Exercising with Benefits Ch. 01

This story started when I was ten. No, nothing sexual started then. My family had just moved from a small town to the city. The move meant my mom had to start working to help pay the bills. So my parents arranged with our next-door neighbour to look after me after school.

Mrs. Thompson was about my mom's age and a very warm and loving woman. She had three children who were in high school at the time so she loved to have a younger person around. She became my second mother. I guess you would say her figure was ample. She was a bigger woman but not what you would call fat. After school we used to bake cookies, read stories and play games. It was great being at her house.

It was during the reading sessions, I first became aware of Mrs. Thompson's breasts. She used to put her arm around me and snuggle me in as she read. My head would end up on her breasts as I used them as a pillow. Mrs. Thompson liked having my head on her breasts. Being so young, you never think about something like this in a sexual way. It was the most natural thing in the world to put my head on her breasts.

It was when I was about 16 that Mr. Thompson left. He took off with his secretary and that was the end of him. Mrs. Thompson was devastated. For weeks, she seemed to always be crying. I did my best to try to comfort her but what can a 16 year old really do?

Maybe a year or so after he left, I came home from school one day and there was Mrs Thompson in a leotard. She was standing in the middle of the living room working out to a tape playing on the television. That first day, I plunked myself down on the couch to watch. The leotard was fairly tight and clung to her body. I could make out the outline of her bra and panties through the material. The gentle rolls of her belly were plainly visible as well.

Now at 17 or so, a young man's hormones are roaring. While I had not really thought of Mrs. Thompson in a sexual way before, it was hard not to as she bent and stretched in that tight leotard. If I remember correctly, I went home early that day so I could relieve the pressures that had built up.

The next day or so, when I came in, Mrs Thompson had me join her in the exercises. She said she didn't want to do this alone. So that became our routine. Whenever I showed up at her house after school, we would exercise together. It didn't take long before the results started to show and Mrs. Thompson began losing weight. I was even feeling the benefits of the workouts.

Being in high school, I didn't go to her house every day. Sometimes a week or two went by between my visits. Often I just went home after school. But when I did go over, Mrs. Thompson often was working out. I must say, over the year or so since she had started this, she had become a knockout. Her figure was fantastic. It was all I could do to keep my eyes off her. I think I went home with a hard-on every time I visited.

When I was 18 and finishing my senior year in high school, I made a point of stopping over most days to see Mrs. Thompson. She was in incredible shape and I love to watch her work out. She would bend over right in front of me. Her crotch was often close to my face. Sometimes she would bend over facing me and I could see down her top. Her ample breasts looked incredible.

I remember that spring, I went over one day and Mrs Thompson was working in her garden. She had on a scoop neck top and shorts. She was turning the soil so I joined in and helped her. Often, she would bend over and I could see down her top. Sometimes she had her back to me and would bend over. Her shorts were tight into her ass crack.

When the soil was turned, she got on her knees and started to plant some flowers. I was behind her and I could not take my eyes off her ass. It was incredible. The shorts were tight enough I could make out her panties lines. My cock was a rock. As she moved, she was facing me sometimes and I had a great view down her top. I could see most of her breasts in her white bra. My cock was in agony. After an hour or so, I said goodbye and raced home to relieve my hard-on.

One day in the summer I went over and Mrs. Thompson was sitting on a chair on the back porch. It was a very hot day. She was sitting and reading a book and drinking lemonade. I sat down opposite her and we talked. I kept glancing at her breasts which I was sure were not encased in a bra. Her nipples were too obvious. Also, her shorts were very loose. As she moved, the material slid up her legs. I was hard again.

Being so young, you think you're not being observed as you sneak peeks. I had convinced myself Mrs. Thompson didn't know what I was doing. At one point she stood up and brought the pitcher of lemonade to me. As she poured it, she leaned over. I had a clear view down her top. I could almost see her complete breasts. When she straightened up, my eyes met hers and I could see she had a smile on her face.

When she sat down, she put her feet on the front of the chair. This pushed her crotch towards me. I snuck a quick look then looked back at her face. She was still smiling. Now as we talked, she moved a little and the material moved on her legs. After a few minutes, I could see down one leg open to her red panties. WOW!!! I wanted to rip those shorts off her body.

As I stared something different was gradually appearing. At first I didn't know what I was seeing but after a few minutes, I realized that the crotch of her shorts was showing a wet spot. I can't tell you what we talked about, as all I can remember is the beautiful sight I was seeing.

As usual, I went home and pounded my meat until I came several times. Not only was this scene re-played several more times in her backyard that summer but I re-played it many many times in my head. Mrs. Thompson had become a hottie!

That September, I started college. My classes were such that I finished about 3:30 every afternoon. The week before I became 19 and I dropped in one day to find Mrs. Thompson had not started her exercises yet. She was glad to see me and we sat and talked for a while. Then Mrs. Thompson said, "It's almost time for my exercises. I bought something as part of my birthday present for you. Why don't you set up the machine with my tape and then sit on the couch. I'll go and get changed." So as she went off to change, I got the tape and television set up then moved to the couch.

A few minutes later, Mrs. Thompson came into the room. She was holding a towel in front of her as she walked. She stopped in the middle of the room facing me and tossed the towel at me. I was busy catching the towel and I didn't see her for a few seconds. When I looked, I couldn't believe what I was seeing. Mrs Thompson was wearing a white leotard. It was stretched tight on her body. She didn't have any underwear on underneath. I could make out the dark areas around her nipples and could see the dark patch of her pussy hairs.

Slowly she turned and moved to the television. She started the tape and moved to the centre of the room. The music started and Mrs. Thompson started working out. She bent and stretched with the tape. As she worked, she started to sweat. The moisture made her leotard become even more transparent. At one point, she laid on the floor. The exercise was to lie on her side and lift the top leg. The way she laid down, her toes were pointed toward me. When she lifted her leg, I had a clear view of her pussy. The leotard was damp and I could make out the outline of her pussy lips.

My cock was so hard. I was absently mindedly rubbing my cock though my pants. Mrs. Thompson stood up and saw what I was doing. She stood there for a few seconds then turned her back to me with her feet spread and bent over to touch her toes. Her pussy was only a few feet from my face. She was looking back at me between her legs. The leotard was stretched tight and pulled deep into her pussy lips. I could see some of the hairs from her pussy sticking out of the leotard. She then put her hands on the inside of her legs and moved them upwards. Her fingers went all the way up to her pussy and then gently rubbed over the material.

Slowly she stood up and faced me again. "Why don't you open those pants and relieve that monster you have hiding in there. I know you want to. I would love to watch." So slowly I pulled the zipper down then reached in and pulled out my cock. I started to rub it. Mrs. Thompson's eyes didn't leave my cock. She reached between her legs and slid several fingers along her pussy. We both were rubbing as we watched the other. I came first. Sperm was shooting everywhere. As the cum was flying, Mrs. Thompson let out a big groan. Her knees buckled and she kneeled on the floor. Her fingers never left her pussy. She threw her head back and pumped her pussy as she came.

When she stopped cumming, we both just sat there looking at each other. Neither of us spoke for a few seconds. Mrs. Thompson suddenly stood up and ran from the room. As she went, she said over her shoulder, "I'm sorry. I'm so sorry." I heard the door to her bedroom slam shut. I took the towel and cleaned up my mess then left.

After that afternoon, I didn't see Mrs Thompson for a couple of weeks. I did try to go over and visit a couple of times but she was never home.

It was about 12:30 on a Friday night. I had been out with my friends and on the way home I stopped and grabbed a burger and fries. I was eating on the front step enjoying the warm night air when I saw a car coming up the street. I watched and as the car got closer I realized it was Mrs. Thompson's car. She turned into her driveway and parked. As she got out, I called to her and startled her a bit. As she started to walk toward me, I could tell she had been drinking because she was swaying a bit as she walked.

What a vision. Mrs. Thompson sure didn't look her age. She had on a short skirt and heels with dark stockings or pantyhose. As she came into the light by our stairs, I could see her blouse was a sheer material and I could make out her black bra. Mrs. Thompson spoke first, "Hi Kyle. How are you?"

"Hi Mrs. Thompson. I'm doing well."

"Oh come on now Kyle. You're a man now. I think you can call me Cheryl."

"Um. I don't know. That would be a little strange. But I'll try Cheryl."

"See? Now that didn't hurt did it?" She smiled as she said that. "I'd like to apologize for the other day."

"Apologize for what?"

"For acting so forward and making you do what you did."

"Why are you sorry? You didn't make me do it."

"I know. But I shouldn't have been so forward and done what I did."

"I don't think you were forward. Besides, you're a beautiful woman and I liked seeing you like that?"

"I am? You did?"

"I've always thought you're beautiful. And of course I liked seeing you in that leotard. You looked incredible."

I think she blushed a little then said, "Why thank you Kyle. I've been so worried the past few weeks. I didn't know what you'd think about me."

"I think you're one of the most beautiful women I know. That leotard was fantastic."

"Thank you. Can I tell you a secret?" I nodded my head. "I had been wanting you to see my in that leotard for a long time."

I almost choked on my burger. "You... you did?" I stammered.

"Yes. I've been watching you for a long time now. I see how you look at me. To tell you the truth, I've enjoyed having you look at me."

"Wow! I didn't know."

"Did you think I wasn't noticing how you looked at me? A woman always knows." She laughed as she said it. "You've made me feel so young and beautiful. I just wanted to give something special to you. So I bought that leotard one size too small so I could show you my body. I don't have to ask if you liked what you saw." This time we both laughed.

"No you don't. You looked absolutely incredible."

"Do you really think so? How do I look tonight?"

"Fantastic. Absolutely fantastic."

"Oh Kyle. You're so wonderful."

All this time I had been sitting on the lowest step with my back against the railing. Cheryl had been leaning against the railing on the other side. We didn't say anything for a bit as I finished my snack when Cheryl finally said, "I didn't get you a real birthday present this year. I'm sorry."

"Hey, you don't have to apologize."

"I know but I feel badly. I haven't missed one of your birthdays yet." As she said this, she slowly lifted her leg closest to the house and put her foot on the lowest step. My eyes followed her leg. It moved like it was in slow motion. Her knee ended up pointing directly at me. When she stopped moving, my eyes looked back to her face. She had that smile again. "I think I have a present for you we'll both enjoy," she said.

Quickly her eyes looked around the neighbourhood. I don't know what she was looking for but my eyes did the same. I heard her drop her purse and I looked back at her. Still that smile was there. I noticed out of the corner of my eye that her leg on the step was moving. I looked down and saw she was moving her knee to the outside. Her short skirt hung like a curtain from the top of her thigh down across her pelvis to her other leg. I looked up at her and she said, "Here comes your present. Have a good look."

I looked back down just as her hand rested on the top of the bent leg. Slowly she started to move the skirt back along her thigh toward her belly. After it moved only a few inches, I could see the top of her black stockings. Then the bare skin of her upper thigh was visible. She stopped moving her hand. I looked up. She was looking at me. Slowly she nodded her head as if to tell me to look back down. I did and then she moved her hand from the top of her thigh under her skirt. She pulled the skirt up and I could see her panties. Cheryl looked incredible with black stockings, white skin and black panties.

Quickly I looked up at her and she just stood there smiling. I looked back down. My cock was as hard as it had ever been. With one hand she held the skirt up. With the other she was gently rubbing across her belly. Slowly her fingers moved lower and disappeared between her legs. Her hand moved in and out as she caressed her pussy.

She did this for maybe a minute before she said, "Kyle, I've wanted you for so long. I've been watching you watch me for years and my pussy gets so wet thinking about you. I want you Kyle."

My brain didn't completely comprehend what she was saying. I looked at her face, which now had a bit of a glazed look to it. I looked back down and she kind of rammed her fingers into her pussy. Cheryl now started to work her pussy harder and harder.

Suddenly she stopped, dropped her skirt and took her foot off the step. She took a step toward me and put her pussy soaked fingers under my nose. "Kyle, I want you to take me NOW!!!! I need your cock in my pussy."

I was shocked. I had never heard her talk like this before. I took a deep breath. The smell of her pussy filled my nose. Then she moved her fingers to my lips and pushed them into my mouth. I immediately tasted the sweetness of her pussy juices.

"Tonight you're mine, Kyle. My present to you is make you into a man. I'm giving you my body and together we'll experience what we've been waiting so long for. Pick up that garbage and come with me." With that, Cheryl turned and headed toward her house.

I quickly followed but it was a little hard walking with my big hard-on. All the way to her front door, I watched her sexy ass swaying as we walked. Her skirt flipped from side to side. I caught up to her at the front door as she unlocked it. We entered into the dark house. Cheryl didn't turn on the lights but just locked the door and dropped her purse and keys on the table in the hall. She then headed upstairs.

I could just make out her form from the street lights outside. At the top of the stairs she turned and walked into her bedroom. I was right behind her and stopped just inside the door. Cheryl went to the bedside table and turned on a little light. Then she went to the window and closed the curtains. Finally, she walked back to me and put her arms around my neck. Our lips met and her tongue quickly followed.

Our bodies were pressed close together. I could feel every curve in her body. Her tits were pressed hard into my chest. My cock was pressing into her belly. I had my hands on her back and could feel her bra. The kiss went on and on.

Cheryl then moved a half step back from me. My hands slid to her hips. She was looking deep into my eyes. Her hands found the buttons on my shirt and quickly it was undone. The shirt hit the floor. Then my belt opened and my jeans were next. Cheryl dropped to her knees and helped me take my shoes, socks and pants off. I was now naked before a woman for the first time.

Without even looking up at me, Cheryl took my cock in her hand. I jumped at the incredible softness of her touch. It was nothing like when I play with myself. Cheryl still didn't look at me. Her other hand cupped my balls. Then slowly, she leaned over and kissed the tip of my cock. Her tongue was next. She licked the tip as she squeezed my balls lightly.

Then without warning, she put my cock deep into her mouth. I was almost balls deep in one gulp. Slowly she pulled her head back as she let her lips caress the sides of the shaft. When she got to the knob, she held it there and licked it with her tongue.

My cock then slipped out of her mouth. She looked up at me and said, "I knew you had a big one. This is magnificent. You're going to make me very happy in a little bit. Now I want you to relax and let my tongue make love to you. When you feel it is time, let your cum shoot into my mouth. Don't worry, I love the taste of cum and I want you to shoot off in my mouth." Her mouth quickly surrounded my cock again.

She started to bob on my cock. Her lips were pressed tight along my shaft and her tongue was dancing everywhere. I don't think I lasted more than two minutes. My cum started to shoot off into her mouth. Cheryl didn't miss a beat and just kept bobbing and sucking. When I was finished, she gave my cock one last kiss and then stood up.

"Did you like that?"

"Oh my God, yes!!!! That was incredible."

"Good. But that is only the beginning." She then took my hand and led me to the bed. She pushed me lightly so I would sit on the edge. Cheryl took a step backward and slowly started to undo the buttons on her blouse. I think each button took about 30 seconds to undo. It was a slow process. She even took the time to undo the buttons on the sleeves. With all the buttons undone, Cheryl stepped closer to me. She turned around and said, "You take it off." I nervously reached up and gently pulled the soft material from her shoulders. She took a step away from me as blouse floated off her arms. I was left holding it.

Next she turned to me and put on foot on the bed beside me. I could see up her leg. She leaded over and started to undo the strap on the shoe. Her eyes never left mine. When the strap was undone, she leaned further and kissed me. "You take it off for me." I turned my head and put a hand on her shoe. She lifted her leg and the shoe was in my hand. After straightening up, Cheryl put her foot on my thigh. She just looked at me. "Don't you want to feel my leg? Its yours if you want."

I looked down at her beautiful leg. Nervously I put my hand on her calf. I could not believe how warm her leg was. The silky feel of the stocking was incredible. Slowly I moved my hand down her calf then back up. When I got to the knee, Cheryl moved her foot off me to the bed so her leg was now straight. I looked up at her and then slowly moved my hand higher. I was on her thigh then the top of the stocking and finally I felt the soft warm skin of her upper thigh. I was in territory I had only dreamed about before. I was only inches from pay dirt.

I could only move my hand a little. I was almost paralysed. Looking at Cheryl, she just smiled at me. She then reached down and pulled the hem of her skirt up and out of the way. We both looked at my hand on her thigh. Slowly she pulled her foot off the bed and my hand slid off her thigh.