XXX I've become a Sissy Cuckold
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This story might seem a little too incredible for some people to believe. However, it is what it is. Those of you that have experienced the same transformation in your lives will perhaps best understand what I'm going through.

For as long as I can remember, I've always been something of a sissy. I can't explain why, but the look and feel of childish, feminine clothing has always excited me. Maybe I was raised too fast but as I grew older, I developed a passion for wearing diapers and babyish clothing.

My wife is fairly vanilla but she's been very tolerant of my aberrations and we've gradually moved to a lifestyle that suits both our needs very well. We sleep in different rooms, she in the master bedroom, and I sleep in an adult sized crib in my nursery (see my pictures elsewhere in this forum). Over the years, I've accumulated a vast wardrobe of sissyish clothing appropriate for a little toddler girl.

We began experimenting in chastity a couple years ago and my wife has used it to punish me for normal infractions. However, when she found traces on our computer that I'd been surfing for porn, she decided to lock me up for a year. That was in October.

Now, a normal woman has sexual desires that need to be fulfilled, and sometimes, a sissy can't provide that. As the weeks went by, and she wasn't being made love to, she started thinking more and more about real men, men who don't wear diapers and sleep in baby's cribs. My wife is very forthright and honest with me and she's confessed that the idea of sleeping with another man while I'm locked up and deprived is very exciting to her. We both agreed that it was only reasonable that she should get satisfaction outside our marriage and she told me about a younger guy at work she's been flirting with.

She's developed a relationship with this man at work and the other day, as they walked out to her car, she let him kiss her in the parking lot.
This has really sparked her sexual fires and our lives are entering a whole new phase. I knew she was going to take it to the next level and that day, she'd assigned me some chores to do around the house and picked out a sissy outfit that I was required to wear. Even though I was excited about what was happening, I had to complete my chores or else risk a trip over her lap and a session with her paddle. In fact, when she came home, the first words out her mouth were, "those dishes better be done..."
My buns tingled involuntarily as I realized how narrowly I'd avoided that spanking.
After setting her keys down, she immediately made me get on my knees and begin orally worshiping her pussy. As I sucked and licked, she told me in great detail what her new boyfriend had done, about how he had french kissed her and brazenly stroked her big breasts (unlike myself, my wife is well endowed and her breasts are 36DDD).

After her first orgasm, she shoved me on the floor, on my back, and mounted my face for a second orgasm. She explained that she was going to be having him sex with him while I was to be kept locked up and deprived. She explained that at some point, she'll lock me in my nursery and invite him over so they can have sex in the master bedroom, while I'll be forced to listen. In fact, she's even asked the guy if he'd be okay with that and he's assured her that he is. I don't know if he's into the whole cuckold thing or if he just wants to shag my wife. Either way, I know I won't be getting any sleep that night. Listening to her moaning in the other room while I'm tucked into my crib dressed like a baby will be so utterly humiliating, not to mention I'll be in constant fear that her boyfriend may want to come in and see how I look. I would be so crushed with shame if that were to happen--I have no idea what I would do or say.

She's since learned that he has a nice, big cock (7") which is much bigger than mine, I know he will be able to satisfy her in bed like she deserves. He sent her a pic of his cock and today, I asked her if I could see it. I guess part of me didn't believe it was really happening but there it was, a picture on her phone of her boyfriend, his big thick cock in his hand.

We're moving in gradual stages right now and she doesn't anticipate having sex with him for a month or so, and the first time will be somewhere else, like a hotel, rather than at our home. But she wants to do it on a night when I'll be at home, so I can think about how she's being satisfied by a real man all night. She wants to take this gradually, because after 12 years of marriage, this sort of thing doesn't come natural for her.
On the other hand, she's already set up a date with him that will be all day next Tuesday--and she told me she doesn't know when she'll be home. I know I'll be on pins and needles all day, thinking about what she's doing. One thing she wants to do is suck his big cock, something she never did for me. I have to confess that the idea turns me on tremendously and it seems to only drive me further into my sissy world.

My wife told me her boyfriend likes satin bras, so tomorrow, we're going shopping to get her a new one. She wants me to pick out her outfit for her date on the night before and I'll do my best to put out her sexiest things.

She's really taking to this like a fish to water and we're both very excited. I know its weird but I love the idea of her being satisfied by a buff, younger man with a nice big cock. She's fond of telling me that I'm nothing but a big sissy who can't meet her needs which is why I'll be at home, dressed like a baby girl, working on her list of chores while she's out with a real man, having her sexual needs fulfilled.

I will keep you all posted, if you're interested, as to how things develop.
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Wannabe_Baby
As always, Bobby, I'm torn. On the one hand, you're a fantastic storyteller and the tales from your life you've posted on this site make for great reading. It's also a top-notch turn-on and something that never fails to excite me. Always interesting stuff. On the other hand, again, I'm concerned about the fact that your entire life is something that, for me, wouldn't be more than a few hours of fantasy. It's a great fantasy but not something I think could be done every day and I'm worried that the day will come when you start to want more but aren't able to get it.

I don't mean to lecture you because only you know how your life is and you do seem to be enjoying it. Obviously, I can't tell you how to live your life. Nor can anyone else, I suspect.
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BabyKitten
That's quite a big step! Hopefully it all works out
Official Potty Training Failure!
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CeeCee
I bet it's a big turn on that she wants to suck his cock but she's never been into sucking yours.

I'd love to hear more about how that makes you feel.
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Baby Bobby__
So today we went bra shopping for my wife. We got a super sexy one at Frederick's and she already knows the pink top she's going to wear for her first date with her boyfriend. She modeled the two for me together when we got home and I was like--wow!! So freakin' sexy! I know he'll be drooling all over her. When she she was wearing her pink top with the new bra, I immediately went to fondle her and she quickly informed me that that particular bra was for "him" only and that whenever she's wearing it, I'm not to touch her. That gave me chills.



We even bought a dildo (I know this sounds kind of funny) because she wants to practice fellatio for when they have their date (she knows she'll be going down on him and she doesn't want to look inexperienced or be awkward). She almost never gave me blowjobs so this will be another thing she'll share only with him.



She told me that she's excited about seeing him at work today so she can kiss him passionately. She also let me read a long series of texts that they sent each other yesterday (they're constantly doing that) and I was able to see the level of excitement between them and the sparks flying. Its exciting for both of us! My wiener has been aching in my chastity device and its hard to concentrate on anything else.
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clarisselovelace
As long as you're both committed to each other, I see no problem with this.
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BabyKitten
You're such a brave sissy. I'd be all pouty if mommy had a new boyfriend. It's not fair...
Official Potty Training Failure!
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Dreamer89
i hope you keep us updated on this situation, it sounds very exciting! and i know i cant be the only one hoping to experience it vicariously through you :P

good luck! i hope everything works out for you!
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Baby Bobby__


Here is a pic of the bra and panties my mommy bought to wear for her new boyfriend on Tuesday. I've been told that they aren't for me and that I'm not allowed to touch her while she's wearing them.

So, last night, she met him for a brief drink after work during which they spent a great deal of time kissing and making out. She told him that she has me in a chastity device and he is totally on board with it.

When she came home, I spent a half hour or so, servicing her while she sat on the couch, texting back and forth with her boyfriend. That was a rush!

The plan is that after their first date, she'll bring him over to our house, but beforehand, she'll make sure I'm dressed for bed (sissy top, diapers and anklets), and put me in my nursery for the night. There will be a baby monitor set up in the Master bedroom and out in the living room with the receiver in my nursery so I will be tormented with the sounds of their wild lovemaking all night and wherever they are.
I know I will be beside myself with the fear that he could just walk into my nursery and see me dressed like the sissy toddler girl I am.
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deewet
This is a wonderfull development Bobby, I just hope you can continue to please your wife any way that you can, especially sharing her experiances with new boyfriend.

Isn't it exciting to be able to share the intamicy (even if it is with your mouth) with your wife as she is remembering her recent experiences with her real man!

I know it will be difficult in your crib listening to your SO becoming so passionate when at home with her man, but just remember, it makes her happy, and maybe in the morning she will share something of him with you.

Maybe if your are really good, whe will take the lock off your device for a few minutes---naa but you can always hope for that.

Dee
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bedwetter41


 
Bobby: Your wife is doing the right thing. Sissies are sissies -- and real men are real men. One belongs in a woman's bed -- and one belongs in a rubber-sheeted crib. It is actually as simple as that! Sissies tend to start as sissies (but sometimes pretend to be actual men in their late teens and twenties) but once they get to know what they are, sissies tend to become MORE sissy as time goes on. Eventually sissies are impotent with a real woman (they are scared and so afraid of non-performance, you see) even if given the chance for adult sex (which most sissies aren't since women aren't interested in them "that way.") This leads to a complete focus on the childish "pleasure" of playing with themselves -- which certainly doesn't make them seem any more "grow up" to the women around! (Most women are frankly kinda disgusted by thinking about a sissy jerking off his tiny little thingy!)
Because of all this -- and bedwetting besides -- separate bedrooms are always in a sissy's near future. Sissy is moved with dispatch and little ceremony into a more suitable little room of his own -- with a little bed (or crib). Also, because of their total lack of sexual prowess, meak natures, lazy demeanor and no competitive forcefulness at jobs and so forth -- sissies do not deserve or get the kind of repect a real man gets (or women get). Sissies decisions are made FOR him -- bedtime -- what he eats, where he goes, what he wears, etc. And any woman in his life is soon openly dating and sleeping with a real man boyfriend -- with pretty much zero concern of what sissy may think about the matter!
As an added bonus to all this -- sissy can be put in chastity. Handled correctly -- this makes the little dear SO obediant and compliant. Soon he can be trained to serve the woman and her boyfriend drinks from a tray -- say "Yes, Sir!" to the real man's orders -- and perhaps spend his days doing the menial household tasks. (One women told me once it was so fun to have her boyfriend head towards the bathroom after sex and find sissy there on his knees in a plastic apron cleaning the toilet. Red-faced, sissy of course had to say "excuse me Sir!" and scurry out, like the little servant he was quickly becoming. She really thought that both of them were simply in their correct "place".)
All of this is simply as it should be -- (and in fact, in a growing number of households --- IS.
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Baby Bobby__
Bobbie, as usual, you put a fine edge on the subject, articulating it so well and so very accurately.

My mommy is a normal woman and normal women have little sexual interest (if any at all) in diaper wetting sissies and their childish behavior. More and more, my mommy sees me as less of a man and more of a sissy who needs to be treated like a baby. I think she's becoming even more comfortable in the change of dynamic within our relationship and has even come to assist me in my sissy attire (she helped me pick out fabric and design a diaper shirt and she's actually complimenting me on my outfits that are humiliating to wear). This is not to say that she finds such sissy wear sexually exciting--not at all. Its just that she realizes there are some guys who should be wearing diapers and dresses and some that should be pleasing women in bed. Unfortunately, I fall into the former category.

At the same time, she never lets a day pass in which she says I'm nothing but a sissy and that I'll never be allowed to please her, which is why she has to get her sexual satisfaction from a real man. Sometimes she taunts me, flaunting her sexy body in front of me and saying "don't you wish you were a real man so you could have some of this?" When I tell her yes, she says that I can forget it because I'm just a sissy.


Today, she's dressing herself in a very low cut, clinging pink top and the white bra pictured above to meet her boyfriend. She's told me she has every intention of servicing his monster cock and he's going to take a picture on her cell phone and send it to me. At the same time, I'll be at home, probably doing a list of chores she'll leave me, and wearing a sissy outfit she's picked out for me.
I know tonight will be a long one in the crib, knowing she's in bed with a real man and getting all the orgasms she can handle while I remain chaste, horny, and frustrated. As usual...
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Ahhh it's been two months, we need an update!
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little_sara
yes,please update
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Baby Bobby__
Hi sissies!

Wow, has it been two months already? I guess a lot has happened during that time...

After Mommy's first night with her boyfriend, things were really going great between them. They were texting each other constantly and I was watching the sparks fly as she told him how much she enjoyed a kiss here, a hug there, and how she enjoyed taking his big cock in her mouth out in the parking lot.

They had plans to come over to our house and spend a night having wild, passionate sex in her bedroom. My nursery is very close by and with her door open, I would be able to hear everything going on. She planned to get me dressed for the night, in my sissy diapers and top, and then tuck me into my crib before he arrived. Since I wouldn't be allowed to go out of my nursery while he was there, it was pretty much a guarantee that I'd be soaking my diapers at some point during the night.

Meanwhile, she'd be getting a nice big cock from a real man, instead of the simpering sissy that she's been married to.

Alas...all our plans evaporated when her boyfriend's wife got wind of their affair. It seems she wasn't on board with the idea despite what Mommy's boyfriend had led her to believe....

So now we are looking for another "Bull" to take his place. We've got several ads up and we're trying to screen out the talkers, wannabes, and guys that just aren't up to her standards. I can certainly sympathize with the last point. She is a hottie and she deserves a hot guy that can please her.

Its hard to say how long it will take us...I know she's anxious and excited about finding the right man for her. I'll keep all my sissy friends here informed about our progress. 
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Baby Bobby__
So here's a quick update; my Mommy has found a man she is very interested in and she'll be meeting him for a first date on Friday. They've been exchanging emails and pics every day for a week and sharing detailed erotic fantasies of what they want to do with each other.

Their first meeting will be out of town so she'll be getting a hotel room to stay the night. They will be spending most and possibly all of the day together, and if she likes him well enough, she'll ask him to spend the night with her.

She bought another set of bras the other day (for his enjoyment, not mine of course) and I took a pic of her in the white one:



I'm confident that she will make a very good impression on her new boyfriend.
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Baby Bobby__
Yesterday, I helped my wife pack for her trip to go see her lover. We picked out a low cut dress, a snug fitting top, her sexiest lingerie, including the new lace bra she bought for her boyfriend, 5" high heels, her birth control and some condoms (just in case).

When we finished, she made me lick her pussy to a shattering orgasm while she taunted me with her plans for her lover. She was very excited to meet him for the first time!


So today, having stayed the night in another town, she met her man in the bar of the hotel she was staying at. I think she had plans to go a little slow with him but to my surprise, in no time at all, she sent me a pic from her phone with her lover's cock buried in her mouth. That can be very frustrating for a sissy locked in chastity to see! Obviously, he had made a very good impression on her right away!


This was followed in short order by a number of other pics showing them having sex from various angles, her riding on top of him, his cock thrusting into her shaved pussy, etc. After viewing these pics, my phone rang and my wife set hers aside so I could listen to the sounds of their lovemaking. It was very erotic, hearing the familiar sound of my wife passionately moaning and crying with pleasure as her lover did her in every imaginable way.


Our two situations couldn't have been any more different. There she was, with a young, muscular stud, who was giving her fantastic sex and multiple orgasms and here I was at home, wearing my sissy dress and diapers, wetting myself as I listened to her being pleasured by a real man. It only drove home how appropriate it was that my little penis was locked up with no plans in the future for getting a release.


On and on, I listened as my beautiful Mommy had orgasm followed by orgasm. I had never heard her cum so much! Obviously, having a real man for the first time made a huge difference--and I couldn't believe how much stamina he had. There can be no doubt that in the future, she will want to get all her sex from him and limit my own access to her even more that she already has.


I guess this is the natural progression of things: hot women who find themselves stuck in a relationship with a sissy soon learn that in order to get proper satisfaction in bed, its necessary to find a real man outside their marriage that can perform all the manly duties that a sissy is so hopelessly inadequate for.
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sissybabysusie1
I think you are doing the right thing its only right she has real men to share her bed.
I love the wholse sissy baby girl cuckold scenario and reading your posts made my tiny 3 inch erection all hard.
I always search for stories that involve sissy husbands dressed as baby girls,frilly pink satin panties matching dresses with thick nappies and plastic pants underneath or baby girl attire such as the vintage babydoll nighties in pale pink chiffon.
.I often play with my tiny little penis while listening to my wife have sex with her boyfreind.Occasionally I have her damp silky white panties stretched over my head....sends me wild.
I hope to read more storys and posts about this subject.I have seen a few good storys on bettys pub some are excellent especially those wrote by babybobby is that you?
I would love to have a collection of cuckold sissy baby storys in paperback and theres a site in the uk called abstories who will publish them and pay you.I will try and send the link.
I have posted some pics of me in my attire on penis size matters look for ( uk ) under small cocks.
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sissybabysusie1
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Baby Bobby__
Hi Sissies,

I have so much to tell. My Mommy's hit it off really well with the guy I described in my last post but due to his distance from us, he seems like an unlikely candidate for us in a practical sense. They still text and email each other but we don't know when they'll get together again.

To make a long story short, she decided she needed to find someone closer to our area and she found another guy online and has been texting him while we were on vacation. They too, seemed to get along well although this guy was clearly more dominant. This guy is much younger but he's tall and cute.

So last night, they finally met face to face in a high class club (I was at home at the time) for drinks and to get to know one another. When she first walked in, he immediately kissed her (which she very much enjoyed) and they sat down in a booth. She told me later that he had his hands up her dress and they kissed quite a bit. Afterwards, they went out to her car where he got her off several times with his fingers. She went down on him and sucked his big cock, swallowing his load when he came.
He then took her phone and sent me a text, telling me what he had just done. I was quivering with shame and excitement but I knew this was inevitable.

Anyway, they had to make a short night of it but he wants to come over to our house on Sunday (tomorrow) if it can be arranged (my [real] mom is coming to stay which might put a wrench in those plans). My Mommy says he intends to sit me down and have a long talk with me which gives me the chills! I get the impression he is a strict disciplinarian and that he is really going to lay down the law with me. There's also a strong possibility my Mommy may put me over her lap and spank me in front of him because he had mentioned I needed to be punished for an earlier misdeed. If that happens, I think I will die with embarrassment!!!

My Mommy told him she is going to move some of my clothes to make room for some that he will leave here, as she expects him to be spending the night fairly often. She also says that he has forbidden me from watching them have sex, and that I will have to earn that right. He may also be taking possession of my chastity device keys.

There will be much to report in this next week. Stay tuned sissies!
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Baby Bobby__
By the way, thanks for the link SissybabySusie. I may submit some of my fiction to them. In the meantime, its exciting to live out the real thing! 
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sissybabysusie1
You are welcome infact if you do have your story published in paperback form I will be one of the first to buy it!Yours is so much better written than mine.
Bobbie hope we can become sissy freinds.Your lifestyle excites me so much and I wait in anticipation for your updates.I hope her boyfreind puts you over his knee and spanks you that would be fun especially with your wife and maybe her freinds watching?Tell me is she going to organise a pretty babysitter for you?Please post more pics please pleaeeeeeeeezzzz.
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sissybabysusie1
http://fantasti.cc/user/sissybabysusie

I have sissy pics some are very naughty ones showing just what a sissy "ickle" baby girl I am if you are easily offended please don't click on the link!
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Baby Bobby__
Wonderful pics, SissybabySusie, although I don't believe a diaper wearing sissy should have the freedom of having his pee-pee accessible as you do. A secure chastity device is just what you need. 


Okay...so yesterday was a long day for me. I spent over six hours cleaning the house in preparation for my Mommy's date with her new boyfriend. She had left me an extra long list that she said had better be done to perfection or I'd be going over her knee for a severe spanking when she got home.
Her boyfriend is coming over tonight and he just sent me a text telling me to remove all my clothes from the Master bedroom to make room for his.

He also told her he wants me to wear sissy panties too, so today, my Mommy is going to buy some especially for me to wear (we haven't yet told her new boyfriend about my already vast wardrobe of baby clothes yet--we thought we'd take it one step at a time). Still, it will be humiliating for me to appear before him, in my sissy panties with my penis so obviously locked up.

A couple of days ago, I made the mistake of asking him if he'd let me out of my chastity device for one orgasm but he immediately told my Mommy who was furious that I was trying to go behind her back. So now, I'm facing a humiliating spanking in front of her boyfriend(!) before they retire to the bedroom for sex. I don't know what I'm going to do--I will be so ashamed, bent over her lap, my panties tangled around my ankles, kicking and sobbing as she spanks me harshly with one of her paddles. He'll definitely be seeing me for the sissy that I am.

I'm very nervous about tonight. 
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Baby Bobby__
I'm back from the store with Mommy and she picked out a number of panties for me to wear from now on when her boyfriend is visiting. Here are two of them;



I tried on the white and pink and and here's how they fit me;



You can clearly see my CB6000S chastity device tenting the panties.



I can't imagine what I'll say or do when my Mommy makes me pull down my panties and reveal what I'm wearing underneath. I think I'll die of shame!!

And I expect my bottom will be getting very red tonight. My Mommy told me to bring our paddles out to the living room;



I'm SO nervous!!
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sissybabysusie1
Well bobby like all sissies we need a good spanking however if your wife has a boyfreind I'm sure at some point she will ask him to place you over his knees and give you a blistering with his large firm hands!. I wonder if your lovely wife/mommy will ask her girlfreinds round to witness the humiliation or even your new pretty baby sitter?
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