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Confessing my sissy cuck fantasies to my Wife

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sissystephanie

Anonymous

#1 · Edited by: sissystephanie
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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 currently being cuckolded, 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 humilat1on 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 humiliat1on.

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 a Bull 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 humiliat1on necessary cuckold angst, 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 humiliat1on 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 humiliat1on and cuckold angst.

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 Mom's 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 dark toe of a nylon stocking! I was not even "jacking off" like a real guy but more like fingering a clitorus, but using my middle finger to massage the nylon material on the underside of my penis, just below the head, almost like fingering a pussy. Not a very manly way to ejaculate. It was so powerful, a complete surprise and quite shocking the first time. I had no idea what I'd just done. It scared me to think I'd done something to my little pecker. So it began, fingering myself to orgasm using a nylon stocking on a regular basis. It felt so wonderful, I became hooked. To this day, anything that deals with cum and feminine feet, polished toes, 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.

That 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 talked me into dressing up sexy so we could go out. I was set up to meet her new lover at the same bar we had first met, unbeknownst to me. 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 cuckold angst is always a good thing and very much expected even if not always appreciated. 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.

Prior to Laura, I developed another relationship with a very well built young lady in our small hometown college one summer. That's another long story for another post that culminated in a threesome with another guy that was my current Wife's boyfriend all through high school so stayed tuned if you're interested.


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YouKnowWho

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#2
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Glad you could post these details. You're doing great.

I think we all hope your wife catches a capable and assertive lover that you can join in with or you find a virile boyfriend to double date along with her and her new beau.

There's a lot to look forward to!
popeye1

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#3
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sissystephanie:
While I am not a cuckold

Great story.

However, I am confused by your statement of not being a cuckold!

You say you have a "current wife", and that she has or had "boyfriends", and that you have had "threesomes" etc. There lies my confusion. This is a precise definition of a cuckold, is it not?

I understand that you have been a "sissy" all your life, but Stephanie, you most certainly are a cuckold, too, and you are posting on "Cuckold Place"... a cuckold site! Please explain further.

PS Congratulations on your first ever original post...well done and thank you.

pops
sissystephanie

Anonymous

#4 · Edited by: sissystephanie
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popeye1
Sorry to be so confusing Pops! My post has been edited to properly reflect I am not currently being cuckolded by an Alpha boyfriend or FWB.

The threesome, I've yet to describe, happened decades ago with my current wife's boyfriend she dated all through high school. I knew my girlfriend in college would occasionally see other guys. One day I walked in on her getting screwed and she was going wild like I'd never seen her before during sex. He looks up and sees me standing in the doorway with my mouth hanging open and speechless then asks if I want to join them. Hell yes I do but as I strip down and start moving my hardening cock to her lips, he stops, pulls out and says, you first pointing at his hard wet cock. It didn't take very much coaxing to have me crawling on my knees before telling me the hold my tongue out. He really enjoyed making me grovel before her that day using his very adequate size cock. She continued seeing more and more guys and even though that one threesome, my first, was a pivotal day, we drifted apart probably from my fears of being discovered as being gay to be quite honest. I didn't know about any of his high school romances at the time nor have I told my Wife of only seven years that I sucked her high school sweethearts cock decades ago. Just imagine my shock when my Wife told me WHO she dated for three whole years in high school. GULP! Oopsie! The memory of his huge cock immediately popped into my mind. Oh ****!!!

So to be more accurate, as in once a cuck, always a cuck. Just like being a cocksucker. Same thing.


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sissystephanie

Anonymous

#5 · Edited by: sissystephanie
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YouKnowWho
Thanks for all your words of encouragement. We have another mutual friend from high school that took us to the Women's March in DC back in 2017 who's a hunky bodybuilder but he's gay. If anyone would ever find out, he would since he's already seen me dressed as a woman day and night over and over again. He loved my long french salon manicure back then. He should see them now.
sissystephanie

Anonymous

#6 · Edited by: sissystephanie
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After my wife's first squirting orgasm from the bigger vibrating dildo She purchased shortly after my sissy cuckold role confession, She's thanked me for the incredible climaxes ever since.

I never had any issue with premature ejaculation until the very first seconds after feeling Her slippery sloppy used pussy after prolonged cunniligus while Her hunky dildo hummed away deep and deeper. After She squirts, Her pussy is soaked and stretched open wide as She coaxing me for sloppy seconds. She thought it was so cute that my much smaller lil pecker sunk barely noticeable so quickly inside Her soaking wet pussy then less than a minute feel me throbbing inside to add my sissy seed, (her giggles were genuine and extremely intense) then again, I squirmed lower, not before a revelation by the sudden lack of reluctance lets me know, my tongue on her cum soaked clitorus has found the right spot. She hands me the dildo after switching on the next higher speed. Sex has a whole new meaning and lasts until She's fully satisfied. As it should be. My own orgasm is simply the saucy juice to fuel our passions.

We've added a couple more since "Bill", the first dildo she bought. Max and Rod are always handymen when necessary.
sissystephanie

Anonymous

#7 · Edited by: sissystephanie
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The first time I entered my Wife's wet pussy after using Her favorite vibrating dildo, Bill (which is 3"+ longer and much thicker than my tiny clit) to give Her a squirting orgasm, the ease of entering Her, along with how 'used' Her pussy felt, made me squirt so quick I could not believe it, then suddenly started shrinking and fell out to which She added She couldn't feel me in Her anymore, felt my softening clit and asked if I had cum already. I shyly admitted I had as I crawled between Her legs for my cleanup duties.

When I suggested we incorporate our friendly purple vibrator into ALL our future foreplay activities, She did not disagree and admitted She really enjoyed the 'purple guy'. Then added, you couldn't stand it if i left you for someone else. I was stunned and almost speechless that my vanilla Wife would actually say it and in my submissive state I could only mutter a feeble, 'guess so' as I cleaned my cum the best I could before using the rest as lube for Bill set on high speed.


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bobbye

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sissystephanie
7. Thanks for sharing. I wanted to ask you if you date any.You are a sexy sissy and would certainly be fun to spend the night with. Be safe.
D
bobbye

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#9
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sissystephanie
You and your story are amazing. Thanks for sharing!
D
bobbye

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#10
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sissystephanie
7 reread your story. So thrilling. Got real hard and wet. Would live to see you naked! Do you and your couple do many pics or sharing? Do you watch much porn, if so what's your fav kind? Always be safe. Your are so sweet to share with us.
D
Cadet5300

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Hot story.
Cadet5300

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#12
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Good story


bobbye

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Posts: 5638
#13 
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bobbye
Would love to see you naked! Happy holidays!
D
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