Serving My Sister III: A Virgin's Cherry

Note : This story is completely fictional!

When the weekend came, I actually thought I'd be getting a break from my new life, and a brief breath of my old one. I couldn't have been more wrong. Friday night before I went to bed, Eileen had ordered that I sleep in one of my new nightgowns; a neon-pink, baby doll gown with black lacing at the top and bottom. She also warned me that I'd be in big trouble if I woke up with a hard-on. That was difficult as hell, considering how arousing I found the satin material to be. But somehow, I managed it.

As usual, Eileen came to my room in the morning to wake me, and get my day started. It was a good thing that I could wake up fast on my own. By the time I was up and sitting on my bedside, my sister was already at my dresser-drawers and closet, picking out my clothes for the day. I watched as she grabbed a pair of white, cotton, Hanes-Her-Way panties, and a white sports bra to match it. Along with those, she grabbed a white, six-hook garter belt, a white corset with black lining on the seams, and a pair of white, thigh-high stockings; she threw the bunch of items at me.

"Get out of your nightgown," she said, "and put those on."

I sighed. "Eileen, come on," I subtly pleaded. "Our parents are home!"

"Which is exactly why you'll wear those under your jeans and t-shirt," she explained, grabbing a black jean mini-skirt, and a short-sleeve, white button down blouse. I lifted the nightgown over my head and off my body, then began putting on the lingerie as I was told. Eileen folded the skirt and blouse and put them in my bookbag. She also put a pair of black, three-inch pumps in the other large section of my bookbag. "We're going out today; you're getting changed when we get there. Now if you'll excuse me, I have to go get changed myself."

*****

Between having cotton panties rubbing against my cock all morning and the way Eileen dressed, not allowing my dick to get erect proved to be the hardest task I had ever faced. She had decided to wear her daisy duke shorts, with a white sleeveless, button down blouse, that she tied off in the front. She also wore her sandy blonde hair in low pigtails, which happened to be my favorite women's hairstyle. I don't know how I managed to get through breakfast with the family and keep it together like nothing was different, but somehow I did. Afterwards, I met Eileen out back, in our screened-in back porch. Granted that provided a little shade, but it was still hot as all hell out there.

"Can I ask you a question, sis?" I asked, and Eileen looked over at me angrily at the way I had just addressed her. "Sorry, 'mistress Eileen'", I corrected myself. Somehow, I got the feeling that I wasn't forgiven.

"I'm tempted to say 'no' for that, but what?"

"Why are you doing this?"

Eileen threw her head back and laughed. "You don't know?" she asked me, almost half surprised that I didn't. "Think back, Jeremy, about ten years. When you were twelve, and I was eight, what did you do?"

That was certainly something I'd been trying my damnest to forget. I had been quite a demon child, very sick and twisted. I could have gone to prison for a very long time for what I did to my sister back then. Thinking back, I sighed. "Eileen, I'm not that person anymore."

"But I'm the result!" Eileen said with authority. "And now you have to deal with it. I may have sworn to keep silent in return for your never touching me again, but I secretly swore to also get back at you. Now, do you wanna question me again?"

I fell silent. When Eileen put it that way, I began to feel like I deserved this. Back when I had promised never to place my hands on my sister again, and she swore silence, I really thought I'd never have to again deal with the situation. I guess no bad deed goes unpunished.

*****

Eileen took me to a motel room later that afternoon, and I knew the purpose was sexual. Why else does anyone 'get a room'? She had me change into the skirt blouse and heels the moment we were inside. She also gave me the go-ahead to get horny. I already was horny, the whole car ride there, but at least I could finally let it show. It didn't take long before my cock was fully erect, and getting pre-cum in the front of my new panties.

Eileen firmly grabbed me by the shoulders and turned me away from her. She pressed her body to mine, and whispered into my ear. "You still want me, don't you?"

"Mistress, I..." But I couldn't get anything more out. I was already far too aroused.

"One day," she said, "you'll admit that. And you won't get me again until you do. For now..." Eileen reached her hand down the back of my skirt, underneath my panties as well, and started fingering my virgin ass. "...we're gonna do something about your 'cherry'."

She pushed her finger in deep, slamming her crotch against me, actually simulating me getting fucked by another cock. With her free hand, she held my body tight to hers, so I could feel her breasts pressed against my back. I couldn't have been stroking myself faster, though I was doing it underneath all my clothes; I hadn't received an order to take anything off yet.

I moaned loudly as I cam, my hot load filling my panties, covering my fingers. By the time it was over, my legs were so weak; I could barely stand. "Get your pants and shirt back on," Eileen told me. "We're leaving."

*FOOTNOTE*
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