Pegging His Man Pussy With My Strap On

Pegging a scared virgin ass was one of my naughty specialties. There’s nothing better than showing a man whose the boss in the bedroom. Now don’t get me wrong, I love a guy taking control but sometimes it makes me so fucking wet to have a guy completely under my control.

Things got rough in bed between Tim and I one evening. It wasn’t long before I began squeezing his balls a bit too hard. He winced and told me to be a little more gentle. This only made me squeeze him harder, my nails digging into his nut sack. “Like this?” I asked and he whimpered. “Aww, okay I’ll stop.” I told him and held his balls tightly in my hand. My nails had left white marks in his balls. I knew they must be hurting, but only a little bit. I had to make it worse. I held his balls and gave them a slap, making him jump. Seconds later he began begging me to stop, as he tried to curl up in a ball. It was fun watching him in pain. I loved listening to him beg. Without hesitation, I did it again making those big balls red. I got a peek of his puckered asshole and lost interest in his balls. His balls were finally free from my tight grip. I allowed him a few seconds to massage some of the pain away before his first anal pegging would begin.

Only a few moments had passed before I pushed him face down and gave his ass a hard slap. He shot me a look of unexpected shock. I commanded him to hold his ass open for me. I let out a little laugh of pleasure. “Somebody is going to get a good ass pegging! I exclaimed, as I got out my strap-on. Slowly I slipped into my beautiful strap on. He knelt there, holding his cheeks apart and telling me this was the right time. I laughed and asked him, “When is there a right time? Better now than later.”

I knew he had never done anal before and he thought it might hurt. I grabbed a ball gag and shoved it into his mouth. I didn’t want to have to listen to his whining the whole time I was taking his virginity away. Slowly I poured some lube into my hand and with the excess I shoved my finger into his ass. Like a little bitch, he cried out, as his hole clenched tightly around my finger. His ass was so tight. I knew he really was an anal virgin and I was going to pop his cherry. If he was like this with just a finger then he’d be ripped in two by my pegging him with my strap on. “Away poor baby.” I said, as rubbed his back to calm him down. I wanted him to relax his ass muscle, so I continued to massage his tight little hole with two fingers. Opening and closing my fingers, I scissored my fingers back and forth until he was looser. He started to enjoy the tight anal massage. He only sighed and let out a little whimper, as I removed my fingers.

He knew what was coming and would only be seconds later that his hole would be filled with something much bigger. I lubed up my strap on and began pushing it into him. He tried to move away and cried out, as I stretched his hole wider and wider. I got all of it in him and began fucking him. Fucking his virgin hole for the first time. In perfect rhythm , he slowly backed up against my body to take the full length. Moaning in pleasure, he rocked back, while I reached around for his dick. He was hard as a rock. I jerked him off while ramming his ass. He let out a loud gasp when I hit his prostate and buckets of pre-cum leaked out of him. I kept going at him. Slowly milking and jerking his dick, as I fucked his ass. He couldn’t resist the pleasure that took over his body, as he groaned and grabbed at the sheets. I felt him tense up, as his dick twitched in my hand. Moments later he started to cum. I rammed my strap on deep in his ass and kept jerking him off while his cum dripped over my fist.

He came for ages, as I used my strap on to milk his prostate dry. I pulled out of him and he just laid there totally exhausted. My hand was all messy and I wiped it clean on his stomach. Streaks of cum covered him, as I took off the strap-on while he caught his breath.

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Raven

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