Serving Kelsey

Kelsey reached down and gently cupped my swollen balls, giving them a firm squeeze. She crawled on top of me and smiled, her deep brown eyes looking directly into mine.

"You know our agreement. You get me and in exchange I get to do whatever I want, right?"

I nodded, my cock swelling inside its tight metal cage.

She leaned down, her lips hovering just above mine.

"Beg me to kiss you," she said smiling.

"Please Kelsey, please. I need your lips so much, I am aching for you, please oh God, please kiss me, please," I whined.

"Do you remember the last time I kissed you?" she asked, her warm breath cascading over my lips.

I closed my eyes and nodded.

"And what did I say?" she prodded, with a hint of cruelty in her voice.

I grimaced and bit and breathed in deeply. "That it would be the last time."

She pulled away, sitting up on my chest and letting go of my swollen balls. She winked, "You wouldn't want to make a liar out of me, would you?"

I shook my head. She just sat on me, looking at me, watching. My cheeks turned pink and I closed my eyes.

She chided me, "Now now now. Look at me. I want you to see me."

She slipped her hand into her panties and slid her finger along her pussy before removing it, glistening wet. "You see what this does to me?"

She held her wet finger to my nose. "Sniff it," she commanded.

She giggled as I inhaled. "One more thing you don't get anymore," she said, smiling.

"You stay right here, understand? I am going to go masturbate. You can listen from here. I know you are all locked up," she added, her fingers pulling on the chain on her neck, revealing the small padlock key she wore reminding me of my chastity, "But even so, no touching. Or trying to touch. It only makes it worse when you tug on the cage. You know that right?" I nodded and squirmed as I watched her walk from the room. Her tight t-shirt barely covering the small of her back and her perfect ass framed by her adorable pink cotton panties.

I sat and listened, tortured by the sounds of her orgasms. For the next 20 minutes, she wailed and moaned, cumming more and more each time.

It had been four months since I moved in with Kelsey and this is what my life has become.

It didn't start that way.

Kelsey and I are as different as you can possibly imagine. For starters, there is almost a 30 year age difference. When I met her, she had just turned 19, I was 48.

Kelsey was working as a waitress and I was coming in three or four times a week for breakfast. We struck up a bit of a friendship. She was the most beautiful woman I had ever set eyes on, the perfect girl next door look, with long flowing brown hair and deep brown eyes. Her full lips were impossible to ignore, but also perfect for her look. A cute perky nose, just a few freckles and a body that was like it was molded out of my fantasies. She was athletic, tall and slender. Her smallish breasts gave her a very youthful appearance, but they were certainly enough to make no mistake that she was a woman.

One day when the check arrived, scrawled on the back was a message. "Call me" with her phone number and a heart. When she walked by I stopped her and pointed to the check. "I think you made a mistake, I think this was for someone else," I told her.

She just smiled. "No mistake. Call me."

That evening after work, it took me a dozen times before I could actually make the call.

When I did, I got her voicemail. Fumbling I left a very tense message. "Hi Kelsey, this is um David. You left your number. I mean I think you did. I was just calling. I just. You said call me so I did."

When I put my phone down, my hands were shaking.

20 seconds later my phone rang. I didn't recognize the number.

"Hello?" I asked picking up.

"Hello," the voice came back, unmistakably the voice of Kelsey.

"You called?" she asked.

I cleared my throat. "Um, yes."

"Well? What did you want?" she prodded.

I froze. I didn't know what to say. My hands were trembling again and my heart was pounding.

After what seemed like an eternity, she laughed. "I'm just messing with you. I know I asked you to call me. I bet you are wondering why."

"Now that you mention it, I was," I responded. Before I could finish she interrupted.

"Do you think I am pretty?" she asked.

"Oh God, yes," I responded, perhaps a little too enthusiastically. She laughed.

"I need to know something David. You have to promise to answer me truthfully. Do you promise?"

I agreed.

"Do you think about me when you masturbate?" she asked very plainly.

I stammered and hemmed and hawed, feeling like a deer caught in the headlights.

"You promised to tell me the truth, David. Now tell me. Do you think about me when you masturbate?"

I couldn't speak. After what seemed like an eternity, I closed my eyes and let out the most embarrassing confession of my life.

"Yes."

"I thought so," she said. "See you tomorrow," she added before hanging up.

I didn't sleep a wink, running through my head every possible reason she might ask me that question, what it meant, why I answered the way I did, what else I could have said, and on and on.

Finally, then the clock read 7:00 am, I crawled out of bed, showered and made my way back to the diner, just as I did every Wednesday morning.

I was trembling as my hand touched the door, opened it and I took my usual booth. I sat down and scanned the room, looking for Kelsey.

My heart returned to a somewhat reasonable rate, as I realized she wasn't there. Alice, one of the other waitresses brought my coffee, then my eggs and then the check.

No sign of Kelsey. I was too ashamed to ask.

I left the restaurant crestfallen, hoping I would see her.

As I opened the door and stepped out, I felt a tug on my coat and turned to see a smiling Kelsey. "Miss me?" she asked, her head tilted slightly to the side.

I nodded and smiled weakly back at her. She wrinkled her adorable nose a bit and said "I thought you might have." She started to walk down the street, gently pulling me along by the arm.

"So how are you doing today my little masturbator?" she asked, laughing slightly.

I turned bright red and stopped in my tracks. She giggled more and gave me a firm tug by the arm.

"Um, fine, I guess," I responded trying to ignore her comment.

"Well that has got to stop. Understand?" she said sternly.

"Thinking about you?" I asked still blushing.

"Oh god no," she laughed, playfully slapping my chest. "The masturbating. I don't mind you thinking about me, fantasizing about me. In fact I want to encourage it."

My head was swimming.

"I need you to promise me David," she said, stopping, turning to me and looking into my eyes.

"I promise," I said, heart pounding again.

"Promise what?" she smiled back at me.

"To stop, you know, what you said," I responded, now blushing more than ever.

She looked at me, a little more directly. "You need to say it. Out loud. Right now."

I nodded, closed my eyes and obeyed. "I promise to stop masturbating, Kelsey." When I opened my eyes, she was grinning ear to ear. "Oh I like it when you say my name, that was hot." She leaned over and pressed her lips to mine, gently and sensually kissing me.

She leaned closer, her lips now just over my ear, whispering in a completely patronizing voice "Such a good little masturbator."

When she pulled away I was looking back at her horrified and ashamed. "Please," I pleaded with her, "pleased don't."

She made the most adorable pouty face and continued in her mocking tone. "When I am convinced you have stopped, I will stop calling you that. Understand?"

I nodded.

She touched my cheek and smiled. "I need to get to class. I'll call you tonight."

I watched her walk away, the sensation of her lips pressed against mine still lingering. My cock was swollen and my first thought was to find some private place where I could relieve the frustration that was building. I thought about my promise and then about her lips.

I went back into the restaurant and slipped into the restroom.

I sat on the toilet and stroked myself until my cock erupted into a wad of toilet paper I was holding. In my mind Kelsey was there, watching, mocking me, calling me names. Her angelic face saying the most humiliating things.

When the phone rang that night, I contemplated not answering. I picked up just before it went to voicemail.

There was a long silence and then she spoke. "Is there something you need to tell me," she asked coldly.

I confessed. "Yes. Yes there is. Just after you left, I went back to the restaurant and did what you asked me not to."

Another long pause. "And what was that?"

"I masturbated," I confessed as a wave of shame came over me.

"And?" she asked. Her tone still sharp.

I froze. "That is it, that is all," I said, feeling genuinely confused.

"No David. That is not all. It isn't even the worst part. You broke a promise. You lied to me. You promised me you would stop masturbating and the first thing you do is run off and jerk off. How am I supposed to trust you?" she lectured.

I felt like a little boy being scolded. "I don't know, I am sorry Kelsey. I won't do it again."

"No, you won't," she said matter of factly. "I am coming over to your place tomorrow at 3:00. We are going to get a few things straight. I have to tell you, I am really on the fence about this. I don't like liars, David."

I tried to explain, but she had already hung up.

I wasn't sure what to do, what to expect or what was happening. All I knew was that my cock was once again rock hard and my balls were swollen. As much as I needed to cum, I decided not to, I tried desperately to focus on something else, anything else.

Another restless night, followed by another breakfast served by Alice. No Kelsey at the diner or at the door.

I cut out of work early, getting home at 2:00, taking a shower and picking out something to wear that would make me feel good. The place was clean and I had a bottle of wine in the fridge.

At exactly 3:00 there was a knock at the door.

When I opened it, Kelsey was standing there, looking somewhat displeased. She had a long coat on and carried a large Coach bag. She pointed to the chair and directed me. "Sit," was all she said.

She took over her coat, revealing a crisp white blouse and a black pencil skirt. She looked almost like an old-style school marm, but also incredibly sexy.

"We have a few things to get straight," she told me.

"I want to make a deal with you. It should be obvious by now that I am looking for a sexual relationship and that I am considering you as the person to do that with. You also can see that you are older than I am. I am guessing 25 maybe 30 years. I get off on controlling older men. The rules are simple. I get to do whatever I want to you. That is going to include humiliating you and keeping you desperate and sexually frustrated. That is my fetish. What you get out of it is being with me. Being near me, close to me, wanting me and needing me. I am going to be your addiction. I won't be good for you, but you won't be able to help yourself."

She looked down at me. "Do you understand what I am telling you?"

I nodded.

"Then say it."

"I understand what you are telling me, Kelsey."

She smiled. "To make this work, you need to be completely honest with me about everything. No secrets. When I ask a question, you won't hesitate or think about it. You will tell me, right?"

I nodded. She looked at me, clearly letting me know I was testing her patience.

"I will tell you Kelsey."

"Now as much as I adore honesty, you should know that you won't get that from me. I am going to lie to you, trick you, and generally fuck with your head. That is what you are signing up for with me. Sometimes I will use honesty to hurt you. Sometimes I will lie to you just for my own amusement."

"That doesn't seem fair," I interjected.

"It's not David. But it is the price for being with me. If you don't accept these terms I will understand. I know this is an unusual arrangement. If you don't agree to everything, we can just walk away. But once you agree to my terms, that is it. There is no escape or negotiation."

She opened her bag and placed a written document on the table. Next to it was a small black bag.

"When I come back tomorrow, I will expect two things. The first is your signature on that contract, which spells out the terms of our relationship. The second is a chastity cage for your cock. There is a lock but no key. Once it is on, I will be the only person able to unlock it."

Kelsey smiled and came over to where was sitting raising her skirt, revealing herself completely to me. No panties, just her gorgeous pussy. She kneeled down and started to stroke my cock through my pants. Soon she was lowering the zipper and sliding my cock out, continuing to stroke it.

She took my hand and led me to the middle of the room and placed me on my back, lowering herself over me, her wet pussy covering my face.

"Masturbate for me," she commanded. I squirmed under her pussy and ass, struggling to breathe as I started to stroke myself.

"I can't wait to lock up your tiny little dick, loser," she hissed. "Smell me, masturbator, lick my wet stinky pussy. Show me how fucking pathetic you are."

The more she talked the wetter I could feel her getting.

"That isn't even a cock, it is so fucking small. You are never getting that thing inside me. I wouldn't even be able to feel it," she continued laughing now.

"Don't you care cum," she commanded.

Soon I could feel her starting to shake, pressing down hard so I couldn't breathe at all. I squirmed and struggled as she yanked my hand away from my cock and started slapping my cock. One hand grabbed my balls, squeezing them cruelly.

I screamed into her as she began to cum, her hand now slapping my cock really hard, the stinging becoming almost unbearable.

Just when I was about to pass out from lack of air, she rolled off me, collapsing into her own state of bliss. Her hand slid down between her legs, as she gently touched herself, giving herself another round of more subdued orgasms.

Her fingers traced over my cheeks, coated in her juices.

"Don't wash your face until I see you again."

"I won't wash my face until I see you again Kelsey," I said. My response bringing a smile to her face.

I looked down at my bright red cock, still hard but too sensitive to touch.

"You won't be able to rub that for a while, now will you?" she giggled.

I blushed more.

She gathered herself and her things and within a few minutes, she was back to her normal appearance, save for a radiant glow that seemed to come from every part of her.

"Tomorrow at 7:00, I will be back. You have a lot to think about masturbator."

When the door shut behind her, I burst into tears, not ever sure why. That night, I tried to masturbate several times, but the pain in my cock was too much. My thoughts would be me hard, but the skin was too tender to touch, creating an intense frustration.

I slept naked, on my back with no covers. My rock hard cock, twitching and aching for relief I couldn't provide.

Against all better judgement, I picked up the phone and called Kelsey. I didn't even know what I was going to say. When her groggy voice answered the words just came out. "Kelsey, I need you."

"I know," she said and hung up.

By morning, the swelling in my cock had subsided enough to allow me to get dressed, though the pain would be a constant reminder of Kelsey throughout the day.

When I got home, I spent the next two hours reading through the contract. I debated with myself back and forth. She was right about two things: this wasn't good for me and I desperately needed it.

Finally, when I was at peace with myself and fully understood what I was signing up for I took the pen and signed my name, just about the line that she would sign below.

I opened the black bag and found four metal pieces. It took a few minutes to figure out the design, but eventually I did. I placed the ring behind my balls, closing it and securing it with a small pin. Next came the cage itself, which was only 2" long, but fit my cock perfectly when it was soft, filling every bit of the cage, but still comfortable. Finally, I picked up the small silver lock. It was unlike any I had seen before. It had a very unconventional key slot and was much lighter than I thought it would be. I sat for 15 minutes before I steeled up my courage to snap the lock shut.

The moment I did, my sore cock began to swell in its cage. At first there was discomfort and then after trying to adjust it, I realized it was starting to be painful. As my cock pressed into the cage and my skin pressed through the openings, it grew more and more painful. I tugged and yanked trying to free myself, to no avail. I ran to the freezer and started to pack my cock in ice, which helped to numb it but not with the swelling. I tried thinking unsexy thoughts, but my mind kept returning to the thought of Kelsey standing there watching and laughing, pointing at me and giggling about the pain my own erection was causing me.

The thought was making things worse.

Finally, after almost an hour, my cock had begun to return to its smaller incarnation, relieving most of the pressure. At 7:00 there was a knock on the door.

Looking stunning, Kelsey stood before me. She took one look at my face and smiled.

She brushed past me and over the the table, where she held up the black bag that had held the device. She turned up upside down and shook it.

"Good boy," she said, smiling.

"Now, about this," she said, tapping her finger on the contract. "I see you have signed."

I nodded. "Yes Kelsey. I have signed."

"But I haven't," she said. It was something I hadn't considered.

"That device you have on is made of titanium. You can't cut it. You can't break it. The lock too. It is on until I decide to remove it. The lock is impossible to pick."

She picked up the contract and looked over it.

"This contract is the only thing stopping me from walking out that door forever, leaving you in permanent chastity with me as a memory. One you won't even be able to masturbate anymore."

She came closer.

"Most guys would be kicking and screaming right now, threatening me, demanding to be released. But not you. All you are thinking is how can I get her to sign that contract? Terrified I might leave. You know I am going to be a nightmare for you, but you are willing to endure that just so I don't leave, aren't you. A deep, sick part of you actually enjoys it. Needs it. Wants to beg for it."

I looked into her eyes and nodded. "I need you Kelsey."

"I know" she said.

I have no idea what came over me, but at that moment, I kneeled down and pressed my lips down to her shoes and kissed them. "Please Kelsey, please sign the contract and make my life a nightmare. You can do anything you want to me Kelsey, just let me be near you. Please."

I felt her press the paper to my back and sign her name. "I'm sorry," she said. It would be the last time she would ever apologize to me.