I loved to look through porn magazines like Mayfair and razzle and often set out to buy a new one, I’d chosen a quiet corner shop I knew had lots adult magazine’s on its top shelf, I hung around browsing till the shop was empty and quickly started to look through the magazines on offer.
I was quite exited when I saw a magazine call stiletto heel, it was a contact mag with lots of adverts with pictures, I had to have it. I was only 16 but the shop owner only ever asked if I was sure i wanted to buy it as he served me and put the magazine in a brown paper bag and gave it to me.
I cycled home and took it to my bedroom, luckily no one was home and I had time to look though it properly wile playing with my cock, I got so turned on by the adverts I couldn’t help slipping a finger in to my arse, it wasn’t long before I came looking at an advert by a male, 40s loves rubber, looking for a younger person to play with, must enjoy receiving anal and giving oral, prefer sissy boy. And there was a phone number.
I was use to wanking over girls but the picture of the man in a rubber mask, gloves and pants made me so hard, I spent the next few evenings getting very turn on over his advert till I got so turned on I had to call him.
I chose to use a phone box and set off in the erly evening my cock all ready hard to make the call, I was surprised when he answered and a well spoken man said hello, It took me a few seconds to reply and say I had see his advert, he asked me to tell him which one and from what magazine so I did and he asked me a few questions about my build and hair colour . I’m slim build with long blond hair I said, he asked me about how often I played with my bottom and if I liked to ware stockings and suspenders. I was honest with him and told him, I loved to finger my bottom whenever I played with my cock and I’d only worn stockings and suspenders once and it made me very hard. it wasn’t long before he asked me weather I’d like to come over on Friday evening and I said yes very eagerly as I was incredibly turn on by now.
He told me he would be waiting for me and when I arrived I was to put on the outfit in the hall that would be on a chair and he gave me his address.
I was so excited all week and when Friday came I couldn’t wait and I was knocking on his door the moment I was expected 8.00pm sharp. The door opened on a very nice hallway and a voice said come in. In the middle of the hall was a chair with clothes on it, I walked through the door and up to the chair, he said don’t turn around as the door closed, I stood still he said now be a good boy and slip in to your out fit, ill help you if you need me to he said. I was trembling as I got undressed knowing he was watching me and I had not seen him yet.
I started with the stockings, black seamed and the black suspender belt then a rubber corset which I struggled with and he helped me in to it standing behind me. The corset stopped just short of my nipples leaving them exposed. Then I saw the rubber pants as I pick them up he said the opening goes at the back, I stepped in to them and pulled them up my legs, the front of the pants had a tight pouch for my cock and balls and he helped me in to them as I pulled them up tight leaving my arse exposed as the rubber held my arse cheeks open. I struggled in to elbow length black rubber gloves and saw a pair of high heels under the chair so I slipped them on one at a time having to kneel down to fasten the straps.
He said stay on your knees and turn round, as I saw him for the first time my head was at his crutch hight, his 7″ slim cock was very hard with pre-cum on the tip, he was waring a pair of pants just like mine but the opposite, his cock was exposed and his arse encased in rubber, he also had black rubber gloves on, i looked up to see his rubber masked face gazing down at me. His hand cupped the back of my head and pulled me toward his cock, I opened my mouth and he pushed his cock between my lips. He very gently fucked my mouth, I could taste his pre-cum and it tasted good. I started to suck his cock as he slipped it in and out of my mouth only using a couple of inches. He pulled out of my mouth and said good sissy now stand up, which was tricky as I’d never warn heels before and he led me tottering to his living room.
He guided me to a large black p.v.c covered sofa and i sat on the edge and looked around the room, there was a coffee table in front of the sofa with a selection of sex toys on it, I recognised a butt plug and a vibrator. He sat down next to me, he said sit back and relax we’re going to watch some porn together and pressed play on his video remote.
I wiggled back on the sofa and he put his left arm around me, he stroked my long hair and my shoulder wile his right hand started to caress my stocking tops, I looked down and i could see the bulge in my rubber pants, I reached down and took his cock in my hand, It felt so hard and he said good sissy. He reach out and picked up a small bottle which he opened and asked me to sniff, i inhaled five times through my nose, the smell of poppers made my body rush, he put the bottle down and lubricated his fingers from another bottle on the table, then he got me to slide down on the sofa till my bottom was exposed over the edge of the cushion.
His gloved hand went straight to my arse hole where he rubbed the greasy lubricant, I let out a moan and he laughed and said I want you to watch the movie I put it together for you, it’s got all the things I’m going to do with you in it and all the different positions I’m going to have sex with you in so pay attention wile I play with you, you can sniff as much poppers as you want to help you relax. I was trembling as I took a few long sniffs and felt his fingers running around my arse hole.
I was trying to keep an eye on the movie while his left arm moved from my hair to my nipple and his right hand worked between my legs. He sat so close to me I could feel him pulling me up tight to him, my bottom relaxed and his finger slid in to me making me moan and he encouraged me saying oh yes good sissy boy let me deep in side you and with a push he was up to his knuckle, it felt so good, I’d never had anyone play with me before and I started to grind against his finger. He smiled and said good little slut, you like that don’t you, oh yes I said it feels so good, he said just wait till my cocks in you. I was still holding his cock in my hand and I looked down at it, his right hand slid back to behind my head and he pulled me close to his masked face and started to kiss me, I felt so helpless with his finger moving around in side me, I kissed him back deeply.
My bottom relaxed more and he worked another finger in to me wile we kissed making me gasp, he pulled his face away from me and said watch. Laid back my legs wide open and watch a compilation of sissy boys being fucked in every conceivable position. He kissed my neck and up to my ear then started whispering filth to me. Telling me the names of the positions I was watching from doggie to cow girl and saying he was going to fuck me like that, there where so many positions, cute lady boys sucking cock and having there bums filled with cock and cum, I’d never see anything this dirty before, he was working his fingers backwards and forwards two fingers up to the knuckles and my breathing quickened, he said good little bitch cum for me and worked his fingers harder and faster making my arse cum around his fingers, I moaned very loudly, he kissed me hard keeping me quite while he made me cum with my arse. I wriggled around on his latex encased fingers. He slowed his pace down till he slid his fingers out of me and immediately picked up the butt plug from the table and started to slowly insert it in to me making me moan some more, my bottom was relaxed enough to except it and it slipped in making me gasp, he massaged the base of the plug making it move around in side me and making me wiggle, he run his hands over my rubber encased cock and ball and said did you make a mess in you pants sissy, I looked at him and sad yes sir, good sissy boy there’s going to be a lot of mess in your pants by the time im finished with you. He run his hand up from the front of my pants up my corset to my nipples and said let’s watch the end of the film and have a cigarette down here then I’m going to take you up stairs in my bed room, I took a cigarette and he gave me a light then poured me a glass of wine,I sat on the butt plug trembling with excitement as I smoked and drank the wine. As soon as he put his cigarette out he started to run his hands over my rubber clad body. I finish my cigarette and drink wile he was rubbing my cock through my pants I was now rock hard and making a large bulge in the restricting rubber.
He said come on sissy and stood up he helped me up the butt plug moving in side me as i stood up, he gave me his hand and helped me tottering to the stairs and up to his bedroom. It was a large room with a king size bed with rubber sheets, his hand was cupping my arse cheek as he guided me to the bed and said sit down, I sat on the edge of the bed and he knelt down and took off my shoes caressing my stocking clad legs making shivers run up my body, he stood up and his dripping cock was at my head hight and I took it in my mouth eagerly, he let out a moan as I started to suck on his cock, I copied what I’d see in the porn and using my tongue on his balls and sucking his cock as deep in to my mouth as I could, I was realy enjoin his cock in my mouth and grinding down on the butt plug in my arse. He kept on encouraging me by saying good slut and telling me how he was going to fuck me soon . I looked up at him while I sucked and licking him. he put his hands on my shoulders and pushed me back on to the bed his cock slipping from my mouth, he straddled me and crawled over me untill his balls where over my mouth and my arms beneath his ankles pinning me down. I was helpless as he lowered his balls in to my waiting mouth, I was so existing as I sucked his balls in to my mouth his cock on my face. His hand went down to the plug in my arse and he started to work in around and in and out making me moan around his balls, I opened my legs wide to give him better access and it wasn’t long before he slid the plug out of me and took his weight off my arms, he slid down my body and took hold of my ankles lifting my legs up high and knelt down between my legs, he said you haven’t done this before have you and I stammered no, he replied I’m going to take your virginity and your going to be my bitch. I watched as he took hold of his cock and started to rub it against my well lubricated arse, it made me sigh, it felt so hot as he started to push it against me, my bottom relaxed and let him in side, I said oh my God as he slid in to me he kept pushing gentle till I felt his balls press up against me. He said there you go little slut, he put his hands on my shoulders and started to withdraw slowly making me moan, he bought his masked face close to me and said good slut and pushed back in to my arse as he pushed his tongue in to my mouth and started kissing me.
I lay there lost in lust his cock slipping in and out of my arse his hand in my hair his other hand caressing my rubber clad body, I put my arms around him and and held on as he took me to a big anal orgasm my arse squeezing his cock, he said good little bitch in my ear, he pulled his cock out of me and told me to get on all fours, I was still breathing heavily from cumming so hard as I roll over and offers my arse to him. I felt his hand on my buttocks then his cock was pushed back in to me making me moan loudly. The next thing I knew he pushed a ball gag in to my mouth and secured it behind my head and started to fuck me hard and fast holding me by my hips. I was grunting and dribbling around the gag as he took me hard. He whispered in my ear your my bitch now and slammed his cock in as far as it would go. I came around him again, I’d lost all control and wet my self in my rubber pants. His grunts and moans filled my ears as I was fucked hard in my arse, I was loving being helpless and taken like a dirty bitch, I found myself pushing back on to his cock wanting more. He said it’s time to show me how much you realy like it and pulled out of me he undid the gag and I gasped in air as he lay back on the bed his head on a pillow, ride me slut he said so I crawled over to him and straddled him bringing my arse up to his cock, I felt embarrassed and he could tell. Take hold of my cock said Geoffrey, so I did and started to guide it to my arse, he reached out and took my nipples in his rubber clad fingers and started to twist and pull them hard making me moan, I slowly sat down on his cock feeling it slide deep in side me till I was sitting on his Lap. Ride me he said, enjoy my cock in you my little bitch. Slowly I started to grind on him then I started to ride up and down forgetting all about my embarrassment, I was now riding him like I’d see in the porn film. He caressed me running his hands up and down my rubber corset, I was in heaven his cock deep in me and I came again this time a hole series of smaller anal orgasim’s shook me he was smiling and said I’m not going to last much longer if you fuck me like that slut. He took hold of Me and rolls me on to my side his cock deep in me and said I’m going to spoon you for a wile, his arms around me he slowly fucked me, it felt amazing being fucked on my side him whispering filth in my ear, I was a trembling mess my pants full of cum and pee I had totally surrendered to him and his cock and he knew it. He said he was going to cum in my arse soon and that I was going to enjoy being filled with his spunk. Once I’ve cum in you I want you to put the butt plug back in to your arse then suck and lick my cock clean, i replied yes sir, he pushed me over on to my front face down on the rubber sheet and started to fuck me hard making me bounce on the mattress. Within a few strokes he lost control and spewed his cum deep in side me making me cum once more, he kept pounding me till every drop of his cum was in me, his last few thrusts felt sloppy and squelchy, he pulled out slowly and rubbed his messy cock around my spunky hole. He slumped back on to the bed and I took the butt plug and pushed it in to my well fucked spunky arse. It sank in so easily. My gloved fingers where all sticky with his cum so I sucked them clean as he watched.
I slid down the bed dripping with sweat and still breathing heavily i started to suck and lick his cum from his crutch licking his balls clean then cleaning his spunky cock. I was even more turn on now i couldn’t help playing with the plug in my arse as I sucked him clean.
He said your such a good little bitch have a few minutes rest and offered me a cigarette he asked me to pour some drinks and we sat and he put on some more porn on the tv.
I was fizzing with excitement as I sat drinking and smoking the spunk in my arse held in place by the plug and my pants looked quite full of mess.
He suggested that we empty my pants next and that he needed to pee, he guided me to the on sweet bathroom and had me stand over the toilet wile he pulled my pants down just enough to let the pee and cum dribble out. He said you are a very messy sissy boy and gave my arse a light spank.
Once my pants where free from pee he pulled them up and said it’s my turn now slut and had me sit down on the toilet, I was looking at his semi hard cock he told me he was going to pee in my mouth and that I could drink it if I wanted to. Straight away he started to pee in my face aiming at my mouth, I felt so submissive by now I opened my mouth and started to drink his warm yellow fluid, I was surprised it tasted good and I started to gulp it down. I looked up at him and he was smiling and saying good slut you are a filthy little whore arn’t you, I nodded and kept my mouth open for him to piss in.
My cock was rock hard in my tight rubber pants, I had no idea I could be this turned on. As soon as he stoped pissing he helped me up and kissed me deeply his tongue exploring every inch of my mouth. He cupped my buttocks in his hands lifting me to tiptoes and spoke in to my ear saying I’m going to fuck you again soon slut and led me still dripping piss back to the bed. I lay next to him holding his cock in my hand his hand between my legs playing with my butt plug. We kissed and roll around on the rubber sheets, I was lost in a world of filth, all I could taste was piss and cum and I could smell the rubber and It was exquisite. My arse ached to be fucked and I found my self begging him for his cock. He smiled at me and said I was hoping you’d be craving my cock by now, which position would you like me to fuck you in slut. I replied doggie and got on all fours and wiggled my bottom at him, I had my head near the foot of the bed so I could watch the porn that was even dirtier than what I’d see down stairs, a cute boy in bondage was being fucked by four men, they where taking it in turns on him one in his mouth and one in his arse he told me it was called a spit roast.
I felt him slide the plug out of me and push his cock back in to my spunk fill hole and he started to pump me slowly and deeply, he bent over me holding me by my hair he started to bite and kiss my neck his body bearing down on me as he fucked me. I could hear squelchy sounds coming from my arse as he fucked me, my bum was dripping cum and I loved it.
It wasn’t long before he made me cum again which made me collapse face down on the bed but he kept pushing his cock in to me, I was moaning and panting as he used my arse for his pleasure.
He fucked me and screwed me from doggie to spooning then he roll me on my back and I opened my legs wide for him and pulled them up to my chest so he could mount me easily, I adored being fucked in the arse and he knew it. With his tongue in my ear he said I was going to be his fuck toy and he was going to use me as he wanted, I said yes please out loud. He made me cum again fucking me hard and deep and when I was a quivering mess on the bed he pulled out and straddle my face pushing his spunky cock in to my mouth and holding my head between his legs. I sucked his cum cover cock as he fingered my messy arse. He said I want you to ride me again bitch and sat down leaning back on the head board, I dragged my self up to him and he said turn around and ride me reverse cow girl this time so I did, squatting over him my dripping arse took his cock so easily I found myself laying back against him grinding on his cock as he played with my nipples his mouth by my ear encouraging me to watch the porn and to enjoy his cock which I did. I made my self cum twice riding him It felt so good I heard his breathing quicken and he held me tight and started to thrust up in to me, I’m going to cum in you again slut. Followed by make me cum you little whore, so I rode him harder and faster bouncing up and down on him all shame forgotten, I could feel his cock start to throb and twitch in side me as he started to shoot his second load in to my aching arse hole.
He was grunting and breathing heavily as he finished in side me and held me tight saying I’m going to stay in side you till I go limp slut. I replied yes sir and felt his cock twitch deep in me. We stayed coupled for five minutes or so untill he slipped out and I couldn’t help my self from turning round and sucking his limp cock clean.
As soon as my lips left his cock he had me lay next to him his gloved hand went straight to my arse and his finger slid in side as soon as it was deep in me he pulled it out and offers it to my mouth, I sucked on it greedily licking his cum from his fingers, he kissed my spunky mouth as he fingered more cum from my arse we lay kissing with cum as he fingered his cum from me, I was loving licking his cum off his fingers and kissing him we laid there till his fingers came out of me spunk free.
I felt totally shatters laying on his bed he said I could sleep if I wanted to but I might have to fuck you later slut and I passed out.
I woke up with his cock deep in me, I was laying on my side and he was gently screwing me, he said welcome back I just couldn’t wait any longer slut, he put his hand over my mouth and quicken his pace. He whispered in my ear that he wanted to cum in me one more time tonight and he was going to use me all weekend, that was enough to make me cum so hard I passed out with him still fucking me.