Mom Teaches Son

That night as I thought about my mom while masturbating, I slowly slid the brush into my ass. I let out a little yelp, hoping no one heard me as I did. The brush made my ass feel pain and pleasure at the same time, with pleasure winning out.

Sticking the brush in my ass also caused my 8 inch cock to get harder, if that was even possible. Since I had never seen my mom naked, but only in panties, bra or a bikini, I couldn't visualize her naked as I slowly massaged and stroked by cock.

What I did visualize was my mom's panties riding up her ass like the woman in the parking lot. Both the lady and my mom shared similar qualities. Both have long brunette hair and long legs. I had always had a thing for long legs. My mom's breasts are smaller than that lady but they are just as firm.

As I thought about my mom's panties riding up her ass, I turned the brush and I pushed it in a little more. My body was feeling warmer by the moment and I could even feel my nipples getting hard. I used one hand to massage, stretch and stroke my cock, as I used the other to massage my balls.

I kept this up over and over, hoping I could make my orgasm wait, but after 30 minutes I shot thick globs of cum on my stomach and chest. I was so drained I didn't even have the energy to go clean myself up, but rather just fell asleep with the brush still in my ass.

When I awoke the next morning, my ass was burning and very sore. I realized that I had left the brush in there all night. When I pulled it out, I felt my ass scream in agony. I could stick 3 fingers in my ass without any resistance.

I just wanted to rest, take a shower and let the water massage my ass. Just as I was about to do just that, I remembered my dad telling me the night before that he wanted me to cut the grass and have it done before he got home.

Since it was already 9am, I didn't want to have to take 2 showers. I put on some blue jean shorts without any underwear. I didn't want sweaty underwear rubbing and sticking to my sore ass. As I was putting on my t-shirt I noticed I still had dried cum splattered on my belly and chest. Knowing I would be sweating and showering soon, I just left it there. I did, however, wipe the brush off, hid it and stripped my sheets off, putting them in the dirty basket.

I quickly ate a bowl of cereal, and started for the door. My mom saw me walking funny and asked if I was ok. Even though I was walking bowlegged and felt like a corn cob had been shoved up my ass, I told her I was fine. She said she would have lunch ready for me when I was done.

For the next 2 1/2 hours I cut the lot, most with the riding lawn mower some with the push mower. I had to switch up because if I sat to long on the riding lawn mower my ass would start hurting. Even walking caused discomfort, especially when the sweat was seeping down between my ass checks. The sweat would hit my raw hole and burn.

When I got in, my mother was true to her word. Lunch was ready for me. I went in my bedroom to change shirts, when I got there my bed had clean sheets and was made up. I was thinking that I hoped my mom didn't smell the musky sex odor from the night before.

As I was putting my shirt on, I noticed the dried cum on me and I smiled. Then a scary thought came to my mind. I was wondering if my mom had found the brush. In a panic, I went to the hiding place and looked. It was still there, wrapped up like I had left it. After a heavy sigh of relief, I put the brush back in its place.

When I returned to the kitchen, my mom was making my sandwich. I asked where sis was and she told me shopping with a friend. I noticed that she had changed from her night robe into a pair of tight, short shorts and a skin tight white t-shirt.

The t-shirt was so tight; I could see her entire bra like she wasn't even wearing a shirt. Upon looking at her, my cock started getting hard. I tried not to stare so my cock wouldn't get hard and become uncomfortable in the confines of my shorts. For the most part, this worked. That and my mom sat on the other side of the counter blocking my view from her.

After I had eaten about my half my sandwich, my mom said she was going to make a cake later and proceeded to start getting everything out of the cabinets. When she reached up high to retrieve a pan, her shorts rode up exposing her ass cheeks from underneath her shorts. The shorts were also riding up her crotch giving me a great view.

My cock grew instantly hard and since I had no underwear on, it was sticking out my shorts leg. I knew I had to get out of there before my mom noticed. As she was still reaching, I left my uneaten sandwich, told her I was going to shower and took off.

After getting in the shower all I could think about was my mom's ass and crotch. My cock was rigid but I didn't stroke it. Instead I used the pulsating shower massage to stimulate my cock and massage my sore ass.

I also squirted off the left over cum from last night, slowly letting it run down my body. Between thinking about my mom and letting the pulsating water massage my cock and ass, I knew I needed to jerk-off but I knew I could wait. I stayed in there until the hot water ran out and my cock went soft. I felt refreshed and my ass wasn't burning or sore.

I dried off and wrapped a towel around my waist. As I stepped out into the hallway to go to my room, my mother called me from her bedroom on the other side of the house and asked me to come there. I said back to her that I only had a towel on and could she wait. She said it would only take a moment.

When I reach her door, I only stuck my head in so she wouldn't see me in the towel. When I looked, my mom was standing there in a very skimpy white string bikini. She said she bought it yesterday but she didn't want to show it to me while my sister was home.

She started turning around, modeling it for me. When she turned, her ass fit perfectly, making it look even firmer. When facing me, I could see the folds of her pussy straining at the material. Her tits were firmly being pressed by the top, allowing her nipples to show ever so lightly. My cock was getting hard fast and was pressing against the door frame.

She asked me if I like it and if I thought it was too skimpy. I stuttered no and said she looked very hot and sexy. She blushed at that and told me that I always knew the right things to say.

Before I could move, she picked up a towel and suntan lotion and walked by me, giving me a kiss on the cheek as she did. She said she would be tanning by the pool if I needed her.

After I heard the door closed, I rushed back to my room and shut the door. As soon as I did, I dropped my towel and started stroking my cock. Luckily for me, my back window faces the pool. I went straight to the window, making sure my mom couldn't see me.

As I watched her, she bent over to put a towel on the lounge chair. Her ass was straining at her bottom and I could make out everything. Her ass was firm and tight. Without even thinking, while I was stroking myself, my other hand was fingering my ass.

My mom sat down and started rubbing suntan lotion everywhere. As she lotion her legs, I almost exploded so I stopped and watched. I continued fingering my ass though. My mom lay down on her stomach, untied the string to the top, along with the strings on both sides of her bottom and spread her legs slightly. I wasn't at the best angle to see straight up between her legs but I saw enough to get my heart racing and my cock wanting attention.

Even though my ass wasn't as sore as it was, I wanted the brush up my ass while I masturbated thinking of my mom. I hurriedly retrieved the brush and as I was standing there watching my mom sunbathing, I bent over the window sill and stuck it in my ass.

My cock jerked up and down frantically. I took a few more strokes as I watched my mom, and then went to my bed. I got on all fours, my ass in the air, my shoulders pushed into the bed, along with my face buried in my pillow to muffle my moans. After adjusting the brush, I balanced myself so I could reach my cock and start my stroking.

I was in pure delight, my ass spread and enjoying the sensation while I slowly but methodically stroked my cock. My mine racing with the thought of my mom, switching visions from her ass checks hanging out her shorts, to the skimpy bikini, to her untying the strings, and to her rubbing lotion over her body.

My mind and body were reacting to the pleasure of her image. Every time I would feel the buildup I stopped, adjusted the brush, and then started again. My mind was a blur, my body soaked in pleasure. I was moaning loudly into my pillow as I couldn't hold the buildup much longer.

Just as I was about to explode, I heard, "whatcha you doing little boy?" My mind was in a fog and it took me a minute to recognize that the voice was my mom's. I thought I had locked the door but in my state of mine, I had forgotten.

I started to say something, to move and cover up but my mom cut me off. "You are in big trouble little boy and you stay exactly like you are or else." What 'or else' could be I didn't know and didn't want to find out. And what was up with her calling me little boy?

Before I could think of an excuse or ponder anything, my mom said, "I guess we found your sister's brush" and yanked it out. I let out another yelp as my ass felt ripped. "So, you like sticking things up your ass?" I didn't answer so she smacked the brush on my ass cheek. I yelped louder as I buried my face deeper in my pillow.

"I asked you a question little boy and I want an answer." Barely audible, I said yes. "What else have you stuck up there?" Nothing mom. Another smack on the ass. "I said what little boy?" Some candles, coke bottle, little things. "Why your sister's brush?" "You haven't been thinking about her while playing with yourself?"

My sister was pretty but I never thought of her that way, even though I did get a hard-on a few times when she was in her bikini or skimpy clothes. No ma'am, I haven't. Another smack, another yelp. "You're not lying to me are you little boy?" No ma'am. "So, why your sister's brush?" Because of the rubber spikes. I knew I was in trouble already so I added that the spikes stimulated my ass better than anything else.

"Hmmm, I can see why." "What got you started wanting to stick objects up your ass anyway?" There was no way I was going to tell her about my cousin. I lied and said one day I was jerking off and I was wiping sweat from my ass crack and my finger slipped in and it felt good. After that I kept exploring and knew that I would like having something else in my ass.

"How old were you when you first starting wanking and putting object's up your ass?" I told her just last year. "Last year!!??" She was taken aback.

"And what or who do you think about when you do these things?" I like looking at dad's playboy books when I do it. "Hmmm, and who do you think of?" A few girls at school and a couple of teachers.

"Anyone else?" No. Another smack. "I asked anyone else little boy?" Since I knew I was totally in trouble anyway, I blurted out, you mom. I waited for another smack but none was coming.

"Since you have never seen me naked, what do you think about me when you masturbate?" I didn't know how to answer so I gave her some examples. When you model for me and I see you in your bra and panties, when you wear skimpy clothes like your shorts today, when you get dressed up to go out, in your bikini... "Ok, Ok, I get the picture."

"I want you to turn on your back." Realizing I still had a hard-on I was reluctant. Another smack on my ass. "I said on your back little boy!" I slowly turned over and laid flat on my back. My cock was still stiff and sticking straight up.

"I see you have your father's genes." "The girls are going to love you." "Ahh, that smell." "That's the same smell from the other day in the car." "You dirty little boy."

"Now you just lay there until I get back and you better not move or your dad will hear about this." "And keep that thing hard!" As she was walking away from me, her bikini bottom was pushing into her crack exposing her ass cheeks.

I was scared shitless thinking of my dad hearing about this. I kept my cock up by massaging my balls and squeezing my head. After about 5 minutes, I heard my mom coming down the hall so I stopped massaging. My mom came in, shut the door behind her and locked it. She was wearing the same shorts and top from earlier and also carrying some sort of big make-up bag.

When she got close to my bed she put the bag on the floor and set next to me. Then I realized she had no bra on and I could see her nipples through the top. They were beautiful and I couldn't stop staring.

"You like what you see little boy?" I didn't know why she was still calling me little boy but I was starting to like it. Yes ma'am, I do. "I'm glad you do." "Who were you thinking about when I caught you?" You mom. She just smiled.

"Your dad used to masturbate in front of me while I watched." "He hasn't done that in a long time and I missed that." "I want you to masturbate for me as I watch." Mom, I can't do that. "Then I guess I will have to tell your dad about all this." I knew I didn't have a choice so I said ok. She said when I was about to cum, that I was to stop and stand up beside the bed.

To get me going, she placed my hand on my cock and guided me through the first few strokes. She then stood up, turned around, bent over and grabbed her ankles. I could tell she wasn't wearing any panties and as she wiggled her ass, my body took over. I started stroking with deep long strokes.

After giving me that show, she stood up, pulled my foot stool over, sat and began opening and closing her legs. Every time she opened them, I could see her a little more. It didn't take me long and I was ready to explode and told her so. She made me stop and stand up next to the bed. She arranged the stool so she was directly in front of me. She told me to shoot my cum on her shirt, not her face.

I started stroking like a mad man and in just 30 seconds I was shooting cum on my mom's shirt. There were gobs of it. She just laughed and said like father like son. Then she rubbed the cum into her shirt. She rubbed most of it on her tits and nipples. I could see the cum soaking through her shirt and her nipples getting hard.

"Now that we finished that part it's time to move on." "You are not the only one with secrets little boy." With that said she put her bag up on the bed and opened it. Inside were a number of dildos in all shapes and sizes. One was huge.

She pulled one out that looked like a penis, about as long as mine and ribbed. She told me to get on the bed on my hands and knees. I needed no prompting. When I was in place, I heard her squirt something on the penis. I asked what and she said K-Y jelly.

She inserted the ribbed penis in me a couple of inches. My cock was getting hard again. She fucked my ass with it for about 10 minutes, in and out, around and around. I was in bliss. During that time, she kept asking me if I liked it little boy. She made me say it out loud, yes, I like it, don't stop.

But after 10 minutes, she did stop. She left it in, got up, grabbed her bag and said for me to soak my sister's brush and give it back to her. She also told me to practice with my new toy; she wanted me to be able to handle all of it.

Also, she told me when I masturbated that I was to think of her and only her. She said she would give me something more to think about later. As she was leaving, she turned and said that I better give her a longer show next time and then she left.

Next time???

By the time my mom left my room, it was getting late afternoon. I so wanted to play with the new toy my mom just gave me for a lot longer but I didn't have time. My thoughts were going a mile a minute as I thought about what had happened. I was still on my hands and knees, the new penis still a couple inches in my ass, stretching it but no pain, only pleasure. What had just happen?

Me jerking-off, my sister's brush up my ass, my mom's image in her skimpy bikini, the build-up of heat from my groin, the sudden realization that my mom was in my room and caught me masturbating, her ripping my sister's brush from my ass, the pain of it being ripped out, my mom questioning me, her spanking me with the brush while calling me little boy, her making me lay on my back so she could she my cock, her comments about my dad and me, her going to her room and returning with the bag, her nipples for me to see, her ordering me to jack-off for her, her making me to shoot my load onto her shirt, my cum soaking in on her tits, her telling me I wasn't the only one with secrets, her telling me to get on my hands and knees, her fucking my ass with it, her telling me to think of no one but her when I jack-off, her telling me 'the next time'...

Too much to comprehend, my head was hurting. The "her" that did all that.....was my mom...

Even with all the thoughts going through my head, I still felt very thrill, excited and horny. I noticed that my cock was hard and rigid, the head swollen to a dark purple color. I was turned on and I wanted more. I slowly stroked my cock, pushing the skin over the swollen head, kneading and squeezing my head between my fingers. All I could think about was my mom...she didn't have to tell me...my thoughts could not think about anyone else.

Questions were entering my mind as I enjoyed every long stroke. What secrets? What next time? My mind drifted in and out as I felt the build-up of cum in my groin. I took the "penis" out of my ass, got on my back and stretched, pulled and stroked my cock towards my face. Did I want to shoot cum into my mom's mouth? Did my mom want me to? Too many questions. When I couldn't hold back any longer, cum that had been building up shot onto my chest and face, with a good amount going in my mouth. I didn't even think what I was doing when I swallowed, and took what was on my chest and also swallowed it while licking my fingers.

I was sweaty and had the smell of sex on me so I took another quick shower. I took my sis's brush in with me and gave it a good scrubbing, since I knew I wasn't going to need it anymore. I tossed the brush on my sis bed as I made my way to my bedroom. When I reached the bedroom, I noticed that my sheets were stripped again, with new ones to replace them. I also noticed a folded up piece of paper lying on my bed. I took the note, unfolded, and read. The note read, "Checked your hotmail account and read emails from mominschool@gpn.com."

I hurried and got dressed and went to the computer room. I could hear my mom and sis talking in the kitchen so I knew I would have privacy for a few minutes. I opened my mail and saw the emails. When opening the first, there were three web links on it and a short note that said, "Before practicing, look at links."

I clicked on the first link...it was a page describing what could happen if anal penetration was done wrong. The second and third link showed the proper way of having anal intercourse or using toys for anal sex. As I read over the first link again, it got me scared and I didn't realize what could happen if done wrong. As I read over the second and third link again, I felt a little better because I knew if I did it right, I would be okay and would enjoy immense pleasure. In fact, the more I read, the more I liked and the hornier I was becoming. My dick was already starting to get hard when I opened the second email.

Another short note, this one saying: "Will be in tonight to tuck you in little boy." "Have a surprise for you." "Have your cock ready for me little boy or you will be punished." "Also, check your email every morning."

My dick grew larger and more erect as I read the note over and over. My dick was straining at my jeans and was hurting. Just then, I heard my dad come into the house. I closed the emails and logged out. My dick was still hard as I walked into the kitchen.