Category: Crossdressing Phone Sex

My Own Private Sissy

sissy phone sex analAs a grown ass woman, well special woman, I don’t ask much for Christmas. But this year, I wanted a sissy. My very own sissy I could dress, humiliate, shame and use.  Not sure why. I think because when I was young, being forced to live as a boy, I was not allowed to play with dolls, and sissies are sort of life size dolls, but better because they can do shit for you. My company here has a site sissy and the girls have so much fun taunting and laughing at her;  I decided I wanted one of my very own. The only thing I asked Santa for this year was a sissy. Sure enough, under my tree was a sissy just for me.

I dressed her as a pretty little sissy shemale helper. It was like she was my private Barbie doll. I dressed her from her pretty red undergarments, to her slutty little Santa dress. Even put a wig on her and did her make-up. She was to be my assistant of sorts. We began with her shaving my body. I like to remain hairless from my head to my toes and everywhere in between. She gladly shaved my legs and all my nooks and crannies.

sissy phone sex tranny dommeShe also cleaned my house, made me lunch, cleaned up the dog crap in the yard… I was in heaven.  Why did I not get a sissy sooner? I played with her on that first day to try her out. Tested her cocksucking skills, rim job ability, and of course had to see what kind of ass pounding she  could handle. She struggled with my cock, it is pretty big, but she understands she is here to do whatever I need. She understands my needs vary from being a sissy maid to a sissy sex slave.

Every day she services me in some capacity. From cooking me dinner, to wiping my ass and everything in between . Her ass still needs some working on. It’s so tight. But daily fucking  and dildo play will loosen that backdoor pussy right up. The best part was now I have a live in pretty toy to take care of my sexual needs. If I want my ass licked, or my balls drained, or I need a tight fuck hole, I have one at my immediate disposal.  My house stays clean, and my cock drained. And, I have the gift of laughter right in front of me too. A sissy is the best gift ever. 

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She Found Him In The Attic

 sissy phone sex melindaWe often get together and laugh at what a little dick her husband has. She always said she wouldn’t cheat so when she needs a good fuck we get together and I fuck her with a big fat 9 inch strap on. but when she found him there the attic, all alone, dressed in a pretty pink baby doll dress with plastic panties and a bonnet, rubbing his pitiful excuse for a cock, she couldn’t believe her eyes. Taking in the scene she saw that  he was surrounded by girls clothes, wigs, makeup and nail polish. He admitted that he loved cross dressing and that he often took her sex toys and shoved them up his ass, pretending it was a sweet pussy just like hers. She said he cried when she began to yell out him, furious that she had been faithful despite his little cock when all the time he was a sissy. I felt so bad listening to her and then something snapped and a look came over her face that sent a chill down my spine. She asked if I would help her. If I would be her accomplice and teach him a lesson. She wanted me to invite the biggest dick I knew over to my house, she would bring her husband and the fun would begin. She would make him dress in that pink dress with the plastic panties and bonnet and make him watch me get fucked while she stood next to him and humiliated him. She would show him what a real man, with a real dick does. And then he would put my strap on around my waist so that he could watch me fuck her like I have for months. She wanted him to know who had been keeping her pussy happy all this time. I have to admit I loved fucking her in front of him, stuffing her pussy full of my strap on and making her cum over and over again making her scream and claw my back. Something I knew he could never do for her. From here on out his name is no longer Bret, he will forever be known as Priscilla.

I will own your whole pathetic life!

blackmail phone sexI am not an easy woman to worship but I am well worth the effort. Believe me, you will treasure every moment spent with me, even the painful ones. I can’t wait to make you tell me everything about yourself, even those private thoughts you’ve been keeping secret for years. I will unearth every single skeleton in your closet and once I do pet, your life will be forever changed. I will own you completely then, you will have to do whatever I ask you to do. Unless of course, you want me to expose all of your dirty little secrets. You will be putty in my hands because you know you will lose it all if you are outed. Even though we both know that being outed is exactly what you want most! Are you ready to give up control and belong to a woman like me?

Let Me Give You a Hot Ass Sex Experience in 2015

Happy 2015 bi curious sluts, fags, cross dressers, sissies, panty boys, fellow shemales, strap on whores, queen queers, and back door lovers. I hope you all get all the cock you want in 2015. Look at me? I am all woman with the exception of a nice 10 inch cock. A cock that loves horny boys like you. My goal for this new year is to get even more cock, and pop even more back door pussies. The majority of the men I fuck are utterly clueless of the heat I am packing in my pretty panties. I love surprising straight men.  I know it is risky not giving full disclosure before we get naked, but part of the turn on for me is seeing their reaction. Knowing that a married man would not only cheat on his wife with me, but let me fuck his ass for the first time gets my cock erect. You may tell yourself that you would never let a guy fuck you, but then you have never met a guy quite like me, have you? I’m actually all woman, well except for that pleasant present between my legs.

I think your new year’s resolution needs to be to relax your mind, and try something new. How do you know you wouldn’t like my cock up your tight ass until you try it? Guys want to fuck women in the ass all the time. Men tell their ladies to just relax and try it for they might be pleasantly surprised. Same is true in the reverse. Trust me, every man whose anal cherry I have taken, has come back for more. You will too.

Let a sexy shemale give you your first hot ass sex experience. I am the best of both worlds. Say goodbye to inhibitions, and hello to heightened sexual pleasure in 2015.

Trapped Sissy Fantasies

Do you fantasize about dressing up in women’s clothing?  Good! I can turn you into a sissy faggot unlike no other.  I love beautifying and turning strong manly men into a fucking sissy. I cant wait until I make you  into a slutty bitch.  After I’ve incest sex2dressed you for the part I take you to a hotel room and let the fun begin.  I have just the right situation for you.  Those two men down the hall they are just itching to fuck a sissy faggot  like you. They paid me well  just to let them stick a cock in you. They are going to want some nasty sex and won’t take no for an answer.  I sit back and wait for the fun to begin.  I get off  watching  you suck your own ass juices off their dicks. They plunge in and they stretch out your tiny little hole.  Don’t you worry your pretty little heart.   I’ll take good pictures for a reminder or for future blackmail when you don’t follow my directions.  I love taking control of every situation and this is no exception.  When these men are done I will find a few more to make you a complete making sissy for the night.  I suggest you hurry along and get dressed for your big event as time is short there are horny men outside.  Comb your hair, freshen up your make up, put on some bright red lip stick check your hose for runs and please don’t forget to grab the lube.

Finally the door opens and the fantasies begin. incest sex1

 

Naughty Secretary Phone Sex: Sissy Training Holiday Party

I have a part time office job. I don’t have to work. I don’t even enjoy working, but this office job is unique. I am paid really good money to simply give “dicktation.” I have no real skills. But, when you can deepthroat massive cocks, you find yourself in high demand. So many women just can’t swallow a huge shaft. Since I am a total size queen and won’t get out of bed for less than 8 thick inches, many well hung corporate executives need my special skill set to get through a grueling work week. I have been the big cock blowjob secretary at an all male law office for a few years now. The smallest cock in the firm is 10 inches; so I would work for free, but I am not going to complain about a 6 figure income a year to suck real men off.

Every year they throw a wicked wild holiday party. They hire male strippers, bring in a celebrity chef and bartender for catering, even hire a few pretty whores to help entertain the guests. Besides the whores and myself, it is an all male, all well hung party. No sissies or tiny dick losers allowed. Well this year’s party was the kinkiest ever. Somehow, two tiny dick losers snuck in. I guess they had huge wallets and thought that would make up for having clit sticks. My bosses recognized that I am too hot as were the hired whores to service anyone with less than 8 inches. No amount of money will make me lower my standards.

Being the mean size queen I am, I suggested we sissify the girls who failed to measure up. I love humiliating tiny dick losers, especially ones who do not know their place. The rented whores joined me. We got them all prettied up and made them suck off the male strippers. Dressed them like pretty sissy Santa sluts.  Even had them bend over and take it in the ass by the real men. I  put on my big red strap on and fucked them like the  sissies they were. The strippers enjoyed humiliating  the sissy fairy fags too because they thought they were better than the rest of us simply because they had money. At this office holiday party, big cock was the only thing that mattered. Last year’s party I was sucking big dick and getting fucked. I did enjoy some of the hot hung strippers, but I spent most of the party training the new sissies to suck cock and take it in their back door pussies like good sluts. Even made them  drink cumnog! Got to get sissies hooked on cum early on in their training.

Even though the office Christmas party was different this year, it was still wicked kinky fun. Only thing I enjoy as much as a big hard cock in my holes, is putting tiny dick losers in their place!

Caught Red Handed

Do you like being a sissy boy?  where do you keep that little secret bag of feminine clothes you’ve gathered out of site from everyone?  Well there it is under the bed. Let’s just take a look of what’s inside shall we. Oh what do we have here your grandmothers panties, your wife’s bra, let’s not forget your sisters silky nitey . Quite the sissy faggot are you.  Why don’t sissy phone sexyou take a few moments turn on that cam and model those items for me let me be the judge.  Nice I like that, spin around and let me see a full view.  Now let’s continue going through the sissy faggot bag of yours.  Hmm I see a dildo, butt plug and some lube, I can see where this is going to go.

Lock the doors turn on the cam more I want to see you suck that dildo.  Suck it like you mean it swirl your tongue around it. That’s right just like a good faggot does.  Now while you are sucking that dildo I want you to get on the floor and lube up that butt plug, suction it to the floor and lower that sweet ass on to it. How does that feel, I can see your cock is responding nicely in those granny panties.  It’s ok if you continuing suck to touch your cock, but only through those panties.  Oh yes look at that pre cum ooze. Go head baby beg for it. Beg me to let you come.  sissy phone sex

Queen of the Queers Sissy Fairy Fag Spreading Holiday Cheer and Giggles

I feel sissy, oh so faggy
I feel pansy and dickless and gay
And I pity any fairy who isn’t owned by a Goddess tonight

I feel pretty, oh so pretty
It’s so sissy how pretty I feel
I’m so sissy that I hardly believe that I’m real

See the sissy girl in that mirror there
Who can that fairy fag be
Such a pretty face, such a sissy dress
Such a girly smile, such a faggy me

I feel stunning and entrancing
Feel like prancing and dancing for joy
For I’m owned by my pretty, wonderful Queen

Look at Goddess Levi’s precious little Sissy Fairy Fag? Pathetic beyond words, right?  As much as I want to shame this silly dickless little girl, I have to give her some props for her charitable heart. She clearly is ALL girl. She spread Christmas joy to the elderly recently with little holiday goody bags. She was Santa’s Fairy elf.  I do love a sissy with a heart. I mean she can’t give back in the sack right? I’m sure Santa has not even seen a package as small as hers, so it is a good thing it’s hidden under all her ruffles and frills.

Personally, I think she is the Queen of Sissy Fairy Fags. My sissies have someone to aspire to be. Goddess Levi’s Sissy Fairy Fag is so pretty in her lace and frills. I can just hear the laughter of the men and women in that old folks home as she skipped and pranced around spreading holiday joy. We all know she spread laughter and pity too. And, I bet she spread her little back door pussy too. She is a total whore, a real sissy slut.

Join me in making fun of the Queen Queer. Trust me nothing YOU do could be more sissy and faggy than what she does. Dresses up like Shirley Temple, sings little ditties, skips and prances and preens, sits in poopy panties and all in public for our amusement. Bet you don’t feel so faggy now for sucking cock and taking a load of jizz up your ass do you? You will never be as pathetic nor as queer as Sissy Fair Fag.

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.