We were having a nice quiet dinner at the I-don’t-care. It was a Sunday. We had just retired from being on the boat for the weekend. We went to the block with some friends. The weather was perfect.
We were in the middle of dessert when Chuck suddenly got silent. I could tell something was bothering him.
“OK, big boy. What’s eating you? You were yourself up until a few minutes ago. So what suddenly became so important?”
“Well, I’ve had something on my mind for the last few days. First off, I’m not sure if I am out of line by asking, and secondly, I’m not sure how you would take it.”
“I’ll take them one at a time. You can ask me anything you want. You should know that by now. And if you don’t ask, you’ll never know how I take it. So I suggest that you ask and we’ll figure out the rest as we go.”
He sat there in silence and I wondered what could be so bad that he wouldn’t even ask me. Whatever it was, it was bugging him. If he didn’t tell me, I’d have to drag it out of him.
“Alright. I’m going to ask. Before I do, please give me anything sharp within arms distance.”
I had to laugh at that one. This must be good. He’s never been afraid to ask me anything or to tell me to do anything.
“I want you to teach one of my customers how to fuck.”
Then it was my turn to keep quiet. I’m not quite sure what I heard.
“Excuse me? Did I hear you right? You want me to teach one of your customers how to fuck? How old is your customer, ten.”
“Haha. No, he’s in his late twenties. He represents the biggest corporation we do business with. To me, he’s worth millions. That boat we were on this weekend is a direct result of his business.”
Now he had my attention. We had a pretty good lifestyle. I certainly couldn’t ask for anything more. If I need anything, I just ask Chuck. He’s never refused to buy me anything.
“Alright then. Please tell me more?”
“Well, it seems that every time I see him and we start talking, he turns the conversation around to his sex life. I don’t know why he thinks I can answer all his questions, but he confides in me. I think I know more about his personal sex life than he does.”
“So he’s an adult male with a bad sex life. Let me guess. You want me to take him to bed and show him hands on all the ways to pleasure a woman.”
“Bingo! You are good. That’s exactly what I want.”
I was going to ask him again if I heard right, but I’m not sure I wanted to hear the answer anyway.
“You have to be kidding me. You would let me teach sex to another man? What’s the catch.”
“No catch. You teach him whatever you think he needs to know. Take as much time as you need, and be with him whenever he needs you.”
Holy crap! I didn’t think I heard him right, but just in case I did, I went over the plus’s and the minus’s in my head. I couldn’t come up with too many minus’s. One big one did come right out and hit me.
“What about our agreement? What you’re saying is, there would be times where I would be alone with him. Right?”
“Yes, I don’t see any other way of doing it. I trust you to do the right thing.”
The right thing? Trust me? he’s asking an awful lot of me. there has to be a catch somewhere. This sounds too easy.
“Alright, before I say anything more, I need some time to think about this.”
“Well, ok, but please don’t take long. There’s a big contract coming up soon and my competition is bugging him. You can seal the deal on a multi-million dollar agreement.
“Oh, sure! Nothing like a little pressure. Ok, I would want to do this anyway so, I want to meet Mr. no sex. And I’ll tell you right now that if I don’t feel right with him, then it’s off.”
He pulled out his cell and quickly dialed a number. It didn’t take long before…. “
“Don, Chuck. Yeah, listen, I think I have a solution to your problem with women. What? Yeah, right. Can you meet us about this time tomorrow? Yes. Where? That’s fine. See you tomorrow.”
I didn’t expect things to move so quickly. I wasn’t sure what to say, but I wanted Chuck to know where I stood.
“That was fast. I want to make sure that we’re on the same page. I have the last say as to if this is going to happen, right?”
“Yes, it’s my idea, but it’s your call. I will respect your decision no matter what it is.”
“Good. Now take me home and let’s fuck. If I had panties on, they would be soaked now. Let me have your napkin… please?”
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We talked about it the next day and we agreed. Chuck was going to try for a threesome for the first time. Based on what happens, then I would either stop it or at least set the ground rules.
I was walking around on pins and needles all day. So many things were running through my mind.
“How do you want me to dress?”
“Ah, how about somewhere between sexy and slutty. Is that possible?”
I thought, possible? Yeah… Probable, “We’ll see, honey!”
I must have tried on everything I had in my closet. I narrowed it down to five outfits. I had Chuck sit in his recliner so I could show him the five and let him pick the winner.
It’s a good thing there wasn’t more.
“Ah, hun? I like number two. The one with the white sleeveless blouse and the black skirt.”
“Oh, ok. I’ll wear that one.”
“Good, now get your cute ass in the bedroom and take care of this fucking hardon that won’t go away.”
It was a good thing that we had an extra two hours to spare. My God, was he ever horny. I wonder what brought that on. Hehe.”
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The place was packed. Summer on the ocean is still the hottest place to vacation. When we told the cute girl who we were, she smiled and looked at me funny before leading us to a table… in a private room… lit by candlelight…with light jazz playing in the background.
I didn’t know who this guy was or what he looked like, but he had class. That was for sure. And also fashionably late.
“Did you know about all this?”
“No, but I do know that he can afford it. Where was this room all these years that we’ve been coming here.”
There was a knock on the door and when Chuck said, come in, a girl that looked like she was sixteen came in.
“My name is Mary. Can I get you a drink?”
I told hubby to reel his tongue in and tell the young lady what we would like. I knew that I would like her naked and spread across the table for an appetizer.
“Yeah, sure hun. A glass of white wine and a Bud… please.”
He needs a little training folks. She wasn’t gone for more than a minute when another knock. This time, it was Don.
I thought I was going to faint dead away. I never in my life expected someone like this to walk in that room. I’ll sum him up in the three words we know so well.
Tall? He had to be six foot six, at least. Handsome? Built like a brick shithouse and in a white tux. His face looked like it was chiseled out of solid granite.
I changed the words around for effect… Dark? The gorgeous man before me was not just dark but black. Never in my life have I seen a black man so handsome. Tall, yes, but this handsome, never.
Intro’s all around and we sat down. A knock and it was the girl with a bottle of champagne.
“I took the liberty of changing your drink order. I hope you don’t mind, Terry?”
Mind to mouth… MOVE!! “Ah, no Don, that’s fine.”
Small talk during the appetizer. Then I asked him what led him to need a woman to teach him about sex.
“I’ll simplify it for you. I was raised in a very wealthy family as an only child, also under the rules of the Catholic church. Sex wasn’t talked about in our house, although I heard it enough from my room at night.
Private all-male schools kept me studying. Now all during this, they were telling me that I’m the ugly duckling of the family. That I should devote all my time to the company. I did and I grew the company to what it is today.
Now I have the time to do things I missed growing up. That included sex. I hope that answers your question, Terry.
Let me say that I expected my husband to take the lead, but he didn’t. I was not sure if he planned it, but I was more than willing to take it.
“You explained it perfectly, Don. Has Chuck told you anything about what I would want for this to happen?”
“A little, but let me say this, Terry. After seeing and talking to you, I will do whatever I have to, to make this happen. I feel very comfortable with you.”
Holy, holy. I would have stripped and bent over the table right then for this man.
I told him that we would have set times to get together. This was due to Chuck’s having to work. He came back with.
“I know you want your husband to be near you when we are together, so I have taken the liberty to have Chuck placed on indefinite leave with full pay. I hope you don’t mind, Chuck. Just call it an extended vacation.
“How the fuck did you manage that, Don? Will I still have my job after this is over?”
“My friend, I’ve had my people looking into your company. If my accountants come back with the figures I think they will; you’ll be working for me anyway.”
“You mean you’re buying the company?”
“It makes perfect business sense. We are your largest customer and your company has limited capital. My people tell me that we constantly have to wait for your service, so if we owned the company with you at the helm, problem solved.
“Wait, wait. Me at the helm? Can you explain please?”
“Of course. When my purchasing manager told me about this rep that wouldn’t take no for an answer, and if we had a problem, they would call you and I would get taken care of right away; I told them I had to meet you. After talking to you a few times, I knew that you would be the man to run the company.”
I just had to butt in, “Don, if I may. How did I get in the picture?”
“I think that I’m pretty good at judging people, and I trusted Chuck. I trusted his word in business, so I knew I could trust him with my personal problems. I must tell you the truth. I was ready to say forget it when he told me that the girl he had in mind was his wife, but when I saw you, I changed my mind.”
I had to excuse myself to go to the lady’s room.. and wring my panties out. I thought that Chuck better be able to get it up more than once when we get home.
We ended that I would think about everything and make my decision tomorrow. Don was also going to think about Chuck being in the same room and even joining, but only if I said it was alright. Everything would happen at our house. I would feel more comfortable there.
We finished and we left at the same time. As I was walking out of the room, Don asked us,
Would it be alright if I kissed you, Terry?
“Of course Don.”
He walked over to me and leaning down, put his hands on my waist and lifted me right off the floor so we were eye to eye. He pulled me to him and kissed me. What a kiss. I don’t think that either one of us wanted to stop. Being the complete gentleman he was, I had to have my tongue introduce itself to his. That didn’t help matters and I put both my arms around his neck and pulled him to me so our bodies met.
I think we both wanted to continue, but I knew that Chuck was right behind me. I wasn’t sure how he was taking it, so Don put me down and we went out to get our cars.
Our car was brought around right behind his stretch white limo. Before we got into our car, they shook hands and Don said something to Chuck that I didn’t hear.
We were on our way home and we were both quiet.
“Well, what do you think about Don?”
“You didn’t tell me that he was black?”’
“You never asked. Would it have changed your mind?”
“I haven’t made up my mind yet.”
Actually, I did make up my mind. This was my fantasy come true, and I wasn’t about to let it pass me by, but I was also being torn up inside.
“What did he say to you when you shook hands?”
“He thanked me… then he told me that he was looking forward to your lessons.”
“Take me home and make love to me, please.”
And that’s what we did. We didn’t fuck; there was the passion of two people that loved each other. His cock felt different than when we just fuck.
I can’t tell you how many times I came, and when we were finished, he fell asleep with a smile on his face that told me that he loved me. Then I turned over and cried myself to sleep.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
The next morning I woke to the smell of fresh coffee. The smell got stronger until it appeared at the bedroom door. The coffee was being delivered by a naked man with a hardon.
“Is that for me, or are you going to piss it away.”
“I got rid of that one an hour ago. This one’s for you, that is if you want it.”
“Come over here and let me have the coffee, please.”
He walked over and stood by my head while I took a sip of the coffee. Then I grabbed his cock, pulled him to me and in my mouth.
“Oh, shit! Your mouth is hot! Fuck! No!! don’t do that, I’ll cum.”
I stopped and took another drink of the coffee, letting it stay in my mouth before swallowing. Then took him in again.
“Shit! It’s even hotter. Oh, crap, crap!”
And he came… and came. I held him in and felt the contractions as he pulsed in my mouth. When he finished, I took him out and opened my mouth, showed him what he gave me, took a drink of the coffee, and swallowed everything.
“Holy shit. Where did you learn to do that!”
“Some things are better left unknown.”
He dropped it and went out of the room. I took my time drinking my coffee and thinking about last night. The more I thought, the more I knew what I was going to do.
I put on a black teddy and went downstairs. Chuck was outside on the deck having his coffee and I sat down beside him.
“Wow! You look good in that.”
“Thanks. So… who’s supposed to talk first about last night and this new venture.”
“Well, let me tell you that Don called me already this morning and he’s coming over tonight.”
“And I guess he expects an answer from me?”
“I think so. But let me say this. He’s been lining up all the stars in our favor. He upped it this morning.”
I sat up straight and said, “What? What did he tell you?
“Remember that he said I’d be running the company after he purchased it? Now he’s saying that if everything works out as he expects it to, I will own the company.”
“You have got to be shitting me! Do you know what this is doing to me? I have never made such a tough decision in my life.”
“I know, believe me, I know. I’m very close to telling him to forget about the whole thing. This is putting way too much pressure on you. You don’t need or deserve this.”
“You know I love you. I love you more than anything. up until you told me this new revelation, I was going to say yes, I would do it. Oh, crap, just give me a few minutes.”
I got up and took my coffee. I started to walk around the pool and think about what I was getting myself into. My thoughts were always interrupted by a picture in my mind of Don holding me in his two strong arms and kissing me.
The thought of me teaching this man, this black man, about sex was overwhelming.
I continued to walk around the pool. I have no idea how long I did that or how many laps I made, but then I headed back over to Chuck.
“I’ll do it. There, I’ve said it. If I change my mind, tell me I don’t mean it. Make me do it. Right now it’s what I want.”
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
I just finished getting dressed when I heard the doorbell rang. I heard Chuck answer, and Don’s deep voice. Only knowing him a couple of hours, and one kiss, but that voice turned me on. I walked downstairs.
I saw him and smiled. He was dressed casually. Slacks and a button-down shirt. I was glad that I didn’t dress sexy for him. I wanted him to see both sides of me.
“I’m so glad you could make it Don. Let’s go out on the deck.”
We went out and sat next to the pool while Chuck went and got us drinks. while Chuck was gone, I got up quickly, went over to him, and gave him a kiss like last night.
“What was that for?”
“Because I liked the one we had last night.”
He didn’t say anything, and Chuck broke the silence when he returned with our drinks. We all seemed a little on edge, so I figured there’s nothing like getting right to the point.
“Don, I’ll teach you everything you need to know about sex and women. I can’t guarantee that you’ll get a reputation with the women, but I will guarantee that you will know everything you need to know. And you’ll have fun learning.”
“Well, then. I would like to purpose a toast? To my new learning job.”
I interrupted him, “No, it’s not a job. Call it anything but a job. I want it to be fun, not a job.”
Don stopped and looked right at me. He was still holding his glass up when he said.
“Yes, Yes, Terry’s right. To a new fun venture.”
We clicked glasses and drank. For the next hour or so, we talked and the conversation started to gravitate to the men and work. I had to do something. It was around ten o’clock.
“Alright, gentlemen. Don? Please come with me to our bedroom, and Chuck, I’m sure you can find something to do.”
This caught them by surprise. They didn’t know what to say.
I got up and took Don’s hand. I led him up the stairs and into our bedroom. I closed the door and made sure I locked it loud enough for Chuck to hear.
“Please, sit on the bed and make yourself comfortable.”
When he started to take his shirt off, I said. “No Don. I’m just going to ask you a few questions. They will let me know how I’m going to proceed. Just like a lesson plan.”
“Oh, and I thought….”
We both laughed, and I hoped it was loud enough for Chuck to hear.
After I got a pad and pencil, I sat right next to him on the bed. I could feel myself starting to moisten. I had on shorts and a tank-top. I did wear a bra. I didn’t know how he would react if I didn’t wear it.
I started asking questions about everything sexual. I needed to know where his higher head was before I could engage his lower head.
What did he think about oral sex, anal sex, giving, and receiving? Foreplay, nudity in general.
It was obvious that he read a lot on the subject, but that was doing me no good.
“Listen, Don. You sure do know a lot about sex, but it’s all technical. I want to know what you think about it. Let’s start at the beginning. Have you ever felt a woman’s breasts? Have you ever seen a naked woman up close? Do you masturbate? I need to know to teach you one subject at a time.”
“I didn’t think it would be so complicated.”
We started to get on a good rhythm and three hours seemed like one. I felt that it was time to wrap it up.
“Before we call it a night, there’s one thing I want to do.”
“Of course. What would you like.?”
“Kiss me again like last night. Only this time, I want you to kiss me like you would your lover.”
He didn’t answer me, but stood up from the bed, took my hand, and helped me to my feet. He was going to pick me up like last night, but I told him no, so he put his big arms around me in a bear hug. Our lips met, and we kissed and kissed, and I reached down to feel his cock through his pants. What I felt made me cream my panties. I knew there would be a wet stain on my shorts.
We broke the kiss and I just smiled at him. He was packing, and I was so horny that I wanted to whip that thing out and suck him off, but I had to restrain myself. After all, I am his teacher. I didn’t want to come off like a slut.
We went downstairs, and Chuck was sitting out next to the pool. I knew he thought that something physical happened, but I wanted him to wait until Don was gone to tell him.
“Your wife is amazing my friend. She made me feel right at home. You’re a lucky man. So, Teach, when is our next lesson?”
“How about in two days. Same time and same place.”
“I’ll be here.”
I walked him out to his car, which was a new black Corvette. When he settled himself in the seat, I just had to have another feel, so I leaned down and kissed him again. While he was sucking on my tongue, I felt him again. Only this time I took my time. He was bigger than I thought. Then he did something I didn’t expect. He felt my tits. Gentle but firm. He was like a kid with his hand in the cookie jar.
“Easy, big guy. Remember, consider her sensitive, unless she asks for harder. Being Tender will always bring them back for a repeat performance.”
I watched him back out and drive away. I walked back on the deck.
“Well, it looked like you two got along well together. Want to tell me about it, or would you rather keep it to yourself?”
“Not tonight. If you don’t mind, I’m just going to go to bed.”
I fell asleep thinking, what the fuck have I gotten myself into.
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