Tag: Crossdressing Phone Sex

Biggest cum shot on my uncle

When you catch your uncle getting the Biggest cum shot you have ever seen on his face you can’t look away. My uncle was on his knees wearing some panties and dressed up like a sissy hoe. It made me think about my younger brother and how I caught him in panties. I was watching my uncle suck the dick so much that I didn’t notice he was sucking on my daddy’s cock. Daddy was fucking his mouth so hard he was choking and gagging. I watched as daddy pushed my uncle down and lifted his legs in the air pushing his panties to the side. It made me think of how daddy fucks me and i started playing with my cunty.

 

Biggest cum shot

I saw daddy push his hard daddy meat deep inside my uncle’s ass. He fucked him hard as i finger fucked my cunty. He gave him some Hardcore ass fucking and I couldn’t help but cum so hard on my fingers. I licked my fingers as I watched my daddy pull his hard dick out and spray my uncle all over his body.

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. 

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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.

I told Daddy about sissy brother wearing my panties and he got his punishment

I know I am daddy’s bratty slut but when I found my younger brother wearing my panties and bra I had to tell daddy. Daddy had a stern look on his face and spoke to my brother alone, before bringing me into the room. When I walked in my brother still had my bra on but no longer was wearing my panties. His ass was red where had been spanked and my daddy had his hard meat out. Daddy let me know how my brother had gotten spanked for being a sissy boy and putting my panties on. He also had to get daddies meat hard like little girls do since he wanted to pretend to be one. But daddy could finish with my brother yet not until he saw for himself like a cuckold slut how little sluts make daddy cum. I knew that meant he was going to use my little hole. He slid my panties off just like he did the ones my brother was wearing and he bent me over. I was a good girl so I didn’t get a spanking. I got yummy daddy licking on my clitty, that always gets my hole wet and ready to fit on daddies meat. Before papa pushed his hard cock inside me he had my sissy brother get close and look so he knew what was going to happen to him next. Daddy fucked my Young bald pussy hard over and over making sure my sissy brother watched every stroke. When he finally started pumping his daddy semen inside me he looked at my brother and made it clear how he was going to be cleaning up the mess he made dad make.

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