Tag: Best sissy trainer

Heaven Has Arrived

adult phone chat linesSissy boys defintley need to get dick sucking lessons from me. Nothing gives me greater satisfaction than training a sissy. I have a client that comes to my house regularly on evenings. He wants to be completely humiliated. He believes because he has a small dick he has to be made feminine in the bedroom for his inability to perform. So I have him dressed in a bra and panties. I make him suck dick. When I bring over some of my very hung friends they allow him to suck their dicks. He has become quite good at taking it in the ass as well. He would make a perfect tranny actually. I think I want to start using the strap on as well that would really excite me to have complete control over him. It’s so empowering to be a woman who dominates men. I feel like I do my part to make men experience their biggest fantasies being fulfilled. A dominatrix with abilities to keep you coming back for more.

You Hungry Cum Slut

Online Sissy TrainingOh, look at you. What a mess! That is going to be the last time I let you go off on your own. Oh, you holes hurt? I bet they do, you are absolutely dripping with cum just look at the mirror. Ugh, you are just sticky all over and got your new pretty red dress all dirty and ripped! What did you do, offer yourself to a gang of horndogs again?  I know you are an addicted hungry little cum slut, but there is a reason we prepare for this type of stuff. Not to mention how disappointed I am by not being there to watch. Giving how sore you seem to be and very lube up by the cum still dripping from your pussy. I think it’s only fair I bring out my biggest strap on and teach you a little lesson for being a bad little slut. Now bend over and give me a smile.

Sissy made me some money

sissy phone sexI sent sissy out to make me some money last night, she didn’t really want to go out she was all scared of getting sick but I didn’t care. I wanted her to make me some money and suck some dick and that was what she did. She stood on the street corner dressed in her sluttiest outfit and I made sure she asked every man she saw if he wanted to party. I made her suck every dick she came across and she had to swallow every drop of cum too. Even if they were coughing and looking sick as hell she dropped to her knees and sucked all those cocks too. She told me later that she felt like the nastiest whore in the world but it had her lil clitty so hard all day long. Since she was a very good girl that sucked all the dicks I asked her to I let her rub that lil clitty until it squirted all over the place. See? I can be nice sometimes.

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.

Come Serve Your Mistress

sissy maid training

Nothing fulfills a Mistress like getting to train a sissy slut maid like yourself. The process from beginning to end is a real treat to witness. They usually come to me all insecure and shy about this role that they know they are meant to fulfill. It’s often some family man with a well respected job as an authoritarian of some sorts, who simple can’t shake the feeling that he was meant to be a submissive little sissy boy. That’s where I come in. I take great pleasure in easing you into my sissy maid training operation. Don’t get too comfortable with the word ‘ease’ either. Now let’s start with the little details you keep to yourself on a daily basis. How often do you fantasize about sucking cock? What kind of cock do you fantasize about? I’ll bet it’s often a fat, long, veiny black one! How many times have you given in to the impulse to slip into your wife’s, girlfriend’s, sister’s or even mother’s panties? These are the things we need to establish in our training session.
Tick tock, little cocked sissy boy. It’s time to step into the role you were meant to fill. The sooner you embrace it, the better it is you’ll serve.

I’m a BBC Sissy Trainer Where Ever I Go

bbc sissy trainerThere is never a dull moment when you are a BBC sissy trainer. I got stuck out of town. I was in another state for a wedding when traveling suddenly became difficult. My plan was to rent a car instead of flying. I had to wait two days for a car to become available. I was in a nice hotel, so I thought I would make the best of it. I went to the hotel bar and met some fellow stranded folks. Charlie was not fuck material. Demure man. Feminine characteristics. Talked like a sissy too. When he asked me to dance in this girly pitched voice, I laughed. I joked that he would probably prefer to suck on a big black cock. He got ashen white. “How did you know,” he asked incredulously. I told him I was a sissy mom and a sissy trainer. I have an innate ability to spot a sissy a mile awhile. Charlie and I talked over drinks. He really wanted a big black cock, so I got him one. When you look like me, finding a black stud is never difficult.  This time, I just had to look around the room. I saw a handsome stud and he locked eyes with me. He was in my room an hour later and so was Charlie. I let Charlie watch first. Like many sissies, he had only seen big black dicks on the Internet. I was there to give him the real thing; I was there to turn Charlie into a black cock faggot. He was chomping at the bit. He had a hard clitty. He was wearing panties. My black stud thought it was funny that I had a little faggot boy watching. He didn’t mind. When I told him, I wanted him to skull fuck the little faggot, he didn’t skip a beat. He pulled his cock out of my cunt and shoved it in Charlie’s mouth. That would be as close as Charlie would ever get to my pussy. Charlie was in heaven sucking my cunt juice off his first black cock. He was a natural. Sadly, I likely won’t see Charlie again because he doesn’t live near me, but at least I gave him a memory he will never forget.

Lily’s Big Debut

Sissy trainingThe men gathered together waiting for Lily and I to come down the stairs. I spent over an hour getting Lily ready, I even put her chastity cage on her clitty for her to ensure it was done right. I surprised her with a blonde wig I bought just for her. Tonight she wasn’t going to just have her first cock, she was going to have as much cock as she could manage to take. By the time I was done with her, she was stunning a completely new person then that man I had known from work. Escorting her down the stairs almost made me feel like I was giving away a bride at a wedding, though instead, I was giving her off to be fucked for the first time like a woman. The three guys I selected would be gentle with my delicate flower, but their cocks will leave her aching. I watched as they gently touched her all over, kissing her and easing her down to her knees. Their cock’s hard and ready for those pink full lips to taste a real cock for the first time. Never once did she look back at me or try to back out. The moment she put the first cock in her mouth I knew Lily was all in and wasn’t going back ever again.

Put on those Silky Panties

best sissy trainer

Michelle tells me that I’m the best sissy trainer that she’s ever had. Michelle came to see me and he was dressed in blue jeans, a sweatshirt and work boots. I raised my eyebrow and told that girl to strip out of that crap right away. He had men’s white briefs on too. I cut them up in a bunch of tiny pieces. Then I put her in lavender silk panties and a white silk nightie. I made that girl put in a thick pink plug and stretch her pussy for later use. She whined but her clit was standing out all hard.
The next training that I gave to Michelle was cum eating. I didn’t want that sissy to embarrass me when she got cum from a real cock. I took a cum covered strap-on and fucked it into her lips. God, that lazy slut hadn’t even made her face up before she came over. I smeared the jizz all over her face with the strap-on and let it dry. That’s how I made her go out shopping. She had a tiny nightie, panties and dried up cum on her whore face. She’s almost ready for real dick now.

My Boss’s Transformation Continued

Sissy trainingOver the next few days, I would slip him a few more pairs of panties with instructions to be wearing a pair each day. Then I observed his behavior. He was happier, more relaxed having someone to share this secret with must have been a huge relief. Each night after work I would stay late (paid of over-time of course) and we would discuss my future plans for him. I took some measurements and we sat down and did some online shopping. I needed to make sure my slut had the proper attire for her debut weekend. Her sissy coming out party had been planned and now it was just getting her ready. First the outfit, we decided on an innocent look as we agreed it would be best given she was a sissy virgin. So white lace panties, garter, and thigh high stockings. A beautiful white satin chemise, with a gorgeous white sheer long flowing robe. The order was placed and set to arrive at my house the day before the party this upcoming Friday. So all that was left was practicing for the big day. I bring my strap-on to work and I’ve been teaching her how to suck cock, and I’ve provided other fun accessories to prepare her sissy pussy for her first time. Soon my new sissy who I’ve finally decided to bestow the name Lily will be more than ready for her big day!