Sissy In Law Pt. 02

"Thank you Mr. Cypress, I...I don't know what to say."

"Don't mention it Brian, what happened to you was bullshit and I'm not going to have my family hung out to dry."

"Well, you won't regret it sir, I'll give you my everything." Brian said making Stephanie choke on her wine at his words.

"Oh I'm sure you will" Cooed Regina as she looked longingly at her husband as she imagined him railing their future son in laws little boycunt. Steve on the other hand kept his face placid as he handed a dark folder with paperwork in it to Brian.

"Now, I've already informed Stephanie, as you will start tomorrow you will be moving in effective immediately. Stephanie has prepared an over night bag for you and she will oversee the cancellation of your lease and moving of everything else to the house over the next three months. She will stay at the apartment while she is finalizing and moving everything. This will allow you to get into the swing of your new role without distractions. Though I'm sure Stephanie will visit from time to time. You will take over the east wing of the house and that way you can fulfill your duties as I need you to without delay. Having branches in foreign countries means sometimes I may need you on the fly and at odd hours to assist me as sometimes we will be working with differing time zones. Any questions?" Steve asked Brian as the two ladies silently ate.

"No sir, it all seems very cut and dry. I will handle everything you give me and more sir." Brian said eliciting more coughing from his fiancé

"Are you alright dear?" Brian said, he brow furrowed with concern.

"Yes, yes, just a tickle in my throat" She lied

"Good, you're driven Brian and I appreciate that about you, you're eager to work hard for me, and I know that you'll find yourself filled with confidence once you get into the swing of things" Steve said and waved the waiter over to order dessert. The four of them continued eating and chatting for an hour more before walking outside to wait for the driver to bring the car around.

"Are you coming to the house tonight?"

"No, I want to get an early start on the apartment so me and mom are gonna go over tonight while you and daddy smoke cigars and talk or whatever it is you men do these days"

"Alrighty, I love you,"

"love you too Brian"

An hour later Stephanie was on all fours while her mother plowed her cunt with a large strap on from behind. The two wouldn't lift a finger to move the apartment, hell they weren't even there. They had taken a separate car back to the house and were having sex in her parents bedroom. they had staff to move the apartment, but they would be spending a lot of girl time together. Stephanie moaned raggedly around her ball gag as the silicone phallus stretched her out almost as well as her daddy did.

~~

"Here's your suite, feel free to ask the staff if you have need of anything, go ahead and get comfortable and once you're all settled in feel free to join me in the den for some cigars if you're not to tired." Steve said as he patted Brian on the shoulder and walked away leaving Brian standing in the doorway to the suite on the east wing.

Brian was excited about the move, he would finally be moving forward for himself, and for Stephanie. Walking into the suite he closed the door and placed his bag on the table and looked around. He realized immediately this must have been Stephanie's suite growing up as everything was extremely girly.

Everything was in soft pastels and the wallpaper was floral, which was one of Stephanie's favorite designs. It made him smile, it was like fate had seen his fledgling fantasies about being a breedable femboy and was giving him the chance to explore it. At least while he's in the master bedroom of the east wing.

Even though Stephanie knew he was bisexual, he had never told her that he had began exploring fantasy of being dominated into being a femboy sissy. Of course he'd never cheat on Stephanie, but he'd never tell her either. It was just a private fantasy of his.

So being here all alone in a proverbial sissy heaven was something that immediately started to make his dick throb. Grabbing his bag he went into his new bedroom, curiosity filled every step and his mind started going wild with fantasies. He walked over to the closet opening it slowly and giggled happily.

There hung rows and rows of the girliest clothes he'd ever seen. It was clearly Stephanie's clothes for whenever she visited, but it stuck him as odd that she didn't dress this way at home. Pushing the thought from his mind he looked through the extremely girly clothes and smiled deeply. Anything he could dream of wearing was in this room. His options as long as he wasn't caught were endless.

Quickly he ransacked her dressers to find all sorts of cute panties and socks and sexy lingerie. Again he found it odd she would need sexy lingerie while at her dads place, but he didn't think too much of it as he was too excited to think clearly.

He was so aroused that his dick strained against his whitey tighties and his nipples started to rub stiffly against his shirt and without thinking about what he was doing he ripped off his clothing and grabbing a pair of extremely girly panties and some thigh highs Brian stood in front of the tall full body mirror and admired at his slender feminine body.

His body was similar to Stephanie's, sure she had wider hips and she had tits, but they had similar sized feet and hands, they were both relatively short, he was only taller by an inch at 5'4. Suddenly Brian shook his head. Being a sissy was just something he found hot, he reminded himself. He was a man and wasn't going to let a fantasy turn his brain to mush.

Besides he was in love with Stephanie and would spend the rest of his life with her. What would he do if they found out about his fantasy. Stephanie was pretty open minded but he felt this would be going too far so he kept it close to his chest. He couldn't risk them finding out. Suddenly he was overcome with shame, though the thought of getting caught crossdressing caused his dick to strain even harder against his fiancés panties.

~~

Steve clipped the end of his cigar with a cutter and began to light it as George his main butler started the fire in the hearth. Looking around Steve thought of all the deals made in his den. It was an opulent office. It showed off his ambition and drive. His families business acumen. How many companies had he taken over, how many marriages had he saved or torn apart in this very room. How many carpets did they have to replace. Steve chuckled to himself. This would be a first, He had never truly feminized a man. Of course he'd push Brian a little tonight, but not too far. He needed to ease the poor sissy into his new role as his cocksucker until the boy was his obedient little fuck slave for the family. The thought was making him begin to strain against his pant leg when Brian knocked on the door and walked in.

"Ah Brian, come in. have a seat son, lets relax and have a chat. Cigar? Whiskey?"

"Sure I'll take a bourbon on the rocks and a cigar any day!" Brian said as he sat down.

"George two whiskeys, one a special on the rocks and please bring Brian a cigar."

"Yes sir," the butler said softly and promptly followed his employers instructions.

"make sure you relax tonight, this isn't a business meeting, were here to enjoy our time, there is plenty of time tomorrow for me to fill you in on your duties."

"Thank you Mr. Cypress."

The two sat in silence for a moment drinking their whiskeys and smoking their cigars. Steve had glanced down when Brian crossed his legs and noticed that Brian was wearing the blue and black stripped thigh highs that Stephanie kept here in her room for when she visited. It was one of his favorites among the many pairs that he loved seeing his daughter in as she spread her legs wide while he bred her with his massive cock. He simply smiled knowingly. This would be easier than Steve originally planned.

Brian was a bit nervous. Here he sat across from his step father smoking a cigar while his dick was nestled in his fiancés panties and his legs wrapped in her dark thigh highs that he hoped Steve didn't notice. It was a risk, but what father pays attention to their daughters wardrobe. He was sure he'd get away with it when Steve didn't say anything. He slowly began to get relaxed the more he drank which led him to drink more and soon the two of them were engaged in a lively and drunken discussion as the fire crackled noisely in the hearth. Well Brian was drunk off his ass, Steve on the other hand knew how to handle his alcohol. He sat and watched as Brian got more and more animated and more than a tad flirty occasionally sneaking obvious glances at Steve's crotch.

"Mr. Cypress...I really am so grateful" Brian said in a drunken slurred voice. The tent in Brian's pants did not escape Steve's notice.

"Good, I expect you to show me how grateful you are with your performance." Steve's words flipped a switch in Brian's mind as he lost focus of the situation and his desires completely fogged his brain

"O I will! I..in fact!! I'll show you right now how grateful I am!" Brain said as he quickly took his clothes off and got on his knees crawling to his future father in laws lap and sat before him his socked feet underneath his cute pantied butt as he began rubbing the already hardening cock through Steve's slacks.

"Brian, you're very drunk." Steve said but didn't stop him.

"I may be drunk but you're hard and this faggot cocksucker takes responsibility very seriously, let me take care of the situation I've caused in your pants." Brian slurred as he unzipped Steve's pants and fished his massive cock out of his pants.

"Oh my...it's...massive..." Brian's eyes shown with desire as he whimpered delicately.

"Brian, you're holding your future father in laws cock. Do you think this is appropriate?" Steve asked sternly. Testing how far he'd go when five sheets to the wind and incredibly horny.

"You're right Mr. Cypress, I'm sorry...I should stop stalling and show you how grateful I truly am!" Brian immediately descended on Steve's massive cock with drunken abandon. Fireworks exploded in his mind and his heart screamed out in ecstasy as his tongue instinctually twirled around the large cock head in his mouth.

"Not exactly what I was getting at. However your slutty little mouth is an exceptional place to start showing your gratitude."

Brian was in drunken heaven. Here he was on his knees wearing his fiances panties and socks loudly slobbering all over her father's cock like a sex starved lunatic. The whiskey had stripped all his inhibitions away and Stephanie nor his masculinity were in his thoughts. All Brian could think about was how good his future father in laws cock tasted in his slutty sissy mouth. He was unabashedly being a faggot and it drove him wild.

Steve on the other called George in to get him another cigar as he was indisposed. The butler didn't blink an eye at what was going on. This was a normal occurrence in the house. Hell one of the tests he had to pass to get hired was to let his employer freely use him for a week straight. His master had even came in one day and fucked his ass while he was on the phone to his elderly grandmother.

Luckily she was so hard of hearing that she didn't pick up hardly any of his slutty moans while Steve was jackhammering into his ass as he came all over his stomach. While it was one of the greatest weeks of his life, he wouldn't disdain another getting similar pleasures.

Quickly he cut and lit the cigar and handed it to his master. After refilling his employers whiskey he silently left the room to take care of the bulge in his own pants and began to daydream about his next performance review with Master Cypress. The sound of Brian drunkenly taking as much of Steves cock in his mouth as he could reverberated down the halls. Steve simply looked down at the sissy faggot without emotion.

"I can tell you're a real cock hungry faggot Brian."

"Yes sir I love cock, Stephanie knows I'm Bi, but she doesn't know I tend to lean towards strong men, especially the ones with beautifully big cocks."

"Do you suck cock often?"

"No sir...not since...Stephanie and..." Steve pushed Brian's mouth back onto his cock. He didn't need explanation. Stephanie had already told him that Brian had squashed that part of himself for the sake of their relationship. Soon he would find it in full bloom on a daily basis.

"Good, I'm glad to hear that, now if you're a good little faggot for me and finish what you started I'll give you a small bonus." Steve said then smiled as Brian's cocksucking became even more eager.

~~

"Hank, thank you for coming by, it's so good to see you. Come have a seat, can I get you a drink? Coffee? Tea? Juice?" Camilla asked?

"Sure, coffee is fine." Hank said as his eyes quickly roved over her curves.

He would never touch the woman but damn if she wasn't fine. It would spell disaster for her, her husband, and the church. He was the head deacon in the church and he wouldn't allow himself to cross that line. He had wondered why the pastor had asked him over as he sat down at the table. He didn't often ask him to come around.

As Head of the Deacon board he knew there wasn't any trouble in the church currently so he just chalked it up to a personal visit. Though even that was odd as they didn't really hang out. Sure they got along just fine and Hank did really enjoy his conversations with David and he would definitely go to bat for them but they weren't close friends.

Bringing the coffee over to Hank Camilla excused herself to go grab David making sure to sashay her hips to get his blood pumping and his mind in the right place for the evening. Slowly she ascended the stairs and knocked on the door to the bathroom. Dianna, her sissy wife was almost ready and she looked ravishing. Camilla was always so jealous of how good Dianna was at makeup, to the point Camilla started making Dianna do her makeup every morning. She took the time to put on all the finishing touches.

"Okay, there you are." Camilla said as she pulled her sissy wife's panties over her little caged dicklette.

"Hank is going to fall in love with you, Hell I already love you and I think I may fall in love with you all over" Camilla giggled and Diana blushed demurely.

"Thank you mommy!" Dianna said

She really was gorgeous. By the time they had finished a couple surgeries and Dianna learned how to do her makeup right she was indistinguishable from a sexy model when she wasn't dressed as her fake male persona. Of course the work out regime Camilla put Dianna through gave her the big bubble butt she decided her sissy slut should have which gave her the curves and the tiny waist she demanded Dianna have. If she was going to Mommy this Bitch, she was gonna Mommy her right.

Standing back and taking one final look she smiled. Dianna was wearing white lace trimmed thigh highs with red T strap wedges and poofy pastel rainbow colored lace mini skirt that barely covered her ass with a white corset cinched tightly around her body. Her hair which she had been growing out was in pigtails and she was wearing a red choker around her neck. Neither one could contain their excitement.

~~

Hank's head started feeling a tad woozy and he couldn't get his raging erection to go away for some reason. If he was at home it wouldn't be an issue, but he was at his pastors house. 'Maybe another cup of coffee would help' Hank thought to himself as he poured another cup of coffee hoping the caffeine would clear his sudden brain fog. Even if it didn't get rid of the issue in his pants. Quickly he downed another cup. Shortly after he sat back down the problem got even worse. He was beyond confused. Yet the high he was on mixed with how horny he was, he didn't even worry about it but leaned into it. Moments later he was passed out in the chair his cock bulging through his pants.

Silently the two women crept down the stairs and tiptoed into the kitchen. Seeing Hank fast asleep Camilla would have to show her master Steve extra appreciation for the pills. The two women both got under a shoulder and together lifted the man up and carried him into the living room where they deposited him onto the couch. Both women were huffing strongly trying to get their breath back. Meanwhile, Dianna couldn't stop staring at Hanks bulge.

Dianna's boycunt ached to be wrapped around it. Ever since Steve and Regina trained her, Dianna couldn't help desiring to have Hanks big black cock. It drove her wild to think of mommy Camilla selling her to Hank to be his free use pleasure bitch. Every Sunday she would pretend to be David and rail against sin like they expected her to, but every time she looked at Hank her little girl dick would stir against it's cage making her wish she was on her belly while he beat her insides up with the tool in his pants. She knew he was miserable in his marriage but was stuck because of reputation and decided to act.

It was a struggle but they finally got his pants and boxers down around his ankles and completely off his body. Shortly his shirt came off as well and Dianna fell even more head over heels for her Head Deacon. So many church meetings, services, and bible studies she had waited, yearned, craved through for this and now it was right there for her to take. Dianna grabbed his thick cock in her tiny white hands and began to slowly stroke it.

"It's not as big at Master Steve's but I'm glad we could get you someone with a sizable cock. Don't want you getting too jealous" Camilla winked at Dianna

"Now open your slutty cockstarved mouth and take your head deacon's cock like a good little girl." Camilla commanded into her ear as she pushed her sissy wife's mouth onto hanks throbbing cock.

~~

Hank was dreaming, 'he had to be dreaming' he thought, but he had just woken up from a dream. How can you wake up from a dream and still be dreaming? He didn't know, but he knew this was a dream. He knew if he was awake he wouldn't be able to handle what he saw.

There he was sitting in his pastors living room couch and on her knees in front of him was one of the most gorgeous little white girls he'd ever seen with his cock deep in her throat as she smiled around his cock at him. Now he knew he was dreaming, cause the pastor doesn't have a daughter, and that's definitely not his wife.

Clinging onto those rationalizations he completely threw himself into what was happening. He was absolutely in heaven. It felt amazing to be in this bitch's fucking throat. Not to mention a cute little white girls throat who looked like she was having the best time of her life. He always had a thing for white girls, he wondered if she had a cute little bubble butt.

"God...baby...yeah...suck that dick girl...show me what a slut you can be for Daddy." Hank commanded as he pushed her head into his pubes and held her there for a few seconds. She didn't even hint at gagging, and a huge grin spread across his face.

Dianna couldn't believe it, Hank had finally woken up while she was deep throating him and instead of panicking or screaming he commanded her to be slutty for him. It was the hottest thing in the world to her. She eagerly deepthroated his cock over and over again to please him until she had multiple sissygasms. Camilla would make her clean the floor later but she didn't care it was totally worth it. She had never been so thankful for Master Steve and Mistress Regina's tutelage than she was at the moment.

"You like having your mouth wrapped around my cock don't you girl? Dianna simply nodded as she continue to impale her face on his manhood.

"God your throat feels so sweet, I almost want to dump my kids in your stomach, but I got a better idea, come pull your panties off and give Daddy that sweet little white ass."