Apartment Sitting

Jack slowly walks up the flight of stairs to the third floor. He could have easily taken the elevator but for one he never liked elevators and on top of that he needed to breath a little more. He was a pretty average guy. He had just shaved his head but always wore a fitted hat. He had a gut but it was just below being considered heavy. So what was this encounter anyway? What was she expecting? Where they really only going to watch a few movies and sleep in. A few days ago this was just another IM on his screen.

"I'm apartment sitting for a friend. I'm kind of afraid to be alone there, do you think you could come and just crash here one or two nights with me. It will be like a big sleepover and we can watch movies all night."

He reluctantly had said sure but never really knew what to think about it. They had originally met on line and in real life had only met a few times and even those were chance encounters and since their last meeting their talks had gotten closer. They had on more then one occasion had internet sex or at least helped each other through words and a few pictures. But what was he doing here now. Was she just looking for someone to watch a few movies and lay around with or was this supposed to be their first intimate encounter? His heart raced as he walked onto the third floor. He quickly surveyed left or right and saw no one in the hallways but realizing he needed to go down the hall to the right to get to her apartment. He quickly took some deep breaths and fixed his hat on his head.

Took the first few steps down the hall.

"This will be nothing. Even if she did want something I will probably just wimp out as usual."

A few more steps

"But what if something does happen. How far will it go? I really don't want to hurt her if she is looking for more then just a hook up."

A few more steps now he can see her door.

A few more breaths, and then there he was, standing in front of the door.

A few more deep breath before a few quick knocks.

It didn't take long for her to answer the door and immediately throw her arms around him in soft hug. She actually seemed a little messy as if she just moved in herself. She was shorter then him but still not that short. With beautiful blonde hair that was about shoulder length and these eyes that Jack always said were blue but in closer inspection were hazel with a green tint. She had an amazing body though. She wasn't an anorexic girl but was far from being any type of heavy. She had a stomach, which Jack always called a tummy but it never seemed to stand out. She had a chest which was big for her height but nothing that would give her back problems in the future.

"Hey Tiff how's it going?"

"Did you find it ok? Well you must have you got here earlier then I expected. I just ordered some pizza for us and was about to jump in the shower. Come in come in"

She ushered him into a pretty decent apartment. He walked into the living room on the right and kitchen on the left and a long hallway straight ahead of him. The living room on the right had a nice flat screen TV probably in the 40s inches. A decent size couch and stretches all the way down the right side with the back wall being opposite to the hallway.

"Thanks for sharing the wealth in the hug then."

"Haha I'm so sorry I was just so happy to see you. I left some money on the counter just pay the pizza man if he gets here before I'm out. Make yourself at home I'll be right back" and with that she walked down a narrow hallway and disappeared into a room off to the left.

Jack walked in and closed the door behind him. He then looked around the living room at pictures and tidbits that were spread around. Tiffany hadn't told him whose apartment it was but from the look of the layout it was a female. The pictures were all different picture but there was one girl in more of them then any other so he assumed that must be Tiff's friend. After the living room he started towards the kitchen before he heard a knock at the door. He quickly answered it knowing it was the pizza man. After taking the pizza and soda and paying the man, he didn't even think to use her money, he took it all to the kitchen and scrounged around to find some plates and cups. A few minutes later he heard the door down the hall open and Tiff come out the hallway in only a white tower. Her hair dripping still all over the floor.

"I knew I smelt the pizza. I am starving," she said as she quickly opened the box and plate and sat down at the table crossing her legs at a speed that Jack didn't know existed. He was a gentleman but wasn't going to refuse a look at someone that came out looking like this. They sat there eating their pizza for an hour or so (finishing in 20 minutes but just talking for the rest of the time). Finally Tiff says, "OK how about I put some cloths on and we can lie down and get a movie going." Jack just nodded as he got up and started putting the plates in the sink and the pizza in the fridge. He heard her go into the bathroom for a few and then go into the room at the far end of the hall. At this time he got some more ice and some water then grabbed his backpack and headed to the bathroom. He used the bathroom and then brushed his teeth, might as well at least not have stinky breath for the rest of the night. He then changed into some sweat pants and a wife beater. After cleaning up he walked into the hall noticing the door to his left was open but instead he headed back towards the kitchen area.

Before even making it to the kitchen a voice came from behind him. "Where are you going?" With that he turned around and started walking back

"What r u talking about the TV is huge in the living room?"

Before she could even say anything he walked into the bedroom at the end of the hall. It was slightly bigger then the living room with a queen size bed in the middle and hanging on the wall another flat screen about the same size as the on in the living room.

"Yeah but now if we fall asleep there is no worries," she says as she lies curled up on the bed in soft pajama sweat pants and a nameless hockey jersey. Jack almost forgot to keep walking. "Well you coming?" she says as she pats the bed. "I already put in a movie."

Jack tossed his back pack down and slid onto the bed. Tiff slid back and started the movie. She was close but in Jack's head all he was saying was "don't jump to conclusions." After a few minutes into the movie she changed sides putting her head at the end of the bed to better see the TV. Jack for the first time tonight saw the soft peak of her butt compared to the frame of her back. He could only imagine holding onto it and caressing it with his hands. Jack tried desperately to keep his now growing member from being noticeable.

About an hour or so into the movie Tiff started squirming. Jack thought at first her stomach was bothering her until she finally looked back and mentioned, "Sorry my back is killing me."

"You know the rules if a back massage is what you're looking for," Jack said. Jack had long before told her, his rules for massages. Always lying down. And always skin to skin. Without even saying anything after this she slid her shirt off leaving her bareback and bra strap facing Jack. Now he had to adjust just to make it not noticeable. He quickly moved to his knees and straddled the small of her back, lightly resting his butt on hers. It was just as soft as he could ever imagine. He started high on her back and into her shoulder. Deep massaging until he got over to her neck which he lightly massaged the back of up to the hair line. After that he slowly worked down from the center out as he moved down her back. When he got to her bra strap he slowly slid his hands under it and kept kneading her back. Finally he made it all the way to the small of her back, having to sit more on her butt to do this. Slowly her started back up her back using different techniques at massaging. When he made it to her bra strap, again he slid his hand under but this time she reached back and just unhooked it. "it's pulling on my chest anyway," she murmured.

He just smiled and kept going. After working on her back and arms for quite awhile he lightly asked, "where do you need more work?"

"Actually my back feels great," she said has a small disappointing sigh left his mouth. He was enjoying himself so much feeling the softness of her skin that he was almost hoping for more. He slowly slid his legs over and got off her when he noticed her reach down, thinking that she was just adjusting her pants he slightly turned the other way to fix his own. When he turned back around he just noticed that she had actually pushed them off. Jack just stared as she laid face down in just these light pink lacy panties. She had her head turned and was just looking at him till she finally giggled and said, "so are you gonna keep going?"

He just smiled back at her and went back to straddling her back. He started on her upper back again but worked fast to slowly move down to the top of her butt. He repositioned himself on the other side of her butt and slowly ran his hands over the outside of each cheek, savoring the feeling. He worked massaging her butt for a little before moving down. Being a little flustered he started on her left foot first. Slowly massaging as much of the foot as he could upside down before slowing working up her ankle to thigh. He kneaded her thigh thoroughly and as he got higher and higher he started to imagine being able to smell the fragrance she was letting emitting. Before long he was at the top of her inner thigh, letting the side of his hand inadvertently massage the outside of her vagina. He could feel the heat and moisture now to go along with the scent. The then moved to her right foot and worked all the way up massaging now the other side of her vagina when he got there. He wanted to get her more aroused then she was already making him. After realizing he was massaging the same spot for a long time he slowly stopped and sighed, lying down next to her. She laid perfectly still and just smiled at him.

"So do you do both sides?" She said with a smirk as she started rolling over.

Jack just lay staring at the curves of her body. Letting his eyes crest from the peaks of her face down the valleys of her neck and then over the crests of her inflating and deflating chest. Something wasn't right though. He thought she was coming on to him yet her bra was still draped on her chest with her arms still in the straps. Now Jack is realizing she is just doing this to take advantage of him. He knew that if she was going to take advantage of him he would take all the steps he could to get as much out of it as possible for himself.

He slowly got up and took the jersey she had bin wearing and draped the sleeves over her eyes whispering, "trust me."

Then he moved to her feet this time he worked her feet and up her legs a little faster then last time but taking special time at the upper thing. Giving her vagina some more attention now and never letting a chance to let his hand just lightly slide over where her clitoris was. He finally saw the full design of these panties. Pink lace with designs of stars and hearts, the fabric almost seemed like it wanted to be see thru but was just on the threshold. As he moved up her second leg and got to her upper thigh he finally noticed how wet he had actually made her. The fabric was soaked and almost looked like it was throbbing for attention. At this time he was unwilling to give it, make her squirm a little for it. He put one hand on each of her thighs and with his thumb traced the semi circle of fabric that lead to her hips. Then he move to the left side of her body and slowly slid his hands up the sides of her body massaging a little above her stomach but well below her chest. He then took her right hand in his and gentle massaged her hand working up her arm. When he got to the shoulder he slowly massaged small circles from one shoulder around the base of the neck to her right shoulder. When he went to move himself over to the right side of her body she spoke, "O fuck it." With that being said she pulled off her bra tossing it to the side. With one fluid motion she reached for the sleeves covering her eyes but jack leaned in holding her hands with his face mere inches from her and whispered in her ear, "let me finish." With this she relaxed and he quickly finished massaging her left arm. He then leaned back and took a drink of water slowly moving over to straddle her stomach. He then started massaging just below her chest again and watched as she slowly bit her lip. Moving up slowly he got to the base of her breasts and slowly massaged the bottoms, while moving in circles to completely pass around the entire breasts. Lightly running his thumb over her nipple every few rotations. Then with out stopping he leaned down and kissed right between both breasts letting the piece of ice he had in his mouth lightly touch the skin at the end of the kiss.

She gasped.

He then kissed slowly down following the same step with the ice. The upper stomach. The belly button. The lower stomach. All the way till he reached her panty line where he kissed once in the center of the top of the fabric. He could feel her straining her hips to get his face lower down towards her vagina and waiting clit but he then moved back up slowly kissing again until he reached the breasts once more. This time he let his mouth over each individual nipple, letting his tongue caress them and then the ice cool down. He could feel her shiver. He then kissed the base of her neck swallowing the small remainder of ice that was left and leaned forward to finally kiss her on the lips. She then kissed him deep and passionately. She explored his mouth with her tongue in dire search of the vanished piece of ice. He slowly pulled away from her but giving light little kisses while he did. She just smiled. He could feel her chest against his slowly moving up and down with each breath. He could feel her arms on his side and slowly looked back to see her slowly rubbing underneath her panties. He slid down her body and with her other hand she slid off his wife beater.

He slowly lifted her hand out from under her panties and kissed just about her clit through the fabric. Slowly he inched down lower sliding her legs onto his shoulders as he slowly circled her clit with his lips through the lace panties she was wearing. He slowly flicked his tongue as he could feel her digging her legs into his back pushing him into her. He started sucking lightly on her clit and pulling away just enough to grab the fabric and slowly start to slide it down her legs. She was dripping wet and he wondered if she already had an orgasm, or two. By the time he got two her knees she had already gotten her fingers back inside of herself and moving in and out. After getting her panties off he moved back up to her pussy where she quickly pulled her fingers out almost ashamed. He just held her wrist and moved her fingers back into her vagina kissing the outside of her vagina as she slowly started back up. He then slide his mouth back to her clit and started licking and sucking lightly on it as he used one had to caress her chest.

It did not take long for her body to start shaking as she let out a loud moan and used her legs to pull his face straight into her and holding it there. When she finally let him go he slowly slid back up her body as he realized she was pulling off the jersey off her eyes and smiling at him. He leaned over straddling her body (standing doggy style over her) and lightly kissed her again. While he was kissing her she wrapped her arms around his shoulders so when he started to lean back he just lifted her with him. This made them both just giggle a little.

"Lean your whole body close to mine," she whispered. He obeyed as she wrapped her legs slowly around the top of his butt. Then as he leaned back up he lifted her whole body off the bed. As she lay dangling under him he started to slowly turn to put her head to the head of the bed where all the pillows where. Before he could get a full 180 degrees around he learned of her little secret. As he was spinning she was slowly using her legs to slide his pants over his butt and start moving them down his thighs. It didn't take long for his penis to be freed from his pants. This made him blush a little but she just smiled and kissed him and started rocking up and down. Due to his enlarged member she easily got into a rhythm that started to get close to penetration. She moved her legs farther down his butt to pull her closer to it and before long she was getting him to enter her on every few swings. Due to the moisture she already had he was sliding in and out with ease. She soon got the hang of it to keep him in her longer by when he did slide into her she would shorten her swings to keep him from falling out. It wasn't perfect but they both loved it.

She finally popped out and stopped swinging, he figured she was getting tired. Before he could even lower her she quickly pushed a swing to her left which knocked him off balance. As he fell to his side he tried to think about what was going on but before anything could be thought up she rolled him fully over now she was on top straddling him. She smiled and ran her hand through her hair pushing it out of her face as she slides her vagina down his stomach towards his penis. She slowly slid him into her and she kissed and lightly sucked on his nipples. This drove him wild, but how did she know. Soon she moved back up and started kissing him again as she bounced her hips up and down. He knew he wouldn't last long and the first breath she took he let her know, "You're driving me crazy and there is no way I'm going to last long."

"I just know you deserve to finish since I already have plenty of times."

She then increased her pace. She wasn't even able to kiss him anymore due to her panting. She would put her mouth on his neck to seem like she was going kiss him but then he realized it was to just muffle her moans. Then she quickly lightly bit the bottom of his ear and just moaned out, "o my god Jack.." Just as she said this he felt her vagina clench around his penis as he lost control and let out shot after shot of semen deep insider her. She just collapsed on him. Neither of them pulled him out of her but he could feel her vagina every now and then spasming with his penis in her. She just laid breathing heavy on his chest. Soon His penis softened and with a last tight spasm from her he flopped out of her. He then kissed her forehead as neither one of them moved and they both just fell into blissful sleep.