Tag: Crossdressing Phone Sex

Sissy Training Phone Sex with Brooklyn: Fitting Room Rendezvous

I have a new sissy in training. I’ve got her looking like the pretty girl she was born to be. I mean she was born with a clit stick, not a cock. From the moment I met her, I knew she was just born in the wrong body. Just because she could not fuck me, did not mean she did not have a role in my world. So, I have been grooming her to be my newest sissy. Today, she dressed herself for my approval. When she picked me up for our shopping trip, she looked gorgeous. She had been paying attention to me in regards to how a whore applies makeup, dresses, styles her hair and does her nails. The true test would be if she could convince others she was a true pretty girl.

We went into Victoria Secret and immediately all eyes were on us. Well, most eyes were on me. But my sissy caught the eye of a pretty handsome man. Now, I have been teaching her how to suck cock too, but technically she is a virgin still. She has only sucked dildos and the like. I gave her a sissy assignment. I instructed her to go find something sexy to try on, and get that guy into the dressing room with her. I wanted her to give her first official blowjob. She did exactly as she was told. As a sissy trainer, I was so proud. I followed them into the dressing room, got myself in the room next door and stood on the seat to look over. I had to watch her give her first blowjob!

I was shocked that she did not seem nervous at all. She was on her knees with his cock out. It was a much bigger dick than I thought by looking at him. I was a little jealous.  Her pretty polished hands grabbed his cock and guided it into her  mouth. She sucked his rod like she had been swallowing dicks for decades. My sissy was making me wet, not just proud. I guess I made some noise as I was rubbing one out watching her pop her mouth cherry. The dude looked up and caught me spying. He wasn’t  upset, but turned on. Told me to get my hot ass on over. I joined them, put the occupied sign on the door and told sissy to guide that nice cock into my cunt.

I twat blocked her lol. If he had a shrinky dink like she did, he would have been all hers, but I am a greedy whore when it comes to a big dick. But she is an obedient sissy, and acted like the perfect fluffer. She got him good and hard for me right there in that fitting room, and he fucked me hard and fast. Dumped a huge load of cum in my greedy cunt. Since my sissy did so well snagging a well hung stud and giving her first BJ, I let her clean my pussy up. I don’t think that stud knew what hit him lol. He was clueless about Sissy’s true nature.

We all walked out of that dressing room together. Both me and Sissy had smeared lipstick on our faces and our well hung stranger had a shit eating happy grin. Sissy gave her first BJ, I got a hot quickie with a real man, a stranger had his cock rocked, and Victoria Secret got almost a grand of Sissy’s money as she bought us both some sexy treats. Not a bad afternoon.

Size Queen Brooklyn

So, a sissy wannabe sent me some pictures of her for public shaming. First, I was like why should I bother when she has never called me. But then I was like the what the fuck, I love humiliating tiny dick losers. And this one has a wife who obviously is a size queen, she just isn’t a dominate bitch yet like me. I have no problem letting my husband know I am going out to get a real man. Hell, I fuck real men in front of him all the time.  But this sissy, Samantha, only recently discovered that her wife has been whoring around on the Internet looking for big cock. See guys don’t delude yourself. Size matters. Some women just prefer to save your feelings and get what they need discreetly. I on the other hand, have no problem being vocal about my needs. I need big cock. I will have big cock. Life is too short not to be sexually satisfied. And this poor sissy’s wife has to be one sexually frustrated woman looking at that pathetic little thing. Good for her for saying enough is enough, or not enough in the case of her husband’s dick!

At least this sissy knows she belongs in panties. I feel sorry for all the women out there stuck with husbands like Samantha. No way she can satisfy a sexy woman. I bet she can’t even please her hand. Women stuck with pin dick pathetic husbands need to take control and get a real man for their bedroom.  Sissy husband’s like Samantha belong in the house cleaning and taking care of household things, they never belong in the bedroom.  Small dick husbands are really more like pets. My husband doesn’t share my bed with me. We have separate bedrooms. I also have a large pet bed for him. That is where he lays when I am entertaining a real man in my bedroom.  I think Samantha’s wife needs a pet bed for her, because it is clear from this picture that she can’t give her any sexual pleasure.

Send me all the pics you want sissy boys and tiny dick losers, but be forewarned, I will use them for my amusement and to empower other women to be a dominant size queen like me.  If you can’t fuck me, you very well better amuse me.

We All Thought He Was A Sissy

He has never made a secret about the fact that he loves to wear girls panties. He will tell you without batting an eye that the way they feel excites him. He will tell you that just the feel of the material rubbing against his cock when he walks that he can’t control the hard on he gets. He will tell you that the way they fit is so much more comfortable then mens underwear, no matter the style, including boxers. In fact if you let him, he will go on and on about the pros and cons of it all.
So we always just thought he was a sissy. None of us would ever think about fucking him, In fact it was a common joke amongst the girls that he must have a little cock to fit in a pair of chicks underwear.
We got drunk last week and I lost a bet and the pay off is sleeping with our local panty wearing sissy.
I wanted to get this shit over with so last night was the night I bit the bullet.
You know that saying never judge a book by it’s cover? Man is that true. When he took off his pants and had on those sheer red bikinis and they outlined his hard dick, I think my chin hit the floor.
I heard the gang gasp from their hiding place and by the smirk on his face, he did too.
He grabbed me like Tarzan and crushed my body to him, kissing me so hard that he took my breath away and my cunt was wet before the kiss ended.
Breathless from the kiss and the feel of that thick and long, hard cock in his panties up against my belly.
I started to undress and he yanked my arms behind me holding them in one hand like a vice and ripping my clothes off with the other before shoving me on the bed and snatching my legs open, burying his face.
A girl had to have taught him this, because he was licking me like a woman would, hitting all the right spots and all the right places.
Just as I was about to explode, he stood up, looking down into my eyes. Grabbing his panties he ripped them off and that dick sprang to life for the first time.
Hovering over me and positioning himself above me his mouth came down on me hard again.
I could taste my pussy on his lips and tongue and then he slammed into me hard. biting my lips as I let out a scream of pleasure.
He held himself in me deep before he finished us both off.
He only fucked me for 15 minutes tops before we both exploded, but it was the hottest fuck I have ever had.
He may be a panty wearing man and we may label that a sissy, but in bed he is a fucking beast!

Sissy Phone Sex with Goddess Brooklyn: The Sissy Games

I love sissy phone sex. Some of my friends don’t understand why because I can’t fuck a sissy. A sissy has a tiny little limp dicklet, like Mistress Levi’s sissy faggot that I get to play with every now and then. Maybe I can’t literally fuck a sissy, but I can fuck with a sissy. That is why I love sissies so much. I have a few of my own sissies, but honestly none quite as pathetic as Mistress Levi’s Sissy Fairy Fag. She is a special breed of sissy. Look at how pretty she is in her pink lace baby doll dress and jingly jangly bracelets that are as limp as her clit stick? She provides me and other goddesses so much enjoyment.

I want to have a sissy fairy contest. You heard of The Hunger Games? I want the Sissy Games. I want my sissies to send me their best pictures.  Use Mistress Levi’s sissy faggot as an example. I am hoping MY sissies are just as creative and pretty. I know they are just as pathetic. Go shopping if you have to. Steal your wife or your daughter’s clothes even. Go on a sissy shopping spree. I don’t care how you do it, just do it. Then I want you to honor me with some sort of tribute. A song, a poem, a special handmade gift… Something that demonstrates you understand your place  at my feet. I will share all pics and tributes on my wall. You see public shaming of sissies is so much fun. Not only do I get to humiliate my sissies, but so do all my hot friends and the world. Because once you are lucky enough to adorn my wall, you are in the public eye for anyone to shame. Even your poor family.

The winner of my pretty sissy contest gets the chance to purchase a pair of my perfect panties for only $25. Normally, the panties of a supreme goddess like me would cost a pathetic loser like yourself well over $100. For the privilege of adorning my wall in your best sissy outfit, you can wear a pair of panties that have been next to a goddess for a steal. I mean it is the closest you will ever get to being in my panties Loser. Mistress Levi’s sissy faggot buys her all sorts of pretty things, sends her tributes, does humiliating tasks for her enjoyment, writes her songs…. I know my sissies can do the same for me.  I know my sissies can be as equally pathetic; can show me the same amount of respect.

So let’s step it up sissies. It’s not enough to just pretend on a phone call that you are a twirling  fairy faggot. I want proof. I want to see pictures of my sissies in pretty dresses, diapers, sucking cock… You get the idea. I will not be outdone my Mistress Levi and her Sissy Fairy Fag. Let the Sissy Games begin.

Look at the little sissy fairy faggot!

sissy phone sexWe have a little house pet here at Fuckalicious and she is the sissiest fairy faggot of them all. She tries to pretend that she’s a man when she goes to work but we all know the truth and the truth is that there is absolutely NOTHING manly about this sissy at all. Honestly I don’t see how she fools her clients into believing that she is a man, I’ve seen her wearing her fake man clothes and do you know what I see? It’s definitely not a big shot lawyer man that’s for sure! I see a little fairy princess that likes to fill her precious little panties with poopy just like a little baby. And you know what? That is about as far from a man as you can get! I have to say though, sissy is very amusing to play with, when she makes her little piggy noises or sings her little songs she makes me laugh like crazy. She really should quit pretending to be a man and just admit once and for all that she is just a poopy loving little sissy fairy faggot and then we could get her a nice big cock to suck!

Sissy Phone Sex with Brooklyn: Do You Know Your Place?

I am a beautiful size queen. I know my worth. Sadly, many guys do not. However, a few do know their rightful place with me and other women like me. Like Goddess Levi’s sissy fairy fag. Some of you tiny dick losers who keep trying to convince me you got what I need, could learn a few things from her special Pet. See, if you have a small weenie, clit stick, pin dick…. you only have one purpose in MY life. That is entertainment. That’s right, small dick sissy fairy fags get to entertain and amuse me. They never get to fuck me.

There are many ways to entertain and amuse a Goddess like me or Levi, as sissy fairy fag has learned. One, you can dress up like the sissy you are and prance, preen and twirl for us.  Put on a pink frilly outfit, white patent leather shoes, matching bloomers and give us a show. We will invite our friends over, snicker and giggle and most importantly, snap lots of pictures to share with the world. You can serve us food and drinks and take care of our every whim because we are so much better than you. So many things you can do for us. Wipe our asses; rub our feet;  paint our toes; clean our houses; pick up the dog poo in the yard; clean the cat litter….. You should just feel honored to have any place in our lives worthless pig.

Second, you can be our personal slave, and by extension, the slave of the real men lucky enough to fuck us. This might mean sucking cock, taking one in your back door pussy, or cleaning out the cum in our lovely holes. Likely all of the above. Let’s be honest. We both know it would be a privilege for you, just like it is for Goddess Levi’s sissy fairy fag, to taste the cum of a real man. Added bonus that you get to be that close to a hot body. It is the only way you can see this fine ass naked. I sure as hell would never let a pathetic loser see me naked. I have standards.

Third, you can spoil us. I mean if you can’t spoil us with your dick, you can at least spoil us with your wallet. Women like Goddess Levi and myself, love spa days, beach trips, designer shoes and handbags, fine jewelry… We should never have to pay for the luxuries in our lives. That’s why we have sissy fag fairies like you. You get the picture. Pampering a Goddess is all the reward you need.

There are many other ways you can be entertainment fodder for Goddesses. Small dick losers, sissy fairy fags, pathetic little babies, twirling mother fuckers…..all make us laugh. And since you can NEVER make us cum, you might as well make us and our friends laugh.

Size Queen Brooklyn: Are You My Stud or My Bitch?

I am a Goddess and you know that. That is why you are reading my blogs, looking at my pictures. And the reason your cock is getting hard. But wait, you may not have a cock, at least not by my standards. I require at least 8 inches of thick solid throbbing working meat to be satisfied.  Anything less is a clit stick to me. And if you have a clit stick and try to call me, you better be prepared to wear panties, or diapers and even prissy little dresses, because you are NOT a MAN in my estimation. I do not fuck anyone who is not all MAN.

If you are not packing the meat I require, that I deserve, then there are a few ways we can still play. You can be my cuckold. My little tiny dick loser who has to fluff the real cock, maybe even guide it into my golden cunt that you can never please. You get to help procure real cock for me. It is an honor and a privilege to provide me with a surrogate cock. You see all those well hung studs at the gym. Bring one home for me to play with and if you do a good job, you get to clean up my cream pie. We both know how good a real man’s cum tastes.

Perhaps I will decide you are better suited to be my sissy. Put your little clitty in panties and dress you up as my life sized dolly. From head to toe you will be feminized because let’s be honest here, what is between your legs is so small it would get lost in boxers. I bet you couldn’t even find it in your tidy whiteys. So really, I am doing you a favor by making you my sissy. You should have been born a girl anyway. As a pretty little girl you can amuse me, entertain me. I can give you a special girly name. I can train you to be a little whore and pimp you out to the real men to be used or keep you all to myself.  So much fun I can have with you as my sissy.  Can dress you, spank you, peg you, humiliate you, exploit you, profit off of you, make you serve and worship me.

I can even make you my adult baby. I mean your pecker is so small it’s infantile. So, diapers are appropriate.  I can put you in a baby bonnet, give you a pacifier, change your diaper, nurse you, punish you when you make a poopy, and most importantly humiliate you. If you have such a small pee pee that it belongs in diapers, my laughter will be heard in the next state and my humiliation tactics will know no bounds.

How we play is all up to what is between your legs.  If you are a real man, then you deserve my pussy and we will fuck like wild animals. But if you are no man, then you get to be my cuckold, my sissy, my adult baby, my slave, my doll, my whore, MY BITCH.

Forced Feminization Phone Sex with Glenda: Grandpa’s Secret

When I travel, my grandpa house sits for me and watches my fur babies. They just love him. So do I. Now, I always thought grandpa was a pretty straight laced guy. You know the kind. Loves beer, Duck Dynasty and football. This last time I traveled, I came home early and got a huge surprise. My burly grandpa, setting on the couch in my clothes with a Pabst Blue Ribbon in his hand. By clothes I mean my pink bra with matching panties and a black garter and thigh highs. When I said hello, grandpa was really embarrassed. Tried to tell me he lost a bet. I explained to him, that although we are family, there are rules in my household like you do not wear my clothes without permission or without consequences. I told grandpa if he was fond of ladies clothing, well he was going to wear them in public all day long.

He tried to argue with me, apologize, say it was just one time. But, I knew this was not true. When I have returned home before I have had my suspicions based on clothes not fitting right. I told him if he could wear my clothes in my house, he could out and about too. I went and got him a blouse, a skirt and a pink bow. Ordered him to put it on.  He kept protesting so I snapped pics of him in my lingerie and said do as I say old man or I send these pics to grandma. He immediately got dressed in my street clothes. Now he didn’t look too hot in them. In fact he looked like a sissy; an out of shape sissy.

I ordered him to take me to the hardware store. I wanted him in my clothes in a manly place. The whole drive he was pleading with me to give up this silly punishment. He was ashamed to enjoy ladies clothing. I told him to embrace his feminine side, to accept the fact that he is a sissy and cross dresser. I reached over and grabbed his crotch and could feel his hard on. I informed him a hard cock on a old fart meant he liked it; that he was enjoying being humiliated. Truckers passed us and honked their horns, waved, some even blew kisses. When we got to Ace Hardware, I instructed him to own it. Walk in chin up, boobs out.

I was so proud of my sissy grandpa. He strutted right in and embraced his femininity.  There were some stares, some snickers, but he never showed embarrassment.  When we got home, I let grandpa jack off on my big tits. He may be a sissy boy now, but he is still a red blooded good old boy who likes big boobs. Grandpa comes over all the time now and we play dress up. I do his hair, his nails, give him boobs and dress him in something pretty. Maybe I can feminize you too?

Tasting the Rainbow

My friends and I decided to attend the Pride parade in our local town; but, we decided to make it more exciting by dressing up. I chose to dress as a male drag queen; and, I wore a dildo just for fun. When we arrived, a gay guy with purple eyelashes and tight shorts approached me. “C’mon, honey, our float is ready!” I laughed but my friends pushed me to follow him. They helped me climb on top of the float, which was tricky with my 7” stilettos and flowing gown. Someone complimented me on my ‘tucking’ abilities and I smiled, waved my hand, and told them that I’d share my trick later. We waved to the crowd and threw out candy, condoms, and cheap plastic jewelry. I felt like a celebrity!
When we got off the float, the same cute guy who had brought me to the float told me to follow him. We went behind one of the large buildings and he pushed me up against the wall. He was lifting up my gown and groping my dildo. I moved away, afraid that he’d figure out it was just a toy. “Oh, you like it the other way, huh?” He bent over and exposed his cute little ass to me; I looked around and didn’t see anyone in the alley, so I pulled out the dildo and tried to shield it with my dress. I spit on the tip of the toy and pressed it between his ass cheeks. He grabbed at a box that was in front of him as I began rocking my hips, pushing further inside of him. He moaned, “Oh, yes, doll. Fuck your little fag.” I was so turned on that the friction from the dildo was going to make me cum. I grabbed his hips and pushed him harder against me until he and I both came. He exhaled, turned around, and said, “Thank you, doll. I will definitely see you around.” He blew me a kiss and left while I tried to absorb what had happened. My friends weren’t going to believe this!

Sissy boy on loan

One of my friends went on an all-paid vacation from her sweet Sissy Boy; and, she asked me to look after him.  I told him that his homework was to memorize all of the songs from Oklahoma!, one of my favorite musicals; then, I told him to meet me at my office.  When he got there, he took off his robe and had done exactly as I asked: he had on a pretty little yellow skirt and a pink top.  I bragged on his wardrobe choices.  Then, I told him to come out on the balcony…this is where he was going to sing his little sissy heart out!  He looked terrified and asked if anyone could see him.  I said, “Of course.  The people who have balconies and even the people below the building.”  I had to coax him, but he relented; I told him that I was going to tape his performance and send it to Mommy.  He cleared his voice and adjusted his hair…and he was ready!  He went out on the balcony and began with the title song; and, before long, he was prancing.  After he had sung the entire track of songs, he started making up his own.  I was so proud and rewarded him by touching his little clitty while telling him that he was such a good sissy, that Mommy was going to be so proud when she saw the video, and that Auntie Monika was so impressed!