Tony loses his virginity to his grandmother. Not an hour later he ends up in bed with his mother. How did it all happen to this 14-year-old boy?
My Disastrous Night 6 - Tony

Tony loses his virginity to his grandmother. Not an hour later he ends up in bed with his mother. How did it all happen to this 14-year-old boy?

When I woke up I was snuggled up behind Grandma, spooning her. Her nightgown was up above her waist and I had my right hand up on her breast, massaging it. Pressed up against her I felt my disk go hard. To make matters worse, as it grew in size it slipped right through the opening in my pajamas, pressing up against her bare butt. I wondered if she was awake, it she knew what I was doing.

I didn't know how I got into this position. When I went to bed it was Dad. Now I was in bed with Grandma, and feeling her up. God she felt so good.

Then Grandma said something. I'm not even sure what she said, only that she caught me. I moved away as I said "Sorry Grandma."

Then she reached around and grabbed my shaft, stroking it up and down a few times. I about fainted with the pleasure of it all.

She rolled over onto her back. "Get over here and fuck me."

I couldn't believe what I was hearing. I wasn't even sure how to do it. I just did as she said. I got between her legs and she guided my dick down between them so that the head of my penis was at her opening. I pressed myself forward and easily slid into her. Oh my God it was glorious. I had never felt anything so wonderful in all my life. It was wet, warm, velvety feeling and snug too.

"Pull most of the way out now and push back in," she instructed. I did, repeating it again and again. Each time it sent chills and electricity outward to the rest of my body, a feeling like no other on the face of the earth.

"Oh Grandma, this feels so wonderful," I told her.

"You feel wonderful to me too honey," she replied. "Now start moving faster and when you push in I want you to push harder, yes baby that's it, you can ever push harder than that." I started really pushing in but still trying not to hurt her when I got near the end of my stroke.

"Don't hold back darling," she corrected me. "Let your body hit hard against mine, yes that's it. Oh God Tony, yes, fuck me hard like that baby, really hard."

I was thrusting in about as hard as I could. I finally had to lie down on her and grab her under the shoulders so I could get better leverage. Then I rocked my hips as fast and as hard as I could. It was a good thing that Grandma had a few extra pounds on her, especially around the hips and thighs, or I might have hurt her.

Grandma screamed out. "Oh God Tony, I'm cumming. You're making me cum baby. Don't stop. Keep fucking me. Oh God baby, yes, yes," she yelled.

To hear my grandma scream out like that because of the pleasure I was giving her, well that was a turn on by itself. My whole body reacted and I climaxed for the first time ever inside of a woman, or girl for that matter. I shot out 4 hard bursts of cum before it dwindled down to nothing. That was the most fantastic feeling I had ever experienced. I only wished that I had been able to do it with Grandma a year ago when I first started masturbating. I spent a year jacking off when I could have been doing this, fucking.

"Thank you honey," Grandma said. "I needed that more than you know."

"That was awesome Grandma," I told her. "Can we do that again sometime?"

"Of course darling but we can't tell anyone. OK?"

"OK Grandma," I promised. "I won't tell anyone. By the way where is everyone? They couldn't be here or you wouldn't have been so loud, I'm sure."

"Well your dad had to return home for a while and will be back in the morning to take you fishing."

"I don't really like fishing Grandma," I told her. "Charlie can go with Dad."

"Charles, well I let Charles go to a friends house. He didn't want to go fishing anyway."

"That bum. Then I'm not going fishing if Charlie's not," I stated. "Grandma, would you take me home now please? If I get home before Dad drives all the way back here I can convince him to just go without me. But if I wait here until he returns he will make me feel guilty about him driving all the way here just to take me fishing, and I'll have to go."

After a little encouragement, Grandma agreed to take me home. An hour later we were home. I waved goodbye to Grandma and went on into the house.

It was the middle of the night and I just wanted to get back to bed. I stripped off my clothes, put on a pair of shorts and hopped in bed. For a while I just stayed still thinking about the wonderful experience I had with my grandmother. I was a bit torn though because on one level it seemed so wrong, like I had sinned. On another it was the most exciting thing I had ever done.

I just laid there on my bed contemplating it all when I heard a muffled sound. I listened more intently and thought it was like someone crying. Was it my mom?

Getting up I walked to my mother's room. The door was shut but I could hear my mom crying inside. I quietly opened the door and saw that my mom was definitely crying. She was in bed with the sheet pulled up over her but still crying.

I walked over to the bed and said, "Mom, what's wrong? Why are you crying?"

"Tony, is that you baby?" she asked.

"Yea Mom," I replied. "What's wrong?"

"Oh everything honey," she said as she sat up in bed, the sheet still mostly covering her but the blanket halfway down the bed.

Mom reached around me and pulled me close, giving me a hug. Normally I wouldn't have thought much about it, having received hugs from my mom all my life. But tonight was different. A little over an hour ago I had fucked my grandmother. Now my mom was hugging me and all I could think about was her tits pressing into my chest and the hard on it was giving me. I put my arms around her and hugged her back, increasing the pressure between us.

"Give your mother a kiss," she said and taking my head in her hands she kissed me on the lips. Now this isn't all that unusual for our family either. But I was turned on with it, unlike I had ever been in the past. I put my arms around her again and held her close. The kiss went longer than usual.

When my mom broke it she exclaimed, "Thanks darling. I needed that."

I could see the tears drying on her face and said, "Mom, you've been crying and I'm going to kiss away your tears." I did too, starting at her eyes and working my way down her cheeks, alternating from one side to the other. When I got to her mouth I kissed her again, gentle but long.

"Wow baby, that was...uh...delightful," she said. I didn't wait for her to say anything else but kissed her again.

Mom gently pushed me away. "Now honey, that's enough, thank you." But I didn't stop. Suddenly yanking the sheet off of her I pushed her back down onto the bed. A second later I had my boxer shorts off and had climbed up onto the bed. "Tony, you stop this right now," my mom exclaimed.

I answered her by lowering my body down onto hers so that my mouth was even with her breasts. Taking one into my mouth I heard my mom gasp. "Tony, we can't do this...Oh God...Tony, please, you have to stop."

But I didn't stop. I sucked her breast hard bringing my teeth closer and closer to her nipple until I was gently biting it. She kept protesting but with not as much effort as before. Then as I moved to her other breast I separated her legs. Though she continued to tell me to stop, she didn't put up any fight physically. I knew she wanted me to do exactly what I was doing. She just couldn't admit it out loud. But what convinced me beyond a shadow of a doubt was when she lifted her own knees into the air, spreading her legs apart for me to fuck her. And that's exactly what I was going to do.

I think my erection was harder than when I fucked Grandma earlier that night. What surprised me though was how easily I slid into my mother, like she had been all lubed up ready for me. But I knew that couldn't be the case. Lubed or not, Mom felt wonderful. I leaned forward and kissed her full on the mouth. Her protests had all but stopped when I first entered her. Now she kissed me back like I was her lover, which at that moment was exactly what I was. I did with Mom what I had learned with Grandma, to slowly increase my speed and power as I repeatedly thrust into her.

Before I was anywhere near cumming, Mom cried out in ecstasy. She had her first orgasm from me and I swore it was only the first of many more. I planned on fucking my mom for years to come.

"Oh Tony, that was magnificent," she praised me. "Let me turn over so you can come from behind." I pulled out of her long enough for her to turn over and get on all fours and then was back inside of her again. This was actually easier because I was able to be up on my knees, holding onto her hips, and pounding into her as hard as I wanted. She didn't keep it that easy for me though. She took one of my hands and had me reach around her waist to rub her pussy. This sent her through the roof though and she was soon climaxing again. Her pussy was spasming around my shaft so hard now that it caused me to climax too. For the first time in my life I was shooting my cum, not in the shower, not in the toilet, but deep in my mother's vagina. Again and again I exploded inside of her as we both were wrapped in our own piece of heaven.

When it was over I went limp and slid out of my mom. We both collapsed onto the bed exhausted.

"Tony, why did you do that?" my mom asked.

"I don't know. It just sort of happened," I tried to explain. "You were in pain and I wanted to comfort you. But when I felt you so close to me, felt your body against mine, my own body just reacted. My mind couldn't keep up and then it was too late. Each time I touched you, kissed you, tasted you, I wanted more."

"I know what you are saying," she replied. "Though my mind knew it was wrong and tried to stop you with my words, my body needed it and wanted it. It wanted you to take me, to make love to me. I wanted you to fuck me Tony. And I don't want it to be our last time either."

We must have fallen asleep soon after. I don't know how long we slept but I woke up to my mom giving me a blowjob. It was light out and I could see her looking at me as she slid me in and out of her mouth. I was hard and wanted to fuck her again. I pulled her up to me to kiss her. As we kissed she slid her body down onto my shaft. I moaned my approval.

"Just lay there and let me do all the work sweetheart," she instructed, so I did just that. She was moving at a rather calm and steady pace. My climax hit me quick and sudden, without warning. Mom knew and smiled at me but she didn't slow down or stop, just kept fucking me at that same smooth rhythm. It was enough to keep me relatively firm, enough that she could keep fucking me. A few minutes later she had to stop. She leaned forward and hugged me tight as an orgasm swept through her body.

Just then I saw my 17-year-old brother Charlie standing there at the end of the bed. He had one finger vertical against his lips, motioning me to be quiet. Oh and he was stark naked with a hard on that was easily bigger than mine. With my mom still hugging me I watched as my brother put spit all over the head of his penis. Then with one swift movement he got up on the bed, straddled our legs, just behind my mom and pressed his erection up against her ass.

"What in the world...Oh Christ," she began to say. Lifting and turning her head she saw who was invading her.

"Uuugh," Charlie grunted as he held Mom tight by the hips and pushed in hard.

"No Charlie, no," Mom screamed. The look on her face was one of terror as Charlie pierced her tight opening and pushed into her ass. Mom was still fighting him. Each time Charlie pulled partway out Mom would squeeze down hard trying to expel him out of her. Then he would thrust back in hard. But I was still inside of her, maybe semi-hard but still there. Each time Mom squeezed trying to get Charlie out, I felt it. It wasn't too long before she had me hard too.

I decided to match Charlie's strokes, rocking my hips up towards my head each time Charlie would thrust inward. The feeling was incredible. It may have just been my imagination but it was almost as if I could feel Charlie. I wondered what it felt like to Mom. Mom's look of horror was gone, replaced by one of someone who couldn't believe what was happening to her. It wasn't a bad look but one of bewilderment yet a growing sense of excitement, gradually moving toward ecstasy.

Charlie had picked up the pace and was really pounding Mom. I had trouble keeping up, sometimes just skipping a thrust. Bear, our German shepherd, came trotting in. He sniffed around our bodies, especially our groins while we kept fucking Mom.

When Bear barked Charlie yelled at him. "Shut up Bear. Can't you see I'm busy?" Bear just jumped up on the bed and continued to sniff us.

"Oh God I'm cumming," Mom exclaimed. Charlie responded by holding on tight and pounding into her ass as fast as he could. I tried to increase my own speed and in half a minute we were both shooting our cum into Mom, me into her pussy and Charlie up her ass.

That's when I realized Bear had his paws up onto Charlie's back and was trying to hump him. "Oh fuck, cut it out Bear," he yelled trying to swipe at Bear while he was spilling his seed into our mom. He wasn't too successful at getting Bear down.

"Bear, oh shit, fuck, fuck," Charlie screamed as he collapsed down on top of Mom and she on me. It all happened so fast. Charlie and I were still inside of Mom, still finishing up shooting our cum. Mom was still in the throws of her orgasm and Bear had apparently penetrated Charlie's ass. A second later Bear was fucking fast and furious. Charlie couldn't get leverage to get him off.

"Oh God no, his fucking knot," Charlie cried. "He's knotted me in the ass, oh shit he's still growing."

"Charlie, you're still fucking me," Mom said with surprise.

"It's Bear. Every time he thrusts he forces me to thrust into you," Charlie exclaimed.

"But I can feel you baby. You're still so hard," she said.

"The fucking dog must be a foot long and he's cumming inside of me."

The whole thing was messed up. Here I was, a 14-year-old boy on my back in my mother's bed, my legs straight out and together. My own mother was face down on top of me, her boobs smashed into my chest, her legs on either side of mine, and my hard dick up her pussy. I was still rocking my hips as best I could. With the hard on I had now I wasn't going to waste it. My older 17-year-old brother Charlie had his left knee on the bed next to my right hip, his other leg was forward with his foot on the bed giving him leverage to fuck my mom in the ass. From her comments he was still in her ass, hard as ever, even after just cumming in her, and laid out across her back. Mounted up on top of Charlie was Bear, out German shepherd, with his apparently long erection all the up Charlie's ass, including Bear's knot. The pressure of Charlie's ass on the knot kept Bear ejaculating into Charlie.

Dogs aren't like humans. They don't shoot out a couple of times and are then done. If the knot is tied and the pressure continues, the dog will continue to spill out off and on until the knot shrinks enough to be pulled out. That takes anywhere from about 15 to 45 minutes.

"Oh God Mom, I'm cumming again," Charlie cried. I wanted in on this too so I doubled my efforts and climaxed right after Charlie finished up. Mom was clearly out of it having intermittent orgams and would probably continue as long as Charlie and I kept it up inside of her. The thing is, every time Charlie would cum, it didn't take him long to get hard again with Bear continually pumping inside of him.

I never got completely soft, but I wasn't getting hard as quickly anymore either. I was finally wearing down. That's when I noticed some young girl standing at the open bedroom door. Charlie saw her too.

"Oh God no. Sam, what are you doing here?" Charlie asked her. Obviously they knew each other. But I had never seen her before. She was pretty but a bit too young for Charlie. She had to be my age or a little younger.

"I should be asking you that," Sam replied. "Fuck Charlie, this is hot."

Mom was looking at Sam now too, just in time to see my dad walk up behind Sam. "My God Kate, what have you done now?"

I knew we were all in for one big explosion, just about now.

The end (when Kate finished her view of the night)

Dear Readers,
What happens now? Kate is physically trapped between her two boys, both of whom are fucking her. She can't hide that. Will Jim walk out on her again, maybe back to Sandra? What about Sam? How will she play into this now? She has a totally different view on things than Jim does. Can she turn him?


Anonymous readerReport

2012-10-11 22:58:21
Not really for me as not into mom son or grandmar and grandson sex but like your style of writing.

anonymous readerReport

2011-05-20 12:58:26
Fuckin' sick & twisted.... I love it!!!

Anonymous readerReport

2010-07-23 12:40:07
dude lighten up it fiction and he do write other stories


2010-05-01 19:57:30
When i was fourteen, i fucked my Mom two to four times a night almost every night. This went on for eighteen months while my Dad was overseas in the Army. Mom said that she chose me rather then an outsider due to sexual diseases. I later learned theat she chose me due to my age and the fact that i had a very large cock for my age. She said that because of my youth, i could recover faster after each bout of sex. Therefore, i could fuck her more often. When we started, my cock was already close to seven inches in length. As the first eighteen months wore on and with me fucking her and her sucking on it all the time i grew fast. By the time my farher returned. My cock had grown to over nine inches and gotten much bigger around. Mom was thrilled with it and she just couldent leave me alone. We continued to fuck fairly steady even after my Dad came home. Mom has a beautiful hot pussy and i loved her for everything she taught me. She was awesome and so sexy. Wish we were still fucking today

Anonymous readerReport

2009-11-07 11:56:24
If you don't like them Sentry4C then don't read them.

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