Category: Best sissy trainer

Sissy Training Women are a Hot Commodity Nowadays

sissy trainingSissy training women are a hot commodity. My daughter is 18 now and about to start college in the fall. Her generation is more fluid and open about sexuality. She knows trans folks and gender fluid people too. She even knows some sissies. She brought this one femboy home this weekend to meet me. He was about as feminine as they come. Born in the wrong body. He wants to transform into a woman. She knew I could help him. He grew up in foster care but was dumped recently because he turned 18. Suddenly, he was homeless and with no money or job. I knew how to help. Femboys can make great money hooking. It is a great side hustle for a few years. Lance is not a transsexual yet, but with the best sissy trainer lending a hand, I could give him a makeover to make guys believe he was as post op shemale. Not all sexy trannies get big boobs. Many men prefer that small but natural breasted look. I am a talented feminizer. Lance was in good hands. My daughter helped me turn her friend into a pretty T-girl. We waxed off all his body hair, especially his pubes. I put him in a pretty blonde wig and a cute schoolgirl outfit. A little plaid skirt, a white shirt tied at the waist and cable socks perfected the look. With the right shading and contouring, I chiseled his face to look very feminine. To test out his new look, we went to the truck stop. I acted as his mommy pimp, and I whored him out to all sorts of truckers. I did not want any money, however. I just wanted to help with some femboy training so Lance could make money and get a place of his own. Lance made bank as Layla a barely legal T-girl. And she will keep making money and growing her skills under my tutelage too. Maybe I can help you get a side hustle too. Never hurts to have a side hustle.

Femboy training turns punishment!

Femboy trainingThe only thing worse than not having a sissy for Femboy training and to use, is have one that is as useless as you! You claim you want this you even beg, but when push comes to shove you barely know how to give fucking head! You are pathetic, a real waste of space.  I back hand you hard across you dumb slutty face. You disappoint me fem boy and I gave you a chance. I should have known you are a little bitch from the size of that tiny clitty in your pants.

Don’t worry sissy slut your punishment will not take long. I got you all dressed up in a black lacy thong. The alpha is horny and jerking his massive hard cock. What the fuck are you doing sissy why haven’t you serviced him yet? You know this is what you were made for, and you are really pissing me off. Do I have to hold your hand through everything, act like this is your first?

Now gag on that fucking rock hard, veiny, cock! Show me that you are good for something! The alpha is so aggressive, and he is sick of waiting. He face fucks you like the whore that you are. Ramming his cock inside you while you beg him for more. you really are lucky the alpha lets you have his cock. If I were you, I’d me thanking him and begging for more training! I mean you clearly need it, and his balls are really heavy.

Now grab his balls and massage them just right. I want him to cum and I don’t have all fucking night. Now suck that cock good, ack like you actually fucking now how. I’m so fucking sick of you bitch you are a worthless little bitch. I beg my paddle and smack your ass hard. You lurch forward from the pain, and you throat get ram hard. Take his cock I don’t care if you can’t breathe! you guess you should have thought about that before embarrassing me!

My Penal Free Pass

Adult phone chat lines

When my man went to prison, he told me not to wait for him and to fuck anyone I want to, even if it’s one of the pervs who calls my adult phone chat lines.  I don’t think I would’ve been able to wait anyway, but it was good to know that I had my papi’s permission.  He must’ve told his best friend to look out for me while he was locked up, because he wasn’t behind bars for a week before his bro came sniffing around my doorstep for some fuck action, and he was definitely not trying to sex up one of my sissies.

I wasn’t surprised, he’s always had a thing for me.  In fact, he and my man were both trying to get into my pants when I met them, but I went with the bad boy and left him to watch from the sidelines.  But ever since I was given the penal free pass, we’ve been meeting up for some freaky fucking.  It really just makes sense.

Do you think I’m going to make my mistress cunt cum on a little clitty having cutie wannabe?  Those bitch-boys couldn’t please a woman if they were made of milk chocolate vibrators!  All they’re good for is taking gigantic dicks in their tight little femboy asses.  When I do fuck them, it’s to humiliate them or to help turn on the stud who is reaming out their rim.  The amount of physical pleasure I receive out of it is minimal, though it does please a little carnal spot in my brain.

I’m going to keep fucking my man’s friend until he tells me to stop.  It’s always fun and he’s pretty hot.  Who knows, maybe when baby comes home from prison, he’ll want to fuck me and his friend at the same time.  It never hurts to ask, right?

 

Day Dreaming Of Your Sissyn Slave Training

While you are slaving away at work, all you can think about is the hard pounding I gave your sissy pussy. You wear a suit and tie all day but deep down inside you like when I dress you up in sissy panties and heels like a good sissy slut. You think about the sissy training and how you love licking my cunt clean. Last night I had a special outfit for you.

Sissy slave training

The moment you saw it your clitty twitch. You put it on and begged your mistress to make you, her bitch. You know you are mistress’s sissy slut property, and you live for me to use you. I love hearing you beg before every sissy slave training session we have. It gets my cunt hot wet and ready to use your tongue. I had you on your knees lapping at my cunt begging for me to fuck you and when i saw your sissy clitty leak i knew you were ready. Your body shook as you saw me put my big black strap-on on. I made you tell me who you belong to before I bent you over and rammed my cock in you. As i fucked you hard i spanked your ass hard, leaving my handprint on your round white ass. Finally, you begged for mistress to let you cum and when I gave you the permission to, your clitty sprayed your juices all over. When done you cleaned up your mess like a good sissy slut. 

You Need My Sissy Training

sissy training

It’s late at night and instead of being at home with your family your pansy ass is here sucking on my feet. You love the taste of my pedicure piggies as I face fuck you with my toes. Watching my Ebony slits get wet as you deep throat my size 7 makes your little pink wiggler pulse. It would be nice if I were able to call that thing in your pants a cock but it’s so small it looks like it should have an areola! I’m going to call it a nipple and start pinching and flicking it like one too. Of course, you moan like the horny slut that you are.

You should be home being a good family man but since you’re here being my bitch. I’m going to spank your bare ass and make you beg for forgiveness. Only a lowlife would neglect his family for their sick perverted fantasy. I hope you know I’ll be recording your sissy ass bent over my knee. The video is mainly an addition to my extensive sissy porn collection but I’ll also be sending this to your wife! The cane against your plush ass is an encouragement to be sincere in your apology. Each lash will feel like lightning spreading across your wide rump! Causing your pain brings me so much pleasure. You should be used to getting treated like fuck meat! After all, you come crawling to me almost every day begging for humiliation.

I should turn you away and make you handle your responsibilities but I enjoy the control I have over you too much. You don’t care if you miss 1 million calls from family and friends. Nothing will loosen the suction your slutty as has on my dildo! That’s exactly how I like it.

Sissy phone tag

sissy phone

My Sissy Veronica was suffering from social anxiety. Sissy V is a shy one who enjoys cartoons and wants to be mommy’s sissy. The only way this sissy doll could release a happy milky out of her peepee hole is if Mommy Alessandra says yes. We both were wearing ponytails and knee-high stockings. Sissy veronica begs mommy for some rubbing action. Mommy grabs her toys and lets Sissy V show her all the practice she’s gone thru. Sissy Veronica deep-throated that big black juicy dildo.

Plenty of giggles and tickles put this sissy girl at ease. After a couple of days without  Mommy, sissy v gets nervous because she needs all the guidance and sissy tasks from the goddess.

I was away for a trip, and we both kept playing sissy phone tag. I kept missing my sissy’s call.

I knew how much stress would put her, so I devised a plan to put my sissy at ease. A  quick task she has to do to become a good girl. Sissy Veronica loves when mommy Alessandra sings her praises.

Sissie’s First Time

online sissy trainingI love having my sissies do whatever the fuck I want. If I say get on your knees and suck this big black dick until he cums you better do exactly that. I told my sissy that he was to go and get some more sexy pieces of lingerie and show me them but he hasn’t yet. What I should’ve done was punish him until he made sure to remember that for next time. But I decided too do something much better this time, I had a room full of big men with big fucking cocks. Unfortunately for you, you haven’t had a nice fat cock inside of you yet because you were so new to training. Well today is your lucky fucking day, you get to have every fucking cock shoved into that tight little ass today. Get on your knees and you better make sure each of these cocks are nice and fucking wet before them shoot their load right into that little ass of yours.

Mistress phone sex/Sissy slave Training

Best sissy trainer

I gagged that sissy slut and gave him some hardcore anal pegging while wearing an all black latex suit! I turned him into my personal whore and fucked his slutty ass. After working him up I put that bitch in a chastity and turned him into a slave of his own mind. I teased and humiliated him! I denied him any sexual pleasures while having him locked away in a vice! Eventually I gave in and pegged his gaping man pussy while his cock was locked away. While fucking that tight little man pussy of his I asked him how bad he would love a real cock deep in his ass right now.. He begged and pleaded so I teased him ever more. I had my hot neighbor come over with his big juicy 10 inch cock and turned that sissy slut into a cuck! I made him watch me ride my neighbors big veiny dick while he begged for a turn. Leaking through the crevices of his chastity.. Telling me how bad he wishes he were me. He told me he would do anything I wanted just for one stroke of my neighbor’s hard cock. Well, I knew that bitch didn’t have a choice but to do whatever I tell him to do so I did not give in. When I was through orgasming all over that hard cock. I took that sissy slut out of his cock cage… I folded him to the point his dick was hanging right above his mouth and stroked his cock until he nutted directly into the back of his own throat! That’s all the pleasure he will be receiving today. Now gargle and swallow!

Sissy humiliation training

Phone Domination Sissy Trainer

I’m your newest addiction Mistress Addilyn. The phone domination goddess of a sissy trainer for big black cock craving sissy faggots. I like to humiliate my slaves. Train you to learn and know your place. My main goal is for your transformation as a sissy cum slut willing to do anything for that BBC cum.

You are already with your foot in the door as they say in the fact that you have the craving. It will take a little work to get you truly ready to serve the Master cock, that big beautiful black dick.

With Mistress Addilyn at your side. Training and scolding you into the good submissive is part of the joys I have. It’s my pleasure to tease and deny you. To make you cage that clit stick and to plug your hole until you are willing to get that fuck hole stretched. A bbc slut is what you will be and dressing for that BBC is how you will start.

Phone Domination

Mistress phone sex whore Remi

mistress phone sex

One of my favorite sissy bitches was supposed to come by today but she couldn’t make it. I still want to watch a little whore get her pussy pounded and mouth fucked though. I’m hoping you can help this kinky, mistress phone sex trainer. I want you to be my little, cum loving slut tonight. I’ll make sure you’re dressed up nice and slutty for the sexy bull-studs I have coming over. No experience needed because Miss Remi will make sure you get all of the training you need. I’ll have you draining every one of those fat, hard cocks into your slutty holes! I can’t wait to sit back and watch them stretch that perfect, little pussy of yours!