Tag: Crossdressing Phone Sex

Forced Feminization Phone Sex with Glenda: Grandpa’s Secret

When I travel, my grandpa house sits for me and watches my fur babies. They just love him. So do I. Now, I always thought grandpa was a pretty straight laced guy. You know the kind. Loves beer, Duck Dynasty and football. This last time I traveled, I came home early and got a huge surprise. My burly grandpa, setting on the couch in my clothes with a Pabst Blue Ribbon in his hand. By clothes I mean my pink bra with matching panties and a black garter and thigh highs. When I said hello, grandpa was really embarrassed. Tried to tell me he lost a bet. I explained to him, that although we are family, there are rules in my household like you do not wear my clothes without permission or without consequences. I told grandpa if he was fond of ladies clothing, well he was going to wear them in public all day long.

He tried to argue with me, apologize, say it was just one time. But, I knew this was not true. When I have returned home before I have had my suspicions based on clothes not fitting right. I told him if he could wear my clothes in my house, he could out and about too. I went and got him a blouse, a skirt and a pink bow. Ordered him to put it on.  He kept protesting so I snapped pics of him in my lingerie and said do as I say old man or I send these pics to grandma. He immediately got dressed in my street clothes. Now he didn’t look too hot in them. In fact he looked like a sissy; an out of shape sissy.

I ordered him to take me to the hardware store. I wanted him in my clothes in a manly place. The whole drive he was pleading with me to give up this silly punishment. He was ashamed to enjoy ladies clothing. I told him to embrace his feminine side, to accept the fact that he is a sissy and cross dresser. I reached over and grabbed his crotch and could feel his hard on. I informed him a hard cock on a old fart meant he liked it; that he was enjoying being humiliated. Truckers passed us and honked their horns, waved, some even blew kisses. When we got to Ace Hardware, I instructed him to own it. Walk in chin up, boobs out.

I was so proud of my sissy grandpa. He strutted right in and embraced his femininity.  There were some stares, some snickers, but he never showed embarrassment.  When we got home, I let grandpa jack off on my big tits. He may be a sissy boy now, but he is still a red blooded good old boy who likes big boobs. Grandpa comes over all the time now and we play dress up. I do his hair, his nails, give him boobs and dress him in something pretty. Maybe I can feminize you too?

Tasting the Rainbow

My friends and I decided to attend the Pride parade in our local town; but, we decided to make it more exciting by dressing up. I chose to dress as a male drag queen; and, I wore a dildo just for fun. When we arrived, a gay guy with purple eyelashes and tight shorts approached me. “C’mon, honey, our float is ready!” I laughed but my friends pushed me to follow him. They helped me climb on top of the float, which was tricky with my 7” stilettos and flowing gown. Someone complimented me on my ‘tucking’ abilities and I smiled, waved my hand, and told them that I’d share my trick later. We waved to the crowd and threw out candy, condoms, and cheap plastic jewelry. I felt like a celebrity!
When we got off the float, the same cute guy who had brought me to the float told me to follow him. We went behind one of the large buildings and he pushed me up against the wall. He was lifting up my gown and groping my dildo. I moved away, afraid that he’d figure out it was just a toy. “Oh, you like it the other way, huh?” He bent over and exposed his cute little ass to me; I looked around and didn’t see anyone in the alley, so I pulled out the dildo and tried to shield it with my dress. I spit on the tip of the toy and pressed it between his ass cheeks. He grabbed at a box that was in front of him as I began rocking my hips, pushing further inside of him. He moaned, “Oh, yes, doll. Fuck your little fag.” I was so turned on that the friction from the dildo was going to make me cum. I grabbed his hips and pushed him harder against me until he and I both came. He exhaled, turned around, and said, “Thank you, doll. I will definitely see you around.” He blew me a kiss and left while I tried to absorb what had happened. My friends weren’t going to believe this!

Sissy boy on loan

One of my friends went on an all-paid vacation from her sweet Sissy Boy; and, she asked me to look after him.  I told him that his homework was to memorize all of the songs from Oklahoma!, one of my favorite musicals; then, I told him to meet me at my office.  When he got there, he took off his robe and had done exactly as I asked: he had on a pretty little yellow skirt and a pink top.  I bragged on his wardrobe choices.  Then, I told him to come out on the balcony…this is where he was going to sing his little sissy heart out!  He looked terrified and asked if anyone could see him.  I said, “Of course.  The people who have balconies and even the people below the building.”  I had to coax him, but he relented; I told him that I was going to tape his performance and send it to Mommy.  He cleared his voice and adjusted his hair…and he was ready!  He went out on the balcony and began with the title song; and, before long, he was prancing.  After he had sung the entire track of songs, he started making up his own.  I was so proud and rewarded him by touching his little clitty while telling him that he was such a good sissy, that Mommy was going to be so proud when she saw the video, and that Auntie Monika was so impressed!

High Class T-Girl Party

Last weekend my shemale girlfriends and I decided to throw a special party for the high society in town. Only way to be invited was by invitation only, no exception. So we mailed the invitations to the mayor of the city, lawyers, doctors, policemen, and anyone else we wanted to invite to our T-Girl sex party. This was our way of giving back to the community by letting them have a guilt free time with me and all of my sexy friends. When our guests arrived we all greeted them wearing hardly anything at all and drinks in our hands as we kissed them at the door. Then they got to hang out with us in a small group while we entertained the rest with some pole dancing and strip teasing. However, as the night got later and cocks got harder, all of us sexy T-Girls decided to end the night out with a cum blown bang fest by playing a sex game with our guests. Me and my girls all stripped naked and stood in a row while we told all of our horny guests to cum and get as much cock sucking tranny cum they needed. I just love to watch our city government get down on their knees and suck my dick so eagerly.

Stuffing that Fuck Hole

My favorite spot to stuffing my big, fat cock is deep inside of your “fuck hole”. Now that could mean one of two places on your body, baby. Either the one on your face with your sexy cock sucking lips or the tight hole that is in your ass cheeks. I am all about shoving my dick all the way deep in it. The feeling of a fuck hole being filled and wrapped up by my cock just makes me want pound it hard while I pinch hard on these firm nipples. I know you fantasize about me and my sexy package deep throttling you until I used you up like a cum dumpster. Let’s face it baby! I am your secret obsession that taunts your every lustful thought. With a sexy Shemale woman like me, what more could you even ask for. So be a good cum whore and have your fuck holes ready for me to ride all night!

Here Kitty Kitty

hot phonesex desireeWe fucked all morning and when I left to get us some breakfast and coffee he was sound asleep. I was very careful to be quiet when I got home in case he was still out. He was such a fucking manly fuck. All take charge in the bedroom despite the fact that I am 11 years his senior. Generally I like being the dominate one in the bedroom as the cougar and my young male friends are subservient to my wishes and desires. It was kind of nice to be told how he likes it and man handled a bit for a change.
I was as quiet as a mouse as I went to the bedroom to snuggle him awake for breakfast.
He was up all right, his back was towards me. He didn’t even know I was standing there watching him, amazed as he looked at himself in the mirror. Dressed in my hello kitty boy shorts, garters, thigh high stockings and a bra.
Well I’ll be damned.
My pussy was instantly wet at the site of him and my mind screamed out for me to take control and make him mine in this hot and kinky situation.
i walked around the bed so he could see me and demanded to know what he was doing. As he tried to stammer an answer I began barking orders. Telling him it didn’t matter what he was doing. he didn’t have permission to be in my panties and now he would pay for his indiscretion. His dick grew three sizes and my pussy was so wet I could hardly control myself.
Breakfast was all but forgotten.
I made him kneel before me and suck my pussy. I told him he wasn’t to say a word. all he needed to do was follow orders.
With his cock standing at attention he knelt in front of me I placed his hands one on each of my ass cheeks to insure he didn’t fondle his cock while he was eating my pussy. I began to cum hard filling up his mouth.
He looked up at me with pussy juice all over his face and I looked down telling him not to move.
I walked around to my dresser and puled out one of my dildos. I made him stand up and turn around , spreading his ass I shoved it inside him.
I let him know in no uncertain terms that he was to hold that in his ass until I told him he could remove it and that now he would sit and eat the breakfast that I was out getting while he was rummaging through my things.
He asked if he could cum to which I replied harshly “When I am ready and I give you permission. right now we eat”
Watching him sit in a chair with a dildo up his ass trying to eat and wiggle into a comfortable position was so funny it took everything in me not to laugh.
But when we were done and got up from the table his hard cock was still poking out from under my hello kitty boy short, I knew he was enjoying this.
I made him clean up the kitchen with the dildo in his ass before I took him in my room, laid him on his back and fucked his dick till it was soft with the dildo still in his ass.
Only then did I take it out before we fucked again. I think he enjoyed it as much as I did!hot phonesex desiree3

12 Trannies+Faggots Galore=Fun

Darling, let me tell you what happened….We met at the club, all of us partying and having a great time. Getting drunk, dancing, laughing and then they asked us the question and you could have heard a pin drop. There were twelve of us,  trannies, shemale divas. And there were 4 of them, cross dressing, cock sucking, slutty faggots. They had long since told us they wanted to be called faggots. They explained that they liked being bottom faggots. They never needed to give dick, they just wanted to lay down and get fucked hard while being called faggots.I guess that should have been our first clue. Any way the bar is about to close and they admit they have never been fucked by a shemale dick and they want to be our bottom faggots for the evening. They want to crawl around the room, begging to be fucked, sucking hard dicks and getting dick slammed in their asses all night. All they wanted was to worship our cocks while being used. Well we had never done anything like that and we have done a lot of shit. We were drunk enough, why the fuck not? It was a night I won’t soon forget, darling!

A Hot Surprise…

I met a guy, earlier this week’s name is Michael. He told me that he had a secret.  I begged him to share it with me.  He invited me over to his apartment and when I got there, a sexy woman answered the door.  She said that her name was Michelle. She had long, dark hair, a seductive look, and she was wearing a sexy, black mini dress and high heels. Her lips were painted red, and she smelled so sweet.  She gave me a kiss on my forehead and told me that Michael would return soon. For the next hour, Michelle and I enjoyed spending ‘girlfriend time’ together.  It was as if we were old friends.  For some reason, I felt like I knew her.  We spoke of the latest fashions, the best places to shop for lingerie, sex toys, and the best salons to visit. We talked about guys, sex, and brushed each others’ hair and gave one another manicures, while we bonded. I kept admiring and complimenting Michelle, because she was so sexy and pretty. I was having so much fun being with her and talking about ‘girl’ stuff.  An hour later, Michael still had not returned, and I had to go home.  I kissed Michelle on her cheek, gave her my phone number, and told her to call me, so that we could get together again.  Later on that evening, Michelle called me and told me that she had something to tell me.  She then admitted that she was really Michael.  I was shocked, turned on, and happy all at the same time. Do you like to dress up and feel pretty? I want to spend time with you. Want to be your crossdressing phone sex friend.

There Once Was a Piggy….

This little piggy cried weeee weee weeee all the way home! Want to know why? Because she is a pathetic little pansy and deserves every superior fuckalicious female to out her and tell the world how pitiful she really is.

I had the pleasure of hearing this little piggy squeal and embarrass herself. Talk about entertainment at its best…Ms. Darla and a few other mistresses joined in making sissy admit that she was such a pathetic little loser and how she really loves it. She just loves to whine and oink! Oink! OINK! like a little piggy for attention. Yup, she loves to be outed and that exactly what I’m going to do.

She has some dirty stinky secrets. That’s right! She is a stinky poo poo pansy that loves to prance around with a lump of shame in her panties. This naughty little sissy loves to dress up in cute little baby dresses with her purse and her shiny gold jewelry. Meanwhile, everyone that sees her is pointing, laughing and snapping pictures. But my favorite secret of all is when she serves me in the most wonderful way. I don’t have to worry about a toilet or tissue paper. I’ve got this dirty little piggy happily waiting to be my toilet slave.

What a dirty little piggy pet she is!

Tinkerbell Transvestite

I am a pathetic pansy crossdresser who is destined to be outed, shamed and publicly humiliated on this site forever. There is nothing I can do to change my fate. All of the girls know who I am and all of my shameful sissy secrets. They know I am owned by Goddess Levi and I must submit to Her wishes, no matter how embarrassing to me. I am such a ridiculous sissy fairy loser I must beg and plead to be treated as I deserve. I must oink and squeal as a piggy pet and I must blubber and cry like a sissy little girl. I must beg and plead to be kept on permanent public display as an effeminate fairy fag for everyone to see and to make fun of me ! Oh, won’t you please tease me and shame me as I admit what a Tinkerbell Transvestite I am ? Oh, please ! I beg of You ! Please out me & shame me & publicly humiliate me as a Tinkerbell Transvestite ! Oh, Thank You ! Thank You So Much !