Sharing Anna
A Fictional Story by Scott Frieh.
A few months ago I asked my wife if she’d ever had an orgasm with me, and she said, “Yeah, I think so. I’m sure I have.”
I calmly removed the harpoon from my heart. To be honest, I’d known already. Anna and I were eighteen-year-old virgins when we started dating, and I still don’t know how I snagged her. She’s a gorgeous strawberry blond with eye-poppingly pert natural breasts, nipples that point like crazy when she’s aroused, a tiny waist, and a butt that men and women stare at openly. I’m Mr. Average, and in some departments, Mr. Below Average.
She had absolutely never cum on my cock. After three minutes inside her, I was ready to shoot, and had to stop thrusting and try not to ejaculate. She’d generally whisper “Go ahead” during minute four.
And I had basically a boy’s equipment, as I knew from bitter experience.
On an August day when my best friend and I were fourteen, we went to his house after football, and his mother said, “You stink! Go shower, both of you!” I thought she meant one after the other, but in Nick’s bathroom he turned on the water and with zero hesitation stripped right in front of me. “Come on!” he said, and being new to team sports and startled to see a friend suddenly buck naked, I peeled off my clothes and got in with him under the spray.
I was relieved that his dick and pubes looked just like mine. We lathered up and scrubbed each other’s backs, and the shock had nearly worn off when he turned around with a boner. It curved up a good deal more than mine—like a banana, I thought—but was otherwise identical. He was oblivious about it. Sex being contagious, my dick started to fill out too. He didn’t seem to notice that either. That afternoon he asked his mom if I could sleep over.
And that was the first of many nights we jacked off together. I was surprised by how long he took to cum, and amazed by how much he shot—he always had to wipe the back of his head somehow. And I was flabbergasted, as the school year progressed, by the out-of-control growth of his penis, which he was more and more thrilled to show me each weekend. “Look out—it’s the Zook!” he’d say as it sprang out to its proud new length. (A guy on our team said Nick had a bazooka between his legs, and the Zook became more or less our mascot.) The last time I let him measure us, it was nearly three inches longer than mine. “Yours will catch up, definitely,” he said. But it was clear I was stuck at just over four inches, while the Zook showed no sign of stopping. By the end of the school year his banana shaft was impossibly thick. His balls were bigger. He had more bush, for Christ’s sake. Did he have a medical condition? Did I? The fact that I was two months older and an inch taller made his much bigger endowment maddening. I could stand to jack with him for a very short time. But after I came, I’d be lying there watching for another fifteen or twenty minutes, waiting for Nick’s big weapon to fire and wondering why the puberty fairy had passed me by. I couldn’t look at it and couldn’t not look at it, so when we were fifteen I stopped doing sleepovers with him. He was very upset and begged me for a year to beat off with him again. “Or just sleep over,” he pleaded. “I’ll keep my underwear on!” This was no solution. In his tighty whities Nick looked like he was trying to shoplift a potato. I quit football so that I wouldn’t have to see his junk swinging in locker rooms and hear the guys’ admiring jokes. We stayed besties, but I didn’t see him naked again for fifteen years.
This spring, the ten minutes that changed our lives came. I was scrolling through a collection of porn stories; the featured one was “Sharing Anna.” I clicked on it for the name, with no knowledge of wife sharing or cuckolding. But turns out it was my kink. It gave me a violent hard-on, and when the narrator’s best friend, not named Nick but similarly endowed, penetrated Anna, I shot a geyser of spunk, then lay paralyzed, shocked by the power of the story over me. When the fog lifted, I determined to give my Anna the gift of a bigger dick.
So when she was unsure if she had ever cum with me, I asked if she regretted never being with a better lover.
“No! You’re fine. I’m very happy with you.”
“But do you really want to go your whole life with one dinky little penis?”
“I don’t think yours is little, and yes, that’s fine,” she said, confusingly.
“It’s unfair. I wish you could have just one experience with a bigger guy who can last more than five minutes.”
“No! I wouldn’t do that, Terry, and that’s that.”
“But if we knew a big guy who was interested—”
“I am not interested at all.”
“…and was willing to show you what you’re missing—”
“Okay, changing the subject. Subject changed.”
So much for the direct approach, but I knew a side entrance.
* * * * *
Nick was the first person we invited over to check out the hot tub. “Not a hot tub guy,” he texted, “but Anna’s jambalaya fuck yeah ur on buddy.”
Nick has big dark Italian eyes, the devil’s eyebrows, and a cleft chin that had slain women in several countries, Anna very much included. I once mentioned that he had girlfriends in three cities and she said, “Well, yeah.” She and Nick had a years-long mock flirtation that was a flimsy cover for the real thing. If she could be persuaded to play with another guy, it would be him. She was so excited about the dinner that she got performatively calm.
She spent the week making sure everything was perfect, and when the big night came, she appeared with her special-occasion hair and makeup. Just before showtime, she changed into a clingy grey skirt and a demure, off-the-shoulder pink top that hugged her boobs. I like all boobs, but Anna’s are two in a million. Luscious globes, unruled by gravity, they test absolutely everyone’s ability to focus on a topic of conversation. She sipped a glass of rosé while she cooked, and whenever she reached for something, her top came up, and her belly button showed. Nick was going to get a raging throbber the second he saw her.
He showed up with a bottle of tequila, which we got into before, during, and after dinner. He helped himself to food and drink and, as the evening progressed, cast long, shameless gazes at Anna. We polished off the pink wine, and I passed around a vape loaded with some insidious kush, so by the end of dinner we were beyond buzzed. Anna was delighted to be near Nick. He told us, frequently losing his train of thought, about a recent trip to London, and yes, he had a girl in that port too; and he traveled too much to think about settling down. I knew this meant he was having too much fun conquering new pussy, foreign and domestic.
“Fuck yeah, Terr, Mr. Suburban Squire!” he said when I showed him the burbling hot tub out back. Then to Anna, “Hey, need help with that?” With her hands and breasts, she was trying to transport a new bottle of wine and three glasses outside. “I can do it no problem when I’m not high,” she said, mock-glaring at me, and as they pressed against each other to transfer the clinking service into his arms I felt like a visitor at the home of a giddily happy couple.
“Go on in!” said Anna, putting a hand on Nick’s shoulder. “You have to take a dip! That’s the whole point!” Nick repeated he wasn’t the hot-tub type, but his resolve had cracked. “Terry,” she asked, “do you have extra swimsuits? Yeah, you do.”
“No suits!” I said.
“Yes, you do!”
“House rule! No suits!”
“I ain’t goin’ nekked,” said Nick, “that’s for damn sure.”
“Nekked or undies, Nicky,” I said, unhitching my cargo shorts. “That’s the law. Come on, you’re the biggest nudist in the world. I’m goin’ in!”
He started pouring chablis and said, “Go on—you two go ahead. I’m the bartender, I’ll catch up.”
I was peeling off my socks when Anna turned, flustered, and walked back to the house, weaving so much I feared she’d smack into the glass door.
“Where’d she go?” Nick asked, tossing his shirt on a lawn chair.
“Uh, bedroom. Maybe she—Oh! A bra, maybe. She didn’t have a bra on.”
“A bra?” he said, gazing at the bedroom door with adolescent fascination. “Why? It’s just me.”
“Well that’s it, I guess,” I said. “She wouldn’t care with some rando she wasn’t crushing on. Come on, hop in. She’ll be back.”
“So I’m—wait—hold on. I’m her hall pass?”
“Uh … I don’t know. Take that up with her.”
He took that in as he dropped his trousers. Apparently he hadn’t changed his underwear since the ninth grade, as he was now standing in a pair of fly-front tighty whities, with a comically overstuffed pouch. So he was good looking, successful, and well endowed enough to wear the dorkiest schoolboy undies without shame; or maybe he just enjoyed the sight of them struggling to contain his meat.
We climbed onto the edge and dunked our legs into the swirling warmth. He held the bottle and two of the glasses he’d poured.
“For me?” I said.
“No, Anna and me,” he said. “Sorry, I couldn’t manage three without spilling in your beautiful thing here. Water’s good!”
The bedroom door slid open, and Anna came out minus her top, her undulating boobs now cupped by a pink bra. We stared at them, hypnotized like pimply teens as she made her way to the tub, very drunk and shy.
“Boys!” she said, discovering us afresh. One of the boys, the muscular, handsome one in bulging tighties who made her face light up, turned and hoisted his body into the water so she could remove her skirt in peace. I followed. She got up on the edge in her beige panties with the tiny bow, surveying the scene. Her nipples riveted Nick, now rigid and very visible in her bra, and I knew for a fact that The Zook was swelling to full size under the water. Anna lowered herself to her thighs into the bubbling warmth; just before the panties touched, her hand slipped, and she fell in with a splash.
“You okay?!” Nick said, swooshing to her side as she regained composure. I climbed out to get my own glass, then got back in at the far end. Nick and Anna were nestled together; he had refilled the glasses polluted by tub water, and they now clinked, grinning like Cheshire cats—a very handsome couple. The water seemed to be swirling us far out to sea as the first stars appeared.
“Anna’s in heaven,” I said.
She smiled. “I am. I got my two boys, my two crazy boys, and I’m drinking even MORE wine.” She threw an arm around Nick’s neck and playfully heaved her legs across his body so they rested on his lap.
“Oh, okay! We’re doin’ this!” Nick flashed me his ladykiller smile. “Cool.”
Anna said, “And we don’t have any life preservers on this tub, so—”
She froze, mouth agape, then looked across the tub at me, wide-eyed; she peered down into the churning water, where her thighs had settled on something astounding.
How had she not known he was hung? He bulged obscenely at pool parties, and in sweatpants was clearly descended from at least one horse. They had pressed together during a slow dance at our wedding, and I assumed the bride had learned why he was called the best man.
Caught—with a boner, with a freakish anatomical secret, with a crush on his friend’s wife—Nick leaned into the moment and nuzzled Anna’s neck, no doubt grinding the object of her amazement between her thighs. Anna leaned back and got lost in a swirl of pleasure.
Alone in the hot tub, I finished my wine slowly, then made my way toward the house, collecting the half-empty glasses and wet bra they’d left when I’d suggested they move the party into the bedroom. Nick had led Anna through the twilight, their transparent undies clinging, his mighty erection leading the way. I’d given them plenty of time to get started, but through the sliding door I saw him standing, still in his underwear, Anna sitting on the bed in front of him in her wet panties. She said something in an incredulous voice, and he replied, “Well, you never asked.”
I came in, and he flashed me that cocksure smile again and whispered, “Surprised.” Anna had stopped in mid-motion, holding open the waistband of his briefs, staring at the huge upturned beast she had freed. The damn thing had definitely kept growing since I’d last seen it. But now, in addition to the old stab of jealousy, it gave me a rush of team pride.
I set their glasses down, then set a towel on the lounge chair and took my seat. Anna was too incredulous to notice me; her mouth was slack, and she was grappling with a new reality. Apparently penises could differ from each other shockingly.
“Is it supposed to be like that?” she asked.
“Like what?” Nick said defensively. “This is … what a man has.”
He didn’t say “what a real man has,” but it kind of hung in the air.
She was still paralyzed.
“All yours,” said Nick.
“You can have fun with it, sweetie,” I said. “Just like sucking mine.” She glared at me, outraged: NO, IT IS NOT.
Nick went back to caressing the nipples he’d finally gotten to fondle in the tub, as his huge tool pulsed at Anna.
She touched its pink tip with a fingertip, studiously, then, convinced it was friendly, leaned in and touched it with her tongue. Apparently it was delicious. Nick exhaled with pleasure, and she took his whole bell-end into her mouth and gave it some affectionate suction. A little moan escaped her, and I saw she was petting herself through her panties.
She leaned in and tried to reach the shaft, and Nick winced. “Ah! Teeth! Watch the teeth.”
She withdrew, said “Sorry!” and kissed the head to make it better. “I’m new to this.” He was too big around to blow. She held the head in her mouth, loving it with her tongue while caressing his thick shaft with her fingers.
I was painfully hard in my boxers. My dick had never been so forcefully rigid, like it was turning itself into metal. I sat on my hands to prevent an accidental shooting.
“Hey, you got, uh…” Nick was whispering at me.
“Huh?”
“Condoms?”
“Uh…yeah, but, uh—”
“Run and get ‘em,” he said.
I wanted to say it wasn’t a good idea, but stood up, a spike in my underwear, fished a box from the nightstand and brought it to him.
“Oh,” he said. “Forgot. Never mind. Thanks.”
Anna disengaged from his knob. “What?”
“They’re his size,” he said. “It’s okay, I’ll pull out.”
He stepped out of his briefs, and Anna let go of her beloved long enough to slide out of her panties.
“I’ve got lube,” I said. “Want some lube?”
He was exploring Anna’s pussy lips with his fingers.
“Naw, I don’t think so,” he said. “We’re good.”
This was insanity. Anna’s vagina was used to me! He would need the whole bottle of Astroglide to penetrate her, if it were even possible. He was about to see how little room she had to work with.
“You want to try?” he asked her, softly. “Want to try some dick?”
“Uh…I do, but…” She was like a wary newlywed.
“Let’s try it,” he said. “We’ll go slow.”
“Uh…okay, try. SLOW. Very slowly.”
She scooched up on the bed and leaned back. Her eyebrows were knitted with worry, but her legs spread into a wide, welcoming V, spreading her meticulously groomed vulva for him.
* * * * *
A few moments later, Nick eased his hips forward, and my lounger officially became a cuck chair. I saw every detail when his big cockhead parted her lips, as he made sure my sightline was clear. Once again my teen J.O. buddy was performing for me.
Even just his dome end was a massive invasion. Anna’s mouth dropped open into an “Oh!” She pushed against his chest and said, “Hold it! Just a second—hold on.”
“Take it out?”
“No, just…”
“I can take it out if you need me to.”
“No, no, it’s good, just…wait a second.”
He held still inside her, and she breathed and tried to relax. He kissed her cheek, her ear, her neck. Eventually she got more comfortable and made a tiny rocking movement, starting to feel some hot pleasure from the pressure of him. He added a little pulsing movement, trying to loosen her up.
He stage-whispered to me, “Tight! You’re a lucky man!”
He slid in another inch and got another “Oh!” I was grateful to her for not saying, “So THAT’S what a penis feels like.” It seemed like every zone of her vagina was going to fire with a different sensation when Nick filled it. Each time he reached a new depth, he’d hold still and let him adjust to him, then pull back very slowly a few times, gently but firmly pushing back to the new limit. Then another little advance.
He was fucking her with half his cock—my whole length and three times my girth—and every slide in and out was devastating to her. She was running her hands up and down from his shoulders to his ass with what looked like frantic adoration.
When I’d first seen his giant banana again, I worried that it wouldn’t fit. Now I worried it would. I kept waiting for him to run out of room inside her. If he somehow got it all the way in and she loved it, would that be her new normal? She more or less enjoyed it when I did it, right? And why did she need tons of lube with me and none with him? Did Nick just naturally make her super wet?
He bumped in another inch—“Oh!” Now he wanted a little ego boost, so he looked worried and said, “Sorry! Did that hurt?”
“No, no, no,” she said.
The worried little boy needed assurance. “Am I doing okay?”
“Yes! Oh my God. It’s incredible! So different.”
“It is? Different?”
“Yes, so filling, I’m filled…I’ve never felt this.”
He didn’t have to look at me. I heard it all.
After overcoming this little obstacle, they now made out passionately like in the hot tub, but now while fucking. Anna’s hands moved chaotically through Nick’s hair; then she started hyperventilating through her nose. He was giving her almost all his fat meat at a good pace, and she was making a little squeaking noise; then his knees cocked up toward her boobs and her feet shot up in the air. She was going to cum, and I was incredibly worried and hard.
She squeezed her face into a knot, held her breath; then her thighs were quivering, her feet shook, and she let out a guttural groan like she was squeezing out a baby. Her face was turned to me as two hot tears ran down her cheeks. Nick swept her hair out of her face so I could see the orgasmic agony on it.
I was insanely turned on as she climaxed, then alarmed because I was going to cum. I yanked my boxers down to relieve pressure and only freed my dick to spurt its tribute into the air, bobbing back and forth, untouched, slinging semen all over the chair and me.
Nick watched with fascination, then Anna grabbed his face and resumed their kissing frenzy as her orgasm subsided. I wiped a streak of spooge off my cheek.
I mopped up my area as much as I could with my underwear. The room looked very different all of a sudden. So now I guess they were going to go on fucking for twenty more minutes or an hour, and Nick, lucky Nick, was going to give Anna another orgasm or four with his big penis while Mr. Below Average sat and watched, ridiculously, covered in a sheen of his own jizz.
Was it just a numbers game? Eight and a half beats four and a quarter, and that’s it? Was he even good at fucking, or did his size and stupid cleft chin do all the work? How had I thought this was going to go? Why in the world was this a good idea? I’d pictured Nick and me giving Anna the gift of sexual joy together. I made the arrangements, and even supplied the penis if you consider that I thought of Nick and got him into the bed with her. She’d have the sexual experience of a lifetime and come back to me, fulfilled and grateful. She’d never have to cheat, because she’d gotten ultimate satisfaction with my blessing. Now I saw this was just Nick in our bed, on top of Anna right in front of me, sticking his Zook into her. I couldn’t stand seeing him jack off—why did I think I could take him resizing my wife?
“That’s it. That’s the whole thing, baby.” Nick was holding still again with the entirety of his big dumb dick inside her. She, too, was deliriously stupid, mussing his hair with her palms, humming vaguely. Then they were rocking together again, and her little squeaks started right away, her second orgasm unstoppable, soon enough after the first that it might have been an aftershock.
She cried out with even greater ecstatic pain this time. Yes, Nick, I’m watching. I’m well aware you’re making her cum again. God, he was hungry for my approval! Did all his girlfriends have husbands who watched in awe of his prowess?
“Multi-orgasmic,” he whispered at me. “Lucky man, again!”
He was the worst man I could have chosen. Too handsome and huge, and she already had a crush on him! Was it possible she wasn’t falling desperately and permanently in love with him? Were we still married?
They lay and cuddled as she recovered, his hard-on still completely in her. He whispered something, and she replied, “Obviously!”
He traced a circle around her nipple with a fingertip as she whispered something back to him and chuckled. He smiled, glanced at me, and said, “Oh well. He means well.”
Most humiliating of all was that this humiliation was getting me savagely erect again. Stupid penis! I pulled my sticky boxers back on to conceal my tiny masochistic excitement.
He got her up on her hands and knees, and she hollered when his bazooka slid into her from behind. This was a new position for her, except for a failed attempt on our honeymoon. Instantly she was starting to cum again, and I didn’t give a shit. She could cum all she wanted. I stared out the glass door at the idiotic hot tub.
She looked exhausted and disoriented when Nick flipped her back down for more missionary, but her master’s cock was still rigid, and she spread for it devotedly. He plunged to his pubes and his big balls slapped her ass as he started driving her toward yet another climax.
“Bro… Come here!”
“Who, me?”
“Get up here! Come up with us,” he said, pistoning away into her cunt.
The husband, an eager cuck with tented boxers, did as he was told and knelt by their rutting bodies on the bed. I don’t think Anna noticed me, but Nick was thrilled to have me in on the action.
“Here we go, bud! Ready?” He sped up the deep dicking, pushing Anna off cliff number four. She plunged into the void, weeping and groaning as her body seized, and I saw up close her eyes rolling and her vulva spasming around Nick’s meat. He pulled out of her with a slurp, got up on his knees, threw his arm over my shoulder, and started masturbating like an Eagle Scout after lights out.
“Whip it out! Get that little guy out. Beat off with me,” he said.
I pushed my boxers down, and we jacked together over Anna’s voluptuous, glistening body, the steam of their coupling thick around us. We came quickly. I splashed a pool onto her belly, and then the Zook blasted hot, pungent man milk onto everyone. The three of us groaned with the force of his climax and stayed locked there, leaning on each other, panting, as the comet tails of our orgasms failed away.
Nick said, “Been a while!” and slapped the back of my head with brotherly affection. “And the three of us are a great couple, right?”
The End.
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