"Gag on it sissy, " said Mistress Sheila, as she thrust her black strapon dildo down her helpless sissy's throat. Her sissy boyfriend had no choice in the matter but to suck it for all it was worth. Sissy Billie was tied sitting on the chair, dressed in sexy lingerie.
"Do you love it, " she asked with a grin. "Tell Mistress how much you love sucking her cock."
Billie had tears coming from his eyes as he tried to breath with a mouth full of strapon dildo. His gag reflex was being tested severely, and drool came out of his mouth as Mistress pulled out.
She slapped her sissy hard across the face. "I said tell me how much you love my cock."
He continued to beg her. "Sheila, please, this was just a little game we were playing."
She slapped the sissy across the face again. "Do I look like I'm playing?"
He wondered how he got himself into this jam and what exactly got into his fiancee. Was this Amanda's doing? Sheila had visited her old high school friend a day earlier. Then, tonight, the two went out together.
Sheila was a vision, though he didn't really like seeing her go out looking like she did. She wore red leather pants that left nothing to the imagination and a red corset top. Her heels were five inch open toed heels, showing off her painted toe nails. Her hair was tied back in a bun, and she wore the brown reading glasses she sometimes used.
When she came home, she was very flirtatious and loving, and he figured it was going to be a night of sexual fun. He was up for that as their sex life recently had gone cold. Then, she asked him to strip naked and follow her lead for the most amazing night of his life.
What was he thinking? He wasn't thinking, at least not with his big head. He let her apply hair removal cream all over his body. Once smooth, she dressed him up in pink lingerie, a babydoll and matching panties, stockings and garters.
He was straining against his panties, and she told him that would have to be taken care of. She asked him to close his eyes. He felt metal against his balls, and opened his eyes. She told him no peaking if he wanted to have some real fun. He went along with it.
Before he realized it, he was locked into chastity. She playfully teased him and told him the release was going to be incredible if he obeyed her. Obeyed, he wondered, but he agreed. She then proceeded to restrain him to the chair. He protested a little but didn't resist.
Then came the makeup and a nice blonde wig over his short black hair. She followed that up by teasing him and calling him her pretty sissy. She took pictures of him, telling him the other ladies would be jealous of her sissy. He didn't like being called a sissy, but his cock strained against the chastity.
When he asked when it would be his turn, she headed to the bedroom, saying it would be right now. She returned with a strapon and told him he would have a turn at sucking her cock. Slaps to his face made him open his mouth and suck her strap on dildo. He thought how foolish he was, but hated how turned on it made him.
She slapped him again. "Do I look like I'm playing?"
"No you don't"
Another slap. "No you don't what?"
What has gotten into her? This is so not like her, he thought. "No you don't, Mistress."
"So, tell me how much you like sucking my cock?"
He shook his head. "I hate it. It's wrong. I just..."
"Wrong answer, "she said as she shoved it back into his mouth, again testing his gag reflex. "You love sucking my cock, and you'll get used to taking it deep. After all, you will be a sissy cock sucker by the time I'm through with you, which is what you were meant to be."
"Mmmmphhh, " was all he could manage in protest, looking up at her beautiful smiling face.
"Suck my cock, and I promise you will have the best orgasm of your life, " she ordered. "Make love to that cock. It's all for you, my little sissy."
To his surprise, he was taking it deep a little better, breathing when he could and sucking it. "That's my sissy, love the cock. This is the real cock of the house from now on."
"Mmmmmphhh, " he protested again.
She laughed. "Didn't anybody ever yell you it's not polite to talk with your mouth full of cock? You are such a slut. I bet they'd love you down at the video store. Maybe we should find out just how good a cock sucking whore you really are."
"Mmmmmphhhh, " was all he could manage. He didn't understand what was happening or why he was so turned on, but he knew he loved her.
She pulled out of his mouth. "Now, it's real simple, my pet. You do what I say, and you're gonna cum like you've never cum before."
"Are you gonna let me out now, Mistress?"
"I'm gonna untie you, but your clitty stays locked until I say, " she said with a grin.
He shook his head. "Then, I'll just leave. I don't have to put up with this."
She pouted, and he knew that look. It was the look that told him he was in trouble. "You walk out that door, and we are through. Don't come back."
"You can't be serious."
This was the part where Amanda instructed her that she needed to be strong to make it work. It was hard for her, because she was in love with this man. She knew he would be happier as her sissy. "I'm very serious, Billie. You have to trust me here, or we have nothing."
He started to cry. He always was so sensitive, another indication to her of his sissy inclination. "But, why?"
"Because I know you're gonna love it. I'm gonna give you a big release that will show you what I mean, but you have to do what I tell you or else."
He looked down, very unsure at the moment. "Okay, Mistress. I'll do as you say."
She smiled and gently slapped his face and then patted his head. "Good girl. Mistress knows best. I won't punish you this time. This time, " she repeated as she looked him in the eyes."
Once he was unbound, she pointed to the kitchen table. "I want you to get up on the table and lie on your back." He slowly did as ordered as he felt her hand slap his ass.
She grinned. "That's my obedient little sissy. There you go."
With her heels, she was at the perfect level of the table. "Stay right there, " she said as she walked to the bathroom and got some lube.
She moved his bikini panties out of the way and liberally lubed his exposed sissy ass. "Mistress, what are you doing?"
"I'm gonna make a new woman out of you."
Before he could get another word out, she lifted his legs over her shoulders and shoved the head of her strap on dildo into his tight pussy hole. He screamed. "Relax, my pet. It will go a lot easier and feel so much better."
She pushed it in slowly and he screamed some more. "That's my girl, take momma's cock. Good girl."
He had tears in his eyes. "Mistress, it hurts."
"It will only hurt for a little while, " she said with a smile and a wink as she moved slowly in and out to allow him to get used to it.
He started moaning a little as he relaxed. "Does my sissy like getting her pussy filled?"
He said nothing, and she shoved it in deeper as he yelled. "I asked you a question, Missy."
"Ow. Yes Mistress."
She continued slowly fucking him. "Tell me how much you love it, Billie. Tell me."
As the words came out of his mouth he could hardly believe it. "I love it Mistress. It feels good."
She smiled. "Good girl. "Tell me where it feels the best."
He moaned again. "Right... Right there Mistress. Oh, yes."
She looked him in the eyes. "Good girl. You see, sissies have a spot in their pussies that makes them feel amazing when you hit it. You can even move your ass against it to help me."
"Let me stoke my cock. Please, Mistress, " he begged."
She shook her head. "I can't do that, " she replied with a smile. "You need to learn to be the sissy slut that you are. This is how you will cum."
"Oh God, " was all he managed as he took her six inch dildo deep. "Please."
"Trust me, my pet. Let it overtake you. You're gonna love it. This will be what you will love the most, not using that pathetic little clitty of yours."
"Please, " he begged without being able to finish the sentence. As the moments passed, he felt the pleasure build, and subside, like a wave washing over the beach, steadily overtaking the sand and submerging it."
"Make a cummies for me, my pet. Cum for your Mistress. Show me how much you love being fucked by Mistress's cock."
"I love you Sheila... Mistress."
She smiled. "I know you do, and you'll be showing me in a bit when you eat my pussy with that talented tongue of yours."
It was too much. He started to slowly leak cum from his caged clitty. Then he felt an orgasm slowly overtake him. "Oh, fuck yeah, " he said as it built up again and he leaked more cum.
She stuck her fingers into his cage and collected some of the cum, placing it to his mouth. "Taste it, my little cum slut."
He complied and she fed him some more as her dildo was still in his violated sissy pussy. He greedily lapped up all she fed him. She laughed. "See, I knew you'd love your new role."
"It was incredible, " he admitted as she pulled out of him. "Wait, new role?"
As he lie on the table, she walked back over to her phone camera with her heels clicking on the hardwood floor. She looked at the pictures before sending them to Amanda. "Oh yes. There's gonna be some changes around here. You are gonna be a good sissy for me, and I will be your Mistress."
"But..."
She held up the phone. "The pictures I took could get into the wrong hands, and you don't want that now, do you?"
It was a bluff. She wouldn't do that to him, but she needed him to believe she would. "Don't you love me, Mistress?"
She walked over to him and kissed him as he stood up. "Billie, you silly little sissy, if you don't know how much I love you by now, then I don't know what to tell you. I love you."
He was confused. "Why did you do this to me then?"
"Because you needed it. Our relationship needs this. If we are getting married, there needs to be some changes for both our sakes. And, you're gonna love your new role."
"My new role?"
"Of course. You are my sissy sub, and you are gonna learn to be a pretty little sissy, just like you were always meant to be, with my help."
He didn't know what to think at this point. He needed a moment to digest all of this. "I'm gonna go take a shower. Can you take this chastity thing off of me?"
She shook her head. "Oh no. That thing stays locked up until I say so, and you'll have a shower later. Right now you need to come to the bedroom and give my pussy the attention it deserves. I am so wet right now."
She started walking to the bedroom as he stood there. He admired her from behind. This was almost too much for him to handle, but he loved her so much.
She made it into the bedroom and yelled back to him. "Billie, get your sexy little ass in here now, before it feels my paddle."
He shook his head and sighed. "Yes Mistress."
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