Although this is not a sequel to my earlier story involving Katie, it is a continuation of my sexual adventures from that point.
Please note it is not necessary to read the first story before this one. But just so you know, Katie was a cougar that I met online and lost my virginity to. On with this story!
With that first encounter, I realized that my experiences with Katie had just begun. We met often, having sex in her room, my room, her car, and even a mall parking lot. However, over the next couple of years, I started getting serious girlfriends, and Katie was given more responsibilities at work. We met sporadically, enjoying each time, but knowing the next was a long ways away.
She had shown me what it was like to have a female in control. Katie often told me what to do during sex, and she enjoyed holding me down while riding my cock. I soon began to fantasize about being in control myself.
When I was twenty, shortly after I broke off my year long relationship with a girl named Natalie, I started to search adult chat sites for female submissives. I talked with a few, but none of them were quite what I was looking for.
One night, as I sat on the couch in my apartment, I pulled out my laptop. Within minutes I found a possible submissive, who listed her name as Jess18. I sent her a quick hello, and she replied, seeming flirty.
“So, I heard you’re looking for someone who can hold you down and have their way with your helpless body? ;)”
It took her a minute to reply, but she said, “Ohhhh yes 🙂 are you that guy?”
“Maybe. We’ll see ;)”
We chatted for about ten minutes. I learned that her name was Jessica and she was a high school student on their cheer squad.
“Oh really? I’m James. Are you a senior?”
“Nope! A junior. I’m only 17. Shhhhh! Don’t tell anyone here :)”
“It’s our little secret. I’m twenty, by the way.”
“That’s cool! What do you do?”
I told her about my desk job, and how I had an apartment to myself (though I didn’t tell her that my parents helped me pay for it). She seemed impressed, and told me that she lives with her parents in Ohio.
“Oh that’s awesome! I live in Illinois!”
We continued talking until about 11:30. She told me she had to go to bed. But before she left, I said, “PM me tomorrow after school!”
She signed off, saying “Of course…sir :)”
I was about to turn off my laptop when I realized how horny I had become. Turning on some porn, I started to stroke my shaft. I came quickly, fantasizing about Jessica being my submissive slut.
The next day at work was tough. I got a lot done, but I kept thinking about Jessica, and if she would be my submissive. Finally, at 5 I got to leave. I drove home and turned on my computer. Sure enough, I had gotten a message from Jessica.
“Hey! It was fun talking with you last night! I think we need to talk more about this dominance thing. It’s been a fantasy of mine to submit to someone. But I’ll talk to ya later!”
I sent a quick reply. “Get on at 9 tonight.”
Having nothing to do for a couple hours, I went to the gym to work out. As I sweated, lifting weights and running on the treadmill, I kept getting aroused thinking about having my own submissive.
I drove back home and took a quick shower. I made myself a quick dinner. As the delicious smell wafted from the microwave, I started to turn on my computer. By 9:06, I logged in. I was greeted by a message.
“Hey! Took ya long enough! :)”
Trying to sound dominant, I replied, “Well, good thing I make the rules and not you ;)”
“Alright, I’m fine with that!”
In almost no time, we got to talking about sex. It turns out Jessica was not a virgin–she had sex with her boyfriend when she was 15. However, he wasn’t very good, and to this day no man had given her an orgasm. I told her about all the things I had done, and she seemed impressed.
There was a slight lapse in our conversation. To move it along (and because I was extremely horny), I sent, “If you were my sub, I’d tie you down and do what I want with your body.”
“Mmmhmmm. I’d be a good girl and please you in any way I can”
We started to have an amazing roleplay, in which I tied her down and fucked her to multiple orgasms. My cock was aching in my pants.
At the end of it, I sent her my number, telling her to text me tomorrow. But, as I logged off, I received a text message.
“That was the best orgasm of my life. Have a nice night…sir. :)”
I turned on some porn, and masturbated, imagining Jessica being my personal fuck slut.
The next day, I went to work as usual. However, by 11 I had received a text from Jessica.
“So…can I be your submissive? :)”
Hiding my phone under my desk, I replied, “Hm…maybe.”
I shuffled papers around, waiting for my phone to light back up. A couple minutes later it did.
“Pleeeeeeease? I’ll be a good girl!”
“Alright, but that means you have to listen to, and do what I say.”
Again, there was a little wait before she replied, “Oh yay! It’ll be fun…sir :)”
“Rule 1: No texting in school. You need to get a good education. I’ll have more for you tonight at 9.”
“Okay see ya then!”
I was able to finish my workday, but my boxers were pushing uncomfortably against by hard cock. Again, I worked out, showered, and got myself food. I even had time to get coffee with an old high school friend.
But, at 8:45, I sat down on my couch to come up with different rules Jessica would have to follow. By 9, I had a sizeable list, though I was only going to tell a couple tonight.
I texted her, saying, “Are you ready for more rules Jess?”
“Rule 2: When you refer to me, you have to call me Sir, Master, or something of that sort.”
“Okay Sir. Any more?”
“Rule 3: No touching yourself without my permission. Rule 4: Tell me if you’re uncomfortable with anything I am telling you to do. And Rule 5: No relationships with other guys while you’re my submissive. You should probably write these down. And there will be more when the time comes.”
A couple minutes later she said she had written them down.
“Good, but you need to remember that this relationship is about having fun. And it is built on honesty. If you break a rule, be sure to tell me. I promise I won’t get mad.”
“Alright. But I’ll do my best to follow them!”
“I think it’s about time to send pictures, if you’re comfortable with that.”
The next text I received was of a beautiful brunette, probably about 5’2″ with what looked like B cup breasts. She was wearing a tank top and yoga pants. I sent one back of myself.
“Man, I have a hot master :)”
“You’re pretty attractive to Jessica.”
We started to roleplay again. This time, I dictated everything that would happen, with her just following along. By the end, I was stroking myself, and I received this message.
“Master, can I pleeeease play with myself? I’m so horny.”
I gave her permission, as long as she sent a picture of her sucking on her finger first.
I received the picture, with her finger sensuously sliding between her lips. It sent me over the edge and I came into my hand.
A few minutes later, she sent me, “That was another great orgasm sir :)”
“It was for me too 😉 but it’s getting late. Talk to you tomorrow!”
The next day, as I ordered, Jessica did not text me until after school. However, right at 3:15, I received a message, saying, “I was thinking of you all day master.”
I told her I was still at work, and she sounded disappointed. However, I got the idea to have her play with herself.
“Alright Jessica. Since you’re so eager to see me, go to your room right now and play with yourself, imagining me taking you at my pleasure.”
“Mmmmm. Okay master :)”
“But, you must do it for fifteen minutes. After that time, you will send me some pictures. Only if they are sexy enough will I let you cum.”
“Alright. I’m in my room now.”
I didn’t text her for fifteen minutes. I sat at my desk, trying to do work, but the thought of Jessica playing with herself while thinking of me kept entering my mind. At the end of the time, I checked my phone to find a picture of her tight pussy getting fucked by one of her fingers. Another picture came that showed her twisting and pinching her nipples.
“Send one of you licking your wet finger, and you can cum.”
I got it, and my cock started pulsing in my pants. Her brown hair cascaded down her bare shoulders as her wet finger was slipped between her red lips. She was looking seductively at the camera.
Not long after, she said, “I came. It was tough to hold off for those fifteen minutes while thinking of you.”
“I need to go. But I’ll talk to you tonight.”
That night, I texted Jessica, asking if she had a webcam.
“Of course! And I have Skype :)”
I sent her my Skype name, and turned on my computer to wait. I was soon greeted by a video call request, which I declined. Instead, I told her to call me back when she had put on the sexiest outfit she owned.
It took nearly five minutes, but finally the call request returned. I accepted, and saw her sitting on her bed, wearing a tight tank top and a miniskirt. I also saw myself, dressed in a polo with jeans.
“Hey master!” she said, quietly. “Can’t talk too loud. My parents are downstairs.”
“That’s fine. You’re looking extremely sexy!”
“Thanks, just wanted to please you sir!”
“Well, it’s working.” I sat there for a second, looking at the beautiful teen in front of me, before telling her to start playing with her breasts.
She gave me a sly smile, and her hands moved up her body to play with herself. Her fingers lightly caressed her breasts. Her hands started moving faster, pushing firmly against her breasts. They slipped under her tank top, pulling it up, and started playing with her nipples. She lightly pinched and twisted them, moaning slightly.
Her hands dropped, but she left her tank top pulled up past her breasts. “Was that good sir?”
I smiled at her. “Yeah. It was great. But we’re not done yet!”
She looked at me, intrigued. “What else do you have in mind?”
There was my opportunity. I put on a mask of severity, and asked, “Do you know what you just did?”
“Uh…no. No sir I don’t.”
“You forgot to call me sir or master. You broke one of the rules. You need to be punished.”
Her eyes got wide, and she looked excited. “What do I need to do, master?” she asked.
“You can start by taking off your clothes.”
She quickly stripped, turning her computer so that I could watch. When she was completely naked, she sat back down on the bed to await further instructions.
“Now,” I said. “Start playing with yourself.”
Her fingers hesitantly moved up her thighs to brush against her pussy. They slid easily, since she was already extremely wet. Jessica started to moan as her fingers made little circles around her pussy.
“Use your other hand on your breasts.”
She started to fondle her breasts, rolling her nipples between the fingers of her free hand. Her other hand continued rubbing her pussy, causing her to moan louder. I could tell she enjoyed having me tell her what to do.
“Finger yourself. Start off slow.”
I saw her slip one of her fingers into her pussy, and her eyes closed in pleasure. She started to finger herself, first with one finger, but soon with two. They started thrusting faster, and she moaned out in pleasure.
“Keep playing with yourself, but tell me when you get close to your orgasm.”
Jessica relaxed backward onto her bed. She continued thrusting her fingers into her pussy, and her other hand switched between her breasts. I felt my cock throbbing against by jeans. In almost no time, she moaned out, “Oh…I’m close!” She closed her eyes in anticipation.
“Stop! You are not allowed to orgasm.”
With what seemed like all her willpower, Jessica removed her hand from her pussy.
“Good. Is someone a little horny?”
“Ye…yes sir,” she moaned out. “Can I please orgasm?”
“No. This is a punishment not a reward. But you can lick your fingers clean.”
Jessica slowly raised her fingers to her lips. She stuck them in, one at a time, and sucked them clean. They came out glistening.
“Alright,” I said. “Start playing with yourself again. But as I said before, you are not allowed to orgasm.”
This punishment continued, and by the tenth time Jessica was told to play with herself, she moaned out that she was close within seconds.
She removed her fingers obediently, but grunted with frustration.
“Do you want to orgasm?”
“Oh…oh yes master! Can I please?”
“Hm…I don’t believe you want to…”
“Yes I do! Please master? I’m so horny. I love being your slave. Can I please orgasm?”
I pretended to think for a minute as she continued pleading.
Her hands flew down to her pussy, and she moaned loudly as she orgasmed. She thrashed on the bed, consumed with pleasure. After a long pause, she sat up panting.
“How was it?” I inquired.
“Oh sir. It was the best!”
“Good. But if you break another of my rules, I will be sure to continue this for hours, and by the end I won’t let you orgasm.”
“I’ll be sure to follow your rules, then, sir.”
We started talking again about how close we lived to each other. It was only a couple of hours for me, so I started seriously considering driving to see her. But, it was getting late, so we said our goodbyes and logged off. I turned on some porn, but didn’t last long. I came, imagining my slave pleasuring my hard cock.
However, before I went to bed, my phone rang, and I saw this message, “My parents are going to be out of town this weekend, sir. Just letting you know :)”
I didn’t reply, but I started thinking about what we would do. It was already Thursday; there wasn’t much time to wait.
I could not focus the entire day at work. At about 3:20, I sent a message to Jessica, asking her when her parents were leaving.
“In about twenty minutes, sir. Then I’m going to be all alone until Sunday afternoon. :)”
I couldn’t believe my luck. This was going to be an amazing weekend. I quickly texted back.
“I’ll be there at 9. Make sure you’re ready!”
“What should I do to get ready?”
I took a while to reply. While at my desk, I came up with a quick list for Jessica to complete before I got there.
“Alright. Here’s what you need to do:
1) Make sure you are clean and presentable (which includes shaving your pussy).
2) Put on another sexy outfit. Make it one where I would have no problem getting ‘public access’.
3) Clean your room. Make it look nice enough for me to stay in.
4) Do your homework. We don’t want interruptions this weekend.
5) If you have time, start cleaning the rest of your house.
6) I will text you when I am five minutes away. When you get my text, stop whatever you’re doing, unlock the front door, and start playing with yourself. Make sure you’re somewhere we can have some fun.”
She took a while to read the whole text. But she replied “Okay master! I look forward to you cumming!”
I left work a little early. I had a different kind of work to do. First of all, I went home to get on my laptop. I got on the internet and looked up lingerie stores near where Jessica lived. There were a couple. Perfect. I then got my keys and headed out to a local sex store.
I returned with my purchases to shower and change. It took me a while to decide what to wear, but I ended up putting on jeans and a button up. With a small spray of cologne, I was ready to go.
The drive seemed to take twice as long as it should have. But I was soon nearing my destination. When my GPS showed that I was five minutes away, I sent Jessica a quick text. Soon I was pulling into the driveway of a large brown house in the suburbs. I got out of the car and walked to the front door, carrying a large bag. It was unlocked. I stepped inside to see a large kitchen on the left, and an even larger living room on the right. The lights were on and the curtains closed. And laying on the couch fingering herself was Jessica.
She was wearing a tight blue tank top with even tighter yoga pants. The pants were pulled down to her knees, showing me she did not have on panties. As soon as she saw me, she got off the couch and pulled her pants back up.
“Hey!!” she said, coming over to give me a kiss.
I stepped away and raised an eyebrow at her.
“…sir!” she quickly added.
I set my bag down and walked forward to kiss her on the lips. My hand slid up her back to softly grip the back of her head. The other slid down to cup her perfectly formed ass. We kissed for a couple minutes before I pushed her away.
“How about you show me around.”
Jessica took me by the hand and led me around. They had a small basement that was just full of boxes for storage. The kitchen was very modern, full of all the latest equipment. The living room, which I had already seen, had two couches and a large comfy chair. There was also a large TV room and a bathroom. Upstairs was her parents’ bedroom, another two bathrooms, and her bedroom.
Her bedroom had a large king size bed, carpeted floors, and a closet on the far wall. The bed had blue sheets and two large purple pillows. Jessica turned and looked at me.
“Well…that’s about it…”
She leaned forward for another kiss.
I laughed. “Wait here. I’m going to get my bag. Just sit on the bed and think of all the things I’m going to make you do.”
As I left the room, she sat down on the bed, her curly brown hair obscuring her face. I carried my stuff up, and found her with her hand down her pants.
“Well, someone’s a little eager!” I said, dropping my bag on the ground and walking over toward her.
She jumped off the bed and kissed me with her soft lips. I felt her hands move all over my body. One of them slid slowly up my thigh. As she continued kissing me, her hand started stroking my cock through my pants.
I grabbed her and tossed her onto the bed. I climbed on top and began kissing her passionately. My hand quickly found her pussy, and I started rubbing it through her yoga pants. I kissed down to her neck and she began to moan my name. My other hand started roughly fondling her breasts. Jessica started moving her hands to unbutton my shirt.
I pushed them away, saying, “Nope, I’m the one in control here.”
To prove my point, I got off of her and headed for my bag. She sat up, confused. I reached down and pulled out two pairs of handcuffs.
“Now get back on that bed like a good girl!”
Jessica lay back down, and I walked over to her. With a click, I secured her left wrist to the left bedpost. I crawled over her to secure her other hand to the right one.
“Mmm. Now someone is completely helpless.”
I leaned forward to kiss her on her lips. As I kissed down to her neck, Jessica let out a small moan. My hands moved down her body, grabbing the sides of her yoga pants. In seconds, they were on the floor. I put some of my weight on her, pinning her to the bed, as my fingers started rubbing her wet pussy.
In between kisses, Jessica asked, “But…how are you…going to get my…shirt off?”
I slid two of my fingers into her pussy. With my other hand, I raised a pair of scissors. Sliding them slowly over her body, I replied, “Like this.”
I began to cut from the bottom of her shirt, making a jagged line of fabric across her torso. I stopped before the last couple of inches and tossed the scissors onto the ground. Reaching forward, I tore the remains of her shirt off her helpless body, revealing her perfect breasts.
My fingers kept thrusting into her pussy as I climbed back on top of Jessica. She was starting to push her hips against my fingers, wanting more. I started kissing her breasts. As I lightly nibbled on one of her nipples, she let out a huge moan and started thrashing under me.
She relaxed, panting, still handcuffed to the bed. I climbed off of her to give her a short break. I started looking through my bag, planning the weekend ahead in greater detail. But soon enough, she had recovered and was ready for more.
I got back on the bed to lay down beside her. My hand started sliding back up her thighs as I kissed her softly on the lips. Then, I started unbuttoning my shirt. I wanted to tease her, so it took a couple minutes for all of my clothes to be in a pile on the floor. Her eyes were fixated on my hard cock.
“Do you like it?” I asked, bringing it closer to her mouth.
“Oh, yes sir!” she replied, opening her mouth obediently.
I slowly guided it passed her lips, and I began thrusting into the mouth of my teen slave. She tried sucking the best she could, but it was difficult laying on her back with her head turned to the side. Small trickles of saliva and precum trickled down onto the bed.
As she sucked on my cock, my fingers found the folds of her pussy and resumed their fucking. Jessica moaned with my dick in her mouth, sending the vibrations through me.
But I didn’t want to finish too quickly.
I pulled out of her mouth and dragged my wet dick down the length of her torso, leaving a damp streak. I grabbed one of the pillows from her bed and, lifting her hips, placed it under Jessica. As I did this, she looked into my eyes.
“Master, I’m so horny. Fuck my helpless pussy!”
“Well…” I said, positioning my dick at her entrance. “I don’t know…I think you need to beg for it.”
“Oh please master! Fuck your helpless slave! She wants to pleasure you with her warm pussy!”
Unable to resist any longer, I thrust my dick into Jessica’s pussy. Both of us moaned loudly, and I started to fuck her.
“That’s right Jessica. Take it. Take my hard cock!”
“Mmmmm. Gladly sir!” she moaned in reply.
I thrusted faster, spreading her legs wide with my arms. She moaned, closing her eyes and tilting her head from side to side. I lightly slapped her across the face.
“Look at me when I’m fucking you, slut!”
She opened them, and gazed at me with her lust-filled eyes. I started to spank her ass as I pushed into her, causing it to turn slightly pink. My other hand roughly fondled her breasts.
“Oh yes sir! Keep fucking your slave!” She continued moaning, wrapping her legs around me.
I grabbed her hips and pulled to thrust even deeper into her pussy. We both moaned as my pace increased. I could feel my orgasm approaching, and I knew she was close too. All of a sudden, she began writhing on my dick.
I quickly pulled out, removed her legs from around me, and crawled toward her face. I stroked my dick as I came, sending my warm cum all over Jessica’s face. We both were breathing heavily.
Rising to my feet, I uncuffed her wrists. She collapsed down onto the bed, exhausted. As I returned the handcuffs to my bag, I saw Jessica reach for her face.
“Don’t wipe the cum off. Leave it on until tomorrow.”
My cum covered slut smiled at me and crawled under the covers. I turned off the light and joined her. I made sure to give her the pillow that we used for sex, so she would be constantly reminded of what happened and would be ready for more in the morning.
We both drifted off to sleep, master and slave.