Road to Becoming a Sissy Bitch Boy Pt. 03

The road to becoming a sissy bitch boy Part 3

After what seemed like an eternity, Ian heard his new name called. "You can come out now Lily". Ian lowered his head, opened the door and slowly walked back into the living room. There in the center of the room was Xander, or at least who he thought was Xander. Dressed in the identical maid's outfit as he was, stood his twin. Their eyes met, and Ian knew it was Xander. Xander's facial expression told Ian he had worn this outfit before, and wasn't really showing any signs of distress. Ian thought "damn, he looks sexy in that outfit". His lustful thoughts for his friend were interrupted by a loud " AHEM!

Xander's mother was sitting in a high back leather chair studded with chrome studs. More like a throne really. Standing by her side, was Xander's stepdad. He was dressed as what only could be described as a Sex Slave. Black leather tight shorts with a flap covering his balls fastened by snaps, leather chest harness and a collar that said "BITCH" on it. Attached to the collar was a chain, that at the moment was in His mistress's hand. Xander's' mother rose, and walked a slow circle around her new sissy maids. She was dressed as the most beautiful Mistress Ian had ever seen. Ten times sexier than any dominatrix he had seen on the internet. She wore a tight-fitting black leather corset, studded with shiny chrome studs. A leather military hat, resembling something one of Hitlers SS agents might have worn from WW1. Black leather boots that were above her knee, with 5 or 6 inch spiked heels. Her leather panties were crotchless, her pussy shaved. Her enormous tits bulged out of her corset, showing as much cleavage as possible, and still stay inside the outfit. From the rear, her thong strap disappeared into her ass cheeks, showing off possibly the nicest ass Ian had ever seen.

She approached each of her new maids, looking them up and down. Using a riding crop, she slapped each boy's stretched out panty bulge, "Very nice" she purred. "Ok sluts, here are the rules" Lily, you will address me as Mistress Madeline. Xander, you will address me as Mommy. But you know that already. The chores I have for you will consist of general domestic duties, providing waitress service for my dinner and luncheons affairs, and, most importantly, my personal entertainment." "My personal entertainment means, anything I tell you to do. Without question, and without hesitation. "Understood?" Both boys nodded in unison. "Today, we will start with some light housework. Get your feather dusters and dust this room. All of it! Ian grabbed his duster and got busy. "How bad could this be" he thought. "Some cleaning, serving some drinks to people I don't know, and I kind of like wearing this outfit. Plus, I get to watch Xander, who at the moment is turning me on big time". "By the way girls, my husband will be referred to as "Hutch". He is my husband, servant and body guard. "Please try not to get him mad, he has quite a temper." Hutch has been a loyal servant, and I will be rewarding him later in the day, so be ready to assist me with him if needed." "Yes Mistress Madeline" said Ian. "Yes Mommy" added Xander.

"Lily, the floor under my throne requires dusting, please see to it immediately." Again, Ian responded with an obedient "Yes Mistress Madeline." he dropped to his knees and crawled over to his Mistresses throne chair. As he dusted, he felt the spikes of her heels come to rest on his back. "Let me know when you're finished there Lily." "Yes Ma'am." "YES WHAT?" "Yes Mistress Madeline". "That's better lily."

"Ok, I'm done Mistress". "Lift up your head lily, look at me" demanded his mistress. Ian looked up just as she spread both her legs wide exposing her shaved pussy. "Lily, stick out your tongue for me, show me how big your sissy tongue can get". Ian obeyed by sticking his tongue out as far as he could. "Now lily, you're going to service your Mistress. You're going to lick my cunt lily. Understand?" "Yes Mistress Madeline" replied Ian. "Xander! Get over here now, I want you to watch this" she ordered. Xander walked over and knelt inches away from his mother's exposed cunt. Ian began licking his Mistress's sweet hole, up, down in and out. Her hips gyrating slightly, a quiet "yessssss" escaping her lips. Ian knew where a woman's clitoris was from the porn he watched, and concentrated on stimulating that area with his long wet tongue. "Good girl Lily, keep going, make mommy feel good" Cooed his Mistress. This went on for almost ten minutes. Ian's jaw was starting to get sore, but he kept servicing his new Mistress. Her legs were now fully spread, one leg over each arm rest. Her hips were bucking up against Ian's face. "LICK ME BITCH, LICK MY DIRTY CUNT" she shrieked. Her hips fully thrusting up against Ian's busy tongue. His entire face was now buried in her sloppy cunt. Her hands gripped Ian's head pulling his face into her shaved hole. "IM CUMMING, IM CUMMING! She screamed. With a series of grunts and spasms, Ian felt her pussy explode. As she reached an explosive orgasm, she actually squirted. Soaking Ian's face and the front of his maid's outfit. She released his head from her grip, and Ian was able to sit up and relax his aching jaw muscles. "Very good Lily, you show promise" Sitting inches away sat Xander. His huge cock was out of his panties, and he was jerking off quietly. Apparently watching his mother get her cunt licked by his friend excited him so much, he couldn't control himself.

"XANDER! WHAT THE FUCK" his mother bellowed. "Did anyone give you permission to jerk off to your mother?" "No mommy" was all he could say meekly. "Get your little ass over to the coffee table. Arms behind your back, and put your head down on the table top. Xander quickly obeyed. Head down, ass up you little bitch" "lily, go into my bedroom, and in the night stand there is a tube of cream marked "anal desensitizing crème". Ian quickly made his way to the bedroom and retrieved the crème. "I want you apply an ample amount to your little friend's asshole. Make sure you get a good amount inside his ass. Deep inside his ass." "Yes Mistress Madeline." Ian shot a large dollop at the entrance to Xander's hole, and rubbed it in. Using his middle finger, he slid it deep into his friend's asshole. Using a circular motion, he coated the inside as best he could. Xander positioned himself for what he knew was coming. Ass up, head down, legs spread wide as he could.

"Lily, now I need you get on your knees in front of hutch. Unsnap the pouch covering his balls and cock." Ian obediently followed her instructions. Hutch's cock and balls flopped out. His cock was much shorter than Ian's, but it had a nice girth to it. "Suck him lily, suck his cock until its nice and hard." Ian grabbed the limp cock and folded it into his mouth. He had to actually suck on it a few times before he felt any response. Then it began to swell. Ian was familiar with the term growers and showers; well Hutch was a grower for sure. Hutch's cock quickly became engorged, getting longer and thicker with every stroke. It became so thick, it barley fit in Ian's mouth. His small hand barely went completely around it. Ian estimated it to be about 8 inches long, and thick, very thick. "That will do lily said his Mistress. Good job lily" "thank you ma'am." Ian gave his mistress a little curtsey, and returned to the table where Xander was awaiting his fate. "Hutch, it's time for your reward. You may have your stepson's ass for 15 minutes. Do whatever you like." Hutch flipped Xander's dress up over his ass, and ripped his panties off with one violent yank. He gave the sissy's ass cheek a hard slap. Xander squealed in pain. The large man positioned himself behind his target of lust, and plunged his thick cock into Xander's ass. Xander let out a loud grunt as he felt his ass being violated. "I hope that crème is working" thought Ian, as he watched his friend take it up the ass from a fully grown man. Hutch was now pistoning in and out of Xander's ass, making an audible "squishy" noise from all the lube. His balls slapping against the boy's ass with every down stroke. Over and over he impaled Xander's asshole with the full length of his thick cock. Animalistic growls, and grunts now emitted from hutch. Xander's arms were flopping around on each side of the coffee table. His body jolted with every thrust. His eyes had rolled back halfway into their sockets, and he was drooling out the side of his mouth. The little disobedient sissy was nothing more than a fuck doll at this point. Ian stood by helplessly watching his new friend get fucked like a piece of meat by a savage beast. Mercifully it came to an end fairly quickly. With a few more loud grunts, Hutch tensed up, and unloaded his seed into his step son's tight hole. Ian could literally hear semen squirting into his friend's asshole. Three or four ejaculations pumped out of Hutch's cock deep inside Xander. When it was over, Xander laid there almost motionless, moaning like a wounded war victim. Hutch simply pulled his semi limp cock from Xander ass, and walked away, leaving a trail of cum dripping from his spent cock. Ian did what he could to comfort his friend, getting him to roll over on to his side. He got him a glass of water, and waited as he slowly recovered. Two large blobs of Hutches cum squirted out of Xander's ass, running down between his ass cheeks and onto the coffee table.

Ian and Xander were now alone. "I think we need to get you into bed" Ian told his friend. He helped him to his bedroom, stripped off his maid uniform, and put him into his bed nude. He threw a blanket over him, and turned out the light.

Before making his way to his own room, Ian stopped and poured himself a large glass of wine. He figured he had earned it. He made it to his room, removed his soaked dress, and sat on the edge of the bed in his black bra and panties sipping wine, and reflecting on the day's events. He slowly shook his head in disbelief, and wondered, what will tomorrow bring?

The story continues, with Ian's Road to femdom.