OK, so I’ve got the little Sissy fuck on a Niteflirt call…
She’s in her little pink nightie again and she’s got the big fucking dildo in her boi-cunt. And I do mean the BIG one. This fucking thing could intimidate Mr. Ed. So this bitch is repeating again and again, in that raspy breath “I’m a sissy, and I’m going to cum in my panties. I’m just a girl and I’m rubbing my little pussy in my sissy pink panties. I’m a girl and I need to be fucked in my pink panties.” She’s called before. It’s always the same pink nightie and increasingly larger dildoes stretching her hole.
Of course, this sets me off on my usual path. Playing the sissy-pimp is what I do. I prepare them to be used by real men. Sometimes I get to it sooner. Sometimes I tease it out. But I always get to it eventually. It’s kind of my thing.
So I tell the little cocklet lover that I know a man with a warm, fat cock. I tell her I want to see him fill her face and boy-pussy full of cum.
Suddenly, this person whom I’ve only ever heard speak in the most sissified voice, drops character and butches up, saying in a manly voice “Hey.. I’m no faggot!”
My apologies, sissy..
Sorry, I misunderstood. Clearly, I misread all those orgasms over toy cocks. I misinterpreted all the times you said how much you love your toy cock. I was mislead by how you said you love having a pussy to fuck.
And now that the apology is out of the way… shut the fuck up and swallow his cock like I told you.
Sissies don’t need a special occasion to get gifts (or get gifts for themselves) but they could sometimes use a shopping guide.
Here are some shopping tips for where to go and what you can get for that special sissy in your life, even if that sissy is you.
I have to admit, when choosing what types of gifts to talk about first, it was a hard choice between panties and anal toys. I gave up trying to decide which was more popular with my pest and went with alphabetical order.
Anal toys are just some of the ways a sissy can separate herself from your everyday, run of the mill crossdresser. While both enjoy their feminine side, sissification takes it a step further, a step sexier, and a step more submissive. So of course, that all adds up to being a bottom.
And now that we have that established, here are some toys for a bottom’s bottom. Whenever possible, insertable sex toys should be made of 100% silicone (medical grade is best.) Silicone is easy to clean and can be boiled to sterilize it. Use water-based lube with silicone toys and if you’re going to share them with a partner, cover them with condoms. Silicone also makes for a nice texture that’s not too hard but is still rigid enough to fuck.
All of the toys I list below are in my personal collection. I’m not a representative of the company and I make no money off of recommending them.
Tantus Perfect Plug A small plug, great for beginners. It’s no thicker than a finger and the silicone makes it comfortable for extended insertion.
Tantus Ryder A larger plug that can take some working up to, but is comfortable enough to sleep with once it’s in. A good intermediate size toy.
Pipedream Anal Fantasy Thruster Once you can take the Ryder, you can take the Thruster.. and oh.. my.. god! The thruster is an amazing toy that does just what it says. Once it’s in, just turn it on and let that boi-cunt enjoy the sensation of getting a steady fucking.. albeit with just a few inches of thrust. Still, I understand it does amazing things to the prostate and from how quickly it works to make my pets cum, I’m sure it does.
Of course, it goes without saying that sissies love panties. Sadly, the panties don’t always love them back. The gussets are too narrow to contain balls. The waistbands are too low to contain a semi.
Fortunately, there are companies who cater to molls with balls and sell pretty, flattering, girly panties with enough room for even a swollen sissy-clit.
It’s a little misleading to call some of these strap-ons since my favorites are called “strapless strap-ons” but the point is the same. Sissies love ’em.
Feeldoe Once again, I’m going to rave about a Tantus product. A silicone toy, the Feeldoe comes in different sizes and you can get them with or without vibrators in them. The feeldoe is the original strapless strap-on and my personal favorite.
Vixen Creations Nexus is another strapless strap-on. Also silicone, it’s good for those who want more insertable inches for the female player.
Male Chastity Devices
Chastity and sissies go together like peanut butter and jelly. It’s a nice little reminder for a sissy that her clitty-cock is a useless little distraction and that she focus on her duties. They serve as a reminder that she’s an owned pet. Best of all, they’re the best way to ensure that an orgasm is actually “hands free.”
cb-300 The CB-X series of male chastity devices are by far the most popular, and with good reason. They’re expandable, shrinkable, lockable, vented, and they come in a variety of pretty colors and patterns. In addition to the standard cb-300, they’re the shorter cb-600, and the Curve for uncircumcised penises. They’re perfect for extended wear.
Sissy Chastity Belt Sometimes, a gurl just wants something more traditional and girly. While the Sissy Chastity Belt isn’t good for extended wear, it’s great for being able to look down and see a perfectly girly shape under those sissy panties.
Cock Cage with Plug Of course, what’s kinky time for if it doesn’t include a little penetration? A cock cage with a plug allows a sweet nancyboy the chance to enjoy some comforting anal usage as she’s locked safely away in her steel cage.
Last but not least, we come to collars. A collar is as personal as a wedding ring and can represent the same commitment between it’s giver and wearer.
I won’t recommend what kind of collar is right for any particular sissy, but I will recommend some of my favorite sites to shop for collars. From the simply symbolic, like an ordinary necklace with a lock charm, to an “eternity collar” that is screwed together around a slaves neck and requires a special tool to remove, to anything in between. It’s easy to find any manner of collar to represent any manner of relationship.
They come in all colors and can be found to reflect your personal interests. Puppy boys can find them with paw prints and dog bone details. Sissies can find bows and sparkles. There are even collars that are made to reflect your favorite fandoms, like comic book or Disney characters.
Sissy dears, I’m going to take a moment and break with my own tradition here and address not you, my beloved pets, but rather, to those poor unwitting bastards that my feminized fuckers have seduced with their sissified charms and tranny-tricks. Why, they’re practically faggotizing poor, unsuspecting straight men on without them even realizing. I tell you, it’s a downright disgrace and a threat to heterosexuals everywhere. No wonder so many people were worried that gay marriage was a threat to marriage everywhere. It seems you actually CAN turn straight men gay, Or at least, gay-ish.
Come on sissy-seeker, you can tell us.
Ok, He-man, so you think you may just have been tapping a tranny? You can tell Mistress. Do you worry you’ve been nutting on nuts? Sucked by a sissy? Pounding a prick? Dicking a dude? Do you have the growing suspicion your sassy toy is actually a sissyboi?
Maybe it’s not even your girlfriend you’re worried about. Maybe she isn’t the one you think is secretly a dude who looks like a lady. Is that it, Petal? Do you think it might be you? Are you feeling a little.. swishy.. on the inside?
In the face of so much potential delicious deviation and tranny transgressions, what’s a poor straight (homophobic) man to do? How is a red blooded, all American he-man to know a sissy or a tranny when he spots one? (or maybe even is one.)
Fear no more, my poor, beleaguered, Trap-magnet. Your homo-erotic nightmares are now at an end, I promise you. All the secrets to telling if your wifey has a willy will be revealed in the following video… You’ll be able to go forth and fuck freely, knowing exactly what she is, what you are and who’s been floating your boat.
Oh, and You’re welcome.
For the rest of you.. my darling pets in petticoats, go ahead and give me a call. We can giggle at the homophobes and have some sissification phone sex fun.
It won’t be long now until I take you. It won’t be long before your boi cunt is mine. I can see the pulse twitching in your neck, as you kneel in silent anticipation of that sissification bliss and consider all that strapon sissy play. I let the moment linger. Then, as though I’ve suddenly turned impatient, I push your head forward, putting you on your hands and knees. I leave you there.
You know better than to look around as I walk away. The only indication you have of where I am or what I’m doing is the click of my stiletto heels across the cool, hard tile as I head toward my magic toy box. You try not to shiver as you think of the things in that trunk. You realize Mistress must be looking your way because I chuckle at your attempt to remain composed in those silly, ruffled, panties. We both know how your tension builds in the minutes before the game begins in earnest. In that brief time when you don’t know what will be coming.
Will Mistress come back with the harness? If so, which dildo will it be? The difference between intense pleasure or simple pain can be measured in less than an inch of difference in girth.
And what if Mistress chooses to make you an animal today? Will you be my playful puppy-boy, with the puppy-tail butt plug in your ass and wearing a collar, all while chasing a dildo as though it were your favorite dog toy? Or will Mistress be strapping a saddle on you and digging in with her spurs?
Your skin ripples in gooseflesh as you consider it.
Out of the corner of your eye, you see flashes of red and black. You bite your lips to keep from smiling. I return to you, the two lengths of rope coiled in my hands and hold them to your face. You kiss the ropes, with your pink cocksucker lips, first one and then the other, and sigh. You wonder what pretty designs Mistress will be tying your sissy ass up in this time before her shimmering strapon is put to use.
It’s my favorite time of the day. The strapon sissy play-date
I couldn’t help but chuckle when I saw this utter Sissy machine in London. It really doesn’t get any more effeminate than a Barbie doll pink limousine now, does it?
Now tell me, what the fuck kind of cock worshiping, demasculinized bitch would get into a flaming pink ride like this one, huh? Can anyone tell me? Beuler.. Beuler.. oh.. shit, that’s right! It’s you. You would hop right into that little queen machine, wouldn’t you, ya little faggot.
I know some of you slutty motherfuckers can’t help but cream your ruffled panties over this shit. but do try to remember, it’s still a limousine, so some decorum might be in order. Oh, I know you want to hang out the sunroof and hoot at all the hotties like a drunk chick on prom night, about to get your fucking ass cherry popped in the back seat, but really now.. we’ve all of age now, and your moment has basked to bask in the tiara wearing, sissy glory of being the little dancing queen of central high.
Of course, slut that you are, it’s too late to pop your cherry in this pink dream on wheels, but you can still celebrate the little sissy
whore that you are. I’m sure we can manage to get you a cock or two in the back seat with you.. and it can be left to you to give the driver ‘just the tip.’
Who’s gonna be first to leap at the chance to be a swhore in the back seat of the Sissy Limo?
An addicted little sissy leaning fanboy of mine had a dream last night. In it, he and his wife were getting tattoos with my mark on them. I love those kinds of dreams.
If there’s one thing I love even more than turning a man into a sissy, it’s him into a sissy and having him also coerce his wife or girlfriend into becoming my little slave fuck-toy.
The image above is a phrase in Hebrew that my ex-lover wears on his back. (Sorry, I couldn’t find a picture of it on his skin.) He was more of a pain slut than a sissy, but being a devoted pet, he took my mark as if I were bestowing a great gift upon him.
The original phrase is from the Song of Soloman where the words “Ani l’dodi v’dodi li” translate as “I am my beloved’s and my beloved is mine.” Though, that’s a statement about a man The female version is “Ani l’ahuvati.” (Thank you to the reader who corrected my weak Hebrew grammar. )
I Wasn’t Always a Sissy Mistress
When I was younger, I thought it would be nice to have the first part tattooed on my lower back. I planned to get the second half done when I was married. It was kind of a romantic reminder that somewhere out there, the man I wanted was waiting, even if I hadn’t met him yet. What can I say? I was young. I probably had Cinderella singing “Some Day My Prince Will Come,” playing in the background when I came up with it.
The first time I was asked what sissy tramp stamp I would put on a slave, the answer was a no-brainer. I would mark a sissy with that phrase. “I am my beloved’s.” What had once been a notion of romantic hope could easily translate into a sign of sissy ownership. I made sure each sissy understood it was part of a longer phrase. They know that intentionally leaving off the second half was accepting that they may surrender to me, but I would never be mutual.
The sissy boys and pseudo-slaves whacked off like mad as they thought about being branded like a piece of property. Then they would forget about it until the next time. Only the one had the balls and the temerity to take my mark. Or was that just the lack of foresight? After all, we’re no longer together.
What became of my marked sissy?
I haven’t seen him in years. I hope he’s doing well. Now he walks around with my mark on his back as a perpetual reminder of how he was owned by me. That said, he knew the story of how I came up with that phrase as my mark, so perhaps he’s changed the message of the tattoo in his mind. Perhaps now he looks at it and thinks, as I used to, “someday my prince will come.” ..After all, I now know my grammar was wrong and his tattoo literally says he belongs to a man.
Heading into the weekend, it’s important for every sissy to know and understand how to express her feminine nature and her inner sissy-whore in every aspect of her being. From how she moves and how she sounds to what she wears and what she puts into her mouth, (no, I’m not talking about cock, you slut!) a good sissy will find ways to tell everyone just who and what she is, even if she’s not dressed in her full, tranny regalia.
Having so many choices to make can lead to a whole, heaping lot of sissy confusion. But never fear, my darling clitty-dick, Mistress is here to help you make your choices in all aspects of your day. After all, what is a controlling bitch for if not to tell you the right and wrong ways to live your life right down to every last feminized detail?
Sissy Cocktail Recipes
1 shot Butterscotch Schnapps
1 shot Irish cream
Blend the ingredients and serve in a shot glass
½ shot Amaretto
½ shot Irish cream
½ shot Peach schnapps
1 /2 shot cream
Mix ingredients and serve in an old-fashioned glass
½ shot Blue Curacao
½ shot rum
½ shot Peach schnapps
¼ shot Sweet and sour
Dash of Sprite
Mix ingredients. Chill with ice and serve in a shooter glass
¼ shot George Dickel
¼ shot Jack Daniels
¼ shotJim Beam
Mix all the ingredients, leaving the grenadine for last. Stir with a swizzle. Serve in a shot glass
1 shot Butterscotch Schnapps
1shot Irish cream
Blend the alcohol and serve in a shot glass. Top with whipped cream.
1 shot Irish cream
1 shot Gran Marnier
2 shots Espresso
Pour Irish cream and Grand Manier in a mug and add espresso. Top with whipped cream.
½ shot Grenadine
. ½ shot Green Crème de menthe
. ½ shot Crème de Banane
. ½ shot White Rum
Layer the ingredients by placing the tip of an inverted spoon against the inside of a shot glass and slowly pouring the drink over the bowl of the spoon so that it spreads over the top of the previous ingredient. Begin with Grenadine, then layer the crème de menthe, the crème de Banana, and finally the white rum. Light the rum before serving and serve with a straw. Drink quickly, of course.
½ shot Sambuca
½ shot Irish cream
Shake with ice, strain into a shot glass
Pink Sissy Alarm
3 shots Vodka
2 shots Lemon Juice
2 shots Raspberry Juice
1 shot water
Mix lemon juice, vodka, and water and pour into a champagne flute. Using an inverted spoon, layer the raspberry juice by placing the tip of the inverted spoon to the inside of the glass and slowly pouring the juice over the bowl of the spoon. It is served layered and the drinker is to put their hand over the top of the flute and shake to blend it to a nice, sissy pink color.
Dick in the Dirt
1 shot Peach Schnapps
½ shot 151 proof rum
½ shot Southern Comfort
½ shot Yukon Jack
Splash Pineapple juice
Splash Cranberry juice
Splash Grand Marnier
Mix ingredients, serve over the rocks in a Collins glass
It’s been a while since I’ve done one of these, mostly because they can be repetitive. But today’s letter from a curious instadom was different enough that I thought it was worth sharing.
For those of you who are unfamiliar with the term, an InstaDom or InstaDomme is someone who hangs a shingle and calls him or herself a Dominant because they think it’s a quick way to get people to give them either money or pussy. These people are different from beginning Dominants in that they don’t bother to learn about the fetish they’re catering to, not having enough interest in the actual kink to do the research before they go looking for submissives to kiss their asses.
You’ll see here that the person who wrote to me seems to be in a gray area. On the one hand, he’s asking for information. That’s a good thing. On the other hand, he’s calling himself a Dom when he clearly has no understanding of the submissive mindset. Perhaps I was too hard on him. I’ll leave it for you to decide and respect your opinion, whatever you think. But his question belied such a lack of understanding, that I’d have been far more impressed if he’d been asking for information without calling himself a Dom. Calling himself a Dom at this stage implies that he’s actively trying to Top someone without the first clue about what might make them tip.
Here’s the letter so you can judge for yourself. The name has been withheld to protect him from his own foolishness.
———– (AKA InstaDom)
Oct 27, 2016 06:38 AM
“Hi there I am sorry to bother you but I was wondering if you could possibly answer a question for me I’ve never been submissive I’m a dom being a dom I can’t understand why a guy would be in thought process of being a sissy or being humiliated I was curious if you could give me some insight “
My Response To Mr. Instadom:
“Based on the question, I’d think you weren’t a Dom so much as an InstaDom who wants to wear the label of Dom in the hopes of scoring some compliant pussy or else a girlfriend who won’t challenge selfish behavior.
Whatever your motivation, anyone who calls himself a Dom without bothering to learn, understand, and empathize with the submissive mindset isn’t worthy of the label.
Or else you’re just so insanely sexist that you can’t imagine men and women could share any of the same needs and desires, whether that be for love, acceptance, or in the case of a fetishist, humiliation.
There are many reasons people come to enjoy submission and/or humiliation. The two are not always the same thing, even in a BDSM relationship. But once someone has developed a taste for the adrenaline rush of humiliation, sissification can be a quick and easy way to get it. After all, in a world where sissy and faggot are the worst things most bullies can think to call a man, it’s hardly surprising the words hold so much power over a man’s mind. Just as women who are into humiliation can enjoy the sting of the words whore and slut, men can enjoy being called faggot and sissy. Of course, calling people slut or bitch is usually directed at women, using them on a man with a sissy fetish can be doubly powerful for its emasculating effect.
With all that said, this just addresses the question as you asked it, with regards to sissy humiliation. There are many sissies who enjoy the fetish without the humiliation aspect. Again, there are as many different reasons men like it as there are sissies indulging in it. Some just enjoy women so much, they want to wrap themselves up in all things girly. For others, it’s a symbol of how much power they’ve relinquished to their Mistress or Master. For some, it can be just an enjoyable exercise in pampering and playing to a degree that usually isn’t afforded to men. Still others will just have had a spontaneous erection at a time in their early lives so that, ever after, the tingles were associated with whatever object they were focused on at the time it happened. If that happens to be some article of clothing, a fetish is born.
There is simply no simple answer to your question. The paths that lead a submissive to their kink is never a direct route from inception to fully fledged creation. A multitude of relationships and experiences will build on the foundation of a fetish to make a very individual submissive with very individual needs and responses.
Now, with all that said, being a Dominant is a responsibility, a burden, and a blessing. It’s not about your needs and wants nearly as much as it is about theirs. Just because I’m in charge doesn’t mean what I do is all about me. Just like with raising pets, I may be an owner, but I’m also responsible for their care. And if I don’t understand them at all, it’s going to end badly for both of us. They need control and you can’t control what you don’t understand.
I commend you for trying to learn something but suggest you spend a little more time on that before you go around calling yourself a Dom, especially to people who know the difference.
The very notion of sissification brings to mind images of weak, unmanly creatures. After all, what could be less manly than to take on the traits and mannerisms of a woman. And to be honest, sissies don’t just take on female mannerisms. They take on mannerisms that are exaggerated versions of femininity. No natural born woman is ever as girly as a sissy in full pageantry.
The reality of it is that sissification takes some serious balls. Of course, it’s easy to imagine the nerve it takes for a man to go out in public dressed as a woman. Those sissy bitches risk ridicule at best and violence at worst . But before a sissy ever reaches that level of confidence and bravery, she has to be brave in front of the mirror. And that’s not small feat.
All you sissification enthusiasts know what I mean. Whether you’ve been out, or your still just dreaming of putting on your first pair of panties, you know the guts it takes to confront your own sissified reflection.
Full on sissification calls upon many of the qualities we think of as being inherently male. A sissy must have the pragmatism to recognize what she wants and the will power will to pursue it. She must be direct enough to present herself as she wishes to be, with no apologies or excuses. And she must have the strength of character to dismiss the opinions of ignorant people who would tell her that she’s somehow wrong or unnatural.
Sissification will make a man out of you, yet.
If a sissy is lacking, or weak in any of the qualities I’ve mentioned, the act of getting all girly will force her to develop them. And of course, Sissies tend to be horn dogs.. another distinctly male trait. As they follow their libido into a pair of panties or onto a butt plug, sissies are indulging that very masculine behavior of acting slutty.
While that last part doesn’t neccessarily make you a better man. It certainly doesn’t make you a worse one.
But as you dress up and make-up, you’ll not only strengthen those masculine qualities which will make you more manly in your day to day life, you’ll also come to have a better understanding of just some of the challenges that face women.
Oh, I don’t mean to say that you’ll suddenly know what it is to be objectified and diminished because of your physical appeal, or make less money than your fully masculine counterparts. And no pair of stilettos will raise you high enough to hit the glass ceiling. But in very small ways, you’ll come to know the women in your life a little better.
You’ll learn the frustration, and some of the discomfort, of having your pantyhose not quite reach your crotch. You’ll understand the ache of wearing high heels to go out dancing. And you’ll feel a sense of triumph when you finally get your false eyelashes on straight.. ort straight enough to hide any mistakes with eyeliner.
And little by little, you become a better understanding, more manly version of yourself, as you indulge the more feminine version.
I know how well you sissies love cock so much, you’d even love to have one on the women you service. She here today, I’ve put together this handy dandy list of tranny porn stars to get your little sissy clitties tingling.
Meet the Trannies
Viewers first saw this tiny little tranny in 2011, when she released four films in her first year. She’s since staked her claim in porn history.
If these names sound familiar, it’s probably because that’s where Lamar Odom had his unfortunate overdose. In fact, it’s Madison who encouraged him to come to the brothel for a night of discreet fun. The Kardashians later received a public letter of apology from Madison for her part in the incident. She wasn’t with him that night and didn’t give him drugs, but felt badly for inviting him.
HBO subscribers may also know The Love Ranch as being the setting for the series Cathouse.
Venu has had an impressive career in the four years since she’s started began making porn. Nominated for AVN awards each year, she’s won three times, so far.
She’s also a clever thing, having a column called Venus Rising. It’s since been turned in to a book called Venus Lux Diaries.
If a Barbie Doll came to life (and grew a cock,) she’d be Aubrey Kate. As perfectly beautiful as she is, it’s hard to imagine she was ever shy. Fortunately for us, she’s come out of her shell and has been fucking and sucking men on film since 2003.
For me, being a genetic female, there’s just something hot about seeing a trans-woman with another woman. It gets even hotter when you add a man to the mix. Sadly, tranny porn is usually something of a sausage-fest with no pussy to be found. For this reason, the delicious Jessica Fox made my list of hottest tranny porn stars. Sure, the bulk of her videos are of her with men or with other trans-women. But this bisexual beauty doesn’t wilt in the face of a pussy.
My personal favorite is Baily Jay. She’s been around since 2010 when she was working under the name Harley Quinn but she’s almost unrecognizable since then. Oh, there’s still the same beautiful, dark, almond shaped eyes and pouty lips. But with the years of hormones and a perfectly shaped pair of new boobs, she’s gone from a cute chick to a gorgeous woman. For those who enjoy girls who are as clever as they are beautiful, a peek at her Twitter will reveal her wit and intelligence.
Her charm has have served her well, getting her guest spots on everything from Dan Savage’s podcast to Amy Schumer’s Comedy Central show.
Best of all, you can chat with her yourself sometimes, since she has a listing on Niteflirt. The listing shows when she’s logged in and feels like playing on phone or cam. I highly recommend clicking one of her Send Mail buttons to get on her customer list. That way, fans can be one of the first to know when she’s available. If you don’t know what to say to her, try congratulating her on the AVN award she got in the mail this month.