Chuck

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Taking on the virgin and learning something myself.
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My name is Marjerie. I'm thirty-nine years old. I was married to George when I was only twenty. He left when I was just twenty-three and Charles was only two. I got an uncontested divorce three years after he disappeared. Charles is the only thing George gave me and the best thing I've ever received.

Charles is now eighteen and just graduated from high school. I have a great job and I've managed to give him everything I could and everything he wanted, except one thing. Charles is going off to university this coming August and he's still a virgin.

A week ago, I was having lunch with Mary. Mary is my best friend from high school and has supported me emotionally, and in other ways, through every crisis in my life. During lunch, I shared my anxiety over Charles' impending departure for school. I shared my concern about the separation and the void I would feel when he left. I also explained my worry about his inexperience and sending him to an environment where he might be embarrassed or worse.

Mary listened to my concern but shared that she thought I was over stressing about Charles' lack of sexual experience. She had gone to college and she was sure that he wouldn't be the only freshman virgin. She tried to explain that, in a coeducational dorm, no one was a virgin by the time they became sophomores.

I thought she might be right but I was still concerned about how difficult his first sexual experience might be. I remembered my first time and how terrified I was. I wanted Charles to have only positive experiences, especially with sex, and I wanted him to leave for school with skill and confidence.

"I really want someone to love him and teach him the right moves. You know, the things a woman likes and those she doesn't," I said.

"That's a noble goal," offered Mary. "However, you're messing with something we've all experienced and we've all done nicely afterward."

"Not all of us. My experience left emotional scars I still carry and I want Charles to have wonderful memories."

Mary considered for a moment and said, "I think I get it. Do you have someone in mind?"

"That's the problem. I don't know any of his friends. He doesn't have a girl friend. He only goes out alone. I think he meets others somewhere but I don't know where and I don't ask him. I prefer to respect his privacy."

"There is one option," said Mary.

"I think I know where you're going and I've already rejected paying someone," I responded. "A professional would be too much too soon and not really be emotionally involved in Charles' experience."

"So what's your plan?"

"I was hoping you would help."

"Whoa. You want me to have sex with your son?"

"You've known Charles from the day he was born. You love him almost as much as I do. You'd be perfect to teach him the things I can't."

"I'm a married woman with a husband and children of my own. How on earth could that work without destroying my life?"

"No one would ever know. You can use my house. I'll go out and leave you alone with him. You don't have to tell me anything about what happens and I'll never ask. Only you and Charles would know and he'll never tell. You and I have been together many times and no one has ever asked a single question about what we 'girls' do. Please think about it."

"I guess that would work," a thoughtful Mary hinted.

"Then you'll do it?" I said hopefully.

"I'll meet him once. Just once. No promises. I'll never speak about it and you can never ask."

"Deal," I agreed.

We planned I would leave Charles home alone while I went away the next weekend. Mary would arrange to go with me, but stay nearby instead.

I picked Mary up early Saturday morning for a supposed weekend long shopping trip to the city. I rented a car for her to use, and no one would recognize, while I drove alone to the city.

* * * * *

"I don't know what I was thinking," thought Mary as she drove to Marjorie's house.

I parked in the empty driveway and looked around. No one was on the street and I saw no one looking in my direction. I couldn't be sure some busybody wasn't watching from behind some window curtains but I had to walk to the door sometime. I stepped out of the car and locked it remotely as I walked to the side door of the house. I knocked gently and then harder when no one came to the door.

Charles opened the door and seemed surprised it was me. "Aunt Mary, I thought you went with mom to the city for the weekend. What are doing here?"

"Can I come in and I'll explain."

Once inside, I tried to explain without giving away my real purpose and, I suppose, maybe avoiding keeping my promise to Marjorie. "Your mom is anxious about your impending move to college. She's trying to get her head around being alone in the house after eighteen years sharing it with you. She's also wondering how you'll adjust to living in a dorm with all the temptations that entails. She respects your privacy and doesn't think you'd be comfortable talking about it with her. She arranged for you to be alone this weekend and for me to come by to see it you'd be willing to discuss it with me."

"That sounds like mom. She's always on edge around me. I just wish she'd just get it out so we could talk. However, I think there's more to it. What, specifically, is she concerned about?"

"Shit," I thought. "This isn't going to be as easy as I hoped."

"Well, your mom thinks that college is a sexual swamp and you, as a virgin, will get swept up and embarrassed without the proper experiences and expectations." "There, I said it," I thought.

"Whoa. My mom thinks I'm a virgin?"

"She told me she has no evidence to the contrary. She said you don't have a girl friend, don't date and usually go out alone. That led her to an assumption about your virginity. Are you telling me you're not a virgin?"

"Come with me, sit down and I'll fill you in, with the commitment you'll never repeat anything I tell you to anyone, especially my mother."

We sat on a half sofa in the den. Charles continued, "I'm not a virgin. Haven't been since sophomore year. I don't have a girl friend since I don't need one. I leave the house alone but I don't spend the evening alone. I usually have more than one girl asking to 'date' me at any time. I don't bring anyone home since it would probably upset mom. I can see, as an afterthought, how she could reach that conclusion but I assure you, that's not the case. And everyone calls me 'Chuck' not Charles. Only mom calls me Charles."

I sat there, amused and silently thinking about the conversation I needed to have with Marjorie. Chuck continued, "However, I think you're here for more than just an explanation. I think mom sent you here to 'educate' me about sex. Am I right?"

"Damn, he's intuitive," I thought. "This is leading somewhere and I'm not sure I don't want to explore it further."

"Your mother wanted you to learn the basics from someone with experience. I see now that's not necessary. I get the feeling you may have more experience than I do."

"That doesn't mean I can't learn something from you."

"Hold on. I agreed to help your mother because she was deeply afflicted. The situation has changed. You could probably teach me something."

"OK," Chuck agreed.

"Wait. That came out wrong. I'm a married woman with a husband and children, one of which is almost your age and I'm over twice your age."

"Yet you agreed to help my mom with my 'problem'."

"I did, but ...," I stammered.

"Let me show you. You can tell me when you have enough information to convince my mom not to worry about me."

Chuck leaned forward, took my face in his hands and kissed me chastely on the lips. He leaned back. "I've wanted to do that since I was in diapers."

I didn't know how to process that. This young man had a crush on me for almost two decades.

He leaned in again. "Remember; let me know when you have enough information." He kissed me again, more aggressively, and I returned the kiss. With the next kiss, he opened his lips slightly and touched my lips with his tongue. My eyes closed and my mouth opened to welcome him. The kiss seemed to last forever. Our tongues danced with each other and penetrated deeply into each other's mouths.

He leaned back and I, reluctantly, did the same. He reached out and unbuttoned the top button of my blouse.

"What are you doing?" I asked.

"What you want me to do," he replied as he unbuttoned the next button.

I didn't know what I wanted but I didn't stop him as he finished unbuttoning the rest of my blouse, pulled it from the waistband of my skirt and pulled it off my shoulders and down my arms. He discarded on the end of the sofa.

He leaned back and seemed to be studying me in my simple bra. "That's it?" I asked.

"No, but rushing spoils the mood. I want to treasure you every step of the way and I want you to feel admired, wanted and very sexy."

"Marjorie thinks this kid has a sex problem," I thought. "She couldn't be more mistaken. I'm beginning to understand why he has so many girls asking him for a date."

Chuck leaned in again and ran his hands down my bare arms and then down the sides of my torso. His touch was soft as silk and my skin, and other parts of my body, began to tingle. With his hands on my waist, he kissed me again, tasting my lips and teeth. When he leaned back, he whispered, "Unhook your bra."

I looked into his eyes and did what he asked. His eyes never left mine as my bra fell into my lap. He leaned in and kissed me again without ever looking down. I was moved by the feeling he wanted to know who I was, not what I was. The kiss lasted forever and he never took his hands from my waist. His kiss moved to my neck and then to my ear, where he kissed and nibbled on the lobe. I threw my head back on the sofa and soaked up the feeling with my eyes closed.

Chuck kissed down my neck, across my shoulder and onto the top of my chest. I never opened my eyes and his hands never left my waist, as he kissed down to and around my breasts. He kissed the top of each breast and then gently licked each nipple. My nipples were up and harder than I could ever remember, almost to the point of pain, as he took each into his mouth and dragged his teeth across them.

He sat up and took my hands in his. "Your turn," he said.

I sat up and looked at him. He sensed my question and pointed to the buttons of his shirt. I unbuttoned each button as slowly as I could while keeping my eyes locked on his. It took real restraint not to just tear his shirt off. When I finished, he held out each arm and I pulled his shirt off and tossed it aside with mine.

I looked down and leaned it to kiss and nibble his nipples. I heard him sigh quietly and, when I looked up, his eyes were closed. I knew I was lost and would never have enough information.

I kissed down his chest until I neared his waist. I reached in and unbuckled his belt, unbuttoned his jeans and pulled the zipper down. Chuck leaned back, lifted his hips and helped me slide his jeans and boxers down his thighs.

His penis was half-erect and the largest thing I'd ever seen, even in xxx-rated movies. I absolutely understood why he had so many girls asking him for a date.

I took his cock in both hands and kissed the head. I had both hands around the shaft, one above the other and there was still several inches left. Neither hand could close around the shaft. I moved my mouth down around the top of his erection. I almost couldn't fit even the head into my mouth and I couldn't touch my lips to my fingers. I could deep throat my husband but trying the same with this monster would suffocate me.

I moved my mouth up and down as best I could while stroking his shaft with one hand and fondling his balls with the other. All the while, I knew I wanted to feel his cock inside me and wondering, at the same time, whether it was even possible.

A few minutes later, Chuck lifted my head off his erection. "Not yet," he whispered.

He sat up on the sofa and stood me up in front of him while he kicked off his pants. He looked into my eyes again as he unbuttoned and unzipped my skirt. I let it slide down my legs and kicked it aside. He looked at me and nodded. I grabbed the waist of my panties on the sides and pushed them down and off my legs. As I bent forward, Chuck held his hands under my breasts and caught each one in his hands. His touch was gentle as he weighed my breasts and I held my position until he lowered his hands.

I stood in front of him, naked and expectant. He looked into my eyes as he ran the fingers of his right hand through my pubic hair to the top of my vulva. I closed my eyes and spread my legs apart to allow him access. He moved his fingers to circle my clitoris and down to my Skene's gland. He gently stimulated both until I began to quiver and needed to sit down.

I sat on the sofa and moved back as Chuck began to kiss and nibble my clitoris. He used his lips and tongue with the exact pressure necessary to maximize my pleasure. As I shifted and wiggled under his attention, he slid two fingers of one hand into my vagina. The internal pressure against the external pressure brought me to climax. I almost fainted with the strength of the orgasm and I flooded his hand, and sofa, with fluid. I had never done that before with anyone and the experience was both exhilarating and embarrassing.

Chuck didn't recoil. He moved his body up mine as he smiled, licked his fingers and fixed his eyes on mine. He began to rub the tip of his erection against my labia, slowly opening my vagina. He rubbed and gently pushed. With each push, my vagina opened a little more and his erection moved further into me.

I was constantly seeping fluid as I felt the head of his cock slip past the entrance of my vagina. It felt wonderful as he moved further into me a little at a time. I guess he was about half way buried when I felt him bottom out in me. I was full beyond anything I'd ever known. I couldn't believe he was actually inside me and I didn't feel pain, only pleasure. His movements were measured as he moved slowly inside me. I knew he didn't want to hurt me and was being extra careful. I loved it and knew I was going to have another orgasm within seconds.

The orgasm left me breathless. Chuck slowly moved completely out of me. His erection was raging. He had me sit up and moved to the center of the room and lay on his back on the floor. He had me sit astride him. I understood what he wanted and I moved my vagina over his cock and pushed down until he entered me again.

I this position, I had control of the depth of his penetration. I moved carefully up and down. With each stroke, I was able to take him more deeply inside me. Two or three minutes later, I moved down and felt his pubic hair on my skin. Chuck's monster cock was completely inside me. I couldn't believe I had swallowed the whole thing. There was no pain, just an enormous pressure and a sense of satisfaction.

I moved up and down slowly and then more quickly as I adjusted to his size and gained confidence with how much movement felt best. Soon I was moving aggressively and nearing another orgasm. I could feel Chuck on the edge as well. I went over the edge, squirting fluid over his abdomen. As my vaginal muscles clamped down on him, he erupted, pumping gallons of semen into me over and over. I felt his ejaculate deep inside my abdomen, higher and deeper than I thought possible.

I collapsed on top of him. I could feel him softening inside me. He didn't fall out of me until I sat up and lifted my body off his and sat on the floor next to him. "Did I pass the course?" he asked.

"You aced the final exam," I responded.

"You can tell my mom to rest easy."

"No. I won't tell her anything and she agreed not to ask. I'll just tell her not to worry. I think she'll make whatever assumption makes her most comfortable and let it drop."

"Thanks. Now we need to clean up and get ready."

"Get ready? For what?"

"Jenene is going to be here around four o'clock," he said.

"I assume Jenene is one of your non-girl friends. I'd better get dressed and leave."

"You assume correctly. Get dressed, but please stay. Jenene would love to learn something and so would Sissy."

"Jenene and Sissy. Two girls are coming over?"

"Yep."

"How long are they going to be here?"

"They're going to spend the night. With mom out of town, I thought it would be fun to entertain. They told their parents they were going to the mountains with friends and would be home Sunday afternoon."

"I'd better go."

"Where would you go? You can't go home. Everyone thinks you're with my mother in the city. Just stay here with us. I think you'll love it."

I got up and took my clothing into the bathroom to clean up and get dressed. When I returned twenty minutes later, Chuck was dressed and he had cleaned and straightened up the room. He looked like he had cleaned up himself as well. I smelled shampoo. He had taken a quick shower while I was in the bathroom and had changed into a pair of cargo shorts and a t-shirt.

I sat in a side chair while Chuck was busy in the kitchen. I couldn't help thinking.

"What am I doing here? I made a commitment to Marjorie. That commitment is already fulfilled. Wow, is that commitment already fulfilled. I could leave now and everything would be okay. I'd never say anything to anyone and neither would Chuck. At least I think he'd never say anything to anyone. I can't be sure. I'm risking everything by staying. I should leave now but can I be certain Chuck won't brag, or worse, to his friends. Maybe everything is already beyond saving.

"What am I doing here? I'm a married woman, with a loving husband and loving children. I'm a conservative woman who goes to church most Sunday's and I support worthwhile charities. I'm risking everything by staying. I should leave now. But maybe it's already too late. Maybe my life is already changed forever.

"What am I doing here? I have a conscience and this is wrong. I have a reputation, a good solid citizen reputation. I'm a respectable person. Staying here offends my moral sense. Staying here could ruin me and make me a pariah forever. I should leave now. I should have left long ago. But I've already done things that offend my personal ethic and integrity.

"What am I doing here? Do I just want more of that enormous cock? Am I really that base, that depraved? Does feeling that good, that full, justify staying? Does having the best orgasms of my life, with the promise of more, keep me here? I should leave, NOW! I'm just procrastinating until the decision is taken away and I can tell myself I was trapped, unable to leave."

The doorbell rang.

I was stuck. I would probably have to stay. Probably what I wanted anyway.

Chuck left the kitchen and went to the door. When he opened the door, two young, and beautiful, teenage girls came into the living room. When they saw me, one of them said, "Oh. I'm sorry. We didn't know you had company. We'll come back later."

"No. Stay. Mary is a family friend and I asked her to stay to meet you," said Chuck as he led the girls over to the chair I sat in.

I stood up to greet the girls. "Jenene, this is Mary. Mary, Jenene," Chuck said by way of introduction. Jenene was about my height with short, blonde hair. "And this is Sissy," said Chuck. "Sissy, Mary," he continued. Sissy was slightly shorter with auburn hair reaching to just above her collar.

While I was shaking hands with the girls, I was thinking, "What do they feed young people these days. These girls have slender, almost athletic bodies and the largest boobs I've ever seen. Both of them."

I sat back down as Chuck led the girls to the half sofa, the scene of so much activity barely an hour earlier. He sat between them, creating a nice tight threesome. Meanwhile, I'm still thinking,"I bet Chuck prefers breasty women and selected these two for their attributes. I'm sitting in a room with three young bodies with the largest cock and four of the largest tits I'd ever seen. I feel like a five-year-old going to Disney World for the first time. Maybe this is why I stayed."

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