1,509 results for sissy training

Heaven Commands You

        adult phone chat lines My sissy boy sucks the most cock. As you know I adore sissy training. I decided to go underwear shopping with one of my favorite sissies. We went to the mall together and I helped him pick out a bra and a thong. Then I ordered him to go to the dressing room.The retail worker said ‘hello, did you find everything you were looking for’ I said ‘yes, my sissy friend here is trying on some lingerie. Could you tell him if it looks good when he tries it on?  “Most certainly, he said. After my sissy came out in his bra and panties, he showed it to the clerk and he said ‘turn around nice,nice, you got a tight butt back there.’ well… my sissy boy said teasingly ‘why don’t you come into the dressing room with me and help me unhook my bra?’ I know they went back into that changing stall together, but I do not think he was helping him with the bra  really because I saw from underneath the stall. He was getting down on his knees and the worker took his cargo pants down. I heard some dick sucking noises. Looks like my sissy friend got lucky at the mall.

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.

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.

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!

Tammie gets a Treat

Sissy TrainingMy sweet little Tammie has been such a good girl lately. Doing everything that was asked of her. She had been our little cum whore at my last penis party and even licked up my creampie pussy without even being asked. She stayed on her little knees and sucked every man and shemale that came to her so that they were nice and hard and ready to go. She politely lifted her sweet ass and let them take turns ramming their dicks or dildos deep inside her. She cleaned everyone up too, leaving not a drop. So, to show her how wonderful I though she had been I got her a special present. Laid on the bed was the prettiest pink dress and matching garters, a pair of silky hose, black heels, toe rings and a beautiful new cock cage. Her eyes lit up when she saw them, and I told her to put them all on. I had her twirl round and round as she showed her new outfit off. Finally, I told her to lay down on the bed because her best present was yet to come. I could see the liquid dripping from her sweet cock cage from excitement as Sandy, the biggest, blackest, most beautiful shemale entered the room. I handed Sandy the key and told her that Tammie was ready to play as I winked at her and closed the door.

Susie Needs Cock Control

Sissy TrainingI often get clients that have a foot fetish. I can totally relate because feet are sexy, especially mine. I had Susie take a nice long bath, removing all that hair surrounding her sweet cunnie and put on some nice soft lotion. Susie then laid down and I attached the cock cage so we could work on a little cock control. Then just to make sure Susie knew how much it would hurt if that sweet little clitty of hers got excited I spread her soft legs and played with her clitty with my toes. I rubbed all around her, even tapping that cage a little hard. Susie was breathing heavy and I knew she was starting to enjoy this. I then put my feet right to her lips and she began sucking on my toes. This is one of her vices and sure enough that little clitty started to get excited only to be held down by the cage. Susie let out a little yelp but kept on sucking my toes. I even saw a little precum coming out of that little clitty. My goodness she must be in pain, but her love of feet has even won over the pain. Hmmmm maybe we need a smaller cock cage to learn to control this fetish.

Brandie gets a Treat

Sissy TrainingSweet little Brandie has been wearing that cock cage for awhile now and every day I remove it and make her watch some shemale porn. And wouldn’t you know it, her sweet little clitty has remained soft every time. Now, one of the most important things in sissy training is rewarding for good behavior. So, I told Brandie that she had been such a good little sissy lately that I was going to give her the best present ever. Her eyes lit up and she guessed a new butt plug. Nope, I said. I did tell her to remove her current sparkly butt plug and take a nice warm bath, paying special attention to her little man pussy. She practically skipped to the bathroom. I had laid out some silky black panties and a matching bra for her to wear under the most flowy sundress I could find. She looked marvelous. I finished her look with some pretty pink lipstick and off we went. I blindfolded her to not spoil the surprise. Once we arrived, I opened the door and guided her in. I removed the blindfold to reveal the most marvelous sex shop around. Her eyes popped as she checked out all the butt plugs and gigantic dildos. She even stopped to look at the sex machines and picked out a sweet little vibrator for her man pussy. We viewed a few of the peep shows and Brandies little clitty did not even perk up. I told her what a good little sissy she had been, and I had an even bigger reward waiting for her. We walked to the back and through the fire exit door to a magical place. An underground sex club. I told Brandie that since she had kept that little clitty of hers in check all week that she was free to play with anything and everyone that she wanted. She smiled like a little  girl and practically ran to the glory hole wall.

Let Me Show You How To Do It!

sissy girl training

Hi. Don’t be shy. You are in the right hands for the sissy girl training you are seeking. I love helping wannabe sissies like you get all the way there. You can only wear so much lipstick and so many pairs of panties before you want to take things further. But you might not always know exactly what to do. That’s why you need a perfect girl like me to help you out. I will do everything I can to make sure you learn how to be the best sissy you could possibly ever be. I won’t judge you, but I can’t like – I might giggle but it will just be because I think you trying to be a good girl is so cute.
Do you think you are ready to be the perfect sissy? I’ll help you learn how to act like a girl, dress like a girl, and fuck like a girl. I will absolutely steer you in the right direction in every single area of your life. I can’t wait to complete the sissy training process on you. Are you willing to trust me to do right with your sissy transformation? Give me a call so we can get started!

You Need A Forceful Queen!

forced sissy training

Oh, you don’t want to be turned into a sissy? I think you do. You keep talking about wearing panties and sucking cock with lipstick on, so I think that qualifies. I think what you need is some forced sissy training and before you know it, you will be ready and willing to be the sissy you’re meant to be. And if not, oh well. You can keep denying your desires all you want, but we both know that you’re going to be secretly glad that I’m helping you transform into a perfect little sissy slut.
I am more than willing to push you down onto your knees to suck cock. You’ve been talking for so long about how you’d love to do it. You want to taste that cum in your mouth and swallow it. At least that’s what you say. I’m here to stand right behind you and hold your head still while he fucks your mouth. You might choke and gag, but that’s okay. I really don’t mind and I don’t care if you mind. This is what you’re meant to be doing so just be a woman and deal with it. That’s just the beginning of your sissy training, but don’t worry. We’ll get to the rest soon.

Heaven



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It’s Heaven here for all your sissy training needs. I am more than willing to help out with making you into my little bitch. You will be made to wear women’s lingerie and I will make you wear a dog collar as well. I will walk you around the house on your hand and knees. I will get out my whip and strike you if you disobey me. Then we will have fun with a strap on. I want you to take all of it in your ass. Don’t be a weak little bitch either. Take all of it like a real whore would. I am going to make you do chores around the house in heels. Fold my laundry. I might even bring my big black cock friends over and they will all take turns letting you suck there big cocks. Think you can handle them? You wont have a choice. Either way you will be talking all three of them in your ass that night. I need my sissy to be a freak that isn’t scared to get wild. When you are further along in your training I will let you have new outfits to wear and be feminine in. But you must be a good submissive little sissy slut nd do exactly what I say to deserve new clothes. As punishment for not being an obedient little sissy boy you will be spanked with a paddle til your ass is nice and red. I enjoy sissy training so much because it gives me control over these messy queens who need some guidance. Trust me you will get an A plus in drag by the time I’m done with you honey. I can make even the most masculine looking man a little sissy slut in the blink of an eye.