Crossdresser Stories Series

Jason was so excited to get home & surprise his lady with her birthday present! Little did he know that he was going to be the first one to try on her gift! Enjoy this CD story and more of my stories in this genre!

“Thank you, Alfred. That is very sweet of you.” “Please don’t mention.” “And Alfred?” “Yeah?” “Could you also assist me with something when you are coming over with the car?” “Sure. Anything.” “Anything?” “Yeah. What would you like me to assist you with?” She was smiling to herself now. “I wanted to get some items from the boutique. I don’t know if I could send you a list of them.” “A boutique?” “Yeah.” “What items would that be?” “Just some things a woman needs to put on every now and then.” “Okay, you mean like clothes?” “Yeah. Clothes. And cosmetics.” “I see. And you think I can do justice in shopping for them for you?” “Yeah, why not? I would send you the measurements and the sizes. Any boutique would be able to get them for you once you give them those measurements and sizes.” “I see. Okay, no problem then. Just send them to me.” She smiled. “That is very sweet of you, Alfred.”

Dylan's first day at work started out like any other day. That was until Sarah entered into his life. Little did he know he was soon to be transformed into an an entirely new man. Order now! Your secret is safe here...

He raised the panties and took a deep breath from them. “You would call me?” “Yes, when I want you to pick up your first check.” “No problem. I would expect your call.” “And Josh.” “Yes?” “When I do call you, I want you to come wearing those things.” He raised the panties and the bra. “I should put them on when I am coming over to see you?” “Yes. Make sure that you have them on. If not, you can consider this whole deal cancelled.” “No problem. I would have them on when next I am coming here.” As he left the office, Josh could not stop thinking of how lucky he was. He had not only won a big account but also won the approval of the MD, a dominatrix. He recalled what Cassie had wanted and he knew that he was not going to relent in fulfilling his promise to her.

“No, you are not going to be naked.” “I am not going to be naked? But you said I should take off my clothes.” “Yes, I know what I said. And you should be quick about it.” Teddy was confused as he took off his shoes and pulled off his trouser. He turned to her, standing only in his boxers and socks. “I am ready.” She shook her head. “No, you are not. What are those?” “My boxers and socks.” “Did I say I wanted them?” He shook his head. “No. but I thought you –” “Will you get out of those things right now?” she spat. Teddy hurriedly pulled them off and kicked them aside. As he stood there completely naked, Laura reached for a sofa nearby. She picked up some items and tossed them over to him. Teddy bent over to pick them up. “What are these for?” “They are for you, Teddy. Put them on.” He held them up. “These are for me?” “Was I speaking in Latin the first time? Of course they are for you. Put them on quickly.” “But they are … I mean, they are not … they are not for men…” “And so?” “How can I put on this stuff?”

“I’ll show you,” she said. She unzipped the backpack she was holding and brought out some items. Andrew could recognize most of the things she pulled out of the bag. There were an overall, shaving sticks, clippers, combs, and other usual tools that barbers made us of. But it was the items she held up that he could not understand. “What are those?” “What do they look like?” she asked as she tossed them over to him. “These are a set of lingerie, fishnet leggings, gloves, and a G-string,” he said as he regarded them. “Yes, they are.” “And what am I supposed to do with them?” “Put them on, Andrew.” He chuckled. “You are out of your mind.” “Really? Okay then. I am out of here,” she said picking up her stuff. “No, no, wait, don’t leave.” “You are clearly not ready to have a haircut, Andrew. And I am not ready to waste my time. So it is best I leave.” He fell to his knees. “No, please don’t go. Please stay here and give me the haircut.” “You must put those things on if you want a haircut and the benefits that I spoke about.” “Sure, no problem. I would put them all on.” “Then do so.” Andrew hurriedly got into the clothes she had given him. When he was through, he turned to her. “Am I okay now?”

Enjoy this CD short story! “No, no, not at all. Please keep on talking. I love hearing your voice and your words.” “You do?” “Of course I do.” “But you said you are feeling dizzy. Are you getting bored with me already?” She sighed. “Mark darling, I am only commending you and the way you make me feel. Don’t you understand?” “Okay, I think I do now.” “So, what were you saying?” “Yeah, it is about the dinner and birthday gift I have planned for you.” “I see. And when would that be?” “Anytime in the evening that would be convenient for you.” “Okay. That means after I close from work?” “Yes, Jenny. What time do you think you would be through today?” “I should be done by seven this evening.” “Okay. So we can meet by, say, eight?” “Eight would be just perfect. Where would we meet?” “There is on hotel on Melrose Street.” “A hotel? You mean The Blue Bell?” “Yes, that one.” “Are you booking a room for us there?” “A room? No, no, no, not that. I am booking a table for us at their restaurant.” “Oh, I see. For the dinner?” “Yes, just for the dinner.” “I thought…anyway, never mind.” “You thought what?” “I thought that you would have booked a room for us there.” “But Jenny, it’s just a private birthday celebration.” “Yes, I know.” “It is not a vacation, Jenny.” “So, is that why you don’t think we need a room together?” “Jenny. What do we need a room for when it is just a dinner?”

“Just a minute,” she said as she rummaged through some of the shopping bags that were on the floor. She soon found what she was looking for. “Put these on.” He collected the items and regarded them. “You bought these from my store?” “Yes, I did. And now I want you to put them on.” “But …but…but these are a lingerie, a garter, a mini-skirt, and a bra.” “And so?” “They are clothes worn by women.” “And so?” “You want me to dress up in them?” “Do you have a problem with your ears? Of course that is what I want you to do.” “But they are clothes worn by women.” She sighed and placed her hands on her hips. “Do you want to see me happy or not?” “Of course I want you to be happy, Kathy.” “Then just do what I have said, okay?” Malcolm picked up the clothes and began to put them up. When he was through, he turned to see her holding a makeup kit in her hand. “Don’t even try to protest.” He looked at himself. “You mean you are not yet satisfied that I am all dressed like a girl?” “No. I will not be happy until you are looking like a girl completely. And that means in both attire and makeup.” “Okay, let us get it over with then,” he said as he sat down on the floor.

The words hit Dan like a thick horsewhip cracking against his exposed skin. He shuddered as he stared at her. There was something cold, distant, and menacing about her gaze that made him realize just how much power she wielded. And yes, she wielded so much power at that moment. He was completely naked while she was still fully dressed. She was his professor while he was her student. What more evidence did he need to confirm just how powerful she was over him? Instinctively, he fell to his knees. “I am so, sorry, Professor. Please go ahead.” “Good. It’s about time you knew how to be obedient.” Dan did not say another word as she began to apply the make-up on his face. She was not in a hurry as she applied copious amounts of lipstick, face powder, mascara, and eyeliners. When she was through, she reached into her bag again. This time, she brought out a single piece of clothing. She handed it to him. It was a G-string. “Should I put it on?” “Yes, put it on.” Dan stood up and slipped into them. Next, she brought out a pair of black high heels. “I am sure that these would also fit your feet.” Dan tried on the shoes. She was right. They fit him perfectly as if he had gone to buy them himself. “Now, turn around and look at me.” Dan turned and looked at her. “How do I look, professor?” She licked her lips. “You look very ravishing, my dear Dan. I could eat you up right now, do you know that?” He smiled. “I know.”

“But I just took off my clothes as you requested. You want me to put them back on again?” “No, not your clothes. Mine.” “Yours?” She nodded and reached for some clothes on the sofa nearby. “Put these on.” “You want me in your clothes?” She sighed. “Do you know what, Mike?” “No. What?” “You really ask a lot of questions for someone who wants to fuck me.” “I am sorry.” “Don’t be sorry, you fool. Just do as I tell you.” He nodded and slipped into the clothes she had given him. They comprised of a mini-skirt, leggings, a bra, and elbow-length hand gloves. “Good, now put these on,” she said handing him a pair of black high heels. He slid his feet into the shoes and was surprised that they fit him. “Now, you need to relax while I apply some makeup on your face.” “Makeup?” he repeated. “You want to apply it on my face?” “Where else do you think I want to apply it?” One glace at her straight face was enough to force him to hold back whatever it was that he wanted to say. “No problem. You can do so,” he said weakly. Alex picked up a kit from a table nearby. She then began to apply mascara, eyeliner, lipstick, and powder on his face. When she was done, she stood aside and regarded him. “How do I look?” he asked when she did not say anything for a long while. “I don’t think I have ever seen a more beautiful girl than you, Mike.” “Really? Can I take a look at myself?” “Sure. Look in that mirror over there by the wall.” He stood up and went to peer at himself. The reflection that Mike saw was not recognizable to him. Quite alright, he was the one standing there. But he was so much different.

Stanley & Claire need a little sugar & spice in their marriage. After years of boring sex, Claire initiates something that will change their relationship forever. Short excerpt from the book... “Hello, Stanley. How are you today?” “I’m okay. And you?” “I am fine. Just busy with work.” He was looking at the printout when he realized that she had not said any other thing. “Claire?” “Yes?” “You are quiet.” “Am I?” “Yes, you are. You haven’t said anything.” “Really? I am so sorry. How is work?” “I already told you that work is fine.” “You did?” He dropped the image. “Are you alright, Claire?” “Yes, of course I am. Why did you ask?” “You are not saying much, considering the fact that you were the one that called me.” “Ohh.” He frowned. “Ohh?” “Nothing.” He sighed. “Come on, Claire. Talk to me.” “But I am.” “You are not talking or saying anything much, Claire.” He heard her sigh. “I don’t know. I just …I just …” “You just what?” “Okay. You know we haven’t said much about what we discussed yesterday.” “Yesterday?” “About our marriage.” He sighed and rubbed his forehead. “Well, what is there to say?” “Stanley, I don’t think we should leave things the way they are and hope that they would get better.” “Would they?” “Would they? Don’t you believe our marriage can get better?” “I don’t know what to think, Claire. I only know what it is right now.” “Stanley, we can improve things in our marriage. We can.”

Enjoy this short CD themed story! He did not make another comment as he slipped into the bra. Elaine knew that he looked awkward putting on the bra over his white long sleeve shirt. .. He quickly hooked it in place. “Okay. I am ready.” “No, you are not,” she said simply. “You still need to get into my shoes.” “Your high-heel shoes?” “Yes. Both of them.” He managed to slip his feet into them. “There, now are you satisfied?” “Let me see. Turn around and face me.” Mr. Daniels turned. He did not know how he looked to her. But he felt stupid and idiotic to be wearing all that women’s attire. “Well?”

“By the way, where are my panties?” “It’s right here,” he said as he reached into his pocket. “Put it on.” He blinked. “Excuse me.” “I said put it on.”

18+ Crossdressing Stories - Hubby Assignment

“I was actually calculating how long I had been waiting to come after you.” She snorted and tossed the G-string at him. “Put this on.” He caught it and held it against his nose. “This smells really nice.” “Thank you. Now put it on.” “You are not serious. Why should I put on your G-string?” “Because I said so. And because if you don’t, then you are not going to get any of this.”

He shook his head vigorously. “I never thought anything like that.” “Then why were you acting up and being difficult?” “Acting up? I wasn’t acting up or being difficult in any way, Kelly.” “You know, things wouldn’t have gotten to this level if you had just been a good girl and not tried to mess with my head.” He blinked. “A good? A good what?” “A good girl.” “Kelly? Are you calling me a girl?” “Yes, that is how I see you, Matt. I see you as a girl.” “But I am a guy.” “A guy who I see as a girl.” “You see me as…as….as…a girl?” She nodded. “Yes. And do you know why?” “No. No, I don’t.” “You were playing with my mind, teasing me and all. You refused to be a man and just continue with your naughty descriptions about me.” “I didn’t refuse to be a man. I am a man, for goodness sake.”

Enjoy this short CD themed story! “Yes, I would. But that is for a medical examination, which is not what I am here for.” “Yes, I know. But what if that was what you were here for? Would you refuse to undress?” “Look, Carol, I don’t have any issues with taking off my clothes.” “Then do it, Arnold. It is for your own good.” He bit his lower lip. “Would I be naked or what?” She shrugged. “You can choose to be naked if you want. Or I could give you another overall to cover up yourself.”

She gazed at him. “I am going to take my bath. I want you to get undressed and wait for me. Is that too difficult to understand?” “I…I…no, of course not. I will get undressed.” “Good girl.” “Good girl?” She nodded. “Yes. That is my pet name for you tonight, Leon.” “I see.” “You don’t mind I hope?” “No, not at all.” “Good. Get undressed and wait for me.” She then allowed the robe to fall off her body while she was still in the living room. She could hear him gasp as she walked into the bathroom. She could imagine him ogling at her naked figure, hoping and wishing to see her from the front. Too bad, he had to just make do with the image of her thick luscious hips as she walked away from his view.

“Here they are,” she said tossing over a bag to him. “What are these?” he asked as he peered into it. “They are the stuff that I spoke about earlier, when I made mention of trying out some things for me. Do you remember?” “Yeah I do. But what are they?” “Go on and bring them out. They wouldn’t bite you.” He pulled them out one after the other. When the bag was empty he regarded all that he was holding. “These are clothes.” “Yeah?” “But they are female clothes.” “Yeah?” He gazed at her. “Yeah? Don’t you think that you made a mistake?” “How?” He sighed. “Betty, are you not following what I am saying? These clothes are for women.” “And I am fully aware of that.” He blinked. “You are? Then why did you bring them to me?” “Because I want you to put them on.” “But…but…but…” “But what?”

“Oh my god, I cannot believe that I am doing this! I, I, I am not gay(he whispered)”. “Oh you silly man. That is a normal response. But wearing a womans panties does not make a man gay.” Barry begins to slide her soft panties up his thighs, and pulls them up around his hips.

Derrick cursed. “I said I am going to put on your clothes, for goodness sake. Damn. Hand them over to me right now.” “Me? You want me to hand them over to you? You must be crazy. Pick them up yourself and put them on.” He shook his head and reached for her clothes. It seemed like he was transfixed or in a trance as he began to peel off his own clothes. First he slid out of his overall, and then his shirt and singlet. Already, his trousers were down on the floor. He was still in his shoes as he began to slide into her clothes. It did not take him any time to get dressed. When he was done, he turned to look at her. Rosa smiled at him as he stood in front of her. She loved the way his masculine body was straining at the bra that was clinging to his chest, the skirt that was around his waist, and the panties he had on. “You really look pretty now.” “I do?” She nodded. “You are such a pretty girl to me, Derrick. Now, come over here and let me take care of you really good.”

He glanced outside at the skyline of the city. He admired the calmness that the view afforded. It was as if the entire city was asleep at that moment already. But he knew better. The city was wide awake and bustling with a lot of activity. “Here is your drink, sir.” He turned to see the same waiter with his order. “That was quite fast.” “I said I was going to be back in a minute. And I kept to it.” “You kept your word. I like that,” he said as he reached into his pocket for his wallet. “Are you paying for it already?” “Yes, I am. Here, have this.” The waiter counted the bills. “This is far more than the cost of the champagne, sir.” “I know. Keep the rest as a tip for keeping to your word.” The waiter smiled. “Thank you very much sir.” As he bowed and left, he poured himself some of the drink. If only people could be like this waiter, he thought. If only people could keep to their word. He took a sip and enjoyed the taste. He glanced at his wristwatch again. 7.23PM. Damn it. Is she going to come at all or not? What kind of delay was this? And to make matters worse, she had not even bothered to call him to give any explanations for the delay. Or had she? He reached for his phone. She hadn’t. There were no calls or messages from her. Where could she be, he wondered as he took another sip. “You are already drinking without me?” he heard someone say.

Enjoy this short CD story! Could she be wearing panties under that dress, he wondered. But her dress was so tight around her ass and he was sure he had not seen any pant lining. It must be a G-string, he concluded. He felt his heart tighten again as he thought about her wearing a G-string. What wouldn’t he do to see her take off that G-string and hand it over to him? What wouldn’t he do? Almost anything. At that moment, the phone on his desk began to ring. He took his mind off Ashley’s body and took the call. The call was for one of their departments. He quickly transferred it and turned his attention to Ashley again. She was flipping through a magazine. He found himself wondering what she was reading in them. Just then the doors slid open and a man with a blue suit came in. He walked up to where he was. “Good morning,” Carl said with a smile. “How can I be of help to you?”

Enjoy this short story by Hellen Heels xoxoxo. He rubbed his chin. “Okay. What then do you do?” She swiped her phone and showed him the screen. “This is what I do.” He squinted as he regarded what she was showing him on the screen. “What is that?” “What can you see?” “Those are…aren’t those…those are female clothes on display.” “Look carefully, Mr. Principal. What do you see?” “I know what I can see. I am sure of it. They are female clothes – bras, panties, leggings, lingerie.” “Okay. Good. Now just a second,” she said as she typed something on her phone. She then showed the screen to him. “What can you now see?” He peered at the screen. “You drew the clothes on her. Yes, that is it. You drew those female clothes on her.” “Are you sure?” “Yes.” “Look carefully, Mr. Principal. Are you sure of what you are saying?” “Yes, of course. It is a woman who is wearing … No. wait. Let me see that picture very well…the woman has a beard and moustache? That is a man.” “And what do you notice about the man in the picture?”

Enjoy this short story! 18+ “What is in that bag?” “Nothing much, just some pieces of clothing that I bought on my way here.” “You bought some clothes?” “Yeah.” “For who?” “For myself, actually. But I figure that the best way I can assess them is to see you in them.” “I don’t understand. Are you saying that those are women clothes?” “Yeah.” “And you want me to get into them?” “What is wrong with that?” He chuckled at her. “What is wrong? Leslie, are you out of your mind?” She shook her head and shrugged. “No. Why should I be? In fact, I think you should be asking yourself the same question.” “Me? How?”

“And all I have to do is to wear your panties from now till tomorrow?” “Yes.” “Okay. I’ll do it. Where are your panties?” “They are right here,” she said, dipping her hand into her bag. Don was frowning as she rummaged through her hand bag. He was sure that she must have been kidding. But when she pulled them out, he gasped. “You must be joking.” “Why would you say that?” “Those cannot be your panties.” “Why?” “Those cannot be a woman’s panties. Maybe a handkerchief, but surely not panties.” She held it under the table and unwrapped it. And then he saw what it was- a woman’s panties. “Are you satisfied now? They are not just a woman’s panties but my own panties, Don.” Still, he shook his head vigorously. “No. I don’t want to believe this.” “And why?” “Why? How can you ask me why?” “I want to know why you are so full of doubt.” “Well, it’s because…because…No, stop it. Do you want to tell me that you are currently not putting on any panties?”

“Okay, no problem. My name is Carl.” “Carl?” the man asked as he peered at a tablet in his hand. “Yes, Carl. Carl Harris.” Carl watched as the man went through the list. He turned to the woman by his side and whispered something. The woman took the tablet and began to run through it herself. Carl saw her expression change into a frown. “Excuse me, is there any problem?” “Just a minute, sir,” the woman said. He looked away and that was when he caught sight of a woman coming down from an SUV. He wondered what it was about her that seemed to hold his attention like a vice. Was it her red body hugging dress that had a plunging neckline and stopped just above her knees? Or was it her black high heels that made her look taller? Or her blonde hair that she had decided to let fall loosely all around her shoulders? Or the long multi-colored nails that she displayed as she ran her fingers through her long hair? Or maybe it was the way she walked, like a model who was so sure of herself and her looks? Or was it her curves which were very pronounced in the tight dress she wore, easily revealing her generous hips and well-endowed breasts? Carl found himself adjusting his tie and pulling at the sleeves of his black suit as he watched her ascend the staircases towards where they were. The man stepped forward to meet her. “Good day, madam. Are you here for the conference?” “Yes, I am.” “You are welcome, ma. Can I have your name?” “It’s Jessica.”

“And for the dress, I can see you in something that would remind us of royalty.” “Like a queen?” Trisha asked, her face aglow with visible excitement. “Yes. Like a queen. The gown would be long and overflowing. But we would give it slits on each side. From the waist down,” Stephanie said. She paused to look at one of her assistants. “Take those notes down, please. We must get Trisha in this design first. Do you understand?” The assistant nodded as he scribbled on his notepad. “Yes, Stephanie. The colors for the hat were purple, orange, and yellow.” “That is right. And the gown would have slits on each side, high up, from the waist down.” The assistant nodded. “I got that. A long and overflowing gown with waist-high slits.” “Good,” she said as she regarded Trisha. “We have got the gown and the hat already. What about the shoes. What kind of shoes would fit Trisha?” “I think she could use a pair of –” the assistant began to say. “Stop,” Stephanie cut in. “Don’t give me your opinion. I want to hear from the new students seated before us. And that includes you as well, Trisha.” Trisha looked around. “What kind of shoe? Gosh, I don’t know what to say.” “It’s alright. Just try to figure out something while I attend to the other students here,” Stephanie said. She then looked around. “Who would I focus on now? Why not you,” she pointed at another young woman. Trisha turned to him. “Can you see that? She already thought of a design for me so easily.” He nodded. “Quite impressive. I wonder what she would think of for me when it gets to my own turn.” “You are a good looking guy. I figure she might choose a corporate outfit for you.” “You think so?” “Sure. It is just natural.”

“Maybe you don’t like my deal after all. Would you like to deal with the cops then?” “No, no, not at all. I would wear them. I would wear the female clothes.” And he did wear them. Moving quickly, he began to strip out of his own clothes. Soon, he was in just his boxers . As he made to pick up one of the female clothes, she snapped her fingers. “What are you doing?” “I want to put them on.” “With your boxers still on?” “Yes, mam.” “Don’t be a stupid girl, Dennis. Have you ever seen a woman put on her clothes over a man’s boxers?” “I don’t…I don’t…I mean, no.” “Good. Then you should not do that. Do the right thing. Strip off completely before you put on the clothes.”

“Maybe you have to get more panties, honey.” She frowned at him. “More panties? But I already have enough of those. Why do I need more?” “Because from now on I want to wear your panties when I go to work every morning.” “Every morning?” “Yes, Laura. Every morning, I want to wear the panties you used the previous day.” She gaped at him. “The ones I have used?” “Yes, dear. So that means you don’t wash them until I have worn them too and returned from work. Okay?” She nodded. “Okay, dear. I understand.” “I love you,” he kissed her and left. As he drove off, Laura smiled to herself. She was glad that he had agreed to do her bidding.