Road to Becoming a Sissy Bitch Boy Pt. 02

The road to becoming a sissy bitch boy Part 2

Ian and Xander stood there by the pool, frozen, like two convicts caught in the search light of prison guards. After what seemed like an eternity, Xander's mother finally spoke. "XANDER!" "WHAT EXACTLY IS GOING ON HERE?" "Mother, it's not what it looks like" whined Xander. "XANDER! NOT ANOTHER WORD. GET INSIDE NOW, AND BRING YOUR LITTLE FAGGOT FRIEND WITH YOU" boomed his mother. Ian thought about making a run for it, but the only exit was being blocked by Xander's stepfather, a large man, who obviously worked out regularly judging by the bulging muscles showing under his tank top. Ian could tell by the look on his friends face he was terrified. Xander lowered his head and walked slowly through the breezeway into the living room. Ian followed closely behind him, avoiding eye contract with either of Xander's parents.

Once inside, Xander stopped and stood in the center of the room. Ian stood at his side, and tried not to panic. "Jesus Xander, what the hell is going on? Don't ask dude, but we are in some serious shit right now. Keep your mouth shut, and whatever you do, don't talk back to my mother." Ian nodded.

Xander's mother entered the room and stood in front the terrified boys. "Boys, the first thing I want both of you to do, is get into my shower, and clean yourselves up. You can shower together since it's obvious neither of you are shy. And toss those bathing suits outside the door so they can be laundered. Xander, your stepfather and I are going to discuss how we're going to handle this while you're showering.

As soon as the bathroom door was closed, Ian took a deep breath, and tried to calm down. "Xander, so what happens now?' Ian asked. "Just do what she says, and when she calms down, I'm sure she will want you out of the house" Ian, I do have to warn you though, my mother is a bit on the eccentric side. I might even call it kinky. Try not to be shocked with what she says. Her bark is almost always worse than here bite." For some reason the word "almost" seemed to stick in Ian's mind. "Come on, we better get in the shower" Xander whined.

They both got into the oversized shower, and let the steam fog up the glass. "You wash my back, I'll wash yours, ok?" said Xander. Ian agreed, and reached for the soap on a rope hanging from the over head faucet. "Hang on a sec, let me get my mom's special soap, I know where she hides it." Xander disappeared from the shower and came back seconds later. "You do me first buddy" Xander asked. "sure" Ian replied. Getting a nice lather going, he scrubbed his friends back, legs and neck. He purposely avoided Xander's ass and balls for fear of another occurrence of what took place by the pool that got him into this mess in the first place. He spun around and handed the soap to Xander, and said "my turn". He heard the soap bar hit the floor, and remembered Xander had some special soap of his mothers. He closed his eyes and felt his friend massaging his shoulders and neck, it felt so good. Xander's hands slid down Ian's body and soaped up his back, gliding over his ass, then down his legs. "you've been a very dirty boy today Ian, cooed Xander. I think you need an extra scrubbing so your clean for my mom." Xander's hands went immediately to Ian's ass. Massaging, squeezing his ass cheeks. Then Ian felt a soapy finger slide between his ass cheeks making contact with his asshole. Ian jumped. "wait" stammered Ian. "Shhhhh, I know what I'm doing, trust me" Xander whispered so close to his ear he could feel his breath. Xander's continued to soap up his friend's ass, and reached further until he had Ian's balls in his hand. Ian did not resist, again this was something new to him, and he knew he liked it. Xander's hand made its way on to Ian's cock. Ian pushed his hips forward and begin grinding it against his friend's soapy hand. "Omg Xander, this is wonderful Ian whispered. "I know buddy". Ian's cock was now fully erect, and twitching. Xander let Ian hump his hand while keeping his other hand busy on his ass. Then, with out warning, Ian felt a soapy finger enter his asshole in one second it was in. He uttered a low high-pitched moan. anal was something completely new to him. He'd seen in his porno films, and heard a lot about it, but never experienced it. He'd heard rumors that it hurt at first. Well, so far so good, he knew he liked it from the moment his virgin ass was penetrated. Xander slid his finger in and out of his friend's ass, feeling Ian's body bucking against his soapy fist. "Omg, I'm getting jerked off and finger fucked at the same time" Ian thought. "What a faggot I've become."

Xander sensed his friend was about to orgasm again, and removed his hand from Ian's thrusting cock. "Ohhh, please" moaned Ian. "That seemed to go pretty well Pal, I think you might be ready for a little more" Xander said. "Yes, yes, more" begged Ian. With that said, Xander took his mother's "special soap" which in reality was a dildo made out of soap, and positioned at the opening of Ian's eager asshole. "Ready?" said Xander, "yes, yes Ian moaned. Xander slowly pushed the tip in, then guided half the shaft into Ian's virgin ass. Ian tried not to scream and covered his own mouth. He saw stars as his tight ass was violated by the soap cock. "Give it a minute buddy, and try to relax. It doesn't hurt for long." Reassured Xander. Ian tried to relax his asshole, but it felt like he had a watermelon shoved up his ass. Slowly, gradually, his friend proved right. The pain went away, and was replaced with a feeling of pressure. Xander pulled the dildo slowly out, then pushed slowly in. Ian's face was pushed up against the glass, taking deep breaths and trying to relax. Xander picked up the pace slightly, and watched his friend's reaction to his first ass fucking. Ian arched his back slightly, raising his ass to meet the toy entering his ass. Xander smiled as he watched his friend start to actually push back against the cock, causing it to slide deeper into his tight hole.

Just as things began to heat up, the boys were jolted with three loud bangs on the bathroom door. "XANDER! YOU BOYS GET OUT OF THE SHOWER THIS INSTANT! I WANT BOTH YOU BOYS OUT HERE IN THE LIVING ROOM NOW". Xander knew his mother well enough to know she meant, NOW. The two boys jumped out of the shower, and looked for towels to cover themselves with. Nothing, not a towel in the room. "OMG what do we do now" gushed Ian.

"I don't know, let me see if my mom will bring us some." Xander cracked the door open, and meekly asked his mother if she could give them towels. "All my good towels are clean Xander, besides, you little faggots don't need to cover up. I'm a grown woman, I've seen a naked boy before. GET OUT HERE NOW!"

Ian couldn't believe he was doing it, but he followed Xander obediently out of the bathroom into the center of the living room. They both covered their privates with their hands as they waited in the empty room for whatever punishment was coming. Xander's mom stormed out of the kitchen and stood directly in front of the two naked quivering boys.

"Ok young men, what am I going to do with the two of you?" Xander, this is not the first time I've had to remind you guests are not allowed in my house when I'm not home. And now I see you have turned out to be a full-blown homosexual." "Jesus, you're so disgusting. I'm this close right now to packing your bags, and putting you out on the street.

"And you, who are you exactly?" "Ian I said quietly." "May I ask how you know my son?" "We are friends, we work together". "I see". "Are you aware Ian, this entire house has a camera surveillance system? "Would you like to watch the camera footage of you jerking off while you sucked another boy's cock?" "No ma'am" Ian's voice now shaking.

"I thought not." "Well, I know where you work, and it won't be hard to find out where you live." "I'm sure there are a few people you know who might be interested in seeing how you like to spend your free time". "No Ma'am, please no". Ian begged. Ian knew if his avid church going mother ever found out he was gay, he' be sitting on the curb next to Xander with no place to live. "Ok then, I think I may have a solution said the older woman."

"For the next two weekends, you both will report here and do chores for me. Chores include whatever I tell you to do, no questions asked. "Or, you can leave and take your chances on what your family and co-workers think about your performance today"

"How bad could this be? Thought Ian. Surely it would be better than the humiliation at work, the alienation from his mother, and possibly living as a homeless person. "I choose to stay and do chores" Ian said quickly." Xander? "Mom, you know I need that job whined Xander." SHUT UP! roared Xander's mother", causing both boys to jump. "What's it going to be Xander?" "ok, ok I will stay and help Ian with the chores." Xander's voice had a slight sarcastic tone to it.

"Alright then, first things first." Now that the two of you are cleaned up, you need to get dressed. I can't have naked little faggots running around my house." Demanded the boss. Xander, go to your bedroom and put on the work clothes I bought for you. You know which ones I'm talking about." Ian, you go to the spare bedroom, and I will bring you something to wear while you're working." Both boys did as they were told.

Ian sat on the edge of the bed, waiting for his new boss to arrive with his clothes. Ian's mother entered the bedroom carrying a pink shopping bag. She handed it to Ian and said, "ok, put these on, and make it quick". Ian opened the bag and his heart sunk. Inside was what looked like women's clothes. A black lacy French maid's uniform to be exact. Panties, bra, crotchless fishnet stockings with garters, the complete outfit. "What the hell, you gotta be kidding me? Blurted Ian. "No questions asked, remember Ian? And by the way, Ian is your name you use out on the street. While you're here, your name is Lilly. Got it? Yes Ma'am Ian murmured. Xander's mom helped Ian into the outfit, fastening the garter clips, adjusting the bra so it fit just right. The dress part of the outfit was short. Very short. No matter how he stood, both ass cheeks peeked out from under the hem line. "Ok, almost done beamed his tormentor." From a drawer in the bureau, she pulled out a blond wig. She quickly put it on Ian's head, and secured it with bobby pins. Out of another drawer, she took eye make-up, and a lipstick case. Bright RED lipstick. After a quick makeup and lipstick application, "Ta Da! You're done" "OH Lilly, look how pretty you are" she announced. Ian stood, and looked in the full-length mirror hanging on the wall. Ian was shocked. Who he saw looking back at him was not him. It was a cheap, cross-dressed slut. Just like the ones he jerked off to on the internet. Except, he actually thought he looked cute in some sick way. Ian felt the satin panty fabric stretched over his cock and balls start to stretch. "Omg no, I'm getting a hard on" he thought. In a matter of seconds his cock was fully erect and poking out his panties through the waistband. "Oh my! What an impressive panty bulge you have Lilly. Why am I not surprised you like this outfit. You're going to be perfect for the chores I have in mind for you. Ian's mind began to race. "What exactly did she have in mind" he thought. Well, it was too late now to worry about that now, he was all in at this point, and he knew it. "Sit here, and wait for me to call you lily, Understand?"

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