Mistress Sarah Gives Evie an Assignment
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Mistress Sarah Makes Evie A Sissy 2 free porn video
"Look at you Evie. You're so slutty in your teddy and stockings,” said Mistress Sarah. Then she looked down at my hard cock and said, "....and your clitty is so big. Excited are, you?"
Mistress Sarah reached out and firmly squeezed my cock a few times. It was a welcome sensation that reverberated though my entire body. Before I could respond, she ordered, "Turn around slut. Let me see that arse of yours."
Ever since I had met Mistress Sarah online, I had dreamed of her fucking me in the arse. I had often used various vibrators and dildos on myself and Mistress knew this, but over the past few months, Mistress Sarah had nurtured a strong desire within me to be taken by her strap-on and so it was thrill for me to turn and show her my arse.
I felt a push on the center of my back. "Bend over slave," ordered Mistress Sarah.
My hands braced on the bed as I fell forward, with my arse on display. Mistress Sarah kicked her foot against the insides of my ankles and ordered, "Spread 'em slut."
Mistress Sarah pulled the fabric of my teddy to the side and gazed at my arse. "Mmmm. Such a tight pussy Evie. I’m going to enjoy fucking you slut. I bought a nice new strap-on just for you."
My arse was tingling and ready for her strap-on. Was this going to be the moment I had dreamed about for months? I begged, "Please fuck me Mistress."
Mistress Sarah replied, "Calm down. I've got some more work to do on you Evie. You want to be nice and pretty for your first fuck don't you?"
"Yes Mistress."
Mistress Sarah moved away from me and sat herself on the bed. And slowly began to play with herself. I knew better than to move to join in unless I was instructed to do so. I watched my Mistress. I loved what I saw. I was completely enthralled. I could not help but stroke my cock as I watched. In one smooth motion, Mistress Sarah pulled up the bottom of her dress and dipped her fingers into her pussy.
I rubbed my cock through my teddy and excitedly watched Mistress Sarah's fingers slowly move in and out. I saw her head lean back and her eyes close from the pleasure. I could see lust in Mistress Sarah's face. All this erotic imagery fuelled my arousal and desire to want more. I was glad to be where I was.
While Mistress Sarah slowly pleasured herself, she looked at me and said, "This is all part of my plan Evie. I am letting you into my world. My world is full of sex, kinkiness, and excitement. It's what you want isn't it? It's what you dream about. The more you obey me and the more you let the sissy slut in you surface...the more I will let you into my world."
Mistress Sarah was quite the sales person because at that moment all I cared about was being in her world. I wanted it bad and I let Mistress Sarah know. Almost begging I said, "I want to be in your world. This is where I want to be Mistress."
"Good girl. Tell me what you need to do."
"I need to obey you and bring out the sissy slut in me."
"Yes. Now tell me you will do it."
"I will obey you and I will bring out the sissy slut in me."
"Say it again Evie."
I repeated, "I will obey you and I will bring out the sissy slut in me."
By now Mistress Sarah's fingers were glistening with juices and she was moaning softly from the slow continuous teasing of her pussy. Mistress Sarah brought her fingers to my lips, I eagerly licked them clean. Her seductive eyes never left mine. They captivated and controlled me.
Sitting forward, "Good girl," whispered Mistress Sarah into my ear. Then she gave me a kiss on the lips. Mistress Sarah looked at me and said, "The slutty girl is already here isn't she? You are slutty Evie right now aren't you?"
"Yes Mistress," I replied.
"That's right Evie. I think it’s time to give you a make-over and teach you to be more prim and proper. There's quite a bit of work to do on you. Are you ready?"
"Yes Mistress. I am ready. I want to be a sissy for you."
"Good. Let's start with the rest of your body hair.” Mistress reached into the bedside cabinet and retrieved a tube of hair removal cream.
I panicked, "I thought we weren't going to do anything permanent?"
"Permanent?" questioned Mistress. "There's nothing permanent about hair removal. It grows back." “It’s your choice Evie, do what I say, when I say it and enjoy your first weekend of many or get up now, get dressed and leave, never seeing me again”
Mistress Sarah savoured the hesitant and concerned look on my face. This was the game she loved to play. She loved to tease and toy with me. But this time I could tell she wasn’t playing. She knew that her body and feminine power could persuade me to do things I would never imagine doing on my own. This control is what filled her with lust to feminize me. Her pussy quivered and dampened knowing she was challenging my will and pushing my limits.
Then Mistress Sarah threw in a real shocker. "Besides, you don't want the hair on your legs to show through your stockings when we’re out in public, do you? Then everyone would know you were a sissy."
My heart skipped a beat. I questioned with alarm, "In public?"
Mistress Sarah replied sweetly, "Why yes my pretty little Evie. I've got to show off my new princess slave. You didn't think I'd make you come all the way here and then hide you away, did you?"
"I guess not," I replied. I knew that a public appearance in full femme gear was inevitable. It was on my mind the whole trip here. It was just a scary thought at the moment.
Mistress Sarah reassured me. "Don't worry Evie, your big debut will not happen until I’m satisfied with you and I am going to transform you into a pretty girl. When you walk by people are going to look twice. Not because they think you're a guy but because they just saw the cutest, hottest girl in the place."
While the words were still sinking in, Mistress Sarah took my hand and led me into the bathroom. I followed with no resistance. I did not have the will or courage to resist. I was completely under her control.
In the bathroom, Mistress Sarah stripped me out of my teddy and stockings and had me stand in the center of the bath tub. Mistress Sarah spread the hair removal cream all over my body from my neck down.
"Your legs are going to look so smooth and sexy Evie," Mistress Sarah said.
I stood in the tub confused at how hard my cock was. I was being emasculated, yet I was aroused and excited. I knew I could not stop what was happening and it excited me. I was so thrilled to be in the presence of a beautiful dominant woman. Her shiny black PVC outfit looked amazing against her skin and the outfit left little to the imagination. I had a perfect view of Mistress Sarah's tits while she was leaning over, covering my legs with the cream. All the sexuality around me was a fantasy come true.
While the cream tingled on my body and worked its magic, Mistress Sarah played with my cock, keeping me aroused. Then she turned the shower unit on and rinsed away the cream, I was left standing hairless and smooth all over.
Mistress Sarah ordered me to towel myself dry before she massaged a scented lotion all over my body, taking every opportunity to tease my cock and play with my nipples. I enjoyed the attention and soon my knees were weak, I was on the brink of orgasm. A constant stream of precum was leaking from my cock.
Mistress Sarah scooped up some of the cum that was leaking out of my hard cock and put it up to my lips. I obediently sucked my cum off her fingers. "Good girl," said Mistress Sarah. "I'm so proud of you,"
I was led back to the bedroom. Mistress Sarah pulled a large white box from under the bed and placed it on top of the bed.
"This is special sissy lingerie for you Evie. I know you want to be transformed into a pretty girl, but tonight you will be just a sissy. This is a necessary step in your training pet. You need to experience all the moments of becoming a sissy so that it will shape who you are and prepare you for the next exciting step of being completely feminized."
Mistress Sarah unpacked the box. She reached up and rubbed her hand across the stubble on my face. ” And I’ve purposely left your face unshaven today to remind you that you are a boy dressed as a girl."
As Mistress Sarah laid each item on the bed, I could see that it was truly sissy lingerie. There was lots of shiny satin, frilly fabric, and silky bows. I imagined the silk would feel incredible against my smooth skin.
It felt surreal to me to be standing there completely aroused and submissive while I was being dressed as a sissy. I was dressed in pink frilly satin panties, white stockings. The white stockings had large silk bows at the top.
Mistress Sarah admired my legs. The stocking enhanced smooth legs. She rubbed her hands along the stockings and commented, "Evie, your legs look so smooth and sexy in those stockings. You put other girls to shame."
I blushed but was actually proud of the compliment. I looked down at my legs and agreed. They looked very sexy. "Thank you Mistress," I replied.
Next Mistress Sarah approached me with a pink satin corset in her hands. In an excited voice she said, "Here's your first sissy corset. Put your arms out princess and I'll help you put it on."
Like a puppet, I obeyed. Butterflies filled my stomach and my cock twitched as Mistress Sarah wrapped the corset around me and pulled the straps very tight. I felt completely emasculated and feminized with the corset on. I was nervous and excited from crossing over this threshold into the feminine world. The tightness of the corset, felt like bondage to me. I felt as if I was being locked into the feminine world and pushed deeper under Mistress Sarah control. But this is where I wanted to be.
"Oh that is so pretty," commented Mistress Sarah. Mistress Sarah's body shivered in excitement to see me dressed so feminine and pretty and to see me so docile and submissive to her.
"My pretty little slave girl," she said with delight and accomplishment.
Mistress Sarah reached down and squeezed my cock through the panties and teased it a bit. She wanted to ensure I remained fully aroused and close to orgasm during my feminization. She knew keeping me aroused allowed me to be easily manipulated and trained to be her obedient feminine slave.
Mistress Sarah pulled a large satin dress from the closet and displayed it for me to see. The dress was the most feminine yet sissy looking maids dress that I had ever seen. It was made of high quality pink and white bridal satin. A white satin apron with pink ribbons was embroidered on the front of the dress. White shimmery lace trimmed the bottom of the dress and the sleeves. The shade of pink wasn’t a colour I would have chosen for myself, my preference was for sexy, sultry, slutty colours, this was definitely a real sissy colour.
Mistress Sarah asked, "Isn't this so pretty Evie. You are going to look so adorable in this."
I was very aroused and extremely excited to please Mistress Sarah. I could not wait to try the dress on. I knew my thoughts and desires at that moment broke all the rules I was taught about being a man but I didn't care. Mistress Sarah had unleashed a new feminine desire in me that I could not hold back. I accepted my new fate to be a sissy and I eagerly slipped into the dress with the help of Mistress Sarah.
Mistress Sarah pulled the dress straight around me and straightened the hems. She slowly walked around her new dress-up toy and admired 'her.' She commented, "What a lovely sight. You are so pretty and cute Evie. Mistress is very pleased with her sissy. Come look at yourself in the mirror."
I walked over to the mirror with Mistress Sarah. As I walked I was aware of many feminine sensations. The tightness of the corset against my chest, the silky stockings rubbing over my legs and stretching against my toes, and the dress rubbing along my thighs and legs as I walked were all wonderful new sensations that reminded me of my feminine state. My arousal grew stronger knowing that Mistress Sarah was purposely bringing out the girl inside me.
I never imagined I would be staring at myself in a mirror, dressed as a sissy. I never would have predicted or comprehended how exciting the moment would be. Beneath the pink shiny dress and underneath my satin frilly panties my cock throbbed harder than ever. I wanted to touch it stroke it desperately but I knew that was forbidden. Instead I flexed it, causing my cock to pulse against the silky sissy panties. I felt completely submissive dressed as a sissy and being with my Mistress who was still dressed in her tight sexy PVC outfit.
I gazed into the mirror like a deer in headlights. I thought I looked silly but I knew Mistress Sarah was pleased with my look and I knew that her pussy was dripping from my obedience and from my sissy look. This alone, made it worthwhile. I would not want to be caught dead dressed as I was, in front of my friends but in Mistress Sarah's world, I was thrilled, aroused, and excited to experience my sissy state.
Mistress Sarah showered me with compliments. "You are so pretty princess," cooed Mistress Sarah. "Pink is your colour sweetie. We're going to have to paint your nails a nice pretty pink to match your dress." "I have the perfect shade," said Mistress Sarah.
Everything happened so quickly. Mistress Sarah had me sit on stool, took my hands and went to work. In just a few minutes I had shiny pink finger nails. Next was a wig with long straight black hair and glossy red lipstick. Mistress Sarah brought a hand mirror up to my face so I could see the results.
I had a good amount of stubble on my face. The wig and lipstick alone did not create a pretty picture. I simply looked like a man wearing a wig and lipstick. I asked, "Can I shave Mistress? Will you put more make-up on me so I look more like a girl?"
Mistress Sarah responded, "Evie, it's good that you notice these things sweetie. Wanting to make your face pretty and girly shows me how well you are progressing in your training and moving along your journey to girlhood. I am so proud of you for that but we will save the make-up and shaving for tomorrow. Remember you are sissy tonight and this is what sissies look like. You make a perfect sissy sweetie."
"Yes Mistress," I replied.
Mistress Sarah commented, "You are quite a sissy boy Evie and tonight you are going to be my little bitch aren't you? Tell me what sissy bitch you are going to be for me."
I knew what she wanted to hear. "I'm going to be your sissy bitch tonight Mistress. I'm going to suck your strap-on and I'm going to let you fuck me with it."
Mistress Sarah laughed and questioned my last words, "Let me fuck you? There's not 'let' sissy bitch. I am going to fuck you. You have no choice. Now say it again slut. Tell me you are going to be fucked."
Mistress Sarah's words were stern and unforgiving, but I loved it. It pushed me further into subspace. I replied, "I am your sissy bitch and I am going to be fucked by you tonight."
"That's my slut," laughed Mistress Sarah. "Now show me your sissy panties. Lift up that cute dress of yours and show me your pretty panties."
I did as instructed. Mistress Sarah slapped my arse and commented on how cute my arse looked in the panties. I was made to bend forward. Then I felt my panties being pulled down to my thighs.
Mistress Sarah said, "This should help keep your mind on what's going to happen later tonight."
I felt something firm poke at the entrance to my arse. Slowly Mistress Sarah pushed a large lube covered butt plug into my arse. The wide plug spread my arse and filled me inside. I moaned in pleasure from the fullness. My cock twitched and dripped creamy cum from the carnal pleasure. Before Mistress Sarah pulled up my panties, she squeezed my cock a few times, causing me to shudder in pleasure. Warm cum oozed out onto her fingers. She spread the stickiness all over my cock and balls.
Somebody's sissy clitty is all wet, isn't it," questioned Mistress Sarah.
"Yes Mistress," I moaned.
Mistress Sarah moved her fingers up to my mouth and said, "You know what to do."
One-by-one she pushed her fingers into my mouth. I eagerly licked my own cum off her fingers. "Good girl, Evie. Lick up all that boy cum. “Mistress Sarah dipped her fingers into her pussy. These too were bought to my mouth for cleaning.
Mistress Sarah announced, "Now it's your turn to help me Evie."
Mistress Sarah told me to undress her. I happily obeyed, enjoying the sight of Mistress Sarah’s firm tits popping out of the tight PVC dress as I pulled it up. I felt like I was unwrapping the sexiest gift in the world. Mistress allowed me a few moments to worship her body. I gently licked and sucked her nipples and I spent a few minutes lapping at her pussy.
It took quite a bit of will-power but Mistress Sarah was able to stop things before it got too steamy. She wanted to have more fun in the bath and she thought this would also be a great tease for her sissy. Mistress Sarah handed me a small plastic basket that was filled with various sex toys and vibrators.
"Follow me Evie," giggled Mistress Sarah.
I followed her into the bathroom. Mistress Sarah looked at me in deep thought and said, "Hmmm Evie, I want you to be kneeling by the tub while I wash, but I don't want you to ruin your pretty sissy dress."
Mistress Sarah helped me out of the dress and hung it on a hanger for use later. I was left in my corset, pink frilly panties, and white lacy stockings. Mistress lightly pulled on the large satin bows at the top of the stockings, admiring them. "These are so cute and pretty Evie. They really bring out the sissy in you. It's so sexy. I love it!"
"Thank you, Mistress" I said enjoying the attention and compliment.
Mistress Sarah had turned on the shower over the bath and stepped in. Mistress Sarah had me kneel by the tub and hold the basket of sex toys. She sorted through the toys and picked out a small pink vibrator. "This will feel good in my pussy," she said happily and then stepped into the bath and pulled the shower curtain across, blocking my view.
Mistress Sarah was already wet and aroused from dominating and sissifying me and so the vibrator slipped easily into her pussy. Mistress Sarah’s pussy seemed to devour it, I could still hear it buzzing even deep inside her. Her eyes closed and she let out a gentle moan as waves of pleasure coursed through her body. I wanted it to be me giving Mistress pleasure, Mistress Sarah had even said, that if I was a good girl, I may be allowed to fuck her. But I knew I had to wait, Mistress was still training me and showing she had total control over my actions. It was exhilarating for Mistress Sarah to have her pet kneeling outside horny and waiting.
The vibrations in her pussy quickly brought her to the brink of orgasm. Her whole body was alive with pleasure.
Kneeling outside the bath, I was intently listening to the buzzing vibrator, the sex sounds, and the erotic moans on the other side of the shower curtain. I wished I was in the bath with Mistress Sarah. Even though I knew I shouldn’t without permission, I reached inside my panties and played with my cock while I listened and imagined what was going on.
Mistress Sarah pulled the curtain back for a moment to allow me a glimpse of the sizzling action. I was eye level with Mistress and had a perfect view of the vibrator slipping easily in and out of Mistress Sarah's pussy. Her wet shimmering body was a prize for my eyes.
I looked up at Mistress Sarah’s face and was immediately drawn to her eyes. Mistress Sarah purposely locked in on me and licked her lips. Seeing me kneeling and dressed as a sissy with my cock in my hands sent her over the edge. It was hard for her to not close her eyes and just sink into the water, but she wanted to see her Evie. She wanted me to see the lust and pleasure in her eyes while she climaxed. When her orgasm faded away she blew me a soft kiss with her lips and let the shower curtain fall back in place, leaving me throbbing and desperate to see more.
It was only a few seconds after the shower curtain fell shut that the pink vibrator was held out for me. "Evie, pass me the white vibrator," ordered Mistress Sarah.
I quickly pulled the vibrator from the basket of toys, it was quite a bit larger than the pink one and exchanged it for the wet pink one. Mistress Sarah ordered me to lick the pink one clean.
"Lick off my sweet juices sissy slut. And I want you to suck on it for a bit too Evie. Sissy's must learn to be good a sucking things” Another fantasy of mine that I had confessed to Mistress, I was bi-curious and wondered what it would be like to suck a cock. “Then you can clean it in the sink with soap and water."
"Yes Mistress," I replied, eager to please.
Willingly I licked up and down the sides of the vibrator, delighted to know it had been in her pussy. Then I pushed it into my mouth and sucked on it. The curtain opened for a second and Mistress Sarah giggled at the sight.
"Good girl," complimented Mistress Sarah.
"Push it in and out sissy. Suck it like a cock," She ordered.
I obeyed. My arousal heightened from the humiliating order.
"Mmmm, So nice. You're a good cock sucking sissy," Mistress Sarah said. Then the shower curtain closed again.
I heard more moans and buzzing as Mistress played with the larger vibrator, I couldn’t see, but could easily imagine that too slipping into Mistress’s wet pussy. As soon as I’d finished cleaning the pink vibrator Mistress Sarah shouted through the curtain, "Sissy, get my strap-on ready. I believe you’re ready to see and feel what I’ll be fucking you with later."
"Yes Mistress", I replied.
"Hurry princess. Put a nice cock in that harness."
I found the harness and a selection of cock shaped dildos in the basket. Quickly I secured a large dildo into the harness, about 10” long and thickly veined. There were even bigger ones waiting in the basket.
"It's ready Mistress," I announced. The shower curtain opened and Mistress Sarah tossed the used white vibrator at me and grabbed the strap-on from my hands.
"Thanks slut," she said. "You know what to do with the vibrator."
The curtain closed but the hot image of Mistress Sarah’s glistening body was still in my mind. I stared at the curtain wishing I could see right through it. Slowly I licked the second vibrator with my tongue and listened intently trying to imagine what was happening just a few inches from where I was kneeling.
A quiet moan from Mistress echoed through the small room. "oohhhh. That's feels so good."
"This is so delicious Evie," cooed Mistress Sarah.
I could hear the sounds of Mistress Sarah fucking herself with the strap-on cock at a steady but increasing pace. As the pace quickened Mistress Sarah's erotic moans became quicker and louder.
Mistress Sarah spoke to me through the curtain. "Hear that Evie....It's what you are going to sound like later tonight. I bet you will scream much louder. I’m going to make you scream and moan like a prissy little girl. Does that excite you slut?"
"Yes Mistress. My clitty is so hard and swollen right now. I can't wait. I wish you would fuck me right now."
"Mmm. That's a good bitch. Pull back the curtain and watch sissy," ordered Mistress Sarah.
I did not hesitate to obey. I slid the curtain back and watched Mistress Sarah pound her strap-on into her pussy. The steamy shower water sprayed all over her wet body. I was too excited to even feel the water splashing onto me. I stroked my cock as I watched, not even realizing I was stroking in rhythm with Mistress Sarah's thrusting.
"This is so hot! God I want to cum," I begged.
Mistress Sarah had not planned on allowing Evie an orgasm yet, but the moment just seemed right.
"Do you want to orgasm Evie slut," asked Mistress Sarah.
"Yes! Please," I begged, hoping she was not just teasing me.
"Get the cup from the sink," ordered Mistress Sarah.
Eagerly I scooped the cup off the sink and got back into position on my knees.
Mistress Sarah said to me, "You've been such an obedient little bitch for me Evie. You can follow me to an orgasm. I want all your cum in that cup, got it?"
"Yes Mistress. Thank you Mistress," I said, thrilled at this chance for release.
Mistress barely finished her sentence when her body started convulsing with pleasure. She pushed the strap-on deep inside her pussy. She moaned loudly and between orgasmic breaths shouted an order to me, "Cum bitch. Cum like a sissy."
I pumped my cock and filled the cup with cum. My orgasm seemed to last forever. When it finally finished, I did what Mistress had seen me do numerous times. I lifted the cum filled cup to my lips but to my surprise he was stopped.
Mistress Sarah yelled, "Wait slut!"
I stopped and looked at Mistress. She stepped out of the bath, and stepped into the harness of her strap-on, pulling it up and settling it in place. To me she looked even more erotic with that large cock bouncing in front of her. She mused out loud, "Evie, you are so eager to drink up your cum. You really are a sissy whore aren't you? I like that Evie. I like that you are eager to be my cum drinking slut. Pour some into your palm slut."
I tilted the cup and let some of the warm cum ooze out onto the palm of my hand.
Mistress Sarah thrust her strap-on towards me and instructed, "Good girl Evie. Now stroke my cock with it. Rub it all over the tip of my cock. That's it pretty. Get my cock nice and sticky. Make a nice creamy 'cocksicle' Evie."
I followed her orders, knowing that the 'cocksicle' was going to be for me. The order from Mistress came quick and sudden, "Suck it slut. Suck my cum covered cock."
I immediately obeyed. I took the cock into my mouth. Mistress slowly pumped just the head in and out of my mouth. Although I just had an orgasm, my cock was hard. What I was doing was so perverse and taboo that it thrilled me. I enjoyed being her fuck toy. Mistress Sarah fucked me mouth and called me her bitch, slut, and cum eating whore. All these humiliating things fuelled my arousal and made me want to be even sluttier.
My desire to be slutty was easily met. Mistress Sarah pulled her cock away and ordered, "Put some of that cum onto your lips. Make them nice and glossy for me." I dipped my fingers into the cum and rubbed them around my lips. "More cum on those lips bitch," she yelled.
I quickly complied, rubbing cum onto my lips until they were dripping. Then Mistress Sarah ordered me to pull out my butt plug. "Dip it in your cum whore. I want it dripping with your cum."
I obeyed. I felt like a whore. I was excited to be a whore for Mistress Sarah.
"Now push it back into your sissy pussy. Evie."
The plug slid back into my arsehole easily. I felt dirty and slutty pushing the cum covered plug into my arse. My cock twitched as the plug pressed deep into me. Having my cum pushed into my arse mentally took me to a deeper level of kinkiness and submission. "I feel so slutty," I admitted with delight.
"Good girl," encouraged Mistress Sarah. "You are a perfect sissy whore now Evie. You've got cum dripping off your lips and fingers and cum in your sissy pussy. That's how a whore feels after a good night with a man. You've got one thing left to do Evie. Show me how slutty you want to be and drink up the rest of your cum."
Mentally I had become her sissy whore and accordingly I obeyed Mistress Sarah's command with great pleasure. I tilted the cup upward and started to drink down the cum. Mistress Sarah put her hand on the cup it forced it back down slightly.
Seductively she said, "Slow down slut. You want to enjoy your creamy treat don't you?"
The creamy goo oozed into my mouth. I felt like a used whore and I loved it.
Mistress Sarah reached out and firmly squeezed my cock a few times. It was a welcome sensation that reverberated though my entire body. Before I could respond, she ordered, "Turn around slut. Let me see that arse of yours."
Ever since I had met Mistress Sarah online, I had dreamed of her fucking me in the arse. I had often used various vibrators and dildos on myself and Mistress knew this, but over the past few months, Mistress Sarah had nurtured a strong desire within me to be taken by her strap-on and so it was thrill for me to turn and show her my arse.
I felt a push on the center of my back. "Bend over slave," ordered Mistress Sarah.
My hands braced on the bed as I fell forward, with my arse on display. Mistress Sarah kicked her foot against the insides of my ankles and ordered, "Spread 'em slut."
Mistress Sarah pulled the fabric of my teddy to the side and gazed at my arse. "Mmmm. Such a tight pussy Evie. I’m going to enjoy fucking you slut. I bought a nice new strap-on just for you."
My arse was tingling and ready for her strap-on. Was this going to be the moment I had dreamed about for months? I begged, "Please fuck me Mistress."
Mistress Sarah replied, "Calm down. I've got some more work to do on you Evie. You want to be nice and pretty for your first fuck don't you?"
"Yes Mistress."
Mistress Sarah moved away from me and sat herself on the bed. And slowly began to play with herself. I knew better than to move to join in unless I was instructed to do so. I watched my Mistress. I loved what I saw. I was completely enthralled. I could not help but stroke my cock as I watched. In one smooth motion, Mistress Sarah pulled up the bottom of her dress and dipped her fingers into her pussy.
I rubbed my cock through my teddy and excitedly watched Mistress Sarah's fingers slowly move in and out. I saw her head lean back and her eyes close from the pleasure. I could see lust in Mistress Sarah's face. All this erotic imagery fuelled my arousal and desire to want more. I was glad to be where I was.
While Mistress Sarah slowly pleasured herself, she looked at me and said, "This is all part of my plan Evie. I am letting you into my world. My world is full of sex, kinkiness, and excitement. It's what you want isn't it? It's what you dream about. The more you obey me and the more you let the sissy slut in you surface...the more I will let you into my world."
Mistress Sarah was quite the sales person because at that moment all I cared about was being in her world. I wanted it bad and I let Mistress Sarah know. Almost begging I said, "I want to be in your world. This is where I want to be Mistress."
"Good girl. Tell me what you need to do."
"I need to obey you and bring out the sissy slut in me."
"Yes. Now tell me you will do it."
"I will obey you and I will bring out the sissy slut in me."
"Say it again Evie."
I repeated, "I will obey you and I will bring out the sissy slut in me."
By now Mistress Sarah's fingers were glistening with juices and she was moaning softly from the slow continuous teasing of her pussy. Mistress Sarah brought her fingers to my lips, I eagerly licked them clean. Her seductive eyes never left mine. They captivated and controlled me.
Sitting forward, "Good girl," whispered Mistress Sarah into my ear. Then she gave me a kiss on the lips. Mistress Sarah looked at me and said, "The slutty girl is already here isn't she? You are slutty Evie right now aren't you?"
"Yes Mistress," I replied.
"That's right Evie. I think it’s time to give you a make-over and teach you to be more prim and proper. There's quite a bit of work to do on you. Are you ready?"
"Yes Mistress. I am ready. I want to be a sissy for you."
"Good. Let's start with the rest of your body hair.” Mistress reached into the bedside cabinet and retrieved a tube of hair removal cream.
I panicked, "I thought we weren't going to do anything permanent?"
"Permanent?" questioned Mistress. "There's nothing permanent about hair removal. It grows back." “It’s your choice Evie, do what I say, when I say it and enjoy your first weekend of many or get up now, get dressed and leave, never seeing me again”
Mistress Sarah savoured the hesitant and concerned look on my face. This was the game she loved to play. She loved to tease and toy with me. But this time I could tell she wasn’t playing. She knew that her body and feminine power could persuade me to do things I would never imagine doing on my own. This control is what filled her with lust to feminize me. Her pussy quivered and dampened knowing she was challenging my will and pushing my limits.
Then Mistress Sarah threw in a real shocker. "Besides, you don't want the hair on your legs to show through your stockings when we’re out in public, do you? Then everyone would know you were a sissy."
My heart skipped a beat. I questioned with alarm, "In public?"
Mistress Sarah replied sweetly, "Why yes my pretty little Evie. I've got to show off my new princess slave. You didn't think I'd make you come all the way here and then hide you away, did you?"
"I guess not," I replied. I knew that a public appearance in full femme gear was inevitable. It was on my mind the whole trip here. It was just a scary thought at the moment.
Mistress Sarah reassured me. "Don't worry Evie, your big debut will not happen until I’m satisfied with you and I am going to transform you into a pretty girl. When you walk by people are going to look twice. Not because they think you're a guy but because they just saw the cutest, hottest girl in the place."
While the words were still sinking in, Mistress Sarah took my hand and led me into the bathroom. I followed with no resistance. I did not have the will or courage to resist. I was completely under her control.
In the bathroom, Mistress Sarah stripped me out of my teddy and stockings and had me stand in the center of the bath tub. Mistress Sarah spread the hair removal cream all over my body from my neck down.
"Your legs are going to look so smooth and sexy Evie," Mistress Sarah said.
I stood in the tub confused at how hard my cock was. I was being emasculated, yet I was aroused and excited. I knew I could not stop what was happening and it excited me. I was so thrilled to be in the presence of a beautiful dominant woman. Her shiny black PVC outfit looked amazing against her skin and the outfit left little to the imagination. I had a perfect view of Mistress Sarah's tits while she was leaning over, covering my legs with the cream. All the sexuality around me was a fantasy come true.
While the cream tingled on my body and worked its magic, Mistress Sarah played with my cock, keeping me aroused. Then she turned the shower unit on and rinsed away the cream, I was left standing hairless and smooth all over.
Mistress Sarah ordered me to towel myself dry before she massaged a scented lotion all over my body, taking every opportunity to tease my cock and play with my nipples. I enjoyed the attention and soon my knees were weak, I was on the brink of orgasm. A constant stream of precum was leaking from my cock.
Mistress Sarah scooped up some of the cum that was leaking out of my hard cock and put it up to my lips. I obediently sucked my cum off her fingers. "Good girl," said Mistress Sarah. "I'm so proud of you,"
I was led back to the bedroom. Mistress Sarah pulled a large white box from under the bed and placed it on top of the bed.
"This is special sissy lingerie for you Evie. I know you want to be transformed into a pretty girl, but tonight you will be just a sissy. This is a necessary step in your training pet. You need to experience all the moments of becoming a sissy so that it will shape who you are and prepare you for the next exciting step of being completely feminized."
Mistress Sarah unpacked the box. She reached up and rubbed her hand across the stubble on my face. ” And I’ve purposely left your face unshaven today to remind you that you are a boy dressed as a girl."
As Mistress Sarah laid each item on the bed, I could see that it was truly sissy lingerie. There was lots of shiny satin, frilly fabric, and silky bows. I imagined the silk would feel incredible against my smooth skin.
It felt surreal to me to be standing there completely aroused and submissive while I was being dressed as a sissy. I was dressed in pink frilly satin panties, white stockings. The white stockings had large silk bows at the top.
Mistress Sarah admired my legs. The stocking enhanced smooth legs. She rubbed her hands along the stockings and commented, "Evie, your legs look so smooth and sexy in those stockings. You put other girls to shame."
I blushed but was actually proud of the compliment. I looked down at my legs and agreed. They looked very sexy. "Thank you Mistress," I replied.
Next Mistress Sarah approached me with a pink satin corset in her hands. In an excited voice she said, "Here's your first sissy corset. Put your arms out princess and I'll help you put it on."
Like a puppet, I obeyed. Butterflies filled my stomach and my cock twitched as Mistress Sarah wrapped the corset around me and pulled the straps very tight. I felt completely emasculated and feminized with the corset on. I was nervous and excited from crossing over this threshold into the feminine world. The tightness of the corset, felt like bondage to me. I felt as if I was being locked into the feminine world and pushed deeper under Mistress Sarah control. But this is where I wanted to be.
"Oh that is so pretty," commented Mistress Sarah. Mistress Sarah's body shivered in excitement to see me dressed so feminine and pretty and to see me so docile and submissive to her.
"My pretty little slave girl," she said with delight and accomplishment.
Mistress Sarah reached down and squeezed my cock through the panties and teased it a bit. She wanted to ensure I remained fully aroused and close to orgasm during my feminization. She knew keeping me aroused allowed me to be easily manipulated and trained to be her obedient feminine slave.
Mistress Sarah pulled a large satin dress from the closet and displayed it for me to see. The dress was the most feminine yet sissy looking maids dress that I had ever seen. It was made of high quality pink and white bridal satin. A white satin apron with pink ribbons was embroidered on the front of the dress. White shimmery lace trimmed the bottom of the dress and the sleeves. The shade of pink wasn’t a colour I would have chosen for myself, my preference was for sexy, sultry, slutty colours, this was definitely a real sissy colour.
Mistress Sarah asked, "Isn't this so pretty Evie. You are going to look so adorable in this."
I was very aroused and extremely excited to please Mistress Sarah. I could not wait to try the dress on. I knew my thoughts and desires at that moment broke all the rules I was taught about being a man but I didn't care. Mistress Sarah had unleashed a new feminine desire in me that I could not hold back. I accepted my new fate to be a sissy and I eagerly slipped into the dress with the help of Mistress Sarah.
Mistress Sarah pulled the dress straight around me and straightened the hems. She slowly walked around her new dress-up toy and admired 'her.' She commented, "What a lovely sight. You are so pretty and cute Evie. Mistress is very pleased with her sissy. Come look at yourself in the mirror."
I walked over to the mirror with Mistress Sarah. As I walked I was aware of many feminine sensations. The tightness of the corset against my chest, the silky stockings rubbing over my legs and stretching against my toes, and the dress rubbing along my thighs and legs as I walked were all wonderful new sensations that reminded me of my feminine state. My arousal grew stronger knowing that Mistress Sarah was purposely bringing out the girl inside me.
I never imagined I would be staring at myself in a mirror, dressed as a sissy. I never would have predicted or comprehended how exciting the moment would be. Beneath the pink shiny dress and underneath my satin frilly panties my cock throbbed harder than ever. I wanted to touch it stroke it desperately but I knew that was forbidden. Instead I flexed it, causing my cock to pulse against the silky sissy panties. I felt completely submissive dressed as a sissy and being with my Mistress who was still dressed in her tight sexy PVC outfit.
I gazed into the mirror like a deer in headlights. I thought I looked silly but I knew Mistress Sarah was pleased with my look and I knew that her pussy was dripping from my obedience and from my sissy look. This alone, made it worthwhile. I would not want to be caught dead dressed as I was, in front of my friends but in Mistress Sarah's world, I was thrilled, aroused, and excited to experience my sissy state.
Mistress Sarah showered me with compliments. "You are so pretty princess," cooed Mistress Sarah. "Pink is your colour sweetie. We're going to have to paint your nails a nice pretty pink to match your dress." "I have the perfect shade," said Mistress Sarah.
Everything happened so quickly. Mistress Sarah had me sit on stool, took my hands and went to work. In just a few minutes I had shiny pink finger nails. Next was a wig with long straight black hair and glossy red lipstick. Mistress Sarah brought a hand mirror up to my face so I could see the results.
I had a good amount of stubble on my face. The wig and lipstick alone did not create a pretty picture. I simply looked like a man wearing a wig and lipstick. I asked, "Can I shave Mistress? Will you put more make-up on me so I look more like a girl?"
Mistress Sarah responded, "Evie, it's good that you notice these things sweetie. Wanting to make your face pretty and girly shows me how well you are progressing in your training and moving along your journey to girlhood. I am so proud of you for that but we will save the make-up and shaving for tomorrow. Remember you are sissy tonight and this is what sissies look like. You make a perfect sissy sweetie."
"Yes Mistress," I replied.
Mistress Sarah commented, "You are quite a sissy boy Evie and tonight you are going to be my little bitch aren't you? Tell me what sissy bitch you are going to be for me."
I knew what she wanted to hear. "I'm going to be your sissy bitch tonight Mistress. I'm going to suck your strap-on and I'm going to let you fuck me with it."
Mistress Sarah laughed and questioned my last words, "Let me fuck you? There's not 'let' sissy bitch. I am going to fuck you. You have no choice. Now say it again slut. Tell me you are going to be fucked."
Mistress Sarah's words were stern and unforgiving, but I loved it. It pushed me further into subspace. I replied, "I am your sissy bitch and I am going to be fucked by you tonight."
"That's my slut," laughed Mistress Sarah. "Now show me your sissy panties. Lift up that cute dress of yours and show me your pretty panties."
I did as instructed. Mistress Sarah slapped my arse and commented on how cute my arse looked in the panties. I was made to bend forward. Then I felt my panties being pulled down to my thighs.
Mistress Sarah said, "This should help keep your mind on what's going to happen later tonight."
I felt something firm poke at the entrance to my arse. Slowly Mistress Sarah pushed a large lube covered butt plug into my arse. The wide plug spread my arse and filled me inside. I moaned in pleasure from the fullness. My cock twitched and dripped creamy cum from the carnal pleasure. Before Mistress Sarah pulled up my panties, she squeezed my cock a few times, causing me to shudder in pleasure. Warm cum oozed out onto her fingers. She spread the stickiness all over my cock and balls.
Somebody's sissy clitty is all wet, isn't it," questioned Mistress Sarah.
"Yes Mistress," I moaned.
Mistress Sarah moved her fingers up to my mouth and said, "You know what to do."
One-by-one she pushed her fingers into my mouth. I eagerly licked my own cum off her fingers. "Good girl, Evie. Lick up all that boy cum. “Mistress Sarah dipped her fingers into her pussy. These too were bought to my mouth for cleaning.
Mistress Sarah announced, "Now it's your turn to help me Evie."
Mistress Sarah told me to undress her. I happily obeyed, enjoying the sight of Mistress Sarah’s firm tits popping out of the tight PVC dress as I pulled it up. I felt like I was unwrapping the sexiest gift in the world. Mistress allowed me a few moments to worship her body. I gently licked and sucked her nipples and I spent a few minutes lapping at her pussy.
It took quite a bit of will-power but Mistress Sarah was able to stop things before it got too steamy. She wanted to have more fun in the bath and she thought this would also be a great tease for her sissy. Mistress Sarah handed me a small plastic basket that was filled with various sex toys and vibrators.
"Follow me Evie," giggled Mistress Sarah.
I followed her into the bathroom. Mistress Sarah looked at me in deep thought and said, "Hmmm Evie, I want you to be kneeling by the tub while I wash, but I don't want you to ruin your pretty sissy dress."
Mistress Sarah helped me out of the dress and hung it on a hanger for use later. I was left in my corset, pink frilly panties, and white lacy stockings. Mistress lightly pulled on the large satin bows at the top of the stockings, admiring them. "These are so cute and pretty Evie. They really bring out the sissy in you. It's so sexy. I love it!"
"Thank you, Mistress" I said enjoying the attention and compliment.
Mistress Sarah had turned on the shower over the bath and stepped in. Mistress Sarah had me kneel by the tub and hold the basket of sex toys. She sorted through the toys and picked out a small pink vibrator. "This will feel good in my pussy," she said happily and then stepped into the bath and pulled the shower curtain across, blocking my view.
Mistress Sarah was already wet and aroused from dominating and sissifying me and so the vibrator slipped easily into her pussy. Mistress Sarah’s pussy seemed to devour it, I could still hear it buzzing even deep inside her. Her eyes closed and she let out a gentle moan as waves of pleasure coursed through her body. I wanted it to be me giving Mistress pleasure, Mistress Sarah had even said, that if I was a good girl, I may be allowed to fuck her. But I knew I had to wait, Mistress was still training me and showing she had total control over my actions. It was exhilarating for Mistress Sarah to have her pet kneeling outside horny and waiting.
The vibrations in her pussy quickly brought her to the brink of orgasm. Her whole body was alive with pleasure.
Kneeling outside the bath, I was intently listening to the buzzing vibrator, the sex sounds, and the erotic moans on the other side of the shower curtain. I wished I was in the bath with Mistress Sarah. Even though I knew I shouldn’t without permission, I reached inside my panties and played with my cock while I listened and imagined what was going on.
Mistress Sarah pulled the curtain back for a moment to allow me a glimpse of the sizzling action. I was eye level with Mistress and had a perfect view of the vibrator slipping easily in and out of Mistress Sarah's pussy. Her wet shimmering body was a prize for my eyes.
I looked up at Mistress Sarah’s face and was immediately drawn to her eyes. Mistress Sarah purposely locked in on me and licked her lips. Seeing me kneeling and dressed as a sissy with my cock in my hands sent her over the edge. It was hard for her to not close her eyes and just sink into the water, but she wanted to see her Evie. She wanted me to see the lust and pleasure in her eyes while she climaxed. When her orgasm faded away she blew me a soft kiss with her lips and let the shower curtain fall back in place, leaving me throbbing and desperate to see more.
It was only a few seconds after the shower curtain fell shut that the pink vibrator was held out for me. "Evie, pass me the white vibrator," ordered Mistress Sarah.
I quickly pulled the vibrator from the basket of toys, it was quite a bit larger than the pink one and exchanged it for the wet pink one. Mistress Sarah ordered me to lick the pink one clean.
"Lick off my sweet juices sissy slut. And I want you to suck on it for a bit too Evie. Sissy's must learn to be good a sucking things” Another fantasy of mine that I had confessed to Mistress, I was bi-curious and wondered what it would be like to suck a cock. “Then you can clean it in the sink with soap and water."
"Yes Mistress," I replied, eager to please.
Willingly I licked up and down the sides of the vibrator, delighted to know it had been in her pussy. Then I pushed it into my mouth and sucked on it. The curtain opened for a second and Mistress Sarah giggled at the sight.
"Good girl," complimented Mistress Sarah.
"Push it in and out sissy. Suck it like a cock," She ordered.
I obeyed. My arousal heightened from the humiliating order.
"Mmmm, So nice. You're a good cock sucking sissy," Mistress Sarah said. Then the shower curtain closed again.
I heard more moans and buzzing as Mistress played with the larger vibrator, I couldn’t see, but could easily imagine that too slipping into Mistress’s wet pussy. As soon as I’d finished cleaning the pink vibrator Mistress Sarah shouted through the curtain, "Sissy, get my strap-on ready. I believe you’re ready to see and feel what I’ll be fucking you with later."
"Yes Mistress", I replied.
"Hurry princess. Put a nice cock in that harness."
I found the harness and a selection of cock shaped dildos in the basket. Quickly I secured a large dildo into the harness, about 10” long and thickly veined. There were even bigger ones waiting in the basket.
"It's ready Mistress," I announced. The shower curtain opened and Mistress Sarah tossed the used white vibrator at me and grabbed the strap-on from my hands.
"Thanks slut," she said. "You know what to do with the vibrator."
The curtain closed but the hot image of Mistress Sarah’s glistening body was still in my mind. I stared at the curtain wishing I could see right through it. Slowly I licked the second vibrator with my tongue and listened intently trying to imagine what was happening just a few inches from where I was kneeling.
A quiet moan from Mistress echoed through the small room. "oohhhh. That's feels so good."
"This is so delicious Evie," cooed Mistress Sarah.
I could hear the sounds of Mistress Sarah fucking herself with the strap-on cock at a steady but increasing pace. As the pace quickened Mistress Sarah's erotic moans became quicker and louder.
Mistress Sarah spoke to me through the curtain. "Hear that Evie....It's what you are going to sound like later tonight. I bet you will scream much louder. I’m going to make you scream and moan like a prissy little girl. Does that excite you slut?"
"Yes Mistress. My clitty is so hard and swollen right now. I can't wait. I wish you would fuck me right now."
"Mmm. That's a good bitch. Pull back the curtain and watch sissy," ordered Mistress Sarah.
I did not hesitate to obey. I slid the curtain back and watched Mistress Sarah pound her strap-on into her pussy. The steamy shower water sprayed all over her wet body. I was too excited to even feel the water splashing onto me. I stroked my cock as I watched, not even realizing I was stroking in rhythm with Mistress Sarah's thrusting.
"This is so hot! God I want to cum," I begged.
Mistress Sarah had not planned on allowing Evie an orgasm yet, but the moment just seemed right.
"Do you want to orgasm Evie slut," asked Mistress Sarah.
"Yes! Please," I begged, hoping she was not just teasing me.
"Get the cup from the sink," ordered Mistress Sarah.
Eagerly I scooped the cup off the sink and got back into position on my knees.
Mistress Sarah said to me, "You've been such an obedient little bitch for me Evie. You can follow me to an orgasm. I want all your cum in that cup, got it?"
"Yes Mistress. Thank you Mistress," I said, thrilled at this chance for release.
Mistress barely finished her sentence when her body started convulsing with pleasure. She pushed the strap-on deep inside her pussy. She moaned loudly and between orgasmic breaths shouted an order to me, "Cum bitch. Cum like a sissy."
I pumped my cock and filled the cup with cum. My orgasm seemed to last forever. When it finally finished, I did what Mistress had seen me do numerous times. I lifted the cum filled cup to my lips but to my surprise he was stopped.
Mistress Sarah yelled, "Wait slut!"
I stopped and looked at Mistress. She stepped out of the bath, and stepped into the harness of her strap-on, pulling it up and settling it in place. To me she looked even more erotic with that large cock bouncing in front of her. She mused out loud, "Evie, you are so eager to drink up your cum. You really are a sissy whore aren't you? I like that Evie. I like that you are eager to be my cum drinking slut. Pour some into your palm slut."
I tilted the cup and let some of the warm cum ooze out onto the palm of my hand.
Mistress Sarah thrust her strap-on towards me and instructed, "Good girl Evie. Now stroke my cock with it. Rub it all over the tip of my cock. That's it pretty. Get my cock nice and sticky. Make a nice creamy 'cocksicle' Evie."
I followed her orders, knowing that the 'cocksicle' was going to be for me. The order from Mistress came quick and sudden, "Suck it slut. Suck my cum covered cock."
I immediately obeyed. I took the cock into my mouth. Mistress slowly pumped just the head in and out of my mouth. Although I just had an orgasm, my cock was hard. What I was doing was so perverse and taboo that it thrilled me. I enjoyed being her fuck toy. Mistress Sarah fucked me mouth and called me her bitch, slut, and cum eating whore. All these humiliating things fuelled my arousal and made me want to be even sluttier.
My desire to be slutty was easily met. Mistress Sarah pulled her cock away and ordered, "Put some of that cum onto your lips. Make them nice and glossy for me." I dipped my fingers into the cum and rubbed them around my lips. "More cum on those lips bitch," she yelled.
I quickly complied, rubbing cum onto my lips until they were dripping. Then Mistress Sarah ordered me to pull out my butt plug. "Dip it in your cum whore. I want it dripping with your cum."
I obeyed. I felt like a whore. I was excited to be a whore for Mistress Sarah.
"Now push it back into your sissy pussy. Evie."
The plug slid back into my arsehole easily. I felt dirty and slutty pushing the cum covered plug into my arse. My cock twitched as the plug pressed deep into me. Having my cum pushed into my arse mentally took me to a deeper level of kinkiness and submission. "I feel so slutty," I admitted with delight.
"Good girl," encouraged Mistress Sarah. "You are a perfect sissy whore now Evie. You've got cum dripping off your lips and fingers and cum in your sissy pussy. That's how a whore feels after a good night with a man. You've got one thing left to do Evie. Show me how slutty you want to be and drink up the rest of your cum."
Mentally I had become her sissy whore and accordingly I obeyed Mistress Sarah's command with great pleasure. I tilted the cup upward and started to drink down the cum. Mistress Sarah put her hand on the cup it forced it back down slightly.
Seductively she said, "Slow down slut. You want to enjoy your creamy treat don't you?"
The creamy goo oozed into my mouth. I felt like a used whore and I loved it.
Libbie
- 07.12.2022
- 43
- 0
- Category:
- Crossdressing
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