Cuckolding stories


by Gilglim

07/24/2016 21:45 in wife

Brooklyn, c. 1988

The landline rings. You answer it. You're alone in the apartment. Your wife Karly is out. Probably with her jazz musician "friend" Jamal, the guy she's been cuckolding you with the past few months. It's the second guy she's openly "dated" in this, the eighth year of your common-law marriage. The first guy, a self-appointed art critic, was a pompous ass in his mid-fifties. The affair was short-lived. For his part the appeal of dating a part-time artist and lowly public school teacher half his age probably quickly wore off; as for Karly, she probably tired of an extramarital sex life that mostly consisted of limp-in-the-mouth blowjobs. He was in his fifties, afterall. Besides, she'd met Jamal by this time.

You immediately recognize the husky voice. It's Karly's older sister Susan. Older, but only by a year. They're the closest of the siblings in a big German family. Well, Polish. Susan is OK to look at and she has a great ass. But she's not cute like Karly. Susan is bigger-boned, thicker. Not fat, thick. And she has a husky voice. At one point she was studying to be a park ranger, as you recall. She's unmarried. She's a straight-talker. Sometimes she can be unbelievably blunt. You've always secretly wondered if Susan was lesbian. A closet lesbian at least. Still, she has a size bigger tits than Karly (not saying much) and she has that great ass...

"Um, Karly's not here," you immediately say. Why would Susan want to talk to you?

"No, I know. She was here. She just left."


"Listen, Karly and I were having a heart-to-heart just now and she told me that sometimes during your guys' bedtalk..."

Bedtalk. That was a quaint little term I hadn't heard in a while...

"'ve confessed that sometimes you fantasize about, you know, fucking me. Well I was telling my sister...sometimes I have the same fantasy about you. Remember that time the three of us went to Rockaway was it? Brighton Beach? And you wore your little red Speedo? I got mileage out of that for months afterward."


"Anyway, I was wondering...this was actually Karly's idea, she's OK with it I mean, how would you like to get together sometime?"


"You could come over here to my apartment in Queens. You remember where it is, right? Right off the G train?"


"I could make dinner and we could drink some wine and...see where it goes. Would you like that?"

Stunned silence.

"Karly says you're a quick-cummer but that's OK...I cum pretty quickly myself. And she says you like kinky stuff. I like kinky stuff too, nothing too crazy but...Anyway, we can discuss all this when you come over..."

You are over six feet tall but at the moment you feel more like three-foot-two. Or the height of a toad, maybe that's a better analogy. Is there anything Karly didn't discuss with her sister?

"How about this Friday? You could come here straight from work if you want. You work somewhere in midtown, right? It's a short ride on the subway. I'll make dinner. You can pick up a bottle of wine if you want, Karly says you're sort of a wine snob so it might be better if you pick it out. Then if you end up spending the night I'll get up and make you breakfast Saturday morning..."

Translation: Maybe we can get another fuck in. Susan has read your mind:

"Karly says your favorite time to do it is in the morning and that way you wouldn't have to take the subway home late at night. But we'll see how it goes. Or we don't have to do it at all the first time. We can just sit. And chat."


Speechless. You. Still. And what was that bit about you being a snob?

"For instance, I'm kind of dying to hear how you feel about Karly dating all these other guys right under your nose. I mean, It must be pretty difficult for you sometimes. Karly says you guys hardly ever fuck anymore and I'm not dating anybody at the moment so, it could really work out well for us." Pause. For breath. "What's this new guy's name? Ahmad? The black jazz musician?"

"Jamal," you say weakly, after the throat clear. Your silence at last broken. Now what?

"Amal, that's right. Did you know he's got a wife and two kids?"

Another throat clear. You've thought about slamming the phone down but that, you decided, would be cowardly. Of course, letting other men bang your wife is cowardly. Or exceedingly open-minded and progressive. Pick one.

"Um Susan, wow, listen...," you finally stammer. "I don't know what to say. Wow..." It's Sunday. This Friday is five days away. Five days to steel your nerves. Or back out. Besides, it's time to give your wife some pay-back, dammit! (This is the pep-talk you're giving yourself.) And what could be a bigger pay-back than fucking her sister? This is MacBeth-grade revenge, pal! Get drunk, fuck Susan (Think she'll let you fuck her up her beautiful ass? Maybe that's a discussion for a second date...), hold a woman in your arms again, especially one with a similar DNA to your wife's...This jerking off in the back row of a gay porn theater in midtown is getting old...

"Wow. OK," you finally say. "Sure. OK. That could"


"I get off around five on...," the day of the week having just gone poof! in your frazzled brain.

"So you should be here no later than six then. I'll make dinner," Susan repeated.

"OK. Right."

"See ya Friday then!"




You re-cradle the phone. Your hands are trembling. Have you ever heard a woman more excited? Or hornier? Well...a naïve Karly maybe. Back in the good old days when you first got together...

Christ! You need a beer. Six beers. Karly'll be home soon. What then? What will say to her? I just made a date with your sister? I'm going to fuck her Friday night? Wait. Didn't Susan say this was all Karly's idea. Well, no. But didn't she imply that Karly had given her blessing? Get him out of my hair, Sue. He's always horny, he's always bugging me for sex. You're single. You're horny. You need a man. Take him off my hands, will you? One night a week at least? He's nice-looking, don't you think? Go ahead. You have my blessing. Is it so much to ask?

You could hear your promiscuous wife now...

The phone rings. You jump. It's your sister-in-law again. Oh god, what now?

Throughout Susan's entire much-rehearsed (you assume) dissertation earlier, or proposition might be the better word, there had been a distinct quaver of nervousness to her voice. Nervousness. Excitement. Raging hormones. Nevertheless, she had plowed through her little speech like a sharp steel blade through soft spring soil.

Now here it was again.

"Sorry. I forgot to mention," she added, as postscript. "I'm a vegetarian. I don't eat meat. I hope that's OK."

Yes, Susan, I know what a vegetarian is. In fact, I know you're one.

"That's fine," you say.

"You sure? Cause I could fix some eggs or something if you..."

Eggs. Sperm...

"Whatever you fix will be fine. Darling," you decide to add. A brilliant touch, even if you do say so yourself. Susan's turn to pause. And you can see, through the phone, the blushing smile breaking out all over her face. You can hear it in her voice. What a brilliant ploy!

"Oh. Great. OK." She giggles uncontrollably. "OK. See you Friday then!"

"See you!"


The voice at the other end lingers, but you hang up. Time for that first beer.

After the hummus and the veggie grape leaves, after the god-only-knows-what kind of casserole that tasted like warm cardboard, and after some kind of flourless wedge of "brownie" that required a steak knife to saw're still hungry.

But that's OK. You have the high-calorie consolation that two bottles of wine can provide.

"This wine is really great!" Susan declares for about the fourth time.

Good, not great. It's only a Beaujolais-Village afterall.

"You sure you don't want another brownie?"

"I'm fine."

In fact, you're starting to drift. Like a high cloud. A warm glow is starting to settle over you. Everything is going to be fine. Just fine.

You're sitting on the end cushion of Karly's ratty couch; she's sitting on the middle. Your body and her body are turned inward a little, toward each other. Knees practically touching. It's awkward. Karly's low-cut stretch blouse bares her modest cleavage. She's wearing a short skirt. Her bare thighs are crossed. She has bigger pores than Karly. Follicles, that is. She's wearing more makeup than you've ever seen her in. Her lipstick is red—redder than the wine. Although much of it now smears the rim of her cheap goblet. You wonder: have I ever seen Karly—Susan you mean, Susan!—in lipstick before? Maybe at that funeral that time?

Susan is speed-talking, nervous. You sip your wine. Another glass (or two) and you'll be ready to lean over and kiss her on the mouth. To silence her. Then you'll feel her little tits. Then you'll...

You marvel at how the spread of Susan's ass on that cushion is so much wider than Karly's. You marvel at it. Can't wait to see it. Pantied, then in the flesh. You can't wait to feel it, squeeze it. Kiss it. Lick her sweaty crack. Plunge your tongue in her...

You have an erection. Is it obvious? To Susan? You wonder if she's noticed. She's talking, talking. You go for it.

You lower your hand onto her bare thigh.

Susan smiles. She interrupts her latest uninhibited topic—about how though she's been spanked before, she's never been whipped—let alone whipped a man the way Karly whips you—doesn't it hurt? A LOT? Does it leave marks? Guess I'll find out soon enough!—to say, tucking a lock of dark hair behind a reddening ear: "That feels nice."

"Baby, you're driving me-"

The phone rings. Before you can even say "Let it!" Susan has jumped up, as if propelled by an errant couch spring. Is this evasion on her part, you wonder? Cold feet?



Immediately—even before Susan cups the phone and mouths at you the words "It's Karly"—you know who it is. WHAT DOES SHE WANT? Jealous? Is this sabotage on her part? Leave us alone, BITCH! I was already halfway to second base...

"No, we haven't done anything yet. We're just sitting here talking."


"You know. About stuff."


"We had dinner and now we're drinking some wine."


"No, he did. It's really good, too."


"I hope so."


"How can you tell?"


"You can? Just by feeling his balls? He lets you?"


"Oh. Well that's good for me, I guess."


"Look, don't ruin it for me, OK? Let it be a surprise."


"It's enough just to have a man inside me again, OK?"




(Susan cups the phone again. Looks at me. Stares. Wide-eyed.) "He does?"


"Is he (mutters something into the phone)?"


"Oh my god. Why does he do that? I don't understand."


"I will. I don't have any though."


"OK. If you say so."


"OK, I will. Thanks for the warning. Bye, sis. Bye."

Susan hangs up. Turns that same wide-eyed stare on you again. Cracks a smile. Tries to. Fails.

"Listen, your wife says I should make you wear a condom tonight."

"What!" jumping up.

"Yeah, she does. She's pretty insistent about it."


"Ask her. I don't know. She was pretty vague. She just said, 'Make sure you make him wear a condom,' that's all."

"Karly's full of shit!"

"But why would my sister say something like that if it wasn't true?"

"To...yank our chain? Ruin our evening together?"

"You think wearing a condom is going to ruin our evening? I thought it was going really well."

"It was!"

"Besides," a smile at last creeping through, "watching a guy put a condom on is a big turn-on for me. It's like...Wow, this is really about to happen. Condoms make me wet."

"They do?"

Susan nodded. "Besides, I've been off the pill for a couple of months now, and you never know."


"Plus Karly says you go to gay theaters sometimes."

"No I don't."

"She says you do. When she has company over, and you let her have the apartment for the evening...she says you go a gay theater in midtown because you like to watch guys fuck. You say it's hot."


"So there's two good reasons we should use a condom tonight, darling."


"And like I say I don't mind them, I really don't. I mean I like it when a guy cums in me, but..." Karly paused. "There's just one problem."


"I don't have any here. Condoms. Haven't had a boyfriend in a while, so there hasn't the need for one." Karly beamed a smile. "But there's a bodega at the end of the block. You passed it on the way here. Do you mind?"

She had you at darling. No, she had you at "makes me wet."

Susan held the just-used, just-removed Trojan (I'd bought two at the bodega—two for two bucks) at eye level and marveled at the receptacle end's white bulge.

"Wow! Karly wasn't kidding when she said you'd have a big load for me."

Except, as it turned out, it wasn't for Susan it was for the prophylactic. On the other hand, one doesn't want to get one's sister-in-law pregnant now does one?

As in just about all post-coital opposite-sex moments like this Susan had a warm and fuzzy glow about her while I...I couldn't wait to get the hell out of her apartment. The sight of the ludicrous-looking stretched-out condom, and my semen filling it, disgusted me. On top of that was the embarrassing matter of how quickly it had come to this conclusion.

"Look," I said, "I'm sorry about cumming so soon."

"No, don't sweat it. It was great. Really."

"No it wasn't...," I muttered. Loser!

"Listen, I haven't been fucked by a man in eight months," Susan advised with typical bluntness. "It was wonderful. You were too horny, that's all. I bet in the morning it'll be a different—you're getting dressed?"

I nodded.

"You want another glass of wine."

"No, Susan, I really have to get going."

"WHY? I thought you were going to spend the night."

"Can't. I promised Karly," I lied.

"Karly didn't tell me anything about you not being able to spend the night."

"No, she wants us to take it slow."

"What slow?"

"At first. Our...relationship."

"What relationship? We're sex partners! At least I thought we were."

"We are. Will be. I'll come back next week. Next Friday. I promise. Maybe we could go out...Are there any vegetarian restaurants near...?" I almost gagged.

"Oh," a deflated Susan replied. "That might be nice." She sat there naked on bed's edge looking down between her thighs. Maybe at the pendant condom the fingers of her right hand still pinched. "Bummer," she declared.

"Yeah. Sorry. But you know how Karly is." (I'd pulled if off! My multi-layered lie!)

I think Susan expected a kiss on the mouth at her apartment door, but I wasn't in the mood. For one thing her lipstick was all smeary. I kissed her cheek. She insisted we hug. I kissed the top of her head.

"I'll see you next Friday then," I said, pulling away.

"OK if I call you?"

"Sure," I replied, with a roll of the eyes. To talk about what exactly?

"Say hello to Karly for me."

"I will."

I beat feet for the G train.

A half hour's wait for the next train, followed by a half hour's ride deep into Brooklyn, and it was a little past eleven by the time I reached our apartment building. As I climbed the last flight of stairs to the top floor I had a deep sense of foreboding. Were those very audible moans coming from the apartment below or...?

They were growing louder. I put my key in the lock. I heard a commotion in our bedroom, down to the right. The light came on. Then like a solo dancer emerging from the stage wings at the Met my wife came running on the balls of her feet. She was naked. Her hands were raised. Had they been raised higher than her little bouncing tits it would have been a surrender pose. She shouted in whisper:

"What are you doing here!"

" here?"

"You're supposed to be spending the night at my sister's!"


"Finished what? Jamal's here! He's spending the night! LEAVE!"

"Where am I supposed to go at this hour?" I pleaded.

"That's your problem! GO!"

The door slammed in my face. The light had been poor but...was that a drying semen drip on the inside of Karly's slender left thigh?

Now what?

As I walked back to the train station I began to formulate a plan. Which is to say, fabricate another lie. This is what I would say to Susan, when she met me at her apartment door with a look of pleasant surprise, cinching a robe around the thickish body I'd so recently fucked. And would fuck again come morning.

"I got halfway home and...I just had to turn back. I felt so bad about the way it ended tonight. Me walking out like that. Fuck Karly. I want to spend the night with you instead. I'm crazy about you."

Susan, eyes sparkling: "You are? Great! Come in. I was just about to pour myself a brandy. Would you like one?"

(I seriously doubt Susan kept a bottle of brandy in her apartment. Besides, I don't drink brandy. But it was a nice romantic touch, don't you think?)

An hour later Susan did indeed meet me at her door. Her eyes were not sparkling, however. In fact, her dark brows knitted a frown. She wore tight jeans and a pullover sweater. Her feet were bare. Casual.

"What are you doing back?" she asked. Her eyes were red.

" halfway home and..."

Susan tucked hair behind an ear. Her eyes narrowed. "Karly's friend was with her wasn't he?"

"Hunh? No! I don't know! I never made it that far. I turned around and came back. To be with you. I...You have company," I observed.

The guy I could now see over Susan's right shoulder was lanky and had a shock of dark Elvis-like hair. Frankly, he struck me as a gas station attendant.

"Oh, yeah," Susan replied. "This is my friend Rob. Rob lives in the building. We hang out sometimes."

Rob, slumped on the couch, gave an awkward little wave. The apartment reeked of weed. Rob held a goblet of leftover Beaujolais in his hand. He was drinking my wine!

Susan glanced behind. "Well, I guess you could come in for a little bit, if you want. Have a drink with us."

"No. You're...I'm intruding. I...You guys..."

"OK then," Susan said, abruptly concluding the matter.

"Next Friday then?" my voice having risen an octave.

Susan leaned closer before closing the door. The second that had been closed in my face tonight. "We'll talk about it," she said. "I'll let you know. Goodnight!"

At least my sister-in-law was polite.

The only hotels that I knew about in New York were either in Manhattan or out at the airports. I couldn't afford the former and I sure as hell wasn't taking the A train out to the latter.

As I once again headed back to the train station an old adage popped into my head. Adage may not be the right word...

For the cost of one subway token, it was said, you could ride the trains all day and all night. You could ride them indefinitely. Theoretically, you could ride them till the end of time. (Or until the next motorman's strike.)

This was one option. I sank my hands in my pockets against the humid chill and discovered, in the right one, the second foil Trojan packet. This led me to a new, improved, truly inspired idea. That gay porn theater in midtown. Wasn't it open 24 hours?

I could settle into a cushy seat in the middle of the last row, ideally one that wasn't damp, close my eyes and ears to all the moaning and banal dialog and perhaps get a half-decent night's sleep. It was theoretically possible, right?

And in fact, an hour later, with my ass at seat's edge (I'd had to kick a wad of tissues forward to the next row) and my head resting on the seatback I'd just drifted off into a kind of cinematic half-consciousness when...

It felt like I was on a see-saw. Someone really big had landed in the seat next to me and I'd popped up (mixing metaphors) like a Jack-in-box. What the...?

The guy was breathing heavily. And he wasted no time, unbuckling and unzipping and pulling it out. He was already hard, and it stood straight up, twelve o'clock high in the flickering projector light. All he needed was an assist. A helping hand. He expected it.
I sighed, inwardly. I was exhausted. I needed sleep. I'd never done anything like this before. But how difficult could it be? What, afterall, is the difference between stroking your own cock and stroking somebody else's? It's just a matter of...familiarity.

"Thanks," my new friend said, as I enclosed his big cock in my fist. His head rolled back. He began to moan with my stroking motion.

"Faster," he eventually said. I shifted position slightly and worked him harder. As I stroked him I couldn't help notice the guy two rows ahead and a few seats down looking over his shoulder, watching this "live" sex show. Would he want one next? Would the news spread around the theater? There's some young guy giving handjobs in the back row? Was I destined to spend a sleepless night wearing my right arm out pleasuring complete strangers? On a night that'd started so promising committing incest with my sister-in-law, was this my new fate?

More to the point, did this make me gay? Technically speaking?

And does fucking your sister-in-law really qualify as incest?

The guy stiffened and let out an urgent groan. He stilled my frantic hand. "I'm gonna cum," he blurted. About time, I thought. Wish I had this kind of stamina. He was out of breath. Another guy was sliding down our row, my way. Oh great. Next!

"I don't want to make a mess," my pleasure-partner panted. "You got a condom on you?"

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