Casey's Submissive Journey Pt. 04

Angie & Debbie (Fag Night) Part Two

After putting on the movie Angie walked to the side of the bed and carefully removed her hat, gloves and shoes. As she did she called Debbie over and told him to lie down and get comfy. He took a sip of his drink, put it on the nightstand, then laid down on his side and watched the video. Soon after he felt Angie's weight on the bed behind him, then felt her snuggle up against his back and hug him from behind. He liked that. They laid together, snuggled and watched the movie for about an hour. At one point Debbie felt Angie's boner press against his ass through their dresses, he liked that even more. A few minutes later she was rubbing his corduroy bulge and purring in his ear. He got the feeling they weren't going to watch the rest of the movie, and he was right.

"Debbie, would you mind if we talked a little bit?"

He rolled on his back and looked up at her. "Of course not Angie. And what would a pretty lady like you want to talk about?"

He said it with a shy smile and it made him sound like a flirt, and she must have enjoyed his flirting because she kissed him passionately for several minutes. When they came up for air, they both shifted to get more comfortable, with Debbie on his back and Angie lying next to him on her side.

She reached down and gently massaged the bulge in his dress.

"I wasn't kidding before Debbie, I want to have sex with Casey too. You see I don't mind doing the homo thing for Audrey, in fact I kind of like it. Not only because it turns her on, but because I really do love cock, and sometimes I like a nice hard manly dick inside me.

I mean, don't get me wrong, I love being Angie, and if given a choice I would want to have sex as Angie 75% of the time, but there is that other 25% too. Actually Casey, I've fantasized about you fairly often over the past couple years, especially when you're in your corduroy pants."

She smiled and gave his bulge a gentle squeeze. Debbie jumped a little in response and smiled back. Hearing his young buddy say that he'd been fantasizing about him was very flattering, in a kinky sort of way.

"Um, Angie, would you like me to put on a pair of man pants for you?"

She laughed. "No-no Debbie, not at all. I'm just telling you things for the future. No, tonight I want my pretty little Debbie, I want to give my horny girl a good hard fucking."

As she said the last part, she gave him a mischievous smile that made her look so damn sexy he thought he might die. His sore asshole twitched in response, but at that moment he didn't give a shit if it was sore or not, he wanted her to fuck him, he wanted to be her bitch.

"Wait a minute Debbie, I want to do something."

She got up on her knees next to him, unbuttoned his dress from the waist down and spread it apart, then pulled his boner and balls out through the hole in his leggings. Reaching over she put her corduroy gloves back on, laid down beside him, and fondled his balls with her gloved hand. That turned Debbie on like crazy. She stroked his boner with her corduroy glove too from time to time, but mostly she played with his sissy balls, she seemed to be more interested in teasing him than jerking him off.

"Actually Debbie, one of the reasons I've been so attracted to Casey is because I've always had a thing for older men. It's a long story, but when I was younger I got involved with this older guy in my neighborhood. I used to go over his house and we played video games and other stuff. I guess he was seducing me from the start, but one day he came on to me and sucked my dick.

I was a scared shitless but it felt really good, so I came back the next day. But that time as soon as I got there he unzipped his corduroy pants, pulled out his dick and insisted I suck him first, and the whole time I was sucking his cock, he said stuff like. 'That's is Jamie suck daddy's dick, be a good boy and make daddy happy or I'll spank your bottom', stuff like that.

Well anyway, I have to admit, it really turned me on and I actually came right in my pants. I don't know why I liked it, maybe because of his corduroys, but I started going over there a lot, and we started playing all these older-guy/younger-guy games. It only lasted a few months, and then he left suddenly. I didn't really miss him that much, but I did miss sucking his dick in his corduroy pants and playing those games. You know like headmaster and student, or kid in jail and the guard, games like that."

She stared intently at Debbie's dick as she played with it.

"I guess it was the first time I saw you in your brown three-piece corduroy suit that I started having the fantasy of you being my strict headmaster. I jerked off a bunch of times to that fantasy, it always made me horny as hell."

She slowly and sheepishly brought her eyes to his, she looked very embarrassed.

Debbie though for a moment, then gave her a shy smile. "I don't know what to say Angie, I've never done anything like that before, but if playing those games turns you on I'm more than willing to give it a try."

He paused and shrugged.

"But you're going to have to tell me what you want me to do, because right now I don't have a clue."

Angie's face lit up like a Christmas tree. "Oh God Casey thank you, thank you, and don't you worry I'll take care of everything, I'll write it all out and give you lots of ideas." Then she kissed him.

Angie was very excited, someday soon she would be sucking headmaster Casey's dick in his Corduroy suit. In fact, she was so turned on that her ball massage morphed into a full-fledged handjob. He liked that. He soon realized though that the fine wale corduroy fabric was a little rough for masturbating, and he worried that his dick might get a sore. However, he also loved the fact that she was jerking him off with corduroy, and after a quick mental debate he let her continue. He wondered if she ever jerked off with her pretty gloves, and he decided he would love to see that. Actually, he would love to put on the gloves and do it for her.

His worries were soon laid to rest a minute later when she let go of his boner and resumed groping his balls. When their long kiss ended, she gazed into his eyes, cleared her throat and looked like she wanted to say something.

"What is it Angie?"

"I, ah, I don't do small talk real well Debbie so I'm just going to say it, I want to fuck your tight little ass sissyboy, and I want to fuck it right now."

He was a bit stunned at first, but after the words sunk in, he thought he might die of desire right on the spot.

"Oh girl, you don't beat around the bush, do you?

She waited him out.

"Well, OK Angie, actually I think I'd like that a lot, but, can I ask you a question?"

"Of course Debbie, what is it?"

"If you wanted to fuck me, why did you start jerking me off? Why start something you weren't going to finish?

Her smile got mischievous again and she wiggle his boner around. "Because Debbie dear, I like my bitches nice and horny when I fuck them, it makes them want it even more. Got a problem with that bitchboy?"

Her tone got suddenly sharp, and it caught him a little off guard. But he loved it.

Getting in the spirit of things, he adopted a sissy submissive attitude. "Well I don't know Miss Angie, my asshole is still pretty sore, Karen raped it really hard last night."

She gave him an amused smile. "Well Daisy May, it's about to get a lot sorer, so what's your point?"

He knew right then he was about to be royally fucked for the second time in 24 hours, and he also knew that he wanted it even more than she did. His asshole clenched several times reminding him of just how sore it really was, and he told his asshole to shut the fuck up.

"I guess there is no point Miss Angie. I just..."

"Well sissyboy, do you want me to fuck your tight little pooper, or not?"

Her face looked stern and he noticed her dress was tenting, he loved the fact that she was horny for his ass.

"Yes Miss Angie, I want it, I want it a lot, how do you want to do it?"

Her mischievous smile returned. "Get up Debbie dear."

They both got off the bed and Angie positioned the corduroy pillows the same way Karen had the night before, one for under his hips, and one for his face.

Then turning to Debbie, she stood with her hands on her hips. "Excuse me dearie, I think you should take off my leggings, it will make fucking you a lot easier."

He shrugged, gave her a look that said "silly me", then stripped out of the leggings. Even though he enjoyed wearing something of hers, he also liked having his cock, balls and ass fully exposed. It made him feel very vulnerable.

Coming around behind him she gave his ass a little slap. "Go ahead bitch, hump the corduroy pillow and stick your ass in the air."

"Aren't you going to lay something over the pillow Angie, you know what might happen."

"Oh, you mean like you might cum all over the pillow and Audrey will cut your sissy little balls off? You mean something like that?"

He looked back over his shoulder and said flatly, "yes Angie, something like that."

"Relax Debbie and stop worrying about Audrey, it's my bedspread and it's my night. You know damn well I would love it if you creamed my corduroy pillow. Now stop your sissy stalling and lay down fag."

Spreading his dress open, he obediently draped himself over the pillow, and as soon as his boner touched the corduroy fabric he started humping it. She let him go for a minute or two, understanding his need to fuck the plush corduroy, and as she watched she removed her dress. Taking a tube of K Y jelly she knelt on the bed behind him, pulled his dress up on his back and gave his ass a stinging slap.

"That's enough pantyboy, if you want to cum, do it when I'm fucking you, not before. Now pull your sissy cheeks apart for me dear."

With his face pushed firmly into the corduroy pillow, he reached back and pried his ass cheeks apart. Even though Angie was beautiful and turned him on more than any fag ever had before, it still felt a little strange to voluntarily give up his ass to another man's dick. To spread your cheeks for a horny cock was the same as screaming, "I'm your bitch." He felt the coolness of the lube on his anus, then immediately felt her finger stab his sore asshole. He jumped and gave a slight squeal into the pillow but she ignored his protests. She wiggled her digit around for a few seconds, and then proceeded to work one, two, and then three fingers in and out of his boy-pussy until it seemed ready to go. He wrapped his arms around the pillow and kissed the corduroy in anticipation of what he knew was coming. Angie quickly applied globs of greased to her very hard dick, then used the leggings to clean her fingers. She was ready.

Her arms came down on each side of him, she kissed the back of his neck and poked her mushroom around between his slippery cheeks. Finding its target, it wedged itself firmly in his pussy, prying his asshole open just a little bit.

"Are you ready to be my bitch Debbie dear? Once I shove it in your pooper I'm not pulling it out until I give you a hot sperm enema. Last chance to say no fag."

She was a little worried because his whole body had completely tensed up, but he pulled his face out of the pillow just far enough to say, "enough talking bitch, let's see if you know how to use that sissy little dick."

She chuckled. "Oh, so you're a fucking smart ass now?"

She shoved about six inches up his ass in one thrust.

His asshole screamed, he bit the pillow and squealed like a little piggy. Angie let out a moan of pleasure, then pulled it out and did it again, getting the same response.

"Still feel like being a smart ass pantyboy?"

She did it again, a little deeper, then repeated the question, but this time she waited for a response.

After a few seconds, he groaned a reply. "I thought Audrey said you had a real dick, now I know why you wear a fucking dress Daisy May."

"Why you little fucking whore."

She pulled her dick out and quickly popped her mushroom in and out of his anus about 30 times, showing him no mercy. Then without warning she buried her boner right to the balls. He squealed and gasped into the pillow during her machine gun raping, then let out one loud groan when she rammed it home. Angie laid down on his back and kept her cock buried to the hilt.

"Are you doing OK sweetie?"

Catching his breath, he moaned, "yes honey, don't worry, I'm fine." He really meant it too. His asshole was hurting for sure, and her mushroom was stretching the top of his rectum inches past where it wanted to be, but knowing the fuck pole shoved up his ass was a real cock turned him on a lot. It'd been a long time since he'd had a real flesh and blood, sperm spitting dick inside him, and he savored the reality.

"Are you liking by dick sweetie?"

"Silly bitch, of course I am, doesn't it sound like it?"

"Just making sure honey, can I do anything for you while I'm taking your pussy for a ride?"

He paused for a moment and purred when he felt her flexing her dick in his rectum.

"Actually Angie, do you have any of your man pants around? I think I might like to kiss a pair while you're fucking my bottom."

That both surprised and pleased her, and she thought for a minute. "No Debbie I'm sorry, all my corduroys are at your house, I mean except for the pair I was using as a sperm rag, but they're filthy."

Without hesitation he said. "Please go get them."

"Are you sure sweetie? They've got sperm stains all over them, and, well, it's kind of a long story but I peed on them a little too. In fact, they're probably still damp, and I'm sure they smell of piss."

She sounded embarrassed by the admission.

"Angie, listen to me, go get them, please get them now honey."

"Alright fag, if you're sure that's what you want, I'll be right back."

She got up, pulled her dick out of his ass and left the room. He enjoyed the feeling of the corduroy against his face and tried to fuck the pillow again, but his cock was a limp noodle from the fucking. After a couple of minutes, she returned and knelt on the bed behind him, then told him to lift his head. She slid a pair of gray, mid-wale corduroy jeans onto the pillow in front of his face, and smoothed them out. She was right, they were covered with sperm stains, she must have pumped about forty loads of jizzum all over them, and he could smell the piss immediately. He lowered his face into the trousers, felt the dampness and the perverseness of his situation made him horny as hell. He was lying with his face buried in a pair of sperm stained, piss soaked corduroy man pants waiting for his buddy to fuck his ass with his big dick. He suddenly wished Audrey was there to add to his humiliation. Angie wasted no time shoving her dick back in again, and right to the balls too. It went in a little easier, but not much. He pushed his face into her corduroys and did his piggy squeal.

"What's the matter dear, did I hurt your little brown ring? Whores with little dicks deserve it hard and nasty, that's the way it works darling. Girls with big dicks fuck girls with little dicks, that's the way of the world."

She obviously swapped nice Angie for nasty Angie when she was gone, but he was kind of expecting that, especially after asking for his man pants like a sissy slut. He could see now that all three of them, Karen, Audrey and Angie liked being dominant ladies, and it seemed they all decided that he was going to be their bitch. She started reaming about eight inches in and out of his rectum, and taunted him unmercifully.

"Look at you sissyboy, you're sucking piss out of another guy's pants while he fucks you in the ass, I mean what kind of guy let's another guy do that? You fucking wimp."

She continued to degrade her bitch for several more minutes, then began ramming his ass hard and fast, she clearly wasn't concerned whether he liked it or not, she was now in full fucking mode. As Angie raped his ass and humiliated him, he enjoyed being her bitch more and more, he liked surrendering his rectum to a dick the same way a woman surrenders her pussy. He enjoyed it when a cock had complete control over him and used his ass for its selfish pleasure. The act of submitting to a horny boner while it used him as a cum-dump was very exciting.

In a woman's case, she let a dick use her pussy because she'll eventually get an orgasm out of it, it's a give and take, her vagina was designed to be fucked by a cock. But a bitchboy's ass wasn't going to give him an orgasm. In fact, a faggot's fucking starts with a lot of pain, a reminder that his rectum wasn't meant to be used by a dick, it was meant to squeeze out turds.

Debbie liked putting on a dress and letting another fag use his ass to empty his ball sack, and being a submissive bitch, he loved sucking the fag's dick and begging for it. The simple fact was, to Debbie it really wasn't so much about the fucking, as it was about being fucked, about being used, being someone's bitch. He really liked it when a lady or a fag used his mouth or ass for their pleasure, he loved being a willing fuck toy. In fact, he'd gladly spend a whole night being a whore without any reciprocation whatsoever. Letting him jerk off with their corduroys when they were done would be reward enough.

Angie had remarkable control and fucked his bottom for an hour or so. She repeatedly told him he was a sissy little queer and deserved to be fucked like a two-dollar whore. She would ream him hard and fast for a while, then suddenly stop for a minute before fucking him again. After a while he realized what was going on, she was doing the same thing he did when he jerked off, stroking himself right to the edge and then backing off, he could do that for hours sometimes. He began to wonder how long she was planned to fuck him though, because the lubrication was wearing thin.

"Angie honey, can you please stop for a minute?"

She stopped fucking but kept her dick buried in his ass. "What is it fag, don't tell me you can't take it anymore, I'm not done with your sissy ass yet."

"No honey, can you just grease us up a little more please?

"Alright Daisy May, I want a sip of my drink anyway, but you're doing the greasing, got it bitch?"

"Yes Miss Angie, of course."

She pulled her cock out of his ass and his rectum let out a long fart. She laughed and gave his ass a playful slap. "Oh my, aren't you the smelly little bitch?"

She got up off the bed and grabbed her drink, then sat in the chair. Her big red dick looked impressive standing straight up, it didn't look the least bit tired. He pushed himself up, took a sip himself, then grabbed the tube of KY jelly and gingerly walked toward the bathroom.

"Where are you going my little fuck-bunny?"

"I'm going to the bathroom, I want to clean up a little before we continue."

"Darling, I'm just going to mess up your little bottom all over again, so why bother?"

"I know Angie I know, I just want to, I'll be right back."

"Well don't take too long Mary Jane, because if I lose my boner I'll make you suck my shitty dick hard again."

She obviously had no intention of coming out of her mean Angie persona.

As he walked toward the bathroom he stared at her dick, it looked as hard as a railroad spike and the remaining lube made it shine in the light. Part of him couldn't believe the whole fucking thing had just been inside him.

"Stop gawking fag, go do what you need to do, and hurry up," He snapped out of it and went to the bathroom.

Sitting on the toilet, he spent a minute deciding if he needed to shit or not, it was always difficult to tell right after being fucked. Sometimes the urge to push out a turd was simply his rectum remembering the dick that just raped it. He stuck his middle finger in his ass and was surprised it wasn't gaping, he could still squeeze it with his asshole. He probed as deep as he could for a few seconds, and once he was satisfied he was empty, he wiped his ass clean and gave it a good greasing. The reality of what he was doing sank in, and the fact that he was acting like a total wimp turned him. He suddenly wondered what Audrey would say if she could see him now, sitting on her toilet in full drag, lubing up his ass for a second fucking by her husband's big dick. Actually, the thought of her being there and humiliating him became very exciting, and he wondered if she would insist on fuck him with her dildo too.