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The Cure for Insomnia (Part 4, Day 3, PM)

"A young man has a sleeping disorder. His best friend’s mom thinks she has a cure.……"

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I fucked her hard and fast. Jenny's body was withering around while I had my way with her. I felt her pussy clench on my cock several times and I knew Jenny was cumming but she was climaxing too hard to mention it.

I felt my cock pulse as it pumped my cum out of my balls and injected it as deep as possible into Jenny's pussy. Jenny felt my cum blast against her cervix sending her body into yet another convulsing orgasm.

Once I had finished pumping every last drop of semen out of my body, I gently placed Jenny's body onto the floor. My cock slid out of her pussy and began to soften after finally being sated. Jenny melted into a puddle on the floor whimpering happily to herself as I got up and head for the shower.

Chapter Four

I stepped into the shower and washed my hair and body. I was innocently washing my flaccid cock when a motion caught my eye. Jenny was in the bathroom with me but I didn’t know how long she'd been there.  She was leaning back against the sink with her bathrobe untied and open. Her head was tilted back and her eyes were closed. She ran her hands all over the front of her body. She wasn't touching herself, but that didn't make it any less erotic to watch.

I kept my head down and only looked with my eyes. I planned to look away if she opened her eyes and looked at me. I didn't want Jenny to know that I was alerted to her presence. I continued to wash myself as I watched her. I saw her open her eyes and slowly move her head toward me so I quickly lowered my eyes to look at what I was doing.

I scrubbed my cock and balls as seductively as I could. Still flaccid, but slowly getting nice and plump. I loved the way it looked in this state, and I could feel Jenny's equally appreciative gaze on me - and on it - as I washed myself.

After spending more than enough time on my member, I decided it would be best to move on, but wanted to keep the show going for her. I turned around in the shower to get some more soap while trying to think of something else to do. I bent down slowly to pump some soap into my hand. I felt Jenny's eyes burning into my ass which gave me an idea.

After getting a handful of soap, I reached between my legs and started cleaning my asshole. I scrubbed my anus with my finger and bent over a little further so she could get a better view.

I made small little circles with my finger, trying to turn her on. I was surprised by just how good it felt. I had never played with my ass before. I continued playing with my ass as I switched from making circles to applying direct pressure.

Without warning my soapy finger slipped inside my ass. I was shocked. I wasn't even trying to do that. I kept my finger there and slowly rocked it back and forth. It felt amazingly good. I pushed with a little more pressure and my finger continued to penetrate my ass effortlessly. I noticed that the further I went, the better it felt.

I continued delving further, stopping every so often to stroke in and out along the way. I had completely forgotten all about Jenny. I was solely focused on the new sensations that I was experiencing.

I made the journey into my rectum as far as I could reach. I then moved my digit around inside my ass making note of what felt good. Suddenly, I grazed over my prostate and sent a shiver through my body.

I did not know why, but I knew that it felt good. I moved my finger around more frantically looking for the same spot. All of a sudden I remembered that Jenny was watching me and I was now fucking my ass in front of her. I suddenly felt embarrassed and ashamed. I was just about to remove my probing digit when I hit the same pleasure spot.

Now I knew where it was, and this time it felt even better when I touched it. I tapped against my prostate causing my finger to slide in and out of my ass. Having Jenny watch me do this was now exciting for me. I wondered if she was touching herself while she watched me.

I felt a strange new pressure in my groin. It almost felt like I had to pee but I didn't want to stop. At that point I didn't care if I did piss myself, I was in the shower anyway.

I had to put my other hand against the wall as my legs were getting weak and shaky. I fingered my ass faster and harder as the pressure built up inside me.

I thought I was just about to pee when my entire body started quivering and cum shot out from between my legs. It was such a strange feeling to ejaculate when I was not hard. I was also surprised because I thought my balls were completely empty by now. The orgasm I experienced was much different than any I had ever experienced before. I figured that it was because I pleasured myself through my ass and not from stroking my cock.

I slowly pulled out of my abused asshole and washed my hands with another pump of soap. I remained bent over as I washed. After washing my hands I stood up and slowly turned around.

I saw Jenny looking at me as she continued to lean against the sink. She was holding herself up with her hands and her robe was still open. I noticed her chest was heaving faster like she was out of breath all of a sudden.

When I made eye contact with her, I pretend to be surprised but not startled, “Oh, hello. How long have you been standing there?” I asked.

“I just walked in,” she lied.

“Did you need to use the toilet?”

“No, I need a shower actually, but I can wait,” she said.

“Okay, I just finished anyway.”

I stepped out of the shower and Jenny pulled a clean towel off the towel rack and handed it to me.

“I also wanted to talk to you about something. Do you mind talking to me while I take a shower?” she asked, as she dropped her robe and stepped into the shower getting her hair and body wet.

“No, I don't mind,” I said.

Jenny turned away, got some shampoo, and then turned back toward me, she then rubbed the shampoo into her hair. I toweled the water off my body while I watched Jenny.

“I want to apologize for my behavior,” Jenny began, “I allowed myself to get carried away earlier and that was unacceptable.”

“What? It's okay, really!” I protested.

“No, it's not. Your mother left you in my care and I took advantage of you. It was irresponsible of me and I will try to control my urges in the future and not take advantage of you, I promise.”

Jenny put her head under the water to rinse the shampoo out of her hair. I knew she wouldn't be able to hear me respond so I just watched in silence. Jenny's breast pushed out as she leaned back under the showerhead. Water and soap trickled down her body, over her luscious tits. It reminded me of the cum dripping down her body as she leaned back and rode my cock.

I rubbed my cock with the towel even though it was mostly dry already. Jenny stepped out of the stream of water, having rinsed out her hair. She looked at me staring at her as I rubbed myself. She didn't say anything she just turned around and bent over to get some soap. Jenny stood back up and started lathering the front of her body with soap, without turning back around.

“What about my treatment? Are you not going to help me anymore?” I asked.

Jenny turned and faced me. I was happy to see her rubbing her tits with soap as she began speaking again, “No, I will still help you, but I must set boundaries. You will have to try and relieve yourself from now on, but I will give you a nightly massage to help you sleep at night. Does that sound fair?”

I moved my towel away from my cock and placed it on my head. I dried my hair while I displayed my swollen cock to Jenny. Her eyes went straight to my cock and one hand slipped down to pussy and she ‘cleaned’ her clitoris in front of me.

“I think I understand. You don't want to think that you are taking advantage of me, regardless of how sexy I think you are, but I respect your decision.”

“Y-You, you think I'm sexy?” she stuttered, “You shouldn't think that way. I'm old enough to be your mother.”

“That just makes you even sexier,” I said under my breath.

“What?” Jenny asked.

“What else was it that you wanted to talk to me about?” I asked.

“Umm, oh! You're mother called while you were asleep,” she told me.

“What did she say?” I asked, “She left a voicemail on my phone that said she had some bad news for me. I called her back but she didn't answer.”

“I can't say what it is, she asked me not to.”

“Okay, and what exactly did she say when you told her I was sleeping?” I asked.

“She told me that it was amazing and that I should continue doing what I am doing.”

“Interesting,” I mumbled, loud enough for Jenny to hear me.

Jenny had finished washing herself and turned off the water. I dropped my wet towel on the floor and grabbed the last clean towel to hand to her when she got out. As she stepped out of the shower, I asked, “And how did you end the phone call? Did she have a message for me or anything?”

“Yes, she said that she loves you and she misses you.”

Jenny stepped out of the shower and closed the door. She held out her hand, expecting me to hand her the towel.

I kept the towel at my side, “And?” I asked.

“And, she said to give you a great big hug and a kiss for her,” Jenny said timidly.

“Oh. When were you going to do that?” I asked.

“I don't know,” she said.

“How about now?” I suggested.

“Umm, okay,” she said and held her arms out for a hug.

I looked at her dripping-wet body and wanted to fuck her right there. I put my arms up and we held each other in a nude embrace. I could feel my body getting flushed as I clung to her naked body. I held on to her for as long as I could. I felt Jenny relax from the hug trying to disengage but I continued to hold her tightly.

“What about the second part?” I asked.

Jenny closed her eyes and leaned in for a kiss. My lips met hers and I parted my lips slightly. Jenny parted her lips to match. I ran my tongue along the bottom of her upper lip. I felt Jenny's tongue move up to meet mine.

As we made out, in a naked embrace, my cock came back to life. It rose as it hardened between our legs. It managed to rub up along Jenny's inner thigh as it stiffened. Jenny parted her legs slightly to give my cock room to grow. It eventually came to rest directly against her pussy.

Jenny was kissing me with passion as she slid her hands down to my ass. She squeezed my ass cheeks slightly and then pulled me into her, causing my cock to press harder against her moist lips. Jenny breathed heavily into my mouth as her lust took over again.

Jenny probably would have impaled herself on my cock right there if she hadn't stopped herself. But instead, she broke away from the kiss and my body. I gave Jenny a disappointed smile and handed her the towel, “Here, you might need this, your pretty wet,” I said.

I saw the look of lust in Jenny's eyes and said, “I'm really looking forward to my massage tonight,” and then I turned around and walked out of the bathroom completely naked and slightly wet from Jenny's wet body pressing against me.

*

Nothing interesting happened for the rest of the day. I went to my room, put on my jeans, and lounged shirtless on the couch. Jenny and I had a nice dinner together, albeit filled with thick sexual tension.

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After dinner, Jenny announced that she was going to go to her room to prepare for bed. I knew this meant that she was going to rub lotion all over her body, an event that I didn't want to miss.

Before leaving the kitchen, Jenny filled a tea kettle with water and placed it on the stove, “When this is ready, will you please pour the hot water into a mug and bring it to my room?”

“Yes,” I said politely and willed the water to boil quickly.

I stood by the stove and looked at my phone. I logged into my Cloud Drive and pulled up a video of Jenny. I watched her as she fucked her wet pussy with one of her vibrators, in bed. I noticed that her camera work could use some help. She appeared to place her camera on the television stand across the room, in all of her videos. This provided a nice wide view of her entire room but made for a somewhat boring static video.

Just then the kettle started to whistle, snapping me out of my thoughts. I was filled with sudden excitement as I thought about what the rest of the evening had in store. I grabbed a mug and carefully poured the hot water into it.

I tried my best to calm my nerves as I made my way to Jenny's room. I kept my eyes on the mug as I walked into her room, being careful not to spill.

Jenny was sitting on her bed, applying lotion to her legs, just like I had pictured. The rest of her body was mostly covered by her closed robe. I walked around the bed to Jenny's side of the room and held out the mug. Jenny smiled at me and told me to place the mug on her nightstand.

After I set the mug down, Jenny opened her top drawer and pulled out a single tea bag, and placed it in the mug. She told me that she was going to finish putting on her lotion while the tea was brewed.

“Why don't you get more comfortable and get under the covers while you wait,” she told me.

I walked around to the other side of the bed and removed my jeans. Jenny watched me as I stripped naked and climbed into her bed. I covered myself with the blanket and my hands went straight to my cock under the covers.

I gently rubbed my cock while watching Jenny rub her hands up and down her legs. I was especially interested when she pulled her robe open between her legs and rubbed her thighs.  I couldn't see her pussy from my angle but just knowing that it was fully exposed next to me was exciting.

Jenny finished her legs and sat up. I was hoping to watch her put lotion on her breasts, but apparently, she did that already and I had missed it. She swung her feet around so they were hanging off the edge of the bed. She picked up the mug and stood up.

Jenny opened her top drawer and pulled out a spoon. She stirred the contents of the mug and then using the spoon, she squeezed all of the liquid out of the tea bag into the mug. She then placed the used tea bag and spoon back inside her drawer and closed it. I watched her as she made her way around the bed over to my side.

“This tea is made of my own special blend of herbs and other ingredients that will help you relax and put you in you in the right state of mind to receive my treatment,” she said, as she walked around the bed.

She blew into the mug attempting to cool the tea to a more drinkable temperature. Jenny stood beside me and held out the mug.

“Sit up and drink this please,” she told me, “It will help you relax. You may find yourself so relaxed that your muscles may not respond and your limbs will not want to move. If you are okay with that, please drink.”

I sat up and took the mug from her. I looked at the tea-colored water and then I looked up at her. Her robe was open slightly and I looked at the exposed portions of her tits and considered asking her for some cream. I laughed internally at my own sense of humor and then took a large sip of the tea. I was never much of a tea drinker but I figured I would do as she asked.

It tasted much better than I thought it would but it left a strange aftertaste. I took another big sip and finished half the mug. I started to put the mug down but Jenny stopped me and told me to finish it.  I took a deep breath and drank the rest of the tea in one go. I was anxious to start the massage and didn't want to delay it any longer.

“Very good,” she said, “Now roll over and lie on your stomach.”

Jenny pulled the pillows off the bed as I repositioned myself. She walked back around to her side of the bed and opened her bottom drawer. She pulled out a metal tray that held four small massage oil bottles. She walked back to my side of the bed and set the tray down on the nightstand.

Jenny pulled the blanket off my body and then poured some oil onto my back. She started rubbing it into my back and kept telling me to relax. I felt my body getting warm all over even though she was only rubbing my back. The tips of my fingers and toes began to tingle and I felt my cock throb below me.

Jenny finished my back and poured oil across my ass. I felt the oil drizzle from one cheek to the other, but I also felt it drip down my ass crack.

My arms and legs were tingling now and they felt limp. I don't think I could have moved them if I wanted to, but I didn't try.

Jenny grabbed both of my ass cheeks and squeezed them firmly. She pushed and pulled them in both directions, but mostly she was pulling them apart, exposing my anus. She then let go of one of my ass cheeks and slid her hand down my ass crack. She pulled one cheek as she kept running her fingers over my anus.

My cock was getting hard now but it was pinned down at a bad angle. I needed to adjust myself but I didn't want to disrupt Jenny. She could tell that I was uncomfortable and wanted to adjust my cock, but she made no attempts to help.

Jenny stopped rubbing my ass crack eventually, but she pressed down on my ass cheek, preventing me from adjusting my cock. With her free hand, Jenny untied her robe and pulled it off her shoulders, letting it fall to the ground.

Continuing to press down on my ass, she climbed up onto the bed and straddled the back of my legs.  Jenny then reached over to her tray to get what I assumed was more oil.

Jenny dripped more oil down my ass crack and went back to rubbing between my cheeks. She started focusing solely on my anus. She moved two of her fingers in small circles while applying a little bit of pressure. I realized that she was mimicking the motions that I had done in the shower.

“Do you like that?” Jenny asked me.

“Mmm mmm,” I moaned in agreement.

After I acknowledged that I enjoyed her touch, Jenny pushed her fingers harder against my anus until they penetrated my ass. I let out a small whimper which was only met with more pressure. Jenny started pushing and pulling her fingers in and out of my ass. I was enjoying it thoroughly but now my cock was starting to hurt.

I was whimpering and moving my hips back and forth trying to free my cock from its current position.

“What's wrong?” Jenny asked, “I thought you liked this.”

“I do,” I said, “But my cock is pinned at a bad angle and it hurts.”

“Oh, okay,” Jenny said as she removed her fingers from my ass, “Let's roll you over, and then we will continue. How does that sound?”

“That sounds good,” I said.

Jenny had to help me roll over onto my back as I could no longer feel or move my arms and legs. A loud slap sound was heard as soon as I rolled over and my freed manhood swung up and slapped my stomach.

Jenny sat over me and looked down at the source of the sound. I looked up at Jenny. She looked so sexy to me as I looked up at her, past her perky tits and hard nipples to her larger-than-life smile.

“I will continue to massage you, but you will need to take care of your erection if you want to be fully relaxed. I don't think you'll be able to sleep otherwise,” Jenny informed me.

I tried to reach for my hardness, but my arms would not budge.

“I can’t move my arms,” I said.

“The tea must be taking effect already. I will help you this time, if you want, but you will need to do this from now on. Is that okay?”

“Yes. Please help me cum,” I begged.

Jenny started massaging my body again. She ran her hands up and down my thighs, teasing me with slight touches along the edges of my scrotum and shaft. Then she began talking softly as she continued her magical touch.

“Feel my hands on your body,” she whispered, “Let everything else go. Think of something that makes you happy, something that gives you relief.”

Jenny drizzled oil from the tip of my cock all the way down to the base of my balls. She then grasped my shaft with one hand and my sack with the other. She twisted and stroked, rubbing all of the oil into my skin. My body tensed up as jolts of pleasure coursed through me.

“Relax. Don’t fight it. Let your body take away the worries of your mind.”

Jenny moved her hands upward, away from my privates. She slid her butt forward and sat on my crotch as she ran her hands up to my chest. I looked down and saw the shaft of my cock pinned to my stomach and nestled perfectly between Jenny's wet pussy lips.

I watched as Jenny's pussy slid back and forth over the top of the shaft of my cock. I could see the tip of my hard cock leaking large amounts of pre-cum onto my stomach as my cock was getting stroked by Jenny's cunt.

I wanted to keep watching but my eyes were getting too heavy to hold open. I tried to look up at Jenny's face but my eyelids wouldn't lift high enough for me to see her.

I could only see Jenny's perfectly manicured fingernails as they ran across my chest now. I tried to speak but my mouth and tongue refused to move.

I felt Jenny sliding her pussy faster and faster across my cock. I watched as she moved one hand down. She collected the pre-cum that had gathered and brought it up to her clit. She played with her nub as she continued thrusting her hips back and forth.

My eyelids grew heavier and became impossible to keep open. I allowed them to fall closed and I focused on my sense of touch.

I felt Jenny rubbing against me and I heard her moaning and breathing hard. I could feel my balls constrict as they prepared to release their contents. Jenny suddenly slowed her motions until she came to a complete stop.

I could feel her moving and shifting her body weight off of me. I felt a little disappointed thinking Jenny was done before I finished. But then, I felt her hold my erection and lift it away from my body. Next, I felt Jenny’s hot, wet pussy plunge down over my cock. She took me inside of her and didn’t stop until she sat on my hips.

Now instead of thrusting her hips back and forth, she lifted her hips up and down, riding the entire length of my shaft. I wanted to match her thrusts but I could still not move, so I just relaxed and enjoyed the ride.

I could hear her moan and beg for my cum. Jenny's pussy felt so plump and tight as it lubed and pleasured my sensitive flesh. My veins swelled into small speed bumps, giving added pleasure to Jenny as she traveled over them.

Jenny screamed, “I'm cumming!” as I erupted inside of her, sending all of my swimmers into her uterus, on their mission to seek out and fertilize her eggs.

Jenny slowly lifted off of me after catching her breath. I felt her clean my cock and pull the covers over me as I drifted off to sleep. The last thing I remember was a gentle kiss on the cheek.

To be continued...

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Written by HoldMyQuill
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