sissy cuckold dreams

I saw the punch coming. A right cross. Thad telegraphed it. I ducked under it and his flying fist met a 2"diameter steel water pipe just behind where my head had been. Cold water I think, from the blood his knuckles left on the bare pipe. I ran.

"Your ass is mine!" Thad shouted after me waving his bloody fist in the air. You'd better run, you sissy wimp bastard. You're going to be sorry you were ever born." And in words more prophetic than either of us knew, he added, "You'll be wearing a dress before I'm through with you."

What a sore loser, I thought, as I raced across the campus. Ok, so I stole his precious Jacquelyn...his gorgeous fiancée. I had wooed her with poetry, flowers, and expensive jewelry, not brawn and bluster like muscle-bound Thad. And, of course, an inheritance from my hard-working grandfather didn't hurt either. But as I would soon find out, Thad had something to offer Jackie that I didn't, something that money couldn't buy, something that turned on her lights brighter than the powerful beam shooting out of the top of the pyramid hotel in Las Vegas. I'm talking about breathtaking sex and thunderous orgasms that came courteous of his big thick cock.

What's the big deal about sex anyway? A couple of inches of penetration, a minute or two of rubbing, and a little squirt at the end... it hardly seemed worth all the fuss to me. Then one balmy night in Florida I learned the truth and it hit me like a blast of artic air cutting across a warm desert: I had the small cockette and staying power of a little sissy boy. The problem wasn't with boring sex, it was with boring little me.

And who am I? My sissy name is Rhonda Dee Ann, formerly Ronnie D., and I'm a cuck-aholic; an obsessive cuckold wannabe with a little penis that gets hard in a nonosecond, and as I found out, is too small to please a real woman. As a submissive I dream of having a beautiful dominant wife to love, cherish, and obey who will cuckold me unmercifully with aggressive well-endowed men. This is the story of my haunting sissy cuckold dreams. The names have been changed but much of it is true, except the dreams, of course. Though, when you think about it, since they are dreams, I guess you could say they are true too, at least true sissy cuckold dreams.

The big shock came at a local lover's lane near the university. That's where it happened; where I first learned that I had a small penis. Until then, I thought my penis was average in size. It took Jacquelyn,my assertive girlfriend,to set me straight. At night, after classes, Jackie's long brunette hair cascaded down over her shoulders and her glasses came off, revealing big brown eyes. Her dresses got a little tighter, a little shorter, and a little more bosom peeked out. The night light softened her smooth skin and darkened her red lips like a gothic vampire. She transformed from a studious-looking library rat into a hard-nippled sex siren. I could even smell her hot moist sex. She would taunt me saying that if I didn't take her to the local lover's lane she would find someone else who would. The thought of her doing this always gave me a hard-on. So of course, I took her there for nearly a month at least four nights a week and Saturday night too. We kissed, petted, and groped in the dark until the car windows on her old Nash Rambler fogged up like a mobile steam room. Then, we stripped each other naked and she fondled and stroked my little wonder into its full 4-inch purple-headed throbbing glory, while I finger-fucked her swollen pussy like a girlie juice machine. When she felt aroused and in her slut state" she would push the front seats down into a bed,the Nash Rambler was great that way... and would lay back with her legs spread and her slick shaved pussy open and beckoning. I went down on her and licked her into a squirming frenzy until she begged, Put it in now Ronnie. Hurry. Please.

I tried, but my excited little swollen cockette usually burst on contact leaving a gooey white blob of cum on her pussy. She never once came from this, of course, and often repeated her plea to hurry up and put it in. Even those times when I did achieve penetration my cock poked its tiny head in like a frightened little boy peering into a mysterious dark cavern for the first time. I usually came within seconds while she still begged me to hurry and get it in. And if she got on top, my little penis either erupted and withered, or slipped out at the peak of her humping excitement. It left her high and dry, and frustrated.

And doggie style,forget it. When my small penis tried to get past her shapely round haunches into her pussy I felt like a donkey chasing a carrot on a stick. My penis poked at the entrance but never really got there.

I tried to make up for my pathetic performance by finger-fucking her and rubbing her clit to make her cum, but with my fumbling inexperienced technique, that didn't happen often. Then one night, after my usual quick cum, I got the humiliation of my life. I rubbed her wet pussy as usual, but she just lay there staring at the dome light on the roof of the car as if she was reading her future in a crystal ball.

Suddenly, she reached down and slapped my hand away and said, "Stop, dammit."As we put our clothes on in silence she said matter-of-factly, "I like you Ronnie, but your penis is just too small for me and you cum way too quick and too little. I need someone bigger who lasts longer."

My face felt flushed and no words came out of my mouth. I wanted to run. We drove home that night in silence. The next day I got a note from her that our relationship was over and that she was going back to her ex-boyfriend, Thad.

Even though Thad wasn't the brightest star in the sky, I knew that he would gloat over his victory. He was arrogant and cocky and hated me for stealing Jackie from him in the first place, just because I could write romantic poetry and he couldn't. But he did have the advantage of being 6'3", with 220 lbs of solid muscle, and I tried to avoid running into him on campus for fear that he would beat me up. I imagined that he would fuck her like a pile-driver to get revenge. He would humiliate her and make her act like a whore just to teach her a lesson. He might even spank her. It maddened me to think that she would love it; love the fact that he took her like a Real Man, not a small-cocked submissive sissy wimp like me.

That was the beginning of recurring nightmares about Thad's giant 10" penis and Herculean staying power. I imagined Thad, the hung hulk, fucking my gorgeous Jackie into ecstasy with long, slow, deep penetrating strokes, my face only inches away as she moaned like a slut: Yes, yes, fuck me like a Real Man Thad, honey. Do you see how a Real Man with a Real Cock does it Ronnie?" I imagined Thad cumming in buckets and ordering me to lick it up wimp," as they both laughed and joked at my little boy excuse for a cock. I hated him as much as I'm sure he hated me and relished his sweet revenge.

After that humiliation, I measured my erect penis and became obsessed with comparing it to the size of items around my dorm room. I found that my erect penis was a half-inch shorter than a Popsicle stick and fit neatly inside an empty toilet paper tube. After researching penis size I discovered that my 4 inches in length measured at least 2 inches below average, in the less than ½ of one percentile bracket. This meant that more than 99.5% of the males on the planet (199 out of every 200) sported a larger penis than me. What woman would want to fuck a miniscule penis,especially one with little cum and no staying power,when there are big men like Thad out there? Jackie, you were right: I was, and still am, a wimp.

I didn't know about cuckoldry at the time, but now that I'm older and looking back, what a classic cuckold opportunity I had. I could have found her fraternity studs and sports jocks, helped her bathe and dress sexy for her dates, licked her pussy into a slutty ready-to-fuck state of arousal, chauffeured her and her stud lovers, and even cleaned her up afterwards with my tongue into one final after-glow orgasm. What a kinky team we could have made,her horny and dominant, me horny and submissive. She could have denied me sex with her or anyone else, and only allowed me release under her supervision She could have demonstrated her power over me with her girlfriends by making me jack-off and eat my own cum in their giggling presence. She could have even fucked Thad like a whore in front of me. It would have been humiliating, but what a turn-on. Such are the twisted dreams of a cuckold wannabe. Jackie, where are you now that I need you? Please come back and marry me and make me your submissive cuckold. It's still not too late.

From the desk of Jacquelyn

My Dearest Ronnie,

It has been a long time. So you say you want to be my submissive cuckold hubby? Is that true? Well, we'll see. We already know how worthless your cock is, but less than a half of one percentile is laughable. Thad will get a kick out of it. We broke up last year because he cheated on me, but he's still a great fuck. He would be pissed if he knew we were talking. He's a professional wrestler now... he's called Big Bad Thad...and he still has it in for you.

I've learned a few things too since college, such as a taste for bondage, but one thing is the same: I still crave big cocks that stretch me to the max and touch me in places you never will. The minimum cock size I accept now is 8, long and 6, in girth at least twice as large as yours. I've also become quite dominant & you will either be shocked, or pleasantly surprised, depending on how submissive you are. I don't want to play games and waste my time though, so let's find if you're serious. I need to know: can you follow instructions and are you are good cuckold material?

There are some gangbang parties coming up in Las Vegas next month. Since you are in Southern California, I want you to drive here to Arizona, pick me up, and chauffeur me to Las Vegas where we will spend a week... at your expense of course... getting to know each other again and testing your cuckold potential. If things work out, there are a lot of wedding chapels there, and it's a great place to have a first honeymoon. (I would cuckold you on our wedding night and honeymoon of course). If you think you are still interested, get on your knees and write me a proper submissive reply.

Kisses, Goddess Jacquelyn

Ah, bondage. How did she know? I've always been a little submissive. As a kid I loved being captured and tied up in the cowboys and Indians game. One time, an aggressive cowboy tied me to a lamppost, unfastened my belt, and pulled my pants down. I didn't complain and secretly wanted him to do more... maybe even forcibly strip me in front of the neighborhood girls. This didn't happen because somebody's mom yelled out that supper was ready. Nevertheless, I felt a twinge in my sissy cockette. I never wanted to bind anyone else, but only imagine that the damsel in distress (helplessly bound naked on the railroad tracks by the evil villain) was me. Some of my hottest masturbation sessions came when I lay self-bound, spread-eagled, and naked in bed looking at pictures or reading stories about beautiful women in bondage. I identified with them.

But why does it turn me on to think about watching my wife have sex with other men? I was curious about my cuckold feelings, and I found out there is a natural explanation for it. It has to do with sperm wars. No, this is not another sci-fi flick; it's when the sperm from another man inhabits Jackie's womb the same time as mine. Although her ovulated egg is good for only 12 to 24 hours, a man's sperm can lay in waiting for up to seven days. Not only that, but she will have stronger orgasms with a lover and retain more of his sperm. All this makes her more likely to get pregnant by her lover than by me.

The evolutionists say it's an adaptive trait forged over millions of years for me to get aroused watching her fuck other men so I can get in there quickly and deposit my sperm to compete with sperm from other men. They say some men get so aroused that they go out of their way to arrange extra-marital sexual encounters for their wives. Sounds like a cuckold fetish to me!

I don't know if sperm competition explains everything, but they are right about one thing. I would get so aroused by it that I would go out of my way to arrange satisfying sex for my horny wife. Being naturally submissive and having a small penis probably also helps. Humiliation (pointing out and displaying my sexual inadequacy) is also a turn-on. So yes Jackie, I'm ashamed to say that your extra dominance and taste for bondage only makes me want you more. I'm so aroused thinking about you having sex with other men that I'm on my knees, begging you to take me back and cuckold me.

From the desk of Jacquelyn

Dearest Cuckold Ronnie,

All right little pussy boy, are you sure you want to do this? Theory is one thing, but practice is another. Just so you know, here's how things will go:

You will make all the arrangements for the parties and the hotel. I want a honeymoon suite in a top hotel on the strip with a king-size bed for me and my lovers and a roll-around cot for you. You will help me get ready for my lovers and when they arrive you will be tightly bound on the cot ,dressed like a sissy, while I entertain my big cocked Real Men in the king-size bed. That's right, a sissy. I know you think you are macho, but if you are to be my cuckold hubby, that has to change. As I said, I am quite dominant, and I want a sissy cuckold hubby. My lovers will be more comfortable having you around if you are a sissy. Some of them may want the attention of two women even if one of them is a fake. And besides, I think it would be fun to feminize and sissify a formerly macho man. Don't you? Do you think you can handle that? Can you be a sissy for me?

I expect you to serve me breakfast in bed, bathe me, shave me, and see that I am dressed as seductively as possible for my lovers. And, even though the hotel has maid service, I expect you to keep our room tidy and clean and to scrub the toilet and the tub, and to make our beds everyday like a sissy maid. I want to see how well you do these things and how much training you need. I will keep a Do Not Disturb Sissy At Work" sign on the door most of the time while you do the cleaning. Your status will be obvious to all the hotel staff. I'm sure the maids will enjoy it.

You will also be responsible for my entertainment. I want to see the best shows and events in town while we are there, and I also expect to dine like royalty. You will chauffeur me (and my chosen lovers) to the best restaurants on the strip. We will dine, dance, and flirt while you polish the car and wait obediently for us.

You will be my chauffeur, my servant, my sissy maid, and my trial cuckold hubby for the week. I plan to have a good time and to get fucked senseless by as many well-endowed good-looking hunks as I can while you watch, listen, massage me, kiss and lick my feet, ass, and pussy whenever I want. You will clean my cum-filled pussy afterwards and lick the asses,even suck the big fat cocks of my lovers,if that is what they want.

By the end of the week I will know if you are good cuckold material. So, how about it? Can you be a sissy? Can you take being bound? Can you watch and listen to me get power-fucked by much bigger and better men than you? Can you lick up their cum? Can you suck cock? Think about it. Be sure you understand what you're getting into. If you still want to do it and are serious, then there is no time to waste. Let me know with a more positive pleading letter if you think you are still up to it, and I will send you more instructions.

Kisses, Goddess Jacquelyn

Sissy? Did I read that right? I'm a macho guy, or at least so I thought. I did try on my mother's nightgown once while my parents were gone and the silky diaphanous material felt delicious. And I've always thought that men's clothes (especially the colors and textures) were as dull as a barren tree on an overcast day in winter. All browns, blacks, and grays. However, even though I liked it, I didn't dare pursue this interest because it would implicate me as gay. It isn't true, of course. I'm not gay and never have been, but it would still be difficult to explain why I enjoyed wearing feminine things. Am I am a secret sissy wannabe too? Maybe Jackie knows more about my secret cravings than I do.

The thought of me bound and dressed in panties like a sissy watching dominant men kiss and fondle Jackie into her slut state until she begs them to fuck her does give me a rock-hard little weenie. Just thinking about hearing her muscular studs grunting like animals and pounding her into the bed and banging the headboard against the wall like a runaway freight train, her screams of ecstasy bouncing around the room and down the hall makes me cum. Damn, I'm so addicted, I'll do anything, even that. Yes Jackie, if that's what you want, I will be your sissy cuckold.

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This sissy is sooooooooooo glad to be in the community. she is learning so much and hopes to get much more training to be a better sissy slut, she loves to submit and please and talk with her sisters.

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