Uncle Dave's Midlife Crisis

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Uncle has to babysit nieces.
8.1k words
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Part 1 of the 8 part series

Updated 10/25/2022
Created 07/04/2004
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mityam
mityam
103 Followers

As I sat at my desk finishing my reports, I wrestled with the images running through my head. Mainly, they were images of naked young girls in various positions. For the past few months I had been trying to cope with the effects of mid-life crisis. While much is made of menopause for women, men must suffer through this psychological dilemma alone. But I fully realize the effects are completely real. The thoughts of lost youth and the promise of the future can sometimes be fairly dismal.

My wife, Linda had told me earlier this morning that she needed to attend a seminar in Seattle this upcoming weekend. Looking ahead I decided several rounds of golf intermixed with some yard work during the day and computer generated self gratification at night would suit me just fine. Our marriage of 24 years had leveled off into endless days of routine behavior. For the past 8 years we slept in separate rooms because Linda says my snoring keeps her awake. I don't know if it is true or if she is just more comfortable sleeping alone. One thing is for sure, our sex life has become damn near non-existent. Now sitting in my favorite chair watching some mindless movie I am soon dozing off.

Through a sleepy fog I hear the telephone ring and Linda picks up the receiver. After a short conversation with the person on the other end I hear her say; "Let me talk with Dave about it and we'll get back with you. I don't think he has any plans this weekend and I'm sure he'll be more than happy to help out." Putting the receiver down she threw a pillow at me telling me to wake up. I open my eyes, looking directly at her and asked what's going on.

"That was my brother, Bill. He and Marlene have an opportunity to go to Florida this weekend and they need someone to watch the kids. I told him I thought you'd be wiling to help out."

"Wonderful, just fucking wonderful!" I thought to myself. Just what I need a weekend babysitting three teenagers. "Linda, the last thing I want to do is keep herd over those bratty kids of your brothers. You know how out of control they can be!"

Linda's brother and sister-in-law had three children. Jamie, Jackie and Robert.

Jamie was 18 having graduated from high school the previous summer. She was a rebel who still lived at home and gave her parents nothing but trouble. She was never a very good student and it came as a surprise everyone that she even graduated. She has a part-time job at a fast food joint but spent most of her time out with her friends. Only seeing her at family functions, she always wore the trashiest clothing, too much make-up and came with an attitude that was impossible to swallow. If she were to clean up her appearance she would be a very pretty girl. Like her mother she was short, 5'-1" weighting about 110 pounds with short dark brown hair. Her 36B breasts fit her body well, breasts that she continuously showed off with low cut tops that always exposed the top of both her bra and tits. Her ass while a little on the plump side, did fill a pair of jeans nicely. She was usually very aloof and always avoided physical contact with family members. And she was always fighting with her two younger siblings.

Jackie, who was born prematurely, was barely six month younger than her sister. Still in high school, she had just turned 18. Unlike her sister, Jackie stood 5'-7" with long legs, a very slim waist, 32C tea-cup shaped tits, a perfectly rounded ass and flowing light brown hair. She excelled at school, was a member of the cheerleading squad and had a very outgoing personality. Like her sister she too wore low cut tops that showed off her young breasts but she was into physical contact, always wanting and giving hugs to everyone in the family. She was also somewhat of a tease. Many times when the family was gathered at our house she would insist on playing pool in the basement taking every opportunity to lean over and let me have a good look on the front of her blouse. Occasionally, she would climb up on my lap and grind her cute little butt directly into my crotch. More than once I am positive she could feel my growing erection pressing against her ass. She usually just smiled and wiggled a little harder.

Robert was the youngest. Four years behind Jackie, he was rapidly taking after his oldest sister. He hated school and was proving to be more than my in-laws could handle. There were times when I felt Bill should grab him and shake the shit out of him, but he didn't.

Linda just looked at me. "What were you going to do this weekend besides play golf everyday? It won't kill you to help Bill and Marlene out. Besides, Robert going up North with a friend for the weekend so it'll just be the girls."

For the next ten minutes we argued the issue back and forth. It soon became apparent I wasn't going to win the exchange so I reluctantly agreed, provided I could watch them on my terms. They would have to stay at our house so I could get some things done I wanted and Jamie would have to behave. Picking up the phone I dialed my in-laws. Marlene answered on the second ring.

"Marlene, Linda tells me you guys want to get away for the weekend and need someone to watch the girls. I'll do it provided they come stay at our house and Jamie agrees to do as she is told without causing any problems!" I said. Marlene went on to say that Jamie had to work both Friday night and Saturday afternoon and since they lived 35 miles away it would be better for me to stay at their house. "Fuck me, now my plans were really shot to hell!!"

"Ok, but I'm serious about Jamie and her behavior. If you can't guarantee she'll do as she is told and agrees to a 1 am curfew, then all bets are off!" I demanded. Marlene agreed to the terms and after finding out their flight left 30 minutes after Linda's it was decided I'd pick them up Friday at 2 pm and drive everyone to the airport. Hanging up the phone, I gave Linda all the details. She just smiled knowing she had won yet another encounter. There were a couple of good golf courses down there and Bill and I had finished building a deck and privacy fence around their above-ground pool so maybe it wouldn't be a totally lost weekend.

The rest of the week went smoothly and before I knew it Linda and I were pulling up in her brother's driveway. Bill came bounding out of the house wearing a pair of khaki pants and the loudest flowered shirt I had ever seen. Getting out of the car I opened the trunk and help him load the arm full of suitcases her had. As he opened the door to get in he told me Marlene was in the house with some last minute details. As I entered the front door I immediately saw Marlene standing in the kitchen. While Bill looked like a typical tourist, Marlene wore a black leather mini-skirt that barely covered her round plump ass, a pair of high heels that lifted that ass nicely and a plunging low cut blouse, which showed off a ample amount of cleavage. For a woman who just turned 50 she looked absolutely stunning in that outfit. Walking into the kitchen Marlene turned and said.

"I can't thank you enough Dave for watching the girls this weekend. Here's everyone's cell phone numbers and well as our hotel and Robert's friends cabin numbers. Jamie has assured me that she will do as she it told and won't be a problem."

As I stood next to Marlene to inspect the numbers I couldn't help but gazed down the front of her open blouse at the tops of her well formed tits. I could see all the way to her belly button and wondered just what Bill was in for over the weekend. Marlene noticed my staring and leaned in and gently rubbed her breasts against my arm. After a few moments she turned and headed for the front door. Following behind her I watched as her ass swayed back and forth. Suddenly she stopped in the archway between the living room and kitchen, I almost ran over her, not realizing she had stopped. Then she reached her left hand behind her and running it up and down my flaccid dick and whispered.

"When we get back I need you to come over and help me with some plumbing. You know how inept Bill can be when it comes to working with his hands!" Then she continued out to the car and walked to the driver side rear door. Bill and Linda were engaged in brother-sister conversation as Marlene slide into the back seat. Neither noticed that she had spread her legs to get in the car giving me a clear view of the tiny red thong panties she was wearing. Marlene smiled as she saw my reaction to her blatant move. The ride to the airport a little less than an hour and everyone made small talk. Stopping the car at the terminal, I popped the trunk and got of my seat. Both Linda and Bill immediately jumped out and headed for the trunk to grabbed their luggage, opening the door again for Marlene she again spread her legs to exit giving me another view of her crotch.

"Hope you enjoyed the view! See you on Sunday." She whispered as she placed a quick kiss on my cheek and walked by.

I gave Linda a quick kiss good-bye, telling her to have a good trip and that I'd pick them all up Sunday. Getting back in my car I drove the hour back to Bill and Marlene's. I dropped my duffel bag in the main bedroom and grabbed a beer from the refrigerator. Turning on the TV, I looked for something to watch and was disappointed at the lack to decent programming available. I decided to explore the rest of the house and headed up stairs to the kid's rooms. Both Jamie's and Robert's room looked like atomic bombs had hit them. Clothing, books and magazines were scattered all over the floors and dressers. Going into Jackie's room I found it neat and orderly. Her dresser had a TV and VCR on top and a computer sat on the desk, everything was in its rightful place. I figured I had time for some web surfing before she got home in a little over an hour, so I fired up the computer and prepared to login. Then I decided to see what type of web sites she visited, opening up her cookie cache, I discovered visits to the usual teenage girl sites. Further exploring produced several porn sites with multiple visits but none within the last couple of weeks.

Closing the cache, I looked for other files within the computer. Finding on marked "JPJ" I opened it. Fifty JPEG files appeared, clicking on the first one I was surprised to see a picture of my niece sitting at her desk wearing just her bra and panties. The picture portrayed a girl of extreme innocence and beauty. As I continued, more pictures of her in different outfits appeared. None was very revealing but the did manage to get my blood pressure rising. With only eight pictures left unexplored I came upon a picture of her sitting topless on her bed. Her young breasts were perfectly formed and capped by extremely large puffy nipples. Two pictures later I was treated to a shot of her laying completely naked on the bed. She had a clean-shaven pussy and looked 3 or 4 years younger than she actually was. I felt my dick starting to harden as I pushed on the last five pictures. Picture 45 revealed her holding a medium sized dildo in her hand resting along the edge of her pussy. By now my dick has as hard as it ever gets. The next two pictures showed her sliding the dildo along her cunt lips once from the top and once from the bottom. Reaching down I unfastened my jeans and pulled my now rock hard member out. Slowly I began to stroke it as picture 49 appeared on the screen and there was Jackie with the dildo halfway up her canal. Just of as the final picture came into view, the dildo completely inserted into her and a look of total contentment on her face, I heard a car door slam. Looking out the window I saw Jackie in her cheerleader's outfit heading for the door.

Panic set in as I tried to both stuff my rigid member back into my pants and close all the computer files and exit the room. Finishing the tasks I raced down the stairs and was standing in the middle of the living room when Jackie opened the front door.

Jackie had spent the entire day in school on pins and needles. She loved her Uncle Dave and enjoyed being around him. He always seemed so laid back and easy going and she was looking forward to spending some time with him this weekend. As her body developed and she passed through puberty, she had developed a crush on her uncle. She made sure to wear tight jeans and shorts and low cut tops when she was around him. She loved teasing him and at the last several family functions delighted in feeling his erect penis whenever she sat on is lap. She took every opportunity to climb up on him and wiggle her butt into his crotch to see if she could provoke a reaction. She always did. Now she was hoping that with him alone in the house maybe she could provoke more than just a reaction. She wanted him to officially take her virginity this weekend. She had used her dildo over a year ago to remove her hymen but she still had never felt the real thing. Hopefully that would all change soon.

Opening the front door, Jackie saw her uncle standing in the middle of the room. Dropping her backpack at the door she leaped across the room and wrapping arms around his neck and her legs around his waist she squealed.

"Uncle Dave, you don't know how happy I am to see you? I was so afraid that someone else would be watching us this weekend. I know we are going to have a great deal of fun!!" Jackie immediately felt her uncle's erection pressing against her covered pussy and pressed back against it. "I wonder what's got him so aroused?" She thought to herself.

I was startled when Jackie jumped onto my torso. Her hands were around my neck and her legs were locked around my waist in a death grip. I was afraid she would feel my hard cock through the clothing and then felt her press her crotch against me. While I enjoyed the feeling I didn't want things getting out of control and pulling her arms from around my neck tried to put her down. As she relaxed her legs slightly she began to slide to her feet but managed to keep her covered pussy tight against my straining bulge.

"What shall we have for dinner?" I asked.

"How about we have pizza and watch a movie. Besides, I'm all sweaty from cheerleading and I need a shower." Jackie replied grabbing her knack sack and heading up the stairs. "The number for the pizzeria is on the refrigerator, call them and I'll be right down."

Finding the number right where Jackie said it was I called and ordered dinner. The pizzeria said they'd be there in 30 minutes so I grabbed another beer and settled on the couch to watch the news. My mind drifted back to the pictures on Jackie's computer as I heard her moving around upstairs. Soon I heard the bathroom door close and the sound of running water coming form the shower.

Jackie reached her room, dropped her bag on the floor and looked around. Seeing everything in its proper place she smile and unzipped the pleated skirt of her uniform and kicked it onto her bed. Pulling off the thick cotton shorts that went with the outfit they soon were deposited with the skirt. Next the sweater came over her head then she turned and admired her young body, covered only with her bra and panties in the full-length mirror. Slowly she removed her underwear and stood naked in the middle of the room.

"I wonder what Uncle Dave would do if I walked downstairs right now like this?" She silently asked herself. Then she opened her door and dashed across the hall to the bathroom. Turning on the shower, she waited for the temperature to adjust and climbed in. As the hot water cascaded over her young teenage body, Jackie was surprised to find herself mildly aroused. Memories of her encounter with her uncle flooded into her mind. She could still feel the firmness of his manhood pressing against her when she jumped into his arms. The image began to intensify as she lathered the soap into her hands and began to wash her body. She never used a washcloth any more enjoying instead the feeling of her own hands on her naked body. As she massaged the soap into her small breasts, she felt the nipples beginning to harden and the slight hint of moisture forming between her legs. Pinching the nipples, she moaned quietly and slowly moved one hand down along her tummy. Reaching her shaven mound, she pressed her palm to the top and ground small circles with her hand, the feeling was divine. She slowly worked her hand down past the mound and was soon massaging the outer lips of her labia. Sliding her middle finger down the crease of her pussy she found the opening she was looking for and swiftly plunged the finger into the wet tunnel. This action started the chain reaction within her body as she finger fucked herself she visualized it was her uncle's rigid cock instead of her finger. Her imagination took over as she raced toward her self-inflicted orgasm, becoming vocal as the ultimate release approached.

"Ooohhh Uncle Dave, donnn'ttttt stooooooooop, pleaseeeeeee don't stooppppp! I'mmmmmmm goooooooinggggggggg to cummmmm! Your cock feels sooooooo gooooooood, I'mmmm cummmmmming!!!! I'mmmm cummmmmming!!!!

Jackie felt her cunt pulse around her finger as her juices flowed out of her. She leaned against the wall of the shower for support and waited for the orgasm to subside. Soon her breathing was back to normal and rinsing off, she shut the water off and grabbed the towel that hung on the wall. As she dried herself, she decided that before the weekend was over she would convince her uncle to complete her journey to womanhood.

"It shouldn't be too hard a task. " She reasoned. " After all, that bitch sister of mine has to work and will probably go out afterwards and get herself fucked anyway. I should have Uncle Dave pretty much to myself for the next couple of days. Besides, if just seeing me got him hard, I sure I can tease him into anything I want!"

Walking back into her bedroom she opened her dresser and selected a pair of white sheer, see-through panties and put them on. Next she pulled her favorite nightshirt over her head, sat down and brushed her hair and then pulled it into a long flowing ponytail. Standing up she looked again in the mirror and satisfied with her appearance headed back downstairs. Just as she reached the top of the stairs the doorbell rang signaling the arrival of the pizza. Jackie waited until the deliveryman left and then bounced down the stairs and into the kitchen.

As soon as I paid for the pizza I headed to the kitchen. Before I had a chance to call out for Jackie, she appeared in the doorway. Looking up, I was stuck by the pure innocent beauty of the teenager standing in front of me. Fresh from her shower, she had a sensual glow, accented by the flowing nightshirt and cute little ponytail she wore. The shirt being well worn and a size too small emphasized the fact she wasn't wearing a bra, as her puffy nipples were clearly visible. As she sat down at the table the shirt rode up her legs giving me a good look at her firm athletic legs and thighs. While we ate, we talked about her school and how excited she was about graduating in June. She didn't know if she would be able to attend college but she was going to try. When dinner was over we cleared the table, deciding to see if there was any movie on worth watching, and headed for the living room. I decided to get comfortable and went into the bedroom and changed into a pair of silk running shorts. I had thought about leaving my underwear on but decided against it considering I truly enjoyed the feeling of my dick rubbing against the silk. I would have to make sure I didn't get aroused by my nimble niece since there would be no way to hide a hard on. I returned to the living room and sank into the oversized couch. Jackie had found "American Pie II" on one of the cable stations and was stretched out on the floor in front of the TV.

"Is this ok with you Uncle Dave?" She asked picking her head up to look around.

"Anything you want to watch honey is ok with me." I replied smiling at the fact the movie contained some suggestive scenes.

mityam
mityam
103 Followers