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Practice Pays Off

"First time out in public dressed as a woman."

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It was a beautiful Saturday late afternoon. I was done with all the things I had to do around the house. My wife was gone for the weekend and I was feeling a bit bored. I thought I would take a shower, shave and pull out the makeup and see if I could do myself any justice in looking passable. Many attempts before had failed, but I was getting a little better each time.

I got out of the shower and was nice and clean, smooth from head to toe and went to the bedroom and pulled on a pair of my Wolford synergy gobi pantyhose. These are like wearing silk and they massage the legs as you move. I tucked my privates and looked in the mirror, I thought, 'mmmmm, looks like a closely shaved pussy.' I pulled on a black lace camisole and went to the bathroom to do my make up.

I put on the moisturizer, then the foundation, some bronzer, and blush, mascara and eye shadow. After each, I looked at myself and thought each step went well. At the end of applying everything I took one of my brushes and blended. I put on my glasses and thought, oh my, I look like a woman. I mean, really, I thought this is the first time I thought I was no longer that man with makeup on.

I sort of strutted to the bedroom to finish getting dressed. I pulled on my skirt and blouse. Pulled on my strappy black sandals and tied them. I looked in the full-length mirror and saw a balding woman looking back at me. I grabbed my wig and walked to the bathroom my heels clicking on the hardwood floors. I flipped the wig in place and looked again in the mirror. Now I know I am no "cover girl model" but I thought, I would never question if I was a woman. 

I was getting a bit stiff in my pantyhose looking in the mirror feeling those soft silky pantyhose being touched by my skirt. I wiggled a few times just feeling the fabric touching my ass, legs, and lower tummy. My tucked cock was starting to strain under the restraints of the crotch of the pantyhose so I thought, I'd better either go for a drive or a walk.                                                                                   

I look okay, I thought. So why not both.

I put some press-on nails on. I grabbed one of my wife's purses and threw my wallet, lipstick, cell phone, cigarettes, and lighter into it. I grabbed my keys and headed towards the garage. I walked around the car and as lad like as possible I sat in the seat, tucking my skirt under my ass, as I had seen other ladies do so many times. I swung my leg up and into the car keeping my knees together. Just practicing, I thought. I didn't want to look like a guy leg in first and then my crotch wide open for everyone to see. Success! My trial period was over.

I arranged things in the car and pushed the door opener to reveal the world to me. I stepped on the clutch, turned the key, then it dawned on me that I would be backing out of the garage into our alley. I thought, the neighbors, what if they see?  Another tingle ran through my body and I shook a little, like when walking out into a cold morning, and you get a shiver.

I decided I was going for it and let the clutch out, the car kind of lurched backwards, I definitely am not used to driving a car that has a stick wearing heels. I needed to concentrate on what I was doing. I backed into the alley swinging the car to exit to the street. 

I live in a smaller town, but we are a bedroom community for a larger city. I felt a little nervous now driving a familiar car through my neighborhood dressed and made up, wig on and people knowing that it's my car. I then thought, well, keep your head down look straight forward and no one will notice the driver's a woman. I pulled from the alley on to the street moving along, not fast but not doddering either.

I kept my head down eyes straight forward. I stopped for the stop sign and drove down the street, to a park about a mile away. My heart pounding, I have visited this park before dressed and with makeup and a wig on, but never in the light of day.

I spotted an empty parking spot and pulled in. I opened the door and slid my legs out. My heels clicked on the tar as they hit, and I got that same chill up my spine. Am I really going to do this? I thought. Before I could think of the answer I was up and standing. I closed the door and realized I forgot to grab my purse.

I opened the door again and grabbed my purse putting it on my right shoulder. I closed and locked the door and started a walk along the paved path by the river. I was strolling along looking at the water and hearing the kids on the upcoming playground equipment. I saw a park bench facing the river and took the opportunity to sit and have a cigarette.                                                                            

I opened my purse and pulled a cigarette from the pack. I grabbed the lighter and went to light my smoke, Now flicking a lighter is a lot different with nails and I had to make several attempts to get it to spark. I held the flame to my cigarette and suck in deeply. 

So far I was just enjoying looking at the water of the Mississippi flowing in front of me. I inhaled again and felt the rush of the nicotine rushing to my head. I had my legs together and tucked somewhat to the side, like I had practiced at home sitting in my office chair masturbating to porn or a good cyber session, to look lad like and give that dainty appearance even though I thought about the words or movie on the screen and stroked my member to it until the cum would blast and land on my pantyhosed legs.

I kept inhaling enjoying the warmth of the now low sun hitting my legs and the breeze cooling them. Just then a man walking by noticed me and said, "Hi."                                                                                                                                                                          

I looked at him and smiled no words escaped my mouth though. I was speechless as this stranger looked at me and didn't even flinch as to my gender. I thought, I must look okay, and a warm flush spread through me. I also just thought to myself, how will I use my voice? I didn't think about that until now. I mean at home I can talk out loud in my regular voice telling my imaginary lover, "to fuck me deeper," or, "right there, yessssss, right there."

But how do I respond to a person asking a question or giving a compliment or just a simple hello? I thought, I can't yell out, "right there, right there," to them. I sat and pondered for a few minutes as I finished my cigarette.

The opportunity arose soon enough as a couple walked passed. Both looked at me and nodded and said, "Hello," in gentle light voices.                                                                                                                                                                                                         

I softly half-whispered, "Hello," back. I was pleasantly surprised that it sounded feminine enough to pass. The couple smiled and whisked by me and continued down the path.

My cigarette done and out, I tossed the butt in the garbage can, and then stood to go back to the car. I stepped on the path and started walking slowly as my knees had stiffened slightly and walking in heels always takes me a couple of steps to get the rust out. I took about ten steps and I heard a voice from behind say, "Look out sexy!"                 

I stepped to the side and turned my head to see a younger guy on a bike coming up from behind quickly. I took another step to the side and he whistled past me saying, "Thank you."                                                                                                                                   

I felt so good him calling me sexy. I got to the car reached into the purse grabbing the keys. I opened the car door and sat down on the seat and swung my legs in just as I had practiced it. I closed the door, snapped my seatbelt in place and stepped on the clutch. I turned the key and off I went.

I was going to go home but thought, this was fun and rather exciting. I thought, maybe just a drive downtown and down Division Street. It was still light and I was feeling very good about how things went in the park.

I drove down Benton Drive to the east end of the city. I turned onto Division Street and headed west. Now Division Street has twenty-six traffic lights from one end of the city to the other and I was not thinking about that as I turned on to the street. I soon remembered as I had to stop for the second time.

After each light, my skirt seemed to ride up just a little higher than the last as I would engage and disengage the clutch for each shift. Before I knew it, my skirt was just below my gusset of my pantyhose showing off all of my thigh. That's when a truck rumbled up next to me and I looked over to see a younger man looking in my window at my legs and giving me a thumbs up and a nod. I smiled at him and felt my cock grow a little as the blood rushed to engorge it. I know from my experience,  the effect of seeing a nylon covered leg has on me. I must have flushed a bit, because all of a sudden it got warmer in the car.

I kept driving on, and the truck stayed with me as the passenger was checking me out, each time I looked over he was staring down at my legs. My cock now straining at the crotch of my pantyhose and I was so glad it was tucked up or would have made quite the bulge in my skirt. My feet worked the peddles at each stop light and my skirt stayed at my crotch. I know that the passenger was getting a good show, because his eyes never left my lap. 

I got through downtown, and headed towards the highway to go back to my little town. I turned on to the highway, and the truck zoomed on, the tension in my pantyhose lessened some. I couldn't help but be a bit turned on though, as I thought about giving that young man a little innocent show.

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I was headed home but was now a little aroused and thought about stopping at the Walmart that was near my house. I thought, I could use a few items and why not do a little girl shopping as long as I looked like a girl? This, of course, got my dick hard again, as I love shopping and this exhibitionism was really turning me on.

I pulled off the highway and into the Walmart parking lot just as the street lights were going on. I parked the car and opened the door swung my legs out and again my heels hit the pavement with that little click that is unmistakable. This time I remembered to grab my purse and started walking to the entrance. 

Now it was 9:15 pm or so on a Saturday night and I thought, the store should be fairly empty, but as the parking lot showed it wasn't as slow as I had hoped. I was thinking, do I still go through with this? I thought. Why not? I am already here.

 As I got to the door there were people everywhere. I passed six or seven already just walking to the door. I had a couple of guys look at me as I walked past them and I know they heard the clicking of my heels, and that was what made them turn their heads. I watched a woman with a baby check me out and gave another smile and said, "Hi."    

I used that same voice from the park and said, "Good evening," back to her. 

I walked to the cart area and grabbed on to one, lowering my purse into the child seat area of the cart. I started towards the grocery department, and walked the aisles. I picked up some things I needed, and bent to grab a can of soup from the bottom shelf and as I turned, I saw a guy looking at me, checking out my legs and ass. As I stood I watched his wife or girlfriend elbow him. A penance for checking me out. 

I moved to the cosmetics and was looking at some lipstick when another customer came up to me. It was a twenty-five-ish girl and she looked at me and said, "I love your shoes."  Then she asked, "Where did you get them?"    

I turned to her and looked at her expecting her to figure out I was no woman but she looked serious, and I said, "Thank you. I got them online."

She then asked, "what site?"

I said, "Shoedazzle".

We talked for a few minutes about the website and how I was a VIP member and some of the perks. All the time my cock was straining in my pantyhose as this really turned me on. We finished our little conversation and went our separate ways. 

At this time I was really hard and there was a wet spot growing in the cotton gusset of my hose. I really need to relieve myself but wasn't sure I wanted to go into the ladies' room. If they saw me jacking off in there I would have my name and picture in the paper and sitting in jail. 

So I thought I would slip into the men's room and find a stall. I would pull my skirt up and my pantyhose down and just relieve myself of this load that was already leaking between my legs.I walked to the front of the store got to the restrooms and looked around. No one was looking as I ducked into the men's room or so I thought.                                                                                                           

I found that I was the only one in there so I went to the first stall and closed the door. It was only a few seconds later I heard a man clearing his throat as he entered the bathroom, I was very still and just had lowered my pantyhose to be able to free my stiff leaking cock from its encapsulation. I heard him walk to the urinal and then it happened, he spoke. I heard him say in a soft almost whisper, "I saw you come in here and I don't know what a woman is doing in here but you can come out or I can get security!"

I froze. What the fuck am I going to do? I thought. I finally said in that soft airy voice, "please don't call security. I'm not doing anything wrong."

He then asked, "Then what are you doing in the men's room?"

I said to the man, "I am a man."

He walked to the stall door. I peeked through the crack as he peeked back. I looked down and so did he as I pulled down my pantyhose a little further and he saw my penis jump to life.                                                                                               

At this point, I thought he would leave me alone and let me be but he stood there, still peeking in. My cock had lost some of it hardness from the goings-on but it still was rather stiff and there was definitely some pre-cum dripping from the slit in the head.

I looked back through the crack and asked him, "Are we okay now?"

He grunted with a question, "Who are you, what are you? What the fuck?"

I told him, "I am a crossdresser and that needed to use the john."

He just stared at me through the crack.

At this point, I was tired of looking at his eyes so I unlocked the door and saw a store employee looking at me as the door swung in. I looked at him and he kept looking at my legs and cock. 

I asked him, "Are you okay?"

He nodded and smiled.

I asked, "Are you going to turn me in?"

He shook his head and then asked, in a very soft voice, "May I touch your legs?"

I said, " Yes, but come in the stall so we don't have company."

He scurried through the opening and past me. I closed and locked the door and in one move he was on his knees holding my leg between his hands. I felt his hands starting at my ankle and work up my right leg. He felt my calf and then my knee and then he hit the back of my knee. I moaned.

My cock growing as his hands sent shivers up my legs to my groin. His hands found my thigh and he softly stroked my thigh, the softness of the Wolford pantyhose captivated his hands and he couldn't seem to get enough of the touch, not that I could blame him they are quite the pair of hose.

Soon my cock was harder than before and again the pre-cum was dripping. A few drops hit his hand and I saw him look at his hand caressing my thigh and he brought the semen sample to his mouth licking the drops off. He looked up and asked, "Can I ?"

I nodded my head yes, as his tongue touched the end of my cock. He licked the dribblings off the head of my cock sending more shivers through me. I moaned louder. He opened his mouth and sucked the head of my cock in his mouth as his hands were still working their magic on my thigh.  

My cock so stiff now that if it slipped from his mouth it would take out an eye. My head was back and I was breathing hard and I knew this guy was going to get a load soon. I could feel the tingle in my balls building and his hands and mouth were doing a great job of hitting every sensory nerve on my cock and legs. My balls were now pulling tight and I grabbed his head. I pulled him on my cock so he couldn't move. I buried my cock as deep as I could without him gagging. I moaned, "I am cumming."

I let six jets of cum enter this man's mouth. I shook from the orgasm. When I could finally open my eyes he was standing against me holding me from collapse. I put my mouth to his and kissed him. My lipstick clung to his lips and the taste of my cum now clung to mine. I licked and then went back to his lips for seconds. He opened his mouth and let my tongue enter and it mingled with his. 

My hands now in front of me, pinned to my body with him holding me from falling after my intense orgasm. I felt his cock pushing against my wrist and turned my hand and lifted up enough to feel how hard he was. I looked him in the eyes and kissed him deeply my mouth opened and the words came out of my mouth without me even thinking, "I want that cock in my man pussy!"

All he could do was nod. I pulled on his belt and then jeans button. I unzipped his jeans and they fell to the floor I pulled down his underwear and stroked his seven-inch gland, and felt him shake. I dropped to my knees this time and took him in my mouth. I slobbered up his cock with all the saliva I could muster up, lubing his member because my pussy was yearning it.  

I was stroking it and the glistening of pre-cum was pooling at the slit in the head. I pulled, again and again, spreading the saliva and mixing it with his leaking fluid. I pulled my pantyhose down to expose my pussy to him. Bending over the toilet I pushed my ass in the air. I felt his fingers touch my lips. I opened my mouth and he put his finger in. I sucked on it and he, in turn, put it to my rosebud. He pushed slowly into me. I relaxed as his fingers stretched me out. 

I felt his fingers leave and his cock taking their place. Putting it at my entrance he pushed into me slowly, pushing past my sphincter.  The head of his cock was in me and we started rocking together slowly. He took my virginity. My life would never be the same and the pain I had felt at first had turned to pleasure.

I felt him rocking my pussy and filling my void with his cock. I felt the heat of him going deeper and deeper each trust. My cock was now standing straight forward, pointing to my face as I looked back under me. I could see his heavy balls hitting mine on each stroke, feeling them touch mine, then slap mine, and once we really got going slamming into mine. 

I felt him tense up and felt his ball sack get tight as it wasn't hitting mine anymore. I heard him moan almost growl as I felt the first eruption in my bowel. I pushed back hard I wanted his sperm deep in me. I wanted to feel his cock ejaculate into my belly. Stream after stream coated my insides and all I could do was pinch up my muscles to milk every drop from this young man.

I felt his member softening in my grip and knew he was spent. I stood slowly letting him slip out of me. I turned and kissed him as he panted. I leaned down and kissed his softening cock and felt it jump just a little. I pulled up his underwear and his jeans. He zipped and buttoned them and looked me in the eye. I looked back into his. He asked, "Can I get your number?"

I said back, "No, I am married and this can never get out."

He said, "I want to see you again"

I said, "You will in a month when my wife leaves again."

He smiled and unlocked the door. He opened the door and slipped out, as he left the room I heard him say, "All clear."

I pulled up my pantyhose and straightened my skirt. I walked out of the men's room and found my cart where I left it. I went to the checkout and paid for my items. I was walking out the door as the greeter said, "Have a great night."

I looked at him and said, "I already did," and laughed.

I made it to my car and put my purchases in the back and sat down swinging my legs in and closing the door. I felt the warm juices coating the inside of my pantyhose as I shifted the car all the way into my garage.

I can't wait until next month.

Published 
Written by gerry15
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