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Popping Her Anal Cherry

Category: Anal Sex
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“Nice meat, Pops…is that hard on for me?”

I opened my eyes, my hard cock still cupped in my palm as I sat nude in my hot tub. My son’s girlfriend, Dana was standing on the deck, smiling at me, naked.

“You’re blushing,” Dana giggled, which made her firm young tits jiggle invitingly. My manhood surged towards greater fullness, bobbing in the water as if greeting our guest.

“After what we’ve shared, I wouldn’t think that my catching you jerking off would embarrass you, and I know that you like seeing me nude. Though I think you enjoy it more when I tease you with just a flash of side boob, a nipple slip, or an up skirt glimpse…”

Her teasing was making my shaft thicken even more as I held it loosely in my fist.

“But you’re Phil’s girl, not mine…” I stammered, much as I had a month or so ago, when she had seduced me in this same spot, demanding that I be the one to deflower her. Phil had not wanted her first time to be with him, since he had also been a virgin. They had decided that keeping it in the family was best.

The sex had been terrific, but ever since, I had kept my distance, not wanting to interfere in their blossoming relationship. Temptation was often an issue, what with Phil and Dana sucking and fucking each other anytime, anywhere. Eighteen year olds have stamina and hormones to spare, and I was hardly in a position to criticize their passion.

I was sorely tempted to suggest that they practice a bit more discretion about where and when they attacked each other. I never knew whether I would come out the sliding patio door to find Dana sucking Phil’s long thin lance in this hot tub, or Phil fucking Dana doggy style on a lounge chair. I had also encountered Phil licking his own cream out of Dana on the dining room table; fucking her from behind pressed up against the kitchen sink; or being ridden cowgirl style by this hot teenager on my pool table.

That did not include the innumerable blow jobs I had witnessed. Dana had sucked Phil in pretty much every room of my house, without even pausing if I entered the room. She always swallowed his load before she would turn and smile hello at me, her teeth glistening.

“Earth to Pops…” Dana giggled, bringing me back to reality.

I realized that I had resumed slowly stroking my shaft, my eyes half shut, images of her nude or half dressed flickering in my brain. The casualness of her fucking with Phil might have made her nakedness commonplace, but a tiny bikini still made her awesomely sexy. I shook my head rapidly, clearing my brain, and moved my arm up and rested my hand on the rim of the hot tub.

“What can I do for you, Dana?”

Her smile beamed brighter. She stepped closer. I could now tell that her nipples were erect inside the fabric of the top. With each breath, they seemed to beg to be bitten.

“Pops…” she began again, haltingly.

I nodded my head once to encourage her. “Yes?”

Dana paused by the tub, which was set into the deck, the rim maybe six inches above the surface. She raised her foot with balletic grace and dangled a toe in the warm water. I was looking straight up into the V between her thighs. The slight motion had moulded the bikini bottom to her labia, creating a perfect camel toe. My little brain commanded my cock to bob in the water, provoking more giggles from my son’s girlfriend.

She nodded her chin once, as if deciding just to say what she had to say.

“Phil and I need another favour.” She paused again, biting her lip. This time, she crossed her arms across her torso, protective body language, but on this occasion, it just emphasized her heaving bosom.

“You know I’ll do anything I can to help you. Phil is my only child, and you are like a daughter to me.”

Dana’s smile beamed out to her ears. She relaxed her arms and stepped over the edge, sliding into the tub across from where I sat. It was wide enough so that our knees were almost, but not quite touching. The watery gap seemed charged with electricity. Gentle waves lapped across the exposed tops of her tits.

“Anything, really?” she asked in her little girl voice.

As she spoke, she slid a few inches closer to me. My cock showed its appreciation by nodding upwards further.

“What do you need? Money is not a problem, within reason.”

I had started a small computer business at the right time, and sold it at even a better time. Now I did a little consulting just to stay involved, and invested wisely. Though far from rich, I was comfortable.

Dana laughed loudly. “Oh, money has nothing to do with it, Pops.”

She grinned, sliding around the bench so that our hips were lightly brushing against each other. If I moved at all, my left arm would rub against her breast. I was still conflicted about going along with deflowering this girl, barely a woman, and was determined not to cuckold my own son. My hormones though thought differently. I could feel my scrotum tighten and the slit at the end of my cock starting to gape. Since I was staring across the deck, not daring to look at Dana, I could not tell whether or not she was fully aware of the excitement she was causing.

“I’m almost embarrassed to ask you this…” Dana hesitated.


“Well, since we’ve been intimate, I don’t see why not, though it is pretty personal.”

“You call me Pops. Don’t you think of me like a father? Daughters should be able to ask their Pops anything.”

Again, Dana chuckled.

“Not this question,” she replied finally. “I can’t imagine many daughters ask their Pops this.”

Now I just had to know…

“Don’t be afraid. I will never judge you.”

Dana squirmed nervously, causing her firm young boob to rub up against my bicep. Electricity shot to my groin, warming me faster than even the hot tub. I chanced a sideways glance. Her nipple was so hard that it was stretching the fabric, exposing a full side boob view. My tongue wet my lips. I thought I might be drooling a little. Most embarrassingly, however, my hand had started languidly stroking my prick without conscious direction from my mind.

“Oh, that’s good,” Dana said, again using that timid voice like a six year old caught sneaking a cookie.

“Out with it then.”

I still was not sure if she had noticed that I had resumed jerking off. If so, she had to connect it to her proximity. Yet she seemed to be the one who was afraid.

“I better get comfortable first,” Dana said, obviously stalling. “I’m feeling overdressed for this hot tub.”

She stood quickly and untied her top, flinging it over her shoulder, not looking back to see where it landed. I noticed she had no tan lines, at least not on her chest.

“That’s better,” she giggled as she sat down, even closer — our legs were overlapping. Any movement would start a game of footsie. A game which, given our situation, could only end up with two winners. I still worried though about whether that would leave Phil as a loser.

“You’re still overdressed,” I joked. “I’m fully naked.”

“So you are…” Dana giggled, now unabashedly staring at my erection. “Don’t worry; it’s nothing I haven’t seen before. And I quite enjoyed it then.”

She lifted her butt and her hands worked that girlish magic, then her bikini bottoms joined their mate over on the deck, in the pool, on a chair – neither of us bothered to look where.

“But you’ve enjoyed Phil since then. Just as much, if not more, I hope.”

“Of course I have. But I still like the looks of yours, Pops.”

“Dana, I only fucked you because you said Phil refused to deflower you. We can’t carry on past that.”

“Is that the only reason, Pops? Didn’t you also fuck me because you find me attractive?”

All I could do was sputter in response. Dana laughed deeply, her firm teen titties jiggling as if begging me to touch them. I resisted. Then I felt her palm brush mine off of my shaft.

“I can tell that at least part of you likes the way that I look.”

Dana slid her dainty fingers up the length of my cock, teasing the underside of my head with a fingernail. Now it was my turn to squirm, but that did not help resist her charms, as it simply resulted in my hips sliding under hers, and she was quickly sitting astride my thigh.

“Okay,” I finally gasped, “I like how you look. Hot young teen bodies turn me on.”

“Do you go into your den and jerk off while I fuck Phil? Oh, I guess you don’t need to say — that pulsing of your meat is all the answer I need.”

She swivelled her upper body and showed me a grin that could light up a city. At the same time, she was busy squeezing my aching manhood.

“Looking is one thing. Thinking is another. But, I …I …”

“You won’t fuck your son’s girlfriend?” Dana completed my thought as she giggled, her nipples drilling into my chest.

“Right,” I nodded. “It was a one time only thing between you and I Dana. I can tell by how you scream that Phil is quite capable of pleasing you. You don’t need an old fart like me messing that up.”

“Of course not, though I must admit that the thought of you picturing me while you come turns me on, Pops. Sometimes I think about that while Phil is fucking me. It makes me come even harder.”

“And louder?”

We shared a laugh. I suddenly realized that Dana was now sitting astride me, my cock rubbing her belly.

“Oh, you’ve heard?” she replied, which led to another round of laughing.

I was aware now of how her nipples were rock hard, and the flap of skin that connected my tip to my shaft was tingling from the friction of her dewy tummy. Maybe I would ejaculate from the rubbing. Cleaning the tub would be less difficult than living with a secret like cuckolding my own son.

It was almost as if Dana could read my mind.

“Don’t explode, Pops, I need you good and hard.”

“I thought I made it clear – you should be saving that tight pussy for Phil.” “Pops, I don’t want you in my cunt.”

“What, then…?”

“Phil wants to try fucking my ass, but is afraid because he’s never tried, that he might hurt me. He figures if you go first, my ass will be ready for his cock, and almost guide it in.”

“Afraid it doesn’t work like that…”

“Well, then, show me how it works, and I’ll teach Phil.”

Dana playfully kissed me on the nose. I noticed the spray of freckles along her nose, which made her seem even younger than eighteen. Her enthusiasm for trying new things was extremely sexy.

“I’m not sure that will work either…”

As soon as I said the words, I wished I had not. What if she asked me to demonstrate for Phil? Although he had watched the end of my one time first time fuck with Dana, I had not known he was there. Some things, a father should not share with his son.

“But, Pops, it has to be you. Phil insists.”

Dana ground her pelvis against my belly, painting her pretty face with a pout. She reached out and grabbed my hands, guiding them behind her, my fingers automatically tickling her vertebrae. She rose slightly and sighed gently as she settled back down, her shapely ass cradled in my palms. Instinctively, I tried to pull my hands free, but I was trapped between her butt and my thighs. My movement served only to spread her cheeks. I knew that this would open both her pussy and anus wider.

“Well, can’t have you taking this great ass out on the street looking to get it fucked, now, can we?” I said. “But we can’t do it in here — warm water isn’t the greatest lubricant.”

“Oh, goodie!” Dana squealed. Leaning backwards, she clapped her open palms together like a little girl on her birthday. “Where will we do it then?”

I knew she really was an anal virgin not from her enthusiasm, but from the fact she did not pick up on my lubricant comment.

“No point going to my bedroom — no lube there, either,” I mused out loud. “Does Phil use any?”

Strangely, this mention of Phil as a young stud, the acknowledgement of their fucking, caused my balls to dance, my weapon to stand straight. I leaned forward and licked a droplet of water off of Dana’s left nipple while she thought.

“No, Pops, my pussy gets so wet from foreplay and licking that he has no trouble sliding right in.” she said, sighing as I suckled her right teat.

“Assfucking is a bit trickier. Good thing he didn’t try that dry — you wouldn’t sit for a week, if he ever got his helmet past your ring.”

A brief flicker of a frown flowed across Dana’s face. She glanced over to the picnic table.

“Suntan lotion?” she suggested, spying a bottle.

“Too many strange chemicals — never tried it, but I’m sure that it would irritate your membranes.”

This time, she pouted pensively.

“I need to do it now — right now – I can’t wait for you to run to the store for supplies.”

She sounded eight, not eighteen, but the way she was bouncing up and down on my lap was charming. My snake was certainly charmed.

“Much more of this, and I’ll be spent before we get started.”

“Oh, Pops…don’t pop yet!”

Dana placed a hand on either of my shoulders and levered herself slowly up and out of the tub. This allowed her nipples to graze across my face, and my breath warmed the valley of her breasts. She ended up standing on the bench, her dripping wet pussy just higher than my head. Droplets bounced off my nose, teasing me with the scent of her excitement.

I craned my neck upwards to try to lap at that juicy cunt, but Dana chuckled and reached down, pulling me up by the arm. We balanced precariously on the bench, her feet planted just outside mine. The space was tight. My cockhead bounced off her belly with each breath, and her nipples once again were drilling into my flesh.

Dana looked up at me, her perfectly white teeth dazzling me with her smile. The humidity had flattened her hair, so it framed her face, emphasizing her youthful vitality.

“I’m too old for a treat like this.”

“Nonsense. You told Phil that the doctor just gave you a clean bill of health.”

Dana’s fingers caressed my bicep.

“You know that’s not what I mean. If I died fucking you, I’d be a happy man. It’s the fact that you’re just too young. I should find someone my own age.”

“If you did, then we could learn from her too. She could teach Phil.”

She rotated her hips, grinding against my erection.

“You really are a dirty girl, aren’t you?”

“That’s how Phil likes them. I think he takes after his Dad.”

Without thinking, my right hand curled behind Dana, and I gently slapped her rear.

“That’s what dirty little girls deserve,” I explained.

“What else do they get?”

Before answering, I gave Dana another love tap, this time with a bit more force. Still, she kept on grinning.

“Nasty little girls get fucked in the ass,” I growled.

This time, I followed up with a pair of powerful slaps, hard enough to force her body tight against mine. I moved to kiss that sweet smile, but she caught my lower lip in her teeth and nibbled. While I paused to lick up the blood that flowed, she twisted away and leapt onto the deck. She giggled as she ran towards the house. I climbed more cautiously, and then gave chase.

As Dana ran towards the house, she stumbled, which allowed me to catch up with her. I scooped one arm around her waist and spanked her butt with the other. She quickly wriggled free with a giggle and ran ahead, turning to grin at me.

“You coming, Pops?”

“Just breathin’ heavy, darling.”

I gave chase, but she was scooting through the kitchen before I was inside the room. She stumbled over a foot stool in the family room, sprawling onto all fours, her tummy balanced on the seat. This presented her naked ass high in the air right in front of me as I entered the room.

“Caught you now.”

Dana just giggled in reply, making no effort to get up and run away. I was too consumed by lust to worry about whether or not Phil, or any visitor, might catch us fucking in this bright exposed room, surrounded by windows on all sides.

I ran one hand along her back, from the curve of her posterior up to her neck, and kneaded her shoulder, while my other fingers massaged her front, stroking along her jaw line, along the edge of her throat, lightly caressing the swell of her tits, barely brushing her excited nipples, and then settling in her belly, rubbing in circles.

Gradually, my fingers worked towards the inside of Dana’s thighs. Her legs spread open as she shifted her feet just an inch or so.

“Fuck me with your fingers, Pops,” she moaned.

First, I teased her labia, plucking at them like guitar strings. Dana’s hips squirmed, and then her rear started humping back, bouncing into my hard cock.

“If you touch my clit, I’m going to come,” she panted.

Instead, I began thrusting into her vagina with three stiff digits, sliding through her wetness below her love button.

“Fuuuuuuuck me…..” Dana growled.

“I’m going to fuck you all right…but in your ass. If you beg for it.”

“Oh, please, Pops, fuck my ass. Make it yours, so that then I can give Phil a nicely broken in ass to fuck.”

I slapped her butt as she humped against me, while the fingers of my other hand drove deeply into her.

“I think you might be wet enough to just use your natural lubrication soon.”

“If I cream, it will be even better. Please…make me climax and then take my ass cherry, Pops.”

Dana was gasping for air as she spoke, wriggling her pelvis, grinding my whole fist into her cunt, and trapping my shaft between her ass cheeks. The revolving action of her hips caused her glutes to polish my shiny lance. I knew that if I did not fuck her soon, my seed would spurt out all over her back, disappointing her and causing me to miss the once in a lifetime chance to fuck her virgin ass.

After the next thrust of my fist into her cunt, I skimmed my hand along the length of her gash, not pushing inside until two fingertips grazed her bobbling little clit, engorged with excitement like the vestigial cock it was. As my thumb and two fingers plunged deep, I twisted her bud.

Dana came with a scream, flooding my fist to the wrist with her gooey goodness.

I eased my body back from her upended ass, withdrawing my arm from between her legs, scooping her ooze along with my fist, coating up inside the curve of her glutes, and finger-painting the pulsing rosetta of her excited little anus.

“Fuck me now, Pops, take my ass cherry, I need it.”

I could feel the spasms of Dana’s orgasms climaxing in a series.

“Are you sure? Your ass is only virgin for one man.”

“You are the man for deflowering me, Pops; you know that, now fuck me!”

So ordered, I pushed my thumb slowly into her ass. Her ass was unbelievably tight but I continued pressing gently so that her sphincter relaxed and opened, then with a grunt, she responded as her muscles spasmed, sucking my appendage deeper. Dana pushed back as my fingers caressed her puckered asshole. Most women, especially those not experienced in anal play, were startled just because of the unfamiliarity, but Dana took to it like a natural. A moan escaped her lips as I began to press my thumb deeper into her tight hole. She pushed her hips backward and I slipped another finger into her. With two fingers, I stretched her ring open.

“Good…” Dana panted. “Make it wide enough to fit that fat fucking cock of yours Pops. Then Phil will have no trouble when he tries.”

My son was a bit longer than me, but not as thick. Our two cocks had pleased his girlfriend in different spots.

“Ohhh, Gawddddd…” Dana screamed as I felt another orgasm shuddered through her body.

This wave of motion pushed Dana’s butt back against the tip of my cock, which had been hovering just brushing the curve of one cheek. The mushroom shaped head slid easily into the warmth of her ass cleavage. My arm blocked it from entering Dana’s anus, but we both enjoyed how she ground her flesh against mine, twisting her hips as only cheerleaders and gymnasts know how. I had forgotten the multitude of joys possible only by fucking a young woman.

“Are you ready for me to fuck your ass?” I asked, and then spanked each of her buttocks twice more.

“Make me ready for your son, Pops, fuck my ass hard.”

“I need a condom” I thought out loud. Anal sex was nothing to fool with when it came to hygiene, and as a responsible parental figure, I had to teach Dana good habits to share with my son.

“I…know…” Dana panted. “Phil…thought…of… that…my purse is on the counter.”

Through herculean effort, I was able to reach across the family room to the counter which separated it from the kitchen, still keeping my fingers kneading Dana’s ass, making sure that it was both open and wet for my fucking. However, when I dug blindly into her sack for the familiar foil wrapper, my hand also located a tube of jelly. Phil had been a boy scout, just like his Dad, and believed in being prepared. Unless it was a case of stray leftovers from one of Phil and Dana’s pool parties. Some of those I had missed chaperoning. I made a mental note to observe them more closely.

I tore a packet open with my teeth, and rolled the rubber down my aching shaft with shaky fingers. The anticipation of deflowering Dana’s anus was so great that I was afraid that even the slight touch of fingers to my flesh would make me explode prematurely. Lube spurted out, slopping off my cock onto Dana’s ass. I paused just long enough to scoop some of the goop into her crevice, trusting that my thrust would push enough gel deeper inside to assure a smooth glide.

“Come on, Pops, quit teasing me, shove that fat monster in,” Dana demanded. She was crazed by passion now. She had to have her ass fucked. She humped against my back in frustration.

I grasped each ass cheek in my hands and pulled them wide. I pressed my cock forward, letting the tip caress Dana’s delicate membrane, pushing against the opening, until the head slipped gently inward. I stopped and leaned forward, nibbling her ear. I shoved again, and my shaft slid part way in. I felt her sphincter tighten around my cock as she pushed her butt towards my belly, forcing me deeper.

“Cripes, Pops, you’re huge.”

Dana screamed. Whether in pain and pleasure, I had no idea.

“Should I stop?”

“Fuck, no, I need to come again. Fuck me more.”

Dana reached back and found my hands resting on her bucking hips. She guided one to her chest and the other to her cunt. I instinctively twisted a nipple a bit more roughly than her clit.

“Well, at least your ass isn’t virgin anymore, and Phil’s pole should slide in a lot easier.”

Dana groaned and thrashed about as I fucked her hard, holding her nipple and clit tightly. I no longer worried about whether I was cuckolding Phil, totally swept up by her enthusiasm.

“Are you going to come in my ass, Pops? I want to feel you fill that condom.”

Her muscles clenched my cock tight inside her, and then relaxed just enough for me to withdraw halfway and pump deep inside her again. I continued pistoning like this for a while. I stroked her nipples and clit.

Dana began rotating her pelvis, milking my cock within her tight asshole. As she swivelled her hips, her sphincter relaxed and I was able to fuck her more vigourously.

“Oh, fuck, I’m coming again,” Dana screamed.

I knew I was not going to last much longer. Dana squealed and thrashed about, barely able to stand, her hands reaching out to the foot stool for balance. I concentrated on fingering her clit, while still pounding my cock into her wide open asshole. I pushed harder, exploring the depths of her bowels. Her body continued responding, in a new sort of dirty dancing as she screamed louder, insisting that I come in her ass.

“Nooooowwwwwwwww,” she groaned, arching her back and reaching a hand up underneath her body to squeeze my balls.

That was all that it took to make my load explode out of my sac, surge up my shaft and burst out my slit, filling the reservoir of the rubber. Dana’s muscles continued kneading my shaft until every drop spewed out. Only when one final climax shuddered through her entire body did she collapse across the foot stool. My subsiding erection slid out of her ass she fell forward. The condom was full, but intact. I had successfully deflowered her ass cherry and she was once again just my son’s girlfriend.

“Thanks Pops,” I heard her moan sleepily as I crept out of the room towards the shower.

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