tagBDSMJessy Trains Jake Ch. 01

Jessy Trains Jake Ch. 01


Jake still couldn't grasp how things had gotten this out of control. There he was, on his back like a whore, tied to his girlfriend's bed, (Was girlfriend even the right word anymore?) dried cum covering his mouth, the word 'slut' written on his forehead with sharpie and most frightening of all, his girlfriend of 12 months standing at the foot of the bed, going in and out of his tight ass with a medium sized strap-on dildo. Jessy moan, no doubt having another orgasm, and said, "Oh slut-boy, if only you had filled my ass like this when we were equals. Maybe things would have turned out differently." At that moment the dildo rubbed against his prostate sending him over the edge. Streams of hot, sticky cum shot out of his abused dick and covered his face and stomach. How could this have happened he thought again.

Three Months Ago:

Jake stood outside his girlfriend, Jessy's house horny as ever. Jessy had given Jake head or at least a handjob around every 3 days since they got together, so her month long birthday vacation (she had turned 19) had been a nightmare. Jake had spent more then one night up making use of his hand and the Internet. He felt a little bad as Jessy had asked him nicely not to look at porn while she was gone. She thought it, "was just gross." But a boy had needs. Jake collected himself and knocked on the door. Jessy's mom answered and after exchanging greetings directed Jake upstairs. Jake knocked on Jessy's door and hardly noticed that the flower decorations on her door were missing. "Enter," came her voice. Jake loved that voice. He opened the door and saw Jessy bent over her suitcase, unpacking. Jessy was a half a head taller than Jake. Jake was on the short side so this only bothered him a little. She had long brown hair and Jake had short dirty blonde hair. Jake's eyes drifted down her body, he loved ever part of her. Her slender, fit figure from running track. Her large, round, supple tits. Her cute ass. She even got a tan over her vacation. Jake on the other hand was pretty white, he hadn't gone out much that month. His phesec wasn't that bad. He was on the skinny side but had some muscles from doing push ups and sit-ups everyday, but no where close to Jessy's athleticism.

She turn around and smiled, her green eyes meeting his blue. She walked up and kissed him hard on the mouth, and to his surprise, squeezed his ass. He was about to say something when she broke away and her eyes went directly to his pants where, already, a bulge was starting to form. "Excited to see me I see." She said with a laugh. "I could say the same to you." Jake replied. "Well, take them off." She stated, a bit more forcefully then normal. Jake didn't need to be told twice but only got his belt and fly half way done before she stopped him. "Wait babe," she said, "My jaw is kinda sore from all the screaming I did at this concert last night, could you maybe.... Rub this one out?" Jake eye's widened and he was about to protest when she stopped him again. "Come on, I'll do it with you." She said skillfully slipping out of her short, shorts and exposing her panties. Joseph could already see a pool starting to form on the material. "It'll be fun." "...alright." Jake finally said. Jessy smiled and kissed him on the cheek as she moved to lock the door.

Jake pulled his dick out through his underwear and began to awkwardly rub the tip. It was about 5 inches long. Jessy turned around and gave Jake a look of slight surprise. "What are you waiting for? Everything off." "You mean... Get completely naked... To jerk off?" Joseph asked slightly nervous. "Don't be a spoil sport babe." Jessy replied crossing the room to her bed, her hand briefly brushed against Jake's exposed cock. This was enough to convince Jake who, although reluctantly, completely stripped down. Jessy crawled up onto her bed and sat there cross-legged. She was still wearing her t-shirt and panties. She regarded the naked boy in front of her. Jake just shifted from foot to foot, uncomfortable in his exposed state. "Come over here," she said suddenly pulling a bottle of lotion off the dresser. Jake complied quickly and Jessy quickly and efficiently lubbed him up, coating his cock with was already hard and dripping with per-cum. In fact, Jake could never remember being this turned on before. Jessy finished and pointed to the spot on the floor right in front of the bed, "Stand there." "Ok?" Jake replied with a slight smile but Jessy did not return the expression. Jake stood at the spot.

Jessy slipped her hand under her panties and began rubbing. Jake took this as his que to get started. He started slowly at first, just continuing to rub his tip but then he start to move his hand up and down the shaft. His body starting to rock with his natural masterbation rhythm. Had he not been so engrossed by his greedy member he might have noticed Jessy staring intently at him, almost forgetting her own pleasure. Then, for good measure, Jake added his second hand, both now moving up and down his lubracated cock. Slowly his eyes started to close his eyes and, to the surprise of even himself, started to let out little moans of pleasure. Like a slutly schoolgirl losing her virginity. Jake could not believe the feeling, it was like he was masterbating for the first time again. But he couldn't understand what was different.

Suddenly, through his lust filled pleasure he heard a voice in his ear. "Hey babe," It was Jessy. For the life of Jake he could not remember hearing her get up. Jake groaned in reply, his eyes still closed and his hands still working away. "Babe, I want us to try something really hot. Could you please.... Try not to cum until I tell you too. I just want us to cum at the same time, that's all." Jake's eyes still remained closed and his brow furrowed in confusion, but his cock suddenly got harder then ever. "Alright," he replied half moaning. He could feel Jessy continue to stand there for some time but soon, the throbbing pressuring in his rock hard cock was beginning to be too much to bear.

Finally Jake asked, "Jessy, can I cum?" In the back of Jake's mind he noticed something strange at that moment, he had never asked Jessy if he could cum before. "What's the magic word?" Jessy answered finally, no hint of joking in her voice. "Jessy can I please cum?" Jake said quickly. "Wait 10 more seconds." Those seemed to be the longest 10 seconds of Jake's life. He started moaning loudly like some whore getting a good fucking. Finally Jessy said, "Get really.... And... Cum now!" Then, as if right on cue, Jake ejacualated with more force the he had ever experienced in his short 18 years of life. His eyes flew open as cum covered his ragging hard-on and dripped on to the floor. He squirted a good seven times before the orgasm was over. This drained him so much that he actually had to lean on Jessy for support. It was at this moment that he realized something strange. He was looking at a mirror! Jessy must have slowly turned him completely around while he was masterbating and he had not noticed. What he saw in the mirror was even more bizarre. There he stood, spent, completely naked and exposed. Cum dripping down his still erect cock and his girlfriend standing next to him, smiling and still somewhat dressed. Jake could not help but feel a sudden change which he couldn't describe.

Jessy gently kissed him and pointed to a box of tissues. "You should probably clean up." She said softly. "Right." Jake replied somewhat embarrassed at what had happened. His face must have turned red too because Jessy said, "Don't be embarrassed. I'm just glad you enjoyed that." She gave him a sudductive smile as he got on his knees to clear up the cum, still naked. "Your jaw will be better tomorrow... Right?" Jake asked nervously. "Of course." Jessy replied. Jake felt a feeling of relief wash over him knowing this would be the last time they did something like this.

Except it wasn't, far from it in fact. Everyday Jake would come over to Jessy's house. And everyday it would be a different excuse or a sudductive use of words. But it always ended the same way. Jake, completely naked, masterbating in front of Jessy until the exact moment when she said he could cum. Sometimes Jessy was fully clothed. Sure most of the time Jake would protest but it didn't take a lot from Jessy to convice him. Jake wasn't really sure why he went along with it. Maybe it was he because it pleased Jessy and he liked to see her happy with him. Maybe it was because, ever since this ritual started, she had wanted to see him everyday. Or maybe because when Jessy told him to cum, he would have the best orgasms of his life. This continued for a month straight. Then Jessy started to have Jake change positions when he masterbated in front of her. Sometimes she would have him lay on his back on the bed. Sometimes she would have have him get on all fours and masterbate. And sometimes he would even have to knell in front of her and work his lubbed cock up and down for her until she finally let him cum. This lasted for two months. For that entire time, the thrill Jake got never faded. But Jessy was still far from done with Jake.

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