Cherry Boy
By Indigo Skye
(MF, rom, first)


“It’s my first time. I’m a little nervous,” Michael tells me, unbuttoning his shirt.

“Don’t worry. I’ll be gentle,” I tell him.  “I know what to do.” But inside, I’m thinking, oh, shit. He’s a virgin? I’m screwed. What the hell do I do now?

“It’s not, uh, a problem…is it?” he asks.

“Of course not,” I smile, stroking his lean chest. “Everybody’s nervous the first time,” I reassure him.  Thinking, why didn’t you ever mention this before? I take him in my arms and give him a lingering kiss.  

“Even you?” he asks, with a crooked grin. Michael’s smile is what attracted me first- like the sunshine after a storm. 

“Yes.  Even me,” I tell him, laughing.  What I don’t tell him is that it was ten years ago, when I was only sixteen.  I’ve had a lot of experience since then, and a lot of orgasms.

“Tell me about it- your first time,” he says, lying back on my bed.

“I lost my virginity in the back seat of my car,” I tell him.  “Not very romantic, huh?”

“Did it hurt?” he asks, toying with one of my curls.

“Yeah.  Not as much as I thought it would…my boyfriend was sweet about it, though.  He was very gentle…but he didn’t really know what the hell he was doing, to be honest with you. There’s not much to tell. He was so excited it was over in, like, five minutes, so there’s not much to tell.”  We laugh together. “Don’t worry,” I tell him. “I’ll make sure you have a lot more fun than I did, my first time,” I say, unbuttoning the fly of his jeans and easing them down to his ankles.  He kicks them onto the floor. 

“I’m sure I will,” he smiles, and we share a long, passionate kiss. 

“We can go slow,” I tell him, stroking the smooth muscles of his chest.  “Are you sure you’re ready?” I ask.  We’ve been dating for a few months, and he had confided that a traumatic breakup with his last girlfriend had made him gun-shy.  I’d just been burned by a savage divorce, and was amenable to taking things slowly.  And so, for the past three months, we’ve been taking it slow, and falling for each other fast.

He nods.  “I’m ready.”  I’ve been waiting for this for ages, or so it seems. The first instant I met Michael, I wanted him. Now, all of my long chats and walks on the beach and marathon make-out sessions were finally paying off. To own the truth, I’d been feeling more than a little frustrated; impatient to take our relationship to the next level. All of that is about to change. 

Michael says, “I love you. I want my first time to be tonight, with you.” He frames my face with his hands and pulls me close for a kiss. “I trust you.” He slides his hands down my back, squeezing my ass, and then reaching under my skirt.  I’m wearing a little pair of pink panties underneath, with lace, and black silk ribbons.  When I flip my skirt up to show him, he swallows hard, and kisses me hotly.  I feel the bulge in his boxers grow, and caress his stiffening cock through the soft fabric.  “Show me how to make you happy,” he whispers.  I nibble at his earlobe, and make him shiver.

“Since this is your first time, why don’t you just lie back and relax, gorgeous?  I’ll show you everything you need to know to get me off hard.”  I slip my skirt off and it joins his clothes on the floor.  I straddle his hips, clad only in a pair of stockings, a black lace bra, and my lucky pink panties.  They say redheads can’t wear pink, but I make it work.

Slowly, slowly, I begin to grind the crotch of my silky panties against his cock. Teasing him a little with my tits, I arch my back and let him kiss my perky pink nipples. He cups my breasts in his hands, sucking and licking my nips eagerly. I feel the hard curve of his cock against my panties, rubbing harder. “Oh, God,” he gasps, his hips thrusting forward.  I reach down, take his cock out, and push my panties aside, rubbing the silken skin of his mushroom-tip over my clit.  I moan, and start to feel my juices spilling sown my thighs.  I bite my lower lip, and begin to tease his cock with my hot slit, grinding hard, and than pulling away at the last possible second. 

Michael loves to be teased, and to tease me- we’ve done everything but sex so far- lots of kissing and cuddling, some oral action, mutual masturbation; you name it. We’ve already had the safe-sex chat, as well, and are dating each other exclusively. We both got tested two months in, when it looked like things were getting serious. We’ve discussed birth-control, as well, and since I’m on the pill we decided in advance to forego the condoms in favor of a commitment. And so, in this moment, I revel in the skin-to-skin intimacy as I rub his shaft down the length of my juicy slit. He tongues my nipples hard, squeezing my tits together.  I stroke his face, and whisper, “Are you ready?”

“Yes.”  I lean close for a deep soul kiss, pressing against his chest and guiding his cock inside me.  He gasps.  His green eyes flutter open and we kiss that way, gazes locked, as I slowly take in the hot length of his shaft.  It leaps and thrusts joyously, hard and fast.  I match his quickening pace for a few minutes, backing off again when it feels like he’s getting ready to come. 

I sit up then, still straddling his hips, and begin to swivel my pelvis in slow figure eights.  “Not yet,” I whisper, when he tries to speed up the rhythm again. “I want this to last all night,” I tell him, stroking my clit with one hand as he watches me with greedy eyes.

“God, Jane, you’re so fucking sexy.  I’ve wanted this for so long, but I was afraid you’d laugh, or…” he’s so shy, it fills me with an unexpected tenderness.

“No. I wouldn’t do that,” I promise, and lean down to kiss him, letting him enter me all the way.  He moans with pleasure, and I grip his ready, hard shaft with my cunt, feeling him twitch and spasm with involuntary pleasure.

“So hot inside you, Jane...I...Oh, damn…” Incoherent with pleasure, he thrusts harder, gripping my hips with desperate strength and plunging in balls-deep, again and again.  I ride his cock, still working my clit furiously with busy fingers, until I come hard.  Pussy-cream drenches his cock and balls with the hot flow of my blissful joy-juice. 

“Fuck me harder…please!” I beg, bouncing up and down on his shaft and coming a second time.  I scream his name as I ride the wave of my orgasm, and he bucks beneath me, “Oh!”  Then he tumbles me over onto my back, without missing a beat, and I wrap my legs around him.  Still locked together in our passionate embrace, we struggle for control.  He holds me there, and starts to fuck me hard.  I spread my legs wide and finger my clit furiously as his thrusts fill me up, bringing me to the brink of another orgasm. 

I feel his pace growing frantic, and hold off, timing my next orgasm to coincide with his.  He cries out and strains against me, than fills me with a steaming flood of white-hot come as we climax together. 

After, he collapses in my arms.  He has tears in his eyes when he kisses me.  “That was so beautiful.  Thank you,” he whispers. I run my fingers through his long brown hair and smile.

“No…thank you,” I say, lifting one nipple up to be kissed.  He suckles softly there, then kisses his way up to my ear.

“You know something?” he whispers, “Next time will only be my second time, ever, and I’m feeling a little nervous.”  He gives me a crooked little grin. “I’m hoping you can help me with that.”

“Don’t worry,” I smile, reaching for his cock again.  “I’ll be gentle.  This won’t hurt a bit...”

© Copyright 2010 Indigo Skye

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