No Such Thing as Bad Exposure

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A late night walk does not go as planned.
2.6k words
4.46
12.2k
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Part 1 of the 2 part series

Updated 06/11/2023
Created 04/21/2022
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One last check in the mirror and I could see the dirty blonde wig looked perfect and my make up was smoking. OK so maybe up close I still looked like me but from a distance I was definitely passable, although I'm not sure a 'real girl" would wear this outfit.

The black leather corset held the top half of my body tightly as the black thong did the same with what in this outfit could only be called the last of my manhood. The leather custom made leopard print skirt and bolero jacket were snug and matched the 6" leopard print stilettos I was wearing.

The skirt and jacket were a parting gift from my ex girlfriend Emma who two years ago told me I needed to find myself before I could ever be truly happy. She was the only person I had ever told about my crossdressing and whilst cool with it she questioned my sexuality, which I also did, after seeing my enjoyment from the occasional finger in the ass during a blowjob. Over time we became more like friends with benefits than a couple and eventually she moved away for work.

We were still friends, talked from time to time and as I said her parting gift was this skirt and jacket. The jacket came to just below my rib cage with a gold zip fastening from bottom to top. The skirt came to just below my knees with the gold zip running over my right leg, this time fastening from top to bottom. Usually I liked it zipped all the way down to restrict the length of my stride but tonight I had it zipped to mid thigh showing plenty of leg (always smooth of course).

After breaking up Emma had encouraged me to get together with a guy to see if I liked it. I never got the nerve to do this but I did discover a thrill from leaving the house dressed hence why I was here now at 10:30pm on a Saturday night checking my makeup in the hallway mirror.

The night had started with me playing wing man to my friend Gregg. He had met a girl in a bar a few weeks ago and we had seen her again last weekend. Some flirty messages had made it clear tonight would be his lucky night if she saw him out again. Not wanting to take any chances on having to get a cab etc he had driven and not long after 9:30 they had gone.

Gregg going left me on my own but after a short cab ride home I was pulling out my favourite outfit and grabbing my makeup case whilst knocking back vodka and coke to keep my buzz going. Now dressed and made up I gave myself a final check in the hallway mirror before going for a walk around my neighbourhood.

My neighbourhood was a new design concept with parking around the outside and pathways crisscrossing between 200 or so houses. This was great for me as whilst I liked the thrill of going out dressed and possibly being seen there were plenty of paths giving options to escape if need be. Normally I could walk the circuit of pathways in less than 10 minutes but in these heels it was more like 15.

Blowing myself a kiss in the mirror I turned and opened the door coming face to face with my friend Gregg!

"Urrrggghh Hi" was all he could say after his eyes went down my body and back up again.

His hand was still outstretched, clearly about to knock on my door, so I grabbed it and pulled him inside. At 6'2" he would normally have been 2" taller than me but in these heels he looked up as I searched my brain for a reasonable explanation of why I might be dressed like this.

As I stood saying nothing he told me how they had gone back to her place, had sex and then she had kicked him out as she had work early the next day. Apparently she was quite kinky so he had wanted to come round and give me all the details. I wondered where I was now sitting on his scale of kinkiness!

Nervously I asked if he wanted to come and sit down and after he nodded I turned and walked through to the living room, the click of my heels echoing off the wooden floor. Asking if he wanted a drink Gregg said he would get them before going to the kitchen.

Going into the living room and trying to cover myself up somewhat I sat and crossed my right leg over my left at the knee but all this did was give Gregg a lot of leg to look at which is what he did as he came in holding two glasses.

Standing up I zipped the skirt down and took one of the glasses. I assumed it was vodka and coke and taking a big swig I found it was heavy on the former and lighter on the latter.

We sat and talked for over an hour with Gregg making several trips to the kitchen to keep our drinks topped up. With the vodka flowing I told him how I had got into this, how Emma had known and helped me expand my wardrobe, that I liked to go out dressed and how it turned me on to know that I might be seen in public like this.

It was almost midnight when I told him the last part and looking at his watch Gregg suggested we go for the walk he had interrupted.

"Come on let's go" he said standing. "Grab a bag, your phone and your airpods as well" in what seemed like an almost forceful manner.

Nervous and excited the items went into a small gold clutch, as did my keys once we left the house. He told me to walk where I normally would and as I began I checked back seeing he was maybe 5 metres behind with his phone in hand. Whilst nervous at being filmed by my friend I gave it my most confident walk although was severely restricted in these heels and with the skirt zipped down to the bottom.

After walking for five minutes we were about to cut across one of the car parks when Gregg told me to walk over to a black Mercedes SUV at the far end of the carpark. Following his instruction I walked towards it but was blinded by the lights of a car pulling into the carpark and as it drove past I noticed it was a middle aged couple who lived a few houses up from me. As I got closer to the SUV the side lights flashed and Gregg told me to get in on the passenger side.

"Oh my god oh my god" I panted as Gregg got in the drivers seat. "Jennifer totally saw me" I said in a mixture of worry and excitement.

"She didn't see YOU, she saw a very tall very hot slut" which calmed me down a bit whilst also exciting me that Gregg had called me that.

Reaching forward he pressed a button to start the car and I asked what he was doing, as he had been drinking, and whose car it was. He told me it was a courtesy car as his was being serviced and his drinks had only been coke. He said as I liked the thrill of possibly being seen he would help me to explore it further before putting the car in gear and pulling away without giving me time to agree or not.

Gregg's phone connected to the car and he played Britney which I sang along to as he laughed. With the car having tinted windows I was relaxed and we drove through the centre of our home town at times being very close to drunk guys stumbling around and girls tottering out of bars in heels as high as mine. I knew many of these people but in the car I felt safe as they couldn't see me.

After driving through the middle of town a couple of times and getting back to the edge Gregg pulled up at the side of the road, looked at me and told me to get out. Open mouthed I shook my head hoping the panic in my eyes told him I was not comfortable doing this.

"We are on the outskirts of town, there is no-one here. All I want you to do is get out, I will drive to the end of the street and after walking the same you can get back in. Put one of your airpods in your ear and I will be able to hear you and you me. If something happens I will be right here OK."

The words were comforting but the tone of his voice told me this was an instruction rather than a discussion so after pushing the airpod into my ear and covering it with my wig I turned and nervously grabbed the door handle pushing the door open. After stepping out and closing the door my phone rang as Gregg began to drive up the street.

Tapping my ear I heard Gregg reassuring me that everything was fine and to enjoy the moment. I could see his brake lights perhaps 100 metres in the distance and walked towards him as fast as I could. I could hear voices and a couple of cars drove past and with my heart pounding I got to the car very turned on by what was happening and glad the heavy leather of the skirt did not make it obvious!

Reaching for the door handle the car pulled away and turned a corner just ahead of where it had been parked as I stood there with my hand still out. "A little bit further" Gregg's voice said into my ear.

He had driven closer to the centre of town but what choice did I have. I loved wearing heels but I was not going to walk 4 miles back to my house in 6" stilettos and this outfit so I walked to the corner and checked it was clear at the same time seeing Gregg had pulled in further ahead at the end of the road.

"That's it girl, put some wiggle in that walk" he said laughing as I made my way towards him, the dull sound of music and voices getting louder with every step.

As I walked he asked how I felt and I told him I was both nervous and excited to be doing this which was when he told me he was going to drive away again.

I begged him not to make me walk further into the town centre but he told me he wasn't going to as all I needed to do was stand on the corner and wait for him to drive back around and he would pick me up.

I realised what I would look like stood on the corner dressed like this but as it dawned on me he pulled away once more.

I stood and waited checking in each direction. A few cars drove past with one clearly slowing down and almost crawling past me. The door of a wine bar up the street opened and four people came out. I hoped they would walk in the opposite direction but only got half my wish as hugs and handshakes were exchanged and the four split into two couples with one headed my way. If that was not bad enough as the couple got closer and came out of the shadows I realised the girl was not just any girl but was my ex Emma!

"Oh my god look at you" she screamed as she saw me.

"Is that Emma?" I heard Gregg asking in my ear but didn't need to answer as she was talking away with him hearing every word.

"I can't believe you came out in this outfit, you are such a slut" she said laughing before introducing her boyfriend Steven telling him I was the ex who liked to crossdress. Clearly she had told him about me and when she said I should introduce myself Gregg said into my ear to introduce myself as Britney. As I did in my best female voice Emma clapped her hands in that girly way and Steven smirked.

"Our cab is picking us up on the other side of the road in a moment - do you need a lift home babe" Emma asked.

Gregg told me to say no and when she asked what I was doing he had me tell her I was waiting for a ride. She laughed and said she could definitely see me getting a ride dressed like this. She said she would message me soon and after saying goodbye her and Steven crossed the road but they were still very close to where I was stood.

My heart was pounding and I heard a car pull up behind me, thankful when I turned to see it was Gregg. He had driven down the road and was stopped at the side of the road facing Emma and Steven but they could not see him due to the tinted windows. He hung up our call and I reached for the handle but found it locked as the window came rolling down to him sitting there with a big grin.

"You know I never asked what you were wearing under your skirt" he said with a devious look on his face, perfectly aware of what this looked like to my ex girlfriend.

I told him I was wearing a black thong but he wanted me to prove it. I told him I couldn't take my skirt off to which he ageed and instead told me to remove my thong. I shook my head and he revved the engine telling me it was a long walk home and the bars would be emptying out soon.

Not wanting to look across to Emma I threw my clutch into the car through the open window and began to unzip my skirt from bottom to top. My hands were shaking and I felt the cold air on my skin as the zip got higher and higher stopping only an inch or so from the top. Hooking my thumb under the waistband of my thong I managed to bring it down enough to let it drop whilst not letting anything else come into sight.

I could hear Emma whooping and laughing across the road before what was clearly the flash from a camera. Stepping out of my thong and bending at the waist I picked it up using the end of my finger and held it up facing my ex and her new boyfriend before the flash went off again. "I want a copies of those please" I said in my most confident voice trying to disguise how embarrassed and turned on I was.

I turned to Gregg and passed my finger through the open window dropping the thong onto the passenger seat and upon doing so he pressed a button to unlock the door.

I climbed in and sat down shaking and panting from the excitement. I looked at Gregg and we made eye contact as he asked if I was alright. I nodded and felt his hand on my bare thigh looking down to confirm that's what it was. I looked back up and as we made eye contact again, his hand squeezed my thigh and he said "Good girl" at which point I was gone.

I had read about no touch orgasms before but never experienced one. As he squeezed my thigh my mouth opened, a girlish squel left my mouth and I came hard over and over again........

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JennifeeheelsJennifeeheelsalmost 2 years ago

The endinf feels very rushed, but i live the rest. ā¤ļø

JentvcdJentvcdabout 2 years ago

This is so Hot as I myself on many occasions

ventured out dressed at night its so thrilling

and exciting and one is so vulnerable that

makes it even more thrilling for sure as you

never know what to expect.

Well Done Keep writing !!!

ShortyMacShortyMacabout 2 years ago

Thatā€™s so hot. I hope you continue with this story. Would be nice to have the two of them wind up having hot sex.

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