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Day 1: Pegging

"Alright, take a deep breath," I told the black bear, patting his ass comfortingly as I rubbed my lubed up silicon cock against his ass. Taylor had been a longtime friend of mine, so when he came to me to ask if I could take his V-card, I felt touched, flattered and nervous. I didn't have much experience being the one pushing myself into others. But the black bear, like I said, was a dear friend. We'd fooled around plenty, so I was willing to push my comfort zone just a bit.

"Ohhhhhh fffffffuck...!" Taylor squeaked as I pressed the tip of my purple dildo against his fleshy ring. It popped in, and I could feel him tense up.

"Don't tense, it'll hurt more," I chided him, gently massaging his back.

"Speaking from experience?" he snarked, and I flushed, rolling my eyes. Holding onto his hip, I gingerly began to push forward. A soft moan flooded the room, and I felt a tingle in my crotch and chest. There was a feeling of...of power. Pushing into him like this. "Oh fuck me..." Taylor groaned.

"Oh, I will," I teased, reaching around to grab at his cock. It was hard and throbbed in my hand, and when I gave it a stroke, I could already feel some wetness dripping from the tip. Gripping it firmly, I gave it a long, slow stroke from base to tip, working the pre around his glans before sliding back down. I could feel him shudder underneath me, his little whimpers sending shivers down my spine.

"Almost there..." I breathed, gently easing myself further into him. His ass slowly swallowed my prosthetic penis, and pretty soon my hips were pressed to his. Grabbing his hips, I gave them a quick squeeze, letting Taylor adjust himself to "my girth." "How you feeling?" I asked. He only nodded and whimpered. "You good if I start...err...humping?" I questioned. Another nod and whimper.

Pulling back, moving carefully and slowly so as not to hurt him, I waited until the very tip of my dildo remained inside him. Then I pushed back in. My stomach flipped when he let out a little mewling whimper. It felt so dominating to be in this position. So powerful.

I began to thrust into him at a slow, yet steady pace. The wet slaps of his ass clapping against my hips as I pounded his ass filled out room. His groans of pleasure were musical. My thighs burned. Holy fuck did my thighs burn. My grunts were a mixture of pleasure tickling me in a new way, but also the lack of exercise that had dominated my life.

Holy fuck this was exhausting.

"Oh my fucking god...harder...!" Taylor squeaked, pushing back slightly. I grinned, panting softly as I grabbed his hips and began to slap at his ass a bit harder. Each blow sent his asscheeks jiggling, and the claps were loud and squelchy as I fucked him. His moans came louder and more frequent. I leaned forward, my wrist burning as I stroked his length underneath him.

This was the most exercise I'd gotten in awhile.

"Oh fuck...oh fuck I'm gonna...cum...!" Taylor squealed, and I quickened the pace of my pumps and strokes. I felt him throb in my hand, and soon my fingers were coated with his warm, sticky goo. His voice went to a falsetto, and I held myself inside him as he unloaded himself onto the bed underneath him.

Pretty soon he was shuddering and twitching, and I carefully extracted myself from him. Taylor sighed and rolled onto his side, and I flopped onto his bed. I was tingly between my thighs, and part of me wanted to get off right then and there. But as I looked at the mess on his bed (the giant cum stain), I giggled and glanced over at him.

"Best clean that up before it stains," I told him.