Memorable Sissy Cuck Moments

Replies are always appreciated.

If any of you are curious about which ones are experiences I lived, which I modified and what ones are fiction, feel free to ask.

YouKnowWho
Do you feel like you were trained,or just evolved?
Very inquisitive about Your truth or or fiction.
Cuck On to where ever it leads.

lynnblack

My experiences were always as the secret lover, open lover or bull in every case.

The sissy theme reflects what happened to the husbands as their wives and I started getting creative with sex and gender play.

I began dating married women from high school. But I was never happy with going behind anyone's back. So in the late 80s, I insisted there would be no secrets. That the husbands either approved of the affair, or it wasn't an option.

This put the wives in a bind, but most of them went ahead with getting their hubbies to agree (and eventually submit) to it.

Making the guys dress, doll up and effectively switch their gender was a thrill to all the participants.

I never planned to hit on an attractive wife. It would just come out at a chance meeting. A switch would go off in my head, and the dance would start.

The ones that fully embraced all the kinky play often became very dominant and demanding to their male spouses. Sometimes becoming crueler than I ever was.

another sissy set

Birthday party

Family reunion

True love

going deeper

Sissies obey strong men and dominant women.

All dressed, but nowhere to go

A treat to remember this moment

Proper oral sissy rules

Dress up and swallow

[b]YouKnowWho[/2#4. All of you sweeties look adorable!
D

YouKnowWho
35#4. DELICIOUS
D

bobbye

Thanks for the feedback.

Not all the husbands in the past were willing to go as far as dressing up or orally servicing me or another of a wife's lovers.

I was a lucky in that. My very first married couple had an insatiably hot wife who loved watching her husband put on makeup and sexy lingerie before servicing us both.

One scenario similar to 35 - 4 came after a memorable night of sex with her. We'd typically include her husband, to watch, clean us up or have him put on a sissy sex show for us.

That night we told him to go to the spare room instead. She and I woke up early and got him up to make us coffee.

When we met in the kitchen, he was dressed for work. I was wearing one of his bathrobes (open in the front). She had pink silk panties and my shirt. We all sat and chatted a while. Her husband was expressing some frustration for not being invited to his own bed the night before. At first, we ignored him and started talking about some of the wild sex we had. When he brought up his resentments again, I had an idea.

He didn't have to leave for work for at least an hour. So I told him to sit and watch while I took her panties and clothes off, stood up and had her start an incredible blowjob inches from his face. About 4 times, she pulled away to kiss him deeply. It really got him excited.

Once he got that way, we could make him do practically anything. She told him to go back upstairs, put on her pink panties, some makeup, jewelry and his favorite wig (he had 3). Last she told him to brush his teeth, return to the kitchen and wait.

She was on fire. Breathing heavy and dripping heavily between her legs. I lifted her onto the counter, and we began a frantic wet kiss. Moving down, I did the same to her super sensitive nipples and finally her (very) hot pussy. Squirming and moaning, she didn't want to orgasm too soon. She wanted me inside of her when she did. That's when her husband came down to the scene still dressed for work, except that everything from the neck up was very feminine.

With him watching, and her looking into his eyes, she let go big. Now she was truly dripping. Whispering loud enough for us both to hear, she said, "F*ck me right now!". I stood and slipped in bare while she hungrily licked her juices off my lips.

I was going slow to keep her frustration level up to 10. Almost silent in her ear, I said, "I have another idea". As I quietly detailed what I had in mind, she started climaxing again just as I let loose. There was more kissing and groping.

Slowly pulling out, we watched as she pushed out our juices onto my softening cock.

He was already late by then, but we weren't finished with him yet. We called him over, had him kneel in front of me, look up in my eyes and nurse on my slimy/cummy dick long enough to make him even more anxious to get on the road.

I told him not to swallow until he got to work. He asked, "What about the makeup"? Wrong question.

I told him to leave the disheveled way he was and to figure it out on the commute... driver's side window open. The idea being that if anyone looked into his car at a stop light, they would see a guy frantically wiping off heavy lipstick, eyeshadow and mascara.

When he returned home after work, she insisted he recall every detail of the ride, if he got all the makeup off (he didn't) and how he liked the taste of our fucking once he got there.

She also told him she wanted to see him do that every morning I spent the night.

So that meme was definitely a real experience.

YKW, Great post. Please tell us more, past or present stories that follow the same theme. This is a great thread.
Thank you...

cuckold_2

You're very welcome. Glad you and others appreciate it.

YouKnowWho

That's an amazing story!!! Thank you for sharing. And please, share more!

I'm not sure who I'd rather be in that story... you or him!

Cuckold sissy life continued

practice makes perfect

No turning back

Introductions

Holiday cheer

YouKnowWho
I have been kenneled up by Black Master with his Pit Bull,having allready been made his bitch,knotted several times left in kennel all night.

lynnblack

Those are important lessons for you. Proper cuckolds need to understand their first job is to please your wives, masters and any cock that needs relief.

YouKnowWho
Yes Sir,Thank You for everything. I wish i can serve You

lynnblack

It looks like you have a (very) deep desire to be completely obedient to your wife and master. And it looks like there are few limits to what you will do to please them. Bravo.

You should be proud you're a genuinely subm1ssive servant to their whims. Trust that any disc1pline or pervers1on they choose for you is for your own good.

You should always be happy and fulfilled satisfying their primal needs.

YouKnowWho
She doesn't know about Black Master.
I think it's more than she would like.
I am totally submissive servant to his whims,and Master and his crew say,Dam Freaky Nasty Bitch.

lynnblack

Then I'm sure you're all those things. Wear them like a crown.

YouKnowWho
Masters name is Bukra,he calls his pitbul Caligula.
When i go to his place,i have become any thing Bukra says for me to be or do and crave their degradation,Bukra and Caligula Are my Masters

lynnblack

Good for you. You need them to push you way past any limits you thought you had. It sounds like paradise for you

lynnblack

It sounds like you've gone into some very dark places with your masters and friends. And you still crave it.

Describe your most memorable degrading moment with them.

If you feel safer confessing it privately, feel free to message me here.

Does your wife suspect anything if you end up staying overnight in your master's kennel or bed?

Do you dress up pretty for them?

Do you enjoy the degradation more as it's happening or afterward?

What other subhuman things have you done for them?

When your fa+her (or any other relative) used your wife, were you ever allowed to watch or serve them both?

If you get any spankings to correct your attitude, what ways do you show your appreciation afterward?

cuckold_2

As a follow up to the above recollection, 10 days later (a Sunday night), I stayed over again They were both ready in makeup and lingerie. I instructed them to be watching some kind of a sissy, cuckold or subm1ssive male video when I got there. They had one on showing a caged, soft guy on his back, his wife over him facing his feet and a very well-hung man f*cking her bare. It was definitely an amateur production. The one on his back had started by licking the woman's pussy, then, following her firm instructions, had him move first to lick the lover's balls, then his ass crack while the f*cking continued. When he finally came in her, he pulled his cock out, fed it to the guy, then we watched her sit hard on his face and rub her full pussy all over his face and nose.

We turned it off and all agreed to try that. First, we had to take the edge off him by having him lay down, help him lift his legs and jerk off into his own mouth. Then the fun started.

We were all sweaty and spent after. We showered together and sent him back to his room again. This time with instructions to get up early, dress in his same outfit with makeup and prepare us breakfast.

We had him wait, watching while I lifted her up, going deep into her incredibly hot pussy. She orgasmed about 3 minutes later. Instead of cumming in her, I had a different idea.

I told him to crawl over to us, take my cock out and lick it like a lollypop. Then start a slow blowjob.

He was definitely going to be late for work again, so his wife called in for him, knowing that company policy required they talk to him anyway.

She told them he had something caught in his throat, and he would be right with them. Bringing the phone over, I put up a finger to give me a minute. As a tease, I said "not yet" loud enough for the HR employee to hear. Then I blasted everything I had into his painted mouth. He knew the rules that there was no swallowing until he got permission. She handed to phone to him and, with a full mouth, spoke to HR as best he could.

We had him leave his sexy outfit on, but put his work clothes over and leave his face that way until after he got in his car, knowing there would be a risk of him having to pull over and get stopped. That would make it even more embarrassing with makeup, "socks" that looked like fishnet stockings, and a full mouth of cum and saliva.

Lucky for him, he didn't get pulled over.

YouKnowWho
Love to.
Will you private message me,so I can respond?
Lots to respond to.

YouKnowWho

Loved the caps and the continuation of the story! You made him start by jerking off in his mouth to "take the edge off"... lol... So much more difficult to accept pain and h-umiliation when you're not "turn on" anymore. Nice move!

Thank you SOOOOO MUCH!!!!

lynnblack

PM sent.

It goes deeper

Anniversary treat

Weekend fun

It turns us on

Drop everything when they call

A few tech issues, but 4 more. Bent a bit darker.

Take charge

An attentive husband

Get used to it!

Future poppa!

Continued

It's good to be popular

Don't hold back!

An exotic show

Don't make him wait

continued

That's my sissy

Slow and sexy

I know this will hurt

It's a compliment