“You comfortable, baby?”
Mia’s eyes were green and alluring as she knelt between my legs. I licked my lips, already leaking with desire and nodded. “R-r-ready as I’ll ever be,” I stammered. The summer day was hot, as a mild breeze blew through the open curtains over the bed. Mia was young and lean, in soft pink panties and no bra, her boyish breasts already glistening from the heat.
“It’s nothing to be nervous about,” she said and, something in the tone of her voice – a calm, steady presence – made me believe her. Mia was strong and confident, a skilled and experienced lover who ran a yoga studio across town. She knew about pleasure, how to give it, how to receive it, how to share it, and since this was all her idea, I was in her hands – literally!
We’d met at a horror movie festival in town, the only two people sitting in a theater at midnight, watching a bad movie about a really bad werewolf firefighter! We’d been dating ever since and, in her expert hands, I’d learned to enjoy the feeling of submitting to her completely. Just, not… this… completely.
“I know,” I said, nodding, naked and vulnerable before her. I was on my back, my knees bent and high in the air, already sweaty from the heat, head propped up with extra pillows to admire her serene beauty and young, caramel skin. “I just… I’ve never done this before.”
“That’s why I bought the most gentle prostate massager for your birthday, Dave,” she said, dragging out the little toy from the gift bag she’d presented it to me in just that morning. “Meet the Purple Pickle.”
I snorted; the description wasn’t that far off: it was soft and purple, with a slightly hooked end – like a fingertip curled to say “come here” – and flared tips on either side of the handle, presumably so Mia could hold onto it during the massage and press it in or pull it out. It was medium length, but looked thick.
“But don’t worry,” she said, lying it aside as she reached for a bottle of coconut scented lube. “We’re going to get you nice and ready before we play with him.”
I nodded and watched as she poured a quarter size dot of lube in her left hand before rubbing it to warm between both palms. When at last she used her right hand to grab my tender staff, it leapt at the touch. “Someone’s ready for this birthday party to begin,” she murmured, licking her lips as she began to stroke me in earnest.
“He’s been ready all morning,” I murmured, watching her expert hands turn my flaccid cock into something glistening, throbbing and magnificent. “In fact, he’s so ready, you could probably just finish him off like this!”
She laughed, squeezing the skin under my tip playfully. “I don’t want you to do anything you don’t want to do, Dave, but… trust me… you’re going to thank me when you have the strongest, biggest, most voluminous and exhausting orgasm of your life.”
“How do you know?” I asked.
“What?” she teased, winking at me. “You think you’re the first guy I’ve given the Purple Pickle to?”
Normally a comment like that would make me feel jealous, even inferior, but somehow knowing I was in good hands relaxed me. In fact, the thought of Mia with other men suddenly turned me on.
“Were your other… friends… this nervous?”
“Sure,” she said, softly, stroking me so gently I could feel her fingers up and down every inch of me. “It’s not easy for a guy to do for the first time, but I’m proud of you for trying.”
I nodded, smirking. “What’s so funny?” She purred, skin aglow with perspiration now.
“I see I’m not the only one excited about this.”
We both looked to see the front panel of her panties damp with desire. She peered back at me with that sexy, knowing expression. “Why do you think I kept them on, baby? I know how much it turns you on to see me get really, hot and dripping wet.” I shivered with her dirty talk, knowing it was just the beginning. “Ready for me to make you ready?”
I sighed and nodded. She’d dabbled in ass play before, teasing around the hole while she jerked me off or spanking me as foreplay, but now she drizzled lube down my tender taint, a delicious feeling in itself, to coat my puckered sphincter with the lube. I sighed at the exotic sensation and she smiled, ignoring me as she began to tempt and tease my hole with first one finger, then two. She was so gentle and persistent, I barely noticed when at last a single fingertip slipped inside my virgin butthole, making me gasp with delight as my cock twitched in ecstasy.
“This is just so stretch you out a little, baby,” she said, and Mia’s voice had taken on a soft, murmuring tone, as if I was no longer there. “You’re so nice and tight.”
I nodded, murmuring as well. “Stretch me, Mia.” My own voice was unrecognizable; hoarse and low.
Our eyes met above my sweaty body and she asked, “Is that what you want, baby? You want me to stretch this tight, tight hole?” I nodded, biting my lower lip as she did just that – squeezed another finger inside my ass. The bittersweet blend of pleasure and pain found me leaking from my cock tip, a clear, fine drizzle that pooled atop my quivering belly.
“If daddy likes that,” she said, leaning forward to tenderly lap at the drizzle with her warm, wet lips. “Wait’ll he sees what happens with a proper prostate massage.” I quivered with delight as she
slid her hands from me and wiped them off on her legs, leaving a glistening trail on those long, velvet thighs. Her nipples were hard, stiff and maroon, making me wish she was closer so I could suck and tease them in return for the pleasure she was giving me. But it was my birthday and Mia insisted that her gift was total indulgence, from start to finish.
I heard the “click” and “hum” of a vibrator and watched her bring the prostate massager into view. “I didn’t know it did… that,” I said.
“Oh it does,” she purred, coating it with copious amounts of lube. “And you’ll thank me for it.”
I nodded and waited as she slid the throbbing toy along my cock. “Ooooohhhh,” I sighed, melting into the already damp sheets. “Jesus, Mia, that’s beautiful.” She ignored me, nodding absently as she dragged it along my balls and down my sweltering taint until it rested against my puckering hole.
“Spread your legs for me baby,” she instructed and, eager to please, I did. “That’s right, baby, here it comes…”
The pressure was intense as the tip of the vibrator, much thicker than her finger, slid past my virgin threshold. I winced with that balance of pleasure and pain, then whimpered as momentum brought it in deeper, another two or three inches. I gasped and bit down on my lip and she held it there, the throbbing intense as my whole body tingled with the effort.
“How’s that baby?” Mia asked and my eyelids fluttered open and shut with ecstasy. “I’ll take that as a ‘good’,” she chuckled and, then, slid the toy an inch or two deeper. I gasped and squirmed and, instinctively, she used the opportunity to guide it all the way in. “Oh,” I gasped as she dragged it gently out. “Is this… what it feels like for you?” I asked. “You mean when you fuck me, Dave?” she asked, sliding it in, then out, then in, then out. “Not exactly, but… feels good, right?”
I nodded, our eyes meeting. I peered down to find her panties thoroughly drenched, to the point where I could see her glistening pubic hair pressing richly against the damp cotton fabric.
“Listen,” she said, sliding the toy the rest of the way in. I could feel it throbbing inside me, deep inside, as the thrilling sensation of being violated made my cock throb and leak. “I’m going to begin getting serious now, you ready for that?”
I nodded, panting. “What… what does that mean?”
“It means I’m going to begin pressing the tip of this toy against your prostate, and you will feel magical, wondrous things, okay?”
“Okay?” I said, nodding uncertainly.
“And at the same time, I’ll be stroking your cock so that you come so gloriously, you’ll thank me forever, okay?”
I chuckled. “I can’t argue with that,” I murmured, nodding.
“Okay then,” she said and, gripping my cock in one hand, pressing a finger against the base of the Purple Pickle with the other, she smiled. “Then let’s get this party started.” I lay back, eyes shut and stinging from sweat. The breeze blew in, the curtains rustled and down the street a car horn honked. I felt the pressure between my legs intensify as she pressed the toy deeper, deeper, until I flinched and felt a glorious ooze of warmth spread from the chestnut sized prostate that hid deep inside. My cock leapt, my heart pounded and she never let up. “Yes, baby,” Mia panted, urging me on, “I can feel your cock throbbing with desire. Feel that, baby, feel it coming, feel it pulsing, you’re so close, baby, so close…”
With every syllable she teased my prostate, pressing against it, pulling away, short tender jabs and long, lingering patches where she left it in place, the throbbing energy making my cock weep as the puddle on my quivering belly filled then overflowed down my sides. I had never lasted this longer before, and credited Mia’s tender hands and gentle pace for the accomplishment. But I knew it wouldn’t be long now and, from the way my body was reacting – flushed skin, trembling limbs, leaking cock, panting breath, little moans and whimpers – Mia knew it, too.
“Come on, baby,” she urged me across the finish line, kneeling higher so I could watch her taut, tiny breasts jiggle with those pert, maroon nipples shimmering with sweat. “Come for me, baby. Come so hard you can taste it on your lips. Come for me, come on baby…”
As her voice grew hoarse and distant I could feel the orgasm swelling, hot and thick and powerful. When it came I screamed, a first, as hot, white, milky ropes shot across my belly, my chest and even onto my chin. I gasped and quaked and Mia knew just how to ease off and lay on as the throbbing toy milked endless spurts from my throbbing, spitting cock.
I gasped as she rode out the tenderness and sensitivity before gently pressing the toy against my prostate one long, last time. My teeth chattered, my cock splattered, my body writhed as I gripped the damp, twisted sheets with white knuckles until I begged her to stop.
“P-p-please, no more,” I panted and, immediately, she slid the toy from deep inside of me. Her right hand still gripped my staff, milky and coated with a generous icing of my own spunk. Tenderly, lovingly, she enrobed my pink, withering cock with cum before bending low and sucking it clean with her ripe, tender lips. When at last I was sated, soft and sweaty and spent beneath her, she slid along my side and kissed my lips. I could taste myself on her, musky and rich, before she slid in the crook of my arm and whispered in my ear, “Happy Birthday, baby.”
I chuckled and turned to face her. “You were right,” I croaked, still struggling to catch my breath. “I’ve never felt anything like that before.”
“I’m glad,” she murmured, eyes drowsy.
“You won’t be,” I teased her, “when I ask you to do it every day for the rest of my life.”
Want more FREE erotic short stories?
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- The Orgasmic Nipple
- Dominating the new girl
- A Prostate Exam with the naughty nurse
- Brutal Dildos: an erotic story about a couple and their shared love for dildos