Jess And The Younger Man

Jess had just celebrated her thirty-sixth birthday and felt about as old and used up as a woman her age could fee. She was tired and worn out and frustrated and most of all saddened as she stared at herself in the mirror. Her hair was much thinner than it had been in her twenties. Her laugh lines were more pronounced. Her breasts were not as full and perky as they had once been, and her eyes crinkled. Where had the time gone? It seemed that her body had gotten older while her mind was stuck in adolescence.

Jess slipped in to her nightgown then clicked the light off and slid into her single bed. The night was warm and she slept with the window open. She could hear the neighbors' television from the apartment next door. She had Jeffrey on her mind.

Jeffrey was the new IT guy at the high school Jess taught at -- a kid, really. He was only 23, and barely that. But he flirted with her relentlessly. He was a really nice guy so Jess flirted back when no students were around, initially believing they were just teasing.

It was behind the safety of an instant messenger on her home computer, that Jess realized he wasn't teasing.

"I'd love to let you teach me a few things," Jeffrey wrote, including a winking smiley. Jess laughed and told him he should behave.

"I mean it," he continued. "I have a fantasy about being with an older woman. And what guy doesn't fantasize about banging a teacher? And you're hot."

Jess blushed. "There are places in this country where I'd be old enough to be your mother."

"Yes, but you're not my mother," he reminded her.

It was nice to be flirted with and Jess found herself warming to this guy with all his barely 23 confidence.

"Girls my age haven't let go of the bull shit, yet," he told her. "I want a woman who knows how to be fucked without crying about her childhood afterward."

Good lord, has he come to the wrong place, Jess thought to herself. She was quite possibly the most sexually repressed person on the planet.

It wasn't that she didn't like sex. She loved it. But her desires were specific and she couldn't bring herself to give voice to them. Lovers would ask her what she wanted, but she was too embarrassed or shy or who knows what to tell them. As a result, they tended to treat her with kid gloves, afraid of offending her or hurting her. This was exactly the opposite of what Jess desired most.

Jess longed to be manhandled. Nothing was more erotic to her than being held down by a lover, knowing she was at his mercy. She loved to feel teeth on her skin and to feel her hair being pulled. She loved to be spanked.

And it was the comfort of hiding in her room with nothing but her computer monitor that allowed her to reveal these things to Jeffrey, despite her better judgment.

Jeffrey had amazing insight for his age. "I think you're afraid to tell your lovers these things because the element of control is what is most erotic to you," he told her. "You want to relinquish control to someone else, yet telling him to do those things defeats that purpose. You are still in control."

Jess wasn't certain that was the case, but the amount of thought and logic impressed her.

"You know," he continued, "I could make you feel pretty powerless, if that's what you want."

Jess felt her cheeks flushing hot. For a brief moment, she could visualize the experience: his long physique pressing down on her, his thick arms forcing her hands over her head as he sinks his teeth into her shoulder, his knee forcing itself between hers.

"I'm too old for you," she said, banishing the thought for the moment.

"You're only 36," he said, "And besides, I'm not asking you to marry me. I just want to fuck you."

Jess could not help the giggle that escaped her at those words. It sounded really tempting. But she'd never had much luck with casual sex. She found it a challenge to keep from getting her feelings tangled up in things. This was just crazy.

And it was here that Jess excused herself and went to get ready for bed.

And now, as she lay listening to the sound of cars passing on the highway, she imagined what it would be like to meet with someone just to have sex with him. No strings attached. After all, those other one-night things -- those were only confusing because they'd had different expectations going into it. In this case, they'd both know that it was only for this one night.

But only for one night? It seems like it would take many times to get to know each other and please each other. Jess began to imagine the things she'd like to do, to have done.

It was difficult for her to imagine it being mutual. Sex, for her, had always been part of at least the pursuit of something deeper than two people simply pleasing each other. She imagined Jeffrey cold and absent, using her body as if she were not in the room.

And then there was the issue of his age. There were 13 years between them. Wasn't this somehow immoral?

But as the night wore on, Jess began to realize that Jeffrey truly seemed to want to please her. His age would really only matter if they were pursuing something more permanent, but this was just one night. What difference would it make?

And Jess could tell him what she wanted from him, what she needed. She needed to feel safe. If this were simply an exercise in mutual pleasure, Jess felt confident that she could tell Jeffrey what she wanted.

Jess could hardly bear to look at Jeffrey the next day at work. Was he looking at her differently? Leering, perhaps? She couldn't tell. But when he wasn't there, her mind wandered to him. She imagined what he looked like under those Dockers and that Polo shirt -- the coolness of his skin -- the fine blond hair on his legs.

She imagined the stamina of a 23 year old and blushed deeply, hoping with all her strength that no one had noticed that blush.

That night when Jeffrey instant-messaged her, Jess could hear her heart pounding in her ears. She was more than a little disappointed when she read his first message. "Hey," he told her. "I'm sorry if I was a bit aggressive, the other night. I totally respect you, and don't mean to make you feel uncomfortable. I'll drop it."

"No," Jess answered after some hesitation.

"No?" Jeffrey replied.

"No," Jess repeated. "I've thought about it, and I think that if we talk about it, this could be really great."

"I think it could be," Jeffrey answered. "As long as we both understand that no strings are attached.

"Of course," Jess answered, with some reservation.

They set a date for the following weekend. They would meet at the Holiday Inn, have a couple of drinks, and go from there. They also agreed on a code word, "halt" which meant "stop, I'm not kidding," in case things got out of hand.

Once the plans were finalized, Jess began to feel uneasy. The thought of being with someone who knew what she wanted and really wanted to give it to her was more than thrilling. But she'd never had sex devoid of emotion, before, and feared this would be cold and distant.

Still, despite her reluctance and absolute notoriety for repression, Jess's sense of adventure would not let her back out on this. On Saturday, she arrived at the Holiday Inn and rented a room for them. She left a key at the desk for Jeffrey and proceeded to room 307. She let herself in, dropped her bag by the door and sat down, nervously on the bed. The butterflies in her stomach were on steroids.

Jess tried to find things to do to pass the time until Jeffrey arrived. She flipped through the channels on the television. She checked her hair and makeup a couple of times. She looked at her outfit in the mirror. "Not bad," she thought. And then, with a sick knot, "for a 36 year old."

Jess's heart began to pound when she heard the lock on the door click and Jeffrey entered, carrying a grocery bag and a backpack. "I picked up some wine," he said, smiling.

Jeffrey put down his bags and pulled out a bottle of wine. He sat down on the foot of the bed, pulled off the foil, and unscrewed the cap. Jess supressed a chuckle as she sat down next to him with the two plastic glasses.

Jeffrey poured wine into both glasses and placed the bottle on the floor. "To fucking," he said, bluntly, raising his glass to Jess.

Jess blushed and her hands began to tremble. She laughed nervously. "To.... yeah," she said, as she drank her wine as quickly as possible, hoping it would calm her nerves.

"Don't be nervous," he said, soothingly, taking Jess's now empty glass from her and placing it on the floor by the bottle. He slid behind her on the bed and began massaging her neck gently. His voice was calm and comforting, and Jess liked the sound of it. "I promise this will be good for both of us," he said, sliding his hands down her shoulders, working the tension out slowly, patiently.

"I am nervous," Jess admitted, relaxing a bit under Jeffrey's strong hands.

"I'll take care of you," he said, quietly, his mouth close to her ear, as he handed her his glass of wine, and continued to massage circles into her shoulders and back.

Jess could feel her face warming. In fact, she warmed a bit everywhere, as the chill of nervousness was beginning to wane. She finished off her second glass, and allowed her body to slump forward, slightly, in relaxation.

"That's more like it," Jeffrey said, softly, as he pulled her hair to one side and began to kiss the back of her neck.

Chills shot through Jess. She felt her skin becoming goose bumpy and she felt her nipples harden. His mouth was so hot.

Jeffrey continued to plant soft kisses on Jess's neck and shoulders, as he let his hands begin to explore her body slowly. He stroked her back and her sides, as he drew himself around her completely, one leg on either side of her. He slid his hands under her shirt and stroked her stomach. Slowly, he let his fingers trace the contours of her ribs, her sides, and the underside of her breasts. He kissed the back of her ear, her shoulder blade; he nibbled the nape of her neck. And then he pulled her shirt off, leaving her feeling chilled and hugging herself.

Jeffrey folded his arms around Jess. He took her hands in his and began stroking the underside of her breasts with them. He left her cupping her own breasts as he slid her bra straps down her shoulders and then unfastened it in the back. "Whenever you're ready to let go," he whispered into her ear, as he ran his fingernails gently over the lines her bra had left.

Already he was a better lover than three quarters of the men she'd been with, simply because he wasn't rushing her. Jeffrey removed his shirt, and slid his arms around Jess. He wrapped his fingers in her fingers, which still clutched her breasts.

Jess arched her back and let her head fall against Jeffrey. She could feel the hair on his chest against her back. This was the body of a man. She could feel his breath on her cheek. She could hear it. She let her bra fall to the floor and placed Jeffrey's hands on her breasts.

Jeffrey squeezed them and pinched her nipples. He bit her neck hard but gently. Jess turned her head to catch his mouth with hers and they kissed.

Jeffrey slid his body out from behind Jess and laid her gently on the bed. He continued to kiss her fiercely, as he explored her torso with his hands. Jess responded to his kisses but forgot she had other body parts and just lay there for a moment before reaching up to stroke his hair.

Jeffrey pushed her hands to her sides as he positioned himself above her, kissing her more and more passionately, biting her neck, her lips, and her ears.

Jess was completely aroused. She felt as if every nerve stood on end. Every part of her sparked with electricity.

Jeffrey slid down Jess's body, leaving a trail of soft bites as he traveled. He bit her shoulders, her arm. He teased her nipple with his tongue and then he took it into his mouth, biting and sucking and taking Jess's breath away completely. Jeffrey began to grind his hips against Jess and she could feel his arousal pressing hard against her. She tried to reach for him, but he still held her hands to her sides.

Jeffrey slid further down her body, biting her stomach, kissing her navel, licking her here and there. He released her hands and slid his hands down to pull her skirt up. Slowly, he pushed it to her waist, kissing and biting her at all times. Jess, eyes closed, lifted her hips so he could push her skirt up underneath her. Before she could lower them, he'd stripped off her panties, and she lay there, completely vulnerable.

Jeffrey began to tease her. He nibbled her thighs. He stroked her pelvis. He blew on her moistness, letting her know he was aware. And then in one movement, he wrapped his arms around her thighs, lifted her hips, and plunged his face into her wet opening.

Jess cried out in surprised pleasure. She reached for his hair, but he held her hands tightly in his own. He plunged his tongue deep into her, sucking and licking, and rocking her whole body with his.

"Oh, my god!" she cried out, realizing she was reaching orgasm already. At this cue, Jeffrey released one of her hands and thrust two fingers inside of her. He found her clitoris with his lips and sucked and nibbled as his fingers plunged in and out of her.

Jess's whole body spasmed with the waves of orgasm. She covered her face with a pillow and cried out into it. Jeffrey continued to suck and nibble and Jess thought she'd die of stimulation. She reached to push him away, but he held her hands again, and she had no choice but to ride the intensity of it.

When the waves subsided, Jess lay limp and stunned, breathing heavily into her pillow. She felt Jeffrey leave the bed for a moment. She was slightly embarrassed to have come so quickly, and she remained under her pillow. Until she heard the zip.

Jess pushed the pillow to one side, and saw Jeffrey standing next to the bed, taking his pants off. She could see his erection, now, as he stood there in his boxer briefs, and she was more than impressed with what she saw. She pushed herself up to a sitting position and pulled him to her by his waistband. She slid her hands up the legs of his shorts and stroked around his hardness, brushing her lips against it, through the cotton garment.

Jess pulled her hands from the legs of his shorts, and slid the shorts down enough to expose him. She stroked him and teased him with the tip of her tongue. She held his testicles in her hand and traced the tip of his penis with her lips.

Jeffrey let out something that sounded like a growl, and grabbed Jess by the hair, jerking her head back. With his other hand, he pressed his dick to her mouth. She could taste the pre-cum on her lips. "Suck it," he demanded. And she did. She took it in as far as she could and sucked him until his knees trembled. He fell against her, then, bracing himself with one hand on the headboard. The other hand, he gripped her hair with. "I'm gonna shoot it all over your tits," he told her, pulling out with a groan. Jess clutched her breasts, as Jeffrey exploded on her, his hot ejaculate dripping down her bosom.

Jeffrey collapsed to the floor and rested his head on the bed. Jess went to the bathroom to wipe herself off. When she returned, Jeffrey was on the bed with a peculiar look on his face. He patted the bed next to him, and with a grin, Jess lay down beside him. She was startled to hear her pillow humming.

"I brought you a present," he told her, pulling a slim, silver vibrator from under her pillow. He ran the thing the length of Jess's body, coming to a rest at the warm mound between her thighs. Then he placed her hand on it. "I want to see you masturbate," he told her.

Jess began to protest, but the look on Jeffrey's face sent a thrill through her and she did as she was told. She slid the silver wand down over herself, stroking herself slowly and gently. She squeezed a breast with her free hand as she let her knees fall outward, opening herself up to the tiny little machine.

"Fuck yourself, with it," he insisted. Jess resisted, enjoying the feel of the vibration on her clitoris. "Maybe you need to be punished?" Jeffrey mused, rolling her to one side, and smacking her hard on the ass.

Jess's eyes flew wide open as she cried out. "Then do as you're told, Jess," Jeffrey winked.

Jess enjoyed a challenge, and frankly, she enjoyed a good spanking. "Make me," she whispered.

Jeffrey laughed the laugh of one surprised by the audacity of another, as he rolled her over on to her stomach and smacked her ass repeatedly until it was red.

Jess begged for him to stop, though the sting was arousing her in ways she didn't know possible. She never uttered the code word. "I'll do it! I'll do it!" she conceded. And when he rolled her back on to her back, she slid the wand inside of herself, as tears rolled down her cheeks.

"That's good," he said, stroking himself back into erection. "That's really good. Don't cum. Just a teaser."

Jess was ready to come again and tried with all her strength to resist the urge, when Jeffrey, took the wand from her and rolled her back to her stomach. Once she'd adjusted, he lifted her hips and guided himself into her, slowly, having lubed himself already.

Despite the lubrication and the priming with the wand, Jess was surprised at how he filled her up. He moved slowly at first, allowing her to get used to him as he gained speed and thrust.

Jess rocked slowly into Jeffrey's girth. It had been some time since she'd been with a man and this was taking some getting used to. It felt so good, though, filling up completely with his heat.

Jeffrey began to move faster. Jess responded in kind. She reached back and stroked his testicles between her legs.

Jeffrey grabbed her by her hair, and began to thrust more and more aggressively into her. Jess moaned with every thrust. She could feel his intensity growing.

With his free hand, Jeffrey found the vibrating wand and held it against Jess's clitoris, stroking her gently in front, while slamming hard into her from behind. The contrast in sensations sent Jess over the top, and she cried out, as she reached orgasm for the second time.

"Fuck, yeah," Jeffrey groaned, gripping her hips tightly to him, as she writhed in pleasure. And as the moment took him, he pulled her onto himself over and over, rocking her like a rag doll, until he exploded inside of her, collapsing against her in ecstatic exhaustion.