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Erotic Short story – The Fitting room (Straight man Crossdressing story)

Published July 7, 2013 by jessicamendez

Those who are new visitors to this blog who came clicking this link trying to find an erotic story you can scroll down to story “The Fitting room”.

If you are a regular reader/follower of this blog, I have a special thank you note for you in the following few lines before the story starts. Please read the update and the results this blog has brought out there, with all your support and love. Jessica loves you back 3261858_f520for all that.

This blog has come way far from where it started and how it began. I only wanted this to be some sort of erotic stories publishing blog and later promoting the erotic books I will be write, but instead I have a lot more values connected with this blog.

There are – confused men (wearing panties), excited wives (of the men who wear panties or didn’t want to at first and now they do), gay, straight, bi curious, cross-dressers, transsexuals – all kind of people playing sex now and then writing me as I try to monitor the increasing traffic this blog is attracting every next day.

I have made lots of friends on facebook now. All you fans, friends, followers, viewers, readers – I am so thankful to you for making this blog such a great success. You all gave me more than I asked for.

Things are heating up for 20th July 2012. According to the few messages filling my inbox many men are trying to pass on the word to the guys around them and every day there are more and more men joining in wearing panties on 20th July 2012. Some have even requested to do it for a week. I guess those are the ones who just enjoy doing it and already had been doing it for years now. hahaha….Thats sweet guys. I am not onto some mission to effect a mass, I just hope my writing can be the way to spread the word that lately how common it had been for men wearing panties in their routine. Only purpose behind spreading the word is so if there are men out there who are hurting inside trying to figure out ways to quit wearing panties as if trying to stay sober, you do not need to stress yourself over such a small issue. It is as simple as doing something you feel comfortable with. New york is having an Underwear run in Central Park. lol. I guess it is time we start organizing Opposite day kind of run – where women wear men’s shorts and men wear panties. LMFAO. okay, I better stay focused.

As far as writing back to everyone is concerned, I have one little problem. I don’t mean to be rude by not replying you on facebook, but I get lots of ugly messages from people who says HI first and then after I reply nicely they all talk shit that they were after… add me expecting all I do sitting on my computer is have cyber sex with someone like them. I have a full time day job and also sometimes trying to give time to my husband, trying to plan another adventure along with him, trying to think of stories, trying to write my book further to bring it to finish, trying to keep updating this blog as the weekend comes – sometimes I am not able to reply you all personally.

I have received lots of e-mails that I have tried replying, and those who haven’t heard from me yet, I promise I am replying you shortly. Just keep in mind that I have often included the sexual topics in my blog which may answer your questions – that is if you think I am good at what I write and you believe my advises lol.

Today I am going to write about a story of a crossdresser visiting this shop where he befriends with the shop keeper lady and while this man is in the fitting room one day, taking advantage of his friends absence in the store another shop keeper has her way with this man.

This was a request from Barry living in UK. What you will read is a fantasy/story idea for Barry, who requested me to work on it few days back. I have changed the characters and the plot to some extent in order to have it appealing for general audience, who may or may not get the kick out of it otherwise.

Words of Concern :

Before we go on I would want to request all the men who enjoy wearing panties or like to cross-dress all the way, please do not do it around your partner if she is not a good sport or may had been requesting you to not do it because she does not like it. As a woman I understand that it is a very weird thing for ladies to deal with, to see their partner dressed up as an opposite sex. Not that I meant to have you turn away before you even get into the mood. I just though to pass on this word so some men who are actually gay are not trying to convince their wives misusing the words written else where in this blog previously. If you are gay accept it and move on, there is nothing wrong with it. Same goes for the ladies. If you are into seeing your men wearing panties or dolled up for sex, please do not push him into it. If he likes it and does it, be happy. But if he does not, please respect that. 

 The fitting room

8 years of hunt and 3 unsuccessful and faithful till it lasted sort of  relationships later, he decided to stay single. While staying committed to the same woman was his strength, it was his weakness of being strongly in touch with his feminine side. Just like any other normal man his penis would want to jump out of his pants too, when he would gaze at the curves like Marilyn Monroe. An added harsh reality to that scene would be that Ryan just wanted to see himself just like Marilyn Monroe.

After Sandra walked out on him last night, like Lucy and Cynthia did once, not able to face the fact, he decided to celebrate today, his 30th Birthday by shopping  for turning his semi cross-dresser’s life into a full show now on.

“Life is too short I thought and so I must think of living it to the fullest now, while I have everything I always wanted gathered around me except that one thing”, Ryan said. His top to bottom shaved body was somehow keeping him more confident today, than usual.

“And what would that be sweety?” Tracy smiled getting the hint already. Tracy had been the biggest support that a cross-dresser like Ryan can find in the suburbs of Portsmouth. “No! You are not ! Are you?”

“Yes, I am and I’m going to need all your help mate. Would you be a sweetheart?” Ryan asked confidently unlike stammering like he always does when he comes in for a pack of panties or sports bra so far.

“What about Sandra?” Tracy was concerned. “Does she know?”

“Well, I am done putting ladies through this. I rather use my time to live the way I want to, though I will be single. I did not find it fair to have hopes high of some nice girl with all the great stuff about our relationship and then breaking it up to her saying I like wearing woman’s clothes? Neh, not my thing.” Ryan ended talking and walked towards the dresses hanging on the rack.

“Those are all half off today.” Tracy yelled as she left the store taking the trash out.

Ryan’s eyes got settled on a black dress. Something that he knew every woman must have. After helping himself finding everything else he needed, he realized he still needed the hair. At the adult store next door, he found the perfect blonde hair wig he always pictured himself in, which he remembers with the photo of Marilyn Monroe on the box.

The very next day Ryan showed up at the store looking for a slightly bigger size of the dress, but surprisingly his bubbly friend Tracy was not around today. Ryan texted Tracy, ” Where d heck r u today?

“Found this chick at the bar last nite, still at her place, just wakin up next to her ;) Carol is filling in for me today” Tracy’s text beeped in right back at him.

Ryan’s biggest support Tracy was not around today as she had met some other girl last night at the bar who was just as curious as Tracy herself about exploring other women. Ryan felt jealous for Tracy having met someone of her kind after all, while he gave up in the middle of his quest.

“What can I help you with?” Carol cooed into Ryan’s ears from over his shoulder, while he is struggling through the rack of dresses.

“Uh, I will be okay I think.” Ryan tried to avoid her company like always.

Carol was in her 30′s who stood 5 feet 5 inches tall, just a few inches shorter than Ryan. Her blonde hair was always found disciplined to stay in perfect places, from her scalp to the few weak curls coming down touching her shoulder, keeping her right ear always uncovered as all her right side of face was kept exposed keeping her beautiful face visible to the best, yet a bit hidden on the left.

Ryan always found Carol attractive, but sadly he did not want to give into any urges only to add her name later to the list as he breaks her heart as well, when he tells her that he wears panties and finds something missing when he doesn’t.

Ryan turned around and passed through Carol making his way into the fitting room.

Carol tip toed behind him after he drew the curtains, “I heard you broke up with Sandra?”

“Damn you Tracy!” Ryan murmured. “Uh, well yeh. There were one or two things we didn’t like about each other. It all happened for good, for both of us.”

“Oh really!” Carol said drawing the curtains open of the fitting booth Ryan was into. “Is this one of the reason?” Tracy asked dominating Ryan as he stood in front of her wearing the perfectly fit black dress.

“What the hell is wrong with you Carol?” Ryan baffled. new-hp-hero.jpg.jpg

“Would you take me, if I say you look hot in this dress?” Carol entered into the fitting room. Circling around Ryan she said, “Think about it, you have 3 minutes, I will be right back” and left him alone.

Ryan had no clue what to do. There was no one around besides him and Carol. He could not even run away without getting that dress off him. After thinking for a couple of minutes he tried to text Tracy, sadly he was too late.

“Here, try all of these.” Carol commanded Ryan standing outside the booth, throwing a bra, a pair of satin panties, stockings and a couple of wigs at him. “Give me a nice show.”

This was now or never, Ryan figured instantly. He started dressing up all over again as Carol left him for a minute again, giving him his space.

Carol came back and to her surprise, Ryan was all dolled up only in just a given minute.

Carol approached closer to Ryan, sticking out her maroon lipstick she started painting Ryan’s lips. Ryan supported keeping his lips apart till Carol commanded, “Press them”.

Carol looked down at the bulge growing between Ryan’s legs under the smooth shiny black fabric. She pressed her hand gently on Ryan’s penis, cupping him totally into her palm. She pushed Ryan against the wall and pressed her lips onto his cheeks first. “You want to fuck me, bad girl?” Carol cried into Ryan’s ears after biting them softly.

Ryan grabbed Carol up in the air and off her feet. Carol wrapped her feet around Ryan as Ryan pushed Carol to the wall now.

After passionately making out for as little as only 15 minutes, Carol tried to calm herself down. “Turn around and to the wall” she demanded. Ryan opened his hands laying them on the wall leaving his back exposing out of the backless dress, showing the black bra he was wearing underneath, he hugged the wall he was facing offering his right cheek to the wall to be kissed and left one to Carol.

Carol unhooked Ryan’s bra and started laying gentle pecks all over Ryan’s back. His body left vibrated and shivering, with every kiss Carol left spreading the current through his body. Carol pulled the straps of his dress off his shoulders….

Tinininininingg…..went the bell as another customer entered the shop.

“Gotta go, but don’t you move! I will be right back to take care of you. okay?” Carol said as she left Ryan hanging on to the wall.

Ryan opened his eyes that he shut tightly when he was lost, feeling more than everything Carol was making him feel. He stayed there for another 5 minutes, letting his hands fall down to his sides now. Carol was taking long and Ryan was losing his patience as worrying thoughts of being caught or seen by someone started bothering his mind. Nervous Ryan felt that as exciting as it had been, it was a very bad idea to get to know any more about Carol into this fitting booth. He thought to start dressing up in his man clothes, but only if he could find it where he left them.

Dorian-Ortiz-man-love-woman-Couples-Love-hot-kumar-Couple-sex-gostaffo-sexy-vamp-NicePics-httpwwwpicformetralbumshowimages283page2-senzual-sex-2-Sexy-Album-mine-ibravo-sexy-stuff-pic-1-Paare-Touching-RubbinHe looked around desperately for his clothes as he heard the footsteps coming closer to the fitting area. Ryan was topless after letting his dress fall off him from where Carol left him hanging. He tried to reach his clothes on the floor outside the fitting booth as if they were thrown away because they will never be needed again.

He stepped out of his booth in his wig, black satin panties and stockings, right then he saw some shadow growing bigger as it approached the fitting room area. He hurried back into his booth drawing the curtains close again.

“Why did you move? I said, I wasn’t done with you.” Carol said, as she stood outside the booth along with Tracy, both of them totally naked, staring at Ryan only in his panties and stockings and the brown curls falling over his shoulders, with his legs spread kind of open.

“You were so right! He looks so tempting.” Tracy said to Carol still staring at Ryan as he only stood there witnessing what he found very hard to believe. “You go first. I want to watch.”

Carol approached Ryan as he dropped his panties down offering his erected cock for Carol to play with.


I think I ended this story happily…although I did not explain the happy ending in details. lol.

Sometimes leaving the readers to picture the fantasy further is the best idea to have them really enjoy their reading time. That is exactly what I felt like doing here today at the end.

I hope that story will help making you feel…uh…Tired !

I tried to write it in a way that it not only pleases the crossdressing straight men, but also the women who are into this and some of the general audience who are open to explore the pan sexual playground.

Please leave you some comments or feedback below….if doing any such thing makes you feel embarrassed than you can contact me personally.

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Hope to hear from you soon. Please write me what you would like to read here, or about your fantasies with some blue print that I may help you bring it alive through one of the stories. I do take requests from all my readers, in order to satisfy them to the best I can.

20th July is coming closer…Get your panties ready men. Because after looking at hundreds of stores and websites selling men’s underwear that can make anyone throw up, there is a number of men and women who are willing to break the boundaries of the fashion world that restricts men’s clothing from adopting more fashion and colours. If you are a man and agree that you wear boring and saggy underwear everyday, please get a pair of colourful panties for yourself and wear it on 20th July. Feel the comfort, the fun, the kink of it and see how it feels. I am a woman who love seeing my man in panties. If you are also a woman and bored looking at your man in same big boxers let’s change it for good .lol. All the best Everyone.

The following links may help you figure out what we are talking about.

Men who like wearing panties

How to choose perfect panties – for men

“Always keep trying something new with your partner. It will not only make the sex better, but will help you grow that bond stronger as you share the exciting memories you are about to make.”


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