Tag: forced crossdressing

Diana Sissy Humiliation Sissy Trainer Extraordinaire

sissy humiliation

Diana Knows sissy men down to a T! This sexy hot milf is the epitome of a sissy humiliation session. Look at her she is all fucking woman and knows he way around small dicked sissy faggots like you. Creaming your panties yet? Sometimes I think her two sissy boys were born into heaven with a sissy trainer Milf like her. Even I would beg under her stilettos. I know you would serve her so well licking the dirt of the bottom of her shoes and begging Mistress to take it easy on you. Diana will not take it easy on you by any means though. Forcing you into little foo-foo ruffled baby doll dresses and tights with flutter panties on. Then her big Bull cocks passing you around to fill your stomach and ass up with so much cum you will be farting it out and belching it for a week. You know if you buck, she has paddles to beat that pale white ass into submission. Go on I dare you to not submit to mistress Diana. That’s right you only need a slight helping to be the gapped ass sissy slut you were meant to be. Her sexy ass knows what a sniveling idiot you become around dominate women like her. Small dick humiliation is what you crave, and she will tell you exactly why you need to be a submissive sissy. Just look at this hot milf, I mean if you need a sissy mommy she can be loving yet dominant as well. Take my word even this genetic female knows that Diana has the sexy pussy you want to drain of all cum. And the big Bull cocks she fucks with leaves my pussy sore for days. SO grab your ice pack, lube and prepare for your ass hole to be annihilated by the one and one Mistress Milf Diana.

small dick humiliation

I made him a real bitch

cuckold phone sexThis little dickie cucky boy wanted to try to be manly but he failed miserably. All I could do was laugh as he strutted around acting like some kind of wannabe tough guy and boy he did not like being laughed at. He tried to get all up in my face like he was gonna do something so I just slapped the shit out of him and told him that he could never be in charge because he was more woman than man. I forced him to take off his fake man clothes and put on a bra and panties. He actually cried can you believe that? We had a whole photo shoot with him in lingerie and dresses and makeup and he claimed to hate it but his tiny clitty was hard the whole time. Of course I didn’t let him touch that little clit and I definitely did not let him cum either. He stayed in his girly clothes all night long too and I think I will make him be a girl whenever I see him from now on.

He Was Due for Sissy Humiliation

sissy humiliation

 

You were due for sissy humiliation at my hands. I made you think I was going to fuck your brains out in my dorm room. I stripped you naked and saw your tiny four-inch cock and began to giggle. Then you heard giggles coming out if the closet and my two sorority sisters burst out with their phones to film your tiny clit stick. I thought I would make it a little even and had us all strip down while we forced you into panties and I sat my naked body on your chest. And put pretty eyeshadow and lipstick on your pretty face. Flashes went off and I had my Sorority sisters share his pretty face.

It wasn’t long before I had on my 8-inch strap-on and was forcing him to suck it! I lubed up and fucked his tiny ass pussy making him moan and whimper! Then I heard whispers as my friend’s phone clicked and they excitedly said they had our man meat on the way to teach our little clit stick sissy a real lesson with a big bull cock. But first, we had to dress our sissy slut up and bring him to the town with us! We put him in a cab with us and told the cab driver all about his strap-on play! We embarrassed our sissy slut so much and when we got to the fancy restaurant, we served him a plate of Vienna sausages and a huge calabaza sausage, which we promptly went to shoving in and out of his mouth in front of everyone! I had no control over the patrons taking pictures of him and where they would go! You know I wouldn’t have had this sissy phone sex story if he had a nice normal cock, he would have had a coed threesome.

 

 

Making a Sissy Maid

Forced Feminization

I love when I get the chance to turn a man into just a little sissy who caters to my every whim. My newest plaything is just too adorable, we play dress up into the cutest little frilly dresses complete with stockings, panties and training bras! He said that he wanted to do anything to make me happy so today we are turning him into a little sissy maid for me to use! I found a cute and sexy little French maid outfit, short skirt and thigh high white stockings made him look perfect! I ordered him to draw me a nice hot bubble bath and he sat at the edge of the tub and washed my feet and legs, then my arms and back, since he was so good I let him wash my chest too. Then he carefully washed my hair, it felt so good to be catered upon! Since he did so good taking care of me that I even let him have some fun after I had dried off. I rubbed his little cock through the fabric of his panties until he came right in them!

You Would Look Lovely In A Dress

Sissy humiliation

The moment I met Ben I just knew he wasn’t the man he pretended to be. The way he would admire my clothes and style in such a way it seemed like he idolized me. Most men have a look when they are undressing me with their eyes. Not Ben, he wasn’t undressing me he was playing out a whole different kind of fantasy in his mind. On the outside he was handsome, strong not a bad man to have on your arm at all. However, I can see past that to what is lurking beneath him. Inside he was delicate, beautiful and I would guess very horny. Most locked away sluts tend to be. So tonight I planted the seed that will hopefully lead to me coaxing out the slut that lays beneath. As we returned to my home after an evening out instead of pulling him in for a kiss, I whispered in his ear “You would look lovely in a dress”. I sent him on his way after that, the look on his face let me know he would be back. And me and my closet of fun will be waiting for him.

Phone Humiliation For The Kinkster

You have that kinkster side to you and better than being the hipster I know you also are and my hipster lovers love my phone humiliation sessions. I love to help their Hipster style out in letting them be as Metrosexual as they desire. It’s ok to desire some cock on the side, and even better to have that open relationship with multiple lovers where you share one another, it’s “The” thing now and as “In” as men being the sissy cocksuckers they have suppressed for so long. It’s all out in the open these days and your a lot cooler to be “In” with the trend. I love to help you realize where you fit in as I am also in that hipster way as a vegan, polyamorous lifestylist. I’m really into indie music and films and can “get” you better than so many others. I love living in the Pacific Northwest and being myself and enjoying life. When I’m not working the therapy lines I am enjoying the mountains and streams with outdoor activities and fucking outside is the best I greatly enjoy being an exhibitionist as much as voyeuristic. I hope we can do a session soon where we can get to know each other!

Phone humiliation

Sissy humiliation. My Sissy Pets

Sissy humiliation

Sissy humiliation is something I share with only the kinkiest of men. My pets fantasize about having a group of women dress them up like a total slut. Take them out to the local bar and later make them perform various dirty sex acts? Some just like to wear their wife’s silky panties and bra around the house while admiring themselves in the mirror. Most all sissies I know love nothing better than putting on a pair of high heels, laying on their back, pulling those panties to the side and getting the wonderful ass fucking that they deserve and crave. Wait, should I call it ass fucking or should I say mangina fucking? Forced crossdressing will lead to you wanting that tight fuck hole of yours pounded and pounded good. Maybe you are a closet panty boy and you need me and my girlfriends to bring the sissy out of you in a big way. There are various degrees of feminization, sissification, and crossdressing.

I have callers that have been crossdressing for many years. Deep down some of them want to fulfill their dream of crossing over and becoming a full transgender female. You deserve to treat yourself and give in to your desires because you work so hard and you only live once. I know you close your eyes and recall how good it feels to slide on those sleek, silky garments, how hot it made you feel to slip your feet into a strappy pair of sexy high heel shoes. So what are you waiting for? Get dressed up and call me! Or even better don’t get dressed. Call me to dress you up! It is so much more fun to get off with someone who understands your every need during Roleplay phone sex.

I offer the best Sissy, Crossdressing, Transgender Phone Sex Around!

 

Phone Sex Therapist for Sissies

phone sex therapistAs a phone sex therapist, I encounter sissies often. There are all sorts of men I won’t fuck. I say no to small dick men, broke ass losers, cuckolds and sissies. I want a masculine man; one with a cock I can feel. Mark was no man. When he showed me is dick, it was like a turtle in its shell. I saw no dick. Just lots of skin and some balls. He was a no dick wonder. He was clearly a sissy. He just needed a sissy trainer. I have mostly cuckolds in my posse of losers, so a sissy was a nice addition. He craved sissy humiliation and training. I took him shopping for panties at Victoria Secret and made him tell the hot sales clerk that he needed pink panties to protect his little clit stick. She snickered at him, but that was what I wanted. The more he was shamed, the more he wanted to please me and any one I wanted him to please. I had him buy the hot sales girl some sexy lingerie she could wear for a real man. I made him buy me sexy things too. All he can do for sexy women like us was buy us things and entertain us. Sissies are a girl’s best friend because they wait on us hand and foot. Plus, they do whatever they are told to do from singing us silly little songs to buying us pretty things for real men. Sissies are growing in number, so we now have a new site of the best sissy trainers around. If you are a shameful sissy, check out SissySlutHut.Com

sissy humiliation

Sissy Maid Stories Are So Hot

sissy maid stories

Sissy Maid stories make my young pussy so hot. I love when I have a hot strong man come begging at my feet for some hot coed pussy. I told Mark that the only way he would be able to get my sweet pussy is if he put on his maid outfit and cleaned my Condo with 6 of my friends Present. ANd he had to keep his big black dildo clutched in his tight ass as he did so! I didn’t want a speck of dust left anywhere. My University Girls came over to drink wine which Mark had to tiptoe in his black heels not to spill one red wine drop on my white carpet. And to humiliate Mark and his small penis under his frilly maid outfit! All night he was serving us and the girls would take turns fondling his little package under his skirt, pinching and pulling that cute little boy dick that never belonged on a grown ass man. We were nice though and ordered some hot cock in the form of all-star football players to give us creampies so Mark the sissy Maid could lap us up like Icecream! 

We Want to Play with a Sissy Boy

best phone sex

My boyfriend and I love pretty sissy boys! We make the best ones get all dressed up and make them our cross dressing faggy slut! I love watching our sissy fuck toy get on his hands and knees to please us! A good sissy always makes sure to suck my boyfriend’s cock and my strap on to get them nice and wet. There is nothing hotter than when my sissy fuck toy sucks, slobbers and gags on my boyfriend’s cock while begging us to fuck his little whore holes.

I love getting my rubber cock slathered in drool so that it can be slimy and wet when I slide it up his rosebud. An eager fuck boy is the best fuck toy! We want our fuck toy sissy to crawl on his hands and knees with his sexy little outfit for us! We want our faggy fuck toy to moan for us while we fuck his tight throat and perky boy pussy!