My Sister's Boyfriend

I never considered myself to be gay or anything like that, but my first time was with my sister's boyfriend. It happened a week ago now. I was at home alone, parents away on vacation, and my sister gone on business. These times were fairly common, so I would use them to indulge in a little habit I had. I liked to crossdress in my sister's clothes. Nothing sexual, I just like the way they make me feel.

So there I was, sitting at my sister's vanity, putting the finishing touches on my make up. I had on a short brunette wig, that looked just like my sister's hair. I wore a red tank top with a black skirt. Underneath, I had a frilly black I slipped my feet into some stockings, and danced in front of the mirror. I wasn't to dressed, but I was certainly cute.

I had some generic pop music blaring for background noise. This may have been a mistake, because I didn't hear Todd, my sister's boyfriend barge in. Todd is a total dumb jock type. He towered over my 5'7" with his 6'4".and is very well muscled. My sister swore up and down that this excused how dim he is.

He shambled into the room, you could liquor on him from across the room.

"Becky, y- you're home".

"TODD! OMYGOD, I can explain", I shouted while jumping back.

"I thought you were out on businesh, did you come back just for me, thash sho sweet".

"Todd, I'm no-" Before I could finish my sentence, he was across the room forcing his tongue into my mouth. I felt utterly powerless in his grasp. His giant hands held my slim shoulders like vise grips. I tried to squirm away, but was too weak compared to him.

I devised a plan to get away, first, I would accept the kiss, he would then loosen his grip allowing me to run away. I started returning the kiss, letting his tongue play with my mouth, while sliding mine here and there. I slid my hands up to his waist a tugged closer. He did let go of my arms, but I was too wrapped up in the kiss to escape.

Despite my initial thoughts, I was enjoying the kiss. I started letting out soft little moans. My little cock was rock hard, straining against the front of my panties. I could feel his stiffening cock against my thigh.

It was like I was a whole new person, like I was some floozy, eager for him. Like my femme persona was controlling me. My mind went fuzzy, I had no idea what was happening to me, or what I was doing.

I started sliding my hand toward his zipper, across his hard abs. I reached his belt, and he broke our kiss. He left me breathing heavy, a single strand of saliva connecting our panting mouths.

"You tashe different today Becky, thash ok I have something for you to tashe".

Before I could register his words, he tossed me onto the ground. I caught my upper half on the edge of the bed. On my knees, I turned in confusion, "did he figure me out, did I make him mad?" I thought to myself. By the time I saw him, he already had his pants off. I could see a large bulge growing in his briefs.

He stepped closer and grabbed my head. I regained my senses and tried to stop him.

"Todd, I can't I'm-"

"Quit being a tease, I'm ready and you promished me the other day" He cut me off, shoving his bulge into my face. I could feel it pulsing in its cotton prison. My femme persona, started taking over again,

I reached up and peeled the briefs down. The smell was musky and intoxicating. When the briefs finally released his cock, the thick, veiny shaft sprung up slapping me on the cheek, splattering precum on my face. It was at least eight inches long and needy for attention.

The sheer size of it mesmerized me. I, almost instinctively, started to slowly stroke the shaft. The radiant heat of the beast had precum dripping from my tiny dicklet.

I brought my head in close and kissed the side of the shaft, smearing precum down the side. Precum was coming out like a fauset, dripping allover me.

I started licking at the head of his cock. I had him moaning, and groaning, but I wanted more. I formed a good seal with my mouth and slid the head in.I bobbed back and forth with the head, popping it in and out, licking at the bottom. I tried going deeper, but I could only manage about three quarters of the dick. My hand managed the last couple inches. I picked up me pace and he stated rocking is hips, spewing a bunch of drunken gibberish.

His dick started throbbing in my mouth, I knew what was about to come, and I wanted it, badly. He shoved me off his cock and started spraying hot cum all over my face. I opened my mouth wide, to catch as much as i could. He stroked torrent after torrent of his seed onto my face and into my mouth. It slowed to drips, so I swallowed and started suckling on hi cockhead.

He reached down and grabbed me by the arms, lifted me up and tossed me onto the bed. On my back, I looked up at him, towering over me, the visage of masculine power. Not wanting our romp to end, I thought quickly.

"Why don't we have a little fun in the back?"

His eyes lit up, when he finally processed what I said. Luckily, I had just shaved my body earlier today. I rolled over, and flipped my skirt up, showing off my toned ass.

I was in completely uncharted waters, I'd never considered playing with my ass before, now I was asking my sister's boyfriend to shove his giant cock up there. He pulled my thong to the side and rubbed his cock head against my hole, lubing me up with a mixture of precum, semen, and saliva.

The feeling was utterly terrific. I wanted it, I needed it, I rocked back and forth, eagerly trying to get him inside of me. Then it happened, he pushed forward, forcing his cock head into my virgin hole.

The sudden intrusion made me howl in pain. He started slowly rocking back and forth, only a couple centimeters each way, but it massaged away the pain. In place of the pain came an incredibly pleasurable sensation.

The the real thing started, with every thrust he pushed deeper into me. Penetrating my tight ass even farther. He grabbed my hips and held on tightly, as he started thrusting harder and faster. I was letting out high pitched girly squeals, begging him to fuck me harder.

Eventually he started bottoming out in my ass, his balls slapping mine with every thrust. I don't think he noticed, because he kept on riding me like a cheap whore. Something snapped in me, I started the day as a fairly feminine male, but I turned into a little sissy bitch.

I lifted my head and looked at the door. To my horror, my sister was standing there, phone in hand filming the whole thing. Before I could react to Becky, I was hit with an absolutely mind shattering orgasm. I filled the front of my thong with cum, it dripped out all over her bed. My ass convulsed as the wave of pleasure rippled through my body. Todd reached his limit, and slammed his dick into me and started cumming, driving even more cum out of my cocklet. I screamed out in ecstasy. Cum started oozing out around Todd's cock.

He passed out and fell onto the bed pinning me down. Trapped under his weight, I had no escape. Becky came over and sat next to me on the bed. She wiped some cum off of my face, and stuck her cum covered thumb into my mouth.

"You know this means you belong to me now, right?" she cooed.

I didn't answer, I just suckled on her thumb.

A wicked smile crept across her face.