Jenna's Ready to Ride

by jenna shoes

Copyright© 2010 by jenna shoes

True Sex Story: This is the second story I post about my adventures. I meet my lover for a second exciting night. My sexy look with a long skirt and western style high heel boots make him want to ride me hard. More that i bargained for...

Caution: This True Sex Story contains strong sexual content, including Ma/Fa   Consensual   True Story   Cheating   Rough   Light Bond   Oral Sex   Anal Sex   Masturbation   Cream Pie   Size   Leg Fetish   .

This is my second story posting. I have been sharing some recent events that occurred in the past few months.

A little bit about myself if you did not read my previous story. My name is Jenna, I am 40, married with 2 kids. I am 5'6" tall and weigh 130lbs. Brown hair in a bob haircut and brown eyes. Good curves where they are needed if I may say so. My main assets would be Long legs and larger breast than the natural average. Still attractive but not a knockout, let's not exaggerate. I work as a top exec in a large company and live a rather conservative uptight life. I have always been loyal to my husband.

I love clothes and footwear and always dress in as sophisticated and classy manner as I can. That does not mean I look dull or do not like to look sexy but I do that while remaining classy. Being in a powerful position for a woman, I have to show confidence to all those around me and may come off as tough. However having a strong exterior means that I have to express my feminine side in other ways. I like to wear high heels and knee high boots but also sexy sophisticated lingerie. For example I wear mostly stockings and rarely pantyhose.

If you like the story or if you want to see what I look like, send me an email. I will send you a picture of me in the outfit involved (no, not just the lingerie!).

After my first affair with Tom, we kept sending texts to each other. I had to become more tech-savvy about hiding signs of my recent "escapades". I knew we would meet again at a soon to come convention and I could hardly wait. It was not love but the thrill of this very sexual encounter was so new to me, I thought about it all the time. Waiting for almost a month was very hard. I surprised myself several times touching my body while thinking about him. As the days came near I was thinking about what clothes to pack but had to wait until the last minute. I did not want to let my husband see that I was packing two different silk and lace nightgowns, various garter belts and even a corset. It would have been a bit suspicious. It was ridiculous as my husband is used to seeing me pack these items but my guilty conscience was playing tricks on me.

For the flight to the conference, I wore comfortable jeans and flat shoes. As soon as I arrived at the hotel resort, I changed to a more elegant outfit. Just as I was making my way out of my hotel room I received a text. Tom would not arrive until the next day due to an emergency. I was sad and disappointed but still tried to enjoy myself as I knew we would have one night together. I chatted with many people and tried to enjoy myself. That evening was a "Western night" event. We were to go to a large place with a live band and local fare. Everyone had been advised to dress in a country western style. I had picked an outfit for that evening but wearing while Tom was not there to see it was a bit of a let down.I have given a nickname to that look in jest "my ready to ride or be rode outfit" I did not know how true that would be. I had on a long tight brown suede like skirt with matching jacket. I had on a leopard print blouse which opens in the front and reveals the shape of my breasts. That was for Tom's benefit but I could hide it with the jacket. I had tall knee high brown boots with a western flair and almost 4 inch heels. Below that I had worn something extra special for the night: a tan colored satin and lace bustier, matching garter belt and panties with tan colored stockings.

The long tight skirt forced me to walk rather short steps and step with one foot in front of the other. The high heels also gave me a very alluring "strut" where my hips swung more than usual. I noticed as I walked through the lobby of the hotel that several men were staring at my behind. That certainly helped to make me feel better!

Once I arrived at the "party" it was the same usual stuff, networking, chatting, exchanging pleasantries. Three men asked me to go dance so I was kept busy and it felt nice to have men desire me. I started thinking that maybe I should just go with another man since I had been dropped. As the evening wore on I decided to go back early but as I walked towards the exit, someone grabbed my butt roughly in the crowd. I spun around ready to slap the jackass. "Hello Dear" Tom said smiling. I was shocked but had to keep my cool. Jumping in his arms and kissing him would be a tad indiscrete. I straightened myself and replied calmly "Oh Hi Tom, How are you? I thought you would be coming tomorrow". "I drove here as soon as I could get away instead of flying"

"Really? well you must have some important business to attend to then" He smiled knowing what I meant. "Indeed, it has to be wrapped up even if it takes all night to take care of that..." I smiled and fought to stay poised. Inside, I was melting, getting so turned on thinking about his hands holding me and him sliding inside of me and ... I had to regain control quickly, I felt like I was blushing and would get noticed. "Well, Tom, it was nice to meet you. Good luck with that deal you need to work out" "thank you Jenna, are you headed back to the hotel?" "yes I am, I have been here for over 2 hours now" "I can drive you back then, I have my truck."

I shuddered as he offered the ride. I knew what would happen in the truck. I knew I would not be able to keep my hands to myself. I was blushing at the thought but started walking to the parking lot with him. "so you like my outfit? I call it my ready to ride look" He laughed "indeed, you look ready to ride darling" I climbed into his large white SUV and noticed the tinted windows. Climbing in there was quite difficult with my tight skirt but I managed to seat there. He started the engine and drove off into the night. I noticed he was not headed for the highway but took a rural road. As soon as we came to a red light, he looked at me, brought me closer to him by holding my neck and kissed me passionately. Our hands were on each other in a flash. I could not help but place one hand on his crotch. He was trying to raise my skirt but its tightness and length prevented him from doing so. "Just to help build the anticipation" I said. I smiled at him with the sexiest smile I could make. Eyes half closed but looking straight at him, my lips apart, hoping to drive him crazy. My hand unzipped his pants and I rubbed his half erect penis. He had to get going as the light was green. As he drove, the desire made me do something I had never thought of before. The cab of the SUV was dark and the windows tinted. I leaned over and pulled his large penis out. I licked it gently watching it grow. He whispered "oh my god". That pushed me further and the lust that was taking control over me did the rest. I proceeded to give him the best blow job I could with as much passion as I could put into it. After a couple minutes, my head was going as far up and down as I could. The tip of his cock making me gag each time I went down. My panties were wet by then and he had not even touched me to avoid crashing the truck. I sensed that the truck was turning and losing speed. I raised up but Tom kept my head down with one hand until the truck had stopped.

"Now we can have each other" he said. I raised up and noticed we were in the middle of nowhere. There were no lights and only the faint moonlight was letting us see our surroundings. Tom turned all the lights off. As I resumed my work on him he was able to reach down and massage my breasts, rub my butt but still couldn't reach my wet panties because of the skirt. I liked the fact that even though this was not practical, it drove him crazy with lust. "You want it don't you? " I asked. "Hell yes baby I want you bad" I smiled and said "I am not ready yet".

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