Here’re 4 sissy punishment  stories for you:)

SISSY GETS PUNISHED ON HIS BIRTHDAY

My lovely goddess of a wife had promised me a memorable treat for my birthday. I stayed on my best behavior that week, in anticipation of an exciting climatic night of pleasure. During the day she texted me ‘hope u are ready for treats.’ I wrote back to confirm and then told her I was doubly thrilled to get not just one but multiple treats. She responded back, ‘Well it’s your lucky day. You’re gonna get not two but three!’

My greedy self was hardly able to concentrate at work that day. By nightfall, she summoned me to the royal bedroom, a candlelit chamber of delights. Locking the door, she revealed herself in magnificent beauty, dressed in black negligee with gold embroidery. She instructed me to strip off my clothes and get on my knees. My cock stood at attention. “I’m going to blindfold you now, and you will do what I tell you precisely. Is that understood?” she asked.

“Yes, my love,” I replied. She wrapped a scarf over my eyes, and then asked me to stand up and step forward slowly while lifting my legs. She was holding something for me to step into. As soon as I put my second foot in, she pulled it up my body. It felt soft and silky. Before I could object, she pulled my arms through the spaghetti straps, leaving me standing in what I immediately recognized as a soft chemise. The night had already taken an unexpected turn that did not bode well for a big, throbbing birthday orgasm.

“You look so cute,” she said as she caressed me all over, “especially the built-in lacy bralette top and the flowing silky material. So girly!”

“I don’t like it,” I replied even as my cock jutted out.

“You don’t like your treat? Why?”

“Because it doesn’t feel manly,” I objected.

“That’s because it’s not manly. Let me be 100% clear, this is what could be described as ultra feminine. Definitely not at all masculine to me. Doesn’t make my pussy tingle. But your cock seems to like it,” she stated, laughing at the obvious discrepancy between my mouth and penis.

“That’s just because I’m in your presence,” I replied, trying to deflect my feelings.

“I appreciate that but you’re not being honest with yourself, once again. We’re going to have to fix that, and what better time than now? Bend over and assume the position!” she commanded, leading me around to the end of our bed.

My wife told me to spread my feet apart and keep my hands locked above my head. She proceeded to whack my bottom hard with her special long hardwood paddle, very hard about 30 times, leaving me howling for mercy. She leaned over to whisper in my ears, “Would you like to admit that you like wearing this frilly women’s chemise? I want to hear you tell the truth about how you prefer wearing women’s lingerie more than men’s boxers.”

I stayed silent. I could not admit it. “Very well then… I have no choice but to interpret your silence as disrespect.” She pulled my chemise up, baring my buttocks while caressing my bottom. “Admit it, or else!” she decreed her ultimatum.

“Oh come on, please don’t drag this on?” I replied. This brought out the bitch attitude in my wife. She disciplined me harshly, paddling my bare buttocks another couple dozen times until I felt the fiery heat and unbearable stinging. She gave out six strokes at a time, very hard, on top of one another on the same cheek. On the bare buttocks, it felt considerably more painful. I could feel my buttocks turning red and tender.

After about 3 minutes of this, she asked me again, “Are you ready to tell the truth now, birthday boy?”

My bottom would no doubt feel the soreness even if merely touched. I knew that I would not be able to sit down without discomfort on anything but the softest surface for a few days. “Yes, I guess so,” I stammered. “I like wearing this kind of clothing because it’s soft.”

“Husband, you need to do better than that,” she said with a hint of strictness over my lack of enthusiasm and gratitude.

“I admitted that I like the chemise. What more do you want?” I shot back in a snappy tone. I realized even as I said this that I should have spoken more respectfully. I had to correct the tonality of my initial impulse reaction. I could not see where my wife was but I knew she was close by. “I mean I admit, dear wife, that you’re right.” I kept trying to dig myself out of the hole.

She didn’t say a word. She didn’t have to. I knew. I felt her tying my ankles to the bed posts. Soon I felt a tapping on my rear end. She was lining up the paddle against my buttocks as if to measure the distance how far to stand from me. I knew I was about to get it, and that it was going to get bad, really bad.

When she started again, it was super hard, relentless. Another few minutes and another couple dozen strokes later, I was regretting ever opening my mouth as another round of paddling brought home a deeper submission all over again. “Please wife, I admit it sincerely. I like wearing the frilly chemise more than men’s boxers,” I pleaded through short breaths.

She leaned over again to whisper into my ears, “Now that’s more like it, husband!” She circled around me, uncertain whether I needed to be punished more. She pinched my buttocks which made me yelp. “I see you appreciate my second gift.”

“I don’t know if I can handle any more of your gifts,” I said. I meant it as a lighthearted comment but the tone came across to my wife as a complaint. I was a slow learner. Another dozen whacks later, I hit rock bottom, muttering all kinds of sincere appreciation for the gift of discipline in between begging her for mercy. She put the paddle down.

“I think that should help keep that attitude of appreciation burning underneath you for some time!” She concluded.

“Thank you very much wife,” I replied in full agreement.

“You know what you are, husband?”

“Sore and sorry?” I asked.

She teased me, “Yes, that you are and will continue to be, but I meant something else. What do you call a man with a small penis, who has his butt blistered by his wife for misbehaving, and who likes to dress in a sexy chemise?”

“I guess you’d call him me,” I admitted. She untied me and took the blindfold off and led me to the full length mirror. She held the chemise up to show me my buttocks, and then turned me around to face the mirror, showing off the full chemise. My face felt nearly as red as my bottom.

“Try again, or else I can continue the Q&A with the assistance of my paddle. What do you call such a man? I’ll give you a hint. Five letters, rhymes with Missy.”

I knew already what she wanted to hear from me. I could not bear to be punished again, so I mumbled softly, “Sissy.”

“Say it again, in a complete sentence, louder!” She commanded.

“Wife, I am a sissy with a small penis whose wife spanks him and who likes to wear a chemise,” I admitted freely.

“Good. It’s about time that you were honest with yourself and with me. I love you for being open.”

We embraced and made out, kissing feverishly. She instructed me not to touch my buttocks, and that there was to be no soothing, no lotion, no ice. She intended to let it sting and burn without relief. I was to appreciate the soreness with every breath as a form of meditation on my submission.

“Lie down on the bed face up” she instructed. I laid down. Soon she tied my hands and ankles to the 4 corners of the bed. I felt humiliated, tied up in this very vulnerable and exposed X-shape position at the mercy of my wife, still wearing the chemise but too sore and humiliated to care. My cock stood at attention. She stroked it lightly, slapped it gently, then kissed it and finally sucked the entire shaft of my penis. My penis stood up eagerly. ‘Finally I would be rewarded with the third treat’ I thought to myself as pain started to shift into pleasure.

My wife had a different idea of the treat though. “Husband would you like a nice juicy orgasmic release?” She asked.

“Yes wife, if it pleases you and if you feel I deserve it,” I replied carefully.

She looked at me with a naughty look. “That’s a good answer, but unfortunately for you, I have decided you do not deserve to get a pleasurable release. You’ve been disrespectful. I think you need to be punished more.”

I thought to myself how could it be that this was not punishment enough? “As you like, wife,” I said obediently, even as my heart sank, dashing my hopes suddenly.

“Yes it will be as I like, and only as I like.” My wife proceeded to stroke my cock ever so lightly around the tip, along the penis underneath, on the balls. Then she took a dollop of lotion onto the tips of her fingers. She rubbed the lotion covered fingers onto my thirsty dick with a few quick strokes. I hardened immediately. But then she stopped.

Five seconds later, she stroked it just one more time. I tugged and twisted my hands desperately to reach my penis but I could not. She laughed as she continued this kind of stingy teasing for an eternity, one or two light strokes, followed by nothing. Sometimes she traced a single finger up and down the bottom side of my penis. My poor cock stood erect at the edge, stimulated repeatedly just enough to almost reach or orgasm but never hard enough or long enough to actually reach climax.

I looked at her with desperation. “Please wife, I need it. I’ll do anything for you…” I begged. I tugged at the ropes holding my hands and legs but I had no way to reach my dick to finish off.

My wife removed her panties and held them up closely for me to see. They were soaking wet. She was getting off on this. “I know you’ll do anything for me…” She proceeded to pull the panties over my head, positioning the gusset just over my mouth, smothering the wetness into my face.

Then she reached into the drawer to take out her vibrator. She lay down next to me, using it on herself for a deep and satisfying fucking experience for herself, enjoying over ten minutes. She took a deep breath afterwards, basking in satisfaction. “There’s nothing I love more than a thick, hard dick, going deep into my pussy. Such a shame that it cannot be yours! All because you’re a sissy dressed in women’s attire, soundly punished by a woman, your buttocks stinging red too sore to sit down on, and now tormented to the edge of sexual desire!” She shook her head. “Would you like to have a release?” she asked.

I nodded my head. Grabbing the vibrator, she turned it to a slow speed, then held it against the bottom side of my penis. I tensed up. She moved the vibrator all over my cock, especially around the tip as my cock grew larger and harder.

I strained against the ropes and tried to buck my hips to feel something more. But she wouldn’t allow me. She would take the vibrator away after a few seconds. She leaned over me, straddling me in a 69 position, sitting on my face with her skirt falling over my head as she rested her pussy against the panties covering my face, while letting her luscious hair drape over my cock.

The feathery sensation of her hair caressing my cock got me very excited. But then she sat up again. She turned up the speed on the vibrator and held it against the bottom side near the tip of my cock. She ran it up and down a couple of times.

I felt a surge of orgasmic energy building. She sensed it also and immediately removed the vibrator. A few seconds later she did it again. She continued to stroke my penis, balls, and thighs all over with super light pressure, alternating occasionally with a firm but very short-lived stroke with her hands to remind me what I was missing. After almost 10 or 15 minutes of this tormenting teasing, my cock felt ready to explode. I wanted desperately to experience a sensual orgasm, with my penis enveloped tightly against her warm, wet vagina, or her delicious mouth, or at least the continuous massaging grip of a woman’s hand.

“Wife, love of my life. Please. Let me celebrate my birthday with a juicy and satisfying orgasm? Please!” I begged.

“Settle down now!” she said, slapping my cock lightly to calm it down. “I know what you’d like is to feel my hand, or my mouth, or my pussy surrounding your desperately hungry penis and stimulating the nerves vigorously over the top, until you erupt into a throbbing fountain of happy ejaculation!! Am I right? Would you like that, husband?”

“YES!!” I exclaimed, “There is nothing I would like more in this world!”

She looked at me lovingly for a long moment as I sweated it out. We kissed. My cock stood at attention. My wife was known for changing her mind sometimes and giving me unexpected pleasures. I hoped this would be one such occasion. I waited patiently as she continued to stroke the very tip of my cock with her fingers, tempting the volcano inside. “Are you ready for it?” she asked flirtatiously.

“Yes, please!! Thank you!” I exclaimed, readying myself to launch.

“Do you deserve it?” she teased.

“Yes!!” I gasped.

“No,” my wife said emphatically, in a sudden reversal. “It’s not happening.” My wife continued teasing me, stroking me expertly with feather light strokes to bring me to the edge. I had to take matters into my own hands, literally. I shifted around in bed and yanked the ropes to reach my hands to my cock, but I could not touch myself.

Finally, she touched the tip of my cock with the vibrator with just enough pressure, and just barely long enough to make the flow of semen start coming out. At the exact moment I felt the sensation, she pulled the vibrator away, leaving my cock trying to throb.

This was the moment when the nerves in my cock craved furious stimulation, friction, and pressure. I cried out “aargh… please love, stroke me!!” But she refused. She touched the vibrator again to the bottom side to keep things going, but only briefly. My cock danced around in the air, with nothing around to touch or caress it. The cum dribbled out uselessly, and with zero tactile stimulation, I did not feel the pleasurable orgasmic spurts that I so desperately craved. My penis just emptied itself involuntarily, with semen running down the sides, cheated out of an orgasm.

A minute later, my penis rested on its side, flipped over in a puddle of my own semen. She cuddled next to me, gently stroking my face and chest, smiling naughtily. My heartbeat was still racing, but for nothing. I was left without the euphoric feeling of an ejaculation. “That was your third and final punishment treat,” she explained nonchalantly, as if it were no big deal, having enjoyed her orgasms already.

“Wife, that was so mean!” I complained.

She shook her head, “Awww, I’m sorry you didn’t get to experience a real orgasm. Well maybe I’m not sorry. In fact, I don’t regret it. This is exactly what you needed.”

“Do you have any idea how hard this is?” I asked.

“Oh yes, I understand, but you should be used to it by now. You know the rules. Rule 1 is that after a paddling, there’s no release for you because the effect of corporal punishment needs to sink in. Rule 2 is that I don’t allow a sissy to touch me sexually, and Rule 3 is that a punished sissy has to suffer a ruined orgasm to go with his tender bottom.”

“That was unnecessary. It’s worse than not having any release, because now it’s been ruined, I didn’t feel the excitement, I didn’t get any pleasure, nor could I please you!” I whined.

“You may not have enjoyed it, but that’s why it’s called a PUNISHMENT. On the other hand, I did enjoy my hard cock vibrating orgasm a lot. Next time, when you show me that you can communicate honestly with me and with yourself, things might play out differently.”

“Yes, wife, darling. I adore you, and thank you.”

I prepared myself mentally to accept my punishments gracefully.

Before turning down the lights, my beautiful Goddess reminded me, “Husband, you’re going to be sore for at least a couple of days so tomorrow night, I will expect you to come to bed at 9:30 sharp. You will need to be dressed in a different outfit that I will set out for you, no questions asked. It will not be a chemise. It will be something much worse, something even more suitable for a sissy like you. After you put that on, you will massage my feet, and use the vibrator on me before going to sleep. Is that understood?”

“Yes, perfectly. It will be my pleasure to serve.” I spent that night feeling more motivated to be truthful, and deeper in love than ever before.

“Happy birthday, dear husband!”