Michael was unsure of this whole thing. As most should be, he was skeptical about a dating service, especially one that centers on sex. Michael delayed for months, but finally decided to try the service. Now, Michael, twenty-five, eagerly waited the date that had been set up. He is quite nervous, as is his usual, but especially so for this date. He sat on the edge of his bed, contemplating the clothing choices before him. Michael is just under five foot nine, one hundred-fifty pounds. He is a stick of a person, his whole body can be described as skinny. His close cut brown hair didn't require any maintenance. "Just Sex" He thought. He breathed deeply and calculatingly finished dressing. Nice but not too nice, casual but not too casual. Michael can't really be described as sexually experienced, granted he is no virgin, but he is by no means a 'ladies man'. However, with the internet, Michael is quite knowledgeable when it comes to sex. He has strengthened his kegels muscles, and can now control himself very well.
His date is quite the opposite. It isn't fair to call her a slut, but she has a lot of sex; A frequenter of the It's Just Sex organization. Jennifer is a shade over six feet tall with shoes on. She is the kind of woman that exists in most offices. She is flirty with the guys, very cute, and quite hot. Her legs seem to go on and on. Simply looking at her is somehow calming. A man could easily be aroused by a woman, but someone appreciating Jennifer will peacefully survey her as if she were a golden sunset. Her long straight brown hair flows as she walks. Her skinny tall frame is accompanied by medium breast. Big enough to be noticed, but not overpowering the image of her. Her bust is well rounded, she likes to wear a large B, but is actually a Small C. She walks so confidently, not looking for approval, nor asking for attention, just her.
Michael left his apartment and hailed a taxi. He paid the driver, and exited toward the bar. "This is it" he thought, walking in with his heart racing. His eyes made a quick sweep of the mostly empty bar, before deciding that she had not yet arrived. He took a stool at the end of the bar. The second he sat down, he spotted Jennifer walking toward him. Jennifer was wearing a blue flowery dress, it was low cut exposing the tops of her pushed up tits. She sat down beside Michael, and looked at him like one would look at a used car. "uhh. Hi" Michael nearly choked.
"Jennifer" She said, smiling warmly and extending her hand. He uncomfortably shook her hand, hoping she wouldn't feel the sweat on his palms.
"Michael" He said. He was sitting facing the bar, she was facing him. She placed her hand on his thigh, leaning slightly on him.
"What'd you have in mind?" She asked him.
"uhh. Well, I thought we could…go back to my place, or your place, and we could uhh have sex" he said, stumbling through the words.
"You don't sound very confident" Jennifer said, pouting her lips. "You want me to take control?" She asked.
"Sure" he said, not really sure what that meant. A moment later he hoped it didn't mean any kind of bondage, but he couldn't say anything anyway.
"Let's go" Jennifer said, grabbing his hand, and quickly turning to walk out, pulling him behind her. Once back outside, Jennifer quickly hailed a taxi, and toted him in behind her. She directed the driver to her apartment. "How's my place sound?" She asked Michael, her voice as warm as ever.
"Great" He replied. They sat in silence briefly. Jennifer's hand again found his thigh. "So uhh, what do you do?" He asked her.
"I am an executive assistant" She said in her official business voice. "And you?"
"Office Technical Manager" He replied. Typical office jobs all around. Jennifer's small hand slowly started to massage up and down his thigh. Jennifer's confident brown eyes gazed into Michael's uneasy brown eyes.
"How big is your cock?" Jennifer asked, back into her warm voice, it was loud enough for the driver to hear.
"Maybe you will find out" Michael said, trying to gain some control in the conversation.
"Maybe" Jennifer said, biting her lip and looking down to where her hand still was. She gently moved her hand, pressing against his jeans, up against his crotch. She felt his cock growing. Her fingers traced the outline of him in his jeans, gently caressing. It gave his cock a tease, to which it responded. Jennifer put her other hand on his neck, and leaned her face right up to his shoulder. "Want me to suck your cock?" She whispered in his ear.
"Now?" He tried to whisper in response, but his voice failed to work, but the expression was more than enough to get his nervous point across.
"Why not?" She asked, using her normal warm voice again. His cock had grown noticeably between her fingers. "Six inches?" She asked him, surveying him.
"Six and a quarter" He said. "Not that I measure or anything" he started to relax a little.
"You didn't answer my question" She said, lightly stroking his cock through his jeans now.
"I wouldn't be opposed to it" He said, smiling. She briefly looked down at his pants, then looked back up at him.
"If I am going to do this, I am going to do it right" She said. Jennifer leaned in a little closer, whispering "I am going to make you cum hard and fast. Don't hold back, I can take it."
That surprised Michael a little bit. Jennifer placed her lips together on his cheek, her still wet lipstick leaving a kiss. She slowly pulled his head toward her, extending her tongue. She lightly licked her tongue across his closed lips, before lowering her head. She unzipped his pants, and pulled his near fully erect cock through his boxers. Her open mouth hovered above his cock. Michael sat back, relaxing, placing his hand on her back, rubbing her approvingly. Her hair obstructed any view downstairs, but he didn't need to look.
Jennifer's tender lips met the head of his cock, caressing the smooth tip of his dick. She opened her lips, sliding her tongue down the side of him, a slow drip of saliva ran down his six inches. Her warm wet mouth embraced him, sliding down his shaft. He shuddered in pleasure as her mouth fully engulfed him. His cock in her throat, her tongue massaged the length of him all at once. Jennifer began swirling her tongue as she slowly moved her head up and down. Michael moaned without thinking. He suddenly realized, his eyes wide, that the driver knew what was going on. He looked up and saw the driver eyeing them in the mirror. He feared she would stop, but she didn't seem to care.
The warm wet sloppy blowjob continued. Michael felt much more confident now. He slid his hand down her backside, lifting the back of her dress up. His hand felt her moist panties, and carefully he tugged on her underwear enough to expose her pussy. His index finger felt her wet lips, whilst her mouth bobbed up and down on his cock a little more feverishly. His finger gently parted her lips, teasing her slit. Jennifer, not to be shown up in any way, started to blow Michael like there was no tomorrow. Her lips slid up and down his shaft, her tongue flicking and massaging all around the head, her cheeks sucked in, her mouth sucking hard on him. Her hand cupped and massaged his balls. Jennifer gently moaned, vibrating his cock slightly.
Jennifer gave superior head. Michael couldn't believe it, but he was already about to cum. He heeded her advice, and allowed his excitement to build. She sensed his proximity to orgasm, and plunged her mouth all the way down on his cock, again deepthroating him. Her tongue milked the length of his cock. Michael exploded in Jennifer's mouth, filling her with jizz. She tried to take it all straight down her throat, but the sheer size of his load backed up into her mouth. She moaned as he did, swallowing everything he gave her.
Jennifer played with his now oversensitive member. She sat up, licking her lips. Michael put his cock away, and zipped his pants back up. "Thanks" He said.
"What do you mean thanks?" She asked. Michael looked at her unsurely. "You aren't going to thank me with words" She said, a devilish smile creeping up on her face.
The driver pulled to a stop. Michael paid the driver and they got out of the taxi. Jennifer held Michael's hand, again toting him, and pulled him into her building. They briefly waited for the elevator, then boarded the empty elevator. Jennifer pressed the button for her floor, and the doors closed. "Want to do it in here?" She asked him.
"Maybe we should go somewhere more intimate" he said, unsurely.
"Don't worry, I was kidding" She said, smiling at him. "But still" She said in a deep sexy voice. She pushed him against the side of the elevator, pushing her body against his. Her hands pinned his shoulders back, his hands held the back of her waist. Jennifer was a few inches taller, and as such, she had the natural control in their actions. Jennifer pressed her mouth against his, her tongue protruding between her open lips. He kissed back, his lips surrounding her tongue. Their mouths melted together, the slight taste of cum lingering. The elevator dinged, announcing their arrival at her floor.
Jennifer walked out of the elevator, not pulling Michael behind her. He stayed against the wall, as if he couldn't walk without her guide. He suddenly realized he shouldn't fall behind, and walked out quickly behind her. She strode down the hallway to her door, and opened it. She pushed the door open, and leaned against the frame, waiting for him to walk in. Michael slowly walked inside. Jennifer pulled the door closed behind her, flicking on the lights.
Michael stood just inside the door nervously. Jennifer grabbed his hand and led him straight to her bedroom. They stood at the foot of her queen sized bed. "Right to the point" Michael said.
"I am going to take a shower. Make yourself at home" Jennifer said. She pulled her arms through the straps of her dress, dropping it to the floor. She quickly walked into the bathroom and shut the door. Michael sat on the edge of her bed. "Why didn't I do this a long time ago" He thought to himself. He pulled off his shirt, tossing it to the floor. "Should I take a peek?" He thought, hearing the shower running. He walked towards the bathroom door, dropping his pants and underwear on the short walk over there. Michael slowly turned the know, cracking the door. Jennifer was in the shower, he could see her silhouette in the curtain. He cautiously walked to the back of the shower, peeking inside. Jennifer's body was glorious. Her natural tone was just the right slight brown that looked perfect. Her smooth skin was so inviting. The water poured over her round ass. Michael was hard again. Now he wondered if he should do something or just wait for her to get out of the shower. Before he decided, she acted. Jennifer's right hand was buried between her legs, and she started to moan gently. He watched a little while longer before deciding he should go out and wait. He closed the door behind him.
Michael dug a condom out of his jeans laying on the floor. He set the condom on her dresser. He sat on the edge of the bed, staring at the bathroom door. The water turned off. A minute later, Jennifer opened the door, wrapped in a white towel. "I thought for sure you would come into the shower" Jennifer said.
"I was tempted"
