timmy spanked

I have yet another pen-pal named timmy. timmy is a little 18 year-old virgin who likes my blog and also likes masturbating to vanilla porn. He asked if we could role play. He requested that I be his Aunt and he would be the nephew caught masturbating and spanked for it. We went back and forth a bit with this role play, and then I ‘kinda ‘sorta took over and just wrote a little story and got lill josephine to illustrate. I hope you enjoy it!

Nephew timmy:
I’m 18 years old and a senior in high school. My parents went on a year’s sabbatical to France, and so I wound up living with my Aunt Julie for the year. I didn’t mind. Since I was a little kid I always noticed how attractive my aunt was, her round and tight ass and her firm breasts. The perfect woman. Once I learned the magic of tugging on my cock I had an obsession with the thought of getting the chance to fuck her. My other friends over the years have gotten girlfriends and fucked them in the process, I was never that fortunate. I just never really got around to it with school and all. Every night I can, when my Aunt isn’t in hearing distance, I jack off to porn on my laptop. My favorite stars are Lexi Belle and Eva Lovia. My favorite category of porn is DPs and I love watching a slut get pounded senseless. This night was no different. I was horny, as always, and I needed to rub one out. I hopped in bed after removing all my clothes and got ready for a jerk session. I flipped open my computer and found a hot video. I had made sure to turn off my lights but I had forgotten my headphones at school and I left the volume on just a little bit. It was better with the sound. I was thoroughly enjoying myself. Lexi wailed on in the video while she was being pummeled.

Aunt Julie:
For some reason I couldn’t get to sleep and woke up at 2am. I slipped on my nightgown and went to the bathroom. On the way there I saw a dim and flickering light through the crack under my nephew’s bedroom door and heard some faint noises. I continued to the bathroom and thought about what I had seen. Can’t he ever stop with those video games? And he has an early class in the morning. No wonder he’s always late and seems so sluggish in the mornings. I made up my mind to confront him about it. I thought I should catch him red-handed so he could not deny it, and we’d go from there.

So on the way back I very quietly opened his door. The room was dark. I was surprised to not see him at his desk. But there he was on his bed with his back towards me. Or, more accurately, as he was fully nude with his bed covers pulled down and his bare bottom facing me! He had his laptop on the bed. At first I wondered what he was doing playing video games without any clothes on and in his bed. And then it dawned on me. What a fool I am! As my eyes became better accustomed to the dark it became very clear what he was doing! OMG! He was MASTURBATING to an Internet video porno!

He was rubbing his penis frantically, writhing his bottom and making moaning sounds as his eyes were fixated on the small screen and his ears tuned in to the dim sexual sounds emanating from the laptop. He had still not noticed that I had entered his room, enraptured as he was in his penile self-abuse.

First of all, that is just disgusting. I understand boys have their urges, but in a bedroom in my house, where I could hear him doing it? And I wash his sheets! Yuck! Well that’s just rude. And at this hour? What about school? As well, I’m a feminist, and what I was glimpsing from a distance depicted actions that clearly were very degrading to women. And how about the young “actress” being exploited? Plus, timmy rarely dated, and now I could see why, if this was his notion of normal sexual relationships! What woman would want him? I decided then and there I needed to nip this behavior in the bud.

I flipped on the light switch and stood there with my arms crossed with what I’m sure must have been a very angry expression on my face.

Timmy turned instantly. His penis still in his hand. “Aunty!” he yelled out. Aunty indeed.

“What is the meaning of this!!?!” I yelled.

Timmy flushed bright red and did not know whether to shut the laptop, run away, cover his bare behind, or cover his private parts. As a result he started trying to do some of each, with a predictable lack of success.

I stormed over and snatched the laptop. Timmy was frantic. He did not know what to do. He tried to pull up his bed covers, but I put my hand on them and stopped that. He would not be getting off that easily tonight! He finally wound up flipping over onto his tummy and covering his bare backside with his hands.

“What are you doing?” I asked him angrily. I knew perfectly well what he was doing, but I wanted him to say it aloud.

“Just looking at things on my laptop, Aunty,” he replied, practically in tears.

“I see. While naked and rubbing your penis? And what’s that called, Timmy?” I pressed.

“M…m…m…masturbating?”

“Indeed! And are you getting ejaculate on your bed right now, timmy? Turn around. Turn around this instant. Get that disgusting penis off your bed covers.”

Timmy rolled over, covering his dick with his hands.

“Are you STILL touching yourself????” I demanded. “In front of ME no less? Put your hands at your sides!”

Timmy did so, uncovering a very erect penis, with a turgid red-purple engorged tip. It was glistening with a mixture of his own saliva and pre-cum. It pointed at a forty-five degree angle up off his tummy, and was visibly throbbing. His testicles were tight, purpled, and engorged.

He lay there with his eyes tightly closed and his face screwed up holding back the tears. His little fists were clenched tightly at his sides, enduring the no doubt abject humiliation of his Aunty getting a clear view of his heretofore secret burgeoning sexuality.

This shaming was deliberate on my part. He needed to feel the shame of his actions acutely, or there would be no motivation to change his ways. Naughty little masturbator.

“That is filthy!” I said. “You should be ashamed of yourself, timmy!”

“Yes Aunty!” he cried out as the tears finally broke loose and started rolling down his cheeks….

Nephew timmy:
I was thoroughly enjoying myself, watching Lexi get pummeled and rubbing my cock, until, to my surprise, my Aunt burst in my room! I was sunk for sure. She caught me red handed. Rather cock in hand as I was mid stroke when she burst in.

“Oh Fuck” was the first thing that crossed my mind. My goose was cooked. No doubt about that. I went from the highest throes of self pleasure to the utter shock and humiliation of being caught masturbating by my Aunt. I just had to watch one more video, dammit. I can never turn down a good vid of Lexi Belle getting pummeled but now I was going to pay for it. I felt frozen and mortified at the same time. I would never be able to touch my cock again without thinking about this moment. When she told me to flip over and put my hands at my sides leaving myself exposed to her, I felt the urge to cry. I couldn’t hold it back and soon began to blubber like a baby. “please Aunty! I’m so sorry”

Aunt Julie:
“Well you should be sorry, young man!”

I put his laptop down on his desk, still open to the porn. I stopped it and reset the video to the beginning. I called timmy over, in the nude, and made him sit in front of it as I stood to his side. As he came over to the chair he tried to cover himself with his hands, “What did I tell you about playing with yourself???” I yelled out and he quickly glued his hands back to his sides, exposing his bouncing penis. I could hardly contain myself from laughing, but kept a very strict face as this was serious business!

“Start the video again,” I commanded him.

timmy hit the play button

“Full screen,” I told him.

The video was entitled “A Young Lexi Belle gets destroyed by a Monster Cock” from a site called “DaughterDestruction.com”.

“Pause it.” I said.

“Is this even legal? How old is she? Many of these young ladies are heavily exploited, young man. I don’t know if that’s the case with this particular actress but odds are she is. Have you researched it at all? No? I didn’t think so. And does this look pleasant to you? Do you think this girl is enjoying herself? Look at the ridiculous heels she has on. Continue it.”

timmy groaned and hit the play button again.

“Oh, very nice, now he’s hitting her. Hitting her on her behind! I can see violence against women has an attraction to you. Maybe I should hit you on your behind and see how you like it???”

“Pause it again.”

“Oh my God. He’s spreading her shaved vagina. And you can see her anus! Do you actually find that sexy??? Continue it.”

“Wait. Pause it there.”

“Now she’s being required to put that monstrosity into her mouth! And just look at his penis. Now look at yours. Do you actually fantasize that your penis is as large as his? Answer me! Do you?”

“no aunty…”

“Well that’s good, as your penis is a fraction of his size. Continue it.”

“Pause it there!”

“Did he actually order her to hold her vagina spread for him? And you think that’s perfectly normal sexual relations do you? Continue.”

“That poor girl. I hope she wasn’t injured by that. Oh well. Now that’s VERY nice. She gets a facefull of his ejaculate. VERY respectful of women.”

“timmy, it’s no wonder you have no social life with girls, nor any sex life. If that is your idea of ‘sexy’ there is something seriously wrong with you, young man. What girl in her right mind would ever go out with a boy who thinks of her in those terms? Answer me!”

“no girl ma’am…” said timmy, tears flowing down his cheeks.

“I am very disappointed in you, timmy. I feel it’s my laxity in discipline that has allowed this to happen. But it will stop right here and right now. You are grounded for a week, and grounded from your laptop for a month. You may use the computer in the living room for your homework, and God help you if I find any traces of porn on that browser!

“yes aunty…”

“Furthermore, there is to be no more internet pornography, ever, in this house, and the masturbation stops tonight. If I EVER catch you at it or even see any evidence of masturbation on your sheets or underwear, you will be very soundly spanked! Oh yes, just like that young lady got her bottom swatted, only much harder!”

“Aunty, please, no…”

“And that starts tonight. Stand up. WHAT did I say about touching yourself??? Hands at your sides!”

I moved the desk chair out towards the center of the room. I told timmy to pick up the laptop and to put it down on the floor to the left of the chair, and to ready the video for one final full screen viewing. I made him stand to the right of the chair at attention as I went to my bedroom to get the stout wooden hairbrush that my mother had used on me. I returned, hairbrush in hand. I knew from first-hand experience that this boy was going to learn the lesson of a lifetime tonight.

As it was late, I was dressed in only my panties with the hastily pulled on sheer baby doll negligee on top. I knew my breasts were quite visible through the sheer top, which only added to poor timmy’s confusion. At least he was seeing a real woman, not some Internet facsimile.

I sat on the chair and pulled the very naked timmy down across my lap. I could feel his still erect penis touching my bare thighs.

“We will be playing that video again, timmy, and you will be spanked with this hairbrush for its full duration. That’s 17 minutes and 50 seconds, young man, of pure fiery hell visited on your bottom. To remind you why you are being spanked, you will not take your eyes off your video the entire time or we will start it again from the beginning.”

I felt timmy wiggle on my laptop, and felt a slippery wetness on my left thigh.

“If you ejaculate on my legs, timmy, you will lick it up after we finish your hairbrushing, and then we’ll have a second viewing while you hold your semen in your mouth as I strap your backside raw.”

timmy stopped wiggling.

“Now hit the play button. I hope you enjoy it, it will be the last internet porn you see in this household.”

With an audible groan timmy hit the play button. At 17 minutes and 50 seconds long. timmy would have an exceptionally sore bottom by the time his spanking was over!

I started in on his bottom with the hairbrush. timmy began crying out with each stroke. His bottom seemed extremely tender. I varied my pace and the strength of the swats according to the severity of the intercourse that poor young girl was enduring.

timmy was struggling so much I had to hold his arm behind his back. He was yelling for mercy as I continued to swat his bare behind and his upper thighs, painting them fire engine red. This boy was going to learn respect for women even if I had to spank him bare across my knee every night for a month!

Very soon I had to even throw a leg across the backs of timmy’s to clamp him into place in order to continue his very well deserved spanking. His bottom and upper thighs were becoming exceedingly red with white in the centers, and he was crying out in a high-pitched voice, for all the world like a toddler or a little girl. I steeled myself to my task. A lesson needed to be taught. A lesson needed to be learned.

When the young lady in the porno was commanded to “hold her pussy open” that’s when I pulled timmy’s cheeks wide apart and spanked inside his bottom crack. Up and down and as close as I could get to his anus. timmy particularly cried out at these spanks. An excellent object lesson.

As the video finally ended with the ejaculate on the girl’s face, well I must say timmy’s face was even more wet from his tears than she was from the semen! And his bottom was red, swollen, and bruised in places.

I made him stand. I laughed aloud looking at how tiny and shriveled his penis was now! Even draped across my bare legs, and now him seeing my breasts through my sheer nightgown, all the sexiness was spanked out of him as he stood crying like a two-year-old and clutching at his sore backside.

I put him back into his bed. He sat down tenderly and immediately rolled over, showing me his bare swollen behind again. I picked up his laptop and went back to the doorway. I reminded timmy that he was grounded from his laptop for a month, and reminded him that if I saw or heard any evidence of masturbation, he would be spanked again immediately, regardless of the state of his bottom. I also told him that until further notice the bathroom and bedroom doors would be staying open while he was using those rooms. In fact I would ask the handyman to remove his bedroom door from its hinges tomorrow.

“And we shall see about what I can do to fix your social life with girls, young man.” With that I turned out the lights and left his room.

I went to sleep to the sounds of timmy still crying and sniffling in his bed.

When I awoke the next morning and went down for breakfast, I noticed timmy immediately averted his gaze from me. That was fine. A little embarrassment and a little fear of me and my hairbrush was a good thing for now.

As I was thinking about it later that day, my thought was that our lovely next door neighbor, Amanda, looked somewhat similar to the “Lexi Belle” from the video. Amanda talked to me about everything, and I knew that she was very sexually adventurous, despite the fact that she was just timmy’s age. While timmy was not particularly well endowed in the penis department, he was a fetching looking young lad otherwise, as Amanda had often commented to me. I was quite sure she would be open to training timmy, with my assistance, on how to better please a woman sexually.

In fact, shaming timmy for his masturbation habits in front of Amanda, and spanking him in front of her as well, would drive home timmy’s lesson wonderfully. A little jeering at his small penis from the two of us would not hurt either. Perhaps Amanda could be made to measure him and look up “average” on the Internet to compare him to.

That would bring him down another peg or two. “DaughterDestruction” indeed. Ha ha!

After that, timmy would be taught how to properly go down on a lady, and receive swats from Amanda when he was not performing! Of course, timmy would not be allowed to use his penis on sweet Amanda. Oh no. I wondered if Amanda would train timmy on how to use his tongue on and inside her asshole? I understand from Amanda it’s all the rage nowadays with young people.

In due time I would introduce Amanda (and timmy) to my strap-on dildo. Then we could make timmy really understand that being forced to deep throat a large penis, and even worse to receive deep, forceful, penetrative sex from it, was really not anywhere near pleasant. That way he could receive a real taste of his own medicine while learning total respect for (and obedience to) women at the same time.

Yes, he definitely needed to experience overly-forceful sex from the woman’s perspective. I would perhaps curl his hair a bit with my curling iron, dress him in pink panties, bra, and heels, and then have Amanda over. I would tell her what a naughty boy he was, masturbating to a movie of a young woman being abused and exploited. I would explain that’s why he was undergoing female empathy training for the next month, in lingerie and heels, and God help him when my period comes!

I would take timmy across my knee and spank him in front of Amanda right on the seat of his pink panties. During the spanking I would scold him in front of Amanda for masturbating to a video of a male with a huge penis having intercourse with a woman. Afterwards I would make him stand facing us and lower his panties so that Amanda could see exactly how little he was sporting down there by contrast.

Then I would bend him over the kitchen table, lower his panties, and encourage Amanda to first give him hell with my strap, and then with my strap-on!