Tag: Crossdressing Phone Sex

Shopping and Crossdressing with Lacey

crossdressing phone sex

Have you ever called anyone for crossdressing phone sex? If not, you must be thinking about it because why else would you be here? I get it. It’s fun to dress up in women’s clothing and prance around. But first, you have to get that clothing. And sure, you could order it online, but that’s no fun. You run the risk of it not fitting properly, first of all. And second, I love sending wannabe crossdressers into a store so they can ask a salesgirl for help picking something out. They won’t steer you wrong and they’ll make sure you pick out something that makes you look amazing.

What color do you think would be best for you? I think you should wear a color that makes you stand out so that more people will see how great you look. But if you absolutely can’t decide, or if you want to blend in a little bit the first time, go with black. Nobody looks bad in black. Oh, and make sure you don’t forget the shoes and makeup. You can just stop by a makeup shop once you’re done with your clothing. Are you ready to look incredibly sexy?

Brittany the Baby Sissy

Adult Baby Phone sex

I just had the sweetest little baby! Her name is Britney and like most sissies she has a kinky little fetish that involves wearing diapers and being carried around like a baby. Britney is a good girl but sometimes she gets very very naughty and requires a spanking! When Brit Brat gets out of hand, we bend her over our knees and spank her little booty! Her clit drips all over our laps but we love it! My favorite thing about our little white sissy is how and she is able to entertain me and the horny friends that I may bring around. Just about an hour ago, Britney was being held down by my 6-foot Amazonian neighbor while her daughter fingered her tight punani. Britney’s clits was dripping with passion as she got filled with dainty little ladyfingers. My neighbor’s daughter got so excited that she began to fist Britney’s little man purse until it exploded all over the sheets! We sent Brittany home limping and dripping and she doesn’t get more until mama says so. I miss her already and I can tell that I am going to enjoy this little baby sissy and all of her nasty little kinks. I hope Brit Brat is willing to take my thick heavy strap-on when she comes to see me again..

Hot Ass Sex with My Sissy Pal Rachel

hot ass sexI am not the only one who likes to have hot ass sex. My sissy gal pal Rachel loves to get big black cocks up her pretty back door pussy. She was born Richard, but she transformed to Rachel in the past year. We share a party lifestyle, a love for pantyhose and pretty lingerie, and of course we have a shared love for big black dicks. Rachel was born for BBC. Her first experience was not necessarily consensual when she was just a schoolboy, but she has grown to realize that with an itty bitty clitty her options are slim. Women do not want a man with a small dick. And they do not want a man who likes to wear their pantyhose and fuck their asses with their dildos either. Rachel is very self-aware for a sissy. I think she has always known she was meant to be a little bottom bitch for black men. She had a hot fuck date the other night and got all dolled up. Look how pretty my sissy friend looks! She did her own make-up and dressed herself for her booty call with big black Ben. I am not her sissy phone sex trainer. I do not think she needs one. I am just like a BFF. We talk about big black cock, clothes, taboo experiences and get high together. Where was she when I was a young girl watching my mother get high and fuck my brother. If we had grown up together, we would both be bigger taboo freaks than we already are because we would have supported and encouraged one another. Rachel is the perfect Thelma to my Louise. Together we talk about some extreme and taboo things. The kind of things we cannot just tell anyone. We are both submissive whores and slaves to those big black cocks and to what ever gets us high.

sissy 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.