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A couple weeks ago my Mom sent me over to Jimmy Holloway's house. I was in my room jerking off when she yelledup to me from downstairs.I’d found a new dirty magazine in Dad's sock drawer. It had pictures of hot women in tight leather outfits playing wicked games with naked guys. The women were hurting the men. I found the first magazine like that six months ago. There were seven of them. I’ve memorized all the pictures in all of them. AndI've grown to really, really like the pictures of women using whips and paddles and big fake penis things strapped to their waists to torment and hurt guys. I don't know why I like it. I just do. It turns me on. Now I can get a boner just thinking about getting paddled by a cruel woman.My Mom can be cruel. It used to bother me. Now I like it.
So I ignored Mom at first when she called me. I just kept jacking off. I knew if I irritate Mom enough she’d spank me. Mommy’s always spanked me butrecently she’s been spanking me more often and much harder than she ever has. She’s been leaving bruises and marks on my bottom that take more than a week to heal. It’s odd too cause Mom started spanking me every day and harder the same time I found that first dirty Femdom magazine in Dad’s dresser. Mom’s gotten good at really hurting me now when she puts me over her lap. Most times now she’ll use a wooden ruler on my butt. Or this leather p[addle she bought just to spank me.
Ever since I started looking at Dad’s dirty magazines I’ve decided I like it when Mommy spanks me. She doesn’t do it often as I’d like her to though.She spanks me maybe nine or ten times a week. And she doesn’t always paddle me hard enough to satisfy this strange need I have. But lately she’s been making me pull my jeans down so I’m just in my undies. That makes me get a boner. And I like getting a boner in front of a woman who’s about to spank me.Even if she is my Mom.
I wear white jockey shorts. I know my Mom can see I have an erection when she spanks me. She stares at my crotch sometimes when I stand in front of her in just my underpants. She’d leer at me and lick her lips and slap her leather whip against her hand and start to giggle. That makes me even harder. So soon after Mom started making me pull my pants down for my spankings I dug out some old underwear that’s too small for me. If I can I try and have that on when I do something wrong so Mom will want to spank me. That way when I’m standing in front of Mom and I get a huge boner, which I do all the time now, well, let’s just say the big hard lump in my crotch is impossible to miss.
Sometimes when I’m really hard the head of my cock even pokes up over the elastic waistband. It seems weird and slightly dirty that I get such a thrill out of standing in front of my own Mommy with my stiff cock headpoking out the top of my undies but I do. Standing there so vulnerable and almost naked makes me feel like I imagine those men in Dad’s magazines feel as they stand in front of a leather clad Dominatrix holding a nasty whip in her hands. I wish Mommy had a bigger whip she could use on me. But at least she snickers and leers at me when my dick pokes out of my undies. I like that. She must like it too cause she laughs a lot now when she spanks me.And she always makes me pull my pants off too. She even manages to get my undies to slid down so most of my cock is exposed when she puts me over her lap. Somehow it doesn’t seem so dirty and perverted getting hard in front of Mommy when she laughs at me like that.
Anyway, I ignored my Mom calling me at first because I wanted her irritated enough to spank me good. And also cause I was so close to shooting off. I was looking at one of my favorite series of photos in one of Dad’s magazines. The woman in the pictures was practically killing the man she was torturing! She had her legs wrapped tight around his neck and she was pounding his balls with her fist. It was hot!
But Mom yelled up at me again and I could tell she was getting a little pissed. So I started to tuck my super stiff and still throbbing dick back in my shorts. I sat looking at the pictures and I just had to turn the page. The last photo takes up the whole page. The woman’s laughing as she’s ramming this giant wooden pole up the guy’s rear end. I almost always shoot off when I turn to that page. And I was about to shoot a huge load of cum when I heard Mom start up the steps. I reluctantly closed the magazine, slipped it under my pillow and went to see what Mommy wanted. She’d never exactly caught me jacking off before even though I did it three or four times a day. I wasn’t sure I wanted my Mom to see me playing with myself. I have a pretty big dick compared to other boys at school but I’m nowhere near as big as some of the men in Dad’s magazines. I mean, I’m only six teen and I have a ten and a half inch cock when I’m hard but guys in Dad’s magazines are much bigger than me. And I’ve seen Dad get out of the shower and I know he’s at least an inch and a half bigger than me. I don’t want Mommy to be disappointed in how little my cock was compared to a real man.
Even so I made sure my boner was showing before I went downstairs. I even pulled my undershorts down some so half of my erection was poking out. Over time Mom and I have sort of developed this little game we play. At least I think she’s playing the same game I am. To me it seems she pretends not to notice I have a hard-on as I lay across her lap for my spanking. Even when I make sure I grind my boner against her thigh. The harder she spanks me the more aroused I get. And the more I push my cock into Mommy’s thigh the harder she seems to spanks me. And the more she laughs and tells me what a lovely big boy I’m getting to be.
I had an orgasm yesterday while Mommy was spanking me. She had to know. I shuddered and moaned and pushed my dick into her thigh over and over again. But she didn’t say anything. She did put her finger on the cum soaked wet spot in the front of my undies after. My limp cock was right under the wet spot and when Mommy touched that spot I shuddered again and got super hard real fast and almost had another orgasm. Mommy laughed, gave me a really hard slap on my behind and told me to go cleanup for supper. Then she pulled me close and slipped two fingers under my underpants and touched my cock and rubbed her fingers up and down the length of my dick four or five times and asked if I needed help getting cleaned up. I nodded yes.
Mommy slapped me half a dozen times on my face and told me to use my words because I was a big boy. She hit me really hard. It stung. I got tears in my eyes and that seemed to disgust Mommy. She slapped me about ten more times, each slap harder than the one before. I was sobbing when she finished. She pulled me close. I was shaking and Mommy hugged me and she slipped her leg between my legs and I felt her thigh move and my Mom started rubbing my cock with her leg and I got real hard but it didn’t help me stop shaking so bad. If anything I trembled even more.
Mommy giggled and her body kind of quivered and she moaned and for some reason I shot off again. Mom put her lips to my ear and whispered to me I was such a big boy. She bit my ear then. It hurt! Mommy giggled again. Andput her hand on my jockey shorts andwrapped her hand around my boner and squeezed it in a really, really nice way. I got a huge boner again and I started to pump my hips it felt so good to have Mommy’s hand stoking my penis like that. That’s when I shot off again.
Mom laughed again, used her thumb and forefinger to kind of milk my dick so all my jism squirted out and when the wet spot on my undies got bigger she smiled and said big boys can clean themselves. That’s when she let her hand slip down to my balls and she kind of cradled them in her fingers then squeezed them real hard. It hurt something awful. I tried to pull away but Mommy held on tight. And squeezed them even harder. She got done squeezing them and wrapped her hand around my scrotum so my balls were all scrunched up and the skin over them was real tight and my testicles showed through my underpants like two tennis balls.
Mommy started to punch my balls. She hit them hard! Really hard. My knees buckled and I felt sick to my stomach and I wanted her to stop. But she didn’t stop. Instead she whispered to me that she’d stop when I made my boy parts behave. I said I didn’t understand. So Mommy stopped punching my balls and put her hand back on my cock. I had a nice erection before she started to fondle my dick again. Even though she was killing me punching me in the balls. When her fingers wrapped around my dick I get even harder. Mommy laughed and said I needed to learn how to control this boy part now that I was a big boy. I was pushing my hips in and out in a frenzy. I needed to shoot off so bad. Mommy let go of my cock though before I could come. And started to pound on my balls again. She didn’t stop until I’d gone limp. She must have slammed her fist into my balls a hundred times before that happened.
Mommy kissed me then. On the lips. And said she wouldn’t tell Daddy about how nasty and bad I’d been in front of her. She said Daddy would be so disappointed to find out his son couldn’t control his boy parts. Then she said a strange thing. She said she was glad I got so excited by pain. She said that’s what she’d hoped would happen to me when she left those magazines in Dad’s sock drawer for me to find. Mommy giggled when she said that and punched me in the balls one last time. She giggled that now I was ready for Ms. Holloway. When she said that I got even harder. Ms. Holloway is real cruel and wicked to her son Tommy. I just can’t resist cruel women anymore. Mommy could see I’d gotten harder. So she ran her fingers up and down my long hard dick and giggled some more.
She kissed me then anddismissed me. Dismissed may seem like a strange word to use but it’s what I felt she did. She dismissed me. She said “You can go now. Go clean up the mess you made. Then I want you to wash my panties my hand. In cold water.”She left me standing there with my erection sticking out of my underwear and walked away. Like I was suddenly invisible.Or unimportant.
I was disappointed of course. Even though she’d given my boner a nice squeeze when she dismissed me. I was a little hurt by her attitude. She made me feel almost worthless. But I went into the bathroom. And I jacked off again before I wiped my cum covered dick and stomach off and washed up and changed undies.While I jerked off I thought about how nice it would have been if Mommy had decided to whip me until my butt was a bloody mess instead of sending me away. That’s what the women in those magazines did. The punched and kicked men in the balls then whipped them and then had sex with them. I thought about that happening with me and Mommy. I thought it’d be wonderful to have Mommy fuck me.I had the most powerful orgasms ever thinking about all that.
I was remembering what Mom did to me yesterday when she called to methis morning while I was jacking off. So I was intentionally slow to respond to Mom’s shout from downstairs when she wanted me to go to Jimmy’s. I was hoping she’d play with my boner again like she had yesterday. I wanted Mommy to hurt me real bad then have sex with me. I thought that’s what happened when women fucked boys like me. In the magazines women like that always get irritated with their men and then hurt them pretty bad and then they fuck them. So I thought if Mommy was irritated with me maybe she’d whip me and bust my balls some and then we could have sex. I even said I was busy with something important so that’s why I’d taken so long to answer her call. I said I probably needed a long hard spanking. But Mom had other ideas. She stood at the bottom of the stairs and she’d just talked with Mrs. Holloway and our neighbor wanted to know if I would come over to play with Jimmy. I didn't want to go.
If Mommy wasn’t going to make me pull my pants down so she could spank me so it hurt then I wanted to look at the photos of hot women ramming those fake cocks down men's throats. And up their butts.I wanted to stay home and look at pictures of women tormenting men. Then I wanted to do somethingnaughty that would make my Mommy pull my pants down so she could spank me really hard and then rub my boner. I'm fifteen. I'm still a virgin. I don't have a girlfriend. I don't really know anything about sex. But I know what I like. And I like cruel women doing wicked things to men. I like getting spanked hard by Mommy and having her touch my boner. I like that a lot. At least I thought I did. And I knew I liked the idea of a cruel woman tormenting me a lot more than I liked the idea of spending an afternoon with stupid Jimmy Holloway.
I knew Jimmy Holloway but we weren’t really friends. I didn’t like him much. Nobody did. He acts weird. He's kind of slow. Like he's brain damaged or something.But his Mom’s is really pretty and sexy and she slaps Jimmy a lot and I like seeing that. I only hang out with Jimmy so I can watch when his unbelievably sexy Mom decided to slap him around real good. SoI told Mom I’d go over to Jimmy’s.Why not I thought. If Mommy wasn’t going to spank me then maybe I could get Mrs. Holloway to spank me. Or at least slap me. She’d done that a couple of times. And for no good reason that I could tell. Of course she hit and kicked and slapped Jimmy all the time. Even in front of me. So I thought maybe she’d be willing to treat me like those evil women in Dad’s magazine treated their men.
Jimmy has the hottest Mom in the city. She has these wonderfully full and luscious boobs that I love to stare at. And she wears skimpy clothes all the time so sometimes I can see her nipples outlined behind her thin cotton tee shirts. Jimmy’s Mom and my Mom had become close friends the last few months. I’d heard them talking about how much trouble it was to raise a teenaged boy one day a few weeks ago. Mrs. Holloway had said something about how often she had to discipline Jimmy. And how the spankings and other techniques she used were having a positive effect on Jimmy’s behavior. Mom had laughed and said maybe she should try some of those methods on me. It was right after that conversation Mom had with Mrs. Holloway that she made me put Dad’s socks away. That’s when I first found the dirty magazines in Dad’s sock drawer. And soon after that Mom started to spank me regularly. And then a week and a half ago she started slipping her hand down my undies when I got a boner.
I knew Jimmy’s Mom did things like that to him too. I’d seen Mrs. Holloway spank Jimmy. And slap him. She beat him something awful. Much harder than Mom beat me. That scared me some but I was also envious of Jimmy some too. His Mom let him swim in his pool naked. While she was out sunning herself and looking at her boy. Jimmy always got a boner when he swam naked in front of his Mommy. At first it was really weird. But then I found those magazines, and Mommy started to spank me, and I got a boner in front of my Mom and that was kind of nice in a way. So I decided maybe Jimmy was lucky he got to be naked in front of his Mom with his big hard dick.
It’s confusing being fifteen and always thinking about sex and women and what the can do to you. Spending an afternoon with creepy Jimmy would be worth it if I could get naked in from of Ms. Holloway and get her to spank me like I’d seen her spank Jimmy. She spanked so hard. It’d be especially good if she spanked me while she was in one of her skimpy little bikinis. She kind of reminds me of the women in Daddy's dirty magazines.Mrs. Holloway not only has big boobs, she has strong looking legs that seem to go on forever. She doesn’t seem embarrassed at all about slapping and spanking Jimmy in front of me or even touching her son between his legs while I’m around.
I’d even seen her punch Jimmy in the crotch more than once. Now I always get hard when I saw that. I tried to do things that would encourage her to slap and punch and spank meas hard as she did Jimmy. But she hadn’t done that yet. She looked like she wanted to last time I was over there delivering a package that got sent to our house by mistake. But she didn’t. I left disappointed which was really weird, being disappointed because I hadn’t got slapped or spanked or slammed in the balls. Sometimes I wondered if I was turning into a pervert. But I’d discovered that getting hard looking at cruel woman hurting men felt so good I didn’t care if I was a freak. I just loved getting boners that hard.
So I might have gone over to Jimmy’s even if Mom hadn’t insisted I go. Because of his Mom and how hot she was and how cruel she could be. I liked that. But I’d never have gone just to spend time with just to be with Jimmy. I’d done that a few times when his Mom wasn’t there. It was boring and stupid and a waste of time.
But that seemed to be kind of what Mom wanted me to do. I asked my Mom if Ms. Holloway was going to be there. Mommy laughed. And slapped me half a dozen times. She said that was none of my concern.
Then Mommy kneed me in the crotch. She only caught my balls a little. It hurt but not as bad as when she punched me in the nuts yesterday. Even so I doubled over in pain. Mommy grabbed a handful of my hair and yanked my head back until my neck was stretched and I was looking up at her. She was laughing again. And only half serious it seemed when she said it didn’t matter why she wanted me to do something, only that she wanted it. I should behave myself and do what she told me to do. Or what Ms. Holloway told me to do she giggled at the end.
Mommy looked at me real serious then. And said I could learn some things from the Holloway boy. Mom said she liked how polite and well-mannered he was. She especially liked how Jimmy treated his Mommy with respect. Mommy said she hoped Mrs. Holloway would teach me to be like Jimmy. My Mom was going on and on about how I should be more like that creepy boy and it was driving me crazy. So I went right then. It was easier that arguing. Plus it was hot outside, at least ninety five and if Mrs. Holloway was home she’d be out by the pool and she'd probably be half naked in some tight little bikini. At least I hoped so.
Mom stood right by me as I slipped on shorts over my underpants. I started to put on a shirt but Mommy said I wouldn’t need it. Then she pulled me to her by slipping her finger under my shorts. I got hard immediately. Mommy felt my boner I know. She unzipped my shorts and told me to take off my undies. She said I would need them today. I did what she told me too. And stood in front of my Mom almost naked, my cock poking straight, pulsing and vibrating it was so hard. Mommy ran her finger from the base of my dick to the end until she was pushing the sharp tip of her fingernail down my pee hole. I shuddered in pain. And in desire. I moaned. And I said ‘Please. Please Mommy.”
“Please what Michael. What does my little boy want me to do?”
“Play with it Mommy. Make it hard. Make it come Mommy. Please. Please play with my cock.”
She laughed then. And stuck her sharp fingernail way down my pee hole and grabbed my dick with her other hand and held my huge boner still while she twisted her finger around inside my cock. It felt like she was reaming out the inside of my cock the way she did with the knife used to core apples for the lunches she used to make for me when I was little. She pushed her finger way down the inside of my cock. I bucked and twisted but Mom had a really tight grip on my dick and I couldn’t get away. It felt like she was cutting my dick in two. I looked down at my crotch expecting to see Mommy had sliced open my cock the way she did bananas when she made banana splits.
But my cock was OK. It was still in one piece. It hurt like hell. Andit was oozing cum. As much as it hurt, as much as I was scared, I was more turned on. That made me feel good some but it also made me feel dirty and worthless and perverted. But I stayed hard anyway. And Mom keep twisting her long sharp fingernail inside my dick while using her other hand to jerk me off and she was laughing and calling me her slutty little boy and giggling about how Ms. Holloway had been right and abusing your own son really was the best way to have fun with a boy.
Mom kissed me then. Usually it’s just a peck on the cheek. This kiss started that way but then I felt Mommy’s tongue licking the corner of my mouth and then she was pushing her tongue between my lips and I liked the way it felt so I kissed Mommy back like that and it made me super, super hard. Mommy broke off the kiss, put her hand over my crotch and felt my cock real good for about half a minute. It still hurt from when she’d reamed it out with her fingernail. Mom felt me flinch. She laughed and whispered in my ear that next time she was going to cram two fingernails down my dick. That got her laughing real hard. Finally she stopped giggling long enough to look at me real long and said it was time for me to go.
“Don’t put your tightywhities back on Michael. You won’t need them anymore today. And leave the zipper on your shorts down too. You’ll just have to try and keep that cock of yours tucked in when you go over to Jimmy’s.”
Mommy took my shirt off me too. She used it to wipe the end of my dick and my leg. I had cum all over me.
After Mommy cleaned my cum off me she told me to open my shirt. She wanted to pre-soak it she said. When I opened my mouth Mom stuffed my shirt in it. She pushed it all in until it was jammed in my throat and I could barely breath. She left it there, grabbed my dick and hustled me downstairs. I was gagging and getting dizzy and halfway down I tripped. Mom kind of pushed me too I think. Anyway, I fell and landed on the hardwood floor with a thud. Mommy laughed. And grabbed me by the hair, pulled me up and yanked my shirt out of my mouth.
“You need to get next door now Michael. But first, take some more of your special vitamins for Mommy baby. You look tired.”
Mommy was playing with my dick when she said that. I was aroused and hard but not nearly as hard as I had been. My dick hurt for one thing. And I’d ejaculated half a dozen times since Mom called to me an hour and a half ago. I was tired. All over. But Mom’s special vitamins weren’t going to help with that. All they’d do is make my dick big. Her special vitamins were Viagra. She’s had me on the stuff for years. I think that’s why my cock is so big. And why I get and stay hard so easily. Mom never says she’s giving me boner pills. She still calls them vitamins. But I’ve seen the ads in Dad’s magazine. I know what those funny shaped purple pills are.
She made me take three pills. I knew from past experience I’d be hard for a day and a half and my cock would get so fat and stiff it’d hurt. But I didn’t complain. Mom’s got me trained with the pills. I don’t even need water anymore. She just pops them in my mouth, flicks my throat with her finger a few times and I swallow. I was frightened when I first realized my Mom was making me take boner pills. But after a few days looking at those magazines I decided real quick that it’s neat having a Mom who likes giving her boy pills to make his cock big and hard. I know Mommy’s going to have sex with me soon. I just have to be good for her and obey her until it’s time.
Mom was looking at me funny when I finished downing the pills. I’d started to fondle myself without even thinking about it. She playfully slapped my hand away, tucked my throbbing and quickly growing dick back in my shorts and kissed me on the cheek as she put hand on my back and gently moved me towards thedoor.
“Have a good time with Jimmy hon. Stay as long as you want. And don’t give Jimmy’s Mom any trouble honey ”she smiled.
Mommy was giggling when she pushed ne out the kitchen door. She told me to take the back way to the Holloway’s. Jimmy lives four house away and if I go through the woods I can get there quick. And nobody sees me.
When I got to the Holloway’s yard and let myself in by the back gate. Right away I heard Jimmy grunting and crying. I hid behind a bush and peeked around the corner. I saw Jimmy and Mrs. Holloway by the pool. Jimmy was in the water. His Mom was sitting on the side of the pool. Her bikini top was way too small for her delightfully large boobs. Her wonderfully tan and round tits were practically spilling out of the skimpy white top. Every once in a while she’d move just so and her nipples would show some. At least I think they did. Or I hoped they did. Anyway, I was staring so intently at Ms. Holloway's boobs that at first I didn't really see what Jimmy’s Mom was doing to her son.
Jimmy had his back to the edge of the pool. He was backed up against his Mom. She was sitting on the deck by the edge. And she had one leg wrapped around Jimmy's neck and she was strangling him! I mean for real! That’s why he was grunting like he was. She wouldn’t let him breathe! She'd grab her ankle with one hand and she’d pull on her leg so it was real tight around Jimmy's neck and she'd laugh and Jimmy would thrash and try to pull her leg loose but Mrs. Holloway would slap his hands away and laugh and pinch his nipples real hard and laugh some more and squeeze her leg so tight around my classmate's throat I couldn't see how he could breathe.Jimmy’s Mom would lean back and she’d raise him up out of the water by this neck and he couldn’t breathe at all when she did that to him.
He’d fight but it didn’t help. Mrs. Holloway had her legs tight around his throat and chest! When Jimmy did fight back his legs would thrash and kick water in the pool and I could tell Jimmy was naked. He had a big cock like me. And he had a boner. Like me. I realized I’d pulled my cock out of my shorts. And my hand was wrapped around it.
Al I could do was watch, mesmerized by the sight. If I'd thought before that Mrs. Holloway reminded me of the women in Dad's dirty fetish magazines I was sure of it now. She was hurting her son! Heck, she was torturing him. And enjoying it too! That was obvious by the way she laughed and the way she thrust her hips and ground her crotch into the back of Jimmy's head. It was erotic. It was sexual. She was getting aroused. Even I could tell that.
I thought Ms. Holloway might have seen me hiding by the bushes a couple times. I'd moved a little too far out from the corner to see better. Jimmy's Mom looked right where I was standing. She kept looking at me for half a minute. And grinned in my direction. I didn't move. I was scared she'd get mad that I was watching. But then she laughed as she turned her attention back to Jimmy and
I stayed where I was and watched. I must have watched for at least twenty more minutes. Jimmy's body was jerking uncontrollably before his Mom stopped choking him. Then finally he stopped fighting so hard. I watched the whole thing. I jerked off too. I couldn't help myself. She was soooo hot. While she was choking Jimmy her bikini top slid down. I could see her tits real clear then. They were fabulous! And with her legs spread wide as she clamped Jimmy's throat between her thighs I could see everything in between there whenever Jimmy fought hard enough to almost get away. I shot off a big geyser of cum whenI heard Mrs. Holloway giggle right when Jimmy's body went into spasms just before he stopped moving. It was about the best orgasm I'd ever had.
As cum dripped off the end of my cock I watched the sexy and cruel Mrs. Holloway relax her legs and giggle again as she pushed on Jimmy’s face and then used both her feet to push her own son’s head under the water. I'd just shot the biggest load of my life and yet I started getting hard again as I heard her delighted little laugh. She was drowning her boy and I was getting off on it! So was she! This was way better than looking at magazines! God she was something. My cock twitched when her hand slid between her legs and she started to stroke herself down there. And I got fully erect again as I watched her causally lean down and grab her son by his hair so she could turn him over and expose his face. She was so deliciously cruel. To her own son no less! A small part of my brain thought Jimmy Holloway was the luckiest boy in the world to have such a sexy and wicked Mommy. That's when she called my name. I practically jumped out of my skin.
"Is that you Michael? Come on out sweetie. I know you're there Michael Baxter. No need to hide darlin. Come over and join me and Jimmy. Or I'll call you Mother and tell her how you jacked off on my rose bush."
She was looking right at me. And pointed to Jimmy floating there in the pool. She called my name again and said she needed help getting her boy out of the pool. Before he drowned. She didn’t seem upset that Jimmy might be drowning. She even giggled when she said he'd drown without my help. Then I’d be my fault her boy died she laughed. What could I do. I went over and stood next to her and waited for her to tell me what to do.
Mrs. Holloway put her hand on my crotch. She felt my dick! I'd already been hard when I walked over to her. Now I got huge. She smiled as my cock grew under her fingers. And started to rub her hand up and down the length of my prick. My knees felt rubbery and it was like I was floating in the pool instead of Jimmy. She slapped my balls then. Pretty hard too. I yelped. And she told me to pull Jimmy out of the water.
As soon as I'd dragged Jimmy's inert body up on the pool deck his Mom leaned over and put her finger on his neck. She smiled. I cocked my head curious about what she'd found and why she was amused. Mrs. Holloway said she couldn't get a pulse. And laughed that she'd stopped her boy's heart again and probably killed another couple millions of Jimmy's brain cells. Suddenly I understood why Jimmy was so screwed up. He wasn’t born stupid. His Mommy made him that way. Having her sadistic fun with him. I got sooo hard and the wet spot on my shorts got bigger as I leaked pre-cum thinking about how wicked Mrs. Holloway must be to do that to her own little boy. And thinking about what it would be like if my Mommy did something like that to me!
I snapped out of my daydream when Jimmy’s Mom asked me if I knew CPR. I told her I did. She pointed at Jimmy. I looked down at him. She smiled and nodded her head. I got up pulled Jimmy out of the water and turned him so he was on his back by the table and chairs near the pool. I bent over Jimmy and started compressions on his chest and gave him mouth-to-mouth. After about two minutes his body heaved, water poured from his mouth and his eyes opened. He was breathing again. It was ragged and it looked like it hurt but he'd be OK I guessed. His Mom must have thought so too cause she told me to leave Jimmy and come to where she was sitting.
“You must have liked watching what I did to Jimmy. It made you hard didn’t it Michael. And it made you come. Would you like me to choke you like that? I could put your head between my legs and squeeze real tight baby. Jimmy knows CPR too. He looks revived and strong enough now to bring you back if I go too far.”
God she scared me! But it thrilled me too! Mrs. Holloway had spread her legs real wide as she asked me things. Her bikini was so small that with her thighs opened wide like that I could see her slit! It glistened! It was wet! And the fleshy parts around that provocative burrow were swollen and distended and looked like they were eager to feel something big and stiff and long slide in. Which is exactly what happened while I stood there. Mrs. Holloway put her hand between her legs and giggled as I watched her slid first one, then two and finally three of her fingers deep inside her pussy. She slid her fingers in and out, in and out. And moaned as she did it. I wasn’t even aware of it but I slipped my own hand down my shorts and started to stoke my cock, my hand sliding up and down my shaft in time with Mrs. Holloway’s fingers sliding in and out of her cunt.
She kicked me in the balls then. And told me I shouldn’t jack off without permission. So I asked permission. She laughed and said no. But I could get on my knees she said. And she told me I could put my head between her legs. And lick her pussy. If I didn’t mind getting smothered a little.
I didn’t mind. I was on the concrete deck on all fours and pressing my face between her thighs before I even thought about what I was doing. My cock was dictating what I did. My brain had checked out. I was going to taste a woman down there! I’d dreamed of this for a couple of years now. I figured she’d let me lick her and tongue her and eat her pussy some then she’d want me to fuck her. With my dick. That’s how it happened in the picture stories in Dad’s magazines.
Mrs. Holloway has strong legs. I got my face between her thighs and she wrapped her legs around my head and pulled my mouth and nose against her crotch so tight all I could was lick and eat her the way she told me to. When I followed her instructions and stuck my tongue deep inside her and wiggled it side to side the way she wanted she’d let me breathe a little every so often. If I failed to please her she grabbed my hair and pulled on it
So hard I thought she’d make me go bald. So I paid attention to what she said and I did what she wanted as best I could. Still, she didn’t let me breathe a lot. I could feel myself getting dizzy and weak. It got harder to obey her. Which meant she let me breathe even less so I had even more trouble obeying her.
I guess I passed out eventually. One second I was poking my tongue as deep into Mrs. Holloway’s pussy as I could and the next I was on my back on the concrete looking up at her standing over me. She was smiling at me and using her bare foot to fiddle with my dick. I had another boner. My balls hurt and my cock hurt the way it does if I jerk off half a dozen times in a row. But I didn’t care. Mrs. Holloway was standing over me naked. And smiling at me.
“Not bad for a first time Michael. But you can do better honey. And you will before summer is over. We’ll have lots of time together baby. I called you Mother while you were ‘resting’. I told her how much fun you and Jimmy were having. And suggested you spend the summer with us. She agreed Michael! Isn’t that fantastic! We’re all going to have so much fun the next three months.”
I was still kind of groggy so I didn’t really understand all that she was saying. But I understood when she sat on the edge of the chaise lounge and spread her legs and pointed to me and then to her cunt. I crawled over to her and got on my knees. I didn’t have to do anymore. Mrs. Holloway put her legs on my shoulders and pulled me in close. Then she wrapped her thighs behind my head and soon my face was buried in her pussy again. And she was whispering to me exactly how I should use my lips and my tongue to give her the pleasure she wanted. I did my best. But I guess it wasn’t good enough cause I passed out again. I lasted longer this time. Or Mrs. Holloway was more patient with me. I know I gave her at least one orgasm. I felt a gusher of hot sticky liquid ooze out of her cunt after I’d tongued her for about five minutes without stopping. It covered my face and made it harder to breathe. Mrs. Holloway didn’t care when I started to gag and struggled though. It wasn’t about me she said. It was about pleasing her. That was my job now. My purpose in life. Nothing else mattered. Nothing else would ever matter to me again.
That first day with Mrs. Holloway was two weeks ago. I think. I don’t remember as good anymore. I’m starting to act like Jimmy. I can’t always make the words come out right when I talk. It scares me. Mrs. Holloway tells me not to worry. She says it’s natural for boys to get a little stupid when they’ve been smothered a lot. Especially if they get choked and smothered enough to stop their heart. I ask her if that happened to me.
She always laughs and asks me if I remember getting smothered. I do kind of. But mostly I remember her smiling at me when I wake up and her laughing when she opens her legs for me and invites me to push my face deep between her thighs. I remember that and it makes me feel good. Because I know how much she likes that. And I know it pleases her when I eat her to a climax. And that’s all I want to do for Mrs. Holloway now. It’s all I want to do for any woman. It’s only what they deserve.
I remember something from a couple days ago, or maybe it was a week. Anyway, Mrs. Holloway wrapped plastic warp all around my body. Well, not everywhere. She left my head free. And my cock and balls. But my arms were pinned to me sides and my legs were bound together and I couldn’t really move at all. I was naked too. Mrs. Holloway made me stand by the edge of the pool and she wound layer after layer of clear plastic wrap around my body. Then when she was done she grabbed my cock in her left hand and played with it till I got hard. It didn’t take long. She’d put me on a steady diet of Cialis and Viagra and stimulants and anti-anxiety drugs that first day Mom sent me over here.
As soon as I got hard Mrs. Holloway started to punch me in the balls. She kept hold of my cock in her left hand, made a fist with her right hand and just started to pound the crap out of my balls. She must have hit me fifty times. I wanted to throw up. But all I could do was back up and even that didn’t help. She’d move forward every time I stepped back. Before long my heels were hanging over the edge of the swimming pool and I had nowhere to go. That’s when she started to punch my balls so hard I was sure I’d puke. I did get dizzy and the only thing keeping me from falling into the pool was Mrs. Holloway’s tight grip on my boner.
When my knees gave out from the agonizing pain in my balls Mrs. Holloway laughed and let go of my dick. I fell backward into the pool. I couldn’t use my arms or my legs. I bobbed around for a few seconds and then I turned over so I was face down. My mouth was under water! I was drowning! I’d turn my head and try to lift it clear and I would for a couple seconds so I’d get just enough air to keep me going another half minute or so,. Then I’d start to sink and my face would slip under water and I’d try to stay calm cause I knew I’d float up soon but it was so hard not to panic. I must have spent five minutes like that and I was almost completely exhausted when I felt Mrs. Holloway’s hands on me. She’d grabbed my cock and balls and she was pulling me to the surface and turning me over so I was face up.
“You have a lovely cock Michael. It’s bigger than my Jimmy’s and he’s two years older than you. I’m glad your Mother wanted you to learn some respect this summer. It means we get to spend some quality time together.”
‘My Mom wanted this for me?’ I sputtered.
My gorgeous sexy tormenter had laughed and said yes, it had all been arranged the week I got out of school. Mrs. Holloway explained how my Mom was always commenting on how sweet and respectful and well-mannered Jimmy was. My Mom had asked and asked how a woman turned her teenaged son into such a nice boy. Mrs. Holloway had said Mom should be careful what she asks for. She may not like the result. Well, according to Mrs. Holloway my Mom had insisted she was willing to do whatever it took to turn me into a boy like Jimmy. The two women had had a long talk then. And come to an agreement of sorts. The day before Mom sent me to Jimmy’s she’d gone to the Holloway’s herself.
That’s when Mrs. Holloway had shown my Mom how she trained Jimmy to be an obedient and good little boy. When Mrs. Holloway told me this story she’d laughed at this part. She’d said Mom hadn’t been squeamish at all about the methods used to make Jimmy behave. In fact, she said, my Mom had been eager to try some of the more interesting torments out for herself. Apparently my Mom has a cruel streak too. She’d used her hands to choke Jimmy and she’d loved it. Mrs. Holloway said if she hadn’t stopped my Mom then Mommy would have snuffed Jimmy without a second thought. At least that’s what Mrs. Holloway told me.
And I believed her. I was wrapped in plastic wrap floating in a pool and the only thing keeping me from drowning was Mrs. Holloway’s hand gripping my cock and balls. The more she told me about how Mom tortured Jimmy that day the harder I got. Mrs. Holloway wasn’t even jacking me off and I got the boner of a lifetime just visualizing my Mom with her hands wrapped tight around Jimmy’s neck. And my neck. I could see Mom doing that to a boy. To me. In fact, I wanted her to do that to me. I told Mrs. Holloway that. She’d laughed and said a boy like me should be careful what he asks for. Especially when he asks a sadistic woman to tell his equally sadistic Mommy to torture him.
Jimmy’s Mom did start to jerk me off then. She pushed me under water too. I could see her looking down at me though the water. She was laughing. And stroking my penis and making me horny and hard and crazy with lust even though I couldn’t breathe. Just before I shot off she dipped her face in the water and kissed me. My lungs were burning from lack of air and my balls ached from when she’d punched me there so many times. And my cock almost hurt from getting jacked off for ten minutes at least. But I kissed her back. Passionately. I loved her at that moment. I kept my eyes open. So did she. I could see she was leering at me as she kissed me and drown me and jacked me off all at the same time.
I came. Big.A geyser of cum shot out of my cock. It was so strong the surface of the pool rippled with my cum. My whole body shook it was so intense. Mrs. Holloway felt it too. She broke off the kiss, let go of my cock and put her hand over my mouth. She had my cum in her hand. I licked it off. She liked that I did that without being asked. I could tell. I was in agony then. I’d swallowed water when I’d climaxed it was so powerful an orgasm. Mrs. Holloway put her hand around my neck and held my face just under the surface of the water. She turned my head so my left ear was above the surface. I heard her whisper that she was going to enjoy drowning me. She was going to enjoy stopping my heart and killing ten million of my brain cells. Sweet dreams Michael she whispered. Have a nice trip my little slut she purred just as I blacked out.
When I came to my head was on the top step of the pool. Jimmy was leaning over me, his mouth just leaving mine. He’d given me CPR. Mrs. Holloway said I’d been out for almost five minutes. She laughed and said I’d probably lost twenty IQ points. My Mommy would be pleased she giggled. Then she asked if I wanted to do it again. I started to cry. And begged her not to. I said I’d be good for her. I’d do anything she wanted. Just please don’t drown me again.
She laughed. And said ‘what if I want you to drown for me Michael. You want to do anything for me so you want to drown for me again don’t you honey?’
It was all so confusing. She looked so good leaning over me. She’s really pretty. Her blue eyes and golden blond hair an her high cheek bones are like a super model. I was on my back, my hands and legs wrapped tight with plastic wrap. I couldn’t move. All I could do was look up at her. Her boobs were right over my face. They’re so big and firm and round and luscious looking. She’d been teasing and tormenting and hurting me for over a week by then. I don’t know, it was all too much for me I guess. I could feel myself getting hard again. I knew it wasn’t just the drugs she forced on me. I wanted to please this cruel woman more than I’d wanted anything before. I needed to please her more than I needed to live. It was odd. I was in love with Jimmy’s Mom. I was in lust with her. She was my life, my reason for being. I just knew it in that moment. It suddenly seemed so clear.
So I asked her to drown me again. I told her to do it slow. To take her time.To enjoy it. And I said I wanted Mommy to drown me too. Could she call my Mom and ask her to come over so she could see what a good little boy I could be. I said I wanted Mommy to drown me too. I got so excited I practically begged Mrs. Holloway to call my Mom so she could come drown her little boy and snuff him too if she wanted.
She laughed a good long time after I said all that. I was a little embarrassed I’d blurted out all those dark secret I’d been thinking these last few weeks. Mrs. Holloway seemed to enjoy my outburst too. Although she did stick out her lusciously plump lips in a pout and asked why I didn’t want Mommy to snuff me instead of her. Didn’t she deserve to have that kind of fun too. I got real embarrassed then. And without thinking I said yes, she deserved to have all the fun she could. You can snuff me too Mrs. Holloway. With Mommy. The two of you can do anything you like to me.
She kissed me again. And crushed my balls till I screamed. Then she pulled out of the water some more. I was so weak I kept sliding under whenever she let go of me. She like that but I could tell she didn’t want me to drown just yet in spite of what I’d said about how she and Mommy could snuff me if they wanted to.
It hurt lying there half in and half out of the pool. The hard concrete edge dug into my back. Mrs. Holloway noticed. And sat on my chest. That made it hurt worse. She giggled and told Jimmy to bring her the phone. She called my Mom right then. And told her what I’d said about how she and mommy should snuff me. Mrs. Holloway listened to what Mom said in reply and laughed and looked at me and said, ‘Yes Tammy, I think it’s time. Come on over lover and let’s have us a fuck and snuff party. Your boy Michael’s ready. And my Jimmy’s been ready since the day I gave birth to the little creep.’
Ten minutes later Mommy was there and she got in the pool with me and Ms. Holloway. Mom grabbed me and pulled me to where the water was two feet deep and then Mommy turned me so I was on my back and she spread her legs and straddled me and used her hand to guide my cock inside her slit.
“I’ve been wanting to do this for a long time honey. Can you fuck Mommy good Michael? Will you fuck Mommy while she drowns you sweetheart?”
I nodded and said yes, yes, yes I would. And I did. Although actually Mommy did most of the work. She used me. She raped her little boy and while she rode my cock like a wild woman she pushed my head under water over and over again and it was scary and it hurt and I wanted Mom to stop and I wanted her to do that to me forever. I didn’t have an orgasm. Mom had four. I’d learned with Ms. Holloway how to tell when a woman reaches climax. Mommy climaxed four times riding my cock. I didn’t climax but I did drown. When Mom’s body started to buck and write that fourth time she leaned over and kissed me hard on the lips. Then she pushed my head under water just far enough my nose was at the surface. Mom was humping me real good and her thrusts and gyrations made little waves that washed over my face and sent water up my nose. I coughed and sputtered and hurt and eventually drowned. Because things went real dark and then all of a sudden I was awake again and Mommy wasn’t riding my dick anymore and my head was resting on the top step of the pool and Jimmy was huffing and puffing and blowing air in my mouth.
After that Mommy and Ms. Holloway played their wicked games with both me and Jimmy. And here’s the crazy thing. When my Mom tortured Jimmy I got jealous. I wanted her for myself. I told her that. I told her I wanted her to have more fun than she had with any other boy. I told my Mom she could do anything she wanted to me. And I begged her to jack me off, to wrap her hand around my cock and make me shoot off. Because I loved that. I needed that. I’d do anything for that.
This morning Mommy and Ms. Amberstarted teaching me a new game. I call Jimmy’s Mom Ms. Amber now. Mommy insisted. My Mom said she and Ms. Amber both own me. And Jimmy too. Mommy says me and Jimmy are nothing but sluts. It mist be true because Mommy fucks me all the time now. Just like those women in Dad’s magazines fuck their little boys.
Mom and Ms. Amber came in my room, this morningwell me and Jimmy’s room and Mom had this contraption on her waist. It was a strapon cock. I’d seen things like it in Dad’s dirty magazines. Gosh, that seems like so long ago that I used to jerk off looking at pictures of cruel women tormenting men. Now I have Mrs. Holloway to torture me. And my Mommy.It’s not what I expected. It hurts lot more than I thought it would. And it’s a whole bunch scarier. But I get huge boners. And Mrs. Holloway makes Jimmy jack me off sometimes. It’s nice having someone else jerk you off. Even if it is a boy.
“Michael honey. Mommy wants to teach you a new game today. I’ll let you eat me later. But I think it’s time you had sissy sex sweetie. A big strong slutty little boy like you can’t stay a virgin all his life. So, here’s what we’re going to do. I want you to bend over the bed. That’s my boy. Jimmy! Julie, help us out. Tie Michael’s feet to the bed posts. Pull his legs apart. That’s it. Pull them wider. I want his hole exposed for me. His Mommy’s going to have some fun with her boy’s ass hole and she wants easy access to that butt.”
Mommy split me in two. At least that’s that it felt like. She just poked the end of her huge fake cock against the outside of my anus then shoved it in. All at once.As deep as it would go. It felt like Mommy rammed that thing all the way up into my throat. She couldn’t have forced it in that far though cause I could still scream. Which I did at the top of my lungs for at least fifteen minutes while Mommy raped me up the butt. I shrieked and screamed so loud I could barely hear Mommy and Ms. Amber laughing. And planning on how they were going to snuff me and Jimmy just as soon as they were doing having fun fucking and torturing our dicks.