# Kinktober Day 1: Pegging Author: LaVojeto Tags: Anal, Bear, Black Bear, LaVojeto, Male/Female, Orgasm, Pegging, Strap-On, brown bear #1 of Kinktober 2023 Happy Kinktober! Wrote this up yesterday; considering I work during the week I'll prolly be a bit late uploading these each day, regardless! These are very short, quickly written stories with no editing or review. Just writing to write. All characters within belong to me **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. Source: https://sofurry.com/s/P1EMVD81 Part of the series Kinktober 2023 Next: https://fse.anthro.fr/stories/2056765-kinktober-day-2-titfucking.md