Sally
Colby’s warm breath on my backside made me shiver. His hands spread my cheeks apart, and then I felt his hot mouth. He sucked gently, his tongue probing my virgin hole. It felt strange, but not unpleasant. I wiggled a little, feeling a strange pleasure building.
“Oh…” my voice trailed off.
His fingers joined his mouth, slowly pushing apart my cheeks as he sucked and licked. His fingers slowly traced circles around my hole, gently pushing inwards. I tensed up, but his soothing words and the gentle pressure made me relax slowly.
“Shh, baby. You’re doing so good,” I heard him say.
Colby’s finger slowly pushed in, past the initial ring of muscle. I hissed, feeling stretched and full. He stopped, allowing me to adjust before slowly pushing in further. He curled his finger inside me, hitting a spot that made me gasp.
“I want more,” I breathed.
“More?” He murmured against my skin, and I nodded.
“Yes,” I breathed out slowly, feeling a strange pleasure building in my belly.
Colby started to move his finger in and out, going deeper each time. I could feel my pussy throbbing in need. I reached down, touching myself as he continued to prep my ass.
“I want your dick, please,” I begged, shamelessly.
“So glad I brought the lube,” he whispered, then paused, grabbing the lube from his discarded trousers pocket.
“Get ready, gorgeous,” he said, squeezing a generous amount onto his fingertips, then slicking up his hard cock before pressing the tip against my asshole.
“Deep breath,” he instructed, and I obeyed, feeling him slowly push inside.
Tears pricked at the corners of my eyes as he entered me, filling me completely. It hurt like hell, a burning, stretching pain like I’d never experienced before. I whimpered loudly, trying to push back against him reflexively.
“Shh, baby, breathe through it,” he said softly.
Colby held still, allowing me to adjust to the intense burning. His large hands rubbed soothing circles on my hips and lower belly.
“Look at me, baby,” he commanded softly.
I turned my head to look at him over my shoulder, tears streaming down my face.
“You’re doing so good, baby,” he added, and I gave a weak smile.
“But… it hurts so much,” I whimpered as he started to move slowly, pulling back slightly then pushing in again.
The burning intensified, making my eyes water.
He froze again, “Baby, it’s always like this the first time. Do you want me to stop?” He asked softly, concerned.
“No!” I retorted, shaking my head.
“No?” he asked again, as if wanting to be certain, and then I nodded. “Okay, we’ll keep going then. You’re so brave, bearing through this pain for me. I’ll make it feel good, I promise.”
I nodded again, and he continued his soothing words. “Just breathe, baby.”
Then, he started to move again, his pace steady but slow, kissing my shoulder gently as he worked his cock deeper with each thrust.
Slowly but surely, the agonizing burn began to morph into an unfamiliar sensation-almost pleasurable. My body adjusted to his size, muscles relaxing incrementally.
His lips continued trailing tender kisses along my shoulder blade and neck, murmuring reassuring words between each thrust. “That’s my good girl…”
I started to relax more, the pain slowly ebbing away and being replaced by a strange, intense pleasure. Each thrust sent waves of sensation through my body, making me gasp and moan.
Colby reached around, his fingers finding my clit and rubbing it in slow circles.
“Oh god,” I moaned loudly.
My body started to move with his, pressing back against him as he thrusted forward. The pleasure built and built, his fingers on my clit and his cock in my ass driving me wild. I could feel my orgasm approaching, faster and more intense than anything I’d ever experienced.
“I’m gonna…” I paused, letting out a soft cry instead.
Colby
Sally’s tight ass gripped my cock like a fucking vice. Seeing her tears mix with pleasure as she adjusted to my size made my chest tighten – I’d never felt so fucking tender and turned on at the same time. Her moans were driving me crazy, making my hips thrust forward faster.
Damn it, she’s so small. Her back curves perfectly, leading to that round ass that’s currently stuffed full of my dick.
I watched as my length slid in and out, lubed up and shiny. She kept moaning louder, taking my length better.
“Does it still hurt, sweetheart?” I asked.
Her hair was messy and sticking to her face from the sweat, making her look even more adorable. She bit her lip, looking back at me with hooded eyes.
“N-not really,” she breathed out, her pink pout begging to be kissed. I leaned forward, pressing my lips to hers roughly.
“Want me to fuck you harder, baby?” I whispered against her lips, pulling back slightly to gauge her reaction.
My hands gripped her hips tighter, feeling her ass cheeks bounce with each thrust. She nodded shyly, making my cock twitch inside her.
“Use your words, sweetheart.”
“Yes,” she whispered.
“Louder,” I growled, starting to slam into her harder.
“Yes! Fuck me hard!” she screamed.
“Say ‘faster’,” I commanded, my voice hoarse with desire.
“Yes, faster please. Fuck my asshole faster.”
I watched transfixed as my throbbing cock stretched her tight little asshole with each powerful and quick thrust.
The way her walls clenched desperately around me, trying to accommodate my girth, was erotic as hell. Her ass rippled beautifully with each impact, turning dusky pink.
I let out a groan appreciatively at the spectacle.
“You’re taking me so well,” I murmured, running my hands over her marked-up thighs and plump backside possessively.
I could feel her getting used to my size, relaxing more with each passing minute.
“Turn over,” I ordered as I pulled out, and immediately she did as I said.
I carefully laid her down on her back, her legs still spread wide open. I used my discarded shirt to bind her wrists gently above her head, leaving her completely vulnerable.
Sally’s legs were so flexible that I could press them back until her knees touched her forehead, exposing her tiny, stuffed hole to me.
“Look at me, baby,” I instructed, pushing my length back inside her slowly, watching as her torn, puckered hole stretched around my thick width.
She whimpered, tears streaming down her face from the intense burn and the unusual position.
“Yes, you’re doing so well,” I nodded, with a small smile.
“I love seeing you like this,” I admitted huskily, my eyes locked onto her gaping, spit-covered mouth and splayed legs.
I slid my hand under her hips, lifting them slightly to change the angle, then untied her wrists which looked quite reddish now. “Now, let’s see how deep I can go.” I pushed forward relentlessly.
Sally’s mouth opened in a silent scream as my length disappeared inside her completely, her tiny hole clenching desperately around the base of my dick.
The sight of her completely dominated and filled had me on the edge. I started to move, pulling out slightly before slamming back in, over and over again.
“You look fucking stunning like this,” I growled, watching her expression as her mouth contorted in a mix of pain and pleasure.
Her legs began to tremble uncontrollably, her body struggling to handle the overwhelming sensation.
“Keep those legs up, princess.”
She bit her lip, trying to hold back her cries as I pounded into her mercilessly. My hips slapped against her ass, the sound echoing through the room along with her muffled screams. I reached down and pinched her clit, knowing the added stimulation would push her over the edge.
Her back arched sharply as she screamed loudly, her ass tightening around me like a vice. She was coming undone – legs shaking, body convulsing, tears streaming down her face.
“Fuck… Colby…” Her eyes rolled back slightly, the sight making my dick swell inside her tight hole. “Can’t take this any longer.”
I leaned down, my voice strained with effort as I asked, “Do you want me to stop?”
My hips slowed slightly, giving her a chance to respond. Her head thrashed from side to side, her breath coming in ragged gasps. “No… please… don’t stop.”
“You sure?” I growled, pulling out slightly before slamming back in, making her whimper and shake her head frantically. “You can take it, can’t you? You like it rough, don’t you?” I snapped my hips forward again, making her scream.
“Fuck me, Colby! Fuck meeee!!” She begged, her voice raw and desperate.
Sally’s hips lifted to meet my thrusts, urging me deeper. Then, I grabbed her throat, applying gentle pressure as I fucked her harder, the bed shaking beneath us.
“Like this?” I snapped my hips forward brutally, making the headboard bang against the wall loudly. “Answer me!”
Sally’s eyes rolled back slightly.
“Yes! Like that!” she screamed loudly, “Harder, baby! Make me scream!”
Her legs tightened around my waist, pulling me deeper.