Tag: Crossdressing Phone Sex

Ride with me

hardcore ass fuckingThis blog is only for men who need a hardcore ass fucking. I need you to ride with me into the sissy whore hall of shame.  Pain freaks come in all shapes and sizes. Just like your cock does. Small dicked men who dress up as biker bitches and sit bitch for some motherfucking Juicy ass cock. You want to dress up in some sissy panties and become a cum dump for some big motherfucking hanging bull dick? Ride baby, come on and swing that pretty little ladyboy ass over my hog and become my piggy sissy. It isn’t often I get a real femmed out flamer who loves to show off that small little clitty and dare anyone to say he is a dude. You know you’re a sissy la-la. You know you only dreams and desires revolve around cock sucking and getting fucked for a nasty trashy mistress. Your the type that craves hot ass sex that fills you with multiple loads of jizz. A real pass around sissy hoe. Let me bring you to the south side and hook up with some of my homies who think a hole is a hole. And that is all you are. A hole to be filled and stretched out around some dark skinned man meat. I don’t blame you for your short cummings or deep inbred cock feigning. I am as big of a whore as you are. You are working with what you have. A tight man pussy and a sweet clitty that bounces around so nice while you’re on top milking my Bros’ ding a lings. Ride that dick for me while i lick his balls and squeeze you little clit stick. Shoot all over your belly you trashy fucking sissy cunt. Let the real man spurt his load inside you anal canal. You know your a darling sissy phone sex bitch who loves this shit!

Crossdressing Phone Sex Party

crossdressing phone sex

Getting calls from crossdressing phone sex lovers like you always really makes me happy. It’s SO much fun to talk about girlie things with someone who enjoys them just as much as I do. I’d LOVE for us to talk about getting all dressed up together and then going out clubbing. Which one of us do you think would get hit on first? We will both look really slutty, so it’s anybody’s guess. I can’t believe you haven’t found a friend like me to fill that role in your life. Maybe if we’re lucky, we can even pick up a guy to share together.

I know that not all crossdressers are into that, but if you are, keep on reading. I want us to scout out guys together and then we’ll start working on them. If you promise a drunk guy a blow job from two women, he’s not going to look THAT closely to make sure you’re really a woman. I find that SO exciting. We’ll be sticking it to the man, and we’ll have a delicious cock to suck. If you’re interested in crossdressing fantasies, get on the phone and give me a call. We’ll make it exactly what you need!

Daddy In Pantyhose With our Furry Friend

Pantyhose Fetish Phone Sex

I watched as our furry friend licked on his asshole, daddy was dressed in my panty hose and stockings with a pink sheer teddy. It surprised me to know he had a pantyhose fetish, but I knew had had been letting our furry friends lick him up. I had found the peanut butter was being used up more often than before.  I didn’t make any noise I just watched as he rubbed the pantyhose and stroked his cock. Our pal’s tongue is wide, so every inch of his asshole was getting licked, then I saw his big lipstick knot cock out and ready. Before long he was mounting him and sticking his lipstick cock into his man pussy. He humped his ass while growling I knew they both were enjoying it. Our furry pal didn’t stop until I saw he started filling him up, that is when I saw my daddy cum all on his hands and down his pantyhose. I now know daddy loves crossdressing and getting fucked by our furry friends.  

Sissy Slut Mistress

sissy phone sexWhen me and your wife show up, you need to be on your knees, wearing the sissy faggot clothes I brought for you. Heels and all. I don’t care if she doesn’t know yet because she’s going to know tonight. You’re expected to be on your best behavior as well. You don’t want me telling her that you’ve been taking ten inch cocks into you sissy pussy while you rub your hard clitty do you? Your fag cock is too small to even count as a cock so you better be rubbing on it right now as I speak to you.

Your gorgeous wife and I walk in while dressed in skin tight clothing and high heels, when she stumbles upon you she’s so shocked to see you dressed up in those sissy clothes, she laugh and giggles while pointing you out to me. I laugh with her while you’re kneeling on the ground I whisper to your wife, I pull a strap on out of my over night bag and tell her to put it on. the rest of the night was spent spreading your ass cheeks and making you our sissy faggot slut, and me making your wife cum over and over again right in front of you!

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.

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.

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! 

Husbands Sissy Closet : Sissy Phone Sex

sissy phone sex

 

Mistress phone sex

S is for Sissy phone sex. My husband loves being my bitch in sissy drag. He wasn’t always my sissy bitch. It took years to get him to this level of sissy play. His small cock did make it easier to buy him panties and nylons though. No one questioned when we went to electrolysis, he was never very hairy anyways. I knew the receptionist had seen many cross-dressing fairies before. Tights garter belts and crotchless panties were added as gifts from me and who can deny making their clit stick husband pretty in a little lip gloss and mascara. Now, look at us. My fairy faggot husband has a closet that mirrors my own and an outfit for any day of the week if we choose. I have a matching sissy closet downstairs in the sissy training play room I use for my useless cocked men who need sissy attention as well. I need to say this though. My husband doesn’t just look like a sissy fag in his ruffles and petticoats, he is very much immersed in the role of cuckold sissy. His cock taking abilities are superior and I am happy to share a cock over 8 inches with him any day. It takes time, discreetness and dedication to a Mistress to be on his level. Come out, come out my crossdressing little dicked men! Time to play with Mistress Brooklyn!

Undress me with your mind

Cock sucking phone sex Don’t you think you’ve stared at my cock long enough yet? I think those lips of yours would look amazing wrapped around it on a cock sucking phone sex call, don’t you? Oh, don’t even try to act all shy now. We both know you have been staring at my pictures and eyeing up my cock for a while. You’re wondering what it would be like to drop down to your knees and slip this amazing hard cock right pass those trembling lips of yours. I’ll start out with telling you all about what sexy number I’m wearing. Teasing you with the red-hot details. I know you want me to be naked, but I’m a girly, girl and love pretty things. I am one hot tranny that loves to dress up sexy. I am going to have on some pretty panties. Something silky that gets my nipples hard from rubbing against them. Yes, I want you to be licking your lips at that image of my sexy body as I slowly undress it for you. You got to work to get to this cock. I want to make sure you’re really ready to suck it down. I’ll have your mouth nice, wet and watering as you watch this cock dancing around your lips. Come to me, lick those lips and open up for my T-girl cock, baby.Shemale phone sex