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Now normally, I would continue on with my story about rough lesbian sex at formal with my sister, but I think I should take some time to introduce my love of pegging. Now technically, what I was about to do with my sister was not pegging. But pegging sissy boys – oh, how I love it. I first started pegging sissy boys as a favor to my boyfriend at the time.
My boyfriend at the time (we’ll call him Chad) was the Pledge Master for his fraternity. He was in charge of their rewards and punishments. That wasn’t his main job, but it was an important one. He took this part of his job very seriously. He was pretty creative and he included me in both his rewards and his punishments. It was not uncommon for me to receive a text from Chad in the middle of the day in which he would tell me to report to the fraternity house closet.
The closet was the room of rewards. In this closet, pledges received their reward from me. Usually I’d suck them off. Sometimes if Chad said they’d been extra good, I’d let them fuck me. I didn’t mind this, but the punishments were what I most looked forward to. You see, Chad wanted to remind his pledges of their place, and if they misbehaved, their place was at the bottom. Or, being the bottom, I guess is a better way to put it.
The night it all started, Chad and I were on a date. He told me he had a present for me and I was so excited. When we got back in his car, he pulled out a strap-on dildo with a bright pink bow around the tip. I got confused. A week before this, I tried to finger Chad’s ass while I blew him, and he did NOT like it. I guess I thought he got me the strap-on so I’d play with my sisters in front of him?
Nope. He did hate me attempting to put a finger in his ass, and that gave him a great idea for a punishment. If he hated having a finger in his ass, he guessed most guys would hate it too. And if they hated a finger, then they would definitely hate a cock. His new punishment? I was going to peg the pledges who disobeyed him. To quote Chad: “If they’re gonna act like a little bitch, then they’re going to get fucked like a little bitch.”
The closet was the room of rewards, so the pegging sissy boys didn’t take place there. Instead, I pegged them in the basement. They knew the drill. Chad just had to tell them to report to the basement so when I arrived, they’d be on their hands and knees. Usually, they’d be fully clothed, because part of their punishment was stripping for me. Apparently, stripping before pegging is humiliating to them. Anyway, I’d come down into the basement and tell them to get naked. I’d watch this happen and usually cheer for them. Or I’d boo them – whichever seemed to embarrass them more.
Once they were naked, I’d use a squirt bottle to spray lube onto their assholes. They were responsible for reaching back and spreading their asscheeks. If they didn’t spread them wide enough, then I wouldn’t get the lube where they needed it. It only took one sissy boy messing up one time before they learned. I didn’t care if it hurts or not and Chad didn’t either. Pegging sissy boys wasn’t all about pain. It was also about humiliation. If it hurt, that was just an added bonus.
The first time I tried pegging sissy boys, I was very timid. Chad sat in the corner and cheered me on, but I was still nervous. I was used to being penetrated, not doing the penetrating. All in all, I was looking forward to it. I liked the idea of being dominant, and pegging sissy boys definitely let me do that!
The boy was on his hands and knees and had his ass up in the air. I was familiar with that position, so I sympathized with him. Your knees can really start to hurt. Anyway, we got him all lubed up and then I put a drop of lube on the dildo. I pushed just the tip in first. He moaned so loud that I think both of us were surprised! He liked it though, because he begged me to push more of the dildo in. I didn’t. This was a punishment after all.
Instead, I took the fraternity paddle Chad offered me and brought it down hard on his ass. He yelped and pushed back against the dildo. By pushing back, he took another three inches of the dildo up his ass. He moaned again like a little slut and begged me for more.
I’ll admit I enjoyed the power. I pushed the rest of my strap-on into his tight ass. He groaned and I watched him grab at his own hard cock. I knew then that I was pegging a sissy boy who got off on a cock up his ass. I fucked his ass so hard that my thighs were sore! He came all over his hand and while I didn’t come, I did enjoy myself. I do think Chad enjoyed watching me pegging sissy boys because his cock was rock-hard.
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Let me share just a couple of the Sissy Pegging Stories I have collected over the decades. Yes, I am that old. Yes, I have worn strapons for that long. Now let’s get down to business.
It is always a delight when I get a new sissy who has never been fucked before, been near a dildo by itself or a strapon, especially if the strapon is being worn by a Fe
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