A Sissy Cuckold to another Sissy


“Christ, Bob!” snaps Julie. You just sigh as you feel your skinny cock throb and spurt into the condom next to her bottom. “What about me?”

“I’m sorry, honey. You’re just too sexy! I came so fast!” you say, blushing in embarrassment that you couldn’t fuck your own wife for more than 30 seconds.

“Are you some fucking teenager dweeb?!” She spits as she glares at you and then reaches for her bedside table. She pulls out ‘Edward’ and ‘Speedy’. You blush in shame. Edward is a big black dildo and Speedy is her vibrator. She settles back on the bed and slowly works the dildo into her pussy. Biting her lip, the thick, realistic dildo slowly invades.

You feel your cock stirring after you put the full condom on the dresser.

“Don’t even touch yourself!” she snaps and you pull your hand away quickly.

Half-closing her eyes, she begins to pump herself with the cock, bringing the vibrator between her legs. Soon the buzz and squelching of her sopping pussy are all that can be heard.

“God, yes, fuck me! Fuck me hard!” she moans, slamming the dildo in and out of her. Your cock is hard again but you know if you got to touch her you’d cum just as quick. You just watch as she orgasms, pleasure fighting with anger on her face.

When she’s finally done, she leaves the toys on the bed, grabs her robe and goes downstairs. The dildo is lying there glistening with her pussy juices and you can’t resist. You pick it up and start sucking. You grab the panties she took off when she first joined you in the bedroom, wrap them around your cock and pump yourself as you pump your face.

At one point you think you hear something but turn around and no one is there. The thrill of risking being caught like this makes your cock spurt again, wetting her wet panties further with a small load.

After putting the dildo back on the bed where it was and stuffing the soiled panties in your pocket, you go downstairs to find her.

“Julie…” you start but she gives you a cold look and you stop. You’d always had these problems having sex with her but you’d both hoped there was a solution. It had been an increasing point of irritation and disappointment. It looks like something has gotten much more serious.

“Sit down, Bob.” You comply.

“Things are going to change around here. You won’t have a choice but I doubt you’ll mind too much. If you don’t get with my program, we’re done. Divorced. I mean it.”

You’re deeply shaken and can’t say anything for a couple minutes. When you find your voice, you squeak in a high voice, “Anything, honey,”

“Good attitude. I have preparations to make. Not sure how long it will take but I’m hoping it will be all set by next Friday night. Be home exactly at 6pm that night. Not early. Not late. Don’t jerk off between now and then either.”

Your face flushes. She rolls her eyes. She’s felt you spurt in bed just from snuggling with her.

“You’re sleeping in the guest room until I see if this will work.”


The next days are excruciating for you. You’re completely distracted at work worrying about losing your marriage and what she has planned. You’d tried a hypnotist and a therapist to help you keep your erections longer and satisfy her but nothing had helped. You’d even taken the little blue pill but apparently you’re in the 7% of men it doesn’t work for.

When the fateful Friday finally arrives, you get home and pull in the garage. You’re about ten minutes early but you can’t wait. Walking in the house, you look around and eventually go upstairs.

“You’re early,” says Julie. She’s at her vanity in the bedroom in bright red satin bra and panties. You’ve never seen them before. She is also wearing a black satin garter belt, thigh high stockings, and really high heels. She hasn’t dressed up like this for you for longer than you can remember.

“I’m sorry. Are we going out? Should I change?”

“Sorry is a completely unacceptable excuse but we’ll deal with that later. You WILL learn to pay attention to what I tell you. _I_ am going out. You are getting changed but you’ll wait in the chair until I’m ready to dress you.”

Looking over you see one of the wood chairs from the kitchen has been moved to the bedroom. It’s in the corner facing the bed. You take a seat, just pleased that she isn’t talking about divorce.

You watch her doing her makeup and you can’t help but admire her. When she agreed to marry you, you knew you were the luckiest guy in the world. Beautiful, voluptuous and with a high libido, dating her was incredible. Watching her put on the last touches of makeup also made you a little envious. Your huge sissy side would love to be dolled up and look beautiful like her but she really would leave you if you ever told her about that.

Finally, she’s stunning and gets up from the vanity. There is something forceful about her as she leads you to the guest room and its adjoining bathroom.

“Get in the shower and clean up. Use this lotion all over your body from your beard to your toes. Everywhere except your hair and eyebrows. Do you understand me?”

“Yea, sure, I can…”

“Yes or no,” she snaps.

“Yes,” you say sheepishly. With no more from her you strip down and start the shower. She walks out with your clothes.

The shower feels good after the long anxious day and the blue lotion feels even better. It tingles as you massage it all over your skin. You pause by your cock and then go ahead and massage in the lotion. It’ll probably turn your hair blue as her punishment or something you guess as your fingers slip back to lube between your ass cheeks.

Your cock starts to get hard as your fingers graze your asshole and you pause, fingering it and enjoying the sensation. Your craving for cock is intense but is likely even a worse idea than confessing you want to be a sissy to Julie.

You gather your self-discipline and start working on your legs. Strangely there is a lot of hair on the bottom of the tub. You’re almost done so you work over your feet and then rinse off the lotion. At least she didn’t want your eyebrows or hair blue.

Rinsing yourself off you are surprised to feel how smooth and sensitive your skin is. All your body hair is washing away with the lotion leaving… pretty skin. Your cock gets stiff as you explore your body, baby smooth and electric everywhere. You’d dreamed of shaving like this as a sissy but you’d never had the balls to try it. It felt wonderful. You couldn’t dream what she had planned for you.

Once you were clean, you step out of the shower and towel off. None of your bathroom stuff is there but it looks like Julie is now storing a bunch of her makeup and bathroom stuff there. You walk out of the bathroom into the guest room.

On the bed there is a pair of panties, a bra, a garter belt, thigh high stockings, and some sort of strap. The garter belt, panties and bra are bright pink satin with white ruffled lace edges. The thigh highs are white sheer with back seams. You’ve never seen a more sissy outfit in your life.

She’d made you femme smooth and left out a sissy outfit. Why? This was heaven but she was upset! Why would she do this? You’re so confused. You touch the panties and the satin feels electric. Your cock is rock hard as you eagerly put them on, sliding them up your smooth legs is a dream cum true. From years of practice, you put on the garter belt and stockings with ease. The bra goes on in a jiffy and you find the strap is a choker of satin over leather with ruffled trim, all in pink with SISSY embroidered plainly on the satin. It had a buckle in the back and just holding that makes you cum, moaning as your cock puddles in your satin panties.

“Jesus Christ, I didn’t even have to force you,” says your wife from behind you. You whirl around, red faced. She is looking at you like you’re even more pathetic and you grimace as that thrills you.

“And you love wearing panties so much you already came, no wonder I could never get satisfaction from you.” She’s wearing a skin-tight white dress that gives plenty of hints about her red underwear.

“Pull down your panties!” she snaps. You comply until they are down by your mid-thighs, trapped by the garter.

“Scoop out the cum.” Your fingers are shaking but you do your best to get it all in your hand.

“Suck all that cum off your fingers and hold it in your mouth!”

“Honey, I don’t…” you protest feebly.

“You don’t go along? It’s goodbye. The big D.”

You bring your fingers up to your mouth and suck the cum off each finger and palm. It’s hot, slimy, and gooey but your cock stiffens as you suck it all up.

“Show me!”

You open your mouth full of cum.

“Swallow it and then show me your empty mouth!”

You swallow, half-gag, and then finish swallowing before opening. Somehow you feel like your life will never be the same, as if you’d needed another sign.

“Adequate. You’ll need to learn how to relish it or at least convince me you do.”

She grabs an object from the dresser and kneels in front of you. Is she going to suck your cock? She hasn’t done that in years but if she’s making you a sissy, who knows what… then you feel the metal cage go on your cock and balls. You hear the click and she stands up again. A tiny key is on a tiny chain around her neck.

“You’d better hope I don’t lose this dancing or something,” she says with a serious face. “Now follow me.”

You can’t help but touch the cock cage which turns you on and keeps your dick from getting hard. It is uncomfortable until your dick gives up trying to get hard and then its fine.

She leads you back to the bedroom where a pair of high heels and a mockery of a dress lie on the bed waiting for you. The dress is almost all pink satin with bows everywhere, puffy shoulders, and a short flared skirt with crinoline petticoats sewn in. The heels are at least 5″ and look more like torture devices.

“Stand still.” She picks up the dress and helps you step into it. As the satin and crinoline slide up your body, your smooth sensitive skin tingles erotically and your cock strains in the cock cage. She feeds your arms into the sleeves and then pulls the dress up all the way. A zipper up the back tightens things even more.

She walks around you, feeling where breasts should go in the dress, looking at how it fits you. She seems satisfied. Stepping behind you, she takes each arm and draws it bent at the elbow behind your back so your forearms are aligned next to each other parallel to the floor. You hear straps and locks and then realize that you can’t move your arms. Another lock goes at the top of the zipper. Instinctively, you struggle.

“Aw, don’t like it? I picked it out of your browser history. Of course you wouldn’t be smart enough to clear it.” Your face reddens. “Oh, I know a lot about you now. Made my decision much easier. Not to mention I deserve much better than a sissy perv like you.”

She helps you into the heels which have ankle straps and their own little locks. All of the locks appear to be worked with the key around her neck. You can’t walk without help as the heels arch your feet so much you feel like you’re pitching forward. She moves you over to the wooden chair and helps you sit in it. Some final strapping and locks and you are firmly attached to the chair.

“Well, that’s done.” She puts a laptop on the bed facing you and turns it on. “I’ll be going out on a date tonight. You will stay here until I come home and whenever I decide to release you.” Hitting a key, the laptop screen lights up with one of your favorite sissy porn videos: a sissy all dolled up being pegged by a buxom mistress. Your cock immediately strains to get hard but just aches in the cage.

“Oh yeah, I saw all the videos you spurt too as well. Pathetic.”

You look up and your wife is gone.

You lose all track of time. You’re in an arousal state from the looped videos but your chastized cock turns the focus of the arousal inward and you gently squirm in pleasure without being able to cum.

To be honest, the dress feels amazing. All the satin tight on your body, the crinoline caressing your bare thighs, the bondage aspects make every squirm and struggle a fantasy cum true.

You don’t even hear your wife arrive home until she’s coming up the stairs with someone.

“Oh, no, you’ll love it. I have the little bitch where I want her.” With that your wife semi-staggers in with another woman. Your wife has obviously been drinking a bit as the other woman is helping steady her. The other woman is black and similarly dressed in a tight, satiny club dress with a bit of black lingerie showing. She’s a little taller than your wife though they are both wearing high heels.

The two women fall on the bed laughing their hands all over each other. Soon they start kissing, passionately. Your wife has never, ever discussed being attracted to other women so this is a complete surprise to you. The sight is very erotic though seeing your wife being passionate with someone else burns. The burning makes you feel even more humiliated and pathetic. That makes your cock try to get hard because being pathetic arouses you but the cock cage prevents it. You’re in a swirl of stimulation, churning emotions, and raging desire.

You watch quietly as their bodies move against each other. The sound of their kissing and the rustle of their dresses are intoxicating. Your wife slides her hand down and pulls the other woman’s dress skirt up higher and higher until her hand finds panties.


You gasp as you watch your wife caressing a huge cock uncontained by black satin panties. Your mind spins as your wife gets up, unzips her dress to let it slide seductively down her body. But she’s not seducing you, she’s seducing this other woman… man.. sissy?!?

“Julie! What is going on?” you finally blurt, unable to stay quiet. Your wife’s glare is fierce.

“What do you think is going on, cuckold? You’re locked up so I can get some real cock and finally some real satisfaction.”

“But… she’s a sissy!”

Now your wife is really mad. She digs in a shopping bag and pulls out a little 5″ penis on a strap with a buckle. Before you know it, she’s pushed the little penis gag into your mouth and strapped it tight around your head.

“Cuckold sissy bitches are silent unless spoken to and they NEVER TALK BACK!”

You cringe at this, your mouth automatically sucking and working the cock.

“I never said I didn’t like sissies. You were always too much of a wimp to even tell me about it. We could have had fun with it though with your cock size we would have gotten here anyway. Gem here is beautiful and crazy sexy AND she’s got a great cock. Everything I wanted. Now stay quiet. I’m letting you watch so there is no confusion whatsoever about your new reality.”

You sit, stunned. Every bit of your new reality is falling on you… every erotic sensation of your slutty smooth skin, the feel of the tight lingerie, your chastised cock, the locked dress and heels, the rubber cock in your mouth, your arms bound to the chair… You watch your wife in her lingerie and heels slip back on to your bed where the other woman, no sissy waits, stroking her… his cock.

And it is an impressive cock, at least 10″ and thick. You couldn’t argue with that. You watch as your wife takes this cock in hand as Gem relaxes back on the pillows and caresses your wife’s body.

Your eyes bulge as you watch Julie lean down and wrap her lips around the head of Gem’s cock. She moans and quickly gets the cock wet with her saliva, stroking the shaft and starting to bob up and down.

Sucking cock! Your eyes bulge and you can’t help but moan around the cock gag. Your wife looks over at you, cock in mouth, and winks at you. Your cock strains against the cage as you watch that beautiful cock sliding in and out of your wife’s mouth.

“Mmmmm, you feel so good, baby,” murmurs Gem. “You’re a natural cock sucker…”

Julie takes her mouth off and firmly jacks his long length. “I love sucking big cock… I used to do it a lot.”

You’re practically vibrating, incredulous. She always told you she didn’t like doing that. Now you know it was just because you’re too small.

She resumes sucking his cock and you are witness to a cock-sucking clinic. After several minutes, she sunk down and took all TEN inches of cock in her mouth and you see her throat bulge as Gem moans in pleasure. She holds there, her lips pressed against his smoothly shaved base and then withdraws with a smack and gasp.

“You’re amazing but I don’t want to cum yet,” says Gem, drawing Julie up to kiss him. Julie’s hand caresses Gem’s ‘breasts’ and she moans. Now Gem gets off the bed and begins to do a sexy strip tease. You see Julie’s hand in her panties rubbing her pussy. Her red satin panties are damp. Gem’s dress slithers down revealing a killer woman’s body: hips, full real breasts straining in a satin bra, narrow waist, great legs. If it wasn’t for the horse cock hanging out of her panties, she’d be all woman.

“I’m going to fuck you, Julie,” growls Gem in a heated but effeminate voice, her hand stroking her cock. Julie eagerly gets on her face and knees on the bed. Gem pulls her over to the side of the bed so he can mount her while standing by the bed, all in full view of you. He pulls her panties to the side and rubs the fat head of his cock up and down on her pussy lips.

Where is the condom? Your wife makes YOU wear a frickin’ condom! you scream in your mind.

“Where’s the condom, babe,” asks Gem as if reading your mind.

“No condom… I want you bare in me… I want you to feel everything…” You shake and strain against your cruel bondage and your cock feels like its trying to bend the cock cage.

“Take it easy,” warns Julie. “I haven’t had a real cock in me in years!”

Gem slowly pushes her cock into your wife’s pussy and soon Julie’s begging for more, deeper, harder. The gorgeous sissy obliges, plunging her big cock into her deeper and deeper until she’s smacking against her full ass. Gem’s breasts bounce with the thrusting while your wife’s breasts strain to fly out of her bra with each stroke.

They get into a rhythm and Julie grips the bed cover with both hands to be able to thrust back and meet each powerful thrust. The smacks of their fucking are loud in the room.

Minutes pass but Gem finally gasps. “Julie, I gotta cum. Where do you want it?”

“In me! Fuck me and fill me with your cum!!”

You’re motionless, in shock.

“OOOOOooooh fuck!” blurts Gem as she holds her cock deep in Julie’s pussy and you know ropes and ropes of cum are filling your wife’s womb. Julie wails as she cums too and you’re overwhelmed. She never came when you came.

You look down, defeated in the pink sissy dress, lingerie and bondage. After a time you look up again and your wife is bringing Gem’s cock back to life even as you see cum oozing out of your wife’s pussy. Once Gem’s hard again, she whispers something into Gem’s ear, causing a devilish grin.

“You sure? I’m damn big!”

“No, I need it. I’ve always secretly wanted it and doing that will make me your total whore. Just… take your time.”

You watch as your wife digs out the bottle of lube from her bedside drawer and pours it over Gem’s cock, massaging the lube all over it. She hands Gem the bottle and then lays on her stomach. Gem pulls her panties down and off of her before she starts massaging your wife’s bottom. She feels the beautiful fullness of each cheek and then explores between the cheek. Your wife spreads her legs wide and you can see Gem’s fingers pushing the lube around and then into your wife’s asshole.

When does it end? you wail in your mind. Julie always refused to even discuss anal sex and here she was going to take the cock of a total stranger, in your bed, as you are forced to watch. The pain of your straining cock has become a background blur to the whole experience.

The process takes a long time but to your shock, you watch Gem’s thick shaft finally sink into your wife’s ass. A torrent of obscenity comes from Julie’s mouth and the urges Gem to fuck her ass deep. Soon the sissy’s cock is sliding in and out between Julie’s ass cheeks, glistening with lube, pulsing with strength.

You are transfixed by the sight and don’t know how long they last before Julie comes screaming and that sets off Gem who pumps another huge load of cum into your wife.

Eventually they lay on the bed, kissing, Gem’s cock finally soft but still big. They whisper and look at you until finally Julie appears to relent.

“Gem wants me to give you a present since you’ve been such a patient sissy cuckold bitch. Do you want my present?”

You nod eagerly, anything.

Gem walks over, unlocks you from the chair and helps you until you are kneeling by the edge of the bed, your arms still bound in the sissy dress. The penis gag is removed. Your wife gets on the bed with Gem behind her and places her pussy and ass in front of you, legs held wide. You see the cum slowly oozing out of both places.

“Swallow it all and you’ll get another prize!”

You lean forward and lap at her pussy, tasting another lover’s sperm on your tongue and quickly realizing that you love it. You lap eagerly at her ass and pussy, tongue thrusting in each to release the most cum. You swallow every bit you get until there just isn’t any more.

“She is a real cuckold, isn’t she,” coos your wife, confiding in Gem. She reaches out a finger to wipe up the cum that is all over your face and slowly let you suck it off her finger. “Should I let her cum?”

Gem whispers to your wife and Julie stands you up, reaching under your dress to unlock and remove your cock cage.

“You can cum if you do it without touching your little clitty and while either sucking Gem’s cock or having her fuck you. Suck?” pause “or get fucked?” You make your choice eagerly clear and soon you are on the bed, face down, ass up as Gem pulls down your panties and starts pushing lube into your hole. Your wife puts a condom on your little stiffy.

Gem is very gentle and patient but you’d been fucking yourself for years with your wife’s biggest dildos so it takes almost no time at all before Gem is grabbing your hips and sinking her whole cock into your ass.

“God damn, what a cock slut!” laughs your wife, idly playing with her pussy lips as she sits back on the bed and watches. Gem is controlling you by your hips and you are helpless in the sissy dress bondage. The feel of a real cock, a thick black cock pounding your sissy pussy is incredible and Gem barely fits her cock all the way in before you moan and cum, filling the condom almost to bursting.

Gem doesn’t stop but starts fucking you, deep and slow. “She’s a tight little sissy slut bitch, isn’t she?” muses your wife. Gem just hums appreciatively. You lose yourself in being Gem’s fuck bitch, feeling all the satin, bondage, and huge cock plowing your ass. At some point, your wife puts a new condom on your tiny dick.

Eventually Gem starts thrusting faster, her grip on your hips is tight and hard. Your body jerks with each thrust and you wish you had breasts to jiggle when you got fucked. You gasp when Gem slams her cock all the way in and you feel it throb and pour cum inside you. That’s more than enough for your dick to spurt again, half-filling the second condom.

Gem withdraws from your ass and you slide flat on the bed, sweating and spent. You moan a little when your wife makes you stand by the bed. You shiver as you feel Gem’s cum in your ass, slowly sliding down and starting to trickle out.

“Open your cum dump mouth, slut,” she spits. You obey and she puts the bulging condoms in your mouth. “Suck out all the cum but don’t swallow the condoms or the cum yet.” You whimper sadly at what’s been done to you but start working the latex in your mouth, getting more and more come in your cheeks. When you’ve done the best you can, you whimper again. She pulls the condoms out of your mouth and wipes the residual cum on your face. She then crouches behind you and pushes your ass open. Gem’s load flows out and into the used condoms.

Your wife stands before you again and you obediently open your cum filled mouth. You have to tip your head back as she strains the cum from the condoms into your mouth so none runs out.

“Swallow all that sperm, slut,” your wife instructs. You start swallowing, gag a little at the heavy musky taste, but keep going and eventually show your wife your clean mouth. You think you feel a little full from the cum!

“That’s your life now, slut,” concludes your wife. “You sleep in the guest room in sissy slut wear. You wear sissy slut underwear and have to risk being discovered. You will not share MY bed and I will fuck anyone and everyone I want to. Sometimes I’ll let you participate, or I’ll let you watch, or I’ll lock you on your bed and you can just listen to what real sex sounds like.”

She continues as your emotions are in an uproar. As terrible as what she is saying is, you feel like you completely deserve it. You aren’t a man who can satisfy her so how can you claim a right to her bed or to keep her from fucking anyone else. She’s sissified you more than you could have dreamed of. She’s made you a huge cum guzzler and you love it all. Your cock is rock hard again as she lays out the new rules.

“I still love you which is why I looked into what you really get off on and I’m going to give it to you. Sissy clothes and smooth skin is just the start. You’re going to love living as a sissy, total slutty dresses and heels whenever you are in the house. You’ll answer the door as a sissy slut if I need you to and you’ll suck off any delivery man which I know you’ll love.”

“All I need to hear is that you love being my sissy slut and we’ll start our new life together.”

You barely hesitated. “I love being your sissy slut, Mistress.”

Julia gives you the warmest and most genuine smile she’s given you in weeks and she hugs you. You can’t hug back due to your sissy dress bondage but you lean your head on her shoulder.

She leads you back to the guest room (which she calls the “sissy room” now), locks you onto the satin sheeted bed, and returns to her bedroom where you can hear her suck and fuck Gem over and over again.

Needless so say, you cum all over yourself.


The End.



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