My Big Day

I met Kim in high school and have been attracted to her ever since. She knew how much I liked her but she never gave me the chance. She liked teasing me. Now, five years later, I'm her sex slave.

It started a few months ago with daily chat sessions. These consisted of me jerking off while she watched. Sometimes she'd let me cum, sometimes she'd deny me my orgasm. After a couple weeks of this we started meeting in person. I would go over to her place and strip completely nude. Most of the time she would wear regular clothes but sometimes it was something sexy, like a corset and stockings, with me always nude.

Our first meeting together she shaved me completely bald. After I was shaved she made humiliating remarks about my bald state. How I looked like a little boy with my 'widdle penis' as she put it. She said I looked cute all hairless and smooth. As she said that I started getting hard.

"Oh, you like me making fun of your penis?" She said with a grin. I just stood there with my cock throbbing in the air.

It went on like this for about a month before she told me we were gonna try something knew. She said I would go one month without an orgasm, but after one month, I only got the chance to cum, there was no guarantee. I would have to be a very good boy the entire month, and absolutely no cumming. She said the last part with a giggle.

"Now make me cum pussy boy." She said as she pushed my face into her pussy. After I had made her cum about eight times, she was satisfied and sent me home with a raging hard on.

The first month went by incredibly slowly. During that time, I would go to Kims house every couple of days. I would clean her place, cook her dinner, and massage her back and feet while she watched TV. After that she would have me eat her out till her hearts content. I would be nude the entire time and my cock would be rock hard and dripping pre cum. She always smiled at me when I'd walk around her apartment nude, cock bobbing in the air. Some days I'd go over her and she'd tie me to her bed, spread eagle. She would shave me, which would leave me rock hard, then playfully toy with my cock. She would bring me to the edge of orgasm and always stop right before I'd cum. When she was tired of this she'd climb on top and straddle my face. My chin would be covered in her cum at the end of these sessions, and I'd always be sent home with a throbbing hard on. After two and a half weeks into my first month, I was at her place cooking dinner. It was about five o'clock. I was in the kitchen and heard the front door open and someone come in. I could hear Kim say "Hi Carla," Carla? Oh no, I thought, she can't mean Carla from school. I felt very awkward then. Carla was a friend of Kims from school who I had a little crush on back then. I had no chance of not being seen as I was in the kitchen cooking, not to mention completely naked and shaved. I stood there thinking about it when Carla suddenly entered the kitchen.

"Hi Slave," she said to me. She opened the fridge and got some wine. She smiled at me, then her eyes went to my crotch and she smiled even more.

"How's it going?" She said. I didn't say anything and Kim joined us from the living room.

"Slave, I believe you've met Carla before," She smiled at me. Yes I replied. "Yes Mistress." She corrected me.

"Yes Mistress." I bleakly said.

"We'll have to work on that,"

"I like how he's shaved," Carla said to Kim. "Do you always keep him like that?"

"Yes," Kim replied, "Always shaved and hairless, like a little boy. Doesn't he look like a little boy?"

"Mm Hmm, but his balls are huge, they look so full." They talked as I continued to cook, not being apart of their conversation but being humiliated and embarrassed.

"They're full of hot sticky cum that he would love to spew out but no, that would make too much mess right now," The girls erupted in laughter and went back into the living room.

After dinner I massaged both their feet. They giggled at my rock hard condition and made jokes about it's size. Then it was time that Carla received my real services. While I was going to town on Carla's shaved box, Kim went to work on my ass. First she plugged it with a butt plug, which I soon found out vibrated, and then started spanking my ass with a paddle. Every now and then Kim would tickle my hairless scrotum. She would give my cock a quick stroke or two and then slap my balls. The whole area was sensitive and it felt like torrents of jizz would ejaculate if only I could cum. I was so close to cumming but there was no way I would. After Carla was satisfied (and she was- she left a huge wet spot on the couch, which turned me on even more), she stood up, weak kneed, and went to the bathroom. Kim took the plug out of my ass. She had me kneel on the floor and locked my hands behind my back. She put a blind fold over my eyes then sat on the couch, pussy facing me. I couldn't see anything. Carla came back from the bathroom. She got down next to Kim and I could hear the juicy sound of something going in and out of Kims cunt. My cock started to grow again. Carla must have hit the right spot because Kim suddenly cried out and squirted all over my chest and groin. My cock was bobbing in the air and was covered in hot sweet girl juice, courtesy of Kim. They uncuffed me and took off the blindfold. They were getting dressed and I was ordered to clean up the place. My cock stayed hard for a long time after that.

"What are we going to do with that thing, it looks like its gonna set off," Kim said.

"Ice him?"

"Yes, and something else," Kim said. I had a pretty good idea what she meant. Five minutes later I was tied to the bed with a bag of ice on my cock. My cock eventually softened and went completely limp. My heart jumped when Kim and Carla appeared in the doorway. They had wicked grins.

I was right; my cock was secured in a chastity device. It was a CB-3000 Kim told me as she untied me. She had the only keys.

"It makes his balls look even bigger!" Carla said. "Oh but they'll get even bigger by next week," Kim said as they laughed at my incredibly horny state.

I didn't see Carla again until a week and a half later, on the day of my big chance to cum. I showed up at Kims house at one o'clock. I was stripped nude, then cleaned her place. After I was finished she brought me into her bedroom and tied me to the bed. She shaved me bald, then without hesitation sat on my face. After about five or so orgasms she got up and told me if I remembered what today was. Yes Mistress I replied. She told me how I was a very good boy this month and that she had a surprise for me. She untied and led me to the living room. She had a small table set up, which she had me kneel on in the doggy position. She locked my ankles and wrists to the corners. Then she blind folded me. I was set up so my ass faced the couch. It seemed like the room had been set for an audience to come see me.

"Here's your big chance to cum," Kim said and I heard her shaking up two dice. "A roll of seven or eleven and you cum, any other number, tough luck." I heard her roll the dice. I didn't even get to see what the dice said. "Aww, too bad for you pussy boy, it looks like you'll have to wait another month."

Then I heard the door open and several girls coming in. I started to panic. Here I was, tied up and on display right in the living room. Kim got up and instructed me to get my face down, ass up. I complied and as she left the room she spanked my ass, hard. She greeted the other girls, which sounded like five or six of them. I heard them come into the living room. I heard all their comments but had no idea what they looked like. I was very small in my CB and they all made fun of that. I recognized Carla's laughter. I was horrified and I thought it couldn't get any worse. But it did.

"As you can see girls, this is my sex slave," Kim said. The girls couldn't hold in their giggling and laughing. "I've denied him orgasms for this entire month and he's taken it pretty well,"

"His balls look huge,"

"Yes, that's true and in a minute, as you're all about to see, I'm going to empty those balls...while denying his orgasm. How exactly? Have any of you heard of prostate milking?"

Some of the girls had heard of it, some had not. One said she knew what it was but had never seen it. When she said that I began to panic. I'd never been milked before and I was going to be milked in front of her girl friends. I felt Kim behind me and lube being rubbed into my asshole.

"The prostate is a gland found inside the rectum. When a man hasn't ejaculated in a long enough time, you can massage it and force semen out, which drips out of the cock," My cock at this point started to get hard. I heard someone say "He's getting hard, well, kind of," and laughed.

"Yes," Kim said, "He can't really get hard, or cum for that matter in his little tube," Kim got two fingers going in and out of my ass. "The prostate is about one to two inches in, and it will feel like a lump about the size of a almond." I felt her hit my prostate, causing my cock to swell against the CB. "Look, he's getting hard " I heard someone say.

"Yep," said Kim, "He must like his ass getting fingered in front of an audience," There were giggles and snickers from the girls. "Now that I have enough lube in him, I can start massaging his prostate." Kims fingers withdrew, and a few seconds later I felt a vibrator being inserted. As soon as the toy hit my spot, my cock tingled. "Now I start massaging the prostate back and forth, side to side. I also use a technique of raking the vibe over the prostate with downward pressure." Every time she did the raking thing it felt like pee was passing through the tip of my cock, which was completely filling it's cage. After a couple times with this, it felt like something was really dripping out of me. I heard ooh's and ahh's from my audience.

"There we go, now it's starting. Every time I do this I force more semen out." The girls must have been hypnotized by my cum dripping cock. I was horny beyond belief. My balls ached and my cock felt like it was going to break out of its prison. I felt like convulsing. I was so incredible close to orgasm, so close! One touch to my cock and I'd explode. But I was kept on that edge forever. I could feel more cum coming out, lots of it. Kim continued.

"See girls? Now its coming out as one long stream and we can milk it all out. The goal of this is that it prevents wet dreams and sort of 'relieves the pressure' if you know what I mean," the girls all giggled. "All while denying him the pleasure of orgasm, but keeping him as close as possible," Kim said. I was overwhelmed with emotion. I was extremely humiliated and dehumanized yet incredibly at peace and tranquil. I could hear questions and answers going on behind me but I couldn't hear. I have no idea how long it lasted but suddenly I felt my erection going away.

"There, now he is done," Kim said.

"Wow, that is a lot of cum," someone said. Kim untied me. She helped me get up and face the girls. I felt dizzy and weak-kneed. She removed my blindfold. My stomach turned as I saw for the first time my audience.

"Now, the icing on the cake," Kim said and she handed a cup to me. I was so dazed I had no idea what it was. I took it with a shaking hand and looked. It was cum. My cum. My cum which actually belonged to my Mistress. Her cum now. I looked at it. I felt everyone's eyes on me and I just wanted to run into a hole and die. But I was overcome with arousal, hopelessly horny. I looked at my Mistress. She smiled at me and gave me an eyebrow raise that was so subtly sexy and dominate it made me gush. I looked at the cup again and brought it to my mouth. I swallowed it quick, for I was owned by Her.