Category: Crossdressing Phone Sex

Pantyboy Phone Sex with a Sexy Shemale Who Loves Femboys

panty boy phone sexThere is no shame in panty boy phone sex. If anyone knows how to make you a sexy femboy, it is a sexy shemale. I have been playing dress up for ions. Ever since I was a little schoolboy, I had a fascination for my mom’s sexy undergarments. She had the sexiest things too. Corsets, garter belts, stockings, teddies and babydoll nighties. I am sure she wore the items for my father. I wore them for me. I loved the way I looked in her sexiest items. I loved the way they felt on my body too. So, there is no shame if you play dress up with mommy’s things, or even your wife’s sexiest items. I have been there and now I am a sexy shemale phone sex slut. I have a friend who is a femboy. He is married, but every time they visit me, he excuses himself to the bathroom, but he plays with my lingerie instead. In the beginning he thought I did not know. I confronted him once, and he spilled the beans. He told me he loves panties, bras and all sexy under things women wear. Now, he comes over once a week without his wife, so I can dress him. I mean look at me. I bet you would not know that I was a tranny if you saw me. I like to dress too. My hair is real, my body is feminine, and I love to help femboys look their best too. I take my friend shopping for girl clothes, and he has a closest in my house for all his pretty things now. We pretend we are just two normal girls trying on different things and supporting each other’s wardrobe choices. If crossdressing phone sex is what you need, I am here for you like I am there for my friend. Sometimes, men just need to explore their fem side in a safe environment with someone who understands.

Young bald pussy got finger fucked watching furry friend fucking

I didn’t know I was going to be playing with my Young bald pussy when I caught my youngest brother fucking ruffus our furry friend. He was dressed in mommy’s pretty lingerie, stockings and had her panties to the side, while ruffus was behind him. I could see that ruffus was pushing his big lipstick cock inside his boypussy. My youngest brother was bucking back on him while pulling on his little dicky. It was small like a big clitty, but he was loving getting fucked by our man’s best friend. I guess they were best friends for a reason. I couldn’t look away and seeing how much they both were enjoying fucking each other, it started to turn me on. I slid my fingers to my cunt and continued to watch. With every pump of puppycock my brother was getting, he moaned louder. 

Young bald pussy

Then ruffus howled out and my brother moaned that he could feel his cock knotting up and filling him up with his semen. When I look my youngest brother hand creamed his hand. I just left to finish my cunt off before he caught me watching.

Stocking Fetish Phone Sex for Sissy Boys and Crossdressers

stocking fetish phone sexDo you enjoy stocking fetish phone sex? I am old school when it comes to my lingerie. I love corsets, stockings and garter belts. Hell, I still wear pantyhose. I love the feel of stockings and pantyhose on my legs. I have a fit body that I am proud of. I have worked hard to have this body. I like to be in shape because many of my lovers are fit, strong, burly black men. I need to keep up! Anyway, sometimes I meet a sissy or a crossdresser who falls in love with my lingerie. I will not fuck a sissy or a crossdresser unless I am donning a strapon, LOL. But I will dress one. I will encourage a sissy or crossdresser to wear lingerie as much as possible. Sissy phone sex is one of the services I offer. I had a random encounter with a sissy at a local café over the weekend. A younger guy, college boy who complimented my style. He said no one his age ever wears pantyhose. I pulled up my dress a little to show him I was wearing a garter belt and stockings and his expression told me all I needed to know. I asked him if he wanted to try on some of my sexy lingerie. He was working, but I live around the block from the café. Once he was off work, he came over. Handsome lad with a naturally feminine body. I could see why he liked women’s lingerie. He confessed that he played dress up in his mother’s sexy things when he was a schoolboy. Once his father found out, however, he got beaten. After that he was afraid to touch anything feminine again. I gave him some of my old garter belts, and several pairs of sexy underwear and bras too. I have plenty of sexy lingerie. So much I can clothe me and any crossdressing phone sex boy every day of the year. I live in sexy lingerie. This boy works a block from where I live, so I am taking him under my wing. He no longer lives at home, so he is free to wear whatever he wants. I can let you play in my closet too if you want to wear something pretty.

Crossdressing Phone Sex is where a sissy uncle is on

I found out my oldest uncle was on Crossdressing Phone Sex when I walked in on him on the phone wearing a nighty and looking like a sissy man. When he saw me, he got on his knees and begged me not to tell anyone. I figured I could use that to blackmail him. I wanted a car, and he was going to get it for me. I told him to show me what he has been doing or I would tell. That is when he pulled out a strap-on and told me I would have to put it on. After I put it on my uncle spread his ass cheeks and slit his open booty hole on the strap.

Crossdressing Phone Sex

He bounced his ass harder than I would on that dildo cock. My uncle then started to whistle; I didn’t know why we were the only ones home. But as I looked up, our big furry friend came running in. our family pet was aware and just laid belly up in front of unc. Uncle took his mouth and sucked all of roary’s cock and balls in his mouth and he didnt stop fucking the strap either. He went hard and fast and I almost stumbled back. Roary just groaned as unc sucked his gooey lipstick cock. Finally, he busted in uncs mouth and i could see unc spraying Biggest cum shot of jizz on the floor. After he was done, I told my uncle he needed to get me a car or I would tell everyone his secret.

Sissy Training Phone Sex op turns friends dad into a sissy

Sissy Training Phone SexI went over to my friend’s house only to be greeted by her daddy! He begged me to put a strap on and fuck him.. He literally admitted to being subscribed to my OnlyFans. He witnessed his daughter sucking on the lips of my pussy after I fucked myself with a dildo.. The pervert can’t shake the thought. He knows about my day job as a Sissy Training Phone Sex operator and said he also checked out my profile.. He wants me to slut him out and turn him into a sissy; then reveal his new look to his daughter.. Of course, I didn’t give up the offer.. I went into the trunk of my car and grabbed the duffle bag with all my toys and costumes.. Lucky for him, I had my makeup bag tucked away in my purse. A remarkable red fit his fair skin and fine lips, so well.. I waxed his beard and even put false lashes on him.. He plans on going to work tomorrow and letting his coworkers know that this is only the start of his transition.. I am going to teach him to love himself for who he is and show off his goods to the entire world.. After he gets his tits done he is going to start making money off his Tranny porn pictures.. We have already started a portfolio! He has a really nice thick cock with a perfect cherry bulbed shaft.. I gave him a hand-job because he got so fucking hard looking at the reflection of himself in the mirror.  Then I smeared his cum all over my 10 inch silicone dildo and had him blow me.. His stained red lips didn’t smear one bit. I made sure to put the 24hr outlast on him so his makeup would still be set for tomorrow.. As for his hair a nice sandy blonde with almond highlights brings his ocean blue eyes out perfectly.. I could totally tell his breast implants are going to come out so well.. he has got the perfect nipples for them. His Big tit photos alone will be enough to show him his worth. 

Daughter Blackmails Sissy Father

Blackmail Phone Sex

You didn’t think I would find you, did you Daddy? I knew there was something wrong when my panties and stockings were going missing. So, I hid under your bed to see what it is that you’re getting into. I can’t believe you’re a full-blown sissy! You’ve been sashaying around in my panties and stockings, picking up random men and fucking them. I heard you talking on the phone with one of your hookups about how you want to get railed by his big fat black cock. I bet Mom has no idea how much of a cock whore you really are. It’s a good thing I have the whole thing recorded on my phone.

Get off your knees, Daddy, or you can stay there if you like. I’m not going to tell Mom about your feminization fetish. I do, however, need you to give me something in return. I need you to come over here and eat my pussy. That’s right! You can’t steal my panties and get away with it. Lick my pussy now or I’ll expose your faggot ways!

Sissy Forced Hypnosis

Erotic Hypnosis Phone Sex

Relax your eyes and give up your mind to my hypnosis. I’m going to turn you from a masculine man into a sexy, feminine sissy. Think that’s impossible? Well, you don’t have a choice. I have your mind wrapped around my finger and I’m going to program you however I like. From now on, you love wearing girly clothes and the color pink. Your closet will be filled with dresses, skirts and tight little tops. You’ll wear loafers for work if need be, but you feel much more comfortable slipping your feet into a pair of high heels. No flat shoes for a girl like you. You’ll be so desperate for women’s clothing that you’ll steal your wife’s favorite dresses and heels straight from her closet.

Did I think I would forget your love of cock? Oh, you don’t like cock? Well, you do now. You love having cock in your mouth. You want it in your fuck hole. You can’t get enough of it. You love being a little cock slut. I can see your little clit getting hard at the thought of it. I can’t believe you just turned a masculine man into a cock-loving sissy slut!

He is going to start a Tranny porn pictures catalog

PhonesexMy roommates Elastrator finally came in the mail.. I had no idea he had even purchased one, I came home to him howling in agony! I was a bit confused, uncertain what the matter was. He was wicked shy and not willing to tell me… Watching him waddle around for breakfast the following morning was a dead giveaway that something was wrong down there. While he was showering I snuck in the bathroom to take a peek.. I could hear him oohing and owing as he rubbed his cock with a luffa..

To my surprise once the suds were removed he had the smallest cock I had ever seen. Then I noticed a big black ball, I was totally spooked! Come to find out he had a ring at the base and was prepping for a home based ball removal. I giggled, and he heard me… He immediately placed his hands over his peewee.. and asked that I leave.. I hid in his closet to find that there were panties I had been missing hanging everywhere. He had been airdrying to avoid getting caught! As soon as he walked in the room and put the latch on I came out of the closet wearing my favorite panties that I missed so very dearly..

I punished him for being a thief. It was clear he no longer had any interest in being a male he wanted to make it impossible for him to ever experience cumming ever again! He told me what was supposed to just be a joke on a Phonesex line with a MILF turned into the ring from the release of the elastrator being stuck around his cock.. There was no way he could have removed it on his own and was ashamed to go to the emergency room! hehe asked if I would be willing to help him. Of course after seeing he had been digging though my hamper there was no way in hell I would be willing to remove that thing! He deserved it.. His balls were black within the next 24 hours they would be completely dead and within 3 weeks they would fall off..

He was already a step closer to victory. Finally embracing the who he wants to be! The only thing I was going to help him with was shop for his own panties.. I had him put on a pair of my leggings and even made it appear as if he had a camel toe. From how much his balls were sweating it looked like he had a Wet bald pussy down there. I walked him into Victoria’s secrets and wound up picking him up a hot swimsuit for him to wear next month.. When we got home he stood in front of the mirror and held it up in front of him.. I could see in his eyes he was pleased, he couldn’t wait and he was so happy that someone was willing to accept the woman he’s been hiding in the closet since grade school.. Come to find out my panties weren’t the first he had stolen from his mom and sisters as well as the neighbors clothesline. This is only the beginning of his new life, we will be sending his Tranny porn pictures to all sorts of porn and modeling sites.

Young bald pussy is spoiled and tells daddy everything

Being daddy’s only Young bald pussy, I always make sure daddy knows what is going on. When I walked in on my younger brother sucking off my older brother while wearing lingerie, I had to tell daddy. Daddy always felt my youngest brother was a sissy bitch. He wants alpha males like him and my oldest brother. So when he found out he brought us to his room. He wanted to show us what an alpha male is supposed to do. He humiliated my brother by calling him names and right away making him suck on his daddy meat. We know when we misbehave, he will make us suck his cock. Then he bent him over and made us watch as he gave him some Hardcore ass fucking. He was going to show him what happens if you are not alpha. He fucked him hard and made him ask daddy to be a girl and not a boy so he wouldn’t have to be alpha. My poor sissy brother squealed like a pig as daddy fucked him hard. Finally, when daddy filled my sissy brother’s ass up he told him he earned his way to be a bitch and will have to dress like one and be one for daddy.

Young bald pussy

Cock Control with BBC for all Types

Cock Control

Alanza is taking Cock Control of a small white cock! Be very careful if you come to play, because you will be giving me the power to undercover your true nature. I have A sort of radar for people who need some BBC training. 

Me and my stallion BBC daddy love forcing sluts, men, and sissies to take cock. I take great pleasure in seducing any and all whores on a massive Black dick!  Being the demonic dominatrix that I am I can convert good girls into all-out cum whores! Call it a skill, if you will. Creating cum dumpsters whenever I need raw entertainment. I love seeing the look of fear on an innocent girl’s face when she realizes she’s been turned out on black cock. 

When I see an under cover sissy who is trying to blend in as a normal guy I can almost instantly tell that they will submit to my dark plans! And that is to make them worship my black daddys monstrous. There is no stopping this whore from getting what she wants motherfuckers! This is my world, and you will be my cum guzzle slut. I take so much pride in seeing my mandingo turn sissies and whores into good little fuck toys for us to play with.

And even some straight men have the urge to suck on a big black dick. I am not one to judge if you just want to worship a BBC with your mouth once in a while!

For all types of Black Cock Phone Sex this bitch knows what you need!