Paying the Debt

Some background for this story. My sister-in-law, Sherri, has been divorced from my brother, Bob, for three years now. I have helped her out several times, even financially a couple times. Helped move her daughter to college and kept her in firewood for her fireplace. I have done several odd jobs for her and she always tells me she will pay me when she wins the lottery. Helping Sherri helped me get my wife to expand her views on sex. I will explain as the story unfolds. The conversations in this story are not word for word but fairly accurate. I have tried to keep the story as true as I can. I don't think I have exaggerated very much in all that has taken place.

This last spring Sherri had a water leak in her bathroom. She called me again to ask my help. I said, "my plumbing fees were very high."

She laughed and said she would just have to owe me.

I told her, "I know how you can start paying me back for all the things I've done for you and it won't cost you any money."

She laughed kind of nervously and asked, "what are you talking about?" She knew exactly what I was talking about. I had mentioned it a couple of times before but never followed up on it.

I said, "you can wear something sexy for me while I worked on your water leak," "Wear a see through blouse or even a button up dress and leave some of the buttons undone." She has a nice figure at 39 years old. Since her divorce she has toned up nicely.

She said, "I don't know if I can do that."

I said, "You can start paying me back for all I have done for you starting today as I requested." I told her it would be easier than coming up with the money to pay a high priced plumber to fix it for her. I said, "I really wasn't into plumbing anyway."

There was a long silence on the phone so I said, "I knew she could do it and would be over in a little while."

When I got to her house she answered the door dressed in a see through blouse and a skirt that buttoned up the front. She also had on a bra. It was a sexy little thing but not what I was hoping for. She smiled and said, "I just had to wear a bra under the blouse."

I checked the leak to see what it would take to fix. She knew I was disappointed. As I left I smiled and said, "I appreciate your effort but was hoping for a little more."

She said, "I will try to do better when you come back but it was hard for me to do something like this."

I told her, "from now on when I asked you to be sexy for me, that meant no underwear of any kind unless I approved it first."

She had a kind of surprised look on her face as she asked, "you mean your going to ask me to be sexy for you again?" I just smiled at her and left to get the parts.

When I came back I went into the house and Sherri stood smiling at me in the same blouse but without the bra. Her nice 35C tits stood out nicely not sagging hardly any. Her nipples were hard as rocks sticking out almost a half of an inch. The dark circle around her nipples were the size of silver dollars.

I said, "that was what I was talking about." She blushed as I stood looking at her tits. I said, "you have very nice tits and that it is a shame to cover up such a sexy body." She stood there for a few more seconds and then with a sheepish smile on her face turned and went into the kitchen asking me if I wanted anything to drink. I smiled to myself as I realized what a big step it had been for her to do what she had just done. I knew I had broke through the barrier and was excited to see just how far I could take her. She fixed us a soda.

I went into the bathroom and started fixing the leak. When she brought the drink to me I noticed she had the bottom two buttons undone on the mid-thigh length skirt. She stood talking to me as I worked. I had a hard time working and looking at her sexy outfit. I said, "you have a very nice body and should show more of it."

She said, "I don't think my body is that sexy and don't think anyone wants to look at me."

I started talking about how exciting it would be to have her wear that outfit out in public.

She said, "I don't think I could do it, that it took a lot for me to wear the blouse without a bra for you." She said, "I know I owe you alot for all the things you have done for me and I really appreciate it very much." She said, "I thought about it and knew I would never have the kind of money it would take to repay you so I decided to try to please you by doing what you asked me to do."

I decided to push her a little farther and said "I really appreciated her doing it for me and would like for her to wear the same outfit and go riding with me." I said "you can cover up until we got away from home where we wouldn't see anyone we knew."

She smiled and said she wanted to please me but....I interrupted her and said. "I knew she did and that I would really appreciate her doing things like this for me." She just stood smiling at me and I asked, "don't you find it exciting to think about exposing your sexy body to strangers?

She kept smiling as she said, "I don't know, I'm not sure how I feel. You have me a total reck inside."

I said "I find it very exciting and thought she did to."

She asked, "What makes you think I find it exciting to expose myself to strangers?"

I said, "I can tell by the way you smile and moved back and forth from foot to foot that it excites you to think about the possibility of strange men getting a look at your sexy body."

She laughed and said, "you think so, huh?"

I smiled and said "I knew so, but knew she didn't want to admit it." I told her everybody had a little bit of exhibitionism in them. She still stood there smiling and I decided to push it a little more as I said "she should unbutton a couple more buttons on her skirt."

Still smiling a big smile she said, "I was terrible" and walked out of the bathroom. I was pleased at how she had accepted my suggestions so far. I could tell it did take alot for her to do it.

I worked on the leak under the sink and she was gone about five minutes and then came back into the room. I smiled to myself as she had two more buttons undone on the skirt. She was reading her mail. She never said anything about the buttons and I never either. There were only three buttons left fastened and the dress spread apart as she sat down on the stool and read her mail. I was excited as I could see her bush between her slightly spread legs. She wasn't wearing any panties as I had requested earlier. She realized I wasn't working and looked to see me looking at her. She blushed as she knew what I was looking at. She said "I should go in the other room so you can finish your job."

I said "no, that I was just taking a break and the scenery in here was what kept me working on this job." I told her I should hurry up though if we were going to have enough time to take that drive I wanted to take. I swear that as I sat on the floor infront of her, she went back to reading her letter and her knees parted about four more inches giving me a good view of her pussy. She was using the letter holding it where she could not see my eyes and I could not see hers. She was intentionally showing me her pussy.

After a couple minutes she stood up and walked towards the door and smiled at me and said "yes". I looked at her questioningly. She blushed even a deeper red as she said "yes, I find it exciting to think about exposing myself to stangers."

I laughed out loud and said, "man are we going to have some fun."

She said she only had one rule to enforce. I sat looking at her as she said again. "I really appreciate everything you have done for me and will do anything you want me to do except, I won't fuck you."

She felt kind of bad about doing what she was doing now because of my wife. Sherri and my wife were friends. Not best friends but friends. I agreed that if she would do everything else I asked her to do I wouldn't ask her to fuck me.

She smiled and breathed a sigh of relief as she said, "I was afraid that was where this was headed."

I said, "I would love to fuck you but will give that up if you will do anything else I ask."

She said, "finish your job" and left the room. I figured that down the road things would work out and I would be able to get all the pussy from her I wanted. I finished the job and cleaned up.

She buttoned the dress all but the two bottom buttons and put a light jacket on and was ready.

I smiled as we got into my pickup truck and headed north to the interstate highway. It was about a half hour drive. While we drove I enjoyed the thought of exposing her sexy body and when we got to the interstate I said, "take off the jacket." She did and I had her slide over in the seat next to me. She smiled as she moved the jacket and slid over next to me. We were about to touch each other for the first time in a sexual manner. My cock was hard as a rock as I thought about what was about to happen. I said, "unbutton all but the top button on your skirt." She started to unbutton it and I had another idea and said, "leave the top three buttons buttoned." She did and I reached down and spread her skirt apart exposing her legs up to just below her bush. She smiled up at me.

I put my arm around her shoulders and slowly slid my hand down her shoulder onto her right tit and gently squeezed it throught the see through blouse. She sat there not moving as I gently pinched her nipple. She was letting me do what ever I wanted and I was really enjoying playing with her beautiful tit. We caught up to a big truck and I said, "here we go." I slowly drove along side of the truck watching the mirror on the truck. I saw the driver look at us and then take a double take as I'm sure he could see Sherri's tits through the blouse. I drove slowly on by the cab. Sherri was sitting there looking straight ahead. I squeezed her tit and asked, "are you O.K?"

She looked up at me and asked, "did he see me?"

I said, "I think he did." Her nipples were hard as rocks. She never mentioned anything about me playing with her tits.

I started unbuttoning her blouse and spread the top apart totally exposing her tits. I squeezed her right tit, then moved to her left tit and squeezed it. Her skin was so soft and her tits were so firm. I loved the way they felt. I pinched and pulled on her nipples as we drove up behind three trucks running together.

I smiled and said, "here we go again" as I pulled out to pass the first truck. I slowed as I came along side of the cab. The driver was getting a good look at her exposed tits and sexy shapely legs. I then passed the second and third truck slowing to give each trucker a good look at her also.

As I played with her tits, she was shaking and I realized she was having an orgasm. I said, "I believe you like exposing herself as much as I do."

She smiled and said "Oh Yes, I can't believe how excited I am." We drove on the interstate for about an hour exposing her to several truckers. I had her unbutton more buttons as we drove beside a truck exposing her bush to him. About half way into the trip I told her I wanted her to strip naked beside the next truck and show her totally exposed naked body to him.

As I pulled up beside the next truck she looked at me and then slowly removed her blouse and lay it in the seat, then unbuttoned the last button at the waist of the skirt and raised up and slid it out from under her and lay it in the seat beside her and sat there totally naked as the trucker looked on. What a turn on it was to see her totally naked. We both were excited as I pulled on ahead of the truck. I said, "I'll pass six more trucks and then we would go home."

She smiled and said, "OK." I looked and saw a tour bus up ahead. When she saw the bus she looked at me and asked, "should I cover up?" I said no way as I came up behind the bus. I pulled out and started passing the bus. The windows were dark and I couldn't see the people looking out but I am sure they could see Sherri sitting there totally naked as I slowly passed.

We drove back home and I enjoyed playing with her tits all the way home. I would pull out on her nipples and move in a circular motion and pull up on her nipple and let go and watch her tits bounce and sway. She let me do anything I wanted. I decided to let her cover up when she wanted to. She surprised me by not covering up until we were almost home. I hugged her and told her how much fun I had had and couldn't wait to do it again.

She smiled and said, "yes, it had been alot of fun."

I will write about more of our sexual adventures later.