Mom's Sleeping Pillbybanana_popsicle©
I've been an insomniac just about all of my life. I actually had to repeat the sixth grade because of it. My Mother took me to see my Doctor, who had no answers other than to say that sedatives were a bad idea. I was then taken to three different specialists over the years. We tried everything. OTC sleep aides, herbal preparations, depriving myself of any sleep during normal waking hours... none of it worked. I was even put on two different anti-seizure medications, hoping they would help? The result would invariably be that I would sleep two or three hours, then wake. And once I awoke, I couldn't get back to sleep. It was determined that I would probably grow out of it.
School was a huge problem. Even though my Mother made my condition known to principals, guidance counselors and teachers; I still caught hell for falling asleep in class. All of them at one point or another downright accused my Mother for the problem. They'd insinuate that she was allowing me to stay up late. This inevitably infuriated Mom. She'd tell them how she was a single Mother holding down a job and doing everything she and my Doctors could think of to try and solve it. But still, there were the remarks.
My junior year in high school, I began having really serious problems again. It looked as if I may fail and be held back once more. I was a wreck over it, and my Mom was at her wits end. I had already been held back once, and was a year older than most of my classmates at 18. I didn't want to be a 20 year old high school grad.
"Jason," she said, "tonight if you wake up, come to bed with me. I'll pet your face and try to help you fall back asleep."
"That won't work," I said. "Nothing works, Mom."
"Hun, when you were a baby, I put you to sleep that way all the time. Give a try for me sweetie, you got nothing to lose?"
She was right. I had nothing to lose by trying.
Mom left her bedroom door open for me; she didn't want me to have to fumble for it in the dark. She also plugged in a nitelight so I wouldn't trip over anything. My clock said 3:30am. I lie there looking at it until almost 4:30, I think. Finally, I gave in and went to Mom's room. The nitelight was convenient, although I preferred total darkness. I found Mom on the other side of her big bed and gently nudged her.
"Mom, Mom!" I whispered.
She opened her eyes, I told her I couldn't sleep.
"Get in with me, hun. I've got to pee anyways." Mom dragged herself out of bed and went to the bathroom. I could hear her stream in the quiet of the night. When she came back to bed, I was lying in the middle.
"On your back, sweetie." Mom said.
I rolled over and Mom soothed my face and hair. I don't know how long it took, but I fell back to sleep. I woke up once more and nudged Mom's shoulder. She dutifully had me lie on my back while she hummed softly and caressed me to sleep.
The morning was good for a change. I wasn't so tired I couldn't function. I didn't fall asleep in school that day, and when I came home I didn't fall asleep on the couch. At dinner, Mom made another suggestion.
"Hun, why don't you just sleep in my bed from now on? That way if you wake up, you don't have to come to me. I'll be right there."
"Sure Mom, that sounds good," I said. "I think I slept good with you last night."
"Good, hun. You know I'll help you anyway I can? I couldn't stand to see you go through another year of school."
"Yeah, Mom. I've been really worried. I think I'd just up and quit before I had to do that."
"You'll do no such thing! We'll get through this. Together," she emphasized.
Mom always made me go to bed at 10pm, every night. Weekend or holiday; no matter. One Doctor recommended that I needed to be on a regular sleep schedule, and not to vary bed times. Mom always tried to go to bed when I did. She didn't want to make any noise that might disturb me. So Mom said goodnight. That was my cue. I went to my room to get ready. Now, normally, I didn't wear underwear with my pajama bottoms. Mainly because I'd jack off at night. Just being able to pull my cock through the slit in the pajamas made it easy. For sleeping with my Mom however, I thought better of that and put some briefs on underneath. When I walked into Mom's room, she still had the lamp on the night stand turned on.
"Get in bed, Jason. I'll turn out the light when you 're tucked in."
I got in the bed and pulled the sheets up to my chin. Mom turned off the light. The room was lit very dim by the nitelight.
"Mom, the light?"
"Sweetie, see if you can't get used to falling asleep with it on?"
I moaned and rolled over, facing away from Mom and the light. Mom spooned up next to me and pet my head. She hummed her little song again, and I soon drifted off to lala land.
This arrangement worked well for about a week. I woke up Mom in the middle of the night, but not because I nudged her awake. I had been kicking in my sleep. Mom woke me up in turn and had me roll over on my back.
"Jason hun, you've been kicking me all night! I hate to wake you up, but I couldn't take it anymore. Do your legs ache?"
I thought about it a minute and decided they did indeed. I was also prone to cramps, sometimes initiated by my kicking. Mom rubbed my calves and thighs. She had to actually turn around in bed next to me to do this. But it felt nice, and relieved some discomfort. So this became a regular part of Mom's cure, along with the face petting and back rubs.
Now I was starting to have yet another problem. When Mom would rub my legs, I would get hard. Not just my typical hard-on I got throughout the course of any day; the painful kind. They would last until I fell back asleep. One night, Mom had been rubbing my thighs when her arm brushed my cock.
"Oh dear," she gasped. "Hun, did I do that to you?" Her tone was more of fear and concern. None of this had any sexual overtones for either of us at this point; looking back.
I stammered a bit and then admitted, "Yes Mom."
"Oh," she exclaimed. "Does it go away?"
"Not really. Not until I fall back to sleep," I said. "It hurts though."
"It's painful?" Mom asked with concern in her voice.
"Yeah, Mom. I just wish it would go away so I could get back a sleep."
"Hun," she said. "Why don't you go in your room and relieve yourself? You'll feel better and your erection will go away."
I didn't quite no what to say. I thought she meant that I go in my room and jack off. But a little voice in my head said that couldn't be what she meant. I guess Mom could see the struggle.
"Go on dear. Go relieve yourself and come back to bed. You don't have to be embarrassed, hun. I know you do it all the time."
"Mom," I stammered.
"Jason, just go take care of yourself. I understand."
With that, Mom rolled over and closed her eyes. I lay there a minute or two thinking.
"Go Jason! Now!" Mom ordered.
I got up and went to my room. Now usually, I did this in the dark, or in the day when Mom wasn't home. If Mom wasn't home, I got out my girlie magazines and jacked off to one of them. So I decided that under the circumstances, being ordered to go jack off; I couldn't get yelled at for being caught with my magazines. I opened one, found a picture of a beautiful young girl, and jacked off. I cleaned myself up with a t-shirt laying on the floor, and put the magazine away. Then I just simply went back to bed with Mom.
"Do you feel better," she asked?
"Yeah, Mom. Lots."
"Did you clean yourself up good?"
"Yes Mom," I said in a dejected tone.
"You didn't use a t-shirt, did you?"
I didn't answer.
"Jason, get a towel from the closet and use it. I'm tired of finding stains on your shirts. I KNOW you do it Jason. Don't be sneaky about it. Just use a towel and throw it in your hamper.
"Ok, Mom," I said.
"And you don't have to hide your magazines under the mattress either. I've known about them for ages," she huffed. "Put them where you put your other magazines. I don't mind, hun."
"Night sweetie, try to get some rest."
So now; the pattern was I'd wake up, Mom would massage me, I'd get horny and leave the room to jack off. It seemed like the slightest touch from Mom would do it, yet even then I still didn't have any sexual feelings for her that I can recall. It was just a simple matter of being touched, and responding. Mom would just say little things like,
"Clean up good," or "Make sure you use a towel!" or "Wash your hands."
She never admonished me or made me to feel strange about it. In fact, one night I noticed there was a new magazine on my dresser. Mom evidently put in there on her way to bed. I was a Penthouse, just like my others. When I came back to bed, Mom even asked if I had found it.
"Yeah Mom, thanks," I said.
"Good, dear." Was her only reply.
It was sometime after this that I developed a bad habit. Instead of going back to bed with Mom after I jacked off, I'd go watch television in the living room. I had done this several nights before Mom caught me.
"Jason, what are you doing?" She asked.
"Mom," I said. "I just can't get back to sleep afterwards anymore. I get wound up and I end up out here."
This seemed to piss Mom off. I could tell she was thinking about something by that look.
"Jason, from now on when you get your erections, don't get out of bed! Just tell me. Now, come back to bed right now!"
I did as she said. She pet me for a bit and I drifted off.
The next night, I awoke. I woke up Mom, and she began petting me. It wasn't long before I had a hard-on.
"Mom, I got it again," I said.
"Pull your pajamas down, hun."
"Right here? With you?"
"Yes hun, pull them down."
I Reluctantly did as she asked, and lie there with my cock bobbing in the air. I had no idea if she was going to hit it, tie something around it? I had no idea what was up. And frankly, I was a little nervous about it to say the least. So you can imagine the shock I got when Mom wrapped her hand around my cock and began stroking me!
"Jason," she said as she jacked me off, "I think the reason you've been getting up is because you have to put physical effort into relieving yourself. I think if I relieve you instead, this won't happen."
I just nodded, looking on in shock.
"Just relax honey. Think about one of the girls in your magazines. Close your eyes, lay still and just let your tension release it's self."
I started to say something, and Mom shushed me.
"Shhhhhh," she said. "Just relax."
At one point, it started to become pretty intense for me. My legs started moving and I moaned a bit.
"Shhhhhh, be still. Don't move or make noise. Just relax."
I tried my best to be quiet and still. Finally I couldn't take it.
"Sssssssst," I hissed through my teeth. My cock jumped and spurted in Mom's hand.
"That's it," she cooed. "All better now."
Mom retrieved a towel that was folded on the nightstand. She carefully cleaned me off, and put the towel on the floor next to her side of the bed. She no sooner did that, than I was asleep. I woke up in the morning with my pajamas down to my knees. I had a horrible thought for a moment, but remembered what happened. I pulled them up, got out of bed, and started getting ready for school. I sat down for a quick breakfast with Mom.
"You sleep well last night, hun?"
"Yeah, Mom. Better than ever!"
"Good Jason. Just don't tell anybody about our little secret, ok hun?"
"Umm, no Mom. I won't."
"Good boy. Finish up and get off to the bus."
That was all that was ever said about it. In fact, I don't recall us ever discussing it further. That night, when I came to bed with Mom, I showed up as usual in my pajama bottoms.
"Hun," she said. "Why don't you just leave them off? Last night you fell asleep with them around your knees. I don't want you to get up to go pee and fall on your face."
"Ok, Mom." I pulled them down and left them on the floor at me feet. I stood at the side of Mom's bed totally naked, and didn't think a thing about it. I got in bed, and wanted to roll over to spoon with Mom, but I remembered my bare cock and stopped. It just didn't seem right.
"You aren't going to cuddle with me," Mom asked? I enjoy it when you do, you know?"
"Mom," I said with a pause. "I don't want to..."
"It's ok, hun. How about if I cuddle to you instead?"
That sounded like a much better alternative. I rolled over with my back to Mom. She playfully pat me on my ass.
"Cute hiney," she said.
"You're such a prude, for a boy."
"Just go to sleep," she laughed.
That night I awoke in a very strange way. Mom was spooned up to me, and she was slowly jacking me off. I could feel her hand in between my back and her belly. It was moving like she was scratching herself. Rather than let her know I was awake; I looked through the slits of my eys and listened.
Mom moaned a little bit. It was a very sweet sound, I thought. Then all the sudden she stopped. Her hand on my cock stopped and let it go, and her hand in ny back stopped moving.
"Jason!" She whispered.
I didn't answer. I thought it best to just pretend I was asleep. Finally after what seemed a minute, maybe two, Mom began stroking me again. The hand on her belly started back up too. It wasn't long before I was getting close to cumming. This strange new twist got me highly excited, and it must have been evident on my cock. I came in a huge spasm. I know I could feel my body jerk. I was trying terribly hard to remain still. I even moaned a bit. Mom kept right on stroking me through my orgasm. I was in heaven. Then, I heard Mom moan again, and her body jerked behind me. Her breathing was very labored, I recall. She was hissing. I, was still coming down off of my orgasm, and lost track of what I was doing.
"Thanks, Mom." I said, not remembering I was supposed to be asleep.
"Jason!" Mom shrieked. "You weren't asleep?"
Thinking fast on me feet, I said, "Mom I woke up just before I relieved myself. I just thought that I had waked up and you were helping me?
Mom was laying on her back now. I was still on my side, facing away from her. Mom was catching her breath.
"Jason, would you tell me if you were lying to me?"
I hesitated for a moment. "Mom I was awake," I said shamefully.
Mom was totally still and quiet for a long time. Finally she spoke.
"Hun, don't feel ashamed. You did what anyone would do. I'm the one that should feel ashamed. I'm sorry, hun." Mom handed me the towel and asked me to clean up.
"I don't understand, Mom." Still not knowing what had really happened.
"Jason," she said slowly, "I feel the need to relieve myself, sometimes. I needed to tonight. Do you understand?"
"I guess so. I'd read about it, but it just wasn't something I thought of you doing. Is that what your hand was doing on my back?"
"Yes, hun." Mom was sobbing now.
"Mom, don't cry," I said. I hate it when you cry?" I pet her head, and smoothed away the tears on her cheeks."
"You're such a good boy," she sobbed. "I feel terrible for taking advantage of you."
Her crying was full bore now.
"No, Mom. It's ok. I understand how you felt."
"You do," she asked carefully.
"Yes Mom, I do. You need to relieve yourself just like I do. There's nothing wrong with that, you said so yourself! I'll even help you if you want?"
Now I know that sounds strange. But I was just a kid who loved his Mother. My Mom had shown me that jacking off wasn't anything to be embarrassed about, and she helped me to feel better when I was in pain. So it just seemed like the only thing to do. Yes, I was turned on by it. I can't deny that. But don't judge me until you've been there yourself!
"That's sweet of you dear." She said nothing further for several minutes. Her sobbing was waning, and her nose wasn't plugged up anymore.
"Perhaps if you could just let me relieve myself when I have to relieve you? Would that be ok?"
"Yeah, Mom! I'd even do myself so you wouldn't have to?"
"Thanks, hun. Thanks. Let's go to sleep now."
Mom rolled over and slept on her side. I cuddled up and spooned her, hugging her to me.
"Thank you hun, she whispered."
We both fell off to sleep.
The next night was a Saturday. I'll always remember that. We were going to bed at our usual time. I walked in and took off my pajama bottoms and got into bed. Mom came in behind me. She stood at her side of the bed and removed her nightie. She was totally naked.
Now I realize that my Mom wasn't the picture of hotness. She was in her early forties, her tits sagged a bit, and she had a round ass and thick thighs. Not what I would call fat today, maybe BBW. But I found her beautiful then, and do now. Her figure hasn't changed much since.
"Am I pretty?" Mom asked.
She smiled at me. "Are you just trying to make me feel good, hun?"
"No Mom! You're very pretty. I love you."
Mom smiled at me and opened the sheets. She got into bed and turned out the lamp. The nitelight lit her body well, and I could make everything out as I lay facing her on my side. Her fat nipples; her dark bush. I was intrigued by it all.
"Would you like to touch me, hun," she asked?
I was floored, and I think Mom knew it.
"Hun, I've touched you. I know it seemed innocent at first. But I was gaining pleasure from touching you. Do you understand?"
"Yeah Mom, but..."
"And since I took advantage of you for my pleasure, I should let you have some pleasure of your own. Do you understand, Jason?"
"Yes, I think so."
"Hun, I'm saying that if touching me pleases you, go ahead."
I lie there motionless. I was afraid.
"Don't be afraid hun?"
Mom took my hand and placed it on her tit closest to me.
"You can squeeze it, hun. I know boys like that." She smiled.
Tentatively, I squeezed it. The feel of it was like a water balloon. It was the hottest thing I'd ever done up until then. Mom showed me how to massage her tits. She showed me her nipples, and how to pull and knead them. She showed me how to cup them. She had me do it to both.
"You're erect Jason," Mom said.
"Would you like me to take care of you?"
"Yes Mom. I would."
"Roll over on your back hun."
I rolled over. Reluctantly, I'll admit. I was enjoying Mom's tits. But Mom did something different. She got in between my legs, with her head close to my cock. Now mind you, I'd read about blow jobs in the magazines. But I had no idea that my Mom ever did that, or that she'd do it to me. So I guess I had a look of amazement on my face.
"Jason," she said slowly. "I'd like to relieve you differently, this time? Is that ok?"
Mom didn't wait for my answer. Her mouth swooped down onto my cock. God, did it ever feel good! She licked it from top to bottom and sucked me with loud slurping sounds. Her hands caressed my balls, which was something she'd never done before. It didn't take but a few minutes of her mouth on me before I was ready to cum. I told her I was getting close, because I certainly didn't think she wanted it in her mouth. When I told her, she removed her mouth from me in a flash, and clamped her finger and thumb around the base of my cock. It actually hurt a bit.
"Shhh, hun.!" She squeezed even harder now.
"Mom that hurts!"
"Did I stop it, she asked?"
"Your cum. Did I stop your cum?"
This was the first time I'd ever heard Mom say that. "Yeah Mom. You did. But I don't unders..."
Mom cut me off. "I want you to save it for me, hun." She let go of her death grip on my cock.
"Save it? I don't understand?"
"You'll see," was all she said. Mom got out from in between my legs and lay down on her back next to me. "Come to me hun."
"What do you..."
"I want you to fuck me, hun."
"Mom!" I exclaimed.
"Jason, get on top of me and fuck me. I know you know what that is. I've looked at your magazines."