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Oliver's Training Begins With Me

Every semester I pick a young man to train in the ways of pleasing an older woman.
“Give me the usual, Tim,” I said. Tim was the bartender at the local college hangout bar.

“Yes, ma’am,” he said. Tim was kind of cute but way too old for me. I estimated him to be in his late twenties. I came to this bar every few months to pick out a college freshmen to be my lover for the semester. I didn’t care for jocks or muscle heads. I preferred the geeky smart types. My name is Cheryl and let’s just say I’m old enough to know how to do everything right. Most men my age try and get me to go to bed with them but they don’t have a chance. Older men are just too damn hard to train.

Tim came back with my vodka martini with two olives and I scanned the crowd of new college students all trying to look cool and fit in. I saw a group of three boys sitting to themselves in the corner. I walked over toward them and then past them to the ladies room. The tight fitting blue jeans I wore gave them a perfect view of my ass. I didn’t have to look to know they were staring at me. Inside the bathroom I reapplied my lip stick and made my way to their table.

“Mind if I join you, boys?”

They all just stared a minute before the cutest one jumped up and pulled out a chair for me. How sweet. I introduced myself and ask them where they were from. Dave told me he was from here and going to study biology. Boring. Mike was from Detroit and wanted to be a history teacher. I was starting to think I had picked the wrong table. Finally, Oliver, the cute one, was from London and was studying literature. That was more like it. Oliver had just turned eighteen and this was his first time out of England. He only knew these two because they were all dorm mates.

After an hour of talking with the three of them I knew Oliver would be the one I offered my services to for the next year. He was a lot smaller than the other two and wore the cutest pair of glasses. I told them it was time for me to get going and asked Oliver if he would see me home. He looked very surprised but agreed happily.

My house was only six blocks away and it was a beautiful August night. Not too hot with the wind blowing in from off the river. I put my arm in his and we talked on the way home. He told me about his parents and that he was an only child.

“Do you have a girlfriend?”

“No,” he said shyly, “I’ve never had a girlfriend.”

When we got to my house I unlocked the door and asked him to come in. He readily agreed and followed me into the living room. I told him to make himself comfortable on the couch and I would bring us some drinks. A few minutes later I returned with two vodka martinis and handed one to him. He was sitting upright on the couch and I sat right next to him.

“Have you ever been with a girl, Oliver?”

He blushed and shook his head no. I leaned over and kissed him on the lips. He froze before kissing me back. I told him I had chosen him to be my lover for the semester and he wanted to know why him.

“Because, Oliver, you need the most help. If you agree to be my lover you will become a great lover. I will teach you the proper way to be with a woman. Not just in bed but in life,” I placed my hand on his leg and kissed him again. “What do you say, Oliver?”

He was so sweet he only nodded his head. We continued to kiss and I moved my hand closer to his zipper. He only sat there and tried not to move too much. I took his hand and placed it on my left breast. He gave it a little squeeze.

“I have a surprise for you,” I told him. “Tonight you will get to have sex with me without worrying about my needs. Tonight is all about you.”

I took him upstairs to my bedroom and turned to face him once inside. I told him to sit on the bed, which he did without question. I knew he would be easy to train. I stepped back about three feet and slowly started to undress for him. I pulled my shirt over my head and tossed it on the floor. My sheer lace bra made his mouth drop open slightly. Next I unbuttoned my jeans and pulled the zipper down. I shifted my hips from one side to the other in order to slide my tight jeans past them. My panties matched my bra and Oliver stared with lust in his eyes.

“Stand up, Oliver,” I said and again he obeyed without question. I pulled his polo shirt over his head and kissed his chest. He was built very nicely for a geek. While I unbuttoned his pants I told him to remove his shoes, which he did, and I pulled his pants and boxers down together. I was pleasantly surprised by the size of his cock. It appeared to be over seven inches. His hair was too thick and we would have to correct that tomorrow.

“Sit back down.” Once he was seated I got on my knees and leaned over and kissed the tip of his hard cock. He moaned a little and I opened my mouth and put just the tip in. I ran my tongue over and under the head and he laid still like he was afraid I would stop at any moment. I took his hands and put them on the back of my head so he could run his fingers through my auburn hair.

I took his cock all the way into my mouth now. I applied the right amount of pressure and started to work my tongue all around his shaft. Soon I was bobbing my head on his cock and from the sounds he was making I knew it wouldn’t be long.

“Cheryl…I can’t hold it…any longer.”

Those words only inspired me to keep going. I picked up the pace and cupped his balls in my hands. He was trying so hard not to cum and I wanted to tell him to let it go, that this was what I wanted, but I couldn’t tell him that with his cock in my mouth. Instead I doubled my efforts and he couldn’t hold out any longer. His body jerked and he flooded my mouth with his virgin semen. I loved the taste of young boy cream. I swallowed every drop and kept sucking until he gave me every last drop he had.

He remained on the bed, breathing heavily, while I continued to kiss his cock. I worked my way up to his stomach, chest, and finally neck. We started kissing, at first I think he was afraid to kiss me because he had just come in my mouth, but when he realized I hadn’t missed a drop the kissing became more passionate.

“Take off my bra,” I said, no need to wait to start all his training. He reached around with both hands and fumbled with the straps. I told him to be calm and to take his time. Then I explained the mechanics of how a bra works. This helped him some and soon he had the clasp undone. He slowly pulled the bra away from my breasts and stared. I took the bra away from him and tossed it onto the floor. He was still staring when I got him behind the head and pulled him to my nipple.

Instinct took over and he sucked my nipple into his mouth. Ordinarily I would had him to work around the nipple before sucking on it but it was his first time and I didn’t want to give him too many instructions all at once. He caressed my other breast while he sucked on the other one. Then, like a natural, he switched. He was already showing signs of potential. I looked down and his cock was hard again. I love how eighteen year old boys can get hard so fast after cumming.

I reached down and lowered my panties to where they were only hanging on my right ankle. Then I rolled over onto my back pulling Oliver over on top of me. I spread my legs for him but he wasn’t quite sure what to do so I reached down and took a hold of his cock and placed it at the entrance of my pussy. I was so wet already.

“Push,” I told him. His hips moved forward and he slid easily into me.

“Oh god,” he whispered as he bottomed out.

“Does that feel good?” I asked. He couldn’t respond with words so he just nodded his head. I told him to take his time and when he was ready to pull out a little and push back in. Again he nodded and slowly, but surely, he began to thrust in and out of me. His cock felt amazing in me and I wrapped my legs around his back. If I hadn’t already sucked him off I’m sure he would have come already.

However, it still wasn’t long before he started breathing heavy and picking up his pace. I told him how good he was doing and when he was ready to cum to put it in all the way and just release it. He kept going for a few more strokes and then he tensed up, drove himself all the way in me, and came as hard as he ever had.

He stayed on top of me and caught his breath while I kissed his neck and chest. The look in his eye was of total gratitude. He rolled off of me but kept his arms around me. He liked to snuggle and I liked that in a man. We continued to lie there for another hour, until I told him I needed to get my rest. I worked for a law firm in the city and had to be in early. He looked saddened but I told him to be at my place at five tomorrow and that cheered him up. I also told him to bring me a copy of his school schedule and to have all his pubic hair removed by tomorrow. Tomorrow I would start to train him on how to take care of a woman’s needs.

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