Greenboro Sex Agency – Chapter Two

My wife and I run an unusual tourism agency called the Greenboro X-Entertainment Agency. We have a house on fifty acres of land in Northern New Jersey. Both my wife and I are expert tour guides. Our idea started when we took a tour of Italy and both my wife and I were attracted to the guide. So we decided to put our affairs together and start a business. “Come and tour New York City, and have sex with the tour guides.” Lots and lots of satisfied customers answered the advertisement, most of them European.

But not all of our encounters were with paying customers. Probably the most unusual happened with the girl we hire to clean our house after a customer has gone. She was a sweet little girl who was painfully uncomfortable with her secondary sexual characteristics: she always wore loose fitting sweatshirts and jeans to hide her newly rounded hips and bust. She lived with her parents and two twin sisters in a house that was adjacent to our lot.

After a two weeks of sucking and fucking, our customers Dave and Moochie had gone away. I was sad to see them go, because I had had most of the fun that weekend. My wife even got the action going thanks to a large black dildo we had named Big Blackie. It was the Wednesday after they had left so Cheryl-Anne had come over to clean. I was pottering about in the kitchen with a drill fixing one of the cabinets, and my wife, Maria was upstairs in the bedroom reading.

I was finished with the cabinet so I went upstairs to check on some other little chores that needed to be done. I noticed that the bedroom door was closed, which was a little strange. As I approached, I heard my wife talking to Cheryl-Anne. Now I had always thought of Cheryl-Anne as a sweet little girl (I think she was fifteen) and honestly had never thought of her in any other way. But as I approached the door something about the tone of my wife’s voice made me approach cautiously. I didn’t want Maria and Cheryl-Anne to know I was listening outside the door. This is what I heard.

Cheryl-Anne said, “but, what is it for?”

My wife answered in a sort of teachy voice. “We use this sort of device in our business, Cheryl-Anne.”

“Your business,” said Cheryl-Anne in a sort of shocked-but-I-am-trying-to-hide-it voice. “But it is so, well, big. Are all men that large?”

“No honey,” said my wife. Her Brazilian accent, always a turn on for me anyway was definitely doing something for me now. “This is larger than most men you will meet. We have a name for it: Big Blackie”

Cheryl-Anne giggled. Then she said, “I’m sorry ma’am. I didn’t mean to pry.”

“That’s Ok, Cheryl-Anne. Sometimes it is good to have someone you can talk to about these sorts of things. I could even show you how you would use something like this.”

There was a long silence then. I admit that I was feeling my own cock at this time through my jeans and it was getting pretty hard. I had never thought of Cheryl-Anne that way, but now I sure as hell was.

“Well,” said Cheryl-Anne in a small, unsure voice, “sometimes at night I get, sort of, well, wet down there. And I have two twin sisters who sleep in the same room as me. I feel ashamed and scared, because I want to touch myself. But I am always too afraid one of my sisters will hear me.”

Maria said in a kind voice, “Are you telling me that you have never yet even touched yourself down there?”

“No ma’am. Other than to go to the bathroom, that is.”

By this time I had a raging hard on, and I am not ashamed to admit I took it out of my pants in order to have better access. I knew my wife, and I knew she wouldn’t let an opportunity like this go by. Especially since she had been somewhat ignored while Dave and Moochie were here.

Now Maria went back to her schoolteacher voice. “Cheryl-Anne, I want you to lay down on the bed. I am going to teach you something. I want you to do whatever I say. At first it will be difficult, but after your first or second orgasm I think you will want to do what I ask.”

The risk of what Maria had just said to Cheryl-Anne frightened me, but excited me at the same time. I guess our entertainment agency had always bordered on the edges of the law, but having sex with a fifteen year old was definitely over the line. I liked it. When Cheryl-Anne said, “Yes maam” my penis throbbed in anticipation.

I could hear the noises of someone getting on the bed, or perhaps two people, I couldn’t be sure.

“Take your jeans off, Cheryl-Anne. Good. No, leave your panties on. Now, what I want you to do is rub the outside of your vagina with your finger. But do not put your finger inside it yet.”

“Yes maam,” said Cheryl-Anne. After a little time she said, “Ma’am, I am getting that wetness again. Is that alright?”

“Yes, Cheryl-Anne, it is alright. I have been watching you, and you play with yourself very well. Now, you know your clitoris, right? It is this part right here. What I am going to do is pull your panties to one side, and I am going to lick that with my tongue. That will help you get even more wet.”

“Yes ma’am,” said Cheryl-Anne in an excited voice.

I had never envied superman’s x-ray vision any more than right now.

“Do you notice, Cheryl-Anne, how hard it is getting, and how wet you are?”

“Oh, god yes ma’am”

“I am about to give you your first orgasm. It will wash over your entire body and you will shoot a little liquid. Don’t be frightened or ashamed, it is natural.”

Then I could hear Cheryl-Anne moaning lowly, and then louder and louder and then finally she yelled out.

“Oh, ma’am that was awesome!” I heard Cheryl-Anne say. After a brief pause she said “But I am feeling a little sleepy now.”

“No!” Maria said forcefully. “This is one of the most important lessons you can learn, Cheryl-Anne. After a man has an orgasm, he usually cannot have another for quite some time. But we women are luckier than that. We can have orgasms over and over again in a short period of time. Now, take your panties off completely.”

“Good Cheryl-Anne. What I want you to do now is to finger your clitoris just like I was just doing with my tongue, yes that’s good. Meanwhile, I am going to put my fingers in your vagina. The penetration will hurt at first, but then it will feel better.”

Again there was silence at the door, and I could only imagine what was happening in there. Then I heard Cheryl-Anne start moaning loudly again, quickly followed by another little scream of pleasure.

“Oh, god ma’am, I did it again, and this time it was even bigger than before!”

“That is very good, very good Cheryl-Anne. Do you have any questions?”

After a thoughtful silence Cheryl-Anne asked, “Ma’am, I still don’t understand Big Blackie. Your fingers inside of me felt good, but Big Blackie is much bigger than your fingers. Where does Big Blackie fit in?”

“I am glad you asked that, Cheryl-Anne. Do you notice that now that you have cum twice – by the way, that is slang for orgasm, cum; spelled c-u-m – how much more open you feel down there?”

“Yes, ma’am I do feel a lot more, sort of relaxed and wet still.”

“Good, because now I am going to teach you what a man feels like with Big Blackie. You are a lucky girl. Most girls learn this awkwardly from boys who don’t know what they are doing. This way is much better. Be warned that Big Blackie is larger than most men. It is going to make you feel very full, but it will be a pleasant fullness. Do you think you can handle it?”

“I don’t know ma’am.”

“Well, we will see. Now lay back and spread your legs as wide as you can. Good. Now lift your pelvis off of the bed a little bit. That will open you as wide as possible and position you nicely. Now I am going to insert this bulbous head. And I want to warn you that since this is the first time, you are going to bleed as I break your hymen. That is natural and the pain will go away quickly.”

Outside the door I could not believe that Big Blackie, the dildo we ordered as a joke, was going to take Cheryl-Anne’s virginity. I started to stroke my monstrous hard on with more conviction.

My wife said, “Now I am just going to part your vagina with my fingers. Can you feel the head of this thing?”

“Yes, ma’am. I don’t think it will fit”

“Oh, it’ll fit, I’ll make sure of that.”

Suddenly I heard a little scream of juvenile pain. And then I heard an even louder scream. And then I heard another, but now there was less pain in it. And then another scream, “I’m cuming again.”

I heard my wife saying in a quiet, reasonable tone. “That is because I am fingering your clit to help you take it all” Then I heard another scream from Cheryl-Anne louder than all the others, but this time not with pain.

For the next several minutes all I heard was intense moaning and the sound of the bedsprings as I am sure my wife rammed that thing deeper and deeper into her. The moaning started low, but started to rise in pitch and urgency. I think my own moaning was getting pretty loud as well. Finally, the sound of moaning and bedsprings reached a feverish pitch and I could tell that Cheryl-Anne was going to cum again. And in fact, I came as well, literally spraying the doorknob with my white sticky sauce. Cheryl-Anne and I had cum together, though she didn’t know it.

After quickly going to the bathroom and grabbing a washcloth to clean the doorknob I slunk downstairs. About a half-hour later both Maria and Cheryl-Anne came downstairs looking as though nothing had happened. I pretended to be working at some papers on the kitchen table, but I couldn’t help looking at Cheryl-Anne as she walked out of the door.

Of course my wife came back and told me all about it, and I told her about how I was listening at the door. And finally I asked her the question that had been burning in my brain, “Did she take that entire thing into her?”

With a satisfied smirk on her face Maria replied, “I made sure of it.”