Mistress Sharon Pt. 01

Dana had just finished moving his corduroy girly clothes from the washing machine to the dryer when the phone rang. Being a closet fag and having a corduroy fetish, he not only dressed often but jerked off with his wardrobe on a daily basis, sometimes two or three times a day. As you can imagine that created a lot of sperm stains, and his skirts and dresses needed to be washed frequently. The caller ID said Sharon Fox, she was his ex-wife's best friend and he hadn't spoken to her since separating from Samantha a year and a half ago.

"Hello."

"Hi Dana this is Sharon, Sharon Fox."

"Yeah high Sharon, what's up?"

"To begin with Dana, I'd like to say how sorry I am about the break-up, and I feel bad about not calling you sooner."

"It's alright Sharon, you and Sam were best friends, I get it."

"No Dana, I don't think you do. You see I haven't spoken to Sam either, I was very pissed off when I found out she was screwing around with Jonathan."

"Oh dear, I'm sorry."

"No, that's alright Sharon, that's what she was doing."

"Well anyway. I always liked you Dana, you know that, I just felt like I was in the middle. Please forgive me for not calling sooner."

There was a lengthy awkward pause.

"Well Sharon, what can I do for you today?"

"Actually Dana, I was hoping to discuss something that's been on my mind for a long time. If it's OK with you I'd like to come over for a little while, it won't take long I promise."

"Well, I'm not busy right now. What would you like to talk about?"

"I'm sorry Dana, I don't mean to be difficult but I'd much rather discuss it face to face if you don't mind, would it be possible for me to come over tonight?"

He hesitated and cleared his throat.

"Um, yeah, I guess so, how does 7:30 sound?"

"That sounds great Dana, thank you, I'll see you then."

"Wait Sharon! Can you give me some kind of a hint? I mean, is there something I should be concerned about?"

"Oh no Dana, nothing to worry about, I just have some questions about the past and they're a bit personal."

"Come on Sharon, you've got to give me something, I'm all curious now."

There was a brief pause.

"OK, it involves corduroy. That's all I'm going to say for now Dana, please just trust me, I'll see you at 7:30." She ended the call.

He slowly put down the phone. He was in a bit of a daze and suddenly a little horny. Other than two girls from high school and of course Samantha and Jonathan, no one else knew about his fetish, at least that's what he thought until now. There were times during his five year marriage that he wondered if Samantha had told Sharon, they were very close friends, but Sharon never said anything to indicate she knew.

Dana and Sam had a very kinky sex life right from the start. She warmed to his fetish right away, and after a short while she not only accepted his sissy crossdressing, she embraced it. In fact, being two years older at twenty-seven and having a lot more experience, it didn't take long before she made him be her sissy little slaveboy. Using corduroy to keep him under control she manipulated him with ease, only allowing him to indulge his fetish when and how she said so.

Over the course of their marriage she became more and more dominant. She used her bitchy persona, "Mistress Samantha" to abuse and humiliate him, and he loved her for it. She occasionally used a strap-on to fuck his bottom too, and sometimes she made him beg to suck her dick before she did it. After being forced to do it several times he confessed that he often fantasized about sucking a real cock when dressed like a sissy. That turned her on a great deal, and one night she made him do it to a friend of hers from work.

Dana was in full drag, pretty drunk and Mistress Samantha had him extremely horny. She orchestrated everything perfectly, and eventually led him into the bedroom where a guy in corduroy pants was sitting on the bed. The next thing he knew he was on his knees and she was humiliating him, making him beg for the guy's dick while he rubbed his face in his corduroy lap. It didn't take long before he eagerly unzipped the guy's pants, pulled out his hard boner and sucked him off like a horny little queer. Samantha reached under his skirt, yanked on his balls and ordered him to make Jonathan's big dick feel really good, all the while insulting him for being a sissy cocksucker.

The next day he tried to blame the alcohol but they both knew it was bullshit. He loved every minute of being a bitch for Jonathan's dick, and after doing it several more times it became a routine. It continued for a year and a half, two or three times a week, and sissy Dana willingly became Samantha's cuck. Well, sort of. He willingly became Samantha's slave and agreed to suck Jonathan's dick, but he did so because his wife promised him her "boyfriend" wouldn't be fucking her. When he found out that wasn't true, he finally grew a pair of balls and ended the marriage. Everything was finalized six months ago.

Hearing Sharon say the word "corduroy" gave him an instant boner, and each time he remembered the sound it got harder. He didn't know if Sharon was privy to any of what went on in their bedroom, the girls were very close so anything was possible, but he felt pretty confident Samantha wouldn't have exposed his cocksucking secrets. He knew his wife made many recordings of him sucking Jonathan's cock, and several of him jerking off with her "boyfriend's" pants. Many times she would humiliate him while they all watched him act like a little pervert on the videos. However, as bitchy as Mistress Samantha could be, he didn't think she'd ever show them to anyone outside of their little ménage-à-trois.

Actually, as he thought about it, the only time he ever suspected anyone knew about his fetish was when Sharon visited dressed in something corduroy, which happened fairly often. Sometimes his wife would tease him unmercifully. She'd make a really big deal about how sexy Sharon's outfit was, pointing out how nice the fabric felt and asking him if he liked it. He always felt extremely awkward and Sharon would give him a sly smile that made him suspicious, but she never said anything to indicate that she knew. He realized he could've easily been imagining things and always chalked it up to wishful thinking, but after today's phone call he wasn't so sure.

Having a few hours before Sharon would arrive, he retrieve one of his corduroy dresses from the closet and spent the next hour or so stroking his seven inch boner with his favorite fabric, all the while fantasizing about her. She was a couple of years older than Samantha, making her several years older than him. A nice looking woman who stood about five-ten and weighed around a hundred and forty pounds. Her shoulder-length, dark-brown hair was always kept very neat, and her blunt cut bangs created the illusion she was wearing a helmet. She wasn't a raving beauty but she was a fairly attractive woman with a nice set of tits and a tight ass.

He did have to admit she was somewhat boyish, she was by no means a delicate flower. In fact, Dana found her large frame and muscular body a little intimidating. He'd never want to get into a physical confrontation with her because he wasn't sure he'd win. Samantha made many comments about her being butch and how her hairstyle didn't help, but Dana always suspected she was a little jealous for some reason. In general, even though she was boyish, it was a nice blend of boyish and pretty, and it worked well.

During his marriage he often dreamed about her when masturbating, and he always liked the fantasy of Samantha and her being co-mistresses. In fact it was the thought of her fucking his ass with a big strap-on sticking out of her corduroy jeans that took him over the edge. He shot a big load of creamy jizzum all over the front of his dress, then enjoyed a few minutes of afterglow before reality returned. He cleaned everything up, then ate a light dinner and had a drink. As he waited he wondered what she wanted to talk about, but he couldn't come up with any plausible explanation.

After initially dismissing the idea, he decided to put on his black jeans, a grey t-shirt, and a vest that matched the pants. Both items were made of a mid-wale fabric that had a very nice feel. With the alcohol beginning to sway him, he decided that if nothing else, wearing those clothes while discussing corduroy with Sharon would give him a big thrill. He did some last minute straightening up and was surprised when the doorbell rang, she was about twenty minutes early.

Downing the last of his drink, he took a deep breath and opened the door. When he did he got an immediate thrill. She was dressed in a pair of rust-colored, wide-wale corduroy dress pants and a matching vest. He'd seen the outfit before, it was one of the outfits Samantha teased him with long ago. The trousers had flared legs and the fabric was very plush, it looked like it'd be heaven to touch. After ogling her momentarily he quickly composed himself, but she'd already noticed the excitement in his eyes, and it was exactly what she wanted. She'd hoped that by mentioning corduroy on the phone it would trigger his obsession and put him in the right frame of mind, and judging by the way he was dressed she knew she'd been successful.

He swallowed hard. "Hello Sharon, come on in." Then retreated a bit so she could enter.

"Hi Dana, thank you. You look very nice."

She took a few steps in then turned and waited, and after a few awkward seconds of eying each other, he showed her to the living room. He offered her a drink, and when he went to get it she settled in on the sofa. The place was basically clean and well-kept, but it definitely lacked a woman's touch. When he returned with the drinks, he sat in the arm chair and they waded through some idle chatter, mostly catching up. Neither of them seemed to be in a hurry. After a half hour or so Sharon felt the time was right, and at the next lull in the conversation she went for it.

"I really like your outfit Dana, and that brings me to the reason for my visit. You know I'm not one who usually beats around the bush, so please forgive me if I'm a bit blunt. As you know, Samantha and I were best friends for a long time, going back long before she met you. We were the kind of girls who told each other everything, and Dana, by that I mean everything."

She made a hand gesture underlining the last word. She then paused to light a cigarette, and he lit one too. She crossed her long legs like a lady, sat up, faced him more directly and struck a confident pose.

"One of the first things Sam told me about you, was your weird love of corduroy. She told me how much it turned you on and how she used it to control you. All those times she embarrassed you with my outfits I knew exactly what she was doing." She gave him a big smile. "And to be truthful Dana, it was fun watching you squirm."

He returned a timid smile, looking both embarrassed and a little nervous.

"She also told me you were one of those sissy little wimps, the kind who wears skirts and dresses, and that she made you be her slaveboy."

His face turned beat red, he looked down and slowly shook his head but didn't try to deny anything. Several seconds later he finally found his voice.

"Sharon, I, I'm trying to get past Samantha. Why are you bringing all this up?"

She softened her voice. "Oh Dana I'm sorry, I didn't mean to upset you dear. I just wanted to tell you that I knew what you and Sam used to do, and I always liked what she told me. In fact, when Samantha used to tell me how much fun she had abusing you, it always made me a little jealous. It sounded like you really enjoyed being humiliated, and it made me wish I had a sissy slaveboy of my own."

He sighed deeply and appeared to melt in his chair with embarrassment. After a minute he did seem to loosen up though, and it pleased her that he never tried to deny anything. Reading him carefully, she decided to try and gain a little more trust before pushing him any harder. She maintained her soft tone.

"Dana, listen to me please. Sam may have been my best friend, but the minute I heard about her and Jonathan it made me sick. I couldn't believe she would do something like that to you, it was a horrible thing to do. I always liked you very much Dana, and you never deserved to be treated so shitty."

He slowly made eye contact and the embarrassed smile on his face was so pathetic she thought he looked cute, like a little boy.

He let out a small sigh. "Thank you Sharon, I always liked you too."

He then sheepishly returned his eyes to his empty glass.

She cleared her throat. "I did say I'd be brief, so perhaps I should get to the point of my visit. As I said earlier, I really liked the idea of having my own little slaveboy, it's a very exciting fantasy. And, well, now that Sam is no longer in the picture, I see no reason why it couldn't be more than a fantasy. If that's what you wanted of course."

He looked genuinely shocked and they locked eyes momentarily before Dana looked away. After thinking for a moment, he spoke in little more than a whisper.

"Sharon, I um, I'm not really sure what to say."

He looked genuinely confused, which was to be expected, she knew she was blindsiding him. However, at no time did he grow a pair of balls and act like a man, in fact he never objected in any way, and that emboldened her. She took a long drag of her cigarette and decided to go for broke.

"OK Dana, let me be more specific. What I want from you is blind obedience, just like you gave Samantha. I want you to be my sissy slaveboy and do whatever the fuck I tell you to do. In return your mistress will take full control of corduroy, and you'll only get rewards if you earn them."

She took another drag and uncrossed her long legs. She then leaned forward and took an aggressive posture.

"And Dana dear, what I want more than anything else in the world right now is an obedient little bitchboy. One who'll suck any dick I tell him to, whenever and however he's told."

He gave her a horrified look and she thought he was going to object, but after a few seconds he simply shut his mouth and returned his eyes to his lap. She saw surrender overtake him and she liked what she saw, his submissive nature was coming to the surface. He then said in a very meek voice.

"Um, Sharon, I don't do that."

She immediately laughed a little, and that shocked him a bit.

"Dana honey, let's not kid ourselves OK? I saw the videos of you sucking Jonathan's dick. You not only do it sissyboy, you love doing it. That was fucking obvious."

He slumped in his chair completely deflated and lit a cigarette, never once making eye contact. There were no secrets anymore, she not only knew he was a cocksucker but she'd watched him do it. He felt totally humiliated and exposed, but after a minute the humiliation wrapped around him like a blanket, it felt good, he hadn't felt it in a long time, and it was sexually exciting.

She sensed his inner wimp was coming out and decided to push harder.

"Please don't look so embarrassed Dana, I liked watching you suck Jonathan's cock, it turned me on. In fact, after I saw you do it a few times I got some queer porno movies, and now watching guys suck each other's dicks gets me very horny. After a while I started fantasizing about you being my cocksucker, just like you were for Samantha. And I figured since you like being a cocksucking slaveboy and I'm looking for one of my own, maybe we could have some fun."

She put out her cigarette. "You know Dana, oddly enough, Jonathan's dick may have been the best thing to happen to both of us. You discovered you're a wimpy little bitchboy who loves sucking cock, and I discovered that I love watching you do it. Sounds a lot like karma to me."

She then went quiet for a moment to let him sort things out, and after a minute he spoke up, but he didn't make eye contact.

"Sharon, I, I'm not sure what to say. Are you really serious?"

She smiled. "Yes Dana, I'm very serious, and I think you'd really enjoy yourself too. You see, my little brother Jody's been living in my house since April, and to put it bluntly, he's a limp-wristed pansy. If you keep me happy and earn rewards, you tinkerbells could wear corduroy dresses and fornicate yourselves right into sissy heaven. Although that would be more of a treat, a reward for good behavior. You'll spend most of your time sucking my boyfriend's dick for me, and I'll humiliate the shit out of you whenever you do. Also Dear, I'm sure Perry will be more than happy to wear corduroy pants whenever you're my little slaveboy."

She released a throaty chuckle, and it sounded very sexy.

"And, if you make him feel really good, maybe you'll get to jerk off with his pants, just like you did with Jonathan's."

He blushed again and his eyes bulged in reaction to her last comment. It was now obvious she knew everything that happened when he was being Jonathan's bitch, and the look on his face was one of total humiliation. Seeing that, she decided to back off a little and give him some time to think. She took a sip of her drink, placed the half empty glass on the end table and shifted forward to the edge of the sofa.

"Alright Dana, I've said all I wanted to say for now, and I thank you for allowing me to do so. Perhaps you should take a few days to think about it, and if you're interested please let me know."

She paused. "Dana, could you please look at me dear."

He raised his eyes slowly.

"Regardless of what you decide, I hope we'll always remain friends, I really do like you Dana."

She stood up and made a very deliberate act out of smoothing her trousers and straightening her vest. He began to get out of the chair, but she motioned him to stop.

"Please Dana, sit, I know my way out."

With that she slowly headed for the door, and even though he was still in shock his eyes remained glued on her corduroy covered ass the entire way.

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He sat for several minutes reviewing what just happened, and the more he thought about it the more he couldn't believe it. Since separating from Samantha a year and a half earlier he hadn't had sex with anyone, so having such an intimate conversation with Sharon made him extremely horny. He made himself another drink and dressed in one of his pretty corduroy jumpers. He then spent the next few hours playing with his sissy penis and feeling girly, and as he did, he fantasized about being both Sharon's slaveboy and her brother's sissy girlfriend. He'd never had sex with another fag before, and that idea was driving him crazy with lust. He eventually ended the evening by jerking off with a pair of Samantha's wide-wale dress trousers, pumping a big load of jizzum all over the front of his jumper. He stole the pants from her closet the day he moved out.

The next day, and the two that followed, he gave serious consideration to Sharon's proposal. That is, when he wasn't jerking off, which he did at least twice each day. At first the idea of being another guy's bitch was difficult, mainly because Samantha betrayed him with Jonathan not all that long ago. However, when he could get past all that, he really liked the idea of being a cocksucker for Sharon's boyfriend, especially with her supplying a lot of humiliation.

After the third day, he decided that if he was going to do it he probably shouldn't keep her waiting, so he made the call. At first he felt awkward having the conversation over the phone, but her arrogant attitude quickly put him at ease. As soon as he expressed an interest in her proposal her mistress persona kicked in and she made it clear who was in charge. He liked that. She instructed him to show up at eight o'clock the following evening, and it sounded like she was eager to get him started on his new life of servitude. She also instructed him to bring a list of any limitations he might have so they could discuss them before getting started. Her final instruction was to dress masculine, no sissy shit on the first night, if things went well he'd get to dress up girly the following night with Jody.