Serving My Sister V: BDSM Party

Note : This story is completely fictional!

It was simple enough to see that the summer season was on its last legs, even without looking at a calendar. The weather had cooled to an average range of upper sixties to lower seventies, but that was still warm enough to wear normal summer outfits. Lucky for me, mistress Eileen had recently bought me a new outfit, a reward for my good service. I hadn't seen it yet, and my sister wouldn't say anything beyond "it's somewhat revealing.

By now, I had become so comfortable being my own sister's slave; I was actually enjoying it emmensely. Yet for some reason, I still could not bring myself to verbally admit it to her. Thus, I had not been allowed to bed her yet. I had pleased myself in front of her, been masturbated by her hand, and had even eaten her out for her recent birthday. But until I could mouth the words "I want you Eileen", my cock would never find her pussy.

Perhaps I would find the courage with my parents gone. As they did near the end of every summer, they each took a week off from work to go on a leisure cruise together. Eileen and I had seen them off early in the morning. Later that evening, Eileen finally brought the bag containing my new outfit to me.

"Put it on," Eileen told me with a smile. "I wanna see how you look in it."

"Yes, Mistress Eileen," I replied, more for formality than anything else. Such unforgotten formailities were one of the things that had earned me this reward.

As I pulled the outfit out of the large gift bag, I felt a wave of emotions wash over me. I didn't know whether to scream with excitement, or cream my panties. I changed slowly, taking the time to make sure each piece was worn correctly. First came my black satin bikini panties, the feeling alone almost enough to make my cock grow erect. Next was a pair of violet fishnet pantyhose, and a likewise colored mini slip. That last item was barely shorter than the black pleated demin mini skirt underneath which it rested.

On my feet were black knee boots, with wide three-inch heels and violet laces. My belly was revelaed under the black middrif halter top, which was completely backless; only a spaghetti string tied together held the bottom closed, as did likewise at the top. I then slipped my arms into violet satin gloves, which damn near reached my shoulders. Completeling the look was a violet wig, its bangs reaching my eyebrows, while the rest of it--hanging from a center-part--fell just below my shoulders.

"Damn, you look sexy," Eileen complimented.

"Thank you, Mistress, Eileen," I answered, fighting back tears of joy. "You don't look bad yourself."

Eileen, of course, always looked beautiful, but tonight she was nothing short of stunning. She had donned her silver jeans that matched her sandal-like high heels, and wore them with a blue, sleeveless button down blouse, which was tied in a knot. Her toenails were polished in blue, while her fingers showed silver and her hair (which she had recently dyed black) was held in high pigtails by blue hair bands.

"C'mon," said Eileen. "We gotta do your make-up."

*****

My make-up had been simple enough: foundation to cover whatever facial hair my razor missed, and purple lipstick to match my wig. This time, when Eileen led me to the car, I had no hesitations; it was not often that my Mistress led me anywhere looking like a male. Although, as a reminder that I was indeed a cross dresser and not a real woman, Eileen never did give me a female name.

She drove us to a mansion, which was owned by a friend of hers. I had been there once before, though I had never seen the inside. I knew I was about to, considering that there were many other vehicles parked, and a few more pulling into the enormous driveway.

"Open the glove box," said Eileen. "There's something in there I want you to wear." I obeyed her without question, finding a spiked choker with a D-Ring in the center, a four-foot dog chain connected to it. I quickly put it on, careful to keep it under the wig and the chain centered.

"Since this is your first bdsm party," Eileen explained, "there's two things you need to understand. First, do nothing without my direct permission. Don't talk, get refreshments, or even go to the ladies' room without my direct permission. Second, you'll meet many other Masters and Mistresses in there. If they speak to you, reply only to questions. Say nothing to comments. Also, be sure to address them properly. Understand?"

"Yes, Mistress Eileen."

*****

It was easy enough to tell who was who at this party. Only Masters and Mistresses conversated, their various slaves merely standing by their sides. Some had only one slave, some had more. Also, I wasn't the only one on a makeshift leash.

The first thing Eileen did was lead me to a couch, where I was to wait for her. I had to sit properly with my legs together, and my hands folded in my lap. After about twenty minutes or so, Eileen came back to me with two women, obviously a Mistress and her slave. The slave looked young, and was dressed in very tight clothes. Her black vinyl pants had only a zipper in front, and her black, short sleeve blouse was open enough to show that she wore no bra upon her size B breasts. Her feet were clad in three inch pumps, and her bright blond hair was in pigtails, likewise to my sister.

Her Mistress was obviously middle-aged, but no less alluring. Especially since all she wore was white lingerie! Her bra and panties matched, both silky with lace, and her stockings were held by a garter belt. Her torso was covered with a corset, and her shoes had been left at the door.

Eileen introduced us. "Jeremy, this is Mistress Vanilla, and her slave, Marlena. And this is my slave, Jeremy."

"Don't worry, Jeremy," Vanilla assured me. "You're not the only incest pair. Marlena is my daughter. She's also a per-op transsexual. You see, I didn't want a boy, so I made a girl of Marlena from day one." Vanilla turned to her daughter. "Go on, show him."

Obediantly, Marlena unzipped her pants (I noticed she wore no panties), reached inside, and pulled out her previously tucked cock. Vanilla smiled at me. "Try it out."

I looked to Eileen for approval. "You heard her," said she, impatientely. "On your knees. And swallow every drop, I doubt our host wants a mess."

I had never sucked a cock before, and I wasn't completely sure I wanted to do so. However, I was much more certain about not wanting to disappoint Eileen. Without question or pause, I knelt before Marelena and took her cock into my mouth. Surprisingly enough, it tasted great! I couldn't believe how much I enjoyed it, nor how quickly Marlena got hard.

She was well trained, I could tell. After a while, my jaw was hurting like there was no tomorrow, and all I had tasted was pre cum. All the while I sucked, I could hear Marlena whimpering, almost pleading for permission to finish. Finally, Vanilla gave her daughter the permission she craved, and her hot cum was fired into my throat with extreme intensity. Her cum filled my mouth so quickly that I had trouble keeping it all in my mouth. Yet I managed to swallow it all, my own panties nearly soaked with pre cum.

*****

Later that night when we left, Eileen simply waited in the car with me for a time. Finally, she looked to me, placing a hand on my inner thigh. "You did well tonight," she said to me. "You deserve a reward." Eileen then lifted my skirt, finding that my precum had soaked right through my mini slip. She giggled. "You naught boy."

Eileen lifted my slip, pulled my pantyhose down, and pulled my panties aside. My cock was wet with my juice, and still stood erect. Without another word, Eileen leaned toward me, and began sucking my cock. She was unbelievably talented, making me cum in less than five minutes! The first two shots, she let fall from her mouth and onto my balls. The final three she held, just before snow balling my own cum onto my tongue. After a passionate, cum-filld kiss, we swallowed our shares.

"Let me help you with that," Eileen offered, looking to the cum she had spit back onto me. She opened her jeans and pulled the just below her hips, then held the front of her panties down, revealing her shaved pussy. With her free hand, she wiped some of my cum onto her finger tips. I knew where this was going, and it scared me. That fear, Eileen knew, also aroused me.

Slowly, Eileen pulled her cum-covered fingers back. Then she did it--she pushed my cum into her pussy, moaning with closed eyes as she did. Unable to contain myself further, I exploded again. Eileen actually allowed some of the fresh cum to land on her fingers, putting that inside of herself as well.

"I'll give you five minutes," she said, cleaning her hand on her shirt. "Then start stroking that mess. I want you to cum again before we get home."

That was the easiest task I had ever accomplished.