed his girlfriend I thought.One day in his bedroom, with me in my usual schoolgirl attire, there was a clothing catalogue lying around; a big thick book full of clothes, Gary had been shopping for new football boots from it. I began to flick through the pages, looking at the beautiful women. Gary came and sat down beside me and closed the book, then opened at page one. We flicked through the catalogue together, commenting on the clothes, Gary would say how he thought I’d look good in certain outfits, making me blush, and I would choose ones that he should buy me. Eventually we arrived at the footwear section, again Gary picked out the shoes, always sky high heels. My cock began to stiffen, as I knew which catalogue section was next, as I’m sure did Gary, page 202, lingerie. “mmmm” said Gary. I blushed. We flicked through the pages in silence. I waited for him to choose an item for me. He stopped at page 207. Black suspenders, panties bra and stockings. My cock twitched.”I bet you’d fuckin’ love to wear that wouldn’t you, you little sissy” was Gary’s response.Although a little surprised by the manner of his comment I said “sure”. I’d come this far, what was the point in being coy about it “I’d just love you to dress me like that”Gary grinned a wicked grin. “Come on” he said, darting from the room. I followed him into his mother’s room. He went straight to her bedside table and opened the bottom drawer. It was full with lingerie. All colours. “I found this lot this morning” said Gary ” sit down”I sat on the bed as he picked through the knickers, “don’t mess them up too much Gary” I said “she’ll know we’ve been looking”Gary quickly found a matching set of lingerie. Panties bra and suspenders, and also a pair of black lace topped stockings. He gathered them up in one hand and thrust them at me….”put them on” he ordered.Slightly nervously I stood, stepping out of the schoolgirl skirt and removing the blouse. Gary handed me the suspender belt. I fastened it first, then stepped into it. Followed by the panties and then with Gary’s help the bra. Gary then handed me the stockings, I slid them up my legs, they felt divine, my cock stiffened. I glanced at the rapidly growing bulge in the front of Gary’s jeans and knew his cock was doing the same.Gary then moved to his mom’s wardrobe….and picked out a pair of black high heels.”Will these fit?” he said….I looked they avcilar escort were a size 6 and I was a 7, but I tried them. They fit although they were very tight. Gary was grinning from ear to ear.”How do I look?” I asked….”hot” was his reply.He picked up the schoolgirl outfit…..handed it back to me….”now this” he saidI put the blouse on and stepped into the short little schoolgirl’s skirt.Gary grabbed me by the hand and led me back to his room. He sat me on his bed and went to his dressing table drawer. Taking out a Polaroid camera.”Smile” he said as he shot off a couple of photos of me.”Oh come on!” I said”don’t worry, they’re just for us to remember today ok?””Ok” I replied. “Lie down he said, so I did…..he picked up his dressing gown from the floor, and removed the belt.”Give me your hands” he said….again I did so…..I was so horny now I’d do anything he wished.He tied my hands above my head to the wooden spindle of his headboard.”Are you horny?” he asked”oh god yes”he stood up, took the camera and fired off two more pictures.Then undid his belt and removed his jeans and pants…then his socks then shirt. He stood before me naked…I could see a long thread of precum dangle from the tip of his fully erect cock.He climbed onto the bed with me. He straddled me before positioning his knees either side of my head, pinning me helplessly to his bed. He began to stoke his cock, right before my face. His cock looked fabulous. The precum dripping onto my lips. “You like this?” he asked….I noddedas he continues to stroke…..I opened my mouth and licked his cock”oh my god”….he exclaimed….”you filthy little sissy whore, I can’t believe you want to suck it!”Again I nodded….He pushed the tip of it between my lips….I tasted him…..It tasted salty. God I was so hard.Gary pushed his cock in and out of my mouth. Slowly at first. Then he got quicker. I closed my lips around it and tried to suck. I licked his cock head and shaft as best as I could. But as he speeded up I found it difficult. His hands grabbed my head and held it steady. All I could do was to keep my mouth open. He was now fucking my mouth. His cock was plunging in and out. His cock head was banging the back of my throat making me gag and cough. My eyes were stinging and slobber was going everywhere. I glanced up at Gary. He was red in the face and sweating. He was grunting and growling as he clearly enjoyed fucking my face.He pulled it from my mouth and began to jerk off in earnest. I could tell he was close”cum in my mouth Gary…” I pleaded…”over my face””don’t worry slut….I’m gonna spray all fuckin over you”With that his hips began to writhe on me….and the first spray of cum hit my face….I opened wide and he forced his cock into my gaping mouth. I eagerly gobbled up the rest of his load…..sucking him clean as he moaned in ecstasy.Gary then wiped the initial spurt of his jizz from my brow and cheek into my mouth….I took it from his fingers.He stood up…grinning he looked at me….the skirt had ridden up revealing my socking clad legs.He untied me….I knelt up. Looking at him I said “can I cum?””Jerk off” he ordered….I hitched up the skirt and fumbled my stiff cock over the front of the panties”Gary grabbed a glass from his bedside table and drank it’s contents. handing it to me he said”Cum in that, don’t get any on my sister’s or mom’s clothes”I positioned my cock into the glass….and with the other hand began to jerk off”don’t cum till I say so” he said….clearly getting off being the dominant maleI jerked off….stopping every minute or so to gather myself and so as not to cum.he made me jerk off for maybe 10 or 15 minutes like that, occasionally taking my precum on his finger, şirinevler escort before feeding it to me.Eventually I begged to cum “please Gary…I can’t hold it any longer””ok slut….cum now….into your cum cup”I spurted shot after shot into the glass. “Oh fuck” I screamed, as cum pumped from my cock, almost half filling the glass.Spent, I looked at Gary”Now drink up” he said “You need to get used to the taste of cum honey….coz you’ll be sucking my cock every day from now on….otherwise everyone will get to see those Polaroids!”I looked at him again. I could see he was clearly enjoying this. I glanced down and saw his cock wasStiff… again! My stomach sank for a moment when I realised the position I was in. I was in my friends Bedroom, in an empty house, with no one due home for four hours. I was dressed like a slut in his mom’s sexy underwear. He had taken photos of me too. He had already fucked my mouth and spunked all over my face. He had just made me cum and he was still horny! What is more, I was loving every minute of it. Another thought crossed my mind. I thought back to the transsexual porno we had watched together. Trannies get fucked up the ass!Gary picked up the cum filled glass and handed it to me. “Go on….slut….drink it all!” he ordered. His commanding voice sent a shiver up my spine. I lifted the glass to my lips, opened my mouth and poured the cum in. The salty cum slid into my mouth. The musky taste was nice and it must have showed on my face…”You filthy slut!…..you love it, don’t you!”I nodded. I looked a Gary. His face was flushed and his cock was sticking up hard. He had that look in his eye again and he was not finished with me yet. “It doesn’t taste as nice as yours” I said. I put my finger in the glass and scooped up the last of the cum. I licked the finger and stared into his eyes. Garry growled and then suddenly shouted “Hands…give me your hands!”. I held them out in front of me. He took the dressing gown belt and tied my wrists with one end. Next he pulled his bed away from the wall a bit and moved the mattress back too. “Lean over the side of the bed…sissy”. I moved on my knees, to the bed side and lay my body on the mattress. Gary took the other end of the belt and walked round to the other side of the bed. He then tied that end to the metal frame of the bed. I was going nowhere.The Polaroid camera came out again and more photos were taken. A few of me in my tied position. He then moved his cock up towards my mouth. I opened my mouth while he photographed me licking and sucking his cock. The camera was empty, so he left me tied to the bed while he went for a fresh film cassette.Gary came back into the bedroom, clutching the camera and a large jar. “What’s that…what are you doing?” I asked. “You!……..That’s what I doing!….I’m going to fuck you!” He replied. Gary knelt on the floor behind me. He started to touch me. He ran his hands all over my ass, body and legs. His hands roamed all over me. I felt great! Up and down my stockinged legs and inside my knickers. He played with my suspenders and twanged them. Then, suddenly, he spanked my ass….hard. And again. And again. I turned my head round to look at him and shouted “owww!” “Shut up slut” was his reply. Next he pulled my knickers slowly down. He continued to grope and spank my ass before he pulled then off all together. He took several photos as he was doing this. Gary came up close behind. He forced my legs open with his knees, as he knelt right behind me. I could feel his cock against my bare ass for the first time. It was so hard! Gary rubbed and scratched my back gently. His hands slipped round the front and into my bra. His fingers tweaked and pinched groped my taksim escort nipples as he groped my breasts. All the time, his hot hard cock was rubbing up and down the crack of my ass. I felt so slutty! He unclasped my bra and gave my back and front a good rub. His touch felt wonderful and his hardon was hot too.“It’s time” he said. The big jar bounced on the bed next to me. The top was now open. It looked like Vaseline. I felt a finger exploring my asshole. Gary rubbed goo up and down my ass crack and he pushed it into my hot virgin hole.And with that I felt a sharp pain in my ass as he forced his big cock into my virgin ass, I had never felt pain like it but I also kind of liked it. Gary kept forcing his cock deeper and deeper not pulling it back just pushing it in deeper until his full length was inside me then he pulled it all the way out and then plunged back in again. The pain was incredible! I screamed out loud! “Noooo….It Hurts! Gary ignored me He just kept on pushing his hard cock in and out of me. I was screaming in time with his thrusts. It felt like he was tearing my guts in two. Gary grabbed a handful of my hard and yanked my head back. His other hand forced my scrunched up knickers in my open mouth, and he pushed my head back down on the bed, forcing my face into the quilt. With one hand gripping my hair and the other hand in the middle of my back, Gary pounded my ass relentlessly. He banged me into the side of the bed. He fucked me like this for ages fucking hard and fast. His thrust moved the bed back to the wall and his continued assfucking was making the bed frame bang against the wall. My ass was still killing me and I was crying my eyes out. But I was just starting to enjoy the feeling. His legs rubbing my stockinged legs and his aggressive grunts and expletives made me feel all sissy and submissive. I felt a sharp pain and heard and loud slap, on one of my ass cheeks. This was followed by many more while he was still pounding his big cock inside my poor damaged ass.He kept hold of my hair and he kept pulling me back on to his cock fucking me even harder and faster than before. I did not think I could take anymore when all of a sudden he thrust his cock deep inside me one more time and held it inside me. I felt his cock unload it’s cum. My asshole could feel his cock twitch as he pumped me full. It felt that someone had turned a hose on inside my ass and it went all slippy. He did not seem to stop cumming for a couple of minutes.His body collapsed on top of me. He was slippy with sweat and I could feel it dripping all over my body. Gary was panting and mumbling. He told me I was his sissy slut and he wanted to fuck me forever. It was quite a few minutes before I felt his cock slide out of my ass. I was so relieved but I also felt so empty not having him inside me. We lay on the bed for about half an hour. I was drifting off to sleep when I felt Gary get up and untie my hands. He lifted me up onto the bed and lay down next to me. We locked each other in a passionate embrace and we kissed and caressed for ages. Gary gently wanked me off. I came on my tummy and Gary scooped it up and put it in my mouth. I licked it off his fingers. I lay back on the bed. I was flushed and spent. Gary lifted my legs up and pushed a pillow under my bum. He wrapped my stocking covered legs around his waist and lay on top of me. And pressed me down into the bed with is weight. It felt fabulous. He French kissed and caressed me again. I surenederd to him. His hard cock was again bumping against my ass cheeks. I moaned with lust, as Gary French kissed me, and I felt his cock enter my ass again. This time there was no pain. I felt so open and slutty. Gary made love to me. I gave myself to him totally. His hot sweaty body on me as his hard cock filled my ass. He whispered lust into my ear as I promised him whatever he wanted. I looked at his face as he spunked deep into my body. The ecstasy and the release as he exploded. I knew then that He owned me, but I owned him too!

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