Pegging a Beginner

May 24, 2026

College Girls, Phone Sex, Strap-on and Pegging

Pegging a Beginner

I had a chance encounter with a man at a bar last night. I walked in with the intention of pegging a beginner, and I wasn’t disappointed. He was wearing a normal shirt with low-rise jeans and work boots, and he seemed to be a couple of drinks in because he was leaning way too far forward to flirt with the bartender. She seemed eager to get him away, and in an act of pity, I decided to catch his attention.

I fluttered my eyes at him as I sat down right nearby, even though there was plenty of space for me to sit elsewhere. He seemed shocked, and did a double take when he pulled off my blazer to reveal a lacy black dress. My tits parted slightly as I lifted up my glass, not breaking eye contact with him until he decided to speak.

Pegging of a beginner, anticipation makes me soaking wet.

He did something different. He stuck his thumb in the belt loop of his jeans to reveal a black thong wrapping around his hips. If he was trying to shock me back, it worked. I broke eye contact to peek at his underwear, and realizing I fell for his bait, I broke into a nasty grin. It was time for us to go. I finished his drink for him, grabbed him by the shirt, and led him outside. He was eager to follow me, like he had been hoping for an encounter like this all night. With this boy toy in tow, I asked him with curiosity: “Has anyone ever pegged you before?”

“No,” he said, shyly. Perfect, I thought, my plan of pegging a beginner was at last coming to fruition. This was the second time he made me laugh, but now, it was out of pity. He was quick to respond. “Why are you laughing? I’m not ready for it yet.”

“You should have thought about that before showing me your little thong,” I said a little too loudly as we passed strangers in the parking lot. I pulled my keys out of my purse and unlocked my car. The back seats were already folded down to make space for sex, and on one of the seats, there was a large dildo. I was pegging a beginner now, but by the time I was done, he would be an expert at taking the strap.

There’s no getting out of it now.

He gasped as soon as he saw it, and mumbled, “I didn’t know they made them that big.” I ignored him while I crawled into the car, and motioned for him to follow suit. Yeah, I know I’m pegging a beginner, I can’t help being a little cruel and choosing the biggest dildo I could find for it.

I lifted up the edge of my dress to reveal that I already had the harness for the strap attached, and it took only moments for me to be ready to pound some ass. “Drop your pants,” I said, and he scrambled to listen. His clothes became decor for the floorboards of the car.

Pegging a beginner no longer.

Then, I had him kneel in front of my strap to wet it with his mouth. “You’d better do a good job,” I warned, “or it’s going to hurt. I don’t use lube.” This seemed to motivate him to really work his throat, and after he let out a harsh gag, I pulled it out. I made him turn around with his ass in the air, and his hole trembled in either fear or anticipation. He isn’t going to be a beginner at pegging for much longer.

I rubbed the head of my strap on his hole while my hand began to caress his balls. When he started to moan and get hard, I could see his ass loosening for me to take. Without warning, I shoved my strap into him and began stroking his cock. He arched his back in surprise, but then I could feel him buck his hips to meet me as we built a rhythm together. Before I knew it, he had taken my length, and left a mess on my car – and I pulled my toy out.

“Clean that up,” I said, dropping the harness. “And stop bothering the waitress. You chose to confide in your mistress. What did you expect was gonna happen? Before you know it, you’re going to be blindfolded at my mercy.”