My second pegging experience from college [MF]
A few weeks had passed since Lila (F22) and I (M18) hung out at her apartment, watched Amadeus that turned into a make out session, and eventually led to me losing my pegging virginity. We slipped into a comfortable Friday rhythm. She would invite me back to her apartment, we’d order pizza, cuddle on her couch for movies, and then eventually make out if we weren’t getting into the movie. This was followed by her inviting me to sleep over, which I never refused. The intimacy was pretty vanilla compared to my first visit to Lila’s apartment but was very enjoyable. Sometimes she would ride me deep and steady while I gripped her hips, her moans filling the room as she grinded down on me, or I would take her from behind with her face buried in the pillows, thrusting hard until we both finished together, sweaty and satisfied. It was always intense and passionate, but something was missing — that raw edge of her dominance that I couldn’t stop craving.
During the week we also started sneaking quick,
risky moments in the practice rooms after rehearsal. I’d look forward to her surprise
visits while I was trying to practice. Sometimes Lila would sit and give some constructive
criticism and other times she would play with my hair while I played, which was
her playful hint that I needed a break. She would push me against the wall,
drop to her knees, and give me slow teasing blowjobs. The thrill of possibly
getting caught made those stolen minutes incredibly hot, but they only left me
wanting more of her control.
That night we were halfway through The
Blair Witch Project when she suddenly paused the movie. She turned to me
with that playful, knowing smile and ran her fingers slowly up my thigh.
“Joseph… I’ve been thinking about that first
night you came over…” she murmured. “Have you?”
My heart jumped. I nodded, heat already rising
in my face. Trying to keep my cool.
“Good,” she whispered as she reached over,
cupped my chin and gave me a quick kiss. “Go to the bedroom. Strip and wait for
me on your knees.”
I obeyed quickly, heart pounding as I knelt naked on the carpet beside her bed. Moments later Lila stepped in wearing only a tank top and panties. The Doc Johnson UltraSkyn strap-on was already buckled around her hips, the thick, realistic dildo swaying heavily with each step. She lit a purple candle before walking towards me.
She stopped right in front of me, the tip just inches from my lips. “Don’t just stare at it cub” she giggled. I froze. I had never sucked a dildo or anything before, and a wave of nervous hesitation hit me hard.
Lila noticed and gently cupped my cheek, her
thumb brushing my jaw. “Hey… it’s okay,” she said softly, her voice warm and
patient. “This is new for you. Just relax. Breathe through your nose, keep your
jaw loose, and take it slow. I’ll guide you the whole way. You’re safe with
me.”
Her reassuring words helped. She lightly rested
a hand on the back of my head and brought the warm tip to my lips. I opened my
mouth tentatively. The smooth silicone was surprisingly warm from her body heat
and had a faint, clean, slightly sweet taste. It felt firm yet soft against my
tongue as I wrapped my lips around the head. The texture was incredibly
realistic — velvety skin-like material with subtle veins that dragged lightly
over my lips. I sucked lightly at first, unsure, but she murmured gentle encouragement.
“That’s it… good boy. Use a little tongue. Nice
and slow. You’re doing so well for me.”
Bit by bit, with her soft guidance and steady
praise, I grew more confident, taking more of the dildo into my mouth. The
weight of it on my tongue, the faint scent of her skin mixed with the scent of
her candle she had lit (it was purple so I think it was lavender), and the
quiet, wet sounds of my sucking filled the room. She gently rocked her hips,
guiding me until the hesitation melted away.
After a few minutes she pulled back, eyes dark
with lust. “On the bed. Face down.”
My heart hammered as I rose unsteadily from my
knees, the taste of the warm silicone still lingering on my tongue. The carpet
was soft under my bare feet for the few steps it took to reach the bed, but the
moment I climbed onto the mattress the sheets felt cool and smooth against my
heated skin, a sharp contrast that made me shiver. I slid the pillow under my
hips like she’d taught me last time, then lowered myself flat onto my stomach,
arms stretched out ahead of me, cheek pressed into the cool fabric. The
position left me completely exposed, ass slightly raised, every nerve already
tingling with anticipation.
I heard Lila step closer, the soft creak of the
floorboards under her bare feet. The mattress dipped behind me as she climbed
up, her weight shifting the bed in a way that made my stomach tighten. Then she
was over me. I felt her knees bracketing my thighs, palms planted on either
side of my shoulders and the heat of her body radiated against my back before
she even touched me.
She lowered herself slowly, deliberately, her soft, warm breasts pressing first against my shoulder blades, then flattening fully as she settled her full weight onto me. The smooth curve of her belly molded to the small of my back, her hard nipples dragging lightly across my skin with every breath, and her smooth thighs squeezed gently against the outside of mine, pinning me helplessly beneath her.
She reached toward the nightstand without
lifting off me. I heard the quiet clink of the lube bottle being picked up,
then the distinct click-pop of the cap flipping open. A thick, wet
squelch followed as she squeezed a generous amount onto her fingers and onto
the dildo. The sound of her stroking it—slow, deliberate, coating every inch
with slick, glossy lube—filled the quiet room, each pass making a lewd,
slippery noise that sent a fresh wave of heat straight to my cock.
A cool droplet of excess lube landed right at the top of my crack and slid down slowly. Then her fingers were there, warm and gentle, rubbing the slippery gel in slow circles around my hole, teasing the sensitive rim until it glistened and relaxed under her touch. The lube was cool at first, almost shockingly so against my flushed skin, but it quickly warmed as she worked it in, the wet, slippery pressure making me involuntarily push back against her hand.
“Relax for me, cub,” she whispered, voice low
and husky against my ear. “That’s it… good boy.”
Only then did I feel the thick, now-glossy head
of the strap-on nudge between my cheeks, sliding easily thanks to the fresh
layer of lube. She pressed forward, slow and steady, the stretch deep and full
in this prone position as the realistic ridges dragged against my walls. Inch
by inch she sank into me until her hips were flush against my ass, her entire
warm, soft body blanketing mine.
Lila let out a low, satisfied groan right against my ear, then pressed her lips to the back of my neck in a lingering, open-mouthed kiss. Her hot breath fanned across my skin as she began to thrust—long, powerful rolls of her hips that drove the thick dildo deep inside me with a slick, rhythmic pressure. Each stroke pulled almost all the way out before sliding back in, the velvety silicone dragging deliciously against every sensitive spot. The weight of her body pinned me completely; her soft breasts flattened against my shoulder blades, her hard nipples tracing little lines across my back with every thrust. Her thighs squeezed tighter around mine, locking me in place.
She kissed me again, this time lower between my shoulder blades, her lips soft and slightly damp. “Fuck, you feel so good like this,” she groaned, voice husky and ragged. Another kiss, then another slow, affectionate presses of her mouth scattered across my neck and upper back as her pace gradually deepened. The wet sounds of lube and skin filled the room: the quiet schlick-schlick of the strap-on sliding in and out, the faint creak of the bedframe, and our shared breathing growing heavier. I could feel the heat of her arousal against my ass, the subtle tremble in her thighs, the way her hips rolled with smooth, controlled power.
Her hand slid underneath me, fingers wrapping firmly around my aching cock, stroking me in perfect rhythm with her thrusts. Every time she bottomed out, she’d grind her hips in a slow circle, pressing the base of the dildo against her own clit and letting out a soft, needy moan right against my skin before kissing me again. Sometimes a gentle peck, sometimes a hungry open-mouthed kiss where I could feel her tongue flick against my spine.
The pleasure built fast and overwhelming: the relentless fullness inside me, the hot drag of the dildo against my prostate with every stroke, the crushing weight of her body molding perfectly to mine, and the constant rain of kisses that made me feel utterly claimed and cared for at the same time. Sweat began to slick our skin where we touched. Her hair spilled over my shoulder, tickling my cheek, carrying the faint scent of her shampoo mixed with lavender from the candle and the growing musk of sex.
I gripped the sheets hard, moaning helplessly into the pillow as the pressure coiled tighter. Lila’s thrusts grew faster, deeper, more urgent, her kisses turning into little nips and breathy whimpers against my neck. “Come for me, baby,” she whispered hotly, lips brushing my ear. “I want to feel you fall apart underneath me.”
The orgasm crashed over me hard. I shook uncontrollably, crying out into the pillow as I pulsed in her hand, spilling across the sheets. Lila stayed buried deep, grinding slowly against me to draw out every tremor, her lips never leaving my neck and shoulders. Kissing, soothing, praising me in soft murmurs the whole time.
She stayed on top of me for a long moment afterward, still buried inside, gently kissing the back of my neck and trailing lazy kisses down my spine while we both caught our breath. “You were so perfect tonight,” she whispered, her voice soft and full of affection. “Taking me like that… letting me have all of you. I love how you trust me.”
Slowly, she eased out of me and rolled to the side. She grabbed a warm washcloth from the bedside table and gently cleaned me up, her touches tender and caring. Then she pulled me into her arms, my head resting on her chest as she stroked my hair and back.
“How are you feeling?” she asked quietly. “Any
soreness? Was that too much?”
I shook my head, still floating. “It was
incredible,” I murmured against her skin.
She smiled and kissed my forehead. “Good.
Because I’m already thinking about next Friday.” Her fingers continued tracing
lazy patterns on my back. “We should watch Hereditary next weekend.
It’s supposed to be even more intense than this one… and I have a feeling
you’ll be nice and relaxed afterward.”
I let out a soft laugh, already excited. “Yeah…
next Friday sounds perfect.”