We made our way down to the waiting car, me wearing the kimono, panties, and sandals, my mother wearing a black velvet dress, deep cleavage but a tall collar in the back, red lining and trim, sharp heels.
I sat across from her in the limo as we made our way through the city. She was wearing a necklace I had not seen before, gold with a small silver key. She toyed with it until she was certain I saw it. I suppose it was a threat to cage me if I didn't do what she expected tonight. But I had no intention of disobeying her.
My stomach was growling because I had not eaten since my bowels had been cleared. But I felt as fresh as a peach, and my skin was smooth from the shaving my grandmother had given me.
My mother reached into her clutch and took out a small green pill and held it in front of my mouth. I opened and she popped it in, and I swallowed. I didn't ask her what it was, but she told me anyway, "It's for stamina." On my empty stomach, I expected it to take effect very quickly.
We didn't speak again. I simply watched her, admiring her beauty. And it didn't take long for me to start stirring in my panties, my little cock and balls tucked back but starting to strain against the material. I remembered the first time she took her breast out for me on my birthday, how I masturbated to her command and came on the floor, how she rewarded me with her panties and this new life I was still moving into. How I later sucked her nipples and licked her lovely pussy until she came. How she took my anal virginity with her strap-on and how she milked my prostate until a long rope of cum flowed out of me. All to prepare me, she said. And so, I could not help but wonder about this next step.
We finally stopped and got out of the car at an understated apartment building. A bellman opened the building door for us and walked us to the elevator. He swiped a card and pressed the "11" key and stepped away before the doors closed. He stole one look at my mother while her head was turned towards me. She still said nothing as we went up, even as the elevator opened directly into a luxury studio apartment.
We removed our shoes by the elevator, and I followed her to the center of the room. She directed me to stand there, facing away from the elevator. Then she untied the kimono, took it from me, and folded it on a chair. I stood in my panties with a full-length wall of window in front of me, curtains open, looking out over the city as the sun was setting and the streetlights were starting to appear, a king-sized bed to my left, and a small kitchen area to my right. The room was tastefully furnished, with no hint as to its purpose.
"You will wait here. A woman will arrive. You will do everything she demands, as if she were me. Do you understand?"
"Yes, Mother."
"I will be watching," she said, and she left. I heard her slipping back into her heels, and the tapping of them into the elevator, the rush of the doors, and then the silence.
I stood looking out the window. There was a taller building across the street, and several apartments facing this one, some lighted, some not. And I wondered what kind of show I would be putting on tonight. The lights in this apartment were soft, but they were on. And I was certain I was in a fishbowl.
I heard the elevator a few times over the next hour, coming and going, but not stopping at 11. The whole time, my little erection was straining against my panties, despite my trying not to think about it. The pill was doing its job, though I suspect the situation would have kept me hard regardless.
Eventually I heard voices behind me as the elevator came and stayed. A woman laughing, the muffled sound of a man's voice. The doors opened and I did not turn around, but I could see an obstructed reflection in the window of a small woman and a very large black man.
.
The man said nothing else, but the woman began speaking, more to herself than to him or to me, "Oh, my, how lovely!"
She had something like a British accent, but it sounded more like an affectation that the rich employ to sound posh. When she walked around to face me, I was surprised that she was much older than I expected. Attractive still, in a Helen Mirren sort of way. White hair cut short. Tanned skin a bit weathered but leading to ample bosom. She appeared to be fit. And her clothes looked expensive. She wasn't wearing a bra under her silk top. Her slacks were sharply pleated, and her bare feet were tiny, with nails painted the color of sand.
"I've been watching the video link your mother gave me, since you turned nineteen," she said. "I saw you watching incest porn, stroking your little cock and sniffing her panties. Listening to your little grunts. Watched you licking up your own cum." I could not have been more shocked. My pupils must have shown it, because it delighted her.
"She insisted that I wait until you turned twenty-one, but I think it was just to get the price up! I've been paying her for the video stream all these years, and now I get the real thing. She promised me you are still a virgin. Is that true?"
"Yes ma'am." Unless you counted my mother fucking my ass with a strap-on, I thought to myself.
"You will call me Baroness."
"Yes, Baroness."
"I will be taking your virginity tonight, and you will never cum again out of my presence. Your cum is mine from now on. I've bought it." I am sure I could not hide my disappointment, and I think that excited her too.
"I am so glad you understand."
Then she stooped over and pulled my panties down, and my little cock sprung out from between my legs. It was so hard it was throbbing. And as she stooped over, I could see down her blouse at her heavy breasts swaying beneath the silk. And I knew I would be sucking on those breasts very soon, and that made my dick pulse that much more. She laughed at how conflicted I appeared.
The black man had not moved from the door and had not said a word.
She led me to the bed and ordered me onto my hands and knees, my ass facing the window, my face towards a chair beside the bed. She stood before me, in front of the chair, and slipped out of her slacks, revealing black lace panties over a shapely set of hips. She unbuttoned the blouse and her tits, while long, were full and very sexy. Yes, there were stretch marks, and yes she showed her age, but all I could see was an attractive older woman, and all I could think is that she was somebody's mother. I wanted one of those breasts lifted to my mouth. But I was not at all comfortable with the position I was in, for good reason.
While my attention was on the Baroness, the black man had slipped around behind me. She was watching my face when I heard him spit and felt him spread my ass cheeks. My fingers dug into the bedspread as he pressed his cock into my ass. She was delighted at the "O" my mouth made, and how my eyes watered as he pushed deeper, rocking his way in by fractions of inches. But my dick was harder than ever.
"I watched your mother train you with that big black dildo, but this is so much better!" I should have guessed that Mother had recorded us, but I had honestly thought she didn't have any cameras in her bedroom.
Then she bent over and took something out of her slacks pocket. It was a condom. She reached underneath me and unrolled it on my little dick, and it barely stayed on.
"I'm collecting my natural lubricant," she explained. And it didn't take too long before I started producing it.
I couldn't help but moan as he pressed against my prostate, "Oh, uhhhh, uhhhh," until she lifted her right breast and pressed the nipple into my mouth. Oh my god, I sucked like a calf. I was trying to milk her as he was thoroughly milking me. Then he just started pounding into me without restraint, readying himself to cum in me.
He grunted once, as he came, pressed all the way up inside my ass. I could feel the pressure of his load filling me up. She just held my mouth on her tit until he was through. When he pulled out, she slipped the condom off of me, slipped off her panties, sat on the chair and spread her legs. Her pussy had full lips, and she spread them and inverted the condom to dump my cum inside, then she rubbed it around with her fingers. She took her time, her head back, enjoying the moment and the exposure. When she was ready, she told me to roll over on my back. I did, still leaking cum out of my ass, and she walked around in front of the black man and climbed on top of me. She eased herself down on my still-hard cock. It was my first time inside a woman's pussy, and she was wet with my own cum, and warm, and better than anything I had ever felt in my life.
She giggled like a little girl, probably at how small I was and how little I could fill her up. She laid down flat on my chest and said, "Grind that little clit into mine."
I went as deep as I could go, but she was the one pressing down and hitting the spot she wanted. She found the right angle, then held still and said, "Jimmy, be a dear and put a condom on and slip inside my ass."
Jimmy went back to his pile of clothes and got what must have been a Magnum. I saw his dick for the first time then, amazed that I had taken it all in. He snapped the condom on and moved behind her. Then it was my turn to watch her eyes roll back as he pressed into her. I could feel him filling her ass and adding some pressure in her pussy for me. He pumped enough for the two of us as I lay still, and she pressed down and moved her hips in small circles.
"I'm gonna cum," I said.
"You will not!" she demanded.
"Please, Baroness! Please let me cum inside you!"
That must have put her over the edge, because she started cumming, "Yeahhh. Yeah! Cum in me Jimmy! Cum now!"
Jimmy blew his load on command, and I was straining to hold mine. I knew I would be punished if I came without permission.
"Please, Baroness! Please, me too!"
