Road to Becoming a Sissy Bitch Boy Pt. 06

Ian lay in his bed thinking about the adventurous weekend he'd had. He thought about new feeling he had stirring around inside him. He wondered "Am I gay? Am I a boy? Am I a girl?"

All he did know for sure was that he liked it. And knew he didn't want it to end. "Maybe he would talk to Mistress Madeline later he thought."

He put on his robe and joined the others in the dining room. Breakfast went as usual, Mistress Madeline reading her newspaper, Xander and Ian chatting and teasing each other about everything.

Finally, Mistress Madeline spoke. "Boys, why don't you change for the pool party, and then see if Hutch needs any help setting up."

"Yes Mistress." They answered.

"Mistress.' Said Ian.

"Yes, little one." She replied.

"Do you know where my swim suit is? I haven't seen it since the day I got here."

"Oh my dear, you won't be needing that ridiculous thing. I've ordered both you and Xander new pool attire. It should be in your room by now."

"Yes Mistress." Ian answered.

When Ian returned to his room, he found a package on his bed waiting for him. He anxiously ripped the package open, and found a White side tie bikini bottom and top. Across the bikini bottom, the word SISSY was printed in pink sparkly letters. "Oh my." He thought. He quickly tried it on, and looked in the full-length mirror. "Damn girl, you look sexy as hell!" he thought. Two days ago, Ian would have been horrified at the thought of wearing this sort of thing in public, now he embraced it. He knew at that instant his life was now different. He was no longer the shy boy who met a friend for a few beers. He was full blown bisexual sissy slave. And he liked whom he'd become. He threw on his robe over his suit, and headed for the pool.

He met Xander as he was walking into the living room. "let's see." asked Xander.

Ian dropped his robe and struck a pose for his sissy friend.

"Oooooh you sexy little slut" gushed Xander.

"I know, right, answered Ian. Let's see yours."

Xander stuck the same pose as his friend did. He was wearing the identical swim suit.

"My compliments on your fashion choice." Joked Ian. The two sissies giggled and continued out to the pool deck. After setting up tables, and foldable chairs, Ian asked, "what do you think the Baxter girls will have to say?"

"Fuck them Ian. We are on our home turf now. My mother isn't going to permit any teasing or rude behavior from either of those two cunts."

"Agreed. Said Ian. Let's just have some fun today."

The boy's finished the pool area set up, and then jumped into the pool. Splashing around and enjoying the day, they noticed guests starting to arrive. Ian recognized a few of the men and women from the night before. Both the boy's waved and welcomed them. Most of them waved back, and said "nice day." "Great to see you two again." And other friendly comments.

Then entered Mistress Jade, and the Baxter twins. Mistress Jade had on a one- piece swim suit, that showed off every curve the voluptuous woman had. The girls wore string bikinis that didn't do much to cover theirs. The men around the pool deck lowered their sunglasses, and ogled the threesome as they sashayed in. Maybe it was the loose-fitting clothes they had on yesterday, but Ian hadn't noticed how sexy these girls were. The same red hair as their mom's, big, firm tits, perfect tight asses, and long tan legs.

"These bodies were meant for one thing only." Ian thought to himself.

Xander glanced over and said, "Well, I see the nut hasn't fallen far from the tree." Both boys laughed.

Upon seeing the boys, the girls waved enthusiastically and said, "Hi Ian, Hi Xander.

"See." Said Xander.

"I guess you were right partner." Ian said.

The girls jumped into the pool, and the four of them swam, splashed each other like they were old friends. After a while, the two girls swam up between the boys, and Ashley said. "What? Aren't you two boys' going to offer the two sexiest chicks' here a drink? Or are you guys just turned on by other boys?"

"NO, no, stuttered Ian. We go both ways, I think. Follow us girls."

The improbable foursome climbed out of the pool, toweled off, and headed for the bar. The girls sat down at a table in the corner of the pool deck, the boy's joining them with beer for everyone.

"So, are you guys gay or what?" asked Dawn. Ashley nodding in agreement with her sister.

"Well, technically we are Mistress Madeline's sissy slaves. And we both love serving her in that capacity. And yes, we both love cock, as you two know." Said Xander.

"But we both are biologically male.." A confused Ian added. So, it's kinda hard to not get excited when we see sexy girls like you two."

"I see, purred Ashley."

"Hmmmmm." Added Dawn.

"Well, our mother told us we were supposed to apologize to you guys, and be nice to you today." Ashley said seductively.

Both girls leaned close to the boys, and stroked their upper thighs, and said.

"We really are sorry about what happened yesterday, we truly are." They lied.

"But regardless of your sexual preference, we are turned on by what's inside those bikini bottoms." Said Ashley.

"We both have to leave with our mother soon, but maybe we could meet up again for some consensual fun out at the barn next week some time?" Dawn offered. Both girls reached under the table, and firmly grabbed the boys' cocks through their swim suits.

"I think I can speak for both of us when I say we'd love to if we can get away with it." Xander said in a squeaky voice. Both boys' now showing visible erections in their bikini bottoms.

"Yes, the consequences of getting caught with you two could be more severe than you could imagine." Added Ian in a tone of voice somewhere between a male and a female.

"Ok, you leave that to us, we can be pretty sneaky." Said Ashley with a chuckle.

Just then, Mrs. Baxter, aka, Mistress Jade walked over and said.

"Come on girls, time to go. We need to get ready for our dinner engagement this evening."

"Yes mother" they both groaned together.

The women said their goodbyes, and disappeared into the house. Mistress Madeline made her appearance at the boys table and said. "Enjoying the party girls"

"Yes Mistress" The both said together.

"Everything ok with the girls now?" she asked.

"I guess so." Answered Xander.

"As good as it can be expected Mistress." Added Ian.

"Ok great. Well, things are winding down here now, and I need to be on a conference call in a few minutes. You girls have another beer if you want, then help Hutch fold up the tables and chairs. When that's done, the table and chairs need to be brought down to the basement storage room.

"Yes Mistress." Said the boys.

After she was back inside the house, Ian said "Basement? I didn't know this place even had a basement."

"Yes it does, Xander said. But Mother keeps it locked up. I haven't been down there since I was a kid. But I have noticed different workers trucks here when I get home from work lately. Carpenters, plumbers sometimes electricians. I guess she's having it refinished or something. I don't ask."

"Ok, whatever" shrugged Ian.

The boys nursed their beers, and talked about what sluts the two Baxter girls turned out to be. As they drained the last beer from their bottles, Xander said "OK bitch, time to get to work."

"Yep." Ian replied.

The two boys started breaking table and chairs down, stacking them in the breezeway. When they were done, Ian Asked "Think it would be Ok we both had another beer? I've got a little buzz going I don't want to end."

"I don't see why not; I'm feeling a little light headed as well."

The boys finished another beer each, then started lugging chairs down to the basement. The door to the basement was unlocked, and slightly ajar. The boys took a few steps in, stumbling around in the dimly lit room.

"Try to find a light switch Ian." said Xander.

The boys groped the walls in the dark when suddenly the door slammed shut with a loud thud. Then the sound of keys turning a deadbolt made a decisive "click." When the lights suddenly came on, both half drunk, bikini clad sissy boys shielded their eyes, and tried to make out the identity of the people standing in front of them. When their eye's adjusted, standing several feet away were Mistress Madeline, Mistress Jade and the two Baxter twins. All of them wearing black leather dominatrix outfits. The two older women held some sort of harnesses, while one the Baxter twins twirled a set of keys around her finger.

"Welcome to my dungeon" Mistress Madeline said in a commanding voice.

"Uh oh, this can't be good." Whispered Ian.

The boys glanced around the room. The walls were all padded, and several pieces of equipment were set up in different areas of the room. All of them resembling some sort of restraint apparatus with BDSM intentions. Chains, dildos, masks and other sexually oriented toys hung from the walls. A fake fireplace dimly flickered in the corner, explaining the small amount of light there was when they entered.

Mistress Madeline was wearing her Usual black leather Mistress outfit. Mistress Jade's outfit resembled hers, with slight differences such as her boots were short, and she wore black fishnet stockings. She also wore a small mask that covered her eyes and nose.

The twins wore identical matching skin tight crotchless leather body suits with 6-inch heels attached to the bottom. Each of them wearing a half mask with cat ears showing through their long curly red hair. Long curling tails extended from each of their asses.

"Dear God." uttered Xander.

"SILENCE" boomed Mistress Madeline and Mistress Jade in unison.

"NOT ANOTHER WORD, EITHER ONE OF YOU. Girls, take our two sissies over to the restraining area, and get them ready." Commanded Mistress Jade.

The boys were walked to the corner of the room, and stripped of their bathing suits. They were both forced to put on tight black leather crotchless shorts, that had large opening in the back. Their feet and legs were spread apart, and leather restraints were locked onto each ankle. Long chains connected the restraints to the wall behind them. Each arm was pulled behind their backs, and connected to similar restraints and chains. A red ball gag harness was placed in each of their mouths, and secured with a buckle behind their heads.

"Welcome Sissies, to the initial training session for my two newest Mistresses in training. I know the four of you are acquainted with each other, so I will dispense with introductions. You will refer to them both as "Miss Kitty" until they have earned their new Mistress titles, and have them formally assigned to them.

"I have been very fortunate to have been given access to Mistress Madeline's dungeon today, and she is here to supervise. So don't bother looking to her for help sissies, this is all part of her program. You two just happen to be in the wrong place, at the right time." Lectured Mistress Jade.

"Kitties, come here and get your training gear." Both girls walked over and took the strap on harnesses from their mother.

"Now, as you can see, there is a dildo on the inside, as well as the outside. One is for your pleasure, the other is for your slave's pleasure, or torture, depending on the session. Each has a remote control on the belt, to control the vibration levels of both dildos, Low, to Intense. In consideration to Mistress Madeline, we will be using lube, and moderate intensity today, I know she wants to continue using her slaves tight little asses in the future."

With that, the girls stepped into their harnesses, and slowly inserted the inside dildos into their wet cunts. Apparently both girls had already become aroused at the thought of what was to come. They strapped them on tightly, and began applying lube the asses of there victims. The girls tested the switches on their belts, and jumped, as the dildos came to life inside them.

"Oh yaaa" Purred Ashley.

"Sweet" said Dawn.

"Kitties, the idea here is to start slowly, lull your slaves into false sense of security. Let them think this is going to be pleasant, speak softly to them.

The future Mistresses slowly slid their dildos into the boy's assholes. Pushing their bodies forward, causing the slack in the chains to be taken up.

"Good sissyboy, doesn't that feel good?" purred Ashley. Xander nodded enthusiastically.

"Oh my, what a good boy you are Lily. It's all the way deep in your ass, and you haven't even whimpered yet "Dawn cooed. Dawn switched the vibrator back on, and Lily's body jolted. His eyes opened wide, and he moaned a muffled "ahhhhhhh" through the ball gag.

"Time to raise the intensity girls" bellowed Mistress Madeline.

Both young Mistresses picked up the pace, spanking their captors, and thrusting in and out of their slave boys' asses. Ian could hear the sloppy sound the lube made as the dildo slapped against his ass and balls. There was no pain, just euphoria he thought. He loved the feeling and he wanted it harder.

Ian tried to cry out, but the gag prevented him from speaking clearly. "Moeh, Moeh he screamed"

"I do believe this one has something to say." Said Mistress Jade. Pointing to Lily.

"I think you're right, Jade. Slide down his gag, let's hear what's on her mind."

"MORE Miss Kitty, please MORE." Lily pleaded.

Miss Kitty rammed her cock harder and faster than before into her sissy cunt.

"FUCK THE BITCH" screamed Mistress Madeline.

"GIVE IT TO HER HARDER, DEEPER MISS KITTY" Commanded Mistress Jade.

Lily was in heaven. Nothing had ever felt this good, or been so sexually exciting than what was happening to her at this moment. Her cock was rock hard, and it slapped up against the front of her leather bondage shorts with every thrust. The vibration setting was on high, adding to the intense feeling Lily felt inside her.

"FUCK ME, MISS KITTY, FUCK ME LIKE THE SISSY FAGGOT I AM. DEEPER, HARDER, PLEASE! Yelled Lily at the top of her lungs.

"Oh my, said Mistress Jade. Madeline, this one appears to be different from the others you've had. I think you may have a keeper here."

"I realize that Jade." Mistress Madeline replied.

In the meantime, Xander continued getting fucked, taking the strap on assault with little or no emotion. Miss kitty continued pounding his hole, slapping his ass, and pulling his ass deeper onto her cock by his hair.

"And this one?" asked Miss Jade. Pointing to Xander.

"Just a good soldier, like his father." Answered Mistress Madeline.

"Unchain Xander, and bring him out here in front Miss kitty." Said Mistress Jade.

Put him in front of Lily, Let's see if she is capable of multi-tasking."

Xander's cock was positioned in front of Lily's mouth. Lily opened her mouth, and began eagerly sucking her friend off. Miss kitty kneeled behind him, and shoved Xander' ass from behind, making his cock go deeper into Lily's mouth. Within minutes, Xander shook, and spurted load after load inside Lily's mouth, groaning through his gag. "GOOD BOY" said miss kitty. Patting him on the ass.

Lily continued getting her sloppy sissy cunt fucked. Taking it like a fuck doll.

Lily could hold back no longer, her body violently shaking, taking thrust after thrust of miss kitty's strap-on. Her cock now standing out on a stiff angle away from her body, began spewing the contents of her balls out onto the mat, and all over her friend Xander.

"IM SORRY MISTRESS, IM SORRY. DON'T STOP MISS KITTY, PLEASE DON'T STOP."

Xander kneeled in front of his friend's limp body, as it slumped over in its chained position.

"Good job this evening ladies, unchain Lily, and go upstairs and get changed. I will meet you both at home later when I'm done here" Mistress commanded the twin Kitties.

Xander, you and Lily go upstairs, shower, and put your sissy maid outfits back on. We will meet in my office in 30 minutes.

"Yes mommy. Said Xander.

After being fucked senseless, Lilly seemed numb, and followed Xander out of the room remaining speechless.

After showering and changing, the two maids sat silently in Miss Madeline's office. Both of them wondering to themselves what the purpose of the meeting was, and what the outcome would be. Ian was also thinking about the fact that it was Sunday, time for him to leave.

Mistress Madeline entered, and seated herself in her office throne chair. After what seemed like an eternity, she finally spoke.

Ladies, you both did well today. First with your behavior at the pool, and second by your visit to my dungeon. Especially you Lilly. You seem to have adapted very quickly to this lifestyle. "

"Thank you Mistress." Replied lily.

"Lily, before you leave this evening, I have a proposal I'd like you to consider. I'm so impressed with you that I'm going to offer you a full-time position here. This type of lifestyle appears to agree with you, and you do it very well. We can discuss the details if you agree, but it would involve moving in and living here full time. If not, you are free to leave, and return next weekend to complete your commitment.

Ian didn't have to think about it very long. He knew this was where he wanted to be, and what he was born to do. He was a full blown Sissyboy now, and he relished the thought of living it full time.

"Oh yes Mistress. I would like that very much. In fact, I would LOVE that. I'm sure I can live up to your expectations if you will let me."

"Very good then. Go home, make any arrangements you need to with your mother. You and Xander can continue working at the coffee shop, on a part time basis, until I have you set up with a business venture Mistress Jade and I are in the process of finalizing now." I will expect you back here, ready to serve in three days."

"Yes Mistress, thank you Mistress Madeline."

Xander and Lily looked at each other, giggled, and gently fist bumped.

"Now, off you go." Commanded Mistress Madeline."

As the girls walked out, Xander turned to lily and said, "Things are about to get very interesting around here."

"I don't think either one of us has any Idea." Lily said with a smile.

THE END.

Any comments, suggestions, or criticism are welcomed.

If anyone has any fantasy's they would like to see come to life in a future story, let me know.

***

Woman's world, you might as well accept that.

Girls put some chairs in the guest house, get changed there, going out to dinner,

Guest house, just built never been in there, used for storage, meetings, overnight guests.

Put the tables in the storage room in the back