Sister is My First

byassslut©

It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to Jamaica for two weeks and asked me if I could keep out of trouble while they were gone. Of course I told them I would be fine. Mom seemed like she did not want to leave me alone and I knew Jack did not want me to go with them on the trip. Now I would love two weeks in Jamaica but I had my reasons for wanting to be left alone for two weeks.

I had been dressing up in my sister's clothes for almost two years at certain times. . Every chance I got I would dress up in her lingerie. Some days I would have fashion shows and wear several different sets of lingerie and try several different pairs of heels with each to see which looked or felt best. The idea of being able to dress for a whole week sent all sorts of ideas through my perverted and dirty mind. My mom finally agreed to let me stay by myself. She said my sister would be checking up on me time to time. My sister, Amy, lives about an hour away, no big deal I thought.

Friday late afternoon, I helped Jack pack their luggage into his car and watched them drive away. I wanted to run back into the house and change. It was all I could do to resist the urge, but I knew I would have plenty of time to dress up. After I made sure they left I went to take a bath. I lowered myself into the water and enjoyed the warm relaxing bath. I felt so feminine and grown up while I pampered myself. After the bath, I decided to shave myself. I took my time and shaved my legs, my underarms and I trimmed my pubic hair into a neat triangle. I had very light blonde hair on my body anyway and I hoped that no one would notice that I have shaved my body. A simple, virginal white lace thong and a matching bra were all I felt my pretty teenage persona needed. The thong felt amazing as it encased my already semi tumescent cock and ran up my ass crack. I stuffed the bra with tissues to give me a little bit of a chest. Fortunately, I felt a slightly flat chested look made me look cute and younger than I actually was as a guy. Next, I found a little grey pleated mini-skirt. Being slightly taller than Sara made the skirt even shorter on me, barely swaying at thigh level. I slipped the skirt on and gave a little twirl. I loved the feeling of having my long, slender legs exposed and easy access to my awaiting crotch. On top, I found a cute pink sweater that just fit perfectly, clinging tightly to my slight curves and narrow waist.

After, I went to my dad's stash of VHS porno tapes. They always had some way hot women always dressed to the nines in hot lingerie sets and most time 2 or 3 some times 4 guys with monster cocks gang fucking the shit out of them. I grabbed one and put it in. The first few scenes were kind of boring, and then it got to a scene where a cute blonde was used roughly by two men. I was already hard and imagining I was the hot blonde being used just turned me on even more. I started to rub my dick through the lacy material. It felt amazing because the front of the thong moved up and down along his shaft While the blonde on the screen was sucking one guy's long hard cock another guy got behind her and shoved his cock into her pussy. I could not help but imagine myself in her place. I pulled my cock out of the thong, wrapped my hand around the shaft and began to stroke it, letting out a little sigh of pleasure. I then thought of something interesting to do.

I found a nice a dildo in my mom's closet a while back. I decided to go get and have fun with it. It was a nice thick 6 inch black dildo. I stuck out my tongue and licked the head of the plastic cock. Closing my eyes wrapping my lips around the tip, I took it into my mouth. Even though it was plastic, I treated the dildo like real flesh and blood. I was careful not to let it touch my teeth as I tried to deep throat. I sucked and licked at the head like a tasty lollipop. I then went grabbed a tube of hand lotion and was applying it while I was stroking the cock. I then positioned the head of the dildo against the entrance to my ass. It didn't go in at first, but I pushed again, and slowly the expanding asshole took the thick plastic dildo in. While I was jerking off, a six inch long black dildo sliding up into my firm tight ass.

"Fuck yeah," I yelled as I was about to come.

"Kurt? What the hell is going on here?" I looked up at the sound of this and was mortified to see that my sister had come into the room and was staring at me open mouthed. I just started at her completely red. I didn't know how much she'd heard but however much couldn't be good. I'm ashamed to admit that I blew my load and came all over my chest. I started to talk, but my sister just help up her hand to stop me.

She just came around in front of me, and asked, "Do you want a real one?" I was too dumbstruck by the whole situation to respond. She got undressed down to her bra and panties. She was dressed in a black bra and panty set with red lace around the top of her bra cups drawing the eye into her seductive cleavage and further red lace around the waist band of her panties. Her gorgeous long legs were covered by black fishnet stockings held up by black and red lace suspenders. The beautiful length and arch of her legs were completed by a pair of six inch heeled black shoes. I looked down at her pretty panties and there was something huge in her panties. Pulling down the waistband of her black panties, she pull out a cock, even only a tiny bit erect, it already dwarfed mine completely. I stared at her cock; I'd never seen another one up this close. There was the biggest cock I had ever seen in my life, including in porn movies. It wasn't fat, but it was very long, maybe 8 inches, and she wasn't even completely hard yet. It came out of such a beautiful, curvy, womanly body. She took my hand in hers and wrapped it around her cock which was already becoming harder, longer and thicker. Not totally feeling in control of my actions I found myself stroking her dick, feeling it grow stronger and harder in my hand. I could feel the warmth of it in my hand which could barely reach around the whole thickness of it. Her cock was now fully erect in my hand and stuck up from her little womanly body in such a strange, new and exciting way.

"Don't be scared brother;" Amy said seductively, "You know you want this. You wanna go down on my big hard cock." I yearned to get a taste of it and that's just what I did. I stuck out my tongue and licked up and down and around the shaft like it was the biggest, tastiest lollipop ever. I opened my lips and let the head slip inside my mouth, teasing the opening with my tongue. All this time, my own cock was getting harder and harder until it was almost as rock hard as his I slurped and bobbed up and down her thick hard beast, my mouth open as wide as it could go to fit something that thick inside it, gradually managing to take more and more inside me. "Oh yes, baby, that's it," Amy moaned, pushing my head further and further down her shaft, "You're a natural honey; you'll soon get the hang of it."

I was now completely gobbling and slobbering all over her cock. I could feel it slip into my throat and I was surprised to find it didn't gag me. It was probably because of all the practice I'd had on my dildo cock. I had been sucking Amy's cock for about twenty minutes when I felt it begin to swell. Her cock began to grow inside of my mouth. It was so thick and hard as it slid to the back of my throat. She than begun to face-fucked me like a man. I let her do it, opening my throat so she could go deeper. I knew that it was coming and that just made me more eager. She then grabbed the side of my head and thrust her cock right down my throat before shooting her load inside me. "Oh god......swallow it all Kurt" and I did just that. It was so thick, warm, and salty and it tasted just delicious. I really am a cocksucker I thought to myself as I swallowed my first cum load.

She withdrew her cock from my mouth and moved behind me. Then I felt a cool, lubricated finger against my ass. Amy then stuck the finger up into my ass. My sphincter had tightened around Amy's finger. She then started moving her finger, massaging my ass, and finally trusting it back and forth, in and out. It quickly became two fingers, then three doing this. I could feel my ass clenching tightly around Amy's fingers but I tried to relax. I found myself pushing my butt back trying to force them further into me. I was really quite enjoying the stimulation of having my ass filled and beginning to long for her cock. I began to stroke my own little dick through the panties. She withdrew her fingers and I felt pretty empty.

I began to beg, "I want you to pop my cherry, and I want to feel your cock up inside my ass. I want to be your slutty bitch."

"Well, I can't say no to that," she grinned.

Amy moved the panties to the side and put the tip of her cock on the entrance to my asshole. She pushed her cock up inside my tight ass I tried to relax but the pain of it was astounding, even the loosening her fingers had given me was no preparation for this. She managed to force about three or four inches of her firm manhood into me and I felt completely impaled. I try to scream out as she pushes into me all the way down to her balls. I felt like I was going to faint. Finally I felt her thighs against my ass cheeks. She reached around and started rubbing my cock through the panties. While rubbing me through my panties and she was saying "That's it, good girl, good little girl; feels good, doesn't it?" I began to notice my cock was already growing hard again. Amy started to fuck me very slowly. My ass felt like it was on fire. She was soon slamming my ass as fast and as hard as she could. Her balls were slapping against my ass as she had push every inch into my anus. Every fiber of my body felt alive with pleasure and stimulation. I felt full and impaled and my prostate was completely stimulated. As pleasure began to replace pain, I began to meet her thrusts.

"Fuck, bitch, this is one tight little ass you've got here, it feels amazing on my cock," she said, "it's so long since I've had a virgin sissy like you."

"It's too painful," I begged, panting breathlessly, "Stop, please, I can't take it, your too big." Soon though, I was crying out a whole different thing, "Oh God, fuck, please, don't stop, harder, fuck me harder! Fuck my tight little virgin ass, and take my cherry!"

"You like this don't you bitch, you little slut,?" she taunted as she pushed deeper into me, "You just love having your ass cherry fucked like a little teenage girl, like a slutty bitch getting violated by your own sister?"

I moaned, "I love to be fucked by your big, throbbing cock, I want to be used as your sissy whore!" She began to slam her cock right into my ass and pull it out again, pumping faster and faster inside me. "Oh yes fuck me with your big cock Amy!" I yelled as her balls were slapping me at ever faster pace.

"You love that cock in your ass. You love getting fucked by your sister, don't you?" she said. I was taking it, and I was enjoying it! I was being fucked up the ass and I liked it; I wanted more.

"How does it feel, letting a girl use your ass like this? Being taken by a cock, so much bigger and thicker than yours," she said as she thrusted deeper and harder back into me.

I moaned in response to her assfucking, "Oh god yeah, I love to be fucked by your big, throbbing cock, I want to be used as your sissy whore! Fuck me! Fuck me like the whore I am." I bucked as much as I could while rubbing my cock. My body shook with pleasure as I was about to cum. I moaned, and finally, "I'm gonna cum," I yelled. I was emptying a load of cum into the front of my panties for a second time. My ass tightened further on Amy's monster cock.

"Bitch, your tight ass is gonna make me cum soon," Amy screams. Amy's thrusts deeper and harder into my vulnerable virgin ass became more and more erratic. Her gasps, grunts and groans were louder and more eager. I could tell that she was close to cumming and I longed to feel her shoot her warm load deep inside me, to fill me with her sticky seed. She pushed deeper into me, her full balls slapping against my round ass.

"Oh yes, oh baby," Amy moaned, "I'm cumming! Oh God! Fuck. I'm gonna fill your virgin ass with my hot cum you fucking slut!" Amy slams into me and starts pumping her thick white cum deep inside my tight little ass. Spasm after spasm after spasm Amy's cock throbs viciously pumping his seed into me. I felt my impaled ass filling up with sticky cum as Amy continued to moan and thrust until the cum started to leak out onto my thighs. Finally, she was finished and let her limp cock slide from my sticky anus. I felt her cock plop from my ass and she rolled off of me. I was lying down on the bed, exhausted from being ass fucked and blowing my load... The pleasure was still circulating through me. It was unlike anything I'd experienced and I knew that this had to happen again. The satisfied look on her face said that it was nearly a guarantee.

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byassslut© 15 comments/ 151538 views/ 31 favorites
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by Anonymous

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by Anonymous05/10/14

u are lucky

I would love to be fucked by a big Dick shemale I love to dress in bra and pantys and girl clothes I do my makeup and paint my toes put my wig on and fuck myself with my dildo I would love for a trannymore...

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by Anonymous12/09/13

Misplaced

I didn't think that this was the section for "Tranny" stories.

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by Anonymous09/05/13

Silly story

Really. I like stories where you have to fill in the gaps in your own mind, but this was a leap too far, the gaps were wider than the grand canyon.
Have another go, but after writing it, put it away formore...

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