All Comments on 'How to Become a Sissy/Cuckold'

by Quietoldie

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  • 33 Comments
MisterteaMisterteaover 7 years ago
"You can learn a lot from masturbating to erotic stories about cuckolds and sissies but don't forget that they are not real."

Well, you certainly learned a lot, but..

AnonymousAnonymousover 7 years ago
I want a Mistress

I'm in the process of arranging for a Mistress to dominate me in every way possible. It isn't my wife (she's not into it) but instead I am cross-dressing for my Mistress Angelique and she will order me to do whatever she wants. I love it.

AnonymousAnonymousover 7 years ago
cocky

When we met my wife thought it was good to have me in charge. I wanted her to be in charge and use me as her cuckold. It took time for her to take control and when she did I was happy and she made me do what she wanted It has ended up with me in chastity and she has her group of bulls to sue and I do have to service them IT IS A WONDERFUL LIFE.

liz33ndliz33ndabout 7 years ago
wish i could have been more open

at the age of forty, I was pitching for my ball team, when a line drive hit me next to my groin. it left a bruise mark on my cock and leg, but left the boys unscathed, then at 55 my wife wanting more sex, was disappointed in my performance, as was I. so she found a guy online and left.

now at sixty, I have developed some scar tissue near the head of my penis, and it makes erections difficult.

the point now? Had I been open enough to offer the cuckold option, we could still be together, and she and I still enjoying sex to the limit in different ways. I read these stories, and they are a fantastic turn-on, wishing it was happening.

cdCindy1cdCindy1about 7 years ago
thanks for the advice

I'm a closet CD but my wife doesn't know. This story is helpful because it gives me ideas of how to let my wife find out about my cross-dressing and my desire to be her bitch. I want her to get fucked by other men with big cocks and then bring them home and feed their big cocks to me. I want to suck cocks in front of her, get fucked by well-hung men in front of her, and then eat their cum out of her cunt after they've fucked her in front of me. Thank you for this story and "how to" help.

AnonymousAnonymousalmost 7 years ago
My wife is a bossy BBW

My wife is a bossy BBW (about 275 lbs) and is definitely in charge in our relationship. She has long brown hair and a big ass and a pretty face. When we have sex she refuses to let me enter her unless I have brought her off orally at least three or four times. Once we did roll playing where she dressed as a man and I dressed as a shy little bitch and she fucked me with a strap on. It hurt, but it felt good submitting to her. I have low T now and can't get it up like I used to. I keep dropping hints that if she wants a lover it would be OK with me. I would LOVE to watch a real stud plow her, and then have her sit on my face so I could do my duty and clean her.

AnonymousAnonymousalmost 7 years ago
Don't make me laugh!

He doesn't need a key to remove the cage. He can CUM while in the cage. And his best move would be to suffer a little embarrassment, go to the police and have them remove the cage ( bolt cutters or a locksmith). At that point the wife goes to prison (it's illegal to lock a person in chastity), he divorces her and keeps all the marital assets. Easy peasy. No man would put up with this bitch. Laughably bad story.

suckermansuckermanalmost 7 years ago
good advice

everyone has their own pressure points but this is a good general guide. we changed our washing powder an the wide elastic on mens pants gave me a rash. I told my wife I wanted to wear panties like hers (very thin elastic and thin cotton) it was only supposed to be until the rash went but I wear womens cotton panties all the time now.not sure where to go next as we have already gone through the cuckold stage and come eout of the other end still together. love to wear a nightie but I dont think I will get there but the panties are fine

spankmehard51spankmehard51over 6 years ago
sensible advice

Every couple is unique but this lays out a good basic approach. Having been a cuckold for many years I have that part down. i have been encouraging and supportive of her dating. And I frequently remind her that I am okay with it, that my small penis and inability to keep from cumming in seconds should not deprive her of her own pleasure. She does not particularly want me to be a crossdressing sissy. But she is quite happy to have me do her laundry and cook her meals. I picked up a couple ideas that might help me encourage her acceptance of my wearing feminine apparel. Thank you!

AnonymousAnonymousover 6 years ago
Sure, the HOW....

But never the why!

Why is that? Why would you want this? WHYYYYYY

can't you even explain it to yourself?

Kerrysub4uKerrysub4uover 6 years ago
Thanks

I too crossdress and wife has no clue. I dream she knows and cucks me. Has me dress for her and her lover's. Become a cock slut for her . Always dressed and used by her and men. She has told me I am fem for a man, not a manly man. Has used a dildo on me and I wish I had the nerve to tell her I dress . She knows of my cuck desires but says she is shy. Love to chat and I'm kerry8866@hotmail.com

Kerrysub4uKerrysub4uover 6 years ago
Cd cindy1

We are so alike . Love to chat sometime. I read your profile. It sounds just like me.

AnonymousAnonymousover 6 years ago
5! HEY ANNONY Hope you read this one!!!

If you would have done this your wife, oh your dead ex wife would loved it. She would have died with a smile on her face!! Go fuck yourself asshole

cdCindy1cdCindy1over 6 years ago
Kerrysub4u

Thanks for the comment. You and I are very much alike. I too want my wife to know that she has a sissy CD faggot husband. I want her to watch me suck cock, watch me get fucked, and then have me watch while she gets fucked in front of me. I hope to one day muster the courage to come out of the closet and tell her. Wish me luck.

AnonymousAnonymousover 6 years ago
Question anwsered: thanks!

For months now I've been asking myself how do I avoid having to fuck my wife? And here, in one profound how-to posting, you answered my question!

Thanks!

"Do this regularly so that actual fucking becomes less and less common. It will be necessary for you to masturbate more frequently. "

AnonymousAnonymousover 6 years ago
cdCindy1 and Kerrysub4u

Gentlemen, my suggestion is that the sooner you tell your lovely wives, the easier it'll be for all four of you. Women can sense when our "husbands" have lost their interest in us.

A flaccid penis does not lie. We know it.

The sooner you get out, the faster we can resume our natural breeding instincts.

Embrace reality: gentlemen, as of midnight tonight you both shall cease and desist, and instead welcome your new dawn as sissies!

A K (the author's mistress)

AnonymousAnonymousabout 6 years ago
Sissy husband vs family life

Marriage is about both family and sex. Raising a family is one part, sex is the other you can keep these two apart. My story runs almost parallel to the first part. I do do more round the house and wear an apron. Though it is not that frilly.

We had less sex, I got addicted to webcams. I start just doing oral for her, as after such much camming I lost some of that old sexual energy to stay hard. She did start seeing guys outside of the marriage. I pretend not to know, I carry on on my sissy path dressing in secret, though it is almost an open secret. She has a red sports car now and I think is very submissive in her other relationships. But I think she finds it very satisfying.

Interestingly we do still have sex, but it is like pity sex, often when she is feeling guilty. She doesnt know that much about the scene, so it is with some amusement that I tell her she is a 'hot wife' and she agrees.

The only time it has been embarrassing was on holiday on St Kitts at a resort. I went out doing water sports (ie sailing) and she had sex with tennis coach. I know because coming back early to the room I could hear them or rather her. I had to wait and see him leave. She encouraged me to doing alot of sailing, diving and kayaking.

Later staff smirked at us or me.

jackbirdjackbirdabout 6 years ago
in the closet

I am 60 years old and in the closet cross dresser. My wife only thinks I am bi-curious. Told her years ago would love to share her with other men. She knows nothing of my cross dressing. She travels for her work thats when I get to dress like a slut. She has used toys on me as she sucked me off. We don't have sex anymore last time was months ago before that years. I have asked her many times to cuckold me. At first she didn't know what it was but years of almost begging she knows what I want tells me no way. I can only dream

AnonymousAnonymousabout 6 years ago
At 63

We love to dress up sometimes. Wife and I play games together with men and women. I love to wear heels,thigh high stockings with garter belt and matching mini skirt . As I sit down my panties show to our guest if they are looking. As I cross my legs I make sure my thigh above my stockings shows. My wife loves for me to been over with my ass toward our guest so they can get a look .

EasypeterEasypeteralmost 6 years ago
Hotty

Love to meet 63 Anno

AnonymousAnonymousalmost 6 years ago
most helpful

I am 62 and have had cuckold thoughts for years. Have been lucky to get my wife to try wife swapping and found she really enjoyed it as much as I did letting her. She has also had a boy friend whom I knew but was not sure if he knew that I knew they had had sex.

LittlebeauLittlebeauabout 5 years ago
Let go of her inhibitions

Great ideas, wives pretend to get the idea slowly. Just might add helping her come out of her traditional shell by enjoying something more relaxing thus releasing her to do things most wives crave and read about. “Up in smoke” just occasionally.

Like the way you let her know other guys check her out after she passes them, mine had no idea how much men lusted after her nice ass until I got her to turn and catch them.

AnonymousAnonymousalmost 5 years ago
Alcohol and becoming a sissy

I was taken back by the comment related to alcohol. My wife is a bossy alcoholic, but not really a dom. She certainly gets mean and self-centered when she drinks, which is daily now. I have a hard time with this because she is unpredictable and can be nasty. She has even slapped me before and once even spit on me. I thought about fighting back, but her attitude really puts me in my submissive, sissy space and I just get quiet and take it. I know she loves me,but I never knew I was just supposed to take it and even encourage it. I will say, the times she has fingered me or had me stand and masturbate for her are times when she was drunk. And she does like to flirt more when drunk, and she is a hottie. She has even had me take a pic of her and a guy she met. The next mory she looked at his pic and masturbated, which humiliated me, but got my little 4.5" very hard.... So, I just wanted to say thanks for the direction. I will not worry about her drinking and just take what she gives me - and wit until she does cuckold me and put me in her panties full-time...

AnonymousAnonymousover 4 years ago
Fantastic

This is amazing. 5 big stars

AnonymousAnonymousover 4 years ago
Thank you

I've been appreciating all your stories.

This one is good, as it gives some nice suggestions. I'm already masturbating more. Your comment, "Yeah pretty much, it might give me a stiffy. I know I've been neglecting you lately" is a good one for me to use now!

Thanks again, CD Sara

AnonymousAnonymousover 3 years ago
It is a possible route

The cuckold route is a wild ride but it is guaranteed to end with divorce and the husband being a transgender mtf having sex with men and stuck on the precipice of sex change operation. Hormone therapy and penis to conversion to clit with testicle removal is the right option

sissyinlwsissyinlwabout 2 years ago

I encouraged my wife to cuckold me. She did and left me for a real man. I liked being cucked. I did find my place in life a sissy cock sucker

AnonymousAnonymousover 1 year ago

My wife Claire Louise cucked me 11 years ago and. I’ve loved every minute of cock sucking ass licking and cum cleaning since. Her numerous black bulls have ploughing me kindly too

AnonymousAnonymousover 1 year ago

We are in our 30s and I have the fantasy of my wife fucking another man. I started screwing her less and less. I do go down on her most nights. At first, when she would start to cum, she would try to pull me up to fuck her, but I would resist sometimes ruining her organism. Now she is mostly satisfied with my tongue. I do fuck her a couple times a month but that's about all she wants it now. I am hoping my plan will make her want to fuck another guy and with me watching.

AnonymousAnonymousabout 1 year ago

If your wife no longer considers you a man because you are a sissy cuckold, it doesn't have to end in divorce. In my case my Wife kicked me out of our (now Her) bedroom 10 years ago when i became Her cuckold, She said there was no reason for Her to share Her bed with me and it would be easier for Her to bring guys home. Two years ago She moved Her boyfriend in and i am now a sissy maid to both, sissy cuckold to Her and sissy slut to him. i couldn't be more content.

AnonymousAnonymous11 months ago

I so loved it oh my god, I am not in a relationship other than friends but I am a care giver for a girl who has a total spoiled daughter and I have to clean up after them. they don't even through things in the trash I have to pick it up, Dogs even poop inside and I have to pick it up. she invites friends over, makes me go out side, and also take her to the store and since I am such a pansy I nam afraid to go in side so I stay in the car. sometimes she and another friend get busy and I can't reach them they don't ever return my call unless she needs me. and if I don't hear from her I sit at home and cry like a baby and play dress up of and put nail polish on I have tons of clothed I wear only panties and women jeans. she has taken Ballet and jazz classes and I want to as well but I want so badly to be near her and at least clean and clean and clean in hopes some day she will take me dancing..Golly I am such a sissy and its even worse now she cut my hair in a bob,, and ooh, whaa! I just love fluffing it up and goin outside in my girly jeans, and of course there is no Bulg! makes me feel like such a pussy especially when I go shopping for panties and bras! anyone need a maid?

AnonymousAnonymous6 months ago

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AnonymousAnonymous4 months ago

I abulutely loved it, I want a woman to make me her Sissy Cuckold, I want to fluff her lover and make him hard to fuck her, and lick and clean her well fucked creampied pussy

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userQuietoldie@Quietoldie
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I am retired and over 65. I would like to make money from writing but a short novel I put out on Kindle has not given me any income. Seeing my words in print in Literotica has been great. My writing has slowed down over the years. The stories I write for Lit are not from perso...