Chapter 3 - What a Pleasant Morning
When Damon woke up he felt arms wrapped around his waist, which was a good feeling, but bizarre. Usually he would have gone home before his female companion woke up, but Elena was different. He felt her hand slide down his body, she was still completely asleep. It then landed still on top of his boxers and rested over of his cock. Just the tiny amount of pressure was enough for him to start getting erect again. Although, most things Elena did gave him a hard on. She started to massage the area that her hand rested upon; she had to be awake now. His erection thickened and lengthened after each stroke upon the fabric of his boxers. It wasn't a particularly thick fabric, but he knew this technique took skill. She was such a little bitch, teasing him all the while knowing that he couldn't do anything about it, because he was a gentleman, at least to Elena he was. To take this relationship farther he would have to be nice, so he let her tease him a bit longer. It was an unbearable feeling for Damon to have to put up with when a girl is stroking him and he can't do anything about it. His breathing was in short rapid succession as to control himself, so that he could show little Ms. Gilbert that he was in charge, not her. All the control in the world couldn't help even the most level headed man to ignore what happened next. Elena had wriggled her way downwards on the bed to where her mouth was right in line with his throbbing erection.
"Elena," Damon flourished, his face bright red. "Well good morning." Damon couldn't hold back any longer as she bit the elastic of his boxers and crawled downwards as his boxers slid down his legs. His erection sprung free as Elena crawled back up towards him and grasped his cock firmly in her hands. "So, this is all mine?" she asked cheekily. "Of course," Damon replied. "Well, I don't remember much, what do you like?" Damon was stunned. Elena Gilbert was asking him what he wanted her to do. This was like having the whole world at his fingertips. "Well," Damon started, "Usually I just let you go for it, but since you need a refresher, you can start by licking the tip." It felt weird to be giving her such blatant directions, but she wanted to learn, and he was definitely willing to teach her.
She massaged the shaft in her hand as she slowly circled her tongue across the engorged tip. Damon's knees buckled, almost hitting Elena in the face, but this just made Elena more confident. She drew letters on the head of his cock. Damon's super sensitive skin tried to depict just what she was writing, but he was too concentrated on the glorious sensation. Elena was getting frustrated and asked "Now what do I do?" "Well," Damon panted, "You are doing a pretty good job, just go for it, surprise me." His husky voice was hard to resist and Elena began to do what she was told. She took a stiff tongue and lapped all the way from the base of his cock to the tip, over and over again. Damon was moaning which sent a pleasant smile to Elena's face. Next, she took almost his entire length in her mouth until it hit her throat. She gagged a little and pulled back. "Well that's no way to learn," Damon sneered with a sexy grin on his face." "But... I," Elena stammered. Damon quickly cut her off my shoving her head hard down on his throbbing penis until she gagged again. He knew he should be gentle, but she'll get her reward soon enough. Another tug on her hair downwards and she had successfully taken all of him into her mouth. "There, see, you did it," he encouraged. Feeling proud of herself Elena attempted a couple more times and succeeded until Damon yanked her hair and pulled her onto the other side of the bed with his rapid speed.
"Damon, please, don't be too rough!" Elena shouted. She had obviously had enough abuse for one day, but Damon wasn't ready to give up just yet. Damon quickly removed her shirt with a succession of two rips. "Damon!" Elena exclaimed, her tank top now in pieces. All Damon could do was wink; he didn't exactly care right now. He sucked at her nipples hard until each one had flushed with blood and was standing at attention. She shivered from the sensation as goose bumps ran down the length of her body. Damon caressed her stomach admiring the tight skin that expanded and contracted when she breathed. HE suckled at her breasts a few more times before moving his hands between there bodies, Damon laying on top, and slid it down her boy short PJ's and inside her panties. They were already moist, undoubtedly from Damon, who she couldn't bare to resist. He started rubbing his finger in between her folds until she was moaning. He slowed his fingers until they reached her clit, which was already engorged with blood. He tugged on it a little which was somewhat painful for Elena, recognized by the loud "Ow!" that spewed from her lips. But amongst the pain was pleasure which sent shivers down her entire body. Damon knew how to play her like a fiddle. She started moving her hips around and around just so her clit could get the slightest taste of Damon's hand. As her hips moved down Damon finally slipped a finger inside her dripping center. She let out a loud moan that indicated to Damon that this was exactly what she wanted.
Quickly, Damon picked up speed, adding an additional finger that filled Elena completely as she was so tight. He pumped in and out of her as she moaned intensely. "Damon!" she managed to croak between her rapid breaths. "Please. I need you!" Damon cocked his head to the side, "Where?" "On my clit!" she exclaimed wildely, unable to control her own voice. Damon was certain that if he did as she wished, she would cum in an instant, and he wanted to drag this out as long as possible. He removed both his fingers from her core and tasted her flowing juices. "Damon, please!" Elena demanded again, "I need you on my clit!" "I'm sorry, Elena, you know we can't do that now," Damon replied. Although she was not going to get her way, Damon would not disappoint. "I'm going to lay here for a second and catch my breath. If you want to please yourself, go ahead, but I will be the one fucking you." Elena understood. She climbed on top of Damon so that she was straddling his body where he had a beautiful view of her chest. "Elena," Damon ordered, "Do not fuck me, sweetie, that is my job." "Damon," said Elena, mimicking the same voice that he used, "I'm not going to fuck you." And with that she placed his penis so that the head was resting on his lower abdomen. She positioned her folds on either side and started grinding on him. Damon was amazed at how skilled she was at pleasuring herself. With each movement, his rock hard cock was applying amazing pressure and stimulation to her clit. Elena was almost dancing in ecstasy rubbing back and forth along his shaft. "Damon! Fuck!" she exclaimed. Hearing her call his name was heaven. Her pace increased as she was bordering on the edge of an orgasm. He felt her pussy flutter and an explosion erupted inside of her. Her climax was intense, but she did not ejaculate. Damon knew he could do better.
Elena collapsed on her side of the bed. Her body felt spineless, like a big ball of jelly. "We're not done yet," Damon jeered. Elena regained her bones in a matter of a minute and was ready for the ride of her life. Damon placed her lying down with her breasts pointing towards the ceiling, so perky and delicate. He crawled on top of her and ordered her to hold her legs spread wide. "Ms. Gilbert," Damon stated, "You may just be the best girlfriend I never had." Elena obviously didn't grasp the joke, but she was too wrapped up in the beautiful sight that was unfolding before her. Damon positioned his erect penis at her entrance which was oozing with desire. With one thrust he only managed to get about half way in. "Holy fuck, you're tight," he replied. Damon thrust another time, three quarters in. A single thrust after, and his entire cock was buried deep inside Elena's tight pussy. Elena gasped when his cock hit her front wall, he was the biggest she had ever seen, or remembered seeing. "Damon!" she yelled, "Don't stop. She tried to meet his thrusts, but they were too powerful, bumping her almost enough for her head to hit the wall. He stimulated her throbbing clit with his thumb, enough pressure to make her head throw back onto the pillow. Damon was ready to come, he had been ready since the moment he woke up next to her, but he wanted to feel her cum.
"Elena," he whispered. "I want you to come for me, okay baby?" "Elena could only make out a small "Mmhm" which was enough of a yes for him. He quickened the pace thrusting into her pelvis harder and harder with each pump. "Fuck! Damon! Please! I'm gonna cum!" she shouted. "Cum baby, just cum!" Damon ordered. And just like that, Elena's walls tightened and fluttered against Damon's cock as her juices started flowing out of her, surrounding Damon's penis, still lodged deep inside her pussy. He felt his orgasm ensuing as her walls kept fluttering. He shot his hot cum out onto her chest that made Elena moan with pleasure as the heated liquid hit her nipples. "Oh god, Elena!" Damon exhaled harder and harder until he had pumped himself dry. This was definitely worth waiting for.