Madam Molly Pt. 02

Molly & Jessie's conversation lasted about twenty minutes, and by the time it was over she'd made it quite clear that when it came to obedience her expectation were very high. She then informed him he was going to be her little slave-boy and amuse her for a while. When she was ready to get laid she'd summon her cuck Tracy back and Jesse would resume his boyfriend role. She told him to finish his drink, ordered him on his feet and then led him down the hall to her husband's bedroom. Once inside she positioned him in front of Tracy's closet and sat in the chair.

"Alright sissyboy, I've been very intrigued by your fetish ever since our first chat, and now that I finally have you here, I want to watch you play with corduroy. I want you to spend a few minutes feeling up his clothes, or doing whatever it is you like to do. See what turns you on in there. See what you might like to play with."

Jesse didn't need to be told twice and immediately began fondling all of Tracy's corduroys. He decided to start with his pants and take his time, he'd then work his way over to the shirts, lederhosen, overalls and jumpsuits. He couldn't believe how much stuff there was. He spotted two three-piece suits he didn't remember seeing the last time. It also appeared there were more trousers, and he liked the fact that Tracy was adding to his corduroy wardrobe. She sipped her drink and gave him several minutes to get himself nice and horny, giving herself a little perverse thrill in the process.

"Well fag, do you like what you see?"

"Oh God yes Madam, very much. I don't know to explain it but doing this turns me on a lot."

"Well it should you little pervert. You're standing in front of a closet and feeling up another man's pants while his wife watches you. How kinky is that?"

"It's very kinky Madam, and I've often fantasized about sneaking into someone's closet and playing with their corduroy clothes. In fact there were two times I, well never mind, but I really like doing this."

"What do you mean never mind? What were you going to say fag? You tell me everything Jesse, slave-boys are not entitled to secrets."

"It's no big deal Madam. It's just that I did play in someone's closet before, actually I did it twice, but that was a long time ago."

He lifted the leg of a pair of wide-wales and rubbed his face with it, and that made him inhale deeply, he was getting very turned on.

"Whose closet, and when? Come on sissyboy, no secrets."

He cleared his throat and kept exploring. "The first time I was just a boy, the family that lived across the street was away and we were supposed to feed their dog. One morning my mom told me to go over and do it, and while I was there I got possessed with the idea of going in my friend's older sister's closet."

"Looking for something to wear fag?

"Actually no Madam, back then I didn't do that, I was just looking for girly corduroys to play with."

"And did you find any?"

"Yes ma'am, a pants and vest outfit, it was a mid-wale done in a pretty floral print. I jerked off with the vest and came all over the pants."

"You naughty little boy. Did she ever find out?"

"I don't know Madam, I guess she must have discovered it at some point, but I never heard anything about it. Many times I've fantasized that she wore it on a date and had sex with a guy while wearing my jizzum."

She let out a seductive chuckle. "You really are a naughty little pervert aren't you? So what was the other time?"

"About ten years later, I guess, I was a teenager. I forget why, but I was alone in my brother's apartment shortly after he got married and I went through my sister-in-law's closet."

"I suppose you found something there to play with too?"

"Yes ma'am I did, and now that I think about it, it's pretty weird. I found a mid-wale pants and vest outfit that time too, only hers was black. That time I did try it on but it was way too big, she had a big fat ass and huge set of tits. So I just jerked off with it, but I was real careful not to cum on it. I saw her wearing it one time after that at a family party and I almost came in my pants when she sat next to me."

There was a brief pause and Jesse rubbed his face with a pair of very soft wide-wale overalls. He liked them.

"Well Jesse, it seems you were a genuine fucking pervert back then, and sitting here watching you get all horny for my husband's pants, I can see things haven't changed much."

"To be truthful Madam, I'd love it a lot more if it was your closet."

"Why you insolent little turd, are you complaining?"

Her voice was as sharp as a knife.

"Are you that ungrateful that you can't see what I've done for you, especially when it comes to your fetish?"

He turned to face her and she could see the panic in his eyes.

"No Madam not at all, I'm sorry, I meant no disrespect. I just meant that I've always liked playing with ladies clothes in the past, this is the first time I'm playing with another guys corduroys. I really do appreciate how much you're indulge me. I'm sorry I said it Madam, please forgive me. Should I kiss your feet?"

She liked that he backed down and groveled.

She sighed deeply. "No fag you stay right there where you are, getting horny over another man's pants, it's where you belong."

She gulped down the last of her drink and put down the glass.

"Now listen to me, and listen good. I know all about you. I know you like jerking off with ladies clothes and I know you want to dress in them, and maybe someday soon you might actually get to spend time in my closet. But that's what you want pantyboy, not what I want, and until further notice I'll be training you to give me what I want. If at some point you learn to serve me the way I like to be served, then you'll find out just how rewarding I can be. Got it?"

He turned back and eyed a pair of pleated mid-wale dress trousers, picturing a big dick sticking out through the fly.

"Yes madam, I do."

"Alright then Jesse, I'm glad to hear you say that. Now I want you to pick out three things. First I want you to select something you'd like to kiss and fondle, then pick out something you'd like to jerk off with, and they it can be the same thing if you'd like. Lastly select a pair of pants you'd like Tracy to wear when you suck his dickie. And yes Jesse, you'll be sucking my husband's dickie very soon."

By then Jesse was horny as hell and had a hard time making up his mind. He felt like a kid in a candy shop, but finally settled on three pairs of trousers. He draped them over his shoulder and stood in front of her.

"Madam I have a question."

"What is it fag?"

"I thought you said you wanted me to be your boyfriend tonight, no sissy shit."

"Go on."

"Well then why do you want me to suck his dick?"

She chuckled. "Who said my boyfriends can't be bisexual? And maybe I like watching my boyfriend act like a little queer from time to time."

They stared at each other for a few seconds, they both knew that was bullshit. After a moment she smirked.

"OK, I admit it, I've never done this with any of my other boyfriends."

She chuckled.

"None of them would ever do it. Actually I'm not sure how Tracy's going to feel getting his dick sucked by a guy. He's always the cocksucker, not them. But that's why I picked you for a boyfriend instead of a real man, I want to try some new things. And quite frankly Jesse, I'm sure you'll love sucking my hubby's little dickie. Now lay the pants out neatly on the bed, then kneel in front of the pair you want to kiss."

Jesse did as told and as he was doing it Tracy appeared in the doorway. Molly seemed a bit annoyed.

"I'm not ready for you cuck. But since you're here I want you to take the rest of your trousers from the closet and lay them out neatly on my bed. Nice and neat bitch, make a nice bedspread out of them. Then make us both another drink. When you're done I want you to stay in the living room and watch TV until I summon you. Got it?"

"Yes Madam."

He half-whispered. "Can I watch the Spanky video?"

Her eyes bulged momentarily, she looked both embarrassed and a little pissed off. "No you may not."

She gave Jesse a slightly embarrassed smile, then turned back and quickly composed herself. Continuing in a pleasant tone she said.

"Why don't you watch the video of Randy fucking you in your nurse's uniform? That one always gets you horny."

"Yes Madam, thank you."

He went to the closet and started collecting his trousers. He wasn't moving very fast and it seemed obvious to Jesse he was stalling to see what she was going to make him do. Molly waited patiently for a minute or two, then shooed him out of the room, and he left with an armful of trousers.

Jesse look at Molly and she smiled back.

"Go ahead sissyboy, show me how much you like my husband's pants."

Jesse felt very weird, he was about to worship a pair of corduroys while someone watched. He'd worshipped his own corduroys a million times, there was nothing new about that, but he'd never worshiped another guy's pants, and never done it in front of anyone else. It was embarrassing and exciting all at the same time.

He'd picked out a pair of grey, mid-wale trousers. They were flat front dress pants and the ribs of the corduroy were firm but had a nice soft finish. He liked that. They were definitely men's pants, there was nothing feminine about them, and for some reason he suddenly found that appealing. The fact that they'd been worn by a guy and had a dick in them made it seem more humiliating. He slowly ran his hands all over them, loving the feel of the fabric. With his face only inches away he inhaled deeply and actually let out a little moan, he was quickly slipping into worship mode.

"Come on sissyboy, kiss them, you know you want to. You've told me many times how much you like to kissing corduroy pants and dreaming about a dick in them. So do it."

He obeyed, and the feeling of the fabric against his face eroded any lingering hesitation. He kissed all around the front, paying special attention to the fly. His eyes wandered all around as he envisioned himself between a guy's legs with his face buried in his lap. Jesse was getting very horny very fast, and that scared him a little. Sometimes when he'd had a few drinks and was worshipping his own pants he'd get a little carried away, and he didn't know how she'd react to that.

"Come on pantyboy, I know you're dreaming about a dick in those pants, show me how much you want it."

The fact that she was watching him made him feel very awkward, but at the same time it turned him on like crazy. He started kissing faster, moaning a little louder and nibbling on the fly. He was now acting like a fucking pervert and he didn't care.

"You want a cock in those corduroys, don't you queerboy? You want to unzip his pants, pull out his dick and suck him off like a good little bitch don't you Jesse?"

He mumbled into the pants, "Uh-huh".

"Oh I know you do fag, and I'm going to make you suck a lot of dicks sticking out of corduroy pants, you're going to become my very obedient little cocksucker."

On top of everything else her words were driving him crazy with lust, and he began attacking the pants with his hands and face like he was possessed. He even started humping his bulge against the side of the bed. She liked that. She continued fueling his desire for dick and humiliating him for another fifteen minutes. At one point he noticed her voice change and her breathing become labored. He turned his head to look at her. She had her pants pulled down to her ankles and was fingering her pussy with great enthusiasm. That sight almost made him cum right in his pants. Not only was it a huge turn on to be humiliated by a woman while acting like a pervert, but the reality that she was getting off on it was thrilling beyond belief.

"From now on fag...Oh shit...I'm going to make you worship a guy's pants and beg for his dick before I let you suck his cock...you little fucking queer...Oh god!"

Jesse buried his face in Tracy's pants and banged his bulge against the side of the bed as he listened to her go over the edge. She wasn't the least bit quiet about it either, and he could tell her orgasm was extremely intense. He didn't cum in his pants, but he came close, and he was sure he must've leaked a bunch of pre-cum into his trousers. After a few minutes of afterglow for her, she looked at him with a pleased smile.

"Oh sissyboy, I liked your show, and you just scored some major points."

She gave her fingers a quick lick.

"Now get over hear and clean up this mess."

He crawled over on his hands and knees hoping she would like that, and as soon as he got near she held her fingers out for him to lick. He did so willingly and even moaned a little as he sucked on them. That pleased her. Without needing further instructions he licked her pussy and mound all over, then bathe insides of her thighs with his tongue, leaving her damp but clean.

"Alright pantyboy you did a good job, now back off."

He did, and she pulled up her pants, zipping them closed just inches from his face. As she did she noticed the lust in his eyes.

"Go ahead pervert, you can kiss them for a few minutes if you'd like."

He happily took her up on her offer and after a minute she started gently stroking the back of his head.

"I have to tell you something Jesse, and I'm not really sure how to explain it, but something weird just happened. Seeing you kissing Tracy's pants and getting all horny to suck his cock turned me on like crazy, that's never happened to me before. Well, maybe because I've never seen a guy do that before, but still. I don't know, something about seeing a guy want a dick so bad that he'd get turned on by another guys pants was really weird. I mean I know you love corduroy and I was expecting you to enjoy yourself, but as I watched it made me feel like all I have to do is tell a guy to put on a pair of corduroys and I can make you suck any dick I want. I could make you my obedient little cocksucker."

She chuckled.

He kept rubbing his face all around the front of her trousers and never objected. She got the distinct impression he liked what he was hearing and toyed with the idea of making him commit to being her cock whore, but decided not to push it on their first night.

"Well anyway. All I know Jesse is that I just had one of the most intense orgasms I've had on a long time."

He liked hearing that.

"And I think you better get used to the idea of doing that a lot in the future. Keep that in mind sissyboy, you just found a way to score big points with Madam Molly."

She chucked again.

"In fact, now that I think about it, I bet it'd turn me on even more if you begged me to do it first. Don't make me force you Jesse, beg for it. Are you getting the picture Daisy May?"

He was indeed, and he wouldn't have to act because he'd love doing it. In addition, having her get horny watching him would make it all the more exciting. He sensed they'd found something special too. He nodded.

She told him to get up and was amused by the bulge in his pants. She told him to sit in the chair and she sat on the bed. They both sipped their drinks and composed themselves a bit. After a minute she started running her free hand around Tracy's pants. She liked the fact that Jesse's had just been rubbing his face against them, she even picked them up and rubbed them against her cheek while giving him a very sexy smile. That excited Jesse. She eventually dropped them on the bed however, and called Tracy in the room.

When he entered she told him to sit in Jesse's lap, she then held up his pants and told him how much Jesse enjoyed kissing them. At first Jesse felt a little embarrassed, but remembering what a wimp Tracy was it passed quickly. Tracy gave Jesse a quick look then lowered his eyes to his lap, but Jesse saw a slight smile and suspected Tracy loved hearing about it. Seeing the two boys with their arms around each other turned her on a lot more than she thought it would.

"Alright sissyboy, let me see you kiss my boyfriend."

Tracy eyes bulged, he'd obviously not been expecting that, but after a moment he turned to Jesse with a timid smile and they kissed hesitantly for about thirty seconds, then broke it off.

"No-no boys, keep going. I want to kiss my cuck like he was your girlfriend at the drive-in movies Jesse."

Tracy looked a little flustered and he wouldn't make eye contact, but Jesse could see the excitement written all over his face. They started out slowly and after a minute the reality of what he was doing started turning Jesse on a lot, the kinkiness of kissing another guy was surprisingly exciting. Tracy seemed to enjoy it from the get-go and pretty soon they were getting hot and heavy. They started feeling each other up and it didn't take long before Jesse was groping Tracy's dick through his pants. Seeing that excited Molly and she told Tracy to stand up. She enjoyed the fact that they kept kissing even as he was getting to his feet, her sissyboys obviously liked making out. She picked up the trousers Jesse had picked out.

"Which one of these did you want the wimp to wear?"

"The light brown Ralph Lauren jeans."

She threw them at Tracy and told him to put them on. Jesse watched him change and for a brief moment he got his first look at Tracy's dick. It was partially hidden under the tail of his shirt, but from what he could see it looked small and hard. Surprisingly he had a very large ball sack, and that made his penis look even smaller. Once he had the jeans on Molly told him to stand next to her, she then turned him around by the hips so he was facing Jesse. Reaching in front of him she started rubbing his corduroy bulge.

"I take it you like these pants Jesse, you seem to like Ralph Lauren jeans a lot, why is that?"

"I don't know Molly, I just do. The fabric they use has a really nice feel to it, and their pants fit nice and look sexy."

"So you think my cuck looks sexy?"

"I guess so Molly, for a sissyboy. I really do appreciate you dressing your cuck in corduroy for me, it makes the wimp much more appealing. Thank you."

"You're welcome Jesse. I do enjoy making my boyfriends happy, especially when do things to make me happy."

She raised her eyebrows as if making a point, and he got it.

She gently patted Tracy's bulge.

"You're going to get a treat tonight cuck, you're going to get your little dickie sucked."

He looked down at her with a look of both excitement and confusion.

"But Madam, there's no fag here to do it."

"No cuck there isn't, but my new boyfriend Jesse is bisexual, and after kissing your corduroys he's very horny to suck a dick. Unfortunately, other than his, there are no real dicks here, so you better appreciate the fact that he's willing to settle for your little penis."

"But Madam none of your other boyfriends ever did that, they never even wanted to see my penis."

"You're right Tracy, they were real men, not queers, but things are a little different this time. You see Jesse is not only bisexual but he's also a closet sissyfag, and he'll be spending half his time with us in drag."

Tracy thought for a few seconds. "Does that mean he's your slave now too?"

"Well yes, but not right now. When he's dressed like a guy he's my boyfriend and you're a cuck just like always, but when he's dressed like a girl he's my fag slave just like you. In fact you two tinkerbells will be putting on fag shows for me when I'm in the mood."

Jesse spoke up. "Um, please make it clear that he's my bitch Molly."

"Relax Jesse, I was getting to that. He's right Tracy, you'll not only be a cuck, but even when you're both my fag slaves, you'll still be Debbie's slave too. His girly name is Debbie. With your little penis you'll always be the lowest wimp in the room. When you're with Debbie you'll be a bitch's bitch, a sissyboy's sissyboy. Are you getting the picture Tracy?"