Tag Archive | Crossdressing

Aaron Stanford Enters a Womanless Beauty Pageant


“Aaron, we have decided to enter you into a very special contest.”

“Oh?  What kind of contest?”  Aaron asked John.  They had been friends for years, and he could see that the oddly mischievous look on his friend’s face. 

“Well, we’ve decided to enter you into a womanless beauty pageant.” 

“Why did you pick me?”  Aaron asked, his face flushing with embarrassment. 

“Well…um…we thought you would have the most fun with it.  The girls are waiting at the salon for you right now.” 

Aaron got up and followed John out the door.  When they entered the salon, he was shocked to see a group of his male friends and their girlfriends there.  “What are you all doing here?” 

“We’re here for moral support,” Amy piped up.  She was John’s girlfriend, and known to be very assertive.  Suddenly, she pulled a several pairs of stockings out of her pockets, and the guys held Aaron down as she tied his wrists and ankles to the chair.  “You’re going to get extensions today, as well as full makeup.” 

Another friend, Rick, pulled out a large pair of scissors and began cutting Aaron’s clothes off of him.  “What are you doing?”  Aaron asked, feeling helpless. 

“Don’t worry; we have a brand, new wardrobe waiting for you before you leave.  Look there!  You still have a penis!  Jamie, why don’t you tuck that useless thing away?”  Jamie walked up to Aaron and made his penis disappear. 

Rick grabbed at the air in front of Aaron’s crotch, and said, “See, you are a woman now.  Nothing there!” 

After a few hours, Aaron was no longer Aaron.  He had become Erin.  They had glued breasts and hips on his body, put on his makeup and styled his hair “Let’s get you all dressed up now.”  Amy retrieved Erin’s new outfit, and assisted him with dressing up.  She helped him put on his pantyhose, showed him how to hook a brassiere, and zipped his dress.    When she was done, she was asked how it felt to have a woman’s body. 

“It feels strange having these breasts.  They keep getting in the way.  Also, it’s awkward to walk in these high heels.”  Erin looked in the mirror, and saw a beautiful woman staring back at him. 

“Time to go to the pageant,” Erin sighed, and they got into their cars.  A few minutes later, they got out and dragged Erin into a strange building.  Erin felt so humiliated; having no control over what was happening to him.  

“I’m so glad it’s you and not me,” John whispered into Erin’s ear. 

“Are we here?”  Erin asked as they walked into a room filled with people. 

“Surprise Erin!  No womanless beauty pageant!  It’s a party.  Now, you had better act as feminine as you can, or else you’ll get found out.” 

It was a large party; an expansive hall filled with a gathering of men and women wearing glamorous dresses and suits.  A young woman stopped Erin and complimented her on her dress.  Erin’s face turned red with shame. 

“Thank you,” she replied.  Her cover was working; everyone thought she was a woman.  Next, a man approached her and asked her for her phone number.  “Umm…ummm…I don’t have a phone,” Erin stuttered, unable to think of a good answer.  She had never been hit on by a man before.

The guy slapped Erin’s behind and laughingly called her a liar.  Did he know?  Did he suspect she wasn’t really a woman?  Poor Erin.  She is sooooo screwed! 




Attention Sexy Texters: Yahoo Pingboxes will soon be leaving our sites

Dissapointed Smile Smiley Clip Art

Hey everyone,

I’m just writing a quick note to all my clients, to let you know that Yahoo will no longer be supporting their pingboxes as of Dec. 14th 2012. 

As we are dedicated to continuing offering you the very best in erotic texting, our Yahoo Instant Messenger will still be operational – you will still see our addresses on our sites – however, we will be replacing our Yahoo pingboxes with an alternative.   

While Yahoo Instant Messenger is still available to you, you will no longer be able to see our availability via Yahoo pingbox. 

We apologize for any inconvenience this may create, and we are currently working on a solution to the issue.

On a sidenote, if you have received a suspicious email from me, containing a link, please delete it.  It seems that my Yahoo email account had become compromised.  The email wasn’t actually sent from me.  If I do send you an email, I will always write something in the subject line. 

I have taken measures to stop this from happening again, but if you do receive more strange emails, please let me know.

E. Crawford

Dear Miss Stanford, it’s time for you to say Brassiere.

Dear Miss Stanford,

It is time for you to say the magical word.  Say ‘Brassiere’ Kathy…say it.  The sooner the word leaves your lips, the sooner I ‘out’ you and make your life complete. 

You aren’t happy as a man.  You don’t quite cut it.  Let me weaken you all over.  Let me bring you to the pinnacle of weakness by removing your testicles and penis.  Allow me to put you on hormone therapy, so that you can experience true womanhood.  Be a real woman, like me Kathy. 

You know you won’t be happy until you say ‘Brassiere’ and allow me full control over your mind, body and life.  I will help you with everything.  I will put you on a strict diet, help you with hormones and listen to you.  I will educate you on everything about being a woman.  You won’t be alone in this process, I assure you.

You will be able to go to work, wearing a pencil skirt, pantyhose, pumps and yes…a brassiere Kathy, a brassiere.  Every. Single. Day.  You will have to get up 30 minutes earlier in the morning, and sometimes cry about what to wear.  You will look down in the shower, and see breasts and curves.  You will do your makeup and hair, and stare at your beautiful, new face in the mirror.  You will ask yourself why you didn’t say ‘Brassiere’ sooner. 

The longer you put it off, Miss Stanford, the harder it will be to make this special transformation.  Let your fears melt away because you are not alone.  I will be here for you. 

So is it a deal?  I know you are close to cracking my dear.   The sooner you crack, the sooner you can have a crack.

Your Mistress,

Eva Crawford.

Erin Returns to the Office

Miss Crawford and Miss Grace have Erin Stanford chained to Womahood in every way.

“Miss Stanford, could you please come to my office?  It’s inspection time.”  I smiled at her when she turned around and looked at me.  Her makeup was perfect, as well as her hair.  She looked impeccable, yet I wanted to make sure that she was wearing everything that I had ordered.

“Yes, Miss Crawford.”  Erin got up from her seat and headed toward my office.  I followed her for the first time, giggling as I saw her struggle with the tight, pinching pumps, short, ill-fitting skirt and tight pantyhose.  I already knew that she would pass inspection. 

As soon as we were inside the office, I closed the door.  “Please stand still, and let me check you over.”  I lifted the hem of her skirt, and noticed that her pantyhose were lacking runs, but crept down her thighs. 

My eyes glossed over her breasts.  “How is that brassiere fitting?  It looks like you have filled them out nicely.”  I reached out and grabbed the right breast, feeling the strange sandbag sensation.  “What is this?”

“Um….err….it’s birdseed Miss Crawford,” Erin stammered. 

“Points for creativity, Erin.  Please walk around the room for me.  Make sure you walk heel to toe, heel to toe.”

“Yes, Miss Crawford.”  Erin began walking, her heels clicking against the tile floor.  Her face belied her secret misery; the hell that she had endured ever since the day I had issued her the new wardrobe. 

She walked across the floor, exactly as I had instructed.  “Very good, I think it’s time you met your new Mentor.”  I told her to take a seat, and I left the office.  I returned with a very well-dressed woman, donning a perfectly fitting skirt suit, pantyhose, black leather pumps and crisp, white blouse. 

“Erin, this is Miss Grace.  Miss Grace is going to take you shopping today for a brand, new wardrobe.”  Erin got up from her seat and greeted Miss Grace with a gentle handshake. 

“Nice to meet you, Erin.  Miss Crawford has told me so much about you.  She has put me in charge of training you to be a woman full-time.  Our first order of business is to purchase you some new, fitting clothes and shoes.  We will follow with a trip to the manicurist and then lunch for a talk.  I think I will be able to turn you into the perfect office girl.” 

Erin looked at me, and I gave her a smile.  “Miss Grace has been ordered to report any insubordinate behaviour from you…and if that happens, you will be back to wearing your tight, uncomfortable wardrobe.  Understand, Miss Stanford?”

“Yes, Miss Crawford.”  Erin’s face was a mix of confusion and relief.  It was time for her to leave for the day with her new Mentor. 

“Be a good girl and do everything Miss Grace tells you…or else it’s off with your head.”  Miss Grace got up and Erin followed her out of the office.  Erin had no idea that Miss Grace had once been a man herself.  I sat back down at my desk and went back to work. 


Oh Honey…Oh Honey…Erin, Your Slip is Showing!



Note to the Reader: This is another humiliating confession from
Miss Kathy S, as required by Ms Eva, to help her remember how screwed she
really is.

I walked back to my desk, face burning.  I had indeed pissed off the boss, and now I was going to pay for it.  How much I would have to pay, I didn’t know yet.  But I should have caught the hint when the young woman who had just whispered in my ear came back and added “You better be careful, or you just might be sitting down when you do your pissing in the future.”

The skirt, blouse, and brassiere were on hangers, so I knew I couldn’t just set them down anywhere; Miss Crawford would get after me for wrinkling the fabric.  There was no closet in my office, only a coat rack.  I hung them up and put the pumps beneath.  The bra cups were stiff and pointing right at me.  I piled the pantyhose on the corner of my desk; it kept toppling over.

A wave of embarrassment rushed over me.  I was so taken by surprise at being offered the opportunity to dress as a woman for work, a fantasy that I had harbored for so long, that I had temporarily forgotten who I was talking to.  Now Miss Crawford had gotten me to admit that I knew my sizes in women’s clothing, and why else would I know them unless I actually wore women’s clothing?  Not only that, but she had provided what I was to wear to the office, although everything looked a size too small…well, except the bra cups, which looked bigger than my usual B cup.  Still, I would have to wait until I got home to be sure; no sense holding them up to me in the office.  I had been ridiculed enough.

I waited for everyone else to leave before me, so I could carry everything home in a bag.  The train ride home that night was uneventful, though I couldn’t be sure that would be the case in the morning.

I got home, stripped, and put on a pair of panties and a girdle.  I started holding the clothes up to me — yes, they were definitely all a size too small.  I tried a waist cincher, but even that wasn’t enough to get the skirt on.  I would have to use a corset.  Only problem with a corset is, I would have to find someone to tie me into it.  And it would have to be at night, since everyone would be getting ready for work in the morning; unfortunately, that would also mean having to sleep in it.  Options were few indeed…time for a phone call…

A half hour later, my mother was at the door, all smiles.  “Hello, Erin.  I do wish you’d call besides when you need my help, but that’s all right, you know how much I love giving this sort of help…”  It was true: she seemed to relish those moments when I had to be “Erin”.  “Now, where is the corset?”

A few minutes of intense struggle, and the corset was in place.  “Now, before I go, put on the skirt just so I can be sure it fits.”  I did as instructed; it just barely hooked and zipped up in the back.  The hem fell two inches above the knee; the kick pleat was even higher in the back.  I was afraid to sit in it, since I didn’t want to ruin it, so I just stood there.  “All right, that will work, but you won’t be walking very fast, and you might not even be sitting at work tomorrow.  Well, I better make like a cheap pair of nylons and run, Erin.  Have a good day at work tomorrow!”  With that, she left.

 I checked the bra — sure enough, the band size was too small and the cup size was too big.  So I found a pair of knee-highs and the bird seed and made myself a new pair of larger inserts.  Finally, I took off the skirt and lay down and attempted to get some sleep, worried that I might not even be able to sit up in the corset.

The next morning I found out how miserable the day was going to be.  I could barely get the bra into place after hooking it in front and trying to work it around my chest, the band size was so small.  The C cups were a size bigger than my usual B; I could feel the straps dig.  The blouse, however, seemed designed for a B cup; it was all I could do to get it over my head and over the breasts and to the top of the skirt.  The skirt allowed very little movement.  The shoes pinched.  And the crotch of the pantyhose kept falling and sagging a couple inches beneath my own crotch; I could just hope for the best, which I was to find out wasn’t enough.

I didn’t dare sit on the train; instead, I endured the indignity of men offering a seat and me smiling back as pretty as possible as I shook my head to decline.  Whichever hand I grasped the strap with, that side’s bra strap and band dug in even more, and that side’s skirt hem inched even higher up my thigh.  I just closed my eyes and tried to shut everything out for the fifteen-minute ride.  And I did, until I heard a booming, deep yet female voice cry out behind me:

“Oh, honey…oh, honey…”

I could feel her shaking her head in the tone of her voice, condescension or pity, but also a stifled giggle.  Then the voice was at the back of my neck.

“Oh, honey…you think you’re small enough to fit inside those pantyhose?  Guess again, honey.  No matter what size you think you are, you better buy what the package says to buy, or the crotch is going to be showing through the slit like it is right now!”

OMG!  Holding onto the strap is hiking the skirt just high enough to…well…you heard what the lady said.  I immediately let go of the strap and did all I could do to balance until the train finally came to a stop.  Then I minced my way out of the station and into the office.