Tag: Taboo phone chat

Riding My Pony Sissy TJ

Mistress phone sex

I got a great pony ride from my favorite Sissy TJ. I dressed her up in a pink pony harness with a pink saddle and a pink Butt plug with long pony hair. I made her prance around like a good pony spanking her with my paddle every so often. I then got on the saddle and rode her for a bit while my BBC friend came in. He walked over as I pulled the plug out and started guiding his big black cock into his tight man pussy. I instructed my Sissy TJ to buck back on to the cock and I sat on the pink saddle as she got pounded away by that big black cock. I played with my clit as I rode my bucking pony watching that BBC slid in and out of her. I did not stop until I watched my sissy get filled up with a big load of gooey thick cum, I couldn’t help but squirt all over the pink pony saddle my sissy was wearing. After we were finished my sissy knew to get to cleaning his cock and my cunt, Sissy TJ knows how to clean up all my messes.  

Sissy phone sex commitment

sissy phone sex

I’m ready to make you enjoy some sissy phone sex. you may be curious, but I will make you a fan of sissy fun.

You will want to have it all the time. Sissies love to dress and take cock, but it goes much more further than that. They love to feel welcomed. I will show you why you were meant to be a sissy rather than a macho man. The first thing is. First, you aren’t an alpha man. I can see you love big cocks, and you want one, but you will never get o to enjoy the perks of having a well-endowed penis. It is okay to be a sissy, but you have to be a good one and be willing to devote yourself to me and show me you want me to teach you.

Making My Sissy Slut Fluff My BBC

Sissy slave training

Sissy phone sex calls are so fun. Being able to feminize you because you have a small dick that I will pull and play with like a big clit. I don’t fuck little cock. I will never put a little dick in any of my holes and you will know that. I will show you I love BBC and if you don’t yet you will. I will have you dress like the perfect sissy slut and you will worship Mistress Gypsy and do as I please. I will you use you as my cock fluffer, getting you on your knees and using your mouth to get my BBCs hard and ready for me. I will be getting fucked by a real cock as you are on your knees massaging his prostate with your tongue. You will do this until he feels me up and then you will lick and suck his hot gooey cum out of me. You are my sissy slut and you will clean up all my messes.  

Be My ‘VIS’ Darling!

Femboy Training

My “VIS” meaning my Very Important Sissies pay extra to have a full day of shopping with their favorite trainer! I start the day with a bit of pampering, we go get our manicures and pedicures as well as some waxing and facials before getting a massage and going for a hair appointment. It is so fun to feel so well pampered before we go spend some serious money on our clothes and accessories. We go to the luxury boutiques and spend a small fortune on shoes, lingerie, corsets, nighties and robes before venturing over to buy some pretty ready-made dresses and outfits. Our last stop is a little couture boutique where we get fitted for a couple of gorgeous custom gowns because every sissy of mine needs to be pageant ready at a moment’s notice! Don’t you want to be my VIS Darling?

Online Sissy Training Helps You with BBC

online sissy training

With me you get online sissy training. My boys, however, get a live-in sissy trainer. They are teen boys now. They live their lives as trans girls. They identify as pan sexual because they like a little bit of everything, LOL. I love helping them explore their sexuality. Now that they are at an arts school, they get to be who they want to be. They can dress how they want too. Now, the school frowns on adult boyfriends. So does the law, LOL. But mommy? I am more liberal thinking. They like black cock. They may have gotten that from me. It is no secret that their mother is a size queen. I love big black dicks. And now so do my two sissy boys. I came home from a date last night. My boys expected me home much later. I planned on it too, but a huge storm was causing blackouts everywhere, so my plans changed. Plus, I wanted to check on my boys. The house was dark when I arrived, but I could see the glow of candlelight, so they knew what to do. They were not alone, however. I interrupted them sucking on big black cocks. Both my femboys were dressed pretty and on their knees sucking two black men close to my age. The men are lucky I am so liberal. Since I am a BBC sissy trainer on the phone, I helped my pretty boys. It is not easy to swallow a foot of cock, especially when the cock is thick too. They were doing a good job for their age and inexperience. I showed them some techniques. I did not want to upstage them, but those were some big black dicks. I had them swallow a teaspoon of olive oil and hang their heads over the side of the couch so their black lovers could stand over them and slide those BBCs down their throats. Just a couple tricks made all the difference. Soon those men were pumping big thick strands of cum down my femboys’ throats. It was a proud mamma moment. Maybe I can help you too.

Full Nasty Exam

I was horny and bored waiting on my friend to get out of quick care. That is when I saw this sexy man going to the back, I decided to follow him to the back. I stole a doctor’s coat and put it on right before I walked into the room, he was in. I told him he needed to undress.

BBC sissy trainer

I watched as he took his clothes off. I examined his body and saw he had a big cock. I told him he needed a full exam and I put gloves on and told him to bend over. I stuck my fingers in his ass, he tried to flinch but I said that I needed him to relax so I was going to help him stay relaxed as my hand reached for his big cock. I stroked his cock and got it hard as I milked his prostate. I told him I needed a sample for the lab and just to keep relaxing. I kept fingerings his asshole which made my cunt dripped as I stroked his throbbing cock. He screamed that he was going to cum so I grabbed a cup and made him shoot his nut in to it. I was going to save it for one of my sissy sluts to drink later. 

Sissy Training Is My Passion!

Sissy Training

My sissies are true cum thirsty sluts trained by a absolute sissy slut trainer queen! My sissies get the best advice on hair, make-up and feminine mystique available. Sissy Training is my passion and I have learned from the best women how to maintain a high standard of beauty and be flawless in my sex skills. I teach my sluts all my secrets so they can go out into the world and be gorgeous cock sucking whores. I start with the basics, helping my girls pick a flattering wardrobe that accentuates their curves and their most attractive features. If they have a great set of tits, it tell them to wear low cut v necks and wrap dresses, If they have a juicy bubble but it tell them to pick a nice short set or tight jeans to advertise their bussys. Then I make sure their hair and makeup are on point, they can either get their natural hair styled to be more fem or buy a long luxurious wig to wear that really makes them feel so pretty. Once they have the look down I get right into helping train their asses to take a big dildo, all my sissies are required to buy a big black cock dildo to practice with. I coach them on how to lube up and stretch themselves out to take all the fat cocks possible in their little tight bussies. They know the pain of having their asses trained will pass leaving only true pleasure behind. I also like to coach on wearing a cock cage so their clits shrink to a more feminine size from taking all the dick in their asses possible. It brings me such true joy to hear about all the cocks that my sissies make cum once they are fully trained in the art of pleasuring men!

Suck those chocolate cocks

bbc sissy trainer

Real sissies love to have the BBC sissy trainer pave the way. I get so committed that I will show you firsthand how to handle juicy black cock. There’s nothing I like more than to show you how to deepthroat appropriately and how to make sure you genuinely are satisfying cock. You will be the object of a lot of domination. Naturally, sissies are submissive, and that’s not going to change. There must be no doubt in your mind that you want to get fucked and used like a cock craving whore. Sissies get a bad rap sometimes of being too desperate.  I will show you how to seem pleasing but not pathetic. You still have to have that factor and charm. A sexy sissy is better than a desperate one.

Best Sissy Slut Fashion Show

I was so horny and excited for the event I had planned for my sissy Tj and I. I was throwing a sexy fashion show and sissy Tj was going to be my runway model. I had invited all my big black bull friends, and they were all ready with big hard ons and balls full of nut. I had picked three outfits for her to strut her stop down the runway. First was the hobble skirt hi heels and collar with nipple clams.

Best sissy trainer

Then it was a one-piece blue lace garter set with matching knee-high lace stockings. Last was our Halloween option and I dressed her up as Marie Antoinette with a with lace once piece corset lingerie piece under neath. What no one knew was she was also wearing a “Lovense” vibrating butt plug that I had full control of, it was part of the perfect ending to the fashion show. With every step down the runway, I turned the vibration up on the butt plug. Sissy Tj knew not to squirm and to put on a good show and the end she was made to strip her Marie Antoinette costume and that is when I turned the vibration to the highest going up and down making her squirm until I had my sissy TJ begging to cum. I was going to let her cum until she swallowed every load in the room. That is what she did over until every bull in the room was drained and that is when I finally gave sissy Tj permission to cum.    

Make Me Proud

Best Sissy Trainer

When my sissies report back to me that they have has their boy pussies fucked I feel so proud! As the best sissy trainer around I truly feel joy when my sluts are out in the world taking big fat dicks in their assholes or down their throats. I always tell them to make me proud, never spill a drop if cum unless it is leaking from that perfectly fucked bussy! They know that I am happiest when they are dressed slutty and fem for all the men around to know what a true sissy they are! I tell them all the time to embrace their inner feminine by staying out and getting fucked all night long, don’t ever leave a hard cock without draining those balls of their cum!