If you read my earlier story in Forced Womanhood 45, you may recall that I had been ‘forced’ into becoming Rachelle by Paul Owen, the VP of IT for our firm when he found my photos and internet history on my company laptop. I had served him and his lovely wife for over a year when they separated and I was released by Master Owen. He gave me a good reference and I moved to Toronto to start with a new data firm. The money was good and soon I started travelling around the US showing off the attributes of the software I helped develop.
My new story starts when I was asked to go to a trade show in Chicago. I love taking the opportunity to dress up on every business trip that involved an overnight stay so I decided to go a day early in order to spend a whole day and night as Rachelle.
I planned on spending four nights in Chicago so I requested a suite on the highest floor possible and was given a room on the 25th floor. I brought my camera along as I was planning to take dozens of pics to add to my already extensive collection. I have learned that dressing up during the day allowed me to use natural light in my photographs, which made them much more convincing.
On this particular trip I intended to dress up and spend a day in my hotel room working and playing on the Internet. I woke up early, flung open the curtains and as the bright sunlight streamed in I knew that I was going to get some great pictures. I meticulously ironed my skirt and blouse and as part of my dressing up ritual, I laid my lingerie out on the bed. I then hurried to the bathroom where I enjoyed a warm enema and a long soak in the tub.
After I shaved thoroughly (and I do mean thoroughly) I spent an hour and a half perfecting my make-up, fingernails and toenails. I prefer to use career length glue-on nails but I packed in a bit of a rush for this trip and brought only the longer formal nail kit. This meant I had to be a bit more careful since the glue was very strong and snagging a nail can be painful at best.
As my nails dried I began dressing up as Rachelle the schoolgirl. This was the only outfit I brought with me on this trip as I planned to go shopping tomorrow for others. Today my outfit was my restricting pink corset, beige lace-top stocking, white lace bra and panties (transparent Calvin Klein) with white anklets and shiny black stilettos with ankle straps. In reality this is not a very convincing schoolgirl outfit; no school in the world would allow a skirt this short and the stiletto heels and extra-long red nails. My skirt was shortened to a length that barely covered my stocking tops and the blouse was a semi-see-through white nylon that did little to conceal my lacy bra. I added a few strands of pearls, some pearl earrings, 4 rings and bracelets as accents. I looked adorable, in a hookerish kind of way. I sprayed on my favorite perfume, Chanel No. 5, as the final step in my transformation.
Admiring myself in the floor length closet mirror my image reminded me more of a school slut rather than a schoolgirl. Nonetheless, I thought, I wasn’t going anywhere and I could take some outrageous photos. I loved the look when I lifted my skirt and slipped my fingers under the waistband of my panties. My long red nails showing through the thin material as they wrapped around my swelling clit is an obscene and fascinating picture I still remember.
I then retired to the bedroom to take some pictures and what a wonderful collection I assembled that morning and afternoon. I must have taken 30 or 40 pics in a variety of positions with all of my toys in each of my sissy holes. I refrained the whole day from playing with my sissy clit and waited to find a willing partner that night on Sissy Chat.
I was playing on my laptop reviewing the photos when I carelessly pulled off one of my extra-long nails. As I glued it back on I noticed I had not covered the entire nail on my index finger with polish. I pranced into the livingroom, opened the polish and gave my nail a quick swipe. Too quick it turned out as I slipped and covered my cuticle with polish. Resolving to remove all of it, I went to the bathroom to soak a Q-tip in polish remover.
Nail polish remover! I could only stare at myself i mirror as I realized that I had forgotten to pack any.
I sat down on the toilet to ponder what I was going to do. The nails, not to mention the polish, were permanent until I used polish remover and I quickly realized that I had no option but to go and buy some. I then worked through my options, go out dressed as Rachelle and try to pass myself off or go out dressed as my male self with long red fingernails. I decided to go with my first choice. At least no one would recognize me, of that I was certain.
Another look in the mirror and I started to change my mind. I looked like a prostitute in a schoolgirl’s uniform with my high stiletto heels, short skirt and long nails. Again I weighed my options and decided I had none.
I checked the phone book and found a pharmacy two blocks away that was open until midnight. Since it was already 10:00, I thought it best to wait until there was as little elevator traffic as possible so I decided to wait until 11:00pm. A few drinks from the mini-bar helped the hour pass and build up my courage as well as gave me time to freshen my make-up and practice my best girlish voice in case I needed it.
I grabbed my Visa, a few dollars and my room key and headed for the elevators. Thank God there was no one in the hall but as I turned the corner to the elevator there was a black gentleman of 40 or so standing alone. He immediately looked me up and down and said “Good evening” in a very friendly and non-threatening way. I returned his hello and stood several feet from him in front of the nearest elevator door. A sideways glanced revealed that he was very neatly dressed with a fashionable, pressed shirt and pants and shining expensive looking loafers. Even in my 4” heels he was at least 6” taller than me. He wore a few impressive rings and a gold and silver Rolex. I stood with my eyes on the numbers as they descended but I could feel him looking me over, especially my freshly shaven, exposed legs.
The elevator in front of him opened and several male voices could be heard talking loudly from inside as he motioned for me to go forward. The chatter stopped when I stepped into view but the tall black stranger squeezed in beside me, standing between myself and the four partiers. The elevator descended and as more people got on, the tall stranger was squeezed directly behind me. I looked up at the mirror in front of me and our eyes met in a long glance. As we stared at each other someone moved and forced him to lose his balance and lean into me. Rather than fall forward I braced myself and pushed back slightly with my ass. I still can’t understand why but I definitely felt his manhood against my ass for a second. With apologetic looks I shifted back to feel him again – he was very close.
In the mirror, our eyes locked again as we both pushed against the other. To my surprise his left hand reached down and found my stocking covered thigh, my eyes jumped open in surprise, but my slight smile betrayed me. His hand began caressing my leg, travelling up under my hem, toying with my garters and stocking tops and feeling for the elastic waistband of my panties. He hooked his thumb under it and started to slowly pull them down. I had to stop him before he went too far and quickly rotated my hips but instead of him getting the message that I was drawing the line, his hand now rested firmly on my pantied ass and he started to gently squeeze my satin covered cheeks. The rushing elevator suddenly stopped and just as swiftly everyone but my tall stranger got off on the 12th floor. We were alone and I noticed that his hand hadn’t moved from my ass. He pulled me to him and asked me my name, “Rachelle” was the only word I uttered.
He smiled and said “Rachelle, that’s a very pretty name for a very pretty girl. Rachelle, you may have the sexiest mouth I have ever seen.”
As I parted my lips to smile and thank him, he pulled me tightly to him and kissed me. His tongue gently probed past my reluctant lips and our tongues touched. My pink and crimson lipstick lubricated my lips as they now sought to draw him into my mouth. I was on fire and I responded with a girlish moan as my arms went around his neck. He ground his crotch into mine and I knew that the moment of truth was fast approaching. We separated as the doors opened and he grabbed my hand and lead me to a couch in the lobby where we sat side by side, his pants touching my legs. He looked at me with such passion that I knew I couldn’t refuse him anything.
“Where were you headed at this hour, out looking for some fun?” he asked.
“Actually I was going to the drug store for a few things,” I replied softly, not wanting to be too obvious with my voice.
“Great, I know the one, it’s a few blocks away. I’ll come with you and maybe we can go to another store nearby to look at some other things,” he suggested.
“OK,” I said, starting to rise but he sprang to his feet and held out a hand to assist and we walked out of the lobby hand in hand.
I had never been outside dressed as Rachelle before and I definitely felt very exposed. A cool fall breeze played with the hem of my skirt and I used my free hand to keep it in control.
I felt much less noticeable since I wasn’t alone on the street. There were still a lot of people around as he led me across the street and down the block. Once we had stepped onto the sidewalk he asked, “So what did you say your female name is?”
“That’s a strange question. Don’t you mean ‘what’s my name’?”
“No you silly sissy, I meant exactly what I said,” he said in a strangely stern tone.
“Well, my name is Rachelle,” I said with hesitation.
“Don’t you mean ‘My sissy name is Rachelle’?” He corrected me.
“Yes, I guess I did,” I replied with a slight smile.
“Good, Rachelle my sweet sissy. Let’s be honest with each other and we will get along much better. You may call me Marcellus for now.”
“We are going to a shop around the corner that should have some wonderful things for you to wear,” he said as we turned the corner and a large neon sign with 3 large letters brightly illuminating it that read ‘SEX’.
I had been there before but never had the nerve to buy anything since it was so wild, all fetish gear, rubber, latex and leather. As we stepped through the door the aroma of strong incense filled my nostrils and the strange ambiance stirred some forbidden feelings.
The aisles at the front of the store were filled with erotic videos and Marcellus led me through them to the back of the store. Hanging on the walls and on all of the racks were an amazing collection of lingerie, sex toys, wigs, outfits, dolls, bondage gear, shoes and dresses.
Marcellus led me around the aisles, gauging my reaction as he held up different outfits to see how they looked on me. He handed me a leather skirt and leopard print see-through top and told me to go try them on. Knowing that my pink lingerie would be very obvious under the top, I told him my concerns in a close whisper and he laughed, “You silly vain sissy. Go change your bra and panties then but choose some sexy ones.”
He said it so loud that all four of the men in the store stared at me as I choose my new lingerie and headed to the change room to change.
With my corset so tight it was difficult bending over to remove my panties but I managed. As I struggled with my new bra, Marcellus handed me a pair of black, platform stiletto shoes with open toes, “Try these on too sissy.” I got my new outfit in place but I really struggled to change shoes. When I re-emerged from the changing room everyone was standing nearby and applause and catcalls awaited me.
Marcellus said, “You look very sweet Rachelle and I think everyone agrees.” He had his iPhone in his hand and took several photos.
“Thank you,” I said, blushing at the audience.
“Now go try these on,” he said as he handed me another equally outrageous but decidedly more feminine outfit consisting of a pink shiny latex mini-skirt and tank top complete with pink platforms and a shoulder length blond wig.
This fetish fashion show continued for nearly an hour and when I got to the cashier the bill was over $1500. Marcellus indicated that I was paying and I obligingly produced my Visa to do so.
When I looked at the items on the bill I noticed something called a CB3000, bondage gear and toys totaling $500 at the top of the page. These must have been the items in Leon’s bag as I was carrying the multiple bags containing my new outfits.
We headed out of the store and I reminded Marcellus that I still needed nail polish remover so we proceeded right away from the adult boutique towards the drug store. Thankfully we made it in time but Marcellus chose several new make-up items for me as well as the nail polish remover.
I made my way to the cashier and started to check out when Marcellus joined me and handed 2 boxes to the cashier.
“This should be enough for tonight wouldn’t you agree Rachelle?” he asked as the cashier took the packs of condoms and rung them in.
“They are the lubricated kind, they are what you prefer aren’t they?” he asked. The cashier stopped and the young girls behind me all waited for my reply.
“Yes they’ll be fine,” I said quietly blushing redder than my lipstick.
“Oh, is this the douche you asked for?” he inquired with a smirk.
I nodded my response and blushed again.
We strolled back in silence but Marcellus did comment that I should use my hips more in my stride, so I followed his advice and started swinging my hips as well as pushing my chest out. I kept my steps as short as possible to keep my skirt under control. Marcellus was deep in thought anticipating the rest of the evening I thought, but as it turned out, he was scheming on my further and complete feminization.