Taylor

By Barbie Sisy

Published on Jun 26, 2008

Transgender

If you want this story continued please let me know.

Taylor by: Barbie Sisy

It was a typical southern afternoon, the temperature and humidity raced to see which would end higher for the day. As evening fell no cooling relief came so I decided to take a trip next to the river where it should be cooler. I let the air conditioning run to cool off my SUV and when that was accomplished, I rolled the windows down and lowered the window in the tailgate. While it was more comfortable with the a/c on it wasn't too bad since tall oaks and pines kept the road sheltered from the setting sun.

This particular road ran within 300 yards of the river. Close but not close enough to be heavily traveled or used as a parking area for people going to the river. I was starting to cool down when I noticed another vehicle with its flashers on pulled off on the shoulder ahead. Pulling next to it I saw a woman in her mid thirties on her cell. She was very attractive with long blond hair and green eyes. Since she was sitting in the car I couldn't see the rest of her and as she looked over at me, somewhat annoyed, I asked if she needed any help. She quickly explained she was on hold but her car had overheated and she didn't know what she was going to do. I naturally offered to look at it to see how bad it was and she agreed by popping the hood. She remaind in the car as I put a rag over the radiator cap and slowly started to twist it off. Nothing happened when I reached the safety setting so I finished taking off the cap and saw a half filled radiator.

Hearing her say that she was not going to sit on the side of the road till morning, I walked back to her door. She informed me that a wrecker could come and get her but not until the morning when the driver came back in. I asked if she lived around here and found out she had a house about 4 miles down the road. We talked some more and I said I thought she could make it if she didn't put the cap on all the way to avoid pressure building up as fast. At that point she got out and walked with me to the front of her car. After showing her she still had antifreeze in her radiator,I picked up the cap to put it back on. My hand felt a sudden shock and I dropped the cap.

I remarked that it was still hot and bent to pick it up with my rag. Placing it back on half way, I volunteered to follow her to make sure she got home without any further problems.

When we got to her house she asked if I would like to come in for a drink. I told her I should be getting back but thanked her for the invitation. We talked for a few more minutes and as I was getting ready to leave she asked if I would let her fix dinner the following evening. She was very attractive but I couldn't understand why she lived so far out in the country. She said to be there around 7 and to wear whatever I was comfortable in and that her name was Taylor.

On the drive back her last statement kept going through my mind. Why would she say that? Did she know? She couldn't. True I was wearing panties under my shorts but my shirt tail fell past my waist and so she couldn't ahve seen them. Maybe it was nothing. Just to be safe the following evening I wore blue jeans over my panties and tucked my shirt in. Better safe than discovered.

When I arrived she took me on a tour of her house ending with drinks on the back proch. I asked what she did for a living and found out that she was an attorney. She was able to choose her cases now unlike when she first practiced. After a few drinks I asked why such an attractive woman would live so far out in the country. While putting the finishing touches on dinner, she explained that she wanted to get away from the big city life. Since her job took her to different cities she wanted a place away from all that. Dinner was great and the company even better. After clearing the table we walked through her garden to a small wading pool. Since she had on shorts she slipped her sandles off and walked right in. Noticing my hesitation, she assumed it was because I had on jeans and she said to take them off. Now I was in a real predicament. If I took my jeans off she would see the silk panties I had on, pink with lace around the waist and legs. Seconds passed and she made no effort to come out so I finally walked in pants and all. Laughingly she made the comment that she thought that would surely have gotten me out of my pants. I said I was fine as I sat on the edge of the pool.Taylor sent several splashes at me and then walked over placing her arms on my shoulders and kissing me. My arms went around her waist as I held her close. After several minutes of kissing and hands exploring each others bodies, she unbuttoned my shirt to my waist. I helped her out of her top and bra and pulled her close. As we were kissing I checked out her bra sitting on the grass- very nice lace underwire. Suddenly she pulled back and said we should head back to her house. I thought we would end up in bed so I would excuse myself first and go to the bathroom, remove my now wet panties and she would never know I had been wearing them. Naturally it didn't work out that way. When we got back she went into the living room and mixed some drinks. I noticed she was very careful not to sit but carried on the conversation while walking around the room.I went along with it thinking she was no longer interested. After finishing my drink I said that I should start back and thanked her for a nice evening. Taylor walked me to my car and I kissed her before I got in. As I started the car she motioned for me to roll the window down. She bent down and said she knew this wasn't I had expected and she was sorry. I told her everything was fine and hoped we could do it again. Saying she would like that she headed back to her house, stopped and said "Come back this weekend." I was more than a little puzzled but she said to come back on Saturday and we could spend the day together. I thought about it and agreed and she said "Bring something comfortable to sllep in" and headed for the house.

On the drive back I jokingly thought which nightgown and panties would Taylor like to see me in. I pictured the shocked expression on her face finding me in bed in one of my beautiful nightgowns or maybe a babydoll, it is summer after all. Since I had a day to decide i started to think about why she had suddenly broken off our kiss. Did I push it along to fast? After all she had been the aggessor, I couldn't arrive at a final conclussion. Friday passed without any answers about what happened or what clothes to take. I thought of calling Taylor to see if she needed me to bring anything but decided against it.

Saturday was another hot day. The weather called for temperatures to be close to 100 with little chance of showers. There was no way I could wear jeans so I decided I would wear a pair of white nylon panties under my shorts. Even if she caught a glimpse she would just think they were regular mens underwear. I was so use to sleeping in nightgowns it was hard to think of sleeping in anything else. I finally picked a beautiful little babydoll gown- lavander with lace around the bust, ruffled straps with matching ruffle around the hem. It also has a matching robe and I choose a pair of matching silk panties with ruffles around the legs and across the back.

I arrived in the early afternoon and Taylor greeted me with a quick kiss suggesting we go inside to take advantage of the air conditioning. Since she had given me the tour previously she said to put my things in the first guest bedroom since it had a private bathroom. The room was very feminine with lace and ruffled curtains, lamp shades and bedspread. Fortunantly they were all white and as I took it all in Taylor said "I hope you don't mind all the lace and ruffles." Did she know? How could she! I had been very careful. My stammered reply came out that it was only for the night.

We passed the afternoon talking about our pasts- where we had lived, schools we went to, jobs we had, our likes and dislikes. I found the courage to ask how she had escaped the marriage trap and seeing her expression I knew I had phrased it incorrectly. She simply replied that she had never found anyone to accept her as she was. I figuared it would be hard to live with a fairly high profile attorney who could be away for weeks on end. When she asked why I hadn't I explained I had on several occassions but they hadn't worked out. Asking if I was hungry, I realized it was after 6 and I was starving. Taylor went to the back porch to start the grill. She asked me to make some more drinks and join her in the kitchen while she prepared dinnner. I listened while she talked about some of her cases and chopped this or opened that. She really was something. Smart, beautiful, great body and extremely self-sufficient. She occassionally brushed against me as she made her way around the kitchen and porch. Nothing overt and she would simply turn her head and smile. Laughing to myself, I thought it was good that I had not worn bikini panties since it may have been painful with my dick getting harder with each bump.

After dinner we wnt out to the garden again. The heat of the day had not gone away and Taylor headed straight for the pool. This time I was ready and followed her right in. The water felt like a warm bath and she sat down trying to find some relief from the heat. As I joined her she took my hand and said she wanted to explain about the other night. I said it was not necessary but that didn't stop her, She said that it had been some time since she had been with a man and that her past relationships had failed because of who she was. I replied that she should be proud of who she was, after all she had accomplished she seemed to blame herself for the short comings of others. Her head rested on my shoulder as she said that I didnt understand all of it. I kissed the top of her head and let it go at that.

Her hand moved to the inside of my theigh and she ran her hand about half way up. Slight panic set in as I thought of her hand going too far up and feeling my nylon panties. Could she tell the difference underwater? What would she think if she could? I was falling for her and was about to blow the whole thing because I couldn't stay out of panties. Great! Her weight suddenly shifted and using her shoulder she pushed me underwater. Soaked and laughing she sprang back to a sitting position and as I emerged from the water she pushed me back down. I did a roll and came back up far enough away to avoid being drowned again. in the setting sun i saw a vision of beauty before me. Wet blond hair, sparkling green eyes, lips that I wanted to kiss and did so. Her hands went under my shirt as mine went under hers. Up and off they both came as I felt her breasts press into my chest. Long passioate kisses that went on for what seemed like hours but were mere minutes. Our bodies pressed against eachother, my hands slid down her sides and around her perfect ass. We stayed body locked for a long time. Our lips closed around the others while our tongues danced and darted back and forth. Suddenly I tasted a salty flavor and wrote it off to dinner but it did not go away. I broke our kiss to see tears streaming down Taylors beautiful face. She jumped up and ran for the house.

I continued to sit in the pool and feel very stupid. What had set her off this time? I was sure it wasn't anything I had done. Now, maybe, I knew why she chose to live in the middle of nowhere and hadn't married. Time to go home thoughts ran through my head as I followed her to the house. When I got there she was no where to be found. I went to her bedroom and saw the door was closed: knocked and said that it may be better if I left. Taylor cracked the door and asked me to stay since it was late, adding she would be much better in the morning. I gave in saying I would see her in the morning.

Smiling she closed her door as I headed for my room. I hung my wet clothes in the bathroom, dried off, brushed my teeth and slipped on my nighty. The satin sheets felt cool against my nylon gown and panties. I had never had any satin sheets but always wanted a set. I got up to turn the lights off and settled back into the cooling comfort of the bed. Replaying the evening in my head I suddenly realized my dick had gotten very hard. When my hand touched it through the nylon it was ready to go. Thinking it would not be good to play with myself her I got up, put on my robe and went to look out the window. A full moon was well on its way in the sky and after watching it climb a little higher I went back to bed.

I don't know how long I was asleep when I heard my door closing. Taylor asked if I was asleep as I heard her footsteps getting closer. My mind raced...what do I do now? What if she turns on the light and sees me there in all my lavander nylon? I simply played like I was still asleep. She drew back the covers and slipped under the sheet. I am dead I thought. Still faking sleep, i rolled to face her hoping my outstretched arm would cause her to stop before she got too close and discovered what I was wearing.

It worked but only for a few minutes. I felt her lift over my arm and slide down it bringing her body next to mine. All I could think of is I'm dead! Since she hadn't actually touched me yet she still didn't know I was wearing a nightgown and panties. I could roll back over, go too far and end up on the floor, very quickly remove the nighty and panties, throw then under the bed and wake up naked. Too late, her hand just went to my side and I knew she had felt lace and nylon. her hand continued down past my ruffled hem and back up over the fuffless and nylon of my panties. What do you say at a time like this? I, being a great conversationalist, managed " Feel better." She whispered yes and kissed me.

This all seemed very unusual to me. A few hours ago she ran crying from the pool and now she was in bed with me and I am wearing a babydoll gown and panties. Her leg swung across me as our kissing continued.

My arm came down to hold her close. As my hands moved across her I could tell she was wearing a satin gown-showoff- and panties. Side by side her right leg still over my theigh, I eased her gown strap down her arm revealing her perfect breast. My fingers felt her erect nipples as she pressed her lower body to mine.

I lowered my lips to her breast, softly kissing her nipples and then sucking on them as her hand played with my equally erect nipples through my gown. The feel of lace and nylon as her finger flicked my nipples was overwhelming. She lowered her hand down my side and waist till she found my dick ready to tear out of my panties. Slowly her hand ran up and down my shaft. She said she loved my panties as I continued to kiss and suck her tits. My hand wandered down her side. I could feel her panty line through her gown and started to bring her hem line up to her waist. I heard her gasp as my hand skimmed across the back of her panties. She felt so good next to me. All i wanted was to make love to her. I had found the girl of my dreams; one that didn't mind the fact that i wore lingerie. As my hand slid down her beautiful ass I felt a lump but didn't think anything about it until my hand went under her leg band and touched her very hard dick.

I was too far gone to care. While I had never been with a person that had a dick my hand naturally glided up and down her saft. She freed my wanting dick from my panties and asked me to move hers so that it pointed up. She then raised her panty leg and my wet dick went past her balls and up to her ass. Her panties held my dick in place as she reached her hand around and held my shaft while she moved her sweet ass up and down its length. The sensation almost made me cum right then. She remarked that I was getting her her panties very wet with my pre-cum and I told her she was fortunate that was all it was.

My dick was ready to explode from the feel of her satin panties and as she raised her ass I felt her stop for a second and then felt my head easity slip into her ass as she lowered her body next to mine.

Automatically my hips started moving back and forth slowly sending me deeper into her. My lips pressed against hers as my hand ran up and down her satin dick while she brushed against my nipples with her fingers. I could feel her body stiffen and knew she was going to cum but I didn't care. My hand continued to stroke her dick as my dick moved in and out of her ass. Her cum soaked her panties and she took her finger and bathed it in her cum before going under my panties and inserting it slowly, carefully into my virgin ass. The feeling of her finger in my ass, her lips on mine and my dick burried in her was too much.

Cum shot into her as I pushed in as deep as I could with one hand craddling her ass while pulling her to me.

Our kisses continued long after we had both found that sought after release. When they ended we lay together starring into one anothers eyes.

"I hope you don't hate me." taylor said.

"Are you crazy." I replied "I wanted to tell you but I was afraid you would freak out like everyone else I was involved with."

"I thought when you talked about people not accepting you it was because of your work. Besides, not to bring this to your attention but I'm here in a nightgown and panties. true a very pretty one but none the less."

"Oh, I saw you were wearing panties when we first met."

"How? When? I was so careful."

"When you picked up the cap thing your shorts revealed some very nice pink panties but you still look like a guy."

"And you are the most beautiful girl in the world."

"Except I have a......"

"A special surprise. Taylor, we are all who we are and that's how we have to live. For whatever reason you happen to be a very pretty girl with a penis."

She explained that she had altered her appearance and when the time came for the final snip, she couldn't go through with it. I kissed her and told her she was perfect just as she is.

By this time my dick had downsized but was still in her panties and I really needed to go to the bathroom.

She released me telling me to hurry back. After closing the bathroom door and turning on the light blinding myself, i considered the 'first' I had experienced that day,

Next: Chapter 2


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