Introduction

The story I am about to share with you took place just a few years ago. My name is Steve and this is all about how I got over the trauma of losing my father. Without going into any gruesome details, the short story of it is that my father was killed in a car accident while I was sleeping in bed. My mother woke me up to tell me the news. Ever since then I have had trouble sleeping because I am afraid that something bad will happen while I sleep.

My mother, Sally, joined a support group for ‘Widows with Sons’. That is where she met Jenny, another widowed mother, and her son Johnny. Johnny was the same age as me and lived nearby.

My parents did not have a life insurance policy for my father, so my mom had to work twice as hard to make a comfortable life for the two of us. Sometimes this meant having to travel and be away from home on short trips.

Jenny's husband was killed on the job due to the company's negligence, so Jenny was paid out a large sum of money and no longer has to work. She used to be a full-time massage therapist but now she only does it occasionally.

Johnny and I are both of legal age, but we are both years behind our peers, socially. The support group mentioned that boys tend to develop slower when they lose their fathers at a young age. I had never had a serious girlfriend, and I was still a virgin. I'm pretty sure Johnny was too.

Johnny and I hit it off immediately and would always hang out at each other's houses and play video games.

When Jenny won her settlement, she bought a new house with a swimming pool in the backyard. His house was my favorite place to spend my summer vacation. My mom would also spend time with me at his house on some weekends drinking wine with Jenny and gossiping about the other moms in the group.

My mom was given a task at work that she would have to travel for a much longer duration. My mother always doted on me and wanted someone to take care of me. She turned to her friend Jenny for help.

Jenny was well aware of my insomnia and all the antics that I got into at night. It turns out my mom knew more about what I was doing at night than I realized. And she shared every little perverted detail of it with Jenny. Jenny had been intrigued by it and even slightly aroused by her stories. Jenny came up with a plan to cure my sleeping disorder.  She wasn’t sure if she’d be successful but she thought it would give it her best shot.

Please sit back and enjoy my story about how an older woman used her touch and seduction to cure me of my sleeping disorder while I was in her care.

Chapter One

When I was younger, my favorite thing to do during the summer was play video games with my best friend Johnny. Our second favorite thing was to go swimming in his pool. My mom couldn't afford a video game system, or a pool for that matter, so we preferred to hang out at his house.

Whenever we went swimming, Johnny’s mom, Jenny, would hang out poolside in a conservative swimsuit, sipping wine and absorbing the sun. Sometimes my mom would stay and join her.  I had never taken much notice of our moms and their bodies until recently. But once I noticed just how hot our moms were, it was all I could see and think about. Looking back on it now, I noticed that as Johnny and I got older, Jenny’s swimsuits became less and less conservative and were more and more revealing.

I had developed a small crush on Johnny's mom, but I never had the balls to say or do anything about it. I just stole small glances at her when I could and I masturbated to her often. My first choice of porn was, ‘MILF porn’. I almost always imagined Jenny as the MILF in my fantasies. Although sometimes my mom would invade my fantasies too.

Jenny was a gorgeous woman with long flowing brunette hair. Sometimes she died her hair a dirty-blonde color which made her look more like my mom. She had the face and body of a twenty-year-old with above-average-sized tits and ass. Jenny was hit on constantly by men her age, but she rejected them all, outright. She told herself that it was because she wanted to care for her son without any distractions, but secretly it was because she preferred younger men.

I was never an unruly son, but I always seemed to be getting in trouble. Most people chalked it up to the loss of my father and let me get away with most of it. My biggest issues always seemed to stem from my inability to sleep at night. This caused several side effects. My teachers would always get upset with me because I would be half asleep in class but I still got good grades because I would be up all night, so I always completed my homework or studied for tests. My mother did her best to keep me happy. She ignored most of my bad behavior in hopes that it would go away over time.

Some nights I would have panic attacks at bedtime so my mom would lie in bed with me and comfort me. Sometimes I would come into her room and she would let me crawl into her bed and spend the night in her bed. This was never weird or awkward for me until I got older and my hormones had taken over my thoughts.

*

Nighttime was always my time. I found so many ways to entertain myself in the middle of the night. I felt like time had been frozen just for me, and I was free to explore the world without any consequence.

My mom tried just about everything to help me sleep at night. She tried hypnosis, sleeping pills, sound machines, aromas, and different foods, but nothing worked.

Eventually, my mom started taking my sleeping pills because I was keeping her awake at night. This led to even more discoveries in my late-night exploring.

My number one way to pass the time was watching porn and masturbating. I started out being as quiet and discrete as possible, but eventually, I turned to watching porn on the living room TV and masturbating on the couch.

I usually only did this on nights when my mom took sleeping pills. She would always tell me when she took them because she didn't want me to worry if I had to wake her in the middle of the night. She didn't want me to think she was dead or something.

I remember one night I was watching porn on TV and lost track of time. I had been at it all night and my mom had woken up the next morning and caught me. She didn't overreact, she was just surprised and asked me if I did it here often. I told her the truth that I only did it when she took sleeping pills and she accepted this answer. She just told me to clean up the mess after I was done. I started jerking off on the couch more often after that.

The other naughty thing I would do at night was sneak into my mom's room while she slept. Sometimes I would go through her things and look for anything sexual. I found out my mom had an extensive dildo and vibrator collection. I realized that my mom never had another man in her life after my father so this made perfect sense, but realizing that my mom enjoyed sex that much was a new epiphany for me.

Other times I crept into her room, and I would find her in all different kinds of undress. Usually, she slept in a t-shirt and shorts. Other times I would find her in a sleep shirt or just a pair of panties. A couple of times, I found her sleeping in the nude with her vibrator still laying on the bed next to her.

Sometimes a would stand over my mom and masturbate while looking at her. I would even reach out and touch her soft flesh. I enjoyed touching her legs and thighs. If her tits or ass were exposed I spent several minutes or hours exploring these curvy havens.

*

I had never spent the night at Johnny's house before but my mom had an important business trip she had to go on, and she would be gone for over a week. She was worried about my welfare while she was gone and wanted someone to watch over me. I told her that I would be fine at home, but I didn't mind spending the week at Johnny's house either.

My mom arranged a lunch date with Jenny to discuss her idea with her.

“Thank you for meeting me for lunch,” my mom said to Jenny.

“It is my pleasure,” Jenny said, as she sipped her glass of wine.

“I wanted to ask you for a huge favor,” Sally explained, “I have to leave town for over a week, and I was hoping Steve could stay with you during that time.”

“Absolutely!” Jenny said, “ He is a pleasure to have around. I would be happy to have him stay with us.”

“Thank you so much, Jenny,” Sally continued, “But you do know he has a hard time sleeping at night. It can become very disruptive at night.”

Jenny replied quickly, “You know what? I was just reading about a special treatment that includes massage therapy and another stimulus that can be used to treat Steve's exact condition. Would you be willing to let me try it out on him?”

“Of course! I've tried everything, feel free to give it a shot.”

“Okay, I just want to make sure you're okay with me rubbing and touching your son like that,” Jenny said, “This particular treatment is still experimental and can be somewhat sexually arousing. The key to this therapy is finding a way to release his, umm, anxiety and allow his body to relax and fall into a deep natural slumber.”

“If you can do that for my Steve, I would kiss you!” my mother said.

“Okay, but I just might take you up on that,” Jenny said flirtatiously, as she finished off her glass of wine and signaled the waiter for another glass.

*

I usually get anxious when my mother has to leave town for a few days, but this time I found myself getting excited. I was looking forward to all the video games we’d get to play together. I also pictured myself swimming in their pool, all day and night. And lastly, I imagined spending lots of time with Jenny. My dick grew hard when I thought about walking around her house and bedroom at night after everyone had gone to bed.

My mom told me that Johnny's mom knew all about my condition and that she knew of a new treatment for my insomnia. She told me that I should let her do whatever she wanted as it could help me get past my sleeping disorder. My mom then told me to go pack some clothes for my visit. Being the teenage boy that I am, I didn't give it much thought. I just threw a few things that I thought I’d need into an overnight bag and I tossed it in the corner of my room. I planned to add more items to the bag before the day of my mom’s trip.

*

The day of her trip arrived, and my mom was going to drop me off at Jenny and Johnny's house before she drove herself to the airport. We managed to get out of the house early and got to Jenny's house much earlier than we had planned. We both went up to the front door and Jenny answered the door in a sexy little white bikini.

“Oh my gosh! Hi guys. You are earlier than I expected. I was just sitting out by the pool reading a book and trying on the new swimsuit I just bought. They say it doesn't leave any tan lines because it's made out of a special material,” Jenny said, “Please come inside. How much time do you have, before you have to leave, Sally?”

Jenny turned around and led the way inside. I couldn't help but stare at her sexy ass, and the way she said ‘Please come inside’ made my dick hard before I made it across the threshold.

“I have enough time for one glass of wine to calm my travel jitters before I have to leave,” my mom said.

“Perfect,” Jenny said, “ I could use one too. Would you like a glass, Steve? Oh, if that's okay with you, Sally.”

“Sure, why not? Let him have his fun. This is a bit like a vacation for him anyways,” my mom responded.

I was surprised my mom told Jenny that I was allowed to drink. She had always been against it in our house. Jenny poured me a full glass of wine and my mom half a glass before she stopped her from pouring more.

Jenny and my mom were chatting with each other while and drank my wine and tried to look at Jenny's exposed body without getting caught. She looked and smiled at me a few times. I'm not sure if she caught me staring, but I thought I played it off rather well.

My mom finished her glass and said it was time for her to go. We all got up and walked her to the door. I was already feeling a slight buzz from the wine but it didn't show. My mom hugged Jenny first, while I just stood there and watched.

When they were done, my mom grabbed me and pulled me into her. I felt my hard cock pressing into her, but I couldn't do anything about it without being obvious.

“I'm going to miss you so much, honey,” my mom said, “Be a good boy and do whatever Jenny tells you to do. Hopefully, I will be back before you know it.”

My mom backed away from our embrace and kissed me on the lips. After our kiss, she backed away again and briefly looked down at my crotch, confirming that it was my hard cock that was poking into her.

My mom then turned her attention to her purse and pulled out a bottle of prescription sleeping pills. She handed them to Jenny, and said, “In case all else fails, you can use these however you'd like.”

My mom turned around and walked out the door to her car. We stood in the doorway and watched my mom get into her car. We all waved goodbye as she pulled away.

*

Jenny closed the door and walked back to the kitchen. She poured herself another glass of wine and then topped mine off to the top.

“That was some hug and kiss that you gave your mom back there. I'm jealous. I never get hugs and kisses like that anymore. Maybe you will honor me with one like that later,” Jenny said to me.

I nodded my head, and asked, “Where’s Johnny?”

“He is away at practice. He is usually gone all day until dinner time, sometimes later.”

“Oh, okay,” I said, a little disappointed I couldn't play video games with him all day but excited that I could spend alone time with Jenny instead.

“How would you like to go swimming?” Jenny asked, trying to cheer me up.

I immediately forget about playing video games with Johnny and told her that I wanted to go swimming. She told me to go get changed. She had made the guest bedroom up for me and told me that I could change in there and leave my stuff in there too.

I ran to the guest room and tore off my shirt. I opened my bag and started rummaging through it. After a couple of seconds, I realized that I hadn't packed a swimsuit. All I packed was four t-shirts and two pairs of socks. I didn't even pack any shorts, pants, or underwear.

I walked back out to the kitchen without putting my shirt back on and told Jenny what I had packed. She laughed and told me that it was fine. She said that I had three choices.

“I can try to find one of Johnny's old swimsuits, or you can wear your underwear, or you can go commando,” she said, “And in case you're worried about skinny dipping, just know that I do it all the time. We have lots of privacy back there so no one will see you.”

No one except her, I thought to myself.

“I guess I will try one of Johnny's suits,” I said.

“Okay. Wait here and finish your wine before it gets warm,” Jenny said as she bounded off to Johnny's room.

I sat and drank my wine. I noticed it was calming my nerves a little and I was starting to like the taste. I never liked the taste of alcohol before but the taste was suddenly growing on me.

Jenny returned quickly and I watched her tits bounce as she jogged back into the kitchen. She handed me a small blue speedo.

“What's this?” I asked.

“Ever since Johnny joined the swim team, it's all he wears now. Did you want to try them on?”

“Sure,” I said, as I headed back to my room to change.

I stripped out of my pants and underwear. I looked at the funny-looking swimsuit and determined which way was front. I slid them up my legs. They were small on me but not totally uncomfortable. My privates left a large bulge in the front of the suit, but there was nothing I could do to change that.

I walked out of my room and started walking toward Jenny. When she first saw me, she said, “Oh, good, it fits.”

Once I got closer to her, she realized that it was actually a little small on me, and she said, “Oh, my! You're apparently bigger than Johnny.”

Her comment made me feel embarrassed, but then she said under her breath, “In more ways than one.”

Her second comment gave me just the right amount of confidence to continue wearing the tight swimsuit. That and the alcohol-induced lowered inhibitions.

Jenny poured both of us another glass of wine and then led the way out to the pool. I followed her and watched her ass as we walked. Jenny set my wine glass down next to one recliner a lay on a recliner across from it, next to her book.

I dove straight into the pool and swam a couple of laps. I invited Jenny to join me but she said she wanted to read her book and work on her tan for now. I kept taking peeks at Jenny's body in her swimsuit, but each time I looked at her, she was already looking at me. We exchanged smiles and I kept swimming.

Once I had gotten tired from swimming, I got out of the pool and sat on my recliner. I didn't bother to dry off, I just let the sun dry me off. I drank my entire glass of wine in one big swig and lay down.

After lying on the recliner for a couple of minutes, Jenny finally spoke, “You should put some sunscreen on, I don't want you to burn. Here, let me do it for you. Roll over, please.”

Jenny grabbed the bottle of sunscreen next to her chair and got up as I rolled over onto my stomach. Jenny sat on my chair, her ass touching my hip. She poured some sunscreen into her hands and started rubbing it into my back.

It felt good to have her touch me like this. I noticed that she wasn't just applying sunscreen to my back, she was massaging my back. I couldn't help but let out small moans of pleasure as she rubbed my body. When she got down to the base of my back where my swimsuit started, Jenny ran her fingertips under the seam of my suit. This small act excited me more than it should have.

Once my back was done, Jenny moved her seat further down the chair and rubbed my legs after getting more sunscreen. Jenny's touch was much softer now. She was running her hands up and down the backs of my legs staying just below my knees.

After that, she moved up to my thighs and spent a lot of time on my inner thighs and below my butt. I could feel my cock swelling in my speedo but I managed to prevent it from getting fully hard.

The last thing Jenny did was push her fingers under the seam of my shorts and rubbed my ass cheeks. Then she pulled her hands out of my shorts and told me to turn over.

I did as I was told. I rolled over and I immediately looked down at my crotch to see how obvious my hardness was. I was not the only one looking at my crotch, Jenny was looking at it too. My cock had grown in both size and thickness. It was lying across my lap to one side and the exact size and shape were clearly defined in the tight speedo.

I enjoyed having Jenny look at my cock, so I quickly closed my eyes and pretended not to notice my condition. After a moment of admiring my cock, Jenny began applying sunscreen to my legs. She started at my feet and then worked her way up to my crotch.

Since the speedo was so short, when Jenny rubbed my upper thighs, her hand was also rubbed back and forth against my balls. I could feel my cock harden further. Just before finishing on my legs, Jenny pushed one hand under the seam of my speedo leg hole and rubbed my scrotum directly. Then she switched to the other side and repeated the same process. My cock continued to grow, to her delight.

Jenny then moved from her position and sat back down, next to my hip. She started applying sunscreen to my face. I could feel her breasts press against my chest as she leaned forward over me. I kept my eyes closed and pictured her tits in my mind as they touched me. My cock was starting to rise up, towards my belly.

Jenny finished my face and ears and moved to rub my chest. She ran her hands over my chest and ran her fingers across my nipples several times. She even gave them a quick squeeze a couple of times. Then she ran her hands across my stomach.  I was feeling highly aroused at this point, but I was also totally relaxed. I don't think I could have moved a muscle if I’d tried.

I felt myself sinking deeper into my chair. I was drifting in and out of consciousness as Jenny's hands roamed my exposed body. The last thing I remember was Jenny tucking her fingers into the waistband of my shorts and feeling her fingertips run along the length of my shaft as she moved her hand across my stomach.

I was in a deep slumber when I started imagining Jenny playing with my cock and giving me sexual pleasure. Jenny could tell that I had fallen asleep and smiled to herself.

Jenny was happy that she was able to get me to fall asleep. She knew it was due to a combination of the wine, the sun, her touch, and the sexual teasing. Jenny removed her hands from my body and started reapplying sunscreen to her own body, while still sitting next to me.

I was having sex dreams about Jenny while she sat there. After Jenny finished putting more sunscreen on herself, she looked back down at me, and then at my cock. What she saw surprised her. My cock had grown to its full hardness and was now sticking straight up, out of my swimsuit.

Jenny marveled at the size and shape of my cock. As she looked down at my cock, she noticed that the hot sun was beaming directly onto it. Jenny didn't want my cock to burn, but she also didn't want to wake me just yet.

“Steve, are you awake?” she asked quietly.

When I didn't respond, Jenny grabbed the waistband of my swimsuit and tried to pull it up over my cock. But it was no use. There were still at least four more inches of cock exposed above my stretched-up swimsuit.

Jenny knew she had to do something else, she pulled the front of my suit back down and tucked my waistband under my balls, to hold it in place. She opened the sunscreen bottle and put some in her hand and then hesitantly reached out and grabbed the shaft of my cock.

Her hand didn't move at first. She just felt the heat and thickness of my cock. She lifted my cock slightly and was surprised by the sheer weight of my package. Jenny had never seen, much less touched, a cock as big as mine. It was bigger than the grown men she had been with, and she presumed that mine was still going to grow in size, due to my age.

Jenny started slowly rubbing her hand up and down my cock. She was not squeezing or jerking me off, she was just letting her hand run over the contours of my hard cock as she spread the sunscreen over every inch. She felt a tinge of guilt for touching me while I slept, but she reasoned that she was performing a necessary task to prevent injury. She covered every surface of my cock more than once, several times, in fact, ‘Just to be safe,’ she told herself.

Jenny moved from my cock to my balls after adding more sunscreen to her hand. She liked how tight my scrotum felt and enjoyed touching the tight smooth skin. It was definitely not the scrotum of an older man. After fondling my balls for a few minutes, Jenny returned her hand up to my cock and wrapped her fingers around it tightly.

Johnny's mom started slowly stroking my cock now. She was no longer using the pretense that she was only rubbing sunscreen into my hard cock. Her free hand moved between her legs and she began rubbing her pussy through her bikini bottoms.

Jenny saw pre-cum forming at the tip of my cock, turning her on even more. Rubbing her pussy through her bikini was no longer satisfying her. She moved her hand to the inside of her bikini and rubbed her swollen clit. After a few minutes, she plunged her fingers into her pussy. As she finger-fucked her pussy, her other hand picked up the pace of stroking my cock.

I was having a vivid dream of fucking Jenny. My cock felt so good. I wanted to release my load inside her pussy. I felt the waves of pleasure course through my cock and I had an orgasm in my sleep.

Jenny watched as my cock erupted and shot cum all over my chest and stomach. She brought herself to orgasm just a moment later while still gripping my cock. Once she had come down from her blissful state, Jenny looked at the mess I had made. Afraid that she would get in trouble, she reached over to her chair and grabbed her towel. Jenny gently cleaned all of the cum off of my body, and then she gently released my waistband from its constraints and moved it back over my deflating cock.

My cock was starting to soften but two inches still protruded from the top of my shorts. Jenny quietly returned to her chair and picked up her book. She did not read it though, she just peeked over it and looked at my body and cock.

Once my cock had descended below the hem of my waistband, Jenny decided that it would be best to wake me up and roll me over.

“Steve! You need to wake up now,” she said but got no response.

Jenny extended her leg and touched my foot with hers. She pushed against my foot with force and called out to me again, “Steve, wake up. You need to roll over or you'll get burnt.”

This did the trick, I opened my eyes slowly and saw Jenny sitting across from me. When she saw that I had woken up she bent her knee and put her foot back on her recliner. The angle that we were sitting across from each other allowed me to see between Jenny's legs and I noticed a wet stain had appeared on the crotch of her bikini bottoms.

I was not able to look closely as Jenny was looking right at me and said, “Sorry to wake you, but you need to roll over or you'll get burnt. Feel free to go back to sleep if you like. I will do whatever I need to, to make sure you don't burn anything.”

Jenny was thinking about how she rubbed my cock earlier and swore to herself that she was just being a good hostess and preventing a bad sunburn. I thanked Jenny and rolled over on my stomach. Jenny looked at my ass and couldn't believe that she hadn't noticed how nice my ass was before. She wanted to touch herself again but thought better of it. She wasn't even sure if I was asleep or not.

I wasn't. I was replaying my dream in my head and thinking about how vivid it was. It could only have been because Jenny was rubbing sunscreen into my body and the sensations were invading my dreams. I lay there awake thinking about my dream and getting turned on again. As I lay there with these thoughts, I was surprised that my cock didn't respond or grow hard in my shorts. I thought maybe it was because of the pressure of the chair against it, preventing the blood from flowing into my cock.

Nothing else happened while I was on my stomach. I was awake and deep in my thoughts while Jenny was fully immersed in her book, stealing glances at me and my ass only when she turned the pages of her book.

After several minutes of sunbathing on my stomach, Jenny said, “It's time to turn over again or go back inside.”

I rolled over and said, “I think I'm ready to go inside. I'm getting kind of hot out here anyway. I think I'm going to jump in the pool real quick to cool off, then I'll go inside.

Jenny agreed and watched me as I got up and jumped in the pool. She looked at my crotch when I got up and was slightly disappointed that I was not hard again, but she was also relieved.

*

After swimming a couple of laps, I got out of the pool and toweled myself off. As I was drying myself Jenny said, “You should go take a shower to get the sunscreen and chlorine off your body. Oh, and I forgot to mention earlier, the guest bathroom is in a state of permanent remodel. I have had to fire the last three contractors and I still haven't found a replacement yet. You will have to use the bathroom in the master bedroom. You can use it anytime you like, day or night, don't be afraid to come into my room at night if you have to. I know about your condition and I completely understand. We just ask that you leave the bathroom door unlocked when you use the shower, in case someone needs to use the restroom in an emergency. And the same applies if you need to go and someone is showering. Are you okay with that arrangement?”

I agreed and asked Jenny to show me the way. Jenny got up from her seat and looked down at her towel. She could see the cum stains that had dried into it. She grabbed the towel quickly and folded it over onto itself, to prevent me from seeing the stains.

Jenny led me to her room and showed me the bathroom. Everything I would need was already there. I stepped into the bathroom and before I closed the door, Jenny said, “I'll be right out here getting changed if you need anything.”

I watched Jenny unhook the back of her bikini top as I was closing the bathroom door. I closed it as slowly as I could but had to close it fully before I saw anything else, otherwise, it would have been obvious that I was trying to watch her undress.

Her bathroom was spacious and decorated with high-end materials. There was a double sink on one wall and the opposite wall contained a jacuzzi bathtub, a large shower enclosed in clear glass, and a toilet right next to the shower. I was surprised that Jenny and Johnny would use the shower and the toilet at the same time as there was no privacy for either person.

*

I started the shower to warm it up before getting in. As the shower water ran, I removed my wet speedo and threw it in the corner of the bathroom where a small pile of clothes and dirty towels was already located.

I looked at my naked self in the mirror. I admired my cock and was proud of how big it had grown in the past year. Watching porn made me think my cock was normal-sized until I had to use the school showers and found out that my cock was three times longer and thicker than everyone else, and I knew it got even bigger when it was hard. I asked a friend of mine at school what he thought about the size of guys' cocks in porn. After teasing me about looking at cocks in porn, he said, “Everyone knows they only use guys with huge cocks in porn. I think they get surgery or something, nobody has cocks that big in real life.”

I thought about his answer and briefly thought about what my life would be like if I became a pornstar. It sounded like a dream job but I knew I'd never be able to face my mother ever again if I did.

While standing in the mirror, my hand went to my cock to rub it absentmindedly, when I discovered that it was covered with sunscreen. I looked at my dick and confirmed that it was completely coated in sunscreen. I racked my brain for how that could have happened.

I questioned for a split second whether Jenny could have put it there while I slept, but quickly dismissed this notion for something more probable. I concluded that it must have run down from my body when I jumped in the pool. I felt my chest and stomach and found that there was almost no sunscreen there, so this was the most likely reason.

I finally stepped into the shower and washed my body from head to toe. I kept thinking about Jenny running her hands all over my body as she looked at my cock, bulging in front of my shorts. I wanted to jerk off in the shower and normally I would have but I kept worrying that someone might walk in on me.

Jenny took her time getting undressed in her bedroom. Subconsciously, she kept hoping that I would walk back out of the bathroom and catch her standing in her room naked. As soon as she heard me step into the shower, she jumped on her bed and used a vibrator to bring herself to orgasm while thinking about me watching her.

Once I had washed my entire body, I stepped out of the shower and dried myself off with a clean towel. I then wrapped the towel around my waist and exited the bathroom. I wasn't even thinking about the fact that I was walking straight into Jenny's bedroom. I just walked right through the door like I owned the place.

I was startled when I saw Jenny lying on her bed. She was wearing a terry-clothed robe and it was clear that she was not wearing anything underneath. Her robe was opened enough in the front to be able to see most of her chest and stomach. I couldn't see the front of her breasts but could see through from the side, and I was able to make out the exposed underside of her right breast.

Her left leg was bent up and the left side of her robe was open. The right side of her robe was between her legs covering her privates but her left hip was left fully exposed and I could see that she was not wearing any underwear. Jenny was using a nail file on her fingernails and never even looked up at me, allowing me to drink in every sexy detail of the half-naked woman in front of me. Coming up with a loss of words but wanting to compliment her, I said, “Nice robe.”

Jenny finally looked up at me and smiled. She said, “Thanks, I left one just like it in your room for you to use whenever you want. It's a little bit older though. It's the one I used to wear until I bought this one.”

“Thanks,” I replied, “That's very thoughtful of you. It will probably get some good use out of me since I forgot to pack any clothes. And it will be perfect for coming and going to the pool.”

Jenny put down her nail file and got up from her bed.  She didn't even appear to be concerned about exposing herself as she moved and slid forward off the bed, causing her robe to slide back and open further, exposing her bare ass and a glimpse of her pussy, until she stood up and her robe fell back into place on its own.  Jenny walk right up to me and leaned in closely. I thought she was going to kiss me until she spoke.

“Mmmm, you smell good,” she said, and then she walked past me into the bathroom and closed the door, leaving it open just a crack.

I watched Jenny through the crack as she started the shower and then dropped her robe to the ground, exposing her nude body before she stepped inside the shower. I couldn't make out any details through the small crack in the door so I made my way out of her room and went back to my room.

I dropped my towel on the ground and opened the closet door. Hanging up in the closet was a white terry-clothed robe, just like Jenny said there would be. I pulled the robe out of the closet and put it on. I wrapped it around my naked body. It was nice and soft. It felt like a fluffy towel or a blanket on my bare skin. I reached down to tie the robe closed but couldn't find a belt. I looked down and noticed that the two belt loops on the robe were broken and could not hold a belt anymore. I figured that this was why Jenny had replaced the robe with a new one. I was not worried about it as I could just hold the robe closed with my hands and the robe was far too comfortable to pass up.

I picked up my one pair of underwear and put them on. I kept the robe on, slid my phone into my pocket, and made my way to the living room. I decided to see if I could figure out how to use the TV since there wasn't one in my room. I was able to figure out the TV rather quickly since it was the same brand as our TV. Next, I pulled my cell phone out of my robe pocket and opened a YouTube video. I selected the required options on my phone and suddenly the YouTube video was now playing on the screen. This meant that I could now stream anything I wanted from my phone to the TV. Just like I do at home.

I was just about to verify that my favorite porn video would work too, when Jenny said from behind me, “Oh, good. I see you already figured out how to work the TV. How would you like to watch something with me? We have a few hours until dinner time.”

I agreed and disconnected my phone from the TV. Jenny went to the kitchen and poured two glasses of wine. It was the first time I was able to look at her, as she was standing directly behind me earlier. I saw that she was wearing the same robe from earlier. I wondered if she put anything on underneath or not.

I continued watching her as she returned with our drinks. I could tell that she still wasn’t wearing a bra, but I couldn’t tell if she had put on panties or not. Jenny stood in front of me and handed me a glass. As she leaned forward to hand it to me, I was able to see her exposed tits, down the front of her robe.

Jenny noticed that I was looking down at her tits and it excited her that I was peeking at her body. She thought she caught me looking at her several times before, but she couldn't be certain. This time though, there was no doubt where my eyes were looking. She felt her body get flush and her pussy moisten. She didn’t know what had come over her, but she was doing everything she could to try and fight it. Jenny turned around and sat down right next to me. Her body nuzzled right next to mine.

“So what are we watching?” Jenny asked.

“Ladies' choice,” I said.

“Oh good, I hope you like sappy romance movies then,” Jenny teased, as she grabbed the remote out of my lap, rubbing against my cock in the process.

Jenny opened one of her streaming platforms and scrolled straight to the romance section. She scrolled through a few movies until a half-naked Michelle Pfeiffer appeared on the screen. The movie was called ‘Chéri’ and it was released in 2009. I had never heard of it but I did enjoy half-naked women.

“Oh, I like Michelle Pfeiffer. How about you?” she asked.

“I do too. I really liked her in ‘Scarface’. She looks like she's still just as sexy now as she was back then,” I replied.

“Oh? You think older women can be sexy?” she asked.

“Absolutely! I think older women are even sexier. They have beautiful curves and luscious tits that get me so excited. It makes me...” I stopped myself when I realized I was explaining how turned on I get to the one woman who gets me the most turned on.

Jenny had heard enough and didn't press me to finish my sentence.

“It's settled then, we are watching older, sexier, half-naked Michelle Pfeiffer,” Jenny said as she snuggled in tighter to me and pressed play.

It turns out that the movie was about a boy's mom who asks her friend, Michelle Pfeiffer to teach her son about what to do in the bedroom. There were a couple of hot sex scenes between the two of them and eventually they fall in love, despite the 20 years that separated them.

While watching the movie, Jenny could tell that I was getting sexually aroused. She wanted to see how far she could push me. In one scene, Michelle Pfeiffer receives a back massage. Jenny watched the scene and said, “That looks like it would feel good right now. Would you mind rubbing my back while we watch the movie? I promise that I'll return the favor.”

I agreed and started rubbing the back of her robe. She sat up and said, “Not like that.”

Jenny loosened her robe over her shoulders and then pulled her arms out of the sleeves. Her robe fell from her body and gathered at her waist. Jenny was turned away from me so I couldn't see her exposed tits but I was able to see the side of her boob.

I put my hand up to her back and started rubbing. Before I got very far, Jenny lay across my lap and supported herself under her arms. I couldn't be certain but I swear one of her hands was sitting right on top of my cock.

I rubbed my hand back and forth across Jenny's back. My hand kept venturing further and further over the sides until I was able to reach the sides of her breasts. I pretended not to notice what I was doing but Jenny was fully aware of my actions. She decided to allow me to have my fun after what she had done out by the pool.

Jenny felt my cock start to swell beneath her hand and she felt herself getting turned on too. The movie ended and she knew her son would be home shortly, so she put a stop to my roaming hands and sat up. She covered her bare breasts with one arm while she struggled to get her robe back on. I grabbed her robe and pulled it up over her shoulders.

She thanked me for being sweet and told me that we better go get fully dressed so her son didn't get the wrong idea. I went to my room and threw on my jeans and t-shirts. I was dressed in seconds but I need to use the restroom. I knew Jenny would still be getting dressed but I really needed to pee.

I went to Jenny's bedroom door and knocked.

“Yes?” she asked.

“I need to use the restroom urgently,” I said.

“Hold on one second...” she said, “Okay, come in.”

I entered her room and saw her standing there in a sexy pair of bra and panties. They were not extra revealing, they just perfectly accentuated her body in the most erotic way.

“This is some new underwater I just bought. I wasn't too sure about it, but judging from your reaction, I can see you approve. You can close your mouth and go use the restroom now,” she said playfully.

Johnny arrived home a few minutes later. Jenny busied herself getting dinner ready while Johnny and I hung out. Every time I saw Jenny I could only picture her in the sexy underwear that she had on under her clothes. It felt like a naughty secret that only the two of us knew about.

After dinner, Johnny and I went to his room to play video games. We played for about an hour until Johnny said he needed to go to bed. He had practice again in the morning and needed his sleep. I left Johnny's room so he could get ready for bed. I looked for Jenny but I couldn't find her. I figured she was in her bedroom.

I called my mom to see how she was doing and to wish her a good night. She told me she was doing good but work was worse than she thought. She told me she would be busy working hard every day and she hoped it wouldn't take longer than she planned. I told her about my day and that I was having a good time. I told her I missed her and we said our goodbyes.

As I was sitting on the couch scrolling through my phone when I heard the shower start. I wondered if it was Johnny or Jenny. As I was considering this, Jenny walked into the kitchen. She told me that she was going to bed after she got Johnny into bed. Jenny walked over to me. She stood in front of me and held her arms out in front of her.

“I'll take that hug and kiss now, that you promised,” she said with a smile.

I stood up and embraced Jenny in a hug. As we were hugging we moved our heads to look each other in the eyes. Jenny leaned her head forward and pressed her lips against mine. It was only a quick kiss but it was still thrilling to kiss this beautiful woman. We continue to hug a little longer. Just long enough for blood to start flowing into my cock while it was pressed against Jenny. It did not get fully hard, but it definitely thickened between us.

Jenny did not respond but she felt my cock grow. It made her pussy wet when she felt it. She wanted to lean in for another kiss but decided against it. Jenny was the first to break the hug, and said, “Good night. Try to get some sleep tonight. If you are unable to sleep tonight, please let me know tomorrow and I will see if there is anything I can do to help.”

I said, “I will. Good night,” as we both headed to our bedrooms.

I stripped down naked and climbed into bed. My hand went directly to my dick. I started stroking my cock as I thought about all the sexy interactions I had with Jenny. I stroked my cock for several minutes but I couldn't bring myself to orgasm. I gave up out of frustration and just lay there staring at the ceiling.

I tried to convince myself to sleep, but it never happened. At one in the morning, I decided to get out of bed and explore the house. I threw my robe on over my naked body. Since I was the only one awake in the house, I didn't bother to close the robe, but I knew I could if I ran into someone.

I started in the kitchen. I went through the cupboards to see what kind of snacks they had. I found a box of cookies and grabbed a handful before putting the box back.

Next, I explored all the closed doors in the house. I found a typical coat closet by the front door. I also opened the door that I knew led to the guest bathroom. When I opened the door I found a large piece of plastic behind the door blocking my path and view of the bathroom. The plastic had a zipper running down the middle of it, down to the floor. This was obviously so you could get into the bathroom without removing the plastic wall. I didn't bother to go any further. I closed the door and continued exploring.

I opened a door that I thought was the laundry room. I was correct but something was off. There was a huge pile of laundry in the room but there was no washer or dryer. I saw the empty hook-up locations but no machines. I thought that was odd but moved on.

After finishing my last cookie, I felt the urge to pee. Jenny told me I could use the bathroom at night but I didn't want to wake her.  I approached her bedroom door and found it was open slightly. I could see that the lights were all out but there was a small light shining inside the room. It looked light maybe a night light was on inside the room.

I pulled my robe closed and slowly pushed her door open. I knew I had permission to enter, but I felt nervous about entering her room while she slept. I saw the night light plugged into the wall next to the bathroom door. I figured this was here so Johnny could find his way to the bathroom at night.

Then I looked at Jenny. The light was dim but it was still bright enough to see Jenny clearly. She was on top of her blankets, completely uncovered. She lay on her stomach so I had a nice view of her plump ass. She was wearing nothing but the panties I saw her in early. She had removed her bra, but I couldn't see anything because she was on her stomach.

My cock began to harden as I looked at her. I let my robe fall open and I grabbed my hard cock. I stroked my cock quietly. I imagined running my cock along Jenny's ass. It didn't take long, I felt the urge to cum. I took a step closer to Jenny as I contemplated shooting my load right there. Luckily, I was able to snap out of it and went into the bathroom instead. I closed the door behind me and stood over the toilet. I closed my eyes, pictured Jenny on her bed, and came after a couple of seconds.

I stood there for another minute as my cock softened and then I filled the toilet with urine. I wiped down the toilet and flushed. After washing my hands I returned to the bathroom not bothering to close my robe. I took another long look at Jenny sleeping peacefully and left her room.

To be continued.