Kevin’s Ups and Downs Pt. 14


When she stood up, I filled my eyes, mmm, the sight of her nude body, and knowing that we had been in the grip of orgasmic completion just a few minutes ago, was intoxicating. Her face was full of joy, her eyes had a glow of sexual satisfaction.

“Now, what to wear? Maybe I should go commando, a short skirt, and my bare pussy, so close to being exposed to the world. Or, perhaps my black lacy thong, what would turn you on more Kev?”

I could see the mischievous look in her eyes, and I replied, “Whatever makes you feel the sexiest, baby.”

She smiled, went over to her dresser, and took out her thong panties and bra, both of them black and lacy. With a grin, she turned her back to me, pulling up her thong, and her purr of pleasure as she wedged the bottom between her ass cheeks made my cock stir.

She started to do her bra, I stepped up behind her and said, “Let me hook that up for you baby.”

I pulled her against me, my hands went around and under the loose cups, and I let my fingers stroke and caress the full weight of her breasts. She purred, pressing back against me, feeling my cock surging against her body. I took her nipples between thumb and forefinger, pulling and tweaking them gently, Deanna’s little moans of pleasure sounded.

“Ummm, I can feel you getting so hard baby, let’s go out for dinner first, you can feast your mind on my tight little pussy, just barely hidden behind my thong. Will that keep your interest baby?”

I growled, “Oh yeah baby, I’ll have a full head of steam on after dinner,” as I hooked her bra together.

She turned to face me, and purred, “That’s the idea, oh yes, don’t want you losing interest too fast.”

I said softly, “Never have to worry about that, you got me until you don’t want me anymore.”

Her voice trembled with emotion as she whispered, “Then I’m going to keep you for a long, long time.”

She watched, smiling, as I pulled on my shorts, packing my hard-on in, then working my pants on, adjusting the crotch, so my cock could subside.

“After dinner, I’ll be happy to help you get right back up, sweetheart, but for now, let’s go get dinner.”

Just down the block was an Italian place called Spago’s, with checkered tablecloths and candles, the romantic mood was perfect. I kept looking at Deanna, my mind thinking about that tiny thong, the lacy panel where her sweet pussy lips were nestled, and that strip of fabric between the cheeks of her ass. Oh yeah, after dinner, I would be right back up, my 18-year-old hormones were in overdrive, eager to make up for lost time.

After dinner, we hurried back to her house, it was almost 7 PM. She turned to me, her clothes flying off. She left her panties on, cocking her hips, so I could drink my fill. With a grin, she turned her back to me, displaying her Queen of Hearts tattoo, and the thong disappearing between the glorious moons of her derriere.

She cooed, “Would you like to pull down my panties sweetheart?”

She didn’t need to ask me twice, and I was on my knee, peeling down her panties, gently unwedging the thong from between the cleave, then kissing those sexy ass cheeks, as she cooed with pleasure. I pulled her cheeks apart, the sight of her tight, pink asshole made my cock throb, as I licked at the tight little pucker, Deanna’s low, continuous moans of pleasure şişli escort filling the bedroom. She moved over to her bed, and head down, ass up, she urged me on.

“Ohhhh, yes, god that feels so good, lick and finger my tight little asshole baby, I want you to take that last cherry! When I’m in the shower, I always play with my horny little pussy. Not just that, but I love to finger my tight little asshole, then shove a finger right up there! Pumping my tight asshole, and strumming my clit was beyond fantastic, I have to keep from screaming with pleasure as I explode! Now, I want you to take that last virgin tightness!”

I eagerly dove in, enjoying her squeals of pleasure as she felt my tongue make contact again. My face was nuzzling between the moons of her spread-open ass cheeks. My tongue swept over the tight pucker, licking at that twitching, inviting opening, then my tongue pressed against her, tightly. The tip of my tongue pushed inside, probing, pressing slightly into the twitching pucker, making Deanna’s body shiver with pleasure.

My cock was now steel hard, holy fuck, the idea that Deanna was going to give me her tight little virgin asshole gave me a raging boner. Sticking a finger in my mouth, I slobbered over it, then applied it, and pushed, slowly, slowly. She let out a grunt, of pleasure I hoped, and my finger glided slowly into the first knuckle. I felt her muscles gripping tightly at my probing finger.

Head down, ass up, Deanna moaned, “Yeah, yeah, oh yeah, oh yes, mmmm, I love getting my asshole fingered, keep fingering my baby, make my asshole all hot and eager for your cock.”

I pushed on until my finger was into the second knuckle. I started to rotate my finger, pushing out just slightly, her asshole was clenching at my finger, and I was doing my best to loosen it up, even just a tiny bit.

After a few minutes, Deanna cooed, “Ok baby, I’m ready, but as they say, be gentle with me.”

The sight of her on her hands and knees, her head down on a pillow, holy fuck, what an amazing sight. She reached back, cupped her cheeks, spreading them apart, displaying the tight pink pucker of her asshole, eager to get her ass fucked. I applied a generous coating of KY to my cock, and spread a large dollop around her tight rim, sliding my finger back inside to spread around the tight clutch of her virgin walls.

“Oh yeah, that feels nice. Kev, take my last bit of virginity, I’m so glad I saved it for my first real boyfriend,” she cooed.

I nudged my cockhead against the rose-shaped pucker, and pushed, slowly, slowly, suddenly the head popped in. Deanna let out a sharp gasp.

“Unnh, unhh, unhh” she moaned, “Hold up just a minute baby, I’m going to need time to adjust” she whispered.

“Take all the time you need baby, it’s not a race, your pleasure is what’s important. I’ll only go on at your request.”

I could see the side of her face, she smiled as my words told her she would not be forced. I brought my hands up, and ran them up and down her back, stroking her awesome body, eager to help her relax in every way. After a few minutes, she urged me on.

“Ok Kev, a bit more, slowly please.”

I pushed, slowly, slowly, I was now halfway in, and Deanna was making grunts, as I reached 5, then 6 inches.

“Another stop, please.”

I froze, waiting for her ass to adjust, fuck, the sensation of her tight virgin ass around my cock was something else. Never had I been in such a tight hole.

Deanna took less time, took a deep breath, and told me what to do.

“Now, bury it, let me have the rest,” she gasped, her hands gripping the sheets tightly.

I grasped her hips, and with a push forward, I was in, right to the balls, Deanna let out a small yelp, and I again stopped.

“Oh my god, my ass is so full. Kev, you’re such a sweet man, any other guy that I gave my ass to would probably end up raping my ass. Now, just a little bit more time,” she cooed.

After a minute, Deanna whispered huskily, “Ummm, mmmm, oh yeah, it’s starting to feel good, give me a slow, loving ride Kev, now that my ass virginity is gone, take it some more.”

I pulled back an inch and pressed forward slowly, getting a slow, gentle rhythm going. Deanna’s sounds were changing over to little gasps and what sounded like cries of passion.

“Umm, yes, oh yes, now that I’m loosened up, it feels better,” she cooed, “Keep going sweetheart, it’s starting to feel real good!”

Encouraged, I started to pull out a bit further, 2 inches then 3, burying it deep, speeding up just a little bit. Deanna was starting to make moans and louder cries of passion, as she urged me on.

Deanna growled, “Now, smack my ass, I want to get my ass spanked while you fuck me!”

On the outstroke, I aimed for that sexy ass tattoo, and my hand connected with the Queen of Hearts on her right cheek. She grunted, and I switched over and gave her left cheek a good whack.

Deanna growled, “More, I want more, give my ass a good spanking!”

Encouraged, I keep whacking her ass, alternating left and right cheeks, as she grunted and urged me on, my cock throbbed from watching the red handprints against the creamy whiteness of her smooth ass cheeks. I gave each cheek 5 whacks, and with her urging me on, I gave her 5 more whacks.

After 10 smacks of each cheek, she purred, “Now grab my hips baby, hold me tight, and really ream out my asshole, fuck, it feels so fucking good!”

Jeez, what we were doing was mind-boggling, I was happy to do so. I could feel the heat of her freshly spanked cheeks against my groin as I kept reaming her, the tight vice grip of her ass was clutching at my cock, working me up to another load. I heard the hot, juicy squelch of her pussy, her hand was cupped tight against her sex, masturbating furiously. I reached around, and gently removed her hand.

“Let me do that for you baby,” I whispered.

I cupped one hand around her mound, her pink, hard clit straining for my fingers, her juices coated my fingers, and I grasped her hand clit, and stroked it up and down, her grunts and cries of pleasure increased, and I could feel a massive load gather. I felt her hand reach back, cupping my balls, and giving me gentle squeezes. I could feel her clit twitching wildly between my fingers, then Deanna hit her peak.

“Fuck, fuck, fuck, oh my fucking god, cumming, oh my god cumming, fill my ass sweetheart fill me, fuck, fuck FUUUUCCCCCKKK!”

She let out a scream, her ass clamped even tighter around my cock, her orgasm making her asshole clench and unclench, and that took me over. I pulled her tight against me, drove in to the balls, and my cock erupted.

My growls of orgasm joined her sounds, as my cock jerked over and over, throbbing wildly and pumping a flood of cum, painting her dark cavern white with my load, both of us shuddering through body-wracking orgasms. When I had unloaded the last gush, I pulled out and flopped down, Deanna joined me and her eyes were close to mine, her smile told me all I needed to know.

“Perfect, so perfect”, she whispered, “just as loving and caring as when you took my pussy virginity. You really are my Prince Charming. I’m glad you’re mine baby.”

We drifted for a while, before she said, “Kevin, you don’t think it’s too weird that I liked getting my ass spanked?” At my assurances that I did not think it was weird, she went on, “I never got spanked by either my Mom or my Dad, they didn’t believe in physical discipline. A few months ago Chris and I were having a sleepover to celebrate our 18th birthday, we were born on the same day. We were fooling around, we were in T-shirts and panties, and she gave my ass a playful smack.”

“I jumped, but for some reason, it felt good. Chris must have sensed it, for she said, ‘Dee, how about if we get naked, and I’ll spank you a bit more?’ It sounded naughty, but it also sounded very exciting. It wasn’t long before my T-shirt and panties were on the floor, and I was on her bed, on hands and knees, naked.”

“I looked back at her face, she had a look of hungry lust, and when her hand made the first smack on my naked cheeks, it stung a bit, but I felt a fireline of lust starting up, and I cooed, ‘Oh yes, spank me some more’ and Chris obliged, each smack of her hand made me start to throb with lust, after 5 strokes on each cheek, my pussy was gushing like mad, then her fingers found my pussy, and she knew what she was doing, in 20 seconds, I was cumming like crazy, soaking her hand as my pussy gushed out my orgasm.”

“After that, she virtually was vibrating, we switched positions, and after 5 hard smacks with my hand on each of her sexy cheeks, accompanied by her grunts and cries of pleasure, I brought her off, enjoying the way her body shook and shuddered, her pussy juices pouring over my hand in orgasmic completion. That was the start of our relationship, we have been lovers since that time, and I hope to continue my relationships, with both of my fabulous lovers. Can you handle sharing me with a girl?”

I replied, “Baby, I’ll be glad to share you, you should have the right to make it with whoever you want.”

She cooed, “Oh yeah, such a Prince Charming. Maybe, if she is up for it, one of these days, she would like to have a three-way with us.”

She smiled, then she lay her head on my shoulder. My mind was really in a whirl. My Mom, who I promised to satisfy with whatever Deanna and I had done, and Deanna’s Mom Anne, who would also be wanting the same as her darling daughter had gotten, I smiled as I wondered if she’d ever had her ass spanked while being butt fucked.

Her Mom had said she wanted exactly what Deanna had gotten, so she was going to get 10 hard whacks on her sexy ass when I buggered her. Add in, her girlfriend Chris, who sounded like she would be up for a hot three-way, jeez, what a stunning turnaround. And, in the times that Monique would be visiting, and I’d have her and my Mom in a three-way, wow. It was an embarrassment of riches, and I hoped my cock would be up for all the hot pussy that was wanting to be satisfied.

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