Tag: panty boy phone sex

Sissy Training Phone Sex is HOT!

Sissy Training Phone SexI love my sissy sessions. The prettier they’re willing to get, the happier I am. She came to my door in the sweetest pale-pink dress, complete with a parasol and some strappy heels. I invited her inside, offered her a drink, and told her that my friends would be by in a few minutes. She told me that her goddess knew where she was, what she was doing, and that she hoped to have an amazing time to tell her goddess all about later. I told her that would all depend on how good a girl she was. When my friends got there, I invited them in, settling them on either side of her on my couch. Tranny porn picturesI told that little prissy sissy that she was to take their cocks out and start stroking them. She was a good girl, doing exactly what I asked of her. Between the fellas and me, we started stripping her pretty dress off, only to find some matching, pale-pink lingerie underneath. I called her a fruity little fag, and made her get down on her hands and knees in that pretty matching set. One of the fellas squatted in front of her, shoving his dick down her throat, face-fucking her. The other pulled those pretty panties aside, pushed a finger up inside of her. He spit on her sphincter and then replaced his finger with his dick, pushing up into her. He stretched her so much, that she was groaning on that dick in her mouth. She was the best little tinkerbell transvestite I’ve seen in a while. Watching her get plowed got me all hot and bothered, too.Hot ass sex

He wishes I’d give him this pussy

Sissy Phone SexOne of my pathetic sissy boys called tonight. He wanted to do an over the phone sex fantasy. I was totally down of course. I can get off to making fun of him on the phone just as well as in person. I lay down in my bed and get relaxed. I make sure and clarify that he is not fucking me on the phone either. He sighs but I know he loves everything I do to him. Otherwise, he wouldn’t keep coming back! He loves to be called a dirty little bitch. He is a nasty slut kitten who loves to take big cock in his mouth and ass. I give him a story. We are at his house. He wanted to have a house party. ( I know how cute and desperate) He leaves it up to me to put it all together. I invited over two of my girlfriends. I will call them slut and whore. Really the names fit them perfect! They are some sluts for sure. ==giggles== I command my phone bitch to strip down naked. He tries to ask where everyone is at but I cut him off. I tell him not to speak if he is going to argue or that will be two lashings added for the next time he is in my presence.  He obeys. It is silent on his end. He likes the whippings of course. He definitely doesn’t want to acquire more than his weekly total. I tell him we brought some toys. The slut pulls out a big black novelty dildo. The kind you are supposed to give as a gag gift. This dirty fucking skank loves those big cocks up his ass. the slut lubes the huge cock up nicely. we don’t want to hurt our little bitch boy toy too much. Just enough to make him cry and cum.  she slips it into his loose slut hole. He instantly begins to moan. Take that cock you little slut kitten. He moans louder. The whore then takes her pussy and spreads her legs right in front of his face. I command him to eat that pussy like it’s Chinese food. ( His favorite I might add.) He buries his face deep into her cunt. She squirts almost instantly. There you go, my little slave, eat that nasty cunt. She cums again and again. He makes her pussy get everything soaking wet. All the while he has that big elephant cock inside his ass. He asks me if he can cum. He is so eager to please. He listens to all my rules and follows them. I reward him with permission to cum. I hear him moan and sigh on the phone. I’m glad he called me. I needed someone to boss around. These pathetic cock suckers brighten my day.

Sissy Training Phone Sex – Luncheon

Sissy Training Phone SexOne of my favorite pansy boys contacted me today for a date. My lovely, evil mind concocted the perfect date, so I told him to put on his favorite intimates, a sexy red dress, and to make sure his bra was properly filled out, and his hair and makeup was done. He met me at the restaurant I requested, meeting each and every one of my requirements with style.

We walked in together, and heads turned immediately. It was a classy establishment, and our dresses were just this side of tasteful. We ate our meal, discussing what his goals were for the rest of the day. Little did he know what was coming.

After the waiter brought the check and he paid for it, I stood from my seat and waited for him to stand from his. Then, right there in the middle of the restaurant, I grabbed his arm and whipped him around to face me. I pushed him to his knees, being the tall fellow that he was, and I pressed his face into my breast. He quickly sprung it free and took it into his mouth like a good little bitch. I whispered for him to free his cock from under that lovely dress and start stroking it for everyone to see. He followed my orders very nicely. What he didn’t expect was for the waiter who had just served us to walk up behind him, get down on his knees, and ram his big dick into my bitch boy’s ass. He squealed into my tit before succumbing to the fucking. It was, indeed, a delicious luncheon date.

Sissy Phone Sex with Sexy GFE Shannon

Sissy phone sexLately, I’ve been getting more and more calls from these sissified men who just want to feel pretty and wanted. I will admit, it gives me a bit of a thrill. Most of the guys I’ve had up til recently had been macho men who just wanted arm candy to walk around and make them look good, someone who would look amazing on their cocks. These sissy men have been treating me like a goddess, and it has been amazing. They will come to me and submit gratefully to my ministrations. They let me bathe them from head to toe, dress them in beautiful intimates and stunning dresses. I get to do their makeup, style their hair, and help them on with their stockings and shoes. Then, I get the privilege of walking out with them, seeing mens’ reactions to the beauty we have created. I get the enjoyment of watching cocks get hard over an illusion that my darling lover had an urge to portray. My favorite part, though, has been getting to take my lovers back home with me, and having friends or even strangers come in and have their way with my lovers while I get to get myself off using whatever appendages and methods I want.

Sissy Training Phone Sex with Shannon

Sissy training phone sexMy sissy boy lover came back to call. My problem was that he came dressed down, looking a little frumpy for my tastes in some jeans and a t-shirt. So, I pulled him inside and put him on the floor. On his hands and knees, I undressed him before spanking his tight little ass for showing up so shoddily attired. When I finally had him down to his bare skin and had sufficiently punished him for his lack of good judgment, I pulled out an outfit I had made him leave here in the past. I handed him the box, and ordered him to get dressed right there in front of me.

He pulled the panties on first, tucking his cock gingerly into the thickest part before adjusting the g-string into his ass crack. Then, he put his bra on, filling it out with the little silicone pads I had found for him. At this point, I told him to stop and follow me. When we got to the bathroom, I pulled a razor and my shaving gel out of the cabinet. I forced him to shave, and watched as he did it. I popped his ass every time he missed a spot, and he missed a few.

Once he finished shaving, I brought him back into the living room, and held his dress up for him. He pulled the sexy, slinky little pale blue slip of a dress up his legs and over his hips. The dress hugged every curve of his sweet body, and his hard cock was a bulge pressed against it. When he had finally finished dressing, I brought out the wig I had bought just for him. It was close to his natural medium brown, but with some natural red shot through it. It was a sleek style that would complement his facial structure. I sat him at my vanity, and watched patiently as he put on makeup, receiving approval for each item before using it. He was such a sexy sissy. When he finished, I rewarded him with my pussy on his face.

Sissy Phone Sex with a Princess

I recently had a call from a great guy. He treated me right from the outset. I never opened a door, never spent a dime out of my pocket, and he made me feel like I was the only girl in the room every place we went.

Naturally, when he called up requesting another date last Saturday night, I said yes. Imagine my surprise when a rather attractive female showed up at my door dressed as well as I was. When he spoke, I instantly recognized what was going on, and we proceeded with our date as planned.


When the date was over, after another lovely night of him treating me like a lady, I invited him up for coffee. He accepted, and followed me directly upstairs. When he closed the door behind us, he immediately dropped to his stockinged knees on my floor and assumed a submissive position. He begged me, right then and there, to make him my little bitch boy. He even shed tears, he begged so prettily.Sissy phone sex

I made him crawl into the living room with me and start taking my shoes and stockings off. Then, I had him kiss my feet and lick my toes. At one point, his teeth scraped across my foot in the process of him licking, so I made him climb across my lap and take a spanking.

I felt his hard cock pressing against my legs as soon as he lay across my lap, and when he got back up, I gave that a quick smack, too. We had lots of fun that night, but I’ll post more about it later. I need to go for now.

Queen Z

adult phone chat You can feel the excitement in the air. I can barely hear myself think with all the nervous chatter that is going on. It’s wall to wall shemales, perfume, make up and costumes. All of us want to win the title of Queen T-iva. Only the prettiest, most talented, glamorous tranny can hold the crown. I am here to tell you that I want to be the Queen Z.
Walking down the hall, make up done to perfection, hair and nails are flawless, I am looking down at the check list on my phone making sure every thing is in order, I didn’t see him coming.
We ran right into each other.
I recognized him immediately, he was one of the judges.
When our eyes met the look was unmistakable. He reached out and began caressing my nipple making it stand up and pay attention.
I could feel my cock growing between my legs where it was tightly tucked away for competition.
“I bet your cock is as glorious as these tits of yours.” he said with a twinkle in his eye.
He grabbed my hand and placed it on his cock. Judging by the feel of it, he was packing a very impressive package there.
He pulled me into the shadows and pushed me to my knees as he freed his dick for me.
There was no mistaking what he wanted and there was no way that I was going to let this prize piece of meat go with out tasting.
I gave him everything I had, pulled every dick sucking trick I know, and sucked the skin off that tube steak of his until his knees were weak and he was filling my mouth up.
Not one drop of his seed was wasted.
I stood and re-adjusted my throbbing cock.
With a wink he turned and said, “I will see you after the competition my Queen.”
My heart skipped a beat.

Sissy Phone Sex Training with Aunt Sheila

sissy training phone sex ffSissy training phone sex is much more fun than I thought it would be for me. I don’t get many sissy calls, but that is about to change because I have my own sissy under my roof. My nephew is staying with us for several months. He is this smart boy who graduated early from high school but can’t start college in the Fall. I thought I was making him a man when I took his virginity, but apparently, I have made him a sissy. I caught him wearing my underwear to his job. When I searched his room, I discovered a slew of missing undergarments of mine. Bras, panties, pantyhose, even some slutty club wear and makeup. This boy was clearly not a man, but a sissy. I confronted him when he came home. He tried to lie to me. To me, the woman who is giving him a roof over his head. I grabbed him, pulled down his pants and gave him an old fashioned bare bottom spanking. Of course I had to remove my pink panties first that he was wearing.

I was enjoying paddling his ass, but not as much as he was enjoying it. Every spank I gave him, he came on the floor. Turns out my nephew is a sissy and a punishment whore. Well, if I was going to have a sissy under my roof, he was going to dress and act the part. I made him clean up his cum off the floor with his tongue. We can add cum slut to the list of things that describe him too. After that, we went shopping for a sissy maid outfit for him to wear and some panties that fit him better. It was like having a daughter. In fact, that is how I view him now. I have changed his name from Mark to Marie. Outside of the house she can be known as Mark, but under my roof, she is Marie, a good little sissy that cooks, cleans and does whatever her Aunt wants her too, even fluff the cocks of the various boys that entertain me while my husband is at work.

spanking phone sex ffMarie and I are in the beginning of our relationship, but sissy training is going very well. I know they say boys will be boys, but some boys were never born to be boys, don’t you agree?

New Year’s Punnishment

sissy phone sexMistress Levi has informed us that our Piggy Pet is in need of attention. I love when Levi sends requests for Sissy’s public humiliation. This time Sissy has earned the title of our New Years Permanent Punishment Pansy. We all know that she begged and pleaded for humiliation and even has to pay for it. We also all know that once she receives what she asked for she will beg and plead for mercy. Silly Sissy will never learn that you get what you ask for from a group of superior females that learned from the best, Mistress Levi. Our Tinkerbell Transvestite deserves public ridicule, perpetual teasing and sissy shame. Come to think of it I think 2016 should be The Year Of Sissy Michael here at WBMT.  The Year of intense humiliation and shame. The Year of  The Piggy Pet and paying for the deserved teasing and taunting by the wonderful women of  WBMT. The Year of the Final Outing, the one that will put an end to the fake man life of our Pansy Princess. We all know that is really what she wants any way Who better to give her the dream she has always dreamed of then us? We can be like her Blue Fairy from Pinocchio and instead of making our Silly Sissy a real boy, we will help her out of the closet so she can be a real girl forever and ever! Your welcome Sissy.adult phone chat melinda1

Humiliation Phone Sex

Humiliation phone sex

Humiliation phone sex really turns you on doesn’t it? I am always happy to entertain my little pet’s fantasies. I love spending our Sunday’s dressing you up. You love putting your makeup on for me. You use red lipstick to make yourself look like a little whore. Then you apply your blush, and eye makeup like a good girl! I taught you so well and your makeup looks great on you. Now what should you wear? What about this cute polka dotted bra? I know you have cute little panties to match. That’s right… Put them on. Oh, how cute my little fuzzy pet looks! You look adorable! Just like a real little girl with an itty bitty clitty. Why don’t you kneel on the ground next to me? You are so cute in that outfit. But I want to see that red lipstick all over your pretty face. Get down on your knees and clean my shoes. Make sure they are shiny. I don’t want you to forget that you are my little pet. Now come, show Princess Paris, what toys you have for our session today…