Engaging Sissy Submissive Stories for Every Fantasy

Engaging Sissy Submissive Stories for Every Fantasy

Get Access to the Hottest 18+ Sissy Assignments Around!

Personalized collection of assignments created just for you. Click below to start your journey!

Get Assignments for 2025

CAROL, CANDY & THE EX PT. 01

It was Monday night and Davie was bored. He’d grown tired of all the online political bullshit, there were no movies worth watching on Amazon, he didn’t feel like playing a mindless video game and he was a little too drunk for reading.

He decided he’d jerk off with one of his corduroy skirts and call it an early night, but before getting to the bedroom his phone distracted him. The caller ID said Carol Robinson, a name he was unfamiliar with. His ex-wife flashed through his mind, her name was Carol, but he hadn’t heard a word from her since their divorce. Being bored he shrugged and answered.

“Hello.”

“Hi Davie, it’s Carol.”

He recognized the voice immediately.

“Carol? Really?”

“Yes Davie, really.”

There was a brief silence.

“Look, I know it’s been like ten years or whatever, but you do remember me right? We used to be married for God’s sake.”

Right away with the attitude, now he knew it was her.

“Yeah I remember you Carol, I just don’t understand why I’m talking to you.”

She was about be a smart ass but stopped herself. She realized old tapes were playing and she didn’t call to rehash old wounds.

“OK look, I’m sorry. I didn’t call to fight Davie, I just wanted to talk to you.”

He was impressed with her apology, he’d heard so few of them. He calmed a bit.

“Alright Carol, maybe we should start over. Hi Carol, how have you been?”

They slowly and cautiously waded into recapping their lives over the past decade and her almost friendly demeanor surprised him. She started by telling him that four years after their divorce her aunt, and sort of adopted mother, passed on and left her everything, making her a very wealthy woman.

He wasn’t surprised nor did it sound like a dig, she sounded genuinely sorrier for the loss than happy for the gain. He asked about her last name and she explained she’d gotten married three years prior. That made him wonder even more about why she was calling.

Without going into much detail, he told her that his work life had progressed well and he had a few relationships but never married. The conversation stayed civil but after twenty minutes of trying to catch up with little in common, he finally inquired as to the point of her call.

“Oh, well, to be honest Davie, I’d like to have a chat with you about something, but I’d prefer to do it face to face.”

“About what?”

“Like I said, face to face, that’s not on the phone Davie.”

She immediately regretted her attitude, it just seem to flow so easy when talking to him.

“OK look, I’m sorry, I’m upset, please just hear me out. I want to talk about something personal, and I thought maybe you could help me with something. I realize it’s been a long time and we haven’t exactly been the best of friends, but I really think you might be the only person on Earth who could understand.”

There was a brief silence.

“OK Carol, what did you have in mind?”

She sighed in relief.

“Thank you Davie. I thought maybe we could meet at Mario’s.”

Mario’s was a restaurant/bar they frequented when they first started dating, it was local and it had very private booths, if you could get one. They agreed to meet the following evening at seven o’clock. At the end of the call she thanked him again and sounded a little scared. That surprised him, it wasn’t often she let her guard down.

Hearing her voice brought back visions of her in various corduroy outfits. It reminded him that even though she wasn’t interested in his crossdressing and bisexual desires (which proved to be touchstones for their split) she was always accommodating when it came to his fetish. She found it cute and amusing and he loved that she did.

He made another drink, went in the bedroom and started jerking off with his blue wide-wale corduroy dress. He remembered the sex they had in better days and eventually splattered a big load of sperm all over it. He then went to sleep feeling content, and a little intrigued by what tomorrow would bring.

****************************************************************

He arrived at Mario’s ten minutes early and got a booth in the back corner. The place was half empty and that surprised him, it used to be a very busy place. Ordering a drink while he waited, he couldn’t help remembering some of the times they had together in that booth. He was dressed in a pair of blue jeans and a polo shirt. He eschewed anything corduroy because he didn’t want her to think he had that on his mind, although apparently he did.

At ten after seven he saw her coming down the aisle and couldn’t believe what he saw. She was wearing a pair of emerald green high-wasted corduroy dress trouser, and a matching vest. It was buttoned up over a yellow long-sleeve turtleneck blouse. The outfit was obviously fitted and done in a plush wide-wale fabric. It was an attractive outfit that looked very expensive. Her blond hair was still short and styled nicely and her make-up was tastefully done. She looked older but pretty much the same, and he imagined he did as well.

Carol was not unattractive but she’d always been sort of a plain-Jane, and even though her newfound wealth had obviously helped in some ways, it didn’t add much in the way of pizzazz. As she approached a slight smile broke through her natural smirk. She slid into the seat and her eyes darted all around the booth before focusing on him.

“Wow, lots of déjà vu. It’s been awhile.”

He nodded with a polite smile but said nothing.

“Thank you for coming Davie, I’m sorry I’m late.”

She flagged the waitress, ordered a scotch and soda and he said he was good. They’d always liked the same drink and apparently that hadn’t changed. They wading into general small talk until her drink came, but once they were alone he broke the ice.

“So what’s on your mind Carol.”

She looked unsure for a moment but quickly pulled herself together.

“I’ve got something going on in my life Davie, I’m going through a difficult time, and based on what we’ve been through I thought you might be able to help me.”

“Yeah, I got that on the phone. But I have to admit Carol, I find it pretty strange that you’re coming to me. I mean obviously it’s not about money, and I’m pretty sure you wouldn’t be coming to me for marital advice. So what’s the deal?”

She took a sip. “Actually Davie, it is kind of like marital advice. Well not so much advice, more like, I don’t know.” She struggled for the word. “Assistance, I guess.”

He gave her a puzzled look. “Huh?”

She sighed. “This isn’t easy for me Davie. Will you at least make me one promise before I go any further?”

He shrugged. “What?”

“What I’m going to tell you is very personal and very embarrassing. I just want you to promise me that if you’re not interested you won’t use it to be cruel.”

He looked a little shocked and lowered his voice. “Oh, you mean like you were when you told Sharon about my crossdressing?”

Her eyes flared. “I can’t believe you said that, don’t blame me because you’re a faggot.”

He sarcastically chuckled and kept an even voice. “You know Carol, if you’d been a little nicer to me in general and channeled your bitchiness into the bedroom where I wanted it, it might have worked for us.”

“Fuck you Davie”

She realized it was dumb as soon as she said it. He slowly shook his head, smiled in disbelief and threw a $20 bill on the table.

“Thanks Carol. Thanks for showing me you haven’t changed a bit, have another one on me.”

He started sliding out of the booth.

“Wait Davie, please don’t leave.”

He heard something in her voice, something desperate, something he’d never heard before. He stopped.

“I’m sorry. You’re right, I was a bitch back then. I didn’t care about anyone but myself. Please don’t go.”

He thought he saw a tear in her eye and after a few seconds he slid back in. She looked down at the table and he gave her a moment to collect herself.

“I’m sorry Davie, I guess with our history I’m just feeling vulnerable and afraid of getting hurt. The truth is I really didn’t want to hurt you back then, I was just very unhappy and took it out on you. And for what it’s worth, I’m sorry.”

He was genuinely shocked to hear her talk like that and let his guard dropped a little.

“Look Carol, why don’t you just tell me what’s bothering you? You called me, I didn’t call you, so obviously I didn’t come here to hurt you.”

She smiled a shy smile, which looked strange on her, then she just let it out. She explained that after acquiring her wealth she tried to fit in with the younger clubbing crowd. The attention she got from the younger girls felt good because she’d never had a lot of friends before.

She also liked the attention she got from some of the guys, but after a while she learned how phony everything was. She did however take up with one guy named Robbie. He was very young and good looking, kind of a pretty-boy but all the girls loved that. They were a very popular couple and she eventually married him, even though at twenty four a lot of people thought he was a gigolo. She took a deep breath, as if the hard part was coming.

“Soon after we were married I found out he was a fag.”

She lowered her voice. “Just like with you.”

He bristled a bit but couldn’t dispute the accuracy.

“He started out just wanting to dress up and play games, but after a while he wanted to do things with dicks like you did. I just couldn’t understand why I kept attracting guys like that.”

Davie suddenly wondered why he was listening to this, but her fragility was so out of character it kept him intrigued.

“Then why are you staying with him? I mean, you didn’t have any problem leaving me, and it sounds like things are similar.”

She almost got defensive but quickly realized it wasn’t a dig, he seemed sincere.

“I know. I gave up too quickly with us Davie, I’ve known it for a long time, and I don’t want to do that again.”

Then she shocked the shit out of him.

“And, well, to be honest, he has this really big dick” She let out a sad chuckle. “And when he does fuck me it’s incredible.”

Davie had no idea what to say.

“But the problem is he’s not acting like a guy anymore. He lets me climb on top of him when he’s in drag, and his dick feels really good, but it’s not the same as being fucked by a guy. You know what I mean?”

She gave him an embarrassed look and they both chuckled.

“No, I guess you don’t.”

It broke the tension and he had to admit that for some strange reason he was actually interested. He wasn’t sure if he should say anything or just keep quiet, so he opted for the latter. They both sipped their drinks and after a minute she continued.

“I don’t want to paint the wrong picture about Robbie, he does act like a guy when we’re out socially, and quite frankly he’s a big hit with the other ladies, but at home he’s dressing like a fag almost all the time. It’s also become clear he wants to have sex with another fag.”

He was amused but didn’t show it. He couldn’t help feeling a little satisfaction at her expense.

“Well Carol, I’m not sure what to say. I’m sorry you’re having problems, but what’s this got to do with me?”

“I don’t know Davie, just tell me what you think.”

He shrugged.

“OK, but the first thing I’d suggest is probably the last thing you want to hear. Maybe you should let him have some fun with another fag. I mean, when we were going through our thing I’d have been very grateful for that.”

He felt funny saying it, but it was the truth. It was also what she’d been hoping to hear.

“Well actually Davie, we did talk about that and he suggested the same thing. But when I told him that in return I wanted to have sex with a guy who’d fuck me like a guy, he wasn’t too keen on the idea.”

He shrugged again.

“I only know what you’ve told me, but it sounds like a fair deal to me. Granted, most guys can’t handle the idea of their wives fucking another guy, but that’s something you guys need to work out.”

“Yeah it sounded fair to me too, but I think I understand what’s bothering him. Robbie’s a little insecure and I think he’s worried I’ll find a new husband or something. I don’t know, in a weird way that’s kind of nice. But that’s where we are right now, at an impasse.”

They sat silently for a minute then Davie excused himself to take a piss, and while he was away they both used the moment to think. He returned with two more drinks, which Carol took as a good sign, and as they sipped them she caught him eying her tits. She liked the fact that her corduroy outfit had finally grabbed his attention, she was beginning to wonder if he no longer had his fetish. She even stretched a little, pushing her tits in his direction.

He spoke first.

“So what are you going to do?”

She knew it was the moment of truth.

“Well actually, I think I’ve come up with a solution and that’s why I wanted to talk to you, I wanted to see what you thought about it.”

He nodded.

“Ideally, I think if I could find a guy who liked being a fag sometimes but still liked fucking like a guy at others, it might work out perfectly. That way he could make us both happy and Robbie wouldn’t have to worry about me wanting a new husband. I mean, why would I want to marry another fag when I already have one?”

She caught him eying her tits again. He took a sip and shrugged.

“Sounds like a plan. Got anyone in mind?”

She looked him straight in the eye.

“Yeah Davie I do, that’s why I’m talking to you.”

He didn’t get it and waited for an explanation.

“I used to be married to a guy like that.”

It took a couple of seconds, then his eyes bulged.

“Wait a minute. Are you saying what I think you’re saying?”

She reached into her purse, pulled out three pictures and slid them across the table. They were of Robbie in full drag and she thought he look especially good in them.

“This is Robbie, otherwise known as Candy.”

He was in shock to begin with and the pictures took it to a whole new level. To be blunt, he or she, was fucking gorgeous. He felt his dick getting hard and his face blushed, he was completely unsure of how to react. She thought she saw lust in his eyes as he stared at the pictures and felt relief. She guessed if he was going to get pissed off he wouldn’t be staring at Robbie like that.

“This.” He coughed. “This is your husband?”

“Yes Davie, that’s Robbie. I never thought I’d say this about my husband, but he’s a good looking girl. What do you think?”

“I don’t know what to say Carol. Are you, are you really asking me to have sex with you and your husband?”

She folded her hands on the table, leaned forward and stared him directly in the eye.

“Yes Davie, I guess I am.”

“Well I, I. You’re serious about this aren’t you?”

“Yes Davie, I am.”

He grabbed his drink and stared at it, he was obviously flustered. Seeing that, she pulled a pen from her purse and wrote her number down on the back of one of the pictures. She then gulped down her drink and slid out of the booth. Leaning down she spoke softly.

“I’m very serious Davie. When we were married you always wanted to have sex with another fag, but that never happen. Well, maybe it could happen now. Call me.”

She kissed him on the forehead, turned and walked out, and his eyes remained glued on her corduroy covered ass the whole way. He shoved the pictures in his pocket, downed his drink and went home in a daze.

He stayed in a state of total confusion for the rest of the night, and before going to bed he jerked off with one of his corduroy skirts while staring at the pictures.

**************************************************************

He spent the next two days in a fog, he even went home from work early on Thursday because he couldn’t focus on anything but Carol. He started drinking as soon as he got home and after his second scotch he put on his orange mid-wale corduroy skirt & vest outfit, along with a white tank-top, bra and breast forms. The wig, make-up and heels followed soon after.

He normally didn’t do full drag on a weeknight, but by then he was obsessed with the thoughts of Carol and Candy. In fact, he’d already made his mind up to call her, he wanted to get some clarification on a few things, and if all went well he knew he was going to give it a try. In addition, the alcohol convinced him that having the discussion while in drag would be fun. At 7:30 he finally got up the nerve and called.

“Hello.”

“Hi Carol, it’s Davie. Is this a bad time?”

“Hi Davie, ah no, it’s not a bad time at all. As a matter of fact I’m glad you called.”

“Oh OK, well I’m glad to hear you say that.”

He was obviously nervous and she liked that he was.

“I’m calling about our conversation at Mario’s the other night, and, I just wanted to ask a few questions. Would that be alright?”

“That would be fine Davie.” She sounded a little excited. “What’s on your mind?”

“Well Carol, this is a little awkward, but, I take from your outfit the other night that you remembered my fetish.”

“Fetish? What fetish?”

“Huh?”

She chuckled. “Relax Davie, I’m teasing you. Yes I remember your thing for corduroy. How could I forget?”

“Oh, alright.” He chuckled nervously. “Well, I was just wondering if it would play a part in the games you wanted to play.”

She cooed. “Oh, I bet you’d like that.

Of course Davie, don’t be silly, there will be lots of corduroy involved.”

He cleared his throat. “Candy too?”

“Yes Davie, Candy too. I told Robbie all about you when I suggested this and he liked the corduroy thing, he said it gave him something to work with. Whatever that means. But no, there will be no problems with your fetish.”

He liked hearing that, and between that and the drinks he loosened up. They spent an hour or so discussing likes and limitations and she informed him that sometimes when they fucked Candy would be their cuck. He said he had no problem with that if Robbie didn’t.

“Don’t worry Davie, he wants it, trust me. But there is one more thing, and I’m not sure if you’re going to like it or not. When you’re spending time with Candy he wants you to be his bitch, he wants you to be submissive to him. I think he wants to be like your fag mistress or something. Do you think you’ll have a problem with that?”

“Well, as long as it’s not like whips and chains and shit, I’m not looking for a lot of pain Carol, especially from a guy. That was never my thing.”

“Oh God no Davie, he’s a wimp, he’s no bigger than I am. You’ve got nothing to worry about like that. He just wants to be in charge, I think it’s kind of an ego thing. Since you’re getting to screw around with his wife I think he wants to screw around with you. I guarantee that once you meet him in person any fears you might have will be gone in an instant.”

They talked things over a little more and she told him that on their first night she wanted him to be in drag so Candy could check him out and get comfortable with Debbie. He could either come dressed or bring his stuff over and dress over there, either way would be fine. She gave him her address and he agreed to come over the following evening.

“Thank you Davie, I really hope this works out for all of us. I’ll see you tomorrow.”

She ended the call and he downed the last of his drink. He was a little drunk by then and very excited. He was also getting nervous, wondering what he was getting himself into. He started rubbing his dick through his skirt as he replayed the conversation in his mind, and shortly thereafter he jerked of with a pair of corduroys while staring at Candy’s pictures. The trousers belonged to an ex-girlfriend and he liked masturbating with them.

************************************************************

Although he was tempted, he decided not to show up at Carol’s in drag. Instead he packed an overnight case with all his girly things and two outfits for his introduction to Candy. He was nervous to be sure, but having made up his mind to go through with this little ménage à trois he was eager to get started.

The house was a McMansion on a large lot with plenty of privacy, he parked on the side and went to the main entrance. The door was answered immediately and he got his first thrill of the night. Standing in the doorway was Carol dressed in a powder blue mid-wale corduroy jumpsuit. It fit her body like a glove and fabric looked like it had a nice soft finish. He liked it a lot.

“Hi Davie, come in. I trust you had no problems finding the place.”

He shook his head. “No, no problems, I’m somewhat familiar with the area.”

She backed off to let him in and he gave her a nervous smile as he passed. Once inside she directed him to a sitting room and offered him a drink.

“I thought we might have a drink before we get started to kind of loosen things up. Is that OK with you?”

“Yeah that’s fine. This is a really nice house, you’ve done well for yourself.”

“Thank you Davie, that’s very nice of you to say, and I’m really glad you’re here.”

She gave him his drink, sat next to him on the sofa, very close, and spoke in a pleasant tone. Over the years he’d forgotten how nice she could be when she wanted to.

“In a few minutes I’ll bring you to meet Candy, but first I’d like to talk about a couple of things real quick. OK?”

He took a sip, shrugged and nodded. He also checked out her jumpsuit now that he could get a closer look.

“First of all, Robbie’s a little nervous, so don’t blame him if things are awkward in the beginning. He’s never been with an older guy before and I think the fact that you’re my ex may be messing with his head. Oddly enough, I think in some ways he likes the idea, but I also think he feels a little threatened by it.”

She took a sip.

“I can tell you this though, he’s really looking forward to having sex with Debbie, and I think you’ll like his outfit. I won’t say much more because I’ve probably said too much already, but just trust me Davie, he’s really looking forward to this. OK?”

He gave her a timid smile. “Yeah Carol it’s OK. I feel a little funny saying this, but I’ve been looking forward to it too.”

She smiled back, took a long sip of her drink and put it on the coffee table. Then turning to him she took his free hand in hers.

“I want to say something else Davie, and I’m not really sure how to say it.”

She kissed the back of his hand.

“OK, here goes. You and I have history Davie and a lot of it wasn’t good, we both know that. It’s also been a long time since we’ve seen each other. I guess what I’m trying to say is I just hope things work out. I know things didn’t go well the last time but those were very different circumstances, maybe this time we can have some fun. Who knows? Maybe we might even end up liking each other.”

She smiled.

“I’d really like that Davie, I’d really like if we could put the past behind us and just enjoy, well, whatever this is. Do you understand what I’m saying?”

“Yeah Carol I think I do. We’ll just have to see how your husband feels about it.”

She took his drink, put it on the table, then wrapped her arms around him and pressed her lips to his. He was momentarily shocked but quickly returned the kiss with enthusiasm. He also used the opportunity to feel her up in her jumpsuit, it had a wonderful corduroy feel and she didn’t seem to mind.

After a minute she broke the kiss but stayed close. She closed her eyes and sighed deeply. When she opened them she gave him a timid smile.

“That was for old time’s sake Davie.”

She backed off, picked up her drink and downed the last of it.

“Now I want you to get acquainted with my sissy husband. If all goes well the next time we get together you and I will be lovers, but new lovers Davie. New circumstances and new fun. OK?”

He smiled. “Yeah Carol, that’s fine with me.”

“Excellent Davie! I’m really glad you feel that way.”

Switching gears she abruptly clapped her hands on her knees.

“Alright big boy, let’s go meet Candy.”

He grabbed his drink and emptied it, then followed her down a hall to a large bedroom. Once inside she open her arms and did a slow turn.

“This is your room Davie. Eventually you can move all your girly stuff in here if you’d like. So get settled and make yourself up pretty, your girlfriend’s in the room across the hall.”

She stepped forward, brought her face close to his and gave him a sexy smile, then reached down and rubbed his bulge.

“Now go seduce my husband Davie, make him so happy he’ll want you here all the time.”

She winked, gave him a quick kiss on the lips and slowly walked out.

He sat on the bed for a few minutes letting the reality of where he was sink in, then he opened his overnight case and let Debbie out to play. To meet Candy he’d selected a beige wide-wale corduroy shirt-dress with a dark brown leopard print. It was knee-length, had long sleeves and buttoned all the way down the front. Underneath he’d wear his red lacy bra and medium sized breast forms. For below he brought a pair of dark brown wide-wale leggings with a hole cut just big enough for his cock and balls to squeeze through. To finish the outfit he had a pair of chocolate brown corduroy Toms wedges.

Once dressed, he spent a few minutes fixing his shoulder-length chestnut wig and applying some simple make-up. When finished he liked what he saw in the mirror. Debbie wasn’t passable and never would be, but for a prancing-nancy he didn’t look half bad. He decided to go full fag and pulled a shoulder bag from his case. It was upcycled from a pair of tan mid-wale corduroy jeans and he liked it a lot. He found it on Etsy two years ago and this was his first chance to use it. He threw in his make-up case and a package of tissues just to give it some purpose.

Feeling good about his outfit, he looked in the mirror, took a deep breath and imitated Joe Gideon.

“It’s showtime, folks!”

He walked through the bedroom and out the door, then knocked on the door across the hall.

“Come in fag.” The voice was feminine but low pitched.

He opened the door and stepped into a bedroom a little larger than the one he just left. Directly in front of him was a king size bed covered in a blue and white paisley bedspread, along with four pillows in matching shams. To the right was a sitting area with two armchairs on either side of a small table. The table had two drinks. The right chair contained Candy, and he was everything Debbie hoped he’d be.

Carol wasn’t kidding, with him being 6′ tall and 175 pounds he had nothing to worry about. Candy was a petite fag probably no more than 5′ 6″ and 110 pounds, with long flaming red hair that obviously wasn’t his. He was very pretty with large full lips, deep blue eyes and long lashes. His make-up was impeccable and looked like it must have taken a while, he’d obviously spent time preparing for the evening. He was definitely passable, but knowing he was a fag Debbie could see a hint of masculinity, although it wasn’t much more than you saw in handsome women like Kathrine Hepburn or Angie Harmon.

The thing that stopped him in his tracks though, was his outfit. He wore a rose colored wide-wale corduroy big-shirt, tucked into a knee length maroon mid-wale skirt. The shirt struggled to contain a rather large set of tits, not clownishly huge, but considerably larger than a girl his size should have. Fags sometimes did that and he always suspected it was due to an insecure overcompensation. However, with his naturally good looks it really wasn’t necessary, so maybe he just liked being a big girl. Debbie wasn’t complaining though, it added a little bawdiness to his Candy persona.

His skirt was a jeans style A-line with two front pockets and a fly. Below he wore pink stocking and a pair of ruby red corduroy ankle boots. He definitely didn’t scrimp on the corduroy and Debbie took that as a good sign. He was smoking a Virginia slims and a soon as they made eye contact he blew a plume of smoke toward the ceiling, then pursed his lips as if evaluating him.

“Come in Debbie and have a seat.” His voice was pleasant with just a hint of gravel in it, which sounded sexy.

He obeyed and sat like a lady, checking out the surrounding. Candy stared at him the whole time and when their eyes met again he had a strange look on his face, a neutral look, as if making up his mind. He then nodded to no one in particular, put out his cigarette and stood, and when he stepped directly in front of him Debbie felt his penis spring to life.

“So you’re the ex.”

He nodded.

“Well ex, I want to show you something bitch.”

That shocked him a little. Then he shocked him some more. He slowly hiked up his skirt, reached under and pulled out his cock, then wiggled it at him. It was fucking huge! He guessed it was a foot long and about two inches thick, although he’d later point out it was “only” eleven inches. Its most notable feature was a large beautifully shaped mushroom. It also had a well-defined frenulum sitting a couple inches down from its knob, and it was so hard it looked like it was made out of wood. In short it was a magnificent cock, one any porn star would be proud to have.

“Take a good look bitch, even in full drag I’m more of a man than you’ll ever be. Do we understand each other?”

When he managed to pull his eyes away, Debbie reflexively gave him a hard stare in response to his tone and slowly nodded. As soon as he saw that Debbie wasn’t intimidated Candy’s flash of bravado faded, he hesitated, then pushed his dick back under his skirt and lowered it.

“Well do you?” It sounded a lot weaker.

Debbie quickly surmised his posturing was meant to cover the fact that he felt intimidated. He took a deep breath, put a smile on his face and spoke softly.

“Yes Candy I do. And if I may say so, that’s an absolutely magnificent cock, and it’s attached to a beautiful lady. One far more beautiful than I’ll ever be.”

He looked unsure of himself, and now a little embarrassed, Debbie could also see he liked the compliment. His whole demeanor softened and he spoke in a pleasant tone.

“Thank you Debbie, why don’t you have your drink and relax.” He sat back down and lit another cigarette.

Giving him a minute to compose himself, Debbie changed the subject by complimenting his room and mentioning how much he liked several of his knick-knacks. Candy seemed to relax a little, but not entirely. Debbie realized the issue had nothing to do with who was prettier, or who had a bigger dick, those facts spoke for themselves. No, he knew what it was about and needed to break through the awkwardness. After a few minutes he took a gulp of his drink and stood up.

“Candy, I’d like to say something to you dear, can I get a little closer?”

He shrugged and nodded. Debbie stepped forward and knelt at his feet, surprising him.

“Miss Candy, can you please do me a favor?”

He sat up and looked puzzled.

“What did you have in mind Debbie?”

“Could you please pull your cock out through the fly of your skirt? I’d really like to see it again, and I’d love to see it sticking out of your pretty skirt.”

He bit his lip and shrugged again.

“OK girl, if that’s what you want.”

Debbie had a feeling he wanted it too. He unzipped his skirt, did a little shifting around and finally got his half-hard sausage poking out of through the fly. It was still about eight inches long and seeing it against the backdrop of his big corduroy cover tits gave him a huge thrill.

“May I kiss it?”

He smiled slowly. “Yeah, go ahead.”

Debbie reached up and grabbed it at its based, then gave his mushroom several kisses and a few licks. After savoring the moment he pulled his hand away and laid both of them on his thighs, gently feeling up his skirt. He backed off, looked up and his face took on a serious expression, which puzzled his new girlfriend.

“Miss Candy, I want you know that I think you’re the sexiest fag I’ve ever seen, I mean that sincerely. I also want to thank you for dressing in corduroy for me, I really appreciate that, it was very nice of you. I’m a submissive sissy by nature, and from the first moment I saw your pictures I’ve been dreaming about being your bitch.”

His pretty smile stayed steady, he seemed to like what he was hearing.

“I realize it’s a bit awkward for us because I’m Carol’s ex and we’ve both been her lover. I just want you to know right up front that the reason I’m here is because I want to serve you, I want to be your bitch, that’s my main desire. I know I need to have sex with Carol in order for that to happen, but I’m doing that so I can be with you.”

He smirked. “Oh, so you’re fucking my wife for my sake?”

“Please don’t be like that Candy, I’m very serious. I mean yes, I’m going to enjoy fucking Carol, I’m not going to lie about that, but it’s not the reason I’m here. Look, if Carol had asked me to have sex with her and you weren’t involved, I would’ve said no. In fact that first night we talked I was ready to walk out until she showed me your pictures. The moment I saw those pictures I knew I wanted to be right where I am now, on my knees worshipping Miss Candy.”

He looked at his dick again and sighed, it was a magnificent cock.

“I’ll tell you something else Miss Candy, I was very happy when Carol said you’d be her cuck. I really like the idea of being close to you when I’m with her, it just seems right. Hell, I’d love to be a cuck for you and her, but I understand that’s not what this is about. I’m just trying to say that my biggest desire here Candy, is to be with you, to be your bitch and make you happy. I’d be happy to serve you even if you didn’t want to reciprocate.”

They stared into each other’s eyes for a moment and Debbie saw a calm come over him. Apparently surrendering to him from the start was the right thing to do, it defused the whole situation. He also realized he was hornier than he’d been in years, Candy was turning him on like crazy.

“Can I suck your cock Miss Candy?”

His look turned playful.

“Do you think you’re worthy bitch?”

He noticed his cock was now fully erect.

“I don’t know Miss Candy, but I do have a confession to make, and after that you can determine my worthiness.”

He paused and his voice got serious.

“I can’t throat cock. So I’m sorry to say I’ll only be able to get about half your cock in my mouth. But I really like sucking cock and I’m pretty good at it. I just can’t give you throat if that’s important to you.”

Candy looked a little amused.

“Can you make me cum in your mouth?”

“Yeah, sure.”

“Do you want to swallow my sperm?”

“Hell yes, I’d love to my queen.”

“Then you’re a worthy bitch. Now suck me.”

He didn’t need to be told twice and started kissing and licking his huge boner all over. He thought he’d died and gone to heaven. Soon he wrapped his lips around his mushroom and slid them halfway down his shaft. Debbie spent the next half hour worshipping his dick and raping his corduroy outfit with his eyes.

After a while he got so comfortable having it in his mouth that he let go and started exploring Candy’s clothes with both hands. He didn’t mind either, and that turned Debbie on a lot. Apparently he was just as accommodating as his wife when it came to corduroy. His big tits had a nice genuine feel, they actually felt real, and coupled with the feeling of the soft fabric it drove him crazy with lust.

Candy didn’t say much to start with, but as his dick got used to Debbie’s mouth he occasionally told him he was a good little cocksucker. Debbie liked that. In addition, once he started moaning and really enjoying himself he tested his bitch’s submissiveness by throwing a little humiliation his way, and Debbie liked that even more.

A half hour into the blow job Candy started thrusting his hips and Debbie had to grab his boner to keep from gagging. He decided to go into full cocksucking mode and bobbed his head up and down his shaft as fast as he could, literally jerking him of with his lips. It only took a couple more minutes before he gasped, groaned loudly and pumped Debbie’s mouth full of thick creamy sperm. He slid his lips up so only his mushroom remained in his mouth and swallowed quickly, then stroked the top few inches with his lips, coaxing his ball sack to give up its treasure. Candy happily obliged, giving him several mouthfuls to swallow.

Debbie was experiencing many different sensations at that moment. The sight of Candy’s beauty and petite sexiness, the feeling of his corduroy outfit, the pleasure of being a cock slut and the taste of his sperm, which he liked a lot.

All those things excited him tremendously, but the one thing that thrilled him more than anything else was the sheer power of his big dick. It was as hard as a rock, it spit out long hard streams, it swelled and spasmed like a well-toned muscle, and on top of all of that it was a foot long.

Debbie’s sissy mind toyed with the idea of having that magnificent hunk of manly meat shoved up his ass right to the balls. It was a scary thought to be sure, but it also turned him on like crazy.

After he shot his load he slumped back and drifted into his afterglow. Debbie gently sucked on his shrinking boner until it was a limp dickie, which in his case was a six-inch noodle. His limp dickie was almost as big as Debbie’s erect penis. He eventually spit it out and rubbed his face around the lap of his soft corduroy skirt.

Part of him wanted to hump his dick against it and cum all over it, but another part was just happy to be in Candy’s presence, to be sucking his cock and feeling up his outfit. He had no idea why such a beautiful well-endowed fag was with a guy like him instead of some young pretty-boy, but he loved the fact that he was.

A minute later he opened his eyes and purred.

“That felt really good Debbie, thank you.”

He looked up and smiled.

“No Candy, thank you. Your cock is gorgeous girl, just like the rest of you. I’d love to suck it every day of the week and twice on Sunday.”

They flirted a bit more before Candy told him to let him up. Once on his feet he gently pushed his penis back in his skirt and zipped it up, he then straightened his outfit and hair. Debbie remained on his knees and watched his every move. Candy was so fucking sexy. He finally put his hands on his hips and gave Debbie a sassy smile.

“I’ve got to tell you Debbie, I really like the idea of you being my submissive bitch, so I hope you were serious before. I really like having my dick sucked and Carol doesn’t let me cum in her mouth, so I just happen to be in the market for a good little cum swallower.”

He returned the smile. “Well Miss Candy, look no further, you just found yourself one.”

He reached down and gently brushed Debbie’s cheek with the back of his fingers.

“Get up Debbie, come on, get up and sit in the chair. I’m going to get us drinks, I’ll be right back.”

While he was gone Debbie collected his thoughts and relaxed. He thought the blow job went well and had a good feeling about the way things were going. He had high hopes that everything was going to work out. Not only had he been excited about having sex with Carol again, but after finally meeting Candy he wanted to be his sissy girlfriend in the worst way.

He returned with a drink in each hand and bumped the door closed with his ass, which was a delight to watch. He handed Debbie his drink, sat down and they both slowly drained their glasses as the made small talk. When they were about half empty Candy put his down, took a deep breath and smiled at him. He looked nervous.

“I like you Debbie, you seem like a sweet girl and you’re not pushy. You’re nothing like what I was expecting, and don’t get me wrong, I mean that in a good way. I just need you to stay submissive for me girl, it’s got to be that way, at least for a while anyway. OK?”

“Yes Candy, I have no problem with that, and like I said before, I want to worship you even if you don’t want to do anything in return. I’m yours to use.”

He gave Debbie a strange look.

“Someday you’ll have to explain that to me fag, but for right now I want to suck your dickie. I assume you won’t have a problem with that, right dear?”

He was a bit shocked, but in a good way.

“Um, no Candy, you’re in charge. Who am I to say no?”

They shared a flirty smile before he got down on his knees in front of Debbie. They kissed and groped each other for a few minutes, then Candy pushed him back and worked his way down his neck to his boobies, kissing and caressing them all over. Seeing him rubbing his pretty face against his corduroy dress drove Debbie insane with lust. Candy kept working his way down until he got to his lap. He then surprised the hell out of his lover. He undid one of the buttons, pulled out his hard penis and re-buttoned the dress leaving his boner sticking straight up. He kissed his mushroom and looked up with a smile.

“That’s much better.”

He winked and gobbled up his dick. Davie never asked Carol if Robbie had experience with guys, but from the way he worshipped his boner he assumed he did. He teased it like a pro and in no time at all he was sliding his plump lips up and down the full length of his seven inches. He occasionally looked up and smiled with his eyes, Candy appeared to enjoy his work immensely.

He savored every sensation for about ten minutes before the sight of this beautiful fag bobbing his head up and down his shaft got to be too much. He felt an orgasm start to rise, and in short order the vision of Candy’s pretty face pressing into his corduroy dress with each downstroke took him over the edge.

“Oh God Candy, I can’t take it anymore”

He grunted loudly and emptied his ball sack into his pretty mouth. Candy seemed a bit surprised at first, he probably wasn’t expecting him to cum so soon, but he had no problem staying with it and swallowed his load balls to belly.

Debbie’s orgasm was intense, so intense that it left him completely drained when it was over. He then spent several minutes in his afterglow while Candy gently sucked his penis into a limp little dicky. After a while he finally spit it out, wiped his lips on his dress, then gave it a kiss and got back in his chair. His limp noodle easily slipped back into his dress and they spent a minute composing themselves and their outfits.

“Thank you Candy, that felt really really good, and I’m sorry I came so fast, you just turned me on so much I lost control.”

He liked hearing that.

“Well dear, I do hope you’ll last a bit longer in the future, a girl likes to take her time when she’s having fun.”

They sipped their drinks and talked for another twenty minutes, and they both seemed much more relaxed. Candy was debating whether to get another round when they heard a gentle knock on the door.

“Come in Carol.”

She entered the room timidly with a shy smile, it looked as though she was both amused and a little turned on by seeing the two of them in drag.

“Sorry to interrupt dear, I was just wondering how things were going.”

Debbie and Candy looked at each other and smiled.

“Things are going very well dear, and we’ll all be getting together again tomorrow night.”

Her face lit up like Christmas tree as she looked back and forth between her fag and her ex-fag. Debbie was pleased too.

“Why don’t you give Debbie and me a few more minutes before we wrap up the evening. OK dear?”

She said OK and headed out the door, but not before taking one last long look at the two men she married, both in full drag.

“I think you just made your wife very happy.”

“Oh I’m sure I did Debbie, and I guess you’re happy too.”

He tried to get a sip from his empty glass, then put it down.

“Candy, look at me.”

He did.

“She’s your wife, and nothing’s going to change that. I’m just entertainment for the married couple, nothing more. OK?”

He initially smirked, but then smiled and nodded. Debbie continued.

“Can I ask you something?”

He nodded again.

“Tomorrow night when your being a cuck, do you want me to leave you alone or do you want me to humiliate you? Carol never told me how you felt about being a cuck.”

His smiled turned a little sassy again.

“That’s a very good question Debbie, very insightful, and it pleases me that you cared enough to ask. I tell you what, start out slow, I’m sure you’ll be able to tell if I want more as we go along. Just remember though, whatever happens tomorrow night has nothing to do with the way things are in here. You do understand that don’t you Debbie?”

“Yes Candy I do, and I think I’ve made it quite clear how I want things to be in here, so you have nothing to worry about girl.”

They got on their feet and Candy gave him a big smile.

“You know, I think I’m really starting to get that Debbie, and thank you.”

They kissed and it sent a bolt of electricity through the both of them, much more than either had anticipated. There was a chemistry. They were becoming sissy lesbo lovers and they both knew it.

Like what you read, Sweetie?
Share with your friends 🎀

Twitter
Facebook
Reddit
WhatsApp
Tumblr

Get a FREE Sissy eBook!

Here’s your chance to claim one of our exclusive sissy eBooks—completely free! 

No strings attached, just pure sissy fun!

Join 1500+ Sissy Girls Like You!

What You’ll Get:
🎀Supportive Community
🎀Tips & Resources
🎀Fun Events

Don’t miss out! Click below to join us today and discover your place in our fabulous community! 💖