Mistress Eve lie naked on her bed with her legs spread wide open, taunting her sissy Britney. Britney, who was her sissy sub wife, was locked in a very tight chastity device and straining to get out. The hormones hadn't effected her down there yet.
Eve had an evil grin on her face. "Come on, sissy Fuck your Mistress. Mistress needs to be fucked right this instance."
Britney was practically in tears. It was torture the way Mistress teased her. Sometimes she would sit on her caged clitty and demand to be penetrated. Of course, Britney could do nothing but cry.
The fact was, Britney would please Mistress in any way she demanded, and she wanted to be able to make love to her. She also knew that she was smaller down there than most and inadequate. It still didn't stop her from wanting to try.
She looked over, desperation in her eyes. "I can't, Mistress. I'm locked up."
Eve laughed in a teasing manner. "Oh, you can't, but it it's because you are a limp clitted little sissy who can't satisfy me that way anymore, not that you ever could."
A tear formed in Britney's eye. "Don't say that, Mistress. It's mean."
Eve patted the side of the bed for Britney to come sit down. "It's the truth, my pet. You know you are inadequate down there, which is why you agreed to be locked up and dressed in the pretty clothes that are suitable for a sissy like you. And, plugged as well. How does the plug feel in your pussy?"
"It's too big, " Britney protested as she sat down next to her, wearing a red bra, panty and babydoll set with stockings and garters. "It hurts."
"Awww, It won't hurt as you get used to it. You need to get your pussy stretched wider, and the other one wasn't big enough."
Britney frowned. "I guess so."
Mistress rubbed her sissy's back. "Do you like the job I got you at the makeup stand at Macy's?"
"Yes and no, " she replied as she moved to Eve's feet and started giving her a massage. "One of the girls doesn't like me and calls me names."
"Well, we'll just see about that. You're a natural at makeup, and Rhonda knows you're the right girl for the job there, " she smiled at her sissy. "You are a natural at massaging my feet too."
Britney blushed and smiled. "Thank you Mistress."
Eve grinned at her. "Another thing you are good at is eating my pussy, and I'm afraid it needs some more attention before Brad gets here. Would you do that for me, Angel?"
Britney climbed between her legs and went to work without saying a word. She loved everything about her Mistress's pussy. The way it tasted, the way it smelled, the way it looked so smoothly shaved. In fact, Mistress trusted her with the task of shaving her pussy, and Britney was proud to have the honor.
"Honestly, I don't know what I'd do without you, my little sissy."
A knock on the open bedroom door revealed Brad in all his sexy glory. He wore a t-shirt and shorts from his work out at the gym. He sported a growing bulge in his shorts as he looked at the ass of the plugged sissy eating the pussy that his manhood was about to invade once again.
Eve spring up from the bed, put her arms around his shoulders and planted a deep kiss on him. "Welcome back lover."
Britney stood up and walked over to the two. "Hi Britney, " he said, planting a kiss on her forehead. "Looking sexy tonight."
She blushed again. "Would you like me to suck Brad's cock to get him ready for you, Mistress?"
She smile at her sissy. "Would you? Actually, you should be asking Brad, shouldn't you?"
She looked up at Brad, who was a bit taller than her. "May I suck your cock so you can make love to Mistress?"
Brad looked down at her proudly. "Of course you can. I like the way you suck my cock."
Britney got down on her knees and released his still hardening eight inch cock from his shorts. "She planted a kiss on it and left her lipstick on the tip. She loved seeing that before she really went to work. She started out with a few gentle licks before opening her mouth.
Eve sat at the side of her bed, proudly looking at her sissy. "She's become quite the little cock whore. You know, I think she wants to be fucked by you."
Britney focused on the Brad's cock, sucking him slowly and moving her tongue around the tip. She hummed a little as she went, knowing how excited it got him She thought about how this hard cock would feel invading her virgin sissy pussy. Could she handle it?
Brad smiled, "Anytime you say it's okay, I'll fuck her good. She has a cute little ass."
"Doesn't she?" Eve was feeling incredibly turned on by the scene. She liked seeing her sissy suck her lover's cock for her, and she wanted her to be fucked to experience the joys of taking cock. She loved her spouse even more as a bisexual sissy slut.
Eve lie on her back at the edge of the bed. "Britney dear, guide him into me."
She took one more suck of his pulsating love muscle and tasted a little of his salty essence. "Yes Mistress."
Brad stood over Britney's Mistress, proudly about to fuck her again. Britney guided his cock into her waiting pussy. "Please fuck my Mistress. I can't satisfy her the way she needs."
"Such a shame, " he said as his cock slid inside her pussy. "Her pussy is so divine. It makes my big cock feel so good."
"Mmmm, it feels so big inside me too, " Eve replied. "Sissy could never fill me up the way you do."
Britney moved between their legs and took turns licking his balls and her pussy lips. "I love it when she does that, " Brad moaned as he steadily fucked Eve.
"That's because my sissy knows her place, don't you?"
"Yes Mistress, " said the sissy as she kept using her tongue.
The love making continued as Mistress called sissy to her side. She planted a passionate kiss on Brad as sissy watched and then gave sissy a little kiss. "How could you ever be happy being anything but my sissy?"
"I couldn't, " Britney replied. "You treat me so well."
Mistress Eve lie back on the bed in the throes of an orgasm as sissy went back between her legs, waiting for Brad to release inside of her Mistress.
Brad came in a tidal wave, filling Eve up with several spurts before puling out. The sissy took his cock into her mouth without asking as she cleaned it of all the love juices. "God, I could get used to this, " Brad proclaimed.
Eve laughed. "You little cock whore. Get over here and clean my pussy right now."
"I'm sorry, Mistress."
Mistress pushed some of his love seed out for Britney to taste. "I may just need to punish you for that. You need to remember who you serve."
Britney kept lapping Eve's used pussy for all she could, savoring all the flavors. She realized she had made a mistake. She was to tend to Mistress's pussy when her lover pulled out unless instructed otherwise.
"I think somebody is thinking too much about being fucked by a hard cock, " Eve said teasingly.
Brad had left the room and returned with a bottle of water, which he had already downed on the way back from the kitchen. Curiously, his erection was still almost there. "I can handle that if you want."
"Brad, don't encourage her., " she said with a giggle.
"I'm just saying, that ass needs a good fucking is all."
Miss Eve started to worry that Brad was becoming a little too comfortable with this situation, and she knew she would probably be moving on from him. She wanted her man to focus on fucking her. On the other hand, he might make a good boyfriend for her sissy.
Her only concern would be if sissy got too comfortable with him and ultimately wanted to leave her. She did love her sissy. On the other hand, if she wanted to be with a man after all, who was she to stop her?
She decided it was time to find out the truth. "Okay, Brad. Fuck my sissy."
Britney looked up. "Mistress, I don't know about this."
Eve wasn't sure either, but she decided to go through with it. "I insist."
Brad took control of the situation. "Here, darling. Get on all fours here on the edge of the bed."
Britney complied and felt the plus being removed from her well lubed pussy. "I didn't tell you two I took some viagra, " said Brad. "I can go all night."
He shoved his hard cock inside Britney, who moaned from the pain. He stayed in that postilion for a few moments. "It's okay. Get used to it. A lot of sissies like you love that."
"It's so big, " Britney moaned.
He grinned. "Thank you."
Eve shook her head. "Typical man." She turned to Britney. "Relax, Angel. It always hurts the first time. Just go with it.,"
Eve got an idea. She lie on her back in front of Britney, with her elbows at the edge of the bed. "Eat my pussy some more, my pet."
Britney was getting used to Brad's big cock invading her tight sissy pussy as he thrust in and out. The taste and smell of her Mistress's pussy was intoxicating. She could never get tired of that.
But, how did she feel about being fucked for the first time? She realized at this moment that the last shred of her manhood was gone. That didn't bother her that much.
She was conflicted, because she knew she was meant to be a woman, but she loved her Mistress with all her heart. She would do anything to please her. And Eve would do anything to help her be the woman she wanted to be, including getting her the hormones for her transition.
This was a right of passage for many sissies and transgender women, the first time being penetrated by a man. Some would chose to have sex only with men, some would want both men and women and some would not want to be with a man, even in transition.
How did Britney feel about this? It actually felt good being fucked like a woman, and she could feel the pleasure build. Unfortunately, she was locked in chastity. She found that if she moved a certain way, it felt better. Could she actually cum this way? Did she want to?
Brad had just cum, and he could last for quite some time this time around. He was thrusting it in deep, and couldn't hide his pride in the moment. "Fuck, you're so tight sweetie. You feel so good."
With Brittney's mouth giving her pussy the right attention, Eve was on the verge of another orgasm. This was an even more amazing moment than she had anticipated. "Just remember, Brad, she's mine."
He laughed. "Of course. But right now she has my cock inside of her pussy."
"What the hell did I see in this guy" she asked herself. "Other than a big cock. Oh God." She was having another orgasm. "Keep doing that, Britney. That's it, my pet."
As Britney was lapping her Mistress's pussy, she felt an orgasm building up. It felt like it was coming, but just a little out of reach. She tried to make it happen. She was desperately moving her pussy around his cock and pushing back."
"Fuck yes, " groaned Brad. "This one likes cock. I think I'm gonna cum."
Britney was feeling it build up and finally release. Her clitty was tightly confined, but she was leaking cum when Brad erupted inside of her pussy. She felt the warm cum inside of her, making a new sissy out of her.
"I'm cumming, " Brad proclaimed, and Britney kept pushing back, inviting his cum inside of her. It hadn't really dawned on her that Brad was not wearing a condom.
It was Eve who sat up and watched as Brad pulled his unwrapped cock out of her sissy's ass. "You weren't wearing a condom?"
Brad panicked. "You didn't say..."
Eve pointed to the door, "Okay, I think you need to leave."
"I didn't know, " he said as he grabbed his shorts and shirt and left. "I'm sorry."
Eve was genuinely concerned for her sissy, who lie face down on the bed, feeling so many things after losing her virginity. Regret was not one of then. "Are you okay, Britney?"
"I'm fine, Mistress, " she said with a smile.
Mistress was horrified about her sissy taking cum inside her pussy. She knew the risks a sissy took with unprotected intercourse. "I'm sorry. He had no right to cum inside you. I don't want to put you at risk."
Britney suddenly realized what had happened, and her clitty started straining against the cage again. "It's okay, Mistress"
Eve shook her head. "No it's not."
"It is, Mistress, " the sissy said with a smile. "The way I see it, I got to take his cum inside my pussy just like you did. I feel so lucky."
Eve was shocked, but admittedly a little turned on at the thought herself. "That may be so, you little slut, but you had better get my permission from here on out to let a man cum inside that pussy, or I'll tan your ass good, understand?"
"Yes Mistress, I'm sorry, " she wanted to play with her clitty so badly in that moment. "You know, it's different than I expected."
"Oh, so you expected it?"
Britney sat up, feeling a little strange with a man's cum inside her sissy bottom. "That's not what I'm saying. It's just... I don't know."
Eve hugged her sissy. "It's okay. Do you like Brad?"
Britney blushed. "Mistress Eve! I mean, he's cute and all, but my heart belongs to only one person."
Eve had to admit to feeling a little insecure after what just happened. "Who is that?"
Britney moved down and kissed her Mistress's feet. "You, Mistress. I love you, and I am yours to do with as you will."
"Whew, that's a relief, " she replied with a laugh. "I was afraid I was gonna have to break in a new sissy. I don't know if I could cope without a sissy keeping things up for me around here."
Britney looked up from Eve's feet. "Mistress Eve, please don't joke about that. I would be lost without you."
"Well, then, " she replied as her confidence came back. "We're gonna have to deal with your punishment.;"
"Another spanking?"
Miss Eve laughed. "You wish. "I may have to lock you in the closet in the dark for a weekend."
"But..."
"Back talk to me again, and I'll tie your ass up first, " she said, quite serious about the threat.
"I'm sorry Mistress. I would never forget my place in the life of my Goddess."
Eve got on her hands and knees. "If you're gonna be kissing my ass, you might as well do it literally you little sissy slut."
Britney smiled and obeyed as a bit if Brad's cum leaded from her stretched hole. "Gladly."
Mistress Eve looked behind her and pushed her beautiful shapely ass in Britney's face. "While you're at it, lick my asshole too you stupid bitch"
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