1,510 results for sissy training

Quarantined Sissy Assignment

Online sissy trainingJust cause there is a pandemic doesn’t mean you girlies can’t make the best of it. If you’re stuck at home wondering what on Earth can you do to continue those Feminization goals well I have just the thing. This is the perfect time to live like your best self. Yes, you may be sitting at home in your frilly outfits and panties, that’s not enough. Let’s face reality you are more than likely going to be home for weeks so wouldn’t that make now the perfect time to go hairless. Let’s get you that soft smooth body just like mine! I’m talking legs, arms, pussy area all of it, needs to go! After all, no one wants to fuck a hairy slut, so seize to the opportunity to go smooth and more importantly please your Mistress. After all, I wouldn’t steer you wrong.

My Sissy Maid Husband

Sissy TrainingTonight, I was feeling a little more naughty than usual, so I made a call and made my sissy husband come down the stairs. He knelt in front of me like he knows he is to do. I handed him some pink silk panties, fishnets and some heels. I told him to quickly dress and meet me in my room. The doorbell rang and I let this gorgeous hunk in and escorted him back. I undressed him and sat him on the bed. I then instructed my cuckold sissy husband to come and get this dick nice and hard for me. He did exactly what I asked and started sucking that big fat dick like the little sissy slut that he is. Once it was hard, I told my husband to watch me fuck a man with an actual dick and not a little clitty like he had. I enjoyed that dick for hours. I took it in my juicy wet bald pussy and my tight little ass, allowing him to unload in all my holes. When we were finished, I had my sissy come over and clean him up nicely. I then spread my legs and motioned for him to come and eat the other man’s cum from my pussy and ass. He always does what I tell him and when he was done, I patted his head like a puppy and told him good boy. He may not be a good fuck, but he really is quite a good sissy maid.

Sissy Charlie Cleans Up Her Brother’s Cum

Mistress Phone SexI have been training Charlie to be my little sissy. She has a micro clitty, so she is of no use to me in that regards. She is so tiny that I could not even find a cock cage tiny enough for her to wear. So, I resorted to a pretty pink bow on her clitty and frilly pink panties with lace on the back. Tonight, I plan on having her be my clean up sissy. She is very dedicated, but I like to push my little trainees sometimes. I invited her brother over to join in on the fun. Kyle walked in and I immediately had Charlie come down and show off her pretty panties. Kyle got the biggest kick out of that and just laughed hysterically. Charlie just hung her little head, but I know she secretly liked it although we couldn’t tell because her little clitty is so small. I led Kyle and Charlie back to my room and had Charlie undress us both. Next Charlie was told to get on her knees and get Kyle hard for me. She was hesitant at first, so I had to smack that little clitty a few times with my hand to get her moving. But once she put Kyle’s dick in her mouth, she started giving him the best blowjob. She was taking him so deep and Kyle was starting to moan. Charlie is not worthy of bringing him to orgasm, so I had to stop her. I could tell she was disappointed as I had her watch her brother fuck me nice and hard repeatedly. He fucked me in my wet pussy and my tight ass leaving his load in both. When we were finally finished, I motioned for Charlie to come over and clean all her brothers cum from my pussy and asshole. She lapped it all up like a little puppy. As a special treat I let her lick her brother all clean too.

Sissy Gets Lucky On St. Patrick’s Day

Sissy humiliation trainingMe and my boy toy thought it would be fun to go out to a pub this St. Patrick’s Day. Didn’t expect it to turn out as fun as it did. I was going up to the bar to get a couple of more drinks for our booth when this guy in front of me was leaning over, exposing the green lace panties he was sporting under his pants. I couldn’t help myself. I reached my finger and pulled up on his panties. He froze and turned around and looked at me. He turned red and didn’t know what to say. So I asked him quietly if he wanted to suck some Irish cock? You know to be festive. He shook his head, yes, and I had him follow me back to our booth and introduced him to my boy toy for the evening. Discreetly we snuck out back behind the pub and I show his panties to my boy toy who just chuckled and started to pull out his cock once he realized what I was up to. I watched as this little sissy cocksucker got on to his knees and started to hungrily lick up and down on my friend’s cock. Slurping and moaning while slobbering all over the head. Giving the sloppiest blowjob I’ve ever seen a sissy slut give. The little bitch started to beg for it in his mouth cause he didn’t want anyone to know. Ha! Slut’s don’t get to make that call. I had my friend finish all over that slut’s face, making him lick off what he could and use his shirt to clean off the rest before going back inside. I could tell he was so embarrassed and worried he missed some. He kept looking around panicky at the time as he kept feeling residue dry upon his face. The rest of our time there we just kept looking at him and laughing at his few moments of misery.

BBC Sissy Trainer Zoey’s Play house rules

BBC sissy trainerAs your young sweet BBC sissy trainer, I must remind you of some rules for our sissyslut playtimes. My boyfriend knows that he has no free will. Much like you have none when it comes to me. I expect you on time from work every night and to come home straight from work. I will check your chastity device and your ass hole to make sure you are not whoring around behind my back. You belong to me. That ass is mine and as I lull you with my voice into a place of relaxation and fantasy, you will admit your deepest and darkest sissy fantasies to me. I know you need your ass hole gapped and your mouth to be the point of every rape fantasy you have. Facial abuse and sissy sluts go hand in hand. But you are mine bitch and you know the rules. NO matter where you are in your sissy metamorphosis you need this BBC Sissy Hypno training Mistress to make sure you are servicing nigger cock the way you are meant to be!

My Sissy Gets Some Humiliation Fun

sissy humiliation trainingOh how my sweet Devina went on for weeks begging for a humiliation assignment. However I wasn’t quite sure Devina was ready to push her boundaries. Then I realized I didn’t actually care so I sent her specific instructions with a warning that if she did not follow through I would disown her from my collections of sissy darlings. She was to meet me at my favorite nail salon at 2pm on Saturday. I knew they would be the busiest than, which made it the prime spot to show off my pretty pet. I should mention instructions entailed her showing up in a dress and pretty pair of floral sandals I recently ordered her to purchase. Much to my surprise my little sissy bitch showed up! A complete stuttering mess and a bit clumsy as she shyly looked at everyone who was whispering and giggling. Never seen Devina this shade of red before, she certainly impressed me. We each got our nails done with bubblegum pink polish and for good behavior I let her out of her little pink clitty cage for the evening. I have a pretty good idea of what she did for her Saturday night.

Sissy phone sex

sissy phone sex

Sissy phone sex is my most favorite thing to do. I love training my sissy girls over the phone and making them rub their little clitties for me. Making sure they’re wearing their pink frilly panties as they make sticky messes for me. When I have them all to myself, I make them dress up for me like the little sissy girls they are. Then I put them on their knees and bring in something they’re not used to seeing. I bring in a real man with a real cock. I make sure they take his huge thick cock deep in their little throats as I turn them into the perfect little cock sucking cum queens! I make sure they gag on him and deep throat him like good little bitches. I love getting fucked right in front of them and making them lick me clean after! Part of making them cum eating queens is making sure they can lick out every drop! My little sissy dolls are the perfect cum sluts.

 

Sissy Phone Sex Valentine’s Day with Dark Chocolate

sissy phone sex

I hope all my phone sissies had a happy Valentines Day. I took a break from sissy phone sex to give my sissy sons a chocolate treat. They are at that age where they have become fascinated with big black dicks. I am sure you understand the fascination. They are big, thick and beautiful. The Internet is full of them too. Anyone is only a keystroke away from interracial porn. I have a black lover named Jerome. He is all stud. He loves fucking this mommy with an audience. He also loves helping me with the training of sissies. I dolled them up for Valentine’s Day. They had on pink frilly dresses. Cute little white socks with Mary Jane shoes. I put bows in their hair and I even put on some pink lip gloss. They know how to suck cock. Every sissy should know how to suck dick. This was their first time sucking on anaconda meat. I am a BBC sissy trainer and it was Valentine’s Day. Not a holiday without love and chocolate, right? I fed my sissies their chocolate treat.. They did good slurping on chocolate cocks. They have a big sweet tooth for big black dicks. I am sure you understand. I do too. This sexy mommy wanted some chocolate too. My sissy boys watched their mommy take that chocolate fuck stick in every hole. They were right there to clean up the mess. It was a lovey Valentine’s sissy day.

Do Want to Wear My Sissy Panties?

sissy pantiesDo you like to wear sissy panties? I have a new sissy and she is not like my other sissies. She is a sexy T-girl. She has a little clit stick and perky little breasts. Honestly, when she sought me out, I thought she was one of my daughter’s friends. She looked like a high school girl. She is a 26-year-old transitioning girl. She heard I was great with feminization. I looked at her and didn’t know she had a cockette, so my feeling was that she was doing a good job herself.  But if she wanted some femboy training, I was happy to help her. Before I dressed her, I milked her little prostate. She laid on her back on my massage table. I lubed up my finger and slid it in her backdoor pussy. She reacted well. She loved having me play with her pea shaped gland. She had a hard cum, a ball draining cum. Once we got that out of the way, her little clitty was even smaller and would fit better in a pair of my sexy panties. She couldn’t believe how many pretty things I had. I have a huge closet. Some of the items are for me, but I have a sissy closet too. I let sissies and fem boys play dress up. My sexy little shemale was in awe of all the bras, panties and stockings I own. I found a pretty pink satin outfit for her. Pretty in pink. She knew how to grow her hair long, develop her titties and shave off her body hair, but she needed me for the feminine touch. I dressed her and gave her some style tips. I also helped her perfect her feminine walk. Next lesson is cock sucking. Can’t be the perfect femboy without knowing how to suck dick.

Femboy Training Princess Zoey

Femboy Training

Your Princess loves femboy training. Imagine your sweet Daughter laughing and pointing when you show her your hard cock. Even as a sweet young girl she knows you are quite small. She refuses to acknowledge that it is a dick. She says no Daddy put panties on you’re a Girl! Small giggles and pointing and running to tell mommy. This is when mommy reveals that you’re a sissy cuck. She teaches me all about how to control you. I find out soon enough that you love sucking BBC with mommy and the day comes that I join you in the Big black dick cock sucking. The first time I get fucked in front of you your wet your panties five times. Now that I am a hot teen Mistress You are a full-fledged sissy who enjoys being my muse for my BBC sissy training of other sissy boys. I am the Princess Mistress to brothers, neighbors, and my cuck sissy boyfriends, all because of one hot daddy sissy!