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?”
It could only have been about fifteen minutes, but she couldn’t check her watch as she had her hands on her head, facing the wall, outside the headmistress, Miss Brigitte’s, office. Fifteen minutes, but it felt like an eternity.
She had started out fourth in a line of miscreants, and now it was down to her. Two girls had already come and gone, dispatched from the office in varying states of distress. Now it was the turn of the third girl, Roberta Jamison, and she had been in there an age. Sissy Miranda was musing on why this might be when, suddenly, the heavy mahogany door of Miss Brigitte’s study swung open, and out stepped Roberta. ‘Your turn now,’ mumbled the girl to Sissy Miranda, ‘she wants you in straightaway.’ Sissy Miranda turned round, managing to raise a brief half-smile to her tear-stained fellow, before knocking on the dreaded door herself.
Miss Brigitte was sitting behind her desk, a fine, crook-handled cane prominently on display before her. This was a weapon Sissy Miranda had become familiar with over the past few years – that and, of course, the strap. She did not know which she hated the most, but having tasted the bite of both, she was at least prepared for their sting: Miss Brigitte couldn’t really hurt her.
‘Well Sissy Miranda, I haven’t seen you in my office for a while,’ began Miss Brigitte. Sissy Miranda remained silent.
‘I assume you have a note?’ continued Miss Brigitte.
Sissy Miranda stepped forward and held out the note she had placed in the top pocket of her blazer.
‘Cat still got you tongue I see,’ went on the Head, as she picked up her glasses and read through the missive.
Sissy Miranda said nothing.
‘Well, this sounds like a very childish offence,’ asserted Miss Brigitte at last, surveying the tall fifth-former before her.
‘Go and fetch me that chair,’ she suddenly instructed, indicating a low wooden chair near the window, ‘and put it in front of the desk.’
Sissy Miranda didn’t move.
‘Do it, right now!’ commanded the Head.
Sissy Miranda’s feet obeyed, despite her mind reeling in confusion: this was not how she took the cane, or the strap for that matter.
Miss Brigitte stood up, waited for the chair to be settled, then sat down.
‘Come here and bend over my lap.’
Again, Sissy Miranda didn’t move.
‘Come here at once,’ continued Miss Brigitte, her voice rising to a crescendo, ‘or I will spank you harder and longer.’
Spank? Sissy Miranda was horrified: she had never been spanked before; never had to lie across the lap of the head mistress – this was too much.
‘Come here!’ ordered Miss Brigitte, and this time the girl did move, approaching the Head and then lowering herself carefully over her lap as indicated.
Before she could do anything else, Miss Brigitte had pulled back her skirt, pulled down her pink frilly panties and slammed her hand down hard on her behind.
‘Ow…ouch!’ issued from Sissy Miranda’s lips in shock, as another blow, and another rained down.
‘Be quiet!’ ordered Miss Brigitte, Sissy Miranda gritting her teeth as the blows increased in intensity; ‘This is not your place to speak!’
Last week, my mom took me up to my auntie Brigitte’s home for Thanksgiving gathering. We got there and gave aunt Brigitte a hug, she was wearing a red sexy dress that made her butt look amazing.
After dinner my cousin Jack and I went down to the basement to play ping pong. We started getting bored with that and decided to start wrestling. It was so funny, we were jumping off couches onto eat other. Jack picked me up and slammed me on the couch. I got up and ran away but he chased me, I stopped and flipped him over my shoulder and he landed on the coffee table and broke through it.
We stopped in silence and didn’t know what to do. Before we could do anything we heard someone coming down the stairs. It was my aunt.
She asked sternly: “What did you do?”
She grabbed Jack by the ear picked him up and said “I just bought this coffee table a month ago.”
Jack replied: “I know mom im sorry it wasnt my fault.”
She said “Oh really then who was it?”
Jack said “It was Charlie he flipped me into it.”
Aunt Brigitte looked at me very angry and asked me if it was true.
I said “Yes aunt Brigitte, I am sorry, we were wrestling and things got crazy”
Aunt Brigitte replied: “WRESTLING?! Jack you know there is no wrestling in this house. That’s it. Both of you upstairs now.”
We went upstairs and were lead by my aunt to my mother. My aunt told my mom what happened and my mom went to the basement and looked at the coffee table. She came back up and said” Brigitte,, you can punish him how ever you want, and Charlie I hope that your aunt spanks you hard, cause if it wasn’t Thanksgiving and I wasn’t in such a good mood, you would be getting a second spanking when we get home.”
Before i could say anything my aunt told her “Kristine, I would like you to join this spanking”. My mom was honored and accepted the invitation. My Aunt said “follow me everyone.” We followed her outside and I knew we were in for that chair spanking bench.
Just before we got into the shed, auntie Brigitte told my mom “I have a new bench to show you”
We got in the wood shed and my Aunt made us strip completely naked. Then she made Jack go under the chair and into position. Jack was naked tied upside down on a chair basically.
Jack’s naked bottom sat high on the edge of the chair. His balls and penis tucked on the underside of his thighs which meant they were visible in his position since he was upside down. Aunt Brigitte pulled a leather strap of the wall which was probably .5 inches thick, about 20 inches long and was cut into 3 long strands. The handle was wooden and the leather itself was very thick.
Aunt Brigitte told me to turn around so i couldn’t see the pain Jack was getting. I stood in the corner facing away as I heard loud cracks and cries from Jack. I felt bad for him but knew I was in for it. His spanking felt like it went on forever. Finally my aunt untied him and told me to come over.
I laid on the pillow under the chair. I put my legs up on the seat and felt my knees get tied to the back frame. Then my arms were tied under the chair. The chair was on an elevated platform that was at perfect position for bring down licks. My bare bottom, penis and balls were all in the air. My aunt then gave me the first lick
I couldn’t see it coming and I was in such a easy position for a lick that it hurts me really bad.
Crack CRACKK Crack
One stroke hit my penis which made me jump
Crackk Crack crackkk
I yelled and cried, another hit my balls which made me scream very loud
CRAck Crack crack CRACKK
Each stroke hurt more and more, I knew my bottom was burning red
Crack Crack CRACKK
Aunt Brigitte gave me about 20 strokes which was 20 less than what Jack got.
but then she handed the strap to my mom and said “Would you like to add your touch?”
My mom rubbed my bottom as I jumped from the pain of her touching it. She said “His bottom is perfectly done” I was glad to hear that and thought my punishment was over. Then my mom said “but lets add some red to his thighs.” Then my mom laid the strap on my thighs, got into a good position and started striking my thighs with the leather strap.
Crackk Crackk Crackk
Thigh spankings hurt a lot
Crack CRACk CRAck
I cried loud
The leather bounced off my thighs and sit spot
My mom turned my thighs as red as my bottom.
She then undid me and told me to put my clothes on. aunt Brigitte said “Next time I spend 300 dollars on a coffee table, I expect it to stay perfect or you will be held accountable” We both sniffled and walked back into auntie Brigitte’s house and tried to enjoy the rest of the day. I still cant sit today from that strapping.
“What did you say there Tony??????????? ………… Repeat that if you dare!!!!!!” A fuming Auntie B stood right in front of Tony. He looked at her, made a big judgmental mistake about the situation and repeated: “Wow, are you getting bitchier lately Auntie B?” Hardly had he spoken those words or she slapped him in his face which left him a stinging red spot. “Ouch, crazy woman. Are you nuts?” Tony said angrily while rubbing his cheek.
“Calling me nuts? Calling me a crazy woman??? First insulting me because of my attitude and now calling me names as well? How dare you speak to me that way bratboy? Even though your in your forties, still haven’t learned to show any respect at all for the opposite sex, do you?” Auntie B was a nice built woman, who was in her prime. She always dressed modern but casual, and three times a day she passed Tony’s room while collecting reports from the reproduction room. Most times Tony said timidly hi to her, while she waved cheerfully to him or looked playfully stern. Until now that was…… Auntie B, raged with anger by his behavior, made her decision. She pushed Tony back into his room, followed him closely and carefully shut the door behind them. Then she said sternly: “I think it’s time for a little discussion, don’t you agree young man?” Tony started blushing, knowing that this was the moment he longed for but at the same time was afraid for. While he sheepishly looked down, he remembered exactly when he had heard her use that sentence before.
Three months ago he had a received a call from Marc, a colleague, who complained about a problem of logging on at the server. Tony had checked everything on the server, but couldn’t find anything strange. In the end he decided to check out the computer of Marc in the hope to discover there something. The door was closed, but being his usual self, Tony rushed in without knocking the door. There he saw Auntie B in the middle of the room sitting in an armless chair with Marc draped over her knee. Tony was completely astonished and stammered “Ehh.. I just wanted to check the client-software on your computer Marc” “Marc doesn’t have time at the moment as you can see” Auntie B said sharply. “We are having a little discussion right now! And didn’t you learn to knock before entering?” Auntie B ended her lecture with a stern: “Close the door on your way out, you rascal and quickly before I spank you as well!!”. After that, she payed her full attention to the jeans of a pleading Marc. Totally flabbergasted and completely flustered Tony walked out of the room and closed the door at the exact time Auntie B ’s hand with an echoing smack contacted Marc’s bottom.
Marc had left the company a few weeks after the incident and both Tony and Auntie B hadn’t spoken a word about it to each other. Since that day though, Tony had dreamed about Auntie B, strong lectures, lots of spankings, and those lovely knees to lay over. But how to get in that situation…. he had no idea, or better said, no courage. Auntie B also had since her little discussion with Marc lots of ideas about Tony, and especially about that naughty bottom of his deserving her special attention. She thought of him bawling over her knee, while she would paint his buttock a nice mix of scarlet red and purple with her hand or leather paddle. Mmmmmmm, when she walked by and saw him greeting her clumsily, she secretly hoped to find a motive to put him over her lap.
That moment had arrived now. In deep thoughts, she had passed his room on the way to the repro and back and had forgotten to greet. Tony was annoyed big time and had tried to catch her attention with this crude remark. That worked, she was very upset now, and determined to teach him a lesson. Carefully Auntie B rolled up her sleeves and snapped to him: “You still haven’t realized what I do with naughty brats, have you? But my little rascal, you will suffer soon the consequences. Because of this insult you will go over my knee and get the spanking of your life!! And on your bare bottom!!” Then I am going to play with your prostate before I bend you over and give you a taste of my strapon. When we are finished, you are getting a golden shower from me and I have a lot of shower to give. We’ll swap spit but not the way you like it. If you are lucky, I’ll straddle your face afterwards and play with your nipples as you act as my toilet paper. I haven’t decided whether to give you a release or not. What I can promise is that I will stroke your cock through the entire punishment and make you beg for an orgasm.
She took the armless-chair and put it in the middle of the room. Then she walked resolute to Tony, took him by his ear and guided him to the chair. She sat down, hiked up quickly her skirt and unbuttoned Tony’s trousers. Then she pulled him in one swift movement over her left knee and pinned him down by putting her right leg over his legs. Without words she peeled the undies from his bottom and without further adue she started to spank those naughty buttocks hard with her hand.
Tony, though having dreamed of this little scene, slowly felt the heat on his bottom build. Stoic he tried to bear his punishment, but her skillful hands got after a short period some painful moans out of him. Auntie B smiled, hearing this, and got out of her leather paddle, took it from the ground, and started now really to put an fire on Tony’s ass.
“You naughty little brat, after this spanking you won’t sit for a week…. Smack slap spank, from the left cheek to the right, smack, spank slap, let’s give that bottom it’s well deserved scarlet red color!!”
Tony started crying “ooooooooohh I.. I am so sorry Auntie B, I was only joking.. r.. really, p… pleaaase, I will behave!!!” “Yes, you certainly will, my naughty boy”, Auntie B said while painting every inch of white skin on Tony’s buttock’s red, “Because if you don’t, from now on we will have just as much little discussions until you do!”
Although Tony pleaded in tears to be good, Auntie B was deaf for his pleas and didn’t stop spanking him until she decided he had enough. When that was the case he laid sobbing over her leg and softly whispered “Thank you for correcting my behavior Auntie B ” She softly caressed his scarlet bottom and said, “you’re welcome Tony, be prepared for lots of little discussions of mine in which you can admire the carpet frequently from now on!! We are not finished yet.”
We still have more S’s to go through.” She leaned over to pick up something and heard the snap of a leather glove, followed by her strong hand separate his ass cheeks. After a cool liquid was applied, her fingers were deep inside him probing his prostate. He tensed up only to feel a hard spank on his bottom. “Sit Still or it will be a lot worse. We have a long way to go.”
“Y.. yes Auntie B, I will “, Tony sobbed.
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.
Longing and Deception
Jo, was spending a rare weekend alone with his Aunt Nancy. His uncle and cousins had just left for bible camp. Jo finally had the chance to try and experience Nancy’s treatments that his cousins had told him stories about and he so much wanted done to him. When Nancy sat down on his bed to tuck him in for the night wearing only a silk nightgown, he complained that he had a tummy ache. She acted concerned. She slipped her fingers down under the waistband of his pajamas and while innocently brushing against his rapidly swelling penis she pressed around on his abdomen.
While giving him a big bosomy hug she told him she knew exactly what she needed to do to make him feel better. However, they would have to wait until she returned from her hospital shift the following afternoon. While he felt her hard nipple press against his cheek thru the sheer silk fabric, his anus twitched in anticipation of the unknown. Once the door shut, Jo pulled out his flashlight and ogled thru the big envelope of porno pages his cousins had loaned him.
The following day, at the hospital, aunt Nancy’s supervisor informed her that she would have to stay for the night shift. Not wanting to leave Jo alone, she called Auntie Brigitte, who introduced herself at church last week as having just arrived from France to serve at the local Catholic girls boarding school as Headmistress and School Nurse.
Brigitte immediately offered to watch Jo overnight at her apartment. Nancy thanked her profusely, but added he had a tummy ache and she was planning to give him his first enemas. Brigitte explained she would evaluate his condition and the academy clinic was well equipped in that area of treatment… (and she was secretly eager for the chance to work with some male anatomy for a change…).
Nancy told Brigitte that if Jo gave her any trouble, she should sternly discipline him. She then proceeded to call Jo from her wall phone and instructed him to pack a small overnight bag and walk the 2 blocks to her new friend’s on-campus residence and arrive at 6pm sharp.
Jo was soooo disappointed!! Oh well, he could just watch the Seahawks game. He threw the big envelope into his overnight bag for some later nocturnal reading. His treatment from aunt Nancy would just have to wait another day.
When Brigitte heard the doorbell ring, Tom offered a disinterested hello, dropped his bag in the hall and immediately went over to her TV and turned on the game.
She moved his bag to the clinic guestroom where an envelope fell out. Her curiosity tempted her to take a peek.
OH MY GOSH!! Another boy just waiting to poke one of my girls on a first date!
Both embarrassed and angry, she marched out to confront Jo:
”Tell me what is in this envelope, young man…”.
Without turning his head from the screen, he told her not to interrupt him until halftime. Now at the end of her patience, she slammed off the TV, grabbed a handful of his hair and struggled to drop his pants. He soon found himself stretched across her lap with his penis trapped between her strong thighs. This wasn’t her first rodeo
”I will ask you again, Tell me what is in this envelope, young man?…”.
When he answered that he had never seen it before, the spanking began and continued for several rounds of repeated questioning and increasing intensity until he could take any more and confessed to having naughty pictures in that envelope.
She stood him up and looked at him straight in the eyes while squeezing his cheeks. She explained to him that he had a choice:
she could either show the envelope to Aunt Nancy tomorrow, or he could let Auntie Brigitte discipline him right now and Nancy would never have to know.
Not wanting to get his cousins in big trouble, Jo agreed to let what happens in Brigitte’s apartment stays in Brigitte’s apartment. How bad could that be, anyway?
Seduction and Discipline
Knowing she couldn’t ave sex with him, she was still relishing the opportunity to torment Jo with her seductive touch and posturing that would arouse his emerging sexuality interspersed by humiliating and uncomfortable medical procedures in a revolving cycle of intensely confusing erotic sensations.
She was well experienced in leveraging the power of the prostate and ready to lead him past the societal humiliation and onto accepting anal bliss…. But first she had to soften up his male machismo for him to be ready to make that surrender.
Sensing his uncontrollable curiosity in the mysteries of a woman’s body she seductively removed her dress.
Picking up her cane and tapping it on her palm, she asked Tom if he liked what he saw; auntie Brigitte now standing defiantly in front of him wearing only a silk bra, panties, garter belt and stockings.
Arranging a stack of pillows on the bed, she grabbed his arm and positioned him spreadeagled over the hump widely spreading his legs. He lets out a yelp as he felt a stinging soap covered butt plug being relentlessly pressured up his anus and lodged into his rectum.
“Don’t you dare let that come out until I decide to remove it”
Picking up the envelope, Brigitte sat down next to him and pulled out a page and showed the first image to him.
And so began his discipline, as she retrieved her favorite cane, paddle and strap and began delivering some strokes before taking a break to show him the next page’s revelations and starting the next round of gradually intensifying strokes. This continued in several cycles before ending with a crescendo of stinging rapid fire impacts that left him whimpering in a fetal position. He was now ready to move on.
Changing her demeanor to mothering care, Brigitte cuddled Jo in her arms, smothering him tight against her chest and asks if he had learned his lesson.
Like a needy dependent child, his bottom stinging with pain, he clamped his arms around her and quietly thanked her. Asking if he could now go back and watch the game. She said NO and explained that they still had more important business to attend to. She told him that aunt Nancy had voiced her concerns about his tummy ache.
Jo answered that after aunt Nancy pressed on his belly she told him she knew what would make him feel better. He expected her to take care of that tomorrow.
“No need to worry about that tonight, Auntie Brigitte! “
To which, Brigitte retorted that she is the academy nurse and Rosie had requested that she evaluate his condition. …..She wouldn’t pass up this opportunity for the world…..
With an ominous smile, Brigitte said:
“Let’s check out Tummy tummy…”
and proceeded to straddle Jo’s face backwards, smothering him with her butt and introducing him to the overwhelming scent of a woman through her silk panties as well as holding him down while sensuously pressing around his abdomen and meandering her hands down to tease his genitals, lightly stroking him, cradling his testicles and pulling on his emerging recent growth of pubic hair.
Returning attention back to his abdomen she mused:
“I can understand why Nancy was concerned”
She got off him as he found himself gasping for air and ordered him up onto his hands and knees, face down on the bed. Snapping on a rubber glove in front of his face, she moved back out of sight and he felt the first-time delicate teasing touch on his virgin anal opening and perineum.
HOW HUMILIATING! He tried to get up but she pushed his head back down
“We aren’t done yet, young man…..”
She firmly grabbed his testicles with one hand and while pulling back for leverage, she slided a finger through his pencil tight opening and deep into his rectum. Working over his prostate for some time and adding fingers, he heard her disturbing results
“this is not good, not good at all…another case of teenage constipation…..”
Pulling off the soiled glove she had him sit next to her for a little talk. Hugging him affectionately she explained
“Jo, I need to leave for a few minutes to prepare some medicine. It will be easier to take if you spend the time trying to relax”
and she disappeared into the bathroom. He figured he knew what would be next. A spoonful of castor oil and a plate of prunes to be eaten during the second half instead of the potato chips he brought.
He couldn’t understand what was taking her so long and started playing with his erection curious about how the anal stimulation had powerfully aroused him. He hears water running…and running….and running and still couldn’t understand what was going on……until……his attention became riveted onto Auntie Brigitte as the bathroom door opened and she emerged wearing only a garter belt stockings and heels.
The elusive mystery of a woman’s triangle was finally revealed accented by a thick patch of curly black pubic hair. But within a blink of his eyes, his attention moved to what she was struggling to carry… A huge bloated wet dripping red hospital enema bag with a flared nozzle that will surely never fit!!
Ordering him to stand, she pressed the warmed wet rubber up against his tummy and genitals and muttered:
“just the right amount”.
Which he noticed, matched the “one gallon” line marked on the bag.
OH MY GOD, NO!!!
She rolled an IV stand next to the bed and was barely able to lift the swaying heavy apparatus onto the hook. Some medicine! Auntie Brigitte sternly ordered him to assume the humiliating position of lying on his back with legs spread wide and drawn up on the edge of the bed while she towered over him testing the flow and temperature on her wrist and dripping down onto his bare skin.
Positioned between his legs leaning over him with her breasts erotically swaying, she lubed up the nozzle, ordered him to take a deep breath and separated his buttocks. She drove the flared form up through his sphincter to fulfill it’s purpose of not falling out and keeping the water in. With a tone of motherly empathy she explained to him this would unfortunately be an uncomfortable but necessary experience while secretly looking forward to watching him squirm and struggle as she controlled the flow of the large enema draining from the bag and meandering relentlessly up the path of his expanding colon .
Sitting down next to him she snapped open the hose clamp and he flinched with the first new sensation of the warm enema entering him and the ominous hint of the building pressure to follow. She grabbed her bottle of baby oil and explained how she would be massaging his abdomen to help distribute the volume as she traced with her fingertips the hardening taught skin while the water moved up the path of his expanding intestine.
Having witnessed many female orgasms from similar treatments of her students, she was curious to watch how erotically arousing the internal warmth and pressure would be for Jo and so, she enjoyed gently caressing his genitals as the water flowed past his prostate.
But unlike women, there becomes a point for a male where the erotic pressure moves the attention from sexual pleasure to surviving the deep discomfort of the remaining bag and as a result.. Old Glory falls to half mast…..
She felt him holding her hand and eventually reaching out to bury his face into her breasts for reassurance and comforting as the bag (now all too slowly) flattened. He winced and panted. Taking pleasure in her opportunity to offer mothering support, Auntie Brigitte whispered softly to him and coached him to take deep breaths and try to relax as she started to stop the flow. She sensed his condition and waited for the cramps to pass and his colon to gradually expand before adding more flow. He struggled with all his bravery to gain the approving touch and motherly gaze from Auntie Brigitte for his attempt to empty the contents of her treatment. Together they watched the bag go flat and the last column of water move down the tube and she clamped it shut for the last time. A motherly hug follows and she helped the bloated boy struggle off the bed and mercifully walk to the toilet for a loooong and welcome enema release.
Returning to the bedroom he asked:
“Now can I watch the game, Auntie Brigitte?”
Totally confused, he was surprised to see her demeanor change back to the earlier punishment. “Now that you are well cleaned out, Jo, I think it is high time for you to experience what these young girls experience when you poke them”.
She revealed a collection of dildo probes from small to terrifyingly huge. A series of erotically deep insertions of graduated size left him glassy eyed staring at the ceiling and humiliated by the arousing and pleasurable effect it was having on him. She buckled up her most challenging strap-on dildo which she affectionately called her “sissy mouth stuffer” and after the thrill of gagging him, repeatedly drove it deep up his rectum over and over while restraining him with a sensuous hold on his genitals.
Pulling out of his now well relaxed orifice, she knew he was ready for the ultimate surrender
“I need to verify the enema accomplished the intended results”
and slowly worked her gloved fist up against his willing sphincter. With some cooperative effort, she felt her knuckles pass through the most difficult place as he sucked her fist up into his rectum. Overcome with emotion and the ultimate arousal, he collapsed onto the bed as she blanketed her warm form over his totally spent body. So much time had passed, the football game has ended
The next morning when he ran out to aunt Nancy’s waiting ride, she asked him how the evening went..
Oh, it was a good evening,
with a reflective smile staring out the window back to a waving Auntie Brigitte…..
“the Seahawks beat the Redskins……”
-with a wink to auntie Brigitte
He arrived promptly at the specified time.
The street was quite a bit different from what he pictured. Instead of high rise condos, he saw mostly single family houses, some duplexes -- trees, gardens -- sort of like an old fashioned neighborhood from a previous generation.
After ringing the doorbell and receiving a cheery "Hello," he headed downstairs as instructed.
Arriving at the door, he stopped, nervously aware of the butterflies in his tummy. Then he knocked. Authoritatively. He was, after all, a captain of industry. People did his bidding all the time -- at work, his private club, even at home. No doubt Miss Brigitte would recognize his natural air of authority at once!
Just then the door opened, and a warm, wide smile greeted him. She was, as he hoped, dressed like his favorite school teacher. Right down to her sensible leather shoes. He realized at once that she was wearing flats because she would soon be wearing her boots.
And then, she spoke:
He goggled, stunned for a moment. Then it hit home -- ego reduction, he had been sentenced to ego reduction. His knees softly fell to the floor. She smiled, a nurturing, empathetic smile and said "Try it again. Your knees didn't really hit the floor very hard at all."
He arose, slightly bowed to her, then fell once again to his knees. "Nice touch," she murmured, referring to the bow. Her voice was a tiny bit husky and he detected a French accent.
She walked behind him, then proferred a long, slim object -- seemingly a fibreglass rod wrapped in linen whipcord. "Kiss the dressage whip, boy." His lips hungrily kissed the length of the rod as he heard her say "This can be made to sting lightly, or remove your sotting ability for a week. Your behaviour tonight, little man, will decide your fate." "Yes Miss."
He only just got the words out when he was slapped -- lightly, but firmly -- across the face. "Call me Auntie B or Madam. Got that, boy?"
"Yes Miss." She leaned over him. He was unaware of his offence. Nerves, perhaps. She calmly removed his glasses, then slapped him much harder across the face. "You were told what to call me." "Yes Auntie B."
She smiled. This was going to be such fun. His primary interest was domestic discipline: corporal punishment in all its glorious forms, scolding, corner time, even hand strapping. And yet, there were the boots. He had a deep-seated need to lose his personal power, to end up on his knees licking her wellies until they sparkled.
She looked down and saw he was already erect. Perhaps some form of manipulation and denial therapy would be helpful, she mused. He did confess to masturbating far too much, while looking at women in rubber rain boots on the rainy streets of his home town. "Men always hate the taste of their semen.... maybe I can use that against him at some point" she thought.
"Boy, get undressed. Then we'll have a lovely chat before we decide anything. I need to know more about what misdeeds you have committed, and how I can help you be a better person. One thing though -- the strap-on is not negotiable. At some point in the next two hours, I am going to restrain you in the arm-binder, and take you from behind. Then when I see you Saturday I am going to do it again, but with a larger dildo".
He followed her into the room, head slightly bent. There were the boots, in need of cleaning, especially the deeply treaded rubber soles. A wooden hairbrush on the coffee table. A bar of Ivory soap by the looks of it. He instantly regretted telling her about his swearing problem.
"Yes Auntie B?"
"Before you leave tonight, remind me to give you some lines to write. I want you to be kept nice and busy between now and when I see you Saturday. An hour or two of repetitive writing will help focus your mind, boy."
He groaned. "You sure are strict with me." And then he smiled. She joined in, and they hugged for what seemed like minutes. Friends, instant friends.
And then she murmured in his ear
I found that little Jewel on youtube."Dressage au Fouet", a remarkable, rare, purely fetishistic film of a mistress disciplining her slave. Made by Jacques Biederer (Ostra Studio), a Paris photographer of high-class erotica. In the '20s & 30s he made elegant (and humorous) "French postcard" type nudes - and incredible fetish pictures (spanking, whipping, S&M, pony play, etc.).