Road to Becoming a Sissy Bitch Boy Pt. 04

Ian awoke to bright sunlight streaming through window. He sat up in bed, trying to clear his thoughts from the prior day's events. Hanging neatly on the chair next to the bed was a white robe. "For me I presume" Ian thought. Pinned to the pocket was a note "breakfast at 8:00 am". He glanced at the alarm clock, 7:48. Good, he hadn't overslept. "God only knows what the punishment for that is" he thought. He put on his robe, and headed out to find where breakfast was being served. Halfway done the hall he intercepted Xander coming out of his room. "Hey dude, you ok?" asked Ian.

"Hey Ian, yeah I'm ok. I've had rougher sessions to be honest." Xander replied. "Thanks for using enough of my mom's desensitizing shit on me last night, it literally saved my ass." Both boys nervously laughed like it was actually funny.

When they arrived at the dining room table, Mistress Madeline was already there. Her head buried behind a newspaper. Without lowering the paper, she spoke. "Good morning boys"

"Good morning" said the boys in unison.

"Hutch has set up a buffet style breakfast on the table in the corner. Serve yourselves and clear your own dishes when you're through.

As they were filling their plates, Ian said, "so I guess things lighten up a bit when were not in our sissy outfits. No Mistress Madeline address, and she called us boys, not girls or faggots."

"That's pretty much it dude, just watch what you say, and how you say it. If she's dressed in the leather outfit, it's best to refer to her as Mistress Madeline, or you know what." Xander advised.

Their new boss lowered her paper, and delivered the boy's duties for the day. "Ian, after you shower, call your mother, and tell her you are spending the weekend over at your friend's house. Make up a convincing story about why you didn't come home last night. Then, you will dress in the clothes laid out for you on your bed. Your first task will be to do the pool maintenance. Vacuum, add the appropriate chemicals, clean out the skimmer and hose down the surrounding deck. And please, make sure you scrub the area where you and Xander unloaded your balls on each other yesterday. SOOO Disgusting." She hissed. "Xander, I have your clothes laid out for you as well, you will report back here for Home schooling." "And boys, separate showers today, I don't want a repeat performance of what went on in my shower yesterday. And yes, I have camera's EVERYWHERE."

"Jesus Christ, Is nothing sacred around here?" Cameras in the bathrooms? Ian thought. "And WTF? Home schooling?. Xander was almost 23 years old. I guess it must be college prep or something" Ian concluded.

Ian returned to his room, and found a brand-new pair of tan coveralls folded neatly on the bed. Next to that was a pink bra and panty set. "Well, at least I get to cover up" he thought. He showered, dressed, and phoned his mom. After convincing her with a believable story, he headed out to the pool area. Thankful that today's work schedule was a least not humiliating. He hooked up the vacuum equipment and started sweeping the bottom of the pool. After about 45 minutes, Ian was sweating his ass off. It was almost 90 degrees and the coveralls he had on were not made for working in this kind of heat. "I don't think I'll be breaking any rules if I go get a bottle of water from the refrigerator." He reasoned. He put the vacuum wand down, headed for the kitchen. Before he made it through the breezeway, he froze. Standing in the middle of living room was Xander. His friend was dressed in the sluttiest school girl outfit he had ever seen. A light blue pleated short, short skirt, A skin tight white top tied together just below the bra. White thigh-high stockings with blue bows on the top of each garter. And apparently, Xander now had tits. Really, really nice tits. Hard nipples poked out through his tight white blouse. His blonde wig was shorter than the one from yesterday, but this one had pig tails on each side tied with frilly blue ribbons.

In front of him, sat Mistress Madeline. Legs crossed, perched on her throne like a strict school master. Her hair pulled back, and tied in a bun. She wore black rim glasses, and held a yard stick slapping it repeatedly into the palm of her hand. Her black leather Dominatrix outfit had been replaced with a black leather bra, and skin tight black leather boy shorts. Her boots were leather, had 6-inch stiletto heels, and only went up as far as her ankles. He muscular, tanned legs seemed to go on forever.

Ian moved back slightly so he could not be seen by either of them, but had a clear view of the scenario playing out in front of him. If Ian could have written a script for a porno film, this was beyond anything he could imagine. He felt his cock swell instantly inside his sweaty panties. He couldn't decide who was turning him on more, Xander, or Mistress Madeline.

"Now Xander, turn to chapter 4 in your handbook, and read the first paragraph aloud." Instructed the sexy school teacher.

"Chapter 4," he started, "Proper conduct at a social gathering for sissies" read Xander. "Sissy boys should never speak, unless they are asked to speak." "Eyes should always be lowered, never making eye conduct with anyone unless ordered to."

"NO, NO, NO shouted Mistress Madeline. Lower your tone, use a softer, more feminine voice. Like I've taught you. Again, she insisted."

This time Xander's voice was high, like a girl.

"Amazing" thought Ian. "This must be sissy school training" Ian concluded.

"Continue" Xander's mom commanded."

Xander finished reading the chapter, sounding more and more like a young school girl as he went. When he was done reading, Xander glanced up at his mother for approval.

"Very, very good Xander" she said. "This will conclude our scholastic studies for today Xander." "Now it's time for an obedience lesson."

"Yes Mommy" Xander said still using his sissy girly voice.

With that, she dropped her yard stick on the floor. "Retrieve that slave boy" she shouted. "And pick it up the way I've taught you". Without hesitation, Xander walked over to the yard stick, turned, and slowly bent over from the waist down, never bending his legs or knees. His skirt rose up, and staring at Ian was Xander's perfect ass. His white panties stretched tightly across his ass, barley covering it.

Before he could straighten up, His mother shouted "FREEZE SISSY". Xander obeyed. Mistress Madeline rose, stood behind him, and gently slid her hand over both of his ass cheeks. Then, without warning "SLAP" her open hand landing squarely on one of his ass cheeks.

"Ouch" cried Xander, continuing to use his girlish voice somehow.

"You've been a naughty, dirty little slut this weekend Xander, haven't you?"

"Yes Mommy".

"You need to be spanked, don't you sissyboy?"

"Yes Mommy"

"You like being spanked don't you" The mistress continued.

"Yes, yes, yes sputtered Xander.

Instantly his ass was spanked three more times, Hard. "You may stand up and face me. Xander quickly obeyed. She returned to the sitting position on her throne and said, "Now, I want you to lift up your little skirt, and show Mommy your panty bulge." "I know how big your cock is, and you know how much I enjoy seeing it stretch out a pair of cute little panties."

Xander did what he was told, and obediently lifted his skirt. His cock was rock hard, jutting away from his body. His panties were visibly stained with pre cum, and barely able to contain his massive manhood.

"Apparently spanking agreed with him" thought Ian. By this time, Ian's cock had also grown rock hard too. Watching his friend being treated like a naughty school girl whore made him horny and jealous. He wished it was him receiving this lesson.

"Very good boy" gushed Mistress Madeline. Now pull your panties down, and move closer to mommy." Xander pulled his panties down to his knees, and staggered to within inches of his teacher. "Now jerk off for me. Show me how hard and how big that cock of yours can get." She commanded. Xander grabbed his cock and began stroking it, jerking off for his mother, inches from her face. After a minute or two, she grabbed Xander's engorged cock with both hands, slowly sliding them up and down the length of its shaft.

Xander let out a sissy moan, and arched his back sliding his cock further into his mother's hands.

Using her son's pre-cum as lube, she slowly stroked his cock, up and down, then moved up to the head of his cock. She formed a circle with her thumb and forefinger and slid it around the tip of his cock. After a several rapid little cock head jerks, Xander started bucking his hips, desperately trying to fuck his mother's fist. "Not so fast slave boy. Mommy has a few more things in mind." Scolded his mom. She stopped stroking him, and grabbed Xander by his hips. She slowly pulled him towards her and kissed the tip of his cock, then opened her mouth, stuck out her tongue, and slid the entire 9 inches of her son's cock into her mouth. Sliding it Slowly in, then slowly out of her perverted, slutty mouth.

Ian couldn't believe what he was seeing. "He got fucked in the ass by his stepfather last night, and now he's getting a blow job from his mom today, is nothing taboo in this house Ian thought?"

After a few minutes on lustful incest, Mistress Madeline pulled Xander's cock out of her mouth, and stared at Xander. After a few seconds of silence, she said "Xander".

"Yes Mommy" he replied.

"I want you to remove Mommy's shorts, and be quick about it" she ordered.

Xander complied, tossing them on the floor next to her throne.

"Now, I want you to stick your fingers in your mother's twat. I want you to slide them deep into my vagina, and tell me if I'm wet."

Xander reached down, and obediently did as he was told. He pulled them out, and held them up to his mother's face. They glistened with the secretions of her aroused genitals.

"Ok son, I want you to fuck me now". I need you to fuck your mother like a dirty whore".

This seemed to stun Xander, He hesitated slightly, but knew he if didn't obey there would be hell to pay. Especially in his mom's present lustful frame of mind. He pulled his mother ass closer to the edge of the seat, and spread her legs over the arms of the chair. He grabbed the shaft of his hard cock, and lowered himself down on top of his mother. He rammed his cock deeply into her wet hole, causing her whole body to slam back into her chair. She wanted it rough, and He knew it. He began thrusting it in and out of his mother's wet cunt.

She let out a low guttural groan, followed with a loud "YES, YES DO IT XANDER. FUCK YOUR MOTHERS CUNT".

This excited Xander, and he picked up the pace, unmercifully pounding his enormous cock into his mother like the dirty whore she was.

"FUCK ME, FUCK ME" she cried as her eyes rolled back into her head. She began grunting like an animal with each stroke of her son's hard cock.

"TAKE IT YOU WHORE, TAKE ALL OF MY COCK, TELL ME YOU WANT IT HARDER, DEEPER" Xander screamed.

"YES SON, GIVE IT TO MOMMY, GIVE IT TO ME LIKE A CHEAP WHORE" she screamed back.

Xander was close to cumming and decided he didn't care about the consequences of Incestual sex. His balls tensed up, his legs began shaking, and with one final thrust, he sank his cock as far as he could into his mother drenched cunt. Load after load of cum spasmed out of his cock into his mother. His orgasm seemed to last 3 or 4 minutes long. He pulled his semi limp cock out of his mother, and watched glob after glob of his cum ooze out of his mother's cunt onto the chair seat. Xander slid off his mom, and onto his knees in front of the throne chair.

Mistress Madeline still panting heavily, opened her eyes halfway, and said. "Not bad slave boy". "Now off with you." "Get changed into your coveralls, and help Ian finish up around the pool. When you boys are done, I think you both have earned a few hours off. Don't let me hear or see either of you doing anything inappropriate, and don't leave the property."

"YES MA'M" squealed Xander as he ran off towards his bedroom..

"Be back here in a few hours, you both will be working a party here tonight" she shouted.

"Okay!" He shouted back.

When Xander got to the pool area, Ian was about done putting the pool equipment back in its closet next to the cabana. "Hey Ian Xander said."

"Hey buddy, how did school go?" queried Ian.

"You know, the same old boring school shit".

"Yeah, Rightttttttt" Ian answered sarcastically.

Xander let Ian know about getting the few hours off, and the scheduled party."Sweet" Ian replied. "What kind of party?, and what will we be doing?" asked Ian.

"Beats me" said Xander. Probably bussing tables, serving drinks, cleaning up, that sort of thing." "The guests who attend my mother's parties are mostly stuffed shirts from one of her clubs, or associations she is connected to. So, I wouldn't worry too much buddy. Xander assured his friend.

"Good, Ian said. Just as long as we don't have to dress up in something ridiculous again".

The boys decide to take a walk, and have a look at the property. Xander's house was on a large piece of land, 5 or 6 acres to be exact. Surrounded by fields and farms. It was nice to be away from city streets and close neighbors where I live thought Ian. After walking for about 40 minutes, they ended up by a river on the edge of the property line, next to a small barn.

"Whose barn is that?" Ian asked.

"Our neighbors, the Baxter's." Xander replied.

"Do you know them?" Ian asked.

"Kind of, I went to high school with the two girls who live there. Twins, Ashley and Dawn." Answered Xander. I never liked them much, they are good looking girls, the cheerleader type that hung out with elite crowd of jocks and other privileged kids. They made fun of me a lot, so I just ignored them."

"I know what that's like, trust me," said Ian.

An hour flew by, spent by the two boys talking about work, life, and avoiding the events that occurred with Xander's mother. Suddenly the sound of off-road vehicles was heard. The boys turned to see two small all terrain ATV's approaching them.

"Oh no, exclaimed Xander."

"What's the matter?" asked Ian.

"It's the Baxter twins, Let's leave, I really don't feel like dealing with those two Rich bitches." But it was too late.

"HI Ya Xander" one of girls cooed in a sickly-sweet tone of voice

"Hey girls" Xander said in a mono tone voice.

"Who's you're friend Xander?" She asked.

"This is my friend Ian. Ian, this is Ashley and Dawn."

"HI Ian" both girls responded in unison, with the same fake sweet tone of voice.

"Long time no see neighbor," Ashley said.

"No, I guess not" Xander replied.

"Well maybe not that long, if you wanna count yesterday" chided Dawn.

Ian and Xander both looked at each other. "Oh no" thought Ian."

"What do you mean?" asked Xander."

"Well, I must say that was some performance by you two yesterday at the pool." Teased Ashley.

Xander stared blankly at the girls and said, "I have no idea what you're talking about."

"Oh, I think you do neighbor. Would you like to see the video we recorded on my phone of your little date with your faggot friend there? Would that refresh your memory?"

"WTF XANDER! DOES ANYTHING GO ON AROUND HERE THAT ISNT RECORDED?" Screamed Ian.

"I'm sorry Ian, I had no idea anyone was around." "Ok, so what do you girls want" asked Xander.

"Welllllllll" Ashley said smoothly. "We could use some help over there in the barn. You help us out, do what we say, and I will let you watch me erase that movie file from my phone." "If not, we could always show it to our parents, who I don't have to remind you are members of most of your mom's clubs. I'm sure your mom will be thrilled with everyone in town finding out what a little faggot you have turned out to be."

"Jesus" Xander said under his breath. Xander turned to his friend and asked, "what do you think Ian?"

"Well, if our punishment from your mother turns out to be only half as bad as what happened to you last night, I say we help the girls out in the barn."

"Agreed." Answered Xander. "Alright, girls, we will give you guys a hand in the barn." Xander whined.

"Ok, follow us boys" said Ashley.

As the girls sped off towards the barn, Ian and Xander walked slowly, side by side. "Is this shit ever going to end Xander?"

"Look Ian, we do a few chores, be nice to them, do what they say. They erase the video, and were outta here."

"whatever" said Ian.

When they got to the barn, the girls were sitting together on a stack of hay bales. "Ok girls, what's it gonna be? Clean out horse stalls, stack bales of hay?" Xander asked.

Both girls giggled at the same time sounding like the brats they were. "Oh no, we have ranch hands that do that work. That's not exactly what we had in mind neighbor." Giggled Dawn.

"Ok, what then?" asked Ian.

"Welllllll, we kinda want to see those big cocks of yours in person. Up close, ya know?" "I don't think the video on my phone does them real justice, if you know what I mean."

"They have got to be fucking kidding me" screamed Ian.

"Calm down buddy, We flash our cocks, get them to erase the video, and we walk. Simple as that."

Xander, I got a bad feeling about this, but I guess we have no choice." Ian said.

"And you will erase the video of us?" asked Xander.

"Yes, we promise" both girls answered.

"OK girls." Xander answered in a defeated tone.

"Ok boys, Strip!" Dawn squealed enthusiastically.

It was at that exact moment, Ian remembered he was still wearing the pink bra and panty set under his coveralls. "Oh, my fucking god" he thought. He knew this was going to get worse than he feared when the girls saw him wearing that. At this point, there was little he could do but obey the command from the girls, and go through with it. As they both peeled out of their coveralls, Ian saw that Xander also had a bra and panties on. His were sky blue, and had a floral print. So, at least there was safety in numbers so to speak.

When the girls saw the boy's sexy lingerie, their eyes opened wide, their mouths dropped open. Then both of them shrieked at the same time "OH, MY, GAWD!? "HOW CUTE!" The girls erupted into hysterical laughter, and all Ian and Xander could do was to stand there, humiliated in front of two gorgeous girls their own age.

Both boy's cocks were limp from the humiliation of the situation.

"Well, I'm certainly not impressed said Ashley."

"Nope, me neither Sis." Replied Dawn.

"OK boys, better get it up, or the deals off" Ashley demanded.

"Can't you guys jerk off or something?" Dawn asked.

"No, I have a better idea, jerk each other off" Demanded Ashley.

"We better just get this over with buddy" Ian conceded. Xander nodded in agreement. They grabbed each other's limp cocks, and slowly started massaging. Both cocks responded almost immediately. Getting stiffer and stiffer. As their cocks grew, it became easier to fully stroke each other up down. Trying not to let on in front of the girls it was turning both of them on.

"Come closer, come closer We wanna see" begged the girls. The boys took a few steps until they were standing directly in front of the girls, about 2 feet away.

"This is awesome!" giggled Dawn.

"YA Think"? said Ashley. "Now, put your cocks together, and jerk them at the same time" she begged.

"I've seen that before, I think it's called frotting or something." Gushed Dawn.

Xander was familiar with the term, having performed this with his Stepfather for his mother's amusement. Xander took hold of both cocks, spit on them, and stroked them together. Ian's hands dropped to his sides, and he stood there getting more and more aroused by the minute.

As both boys' eyes were glued to their own cocks, they failed to notice both girls had shimmied out of daisy duke shorts, and were now sitting with their legs spread wide open, masturbating each other cunts. Ian noticed first, and tapped Xander on the arm. With a head wag, he motioned to the girls. Both boys were now watching the girls, fixated on the lesbian action going on between their legs.