Tag: forced crossdressing

Mature Phone Sex Women

mature phone sexMature phone sex women know more things than coeds. That is just because with age comes experience. Younger girls are tight and giggly. They may not care about size. Your cock may be a tight fit in a coed’s pussy. But do young girls get your kinks and fetishes? Likely, no. Case in point. I have a therapy client who is a crossdresser. He is my age, in his 50s. He was a 20 something sugar baby girlfriend. She is for appearances. Not that he does not like banging her. Of course, he does. She looks good on his arm at work events and when he travels too. But he cannot be his complete self with her, so where is the fun in that? I do not want to be his girlfriend. That is not what this is about. I believe full hardheartedly in embracing your kinks and fetishes. You like to wear women’s clothes and fantasize about sucking cock? You should go for it. And hopefully you can trust your partner with those deep dark desires. But when you cannot trust your partner, or your big reveal does not go well, you can get some phone sex therapy. My client came out to his sugar baby, and she did not understand. She laughed at him. She shamed him. And she threatened to blackmail him with his employers. She just saw it as an opportunity to exploit him, not support him. So, I told him to find a woman his age that he could share this with because older women are just more accepting of things that fall outside the box. For now, he is without a female companion. As his therapist though, I am helping him explore his bi-side. I am taking him shopping. I am helping him dress. I have even provided some cock for him to practice on. He says he does not need a girl to share his kinks with when he has a phone sex therapist.

Small Dick Cuckold Humiliation With Daniella

Being a Sexy dominatrix is always a fun roleplay. My last Small dick humiliation session have me playing with my Shave wet pussy. I dressed him up in a slutty nurse outfit, he had not done any crossdressing yet but I wanted to see him like the perfect slut. I pulled on his little dick as I asked him if he was ready to see me get fucked by a big black cock like a Sexy babe like me deserves. He nodded as I stroked his little dick and edged him onto submission. When my bull walked in, I made my sissy prance around as I called him names and humiliated him showing off his little dick and tight white asshole. We used him as a fluffer for my bull’s BBC. He sucked his cock good, had him leaking before he shoved in my wet cunt. As he fucked my sissy cuckold slut watched as I played with his little cock pushing him to the edge every time but not letting him cum.

Small dick humiliation

When my bull was ready to cum, he pulled his BBC out of my gooey cunt and sprayed my little dick slut all over his face. Now he begs for facials every time he sees me.  

Dominating Queen and Sissy Bitch

Forced crossdressing Divina

“Do what the fuck I say or else! Drop to you fucking knees and bark like a dog you fucking sissy punk!” My sissy was such an obedient bitch. He does and wears whatever I tell him too. Tonight, I forced him to wear some high heels, fish net stockings, a leather skirt and a white bottom top, with a tiara on his head. I wanted him to be my little princess slut. After he was done eating the all the guys cum out of my filthy nigger pussy, I made him get on all fours and crawl around the house. I even put a leash on him and took him outside for a while. Even though he is a piece of shit, it’s great having his sissy tight ass around. Everything about him turns me on. The way he eats my chocolate pussy. The way he sucked my toes and eat my ass. The way he sucks all my friends’ cocks and give them rim jobs. I love a man that knows how to be vulnerable and let his queen run the show. You want to be my next sissy cunt baby? Call me, I am ready to dominate your ass.

Black Slut & Sissy Boyfriend

Sissy humiliation

 

Tonight, I fucked my sissy boyfriend. He loves when a black bitch like me dominates him. He lets me do whatever I want to his body. He is such a nasty whore. One time he was being a bad boy, so I made him suck my toes. He has a major foot fetish which I don’t mind because I have beautiful feet. Another time I made him eat me and all my friends wet black pussies and assholes. He begs me to humiliate him all the time. I make him wear lingerie and stockings too. For a sissy boy he sure does have a great ass. “Yes, fuck me, Queen! Fuck me!” I make him call me queen. I deserve to be treated like nothing less. If I had a real cock, I would shoot my load deep inside him. “Hmm you like that?” I smack his big black ass. His asshole was so wet too, I could see it creaming up on my strap. I take the strap off spit on it and shove that strap cock deep into his asshole. He loved when I fucked him hard. His asshole getting wetter and wetter. My pussy was getting so wet at the sight of me going in and out of his tight ass. I take my vibrator and put it inside of my pussy so I can cum with my sissy bitch. “Oh! Fuck yeah Queen, I’m going to cum right fucking now.” “Come on you sissy loser, cum for me.” We both came same hard. I take off the strap and my pussy’s full of cum. “Now come over here and clean this mess up you cum guzzler.” He dropped to his knees and cleaned my pussy dry.

Forced Feminization

Forced Feminization

Forced Feminization would be both a dream come true and his worst nightmare depending on how he looked at it.  Bill was known as the strongest man in town as the Sherriff, but he had a dark dirty secret.  He was the town’s biggest sissy in training with Mistress Glinda.   He lived every day in fear that his secret would be revealed, and he would be outed as being the little sissy that he was.  

Every Friday night Mistress Glinda would invite over friends to share in the humiliation and degradation as he was forced to wear the French Maid outfit and serve cocktails to the ladies.   The ladies loved to see just how far they could push him especially about his little cock. Each week after the guests left he was either rewarded or disciplined based on his behavior that evening.   He understood his place and always bowed down to Mistress Glinda no matter the outcome.

Sissy Humiliation: Richard Needs To Come Out of the Closet

sissy humiliationI love to give Richard sissy humiliation. He is a pathetic sissy boy with a tiny white boy penis. See the cock I am sucking in this picture? Richard wishes he was half as big, LOL. I love chatting with Richard because he is such a girly sissy. Plus, he knows size matters. Richard is a black cock faggot. I think he has always been one. He admitted to me that he let a black neighbor man fuck him silly when he was just a young teen boy. How hot is that? I think many white men try to be straight. Family approval and fitting in with their peers matters so much to men at a certain age. But Richard has had a series of failed relationships. That has to do with his itty bitty clitty though. Although, he does love to cross dress. He has such a fem body, that when I saw the pictures, I thought it was one of his ex-girlfriends at first. I mean I think Richard was born in the wrong body. I think he just needs to barge out of the closest and let everyone know he is a sissy faggot who is addicted to those monster black cocks. They the only things that make him cum. Likely, the only things that made his ex-girlfriends cum too. He needs to be out of the closet.  When women find out he likes to dress up in their clothes and a be a bottom bitch for a big black dildo or the real thing, they have zero respect for him anyway. It is only a matter of time before he sabotages another relationship by dressing up in her lingerie and admitting his need to be dominated by black bulls. It is only fair to the women that Richard come out of the closet and admit he is a beta bitch for black bull cock. Those women do not need to waste their time with a poser. I love being Richard’s phone sex therapist. Is he a cool guy? Yes. But he is such a pathetic little BBC loving pansy too. If he just came out of the closet, he could be a black cock faggot 24/7.

phone sex therapist

Phone Sex Therapy Cuckolding Mistress

Phone sex therapy with a cuckolding mistress is exactly what you need. I know who you are, you with that little penis. It’s so surprising that you even get married. You sure must’ve fooled your wife well thanking that she was going to get fucked properly by you.or maybe she just married you for money. Did you marry your wife young before she even experienced a real man.?

It’s always surprising to me knowing that some of these men I’ve been married for years and the surprising thing is is how did you please your wife? I mean did she never have sex before or what? It’s some thing I’m still trying to figure out when I get pictures of these men and their little tiny clits, like how the fuck can They even fuck with that thing.

Honestly, men that get into cuckolding are doing a good thing for their wives. They must really do love their wives. I mean to allow them to get real pleasure finally. It’s great.

 

Phone sex therapy

Richard Sheets BBC Faggot

Best phone sex

The best phone sex is outing a BBC pantyhose wearing fuck whore. Richard sheets is that fuck whore. A dirty little slut who wears pantyhose and loves big black cock. Richard is such a little faggot whore who loves to get fucked retarded by big daddy dick. Look at the little faggot.

These big black cocks that fuck my sissy faggot keep the fuck out of his little pussy. The best part is big black daddy gets off on hurting little white sissy faggot. Richard is a stocking loving sissy faggot for big fucking black cocks. The only use I have for this little faggot is to humiliate him.

Richard moans like a little Beta bitch when that big black cock fucks his little faggot hoe hole. My little cocksucker admitted that he likes to beg for that cock. In fact he lets his big black daddies fuck him bareback what a pathetic little slut huh?

Cocksucking phone sex

Gwens Forced crossdressing

forced crossdressing One of my specialties is forced crossdressing. And this time of year is amazing for men who need to be dolled up and slutted out. Now look at this picture, one of these isn’t like the other. One of these sexy vixens is a shemale sissy, with a tiny dick. Can you pick me out here posing with a few friends after we took turns making our sissy slave whore into a beautiful slutty fuck doll! I have so many ideas on how to make you the perfect princess with a penis! Stockings, short little sexy Christmas dresses, silver cock cages with bells hanging from your balls. As you learn how to walk with a swish to that ass and balance in heels over six inches. Shaved, lotioned, and prim all sexy and feminine. But as you look at the part there is more sissy maid training that must happen. Just like our little sissy ladyboy, we had to teach her to clean out pussy, to take a dildo up her sissy pussy and submit to not only women, but a nice big fat juicy cock one day soon. It’s up to sexy sluts like me to make the perfect princess despite having a cute little penis! Perhaps you in your little slutty Christmas outfit can cum see me and submit the was a sissy la-la should! There is much sissy fun to be had with this Mature Domme Momma!

Forced feminization by Gwen

Forced feminization

Forced feminization was on my mind as I looked at Steven. He was a non descript man reaching his forties, and this speed dating thing was overlooking him. The fact that he was roughly my size intrigued me. A smaller stature looks well dressed up in pretty playthings! Divorced, no offspring, just him trying very awkwardly trying to talk me up. “We don’t get a lot of pretty women like you at these things..” he said shyly. I smiled and asked if he ever considered that he might not ever find his match this way? The nervous laugh, and the way his eyes darted down, told me he was out of his league. And when asked why I needed a dating service I smiled and told him.. “I’m just bored, I like to see the regular men and how they try to get a date. My pussy ached to put him in panties and lead him around like a puppy pet. 

“How open minded are you Steven, Would you like to come back to my place for drinks and…something different? 

And that’s how our night started. I took him home and Liquored up this very regular man up. Then I laid out some satin panties and bras and told him to change and put on a show for me. He bucked and asked to leave, I just spread my legs and told him if he played my game he could taste me. Again he stopped and stared and I got up and walked over to him and pushed him to his knees! “Obey me, or I will spank you and take pictures! I’m sure everyone would love to see you spanked by a hottie! 

I spent the rest of the night guiding Steven into becoming Stephanie with forced crossdressing and my excellent strap on skills! Care to become my next project baby?