The Trainer

The sun was so hot for July, no wind blew and it was simply sweltering as Jim sat at the edge of the pool with his feet in the water. He watched people swimming and diving and just hanging out much like he was. Some drank mixed drinks, while others lay about sunning themselves. It reminded him of how Lizards would sun themselves on Rocks for warmth. He couldn't help but smile at the thought of that big older lady laying on her back in the far corner of the pool in her two piece which was obviously outdated and too small for her swelled body. She had a white towel covering her face and although the folds of flesh lay exposed to the world, she lay without a care in the world. He noticed her subtle nuances and noticed pretty quickly how her bikini bottom was pressed against her pubic mound tightly to reveal the outline of her vagina as she lay there. Whether or not she was aware of it was unknown, but Jim thought that she probably knew and didn't mind this little slice of exhibitionism. Most people didn't as long as they thought nobody noticed yet secretly hoped it was on a Times Square billboard at mid day.

Jim thought about his wife Marie and their two kids who were in Nevada visiting family and how it was going to be three long weeks until they returned. He wondered to himself if after week two the sight of the older, overweight woman in her two piece bikini would be attractive to him after a three week dry spell and then decided that it'd been only two days and she was already starting to look good.

He stood and walked back over to his lounge chair and sat down and lay back. He threw his sunglasses on and drifted off to sleep for a few minutes only to be awakened by the mother of one of his daughter's friends. Jim sat up, and removed his sunglasses to meet the mid forties mother of three. She was a bit chubby, Jim could tell she'd not worked out in ages, hell to be honest neither had he. She stood a mere five foot six, with blonde hair and pouty lips. She wasn't a supermodel by any means but she wasn't dog ugly either, she was just your everyday run of the mill woman.

"Mr. Richards?"

Jim smiled and extended his hand to her. He never passed on a chance to touch someone. "Jim" He stated as their palms collided in a light handshake. Jim held her hand as long as possible and then released her, "What can I do for you?"

She too wore a bikini, which was pink but a one piece and clung firmly to her heavy bosom and without straining to see, Jim could easily see the razor stubble at her bikini line and knew the curtains didn't match the drapes as they always said. He didn't care, she was female, and smelled of honey suckle and for now her nipples straining against the spandex suit was all it took to keep his undivided attention.

She said, "I would like to ask a favor as it were, is there somewhere we could talk privately?"

Jim said, "Of course, would my apartment be alright?"

She nodded her affirmation and Jim got to his feet, gathered his things and walked shoulder to shoulder with her out the pool gate exchanging pleasantries into the apartment complex parking lot. Outside the gate, he again reaches for her hand, which she offered without resistance. He felt her smooth flesh and drew close enough yet again to smell the perfume on her. He inquired, "And your name is?"

She smiled a huge smile and returned, "Sorry, I'm Caroline. Bethany's mother."

Jim smiled back as he released her hand, "Well, Caroline, It's a pleasure to meet you. Since we've moved here, I've wanted to meet you. After all your daughter spends more time at our apartment than she does yours, but we love having her."

He led Caroline to the door which he graciously unlocked and opened allowing her to enter first. As he entered behind her he noticed her daughter Bethany was in tow and let the tall lanky girl inside as well. She was two inches above her mother's height and nearly as tall as he but she didn't have any of her mother's physical traits yet. Jim said, "Bethany, make yourself at home, you know where the kitchen is if you need anything and the computer in the back is working if you'd like to get on the internet while your mother and I get acquainted a bit."

Bethany didn't answer just went to the task of fixing herself a drink and she momentarily disappeared down the hall. Jim held out his hand in the direction of the couch.

"Please have a seat. Make yourself at home."

Caroline easily seated herself on the end of the couch, while Jim in his wet shorts stood at the edge of the chair mere feet away. He asked, "Now, may I offer you a glass of wine Caroline?"

She giggled, Jim could easily see she wasn't accustomed to this type of treatment, "Yes, she replied.

Jim entered the kitchen and poured her a glass of white wine and returned it to her which she graciously thanked him for.

Jim stated, "Caroline, would you mind if I changed out of my shorts and into something dry?"

"She gave him a look up and down and replied, "Of course not..."

Jim eased to the bedroom after excusing himself and proceeded to change clothes and soon uttered, "Damn it!"

Caroline stood and walked to the end of the hall where Jim stood in his bedroom doorway wrapped in a beach towel. He looked at her sheepishly and said, "I'm sorry. I haven't done laundry yet, everything's out in the washing machine wet also. I'm sorry Caroline. If you'd like to come back later we can talk then."

She said, "No, it's all right, just wear the towel and I'll be on my way. It won't take long I promise."

Jim returned to the living room in only his beach towel and sat across from her in the recliner.

"Jim, I need a favor. I know that you and I don't know one another very well but Dennis and I are going away for the weekend and we need someone to keep an eye on Bethany. I know I'm probably being overprotective and yes she's eighteen now but I still don't trust that she won't have a bunch of boys over or worse leave the house unlocked and someone to take everything we've got. Bethany's a smart girl, just a little air headed. Would you be interested in anything like that?"

Jim said, "Sure Caroline, if you can just provide her with some money for food and stuff. I don't really have a lot but I'll take care of her and feed her and watch her. If she's anything like my kids, she'll spend all weekend facebooking™ and myspaceing™ and instant messaging until her fingers are ready to fall off. Still for you, I'd be happy to give it a shot."

Caroline exhaled a sigh of relief and said, "Thank you so much!" She quickly reach into her cleavage and produced a fifty dollar bill and handed it to Jim who was doing his best to keep the towel clenched tightly. Jim replied, "Thank you."

He sat back down as Caroline took a final sip of her wine and said, "Jim now on a serious note, Bethany's a bit of a voyeur so you might be careful around her if you know what I mean. Jim replied, "Of course, I'll remain dressed at all times."

Caroline said, "That's not necessary she is after all a high school senior now, I guess what I'm asking is that my daughter is not like other girls her age, she's very sexually active, I mean to the extremes and she's prone to tease and show parts of herself that she shouldn't show as long as it's a game to her. Dennis although is her step father but that didn't stop her from peeping him in the shower and taking cell phone pictures of him and then doing well, you know in her bedroom to those pictures later!"

Jim nodded as if he knew exactly what she meant and finally asked, "So what you're telling me is that she likes to watch and then take pictures and then masturbate to those pictures later?..."

"Bingo!" Was Caroline's response.

Jim growing ever more concerned said, "Caroline, I have to be honest, I'm the type of guy that is finally away from his wife after twenty years and I was hoping to spend most of my time comfortable if you know what I mean."

Caroline giggled and wiped her nose laughing and said, "Well, that's alright too. I suppose now would be a good time to call her bluff. I mean I want you to just show her what she wants to see without making her work for it so to speak. I think this way she won't be so inclined to voyeur us all when we get back and she's know exactly what she's going to see."

Jim said, "And you think that'll stop her? What if it only fuels the fire?"

Caroline leaned close to him and whispered, "Listen Jim, it's like this I'll be blunt. My daughter's a pervert. I think if this weekend she were allowed some indiscretions then when we get back she'll have it out of her system and we can move on. Plus she would have some necessary experience. Now quietly I want you to work with me here..."

She reach down and lifted the edge of Jim's towel and said, "Oh, Nice. Very nice Jim." As she peered at his testicles and flaccid penis, as if sizing him up for her daughters tender cunt. "That will work just fine."

Jim drew upright and said, "Excuse me?"

Caroline said, "Listen I was hoping that you wouldn't be TOO endowed. That way if Bethany chooses to well you know that her first experience wouldn't be traumatizing."

Jim whispered back, "Intercourse?"

Caroline nodded and said, "Now we're on the same page. She just needs to be taught..."

Jim said, "I know it's none of my business but this training so to speak wouldn't be so that Dennis would be a twice lucky man when you return from your trip does it?"

Jim refilled her glass with an easy smile and awaited an answer.

She blushed visibly and said, "Maybe..."

Jim laughed out loud and said, "A woman after my own heart! Believe me Caroline, I wish I'd started mine young and I'd be a very happy man you know."

She said, "So true, my new friend, but this is just part one of the training, I'm hoping to find another woman possibly older to train her in other ways as well."

"Double your pleasure, double your fun huh?" Jim retorted.

With an evil grin she replied, "You got it. If mama aint happy, nobody's happy."

Jim said, "So Caroline, tell me if you don't mind; how on earth did you get started with all this?"

His deep brown eyes stared into hers'. She found it hard to break his stare as he awaited an answer. She began, "Well, I guess it stems from my own childhood where it was very common in my home and until now I've had that urge but never have acted on it and I suppose I'm wrong but society condemns interfamily relationships but I lived through some and from my experience there was no trauma, no forcefulness, no bad repressed memories, just pleasure. I was one of those kids who had the rare opportunity to pleasure both my mother and father. I was an only child. We lived out on this big farm and we all slept in the same bed, showered, bathed and did most everything together so when sex time came for mom and dad, well it was just what it was, an expression of love and nothing evil or dirty was ever implied so when I got old enough I was introduced to it and it was one of those things at first confused me. Mostly by my own feelings, but soon afterward mom and I talked it through and from then on it was just a very joyous experience."

She finished with the most sheepish look on her face and dropped her head as if ashamed of what she'd just said.

Jim stood and moved beside her and lifted her chin with his finger, "Never be ashamed of who you are Caroline. I'd be honored to teach her for you. Don't worry about a thing. Ok?"

Caroline pulled at Jim's hand and placed it on her left breast which was full and firm. Her nipple pressed hard through her bikini top and his other hand on her thigh and closed her eyes and leaned in sticking out her tongue for acceptance. "Take me daddy. She whispered."

Jim drew close and as his tongue touched hers, she shivered and orgasmed instantly. Sliding to the edge of the couch, Jim pulled aside her bikini bottom and exposed her pussy which was shaved and very plump and tight. Easily he slid a finger inside his new found friend and she threw her head back. His finger's pace quickened, as the juice from her pussy ran freely and she came over and over again wetting the floor. Jim whispered in his deep voice, "Do you like daddy fingering your pussy Caroline." She moaned and moaned as her thighs shivered and a huge squirting orgasm struck her. Her eyes rolled into the back of her head as a spray of fluid exited her pussy covering the coffee table. She bit his arm to quiet herself from screaming out so as not to alert her daughter in the back room on the computer.

Jim allowed her orgasm to subside and allowed her to recompose herself as he stood and moved back to his chair and asked her, "How was that?"

With a star struck look in her eye she replied, "Oh my God Jim. I'd marry your ass. Oh that was so hot and so good! Can we do that again some time?"

Jim smiled and said, "Sure. I'd be happy to Caroline."

Caroline readjusted her bikini bottom and top and stood. She called out, "Bethany?"

The young blonde haired girl appeared around the corner, as Jim wiped up the coffee table mumbling about being clumsy and spilling a drink to divert her attention in case she could smell sex in the air; and said, "Yes mom?"

Caroline said, "Come here sweetie."

The girl walked over and got a very warm loving embrace from her mother who even dropped down to pop kiss her daughter on the lips.

She led the girl to the couch and sat down and said, "Bethany, Jim has been nice enough to agree to watch you while Dennis and I go away for the weekend. I want you to listen to him, learn from him and do exactly as he tells you. I do not want you blowing my phone up all weekend long. I've given Jim some money for food and stuff so you guys go get what you need and spend the weekend watching movies and stuff and ya know just hang out."

Bethany nodded her approval, again kissed her mother and Jim led her to the door. Jim stepped outside where Caroline kissed him deeply and buried her face into his muscular chest and said, "I'll thank you properly when we get back Jim."

He smiled at her and said, "I'm counting on it." With that he watched her walk away. Her body was plump and fabulous. He couldn't wait to get his hands on her again and bury his cock in her mouth and make her beg daddy for more.

He snapped out of his fantasy and re-entered the apartment holding his towel. He rounded the couch where the girl still sat, Jim said, "So Bethany, I'm Jim. Now this weekend it's just you and me. What do you like to do?"

She said, "I like to watch TV, the Computer, Swimming and that's about it."

Jim noticed that she was wearing Jeans and a pull over tee shirt, and some sandals. Jim said, "So Bethany, I'm just going to wear my towel for a while is that ok with you?"

"Sure. I don't have a problem with it." Was her reply.

Jim sat down in the recliner and didn't bother closing his towel very much. He tried to be coy but he could see the girl suspiciously eyeing him. This game of cat and mouse continued into the early evening when Bethany asked, "What's for dinner?"

Jim thought and said, "How about we order a pizza and catch a movie here? Do you want to do that?"

"Sure." She replied.

Jim gave her a twenty dollar bill and the phone and let her call it in. He showered while she waited in the living room. He heard her through the door, "Pizza's here!" Jim tugged the door open wearing only a towel around his neck as the girl stood in amazement. She tried to speak but could not utter a word. Jim was somewhat aroused but somewhat ashamed standing nude before the girl and asked, "Too much?" She didn't answer. He said, "I'm Sorry; let me put some shorts on..."

"No..." She responded. "It's Ok. Really."

With that Jim tossed the towel on the bathroom counter and followed her up the hallway. Arriving at the counter, Jim said, "You know Bethany, we're not having any visitors tonight, you can feel free to kick off your shoes or whatever and get comfortable."

Still being standoffish she kicked off her shoes as Jim grabbed the paper plates and the duo enjoyed the pizza. After Dinner they decided on a movie and Jim lowered the lights and sat on one end of the couch and she on the other end. Minutes into the movie Jim noticed she had indeed unbuttoned and unzipped her pants yet had her t-shirt pulled down to hide it. Jim didn't say a word and as the movie progressed he noticed she'd worked up the courage to take the pants to her knees and watched out of the corner of his eye as she kicked them off. Every second or two, she'd glance at Jim and then back at the movie. She soon mustered the resolve to take her T-shirt off and simply sat there in her bra and panties.

Without looking at her Jim said, "Thank You."

She replied, "What for?"

Jim said, "Well, ya know getting comfortable. I was feeling a little out of sorts being the only one comfortable."

"Are you sure it's ok? You're not going to tell my mom are you?" She asked.

Jim smiled and looked at her and said, "Of course, what do you think your mother and I discussed earlier. She gave me express permission to let you wear anything you choose no matter how much or how little of it after all you're old enough to make your own decisions."

She smiled at the sound of that and reach behind her and unclasped her bra. Of course her breasts were just beginning to develop and were not much more than swollen nipples or puffies as they were refereed to. Then without warning she stood and rolled her panties down to her knees to reveal her pubic hair. Wispy, thin and blonde in color Jim could easily see her labia and how it was drawn close to her body and oh so puffy.

His cock stood at attention as she sat back down noticing his erection. "Did I make it do that?"

Jim smiled and said, "I can't lie Bethany. Yes you did."

She smiled. Jim said, "Now why don't you slide over here and we can keep warm together. If you want to, I'll show you a thing or two..."

She slid close to him; soon he felt her velvety smooth skin come into contact with his. His heart beat faster as he slipped his arm over the back of the couch and allowed his hand to rest on her shoulder. He glanced down past her breast to her flat stomach and long legs.

Jim said, "Go ahead and touch it...."

She gingerly reach out touched the tip of his cock running her finger across the slit and then grabbed it and held onto it.

"It's pulsing!" She said, "I can feel it in my hand!"

The look of pure fascination was upon her face as he held firmly to his member looking with awe at the swollen purple head of his cock. "Is this the first time, you've held one?" Jim asked.

She nodded her affirmation and stared deeply at his cock never missing a thing as she watched every little movement, nuance and action.

Jim smiled and said, "Want to try something else?"

"What?" was her reply?

Jim thought for a moment and said, "All right, lie down, rest your head on my leg, get comfortable and let me know when you're ready..."

She wiggled into position and nodded her head signaling her readiness.

Jim said, Ok now what I want you to do is to put the head of it in your mouth and just lick it like a lollipop..."

He watched as she extended her tongue and touched the tip of his cock licking the pre-cum from the head. She did it over and over without hesitation. He stroked her hair and shoulder as she worked. Jim said, "Now Bethany, put a little more and more into your mouth each time until you have it all and without using your teeth, suck on it. In and out. Just take your time and practice..."

Jim smiled as she lay in his lap facing him, he watched as she slid his dick in and out of her mouth gingerly and softly, once in a while he'd feel the scrape of her teeth and wince, but mostly chalked it up to her inexperience. He noticed how pretty she was and how absolutely perfect her body was, he reach down and touched her exposed nipple. She stopped completely and froze. He'd forgotten she wasn't used to being touched, save only by herself.