Sissy Step-Dad Pt. 05

With the help of her gay friends, Mandy had connected with a man who agreed to dominate and use her sissy step-dad for his sexual pleasure. She was thrilled when she received the text from Bill that she had been waiting for.

"I can be available Friday morning if that still works. Contact me to discuss our plans. I'm looking forward to having your step-dad on his knees in his panties!"

Mandy wasted no time before calling Bill. They discussed their ideas and Bill had some specific requests.

"I want your step-dad wearing a bra, thigh high stockings, and some big granny panties with a floral print. It doesn't matter if they are cotton or nylon. He'll look like a sissy in either. I also want him wearing a wig, bright red lipstick, and blue eye shadow."

Mandy was certain her step-dad had the floral print panties and a wig. She wasn't sure if he had the stockings but said she would get some for him. She also agreed to have the lipstick and eye shadow for him to use.

Bill and Mandy talked about how things would begin. After getting Bill involved he would take things from there. Mandy could make comments but otherwise she was simply going to be there to watch.

Mandy was in agreement. The main thing she was interested in was seeing her step-dad completely embarrassed and totally humiliated by having to pleasure a man for her.

"Oh he will definitely feel humiliated, especially with having his step-daughter watching him do the things he will be doing."

Bill then gave Mandy some details of what to expect.

"The first thing I always make my sissies do is to masturbate and cum while they admire my cock."

Mandy was surprised and a little confused.

"Why do you allow them that pleasure right away? Isn't it better to make them wait?"

"Sissy guys are horny and aroused when they fantasize about sucking cock. After they cum they lose the desire. They then feel the full humiliation of taking a cock in their mouth and are usually disgusted by getting it filled with a hot load of semen."

As she listened to the explanation Mandy agreed that it seemed to make sense.

Bill continued by putting it into a different perspective.

"If you've ever sucked a cock when you didn't want to, how did you feel?"

"I just wanted to get it over with."

"Exactly!"

Mandy laughed and shook her head in agreement as she fully understood.

As soon as Mandy had finished talking to Bill she sent a text to her step-dad. She instructed him to be home and available at 11AM on Friday for a session with his mistress. He replied in his typical manner.

"I'm very sorry Mistress Mandy but I have other plans on Friday."

As was always the case Mandy responded with a more stern tone to her message.

"You WILL be home slave or you WILL pay the consequences. I don't need to tell you what they are. You have no choice. I will be at your house at 11AM and you will be there waiting for me."

Dan didn't respond to his step-daughter's text immediately. After about a half hour he conceded and agreed to her demand.

Mandy was absolutely overcome with delight. For almost twenty years she had put up with disrespect and put downs by her step-dad.

She had already found great pleasure over the past few weeks with the humiliating things she'd made him do. The upcoming Friday would be the best yet. Mandy could hardly wait for the day to arrive.

Later that day Mandy again texted her step-dad. She inquired whether he still had the wig he had worn in some of the pictures she had seen. He acknowledged he did. Mandy instructed him to have it available on Friday. She also informed him of the bra and style of panties he was to be wearing when she arrived.

Mandy informed Bill that everything was confirmed for Friday. He was almost as anxious for the day to arrive as Mandy was.

"I haven't cum in almost two weeks waiting for this fun. I also have some Viagra that I will be using. It's not because I need it but it will help to keep me hard for an extended amount of time. When I'm done your step-dad will know what a true sissy he is!"

Mandy and Bill met on Friday morning at a McDonald's near to where her step-dad lived. After again going over their plans for the day they drove separately to his house. Mandy went inside to get things started. The plan was for her to text Bill when she was ready for him to come inside.

When Mandy arrived her step-dad was waiting for her dressed in the manner he was told. He was wearing a pink bra and cotton granny panties.

The panties were pale pink with a darker pink floral print. They were also a size too big and her step-dad had them pulled up past his belly button. Mandy knew they were perfect. Her step-dad looked every bit the fat sissy that Bill was wanting.

Mandy smiled at her step-dad.

"Very nice slave. I really like those big sissy underpants you're wearing today. You followed your orders very well. Now greet Mistress Mandy in the appropriate manner."

Mandy turned and bent over. Her step-dad knelt behind her then kissed her cheeks and smelled her butt through her pants in the manner he'd been taught.

When Mandy was satisfied by her slave's greeting she informed him of the fun she had planned for him.

"Today you will be the sole contestant in Mistress Mandy's sissy beauty pageant. I want to see just how much of a pretty girl you can be. I've bought you some sexy stockings to make you even prettier for this event."

"Take the stockings and your wig to the bathroom. Here's some lipstick and eye shadow also. When you've finished your make-up and dressing, wait for me to request your presence."

Her step-dad was apprehensive as he took the items then walked down the hallway to the bathroom.

As soon as her step-dad disappeared into the bathroom Mandy sent a text to Bill.

"You can come inside. My step-dad is getting dressed. I can't wait to see him with your big cock in his mouth!"

Bill responded with a smiley emoji. He was already opening the door when Mandy received it.

Mandy placed a kitchen chair in a corner of the front room for Bill. It was positioned in a spot where her step-dad would not notice it as he entered the room from the hallway.

After giving her step-dad some time to get ready Mandy knocked on the bathroom door.

"Is my beauty contestant looking pretty and ready for the competition?"

"Yes Mistress Mandy, I'm ready."

Mandy opened the door to view her step-dad. She couldn't be more pleased with the way he looked. Medium length dark brown hair, bright red lips, and way too much blue eye shadow. He had on the stockings with his panties pulled up high on his fat belly.

Her step-dad was absolutely non-passable as a female but looked every bit the fat sissy slut that Bill wanted him to be.

"Very pretty sissy! You should have no problem winning this beauty pageant."

Mandy gave him the instructions for what she wanted him to do.

"Wait for a minute then enter the hallway. Come to a stop five feet back from entering the front room. At that point you need to mentally prepare yourself for your entrance."

"When I motion to you, put one hand on your hip and rub your wee-wee through your panty with the other. Keep your chin up and focused on me as you strut into the room."

Dan was suspicious of what the beauty pageant routine was about.

"I suppose you have Miss Megan and Miss Brittney waiting to see me dressed like this?"

Mandy assured her step-dad that her friends who had helped humiliate him the prior week were not there.

"Don't be so suspicious. This beauty pageant is just something to help you feel like the pretty girl you want to be."

Mandy went back into the front room. She stood on the far side directly in view of the hallway. A minute later her step-dad appeared in the hallway and walked to where Mandy had instructed.

Mandy's stomach was churning with excitement. She motioned her step-dad to come into the room. Dan raised his chin, put a hand on his hip then started rubbing his wee-wee through his panties.

His eyes were focused on his step-daughter as he walked with a sexy strut into the room. Mandy was biting her lip trying to keep a straight face. In the corner of her eye she could see Bill grinning.

When her step-dad was half-way across the room Mandy motioned him to stop.

"Oh my goodness sissy, that was absolutely wonderful. You look so pretty. If the pageant was judged strictly on looks you would have already won."

"Like all beauty pageants however, you must compete in a talent competition before the final judging. What talent have you chosen for the pageant?"

Dan looked confused. Before he could say anything he was startled to hear a man's voice from behind him.

"I don't know the talent he's chosen but I do know a talent that he's going to show us."

Dan quickly turned around.

"Who the fuck are you and what are you doing here? Mistress Mandy, this isn't right. You can't just bring someone into my house that I don't know."

"Oh but you do know him sissy. This is an acquaintance that you were apparently anxious to meet a few years ago."

Bill stood up and walked towards Dan.

"That's right sissy. Remember Craigslist? You contacted me two different times. We were supposed to meet. You wanted to suck my cock."

Dan was visibly nervous and shaking his head.

"No, I don't think so. You have me confused with someone else."

"There's no confusion sissy. I still have your e-mails and I have the pictures you sent me. Now after all this time we finally meet. You're finally going to do what you wanted to do. You're going to suck my cock."

Mandy walked across the room and sat down on the sofa. Dan looked at her and pleaded. She wasn't about to have any mercy on her step-dad.

"This is all your own doing sissy. This is what you've wanted. It's now what Mistress Mandy wants too. I'm just here to watch as you fulfill your fantasies and desires."

Bill reached out and squeezed Dan's chin.

"You know, I don't like when a sissy doesn't keep his word. After you stood me up the first time you begged for a second chance. I gave you that opportunity and you stood me up again."

"Shame on me for getting fooled twice. Whoever thought there would be a third time? This time will be the charm."

Bill walked back and stood by the chair. He looked at Dan as he took off his clothes.

"You looked really sexy strutting into the room panty boy. Seeing you in your pretty sissy underwear and stockings has made me horny. Since you have me all worked up you're going to help to solve that problem."

Bill removed his underwear and sat down. He spread his legs to fully expose his thick uncut cock hanging below his big belly.

"Put your hand on your hip sissy and rub your wee-wee through your panty as you strut to your Master."

Dan looked towards his step-daughter and saw the grin on her face. He hesitated and took a deep breath. After a moment he put his hand on his hip. He started rubbing his wee-wee and slowly strutted towards Bill.

Never in his life had Dan been so nervous. After all the embarrassment Mandy had already caused her step-dad, she was surprised at how red his face appeared to be.

Dan stopped a few feet in front of Bill. He was instructed to move closer until he was standing between his Master's legs.

"Take my cock in your hand sissy. I want you to know what it feels like to hold a cock instead of the little wee-wee in your panties that you're used to."

Mandy noticed her step-dad's hand was shaking as he reached for Bill's cock. Dan's entire body was trembling as he took it in his hand.

"Oh god, it does feel big."

"You may think it's big now panty boy but it gets bigger."

Mandy was fully enjoying seeing her step-dad with another man's cock in his hand and she knew the show was going to get better.

It didn't take long before Bill's cock was aroused enough that the head began to peek out from inside the tip of his foreskin.

"Pull your panty down sissy and rub your little clitty while you hold my cock."

As Dan rubbed his little wee-wee he was getting more aroused.

"Oh yea, that's it sissy. Show Master how your little clitty gets excited for his cock. Now push the foreskin back so you can see the full head."

With his foreskin back, Bill's shiny pink cock head was out and fully exposed.

Mandy had seen a picture of Bill's cock but it now looked even bigger to her. She was certain that his big mushroom shaped cock head was bigger around than any man she'd ever been with.

Her gay friends had told Mandy that the head of Bill's cock was at least two inches in diameter. It looked at least that big. She was already trying to imagine seeing her step-dad put it in his mouth.

Dan had his eyes focused on Bill's cock. It was obvious by his facial expression that he was in awe of the size.

Bill was leaning back in the chair watching Dan.

"Alright sissy, now slowly jerk your little wee-wee to show Master how much you like his cock."

With no hesitation Dan began to stroke his little penis. It took very little time for him to get hard and become fully erect.

"Now rub it on Master's cock sissy."

Dan crouched down to get his wee-wee at the same height as Bill's penis. As soon as he started to rub it on the big shiny head of Bill's uncut cock Dan moaned with pleasure.

"That's it sissy, rub your wee-wee on Master's cock. Oh yea, rub it. Now place your hands on your hips and keep rubbing your little excited wee-wee on my big cock."

Mandy could hardly keep from laughing at seeing her step-dad thrusting his hips as he rubbed his excited little penis on Bill's thick cock. Despite his embarrassment it was obvious that he was extremely turned on by what he was doing.

Over the next minute or so Bill continued non-stop talking to encourage Dan's arousal.

"Oh yea sissy, keep rubbing it. Rub your excited wee-wee on my big cock. That's the way to do it sissy. Rub it on Master's cock."

It didn't take long before Bill noticed visible pre-cum in the slit of Dan's excited penis.

"Oh yea sissy, now jerk it. Jerk your wee-wee for Master!"

Dan grabbed his excited penis and began to stroke it.

"Jerk it sissy. Jerk it for Master. Now faster. Jerk it faster and make yourself cum all over Master's big cock!"

Dan groaned loudly as a thick stream of cum shot on Bill's cock.

Mandy had never seen her step-dad so aroused. As Bill continued talking Dan kept moaning and jerking his excited wee-wee, covering his Master's cock with a massive amount of thick white cum.

"Oh god yes sissy, squirt it all over Master's cock. Squirt it all over and show Master how much you love his cock!"

Mandy could see the pleasure in her step-dad's facial expression as he ejaculated. As his excitement subsided Dan sighed and looked at his cum on Bill's cock.

"Oh sissy, just look at all that creamy cum. You did well showing Master how much you like his cock. Now get on your knees. It's time for you to lick up all that delicious cum you made for Master."

Mandy could see the nervousness in her step-dad's face as he knelt in front of Bill. It was obvious by his hesitancy that he no longer felt the excitement he had been feeling a moment before.

"Lick my cock sissy. Lick my cock and balls. Clean up that mess you made from getting so excited."

After taking a deep breath Dan began to lick up his cum.

"That's it sissy. Lick your Master's penis. Take it in your hand as you lick it. Lick the head and lick the shaft. Oh yea. That's it. Up and down and all around. Clean it good sissy. And don't forget to clean my balls. Oh yea, that's the way to do it."

Mandy bit her lip to keep from laughing. She had been planning this for such a long time and now she was actually watching her step-dad licking a cock.

When Dan had finished cleaning up his cum Bill's cock was hard and standing fully erect.

"I really love how well you cleaned up the mess you made on my cock sissy. Now that you've had your pleasure it's time that I have mine."

Bill ordered Dan to stand.

"Alright sissy, now just like you did before. Put your hand on your hip and rub your wee-wee through your panty. Strut across the room and stop in front of your step-daughter."

Dan did exactly as he was told. When he stopped in front of where Mandy was sitting, Bill stood and walked over next to him. His eight inch cock was hard and standing at full attention.

"Now face me then get on our knees sissy."

Bill moved directly in front of Dan with Mandy sitting to the side of them. She had the perfect view for watching the show she'd been waiting for.

"Put your hand around the base of my cock and lick the head."

Dan was extremely nervous as he gripped Bill's thick cock. He put his tongue against the shiny pink head and started licking.

"That's it sissy. Let your step-daughter see how you like to lick a man's penis. Lick all around the head. Lick in the slit too."

Bill put his hands on Dan's shoulders. For the next few minutes he enjoyed watching his sissy lick his cock.

"Oh yea sissy, I like how you lick your Master's cock. Now stick your tongue out with your mouth open and hold Master's cock on the flat of your tongue."

As Dan followed Bill's instructions he closed his eyes. He started to take short quick breaths. Mandy could hardly keep from laughing as she watched intently.

"Alright sissy. Lower your mouth over the head of my penis and wrap your lips around the shaft."

As he watched Dan's mouth cover the thick head of his penis Bill moaned with pleasure.

"Oh god yes, now suck it sissy. Suck Master's cock!"

Mandy was grinning with delight. She could hardly believe this was really happening. She was watching her sissy step-dad as he sucked a cock.

Bill pushed his cock deeper into Dan's mouth then began to slowly work it in and out.

"You may have avoided this before but not today sissy. You're finally sucking my big cock just like you wanted to."

Mandy laughed as she watched the expression on her step-dad's face. His mouth was open wide and his red lips were stretched tight around the thick cock as Bill moved it in and out.

Bill took his time enjoying the full pleasure of making Dan suck his cock. He continued making comments while he slowly fucked his sissy's mouth. After several minutes he smiled at Mandy and began to increase his pace.

"I have to say sissy, for never doing this before you are a good cocksucker. Now you need to learn the full technique of giving your Master pleasure."

"Grip my cock at the base between your fingers and your thumb. Now slowly jerk it and use your other hand to massage my balls."

Dan did as his Master instructed. Bill began to moan and placed his hands on his sissy's head.

"Oh yea sissy, you're making your Master's cock very happy. Oh my goodness yes, keep that up and you'll get a nice mouth full of delicious semen."

"Now show Master how much you want it. Rub my balls and jerk my cock fast!"

Dan stared jerking Bill's cock faster as he rapidly massage his balls. Suddenly Bill groaned loudly. He pulled Dan's head tight against him as he shoved his cock deep into his sissy's mouth.

Even though it happened quickly Dan was fully aware of every sensation as if it were in slow motion. When he felt Bill's cock begin to throb and pulsate he knew there was no way to stop the now inevitable.

Almost immediately that big cock was deep in his mouth. Dan felt streams of warm fluid squirting against the roof and flooding the back of it. It had a salty bitter taste. He was trying to swallow it but there was so much that it was filling his mouth.

As Mandy watched her step-dad's face she could tell the exact moment when the first stream of Bill's cum entered his mouth. She was ecstatic and his expression was priceless. What made it even better was she was holding her phone and capturing the moment on video.