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When does a cuckold become a "sissy"?

  • Thread starterAliasBilly
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AliasBilly

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May 15, 2020
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I think the words get mixed together some. I don't think I'm a sissy. Most of Mrs. Billy's boyfriends never met me. Of those who have met me, many don't want me around when they're banging her.
A few enjoy me hanging around, masturbating in a corner or "cleaning" them up. Am I a sissy if I have _ANY_ sex with her boyfriend? Do I have to crossdress or something?
 
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When you clean them or there is touching yes , Just sitting watching wife get fucked by a REALMAN. You just a cuckold.I ama very bisissy cuckold for 45 years .panty boy for 55 years and love it
 
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AliasBilly said:
I don't think I'm a sissy.
You don't...?
AliasBilly said:
Most of Mrs. Billy's boyfriends never met me.
How can your wife's lovers fully enjoy fucking her, if they haven't met you so they can properly humiliate you as her cuckold (and, possibly, her sissy cuckold)...?
AliasBilly said:
Of those who have met me, many don't want me around when they're banging her.
You must feel left out....
AliasBilly said:
A few enjoy me hanging around, masturbating in a corner or "cleaning" them up.
It must be a relief to be allowed to participate....
AliasBilly said:
Am I a sissy if I have ANY sex with her boyfriend?
Beats me. Whether you view yourself as a "sissy" (or not) is up to you.
AliasBilly said:
Do I have to crossdress or something?
If you want to cross-dress, go for it. You might introduce your sexy wife to:

Femme Your Hubby — Installment # 1
http://adult.hypnoticwishes.com/gallery/femme-your-hubby1.php

then ask her if she would like to assist you by guiding you along those lines.
 
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AliasBilly said:
OK, I told her about the question. She says I'm not a sissy, but neither am I "enough man" for her.
Sounds like strongly-qualified praise.
AliasBilly said:
The size of my penis is something we've talked about for years - her view is that I would be enough for some women, but not for her.
That was pretty blunt.
AliasBilly said:
She asked me if I felt bad about the times I'm not in the room when she entertains, and I said yes, I prefer to see her than to be shut out. She promised to ask her men to let me in in the future.
Nice....
AliasBilly said:
About the sissy issue, she suggested the next time i'm in my corner watching, I wear lipstick and see what happens. I'll come back and let you guys know.
—Bill
Sounds like your sexy hotwife has perceived your interest and is starting you down the road. Please keep us filled in.
 
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AliasBilly said:
[My wife] told me she's doing me a big favor; she's going to sleep with "Bob" instead of "Fred" tonight because Bob agrees it would be hot to have me in the room, wearing lipstick.
Your sexy wife is right. She is doing you a big favor.
AliasBilly said:
(Fred is in the "I don't want the cuck around" group).
Oh well.... I suppose you can't expect your wife's lovers to all have similar sexual inclinations.
AliasBilly said:
Bob said "I'm a sick fuck," but it will be fun to tease me.
No doubt. And, good — Bob seems to have the right attitude.
AliasBilly said:
Funny thing is, I kind of think Fred is the better-looking guy and Bob is just a normal guy.
Whatever....
AliasBilly said:
I don't get to pick them, however.
No, of course not. Your wife should properly insist that selecting the other men she wants to fuck should be entirely up to her (as she does, it sounds like).
AliasBilly said:
I think Mrs. Billy is looking forward to this even more than I am. She made me shave my body hair this afternoon. It hurt more than I guessed it would, what with nicks and scratches.
Very good. Your wife has moved you another step down the road toward becoming her submissive sissy cuckold (as opposed to you being merely her cuckold). If you continue to cooperate, and give her positive feedback, she will get you there.
 
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AliasBilly said:
She [my wife] told me she's doing me a big favor, going to sleep with "Bob" instead of "Fred" tonight because Bob agrees it would be hot to have me in the room, wearing lipstick.
How's it going, AliasBilly? Did you take your first step toward becoming your wife's self-acknowledged sissy cuckold by sitting in your chair, watching while wearing lipstick and with your body shaved, while your wife fucked her lover Bob...?

If so, did you feel like that was the right situation for you to be in...?
 
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Thanks for the update, AliasBilly.
AliasBilly said:
That was the first giant step forward right there - none of [my wife's] lovers have ever spent the night before. Bob took my place in the big bed....
Very good....
AliasBilly said:
He was thrilled that I was wearing lipstick as he suggested, and I have to tell you I looked like a pathetic clown.
Or a cuckold who is learning to become his wife's submissive sissy....
AliasBilly said:
But the pleasure he got out of seeing my red lips was nothing compared to his glee that Mrs. Billy had shaved my body hair and made me look like a girl all over.
Nice....
AliasBilly said:
Bob made me sit naked in the chair mainly because of the shaving. He never much wanted to see any of my naked body parts before this. But hairless and lipsticked, perched in a chair? He really seemed to get off on it. To the point he was distracted, and Mrs. Billy started to tell him to pay attention to her.
Hm.... sounds like Bob may be bisexual. There's nothing wrong with that, of course.
AliasBilly said:
He tried, but my hairless little erection kept distracting him and she got up and made me put on a pair of her panties.
Totally appropriate....
AliasBilly said:
Just before going back to bed with him, she picked her bra up off of the floor and put that on me, too.
Also totally appropriate....
AliasBilly said:
Then she started to blow him again. Which meant she couldn't see his face. I started to get a little giddy and disconnected from reality - I mean, I was wearing lingerie and lipstick, playing with my cock, while Bob seemed too interested in me. I vamped for him a little, just to see what would happen.
What does "vamped" mean...?
AliasBilly said:
He and I had never had sexual contact before tonight, and it was sort of a joke to me. So I pulled my shoulders back, thrusting my empty bra at him, and pursed my lips, and wriggled my ass in the chair.
I don't think you really viewed it as a joke. It sounds like you too may be bisexual. There's nothing wrong with that either, of course.
AliasBilly said:
But time ran out and my wife climbed up on top of him and gave him a cowgirl ride that made him forget all about me.
Good for your wife.
AliasBilly said:
After he orgasmed, they pretty much just rolled over, ordered me to turn off the light on my way out, and sent me to the couch while they fell asleep.
What?! Bob did not bring your wife to orgasm?! That was unfortunate....
AliasBilly said:
I don't think it would be quite true to say I was disappointed. It was what it was, and in a sense it had been way more intimate for me than any previous encounter my wife had let me witness. I went to bed happy.
Good....
AliasBilly said:
A few hours later I was awakened by Bob kneeling on the sofa next to me, rubbing his sticky dick over my lipsticked mouth. I awoke slowly and just let him continue for a minute or two. He whispered "let me in, Billie" and I did. I would like to make it a big story but it was all over quickly - I opened, I nibbled and sucked, he dumped a small load in my mouth, and he was done. He leaned over me to whisper, "Don't tell your wife and maybe we can play again."
Ah ha.... more evidence that Bob is bisexual.
AliasBilly said:
None of what happened Thursday night, the cross dressing, the lipstick, even the blow job, none of it was as surprising to me as what I did then. I pulled his head to me and I kissed Bob like a woman.
Ah ha.... more evidence that you are bisexual.
AliasBilly said:
I'm not sure why - I have played games with guys before, but I never ever kissed a man or wanted to.
You followed your instinct. There's nothing wrong with that.
AliasBilly said:
Until Bob said we might play again. That triggered something. Who knows if he meant it?
I think you can assume he meant it. You've successfully taken important initial steps toward feminization — i.e., toward becoming the submissive sissy cuckold that will appeal to both your sexy wife and her lover Bob.
 
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Hello Billy - don’t get wrapped up in words and stereotypes. Just do what feels good, go with the flow and let yourself go. You will soon cum to love being slutty cumdump.
I was like you reluctant at first but with guidance of understanding adventurous wife now Mistress I wouldn’t trade my life with anyone
 
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Hi Billy. I know what you mean about kissing being gayer than cocksucking. I write porn on Literotica, and in one of my stories I wrote:

"There is something irrevocably and totally gay about letting another man French kiss you. Everything that had come before was just "curiosity", or "bisexuality". But taking another man's tongue into your mouth and sucking on it was just the most gay, submissive thing a man could do. It made you a sissy to your soul. It eradicated your very masculinity, now and forever. I know this because I gave up my struggle and sucked Paul's tongue into my mouth. The instant I gave in I didn't merely relent, but I collapsed. I sucked Paul's tongue like it would save me from drowning. I think my little balls tingled as they became, in that moment, forevermore useless to me. I may not have just become a woman, but I knew in that moment that I wasn't a man anymore, either. "

Did you feel at all like that?
Don
 
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You described many things being done TO you, but only one thing you initiated - kissing the man who cuckolded you. I think you have several things at risk now. I hope it turns out well for you. Please keep us in the loop.
Don
 
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when you're competing for cock with your wife?
 
One of wife's first bulls suggested to her that I wear her stockings and panties as I watched them. Over time I have been femininized. Most of her bulls are happy for me to be dressed as her sissy cuck. A few will have her on her own. Which is fine for me.
 
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AliasBilly said:
I'm still trying to digest the things that happened Thursday night when Bob slept over.
That's the first giant step forward right there - none of her lovers have ever spent the night before. Bob took my place in the big bed and I slept on the couch.
He was thrilled that I was wearing lipstick as he suggested, and I have to tell you I looked like a pathetic clown. But the pleasure he got out of seeing my red lips was nothing compared to his glee that Mrs. Billy had shaved my body hair and made me look like a girl all over.
Bob made me sit naked in the chair mainly because of the shaving. He never much wanted to see any of my naked body parts before this. But hairless and lipsticked, perched in a chair? He really seemed to get off on it. To the point he was distracted and Mrs. Billy started to tell him to pay attention to her. He tried, but my hairless little erection kept distracting him and she got up and made me put on a pair of her panties. Just before going back to bed with him she picked her bra up off of the floor and put that on me, too. Then she started to blow him again.
Which meant she couldn't see his face. I started to get a little giddy and disconnected from reality - I mean, I was wearing lingerie and lipstick, playing with my cock, while Bob seemed too interested in me. I vamped for him a little, just to see what would happen - he and I had never had sexual contact before tonight, and it was sort of a joke to me. So I pulled my shoulders back, thrusting my empty bra at him, and pursed my lips, and wriggled my ass in the chair.
But time ran out and my wife climbed up on top of him and gave him a cowgirl ride that made him forget all about me. After he orgasmed they pretty much just rolled over, ordered me to turn off the light on my way out, and sent me to the couch while they fell asleep.
I don't think it would be quite true to say that I was disappointed. It was what it was and in a sense it had been way more intimate for me than any previous encounter my wife had let me witness. I went to bed happy.
A few hours later I was awakened by Bob kneeling on the sofa next to me, rubbing his sticky dick over my lipsticked mouth. I awoke slowly and just let him continue for a minute or two. He whispered "let me in, Billie" and I did. I would like to make it a big story but it was all over quickly - I opened, I nibbled and sucked, he dumped a small load in my mouth, and he was done. He leaned over me to whisper "Don't tell your wife and maybe we can play again."
None of what happened Thursday night, the cross dressing, the lipstick, even the blow job, none of it was as surprising to me as what I did then. I pulled his head to me and I kissed Bob like a woman. I'm not sure why - I have played games with guys before, but I never ever kissed a man or wanted to. Until Bob said we might play again. That triggered something. Who knows if he meant it?
SO HOT! I would have been disappointed though that Bob didn't say, " get over here sissy boy and clean us up. " THEN! him spanking my panty ass say "get out now sissy boy". So I'm guessing that your wife only likes seeing you as a cross dresser kind of cuckold, but not a cock sucking cuckold sissy.
 
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You need to get a second opinion. Upload a photo here wearing your panties and lipstick.
 
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My wife used my dressing as an excuse to cuckold me with a real man and told him and all her workmates about my nasty little habits.

DA1635A5-AA64-4E68-AE5D-CD4F893DE810.jpeg
 
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siss4it37 said:
My wife used my dressing as an excuse to cuckold me with a real man and told him and all her workmates about my nasty little habits.

DA1635A5-AA64-4E68-AE5D-CD4F893DE810.jpeg

She doesn't need an excuse or your permission to cuckold you! You presenting her small deckle is all the reason she needs. You can never satisfy her with such a small dicklet. Girl's godda do what a girl's godda do. Of course she told everyone. Nothing wrong with advertising that she needs a good fuck. I'll bet more than one of her workmates have fucked her. You have to learn to be content with cleaning her cum filled pussy and painting her tonails.
 
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AliasBilly said:
Last week of May Mrs. Billy and I had a fight - about him, of course, the guy I call "Bob " here.
Oh oh....
AliasBilly said:
.... My wife threatened to make Bob scarce if he was going to pay more attention to the lipsticked version of me than to her. I actually had to promise her that I wouldn't try to attract him.
Oh my goodness....
AliasBilly said:
She also read him the riot act, told him his behavior toward me made her feel bad. She told him it was fun at first to torment me, but she expected most of his time and attention when he visited.
Hm.... the "riot act," not to be confused with the "insurrection act"? There seems to be a lot of discussion of the latter these days, by a certain person who considers himself the "president."
AliasBilly said:
I feel like I'm cukolding her, tempting away her partner.
Oh my.... but, on the other hand, you might reason that "fair is fair."
AliasBilly said:
So he visited Saturday, and while they didn't shut me out, they made me stay in the living room while they had sex in the bedroom with the door open. True to his word, Bob ignored me most of the time.
Very good. Your wife had apparently resolved the problem....
AliasBilly said:
After she fell asleep, he tiptoed out and got into the foldout bed with me. I sucked him again, this time in a better position, me on my knees with him on the couch.
Hah! But you and your wife's lover fooled your wife....
AliasBilly said:
Just before we called it a night he played finger games with my hole and sucked my much smaller penis to (another) orgasm. Then he went back to sleep the rest of the night with my wife.
Your ass has been saved, and his too, by your wife being a sound sleeper....
AliasBilly said:
I guess I'm sort of a sissy, but then he is, too, and he's our bull.
I guess so. But, you pays your money and makes your choices....
 
HI AliasBilly,

How is it going? Was your hotwife sexually satisfied over the weekend? I hope....?

Regarding your comment:
AliasBilly said:
Last week of May Mrs. Billy and I had a fight - about him, of course, the guy I call "Bob " here. She has another lover who won't even let me in the room when they're at it, and my wife threatedned to make Bob scarce if he was going to pay more attention to the lipsticked version of me than to her. I actually had to promise her that I wouldn't try to attract him [Bob].
You should never fight or argue with your hotwife. A way to restore her good feelings toward you might be to persuade her to allow you to become her asskisser. As you may know, there are thousands of nerve endings around the anus. Some women can orgasm from analingus. Your hotwife may find she is among them. At the least, she is likely to find it pleasurable. An illustrative video, suitable for both you and your hotwife to watch, can be found by entering this link into your preferred search engine:

Facesitting and Asslicking video:
https://www.thumbzilla.com/video/ph5ed02872d452d/facesitting-and-asslicking

(if you find you cannot link to it from this forum}. (I tried it, and found it is possible to link to it from this forum.)

—Custer
 
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What a beautiful ass she has!
 
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AliasBilly said:
Am I a sissy if I have _ANY_ sex with her boyfriend? Do I have to crossdress or something?
When you start competing with your wife in sexy outfits and the bull's attention
 

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