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.
