Well, having disappointed myself and especially displeased Mistress Christine a couple of months ago by not getting all femmed up and going to purchase new eyeglasses, Mistress Christine gave me a new assignment. This time lacy was traveling, a five and a half hour drive and would be driving through Indianapolis IN. Not to challenging until Mistress Christine laid down the rules. lacy would be wearing pantyhose, panties, 42 D cup bra with breast forms, waist nipper, womens slacks, and a womans blouse. Oh and of course heels with open toes so her bright red toenails would show through and matching cocksucker red lipstick. After leaving from work lacy ducked into a restroom and changed into her slacks, bra, breast forms and blouse. Walking out I was aware of every little detail of the walk to the car. It was unnerving, humilating, and exciting. Good thing I was wearing a pantyliner to catch the drops and keep my panties and slacks dry.
Arriving in Indy, I drove to the mall and forced myself to go into a shop named Lover's Lane, looking around, I heard the pretty clerks giggle as I minced over to the lingerie section. Several times they came over and asked if I needed help in finding something. None of the outfits caught my attention, but two red wigs really did. Being a real redhead I found them to tempting to resist and bought both, one shoulder length that turns under and a longer curly one. The clerk said I hope you enjoy these and invited me to come back anytime.
Now walking into the mall I headed straight for the shoe store and Lane Bryant. The clerks again giggled embarrasing me so much when they did. But they helped me find a lovely purple ruffled blouse with a black lacy cami to go underneath and a black skirt. Unfortunately I chickened out and did not ask to try them on. Later I will out how much this displeased Mistress Christine along with the fact I hadn't taken my purse in.
On to the shoe stores, looking at the shoes in several store I finally found some that I wanted. Walking on inside the clerk, grinned broadly, and I am sure she was stiffling a laugh. Approaching me she asked if I needed help and I pointed out a couple of pairs that I was interested in. One a pair of black higheel clogs with studs and little chains on them, and the other a pair of highheel knee high boots. She was great helping me try them on and then making some trips to the back to get different sizes and colors. I tryed them on and walked around the store as she suggested. I know she was looking at me and having a good time with this. Deciding on the two pair I wanted she showed me some leggings but unfortunately didn't have my size. Paying for my selections she like the other told me to enjoy them and that they looked good on me and invited me back.
Now for the long drive to my final destination, oh dear, I realized I had to get gas. Mistress Christine had certainly know I would have to to this in femme. Going to the gas station, I had to screw up the most courage ever as there were plenty of people, men, women, teens, all looking at the guy dressed in femme and heels, with lipstick filling the car. I wanted to crawl under the car, but had to stand there. When I got back in I almost came.
The drive was torturous, being dressed up and so sexually arroused and not able to play with myself until I got to the hotel. Finally arriving at the hotel I had to walk in dressed like that and sign in for my room. As usual the clerks go their giggles in and the guy at the counter did a smirk and kept looking in disbelief. The clerks gave me the key and told me about the complimentary cocktail hour and breakfast. Humilated and aroused at the same time I was litteraly dripping at the crotch. Getting to the room and carrying all of lacy's special suitcases and new purchases wearing heels was an exercise in obedience as well. Especially with others around.
Changing into a new outfit, blouse, nipper, panties, hose, and knee high boots I anxiously called Mistress Christine. Mistress made me tell her all about all of my adventures. She was so pleased with me until Mistress found out lacy had failed to take her purse in and had not tried on her purchases at Lane Bryant. Mistress was really disappointed. She then proceeded to put me through a series of stroking sessions while kneeling on a ruler, spanking myself with a leather paddle, and then it got really tough. Kneeling on the ruler stroking, sucking my big dildo, and spanking myself. Then a series of twenty strokes wanking and counting each stroke without cumming. Next lacy had to remove her buttplug and insert the dildo, kneel on the ruler and stroke. Then fuck herself with the dildo numerous time and then sit on it to stroke.
Mistress had lacy begging to cum but her real punishment must happen first. Nipple clamps were now attached and tied off to the coat rack in the hotel room, and hands handcuffed behind the back with the keys on the other side of the room. Standing there in heels, dildo inserted up to the balls, highheel boots, red wig and aching for release. Mistress Christine began telling lacy how disappointed she was in her for not completing her assignments to the letter. Lacy had to promise that from now on she would always try on outfits before buying and always take her purse when shopping. Mistress Christine's voice then suggested that lacy go ahead and undo her handcuffs. But Mistress the keys are on the bed. "I know lacy but you only have one way to get out of this, pull the nipple clamps off by stepping backward." I couldn't do it, it hurt terribly as I pulled back a little. Mistress Christine kept telling me how much of a slut I was then telling me to pull the clamps off. Finally i pulled and pulled and they came off one at a time. I wanted to scream and cry at the same time. But I knew this was a punishment and had to comply. Mistress then reminded me of my punishment and requirements to carry my purse and try on clothes and how humilating it is for me to do this. All things were right with the world at that moment.
I owe her so much.
