Road to Becoming a Sissy Bitch Boy Pt. 05

Xander and Ian arrived back at the house around 1:00pm. The smell of barbeque smoke was in the air. There stood Hutch, dressed a black leather thong, and his usual chest harness cooking hot dogs and hamburgers on the grill by the pool.

"Welcome back boys" said the Mistress of the house. "Just in time for lunch, and a swim".

"Hello" echoed the boys. The Idea of swimming was perfect for rinsing off all this dried cum thought Xander. Both boys stripped off their coveralls and quickly dove into the pool. Swimming in their bras and panties didn't seem like an odd thing for either of them at this point. After a few laps, they got out of the pool, toweled off, and went to the buffet table. Filling their paper plates with food, they sat down at the picnic bench facing away from their Mistress.

"We've got to tell her" Said Xander.

"No fucking way dude" argued Ian.

"Hey, I know my mom, and if she finds out later, we're dead meat. We will just explain we were blackmailed; she might be more lenient that way. And I know my mom has no use for those girls, trust me".

"Tell me what?" came the voice of Mistress Madeline standing a foot behind the two pool panty boys.

"Oh shit" Ian uttered. He looked at Xander and said "ok dude, I guess it's worth a shot."

The boys went on to explain the details of their recent trip to the barn, and their experience with the Baxter twins. Careful not to leave any details out. To their astonishment, she sat there, pondering what had just been said.

"Hmmm, Lesbians you say?" Both the boys nodded frantically. "Ok, thank you for being honest boys. I'm sorry you two had to go through that. Don't let this bother you, I know her mom, I know her mom VERY WELL. I will have a discussion with her tonight at the party, and will get this fixed. Don't give it another thought." Both boys sighed with relief. "Now, finish your food, then give Hutch a hand cleaning up the pool area from lunch.

"Yes Mistress Madeline" Ian said happily.

"Okay Dokie Mom" said Xander. He received a stern frown from his mother, but apparently she was willing to let that one go.

After lunch and the cleanup, the boys reported back to the boss for further instruction. "Ok girls, back into your sissy maid outfits. We have a lot of work to do today to get ready for my event this evening." Both boys disappeared to their bedrooms.

As he was dressing, Ian thought, "I kinda like this outfit." The inner Sissy in him was now starting to take full hold of him, and he knew it.

The two sissy clad maids helped set up tables, chairs and a large screen TV that was wheeled into the Party room. Trays of appetizers were arranged and put into the large refrigerator. Boxes of expensive cigars were opened, and set up on one of the tables next to the bar. Liquor and mixers were stocked behind the bar, along with glasses.

"What kind of party is this? Ian asked

"I'm not sure exactly, but I know we will be showing the playoff football game on the TV, and the guests are all big wigs Investors for one of my mother's business Ventures."

"And our duties are.......? Asked Ian.

"Serve drinks, and cater to the guest's requests is all my mom said."

"Dressed like this" Ian asked.

"I guess so, she didn't really say."

"OK with me, I'm starting to like this slutty little outfit." Said Ian. "And I don't mind telling you, you're turning me on in yours" Ian said with a sly grin. Xander gave his friend a gentle pat on his pantied ass, and continued working.

An hour before the guests were scheduled, Mistress called all the servants together for last minute instructions.

"Everyone" she said in a loud voice. "Kitchen staff, be ready for the caterers, they will be dropping off food that needs be set up on trays for serving. Hutch, make sure the bar is stocked and napkins and drink stirrers are available. And put a tip jar out for yourself, those will be yours to keep if you do a good job bartending. Lily and Xander, you two will be serving drinks, bussing dirty plates and glasses. Make sure ashtrays are cleaned, and both of you have lighters to light my guest's cigars. And remember, if any of my guests have special requests, you do everything in your power to make sure it happens. When the half time show begins, you are both to go to your rooms and change into the new outfits I bought for you." Everyone nodded, and moved off to complete the party preparations.

While setting up the food trays, Ian looked at Xander. "New outfits? Special requests? What's up with that Xander? Ian asked nervously.

"Hey, it can't be anything worse than what we've been forced to do so far, right" Xander replied.

"True" Ian replied.

As the guest's started arriving, Mistress Madeline stood at the front door, dressed in a full-length black satin dress slit up the side almost all the way to her waist showing off her long seductive legs, and her bulging tits. She welcomed them in, and had Lily and Xander escort them into the party room. Ian had his ass pinched a few times, causing him to giggle like a girl to the delight of Mistress Madeline who nodded in approval.

The party ensued, the football game playing on the TV, Drinks being served by the sissy maids, and food trays being shuffled in and out of the room.

"The liquor is really being gone through, don't ya think?" Said Ian.

"Hell yeah, these guys are starting to get drunk, but they are all behaving themselves" Xander replied.

The guests consisted of middle-aged men dressed in expensive suits. A few of them had women with them, mostly in there 20's and obliviously not their wives. One woman who was in attendance alone, spent most the party sitting at Mistress Madeline's Table. The two women engaged in a whispered chat, neither of the maids could overhear. Xander and Ian deduced this must be Mrs. Baxter, Ashley and Dawn's mother.

As half time approached, Mistress Madeline motioned the two sissy maids over, and said. "Ok girls, time to get changed, and remember what I said, I want smiles on all my guests faces when they leave here tonight.

"Yes Mistress" both boys said together. When lily returned to his room the first thing she noticed was a large jar sitting on the night table marked "TIPS" in bold letters.

"I wonder what I'm supposed to do with that?" she thought. The next thing she saw was a uniform laying folded on his bed. A cheerleading outfit to be exact. Along with it, the same tight half back white panties Xander had on with his school girl outfit. Also, Hooter girl shiny pantyhose, and a new bra, with silicone breasts already implanted in the cups. A wig with a large pony tail tied in a bow, Pom Poms and white girl's sneakers completed the outfit.

"Sweet" thought lily" She dressed quickly, and was almost ready when the door opened. Dressed as a cheerleader as well, but for the opposing team stood her friend Xander.

"Look at you! You sexy little slut" said Xander. lily grinned from ear to ear feeling as feminine as she had in her entire life.

"A few last touches" said Xander. He took out make up, and applied it to lily's face. Then some pink lip gloss, and sparkles for her eyelids, cheeks and hair.

"Ok girl, let's go" said Xander. Both sissies bounced out of the room, and skipped down the hallway hand in hand. As they entered the party room, everyone stopped talking, all eyes were on the two sissy cheerleaders. Then, after an awkward ten seconds, the room erupted in applause, whistles, and catcalls.

The two slutty cheerleaders looked at each other, giggled, then curtsied to the men clapping for them. Instantly they both knew what they were supposed to do next. They attempted to cheer the football teams on, bouncing around jumping up on tables and cheering the men on, then shaking their fake tits up and down in the half shirts that showed most of their abdomens. They lifted their skirts and grabbed their panty bulges to the men's delight. They moved from table to table, shaking their pom poms and sitting on men's laps when asked. Both sissies had men slide their hands up into their blouses more than once, giggling and jumping up quickly before a firm grip could be established.

Mistress Madeline sat at her table beaming with pride, and approval.

"Those two are incredible "said Mrs. Baxter.

"I know" said the Mistress.

"I wish I had a few like them in my harem" added the mother of the twins."

"Just lucky I guess" replied the Mistress. "I might consider sharing them for an afternoon, or an

evening if you take care of that little problem we discussed." Mistress Madeline suggested.

"Not a problem Madeline, consider it done. I will have a little chat with them tomorrow morning."

"Thanks" said the proud Mistress.

The game resumed on the TV, the two slutty cheerleaders went back to serving drinks, lighting cigars and emptying ashtrays. As Lily was heading into the kitchen, she felt a tap on her shoulder. She turned, and saw a tall, handsome man standing behind her. "Yes Sir?" she said.

"May I see you somewhere privately, where I can ask you something my dear?"

"Yes sir" Lily answered quickly. "Right this way sir." She led him down the hall to her bedroom. They both entered, and he closed the door behind them. "What can I do for you sir" she asked.

"Well, my host told me that if needed help with anything, you would be the one to take care of it."

"Yes sir, I absolutely can"

With that, he reached down and unzipped his fly, and pulled out his hard, 6-inch cock. "Can you take care of this miss?" he asked.

"With pleasure Sir," Lily said enthusiastically. She dropped to her knees and took his stiff cock in her mouth.

"Oh my "he cooed." Lily sucked his cock like a pro, using her tongue, she flicked the tip, causing it to jump. Her wet mouth slid back onto his cock taking the full length of the shaft. Her head bobbed up and down, her hand slid up and down the length of his cock, jerking him off into her mouth.

"Is this what you had in mind sir, is this how you like it?" Whispered Lily.

"Oh yes, yes, suck it you dirty slut" he groaned.

Lily pulled his stiff little boner out of her mouth, and spit on it. Then jerked it until it made the sloppy squishy noise that could only come from a wet hand job.

"Please, please he begged" she guided his cock back into her mouth and allowed him to finish by face fucking her. His hips thrust forward then pulled out, over and over. Then, with a loud grunt he came. His cum shot out of his cock landing on lily's tongue. She looked up at the man, opened her mouth, stuck out her tongue showing him the creamy deposit he made inside her mouth. Then she swallowed.

"About 6 minutes," lily guessed. "Not bad for my second blow job."

The man zipped up his fly, straightened his jacket and combed his hair in the mirror. "Thank you sweetheart, that was wonderful" said the grateful guest. Before leaving, he stopped by the door, removed his wallet, and put money in the tip jar on the night table. Then he was gone, leaving Lily still kneeling on the floor.

She stood up, grabbed a few Kleenexes wiped off the edges of her mouth. Looked in the mirror, checked her make-up and hair. Satisfied, she started to leave, but decided to check the contents of the Tip Jar. Astonished, "Holy shit" escaped her mouth." She reached in an pulled out 2 crisp 50-dollar bills. "This works for me" she thought." She returned to the party and resumed her waitressing/cheerleading duties.

Xander wandered over, noticing she had been gone said "where ya been girl?" She leaned over and whispered in his ear. His eyes got big, "OMG NO WAY" he said.

"Way!" she answered.

The two friends started giggling like little girls. As the two celebrated Lily's good fortune, another guest walked up, put his arm around Xander's shoulders, and whispered something too low for Lily to hear. The two of them started walking toward the bedroom hall. Xander looked back at Lily and gave her the thumbs up sign.

"This could be a very, very good night thought Lily.

Lily and Xander made multiple trips to their bedrooms that night, servicing just about all off the men in attendance. They were careful to never be gone at the same time. Lily even had a couple request private time. She escorted that couple back to her room not knowing what to expect. While she had her man on his back and sucking his cock, the woman took off her dress started playing with herself as she watched Lily sucking her date off. After shaking and spasming a few times, the man came in Lily's mouth. "Is there anything else I can do for you folks?" asked Lily.

"No, that was perfect" replied the scantily dressed woman. That couple tipped $150.00.

Xander even had a gentleman request she watch him, as he jerked off in front of his date.

By the end of the evening, both Lily and Xander had earned more money than they could have made working at the coffee house in 2 months.

As the evening began to wind down, with some guests saying their goodbyes, Mistress Madeline approached the girls. "Girls, I just wanted to tell you both what a good job you did this evening. That little half time show you two put on was over the top, much more than I expected." "Whatever went on in your bedrooms seems to be sending our guest's home with smiles. And yes, the tips are yours to keep."

"Thank you Mistress," chimed both girls.

"Tomorrow we will be having a pool party to celebrate the completion of Lily's first weekend of her service commitment. You both will be free to enjoy yourselves" The two cheerleaders smiled, and gave each other a little high five.

"I do however have one final request from a special guest I need you both to attend to." Instructed the party host.

"Yes Mistress Madeline." Answered Lily.

"Of course mommy" added Xander.

"She is waiting in my bedroom. You will both report to her now, and extend the same obedience and respect you show me. She is a fellow Mistress, and will be addressed as Mistress Jade."

The girls nodded, and started down the hallway. "I don't think we will be getting tipped for this one Xander" said Lily.

"Me either" answered Xander.

As the girls opened the door to the Master Bedroom, there sat Mistress Jade completely nude on the bed. "Hello slaves? she said in a commanding tone.

"Hello Mistress Jade." echoed both girls.

The woman addressing them was stunning. Her fire red hair flowing over her shoulders half covering her tits. Although they were most likely surgical implants, they were perfect, and neither Xander nor lily could stop the erections that were beginning to form in their panties. Apparently both boys retained some bisexual tendencies despite all the sissy training they had received.

"Ladies, I was impressed by your performance's this evening. You're Mistress is being extremely gracious by letting me borrow you for a short while."

Both girls curtsied, and thanked the Mistress.

"As I'm sure you are aware, I am Ashley and Dawn's mother. I understand my daughters were unkind to you today. I heard they made you both do thing's against your will. Is this true?"

"Well, it wasn't all that bad Mistress." Said Xander.

"Well, it was against your will, and there was blackmail involved, that's all I had to hear. Both my daughters are spoiled brats, and have been warned before about this sort of thing. "You will have an opportunity to hear their apology in person tomorrow."

"Yes Mistress" both girls answered.

"This evening you were slutty girls. Right now, I need you to act like a couple horny young boys. You can be my sissy boys for a while." "Both of you, remove your uniforms. But keep the panties on. I like them."

"Yes Mistress" the boys answered.

"Now let me see your tongues boys. I heard you two have nice big tongues." Both boys suck their tongues out for their mistress. "OK, both of you, on your knees, crawl over here." She ordered. "I want two sissy tongues in my cunt now!" Both boys lurched forward and began licking the gorgeous woman's twat. "Yes, Yes, get them both in there." She moaned. She lifted her hips and spread her legs wide so that both boys had easy access to her wet hole. Both her hands were around the back of the boys' heads, as she rutted her cunt against their faces.

This went on for several minutes, her hips keeping up with a constant rhythm, and moans of lust getting louder, and more frequent.

"GOOD BOYS, KEEP GOING, LICK MY FUCK HOLE. SUCK ON MY CUNT YOU LITTLE BASTARDS" she screamed..

"NOW YOU!" pointing at Xander. "Lift up my ass and stick your tongue in my ass." The boys jockeyed into position so that their nympho Mistress had their tongues in both her ass and cunt. After she seemed to have her fill of rimming, she screamed. "Everybody up" the boys jumped off the bed, and stood at attention. "YOU!" pointing at Ian. "Back on the bed, lie on your back" Ian assumed the position. She slowly climbed on top of Ian and straddled his hard cock. She slowly lowered herself down until the entire shaft of his enormous cock was inside her tight hole. "Ahhhhhh good boy." She moaned. She began a rocking motion sliding her wet cunt onto Ian's throbbing hard cock. "Give me that cock boy, fuck me, ram it into me" she demanded.

Ian thrust his engorged cock in and out of his Mistress. "What a tight cunt for an older woman" thought Ian.

"YOU!" now pointing at Xander. "Get behind me, and play with my tits. Squeeze them, pinch my nipples." "YES, YES, PLAY WITH ME BOYS, FUCK ME LIKE THE GODDESS I AM." The boys continued fucking and fondling their goddess until she screamed. "YOU! in the back. Ram your cock in my ass!" "Did you hear me? I need a cock in my cunt and I need one in my ass!"

Xander didn't hesitate. He bent his goddess forward so her asshole was exposed. He guided his cock to her back door, and shoved it in hard.

"UGGGH" she grunted. "OH Yaa" she said in a muffled voice.

Xander pounded her ass in and out with powerful thrusts. Ian arched his back and shoved his cock as hard and deep into her as he could. The boys were literally fucking the hell out of this slutty woman.

Good thing both boys had a good grip on her, because she no longer had control of her body. She was being thrown around like a rag doll at this point.

"GIVE IT TO ME BOYS, USE BOTH MY HOLES" she bellowed.

Xander shot his load first. "Wow, I'm cumming quickly, it must be the size of my cock, and the tightness of her asshole," He thought. With a triumphant "IM CUMMING" he let his load shoot into his neighbor's asshole. He then just wrapped his arms around her neck, and hugged her from behind. He held on, feeling her body shaking, shuttering.

"OOOOH YOU WONDERFUL BOY'S, YOU SEXY, SEXY BOY'S" she screamed. Her orgasm erupted, and she spewed onto Ian's stomach.

Seconds before Ian's cock erupted, she slid off his cock. She grabbed it, and finished him off with her hand, her face inches from the tip of his cock.

"OH SHIT" yelled Ian, shooting cum all over his Mistress face and tits.

Xander rolled over on to his elbows, his head turned towards Ian's, "Well, that was different." He admitted.

"Thank you boys, that will be all for this evening. I will see you both tomorrow at the pool party. Now off to bed with you."

"Yes Mistress Jade, and thank you." Said Ian.

"Yes Mistress Jade." Echoed Xander.

Both boys lay in their beds, pondering the erotic events of the evening, and their unexpected financial windfalls. Exhausted, they drifted off to sleep wondering how they were going to face the Baxter twins the next day.

NEXT, THE CONCLUSION .