I do love a good sissy training tale :)
“Please what Nick? Or is it Jessica right now?”
“God. Please…I need….to cum.”
Ms Brigitte laughed, softly at first, and then louder, knowing what that would do to him. It excited him almost as much as it did when she called him names. Names like Jessica.
“Right now? Does my little slut Jessica need to cum right….this….instant?”
“Please…please. Now…and…I just…I need to cum MORE.”
Now she REALLY laughed. She knew this was coming (and she laughed at her own pun), but just hearing that from Nick’s lips, from his painted red lips…it filled her with a warmth that she savored.
“What ever do you mean, sweetie?”
“I…I…I’m just all tense and frustrated all the time. I just can’t concentrate. Please, can I PLEASE cum more often?”
“Ooooh. That is a VERY big request for a sweet little girl. But you know I do love when you ask me things. That pleases me very much.”
“Please…PLEASE. I just need to cum more often. Please. Will you please let me?”
“Hmmm. I suppose we could work something out. And I’m even feeling generous. What if I even offered to let you wear boxers again?”
Nick blushed visibly. “For real?”
“Yes Nick…I mean Jessica.” Did he just blush even harder? It was so freaking delicious.
“What do I need to do? Please…PLEASE.”
It almost sounded like his voice was getting higher…this was intoxicating.
“Well Jessica…I have been thinking. You’ve been pretty good whenever you’re my sweet little girl. And you’ve been learning do to SUCH slutty things when I make you be my whore….but…well..there’s a difference between learning…and training, isn’t there?”
He couldn’t answer. It was too much. Just too much.
She went on. “You see Jessica, I’ve been thinking. You wear panties for me every day. You are…used to it. But I don’t want that. I want you to CRAVE it.”
“Actually Jessica – I want you to crave more than that.”
“So…here is what I am going to offer you. You can cum…any time you want. And I mean that – you can spend all day in your princess bed and just touch your little clitty all day long if you want, and I KNOW you want to.”
Nick/Jessica couldn’t hide it. He blushed…but nodded.
Ms Brigitte smiled. He was too precious. “You can cum any time you want. BUT…and pay attention to this – you will ONLY cum if you are wearing panties.”
She wasn’t finished. “Panties…and heels.”
“I…I don’t understand.”
“What’s to understand sweetness? You can cum every time your little heart desires, but you will put on clean panties…and pretty shoes, before you do.”
“I….I can do that,” Nick stammered.
“Shhh….shhh….hold on. It’s very important for me that you understand this. And that’s because I want to enjoy this gift you’re about to give me as much as possible.”
She stroked his face. “Oh yes. Because you’re going to agree to this. We both know you are. But you’re going to agree to it with full knowledge and acceptance of what you’re doing.”
“You see…Jessica. I am going to train you. I am going to train you to YEARN to wear panties. I am going to train you that every time those sissy panties touch your little clit, and every time you walk around in slutty heels that make your feet ache to deliciously….that you will feel pleasure.”
“I am going to TRAIN you to associate panties…and heels…with cumming. I am going to train you, so that every time you touch your little clit, you go further and further down that rabbit hole. You can fight it all you want, but we both know it will be inevitable. One day you will wake up, and you will simply want to wear panties and heels for me. And I am betting that day is very, very soon.”
“Put simply Jessica – I am training you to have a women’s shoe fetish. Among other things.”
“Three other parts to our little deal, before you go up to your little canopy bed. You can cum whenever you want, but after you do you will send me a picture of your pretty little feet in whatever heels you are wearing. And after you cum 10 times….I expect you to buy a new pair of heels. I cannot WAIT to see how big your shoe collection gets in the next 3 months.”
“Three months? Why 3 months?”
“Because, Jessica – in 3 months…you’ll only get to cum if you’re wearing panties and heels….and a skirt.”
I just love dressing up my sweetheart sissy girl, Jessica. Besides, the transformations that stick are the ones that start out subtly and work their way in.
Have you ever found yourself being transformed into a sissy through sexy lingerie and tease and denial?”
Here is a story that my slave Tony wrote for this journal
Auntie B had just finished a very long over the knee spanking. My cock was hard as a rock from all the tease and denial Auntie B likes to do during my punishments. She had a smile on her face when she looked down at my member. Of course, the penalty for not staying hard is an automatic 100 extra strokes with whatever she is using at the time.
“Get up and stand in that corner hands on head” she commanded and still crying freely I rushed to comply. As I stood displaying my well spanked bottom and trying to control my tears, I heard the punishment drawer open and the leather paddle was placed on its hook. I trembled visibly as I heard Auntie B withdraw something else from the drawer.
“Turn around” Auntie B ordered. She was holding the lubricant in her hand. “You’ve earned a release before bedtime but you will earn it, or there will be more punishment. Right now, I need to use the ladies room and make sure my panties are nice and soiled when I am finished. When I return, those moist panties will be wrapped around your face so you smell my scent during your orgasm. I want to see you kneeling in front of the spanking chair as I enter the room.” SLAP! “Now face the wall again please. Will you never learn that in the bathroom every time I find the toilet seat up, I will spank you again after dinner as another reminder? It’s a simple rule seat up, pants down.”
When she returned, she came and stood in front of me with a satisfied smile on her face. “I just took a nice long pee and wiped myself thoroughly with my panties. Don’t worry though, I made sure all of my scent is all around my panties. Here, see for yourself.” With that, she removed her panties and wrapped them around my face, making sure the most pungent part was right in front of my nose. Then she sat down in front of me and leaned forward. She placed her hand on my cock and began to stroke it a little. When I was ready to explode, she pulled away.
“Put some lubricant on your cock and start stroking your cock.” She began to rub and squeeze me nipples. HARD. “Here is how this is going to work. I am going to continue to work over your nipples. You will have 30 seconds to cum when I tell you to get started. If you don’t cum in 30 seconds, you go back over my knee for the same amount of time and I will get in as many hand spanks as time allows. After that, the seconds go up 15 seconds at a time. In other words, if you don’t cum in the first 30 seconds you will have 45 seconds in the next segment or its 45 seconds over my knee and so on. How bad do you want to cum pet? You better get it done quickly. Remember, you have another spanking coming after dinner before you go to bed: Her smile went right through me. “Get started!”
The big day had finally arrived. I was about to meet Auntie B. I hadn’t slept in three nights in anticipation. Was the build up too much? Would the wait really have been worth it? I couldn’t get her pictures out of my mind as I walked up to the door. When I heard the locks tumble and the door knob turn, all my questions we answered in the next five seconds. There stood Auntie B. As intimidating as I thought she would be, but much prettier than I ever could have wished for. She had written me through the weeks with some fantasy choices. I thought they were meant to be just a fantasy.
Choice number one. I will take you over my knee and spank you very soundly for 35 minutes with my hand, or you can have a 15 minute spanking with the instrument of my choice and you will count. I knew that either meant the hairbrush or the strap and I hate counting out loud. It breaks my concentration. This was an impossible choice. She told me her hand is like iron but her instruments can be very painful as well. Then she added another twist as she looked me right in the eye. If you choose my hand and I feel you are wiggling too much or getting out of position, I have the option of getting the round leather paddle, locking you over my knee and adding another ten minutes. I knew I was making a mistake when I chose her hand and saw her face light up with a huge smile.
Choice number two. I will squeeze, bite or pinch your nipples for thirty minutes or you can choose to wear clamps during your entire punishment. If you choose the first option, that doesn’t necessarily mean I will do the entire thirty minutes at once. I might choose to bind you to a table and just do ten minutes while I tease you. Then I might decide to do five minutes four more times. Auntie B was loving every minute of this. I told her I absolutely hate nipple clamps. I can’t concentrate when those damn things are on. I knew it was a mistake but had little choice when I chose not to have the clamps. Good boy, she affirmed.
Choice number Three. When I am through spanking you, it’s time for a little humility. I can both keep you over my knee and violate your prostate for as long as I want, or I can take a butt plug covered in stinging ointment and be much rougher for 10-15 minutes. If you choose the first option, I have the choice of putting a butt plug inside you before dinner tonight and making you use it all through dinner. I didn’t know what to say. I wanted this to be over and not worry about it all day but that ointment can be very harsh as well. Plus, what if she inserts more than one finger? BTW, if you select the first option, we will come back here after dinner, I will remove the plug and you will be spanked by my hand harder than I have ever spanked you before. I was beside myself. Auntie B had her hands on her hips as she tapped her foot. Well!! I guess I’ll take the first option, I softly said as I was staring at the ground. She walked toward me, grabbed my chin and put her face right in front of mine. That was your first mistake!! Now open your mouth. She gave me another cup of coffee.
Choice number four.The choices wouldn’t be complete without my fucking your little ass. Here I have two strapons. I will you bend over the bed or fuck you doggie style with the smaller dildo until I am tired, or I can use the larger one and fuck you very hard for 10 minutes. I was spent and didn’t know what to say. I figured by this time she might be tired so I chose the first option. This was a no win choice. I just hoped that by then she remembers it is my birthday.
“Hello Tony. Please come in.” Her voice went right through me. I gingerly stepped in to the room as she came closer to me. SLAP! There it was a slap right across the face. Not too hard but just enough to get my attention. As she moved closer, she grabbed my chin and put her face close to mine. “You have been having a lot of fun lately haven’t you? You have been looking at my pictures choices and masturbating too” “Yes, I mumbled.” “Well honey, the party is just beginning. Open your mouth and put your head back.” As she spit in my mouth, she said, “that’s the only spit swapping you will be getting for awhile.” With that, she grabbed me by the ear and led me into the room where there was a small foot stool. As we moved closer, in one fell swoop, she put her foot on the stool, pulled me over her thigh, and held me tightly by my hip. She then began spanking me very hard over my pants.
As I stared down the back of her leg, I couldn’t believe how strong she was. My face was sore but all I could think about was the spanking I was getting. Are you kidding me? I’ll never be able to take this on my bare bottom. She continued to spank and scold me. Just when I thought I couldn’t take anymore, she stopped and stood me up. She had my full attention and she knew it.
She grabbed me by my hand and walked me over to a chair that was in the middle of the room. As I stood in front of her, she began to unbutton my shirt. After she had taken it off she moved her head t my chest. Her hair smelled wonderful. She began to pinch my nipples and then I felt a great deal of pain. I almost buckled. She smiled and then sat in down front of me. . “I have had a long day and I am hungry Tony, so here is what we are going to do. I am going to put you over my knee and give you a very hard spanking. THEN, we are going to dinner so I can watch you try and sit comfortably while eating. When we are done, we are going to come back here. This way, I can take as much time as I want giving you the discipline and training you deserve as we go through all the choices that I sent you. Before each scenario, you will go back over my knee so I can make sure your ass is sore through the entire session. Any questions?” I didn’t know what to say. “No.” was all I could think of. “Good. Let’s get started.” As my pants fell to the floor and my underpants followed. Then she gave my manhood a very hard squeeze. It’s funny how things always seem more pleasant in a story, than when they actually happen. It certainly didn’t feel funny when she stopped squeezing to pull me across her knee for the first of many bare bottom spankings. True to her word though, she did give me a warmup with the proper scolding and concentrated on my cheeks. I couldn’t help but think how such soft hands could hurt so much. “Whew, I’m hungry. Let’s go eat.” she said.
The restaurant played out just as she thought it would. She was beaming with confidence and was quite the lady. She was very bright and wonderful to talk to. I couldn’t take my eyes off her face. No one else in the room knew that I was completely hers. My bottom was sore and kept reminding me that the person across from me was going to be giving me the punishment of a lifetime in about another hour and I didn’t care. Although I tried not to show it, I was nervous and a little afraid. At the same time though, I was at peace with this woman. It was like no one else could do me any harm as long as I was with her. I was hers to punish and no one else could.
When dinner was over, we did exactly what she said we would. We went back to her place and covered every choice. Plus, my bottom was spanked between every event.
We were both very spent by then and I went and took a shower. When I came back out, she had a sinister smile on her face. “Tony, I have one more choice of my own.” “What’s that?” I inquired. “Would you like to spend the night with me? I’m not talking about sex, even though I might have you please me at some point. What I am talking about is spending the night together while spooning and cuddling.” “That’s an easy choice.” I said. “Well that’s the tricky part.” She came over and held me to her chest. “There may be a bedtime or morning spanking in it as well.” I knew I couldn’t take much more spanking but as I had her arms around me, I knew which choice I wanted. After the punishment I received, the thought of being in her arms for a night was too much to bear. I would do anything for her. I felt sense of security and protection with her that I haven’t felt in a long time. “Yes. Please Sage. I want you to hold me all night.” “Ok Tony, let’s go by the hotel and get your things.” She patted me bottom as we broke apart.
The rest is up to your imagination.