Casey’s Submissive Journey Pt. 08

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Mistress Betty – Part Two

When Karen returned from the kitchen she was holding a drink in each hand and the sight awaiting her not only shocked her, but stopped her dead in her tracks. Betty had her skirt pulled up on her belly and Debbie was between her legs licking her pussy. Betty’s face was upturned, her eyes were closed and she had a very contented smile. It was obvious she’d not only warmed to the idea of having her pussy licked, but she seemed to be enjoying Debbie’s efforts a great deal. That wasn’t really surprising though, Karen knew Debbie was quite skilled at cunnilingus.

She stood still for a minute soaking in the whole scene, and as she watched she found herself getting a little upset with both of them. Part of her didn’t like the idea that Betty would let Debbie lick her pussy and not her, but she chalked that up to a pang of jealousy. She knew she’d get her chance soon enough. She was upset with Debbie on the other hand for an entirely different reason. He knew full well he should wait for her permission before licking any woman’s pussy.

She managed to put all that aside though when she realized how silly her husband looked. She not only made him dress up like a fag but he looked like a complete fool being on his hands and knees with the silly antlers on his head. He looked like Rudolph giving Betty a Christmas lick. As she watched she was proud of herself for setting the evening up without any help from Audrey, her mistress skills were getting better and better. She not only managed to arrange an evening of sissy degradation for her husband, but made it happen in front of another woman, which she knew enhanced his humiliation tremendously. However, as good as all that felt, what really gave her a thrill was the sight of Betty’s stockings and garter belt. It told Karen she had come with the intentions of doing more than just watching.

Betty was letting out little moans, and Karen knew Debbie’s tongue was earning her points with her new girlfriend. She loved the fact that Betty was comfortable enough to enjoy such an intimate moment in front of them, it takes some ladies a long time to build that level of trust. She just wished it was her down between Betty’s legs instead of her husband, licking Betty’s pussy had been on her mind ever since the first night she saw her at the Club. She took a deep breath and continued walking in as if none of it surprised her.

“My my, what have we here?”

Betty opened her eyes and her face suddenly looked apprehensive. “Um, sorry Karen, he said you wouldn’t mind so I told him to do it. Is that OK?”

Debbie never stopped licking and Karen smiled, putting her at ease. She handed Betty a drink.

“Relax dear, it’s perfectly alright. I’m glad you decided to try out my fag’s tongue, I think he’s quite good. Do you agree?”

Betty took the drink, nodded, then giggled like a little girl, which Karen found very sexy. Karen sat on Debbie’s back as if he were her pony, and gave Betty a seductive smile.

“However Betty Jean, he’s not nearly as good as his Mistress.”

Betty held her stare for a long moment before putting her drink down and laying her head back. Karen was sure she scored another point. She closed her eyes and moaned a little, it was obvious Debbie’s tongue was serving its purpose well. Karen quickly found herself fighting off a strong urge to reach out and grab Betty’s tits. So to keep from possibly making a mistake, she reached back and gave Debbie’s ass a hard slap instead.

“I’m very glad my bitchboy is making you feel good dear, and I want you to feel free to use his mouth whenever you’d like. However, his sissy little balls will be getting a good hard slapping a little later on. He really should have waited for my permission before servicing another lady’s muff, and he knows better. It seems to me the little shit is getting too big for his britches.”

Betty looked at her but said nothing and her face had a dreamy expression. A look that told Karen her orgasm wasn’t far off.

“In fact dear, I think I’m going to shove my dick up the bitch’s ass right now and remind him who’s in charge here. Do you mind?”

Betty was breathing hard and losing focus, she just moaned and shook her head. Karen slid off Debbie, pulled a tube of KY jelly out of her bag and lifted Debbie’s skirt on his back. She gave his ass and her dildo a good greasing, then worked a couple of fingers in and out of her husband’s tight pussy. When Debbie was properly lubed and loosened, Karen positioned herself behind him and pressed her fat mushroom against his brown ring. She was just about to ram it in when Betty went over the edge and started swearing at Debbie.

“Lick it bitch, oh God lick my cunt you fucking faggot, make me cum or I’ll kick you in the balls!”

Debbie complied and Betty had a very intense orgasm, flooding his mouth and face with her warm juices. Not wanting to ruin Betty’s orgasm by distracting Debbie, Karen waited patiently for Betty to finish before fucking her fag. Actually, tuzla escort she kind of enjoyed watching her new friend lose control.

Debbie continued licking Betty’s pussy after her orgasm had faded. He did it gently though, and watched her body language as all ladies were different. Some like continued stimulation, others like just a hint of it, and yet others don’t like any at all. In her case, it seemed she liked a little gentle licking. When Betty opened her eyes she had a big smile on her face and Karen asked excitedly.

“Did that feel good dear, isn’t my fag a good pussy licker Miss Betty?”

She thought Karen seemed a little too excited, she almost sounded like a proud mother, but by then she really didn’t really care because she was captivated by this perverted couple. With her orgasm over she began feeling embarrassed about being so exposed in front of strangers, but she quickly dismissed her concerns. Karen had a dildo sticking out of her pants and she just watched her girlied up husband lick her pussy, so there really was no reason for her to feel embarrassed.

She cleared her throat. “Yes Karen, your fag does a very good job, thank you.”

“Oh you’re more than welcome dear. I think of you as a friend now, and I always share my pussy licker with my friends. Listen Betty Jean, could you do me a favor and sit up straight?”

Karen pulled Debbie back by his shoulders to give her some room.

“Sure Karen.”

She sat up, pushed her skirt down and took a sip of her drink.

“Thank you dear. I’d like to let my fag bury his face in your corduroy lap while I fuck his bottom, it’ll give the pervert a thrill. Would that be alright Betty Jean?”

Betty smiled and raised her glass.

“Anything for the lady who’s going to get me into the Sisters of Cordella.”

She looked at Debbie.

“And for that very nice licking I just received, I think the bitch deserves a reward too, come here pantyboy and kiss my corduroy crotch.”

She spread her legs and smoothed her skirt over her mound. Karen was getting very turned on by how quickly she was getting into their sex games. Debbie leaned down and Betty grabbed the back of his head, forcing his face into her skirt. Once his face was pressing against her crotch, she gently but firmly grabbed the sides of his head.

“Go ahead Mistress Karen, please show me how you fuck your dickless fag. I’ll keep him in place while you take care of business.”

Karen was again pleasantly surprised. She also started getting a sneaky suspicion that Betty might be a little more versed at Mistress/fag discipline then she’d let on.”

“Thank you Miss Betty. Here it comes Tinkerbell.”

She grabbed his hips and shoved the fat mushroom of her dildo in his rectum without a hint of caution, along with a few inches of hard boner. She wanted to pop his cherry a little extra hard so Betty could hear him squeal, she was interested to see what her reaction would be. Debbie pushed his face into the soft wide-wale skirt and did indeed let out a muffled squeal. Even though he’d been anticipating getting it hard with Betty watching, there’s no way to prepare for that initial pain when your asshole is suddenly split wide open. He knew because he’d tried and failed many times before. After hearing his unmanly squeal, Betty laughed.

“Wow Karen, I see you don’t believe in being gentle with your fag. Do you ever give it to him easy?”

Karen smiled, pulled her mushroom out and popped it right back in, getting another squeal.

“Sometimes I do Betty Jean. But when fags get too big for their britches and lick pussies without permission, they deserve punishment, not pleasure.”

She popped his asshole again.

“They need to be reminded of what they are, lowly cocksucking fag shit.”

Again, she gave him something to squeal about.

“Actually Betty, if you’d be so kind, please hang on to him tightly for a minute.”

She did, and Karen popped his asshole about thirty times in thirty seconds. As he grunted and squealed into her corduroy mound, Debbie wrapped his arms around Betty’s hips and held on for dear life. Betty grabbed his shoulders and held him down, marveling at how nasty Karen was treating his shitter. When Karen finished her machine gun raping, she shoved the full length of her dick up his ass and rested. Betty looked up at her, their eyes locked and Karen saw what she was looking for.

There was no pity for Debbie, she was simply waiting for what came next, and that told Karen that if she didn’t already have some experience as a Mistress, she was definitely a good prospect. Karen was very aroused and decided she had to take a chance. With her cock buried to the hilt in her husband’s rectum, it allowed her to lean over him and get her face near Betty’s. Betty watched her draw near and never broke eye contact. When their faces were just inches apart Karen seductively licked her lips and asked. “May I?”

Betty knew what she wanted, and göztepe escort the truth was she wanted it too, she slowly nodded once and Karen did the rest. She gently cradled Betty’s face in her hands and kissed her. First a gentle kiss on her lips as she stared into her eyes. Then closing them she pressed her lips firmly against Betty’s and they kissed passionately. They did so for a couple of minutes, eventually swapping tongues and forgetting about Debbie. However, having Debbie’s face rubbing around her crotch as he whimpered and groaned made it more difficult for Betty to ignore him. She finally pulled back and Karen was turned on by the shy look in her eye, she looked like a teenager who just got kissed for the first time.

Her voice was sweet and barely audible. “Maybe you should get back to fucking your fag.”

Taking the hint Karen smiled broadly, gave her a quick peck on the lips and did just that. Straightening back up She gave Debbie’s ass a slap, pulled her dildo all the way and buried it again.

“Still with me faggot?”

He squealed and gave her a muffled “uh-huh.”

She started fucking his ass with a slow steady rhythm and talked to Betty as if he wasn’t even there. Although every now and then she’d painfully pop her mushroom in and out of his tight asshole a few times, just to keep him on his toes. She explained in a casual manner what a pathetic sissyfag her husband was, and how much she enjoyed making him worship other men’s dicks for her amusement. As she degraded and embarrassed him she would occasionally order him to answer questions that were designed to humiliate the shit out of him.

Betty remained quiet at first, but soon started to ask questions of her own, and she threw a few nasty comments his way too. Karen liked that a lot, and in truth so did Debbie. He loved it whenever Karen fucked his bottom and put him in his place, and having Betty participate in the fun added a multi-Mistress dynamic that was very exciting. He especially loved it when Betty made references to corduroy, if nothing else it seemed like she was starting to understand the power it had over him. After about twenty minutes of that, Karen increased her pace and started fucking him hard and fast, bouncing his mouth around Betty’s mound. Betty held onto the back of his head, and kept his face jammed in her corduroy crotch, which was just fine with Debbie.

She looked up at Karen with excitement. “Go ahead girlfriend, give it to him good, fuck the fag!”

That thrilled Karen to no end and she proceeded to rape his ass as hard as she could for about ten minutes. Debbie squealed, held on to Betty and just took it like a wimp, weakly groaning “no” into her skirt the whole time. Betty however, suspected he was enjoying every minute of it.

“You love it don’t you? You fucking wimpy queer. You wish it was a real cock, you want a load of hot sperm up your ass don’t you Mary Jane?”

Between her taunting and Karen’s pounding he slipped into fag heaven and went limp as a rag doll. She could have fucked him for hours and there was nothing he could have done about it, he was completely vulnerable, his ass belonged to her. Karen didn’t want to wipe him out just yet, that’s why she didn’t use one of her really big dildos, she had more plans for him before the night was over. So when she sensed that fag paralysis was setting in, she banged him a few more times and finished by burying it to the hilt.

That gave her another opportunity to bring her face close to Betty’s, and even though she still saw some apprehension she also saw lust in Betty’s eyes. She didn’t bother asking this time and just kissed her, and Betty kissed back immediately. They wrapped their arms around each other and kissed passionately for several minutes, this time completely ignoring the limp pantyboy between them.

After separating and catching their breath, Karen spoke first.

“Well Betty Jean, that gives you a little taste of what an obedient slut my sissyboy is. I hope someday he can help you achieve your goal. I think you’ll find he’ll be a very useful tool when training your fag. Isn’t that right Debbie dear?”

She slapped his ass and Debbie yelped. “Yes Mistress, I’ll serve Miss Dickman in any way she wants.”

“Oh I know you will Tinkerbell, Betty Jean is my friend, and you will always make my friends happy.”

She looked back at Betty. “I tell you what Betty Jean, let me send my fag on his way, then we can settle in and talk a little more. Would you like to see him do anything else before he goes? Anything at all dear?”

Betty shrugged, then shook her head no. Karen abruptly pulled her dildo out of his ass and that got a loud moan. Betty wondered if it was a moan of relief, or disappointment. Karen moved back and stood in the middle of the room with her hands on her hips and her dirty dildo sticking straight out.

“Come over here bitch.”

Debbie didn’t move.

“Betty Jean, would you kindly give the bitch a little push?”

“Sure üsküdar escort thing dear.”

She grabbed him by the shoulders and pushed him up into a kneeling position. Once up he wouldn’t look at her, he stared down at her lap. His wig had shifted a little, and between that and his sissy antlers he looked pathetic, but even though he seemed humiliated she thought she saw lust on his face as he stared at her skirt.

She straightened his wig and said. “Look at me fag.”

He didn’t, and she looked at Karen somewhat puzzled.

“Look at Mistress Betty bitchboy. Do it or I’ll squeeze your sissy balls and make you cry right in front of her. Now do it!”

He slowly brought his eyes up to hers and Betty could see the humiliation written all over his face. She also saw his age through the make-up, and it felt strange to be abusing an older man. Her ex-husband was a few years younger than her, and her current boyfriend, and fag prospect, was half her age. Well almost.

She then gave Karen a thrill. She cupped her hand under Debbie’s chin and moved her face close to his. “Tell me Tinkerbell, do you like sucking dick?”

He just stared at her, and after a few seconds, Karen said. “Answer her Debbie.”

He slowly nodded and Betty giggled. She then gently ran a finger around his lips.

“Oh, I bet you do. I bet you love having these lips wrapped around a real man’s cock, sliding them up and down, jerking him off with your sissy mouth. I bet you cum right in your corduroys when you’re sucking dick. In fact, I bet you’d even kiss his ass and beg for his jizzum if your mistress told you to.”

She found herself enjoying his humiliation a lot more than she thought she would.

“Well Debbie the fag, I have a sissyboy of my own, he’s got a pretty little six-inch dickie, and I think I’d like to watch you suck it. I bet that sounds really good right about now, doesn’t it Princess Penis Licker?”

He was mesmerized by her and slowly nodded.

“Do you know what else Tinkerbell?”

He shook his head.

“Well fag, he’s got a pair of corduroy pants, and I bet you’d like to suck his dick when he’s wearing them. Wouldn’t you, you fucking little cocksucker?”

Both Debbie and Karen were blown away by how quickly Betty picked up on everything, and how well she delivered her taunts. Karen wondered if it was just the alcohol talking, but she didn’t seem drunk otherwise. Debbie nodded again.

“Well Debbie dear, if you give him a really good blow job, maybe I’ll let you jerk off with his pants.”

Karen suddenly felt things between Betty and Debbie were moving along a little faster than she liked.

“OK Betty Jean, you just might get a chance to see that very soon, but I think the idea of sucking Dana’s dick is getting my fag overheating, so could you please send him over here?”

Betty held Debbie’s eyes for a long moment, then gave him a smirk.

“Go ahead sissyboy, do as your Mistress said, move it!”

He turned, crawled in front of Karen and she instructed him to remove her cock, which he did immediately. He unbuttoned her pants, pulled them down and unstrapped the dildo. After pulling her pants back up she patted his head like she would a puppy, then told him to go wash the dildo. She reminded him to stay in drag because she wasn’t finished with him yet, then told him to bugger off and wait for further instructions, which he did obediently.


Karen went to get them fresh drinks and while she was in the kitchen Betty straightened her outfit, then they both settled in on the sofa again. They exchanged a few thoughts about what just happened and seemed to be getting comfortable with each other. In fact, after the kisses they exchanged Karen was certain they would soon become lovers. After a short while the conversation arrived at an awkward silence, so Karen decided it was a good time to get into the nitty-gritty of why Betty was there in the first place.

“Betty Jean, can we talk turkey?”

Betty smiled and ignored the impulse to make a corny joke. “Sure Karen, what’s on your mind?”

“What’s on mind is this. After what we’ve discussed so far and tonight’s little demonstration, can I assume you’re serious about training your fag?”

Betty took a sip and looked down at her glass for a moment, then remade eye contact.

“First of all Karen, I want to thank you for having me over tonight. What you just showed me turned me on a lot, and you’re obviously good at this because you have a very well train fag, my compliments. I know I could never train Dana well enough to get into the Lady’s Club, hell, I’m not even sure I can talk him into trying. So yes Karen, if your offer still stands I would like to take you up on it. I would be extremely grateful if you let me use Debbie to train Dana, if and when the time comes. I would also be grateful for any words of wisdom you could provide, you obviously know what you’re doing and I’m just a beginner.”

Karen was thrilled that Betty was genuinely interested, and at the same time filled with pride at how far she’d come in a relatively short time. She thought back to when she knew nothing and Audrey was teaching her the ropes.

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