Tag: sissy training

We Love Sissy Phone Sex

sissy phone sexMy daughter and I love sissy phone sex. We get to pretend there is another girl in the house. Morgan loved dollies when she was younger. She had a huge collection of dolls, and she would dress them all. Having a sissy in the house is like having a life-sized dolly. Yesterday, I brought home a sissy to play with us. I met him on a sissy site. Turned out he lived nearby. Morgan was so excited that she jumped up and down. She ran to her room quickly and came back with her make-up bag and some sexy clothes. This sissy had a small, feminine frame, making it easier to dress her in our things. We are both slim. So not every sissy would be able to wear our clothes. I was a make-up artist for years. I worked for Vivid studios and did make-up for their porn starlets. I know how to make a woman look slutty. Plus, I can retouch that makeup after a few dozen cum shots to the face. I had this sissy, with my daughter’s help, looking so pretty. My daughter dressed her in a pink laced and ruffled dress she wore for Easter one year. The main reason we have kept so many of Morgan’s pretty dresses from her youth is for sissy training. I mean you never know when you might meet a sissy, right? We had this boy transformed into a total femboy. Morgan called some male friends she knows to give our sissy a proper introduction to the sissy world. When the friends arrived, they bee-lined to our sissy gurl. I am not sure they knew she was not born a girl. I mean Morgan and I do good work. Our pretty little femboy chugged all their cocks and their sperm too. She popped her sissy hole cherry too. It was a proud sissy trainer moment. This sissy mom enjoyed the show.

Sissy Training w/ Mommy & sister

sissy training

He needed his sister and mommy for sissy training. We had just come home from shopping and Daisy went to her room to change. I heard her scream and then began laughing her ass off. I had to go see what all the fuss was about. And there my son was. In her dirty panties and my big bra with lipstick smeared across his face. 

 

The best part was his little clit stick sticking up out of her panties because they were too small for him. The big cups on my bra were comical as he tried his best to keep it on. My son had embraced cross dressing in an attempt to deal with his little dick. 

I told Daisy to get the emergency sissy kit we have for some of our Johns, I knew just how Daisy and I could help our sissy kin evolve into a cock sucker little sissy slut! 

I sent a mass message for an emergency cock for him to suck too! If we were going to do this right, it would be the sissy phone sex talk of the town! 

Last Swim Party

Mommy Phone sex You ready for this taboo mommy phone sex tale, daddy?

My daughter’s best friend was having a birthday party. The last swim party of the season, I had to bring my sweet princess to see Sandy and have some fun in the pool. Her Daddy met us at the door and said that we were going to have to wait a while because Sandy wasn’t ready yet. But he has something sexy for mommy to wear. A nice stars and stripes Bikini that showed off my beautiful D tits and shaved mommy pussy poking out the sides! 

My Princess was so happy to be playing in the pool with her own little bikini riding up. 

Then low and behold comes out little Daniel in his own Hot Pink Bikini and lip gloss. His little pink peter was hanging out the sides along with his hairless balls! If you know this P-mommy, you know I can’t resist a sweet young sexy boy like that! I bent down and kissed him on his lips. Yes this boy had already undergone some sissy training from his own Handsome daddy! In no time at all I was sucking a little boy dick as his daddy finger fucked his ass. My daughters best friends daddy moaned out loud “Can I touch you daughter!” Of cuking course he could, we would share our slutkins and get off hard at the last pool party of the season!  

Sissy Phone Sex Fun

sissy phone sexMorgan and I love sissy phone sex callers. Morgan always wanted a sister so having a sissy boi is the next best thing. She brought home a sissy boi she met online. They were on Reddit in some chat room for sissies and one of the guys lived only 20 miles away. Small world, right? Between Morgan and I, we have a ton of pretty things in our closets. We are girly girls. Lots of pinks, purples, satin, silk and Lacey items fill our closets and drawers. I was a professional makeup artist for a couple decades. I can make anyone look pretty. She brought sissy Tammy home and we played dress up. It was like her having a life size dolly to play with. Morgan dressed Tammy. I did her makeup and hair. We are a great team. Once Tammy looked the part, it was time to act the part with a trip to the glory hole. All dressed up and ready to suck cock, we took Tammy for her debut as a sissy to the glory hole. She was so excited to suck cock. She has lacked the courage to do it on her own. Just like our sissy training callers. That is what we are here for. Morgan and I love training sissies. Tammy got her belly filled with cum. It was a beautiful sight.

Jan and Daisy love Sissies!

sissy phone sexSissies love a hot two girl sissy phone sex call with a mommy and daughter whore team. I love showing Daisy how sissy men can be here and in our personal life. We recently had a very petite man come over and bring a duffle bag of female clothes and ask if we could dress him up and call one of our big dick friends over. The Only thing is Daisy knew his daughter and her mom, he was married and a closet sissy case! A truck driver no less. And when pressed for information we discovered that when he was home off the rig he would let men cum in his ass in his marital bed. We laughed and told him we would keep his secret, but he began to cry and said he needed to be exposed for the sissy whore he is. He had been doing this two long and wanted Daisy and I to let his wife and daughter know he was really a fag and only wanted cock. I told him first he would need to prove it as my big black boyfriend came over and showed him what a real dick looked like. In his ass and throat. I think we will toy with this sissy a bit longer before we let his family know just what a sissy bitch he is!

Sissy Phone Sex Fun

sissy phone sexI enjoy sissy phone sex calls. I am an old-fashioned woman. By that I mean I am a fan of classic lingerie. My daughter wears a thong and thinks that is lingerie. I have a closest full of old Maiden Form and Vanity Fair bras and panty sets. I have slips, and pantyhose. I have baby doll nighties and corsets and garters. I have a few long night gowns with the slits up the side too. I picked up this young man this week. He was not jailbait, but he was younger than my son and daughter. I thought we were going to fuck. He was handsome and eager. When I went to get us something to drink, he raided my closest. I was not prepared to come back with drinks and find him in a pair of my panties and a matching bra. He did not want to fuck me. He wanted help dressing. He told me mature sexy women have the best lingerie and they know how to look sexy. I could not argue with that logic. I decided that I would have my boyfriend’s son coming home from school soon, so I could fuck him. This was a young man who needed some help exploring his femboy side. I was a little jealous of his body. He was lean with long legs. Not very muscular. His body was naturally sort of feminine. I should have seen it coming, but I guess I was just too horny to think about him being a femboy in need. The day turned out great. I helped him dress. I taught him how to walk in high heels using a garter belt and stockings to keep him centered. I gave him some make-up tips too. Dressing him up reminded me of how much I loved helping my daughter discover her girly side when she was younger. The boy needs sissy training, and I will give it to him. He is coming by again tomorrow.

Daddy Dick Vs Husbands Clit

sissy trainingI’ll never forget the time my daddy showed my Husband what a real man’s dick was like! We had sat down for Sunday dinner and I was playing footsie under the table with daddys cock. Now up until this time I was sneaking out behind my Husbands back to fuck daddy. I couldn’t help it, daddies dick was so big and the first cock that had ever fucked me. My marriage was just a cover up for my incest life. My husband was so dumb to think I wouldn’t fuck my daddy while he was at work. How could he have been so blind to think I would fuck his four inch dicklette and be satisfied. I wasn’t a virgin when we were married and my pussy was already well accustomed to my own daddies 8 inch cock.
My husband dropped his napkin and saw me playing with daddys dick under the table. He was outraged and My daddy took control. You don’t yell at his princess!
My daddy pulled my husband back in his chair and whipped out his cock. I was commanded to suck off my own fathers cock right in front of my new husband. The thrill I got as My pussy gushed in my panties was like no other! I sucked and slobbered until daddy laid me on the floor and showed my husband how much I loved his big fat poppa Cock! My husband has never been so humiliated, and has never tasted a dick before then. But you bet your ass he sucked my juices off my daddies cock that night!

Our sissy phone sex Is Hot!

sissy phone sex

If your looking for a sister and mommy for sissy phone sex we got you covered! Daisy has a sissy brother we just love fucking with. We have known he has been stealing panties and bras for a while now. I had to calm Daisy down because she was pissed that some of her more expensive stuff was going missing. I made a plan to catch him! I told her we could make him a slut just like her and she would get her revenge soon enough! 

The time was right and I had our strap-ons ready and snuck up to Daisy’s room when he least expected it. Caught in sheer nighty, red thongs and a red bra smoking a joint as he played with his clitty stick. He was so surprised that the dildo in his ass came flying out across the room. After we gathered yourself from laughing Daisy shoved that ass juice cover dildo in her brothers mouth as I prepared myself and my dick for some hardcore sissy training. My son would become the ultimate sissy fag with me and his sisters help!

Encouraging My son to suck cock

sissy phone sex

I recently walked in on my younger son sucking off his older brother. Now at first I was a little upset as this sissy phone sex tale goes on. I didn’t know what to do. I yelled, shut the door and put my hand over my mouth. My heart was racing and my mommy cunt throbbing!  Was this normal brother behavior? Why did I find this so arousing?  Did this go on behind suburbia doors and no one just talks about it? I had such guilt for the way I acted. And even more guilt for being so horny I masturbated to the vision of my son sucking his BIG brother’s cock off.  I even went to the school guidance counselor to ask for help. He said to just act like nothing happened.  I didn’t notice any cock sucking for a couple of weeks. 

 I came in from grocery shopping and heard moaning. I knew that was my boy sucking on his brother’s cock again. I quickly ran to his room and stripped down to my bra and panties.  Would encourage my son this time. I would make up for the way I acted. And as I pushed the door open I saw my son on his knees with a ten inch cock down his throat. He looked so happy as I looked up and it wasn’t his brother! The Guidance counselor was telling my son to suck daddies’ cock! Daddies big black cock. And this Momma wanted her some of that BBC too! 

mommy phone sex

Mommy phone sex for sissies

mommy phone sex Mommy phone sex of feminizing and degrading my submissive son and husband! I know exactly what pretty boys need to feel like a tender little sissy slut. Are you ready to explore every nook and cranny of your female transformation? Its nothing to me to bend over my small dicked husband or my little son and put on my deluxe vibrator 5000 Strap-on and turn them into quivering piles of sissy hole fuck whores? Too much?
Perhaps your a closet faggot in need of full dress in pretty panties by your wife , mommy or sister? We all know you steal and wear dirty playthings out of the laundry room. Naughty boy!
Mommy Isabella is here teach you everything a sissy phone sex slut should know. Lets fine tune your oral skills. Down on your knees like a good slave, look at my phallus and call it mommies cock! Yes I know it’s bigger than your pathetic excuse for a penis. So suck it and take constructive criticism as I teach you everything you should know about pleasing men. Real men. Yes you will be dressed to the nines and feeling sexy and just like a girl! But what I am worried about tonight, is that mouth learning fellatio. It’s just like a real man’s cock and you better learn how to suck it! Sissy Training by family is the best kind.