Jessica

By John Nail

Published on May 7, 2009

Transgender

I thought I would tell you my true life account of this wonderful beautiful lady Jessica who happened to be transgendered. I really fell head over heels for her and well you will find it was bitter sweet. I would love to meet another lady like her. I would love to hear comments from you transgendered ladies and especially if you might be interested in giving this guy a chance lol. You can email me at wyojohntop@yahoo.com

Hi, my name is John and I was about 22 years old and was loving it here in Cody,Wyoming. I was single and enjoying my life.

I had just helped on a hay bucking and stacking crew and the day before I had worked on saddlebreaking a horse which a friend of mine and I shouldn't have tackled to begin with. That horse had thrown me against a barn wall the day before and I had just helped bucking and stacking about 5,000 bales of hay with a crew of about 12. I was really sore that day.

I stopped by a convenience store called Maveriks to fill up the truck with gas my 77 Ford F250 4x4 and the next thing I knew this sports car pulled up beside me.

Out of this car stepped out this absolutely beautiful lady about 5'06" about 115 lbs. brunette hair dark complexion she looked Latino and a blue dress with 4" heels. I got done filling up the truck and went into Maveriks. I got me a Pepsi and got in line and got lucky I was right behind that beautiful lady.

She turned around and said," Hi you are that sexy cowboy that was filling up that truck. "

I blushed and got self conscious, because I was in my well worn Wranglers and

boots that long ago last their original color and became plain brown and the western shirt I was wearing had stains on it and my cowboy hat that has definitely seen better days.

We started talking about what I have been doing for the last couple of days and than I got to the part about the horse throwing me against the barn wall.

She said," Ouch are you alright?"

I said," Yeah, I am in a little bit of pain but I will be going out tonight and I was able to get up and dust myself off."

She said," Wow it is true you cowboys are tough aren't you. I wouldn't be able to get up for at least a week after that."

I smiled and said," Well we had a job to do and I was determined to see it through."

She said," I am new in this town and I have finished putting things away and I want to have some fun and I would love to go out with you."

I was stunned, I couldn't believe what what she just said.

I stammered out," I-I-I w-w-would love to go out with you tonight."

She laughed and said," Here is my number and call me when you are ready to pick me up."

She handed me a slip of paper and headed out to her car and than I paid for my gas and pop and headed out to my pickup.

I started up and the dual exhaust came to life and I headed out of Mavericks. I headed home and made a couple of sandwiches and some chips for a quick supper. I went into my bedroom and got out a pair of good Wranglers, a nice shirt and my dress boots and a clean pair of underwear. I went into the bathroom got a quick shower and got out and shaved dried off and went into my bedroom got dressed. After I got dressed my roommate came in and looked at me.

He said," Looks like you are going out tonight."

I said," Yeah I have to make a call first and will talk for a few minutes."

I picked up the phone and dialed.

I said," Jessica this is John how are you? Yeah I am ready to pick you up are you ready?"

She said," John I am always ready for my new cowboy."

I hung up the phone and went back to the living-room and Russ my roommate was smiling.

He said," Jessica now I am intrigued and where did you meet her?"

I said," I met her at Maveriks when I filled the truck up with gas. She is absolutely beautiful she just moved into town about a couple of months ago and was busy putting things away and now she wants to go out and I will be going out with her. I think she is Latino, she has shoulder length brunette hair she is about 5'6" about 115 lbs."

He said," Wow you have struck gold."

I said bye and headed out to the truck.

I started it up and headed to Jessica's and within 10 mins. I was pulling up the driveway and than I headed to her door and knocked..

She came to the door with the most beautiful smile and she said," John, come on in and let me find my shoes and we will be out."

She came out wearing about 4" heels and looking absolutely beautiful. I noticed without heels she was about 5'2". We went out to my pickup and I held the door open for her and helped her in since it was a 4x4. I went to my side of the pickup and climbed in and started up the pickup.

She giggled and said," I love the sound of that."

I said," Thank you it is duell exhaust with soft glass packs they are not as loud as the hard glass packs and they don't get snagged like mufflers might."

She said," I love real men, men who don't mind getting dirty and clean up well like you."

Since she hadn't eaten yet we went to a local steak restaurant

I held the door opened for her and went inside.

The restaurant was semi-lit and it wasn't fancy but boy did they cook delicious steaks.

I held the chair for Jessica and helped her to push the chair to the table.

After I sat down Jessica said," Thank you for being such a gentleman. I like this restaurant, I like the rustic setting."

I said," If I am not mistaken this restaurant was built shortly after Buffalo Bill built Cody. I just know I love their steaks they have a flavor you can't get in any other restaurant."

We gave our orders to the waitress and after that Jessica was looking at me.

She said," You are such a handsome man."

I blushed I never had a woman say that to me.

The waitress came back with our drinks me a Budweiser long-neck and Jessica a glass of wine.

After the waitress put our drinks on the table and left Jessica reached across the table and grabbed hold of my hands.

She said," I am getting feelings for you that I don't remember ever have feelings for a man."

I said," I am flattered, but what did I do to get those feelings? This is our first date and I am just a guy who loves this area. "

She said," I believe I am getting those feelings because there are no pretensions about you. Men I have dated in the past have put on airs to impress me, you are not that way. Other than your nervousness around me you have this air of self-assuradness happy and content in your spot in life."

Our meal was brought to our table and we start eating. We were making small talk and commenting how delicious our meal was. We got done with our suppers and I drank the last of my beer and the waitress brought our ticket and I paid for our dinner and went to the truck

I helped Jessica and I got in the truck and I started up the truck and started down the street after leaving the parallel parking area.

Jessica said," I love the sound of your truck it sounds masculine."

I looked at her with surpise and said," I have duell exhaust on this truck and soft glass packs the soft glass packs aren't as loud as the hard glass packs and they don't get snagged as easily off road.. I know a perfect place to go dancing tonight."

She said," I am going to love tonight it has been so long since I have been dancing."

We drove for about 5 minutes and pulled into the gravel driveway and I put the pickup in gear after parking in one of the slots.

After parking the truck and helping Jessica out and closing the door we started heading for the building.

On the way in she pointed to the sign above the door and asked,". What is that lady on the sign?"

I said," You won't believe it but here goes. She was a madam."

She gasped and said," That can't be true. Are you telling me she was running a?"

I said," Yes she ran a brothel and from what I understand she was the wealthiest person in the area."

She laughed and said," I can see that, I bet there were alot of horny cowboys coming off the trail."

I laughed and said," Some dignified husbands also visited her business. Including one of the former mayors and governor also from what I understand."

She laughed and said," Did she keep a little black book?"

I laughed and said," I wouldn't be surprised if she did."

We walked up to the door and I paid the cover charge and we went in.

I ordered a Budweiser long neck and she ordered an orgasm.

We got to the table and I set my beer down and went over and pulled the chair out for Jessica and than I helped push her to the table.

I looked and the band that was than called Rocky Mountain Oysters and now they are called Cody.

As they were setting up I said," This is Rocky Mountain Oysters this is a really good band."

As they were tuning their instruments and other things Jessica and I chatted and than they were ready and they started playing the song by George Strait called Amarillo by Morning. I took her out to the dance floor and taught her how to do the western style two-step and within less than a minute she was dancing like a pro.

After the song we sat down and enjoyed our drinks and than a couple of minutes and than as another song started we danced some more.

We danced and drank some for the rest of the night and before we knew it it was closing time.

We made our way to the truck and I helped her in and I got in.

As I was starting up the truck I heard Jessica humming out the song Amarillo by Morning. I smiled this is a dream come true for me going out and having a very beautiful woman at my side.

I got to her house and I helped her out of the pickup and walked her to the front stoop and we kissed passionatly for about 5 minutes by her front door.

Than we both pulled back and she smiled at me," I think I am going to hold onto you cowboy."

I turned after waviing bye time and made my way to my pickup and after getting in I saw her look at me and I waved one final time.

I than back out of her driveway and than put my pickup into gear and than started to head home.

I arrived home about 10 minutes later and I made my inside. After going into my bedroom I was undressing to my underwear and smiling.

I fell into a deep blissful sleep about 10 minutes after my head hit the pillow.

Next: Chapter 2


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