Dating App

My name's Ben, I'm 21, I'm 5'6 and slim. I've only ever been on dates with girls, I had a short 6 month relationship but that's the most serious it's been. I would say I was curious about sex with men but was always more into girls. I would imagine very submissive women, a face full of make up and them being overpowered by a huge, strong guy when I masturbated. The problem was, as I said, I'm only 5'6. It's not easy to find a girl I'm that much taller than. I'd been single for about 4 months when I decided to switch my tinder details to look for men and women just to see where it took me. I was always clean shaven and slim, I'm not ugly so I thought I would do ok on there. After a few weeks I had very few matches and the conversations went absolutely nowhere. I began to think I was purely straight and maybe I was just confused. One saturday morning I woke up to see I'd been super liked by a guy called Carl, he was also from London, mixed race, he's 6'3 and a gym freak by the look of it. We chatted for a couple of days before he asked me to meet for a drink.

Friday came around and I went to meet Carl in Soho for a few cocktails, when I saw him I couldn't believe the size. My neck would be aching by the end of the night from me looking up at him. He was very polite, we sat and laughing for a few hours. I explained how it was my first date with a guy and how I'd only ever been with women before. Carl worked in insurance and was pretty comfortable financially to say the least, he invited me round his apartment the following weekend for dinner and we left it with a hug at the train station. We carried on speaking through the week and it started to get flirty, Carl started to hint at me being his dessert and asking if I liked a big load of cream after my main course. I was nervous to be honest, seeing as I'd never even seen another mans dick in real life.

The next saturday I made my way to his apartment in Fulham, it was beautiful outside. I couldn't believe my eyes, I could only dream of affording somewhere like this. He buzzed me up, when he opened the door his stood there in a plain t-shirt with his biceps bursting out the sleeves and a pair of grey joggers. I looked down and couldn't help but see the outline of his dick. It was so big I couldn't make out if it was erect or not, mine wouldn't reach that size on it's best day. We ate dinner and it was lovely, we got along so well and had so much in common.

"Let me get the dishes for you, you've made such an effort with the cooking." I said. I picked up the plates and made my way to the kitchen.

"Are you trying to worm your way in already? I could do with a little house wife to look after the place while I'm at work you know?" Carl said and we both laughed.

"You won't find me in a dress anytime soon, sorry to disappoint you Carl!" I laughed from the kitchen.

"Really? I think it would suit you." He said from the dinner table in the front room. As I washed up I called Carl.

"Do you want another wine Carl?" I said.

"Not right now babe." I heard right behind me. I splashed the water all over my clothes.

"Oh my god Carl. That scared the shit out of me." I laughed. I turned towards him and his body was now pressing me up against the sink.

"Thanks for doing this babe, you didn't need to." he whispered looking me up and down.

"Looks like you're all wet now." his hand started to drift down my waist and round onto my bum.

"Why don't you get changed, I have some spare bits in the bedroom." he said. I went to protest but before I could let a word out he leaned his and started to kiss me. This was my first kiss with a guy and I didn't know what to do, even if I wanted to move I couldn't. His body was twice the size of mine and he pushed against me. He had one hand squeezing my ass cheek and another holding my head, his tongue made his was in my mouth and my knees went weak. He took total control and was touching whatever he wanted to touch, I was loving it. His hand started to unbutton my trousers and they dropped, he started to play with my dick and it was already rock hard. I'd never really imagined doing this before but now it all made sense.

"On your knees." said Carl. Suddenly his sweet, charming voice turned to a dominant one. I fell to my knees and his joggers dropped down. In front of my face must've been at least a 7 inch dick and panic set in, his thumb made it's way into my mouth and I started to suck.

"Good girl." said Carl.

"Open wide." he said and he pressed the head of his dick against my lips. I started to guess what my technique was supposed to be, I sucked and started slurping as much as I could while he held the back of my head. He pushed and forced his dick down my throat, my eyes watered and I started to gag, he pulled out before I almost threw up.

"Maybe we need a bit more practice bitch." Carl said as I tried to get my breath back. He grabbed my hand and led me to his bedroom where I sat on the bed. Carl started to go down his waredrobe.

"My ex left a lot of clothes here. Put these on, no arguments." he said. I almost started to regret coming to his apartment now, I'd never been with a guy and this went from 0 to 100 in one night. He threw some black shinny leggings on to the bed, a matching satin, pink bra and knickers with a crop top.

"Your ex was a girl?!" I said confused.

"What do you think? Hurry up bitch." he said.

"I'm not so sure about this you know Carl." I said. Carl put his hand around my neck and started to whisper.

"We both saw how hard you got in there from me telling you what to do, you love it slut. So follow my instructions." he said and he chucked a pair of black heels at my feet. He left to go to the bathroom and I quickly got into the underwear, leggings and black crop top. Luckily the heels fit just fine. Carl walked in completely naked head to toe, it was like his body had been built as example of what a man should look like. He had a beautiful six pack, huge biceps and towered over me.

"Not bad for a first try babe." he said. Carl walked over to me and spun me around. He started to rub my ass, his hands made their way around to my dick then he pulled my leggings down slightly and bent me over the bed.

"Arch your back." he said. I felt a wet finger start to poke at my bum hole, he massaged it until I began to push back onto it.

"That's it babe, take it." said Carl. His finger was probably the same size as my erect cock. He slowly moved in and out and I began to let out high pitched squeals that I didn't know where in me. Suddenly he pulled out and I knew this was the moment. My first dick, I felt like I wanted it so much in the moment. He slowly pushed his dick into my bum and it was agony, it just kept going and going, I didn't think it would ever all be in. Finally Carl stopped pressing and I could feel his ball sack pressing against my bum cheeks.

"You feel that slut? Can you feel my balls pressed against you. Can you feel my dick twitching inside you while you're bent over my bed dressed as a little sissy?" he said.

"Yeah I can feel that." I said in a soft voice.

"I didn't hear that sissy. Tell me again but in a womans voice, tell me what you want now." he said. I was so horny at this point there isn't a thing in the world I wouldn't have done for him. I put on my best girls voice and told him I felt it in me.

"I can feel it, it's so big. I want you to start fucking me. I want you to cum in my bum." I said. I shocked myself, I didn't even know where that came from.

"Oh, she's an eager one." he said laughing. Carl grabbed my hips with both hands and started to swivel his hips around so it was stretching my hole but he wasn't move in or out. He pulled my hips towards him hard, I'm sure I could feel his dick touching my prostate.

"I'm going to make you my slut Lacy, next weekend you'll truely feels what it's like to be used. I'm not fucking you while you look like a cheap sissy whore though. So let this be a taster for you. You know where your place is now, this is where you belong hanging off of the end of my cock bent over begging to get fucked." Carl said. He pushed me onto the bed and his cock came out as I let out a grown. He walked into the front room and I felt so humiliated and degraded. I got changed and walked into the front room where he was watching TV.

"I'll let you know where we are meeting next Saturday." he said to me without taking his eyes off the screen and I made my way out. I couldn't stop thinking about that night through the whole week, every day at work I would go into the toilet to masterbate at the thought of being bent over with Carl's dick in my ass but I hadn't heard a word from him since then.

Friday evening finally Carl messaged me to tell me that I'd be meeting him in Westfield at 9am Saturday morning and I did as instructed. First he took me to a salon where I was waxed from head to toe, Carl took me to a tanning shop next and glued some fake tits to my chest and I came out looking like I'd been on holiday for a month. We walked into Ann Summers with a large jumper on to cover the boobs and I was talked through what would be best for me after Carl embarrassingly explained my situation, the girl handed me pink, satin, french, frilly knickers with a matching corset. I tried it on a tucked my penis between my legs.

"Here try this while you're there." she said passing me a dress into the changing room. She gave me a black, latex dress and a pair of black heels. I looked in the mirror and my body looked sexy as fuck. I had a perfect hour glass figure, my corset sucked my waist in tight and my tits were bursting out of my corset and dress. I slowly wobbled out of the changing room in my heels to Carl and the girl in the shop.

"I love it." she said looking at Carl.

"Yeah. When she's finished I can see her being something special. We'll take it all." he said.

"Carl, I can't walk out of this shop in a dress, I'm a man in a dress. Someone I know might see me." I protested.

"Shut your mouth." he said. Carl pulled me into the dressing room and pulled out a butt plug he must've bought while I was changing, he started to rub my dick and I came almost instantly all over the plug, he smeared it and pushed it into my bum. I opened my mouth wide and closed my eyes. He then grabbed my limp dick and placed it into a small metal cage, locked it and tucked my cage back into my knickers. It was like an out of body experience where I can only stand and watch what he was doing to me. I pulled my dress down and we walked out. I kept my head down as Carl took me outside and in a shop close to next door.

I had a long, dirty blonde wig glued to my head and styled before the woman gave me long french tip nails, she painted my toenails pink to match my knickers too. In the next two hours I had my ears pierced with some small studs put in, my eyebrows were plucked into a thin line and an arch. My lips were pumped with filler and my face was caked in make up. False eye lashes were put in too. I came out looking like a girl who would reject me in a flash. I thanked the lady and I walked out a new person, my hips swaying and unrecognisable from who I was this morning.

Carl put his arm around my waist and we walked through the shopping centre, I was getting stares from guys left right and centre. I felt so hot walking with my man. He took me shopping for a bracelet, necklace and some rings as well as a new handbag. I felt like a spoilt brat. I'd never been treated like this is my life, I normally struggled to find a girl and when I did I would half most meals with her and not buy her many gifts. Now I'm being shown how to treat a woman by a real man. With every step my tits were bouncing and the butt plug was shifting inside me. If it wasn't for this cage I'd be erect again.

When we left we got into his Ferrari to drive back to his place and I thanked him.

"Thank you so much for today Carl, I feel like a different person. I never knew this was what I wanted but I look so hot, I hated how I looked before." I said smiling.

"How about showing me how thankful you are, let me see how good those lips I paid for feel." he said as he unzipped his jeans. I leaned over as he was driving and started to suck his cock. I felt like an actual whore and I loved it, I sucked his dick all the way home without him cumming and we made our way up to his apartment.

"Ok, you want to see how it feels to be a woman? I'm going to show you how it feels bitch." he said walking through the door. I started to kiss him and threw my arms around him, but Carl aggressively pushed me back and I stumbled on my heels and fell onto the sofa. He pulled his trousers and boxer shorts off as I tried to find my feet again.

"Get your pussy over here bitch." he shouted. I stood up and leaned on the arm of the sofa to find my balance then suddenly I felt Carl lift my dress up from behind and he spun me around to face him. Before I could do anything about it he lifted me up and threw me over his shoulder.

"Oh my god Carl, you're so fucking strong. I love it!" I said laughing.

Carl pulled my knickers to the side and pulled my butt plug out. I let out a big moan.

"Oh wow. Carl be gentle with me please, it's my first time, maybe if I'm bent over it might hurt less." I suggested while bent over his shoulder.

"You honestly think I spent all day transforming you into my little fuck doll, spending all that money for you to tell me how I'm going to fuck you? You're as thick as you look slut." he said. He started to lower me down his chest and the head of his dick began to poke my ass. He found my hole and started to make his way in, he now had one arm on my lower back holding me against him and one on my right thigh holding me up. His dick was deep inside me when he began to make me bounce.

Both of my legs were now wrapped around his waist and my arms over his shoulders. Carl was lifting my body in the air and every time gravity pulled me back down I was being impaled by his monster cock. He was fucking me deep and hard, I started to scream. My head flew back and I closed my eyes, I screamed with every pump. My tits where pressed against his chest, the feel of the latex rubbing against his body was making me hot and flustered. I couldn't handle so much pleasure at once. I had absolutely no control over what he was doing.

I was being thrown around like a rag doll, bouncing up and down on his cock until he didn't want it anymore. We were both sweating, my forehead rested on his as he stopped for a quick break before going again. He collapsed onto the bed and his body engulfed me, if someone walked in the room they would just see him on all four with some legs sticking out the sides with my heels in the air. He fucked my bum hard missionary and my heels stayed pointing to the sky the whole time. I began to think Carl would never cum, he fucked me for around 25 minutes before he pulled out and bent me over on all fours, I was fucked again and spanked for the next five minutes.

Two weeks ago I wasn't sure I was even bi, now I was on all fours having my bimbo brains fucked out and begging for me while dressed as a slut. He kept going and going, he's a machine and my bum cheeks just kept slapping against his balls. He reached for both of my arms and pulled both of them back behind me. He lifted me towards him and I could almost feel his chest against my back, we were both now on our knees and his dick is buried in my ass while he gives me short sharp thrusts. The sound of my ass cheeks slapping his balls made my chastity cage twitch hard. He grabbed me around the throat and started to choke me before he let out a moan.

"Ahhhhh, fuck! Little slut! Fuck!" he shouted.

Finally Carl pulled out and push me onto my back. He stood up next to the bed and grabbed the back of my head, he slammed his dick into my mouth and exploded his huge load down my throat. I started to choke and swallowed as fast as I could, Carl was bent over the bed while I was laid on my back, his hand underneath my head and I had nowhere to go. More short sharpe thrusts came as he emptied into my mouth, with his balls resting on my chin he just stayed there letting me take every last drop. He held my head on his dick until it was almost flaccid.