Mistress Sarah makes Evie a Sissy 2
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Mistress Sarah Gives Evie An Assignment free porn video
Mistress Sarah led me back into her bedroom and sat naked in a chair in front of a large dressing table. She ordered me to fetch my maid's dress. It was time for me to learn how to properly dress her for a night out and she wanted me in full sissy attire for the event.
Mistress Sarah watched me step into my sissy dress. She told me to turn around slowly for her as she pulled down on the pink silky fabric, ensuring the shiny dress cascaded around my legs smoothly and wrinkle free. She then passed me a pair of 6” black heels.
“These will fit you and finish off that outfit quite nicely. Then walk around a little and let me see you,” Mistress Sarah said. I had worn heels before and was quite comfortable in them.
She leisurely caressed her own breasts as she watched the show. Her thumbs rubbed over her nipples, causing a brief shiver through her body. It was an arousing sight to see her sissy showing off for her. Each time I leant forward, Mistress Sarah was rewarded with the sexy image of my panties.
To Mistress Sarah, I did not exist anymore, at least not on the surface. I was tucked away deep inside Evie. That's where I belonged and Mistress Sarah intended on keeping me tucked away as long as possible. Evie was her creation and she needed to thrive and be free.
Mistress Sarah's pussy began to dampen as she admired her silk covered sissy. I looked pretty and docile draped in pink and white satin. The pretty silk bows all over the dress looked cute. Aside from my face, I was a sissy, her sissy. Mistress Sarah loved this image. The image of my strong arms disappearing into soft silk and lacy fabric hit an erotic nerve within her that caused her pussy to quiver in pleasure.
Needing to satisfy the heat between her legs, Mistress Sarah's right hand slid down to her pussy. She lightly traced her fingers over her soft pussy lips as she reminisced about her first days with Evie. She remembered how, although very willing, I had no direction or goal. I admitted I was a panty boy, but wasn’t completely sure what I wanted from it. However with carefully planned teasing and seduction, I was on my way to being a real sissy, her sissy. Mistress Sarah's fingers grew wetter as she played with herself.
Standing up to pee never crossed my mind anymore. Mistress Sarah had told me that girls sit down to pee and as a sissy I should do the same. Mistress Sarah took great pleasure in knowing that her power and sex appeal were the reason for all this. Evie was her creation and her property. She would continue to mould and shape my mind and body into a pretty submissive femme boy.
With her excitement building her patience grew short. "Evie. Come to me," she demanded. "Kneel at my feet," ordered Mistress Sarah.
I knelt down in front of Mistress.
Mistress Sarah spread open her knees, revealing her wet and swollen pussy. The smell of her pussy was strong and delicious.
"You have been naughty getting me excited like this. You need to take care of this problem and quickly so I can get ready," ordered Mistress Sarah.
I didn’t know what Mistress Sarah was getting ready for, but I certainly didn’t need telling twice to eat her pussy.
Mistress Sarah guided my head between her legs. My tongue licked up and down the length of her shaven pussy several times. Then it disappeared into the hot wetness. Mistress Sarah held my head against her pussy and moaned in delight as my tongue probed deep inside her.
My cock hung below me hard, throbbing, and untouched. This did not bother me for I knew my purpose was to serve and please Mistress. That in itself was rewarding for me. Also I was still getting pleasure from the plug that was still pressed tightly into my arse. I rocked slightly on my knees as I tongued Mistress's pussy, causing the plug to press against my panties and push deeper into my arse. I savoured this simulated fucking sensation in my boy pussy.
Soon Mistress Sarah erupted into orgasm. I pressed my mouth and nose into her tight wet hole and used my tongue as best I could to satisfy her orgasm. I kept licking and licking until Mistress Sarah finally pushed me away.
I was still very horny, and attentive. Although my cock was hidden beneath the sissy dress, the expression on my face must have been filled with arousal. Mistress wanted to have a little fun and so she ordered, "Lift up your dress, princess. I want to see your sissy cock. I bet it's so hard right now."
"Yes...very hard Mistress," I admitted as I slowly lifted the hem of my dress.
My cock was twitching on its own from all the excitement. Mistress moved her foot to my cock and gently rubbed the underside with her toes. She teased, "Aww. Look how excited my little bitch is. Poor Evie didn't get to cum."
I pushed my cock forward, humping her foot.
Mistress held her foot firm and said, "That's it, slut. Hump my foot. You are so desperate to cum aren't you?"
"Yes, Mistress. Please may I cum," I begged. I rubbed my cock up and down the underside of her foot.
Mistress Sarah's other foot joined in on the teasing. Both her feet cupped my cock as I humped away.
Again I begged, "Please Mistress, can I cum? I'm so close!"
Mistress Sarah quickly pulled her feet away and laughed. "You've already had an orgasm once today, Evie. I think that's enough. I want you to stay hot and horny all night. That way you will be begging me to fuck you with my strap-on later. And, anyway, now you’ve got to help me get ready. I’ll be going out for a while.”
For the next half-hour all attention was on Mistress Sarah. She ordered me to pick out four or five panty and bra sets from her lingerie drawer. While I gathered these items, Mistress had a quick shower and dried her hair.
"Let's see what you picked out, princess," said Mistress Sarah, brushing her long hair. "Hold them up one at a time for Mistress to see."
Mistress Sarah had a large collection of bras and panties. I had tried to pick a variety of styles and colours, hoping that at least one set would satisfy her. I started with a purple lace bra and matching thong.
"Mmm. I love that set," cooed Mistress Sarah. "Sexy choice, princess, but let's see what else you picked."
I held up each panty and bra. Mistress Sarah giggled a few times and complimented on how cute I would look in some of the items. She finally settled on a black lace bra with black silk boy shorts.
Mistress Sarah ordered me to put these on her. I knelt before her and slid the panties up her legs. She lifted her arse slightly off the chair, allowing me to pull the panties all the way up. Next I picked up the bra. I had taken many bras off girls in the past but had never put one on a girl and so I felt a little awkward.
Mistress Sarah noticed my uncertainty and hesitation. She joked, "Don't be scared Evie. It's just a bra. You can do it. Soon you'll be a pro with bras, dear. They will become a regular part of your wardrobe, pretty. We don't want your tits getting saggy do we?"
My cock twitched at the comment. I did not know how serious Mistress Sarah was about me wearing bras all the time. I had always preferred corsets and basques, but for some mysterious reason the idea excited me. I could not imagine how it would be possible but at the moment it seemed thrilling.
Mistress Sarah stood up and put her arms out for me. I slid the straps up her arms. It almost seemed cruel to be covering up such beautiful tits. Before the bra covered her tits, Mistress Sarah ordered, "Kiss them."
I gladly leaned down and gave each of her nipples a soft kiss and gentle tongue licking. My cock was raging hard beneath my sissy dress.
"Mmmm. So nice," moaned Mistress Sarah.
After enjoying her tits for a few brief seconds, I moved behind her and pulled her bra up. To my surprise, I managed to clasp the bra shut with only a slight bit of fumbling.
"Good girl," she said in a complimentary tone. "Now let's get you started on my hair."
Mistress handed me a brush and told me to start brushing her hair. Almost immediately Mistress Sarah ordered, "Harder! Don't be such a sissy!"
She laughed at the unintended pun. "Oh, that's right... you are a sissy. Try to be more like a man when you brush hair. I know it will be hard for you, pretty, but just try."
I blushed at the humiliating remarks and giggles. My red face seemed to be a visual gauge on my arousal and submission. The deeper I blushed the more my cock swelled and the more submissive I became. Obediently, I firmly brushed Mistress Sarah's hair. I felt like a slave worshipping a goddess.
Mistress Sarah did her own make-up, but told me I would need to learn this. In between brushing hair, I had to fetch various make-up items for her. Although most of the items were within easy reach, she still required me to fetch them. This served to reinforce my obedience and slave status.
I found the experience to be very gratifying. I enjoyed pampering my mistress and was eager to learn about make-up.
After Mistress Sarah's hair and make-up were done, I was sent to the wardrobe and told to pick up a simple black top and a tight black skirt. While Mistress Sarah quickly slipped into these I popped to the loo for a pee. On returning from the toilet I heard Mistress Sarah speaking, “Okay, see you in about ten minutes.”
My heart was racing. Was Mistress Sarah inviting someone round? I wasn’t sure if I was terrified or excited that someone else would see me dressed as a sissy.
Walking back into the bedroom, I thought Mistress Sarah looked sexy and flirty. "You look incredible, Mistress," I said.
"Thanks, slave. I’m sure I'll make a few cocks hard while I’m out. What do you think, Evie? Will the guys being dreaming of fucking me tonight?"
"Most definitely, Mistress. I want to."
Mistress Sarah laughed and looked into my eyes. "Silly Evie, you're just a sissy boy. I know your little clitty is all hard and swollen underneath that pretty dress but when I'm out I flirt with real men."
I was a little hurt. Mistress had always admired my cock and had often said that she’d enjoy me fucking her. For a brief moment, I wanted to show her that I could be a real man but part of me was excited at my predicament. There was a strange thrill in being humiliated and knowing that I was her servant, preparing her for an evening of flirting and possible sex.
I was confused at these emotions. Before I could get my thoughts together Mistress continued, "Don't worry Evie. You are special to me. You’ll get to fuck me, but I get to fuck you whenever I want and I am so looking forward to it."
My cock throbbed in my panties. "Me too, Mistress. I can't wait."
"I know, sissy. You are a slut aren't you? Tell me that, Evie. Tell me how bad you want me to fuck you."
Mistress Sarah's orders energized me with lust and excitement. "I want you to fuck me real bad, Mistress. I want to be your slut."
"Mmm. Are you my bitch?"
"Yes, I am your bitch. Please fuck your bitch," I begged, my cock throbbing harder by the minute.
"I'm going to fuck you hard, bitch! That's what you want isn't it?"
Overcome by her authority I replied, "Yes. Please fuck me hard! Fuck me anyway you want to."
Mistress Sarah's tone softened, "That's a good bitch. Oh, and I have a little assignment for you while I’m out."
"Assignment?" I questioned.
"Yes precious," replied Mistress Sarah. "I have come up with some wonderful assignments for you to help with your femme training. I’ve even made you a cute diary for you to track your progress and express your feelings through the transformation. Take a look."
She held up a small book. On the cover, in pink glitter, it said Evie's Diary. Seeing my female name on the cover added a new sense of reality to what was happening to me.
Mistress questioned, "Isn't it cute, Evie?"
"Yes, thank you, Mistress. It's very pretty." I was impressed at her thoughtfulness.
Mistress Sarah then explained my assignment. "Evie sweetie, on the first few pages of your diary I have started a few entries. While I am out, I want you to finish the thoughts that I started. Be sure to fill all the blank pages in between entries, okay princess?"
"Yes, Mistress," I replied.
"Some of the items you can start on right away. For example, the first page in your diary says, 'When I first saw Mistress Sarah I felt...'
"You need to write a paragraph to complete that thought. You already know enough to do that. However a few pages back the entry says, 'I went through Mistress Sarah's panties and tried them on. My three favorite pairs are....'
"Now you have not done that yet so obviously you can not complete this page yet. What do you think you need to do to complete this page?"
I said the obvious answer, "I need to go through your panty drawer and try on your panties."
"You got it! That is your assignment tonight, Evie. Tonight is all about discovering the feminine world and the girl within you. I want you to explore through all my stuff while I am out. In order for you to blossom into womanhood you need to discover and experiment with girly things."
"Girls don't become women overnight," she added. "The same applies to sissies. Now you need to let Evie run wild with those desires and discover the wonderful world of womanhood. We are much more sensual then men. A woman's world is full of pretty scents, and soft fabrics..."
Mistress Sarah continued explaining the assignment, "I want you to explore all those wonderful things. Go through my make-up, experiment with my lipstick and glosses and try on my panties, bras lingerie, skirts, dresses, and anything you can fit into."
I was becoming even more excited and aroused from my assignment. All these things seemed fun and exciting to do.
Mistress Sarah added, "Don't forget about perfumes and lotions. I want you smelling pretty for me later. Fresh like a virgin for your fucking. Okay, princess?"
"Of course," I replied in an erotic daze.
Mistress Sarah continued, "Nothing is off limits Evie, with one exception. You’re not allowed to cum. Explore it all. Take your time as you explore and discover these things, Evie. Think only of your senses. Pay attention to the scents, pretty colours and delicate fabrics. Submerse yourself in this secret dreamy world one step at a time. Make notes in your diary. What things do you like? What appeals to you? What makes you nervous or uncertain?" Mistress Sarah questioned, "Can you handle it, princess?"
"Yes. Thank you for this wonderful assignment. This is going to be fun."
"Of course it will be, dear. Everything about being a girl is fun. Once you enter my world you are not going to want to turn back."
"I'm already starting to feel that way," I admitted, somewhat surprised.
"Now, I wouldn’t want anyone to meet you when you're not looking your best," Mistress said as she began to apply red lipstick onto my lips.
My heart pounded in my chest. I was very nervous about meeting other people while dressed as a sissy.
Mistress picked up a blush brush and said, "A little blush with your red lipstick will give you the perfect sissy look."
She brushed the blush onto each cheek and inspected her work. "Perfect," she said.
Mistress made me look into the mirror. "You look like a boy in a wig who has been playing with make-up...a sissy boy. Any more make-up and you would start to look like a pretty girl."
I thought I looked silly. With more make-up I might just pass as a girl. I lightly protested, "I'd rather have the pretty girl look."
Mistress Sarah giggled at my embarrassment. It was the reaction she hoped for. "Aww. That's so cute, princess. I know how bad you want to be a girl but you've got to grow into that. Right now you're just a sissy. Be the best sissy that you can be and then maybe you can progress to the next stage of your training. Understand?"
"Yes, Mistress," I replied.
I understood what she was saying but my mind was swirling from all the mind games Mistress Sarah was playing with me. I wanted to progress to the next stage of training because I was having fun and I was in heaven being under her control. What made my mind flip was when Mistress said how much I wanted to be a girl. I questioned myself; did I really want to be a girl or was being a girl just better than being a sissy and that's why I wanted to be a girl?
My mind was both confused and excited. I enjoyed wearing the lingerie and silky dress. I actually felt sexy in my lingerie. I was even impressed at how good my legs looked when they were completely hairless. Deep down I think I was looking forward to being completely feminized. These thoughts would have never occurred to me prior to meeting Mistress Sarah. In a matter of months she had changed who I was.
Even my fantasies had changed. My fantasies were now all centered around being feminized and being Mistress Sarah’s play toy and servant. As I contemplated all this and realized how much I had succumbed to the power and control of my Mistress, a strong wave of arousal washed through my mind and body. I was in a great place.
“Before I go out, I think you deserve a little treat, just to keep you aroused,” Mistress Sarah said.
Mistress got to her knees and slipped her head under the hem of my dress. I could feel her soft hand release my already hard cock from my panties. Her lips circled the head of my cock as her tongue lapped up my pre cum. In one slow continuous motion, she took the full length of my cock into her mouth and throat. Her hand reached round and pushed my butt plug hard inside me, causing my cock to go even deeper into her throat. I was seconds away from cumming, exploding into her mouth. Mistress Sarah could sense this and pulled slowly away.
Just as Mistress Sarah’s head reappeared from under my dress the doorbell rang.
“Be a dear and go and see who’s at the door,” Mistress Sarah said.
I was at the bottom of the stairs before I realised what I was about to do. From the neck up I was definitely a guy, including the stubble. From the neck down I at least looked like a girl, apart from the obvious tenting in my dress caused by my very erect cock that Mistress hadn’t tucked back into my panties. I was a sissy. I started to turn and go back up the stairs, but Mistress Sarah was standing at the top step.
She very clearly mouthed the words, “Do it, sissy”
Nervously, I turned back to the door and opened it. The look on the guy's face was shock as he looked me up and down. Stammering all he said was, “Taxi for Sarah!”
Turning back to the stairs, I said, “Mistress, your taxi is here.”
From where I was standing I could clearly see up her skirt and the outline of her pussy through her panties and I’m sure the driver could see it too. Mistress Sarah could be such a tease when she wanted to be.
Mistress Sarah gave me a kiss on the cheek and squeezed my erect cock as she walked past, saying, “Don’t forget Evie, no cumming. Maybe you should start with a bubble bath and calm down a little. Spend twenty minutes soaking and thinking about how wonderful everything is right now. Then clean yourself up and go have fun."
For the first time since I arrived at Mistress Sarah's house, I was left alone in silence. My cock was still throbbing from all the attention. It continued to throb as I thought about my exciting assignments for the night. I picked up the diary with my feminine name on it and opened it.
Written in pink ink on the first page was, ''When I first saw Mistress Sarah I felt...." The remainder of the page was left blank for me to fill in.
Immediately my thoughts went into action. I picked up the pink pen and started writing how exciting and nervous I was earlier in the day. I easily filled up the blank page. It was good that only one page was left blank. Otherwise I would have gotten carried away and filled the whole journal on the first entry.
On page two, purple ink spelled out, "Today Mistress Sarah dressed me as a sissy. I wore...."
Several lines were left blank and then it read, "My favourite part about being a sissy is..."
I thought it would be cute to match the ink colours on each page. I put down the pink pen and picked up the purple one. I described my sissy dress and sexy lingerie. Then I described how exciting it was to show off my pretty clothes to Mistress. I admitted to loving all the attention as well as being covered in silky, soft clothes.
I found that I was completely aroused at writing my thoughts in my diary. Reliving the erotic fun earlier in the day caused my cock to swell and throb in my panties. It was like Mistress Sarah was teasing me without even being there.
The next page had the sentence about trying on Mistress Sarah's panties. I could not wait to do this. Suddenly I remembered that Mistress Sarah ordered me to take a bath before I began. Realizing I was already disobedient by first writing in my diary, I quickly put it down and headed upstairs to the bathroom so that I could get back on track.
I was enthused about my assignments and really wanted to please Mistress Sarah by diving into the feminine world. Her words echoed in my head, 'You need to discover and experiment with girly things....a women's world is full of pretty scents...you need to submerse yourself in this secret dreamy world."
With her words of motivation, I was eager to experiment. I turned on the water to fill the bathtub and then explored the bathroom. I discovered bath salts and many scents of bubble bath. There were fragrances of Cucumber, Sweet Pea and Cherry Blossom. I smelled each one. Each scent that I inhaled softened my mind and melted me further into the feminine world. I loved the Cherry Blossom fragrance and decided to use this for my bath.
As the water filled and the bubbles foamed, I lit all the candles that Mistress Sarah had placed around the bathroom. I turned off the lights and with a slight sigh at the loss stripped out of my dress and lingerie. Finally I eased myself into the bath.
The hot water surrounded and soothed me. The soft glow of the candles and the pretty scent from the bubble bath relaxed me. 'I could get use to this,' I thought.
To my surprise, as I relaxed and my mind cleared, my arousal grew. There was so much arousal pent up inside that my cock hardened beneath the suds and beckoned for me to stroke it. I played with my cock and thought about how much fun I was having as a sissy. This was something I could never admit to my friends. It challenged my own principles but I was undoubtedly enjoying what was happening. I knew that I was deeply entangled in Mistress Sarah's seductive web and would not be able to escape. For reasons unknown to me her power and dominance fuelled my arousal.
I soon realized that soaking in the tub would lead to my demise as I would surely stroke myself to an orgasm. I made the hard decision to stop and move on with my assignment. After my bath I went right for Mistress Sarah's panty drawer and lingerie chest. Even though I had her permission, I felt naughty and perverted going through her panties and bras.
I admired the many varieties of panties. I tried on silk, cotton, lace, and even mesh panties. There were boy shorts, thongs and French cut styles. Each time I slid on a new pair of panties my cock throbbed. I took my time, paying attention to their feel and look. The silk panties felt smooth and wonderful against my cock. Her thong panties tickled my arse. I loved how they felt when I walked and pranced around the room in them. Mistress Sarah had quite a selection of fur panties, which I enjoyed. The fur was on the outside of the panties but I could not resist turning one pair inside out and sliding them on. The fur felt amazing around my cock balls, and arse.
I was horny and in a rare mood and was really enjoying the fur. I lay on my stomach on Mistress Sarah's bed and slowly began to hump the bed. The soft fluffiness all around my sensitive areas was mind blowing. My entire body shivered with pleasure as my cock and balls rubbed over the fur. It only took a few seconds to bring myself to the edge. It was hard for me to stop. I was desperate to cum and knew it would be amazing to orgasm with my cock buried on the soft fur.
For a moment I thought I’d gone too far. I could feel an orgasm coming on. I quickly raised myself up to my hands and knees to relieve the pressure on my cock. I struggled and concentrated on not cumming. I did not want to be disobedient. It took all my energy and focus to hold back and fortunately I was able to stop my orgasm. I slid off the fur panties and made a note in my diary about how much I loved them.
Next I moved onto bras. My shoulders were broad and so I could not fit into Mistress Sarah's bras and night gowns but I held them up to my body and admired them. I managed to slip into one black silk teddy that was obviously over-sized for Mistress Sarah. I enjoyed how the silk fabric contoured with my body.
I made notes and comments in my diary while I played dress-up with Mistress Sarah's lingerie. I noted my favourite colours and styles. I commented at how sexy Mistress Sarah's red corset was. I even admitted that the thong panties felt nice rubbing along my arse.
The next few pages were presented like a self interview.
'My favorite perfume is....'
'My favorite nail polish is...'
'I thought I looked sexy in the following outfits....'
'I experimented with Mistress Sarah's make-up. I really liked....'
'I think my lips look sexiest when they are the colour...'
'When I go to the night clubs I want to wear....'
I continued through the diary, experimenting with all the girly things and completing the sentences. I felt naughty and excited exploring all the girly things. My cock continually swelled and contracted as I played with Mistress Sarah's belongings.
I loved the fire red nail polish and glossy red lipstick. Although I could not squeeze into many of her clothes, I imagined myself as a sexy girl and thought about how much fun and sexy it would be to wear some of her skirts and low cut tops. As I immersed myself into her things, my mind transformed further into the feminine world. It had a brainwashing effect on me. Mentally I was starting to think as a female. I even convinced myself to start losing weight so that I would look sexy in Mistress Sarah's clothes.
I was having so much fun that I barely noticed the time go by. My phone rang and I was thrilled to see that it was Mistress Sarah. I answered it quickly.
"Hello, princess. Are you a woman yet?"
I blushed even though I was alone. "Getting there, I guess."
"Yes you are, doll. You're almost past the sissy phase of your training. Are you excited about that?"
"Yes, Mistress," I admitted, not even sure what to expect next.
"I just need to pop your little cherry for you to graduate to the next level of your training. Are you ready to be fucked by my strap-on, sissy?"
My cock swelled harder than I ever imagined as I realized the moment of my deflowering was approaching fast. "Yes, I can't wait."
Mistress Sarah told me how the taxi driver had been very quiet in the car, so she had moved to the middle of the back seat and slipped her fingers into her pussy. The driver had watched her every move in the rear view mirror.
Mistress Sarah then gave a few orders, "I’ll be coming home soon slut. Clean up all my things that you played with. Make sure the place is nice and tidy and then get back into your sissy lingerie and dress. Be kneeling by the door waiting for me."
"Yes, Mistress."
“And make sure you touch up your make up.”
Mistress Sarah watched me step into my sissy dress. She told me to turn around slowly for her as she pulled down on the pink silky fabric, ensuring the shiny dress cascaded around my legs smoothly and wrinkle free. She then passed me a pair of 6” black heels.
“These will fit you and finish off that outfit quite nicely. Then walk around a little and let me see you,” Mistress Sarah said. I had worn heels before and was quite comfortable in them.
She leisurely caressed her own breasts as she watched the show. Her thumbs rubbed over her nipples, causing a brief shiver through her body. It was an arousing sight to see her sissy showing off for her. Each time I leant forward, Mistress Sarah was rewarded with the sexy image of my panties.
To Mistress Sarah, I did not exist anymore, at least not on the surface. I was tucked away deep inside Evie. That's where I belonged and Mistress Sarah intended on keeping me tucked away as long as possible. Evie was her creation and she needed to thrive and be free.
Mistress Sarah's pussy began to dampen as she admired her silk covered sissy. I looked pretty and docile draped in pink and white satin. The pretty silk bows all over the dress looked cute. Aside from my face, I was a sissy, her sissy. Mistress Sarah loved this image. The image of my strong arms disappearing into soft silk and lacy fabric hit an erotic nerve within her that caused her pussy to quiver in pleasure.
Needing to satisfy the heat between her legs, Mistress Sarah's right hand slid down to her pussy. She lightly traced her fingers over her soft pussy lips as she reminisced about her first days with Evie. She remembered how, although very willing, I had no direction or goal. I admitted I was a panty boy, but wasn’t completely sure what I wanted from it. However with carefully planned teasing and seduction, I was on my way to being a real sissy, her sissy. Mistress Sarah's fingers grew wetter as she played with herself.
Standing up to pee never crossed my mind anymore. Mistress Sarah had told me that girls sit down to pee and as a sissy I should do the same. Mistress Sarah took great pleasure in knowing that her power and sex appeal were the reason for all this. Evie was her creation and her property. She would continue to mould and shape my mind and body into a pretty submissive femme boy.
With her excitement building her patience grew short. "Evie. Come to me," she demanded. "Kneel at my feet," ordered Mistress Sarah.
I knelt down in front of Mistress.
Mistress Sarah spread open her knees, revealing her wet and swollen pussy. The smell of her pussy was strong and delicious.
"You have been naughty getting me excited like this. You need to take care of this problem and quickly so I can get ready," ordered Mistress Sarah.
I didn’t know what Mistress Sarah was getting ready for, but I certainly didn’t need telling twice to eat her pussy.
Mistress Sarah guided my head between her legs. My tongue licked up and down the length of her shaven pussy several times. Then it disappeared into the hot wetness. Mistress Sarah held my head against her pussy and moaned in delight as my tongue probed deep inside her.
My cock hung below me hard, throbbing, and untouched. This did not bother me for I knew my purpose was to serve and please Mistress. That in itself was rewarding for me. Also I was still getting pleasure from the plug that was still pressed tightly into my arse. I rocked slightly on my knees as I tongued Mistress's pussy, causing the plug to press against my panties and push deeper into my arse. I savoured this simulated fucking sensation in my boy pussy.
Soon Mistress Sarah erupted into orgasm. I pressed my mouth and nose into her tight wet hole and used my tongue as best I could to satisfy her orgasm. I kept licking and licking until Mistress Sarah finally pushed me away.
I was still very horny, and attentive. Although my cock was hidden beneath the sissy dress, the expression on my face must have been filled with arousal. Mistress wanted to have a little fun and so she ordered, "Lift up your dress, princess. I want to see your sissy cock. I bet it's so hard right now."
"Yes...very hard Mistress," I admitted as I slowly lifted the hem of my dress.
My cock was twitching on its own from all the excitement. Mistress moved her foot to my cock and gently rubbed the underside with her toes. She teased, "Aww. Look how excited my little bitch is. Poor Evie didn't get to cum."
I pushed my cock forward, humping her foot.
Mistress held her foot firm and said, "That's it, slut. Hump my foot. You are so desperate to cum aren't you?"
"Yes, Mistress. Please may I cum," I begged. I rubbed my cock up and down the underside of her foot.
Mistress Sarah's other foot joined in on the teasing. Both her feet cupped my cock as I humped away.
Again I begged, "Please Mistress, can I cum? I'm so close!"
Mistress Sarah quickly pulled her feet away and laughed. "You've already had an orgasm once today, Evie. I think that's enough. I want you to stay hot and horny all night. That way you will be begging me to fuck you with my strap-on later. And, anyway, now you’ve got to help me get ready. I’ll be going out for a while.”
For the next half-hour all attention was on Mistress Sarah. She ordered me to pick out four or five panty and bra sets from her lingerie drawer. While I gathered these items, Mistress had a quick shower and dried her hair.
"Let's see what you picked out, princess," said Mistress Sarah, brushing her long hair. "Hold them up one at a time for Mistress to see."
Mistress Sarah had a large collection of bras and panties. I had tried to pick a variety of styles and colours, hoping that at least one set would satisfy her. I started with a purple lace bra and matching thong.
"Mmm. I love that set," cooed Mistress Sarah. "Sexy choice, princess, but let's see what else you picked."
I held up each panty and bra. Mistress Sarah giggled a few times and complimented on how cute I would look in some of the items. She finally settled on a black lace bra with black silk boy shorts.
Mistress Sarah ordered me to put these on her. I knelt before her and slid the panties up her legs. She lifted her arse slightly off the chair, allowing me to pull the panties all the way up. Next I picked up the bra. I had taken many bras off girls in the past but had never put one on a girl and so I felt a little awkward.
Mistress Sarah noticed my uncertainty and hesitation. She joked, "Don't be scared Evie. It's just a bra. You can do it. Soon you'll be a pro with bras, dear. They will become a regular part of your wardrobe, pretty. We don't want your tits getting saggy do we?"
My cock twitched at the comment. I did not know how serious Mistress Sarah was about me wearing bras all the time. I had always preferred corsets and basques, but for some mysterious reason the idea excited me. I could not imagine how it would be possible but at the moment it seemed thrilling.
Mistress Sarah stood up and put her arms out for me. I slid the straps up her arms. It almost seemed cruel to be covering up such beautiful tits. Before the bra covered her tits, Mistress Sarah ordered, "Kiss them."
I gladly leaned down and gave each of her nipples a soft kiss and gentle tongue licking. My cock was raging hard beneath my sissy dress.
"Mmmm. So nice," moaned Mistress Sarah.
After enjoying her tits for a few brief seconds, I moved behind her and pulled her bra up. To my surprise, I managed to clasp the bra shut with only a slight bit of fumbling.
"Good girl," she said in a complimentary tone. "Now let's get you started on my hair."
Mistress handed me a brush and told me to start brushing her hair. Almost immediately Mistress Sarah ordered, "Harder! Don't be such a sissy!"
She laughed at the unintended pun. "Oh, that's right... you are a sissy. Try to be more like a man when you brush hair. I know it will be hard for you, pretty, but just try."
I blushed at the humiliating remarks and giggles. My red face seemed to be a visual gauge on my arousal and submission. The deeper I blushed the more my cock swelled and the more submissive I became. Obediently, I firmly brushed Mistress Sarah's hair. I felt like a slave worshipping a goddess.
Mistress Sarah did her own make-up, but told me I would need to learn this. In between brushing hair, I had to fetch various make-up items for her. Although most of the items were within easy reach, she still required me to fetch them. This served to reinforce my obedience and slave status.
I found the experience to be very gratifying. I enjoyed pampering my mistress and was eager to learn about make-up.
After Mistress Sarah's hair and make-up were done, I was sent to the wardrobe and told to pick up a simple black top and a tight black skirt. While Mistress Sarah quickly slipped into these I popped to the loo for a pee. On returning from the toilet I heard Mistress Sarah speaking, “Okay, see you in about ten minutes.”
My heart was racing. Was Mistress Sarah inviting someone round? I wasn’t sure if I was terrified or excited that someone else would see me dressed as a sissy.
Walking back into the bedroom, I thought Mistress Sarah looked sexy and flirty. "You look incredible, Mistress," I said.
"Thanks, slave. I’m sure I'll make a few cocks hard while I’m out. What do you think, Evie? Will the guys being dreaming of fucking me tonight?"
"Most definitely, Mistress. I want to."
Mistress Sarah laughed and looked into my eyes. "Silly Evie, you're just a sissy boy. I know your little clitty is all hard and swollen underneath that pretty dress but when I'm out I flirt with real men."
I was a little hurt. Mistress had always admired my cock and had often said that she’d enjoy me fucking her. For a brief moment, I wanted to show her that I could be a real man but part of me was excited at my predicament. There was a strange thrill in being humiliated and knowing that I was her servant, preparing her for an evening of flirting and possible sex.
I was confused at these emotions. Before I could get my thoughts together Mistress continued, "Don't worry Evie. You are special to me. You’ll get to fuck me, but I get to fuck you whenever I want and I am so looking forward to it."
My cock throbbed in my panties. "Me too, Mistress. I can't wait."
"I know, sissy. You are a slut aren't you? Tell me that, Evie. Tell me how bad you want me to fuck you."
Mistress Sarah's orders energized me with lust and excitement. "I want you to fuck me real bad, Mistress. I want to be your slut."
"Mmm. Are you my bitch?"
"Yes, I am your bitch. Please fuck your bitch," I begged, my cock throbbing harder by the minute.
"I'm going to fuck you hard, bitch! That's what you want isn't it?"
Overcome by her authority I replied, "Yes. Please fuck me hard! Fuck me anyway you want to."
Mistress Sarah's tone softened, "That's a good bitch. Oh, and I have a little assignment for you while I’m out."
"Assignment?" I questioned.
"Yes precious," replied Mistress Sarah. "I have come up with some wonderful assignments for you to help with your femme training. I’ve even made you a cute diary for you to track your progress and express your feelings through the transformation. Take a look."
She held up a small book. On the cover, in pink glitter, it said Evie's Diary. Seeing my female name on the cover added a new sense of reality to what was happening to me.
Mistress questioned, "Isn't it cute, Evie?"
"Yes, thank you, Mistress. It's very pretty." I was impressed at her thoughtfulness.
Mistress Sarah then explained my assignment. "Evie sweetie, on the first few pages of your diary I have started a few entries. While I am out, I want you to finish the thoughts that I started. Be sure to fill all the blank pages in between entries, okay princess?"
"Yes, Mistress," I replied.
"Some of the items you can start on right away. For example, the first page in your diary says, 'When I first saw Mistress Sarah I felt...'
"You need to write a paragraph to complete that thought. You already know enough to do that. However a few pages back the entry says, 'I went through Mistress Sarah's panties and tried them on. My three favorite pairs are....'
"Now you have not done that yet so obviously you can not complete this page yet. What do you think you need to do to complete this page?"
I said the obvious answer, "I need to go through your panty drawer and try on your panties."
"You got it! That is your assignment tonight, Evie. Tonight is all about discovering the feminine world and the girl within you. I want you to explore through all my stuff while I am out. In order for you to blossom into womanhood you need to discover and experiment with girly things."
"Girls don't become women overnight," she added. "The same applies to sissies. Now you need to let Evie run wild with those desires and discover the wonderful world of womanhood. We are much more sensual then men. A woman's world is full of pretty scents, and soft fabrics..."
Mistress Sarah continued explaining the assignment, "I want you to explore all those wonderful things. Go through my make-up, experiment with my lipstick and glosses and try on my panties, bras lingerie, skirts, dresses, and anything you can fit into."
I was becoming even more excited and aroused from my assignment. All these things seemed fun and exciting to do.
Mistress Sarah added, "Don't forget about perfumes and lotions. I want you smelling pretty for me later. Fresh like a virgin for your fucking. Okay, princess?"
"Of course," I replied in an erotic daze.
Mistress Sarah continued, "Nothing is off limits Evie, with one exception. You’re not allowed to cum. Explore it all. Take your time as you explore and discover these things, Evie. Think only of your senses. Pay attention to the scents, pretty colours and delicate fabrics. Submerse yourself in this secret dreamy world one step at a time. Make notes in your diary. What things do you like? What appeals to you? What makes you nervous or uncertain?" Mistress Sarah questioned, "Can you handle it, princess?"
"Yes. Thank you for this wonderful assignment. This is going to be fun."
"Of course it will be, dear. Everything about being a girl is fun. Once you enter my world you are not going to want to turn back."
"I'm already starting to feel that way," I admitted, somewhat surprised.
"Now, I wouldn’t want anyone to meet you when you're not looking your best," Mistress said as she began to apply red lipstick onto my lips.
My heart pounded in my chest. I was very nervous about meeting other people while dressed as a sissy.
Mistress picked up a blush brush and said, "A little blush with your red lipstick will give you the perfect sissy look."
She brushed the blush onto each cheek and inspected her work. "Perfect," she said.
Mistress made me look into the mirror. "You look like a boy in a wig who has been playing with make-up...a sissy boy. Any more make-up and you would start to look like a pretty girl."
I thought I looked silly. With more make-up I might just pass as a girl. I lightly protested, "I'd rather have the pretty girl look."
Mistress Sarah giggled at my embarrassment. It was the reaction she hoped for. "Aww. That's so cute, princess. I know how bad you want to be a girl but you've got to grow into that. Right now you're just a sissy. Be the best sissy that you can be and then maybe you can progress to the next stage of your training. Understand?"
"Yes, Mistress," I replied.
I understood what she was saying but my mind was swirling from all the mind games Mistress Sarah was playing with me. I wanted to progress to the next stage of training because I was having fun and I was in heaven being under her control. What made my mind flip was when Mistress said how much I wanted to be a girl. I questioned myself; did I really want to be a girl or was being a girl just better than being a sissy and that's why I wanted to be a girl?
My mind was both confused and excited. I enjoyed wearing the lingerie and silky dress. I actually felt sexy in my lingerie. I was even impressed at how good my legs looked when they were completely hairless. Deep down I think I was looking forward to being completely feminized. These thoughts would have never occurred to me prior to meeting Mistress Sarah. In a matter of months she had changed who I was.
Even my fantasies had changed. My fantasies were now all centered around being feminized and being Mistress Sarah’s play toy and servant. As I contemplated all this and realized how much I had succumbed to the power and control of my Mistress, a strong wave of arousal washed through my mind and body. I was in a great place.
“Before I go out, I think you deserve a little treat, just to keep you aroused,” Mistress Sarah said.
Mistress got to her knees and slipped her head under the hem of my dress. I could feel her soft hand release my already hard cock from my panties. Her lips circled the head of my cock as her tongue lapped up my pre cum. In one slow continuous motion, she took the full length of my cock into her mouth and throat. Her hand reached round and pushed my butt plug hard inside me, causing my cock to go even deeper into her throat. I was seconds away from cumming, exploding into her mouth. Mistress Sarah could sense this and pulled slowly away.
Just as Mistress Sarah’s head reappeared from under my dress the doorbell rang.
“Be a dear and go and see who’s at the door,” Mistress Sarah said.
I was at the bottom of the stairs before I realised what I was about to do. From the neck up I was definitely a guy, including the stubble. From the neck down I at least looked like a girl, apart from the obvious tenting in my dress caused by my very erect cock that Mistress hadn’t tucked back into my panties. I was a sissy. I started to turn and go back up the stairs, but Mistress Sarah was standing at the top step.
She very clearly mouthed the words, “Do it, sissy”
Nervously, I turned back to the door and opened it. The look on the guy's face was shock as he looked me up and down. Stammering all he said was, “Taxi for Sarah!”
Turning back to the stairs, I said, “Mistress, your taxi is here.”
From where I was standing I could clearly see up her skirt and the outline of her pussy through her panties and I’m sure the driver could see it too. Mistress Sarah could be such a tease when she wanted to be.
Mistress Sarah gave me a kiss on the cheek and squeezed my erect cock as she walked past, saying, “Don’t forget Evie, no cumming. Maybe you should start with a bubble bath and calm down a little. Spend twenty minutes soaking and thinking about how wonderful everything is right now. Then clean yourself up and go have fun."
For the first time since I arrived at Mistress Sarah's house, I was left alone in silence. My cock was still throbbing from all the attention. It continued to throb as I thought about my exciting assignments for the night. I picked up the diary with my feminine name on it and opened it.
Written in pink ink on the first page was, ''When I first saw Mistress Sarah I felt...." The remainder of the page was left blank for me to fill in.
Immediately my thoughts went into action. I picked up the pink pen and started writing how exciting and nervous I was earlier in the day. I easily filled up the blank page. It was good that only one page was left blank. Otherwise I would have gotten carried away and filled the whole journal on the first entry.
On page two, purple ink spelled out, "Today Mistress Sarah dressed me as a sissy. I wore...."
Several lines were left blank and then it read, "My favourite part about being a sissy is..."
I thought it would be cute to match the ink colours on each page. I put down the pink pen and picked up the purple one. I described my sissy dress and sexy lingerie. Then I described how exciting it was to show off my pretty clothes to Mistress. I admitted to loving all the attention as well as being covered in silky, soft clothes.
I found that I was completely aroused at writing my thoughts in my diary. Reliving the erotic fun earlier in the day caused my cock to swell and throb in my panties. It was like Mistress Sarah was teasing me without even being there.
The next page had the sentence about trying on Mistress Sarah's panties. I could not wait to do this. Suddenly I remembered that Mistress Sarah ordered me to take a bath before I began. Realizing I was already disobedient by first writing in my diary, I quickly put it down and headed upstairs to the bathroom so that I could get back on track.
I was enthused about my assignments and really wanted to please Mistress Sarah by diving into the feminine world. Her words echoed in my head, 'You need to discover and experiment with girly things....a women's world is full of pretty scents...you need to submerse yourself in this secret dreamy world."
With her words of motivation, I was eager to experiment. I turned on the water to fill the bathtub and then explored the bathroom. I discovered bath salts and many scents of bubble bath. There were fragrances of Cucumber, Sweet Pea and Cherry Blossom. I smelled each one. Each scent that I inhaled softened my mind and melted me further into the feminine world. I loved the Cherry Blossom fragrance and decided to use this for my bath.
As the water filled and the bubbles foamed, I lit all the candles that Mistress Sarah had placed around the bathroom. I turned off the lights and with a slight sigh at the loss stripped out of my dress and lingerie. Finally I eased myself into the bath.
The hot water surrounded and soothed me. The soft glow of the candles and the pretty scent from the bubble bath relaxed me. 'I could get use to this,' I thought.
To my surprise, as I relaxed and my mind cleared, my arousal grew. There was so much arousal pent up inside that my cock hardened beneath the suds and beckoned for me to stroke it. I played with my cock and thought about how much fun I was having as a sissy. This was something I could never admit to my friends. It challenged my own principles but I was undoubtedly enjoying what was happening. I knew that I was deeply entangled in Mistress Sarah's seductive web and would not be able to escape. For reasons unknown to me her power and dominance fuelled my arousal.
I soon realized that soaking in the tub would lead to my demise as I would surely stroke myself to an orgasm. I made the hard decision to stop and move on with my assignment. After my bath I went right for Mistress Sarah's panty drawer and lingerie chest. Even though I had her permission, I felt naughty and perverted going through her panties and bras.
I admired the many varieties of panties. I tried on silk, cotton, lace, and even mesh panties. There were boy shorts, thongs and French cut styles. Each time I slid on a new pair of panties my cock throbbed. I took my time, paying attention to their feel and look. The silk panties felt smooth and wonderful against my cock. Her thong panties tickled my arse. I loved how they felt when I walked and pranced around the room in them. Mistress Sarah had quite a selection of fur panties, which I enjoyed. The fur was on the outside of the panties but I could not resist turning one pair inside out and sliding them on. The fur felt amazing around my cock balls, and arse.
I was horny and in a rare mood and was really enjoying the fur. I lay on my stomach on Mistress Sarah's bed and slowly began to hump the bed. The soft fluffiness all around my sensitive areas was mind blowing. My entire body shivered with pleasure as my cock and balls rubbed over the fur. It only took a few seconds to bring myself to the edge. It was hard for me to stop. I was desperate to cum and knew it would be amazing to orgasm with my cock buried on the soft fur.
For a moment I thought I’d gone too far. I could feel an orgasm coming on. I quickly raised myself up to my hands and knees to relieve the pressure on my cock. I struggled and concentrated on not cumming. I did not want to be disobedient. It took all my energy and focus to hold back and fortunately I was able to stop my orgasm. I slid off the fur panties and made a note in my diary about how much I loved them.
Next I moved onto bras. My shoulders were broad and so I could not fit into Mistress Sarah's bras and night gowns but I held them up to my body and admired them. I managed to slip into one black silk teddy that was obviously over-sized for Mistress Sarah. I enjoyed how the silk fabric contoured with my body.
I made notes and comments in my diary while I played dress-up with Mistress Sarah's lingerie. I noted my favourite colours and styles. I commented at how sexy Mistress Sarah's red corset was. I even admitted that the thong panties felt nice rubbing along my arse.
The next few pages were presented like a self interview.
'My favorite perfume is....'
'My favorite nail polish is...'
'I thought I looked sexy in the following outfits....'
'I experimented with Mistress Sarah's make-up. I really liked....'
'I think my lips look sexiest when they are the colour...'
'When I go to the night clubs I want to wear....'
I continued through the diary, experimenting with all the girly things and completing the sentences. I felt naughty and excited exploring all the girly things. My cock continually swelled and contracted as I played with Mistress Sarah's belongings.
I loved the fire red nail polish and glossy red lipstick. Although I could not squeeze into many of her clothes, I imagined myself as a sexy girl and thought about how much fun and sexy it would be to wear some of her skirts and low cut tops. As I immersed myself into her things, my mind transformed further into the feminine world. It had a brainwashing effect on me. Mentally I was starting to think as a female. I even convinced myself to start losing weight so that I would look sexy in Mistress Sarah's clothes.
I was having so much fun that I barely noticed the time go by. My phone rang and I was thrilled to see that it was Mistress Sarah. I answered it quickly.
"Hello, princess. Are you a woman yet?"
I blushed even though I was alone. "Getting there, I guess."
"Yes you are, doll. You're almost past the sissy phase of your training. Are you excited about that?"
"Yes, Mistress," I admitted, not even sure what to expect next.
"I just need to pop your little cherry for you to graduate to the next level of your training. Are you ready to be fucked by my strap-on, sissy?"
My cock swelled harder than I ever imagined as I realized the moment of my deflowering was approaching fast. "Yes, I can't wait."
Mistress Sarah told me how the taxi driver had been very quiet in the car, so she had moved to the middle of the back seat and slipped her fingers into her pussy. The driver had watched her every move in the rear view mirror.
Mistress Sarah then gave a few orders, "I’ll be coming home soon slut. Clean up all my things that you played with. Make sure the place is nice and tidy and then get back into your sissy lingerie and dress. Be kneeling by the door waiting for me."
"Yes, Mistress."
“And make sure you touch up your make up.”
Mikhaela
- 05.09.2020
- 48
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- Category:
- Crossdressing
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