Cyber Playmate to Hotel Roommate

The day was here: the day Bill and Jenna would finally meet each other and consummate their online relationship, if all went according to plan. They had talked for months over the computer, but this was the first time they were ever going to see each other in person. They hadn't even exchanged pictures. Jenna knew she wanted Bill, but she thought seeing his face and obsessing over his picture would get her too nervous go through with the meeting. He made her laugh, he listened to her, and he had a Southern gentlemanly charm about him— things men of her age knew nothing about. She was confident enough in her own appearance that he would enjoy her, but she was secretly concerned that she wouldn't match the image he had created in his mind over the long months. Bill wanted to see Jenna, but, like her, he had fallen for her even without an image. She was smart, sassy, vivacious, and, above all, still possessed the fun characteristics of youth. So they decided to appear to one another as strangers for their first meeting, which excited them both.

Bill was stuck in a bad marriage. He had done everything he could to save the relationship, even gone to counseling multiple times. He was tired of trying with his wife and bending over backwards to make her happy, but he stayed for his children. He was a good man and a great father; his story was cliché, but true. More than anything, he wanted to feel alive, like a man again, and knew Jenna could fulfill that desire. Jenna was only 22 years-old, still a college student, and Bill was more than twice her senior. She had gotten out of a bad relationship some time ago and wasn't looking to meet anyone; Bill had ended-up being an appreciated surprise in her life. Even though there was a large age difference between them, they had discovered they had several things in common. In fact, they complimented each other's personality quite well. They were both quick-witted with a great sense of humor, and they genuinely liked each other's company online--and not only during their numerous cyber sessions. They had wanted this meeting for a long time, but it took a lot of convincing on Bill's part for Jenna to consent to meet him because his home life. Finally, though, she had relented and given in to his repeated requests.

They planned to meet for dinner at fancy restaurant inside a hotel in a city between their respective towns. They would meet in the restaurant's bar at 5:30 pm. Jenna chose the time because she believed it was lucky to meet at half past. Bill told her he would be there waiting with a rose, so that she would know it was him--and, he joked, so that she could quickly disappear if she didn't like him. The thought of a man nervously holding a rose made Jenna laugh, but she cared for him too much to tease him. Jenna showed up 45 minutes early, figuring Bill would arrive 30 minutes early, which he did. She sat in at a corner table, her tan legs crossed beneath a tight, black skirt. She read from a section of the newspaper that was on the table and occasionally looked up at the man with the rose. Bill saw the woman in the corner and wished it would be Jenna. He knew it couldn't be because of the time; he wondered if the excitement he was feeling for this woman would be mirrored when Jenna arrived. He wondered why he decided on the rose, doubting himself. He looked at the woman again. He was getting hard.

"How can I greet Jenna with an erection? What will she think of me..."

Bill was lost in his thoughts, wondering if she would like him, would want him, when he suddenly realized he never thought about not liking her--physically.

"Shouldn't all 22-year-olds be with other 22-year-olds?" he began to wonder.

Jenna continued to watch him. He was nervous. She played by occasionally crossing and uncrossing her legs, pausing a moment when they were uncrossed, before sliding them together again; it appeared to that she was innocently attempting to get comfortable—though it was far from the truth. The third time she shuffled, she caught Bill's stare. She felt a tingle throughout her entire body when her eyes met his. She could tease him, and herself, no longer; she liked him--the touch of gray in his hair, the worry in his eyes, the sweat he quickly brushed from his brow. Jenna was ready for the evening with Bill to begin, very ready.

After 15 agonizing minutes, Bill slowly finished his bourbon and laid the glass on the table. As he did, he sensed the shadow of someone next to him. He looked up and saw the woman who had begun giving him an erection.

"Hi, Bill," Jenna said smoothly.

His mouth fell, but he quickly regained himself. "Jenna?"

"Yes," she smiled as she picked up the rose and smelled it.

"Damn," he confidently stated, while shaking his head, taking her hand and lifting it while he checked her out from head-to-toe. "You are gorgeous," he said with a smile, turning on the playful Southern charm Jenna expected from him. He clearly no longer cared about the huge erection filling his pants as he stood to hug her. After a quick hug, he pulled away again to look at her.

"God, woman..." he muttered.

"Enough already," Jenna replied, blushing, and suddenly feeling like she no longer had the upper hand. "I'm hungry."

They both smiled.

Bill and Jenna got to know one another in person over dinner, even though they already knew each another quite well. Their gaze barely broke away from one another. Jenna thought Bill was quite handsome and liked the thought of being with an older man whose feelings and expectations she knew and matched. Bill thought Jenna was striking. He had fallen for her candor and wit long ago, but her beauty was the icing on the cake. She wasn't the least bit vain, though he thought she easily could have been. Dinner passed quickly, somewhat nervously, both of them eager about what would be coming later. After the meal ended and Bill left the waitress a generous tip, he turned to Jenna.

"So, do I make the grade?" he teased, though he actually was quite concerned. She took a moment to respond, and he suddenly felt a bit foolish.

Jenna smiled and looked down. As she did, she ran the side of her high-heeled foot up the leg of his pants. She looked up and replied, "You passed with flying colors."

He took her hand and led her from the restaurant. He was dying to get her upstairs and wondered if she felt the same way. As the door to the empty elevator shut, he quickly discovered she did. Jenna pressed her body against his and gently rubbed the crotch of his pants which made his cock spring to life.

"Can you eat any slower?" she breathed before she roughly kissed him, inhaling the scent of his musky cologne.

"If you want me, too," he teased. She rolled her eyes, raised her eyebrow, and flashed a wicked grin at him.

Bill unlocked the hotel room door and walked in as Jenna followed close behind. He turned on the lights around the room, and Jenna watched him. She could tell that he was a little anxious--or perhaps it was excited. The wetness between her legs betrayed the calm attitude she was attempting to display. As he crossed in front of her, she reached out and grabbed his arm, pulling him toward her. She wrapped her hand around the back of his head and pulled him down for a kiss. As their lips pressed against one another's and their tongues laced together, Jenna's nipples began to harden. She pressed into Bill and could feel his excitement as well. He wrapped her in his arms and held her, and she felt so safe. His hands pressed up and down her back, making it arch and press into him more, before tracing their way down to her ass, which he cupped and squeezed.

She took a step back and began leading him to the bed--their eyes locked on one another. She walked backwards, pulling him to her, and Bill wondered how this woman--this girl--could cast such a spell on him. Jenna sat him on the bed, and Bill gave her body a once over, like he had been doing all night. He started at her feet. She was wearing black high heels with straps around her ankles; no panty hose were needed on her tan legs; a snug-fitting black mini skirt covered the parts he was dying to taste; and a tight, silk, white button-down blouse was begging to be removed. Her dark brown hair was twisted up but a few strands had fallen down since they kissed.

"She is perfect," he thought, amazed by his luck and the fact that this college girl would want to be with a man in his forties--his upper forties.

Bill's stare weighed heavily on Jenna. She knew he was risking a lot to be with her, and she suddenly felt a quite uneasy, wondering if she was meeting his expectations. She had been waiting so long for the day he would finally take her and hoped he wanted her as much as she wanted him. As he sat on the bed, she parted her legs and straddled him, hovering above his crotch. Her breasts were so close to his mouth; she yearned for him to lick them, to swirl his tongue around her hard, pink nipples and to bite them just to make her jump. She bent down to kiss him again, and he eagerly responded. Jenna wanted to feel Bill inside her, and it was taking every ounce of control she had not to fuck him right away. She broke the kiss and backed away.

Bill didn't want her to stop, but as she stood before him, he noticed she was unbuttoning the top button of her blouse. He loved the way her hand methodically moved from button to button; she used just one hand. If she struggled with a button, she was patient to work it through. He could see glimpses of her white bra. It was covered in lace, and Bill was happy she chose to wear white for him. It made her tan stand out more; it made him hard remembering the innocence of her age; and it made him feel like she was honoring their first time together--a first time of many, if he had his way.

Jenna pulled her blouse off and stood before him in her bra. She knew her ample C-cups were overflowing in the tight bra she purposely chose to wear. The chill in the room shocked the heat from her body and made the light hair on her arms stand on end. She reached to her side to unbutton her skirt. It fell to the ground, and she kicked it aside. Jenna was wearing a pair of very thin, very small, white lace G-String that matched her bra. She stood before him, as if asking him to grade her now, searching his face for approval.

"Damn, Girl," he whispered again with a smile and a shake of the head.

"He likes me," she thought, as rush of heat passed through her body and between her legs.

Suddenly, Jenna realized that she was still wearing the black high heels, which didn't match her bra and panties. Getting them off would be too tricky at the moment, so she left them on. She reached back and undid her bra, tossing it to the side and releasing her soft breasts and hard nipples. The cool air quickly made her nipples even harder and caused a shudder passed through her. She took both of her hands, placed them on her hips, and slid down her panties. Bill loved that she didn't bend her knees to remove them; she kept her legs straight and just wiggled them off when she could no longer reach. She stepped out of them with one foot and then circled them around the other ankle before kicking them away.

Bill's jaw dropped as he eyed the gorgeous, young girl before him. It was at that moment he realized that she was finally completely his for the taking, and he didn't know how he was going to keep from cumming at that very moment. His eyes soaked up the beauty of her full breasts, and his mouth watered for her perfectly shaved pussy. Then she added a final torture: she pulled her hair and made it all cascade down around her shoulders in large, soft curls. What she told him was right: she did look sweet and innocent, but Bill knew she was far from it. Even though Bill was more a sensual, slow lover, he found himself wanting to jump up, grab her, throw her on the bed, and ram his cock inside her—deep inside her--fucking her hard enough to make her scream. Yet, there was something about her that made him want to be gentle with her, too, even though he knew she preferred things rough. He couldn't wait to see her face when she came, when he made her cum.

Bill stood up from the bed, and Jenna placed his hands on her sides. He eagerly ran them along the curve of her hips and up to her breasts. He cupped her soft breasts and then lowered his mouth to kiss them. He felt a shiver pass through Jenna the moment he put his mouth to her. He then began to suck and massage her tits. Jenna let out a moan and threw her head back. His mouth was around her nipple and his tongue was flicking across it. Her leg instinctively lifted and she pressed herself against him. Without missing a beat, he reached down and grabbed her knee, grinding himself against her.

"Bill..." she purred, between the sense of pleasure she was getting from him sucking her breast and the excitement of finally feeling his hard cock between her legs.

He suddenly started sucking her nipple hard, very hard, the way she told him she liked. He let go of her leg and put his hand on her pussy. She was so wet that his finger slid right inside her. He started with one finger... then two.

"Ohhhhhhhhh, God..." Jenna gasped, her legs weak.

She grabbed his head and practically shoved her tongue down his throat. Jenna wasn't one for foreplay, but thought Bill would like her to take her time. She wanted to do what she thought he wanted, but she was having a harder time fighting her urges than she expected. She was dripping wet for him and all she could think about was him filling her with his hot cum. She began unbuttoning his shirt. Bill liked allowing Jenna to be in control of this encounter, and it was making him even harder seeing how much she wanted him. He looked into her eyes as she looked up from his shirt. Her gorgeous eyes were so focused on him--so intent; he knew that there was nothing he could do to stop this night even if he wanted to, which he didn't. He raised his wet fingers to her mouth, and Jenna quickly opened her mouth to receive them. Bill knew she was hungry for him, and he was in heaven.

Jenna kissed down his bare chest and fell to her knees to unbutton his pants. His heart skipped a beat as he saw her on her knees before him. He noticed her once steady hands were now shaking a bit. She went to grab his boxers along with his pants to pull them both down at once, and her nails scratched down Bill's thighs as she did. The surprising bite of pain made him grit his teeth. Before his pants were even to his knees, Jenna had enveloped his already hard, slick cock with her warm, wet mouth. Bill wasn't expecting that she would grab him so quickly, and he took a step back.

After hungrily bobbing her head on his cock several times, Jenna regained control of herself and slowly traced her tongue underneath his shaft while staring at him with her big, brown eyes. He held the back of her head and pressed her to him. She rubbed his cock against her lips and face before taking his head in her mouth and sucking him again. She then licked his tip, tasting his pre-cum. She lingered there, as if she wanted more of it. Bill grabbed his cock and stroked it, pushing some out for her and watched as she quickly licked him clean. She was starting to slowly take him in her mouth, sliding her soft, full lips over his cock. She liked seeing how far she could get his dick down her throat and loved hearing him grunt when she took all of him. When her lips reached the base of his cock, she struggled not to gag, then slowly came back up for air--going down, then up, down, then slowly up until she had a rhythm in place. Every time she would reach the head, she would swirl her tongue over it and Bill would whisper her name. The amount of time it took her to take his whole length down her throat made it seem like Bill had the biggest cock she ever had the pleasure of sucking.

As she went down on him, taking him deeper and deeper each time, Bill felt consumed by the urge to fuck Jenna's pretty, little face. They had been planning this encounter for so long, and he had listened to the things she told him she liked and fantasized about. For months he didn't know if he could fulfill the desire she had for rough sex. But as he watched the fine, young piece of college ass before him, on her knees gobbling his cock and licking every drop of him, he was consumed with lust. He grabbed a handful of her hair and pulled--hard. Jenna opened her mouth to cry out in pain, and Bill rammed the entire length of his cock down her throat. Jenna choked and fell back. He grabbed the back of her head and held her in place while he fucked her mouth. She was trying to take him in but was having a hard time breathing. She was careful to wrap her lips around her teeth, but Bill was getting the better of her, pumping his hard member into her mouth harder and faster than she had ever had it. Jenna had fantasized about a man controlling her like this, using her simply for his pleasure for so long; she never thought Bill could do it, though. The struggle made Jenna's body tight with pleasure, and she felt like she was going to cum.

Bill was also feeling an orgasm building and knew he was very close to exploding in her mouth. He wasn't thinking about anything but shooting load after sticky load of his hot cum down Jenna's throat. He looked down, though, and saw her struggling to keep up with him. He fought every primal urge in his body to pull out from her throat, which he did and screamed an angry, "FUCK!"

Jenna fell to her side. She didn't know what she was feeling. She never would have expected Bill to lose himself like he did, but she liked it. She had also never come so close to an orgasm without someone touching her clit. Her heart was racing and she was still trying to catch her breath when Bill lifted her up and carried her to the bed. He threw her down on it as if she were something he was discarding. Jenna ate it up. As she fell, her legs spread open exposing her bare pussy.

"I don't know what you are doing to me, Jenna," he said as his fiery eyes looked down upon her.

"I don't know what I am doing either, but I know what I want you to do," she replied as she spread her legs wider.

Bill didn't need an invitation to dive into to her waiting snatch. She was covered in her own juices, and he loved the way she tasted. He stretched his tongue as deep inside her as he could, and Jenna moaned. God, did she moan and groan. He ran his hand along her thigh and down her leg. She was so smooth, and she still had on her black high heels. As Bill came up for air, he looked at her. He could tell how bad she wanted him, and he liked being wanted, being the only man in the world who could give this hot, little girl what she wanted at this very moment.

"Please, please don't stop, Bill," Jenna suddenly begged.

"I thought you told me you didn't like oral that much," he grinned, before plunging back inside her sweet cunt.

Jenna's gasps filled the room. She would feel Bill lick all along her inner lips, and then she would wait for him to tongue fuck her. Every time he slid his tongue inside her pussy, she bucked her hips toward him and tightened them around his face. She could sense that he liked the power he had over her, because he was tormenting her mercilessly. Getting her excited, and then pulling away. Jenna knew her moans revealed her desire, so she bit her lip to try to stop them. As she did, Bill's tongue finally brushed her clit for the first time. She jumped and cried out, grasping the sheets of the bed in her tight fists. Sensing his cue, Bill began an all out assault on her throbbing clit. Sucking it, licking it, nibbling it... Jenna pressed it to his mouth. She had never had a man make her cum this way, and Bill had been right when he promised that he could. He slid one finger, then two inside her, all the while never letting up on her clit. Jenna's nipples hardened, she felt every hair on her body standing on end... it was starting... she could feel it in her toes... then her thighs... and belly...