I Knew It was Silly

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My idea was crazy.
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Cheryl and I have been friends since she was in the 6th grade and I in the 8th. I am nearly 3 years her elder. By the time we reached high school we were still best friends and figuring out we maybe were to be more than just friends. We had our first date when she was 16 and I going on 19. When Cheryl was 18 and a senior in high school and I in my second year of college we had sex for her first time.

That first time opened a new world for us and brought us to the reality that we would spend our lives together as man and wife. I have always had the pure instincts of the nearly perfect mate, but not quite? I knew something was slightly off, but not for sure exactly what?

From the time we were children I found excitement in Cheryl playing with other boys. I sometimes found it cool if she went off to play with little Johnny who lived next door. Even once we had become lovers I was still kind of turned on by her being close with other guys. We even talked about if from time to time. Cheryl told me how silly she found it.

She used to tease me about it. Saying I was just a silly boy that enjoyed being jealous. But I knew being jealous turned me on lots. Just before we became engaged I did suggest to her that maybe just to be completely sure of things that maybe she should date a bit?

We talked it over at length in detail. Not to the point that she should explore sex with others, but we did leave that open to be explored if desired. I did understand that as far as I could tell I really had no bad feelings about Cheryl exploring sex if she wanted. As she began her third year of college, I had graduated and moved on to a job. Her college was a 4 hour drive from where my job was so we were forced apart for periods of time.

I then made the suggestion she could be free to date and we could make sure before we were married. She just laughed and poked fun about me wanting to be jealous again.

Cheryl is 5' 2" and 118 pounds. Which some would say is 15 pounds too much if you haven't seen her. It isn't all in one place at all. Her boobs are a big B cup or a medium C cup of a small petite woman and it isn't in her ass that matches her boobs very nicely. It is just all over the full package of a fully stacked little very pretty young woman. With short blonde hair and green eyes.

Cheryl came home nearly every weekend for her first two months at school that year until she figured out it would help her classes if she didn't do it every weekend. She stayed up at school for a month before she came back home again. And when she did she told me first thing.

"Well I did what you ask."

"You did what that I ask?"

"I am dating now."

"Wow, Cool, how many guys are you dating?"

"David be serious, I am dating just one. A guy in one of my classes ask me out a couple times and I finally told him yes."

"And how many dates have you been on so far?"

"Well besides just lunch a couple times I have been out with him six times."

"Oh Wow, you must have gone way past the good night kiss stage and on into the suck face while fondling your tits stage."

She laughed and looked guilty not looking me in the eye.

"You may want to be somewhat jealous?"

"Oh so you have gone past that stage and into the fully naked for him stage?"

"No not quite that far just yet but he has fingered me a couple times now."

"And you are sucking him by now?"

"I have given him a couple of blow jobs, yes."

"Sounds like you could be very near the panties off and legs up soon?"

"I have not gotten quite there yet. David I love you and I don't want to screw us up now."

"But you do wonder if I want to be jealous enough to see what it is like when you fuck someone else?"

"Well if, I keep seeing him that could happen?"

"Keep seeing him."

"You think you really will be okay if that happens?"

"We can just see how jealous it makes me?"

"His name is Dennis Jerry, and I may make you very jealous?"

When Cheryl went back to school that week I knew things could change somewhat because I knew she would probably fuck Dennis when she got back there.

She didn't call for a few days and when she did she ask first thing.

"How jealous are you?"

"How jealous do I need to be?"

"You need to be very jealous."

"So you are doing it?"

"Yes I am."

"Then I am VERY jealous."

"A bad very jealous?"

"No I don't think so, maybe a very curious jealous?"

"Oh God that is a relief."

"Is it fun?"

"Yes I must admit it is. You remember when we first started doing it. We couldn't do it enough. That is the way this is."

"I had hoped you could have a fun time with it."

"I love you David, and you are very silly."

Cheryl continued fucking Dennis the rest of the semester and she spent only part of her break at home with me. The other part she spent with Dennis. Second semester she moved in with Dennis. We had talked about it and I knew she wanted to explore the relationship with him further. So I encouraged it.

She had a very solid relationship with Dennis and a great sexual relationship with him. She lived with Dennis the full semester and when it was coming to an end I knew she'd begun to struggle with it ending. Maybe the only miss step in their relationship was that he encouraged her to have sex with a couple of his friends, which made her unsure of just how serious he was about her.

I had told her maybe to find out how he really felt she needed to have done as he wished?

"You think I should have sex with them to see how he reacts to it? How would you feel about my having sex with others?"

"I would become instantly very jealous."

"Bad jealous?"

"No probably just wildly jealous."

"You are so silly. So you really think I should let them have me? They will still be over a few more times before semesters end. There are usually Two of them but sometimes there are 3 or 4."

"Does he tease you about it every time they come over? And in front of them?

"Yes every time and right in front of them."

"Maybe he just loves to tease you in front of them and he is just teasing you?"

"I thought that was it too, but I decided to call his bluff and he began to fondle me in front of them. So I let him do it. And he soon had my blouse unbuttoned and was opening it in front of them. I don't always wear a bra and I wasn't that day. He knew it and he opened my blouse for them."

"He showed them your bare breasts?"

"Yes, he held it wide open for them. There were four of them that day and he held me there for them to look and he whispered to me to let them have me."

"So he is not just teasing?"

"No, he really wants me to do it."

"So he likes you to go braless?"

"Yes, he loves the way they look naturally he says."

"Well he's right they do look very nice that way."

"You are so silly."

Dennis had come home and she said he was getting very jealous so we hung up. She had told me all of this while we were on the phone. I knew she had nearly a month left to decide what to do about Dennis.

We were moving very near the end of semester and I had not heard anything from Cheryl so I just waited. I knew she would be home very soon. And she was. I knew the end of the semester had come and she would come home to see if not me then her folks. And when she did she came right to me.

"David, Dennis has ask me to come with him to LA. He has a job out there and he wants me to live with him out there. I am not quite ready to give him up yet. He has ask me to marry him and I need time to think about it."

"When he ask you to marry him what did you say to him?"

"I said yes."

"So you got your problems with him worked out at school?"

"Yes, you were right as usual and I did what you said. I ask him if it was really what he wanted and he said it was. So I told him I'd do it for him."

"You fucked the guys he wanted you to?"

"Yes, I fucked all four of them and I did it nearly every day since we talked about it."

"And it was fun?"

"I really enjoyed it. That was when Dennis ask me to marry him."

"Are you getting married here before you go out there?"

"No, we will come back here if I decide to really marry him."

"Does he have friends out in LA he wants you to do it with too?"

She looked funny for a bit before she answered me.

"He has friends in Denver he wants me to be with on our way out there. But yes he does. In fact he wants me to stay with some friends of his when we get out there while he has to go for some training for his job. How did you know that?"

"Just a guess Cheryl."

She left the next day with him. My guess was that Dennis was grooming Cheryl to prostitute for him. That his friends at school were helping him to groom her for his wants. And yes I thought he would marry her and once he had her with enough men he would tell her how much they could make and get her to do it openly for him.

Cheryl had been gone nearly 3 months when she came home. She came right to me.

"David did you know what he was doing with me?"

"I can make a crazy wild guess."

"He did want you to marry him?"

"Yes, and he still does."

"And you, do you want to marry him?"

"Maybe I do, I am not sure I can do what he wants me to?"

"Why not Cheryl if you love him?"

"How many guys have you fucked for him now Cheryl?"

"I don't know David?"

"Yes you do Baby. You did the four at school lots."

"And I did 4 in Colorado on our way out to LA."

"He wanted you to be with them the one time on your way out?"

"No, I was with them several times while we were there. And I did it again yesterday on our way back."

"And while you were in California?"

"David, he set me up with guys on a regular basis out there. Guys were paying him to see me. Some of them were fucking me once a week and a couple more than that."

"How many Cheryl?"

"Oh, I don't think I can say it. It was a lot of them."

"Cheryl it wasn't a big thing really it is just fun sex. Was it fun Baby?"

"It was. I enjoyed doing it. It made me feel so sexy they paid him to see me that way."

"How many regular customers did you have Cheryl?"

"The week we left to come back here I did a new guy and he was my 19th."

I took Cheryl to bed and we had the best sex we'd ever had. Dennis had gone on east to where he was from and did not return. Cheryl went back to school for her last year. Dennis had not only made my wife to be a prostitute but she had become a whore too enjoying variety in partners. I did check up on Dennis and found he was in jail out there.

Not long after school started that year she came home and told me she had a new boyfriend. She laughed then.

"Do you remember a guy named Donran Johnson you were in class with your last year here?"

"Big black guy 6' 4" and 250pounds played tight end. Sure I knew him."

"He could be a bit more than the 250 now, he is a very big guy. He is back in school to finish his degree. And he is looking for a room mate to share his house and has ask if I might be interested? He knew I lived with Dennis last year. And he knew Dennis is a pimp. And he knew Dennis was trying to groom me for what he wanted. And he knew I went to LA with Dennis so he figures I did it. David have you looked me up on line out there in LA?"

"No I haven't."

"Well Donran has and says I have great looking tits. He showed me the pictures. He wants to post me back here like that for black guys."

"Has he fucked you yet?"

"After he showed me the pictures of me as an escort in LA, yes I let him."

"Did you pose nude for him?"

"Yes I did."

"Has he posted them yet?"

"He says he will put them up on his web site tomorrow."

"You are going to let him pimp you at school?"

"He already is. I am seeing three of the guys on the football team now."

"They know he is pimping you?"

"Yes all the black guys on the sports teams know I fuck for money now."

"Are you moving in with him in his house?"

"I already have and they come here to fuck me."

Cheryl finished her final year at college living with Donran and he pimped her. I had thought we might have a problem with her leaving him after school but he let her go.

We were married the next spring and started our family soon after.

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Buster2UBuster2Uover 1 year ago

I Love this Story! So Scary! My heart started beating so fast out of fear that David was going to loose the love of his life by encouraging her to date other! Whoa, Then she becomes a hooker call girl prostitute? Whoa, So Hot she was getting so many miles on that pussy that she must have been a fantastic fuck when she finally came home. But with all that experience could she remain satisfied with just one man when she got married? But the idea sure sounds hot. 10 stars to writer. I love a happy ending. Thank You.

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