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Exercising with Benefits Ch. 01

By: Bigguyyyyy



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.


Exercising with Benefits Ch. 01



Next her other foot came up as she put her second shoe on the bed. We repeated the undoing and removal of this shoe. Before I could put my hand on her thigh, she had already pulled the skirt up. I was quickly up her leg and on the soft skin of her upper thigh. But this time I was on the inner part of the thigh. My finger tips were only half an inch from her crotch. Cheryl reached down and put her hand on mine. I froze and looked at her. She just smiled. Then she pulled my fingers upward and the tips touched her panties. She kept pulling and the tips slid along her panties. The panties were wet. The heat coming from her pussy was intense.

"Touch me Kyle. Run your fingers along the panties and enjoy." Who was I to argue? My fingers were sliding along her panty covered pussy. I could feel her soft thighs and the silky material of the panties. The wetness of her pussy was soaking my fingers.

After a few minutes, Cheryl took her foot off me and stepped back. She reached to her side and undid the button on her skirt. Then the zipper went down. Cheryl shimmied her hips and the skirt slid down her legs. I could hear the material sliding over the stockings. She stood there only wearing her bra, panties and stockings. She let me drink in her beauty. Slowly she turned so I could see her from all angles. Cheryl then walked to her closet and hung up her skirt. She came back to me and took her shoes and blouse. All I could do was sit and watch this beautiful woman walk around in her underwear. What an incredible sight.

Cheryl then came and stood in front of me. She had that smile again. She turned her back to me and her hands came up and unhooked her bra. Turning to face me, she held the bra in place. Then slowly it slid off her shoulders and down her arms. From my angle, I couldn't see her breasts until the bra was almost completely off. When it was, she flipped it onto the chair beside her.

Cheryl just stood there and let me look at her tits. They were awesome. The circle around her nipples was a nice dark brown. Her nipples were about half an inch across and maybe half an inch long. Cheryl then walked toward me. She put her legs between mine and forced my legs open. Her hands went behind my head and she pulled my mouth to her left breast. The nipple slid between my lips. I was sucking her like I was the hungriest baby in the word.

I reached up and put my hands on her hips. The feel of her soft skin and silky panties was incredible. Slowly I moved my hands around her until I had a bum cheek in each hand. I then switched breasts and put the other nipple in my mouth. Cheryl let out a moan. Her knees buckled a little and she slumped down with the pleasure I was giving her.

My fingers moved down buns and went between her legs. I started to play with her pussy lips from behind. "God Kyle. That feels incredible. I've waited so long for you to do this to me. You're certainly not disappointing me."

With that encouragement, I put on finger inside the leg of her panties. Then I slid it forward. Suddenly, I was touching her pussy. My first pussy and it was so wet and hot. My finger easily slid along until I was touching the opening to her pussy. Cheryl flexed her knees so she opened up for me. My finger slid in her hole a little. "God, God, God!!!!! Fucking incredible. Keep going Kyle!!!!"

My mouth was moving between her two breasts. I was kissing and licking them. I slid more fingers inside her panties and along her wet pussy lips. I was in heaven!!!!!

Cheryl then pulled back from me. My lips left her tit and my fingers pulled out of her pussy. Without talking, she moved to the side of the bed and pulled the covers down. She lay on the bed and reached out for me. I stood, turned and crawled over the bed to her. "Take them off love." She lifted her hips and I pulled her panties off. Cheryl lay there now in only her stockings. What an incredible sight.

Looking at my cock, she said, "Looks like you are ready again." I looked down and could not believe what I saw. My cock was hard as ever. It had refreshed and was ready for action. I didn't even feel it get hard. I guess Cheryl knew what to do to get me ready again. She reached up for me. "Come on love, lay on me." She opened her legs and I crawled between them. As I lay on top of her, she reached between us and grabbed my cock. I was now at the entrance to her womanhood. "Push babe. Enter me. I'm all yours." So I pushed. 

It was a little tough getting started. I had to pull out then push back in several times because she was so tight. Finally I pushed in and was balls deep in her hot pussy. I just lay there. We both had to rest and just hold still. Cheryl had not been fucked in a long time (so she told me later). For me, this was my first time. I couldn't believe how hot, wet, soft and incredible she felt wrapped around my cock. My hand had never felt this good.

I decided to move and I started to pump in and out of her. Slowly we got into a rhythm. It wasn't long before I was pumping her for all I was worth.

Cheryl had her eyes closed. I leaned down and kissed her face. Her tits were pressed hard into my chest. A little smile appeared. My cock was hammering away at her. Cheryl was pushing back up to meet my thrusts. I kept pumping. Then I heard a scream came from her lips. I stopped. "Are you alright?" I asked.

"Don't stop. Don't!!!! Keep going." So I kept pumping. I think maybe 5 more minutes went by and I felt my second cum of the night starting. I pushed in hard and deep. My cum shot into her pussy. When the first blast hit her, Cheryl let out another little scream. I pumped a few more times then pushed in hard and held still. My orgasm was very powerful.

When it was over, I collapsed on top of her. We just lay there for a while not moving. Finally, I lifted my head to look at her. Cheryl opened her eyes and smiled. She kissed me. "Wow!!! That was unbelievable. In a way, I am sorry we waited so long. You're a fantastic lover young man."

I just smiled. What can one say but "Thank you!

I rolled off of her. Cheryl rolled onto her side to look at me. "From now on, you can have me anytime you want. I'm yours for the taking. Besides, I have many things to teach you."

We kissed and Cheryl's hand found my cock again. "Oh!!! Someone needs to get cleaned up before he goes home." Cheryl then moved down and sucked my cock into her mouth. She licked and sucked until my cock was all cleaned up. "Now young man, you should be getting home before your parents find out you're still not home. Don't want you to get grounded."

As I got up and put on my clothes, Cheryl just put on her panties. What an incredible sight. Beautiful woman with that just fucked smile of contentment standing there in her panties and stockings. My cock got hard again just looking at her. I walked over to her and took her in my arms. We kissed deeply and passionately. When I pushed my cock into her belly, Cheryl pulled back. "No, no mister. We've had enough fun for one night. You've have got to be running along."

"But you just said anytime."

"And I meant it but it's late now and we don't want you to get in trouble."

We went to the door. Cheryl flicked on the hall lights. As I followed her down the stairs, I had the pleasure of watching her ass wiggle as she walked. At the front door, she turned to me and we hugged. Our lips met again for another passionate kiss. I pushed my cock into her belly and Cheryl pushed back into me. I reached down and cupped her ass cheeks. I think we kissed for maybe 10 minutes. It was incredible.

Finally she pulled back and asked me, "So what are you doing tomorrow night?"

That is the next part of the story.



Exercising with Benefits Ch. 02



When I got home, of course the house was silent and mom and dad had no idea where I had just been or what I had done. I took a quick shower and headed to my room to sleep.

I must tell you though that sleep did not come easily. All I could think about was Cheryl, her fantastic body and the incredible sex we just had. I truly wanted to head back over and repeat what we had just done. But I knew I would have to wait.

Surprising, my cock was responding to the thoughts I was having about Cheryl. It was growing nice and long again so I took the opportunity to play with it until I was able to squeeze out another round of satisfaction. Sleep came quickly after that.

The next morning, I woke about ten and went downstairs. Mom was in the kitchen and dad was reading the paper. We exchanged the usual morning pleasantries and they asked me about where I went what I did the night before. Even though I was on cloud nine with happiness, everything was the same boring stuff as every Saturday morning.

The only exception for me was that I kept looking out the window toward Cheryl's house. Mom noticed me looking and asked if everything was alright. I told her it was and that I was just thinking about calling some of the guys and getting a basketball game going at the park. The weather just looked a little iffy was all. That seemed to satisfy her.

Time was killing me. It moved so slowly. I had to get out and do something or I would scream. Early in the afternoon, I headed to the park with my basketball. All the way there, I was hoping none of my friends would be there because what I really wanted to do was head back to Cheryl's.

The basketball court was in a little valley at the park. As I crested the hill beside the court, my heart sank as three of my buddies were there. When they saw me, they were so happy because we could play two-on-two. What could I do but join in.

I do love basketball and really have a good time with my friends. It was just that I had something else on my mind. It must have been obvious as my buds asked me a couple of time what was wrong. Apparently I just wasn't there. They said my thoughts were somewhere else. They started joking with me and trying to figure out what it might be. A team of wild horses couldn't have pulled it out of me.

I must have had a good time as 2 hours flew by. The four of us then headed to a local shop and ordered shakes and fries. As young men usually do, we BS'd each other, made jokes and cut up each other for the rest of the afternoon.

When it was time to head home, they tried to make plans for that evening but I backed out. Told them I wasn't feeling too good as a headache was starting. They, of course, tried to joke me out of it and tried to get me to meet them that night. I had other plans though.

All I wanted to do was connect with Cheryl again. She had filled my thoughts all day. Does every guy go through this after his first time? I didn't know but I knew I wanted more of her. I needed to talk to her and make plans if possible.

Thinking about how to accomplish this (this is in the days before cell phones became so popular) I remembered the walkway beside her house. I didn't want to walk home the normal way and possibly having mom or dad see me sneak over to Cheryl's before coming home. If I took the long way home, it would get me to the far end of the walkway on the street behind our houses. Then I could jump the fence beside the walk and get to her back door.

That is what I did. It was not that a long walk and before I knew it, I was beside her house on the walkway. There was a 4 foot high chain link fence along the path to keep people out of the neighbor's yards. It was easy to hop over it and duck behind her house without being seen.

I pushed the door bell button beside the back door. It took a few seconds before Cheryl arrived. The door opened with a little swoosh sound as the air rushed in to fill the vacuum caused by the door opening. I opened the storm door. As I stepped in, Cheryl said, "I was wondering who would be at the back door."

"Just me," I replied. "Trying to avoid the parents seeing me."

"Ashamed to be seen with me are you?"

"I'll show you ashamed," I retorted. Stepping forward, I wrapped Cheryl in my arms and pulled her in for a hard, tongue in the mouth kiss. My hand found her butt and pulling her toward me. My semi-hard cock pressed against her mound. We stood there kissing for a couple of minutes.

My hand on her butt had made its way lower and was tickling between her legs from behind. I loved to feel that crease where the butt cheek meets the top of the leg. It felt great to have my little finger buried in the skin of that fold.

When the kiss ended, I looked at Cheryl. Slowly she opened her eyes. They looked kind of funny, almost glazed over with a kind of far away look. "WOW young man! That was some kiss. Hope you got more of those stored away someplace."

"That's why I'm here. I was wondering what you're doing tonight?"\

"I was hoping you'd tell me," she answered.

"How about I come over?"

"I'd love that. What would you like to do tonight?"

"Well after last night, I think we can find a thing or two to keep us busy."

"Maybe! You just might be right. How about 7:30? Is that good for you?"

"Perfect. I'll see you then." Somehow we just melted together again. Our lips met and our tongues danced. It was both sensual and satisfying. There was no rush in the kiss, just relaxed enjoyment.

"When you come over, let yourself in this door. I'll leave it unlocked"

"Ok!" There was one more quick kiss then I turned and went out. Glancing back to Cheryl and we both smiled.

I quickly covered the short distance between the two houses. Maybe I was too quick in getting home as I was still semi-hard as I opened the front door. Cheryl makes me hard so easily.

Time started to drag again the moment I entered our house. Mom was making dinner; Dad was watching golf on TV. Simple greetings were exchanged and the usual questions about my afternoon activities. I then headed up to have a shower. Playing basketball had me made me sweaty. Now it was time to clean up to tonight.

Dinner was boring. The small talk was almost non-existent. My thoughts were in another woman's house. We ate and I washed up the kitchen. Why not? Good way to waste time. About 7:15, I made sounds about getting ready to head out. Again, questions about my planned activities. Nothing exciting. About 7:25, I left the house. Mom and dad were both watching TV so I could easily head to Cheryl's without being seen.

As promised, the back door was unlocked. When I entered, I called out, "Hey Cheryl."

"Hi Lover."

"Where are you?"

"Here. In the living room."

I went upstairs to the living room and there was Cheryl. I froze in my tracks. I would bet my jaw had dropped as well. There stood Cheryl in the white, too small leotard. Her exercise tape was playing. She had been exercising for a while as her leotard was a little damp.

"Come on Lover. Join me. I think we'll both need to be in good shape for all the loving I'm hoping you want to give me." I didn't move so Cheryl continued. "Come over here and help me out." I felt more like a zombie than anything else. Cheryl in that tight leotard wanting me to help her was all it took. She looked incredible.

As I got beside her, her arms went around my neck and another tongue sucking kiss started. This time, my hands were all over her back and down to her butt. I pulled her into me. Her breasts flattened against me. My cock pressed into her mound.

I felt her starting to sway a little. At first I didn't know why she was doing that but then I felt how my cock knew what to do. It was getting harder as the swaying was rubbing her hard mound on me. I was hard in only a few seconds. "Mmmm! That's what I've been waiting for today," Cheryl said.

Somehow we managed to end the kisses. Cheryl turned to look at the tape. They were doing bend-overs where you try to put the palms of your hands on the floor. With me behind her, Cheryl bent over. There right before me was that perfect white covered ass. I stepped up and pushed my cock against her. This time it was me that started to move. Up and down I went as I pressed harder and harder into her.

"Oh My God Kyle! That feels incredible. Take that wonderful cock of yours out and let it play." How can you resist a request like that? Stepping back a little, I quickly shed all my clothes and tossed them onto the couch.

Looking at Cheryl, she had not straightened up. Her butt was still high in the air and pointing at me. I could also see that her leotard was wet around her pussy. She was ready.

I stepped forward. Taking my cock in my hand, I touched the tip to the crotch of her leotard. Pre-cum was leaking already so I mixed this with her juices on the material. I smiled to myself as I thought, "Good thing they're white. Won't see the cum as easily."

The feeling was incredible. Her hot juices on the material was stimulating me. With one hand on my cock to guide my missile to its target, my other hand was on butt cheek enjoying the roundness and firmness.

After a few minutes, Cheryl's hands came up off the floor. She reached behind herself and found the edge of the leg opening of the leotard. She pushed the material over. Her pussy was partially exposed to me. My tip now touched hot, wet, soft pussy. It was easy for it to slide between those big soft lips. As I pushed forward, the tip slid downward along the valley.

The leotard material was still partially covering her womanly treasure so I took my hand off her butt and used it to pull the material all the way to the side. She was completely exposed now.

Pulling back, I now slid up her lips. Forward again but this time, the tip found the opening it had been seeking. With a little push, I started to enter her. At first, her muscles pushed back. Then they opened and I was inside.

Oh! The feeling was incredible. How can one describe the pleasure and joy being inside a woman brings? All my emotions and feelings were passing though my hard on and into this beautiful loving woman.

It did not take further encouragement to begin to stroke in and out. Slowly at first as the sensations were almost too much. Cheryl's love tunnel was hot but felt like velvet around me. I could feel her tightening her muscle ring as she gripped me on each stroke. Why had we waited so long for this to happen?

After a few minutes, I started to increase the speed. I needed to increase the speed. She felt incredible and I needed to have her harder and faster. My hands were now on her hips as I began to pull her back to me with each stroke.

Cheryl was making a grunt with each in-stroke. I was now slamming her hard and she was loving it. What a feeling of power!

It began suddenly. My balls tightened and the first shot erupted from my cock and into Cheryl. She screamed as my hot juice hit her deep inside. Another thrust and I was as deep as I could go. Both hands on her hips held her tight. My second, third, fourth and fifth blast shot into her filling her with my hot cum.

Cheryl screamed and then I could feel her pussy start to quiver around my hard cock. I was just about finished when I felt her knees give out. Down she started to fall with me still buried deep inside.

Somehow I managed to move down with her. We ended on the floor, Cheryl on hands and knees. Me on my knees.

For some reason, I started to pump her again. I was not soft yet. It just felt good. All the nerves in my whole body were now centered in my cock head. I could only stand it for a few seconds. The sensation was incredibly intense.

I felt my cock start to soften. It then fell out of her with a plop. The combined juices in her made an almost obscene noise as I came out.

Cheryl didn't move off her hands and knees. I sat back with my butt on my heels. I just sat and reveled in the intense feelings I was experiencing. I also had a great view of Cheryl's naked pussy. Our juices were slowly seeping out of her and down her thighs. What an incredible sight.

After a few seconds, Cheryl turned her head to look at me. "Wow young man! That was unbelievable. I should have started this a long time ago."

"I was thinking the same thing."

"Why didn't you then?"

"I never imagined that you would be willing. Besides, you're Mrs. Thompson. You're my second mother."

"You never have thoughts about doing this to you mother?"

"Well... I ... um..."

"I'll take that as a 'Yes'. All boys want to fuck their mother."

"Well did you have thoughts about doing this with me?"

"Hell yes! I've had them for a long time now. I just didn't want to hurt our relationship."

"Hurt it?" I asked? "I think you improved it."

At that point, Cheryl rolled off her hands and knees and lay down on the floor. She reached out with her hands for me to lay with her.

I lay on my side facing her. We started kissing immediately. My dick instantly started responding to her affection.

After a few minutes, Cheryl said, "Come on Lover. Let's go upstairs where we'll be more comfortable." So we got up, turned off the TV and headed upstairs. I was following Cheryl. Her ass was wiggling in a different way as her leotard was still pulled to one side. It was one of those sights one never forgets.

When we got to the top of the stairs, Cheryl took my hand and led me to the bathroom. Once inside, she turned to me and started another long, tongue in mouth soul sucking kiss. I know I was enjoying it as I quickly started to grow again. Cheryl felt it hit her stomach. Her hand came out and she started to stroke me. Long slow strokes as our tongues were lost in each other's mouth.

Without stopping the kiss, Cheryl mumbled, "Take off my leotard." My hands went to her shoulders and I tried to hook my fingers under the shoulder straps. That was a little difficult as the suit was tight. So I moved to her back where the material scooped around to head to the two straps. It was easy to get my fingers in there. I then slid them up the straps as high as I comfortably could. I pulled the material out and off her shoulders.

As I pulled down, Cheryl lifted first one arm then the other out. When that was done, her breasts became exposed. She pushed her breasts into my chest. What an unbelievable feeling. I moved my hands from the shoulder straps to the body of the suit and started to push it off her hips. It was a little difficult but I managed.

Once past her hips, the suit almost fell by itself to the floor. Cheryl, once she was naked, stepped into me. Her hand on my dick took it and aimed it to go between her legs. Lifting one leg a little, it was a simple matter to slide me along her hot cum covered lips.

Her hand released me and then her leg came down. We had not stopped kissing this whole time. We then started to hump each other with my dick sliding along the outside of her pussy without entering her. She was well lubricated and, with the heat coming from her pussy, all I know is it felt great.

I have no idea how long we stayed like that. I just know I was totally enjoying being with her.

Cheryl broke off the kiss, opened her eyes and looked at me. She had that funny look again. For several seconds she just stared at me. "I would like to clean up a little. Why don't you use that towel and face cloth and clean yourself a bit?"

I turned to see the items she had mentioned. Looking back at her, I gave her one last quick kiss. We released each other. I turned to the bathroom sink and Cheryl went to the bathtub. I turned on the warm water as Cheryl turned on the shower. I could see her in the mirror over the sink. Wetting the face cloth, I started to clean my dick from our combined juices. I didn't pay much attention to what I was doing as I was watching Cheryl.

Cheryl climbed into the tub but did not pull the curtain closed. She removed the shower head from the wall and started to spray herself from the waist down.

After rinsing out the cloth, I finished washing my dick. Next I started to slowly massage my balls with the warm cloth.

Cheryl squatted down in the tub. She took the shower head and aimed it at her tender pussy. I had never seen anything like this before. In fact, I have never even thought about how a woman might clean herself. Cheryl put her hand over her pussy as the water continued to spray on her. The pussy hairs were wet and matted. The water made them darker.

I was fascinated as she massaged those big soft lower lips. Her hand moved from her mound to where I would imagine her butt hole was. Up and down she delicately massaged with the warm water playing on her. She even spent time rubbing and rinsing the forest of hairs that protected her pussy.

I turned off the water, squeezed the cloth then took the towel. Turning to her, I started to dry my balls and dick as I continued to watch her with great fascination. After a bit, she started to rub the inside of her thighs. It took a few seconds for it to register that she was cleaning our juices off her legs.

Finishing, Cheryl stood, hung up the shower head and turned off the water. "Did you enjoy that?" she asked.

"I have never seen a woman like that before."

"Did you like watching me?"

"Yes!"

"Any time you want Lover. You can fuck me then I will wash for you. Would you like that?"

"You bet. I think you're so sexy! So beautiful!"

"Thank you Kyle. You're pretty sexy yourself," she said as she stared directly at my hardening dick. "Bring that towel over here."

I walked over and handed her the towel. She started by drying her lower stomach then her butt cheeks. Next she squatted a little and put the towel between her legs. Gently she patted dry her pussy. Her foot them came up and rested on the top of the tub wall. Cheryl started at her pussy and dried all the way down to her toes. Then she did the other leg.

"You still liking the show?"

"I'm loving it. I never knew showering could be so sexy."

"Oh you have no idea yet my love. I have much to teach you." Finishing the drying, she held out one hand for me to take. Like a gentleman, I assisted her climbing out of the tub. With both feet on the rug, Cheryl gave me a quick kiss on the lips. Her hand wrapped around me and she gave me a quick stroke. "I'm glad to see he has recovered. Let's see if we can tire him out. What do you think?"

I reached out and put two fingers between her legs. My move surprised Cheryl but she quickly recovered and smiled. She turned and hung up the towel and face cloth. Taking my hand again, she led me to her bedroom. The sheets on the bed were already turned down and ready for us.

As we neared the bed, Cheryl turned to face me. The kiss was hot and intense. Her hand found me and she started to stroke. I was already hard but the stroking felt great.

Without warning, Cheryl dropped to her knees and almost before I knew what she was doing, my cock was in her mouth. "Oh My God!" I exclaimed. I had never felt anything like this. Her tongue was rubbing around my head. Her hand was still stroking my length. Her other hand found my balls and she started to gently rub them together and play with the soft sack.

While fucking was better, this was a fantastic second.

My hands found the top of her head and I wrapped my fingers in her hair. Slowly Cheryl started to move her head back and forth. She was fucking my dick with her mouth. I started to pull her head onto me harder and harder. I could feel my tip move into the top of her throat then back out again.

She somehow knew I was about to blow. She pulled back from me and asked, "Do you want to dump this load in my mouth or in my pussy?"

The question caught me by surprise and it was a little difficult to think. "I'm not sure."

"Is this your first blowjob?"

"Yes!"

"Then the mouth." Without saying anything else, Cheryl resumed her work on my dick. I didn't need to urge her on by pulling her head but if felt right to have my hands in her hair and to be pulling her as she worked.




Exercising with Benefits Ch. 02



I think I put my head back and closed my eyes. I do know I was lost in a land of lust. But lust for the woman working her magic on my dick. It was not surprising I only lasted a few minutes more. Even though I had cum only about 15 minutes before, I could feel it start to bubble in my balls. 

"I'm going to cum Cheryl!" This caused her to increase the speed of the mouth fucking. She also started to seriously rub her tongue along the bottom side of my dick; the tender sensitive side. I could not take it any more. My cum shot out of my mouth. Cheryl was sucking hard and holding me as deep in her mouth as she could. My cum shot out of me and right down her throat. Four or five good hard shots erupted deep into her mouth.

There were another 10 or so mini quakes which Cheryl took and swallowed with ease. She did not stop working on me even though I was finished. She continued to suck and lick me. Finally she let me fall out of her mouth. As my tip passed her lips, she gave it a big kiss.

I reached down and helped her to her feet. The kissing started immediately but only went on for a few seconds. Cheryl broke the kiss and said, "My turn." I didn't know what she meant. She crawled onto the bed and lay in the middle. She was spread eagle so I could see how swollen her female lips were. "It's your turn lover. Time you found out what a pussy tastes like and how to make me cum."

Slowly I climbed on the bed and moved between her legs. Her pussy was wet, red and the lips were puffy and open. Cheryl reached down and opened her lips further with her fingers. I could see for the first time, the entrance to her love tunnel. She moved her finger so it was touching this little piece of skin. "This is my clit. That is where you should spend a lot of time. Kiss it, suck it, rub it with you tongue. Think of this as my dick and try to do to me what I just did to you. Go ahead, I'm all yours"

I lay on the bed and had a good look at her sex. I had never seen one this up close before. Gently I reached out and touched her hairs for the first time. They were strong and wiry. I let my finger move through them then I closed my fingers. The hairs were trapped. Slowly I lifted my hand as I kept the hairs trapped. I loved the feel of those hairs pulling against my fingers.

I did that a few more times before I moved my fingers to her big pussy lips. I actually traced a path from her mound to those lips, following the line of hairs. For some reason I was fascinated by the hairs.

Once on the lips, I tried to do what Cheryl had done. I tried to open the lips so I could see her pussy better. From my angle, it was difficult. Suddenly, Cheryl's fingers appeared over her mound. She expertly moved to her lips and spread them for me. "Have a good look Lover. My pussy is now your pussy."

The opening to her belly was right there. I let one finger touch her. I wanted to slowly put my finger inside. It was a little difficult as my finger was dry. "Lick it baby. Make your finger wet." So I did then I tried again. This time, my finger slid in easily. "Oh baby. That feels so good. Wiggle it around and explore inside of me." That's just what I did.

Cheryl's breathing started to get a little ragged. "Yes baby. Just like that." A few second later, "Baby, kiss my pussy. I need to feel your lips and tongue on me. Kiss me baby." I moved up on the bed so I could put my lips on her. My first kiss was not very well done. I was in a bad position with my arm bent and my finger in her. It was difficult.

I let my tongue slip out. I gently licked her clit. "Oh yes baby. Again." So I did. Her clit became my center of attention. Cheryl had told me to lick and suck it so I did. I wanted to make her cum but I was not sure how to do it.

To get into a better position, I turned my hand palm up and kept my finger inside of her. I pulled my body into a better angle. Cheryl let go of her lips and moved her hand away. I started to cover her pussy with kisses. I kissed everywhere. Those big lips tasted good so I sucked the swollen flesh into my mouth.

I had almost forgotten about the clit so I moved my tongue to it. I put the top of my tongue on the tip of the clit then I pushed my tongue downward. The roughness of my tongue scrapped over the tip. Cheryl let out a moan then, "Oh baby. That's it. Do that."

At that moment, for some reason, I remembered my finger buried inside of her. I moved the tip so I could explore again. I found this soft spongy area right behind her clit. I pushed on it as I moved my tongue. Cheryl let out a scream. "Holy shit baby. Do that again." So I did. I did it fifteen or twenty more times. Each pass over her clit made her scream a little louder and a little longer.

Suddenly, Cheryl started to shake. I could feel her pussy muscles gripping my finger. It felt like she was trying to pull my finger deeper into her belly. Her whole body went tense. My head was trapped in the vice of her legs. I was not sure what was happening so I stopped licking and playing with the spongy area.

A few seconds later, Cheryl relaxed. I pulled my finger out of her. It was followed by a small river of juice. Seeing the liquid move down toward her butt, I decided to save the sheets from getting wet. My tongue came out and I licked her big lips so I could drink up her juices.

Cheryl's reaction was to stiffen again. I was again clamped between those thighs. This time I kept licking around her secret tunnel. The more I licked, the more Cheryl screamed and the more juice I had to lick up.

My head was starting to get a sore from being squeezed so I stopped licking. Eventually, Cheryl started to relax. When she seemed to be completely relaxed again, I gave her one last lick. She jumped and gave a little yelp as I did. I had surprised her with the lick.

I moved from between her legs and worked my way up to the pillows so I was beside her. We turned to face each other. Cheryl had this far off dreamy look in her eyes.

Nothing was said for a while. We just looked at each other. Finally Cheryl said, "Kyle baby. That was incredible. Thank you."

"You don't have to thank me. I just did what you told me to."

"Yes baby you did. But I want to tell you, you are the first man I have been with since Mr. T left. I have wanted this for a along time but I was afraid of approaching you. Maybe some of my reaction tonight has been a build up or desire but Mr. T never kissed my pussy like you did tonight. In fact, no one has ever done that to me before. Even my high school boyfriends never did it to me. So it was both our first times tonight. Did you like kissing my pussy?"

"I loved it. I especially loved to see how you reacted. It made me feel good to know I was making you feel good." Cheryl put both of her hands on my face and then she kissed me.

"You've always been a special boy. Tonight you proved just how special you can be." We just lay there looking at each other.

What was time? Who knew how long we lay there just looking at each other? I touched her breasts after a while. I didn't really have a plan, I just felt like touching them. Cheryl responded by rubbing my chest and playing with the few hairs that had sprouted there. Our kisses were soft and tender. They were a bit playful also.

With her hand on me, I could feel myself getting harder. Slowly Cheryl stroked my rising cock and I played with her breasts. "Are you ready? Can you make love to me?" she asked?

"Yes." I rolled over on top of her. Everything was gentle and easy. There was no hurry in our actions.

Cheryl pulled her knees up to her chest and I had her whole love area open to me. With a few soft strokes of my tip up and down her pussy, I could feel she was ready for me to enter. Her wetness was being spread by my stroking. I was able to find the entrance to her tunnel of love by myself and with one push, I slipped inside.

"Oh lover, this is fantastic." It took several strokes, each going in deeper, before I was completely inside. At first I didn't want to move. I just enjoyed the feeling of her hot body wrapped around me. We kissed and her arms hugged me.

I pushed up on my hands and started a gentle stroking. Each stroke was not urgent but loving. She had her eyes open and I enjoyed looking deep into them.

We kissed and make love for who knows how long. Eventually, my arms were too tired and I flopped down on her. Cheryl tugged me to the side and we rolled over so she was on top of me. I don't know how but we did it but we made the move without me pulling out of her. Sitting up there, Cheryl put her hands on my chest and started to ride up and down on my cock. With each down stroke, I felt her grind her clit on me. The look on her face told me she was enjoying every minute of our love making.

After a while, I could see she was getting tired. I pulled her down to lie on my chest. We kissed and hugged. It was easy to pull out of her. Cheryl looked at me in surprise. I pushed her side to get her to roll off of me. Once freed, I got up on my knees. I used my hands to push her hip to give her the idea I wanted her on her hands and knees. Cheryl quickly moved into position.

I went in easily again. This position was the best in my opinion. Once in her and making love again, the urge to go faster and faster came over me. While we had done this earlier in the evening, this time felt different. I can't explain it. It was just different. I put my hands on her hips and started to drive into her harder. I could feel her wonderful breasts swinging under her as I thrust. I think it made me feel hotter knowing I was making them swing like that.

We both wanted this cum. Cheryl was giving me encouragement. "Harder baby. Let me have it. Cheryl wants her man to give her his love. Fuck me baby."

While all this was new to me and hearing her talk like that was totally strange, it made me want to give it to her harder. I could not stop now. I was pounding her hot pussy for all I was worth and it felt incredible.

My balls let go and I filled her pussy with my cum. Cheryl screamed loudly as I shot into her. The hot cum hitting her insides seemed to always make her explode in orgasm. I was glad to know that fact.

When we were both finished, we laid on the bed again. We were two lovers now and not Mrs. Thompson and Kyle. Somehow it felt great.

Unfortunately, I had to leave and go home to sleep in my bed. It was not easy to leave. The one thing that helped was when Cheryl said to me at the front door, "Thank you for last night and tonight. You've woken up a woman who's been asleep far too long. I want and need your loving."

"I think I'm the one that should be thanking you," I replied. "You are the most beautiful and sexy women any man could hope for."

"Thank you my love. But remember one thing. While I'm yours now, we can't do this all the time. You're young and you need to find girl friends your age. That is a must. Also, you need to be with your friends. You can't ignore them. Just don't tell them who you're making love to. They'll try to find out. Please protect my good name. And who knows, some day I might find a new man and start dating. That would be nice."

"I promise to never tell anyone."

"Thank yo Kyle. From now on, if you want me, just come and take me. You're the best lover I've ever had and I don't want to stop." There was a short pause, then, "Oh yeah! I have a present for you." She turned to the table beside her and picked something up. As she lifted her hand up, she said, "Here." I held out my hand and she dropped a key into it. "That's for you to use whenever you want to have me. Let yourself in and come and make love to me."

With one more long kiss, she then broke it off, swatted me on the butt and said, "Now scoot. Get out of here before I have to call the cops."

We both laughed and I headed home holding my precious key in my hand.

Epilogue

Over the next few years, I did use that key often. Yes my friends wanted to know who I was fucking and they tried hard to find out. I never told. Cheryl was too special to me to do that to her.

There were some great times between us. Like the time mom and dad went away for a week long vacation and left me home alone. Well I wasn't alone for long. Cheryl took a vacation from work and moved in with me for the week. We shared my ¾ size bed. Neither of us wanted to soil mom and dad's bigger bed. We didn't mind though. The bed made us snuggle closer together all night. We spent most of the day time and all of the night naked and enjoying each other.

After I finished school and started working, I did find a girl to date. Things progressed as one would hope and we got married. That was alright as Cheryl found a man to date also. She married him.

I don't really want to admit this, but Cheryl and I kept our relationship going for many years after our marriages started. Sometimes it was months between visits but that only served to make the times together more special.

The last time I was with her was the day before my wife and kids and I moved across the country for my new job. It was a sad time for both of us but we knew it was time.

I think of her often. I know I will never forget her.

I have been very lucky in my life. I have had three women I have loved deeply: my mother; my wife and Cheryl.

Could a guy be any more blessed than that?