Tommy Gets Lucky

“Rebecca Stevens is going to be dropping off a package for me around 11:00. Will you answer the door and put the package on the kitchen table for me?” Susan called to her son, Tom.

“Sure, no problem,” Tom called from upstairs. Tom was Jim and Susan’s 20-year-old son who was home during a break between his first and second year in college. He had grown into a nice-looking young man, standing nearly 6′ and weighing 170 lb. He had nicely trimmed dark brown hair and deeply set hazel eyes. He kept himself in shape by working out daily at the college health and fitness center as well as 2-mile swims, 10 mile running and intense 40 to 60-mile bike rides to train for triathlon competitions. He focused on strength and stamina building for the long grueling competitive events.

Rebecca Stevens, a longtime friend of Susan’s, was 48, and had been divorced for nearly six years. Even though she was more than twice his age, Tom had often fantasized about having sex with Rebecca. She was a petite woman, standing only 5’4″ and weighing less than 115lb. Despite her small stature, her breast size was a full 34C. She kept her auburn hair trimmed short, and with her black rimmed glasses, she always reminded Tom of a prim and proper school teacher. Tom was convinced this was part of her turn-on for him.

During the past six years or so, Rebecca would often drop by Jim and Susan’s house once or twice a week. And during her visits Tom would try to sneak peeks of her thighs as she crossed and uncrossed her slender legs and adjusted her skirt while sitting on the couch. At times she wore her semi-transparent white blouse, revealing her bra and well-formed breasts which would drive Tom nearly crazy. More often than not, after, or even during these visits, Tom would make an excuse and rush upstairs to his bedroom and lock the door. With Rebecca’s image planted squarely in his mind, he would slide out of his pants, and after just a few furious strokes on his cock, would cum what seemed like gallons.

Now he was a sophomore in college and living on campus. And though he had been involved with two or three girls his same age, all of it consisted of just heavy petting. He had truly enjoyed getting his hands inside their blouses, unhooking their bras and feeling up their luscious young tits, while they would open his pants and pull out his stiff cock and stroke his dick to a full-fledged orgasm which he spurted into his handkerchief, even once, into pretty blonde Betty Litz’s cocksucking mouth. Nonetheless, he was still a virgin.

And to be honest, during more than one of those heavy petting sessions, he closed his eyes and imagined the girl he was with was Rebecca, or even her daughter, Vanessa, who was now an 18-year-old senior in high school. Was it normal to fantasize about an older woman, or another young teen whom he had never even dated? If not, he didn’t care. Rebecca’s and Vanessa’s visions had provided him with many nights of orgasmic ecstasy.

The thought of seeing Rebecca again after a 3-month hiatus was arousing, even if it was just for a moment as she dropped off her package for his mom. ‘I have a package I’d like to give her’, he thought, and smiled.

It was only 9:00am and Rebecca wasn’t due to arrive for another two hours. He couldn’t wait that long. He searched in his closet for his stash of porn videos and selected one. No one was home, his father was out of town on business, and his mom wouldn’t return before 4pm. ‘Why not just watch it on the wide screen downstairs,’ he thought.

Tom finished unpacking his clothes and took a shower. He put on a pair of sweat pants and escort headed downstairs with the video. It was 9:45. That gave him plenty of time to watch the video, jerk off, and hopefully be able to answer the door without a raging hard on pointing at Rebecca as he received her package.

Tom put the video in, rewound it, and hit the play button. He fixed himself a coke, and then walked back upstairs to get a small jar of Vaseline from his parent’s bathroom to assist him at the right time. He could hear the faint sound of moaning coming from the downstairs television.

“Damn, where is it?” Tom said aloud, as he rummaged through four or five drawers. After searching for several minutes, he found the jar sitting almost directly in front of him on the sink counter. “Finally,” he muttered, as he took the jar and a towel, then headed back downstairs.

As Tom came down the stairs, he caught the faint smell of something different. It was perfume, but not his mother’s. At the bottom of the stairs, he stopped. He found the source of the perfume… Vanessa Stevens. She was standing just beyond the foyer, no more than three or four steps inside the family room. She was staring at the television.

When Tom saw her, he tried to turn quickly and run back up the stairs. Then he heard her voice. “Tom?”

Tom tried unsuccessfully to hide the towel and Vaseline.

“Vanessa, I…” he stammered. He could feel the heat rise in his cheeks.

“Tom, I’m sorry, I didn’t know you were home. My mom told your mother I would be dropping off a package for her at 10:00 this morning.” Evidently Tom’s mom had misunderstood the time. “The door was unlocked so I… I’m sorry. I guess you’re enjoying some videos?” The young teen looked a little uneasy at confronting him while his porno video played in the background.

Tom was caught with a porno video playing right in front of his mom’s friend’s daughter, and not only that, but it was the sexy daughter of another woman he had secretly fantasized about for years. And he was standing directly in front of her, wearing only a pair of sweat pants and holding a jar of Vaseline only partially hidden by the towel he was holding.

“Vanessa, I’m sorry about this,” Tom said, as he avoided eye contact while his vision switched back and forth from the slut getting railed on the TV to the sexy teen standing in front of him. He wanted to get to the video and shut it off. He had never been so embarrassed in his life. “I’ll turn that off,” he said, starting to make his way around where she was standing.

“It’s ok if you want to leave it on,” Vanessa said convincingly.

“Huh?”

“I don’t mind, I’ve seen them before,” she said. Tom stopped and turned to face her. She had an enthusiastic expression on her face Tom had never seen before.

“You… have?” he asked.

“Of course!” Vanessa moved toward him and touched his arm with her hand. “Have you ever watched one of these videos with a girl before?” she asked.

“Uh, no,” he stammered.

Vanessa knew Jim was out of town until the next day and Susan wouldn’t be home until late in the afternoon. She slowly ran her hand along his forearm. “Would you like to watch one with me? We could enjoy it together,” she asked in a soft voice. “Would you like to have some fun with me?”

Tom couldn’t believe what was happening. “I would like to watch one with you very much,” Tom said.

Vanessa walked back and locked the front door and closed the blinds in the family room. She took the jar of Vaseline from Tom and said, “I don’t think we’ll be needing this,” as she set it on the coffee escort bayan table. His head was spinning. She took him by his hand and led him to the couch.

Vanessa was wearing a pullover tunic style short dress with a short skirt. Her skirt slid up to her mid-thighs when she sat down, and through her tight top he could see the outline of her nipples. Obviously, she had no bra today.

On the television screen a man was slowly licking a blond woman’s breasts, and she was moaning with pleasure.

Vanessa asked, “Have you ever done this to a woman before?”

“Yes, a couple of times,” Tom answered. “They always seem to enjoy it.”

“Would you like to do this to me?” she asked. She didn’t wait for his answer, and was already pulling her shoulder straps off her shoulders.

“Oh yeah,” Tom said. He was already getting hard as he saw her bare breasts come into view.

Vanessa slipped down the top of her dress and then let it fall to her waist. Her beautiful full breasts and bright pink nipples were now in view to Tom.

Tom gasped. “They’re wonderful, more beautiful than I ever imagined.”

“Then be sweet to them and eat them up,” Vanessa sighed and moved towards a leather loveseat in front of the widescreen TV. “It’s playtime. Come and sit with me.”

Tom sat on the couch while Vanessa sat across his lap and he cupped one breast in his hand while he kissed and licked between her breasts, moving from one to the other, kissing, licking and sucking while Vanessa cradled his head in her hands. She began to moan softly as Tom suckled each nipple in turn, feeling each in his hands as his lips moved back and forth.

Tom slid his hand along her bare right thigh while he continued licking her breasts. She opened her legs slightly. Vanessa pulled his face away from her breasts momentarily and kissed him deeply. Their tongues were rolling and exploring each other.

“Have you ever had a woman do that to you?” she asked, pointing to the screen. The blond woman in the video was now sliding her lips up and down the shaft of the man’s huge cock.

“Uh, not really, I had a girl touch me down there before, I really enjoy a handjob, you know.”

“Then it’s time for you,” Vanessa said, as she slid her hands inside the waist band of his sweats. Within seconds, she had pulled down his sweats and Tom’s straining 7-inch cock was released.

“Oh, how nice and hard you are,” she said, as she gently cupped his balls in her right hand and lowered her lips to his shaft. The feeling of her warm moist lips and tongue on his cock was incredible. He told her to stop or he was going to cum right away. Vanessa looked up, smiled, and said, “You just relax and enjoy this. If I can bring you off once, then we’ll have time to do it again.” A moment later the sensation was too great, and Tom felt the pressure in his balls pass the point of no return. He groaned loudly, and felt the release of spurt after spurt of hot cum as she held her face to his cock and he shook with pleasure. Vanessa swallowed most of it, but there were a few droplets that fell on his thighs.

“Now it’s my turn,” Vanessa cooed. “I hope you’ll man up to going down on me.” She stood, sliding down the rest of her skirt, letting it drop to the floor. She stepped out of her black lace panties, revealing her neatly trimmed dark bush. When she reclined on the couch and spread her legs, Tom could see small beads of wetness surrounding her pussy lips. Tom dropped to his knees, put his hands on her small hips, and pulled her gently to his mouth. Her musky odor was causing his cock to swell again. bayan escort Moving his hands, he used his fingers to gently spread her lips and began licking her wetness, letting his tongue caress slowly up and down her slit. She raised her hips to give him better access.

“That’s right, Tommy, just like that,” she moaned. When his inexperienced lips and tongue found her clit, she cried out, and convulsed with her first orgasm, holding his head firmly and grinding her pussy against his face. When he pulled away, his lips and chin were covered with her juices.

Tom was rock hard again and now wanted to fuck Vanessa Stevens more than he had wanted anything else in his life. He stood and positioned himself above her on the couch. Vanessa was more than ready too. She reached between them and stroked him two or three times before guiding him to her opening. She gasped when the swollen head of his stiff cock entered her. She felt like an animal in heat now. She wanted and needed this young man to possess her. She needed him deep inside of her, and to fuck her until she screamed.

Vanessa reached around his body and pulled his ass forward, burying him into her completely. Her pussy felt warm, wet, and gripping. Because she was petite, Tom tried to prevent placing all of his weight on her, but she continued pulling him into her.

Tom reached under her and squeezed her ass as he pumped in and out of her.

“Oh… God,” Vanessa panted, as her young lover quickened his pace. “You… are… so… good!” she said between thrusts.

Tom could feel the pressure in his balls building again. Vanessa knew she was about to explode with her second orgasm. The world became a blur. Both Tom and Vanessa were reaching the peak of ecstasy as they held each other, locked in a rhythmic embrace. Tom made two more long, quick thrusts, and then buried his cock as far as he could deep inside of Vanessa’s cunt, and groaned deeply. She felt his cock begin to spasm, and this sent her over the edge. She buried her face in his chest and screamed out her pleasure, as wave after wave shook her young body. Tom could feel her pussy milking him as he released his load.

They relaxed in each other’s arms for several minutes, and then went upstairs to take a shower together. Once in the warm shower, they washed each other’s young bodies with a growing passion as their hands massaged each other’s genitals. Vanessa dropped to hind her and greased her asshole with slippery shower gel, her knees and took Tom’s stiff cock between her lips and sucked him feverishly. “How about it, Tom? Do you think you can do me again? Have you ever done anal on a woman?”

“Oh my god, not yet, but I’d love to try. Is it OK if I fuck your ass?”

“Go ahead, Tom. I want you to give it a try. Use some shower gel on your fingers to grease my asshole, then slowly force your cock inside and start assfucking me slowly.”

Vanessa dropped to her knees and spread her cheeks while Tom knelt behind her and greased her asshole with the slippery shower gel. He thrust his single finger up her butt, then two fingers together to try to stretch her tight anal orifice. “Are you ready, ‘Nessa? I think we can do it now.”

While they were drying off Tom confessed his long-term fantasy about her.

Vanessa smiled and said, “You’re not the only one with fantasies. Would you like to take me out for a date on Saturday? My folks are going to my Aunt’s home for a visit for the weekend.”

On her way out the door she stopped and said, “Oh by the way, I left your mom’s package on the kitchen table. Tell her she doesn’t have to thank me, I think it was a great trade.”

With that, Vanessa walked to her car, and Tom watched her drive away until she was out of sight. He closed the door and thought, ‘I’m the luckiest guy who ever lived. I can’t wait till Saturday night.’