by Steve256 ©
My sister and I had never had a calm relationship. She was my parents' favorite. Always pretty from an early age, she blossomed into a true beauty. By the time we reached high school (she's a year older than I), she was the most popular among the 'in' crowd. A champion cheerleader, with her classically beautiful face, long flowing brown hair, and perfect body, Sarah was destined to be voted 'Best Looking'. All of this attention and ego stroking, however, made her a real bitch. I was painfully shy and extremely introverted. Sarah constantly teased me, saying that I was a wimp, that I would never get a date, and that I was probably a 'fag'.
In the pain and confusion of my adolescence, I turned to cross-dressing as a release. By the time I was eighteen, I was proficient enough at dressing up that I could probably pass for a real woman. During my teens, I spent hours in my bedroom, dressed in silky panties and thigh high hose, masturbating. My fantasies ran the gamut from being seduced and dominated by a powerful man to being humiliated by a true dominatrix. These were the dreams that got me off, and these fantasies were a lot better than the two real life sexual experiences I had. They both involved a chubby, near sighted neighbor's daughter. The first incident ended in premature ejaculation, the second with my vomiting in her lap after too much to drink.
One spring afternoon when I was eighteen, I knew I was going to be alone in the house, and couldn't wait to get dressed up. My parents were away on vacation, and Sarah wasn't due back from college for another two days. I got my makeup perfect, just like those fashion models in the magazines. For my lingerie, I chose satin panties with lace trim, a satin lace bra, nylon hose and a matching garter belt. Over all of this I wore a shimmery lycra mini-dress. The final touch was a pair of three-inch toeless pumps. When I was done getting dressed up, I admired myself in the mirror. I was quite a vision. So much so, that my cock began to swell and I had to masturbate. I lay down on my bed and stroked my cock and massaged my asshole. Soon I was writhing in ecstasy, my lap soaked in pre-cum. I was so caught up in my reverie, that I didn't hear the front door open and close. Suddenly, though, I heard footsteps coming up the stairs and two voices. It was Sarah and her boyfriend Brad, back from college early.
I overhead Brad say something about "your weirdo brother, Michael". Then, Sarah said something about how I must be napping, and that they should barge in and surprise me. Flustered, I quickly pulled my dress down. Sarah didn't know about my hobby, and it was going to be doubly embarrassing being seen by another man like this.
As my mind raced, I saw my doorknob turn, and in barged Sarah, with Brad right behind her. First, she did a double take, probably amazed that there was a woman in my room. Then she realized it was me, and gasped.
"Michael! Oh my god!" she started, "Or, maybe I should call you Michelle! You little sissy!"
Brad just stared at me in amazement, at least partially at the fact that I resembled a fairly attractive woman, albeit with a hard cock under my panties and dress.
"Oh boy!", Sarah said, "What if mom and dad knew about this? You little sissy!"
I was totally flustered. I didn't know what to do. My eyes darted back and forth between Sarah and Brad. My mother was a very religious woman, and my father was extremely conservative. If either one of them knew about my cross-dressing, there would be hell to pay.
"Please, Sarah!" I stammered, "This is embarrassing enough being caught by you two! Please don't tell mom and dad! I'll owe you big time, I promise!"
Sarah said, "Well, my spring break started early, and I hoped to be alone with Brad, if you know what I mean. Here's the deal, I don't tell mom and dad about their sissy son, and you don't tell them that I fuck Brad in the house. Deal?"
My sister, for the first time in my life, sounded almost fair and rational.
"God yes, Sarah!" I said, "Thank you! I owe you!"
"Goddamn right you do!" her normal tone was back, "So, I think you're going to start paying right now! First, stand up so we can get a good look at you."
I stood up, still full aroused, and pranced around my bedroom, allowing them to look at me from all angles. Even though I had always resented my sister, at this moment her looking at me was turning me on. She was one of the most beautiful women I had ever seen, even if she was a total bitch. I guess I had always been kind of jealous of her. Now, for some reason under these circumstances, her beauty was arousing me.
Sarah said, "Now, Michelle, take off that dress so we can see what kind of undies you like to wear."
I did as I was told, slipping the mini-dress over my head, revealing my lingerie set. Brad's eyes widened. Sarah giggled as she looked at the head of my cock poking through the top of my panties, oozing pre-cum.
"Well," she said, "if you want to be a girl that means you're going to have to act like one. First, you're going to have to prove that you can suck cock!"
She made me kneel in front of Brad so that my mouth was right in front of his crotch. She then unzipped his pants and pulled out his prick. It was much bigger than mine, probably seven inches in length and almost two inches around. When it sprang out in front of me, I realized that I like the way it looked. The shaft was swelling, and the large purplish head looked like it was begging to be kissed.
"Go on! Suck it!" Sarah said.
For some reason, this really turned me on, and I decided that I would try to give him the best blowjob I could, just like all those girls in the porn videos I had seen. I took his shaft in my hand and gently ran my tongue over the head. Then I briefly suckled his balls. I returned my attentions to his dick itself, and began guiding it down my throat. It took some work, but soon my nose was buried in his bush. I pulled back, and heard him moan as I began to fuck my mouth with his gorgeous cock. I was blowing him for all I was worth and I thought he was about to come, when Sarah grabbed my hair and pulled me off him.
"Okay." She said, "So, now I know you can suck cock like a little slut! It's time for me to get some pleasure! Brad, baby, get on the bed."
He did as he was told, and she began to get undressed. As my sister took off her halter-top and pulled down her jeans and panties, I almost began to drool. Forgetting that she was my bitch sister, I was totally consumed by lust at the sight of her naked body. I almost came as she mounted herself atop Brad's raging hard on. Soon, she was humping his delicious dick, and in between moans, she gave me my next instructions.
"Michelle..." she panted, "I want you come over here ...and tongue my asshole while Brad fucks me."
It was unbelievable! My own sister, a total babe, but a total bitch too, wanted me to tongue her gorgeous ass! A restrictive thought about incest quickly passed. I was more interested in doing what she said, so that she wouldn't have any reason to tell our parents anything. At the moment, what I was most interested in was getting my mouth on her asshole. I quickly got on the bed and began licking her asshole while she was grinding on top of Brad. I could feel her shake while I did this, but it wasn't enough.
"Come on you little sissy!" she said, "You can do better than that! Get your tongue up in my asshole! Tongue fuck it!"
I eagerly drove my tongue up her asshole. The taste was acidic and it burned, but I didn't care. I was too turned on. Sarah began to shake and I realized she was coming. As she cried out in ecstasy, I though I would come too, but I decided to wait. This was too good! Sarah got off Brad, who was still sporting a massive hard on. She instructed him to stand up as before, and told me to get back on my knees and blow him until he came.
Quickly we both did as we were told. I think he liked the way I sucked cock! As I took him back in my mouth, I began to stroke my own cock with my free hand. As I feasted on Brad's incredible cock, Sarah mysteriously left the room. I didn't really care because I was too into sucking on this great prick. Brad started to moan more loudly, and I reached the brink. With most of his cock in my mouth, I felt my balls tighten, and then I was hit with the most incredible orgasm I had ever had. My semen came shooting out in hot spurts, drenching my belly, bra and throat.
Seconds later, I felt Brad's muscles tighten while his cock began to twitch violently in my mouth. The first boiling stream hit the back of my throat, and then his dick was gushing hot cum inside my mouth. I swallowed as fast as I could, but he was like a fire hose. While I gulped down a huge mouthful of his delicious come, I had to pull his cock out of my mouth. He kept coming, tremendous rivulets of pearly white come shooting all over my face, coating my chin, nose, and cheeks.
As I slowly stroked the last drops of jism out of his cock, I heard a familiar click and whirring. I looked up and there was Sarah with a Polaroid camera in her hand. She had just taken a picture of me kneeling down in my bra, panties and stockings, coated from my waist to my face in huge globs of cum!
She said, "Just a little insurance, Michelle."
To Be Continued...