I was never enough for her

babyryan

Thanks.

It reminds me of a few key incidents in the past.

With one couple, once I proposed the idea, she at first said she wasn't into it. Then, once she thought it over, said she'd be ok on the receiving end.

That's where it got interesting. I knew a young lesbian couple that had an open relationship. One of them agreed to attend a variant on Trivial Pursuit where wrong answers would cause you to take off an article of clothing.

Most were down to nothing when the rules changed, and wrong answers required a specific sex act.

She (the wife) went into it full steam. And despite her initial shyness, went at it with the girl like a pro. She ended up reluctantly admitting it was wildly hot. Especially as her husband was practicing his oral skills on me as they were moaning together.

On a different note with the same couple, the wife and I hatched a plan where we would propose a 'double date'. Thinking he'd get to have some pussy, he agreed. It took over two weeks to arrange. (too many details).

The night it happened, I knocked on their door and he answered all dressed for dinner. But there was no girl with me, but a well-built fellow. The husband's confusion was bright as day. Per arrangement, my guest took over and suggested that hubby had a choice of dressing in drag or not. But he would be staying the night with him in the guest bedroom while his wife and I had the master bedroom.

Later the following morning, we pressed him for all the details of the night. Starting off slow, he eventially opened up about how assertive the guest was and how much he loved doing everything he wanted.

It opened up a lot of doors for them and gave me countless ideas for future encounters with them and other couples.

Youknowwho, I can imagine how embarrassed the husband must have been when you did not bring a girl over. IM very curious did he end up dressing feminine for his date?

Not that night. But he admitted the following morning he regretted not dressing up feminine for him.

We set it up for him to dress that way more often to break the ice. It got to the point where it was natural for him to dress up once he got home and on the weekends. We all enjoyed that.

My very first post here details a few of the outcomes.

babyryan

Important thing was, despite the social norms of the day that dictated more conventional behavior, we all had fun, we all learned something and broke a lot of boundaries.

babyryan

babyryan

Important thing was, despite the social norms of the day that dictated more conventional behavior, we all had fun, we all learned something and broke a lot of boundaries.

I understand his hesitation to dress. And I understand why once he did it he had to keep doing it. The more feminine I dressed, the more submissive I became, or the more submissive I was able to act on anyway. There was a connection between dressing and acting more feminine and then needing him to spank me. Once I have been stripped and spanked I know I am ready to passionately kiss and suck his big cock for him

babyryan

You are in a good place. I'm sure you miss being the way it was now and then. But you are also excited about what's in store for you now.

Having a capable, virile and assertive bull making your most intimate decisions for you and your sensual wife helped you accept your new position. You are a natural.

Stay open to new demands and even more extreme acts of **********. The thrill will continue as long as you progress in your role as a willing sissy. If it gets too routine, the magic begins to fade.

If you sense that happening, you may want to consider opening the dialog by suggesting your willingness to try new, 'forbidden' and unconventional things to make him happy. Be ready with a list of suggestions should he ask.

I've had some experience with that if it will help you keep the excitement going.

I have been hesitating for a bit, to ask for a list of suggestions. They have in no way run out of humiliating ideas to impose on me but asking the group for an embarrassing list of suggestions seemed appropriate at this time.

babyryan
Here are a few suggestions for you...

You get dressed up and go out of town together as a trio. He takes both you girls to a nail parlor and has the tech do both of your nails as he directs. He watches and pays at the end of the session.

You all go to a gym with a sauna and the two girls wear bikinis and you join your bull in the sauna. Both you girls take turns rubbing his skin with cool water/oil even when others are there watching as his cock grows in his speedo's.

You all go to a gay bar/cross-dressing bar and spend the night there. Your wife and you attend to your bull stroking him, blowing him in a dark corner/booth etc and you are made to find someone else to bring to the table and stroke/blow while they watch.

You all go to a dept store to the lingerie dept with you fully dressed as Renee. They choose new lingerie for you to wear and you have to model it as you come out of the changing room, in front of the sales assistant etc. Then you go to the shoe dept and they choose shoes for you, the higher the better, and you have to again model them in front of your bull, wife and assistant. Your dress should be very short and show off your stockings and garter belt easily to the assistant.

I've done this with several cuck sissies, and while it is very embarrassing for the cuck, it is a huge turn on for everyone concerned, usually ending in a mammoth fuck and suck session, beginning in the car as we drove home.

I know you will be reluctant, but as the cuck you should have no say in the matter and follow your instructions to the letter.


pops

popeye1 thank you for such excellent suggestions that should push every sissy cuck's buttons! Especially whenever locked up in a much needed cute button chastity cage!

Make sissy grow and polish with french manicure Delete attachment #1

babyryan
You are such a babydoll Renee! popeye1
Popeye's suggestion of going to a nail salon for a full set of acrylic nails should be a humbling experience to give you plenty of time to appreciate how pretty your nails will look wrapped around His hard cock. Your toenails should be polished a vivid red though.

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All great suggestions so far.

Here's a few, based on two couples I had the pleasure of educating.

First, I want to point out how important it is for you to take the subm1ssive initiative with your bull and wife.

Tell them unprompted how grateful you are for him fucking you and your wife. How thrilled you are when he uses you for his pleasure. How good you feel when he unloads his manly cum into your pussy or your mouth. Tell him he is welcome anytime to use you as he pleases. That will set the tone down the road. Tell him how magnificent his cock is. How naturally feminine he makes you feel in his company.

Once that stage is set, you can propose a series of acts to prove your new-found devotion.

I can only point out what I've instigated in the past. But it runs the range from moderate to extreme.

Give them ideas that can be easily checked off and modified at their discretion. View everything you present that they agree to as an absolute rule.

List a number of options from your own imagination, running from mild to completely subserv1ent and unconventional.

These are suggestions from my past. Some have brief context added.

Feel free to ask me for details on any of this. I'd be willing to elaborate in the best way I can.

1) Tell him you don't just belong to him. You belong to his cock.

2) Go to a distant motel where you won't be recognized. Your wife and you in the sluttiest clothes possible.

3) Drive to work your together with your wife and him in the back seat. Park in a less populated spot until they finish. Then continue to work while both of them emerge disheveled from the back and sit in the front before leaving for home.

4) Have her drive while you and he are in the back. You blowing him to completion, holding his cum until inside. Then swallowing it before greeting your co-workers.

5) Offering to put on an erotic show with another sissy (this is not as easy as it sounds) to entertain him and her. Work up to a mutual cock-sucking and a French kiss with semen still in your mouths.

6) Get ready for work while he and your wife fuck. When you're done dressing and brushing your teeth, wait for them to finish. Suggest you can clean his cock before you leave. Then continue to work with the combined taste in the next few hours.

7) Suggest you call him once a week from work to thank him for fucking your wife and to beg him to let you suck him off.

8) Suggest to him you'd be willing to take off work early, dress up, act especially girly and accommodating before he arrived. And continue as your wife returned home.

9) Go to a distant makeup and nail salon as Popeye suggested where you won't be known. Wear modest clothes with a button-down shirt. Sit in a chair and unbutton a few, revealing a lacey camisole. Ask for a full job of nails and makeup.

10) Go to an adult shop where you will scan the cuckold and sissy sections while he has your wife model different outfits for him. Then you pay for all the items.

Feel free to pick and choose from the above. If you want more extreme examples, please ask.

sissystephanie

Well Stephanie isn't that just a very cute sissy clit you have there!

I'd really like to have you and Babyryan come over and give a real gurly show for me. You both dressed up in white fishnets, open crotch panties and garter belts with stiletto shoes and a black studded collar and chain for me to keep you both in check. Have you work on each others cllttys while I stoke my cock to full attention.

Have you both then work your mouths over my smooth cock and clean the precum that's been leaking from my cock, for me. Have one of you work your tongue around my ass while the other sucks me off. Then hold my cum in your mouth and snowball each other while I sit back and enjoy the sight.

Then you could both slide over and clean my cock of anything that's left over and get me ready for round two.

You look so feminine and sexy and ready for use.

You are one of the best I've seen on this site, you and Babyryan would make great slutty cuck twins.

If you have anymore pics please post them to me on this site. Cant wait

pops

popeye1
Thank you for all the kind words of encouragement Pops! It's very comforting to know that I'm considered in such fine company and certainly appreciate the gracious compliments. The idea of no condoms and feeling Bull sperm running down our balls while having to spread our gaped holes in front of a low window must make a believer out of any hesitant sissy!

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Practice makes perfect with both makeup and cocksucking!

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babyryan

You seem to have gone quiet there babyryan. I hope all this attention and suggestions have not scared you away? Maybe you are just too busy swallowing black cum or licking ass?

Keep us posted on what is going on.

pops

I did find myself on the receiving end of a bare bottom spanking followed by a thorough buttfucking ... one that left me open, wet and properly in my place.
sissystephanie you are right that practice makes perfect.
The humiliating suggestions left made me blush badly thinking about how exposed I would be during these outings.
The task of having to call him from work and thank him him for fucking my wife and then having to beg to suck his big black is really embarrassing

babyryan
That's a good girl. Did you spread your cheeks apart in front of the low window again while His jizz coated your little nuts?

sissystephanie, luckily for me, I was not required to spread my cheeks apart in front of the low window. I was plugged so that his cum stayed inside me longer though.

babyryan
Was it hard keeping the plug from wanting to slip out after He gaped your pussy hole? Or did you have to wear a really thick plug?

sissystephanie I have a few plugs. Some of which are thin and at this point do slip out But I had a thicker plug in with a tapered base. So it fills me up and stays in place.

Since you seem to be taking spankings and big hard cock on a regular basis, has your pussy hole flowered out? Has your wife noticed or commented that your used cum filled gaped hole started having a pussy lip likeness ?

babyryan
Maybe you should cross post in the Ruined Hubby group too! ☺️😧😳

babyryan

Glad you are considering some of the suggestions here. You look very content and natural with your bull's cock plunging into your happy lips. You're doing great.

sissystephanie

Just wanted to point out that you and babyrian are in the very best place.

You both look totally natural with a big dick sawing in and out of your mouths. And I'm assuming those dicks are the same ones pleasuring your wives.

It appears you two are just as content when they are giving your sissy pussys a workout too.

Feel free to offer your deepest experiences and confessions.

You are a credit to your unique role as cuckold, sissy and subm1ssive.

My lovely Wife was just telling me yesterday that I have really earned my woman card. Thank you for such gracious compliments. Dressing full time for almost six months in isolation now has really offered Her a wholly new prospective of how I've comfortably settled into womanhood recently. She's certainly noticed and even made comments that my feminine movements and behavior look so natural lately. She was kinda embarrassed to admit She also harbored cuckold fantasies after I finally one day couldn't stand it any more and confessed my sissy cuck fantasies to Her. She held me and let me know it was okay. With no Bull, anyways yet, the next day She took me dildo shopping. She bought a three speed realistic shaped cock bigger than my little pecker, named 'him' Bill and now Bill makes Her orgasm while I'm sucking Her clit. Something I seldom could do on my own. We also have three remote control rechargeable plugs with dual motors that when all fully charged will last almost an hour to jackhammer my pussy for that freshly fucked feeling and if lucky, that elusive sissigasm that leaves me even hornier after all my sissy juice slowly and completely oozes out leaving me horny, high and dry. With the improvements in our sex life during this pandemic, I really wish my feminization had evolved more prior to this crazy isolation.

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babyryan

So come on, and tell us which of these many excellent suggestions you are going to do first?

I, personally, am expecting you, as a cute, obedient and sub sissy, to work your way through them all, and report back here on how they went and what the end result was?

I expect all those who have contributed to, and enjoyed your thread here, are waiting with baited breath for you to give us a detailed update on your progress, the emphasis being on "detailed"!

pops

So, Stephanie, is it not about time you started your own thread and told us about yourself, how you became Stephanie and some of you adventures as a sissy cuck? Many, I am sure, are keen to hear your story and comment on it.

I would love to see some pics of your wife and hear of her adventures too.

I love playing with hot wives and dominating their sissy cucks, its become a way of life for me over the decades, and my own hot wife, Jasmine, has had many adventure too over the years.

So come on and start a thread and fill us in on your story.

pops

popeye1
Thank You for asking me to start my own thread. Wow. Maybe my reality should be exposed if it helps other cucks understand this natural selection process. I'll reply here before transfer to my own thread.

While I am not a cuckold, it is certainly a very hot topic and as a feminized sissy, I can definitely relate to the inadequacies many cuckolds must experience when it comes to sexual prowess and wives' sexual satisfaction. The delicate balance to strive avoiding the attack on a cuckold's self esteem seems to be a major dilemma when it comes to maintaining an ongoing relationship that is not only suitable but agreeable for all involved.

Everything I have read with regards to cuckolding advice, is about maintaining communication. It only seems logical that these same lines of communication apply to the cuckold's desired *********** as well. Just like my self-imposed feminization, I do not always 'get my way'. I think the same probably applies with the cuckold's mindset when it comes to ***********.

Of course, there are certainly extremes in many fetish activities, but communication upfront, building that aforementioned friendship, explores the realms a couple is willing to reach. I dare say You are quite competent as an Alpha Dom to gradually push the limits a cuck couple once those hard limits are discovered.

As a sissy, again I know I do not always get everything my way. It doesn't break down my self-esteem, but helps me know where I stand with my wife. I would imagine as a Bull, You would take delight sitting down with a cuckold husband and letting him know, up close eye-to-eye, that there will be times that he WILL experience great shame and ***********, necessary ***********, which is why he is a cuckold to start with. It is part of the whole cuckold experience from my viewpoint of cuckold angst.

There are as many different type cuckold relationships as there are fetishes I suppose. As the old adage goes, "different strokes for different folks". So the type and amount of cuckold *********** must vary as a parabolic curve of degrees, according to particular tastes and fetishes.

I for one, would certainly entertain the feminization aspect, to some degree, and open discussion, where appropriate cuckold candidates apply themselves, for the more extreme cuckold ***********s.

As you will see, I was literally 'born this way'. The true conquest of the natural mating selection.

I discovered from a very early age that I was not like normal boys. You see, i have been a sissy all my life. I polished my own toenails the first time when I was five years old. This progressed to trying on my ******* stockings and girdles eventually. Then her high heels when I was a few years older. Long story short, the more opportunities I had to dress as a girl, the more I wanted to look and act like a girl. So I have always been a sissy. It's as if I was born this way, since I've been trying to be a girl and now a woman, for so long.

My very first orgasm was into the ********** toe of a nylon stocking! I was not even "jacking off" like a real guy, but using my middle finger to massage the nylon material on the underside of my penis, just below the head. Not a very manly way to ejaculate. It was so powerful, a complete surprise and quite shocking the first time.

It felt so wonderful, I became hooked. To this day, anything that deals with cum and feminine feet, heels or stockings consumes my many fantasies. Vintage stockings are my addiction! I become weak in their presence and even swoon rolling them up my very own shaved legs.

So when did cuckolding really start for me? Maybe not true cuckolding but pure simple rejection! As I started dating, I faced obvious dilemmas and debacles. More than a few relationships ended very early, with gorgeous young women, that always seemed to let me know I did not measure up. Even on a couple breakups, I faced my competition. One beautiful lady in particular, Laura, just told me up front, she needed a man with a big cock. We had even been engaged for six months and I caught her cheating. Looking back, such a shame things didn't work out for us as a young couple.

The was way before the Internet. We had no idea the meaning of cuckolding. Although she seemed very comfortable and honestly happy to witness me grovel before her during our breakup. I may not have ever been a married cuckold back then, but I feel I do have just a taste of what real cuckold's experience.

When I say a taste, that is an understatement. Soon after our first intercourse and eventual engagement, Laura cut me off from having sex until marriage. She did not cut me off from eating her pussy. More than a few times, I would come home from work and she would be ready for me to bring her to orgasm with my tongue. I must have ate dozens of creampies before I had even knew what the term truly meant, in the context of cuckolding.

We had met on New Year's Eve while I was watching a drag show at a gay bar. I was fully dressed up looking as sexy as she was in our short skirts and spike heels. So she knew all about Stephanie from the very beginning. The night she ended our relationship she ******* me to dress up so we could go out. I was set up to meet her new lover at the same bar we had first met. He came up to our table and without as much as an introduction told her to come with him and leave. He sneered at me as she rose up to peck me on the cheek with a kiss and yelled into my ear over the music, "I'm leaving, he has a really big cock. Why don't you find one too, honey". We only saw each other one other time after that night and I was heartbroken.

I had 'experimented' with men before I met Laura. Her words would not leave my mind! So I did. I went out searching for a man. Not just any man but someone to build a relationship. I decided I must be gay even though I still desired woman. I had very little experience when it came to gay relationships. Gay guys wanted other masculine gay guys. I was nothing like that. Gay bars became my hangout for Stephanie. Night after night on weekends I would go home alone after the bars closed. Finding anyone to start a relationship seemed hopeless. I knew one thing, I was ready for cock. Not just any cock either, I wanted a big cock just like Laura was getting every night, and I wanted it to hurt oh so good. To be the squirming whimpering sissy I knew I had become. I felt so defeated.

Finally I found HIM, or He found me. So I thought. Turned out it only lasted a few weekends. I learned (was taught) what serving a real cock was all about!!! He was big, huge. Over 6'4"+ and towered over me even when I was wearing heels. He was Black, too. He had the thickest cock I had ever laid my eyes on. I have no idea how wide his cock measured but it was all I could do to fit it in my mouth. First thing he did was teach me to get over my gag reflex. There was no way of knowing that weekend would change my life forever and make me not just love big hard cocks, but crave them now every single day. He knew what he was doing and knew I would be needing and wanting cock all the time. Nor did I realize my body was even capable of pleasuring a cock for that length of time. He taught me how to drain a man's balls that night, with no relief until he was bone dry.

The details of how I was 'turned', from being capable of doing the fucking, into being totally fucked, well... First off, let me say that having the open dialogue to ask me how long I've wanted to be a woman is pretty important. I didn't just open up the closet one day and think to myself, hey, I want to be a woman today, or at least look like one. I think the longer i harboured feeling like or at least wanting to become a sissy, the deeper I relish serving as a submissive and be willing to make a strong commitment to come completely out as a woman full time nowadays.

So there I find myself that fateful day, my day of realization, on my knees. Like I said before, I had sucked cock already but it was just okay in the past. I had a take it or leave it attitude. It sure seemed right as a submissive sissy, but other than a mental relief, I can't say there was an actual sexual feeling of satisfaction. Well that's because I had never been properly used before. While on my knees for almost a half hour, licking, kissing and sucking a massive Black cock, I started getting really tired. He was enjoying my attempt to make him cum, but I was having doubts I could go on much longer. We eventually move to the bed as I continued sucking his cock with added vigor hoping he would soon reward me with a mouth full of thick potent creamy jizz.

In a loving way, he told me he way just getting started with me and he wanted me to feel like a real woman, "baby girl". My mouth was getting so sore being stretched open so wide. I was moaning and whimpering on his big hard cock as he began rubbing my butt cheeks. Needing a slight reprieve, I ask if I could please lube myself for the inevitable fucking I was about to receive. He was a true gentleman and treated me with much grace and careful consideration. He never spoke one ill word or derogoratory term. After I was prepared, he gently eased his lubed cock into my pussyass. Slowly a little at a time, inch by inch. Never rough, just as gentle as he could be. I opened up and felt him slowly sink into me until I was stretched wide open by his massive thick cock. He asked me if I was okay! I moaned, oh yes, honey, I'm good. Then he slowly pulled back and started a slow steady pace. I was on my hands and knees to start. Then he started picking up the pace. I started to realize I had never been fucked like this before. He kept going and going. Before long my knees and wrists were tiring out so I rolled over on my back. When my legs went up high, the hard fucking started. I never felt so helpless before, but it felt so right!!!! I was getting really fucked and not just some wham bam thank you mam, either.

Just like my mouth had got tired and sore, after almost a half hour I was afraid my pussy would get raw and wanted a break. He said he was just getting going real good. I begged to suck his cock more, now that my jaws had a little rest. In no time I was nestled next to him sucking his cock again, getting a taste of myself. Good thing I had done 3-4 douches with the enema bag until I was emptied clean or that would have just been gross.

I kept sucking on and on, trying to get him to spurt a river of thick cum in my mouth. A slight hint of yummy pre-cum would ocassionally linger for a second or two just to tease my hunger for more. Then went on and on and on. Again my jaws felt so tired and worn out. His cock had been so hard for way over an hour. I started to plead for another break. He ask me if my pussy was ready for more so I reached for the KY again on the nightstand.

Back and forth with maybe a 45 minute break to grab a quick bite to eat, I was constantly full of glorious hard thick cock until early morning. I was limp when he finally jerked off on my face and over my mouth to be sure I got plenty of cum to just lay there and savior. I had never been fucked like that before by anybody. He took his time and made sure I was so physically exhausted that I knew I had been royally fucked!

The next day my pussy was still tingling and jaws still sore. I was so weak yet happy! I had never felt like more a real woman in my life. I also felt very well used. Wearing my nylons and garterbelt seemed so natural for once.

I couldn't wait to meet him the next weekend. He made me feel like some schoolgirl wanting for Friday night to fix herself up and go out on a date. We were both looking forward to it. Our next hookup was even better. He became much more verbal and rough. Probably at my instigation. Now it was hotter to admit I loved his cock. He would constantly ask me if I wanted more of this cock, or you gonna show me how much you like this cock sissy? He was really getting into being the Alpha and he fit role perfectly. I probably did more than I ever had in the past to look more feminine for him. Going to the nail salon for french manicures was getting a little expensive but at least my toes still looked pretty good. My eyebrows were waxed a bit thinner as well. He always noticed the little things too. Like when I changed color polish on my toenails. Commenting on my choice and style of clothes.

Sadly, he was transferred out of state and we've never reconnected. He went from being a total gentleman to being more and more aggressive. I think his transformation to a true Alpha was bolder than my feminization, but obviously quite necessary.

So yes, the *********** is always good! Very much needed and appreciated as well. The coercion is a necessary act that makes us feel like a sissy! The more we feel like a sissy, the more we want to act like one. That certainly means acting more and more like the perfect cocksucker, too!

Sorry for the long lengthy post. Sometimes the details are in the pudding as they say.

Like Laura, I told my wife on our first date that I am borderline transgender or maybe even more now.

sissystephanie, wonderful post. I know how you felt when you finally had your white asspussy broken in by a big black cock.
Regretting it already I will be calling my wife's lover from work this week to thank him for giving my wife the big black cock her body needs and to beg him to allow me to duck his superior black cock when I get home I will be telling everyone how this made me feel when I do it.