Jess Finds Herself in a Contest Ch. 02

Once inside the house I tossed all of my stuff onto the entry way floor, locked the door behind me and headed straight for the bedroom. I have a small array of toys in our sex drawer. I knew exactly which one I was going to use. I pulled off my shirt as i walked up the stairs. That went flying somewhere, no idea where. As I entered the bedroom I kicked my shoes off, slipped my hands down either side of my workout pants and slipped quickly out of my workout pants. By the time I got to the dresser i was wearing only tiny white workout socks. I left a trail of clothes into the bedroom.

I opened up the drawer and grabbed the Doc Johnson dildo. It's a light brown model, 10 inches long and 7.5 inches in circumference. When Jake and I were at the adult store we were looking for something big to add to our collection. I already had a little pocket rocket that was excellent for stimulating my clit, and a six inch hard plastic vibrator, but I needed something that was life like. I said if we were going to get something realistic lets get something big. That turned Jake on. The store was all out of white flesh colored ones so we went with the light brown one. Somewhat convenient for the moment. If only we'd grabbed the darker model I thought to myself.

We didn't use the Doc Johnson very often, occasionally when the mood would hit one of us and we were feeling particularly naughty one of us would bring up using the "big cock" to work my pussy really good. I had never used it by myself before. Doing this made me feel particularly naughty. As I pulled it from it's bag I realized that the silicate powder that it's covered in to keep it from drying out was standing in the way of me getting what I wanted.

Damn it. I thought to myself. I needed to wash it off with the toy soap. Before I headed to the bathroom I grabbed the lube so that I could get started as soon as possible. I quickly rinsed it off in the bathroom, making sure I got all the powder off, then gave it a quick once over with the hand towel. Seconds later was on the bed and scooting towards the headboard. I reached down and yanked my socks off and then reached down with my free hand and used two fingers to spread my labia. I was pretty wet already and my two fingers slid inside of me easily.

The toy was in my left hand and the lube was on the bed right next to me. I was working my right middle finger and ring finger in and out of my pussy. I quickly worked my fingers all the way inside of me. When I pulled out this time I moved my index finger over to join the other two. Now I had three fingers working in and out of my pussy. In no time i was shoving my three fingers as deep as i could inside of me. It still wasn't enough. Time for the big cock.

I was wet enough that I might be able to go without lube. Jake and I would usually use the toy before we fucked. Normally Jake would go down on me first to get me nice and wet, but we still needed lube to make it a little more comfortable. I grabbed the big cock by the base, I had a firm grasp on the giant balls and the suction cup at the very bottom of it. I then began to slap the large head against my clit. My clit exploded with sensation from the large, heavy tip smacking against her. I then placed the large head flush against my pussy. I slowly started to push the tip in. While i was pushing in i started gyrating my hips. This happened without even thinking about it. Slowly i was getting used to the feeling of it stretching me. I kept pushing the big cock further inside me, all the while moving my hips in a rhythmic, circular motion. It felt fantastic.

Once I got the head inside, I started to slide the big cock further into me . I began to feel a little discomfort from the friction. Damn it, I thought to myself. I was hoping i wouldn't need lube. I pulled the big cock out and grabbed the lube with my left hand. Flipping the top open with my thumb I gently squeezed the bottle while running it up and down the shaft, taking care not to make a mess. Once the big cock had a nice strip of lube along the entire shaft I flipped the lid closed, tossed the lube across the room, and used my left hand to work the lube around the entire girth of the big cock. Once I was satisfied that he was nice and lubed up I plunged the head and the first few inches inside of me.

"Fuck" I said out loud. The feeling was a shock. I took a deep breath, lifted my head slightly and looked down at the big, light brown cock inside of me. I then began to let my mind wander. I closed my eyes and pictured Dante's chest and abs. I then built a complete picture of him in my head. His handsome face, muscular arms, perfect chest and abs, then I imagined that this 10 inch cock that was just barely inside my pussy was his. As I fantasized about that my pussy started to tingle. "Give me that cock Dante." I said out loud. Then pushed it further in.

I then imagined that him and I were alone together in the training room. Instead of turning and walking away to change after I teased him with my ass, I turned back around and ask ed him, "Do you want this ass?" He doesn't beat around the bush or play shy. He just walks over to the door, lock it, then comes back to me and takes me.

"I don't just want that ass, I'm taking that ass" He says to me. While I played the dialogue over in my head I slid the big cock further in. It hurt a little despite the lube. I could feel it pushing on the walls of my pussy. It had been too long since we'd used the big cock I thought to myself.

I looked down and saw that just over half of the big cock was inside of me. Jesus, I thought to myself. I thought more of him would be inside of me by now. I let me mind get back to my fantasy. Dante tears my clothes off and tells me to get on the floor. I do exactly as he says. When I'm down on the floor he takes his clothes off showing me his beautiful body and his giant, beautiful black cock. We are staring into each others eyes and he moves towards me and tells me to suck his cock. I do exactly as I'm told.

I pulled the big cock out of my pussy and moved it up to my lips. I pushed it into my mouth all the while fantasizing that it's Dante's cock and we're in the workout room. I worked the big toy as well as I could, but was only able to get about half of it into my mouth before I started gagging. I guess there is one drawback to a really big cock, it's much harder to give head. I bet anal is completely out of the question. I worked the cock as good as I could, getting it nice and wet with my saliva and pushing it as deep as I could into my mouth. My eyes were watering and my jaw was starting to get sore. Back to the fantasy dialogue. "Dante, please fuck me with that beautiful cock." I beg him.

I then moved the big cock back down to my pussy and pushed it in as far as I could. The feeling was so intense, and so much of a shock to my insides that I let out a deep sigh and my entire body shuttered. The head of the big toy was pressed firmly against my cervix. I left it in at the same spot for a good minute letting my pussy get accustomed to the girth. I looked down to see how much was inside me. I didn't feel the balls against me yet, so I knew it wasn't all the way in. I saw that there were maybe two inches left, but it was already bottomed out and pressing hard against my cervix. I imagine myself looking up at Dante, "Sorry Dante. I'm not used to such a big cock. You're going to have to take it slow. But I promise, my pussy will take all of you. You just need to slowly work my tiny pussy out, and stretch her" The thought of saying those words to him had me more turned on than I'd been in a long, long time.

What would Dante say to me? I asked myself. He's a stud, he's probably fucked lots of his married white students. He's used to having to take it easy on us. "Just lay back and relax baby. I'm almost all the way in. I'm just going to push a little more and your pussy will expand to take all of it." As i imagined these words I pushed the big cock further inside of me. I was biting my lip and curling my toes as I felt the tip pressing harder on my cervix. I felt as the back of my pussy was giving way. She was growing to accommodate Dante's giant black cock.

I then felt the balls pressed up against my ass. A smile crossed my face. "You feel amazing Dante." I said out loud. I kept the big cock all the way inside of me letting my pussy adjust. It started to feel more comfortable. After another minute it felt natural, it felt just right, like my pussy was built for this big black cock. "I told you I could take it all."

What would Dante say to me? I wonder. "Jess, your pussy feels amazing. I've wanted you since the moment I saw you. Your pussy feels like home to my cock." As I imagined his words I began fucking my pussy hard and fast with the big cock. I was pulling it all the way out so that the head just touched the entrance, and then slamming it all the way in. All the while i was gyrating my hips back and forth. The feeling was intense. Being this full felt so different, so good.

A minute into pounding my pussy I felt that buildup. My body started to shake and I began fucking my pussy as fast as I could. When I finally came I plunged the big cock all the way in and kept pressure on it leaving it all the way inside of me. I was gripping the big cock as hard as I could. My other hand was gripping the sheets tightly, and my toes were curled at the end of my extended and flexing legs. My back was arched and i was lifting my hips and crotch into the big cock as my entire body shuttered. "FUCK" I screamed out loud.

The orgasm lasted a good 45 seconds. It felt great not having to be on top to have a vaginal orgasm. There is something slightly more fulfilling about being able to cum like this when I'm not in charge and controlling the motion. It feels like I'm being taken, instead of the one doing the taking. I like the thought of that. The thought of being more submissive than I normally am, and of being taken by an aggressive man with a giant cock. The thought of Dante taking me.

I lay there for a minute after my orgasm ended. The big cock was still all the way inside of me. Fantasizing about Dante fucking me, ravaging me, having me any way he wanted me. I then slid the big cock out. As the length of it slowly exited me it tickled and my body writhed at the feeling. The cock seemed so long. Finally it was all the way out. I wasn't sure where that whole thing even came from. It was so unlike me. But it sure felt good.

After laying there for a minute longer I scooted off the bed and got to cleaning up my mess. What to do now?

-----

"So, how's the training with your new girl Jess?" Sarah asked me.

"She's a natural." I told her. "You know she's 42 years old?" I asked Sarah

"No way," Sarah replied. "She doesn't look a day over 30."

I'd worked with Sarah at Everyday Fitness for the past two years. We were pretty tight. Nothing inappropriate. It's best not to get involved with co-workers or trainees. I found that out the hard way. When I first started working as a personal trainer the sheer volume of pussy that threw itself at me was irresistible. I slept with several co-workers the first year I was training. Obviously when the sex stops, or when a girl starts getting serious, problems occur.

Even worse than sleeping with your co-workers is sleeping with women you are training. I made that mistake three times. Never again I told myself. One of the three turned out well. A single lady in her mid 40s. I was 23 at the time. She had an amazing body, and fucked like she was a pro. She was very successful and we had a good run for almost six months before she ended up breaking things off when she got serious with a guy that was better suited to her position in life. There were no hard feelings, and we still occasional kept in touch, in a purely professional way.

She was my first. Since that turned out so well I figured, why not take advantage of all the opportunities. The next one was just a few weeks later. That one turned out relatively poorly. Her name was Nicole. She was about my age, and had a few pounds more than my typical girl, but she did have an amazing ass and hips. I'm a sucker for that. We kept it going for about two months before I had to break things off. Towards the end Nicole would stick around after her workouts and try to non-nonchalantly watch as I trained other women. She started getting upset when I would work closely with other attractive females. Some co-workers noticed her hanging around and shooting daggers at the other women. They figured out what was going on and warned me that I needed to end it before things went too far south.

I wasn't particularly attached to Nicole, and kind of had my eye on another woman, so I followed their advice. Nicole was pretty upset but eventually she just stopped coming to the gym. The other woman that I had my eye on was the real nail in the coffin. Her name was Juliana. She was a few years older than me. She was amazing. A beautiful, tall brunette with great curves and great tits. She was married. I trained her for about a month and a half before we started fucking. We both got very into it very quickly. We were fucking everywhere, in her car, in my car, in her house, in hotel rooms. We were having sex for about two months before things took a turn in the wrong direction. Juliana started to get serious and one afternoon after we had finished fucking in a hotel room she told me that she wanted to leave her husband and be with me.

I really liked Juliana, but I also wasn't into destroying anyone's marriage. Juliana then told me that she had gotten kind of careless with the credit card bills and that her husband had found out. She admitted what was happening and told him that she wanted to get a divorce. I put the brakes on our relationship, but it was too late. The ordeal came to a head when her husband confronted me at the gym and the staff had to keep him from throwing punches. I ended up getting fired. Rightfully so. I also nearly had to get a restraining order to keep Juliana from stalking me. She eventually got a divorce from her husband because of our affair. I told myself that that would never happen again.

After i was fired I moved from Atlanta to the Florida Panhandle to get a new start. I have been here for about five years. And I've been good for five years.

"Be careful Dante." Sarah told me. "I can see it in your eyes, and in hers. There's chemistry there. You told me how things went the last time you slept with a student."

"I know, I know." I told Sarah. I sighed and let out a deep breath. "I dig her. But I know that we can't let our ridiculous chemistry turn into more than what it is now. I need to find a booty call ASAP to keep my mind from her, and to keep my other head from making me do something stupid." I continued.

Sarah Laughed at that. "I'll help keep you honest. I'll peek my head in during your personal sessions to make sure you guys don't get carried away. I know how hard it can be when you're in the training room alone, watching a girl with an amazing ass do squats right in front of you. The she does something just a little wrong and you need to put your hand on her to make a correction. Next thing you know you're shacking up in a hotel room. Am I right?" Sarah said to me with a scolding tone.

"I know, you're right." I told her. I wonder to myself how I am going to keep this in check for the next seven weeks of training leading up to her competition.

At home that night, when I was in bed and getting ready to sleep I pulled out my phone and started scrolling through pictures. I came to the pictures of Jess and looked at them with lust in my eyes. I felt my cock jump slightly. I reached my hand down and grabbed my cock and gave it a squeeze. Seconds later I'm scrolling between her different poses and tugging hard on my cock. I'm imagining what she must feel like. How tight and wet her pussy must be, and how that amazing ass would look bouncing up and down in front of me.

When I touched her today she definitely felt a spark. I did too. I know she wants to fuck. I don't know if she's ready to, but i know she wants to. I kept stroking my cock as I imagined how the pale white skin of her perfect rounds ass would look bent over my bed. And how it would look with her reaching back and spreading her ass cheeks and pussy so that I could stick my black cock inside of her.

Seconds later I'm ready to come. I reached over and grabbed my hand towel, slipped off the bed, and started stroking my cock furiously. The final thought as I came into the towel was of Jess. What am I doing? I asked myself. I know that letting things get physical with Jess is a terrible idea. For my job and for her marriage, but my desire for her is almost unbearable.

-----

I felt a little guilty Friday night when Jake and I were having sex. I'm sure every person in a relationship sometimes imagines sex with another person, but I knew this was a little over the top. Jake had already expressed a twinge of jealousy over Dante, and there I was using the big cock to pound my pussy fantasizing about Dante. It turned out that I couldn't keep my mind from wandering to Dante that night. While Jake was fucking me I found myself thinking about my session earlier in the day. Naturally my mind then wandered to Dante. I wanted to feel like I did this afternoon.

"Honey, do you want to use the toy on me?" I asked Jake.

"Of course I do. You feeling a little naughty?" Jake asked me.

"Just a little." I lied.

While Jake went and got the big cock ready I laid on my back and played with myself. When Jake walked back with his hard cock sticking straight out in front of him and the big cock in his hand, I rolled over onto all fours and wiggled my ass back and forth for him.

"Come on baby, give it to me." I told him.

Jake gladly obliged. I loved that he got off on that. I didn't always want to be filled by a big cock, but when the mood struck it was good to know that it turned him on just as much as it turned me on. Jake left me wet and worn after pounding my pussy furiously with the big cock. All the while I had my head buried in the sheets and visualized Dante pounding me doggie style. After I came I felt bad about asking him to use the toy so that I could fantasize about Dante fucking me. I briefly toyed with excuses that would make me feel better about it, but in the end just thought, what's a girl to do? When you need a big cock, you need a big cock.

To make up for my little trickery I told Jake to sit on the edge of the bed. Once he was there I climbed on, slipping both of my legs behinds his back. I grabbed his shoulders and began grinding on him. I didn't stop until our loins were both red and sore. I could see in his eyes that he was holding on for dear life, trying not to cum. We ended up cumming together. Jake isn't packing anything near what the big cock is, he's five, maybe six inches, but he does know how to work it, and has pretty damn good control. Overall It a was pretty damn good session if I do say so myself.

The rest of the weekend went well. I was disciplined and stuck to my routines. I was excited about Monday. Excited to keep working on improving my body, and excited to see Dante. Sunday night when I put my gym bag together I decided to pack a somewhat sexier workout outfit. Instead of my usual yoga pants, sports bra, and T-shirt, I decided to pack my short pink workout shorts and my stand-alone sports bra. As I'm zipping up the bag I realized that I was consciously going down a dangerous road. I even told myself to keep it under control, but in the end my interest in seeing where this went got the best of me.

Monday's training session didn't exactly go as planned. I arrived full of energy, excited to work out and excited to see Dante, but he was kind of reserved. He wasn't unfriendly, but the normal connection just didn't seem to be there. He seemed to be all business. After a while it started to distract me and it took all i had to focus on the exercises instead of the business-like vibe. When the class ended I thanked Dante and stood there for a minute waiting to see if he had anything else to say. After a few seconds there was nothing.