A Sissy Cuckold to another Sissy

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Gemsissy
Gemsissy
199 Followers

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.

Gemsissy
Gemsissy
199 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
16 Comments
AnonymousAnonymous4 months ago

Love this i became a sissy in my early teens and loved being in girls clothes. As the only male in the house and having 3 sisters i had lots of choice on what to borrow and wear. I became more and more curious and wanted to have sex as a girl. Masturbating in panties was hot but i felt i was missing something. I had dressed for a friend and gradually that became more sexual and his was the first cock i sucked and tasted semen which i liked a lot. He was the first to fuck me anally and once the initial pain subsided and he was fully inside me felt better and better with each thrust into me. We didnt use condoms and i felt good every time he gave me his load in me. Sex was as often as we could do it and not nearly enough for me so much that some nights id slip out of the house with a bag packed with girl clothes and head to a park and change into my girl clothes. I knew the park had a reputation for gay men to meet other men and it was true as i had more than enough cocks offered to me and most nights sucked some and got my ass filled as well. It was dark and i enjoyed what i got from men of all shapes sizes and ages and went home smiling and semen dripping out of my anus. One night i was bent over sucking a cock whilst another was fucking me in the toilets my favourite place when it was wet or cold outside. The guy behind me just finished and had nutted in me and i was still sucking the guy in front when i felt another cock pressing against my anus and the guy i was sucking commented impressive cock its big she will enjoy it. He began pushing into me and i realised he was big and i was struggling to take it properly. I felt cold liquid being poured on my ass and him push again stretching me and beginning to open me wider than id ever opened before. Then he spoke and told me this bbc is going to fuck you to heaven and back. He began going slow and deeper each time and it hurt but he kept pushing and i swore he was in my stomach he was that far inside me then he began long slamming strokes lifting me up with his cock and id never been fucked this way by anyone before. Several minutes it was like this before he said he was cumming and i felt his cock expand and twitch inside me as he pumped rope after rope of semen into me. He lifted me off and i was that weak i almost collapsed and felt a stream of semen run down my legs my anus was wide open and clearly full. He turned me and told me to lick him clean and i was in awe at the size of his cock and his huge balls which i licked totally clean. I have had him fuck me since that several times and love how much cum he gives me everytime. He is asking me would i like him to bring other men to enjoy me soon to which i have said yes so newyears eve this year may be interesting more than it usually is for me. SissyErica in the UK

jennifurzoejennifurzoe7 months ago

This sissy is just so very much jealous that she's,well crying but in also feeling happy for the Wife of Superior Gender and her new sissy.🩷♀️💜

Sissyjackie2008Sissyjackie2008about 2 years ago

This story is so hot. i too am a married bi sissy cuckold and maid to my lovely wife.

cdCindy1cdCindy1over 2 years ago

Every time I read this story it turns me on so much. I wish this would happen with me and my wife. One of my favorite lines is:"

"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."

I would love to live full time as a sissy, answer the door totally dressed so everyone will know that I'm a sissy, and also of course sucking off every delivery man -- and all the neighbors too.

Please tell us chapter 2. I can't wait.

Hugs & kisses,

cdCindy

AnonymousAnonymousover 3 years ago
Pretty good.

I like how everything escalated so quickly. A great fantasy. I really liked it. Thank you.

Show More
Share this Story

Similar Stories

A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
Wife's Idea Wife teaches Hubby new tricks.in Group Sex
Her Presents She had a number of surprises for him.in Fetish
Willingly Cuckolded for Love A happily married couple both submit to her Dom ex-lover.in Fetish
My Girlfriend Made Me a Sissy A guy is transformed into a sissy slut.in Transgender & Crossdressers
More Stories