Discovering hubby might want to be cuckolded

Glad to hear it's working out for you. Love reading your descriptions. I hope your hubby loved it as much as you, even not letting him out of his cage.
 
This past weekend, we had another cuckold experience. Hubby had been thinking about it a lot and set up a more elaborate situation. I was wanting some real male attention so I agreed to it. I had fun getting dressed up to 'please'. Hubby dressed in sissy lingerie but under guy clothes.

We went to a restaurant where he sat at the table next to me but not with me. Gary joined me and we had a nice dinner that got flirty. Hubby was watching everything but couldn't say anything or get close to us. I started teasing Gary's legs with my foot slipped out of my high heels and I saw that hubby was squirming.

Although I was tempted to do something crazy in the restaurant or restaurant bathroom, I kept it under control. We left hubby to pay the check and went outside. Gary started kissing me next to his car and I enjoyed that very much. I got in Gary's car and hubby drove our car home. We waited in the driveway a little bit, kissing and me caressing his cock which had extended down his pant leg. I knew the car would be too cramped so we went inside.

Going up to our bedroom, we saw hubby in his new sissy dress, heels, and wig. I knew he had locked the dress on himself and he'd been in his cock cage for weeks. We ignored him. I did a little strip tease for Gary and then he got undressed for me. I gave him a short blow job because his cock is just so gorgeous and suckable, but we quickly got to what we really wanted.

As requested by hubby, I teased about not using a condom but then made sure we did and Gary got to work. I'll admit that I forgot about hubby squirming in the corner. I just loved what Gary was doing to me, how he felt on me and in me. Each time he came, we made hubby drink the cum from the condom.

When we were spent, I led hubby to the guest room and cuffed him onto the guest bed. I made plenty of noise welcoming Gary to sleep with me and we spent the night. (We fucked again around 3am but I think hubby was asleep)

In the morning, after Gary left, I released hubby and unlocked his dress so he could use the bathroom. He was begging me to take his cock cage off and let him cum but he still waiting for that.

This was much easier than the first time, emotionally for me, and I am still grinning from how pleasurable it was. A female friend at work commented that I must have gotten some, LOL.

Very hot!!
 
Has your wife had many lovers? Are you always present? Are you sissified?

Yes lots. No I haven't been there to watch her every time. In fact I would say I watched her on only around 30% of the time. The reason being that she finds that the guys she fucks are uncomfortable with hubby being there. She claims they are more relaxed and this makes the sex better and more enjoyable.
I am a crossdresser but unlike your man I still fancy my wife and we always have "reclaiming " sex. That is After I have done my most important cucky duty and licked her will filled cunt clean.
Happy to answer any more questions you may have or you can pm me.
Happy Friday x
 
This past weekend, we had another cuckold experience. Hubby had been thinking about it a lot and set up a more elaborate situation. I was wanting some real male attention so I agreed to it. I had fun getting dressed up to 'please'. Hubby dressed in sissy lingerie but under guy clothes.

We went to a restaurant where he sat at the table next to me but not with me. Gary joined me and we had a nice dinner that got flirty. Hubby was watching everything but couldn't say anything or get close to us. I started teasing Gary's legs with my foot slipped out of my high heels and I saw that hubby was squirming.

Although I was tempted to do something crazy in the restaurant or restaurant bathroom, I kept it under control. We left hubby to pay the check and went outside. Gary started kissing me next to his car and I enjoyed that very much. I got in Gary's car and hubby drove our car home. We waited in the driveway a little bit, kissing and me caressing his cock which had extended down his pant leg. I knew the car would be too cramped so we went inside.

Going up to our bedroom, we saw hubby in his new sissy dress, heels, and wig. I knew he had locked the dress on himself and he'd been in his cock cage for weeks. We ignored him. I did a little strip tease for Gary and then he got undressed for me. I gave him a short blow job because his cock is just so gorgeous and suckable, but we quickly got to what we really wanted.

As requested by hubby, I teased about not using a condom but then made sure we did and Gary got to work. I'll admit that I forgot about hubby squirming in the corner. I just loved what Gary was doing to me, how he felt on me and in me. Each time he came, we made hubby drink the cum from the condom.

When we were spent, I led hubby to the guest room and cuffed him onto the guest bed. I made plenty of noise welcoming Gary to sleep with me and we spent the night. (We fucked again around 3am but I think hubby was asleep)

In the morning, after Gary left, I released hubby and unlocked his dress so he could use the bathroom. He was begging me to take his cock cage off and let him cum but he still waiting for that.

This was much easier than the first time, emotionally for me, and I am still grinning from how pleasurable it was. A female friend at work commented that I must have gotten some, LOL.


Hi Annie I’ve been reading your thread with great interest. From chatting and opening about your desires and sexual needs you have moved on and greatly enriched you and your husband’s sexuality. Isn’t it so exciting and liberating.
I’ve embrased my kinkyness since my forties when I started to enjoy the feel of cross dressing in lingerie and exploring my bi and voyeuristc side. Unlike your lovely hubb I’m not cuck but I love arranging and watching my gf with othe men and women. We also like an element of bondage and SM
Like you exploring our sexuality has been wonderful. Tc
 
A couple weeks ago we had another overnight. I had planned ahead. It began as an evening of my dolled up sissy hubby being able only to watch Gary and I having a nice little sex marathon, unable to say anything due to the ball gag or interfere because he was locked to the chair. When Gary and I wanted to go to sleep together, I led sissy back to the guest room and strapped her down to the bed firmly. I pulled her panties down and slid a large anatomically accurate cock dildo into her pussy and pulled the panties back up over it. Her clit was a mess of precum and cum (the little slut had cum from watching us and her own humiliation) but it stayed in its cage.

The next morning, Gary went in to wake sissy by having her suck his cock. After that, he left and I finally released hubby. He said it was such an erotic night. He was very grateful.
 
Find that lustful desire and express it. Show him how much you enjoy it. Find out what he likes about it - and play to that, especially if that pleases you too. And when you toy is done fucking you and gone, make your sissy lick you clean.
 
A couple weeks ago we had another overnight. I had planned ahead. It began as an evening of my dolled up sissy hubby being able only to watch Gary and I having a nice little sex marathon, unable to say anything due to the ball gag or interfere because he was locked to the chair. When Gary and I wanted to go to sleep together, I led sissy back to the guest room and strapped her down to the bed firmly. I pulled her panties down and slid a large anatomically accurate cock dildo into her pussy and pulled the panties back up over it. Her clit was a mess of precum and cum (the little slut had cum from watching us and her own humiliation) but it stayed in its cage.

The next morning, Gary went in to wake sissy by having her suck his cock. After that, he left and I finally released hubby. He said it was such an erotic night. He was very grateful.

Ignore my post, you obviously have it down. Good Work!
 
A couple weeks ago we had another overnight. I had planned ahead. It began as an evening of my dolled up sissy hubby being able only to watch Gary and I having a nice little sex marathon, unable to say anything due to the ball gag or interfere because he was locked to the chair. When Gary and I wanted to go to sleep together, I led sissy back to the guest room and strapped her down to the bed firmly. I pulled her panties down and slid a large anatomically accurate cock dildo into her pussy and pulled the panties back up over it. Her clit was a mess of precum and cum (the little slut had cum from watching us and her own humiliation) but it stayed in its cage.

The next morning, Gary went in to wake sissy by having her suck his cock. After that, he left and I finally released hubby. He said it was such an erotic night. He was very grateful.

Such a yummy story. Not sure whom i want to be most, you, him, or gary
 
A couple weeks ago we had another overnight. I had planned ahead. It began as an evening of my dolled up sissy hubby being able only to watch Gary and I having a nice little sex marathon, unable to say anything due to the ball gag or interfere because he was locked to the chair. When Gary and I wanted to go to sleep together, I led sissy back to the guest room and strapped her down to the bed firmly. I pulled her panties down and slid a large anatomically accurate cock dildo into her pussy and pulled the panties back up over it. Her clit was a mess of precum and cum (the little slut had cum from watching us and her own humiliation) but it stayed in its cage.

The next morning, Gary went in to wake sissy by having her suck his cock. After that, he left and I finally released hubby. He said it was such an erotic night. He was very grateful.

Gary was one lucky guy to find such a hot couple. So jealous 🤐
 
@ SweetAnnie40

I have loved watching the evolution of your relationship through the lens of this thread. I'm not a sissy nor a crossdresser, but I have been cuckolded. I love it.
 
@ SweetAnnie40

I have loved watching the evolution of your relationship through the lens of this thread. I'm not a sissy nor a crossdresser, but I have been cuckolded. I love it.

Thank you. Any suggestions for cuckolding my sissy hubby further?
 
Thanks for the feedback. Lit is a pretty nice community. Yes, we do communicate a lot. Every once in a while one of us reaches a point that we're still nervous about sharing but I think it all comes out eventually.

I've asked him about his feelings about me dating this woman and how turned on it seems to make him. He admits that it gets him very excited thinking about me finding pleasure with her. So far he can't explain why. He's becoming more open about wanting to suck a real cock (and be fucked) but we're still exploring the layers there.


Fascinating situation. Thank you for sharing, Sweet Annie.
May I ask how he came out to you as a sissy? (Asking for a friend. ;o)
 
A couple weeks ago we had another overnight. I had planned ahead. It began as an evening of my dolled up sissy hubby being able only to watch Gary and I having a nice little sex marathon, unable to say anything due to the ball gag or interfere because he was locked to the chair. When Gary and I wanted to go to sleep together, I led sissy back to the guest room and strapped her down to the bed firmly. I pulled her panties down and slid a large anatomically accurate cock dildo into her pussy and pulled the panties back up over it. Her clit was a mess of precum and cum (the little slut had cum from watching us and her own humiliation) but it stayed in its cage.

The next morning, Gary went in to wake sissy by having her suck his cock. After that, he left and I finally released hubby. He said it was such an erotic night. He was very grateful.

O my God! This may be the hottest thing I've ever read.
 
Fascinating situation. Thank you for sharing, Sweet Annie.
May I ask how he came out to you as a sissy? (Asking for a friend. ;o)

It sort of all came out in a rush. She'd been moody for a couple weeks so I was asking her what was wrong. She "confessed" to me... how she got started... what she wanted... how she was terrified I wouldn't understand or would want a divorce or wouldn't love her any more. We talked a lot as I tried to get my head wrapped around it. It didn't change that I loved her but it gave me a way to help her live her truth in a very sexy and pleasurable way.
 
So Hubby is a happy cock-sucker now for several months, also receiving a nice big cock in his sissy pussy. He also enjoys being tied up and forced to watch as our shared lover has sex with me. He often cums (usually because he's fully dressed as a sissy... well, that's all the time in the bedroom anymore... but he's sitting on a nice big cock dildo affixed to the chair so he bounces and fucks himself and cums as he watches Gary and I do everything we want. Ball-gagged so he doesn't interrupt us).

Now he's starting to ask for more extreme cuckolding. I haven't found a new lesbian lover in real life :)() and he seems to want to see me with more big cock men and humiliate him more. Gary, our regular sex play partner, is too much of a friend now. I think hubby wants me with strangers.

Any guidance on how to proceed? I wasn't really looking to find more male partners but Hubby's inability to fuck like a man anymore leaves me... hungry for a real good fuck. So I'm at least entertaining the idea...
 
So Hubby is a happy cock-sucker now for several months, also receiving a nice big cock in his sissy pussy. He also enjoys being tied up and forced to watch as our shared lover has sex with me. He often cums (usually because he's fully dressed as a sissy... well, that's all the time in the bedroom anymore... but he's sitting on a nice big cock dildo affixed to the chair so he bounces and fucks himself and cums as he watches Gary and I do everything we want. Ball-gagged so he doesn't interrupt us).

Now he's starting to ask for more extreme cuckolding. I haven't found a new lesbian lover in real life :)() and he seems to want to see me with more big cock men and humiliate him more. Gary, our regular sex play partner, is too much of a friend now. I think hubby wants me with strangers.

Any guidance on how to proceed? I wasn't really looking to find more male partners but Hubby's inability to fuck like a man anymore leaves me... hungry for a real good fuck. So I'm at least entertaining the idea...



There are a couple of ways to proceed.......your sissy seems to be please to see you pleasured by others, we know that.........that is a given and so far it has only been with men. We know he gets a thrill out of the seeing the excitement you are enjoying with other lovers, and that wouldn't change. I think when he see’s you with a man, it is competition and the humiliation of not being as good as a lover. I am sure you are a bit more excited and vocal doing it with someone else, and that is something he notices and I would imagine it is a total turn on for him as well. I bet he cums riding his dildo the same time you do or when your lover cums, you are just too preoccupied to notice that. It also is good for him because your lover can also administer some enjoyment to your sissy as well, and we know he loves that too.

The other road would be if you found a woman that could accept you as a couple. The perfect match would be a dominate Mistress who would be able to dominate both of you. And here is where the dynamics change, when she is working with you, getting you excited with her sweet torture.

https://cdn02.**********/uploads/photos/2018/12/42215/bdsmlr-42215-FrTKeVL7KA.jpg

Your sissy has no way to compete with that she is a woman and even though his is dressed like that, he really does not have the knowledge to all your “buttons” because she is a woman and knows. This would be a real insecurity for him. And I would pretty much figure you would be much more turned on with her doing what she is doing to you. That will not go unnoticed….if you’re a little shy in front of your sissy, he can always be blindfolded and only able to hear the sounds of your passion.

Like Gary she could also take your sissy with a strapon and both of you could ridicule him while he is getting fucked, I’m sure you could make use of his mouth with your pussy and would enjoy the situation even more.

https://cdn02.**********/uploads/photos/2019/01/66022/bdsmlr-66022-n2WE4DmyaK.gif

I think it is good that you are finding your passion in another women, you have wanted this for a long time and you need to fulfill that. I think at some time a dominate couple that is Bi would really fit the bill for both of you, she’d be in control of you and he’s be working over your sissy…or the situation could also be a 2 on 1 and both Dom’s could be working on you or your sissy. It’s a big world out there and the possibilities are kind of endless and just depends what you both want. I always got a lot of enjoyment watching my wife being pleasured. I guess voyeurism is my weak spot…most men are like that. it’s one of the reason video porn is so popular with men.

I hope what ever you do.......you will share it with the people who care about both of you :rose:
 
I find as a fetish cucking to be quite intriguing and hot. The real thing though is pretty psychologically deep on a whole bunch of levels.

IMO, many many men would love to be in the room watching (but not allowed to touch) while their wife is handled by a stud. I don't know where the line is though between this and actually being a cuck. Food for thought.
 
I find as a fetish cucking to be quite intriguing and hot. The real thing though is pretty psychologically deep on a whole bunch of levels.

IMO, many many men would love to be in the room watching (but not allowed to touch) while their wife is handled by a stud. I don't know where the line is though between this and actually being a cuck. Food for thought.

The line is......both are deeply in love of one another and they do it to please one another collectively. The act is for purely pleasure and the enjoyment comes from knowing after it's over they are still together as one, because sex isn't love or if that were the case senior citizen divorce rates would be out of the roof.......just saying
 
We've got tentative plans for this weekend to amp up the cuckold scene a bit and see how we all feel about it. Gary will be coming over, hubby will be full-on sissy and restrained in a chair in our bedroom. He will have a cock in his pussy to squirm on. Gary and I haven't been together in quite awhile and I'm rather pent up. I'm going to lay on the cuckold talk (so much bigger than you, god you never made me feel this way, etc.) I don't know if Hubby will like it as much as he thinks he will but I said I would try it once.

All of this is possible because our son and his girlfriend are taking a weekend trip to visit friends so we finally have the house to ourselves for some unrestrained erotic pleasures (well, unrestrained for Gary and I lol...)
 
Great thread

I 'shared' my wife inadvertently a few years ago when we were temporarily separated and she got a boyfriend. Once we worked everything out and got back together, our sex life changed because of her experience with him. Since then, we (mostly me) have researched cuckolding and I find it intriguing. So far, she's not interested . . .
 
We've got tentative plans for this weekend to amp up the cuckold scene a bit and see how we all feel about it. Gary will be coming over, hubby will be full-on sissy and restrained in a chair in our bedroom. He will have a cock in his pussy to squirm on. Gary and I haven't been together in quite awhile and I'm rather pent up. I'm going to lay on the cuckold talk (so much bigger than you, god you never made me feel this way, etc.) I don't know if Hubby will like it as much as he thinks he will but I said I would try it once.

All of this is possible because our son and his girlfriend are taking a weekend trip to visit friends so we finally have the house to ourselves for some unrestrained erotic pleasures (well, unrestrained for Gary and I lol...)

A hot adventure to be had for sure
 
I'm open to suggestions for language or sentences I need to be vocal about while it is happening.

"Oh him? He's just a pathetic sissy bitch. He can't get hard like a real man."
"God, Gary, your cock is amazing, so much bigger than his mincing weinie."
"I've never been fucked this good... you're so much better than he ever was."
 
We've got tentative plans for this weekend to amp up the cuckold scene a bit and see how we all feel about it. Gary will be coming over, hubby will be full-on sissy and restrained in a chair in our bedroom. He will have a cock in his pussy to squirm on. Gary and I haven't been together in quite awhile and I'm rather pent up. I'm going to lay on the cuckold talk (so much bigger than you, god you never made me feel this way, etc.) I don't know if Hubby will like it as much as he thinks he will but I said I would try it once.

All of this is possible because our son and his girlfriend are taking a weekend trip to visit friends so we finally have the house to ourselves for some unrestrained erotic pleasures (well, unrestrained for Gary and I lol...)


If I were you I's kind of keep track of the time and see how fast he cums grinding on that dildo..... that talk should push him over the edge. It all centers on that he knows what you are saying is to heighten his pleasure....Some cuddling after the playtime will set him at ease too. I hope you have time to let us know how the weekend went :)
 
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