Tag: Best sissy trainer

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!

The Beginning Of My Boss’s Transformation

Best Sissy TrainerI work in one of those standard boring offices with a nine to five gig. It fits me most of the time, however lately my boss has been a major buzz kill. He’s starting to complain the clothes I wear are no office appropriate. He went as far as to tell me that my skirts are to distracting for the males in the work place. I’m use to sexism but nothing has really changes until this last week, and I’ve been racking my mind as to why. And a thought occurred to me, last week in the break room I spilled some coffee on my blouse and since I was the only on in there I went ahead and did a quick change. But if that perv was watching the camera then he may have seen me in my pink bra looking through my bag for another top. However, it doesn’t explain his recently attitude toward the way I dress…unless he was jealous. I easily pick up on those kinds of things. So I tested my theory and waited for most of the office to clear out before requesting a meeting with him. I shut his door and pulled the blinds down while he gave me a puzzled look, and then I threw a pair of lace pick panties on to his desk. “Put them on”. He blushed and cleared his throat. “Excuse me?” he attempted to question me. I laughed at his attempted to cover up what I already knew. “I said get you sissy boy ass up and put on the panties, I was very careful to get a pair I was sure would fit you”. The room fell silent and for a minute I thought maybe I was wrong. Then he picked up the panties and started to feel them in his hands and smiled. “How did you know?” he asked. “Because all sissy sluts act jealous around me. I’m everything you want to be, and if you do exactly as instructed I can get you as close as possible to being just like me.”. The happy look in his eyes told me exactly all I needed to know. Now the fun part can begin.

Cucksucking 101

Sissy Girl TrainingWatching a sissy suck cock can be so amusing. The cock hungry little whores just try to swallow the things which may make the guy cum but won’t necessarily be a mind-blowing blowjob. It lacks a key ingredient that linger with a man after he gets his dick sucked. That my sluts is the art of the tease. If you want to ever be considered among Arabelle’s darlings then you will listen to my advice and learn to utilize it. Any man can find a whore on a street corner to devour his cock for a quick 5 minute nut, but a real woman no matter how salacious have class. I can give a man a blowjob that will have his mind reeling because I know how to take my time. I know how to use my skills to tease every inch of his cock and balls. While still catering it to what he likes. You need to listen to the sounds he makes, test out his super sensitive areas and see how you can make him squirm beneath you for a change. That’s how you become the best cocksucker you can be.

Forced Sissy Training Karaoke Cock Sucker

Forced sissy training

  This little cock sucker deserved the forced sissy training she got. Last night at a karaoke club my friends drug me off to had the most pathetic guy up there. He practically embodied the need to be a little bitch and the way he nearly sucked that microphone had me thinking. I gathered a few friends, we were tipsy and in a fun mood. We made up a glory hole in that clubs dank bathroom. We pulled that little bitch in there and made him go to work. I knew he really wanted to suck a real cock and he got one. Now he is my bitch and I get to dress him up and train him to be a good cock sucking sissy slave. I think you should stay tuned and see how this plays out. Maybe you are wanting the same?

 

Comply Or Perish

mistress phone sex

No matter how many disobedient boys I talk to there always seems to be another one in need of correction. It’s a good thing that there are lots of Dommes that are ready to take the whip to them and correct their behavior. I can only imagine the perverse things that you’ve done that you need to confess. Confession is good for the soul. Come to me and kneel and tell me what you’ve done. I’ll go from there in deciding how to deal with your actions. I’m not a kind Mistress either, I will bring you a great deal of pain.
If you’re sitting there stroking your hard cock and thinking of Mistress phone sex take your goddamn hand off of it right now. That is not for you to touch without permission. Boy, you are going to be a lot of work aren’t you? That’s OK, I am a strong Mistress and I’ll make you crumble at my feet in worship. It’s actually your good luck that you found me. I’ll bleed the bad right out of you and baptize you in blood only to have you reborn as my servant. Your body, mind and soul will be mine.

Princess BBC Sissy Trainer Zoey

BBC sissy TrainerHaving a boyfriend and daddy that need Me as their BBC sissy trainer makes me very wet and Cumming constantly. I love feeding them Big black dick anytime I feel like it. My sissy lala boyfriend and I were studying for a major test and my pussy began to throb from out of nowhere. And that is when I heard our neighbor Shawn and daddy talking downstairs. My pussy had BBC radar I swear! I got up and told My Boyfriend that we needed to put on our prettiest panties and nothing else because I was going to get at least one of us fucked! I ran downstairs dragging my sissy BF. I Was so excited that I ran right into Shawn. AL 6 foot 5 inches of chocolate man meat! My tits pushed into his chest as he looked from me to my Boyfriend in his sissy panties. My daddy had stopped in the hallway knowing what his baby girl mistress what up too. Shawn looked to daddy saw his face and back to me. He laughed and said little cuckold mamma you run this fucking house, don’t you? That when momma came in from work and said yeah she does now are you going to fuck her like she deserves Shawn? Momma is so good to me. We fucked all Saturday night me and momma sharing his 10 inches while Daddy and sissy boyfriend watched, jack off and cleaned us up.sissy panties

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.