Walk a Mile in Her Shoes (And More)

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“What stupid, misogynistic, asinine things to say!” Screamed Shanna. “Right now I can’t stand you!”

My girlfriend stormed off leaving me at the bar completely stunned. “Wha? What did I…?”

Rather than an enjoyable evening with the high expectation of getting lucky, it turned out to be a night of sleeping by myself. I flipped a twenty to pay for the drinks and chased after Shanna but she was already nowhere to be found. The guys having a smoke in front said. “If that was your girlfriend, she jumped in a cab and took off. She didn’t look very happy.”

I got into my car and just started shivering. I have no idea why. It wasn’t that cold out but I guess the thought of losing her was just too incomprehensible. I sat there with the engine on and heat blasting out and thought of what had transpired. “Oh my god! She’s right!”

I drove home hoping to apologize to her but found my apartment empty. Not empty of contents; empty of company. I guess Shanna was pretty furious at me and had opted to go to her place. I called her cell but my ring was cut off. I decided to send her a text and hopefully she’d at least look at it.


“You were right. It was stupid, inappropriate, inconsiderate and unthinking. I’m not sure where that crap came from certainly I spoke without my brain working. Women do suffer more than men and the items I used were incomparable to what is real. I hope you know that I don’t believe or think like that.”

“I know an apology is nothing without action but I’m so sorry that I was such an idiot. While I can’t take back the stuff I said, I also know it will take a while but you will never forget how I hurt you. I hope somehow you will forgive me even a little bit. I don’t know where to start. I wish I knew how to fix this. Fix us. I am so sorry.”

“Will you please message me and let me know you got home safe?”

Shanna wasn’t too far from the bar we left, but it took a couple of hours before I got a response. All I got was: “Home.”

I wanted to call and talk with Shanna but decided to give us some room. Not so much for her to calm down but to let the situation settle a bit; hoping she’d think over my apology and forgive me. A couple of days later.

“Buzz! Buzz!” A message on my cell. It was from Shanna. “You are right! I can’t forget what you said. It was hurtful and I was very upset with you. If you want forgiveness and how to fix it, come to my place tomorrow afternoon and you must do as I ask or we’re done!”

I read it again and again before replying. “Yes, I agree. I will come by your place and do as you ask.”

That evening I was antsy and nervous not knowing what to expect. I had difficulty falling asleep. When my alarm jolted me awake I felt I had just fallen asleep. Friday was still a work day so I made my way into my office. Didn’t get much done that morning. I told my super that I had a doctor’s appointment and needed to leave at lunch.

I drove over to Shanna’s place and found her waiting. She was wearing a plain tee and jeans; had very little make-up on and still had a little fire in her eyes.

“Shanna. I want to apol…” Was all I got out, before she told me to be quiet.

There was a knock on the door. With a nod of her head, Shanna motioned for me to get it. I opened the door and saw Greg her neighbour. After Shanna nodded for him to come in, I looked at her to see what was happening.

“Greg is here as part of your apology and to make you understand what it is to be a woman.” Shanna told me. I looked back with questioning eyes. “He’s going to convert you. Do as he instructs. He speaks for me.”

Greg was a cross-dresser. I’ve seen some amazing picture of him in drag. Even live and close up it was difficult to tell she was a he. His first instruction was “Strip!”

I looked at Shanna. Her return glare told me I’d better obey or we’re done. In front of both of them, I took off my clothes in the middle of the living room. Shanna announced. “I’ll be back in an hour.”

“Shower!” Greg followed me in. He instructed otele gelen escort me to wash and then in a surprise, handed me a razor and said to shave “Everything!”

Greg allowed me to keep my eyebrow but that was it. I was bald and hairless everywhere else. I dried off. Having no hair felt strange yet arousing. I followed him into Shanna’s bedroom and thought “Uh oh! What’s happening now?”

“Put this on.” Greg handed me what looked like a thong with a tiny tight fitting pouch. I slipped it on and followed Greg’s instruction and pushed my cock inside me. When the straps were pulled taut around my waist and between my ass crack, my balls were squeezed together and made me look like I had a fat camel toe.

I was kind of concerned about what was happening but Greg reminded me what Shanna had said so I just shut up and let Greg do whatever which included him painting my finger and toe nails a bright red; my right index finger was sparkly.

Next were tiny girl panties. Fiery red when pulled up only accentuated my “pube.” Greg rubbed my chest with some cold liquid and attached on some silicon breast forms. I held them there until the glue set before Greg helped me on with the fiery red lace bra. When I let go of my boobs, they felt very weighty. They were definitely bigger than Shanna’s C’s. The nipples were hard and about the size of cranberries. Some touch up toning and you couldn’t tell they were not part of me.

Then came stockings and garters. Again Greg helped me on with them. I felt some stirring between my legs as the silky nylons slid up my hairless legs but the pouch kept control of my excitement.

Greg sat me in a chair next to a table covered with make-up. He worked on me for almost an hour; shaping my eyebrows, gluing on long false eye lashes, full foundation and full make-up. Bright red lipstick with a darker lip liner.

He stood back, smiled and admired his work. Satisfied, he opened up a box and pulled out a wig. He secured it on my head and let the long, deep red hair cascade over my breasts. Greg said pointing at the mirror. “Take a look.”

I turned slowly and was amazed at the transformation that was me. My mouth dropped. I knew it was my reflection in the mirror but I didn’t recognise the female at all.

“Amazing, eh?” He asked not really expecting an answer. “What size shoe do you wear?”

“Uh… Seven.” I had small feet.

“Try these on.” Greg handed me some shoe. They slipped on perfectly. “They are only two inch Cuban heels. Stand and try to walk.”

Even so, I nearly fell as I first stood but Greg helped me with that and told me how to walk. Within about ten minutes, I was able to walk reasonably well. My ankle only buckled every now and then. I was pretty proud of myself.

Greg handed me a blouse. It was white and opaque. When done up my big breast protruded and my pointy nipples jutted out even more. Greg undid the top three buttons and adjusted my cleavage. The skirt was tight and short. It barely covered the tops of my stockings. As I walked around, I could feel the hem start to climb upwards. I kept having to pull it down.

“I’m back!” We heard coming from the living room.

“Go!” Greg pointed me towards the voice and then called back. “She’s coming out!”

Now it struck me. I was dressed and transformed into a woman and was about to face my girlfriend. Fear struck my gut hard. His stern pointed index finger told me I’d better move.

Slowing opening the bedroom door and peeking through, my first sight was of Shanna bouncing impatiently on one foot in the middle of the room with arms crossed under her bosom. When she first notice my face, her mouth dropped. As I emerged from my hiding place, you could see the shock at what she saw. “Holy shit! Greg, you did an amazing job! I can’t even tell he’s a she… he… she!”

Greg and Shanna made me parade and model around the room. I confidently strode around until I carelessly buckled my ankle again and brought me back to earth. türkmen escort Shanna whispered something to Greg. He shook his head and left leaving the front door to Shanna’s apartment open. A few minutes later, Greg returned with a shoe box. He opened it up and handed me a different pair of shoes.

I kicked off the old pair and slid my nylon tootsies into the new ones. They were almost the same shade red only shinier. The open peep toe exposed the painted toe nails under the stocking I was wearing. When I stood, I nearly fell again. The steel heels were much higher; four and a half inches and thinner, much thinner.

“Perfect. Thanks, Greg. I owe you.” Shanna hugged Greg before he left. “Well… Um what should I call you?”

“Cheryl. I always loved the named Cheryl.” Spilled out of my mouth.

“Well Cheryl. Are you ready?” Shanna asked.

“Er… Ready for what?” I timidly asked.

“To see what it really feels like to be a woman.” Shanna explained. “In public.”

“What? I can’t go out in this?” I protested. Now that I think of it, going out excited me. “This is humiliating.”

“Okay, I won’t make you do anything you don’t want.” Shanna said then held the front door open and reminded me. “You can leave now but we’re done. Forever.”

My head bowed; my shoulders and ego deflated. I loved Shanna too much and felt my defiant spirit leave me. I didn’t move.

“You staying?” I meekly nodded affirmatively to Shanna. “Good. Stay.”

She went to her bedroom and came out a few minutes later. “Remember the time you had me wear this remote vibrator in public? Well I think it’s your turn this time. Pull up your skirt.”

I stared at the familiar looking tear drop shaped toy. I had her wear it and I would turn it on at random times and enjoyed watching her squirm. On the way back to the car, she actually came.

“Er… but that goes in a vagina.” I explained as I raised my hem around my hips before referring to my fake slit. “This isn’t real.”

“Not going there!” Shanna motioned for me to turn around. “Bend over.”

Shanna pulled my panties aside enough to expose my hole. I felt her squirt some cool slippery lube inside and then place the toy at my rear entrance. “Ready? You should be used to it after all the times you had me fuck you with my strap-on!”

The increased pressure told me it was going in whether I liked it or not. Slowly, the vermilion toy stretched my hole open before slipping inside me. Shanna pulled my panties back into place. I stood up and pulled my skirt back down. I nearly doubled over and fell as there was a sharp buzz up my ass. Shanna smiled. “Guess it works!”

It was late evening when we left her apartment. It was a warm fall evening so no need for coats whici meant my boobs and nips were prominent as we walked down to her VW Cabriolet. With the rag top down, Shanna drove. As she did, I found it difficult to keep my skirt from climbing. A couple of times, we waited for a light and the driver in the SUV beside us got an eyeful of my legs and stocking tops.

Shanna drove around for a while. It wasn’t the worst part of town but was rough around the edges. She stopped the car. “Get out!”

“What? Here?” I responded in fear.

“Yes, here!” There was an extremely hard reverberation in my bowl that made me double over. “I won’t ask again. Get out.”

I opened the door and stepped out. A cool gust blew up my skirt. I closed the door and looked at Shanna.

“I want you to feel what it’s like for a woman by herself to walk and deal with all the other fucking idiot males out there.” Shanna pushed the door lock button. Just before she drove off, she told me. “I’ll meet you at Church and Isabella.”

I watched Shanna drive off leaving me in a wake of dust. It was at least ten blocks from where she left me to the meeting place. I had no purse, no money, no phone. No one. I thought. “The sooner I get this done the faster it will be over.”

As I took a few steps, I was reminded of the evi olan escort invasion up my butt. Less than ten strides, I heard a call from a passing car. “Hey honey! How about putting your lips around my hard dick!”

I wanted to punch the asshole in the face but the drove off too quickly. A few more steps and I grunted when there was a small jolt up my own asshole. I looked around but saw nothing and continued my trek. Every ten or fifteen steps, there was a jolt. Every jolt was a little longer or a little stronger making my knees buckle each time.

The quickest way would be through the park. I’ve done it many times before as a male. I didn’t feel threatened at all until I got about a quarter way through. Some rubbie guy came up to me. Unshaven, unkempt he stood before me. His shoddy trench coat open. I looked down to see his filthy cock sticking out of his pants; he was jerking himself off as he gawked at me.

I tried to walk around him but with each step there was a powerful shock which prevented me from doing so. It had to be Shanna controlling it. I looked around but saw no one else.

The bum was standing right in front of me. He reached for my hand which I pulled away but was immediately reprimanded by another reminder in my rear. When I didn’t move, he grabbed my hand again and placed himself in my palm. This time a gentler vibe prodded me to stroke him. He felt nice in my hand.

As I jerked him off, he brought both hands up and grabbed my tits. Luckily his came pretty quickly. Unfortunately for me, he came all over my legs and feet. I couldn’t believe the amount that came from his dick. When he was done, he just quickly scurried away. I was left standing there with his hot spunk dripping down. My white blouse soiled by his grimy hand prints.

I had nothing to clean up his mess with and started on my journey again.

Almost through the park, I smiled at a nice looking guy who smiled at me. Suddenly there was a strong pulsing pattern that made me winch and double over. The some called gentleman came to help but ended up groping my breasts. I felt his hand go under my skirt and finger my fake slit. But when he felt my appendage, he realized what I was and took off yelling back at me. “You fucking perv!”

I took more public crowded paths and made my way uptown. Passing bars and clubs, guys smoking outside would give me kissy sounds and wolf whistles. I was relieved to finally reach our meeting place, but Shanna was nowhere to be found.

I stood on the corner where I was approached by a number of men asking if I needed a “date” tonight. I tried to fend them off but when a cop car stopped, they scattered. One of the cops got out. “Hey honey. You’re new. I don’t recognise you.”

I didn’t know what to say or do. I looked around scared to see if I could find Shanna.

“I need to take your info.” The cop said. “Get in the back.”

I got in but he followed me in. The driver cop pulled away. I tried to look for the cop’s name tag but he had removed it. He told me to call him “Officer Dan” as he took my name and other info. Then he told me that “You will need to pay for our protection.” And grabbed my boobs.

He looked at me. His hand went between my legs and found my package. “Wow. You did a great job. I couldn’t tell you were a fake girly girl.”

Taking me by my hand, he guided it to his zipper and made me pull it down. He feed his hand inside and made me pull out his cock. It was big, thick and uncut. He grabbed the back of my head and pushed me down towards his crotch. He didn’t have to try very hard. My mouth automatically opened and I took as much of him as I could. I bobbed my head up and down sucking him as hard as I could.

When he came, he came hard and plenty. I tried to swallow it all but some leaked from my mouth or shot out from my nose.

Satisfied, they dropped me off back at my corner where I found Shanna. I didn’t tell her anything about any of the activities that occurred during my journey but from her smirk, I think she already knew. We drove back to her place. “Well I hope you understand what women have to deal with.”

She didn’t let me clean up or change before we went to bed. She fucked my ass with her strap-on until I came and came. Resting afterwards, I thought about “what women have to deal with.” I now understand but really didn’t mind.

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