Category Archive: Crossdressing Phone Sex

I Like Sissy Phone Sex Cross dressers

sissy phone sexI love sissy phone sex. Sissies are the same breed as cuckolds. My half-brother is a cross dresser. He was always getting in trouble when we were younger because he would steal our mother’s clothing. My mom had to enforce a rule of no borrowing clothes without permission. I stole my mother’s clothes too but I never stretched them out. I rarely see my brother theses days, but he is here for an impromptu visit. He had a date last night, so my husband and I had a date night too. I was shocked when my husband took me out to a fancy restaurant in downtown Chicago and I saw a woman in a pink floral cocktail dress from Betsy Johnson. It was just like the one I had bought two days ago. Her dresses are expensive and limited, so it was odd to spot another woman with the same dress so close to when I bought mine. I tapped the lady on the shoulder to compliment her dress and the woman was my brother in drag. It was my dress. He was on a date with a man. I doubted the man knew his date had a cock and balls. My brother makes a pretty girl. I am almost jealous sometimes. I just apologized for interrupting their dinner and my husband and I ate and left, ignoring them. I got my revenge when he came home. I made him my sissy. I made him take off the dress and put on one of my pink nighties. I painted his toes and nails hot pink to match.  I broke out the strap on I use with my husband and fucked my brother’s sissy ass. Sissy boys love it up the ass, right? His ass was tight for a sissy. I was trying to punish him, shame him, but he had a hard little dick.  He liked the ass pounding he was getting. While I fucked his ass, I milked his cock. I love milking sissies. Maybe my brother did not learn his lesson, but we had fun. I forgot how much I love crossdressing phone sex calls and pegging sissy asses.

Hot Squirting Pussy For Sissy Bois!

hot squirting pussyTell me how much you love seeing my delicious little Hot squirting pussy all stretched out in front of you. Heard you wanted to join my whores, well you got to learn to be a bad bitch like me! I love that I keep your little clitty locked up in a cold, steel chastity cage. It fits perfectly under those pretty lacy panties. You wore your mini-skirt and my favorite stockings today; what a good girl. Mamacita Alanza is gonna reward you, perrita. Mirame, look at me. You see this Torro cock, right here? This big Alpha bull cock is going to fuck me right in my tight fucking twat! I’m dripping at the thought But you need some cock training, don’t you? Open real wide, say AH! Good girl! Take that BBC monster man meat and swallow it whole! I need you to choke on that beast of a  BBC baby boi! Take it all the way down, you want to be a bad bitch then do as I say! I will make you the high rolling paid slut you were always meant to be! Get him so hard! Now watch me bounce and grind all over him. I know you wish you could play with your clitty, but sissy whores don’t get to cum unless I decide you do. Got it, bitch? You are my sissy phone sex little bad bitch and I’m going to put you in your place! sissy phone sex

Making You A Sissy Princess!

Sissy Phone SexYou want to become a sexy sissy princess don’t you? However you’re not quite hitting the mark, clothes never seem to fit right, makeup is a mess and caked on. Poor you, you have no proper guidance. Too embarrassed to show off cause you need help. Come to me I’ll make you a pretty, proper little sissy princess. Let’s get you in the proper attire, nylons, silks and sparkles. Your new look is going to make any man hard and earn you the big dick that a real princess deserves. I know how to make that happen, as a princess never settle for average if he isn’t packing we’ll send him home. When you look like a princess, you’ll learn there is always a bigger dick around the corner. So be prepared for what doors this transformation is going to open for you. Just come to my boutique of proper sissification and ask for the princess package!

I love your dress

crossdressing phone sex

Crossdressing phone sex holds a special place in my heart. There is something sexy about a man who is trying to find himself as he dresses in a pretty bra and panties, or maybe stockings and heels. Usually these are stolen from a female in their lives such as a sister, mom or wife. They try to only dress when they know that they will be alone, admiring their body in the mirror as they turn back and forth. Maybe they even go so far as to try to apply some basic makeup like mascara and some lipstick. Not all of them want to be fucked by another man but there are some who will continue down the road of humiliation and sissification. They will start to get more bold with when they are dressing, the excitement of knowing that they could be caught egging them on. Then the day that someone comes in they look scared and surprised but deep down had wanted to be discovered all along. They want the punishment and the anger from that loved one so that they can use that to fuel their depravity. The others are confused and looking for some re-assurance that it’s ok for them to wear pretty things too. To have a friend or loved one take them by the hand and show how to fit items, what to shop for, help apply makeup and maybe even do their hair. No matter which side of the road that you are on I am looking for you and can help with either destination!!

Small cocks need not apply

small cock humiliation phone sex

I don’t get very many calls for it but I enjoy small cock humiliation phone sex. I have fun rounding up some girlfriends and we all laugh and point at your tiny cock and ask how you could possibly fuck anyone with a cock so small. I would allow you into my bedroom but only to prepare my pussy for a real cock to use. You would sit on the floor or a chair with your tiny cock in a cage and would not be able to touch it unless I allow you to. Once my pussy has been satisfied I will call you over to clean his cum from my cunt. You will moan as your tongue comes into contact with my gooey center and continue to lick until there is no baby gravy left. If I feel that a good job has been done then I may let your mini meat rocket out so you can dribble into your hand and then clean it up. If you don’t do a good job then I will keep you in that cage for a month with no relief. Real men are meant to wear the pants and since you have that pathetic excuse for a cock you are no real man. You are a pretty boy with an overgrown clittie that will now be kept in panties and a skirt so you no longer are confused about being male.

Boss Bitches For Your Hardcore Ass Fucking

Hardcore Ass fucking

Who is a sissy cock sucking faggot who needs Hardcore ass fucking? You are! Meet Harley! Once you meet her you will never go back! Mistress Harley is the Hardcore Bitch to put you in your place. I am proud to welcome her to our Dominatrix family! You will be worshiping her  and submitting on a whole new level. Feet worship, big black strap-on worship and cum eating even! Women like us know how to please that submissive side of you. Look at her body, you will be begging to slurp hot creamy cum loads of other men out of her pussy! That is if she lets you. See, you may not know what you have gotten yourself into. But I know you will be enamored and completely under bad ass bitch Harleys spell.  Even if you only had fantasies of serving a hot female, cum and find you a new kinky side of you and a new sexy Domme bitch to train your sissy faggot ass!  Black cock lovers, feet men and crossdressers beware you will have a new A -dick-ion. Don’t be shy little slut, Mistress phone sex is where you can let go of all your manly cares and be the sissy faggot with your ass fucked the way it should be!

mistress phone sex

Mature Phone Sex Size Queen

mature phone sexI am a beautiful mature phone sex size queen. I know my worth.  So many men do not understand that they lack what I need. However, a few do know their rightful place with me like my husband and a few callers. Some tiny dick losers, however, think they have what I need with a 4-inch nub. Men like that need to learn a lesson or two from some of my phone pets, or even my husband. If you have a small weenie, clit stick, pin dick or a limp dick, you only have two roles in my life. You can be my cuckold or my sissy. My husband is my cuckold. I love sissy phone sex too. Sissies are highly entertaining. There are many ways to entertain and amuse a Goddess like me if you are a sissy. You can dress up, prance, preen and twirl for me.  If you fight dressing for me, I am not against forced feminization. I will put you in a pink frilly outfit, white patent leather shoes, matching bloomers and force you to perform for me while I record your humiliation. I will invite a few sexy friends over to snicker and giggle at you too. You can serve us food and drinks. You can paint our toes and nails. Hell, you can clean my house. You should just feel honored to be in my presence. If you choose to be my cuckold instead of my sissy, that means you will be sucking cock, taking cock in your back door pussy, and cleaning out the biggest cum shot in my pussy. Again, you should feel grateful I let you anywhere near my hot holes. It is a privilege to clean me up and it is an honor to taste the cum of a real man. There are ways you can still be in my life if you lack the cock I am worthy of having inside me.  Small dick losers, sissies and, cock sucking fags can never make me cum, so you might as well make yourselves useful somehow. So, are you my sissy or my cuckold?

Princess Phone Sex Mommy Rita

I’m mommy Rita and I love being a nurturing mommy for sissy sluts. I have a couple of pageant slut daughters and a young sissy son. We are always playing pageant with naughty boys that my girls love assisting in sissifying them. I have boyfriends that come by and love to help me with my sissy training as much as they like to assist me with the little pageant whores lessons in pleasing dick. If you need some training in being a cock sucker then we can work on you with that. Maybe you are already a naughty panty wearing pervert and just want to jerk off and watch the pageant whores perform for you. They always need training for their next pageant. My son really needs to have his little tight bum hole trained as well. I bet it would be fun if you wanted to play priest and try converting my deviant filthy family into the purity of your religion. I bet, however you could not hold back on your pervy desires when you see all three of them in their pageant wears.

Princess Phone Sex

Sissy Phone Sex Sluts Welcome

Sissy Phone Sex

That’s right all sissy phone sex sluts are welcome to my sexy domination! I was at the farmers market and saw the most pretty female trying to be a man. What I mean was her face looked like an angel and she clearly didn’t belong in men’s clothing or trying to be masculine. And no this wasn’t just a gay boy, this was clearly a male species stuck in a body and life they did not want.  A wife and brats tagged along as he carried fruits and vegetables and muttered yes dear. His gaze would go to the big burly farmers unloading trucks. He was in need and I knew it. I got close and purposefully bumped into him. I smiled as he was so sweet and apologizing. My eyes caught his as his little family left him behind. 

“You should be only sorry that you are not on your knees in pretty clothes sucking that farm hand off for me.” My words stunned him, but he was almost hypnotized by my voice. “Is your clitty hard? If so here’s my number.”  No one paid attention to us as i passed him a card and loudly proclaimed that I could help him redecorate. I would be redecorating  his life privately for sure. 

It took two days for my new sissy slut to call me for an impromptu Phone sex chat of sorts. He was miserable and perked right up at me telling him I had a black cock appointment. I offered the address and took his male clothing size. I had just the perfect sissy slut outfit for the first sissy lessons with me and a black dick! 

Pantyhose Fetish Phone Sex With Brooklyn

Pantyhose Fetish Phone sexPantyhose Fetish Phone sex s one of the most erotic for me. I love the way nylons feel against my skin making my long legs shimmer. I have so many pairs. My favorites are the thigh highs that give me an extra sexy look when my dress is short and play peek a boo when I walk or bend over. I enjoy a man who masturbates with my dirty pantyhose, and stocking. I know that I love to slip my finger down while no wearing any panties and play with my pretty pussy under my pantyhose. Are you a panty and hose wearing man. I think that is sexy as fuck honestly. The way a cock looks all mushed up in the tightest silkiest pair! My neighbor loves to buy my used stocking and stinky worn for three days pantyhose to jack his cock off. He buys them and then sends me pictures of himself in them and his cum stains. Today he sent me a message asking if he can have a pair that had large cum stains from my husband. Little does he know the cum stains will be from another man. I wish I could tell him that my own submissive cuck husband enjoys the same things as he does. But We have to keep appearances…

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