TITLE    : Euphoria Resort Ch. 02
STORYID  : euphoria-resort-ch-02
SUMMARY  : Sissy Tiff is signed away into training.
AUTHOR   : sissyashley4bbc@lit
DATE     : 2023-07-14
CATEGORY : transgender-crossdressers
FLAGS    : h
TAGS     : |cuckold|feminization|bbc|sissy|black cock|black man|interracial|big black cock|dildo|chastity|


A continuation of my previous story. all characters are adults!

I was moaning uncontrollably as Walter pounded my poor little asshole on the desk. My actually asshole had gone numb from the assault, but it was the constant hammering of my prostate that had me in a constant state of pleasure.

"You need to quiet down," Vanessa said, "if you can't do it on your own, I'll have to place a ball gag around you. I need to go over next steps for yourself and Jess."

"I'm sorry, its just that...ugh" I moaned again as Walter continued to dig his big black cock into me, searching for his own orgasm.

"Don't worry sweetie, lets just go ahead and put this on you so we can get on with it," she said calmly as she slid an elastic band around my head, placing a rubber ball gag in my mouth.

"That's better," she continued, "sometime's these sissies have a hard time controlling themselves. They just need a little guidance, that's all. OK, so you both are probably curious about what is next. Jess, I'll start with you. Over the next few days, you are going to enjoy the good life!"

She handed Jess her tablet.

"Scroll through these men and select who you would like to be partnered with. We'll take care of the rest! The men have all been carefully curated by the resort and are STD free, so no worries there. You will see they come in all different shapes and sizes."

Jess blushed, "so I am to have sex with whoever of these men I choose?"

"Only if you want to feel what it is like to have sex with a real man. As you have witnessed today, that is no man you have been sleeping with."

"What if I don't like the one I choose?" Jess asked.

"Great question! You will have a sissy maid waiting on your every need. Should you want a different man, or men if you want to get frisky, just ask and your sissy will retrieve a tablet for you to make your next selection."

"A sissy maid?" Jess asked curiously.

"Yes! Many of the sissies who come here end up signing contracts to live here full time and work as maids."

"I see, is that what his training will be?" Jess asked, nodding at me as I continued to get fucked on the desk.

"Correct, I'll get to that soon. If I could make a recommendation though for you, start with someone about 8 inches. No need to dive into the deep end here. 8 inches will be double the size that you are used to, and if you are craving more, just ask your sissy maid to bring you the tablet and you can choose someone bigger. Take your time, enjoy it!"

"That makes sense," Jess said as she tapped the screen and handed it back to Vanessa.

"Great choice!" Vanessa said, giving Jess a wink as she looked over the selection she made.

I tried, but I couldn't quite see the screen from my vantage point.

"Walter, are you almost done there?" Vanessa said calmly over her shoulder.

Walter didn't say a word, but he grabbed my hips tight and slammed the length of his big black cock into my ass and roared, cumming deep inside of me.

I felt his hot cum coat my insides. I shuttered in pleasure from the feeling of his big black cock, pulsating inside of me as his own orgasm left his body and poured into my ass.

It was too much for me, my whole body tightened up and my ass instinctively clenched on his big black cock, milking every last drop from him.

As my body writhed on his big black cock, I had my second orgasm.

Cum oozed out of my lace panties.

"Ah look, a 98!" Vanessa said, showing the tablet to Jess. "Your sissy over there has a really impressive sex drive. I'm glad we are able to reorient it properly, to be useful. Unlike before."

Eventually, Walter pulled out, and I felt a river of cum leak out of my ass. I felt so empty. My ass opened and closed, trying to hold onto his cum, but also recoiling after being stretched to unthinkable levels.

"Walter, come sit on the couch next to Jess," Vanessa instructed, "and bring your sissy."

Walter grabbed my hand and helped me to my feet. My knees were weak from the orgasms I just had. He walked over to the couch and sat down. As he sat, he put his hand on my shoulder, ushering me to my position, kneeling on the ground in front of him.

I was now staring directly at the big black cock that took my anal virginity, the big black cock that gave me a perfect 100 orgasm.

I was mesmerized.

It was truly enormous. Even after cumming, it remained hard as a rock. However the weight of it didn't allow it to stand straight up in the air. It leaned back towards Walter's belly.

I couldn't believe this was just inside of me.

"Why don't you clean your man off and I'll go over your arrangement with Jess here," Vanessa instructed.

I nodded as Walter grabbed my head and placed my mouth at the tip of his big black cock.

My instincts took over. I wanted him to feel good. I licked the underside of the head and opened my mouth wide to take the head into my mouth. My tongue swirled around the head as best I could, but there wasn't much room for me to operate given he took up my entire mouth.

I pulled my mouth off the head and worked my way down the shaft, licking him clean.

"Good girl," I heard him say as he kept a tight grip on my head.

"Ok so as you see, your sissy here is a natural," Vanessa started. "Usually we need to have phase 1 of sissy training, which is essentially what happened this morning. I think your sissy knows her place. Speaking of which, do you have a name in mind?"

"A name?" Jess asked, staring at me as I continued to explore his big black cock with my mouth.

"Yea, Tim doesn't work. He needs a feminine name. I recommend a play off of Tim as a reminder for what he was and what he has become."

"I see, how about Tiffany? Tiff for short."

"Love it, nice and slutty. Do you like it Tiff?"

"Yes," I tried to say, but only "mmph" came out as my mouth was full of big black cock.

Vanessa continued, "since Tiff is has completed phase 1 we will move right on to phase 2. Reorientation and training. Since you are married, Tiff is your sissy. You own her. It is up to you how you treat her. But remember, she has zero leverage over you. Tim's life was over the second he came all over Walter's big black cock."

"I agree," Jess said.

"So for the next little bit, you will get a sissy maid, and Tiff will go into intensive training to prepare for her new life as your sissy. I won't go into all of the details, but after training, Tiff will join the sissy maid being assigned to you as an apprentice. From there, it is really up to you."

"I see, so we wont be seeing each other for a while?" Jess asked.

"You might come across each other, but it is unlikely. We try to keep the trainees with other sissies for bonding purposes. Additionally, if you ask your assigned sissy for her tablet, you will be able to check up on your sissy's training. We consider Tiff your property, so you should be able to check up on your property."

Jess nodded, "is there anything I should know about my sissy maid for the next few days?"

"Another great question," Vanessa said, "and I'm glad you are getting into your new role and discussing rules for sissies. Short answer, you will be getting one of our best sissies, so I don't expect any issues. She is yours to do with as you please, she cannot say no, so feel free to get creative. Just as Tiff will be in training, this is time for you to figure out what kind of owner you want to be. The only rule that sissies sometimes need help remembering is that they are not allowed to satisfy their own sexual urges unless either you allow them to, or you are having sex with a man. Sissies are NEVER allowed to touch their little penises, but they are allowed dildo play when you are having sex."

"I see, this is all so wild to me," Jess said.

"Don't worry, you will get the hang of it," Vanessa said.

I heard the door open and saw Jess's face light up out of the corner of my eye.

"Ah perfect!" Vanessa said, "Jess meet your new man, Sean. He'll take you to your room, have fun!"

I tried turn my head to get a glimpse of him, but Walter held my head in place, firmly on his big black cock.

I heard Jess giggle and the door close, she didn't even say bye.

"Ok thats enough Walter, thanks," Vanessa said.

Walter pulled me off of his big black cock, put his pants back on, and left the room.

I stayed kneeling on the floor.

"Your trainer will be here in a minute, do you understand your new role?"

I looked down at my cum drenched panties and nodded my head.

"Good," Vanessa said, "one less male imposter in this world is a good thing, don't you agree?"

This was all moving so fast I didn't have time to think, so I nodded my head in agreement.

The door opened, in walked an extremely sexy woman in a very short french maid outfit.

"This is Lexi, she will be your teacher. She is one of our best sissies. How long have you been with us now, Lexi?"

"3 years m'am," she responded.

"Lexi was just like you 3 years ago, a failed man looking to start fresh. Look at her now! You would never know under that skirt there is a little white penis, just like yours."

Lexi lifted up her skirt, slid her panties to the side to show her tiny, shaved white penis.

"Now compare that to Walter's big black cock," Vanessa said. "What woman could possibly get pleasure from a little white penis? Best for everyone if little white penises were to be kept in panties!"

I shook me head in agreement.

Vanessa went behind her desk and pulled out a box with a pink collar in it. I knelt silently as she walked over to me and wrapped the collar around my neck. I couldn't quite tell, but it sounded like there was a small padlock on the back.

She clipped a pink leash to a ring on the front of it and gave it a tug. I instinctively stood up as she handed the leash to Lexi.

"All of our sissy trainees are kept on leashes," explained Vanessa. "It let's our other guests and employees know that you are new so they cut you some slack. Eventually you won't need a leash though. Hopefully, you get to that stage sooner rather than later."

I nodded. This all felt like dream. I was broken beyond the ability to protest. I was just going with the motions.

"Lexi, help Tiffany into her new heels and escort her to her room."

Lexi set a pair of pink heels on the floor and steadied me as I stepped into them. It took a second to catch my balance, as I stumbled backwards, but Vanessa gave my leash a short tug forward and I caught my balance.

"You will get used to them quickly," Vanessa said. "And I almost forgot, the most important piece of all!"

Vanessa grabbed my little, exhausted, penis, and removed the monitor on it.

"You won't be needing this anymore!" She said with a wink. "What's more important now is to keep you focused and not let that tiny little penis of yours get you sidetracked."

She then started to slide a pink plastic cage over my tiny penis.

"What is that? Please don't! I dont..." I panicked.

She ignored my protests and slid my little penis all the way in and clasped it shut with another lock.

"This is non-negotiable," Vanessa said sternly, "maybe Jess will unlock you, but until you graduate from training, or show you have learned your place, you will be locked up. You sissies are highly excite-able, we can't have you playing with your little white penises all day. You have work to do!"

I wanted to cry. What was happening? This was all moving too fast.

"Lexi, please take Tiffany to her room. And have her deliver her key to Jess on the way," Vanessa instructed as she handed me the key.

Lexi took the leash from Vanessa and led me out the door into the bustling hotel.

I was so embarrassed. It was one thing to be in the confines of Vanessa's office, it was different being out in public.

I did the best I could to keep up with Lexi, but I wasn't used to the heels. I just kept my head down, watching my feet to focus on my steps. My calves felt tired from the heels.

After an elevator ride and a few turns down various hallways, Lexi knocked on a door.

"Come in," I heard a man say.

Lexi opened the door and roughly pulled me along with her. I stumbled forward, but caught my balance. As I lifted my head, I saw Jess laying on the bed, curled up to a handsome naked man with a cock much bigger than mine.

I felt humiliated. I looked down in shame. I knew I could never satisfy her the way he would be able to. He was much more of a man than me.

Jess giggled.

"How's your training going Tiffany?" She asked.

"I...I...I'm just starting," I responded meekly.

"Well get on with it, are you here to give me something?" She prodded.

I reached out my hand, holding the key to my penis cage.

"Bring it here," she demanded.

Lexi walked me over to the bed and I handed it to her. Jess laughed and held the key in front of her face. As my key dangled in front of her, a wicked smile came over her. Indifferently, she threw my key over her shoulder.

I looked down at the floor in shame, as I heard my freedom hit the floor, discarded.

"Hopefully the maid doesn't accidentally sweep it up and throw it away. You'll be locked up forever sissy!" Jess said.

I moaned in embarrassment, looking at her. When looking at her, I couldn't help but notice the meaty cock that her man was sporting. Instead of my sexy wife, my eyes were drawn to his big cock.

"He's big, isn't he?" Jess said, giving her new man's cock a couple long, slow strokes. "It feels so different in my hand. I wonder what it's going to feel like to have a real man inside me for the first time. Do you think it will feel good?"

"I'm sure you will like it," I responded meekly.

"Looks like my little sissy maid is ready for the show to start too," she said nodding at the sissy kneeling at the foot of her bed. "What's the rule again Sissy Maid?"

Her sissy knelt with perfect posture. She spoke proudly and confidently as if reciting from a handbook. Eager to impress.

"Unless given special permission, sissies are only allowed to ride their dildos when their mistress is having sex," the sissy maid responded obediently.

"And do you have your favorite toy ready?" Jess asked.

"Yes, mistress," the sissy responded eagerly, holding up a fat black dildo.

"What's with you sissies? You are all obsessed with big black cock!" Jess laughed.

I blushed. At least I'm not the only one to be completely broken by big black cock.

Jess rolled over on top of her man, leaning forward to give him a kiss. His big hard cock was rubbing against her pussy.

"Tiff, come give me a hand before you go. Guide his big cock into my tight little pussy," she requested.

I froze.

"NOW!" She commanded.

Lexi tugged on my leash and I crawled onto the bed and reached out, grabbing his big hard cock with my left hand. It felt warm, much bigger than my own. As I had done many times before with my own little penis, I lined the head up with her pussy, rubbing it up and down her pussy. I gripped his cock firmly as she slowly slid down, moaning with every inch.

I heard the sissy maid moaning too, she must have also been sliding down her dildo.

"Oh my god!" Jess moaned as she flung her head back, "I cant believe I have been missing out on having sex with a real man. This doesn't feel anything like the boring sex we used to have. I can actually feel him. I might actually have an orgasm! Get out of my sight Tiffany."

I felt a tug from my leash as Lexi pulled me off the bed and hurried me out of Jess's room. The door closed behind us as moans of my wife's pleasure echoed in my ears.

"You aren't supposed to touch your mistress's man, but i guess you aren't a full sissy yet," Lexi said.

She almost sounded like she was mad at me for breaking a rule. It should be me who was ashamed of guiding a man into my wife, not being scolded for doing so.

I was ashamed and in a daze as Lexi led me through the hotel, eventually ending up in hallway that was completely purple.

"This is the sissy wing," Lexi explained, "all of the sissies and sissies in training live here when they aren't on duty. There is a sissy only gym at the end of the hall, and a private sissy rooftop pool. They really treat us well here. Alright, here is your room."

Lexi opened the door and led me into a beautiful ocean view room. It had a large bathroom with a rainfall shower, tub, and vanity. A massive king bed, and an enormous walk-in closet.

"You will find that everything in this closet fits you perfectly. They they have been hand selected for you to help with your journey as you find your style. Dresses, shorts, tank tops, bikinis, and my favorite, the lingerie!" Lexi squealed as she opened the several drawers in the closet.

Each drawer was perfectly organized and packed with bras, panties, corsets, you name it.

As I sifted through my new wardrobe, I felt blood rush to my little penis. It twitched in the cage, trying to come to life, but to no avail.

But then I felt something else. I no longer felt the twitch in my penis, all I felt was an ache, almost an itch, deep inside my ass. Somewhere that only Walter had touched. It was almost like my body realized I wouldn't get pleasure from my little caged penis, but if I was horny I could still get pleasure from my ass.

I clenched my butt cheeks.

"I know that face," Lexi said, "we've all been there. Are you getting turned on looking at your new clothes?"

"I don't know, maybe?" I responded. "I just feel this itch deep in my ass right now. Is something wrong?"

She giggled, "no sweetie, that's just your body telling you that you need to get fucked. You need a big black cock in that tight pussy of yours."

She playfully pinched my ass.

I squealed and closed my eyes. Images of Walter's big black cock filled my brain. I moaned and squeezed my ass together, remembering what it felt like inside of me. I could still feel him, like a big black ghost cock.

"I guess I should show you the best part!" Lexi said walking back over to the bed, breaking my trance.

She bent over and opened a door on the night stand. I walked over to a look in, it was stocked with big black dildos. Some longer, some thicker, all enormous.

"What am I supposed to do with those?" I asked.

"Do you really have to ask?" Lexi laughed. "These are the only way you will be getting off, unless you are lucky enough for the real thing."

She picked one up and handed it to me. It was so heavy, and thick. Much like Walter's big black cock. But it lacked the warmth that his big black cock gave off.

"Your little white penis is no longer a source of pleasure for you. The only way you will be able to get off is when you are impaled on a big black. But you aren't free to use them either. And there will be repercussions if you get caught. So don't get caught."

She whispered and winked to me at the last part, like someone was listening.

I stared at the dildo as her words washed over me. The ache in my ass grew stronger. I let out another moan as I unintentionally worked my hand up and down, feeling its size, exploring it's shape.

She broke my daze, walking up to me, "it's not as good as the real thing, but it does the trick, trust me."

By the time she finished her sentence, she had her hands on the big black dildo and was standing right in front of me. She pulled close, I felt her little penis press against my cage.

"And if you play your cards right," Lexi whispered, "you can get your little sissy penis unlocked. Us sissies like to have fun with each other on our down time too you know."

She kissed me. Our tongues danced. She felt so soft. It was much different than the dominant kiss Walter gave me, but also different than when I pretended to be masculine with Jess, it felt equal. She led, but it felt equal. It felt comforting. Like she was teaching me.

We kissed and she pulled her body up against me tighter. I felt her little penis stiffen and was jealous. She held me tight. I felt so good.
<hr pg="2" />Next thing I knew, I felt a prick on my neck and everything went black.

Groggily, I opened my eyes. "What's going on?" I said as Vanessa walked over to my bed.

I tried to sit up but was restrained.

"Just relax little Tiff," she said in a comforting yet stern voice.

She sat on the bed next to me and continued, "you are probably confused. Let me fill you in. You have been under anesthesia for 2 days as some modifications were made. All at the request of your Mistress, Jess. Do you understand?"

"What modifications?" I asked nervously.

She reached to my nightstand and picked up a big black dildo, it looked the same one I was admiring at my last memory with Lexi.

"This really is huge, isn't it?" Vanessa asked.

I felt my penis twitch. I wasn't caged. I was free. My penis grew and I felt it push against a lace material.

"I love how your little white penis can't even free itself from these skimpy panties, it is so small, so weak, so delicate. So feminine," she said.

My penis twitched again. Now fully aware, I felt my arms and legs tied down. I couldn't lift my head.

She reached into my panties and grabbed my painfully hard penis with her thumb and forefinger.

I moaned.

She kept stroking as she talked to me, "as i was saying...in terms of modifications. First, your lips were too thin, we have applied a light botox to them to help give you a sexy, pouty look. Next, permanent make-up was applied..."

She saw a look of fear in my eyes, but calmed me down by shushing me while still stroking my penis with her thumb and forefinger.

She continued, "Don't worry, it isn't actually permanent. It only lasts about 3 months. Jess is very considerate and paid extra for this. She wants you looking your best and doesn't you worried about spending time doing make-up or even worse, doing it poorly, but rather focusing on your training and your new you."

I nodded my head. I felt like I wanted to cry. But this is what I signed up for when my body betrayed me. It is really for the best.

"Right? Not so bad at all," Vanessa continued, reading me like a book. "The next one is minor, but we added extensions and died your hair platinum blonde. Jess thought you would find it fun and more fitting with your new look. And of course electrolysis everywhere besides the top of your head and eye brows. And finally, for the grand finale, your new boobs! Jess almost went big for you, and I mean BIG! She almost gave you double D's, but decided a nice perky B-cup would be more fitting for the current stage of your journey."

Before I could even talk, she pushed a button on her tablet and my ceiling became a mirror.

I was speechless as I stared up at a gorgeous blonde, staring back at me. My boobs looked amazing. They framed my body and gave me a slim but curvy figure down through my hips. I bit my lip as she continued to rub my penis in my panties.

"Are you close to cumming?," Vanessa asked.

"If feels so good, but no," I responded, staring up at myself, the gorgeous blonde being jerked off by a beautiful brunette.

"Do you want to cum?" She asked.

I nodded eagerly.

"Let's check on Jess first, maybe seeing your sexy wife would help put you over the edge," she said before looking over at her tablet.

She tapped the screen and the mirror above me flipped to a video of Jess being tag teamed by two black men. She had her head flung back as she rode one black man while another squatted above her and pounded away at her ass.

I was jealous, and sad, but my penis twitched.

"This is a live stream of her room right now," Vanessa said.

I watched in horror, but also transfixed by the video above me. Vanessa scrolled through her tablet with one hand, stroking me with her other.

"Let's see here," Vanessa continued, "it looks like Jess has been averaging 7 orgasms a day. Like you, she prefers black men with big black cocks! She tried a black man that first night and hasn't gone back yet. Tyrone, the black man fucking her now, has been one of her most compatible lovers. She got an orgasm score of 91 with him. However, Malik, who isn't there currently got her over a 95! That's great considering how low her scores were with you, isn't it? Wait you know what?"

"What?" I said.

"Well, are you close to cumming?" She asked.

"No, m'am," I responded.

"Let's try a different route then," she said as she let go of my little white penis and tucked it neatly back into my panties before patting it gently on top of my panties.

She continued, "You sissies usually lose all ability to cum from touching their penis, but I didn't expect it to happen this quickly. You might not need to be caged at all. It's not like it will change anything, right?"

She picked the big black dildo up and moved in between my legs.

"Maybe this will help?" She asked seductively before moving the back of my thong aside and rubbing it against my asshole.

"No, no, I can still cum," I said.

"You are right, but only from big black cock," she said as she leaned forward, pressing it inside of me.

"I know this isn't as big as Walter, but this is a replica of Tyrone's big black cock, the man you are watching fill your wife along with his friend Jamaal," Vanessa said.

I moaned and looked up at the screen. She looked so hot taking those big black cocks. Hotter, sexier, more feminine than she ever had with me.

I continued to stare as she slid inch after inch into my ass.

"I think I'm going to cum," I moaned, grasping at the sheets.

She stopped moving.

"Not yet sweetie," she said, "I have a treat for you being such a good sissy."

With that she leaned forward, leaving the big black dildo inside of me, and unhooked both of my hands. Immediately my hands went to be bra covered breasts.

I moaned as I kneaded them.

"Don't they feel good?" She asked as she turned her attention back to my ass.

In and out she went. I couldn't tell how

Much of the dildo was sawing in and out, but my asshole was going numb like it was with Walter, all the pleasure coming from deep within me. Where only a big black cock (or dildo) could reach.

I grabbed both of my new tits and bit my lip. I could feel the pressure of an orgasm building. I watched my wife shutter with another orgasm and let out a squeal. I couldn't keep it in any more. I felt my whole body tighten up as I tried not to cum.

"It's ok Tiff, cum for me," Vanessa said.

And with one swift move she positioned one of my legs up against my shoulder, pulled the whole dildo out, and shoved it all the way back in.

"Oh my god!!!!!" I screamed as I felt ropes of cum shoot out of my penis, leaking through my panties.

My body relaxed as my breathing deepened, oxygen flowing back to my muscles. Recovering from my sissy crunching orgasm.

"That sure didn't take much time!" Vanessa said, "you have it easy with me. But black men aren't going to stop after you cum."

She pulled the big black dildo out of my ass and slapped it on my panty encased, softening penis.

"See, it still works, just not like you used to," she said as she rubbed the big black dildo on my tired little penis.

I moaned in embarrassment. My penis was so small next to the dildo.

"How's your wife doing up there?" Vanessa asked.

"She seems to be happy," I said, embarrassed.

"Happy, fulfilled, sexual, euphoric. Plenty of adjectives you could use to describe the your wife's current state. She is finally experiencing what sex with a man is like. Just like you!" Vanessa explained.

I nodded. It made me sad, but I was also recovering from my own mind bending sissy orgasm and knew I could't compete with her new men. I was so small. So gentle. So fragile. So sensitive. So delicate. I couldn't compete with men like Walter, Tyrone, Jamaal, or whoever Malik was, walking the earth. I was best served to serve, gathering whatever pleasure I could along the way.

Vanessa interrupted my tailspin, "why don't you close your eyes sweetie, you still need to recover and you have a big next few days."

I closed my eyes and drifted off asleep as images of big black cock flashed across my eyes.

I'm not sure how long I slept, but Lexi woke me up, "time for your real training to start! Love your new tits by the way!"

She held up a bright pink puffy maids skirt and crop top and tossed it to me. Behind it was a matching pink thong and bra.

"Go shower, then get dressed!" She instructed.

Next thing I knew, we were out the door. My training had started. I quickly learned life as a sissy wasn't all just orgasms at the hands of black men and big dildos. I learned how to properly clean a room, work out to maintain my figure, eat healthy, coordinate clothing, and most importantly, attending to a mistress.

It was a lot of attend to a mistress! Dining reservations, laundry, making sure she had her bikinis ready for pool, workout clothes for the gym, coordinated outfits for a night out. Tickets for shows. Even her sexual encounters. I had to make sure she had who she wanted, when she wanted it. A lot of the black men were in high demand, so it was important to think ahead and anticipate her wants and needs.

There were also little things that I needed to learn to personalize a mistresses experience. Does she like a bath after sex? Does she want her man to linger for a cuddle? Or was I to usher them out? Should I have weed for her? Wine?

I was there to make her life as easy and enjoyable as possible.

And what is in it for the sissy? Besides riding your dildo during your mistresses sex, the happier you keep your mistress the more generous she might be. No tipping, but she could purchase time off, or nights with a real man for me. There were plenty of incentives.

Most sissies managed one mistress, but the best sissies supported small groups of women who were there together. And occasionally, a sissy would get to support a man. But those opportunities were few and far between as this was more of a sissy factory for women than anything, with real men on the payroll to take care of the sissy's wives.

I lost track of time, but it must have been a week of intensive sissy service training, workouts, and dieting. Every day, I grew in confidence and ability.

My body transformed. My waist shrunk, my hips and ass grew. My blonde hair got long and thick. I loved how my soft blonde hair bounced as it laid on my perky tits as I walked in my heels.

I was always horny. My new sexy wardrobe felt amazing on my smooth body and made my little white penis tingle every time I slid on a pair of panties, or clasped a bra.

I was kept on edge at all times but without any release. A few nights I debated using a dildo, but decided against it after what Lexi told me. I didn't dare touch my penis since I was so generously left free by Veronica.

The training program was 100% sissy run and led. During the week, I bonded with other sissies. Every now and then we had fun events like movie night...which was usually interracial porn. We even had sissy book club where we would read stories about feminization and cuckolding and talk about our experiences.

It was embarrassing, but freeing to talk about how I was unable to pleasure my wife and how Walter had fucked the man out of me. All of the sissies knew Walter, but only a hand-full have had the pleasure of being fucked by him.

Those who had been fucked by Walter all shared a special bond. I quickly learned that not every sissy could take him, regardless of training.

However, I had not had any contact with my wife, Jess. I had not spoken to her or even been able to see her since Veronica last showed me the video of her being tag teamed by two big black men.

When I had downtime for my thoughts, mostly just before bed, I wondered what she was doing. Did she miss me? Was she so overwhelmed by her new found sexuality that she didn't even think of me? Was she even still here? If I had been keeping track properly, tomorrow was our last day here. What was going to become of me? Of us?

Somewhere during my thoughts, I fell asleep.

The next morning I was woken up my Lexi as usual.

"No training today, but you have an important meeting to get to. Get dressed as you wish and head to Veronica's office in 20 minutes," Lexi said as she unclipped my collar for the first time since it was put on.

"Does this mean I am no longer a trainee?" I asked.

"It means you are ready to be a full time sissy if that is what has been decided," she said as she turned around and walked out.

Quickly, I hopped into the shower, keeping my hair dry as I did not have time. I was so lucky that Jess paid for the make-up, it made getting ready so much easier.

I dried off and went into my closet. I chose a light purple thong with a small flower on each him, followed by a matching bra. White heels. A stretchy white mini skirt, and a white tank top. The purple bra barely poked out over the neckline. My blonde hair laid down over my perky tits.

I walked quickly to Veronica's office and knocked patiently when arrived.

"Come in!" I heard her say before entering.

"Very prompt, good sissy," Veronica said looking up at me from her desk before looking back to her tablet.

"Just going over a few things here before Jess arrives. Have a seat," she said

"Yes, m'am," I said, taking a seat and crossing my legs like a woman. Sitting up straight and slightly popping my chest out. It was important for a sissy to have good posture.

I knew better than to ask what was happening. I am at the bottom of the ladder. Dressed like a sissy. My little white penis hard in my panties, but so small you could barely make it out in the confines of my thong and skirt. Yet when I crossed my legs and squeezed, I could feel it. It felt so good.

The door swung open, in walked Jess. She was holding a mimosa, she wore a sexy black bikini with a white sarong and had sunglasses on. She wore high heeled sandals.

There was a towering black man behind her.

She turned back towards him and placed one hand on his chest. He grabbed her ass with one hand and gave it a squeeze.

"This shouldn't take long, meet you back in my room in 30?" She asked.

He nodded and gave her ass a playful slap. They both giggled before he pulled her in for one deep kiss.

Before she turned around he looked at me and laughed. Embarrassed that I was watching and made eye contact with him, I looked to my feet.

Jess turned and faced me. She looked different. She had never looked hotter.

"Well well well, look at you my little sissy! They really did a number on you. Did they make you wear this sexy little outfit?" She asked.

"No Je..." I started.

"Jess? You don't call me Jess anymore. You call me Mistress. Or Mistress Jess, have you forgotten your training?" She interrupted.

"Sorry Mistress. No, Mistress, I picked this outfit out. And no, mistress, I haven't forgotten my training," I said, looking at my feet.

I squeezed my thighs, my little white penis was painfully hard in my panties from what I just saw and this interaction.

Veronica chimed in, "have a seat Jess. As you know from our check-ins, your sissy has been a perfect trainee, one of our best. High marks across the board. If you are open to it, we are more than willing to accept her into the sissy program in a permanent position. As payment, you would receive an annual payment of $250k and 12 weeks free at the resort, every year. During the 12 weeks, you would have priority access to your sissy, if you so choose."

Jess took a sip of her mimosa.

"Seems like an easy choice to me," she said, where do I sign.

"Mistress, may I speak?" I asked as this reality sunk in.

"Oh just this once I guess sweetie," she said, patting me on the thigh.

"What about my job? Our house? My family?" I asked.

Jess laughed, "Too many thoughts in that sissy brain of yours! Shortly after you came all over Walters big black clock, we sent in your resignation, sold the house, and notified your family of your transition. This is a done deal, there is no alternative. All of our money sits in an off shore account under my name. I will be purchasing a beach bungalow for when I am not here. And you, well obviously you will be staying here."

Veronica handed her the tablet and Jess promptly signed.

"Very good!" Veronica said, "welcome aboard sissy!"

Jess stood up, "I plan on staying here for the next four weeks until my new house closes. It has been a pleasure Veronica, thank you for all of your help through this process."

"It is my pleasure," Veronica said.

Then Jess turned to me. Gone was my loving wife. Here was my Mistress.

She snapped her fingers and said firmly, "With me sissy, NOW."

I scrambled to my feet as she handed me her mimosa to hold.

I held it with two hands, one underneath, and one holding the flute, not to spill as I had been taught.

She reached down and cupped my hard little penis.

"So pathetic," she said as she turned and walked out as I followed close behind.

"Mistress," I said, trying to keep up in my heels.

"Yes, Sissy?" She responded.

"Mistress, for me to do my job well, I need to know a few things. Do you mind if ask you a few questions?" I asked politely.

"Yes, but Malik is in my room and all I can think about is his big black cock. I am literally dripping wet right now, we can talk in a few minutes," she said, picking up her pace.

Malik! The man who had given her her best score. I was envious but turned on by the thought of seeing them in action.

I tried my best to keep up, but I was still new to heels. I felt my hard little penis in my panties as my hips swished back and forth.

Eventually we got to her room. The same room from a while ago. Malik was lying naked in bed. His big black cock hung over his thigh.

"What do you think sissy?" She asked, not really looking for an answer.

"I understand why you like him," I responded meekly.

I closed the door behind us as she crawled onto the bed towards him.

I noticed the cushioned bench at the base of the bed and took my place as I learned in my training.

I watched intently as the scene in front of my unfolded. She had taken Malik in her mouth and his big black cock was rapidly growing. She moaned as he reached over her and slid is finger into her pussy, rubbing her clit. She wiggled her ass to let him know she liked it.

Their non-verbal communication was impeccable. They were on the same page, letting each other know with noises and movements what they liked. Before with sex I would just try not to cum in the first 10 seconds and tell her I loved her. This was different. This was what sex is supposed to be.

She got stopped worshipping his big black cock and stood over him, pulling her bikini bottoms down, kicking them to the side. Slowly, she squatted down. His big black cock was knocking on the door to her pussy.

I couldn't see her face, but she leaned forward and whispered something in his ear. He smiled.

Slowly, she swung her knees around so she was facing me.

She wanted me to watch. She wanted me to see the pleasure take over her face as she sunk down his big black. She wanted me to see what a real orgasm is. What a real cock can do.

She reached down, grabbing his big black cock. Without breaking eye contact with me, she slowly began to lower herself down. With every inch, her mouth opened further. It was an involuntary reaction to pleasure until she sunk all the way to the bottom.

Slowly she rotated her hips.

"He's so deep inside of me," she said as she rotated her hips, fully impaled on his big black cock, "don't you want to play with your little white sissy penis? Isn't that the rule?"

I stared at her and reached into my skirt.

"Take your skirt and tank top off," she instructed.

I obeyed.

I knelt there in my purple panties and bra. Staring at my wife ride her man's big black cock. I reached into my panties with one hand and started jerking off.
<hr pg="3" />I couldn't help it, but my eyes eventually wandered from her sexy face and tits to her pussy and more importantly, Malik's big black cock. It was so thick, stretching her pussy unlike my penis ever could.

I bit my lower lip as I rubbed myself as best I could. I just couldn't quite get myself over the edge, much like the other night with Veronica. I stared hard at Malik's big black cock. I was envious. I felt an ache deep inside my ass.

I moaned and clenched my ass cheeks together. My purple thong hugged my hungry asshole. I needed something inside if me for release.

"What's wrong sissy? Can't cum anymore?" Jess asked me with a wicked smile on her face as she rode Malik's big black cock.

"Mistress...mistress," I said.

I played with my little penis faster, my penis head rubbed against my panties.

I moaned.

"I just can't cum in my panties," I said, defeated.

"Why not?" Jess said in between her quickening breaths.

"I need something in my ass, something big, it aches," I said.

"What aches sissy? Is it your sissy pussy? Walter really did fuck the last ounce of manhood out of you, didn't he?" She responded.

I nodded my head in agreement. I couldn't look her in the eyes. I just stared at Malik's big black cock sawing into her.

"I think my last sissy left her big black dildo here. She was a total doll and I let her keep one here so she always had access. She was so attentive. So thoughtful," Jess said.

There was a pause. Just moans as Jess grabbed her tits and rode Malik's big black cock.

Then a lightbulb from my training went off. Mistresses love a begging, pathetic sissy.

I looked up at her with big doe eyes.

"I can be thoughtful, Mistress. I can be attentive. I can be the best sissy for you and your men. May I please have the big...black...dildo for my sissy needs and I promise you wont regret it," I begged calmly.

I felt pre-cum ooze out of my little penis.

"Oh fine, check the dresser. Top drawer," she instructed.

I stood up, my hard little penis standing at attention in my purple panties, and walked over to the dresser.

Opening the drawer I saw all sort of sexy lingerie, a few joints, a piece of paper with names of various men, and a big black dildo. I picked it up and felt a rush of energy course through my into my ass.

I moaned. My knees went weak. I hurried back to the padded bench.

Kneeling, no more than 3 feet from my wife as she rode Malik's big black cock. I held the big black dildo down, shifted my thong to the side, keeping my penis tucked in, and positioned it to my asshole.

"Mistress, may I?" I asked with my doe eyes.

"Yes, sissy, enjoy the show," she said as she bounced up and down on Malik's big black cock.

Slowly I worked my way down the big black dildo. It had been too long since I had anything inside of me. Pre-cum leaked out of me with every inch, making a noticeable dark purple spot where the tip my penis rested in my panties.

I moaned and worked my way down further. When I was about two-thirds down I lifted myself back up before sinking all the way down.

BANG! Immediately I came. Rope after rope of cum shot out of my twitching penis. I pulled the front of my panties to the side, freeing my little penis as it twitched uncontrollably.

Jess giggled as I lost my breath and blushed a deep red. My whole body shook.

Once I caught my breath, I started riding again, going for round 2. Hell, they were still going and I wasn't sure when I could have something so big inside of me again.

Malik roared and pulled her hips down, taking the dominant role for the first time. She squealed in delight at what seemed to be her second orgasm of the session as his cum flooded her insides.

"Oh my god, so much cum, its so hot, it feels so good Malik," she moaned.

I rode furiously, knowing my opportunity could end at any minute.

She laughed, "don't be in such a hurry sweetie, we are just getting started. Keep that big black dildo buried deep inside your sissy ass."

"Thank you Mistress," I said in between breaths as I rocked up and down on my new toy.

They moved to doggy style. Malik didn't miss a beat even though he just came.

"Amazing rebound time, right?" She said, winking at me.

I nodded.

"So you had some questions for me?" She asked.

"Now, Mistress?" I asked.

"Yes, now," she said, seemingly annoyed.

She moved a pillow under her so she was propped up effortlessly. Malik slowly knelt behind her, slowly fucking her with the entire length of his cock.

"We aren't going anywhere, Malik can go all day," she said with a smile.

"Yes, Mistress. He sure is a specimen," I responded.

She moaned gently from the slow fucking she was receiving, much different from her wild ride minutes ago

"So go on," she said.

"Yes, Mistress," I said as I continued to gently ride my big black dildo, "first, what is the most important thing I can do to make your stay here enjoyable?"

"That's easy," she said, "making sure I have access to the biggest black men at the resort. Malik here has been my favorite, but he leaves in a couple of days, so I will need you to find me a replacement. And make sure you know when Malik is returning so I can coordinate."

I nodded, embarrassed by the reality that I would be coordinating lovers for my wife on an ongoing basis.

I addressed Malik, "Sir, would it be OK if I work with our resort coordinators to have early access to your calendar so that I can make sure my wife is here to get fucked by you?"

My wife moaned loudly, closing her eyes and smiling. The reality of me lining up partners for her must have hit her as well, and she enjoyed it.

"I think that can be arranged," he said confidently, smacking my wife's ass, "she is such a hot piece, definitely my favorite fuck yet."

He leaned over her and turned her head to the side, giving her a deep kiss before kneeling back up to properly fuck her.

She moaned, melting back into him to get every inch.

"I can't believe you gave this up, sissy," he said.

"I...I...I just couldn't give her what you can," I said, slowly riding my big black dildo to match his rhythm.

They both laughed as my little penis began twitching back to life in my cum soaked panties.

"It's like fucking a virgin," Malik said before slapping my wife's ass again.

She moaned again. I thought about how small I was compared to him. How he was able to stretch her and reach places I couldn't hit in my wildest dream.

I moaned as I slid down my big black dildo, wondering if she was thinking about the same thing.

"Mistress, may I examine his big black cock to understand what expectations of size you have for when Malik leaves?" I asked.

Jess laughed.

"Well you are riding him," she said, smiling at me.

"What do you mean, Mistress?" I asked, confused.

"As I said earlier, my previous sissy was so good, so I rewarded her with dildos that were exact replicas of the numerous men I was with. Right now, you are sliding your sissy ass down on the Malik prototype!" She told me.

I moaned again, knowing that we were enjoying the same big black cock.

"The exact same? It's so big," I said in between soft moans.

"The exact same. Isn't it hot knowing we are enjoying the same big black cock," she moaned pushing back against him.

I shook my head.

"Obviously, the real thing is for me. But I always want you to know what it feels like to have a real man inside of me," she said.

"Yes mistress, thank you mistress. That is very thoughtful. I'll plan on taking measurements to ensure your standards are met. Do I have your permission to work with the sexual exploration staff to create replicas for all future partners?" I asked.

My little penis twitched in my panties knowing that not only would I be setting up her sexual partners, but I would be closely acquainted with their big black cocks. Measuring them. Studying them. And ultimately, feeling them inside of me.

I bit my lip as I rode Malik's replica. I thought about the consequence of this. The bigger the partner I could find and reserve for my wife, the bigger the dildo I could ride as I chase sissy bliss.

"I'm going to find you the biggest black cocks you can ever imagine, Mistress," I said.

"I know, Sissy, that's the point. It's like dangling a carrot in front of a horse. You get the biggest black cocks for me, and in return you get the biggest black dildos. You don't to have some needle thin white dildo, do you?" She asked.

I shook my head no. It sounded horrible to be honest.

"Well neither do I...at least anymore that is," she laughed as she reached out and gave the head of my penis a flick.

She laughed as I immediately came from the embarrassment, her touch, and the Malik's replica buried deep inside my ass.

I was in awe of her ability to step into this new role of being my dominant mistress. She understood my psyche. She knew I needed guidance and she knew how to pull my strings to get what she needed out of me. At that moment, I think I loved her more than I ever have. Our new relationship fit us both perfectly.

Malik came deep inside of her again, and slowly withdrew. Meaning my time with his replica was over. It would be unfair for me to have it inside of me when she didn't have the same pleasure. That was not my role, my purpose.

"May I draw you a bath Mistress?" I asked, shivering as cold air flooded into my gaping ass hole.

"That would be lovely. With lavender salts and a glass of sauvignon blanc," she said as she cuddled up next to Malik.

Her hand stroked his (finally) softening big black cock as she laid on her side, one leg draped over his. Her head rested on his muscular chest.

I heard them giggling and kissing as I stumbled to the bathroom in my heels, purple bra and panty set to prepare her bath.

Once prepared, I turned down the lights, lit a few candles and called for Jess, "Mistress, your bath is ready."

I heard one last kiss and in she walked. I couldn't help but notice cum dripping her pussy. She noticed me staring.

"Come here, lay down sissy," she said, pointing to the floor and snapping her fingers.

Without thinking, I laid on back.

She squatted over my face and lowered herself down until her freshly fucked pussy rested on my mouth.

She smelled of sex, but in a good way. It made my little penis twitch. I wanted to lick her but I didn't dare, not without her permission.

After rubbing her pussy across my lips and nose, she broke the silence.

"Lick," she commanded.

I stuck my tongue out and she immediately pushed, flooding my mouth with Malik's cum

"Don't spill sissy, there is a lot! Malik is a heavy cummer," she told me as I quickly lapped up his cum.

It tasted good, better than I expected. I wanted more. Between Malik's cum and her sitting on my face, I was having a hard time catching breathing.

"You always were good with your tongue," she said as she eventually stood up and climbed into the bath, leaving me on the floor.

I didn't know what to do, I just laid there. That was my last order.

"You are quite the dumb sissy. Go on. See if Malik needs anything then go get cleaned up. You look repulsive in those soaked panties. Tidy up and prepare my calendar until Malik leaves in a few days. I'd like to see your proposal by 5pm. I dine at 7," she said looking at your watch, "it's 11 now, that gives you 6 hours. Plenty of time for an eager new sissy. And don't forget to thank Malik."

She closed her eyes and sunk into the tub. I took that as my dismissal.

I walked out to the bedroom, Malik sat up in bed smoking a joint.

I walked to the bed and stood in perfect posture, just as I was taught when addressing a superior.

"Sir, I just wanted to say thank you," I said.

"Oh yea?" he said, releasing a cloud of smoke, "for what exactly?"

I made my big dumb sissy doe eyes, "well sir, for taking care of my wife. And fucking her long enough for me to cum twice too."

He interrupted, "seems like you should be thanking my big black cock, why don't you talk to it."

He grabbed his enormous flaccid black cock with one hand, and waved it around.

My eyes followed like he was a hypnotist.

"Sir, the rules are I cannot touch my Mistress's man," I stated confidently.

Even though I wanted to reach out and grab his big black cock. I stood tall, puffed out my perky chest, and was proud of my restraint.

"I'm not telling you to touch it. Why would I want some dumb sissy when I have his sexy ass wife? I'm telling you to get close and talk to it, thank it," he demanded.

That was within the boundaries of the program's rules. I walked to the foot of the bed and turned to face him. He spread his legs wide so his big black cock laid lewdly towards me, like a 3rd leg.

I crawled up on the king size bed and slowly, seductively crawled toward him. I made sure my head was low and my back reverse arched up to my ass, just like I was in elite doggy style position. I wanted him to find me sexy, not just some dumb sissy.

Not taking my eyes off his big black cock, I inched closer to him. I felt my little penis stiffen yet again in my wet, cold panties as I settled in, no more than 3 inches from the head of his big black cock.

His big black cock took up my entire field of vision.

If I stuck out my tongue I could lick him. Instead, I licked my lips, bringing myself tantalizingly close to him.

I took a deep breath and started saying thank you the best I knew how, "Malik's big black cock, thank you. Thank you for bringing my wife such pleasure.

Pleasure that I could never give her. Thank you for staying hard and lasting so long through two orgasms, allowing me to take care of my sissy needs. I thoroughly, deeply enjoyed having your replica inside of me. I am so happy that my wife gets the real you, but I am grateful for my experience with your big black dildo replica. I look forward to the next time I get to see you fuck my wife."

"That's a good sissy. Why don't you take one big sniff while you are down there then you can get out," he said.

I exhaled before taking this biggest sniff of his big black cock I could. It was intoxicating. Sissy synopsis fired in my brain and I felt my little penis twitch and fire blanks into my panties. There was nothing left in my little balls.

"Oh my god, did you just cum from sniffing his big black cock?" Jess yelled as she broke out into laughter.

I raised my head and saw her standing at the head of the bed, handing Malik's joint back to him.

I turned bright red. I was so embarrassed.

"This one is something else," Malik laughed.

Jess continued my humiliation, "Your ass is literally shaking, convulsing in orgasm from praising and sniffing Malik's cock. A real man's cock. A big black cock! I mean, good for you, but this is next level sissyness. Get the fuck out of here before you accidentally cum again."

I ran out of the room, I had work to do. I wanted to cry. But the humiliation also made me so horny. I just had 3 great orgasms in the last 30 minutes. But I was also embarrassed.

Its hard being a sissy!!!

To be continued...it you all like it!

