Brian and Alice - Dir Shemale Stories

By Kinky Monkey

Published on Dec 11, 2009

Transgender

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This story was inspired by one written by another author about a shemale called Tina. I've just made it more hardcore. k1nkymonkey@hotmail.com


Brian meets Alice, a tall sexy asian chick in a bar. Brian is bi and Alice is horny. They get talking in a bar and as they get drunker the conversation turns to sex. Brian admits that he's bi, but is more into women because although he can find cocks a turn on, he's not really into men. Alice admits she's not entirely a girl, and has something extra in her pants, which only serves to turn Brian on more. One thing leads to another and they end up back at Brian's place, and start making out. Here's his story...

The making out didn't last for very long. Alice soon rose to her feet pulling me up with her. Once I was standing, she knelt down, and undressed me, fingering my erection through my boxers. She kissed my cock through the silky material, sucking a little on the wet patch caused by my pre-cum. Then suddenly pulled away and looked up at me as something occurred to her "By the way, do we need to use condoms, cos I don't have any with me?" she asked. "Well yeah I usually do. Might as well be safe right? I've got some in my wallet though so don't worry."

I reached over and pulled out my wallet. "See here's a couple. They should last us" I said. Still kneeling on the ground, she rocked back on her haunches, took them from me and stared at them, looking a little worried.

"Err well, I don't think these are going to be big enough," she said.

"Ah don't worry I've already tried them," I said. "They're extra thin for maximum pleasure too" I winked at her. "Joking aside though, I know they're japanese, but I've tried them. I'm not small and they're easily big enough and pretty comfy" I said as freed my cock from its confines to make my point. Alice fingered my 7inch erection, running her slim fingers along its length. She looked more uncomfortable before finally mumbling "Erm well they're not going to be big enough for me".

"Huh? Sorry? Don't worry. They're really normal size. I've never had a problem"

"Erm yeah I know baby." She stretched my cock out. "I can see they'll be fine for you, but your prick is pretty small compared with me. Mine is a lot bigger than this." She fingered my length. "I don't think these condoms will even go past the head."

It took me a second to process what she meant. "Are you serious? But you're Asian! I always thought..." She shook her head at me slowly. My cock pulsed in her hand. I'd never seen a cock too big for a normal condom. I didn't know whether to feel emasculated or horny, but horny won. "Oh my god! Really? Can I see it?"

Slowly she stood up, pushing me down to the bed so that I was sitting eye-level with her waist; my heart beating faster as she slowly pulled down the zip on her jeans and then bent over to push them down. When she stood back up, I could see her lacy underwear bulging at me.

Alice hooked her thumbs around the elastic waistband of her panties and began to pull them down. The first thing I noticed was the sizable patch of dark pubic hair. It was natural, not shaved. Most asian shemales shave to make their cocks look bigger, but I was beginning to guess Alice didn't need the help. She continued pulling her panties down and I saw the wide base of her cock where it met her body just below that thick forest of hair. She kept pulling and more and more inches of girl meat were revealed. At last, her purple head sprang out. She kept pulling her panties down to her knees and then stood up straight for me to inspect her.

It was glorious. Her cock had to be at least 8 inches long in its soft semi-erect state. It dangled down, thick, but proportionate for its length. No wonder the condom wouldn't fit when she fully erect. I wondered if I could get it in my mouth. She had been circumsized and her organ was capped with a big flared purple head. Her sack too was a sight to behold as well. It hung low between her firm long thighs, the weight of her huge balls being pulled down by gravity, and covered in long, curly black hair. It was erotic and mesmerizing.

But don't get the impression that this enormous package and the hair did anything to detract from Alice's beauty. In fact, the opposite was true. Her cock and her nuts provided the perfect contrast to the rest of her - making her seem even more alluring.

"Do you like it?" she asked "I mean especially as you're going to have it naked inside you since the condom won't fit. Are you ok with that?"

That stopped me too. I hadn't imagined Alice would be the one fucking me, but then looking at her large organ I knew that she could only be a top with something that size.

"Alice, it's really intimidating" I said, and added, "but in a good way. A very, very good way."

"Thank you," she said, blushing. "You don't think it's too big?"

"I just hope you don't think mine is too small!" I said holding my cock out to hers. She lifted her semi-erect cock up to mine and looked embarrassed when she noticed she was already at least an inch longer and easily thicker without even being fully aroused. We both laughed. "But I like your cock. Its smaller but its so cute" She teased, but when I pouted, she kissed me before squeezing it and adding. "And its still manly to me."

I reached out and cupped those heavy testicles, savouring the feeling, and then bent down to kiss and lick her ballsack so that I could feel the hairs tickle my tongue. I lapped at the underside of her cock and Alice began to moan.

She began to thrust her hips gently as I squeezed her into my mouth.

I pushed Alice down to the bed, face-down, and spread her legs as wide as she could on the narrow mattress. I knelt between her feet and lowered my face to her lovely rump. I dove in without bothering to use my hands. I found the hole at once and began burrowing as deep as I could with my tongue.

As I licked and sucked her asshole, she began to raise her body to a crawling position. I'm not even sure she was conscious of doing it. Regardless, she was soon on her knees, with her face against the pillow. Her beautiful, egg-like balls dangled right before me, teasing and tantalizing me. I reached out and cupped them in my hand, fondling them gently as I continued probing her nether regions.

I was scared but couldn't help looking forward to sucking on those heavenly balls and that divine cock, and feeling the latter inside me. I turned her over and saw that she was now almost fully hard. I gasped at the increase in size. I'd been impressed before, but it never occurred to me that her cock would get so much bigger. She giggled at me.

"Sorry hun. You reminded me of my brother when we were young. Its obscene isn't it? My brother nearly had a heart attack when I first entered his bed as a teen."

"You used to fuck your brother?" It threw me off guard, but my cock got even harder.

"Oh no. Sorry I didn't meant to tell you that!" She sat up aghast.

"No, no don't be silly. That's so horny. My cock's about to burst!!" I took her size in both my hands. "Tell me more"

Still looking at me, she thought about it, then I felt her twitch and expand a little more. This was obviously making her hornier too.

"My family realized I was going to be a girl when I very small so I always looked and dressed like one, grew breasts and everything as normal but only my mom knew something was different about my cock. I remember her helping me dress one night when I was 8 and telling me that my cock was already much bigger than my brothers, poor guy. We giggled about it but I think she must have assumed that I'd just reached full size quickly cos I was already about 5 and a half inches I think."

"Anyway I started growing breasts and pubic hair at about 13 and by 14 was already huge but only I knew about it. Then one day I noticed my old brother masturbating over a picture of naked breasts and moaning my name. He was 18 and almost fully grown by then. I got really hot and hard and for days the thought kept me excited and horny, and finally one night when my parents were away I gave into the pressure."

"I was really horny and I couldn't sleep so I crept round to his room and looked in. I could hear him sleeping with his back turned away from the door so I entered really silently not to disturb him. I was already nearly hard and I was conscious of the huge tent my cock was making in my nightie but I was too far gone to care."

"I knew he always slept naked so I shucked off my nightie and slipped under the covers behind him and pressed my breasts into his back while slipped my hand around his chest and down his belly. I was a little surprised that I could hold his entire prick and balls inside one hand. He was grown up but they felt so small to me."

"And that's when he woke up. Shhh its me Alice, I told him. Its ok. I'm really horny."

She laughed as she remembered, her cock now throbbing in my hands, precum leaking onto my lips as I kissed her hole. The head could now barely fit in my mouth. There was no way I could deep throat her, so I just kept stroking and licking.

"He went completely stiff as he thought about what to do, and then as realization dawned I felt his cock go hard in my hand. This was my first cock other than mine and it felt strange that it was so slim and short and yet so hard. It felt like a finger to me, but of course that's only because I was used to that." She said pointing at the organ I was savouring.

"Don't stop" I breathed.

"Anyway as I fondled him, he slowly came to life. Up to this point I'd kept my groin well away from him because I didn't know how he'd react. I knew he knew I had a cock but I know he thought of me as a sister. But the weird thing was that he moved his hand back and went straight for the area between my legs rather than my breasts. I froze while his hand moved back, and then hit the tip of my cock. I can still remember him feeling around it like he wasn't sure and then starting to move down the length, as I squirmed closer to him. I remember the audible gasp as he realized it was really my prick he was holding. It was about the length of his forearm by the time he got down to my balls. In my hands his cock began to throb and suddenly exploded all over my wrist, but I never let it go. I just moved closer. I knew I had to fuck him. I was sooo horny. I think he knew what I was going to do, and I could feel his heart-rate go."

"with my cum filled hand I lifted his right leg away from his body and moved a little down so I could position my cock at his entrance."

"The amazing is neither of us had done this before and we didn't even know what lube was, but somehow I knew I could enter him this way and so did he."

"I mean I wasn't much smaller than I am now but somehow he still took it." I tried to enter but obviously failed, and then being young and impulsive just lifted his leg higher and then just shoved. Wow he screamed but I was in. The feeling was so awesome. I kept pushing until I'd got about halfway and then I could feel it wasn't going any further. So I just pulled out a little and pushed in again and it felt so good. We were fucking! He was still crying a little, but now I could hear moans and when I slipped my hand round his front I could feel him hard again."

"I could feel his bigger frame arching against me every time I entered him deeper, and it gave me a real thrill to know that my older brother was so under my power – impaled on my cock like that. I held his cock and felt so in control, and then it was all over. I had the most powerful orgasm I've ever experienced, and it felt like I was coming forever inside him."

"When it was over we just lay there. My cock still buried halfway inside him. I was just clinging on to him as I trembled from the power of it."

Finally I pulled out and we both lay there on our backs in the dark. Just breathing.

"Then suddenly he turned the lamp on and rolled over onto his side to face me, his eyes staring at my now slick limp cock."

"In the light I could see I he was hard again, but his fully extended prick wasn't even as big as my soft one." That's when I saw his face and it looked just like yours when you first saw me. It was so lovely.

"He just reached out and lifted it. We still hadn't spoken as though it would break the spell. I lay back staring at his thick pubic hair – he had a lot more of that than me as he was older.

And somehow I just got harder again in his hands. His expression kept getting more and more wide-eyed as I expanded to my full length in his hands. My cock had gone almost upto my breasts. And then I don't know what made me do it but I just pushed his face towards my cock, and he just opened his mouth like it was natural and began to suck it clean.

I was still so horny and I had to feel that tightness again so I moved and sat up and pushed him on his back. I think he knew instinctively what I was going to do and made room for me between his legs. Now my huge girl cock hung over his belly, dwarfing his, and his eyed were just fixed on it. I stepped back and for some reason he just lifted his legs up, just like a woman – of course I didn't know that at the time, but it was so erotic. He was just offering himself to me, completely under my power. This time it was easier to enter him and even though there were tears they were accompanied by moans all the way. I remembered bending him over and fucking him so hard. I feel bad now, but how could I have known! I'm pretty sure he loved it. This time we lasted much longer. He came about halfway through, spurting all over his own chest, and then he came again – less this time, and then he began to have dry orgasms until finally he pleaded with me to exit almost just as I was about to cum. I was already pulsing as I pulled out and spurted from between his legs on to his face, and then stepped back from the force of it only to continue cumming all over his cock and belly. It was so wrong to see my brother lying spread eagled on his back with his cock covered in my cum, but it was so erotic."

"I fucked him for years after that. By the end he could take all of me. And very few people can say that. He used to walk around in just a tshirt when my parents were away so that I could enter him whenever I wanted"

Alice and I switched places so that now I was the one lying on the mattress. I was on my back and Alice was on top of me. Alice's hanging scrotum was suspended over my chest. I marvelled at the size of her balls and the sleekness of the cock which hung down over my face. I knew I couldn't keep staring at them without touching them, so I distracted myself by lifting up my head and kissing her tip.

Slowly she moved her hips backwards, her face still over mine eyes locked with me, until finally she was half lying over me her long pubic hair brushing against my thighs as she lay the swollen, pulsing head of her cock in between my thighs. I felt her pee hole steadily leaking precum onto me.

She lay on me and we kissed passionately, grinding our cocks together until slowly I pushed her away and pulled her up my body again, until her cock was within touching distance of my lips. I lifted my face, taking the top of her dick into my mouth. It felt steamy hot inside and I released a moan that was muffled by the flesh which was currently buried in my face. I ran my tongue all around the shaft, savoring the taste. I moved down again, taking more of her inches, and soon was bobbing up and down.

She reached back and began to fondle my balls with one hand. That pushed me closer to the edge than I wanted to go right now. Still, it was hard to break away from this incredible sensation,

"I want to feel myself inside you," she said. "Are you ready?

"How . . ." I began. "I mean, what do I do? You're huge. I can feel how big you are just lying on me. How do we do it?"

"Depends on what position you want to be in. Do you want to be on your hands and knees? Or on your back like a woman? Or like a spooning position, on our sides with my front against your back?"

"I want to be on my back, I think."

"Great. Good choice."

She rolled off me as I excitedly swung my legs up, kicked off my shorts, and lay naked before her. She smiled at me and reached up to fondle my package for a moment before moving between my legs. Her long hard dick fell down against my stomach. I admired the beautiful girl about to fuck me, her stunning black eyes, perfect breasts, flat stomach, and her magnificent girlhood.

The tip of my cock touched hers and a string of her precum stretched out between us as she lifted herself. I took it in one hand to keep it steady and carefully moved my hips forward. Her tip touched the sensitive area between my cheeks and I sucked in air with a hiss, but she smiled at me, encouraging me. She forced the tip through the stretchy ring, groaning until the head was inside me. I could barely breathe as my sphincter tried to expel the massive invasion. I pushed harder through the sphincter, knowing it would hurt at first, but feel delicious once it was past this final wall. Alice closed her eyes and clenched her teeth.

Finally, it broke through, and the rest of her cock slid halfway inside me. It felt like I was being separated by her cock.

"It's nearly threequarters in," she breathed. "How does it feel?"

"I can't describe it," I whispered. "Amazing. Wonderful."

"It feels that way for me, too."

She kissed my ankle and began to withdraw her cock from inside my bowels. She took it about halfway, then eased it back inside. Back out halfway, back in again. She would suck in breath as she entered and exhale as she withdrew. I told her to try to breathe normally and, as soon as she began to do so, there was a change in her posture. She seemed much more open, somehow. I took this as a good sign that it was time for the real action to begin.

She began to pound me faster, being careful not to do it so fast that I blew my load before we'd had time to savor this as much as possible. Alice closed her eyes and I took the opportunity to admire her breasts as they bounced ever-so-slightly up and down. The loose skin of her scrotum was pulled tight by gravity, showing the outlines of her testes underneath, and I practically drooled. I wanted to pop them in my mouth and suck on them like a nursing baby.

Soon, the room was full of the sound of her sack slapping against my butt as her pace increased. At first, her hands were jacking me off until my moaning became so loud that she used her hands to cover my mouth and muffle the sound. But she seemed to forget about noise control and, within minutes, her hands were massasing her breasts and holding my ankles in place. She started moaning so loudly that people on the other side of the wall must've heard us but neither of us was concerned with that.

I felt an orgasm approaching but she slowed down to the light pace of earlier. Her moans turned to sighs. She spoke unintelligible words as if she were talking in her sleep. Her hands wandered all over my chest and up my legs, enjoying touching my body as she made love to me like a woman. Without warning, she increased her pace again, and I was suddenly groaning with near-orgasmic pleasure.

"I'm getting close," I said, as she pounded me faster than ever.

"Please, Brian . . ." she murmured.

"What is it, Alice?" I asked.

"I need to cum," she said. "I need to cum but I want to cum on you. I want to see your cock covered in me"

"Do it," I said. "cum on me."

"Are you sure," she protested, but weakly.

"Please," I begged. "We need to cum. Let's cum together."

"OK," she whispered. "Just hurry."

She pulled out. I could feel my balls churning. I grabbed Alice's massive dong with one hand and began to jerk it. She cried out as a long, sticky burst of white cum shot from her cock and splattered across my chest. Another one followed. I kept jerking her until my hand, cock, balls and belly were covered with her huge load of semen, then I quickly grabbed my own cock. Using her cum on my cock as a lubricant, I jerked myself off, until I shot my own load right at Alice's gorgeous package.

While Alice rolled over and lay there, panting heavily, I leaned down and began to smear my cum over her cock. I then licked the jizz from her body. I slurped up the first load and a few scattered ones that landed on her tits. I drank thirstily from the white pool of her navel and even licked up the last remnants that had dripped into her pubic hair.Once I had finished it all, I collapsed down beside her. Alice snuggled against me and put her arm around my shoulders.

"See, that wasn't so bad, was it?" she asked.

"I felt like I was going to explode if I didn't cum," I said with a small Laugh as she slipped her hand between my legs and fondled my cum soaked cock and balls. "My cum feels so nice on you" she murmured. "Don't you now feel like my little baby?" I just snuggled up closed to her and let her hold my smooth shaved prick in the palm of her hand as I slipped my hand back over the base of her fat hairy worm, and tried unsuccessfully to cup her big balls in my hand.

"We should probably clean up," I suggested. "The floor above yours is a men's floor, right? I'll go use that shower."

"Why not use the one on this floor?" she asked.

"Isn't it just for girls?"

"Sure, but no one is going to be taking a shower at this hour. Come on. I'll sneak you in."

Alice smiled mischeviously, then climbed off the bed. She grabbed a towel and wrapped it around her body, just under her arms. Her prick was outlined under the towel even though she was now soft. I pulled on my boxer shorts. She grabbed her shower basket and, together, we crept out into the hall and towards the door leading into the bathroom. Alice told me to wait. She went inside and emerged a moment later. "All clear," she said. She had that mischevious grin again.

She took my hand and led me into the bathroom. We went to one of the shower stalls and pulled the plastic shower curtain behind us. There was a small cubicle for changing. Alice stripped off her towel and hung it on a hook, allowing me a moment to admire her body before she began to tug at my boxer shorts. I quickly stepped out of them and hung them up as well. Alice began to run the water and we stepped into the shower.

Our arms found one another's bodies and we began to kiss more passionately than we had before. Our cocks became hard again and bumped together as we made out beneath the stream of hot water. Once we were satisfied, we began to scrub our bodies with soap. As Alice reached down to clean off my spunk from her balls, I grabbed her wrists. "Let me do it," I said. Alice nodded, and handed me the soap.

I washed her cock and her balls thoroughly, covering them with a rich, thick lather. Alice leaned back against the wall of the shower stall and smiled contentedly. I got my first close up look at her as she began to swell in my fingers. Her cock was about 6 or 7 inches completely soft and about six inches round, and then as it swelled up it doubled in size. I estimated at least a foot long, with a big flared head, and a girth too thick for my fingers to circle.

"Can I suck it?" I asked, once the soap was all washed away. The snake between her legs was fully extended. I couldn't believe she'd had that in me

"No." She said stepping closer and kissing me as she slid her arm round my back and grabbed my ass cheeks, pulling my groin into hers.

After a few minutes of passionate kissing and cock grinding, she spun me round and pressed me against the shower wall, coming up behind me and nipping my neck, whispering "mommy's so hard. Can't you feel it" her huge member entered under my butt cheeks, between my thighs and protruded out under my balls, trying to lift my whole body up as it throbbed under me. I looked down as she pressed her breasts and hard nipples into my back and ran her hands over my chest and belly. I could feel her wiry asian pubes pricking my cheeks and under my shaven hole. I still couldn't believe how big she was, even more shocking because of her medium sized asian build. She was shorter and smaller than me, but her thighs seemed long and lightly muscled, now I knew powerful enough to handle the horse cock that hung between them. I felt them now, pushing against me. I knew what she wanted, and my cock sprang to attention.

"I don't think I can take you standing" I whispered in trepidation, because I knew she had me and was going to try anyway. I felt like her brother must have that first time.

"But its something that I've always wanted to try," she said. "If you cant handle it, that's alright. I've always wanted to take a man standing. Just don't think I'm a freak."

"But I'm not going to force you" she whispered huskily as she slid her hard organ up and down between my spread thighs, her hands now fondling and teasing my erection til I was ready to blow my load. When she suddenly stopped. I gasped. "No, don't stop". She whispered into my ear. "Say please." "Please baby, please"

"Tell me you want me to rape your sexy manhole even though you think it won't fit." I trembled. She had me. We both knew she was going to take me in there, and I really needed to cum.

"Please be gentle"

"TELL me!"

"Please. Rape my hole. Now!"

She slid her hands round the front of me and under my wide spread thighs pulling them hard apart, and lifting my ass out towards her, forcing my weight against the wall as water sprayed down over us. There was no lube this time as she positioned herself. Standing I just couldn't make room for her to enter.

I turned my head back to look over my shoulder at her. "We need to be lying down" I shouted over the water sound. She could feel my nervousness.

Biting my neck she gripped me harder. I could feel her frame tense and lithe muscles ripple, reminding me of her manhood. This time there was no mercy as she thrust violently into me. Her massive flared head sank into my hole and I screamed. I couldn't help it.

"Shhh. Baby its only me."

And then she stepped closer, using her body weight to force in, virtually lifting me off the floor as she impaled me further. It felt like she was tearing me apart as ripped her huge cock into me, but I could feel it entering deeper. And deeper. And deeper. Finally she stopped. I was crying. Tears rolling down my face. It felt like I couldn't move.

She laughed at me and slipped her hands round to cup my cock and balls and squeezed them. "Stop crying, you little baby. I'm inside you now. A few more inches and I'll be fully buried in your tight little butt. Don't you love that?"

And then she just began to thrust. At first my whole body jerked in unison as she seemed to fucking me like something on the end of her prick, but then I loosened up a little. The tears cleared, and she was now entering and exiting my hole while my prostrate felt every ridge in her cock. The tears gave way to orgasmic pain and pleasure as she raped me wantonly. I knew she was lost to her own pleasure.

"I'm nearly there baby" She shoved harder and I felt her hard pubic hair touch me for the first time. And then with a massive grunt that nearly lifted me off my feet I felt the full thick matting up against me, and the fucking stopped. All I could hear was heavy breathing. She whispered. "I'm all the way in. Can you feel me"

"Like you're about to exit my throat" I tried to laugh!

She began little thrusts like she was worried she'd never get that deep again, but soon gave way to full fucking, grabbing my erection and maneuvering me using it. "AAAah I'm coming I yelled as I spurted all over the shower wall." Gasping with relief.

And then as I made to relax I realized that she was so massive inside me that my cock just wasn't softening. I could hear her giggle behind me. "Hun, you're only going to stop cumming once I leave your ass. You're never going to be able settle for anything smaller after this."

And I knew she was right when she unexpectedly pulled out leaving me empty and feeling like something missing. As i turned disappointed to look back at her in question, she spun me round to face her.

"Don't worry baby. I'm not done. I just want to see your face as I take you." She pushed me back a little, pulling my hips towards her, and spread my legs further apart with her feet and stepped in closer. I looked down and past my still erect cock saw her monster bobbing between us. I felt like such a little boy in comparison. Untrimmed and hairy, without the context of her figure and breasts it looked like a giant mans cock swinging over mine. she hefted it and aimed her hips up and forward so her cockhead nestled under my balls and at my still open hole. she positioned herself and forced her cock up me. for a moment it looked like we were connected by a long thick rod until she closed the gap

She fucked me long and hard. face to face. forcing me acknowledge her power and dominance. I had two dry orgasms without her even touching my cock, before she finally blew her load in my ass. She pulled out as she softened and I collapsed to the ground in the shower. "

she helped me up and kissed me and helped me cover up as i was still shaky from her pounding. "Come on baby lets get you back to bed." We got back and she was hard again. She laid me gently down on my side and then slid a hand up the inside of my thighs to my prick and held it. "Mommas big cock owns your little clit right honey?" I mumbled an acknowledgement, exhausted from the multiple pounding I'd taken. She pulled my leg up and forced herself inside me again. It brought tears to my eyes. "Shhh baby. From now on we're always going to sleep like this. My big cock buried deep inside you." And I knew she was right, and I wanted it. We snuggled up. Her foot long snake hibernating inside me until the morning when it would wake and own me again. I smiled in anticipation and drifted off.would wake and fuck me til it spurted its seed deep inside.

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