Getting Courage

I am Colleen, when I get all dolled up. I have been crossdressing secretly for all of my adult life. Derp down I so wanted to go out in public as Colleen. But being the late 90's, it still wasn't accepted as much as it is today. I settled for walking around my house as Colleen for years. Always wishing and dreaming about going somewhere, anywhere, as Colleen. I wanted to go out as Colleen every time I became her.

I remember that Sunday evening quite well. I had been Colleen all weekend. Starting from Friday night, when I got home from work. I changed the moment I got home. Shedding my male work clothes, and dressing in my beautiful, soft, silky clothes as fast as I could. I slept that night in a pair of tan pantyhose and a white cami.

I spent all day Saturday in the same tan pantyhose, a t-shirt, a short jean skirt and heels. Living alone in heavily wooded lot, I was able to go outside with out worrying about being spotted. I spent a fair amount of the day outside doing yard work. But that evening, the urge to go somewhere struck. I sat on my back porch, with a glass on wine, pondering about where I could go. What would I do? I poured myself another glass on wine, and gave up on going out that night.

Sunday morning, I got up and took a long bath. I shaved my legs smooth. When the water cooled off, I got out and dried myself off. Then I put lotion all over my legs, and got ready for another day as Colleen. I painted my toe nails a deep cherry, and waited for them to dry. Since it was Sunday, I dressed up a bit more. I started with a new pair of No Nonsense Sheer and Silky suntan pantyhose.

I had never worn them before. To this day I recall how smooth they were. So much silkier than the Legg's I would normally wear. And the light shimmered off them like a much more expensive brand. I stepped into a black skirt, that had a slit up the right side. I just had to let those shiny pantyhose be seen, along with most of my thigh. It was quite the slit. I put on a white lace bra, and filled it with my homemade breasts.

After much experimenting, I found that a condom filled with water made nice breasts. And the knot looked like nipples. They were quite durable, and would last me a few weeks. But I hated when they would suddenly burst. I never knew when it would happen.

I sat down and applied my make up, and chose a light brown wig, with wavy hair that went past my shoulders. Then I chose a red, silk blouse. Lastly I slid my feet into a pair on 4 inch peep toe heels. I looked at myself in my full length mirror, and saw that I had truly outdone myself. It was the most I had ever looked like a woman. I never, to that day, felt, or looked more like a woman.

I spent the day doing small projects around the house. And looking in a mirror every chance I got. Colleen was never so striking, or so convincing. Around 7 that evening, the thought to go out wandered through my brain. I usually had that thought after a couple of glasses of liquid courage. But I hadn't had even a sip so far. Would this be the night I finally do it?

I went up to my bedroom, and touched up my make up. I applied fresh lipstick, combed my hair, and looked at myself in the mirror. 'Ok Colleen. It's time for you to step out into the real world.' I thought.

My heart was already racing as I picked up my purse and removed my car keys. I stepped outside and locked the door behind me. I got to my car, sat down, closed the door and started it up. I was so nervous. I had never gotten this far before. I sat there, the car running, my hand frozen on the shifter.

'Just put it in reverse, and go to the park. It will be almost dark when you get there.' I still couldn't move my hand. I looked at my hand. My red finger nails were shaking, and not from the car. I took a deep breath, and suddenly the car was in reverse. I turned the car around, and began to head toward the street. As if in a dream, I found myself going out of my driveway, and down the road.

I quickly discovered that heels are quite difficult to drive in. But soon I was getting the hang of it. Before I knew it, I was pulling into a deserted parking lot at the park. I went to the far end of the lot, and parked. I sat there a few minutes, just thinking.

'Colleen, you have come this far. All you have to do is open the door, and step out.'

I looked at myself in the rear view mirror. Colleen looked ready to go. I took a deep breath, opened the door, and stepped out of my car. My heart was racing in my chest as I took my first few steps away from my car. The feeling was so liberating as I walked further from the safety of my car. The light breeze on my legs felt better than it had ever before. The sound of my pantyhose swishing, along with my heels clicking, was like music in my ears.

I was so excited, that I even began to feel a stirring in my groin. I was glad I had tucked myself away. That decision made my feel even more like a woman, because I soon felt a damp spot growing in the gusset on my pantyhose. I was in heaven. I walked towards some picnic tables and benches, wishing I had done this years ago.

I stepped onto the grass, and headed for a bench. I had to take my time to keep my heels from sinking into the soft ground. I eventually got to the bench, sat down and crossed my legs, allowing the slit to fall open. I slowly ran my hand up and down my silky thigh. Colleen was finally out, and free.

I sat there, watching a beautiful sunset, still not believing that I, actually Colleen, was sitting at a park, in public, dressed as a woman. But as incredible as I felt, I was glad that I was alone. I wasn't sure if Colleen was truly ready to be seen yet. I felt that I was passable, but I still had a small amount of doubt in my head.

The last of the colors were fading from the sky, and it was getting cool. I was ready to leave. I stood, and made my way back to my car. My walk was more confident going back. My heels clicked with more confidence. My stride was more lady like. I felt my hips swaying, my little ass wiggling. This was a perfect evening. Nothing was going to ruin it.

I got in my car, and turned the ignition on. Nothing. I tried again. Still nothing. I was wrong about a perfect evening. I had a dead car, and I was dressed as Colleen. Now what? I was alone and it was getting dark. I had no way of getting help, and I wasn't sure how to get any. I was in a tough spot.

I walked around, not knowing what to do. I didn't even see a pay phone. Not that I could call any of my friends, and have them meet Colleen. It was now dark, and I still had no idea what to do. I thought about walking home, but not in 4 inch heels. That would be insane. It was getting cooler, and I was walking in the parking lot to try and stay warm.

Suddenly I was bathed in light. I froze where I was. It got brighter and brighter. Then I heard a vehicle approaching. I was elated, but also scarred. A small pick up truck drove past me, and parked. I noticed a the driver checking me out as he passed by. He got out and stood by his truck. I knew I had to ask him for help. He just stood there as I began to approach him.

"Hi there. I was wondering if you might be able to help me?" I said in my best female voice. "My car won't start, and I need to get back home."

He looked me over in the moonlight. I saw a smile growing on his face. A slightly devious smile, creeping across his face as he looked me up and down. Concern was starting to grow in my mind. What I gotten into?

"Sure ma'am. Is that your car over there?"

"Yes. I would be grateful if you could help me."

He got back in his truck, and drove over next to it. The prick didn't even offer to take me over. He got out and watched me walk across the lot, to my car. That devious smile on his face the whole time.

"So what seems to be the problem?" he asked.

"It won't start."

"Sounds like a dead battery. I work at a near by garage. Hop in and we can go get some jumper cables."

I couldn't say that I was excited about his idea. I liked that he was trying to help me, but being alone with him....

"Well do you want help or not? You can at least stay warm in my truck."

That was a good point he made. I was quite chilled. The thought of a warm vehicle did sound inviting. He was standing there looking at me, next to the open passenger door. Against my better judgement, I walked to the open door. I began to feel the warm air, spilling out, and flowing across my chilled legs. I put my left leg inside the warm cab. I felt a sudden rush of cold air on my right thigh as the slit in my skirt opened wide. His eyes were glued to my leg as I quickly pulled it inside. And there was that damn smile again. I knew he got to see quite a bit of my nylon covered leg. The slit went past my mid thigh, plus my skirt hiked up a bit as I got in. I felt embarrassed, yet also a bit turned on. As he walked over to the drivers side, I could swear that I saw him adjust himself. Was I, Colleen, turning this stranger on?

"By the way, I'm Andy." he said.

"I'm Colleen. Thanks for helping me. I didn't know what I was going to do until you showed up."

We drove out of the park, and towards town. I noticed that Andy was glancing at my legs quite a bit. I was enjoying the feeling of his eyes on my legs. I felt butterflies in my stomach every time he looked. Was this what it was like when a woman tuned a man on? He casually put his hand on the head rest behind me. As we talked, I felt his fingers lightly brushing my hair. His fingers made their way, through my hair, to the back of my neck. He did have a light touch, and I was enjoying it.

We got to the garage all too soon. Andy got out, and quickly came over, and opened my door for me.

"I'll wait here, if you don't mind." I said.

His eyes were again glued to the open slit in my skirt. His gaze went from the top of the slit, down to my heels, and back up. I pulled the slit closed, as best I could, as he looked back up at my thigh. He shrugged his shoulders, and headed for the door. I saw him clearly adjust his crotch as he walked away. Once he was inside, I had to adjust myself. I was also getting a bit excited. I think it was from the affect I was having on Andy.

Andy returned a few minutes later with the cables. He opened my door, and put them on the floor near my feet. I clearly felt his hand brush against my right calf. It lingered a bit too long to be an accidental touch. He clearly meant to touch my legs. Then my thoughts were confirmed. I felt his finger tips, ever so lightly, tracing the outside of my ankle, and slowly creep up to my knee. Andy let his fingers linger there for just a moment too long, before removing them. The butterflies returned in my stomach. Andy had turned me on like I had never been turned on before.

When he stood up, I noticed the effect I was having on him. The front of Andy's jeans were stretched out. I clearly saw the outline of a stiff cock. Upon seeing that, my own cock spewed a bit of precum. Well more that a bit. I felt the sudden wetness in the crotch on my pantyhose. It was like Andy touching my legs, and seeing the effect I was having on him, gave me a mini orgasm. What was happening to me? I had lots of emotions rushing through my brain.

Andy stepped away, and went to the drivers side. He got in and we drove off. I noticed his hand on the seat, very close to my left thigh. Could I let this go any further than it already has? I did enjoy his gentile touch. But I didn't want him to go to far with me. And I didn't want to go to far with Andy. Or did I? I wanted to feel his hand on my thigh. I couldn't get the way it felt when he first touched me, out of my head. It was almost lovingly. And the sight of his hard dick in his pants. Knowing that Colleen had done that to a man.

He was so subtle, that I almost missed it. Just a light touch on the side of my leg. It was just below the hem of my skirt. My leg seemed to tingle where Andy touched it. It felt wonderful, and I wanted him to touch more. I turned my seat a bit, leaning my legs a bit towards Andy. His hand was quickly on the hem of my skirt, with his fingers now caressing the inside of my thigh. Electric waves shot straight up to my groin. I was truly Colleen now. And I was starting to think that she might just be a slut.

We got back to my car all too soon. Andy got out, and opened the door for me. I slowly slid out, letting my skirt ride up a bit on my legs. Andy had me get in my car and asked me to open the hood. I tried to find the hood release, but couldn't. Andy reached in, right between my legs, and popped the hood open. I closed my legs a bit, letting him get a good feel of my pantyhose. He gently removed his hand, letting his fingers glide along my thighs. Then he quickly hooked the cables up. He stood next to my open door.

"Your dome light is on. That's a good sign." he said. I noticed that he was once again looking at my legs. "Give the battery a few minutes to charge. Then we'll see if she will start."

Oh, she was already started. And I think Andy knew it. I just didn't know how to stop it. Or if Colleen even wanted to stop it. Andy spent the next few minutes with his eyes glued to my legs. I could clearly see his cock growing again in his jeans. I had to admit that it was impressive looking.

"Ok. Lets see if she'll start." he said.

I turned the key and my car came to life. I was happy, but also a bit sad. I was having a fantastic time with Andy.

"Thank you. How can I repay you?"

"Don't worry about it." he said. Andy sounded a bit sad.

"Please let me do something for your kindness. There has to be something I can do for you."

"Well..."

"What is it? Try me."

"A few years ago, I had a girlfriend. She didn't want to have sex, but she would rub her feet on my dick. I really enjoyed it when she was wearing nylons. I don't suppose you would..." his voice tailed off.

I got out of my car and led him to a near by picnic table. We sat down. and I turned to face him. I gently placed my heels on his thighs. He put his hands on my calves, and slowly caressed them. He slid a hand down to m right heel, and ever so slowly, removed it. He guided my foot to his manhood. It was hard as rock. And to be honest, so was mine. But mine was neatly tucked between my legs.

"Andy, take it out."

He stood up and quickly undid his jeans. He pulled them down far enough for his cock to spring free. He sat back down, but his dick stood tall and proud. I slipped my left shoe off, and put my feet around his pole. I felt it throbbing as my feet touched it. It twitched and quivered every time I moved my silky pantyhose up or down on it. Andy took hold of my feet, and pressed them tighter against his throbbing monster. He began to slowly thrust against them.

Here I was, dressed as a woman, with a complete stranger, fucking my pantyhose covered feet, in a park! And I was loving it! I could feel a damp spot in my crotch, growing by the second. My own dick was tingling, and threatening to cum.

This still seemed unreal to me. If it was a dream, I was loving it. As I watched his rod gliding over my pantyhose, a big drop of precum was building on the tip of his cock. It then slid off, and ran down his shaft, and onto my toes. It was a nice warm feeling as it soaked into my nylons. I put my hand on my right thigh, and began to gently rub it through my pantyhose. I wanted to rub my own dick, but I knew that would have to wait. I knew the gusset of my pantyhose was soaked clean through, and the wet spot was still growing around my gusset. Colleen had a slutty side, and it was now on full display.

Andy began to moan and his pace was quickening. I wanted this to last as long as possible. But Andy had other ideas. He groaned as his cock began to spasm. I knew what was about to happen, as did he. And happen it did. Andy cried out as a long stream of cum erupted out of him. I watched it blast into the air, make an arch, and hit me right above my knees. Then another, and another rocketed out of his huge manhood. Both splattering on my knees. Andy let out a couple of grunts, then another massive wad erupted from him. Shooting skyward, and landing all over my knees and calves. He slowed down, having a few more spurt out, landing on my ankles. The last of his discharge, oozed out and flowed down onto my toes, quickly soaking through my pantyhose, and around my toes. I felt his hot cum running all over my pantyhose and soaking into them.

It was a completely new feeling for me. I, or actually Colleen, had made another man reach orgasm. I looked at the proof as it dripped down my legs and around my toes. Long dark streaks and big white globs of Andy's hot cum all over my pantyhose. But I knew I had to get going.

"Thank you Colleen. I really enjoyed that. Sorry about the mess on your nylons."

"Don't worry about it. It was my pleasure. I never did that before. But I did enjoy it." I said as i slipped my feet back into my heels, causing his cum to squish around my toes. I stood and told him that I had to get going.

"I don't suppose that you would want to meet again, maybe in a couple days?" he asked.

I thought for about it for a minute before I answered.

"What time do you finish work?"

"Around 9 most nights. I can drive by in a day or two, and see if you are here."

"I'll think about it. Maybe we will meet again, soon." I turned and headed for my car. I had a feeling that Colleen was going to get her legs covered with Andy's cum again soon, very soon.