Educating Our Youth Ch. 07

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cindyexposed
cindyexposed
2,343 Followers

"Yes." Was his short, curt answer.

Stephen stood there naked, his penis flaccid, hanging down in front of him. It dawned on me that this was the first time he did not grow erect immediately in my presence. That fact alone irritated me beyond belief. He spends two hours with that bitch Stacey and now he no longer gets aroused standing naked in front of me. I did not like this development one bit.

"And?" I pushed to get additional details.

"And what?"

"How did it go? Did you enjoy your experience with Stacey? She seemed to be walking on cloud nine when she left moments ago. It appears you 'did her some good'. I think you have a new member to your fan club." I realized I was talking too much; I was talking too much out of nervousness. I decided to shut up and let Stephen speak.

"It was nice, I had fun."

"Did you use a condom?"

"No, Stacey said I did not need one, she is on the pill."

Stephen was not going to volunteer a damn thing! If I was going to get nay information, I was going to have to drag it out. "OK. Tell me what happened."

"We talked for a while, then we started kissing, and we had sex." He paused, thinking what to say next. "It was different than it is with you."

"How so?"

"With Stacey, it was really obvious that it was about the sex, not about me. I mean, the sex was great and all. But after you and I are together, I feel great. And I know you care about me, and I know that I love you. But with Stacey, I don't know. After we each climaxed, I knew that was it." He shuffled his feet a bit, and continued, "I'm not complaining or anything. It was fun. But with you it's not just fun, it is beautiful."

"Stephen, that might be the nicest compliment I have ever received from anyone. Thank you. And yes, what you and I have is beautiful. And special. And don't you ever forget that."

I walked over and hugged him; and I felt his penis throb upward as I did. "I am glad to see he still likes me.", motioning towards his penis that was swelling and growing slightly now as I hugged Stephen.

"Cindy, can I ask you something without making you mad?"

"Oh my, that sounds like a loaded question; but yes, you can ask me anything you want; and I promise I won't get mad"

"Have you ever had anal sex?" he asked sheepishly.

"Oh my God!" my minded raced to the obvious conclusion about what was behind this question. "Did she put you in her backside? I can't believe it. No wonder she said you were almost 'too big'. Well you certainly crossed another bridge today, huh?"

"We didn't start out doing that. We did it the regular way at first. And she really seemed to like the way we were doing it."

He was struggling with telling me this, but he wanted to discuss it with someone. As I write this, I realize that it was a great compliment for Stephen to trust me enough to share this with me; but at that moment I was irritated and very, very jealous that he had fucked Stacy 'bareback' and then he had cum in her ass. But I worked hard not to let my jealousy or irritation show.

I just said, "Continue."

He took a deep breath and said, "Well, after she came the first time, she climbed off me and asked me if I wanted to try something different."

"And of course, you thought 'why not?' right?" By my tone, it was clear that I was not pleased with this development.

"Yeah something like that. Don't be mad. I did not know what she was going to do at first. She got on all fours and told me to move up behind her. She took a tube of lubricant out of her purse. She handed the tube to me and asked me to put some on her backside."

"Which you were only too willing to do?" I was noticeably pissed now.

Stephen looked away, and nodded his head. "I did not really know what to do. So I did what she asked. I put some of the gel on her anus, and then I worked it all around with my finger. I thought that she just wanted me to finger her bottom. She seemed to like my finger touching her back there."

"Stephen, you can say asshole. I mean you did just fuck my friend in her nasty asshole. I don't think you need to be so prim and proper to use socially polite terms like 'bottom'. Just say asshole." I felt bad that I was letting my jealousy show through with this irritation.

Stephen sat there silently, staring at the floor.

"OK, I'm sorry. Use whatever terms you want. I guess I am just a little jealous. I know I have no right to be, but I am. Continue.

"You're jealous?" Stephen asked with a smile that revealed a combination of pride and relief.

"Yeah, I am a little surprised myself. But I am a little jealous you did that with Stacy." I said, shaking my head with amazement that I had revealed my feelings about this. "Stephen, you are very special to me. Go ahead and tell me what else happened. I am not mad at you."

Stephen nodded as if he understood, and went on, "She then had me kneel behind her and she took my cock towards her bottom and she told me to keep very still and not to push too fast."

He looked at me to see if I was repulsed, angry or worse. I guess he decided that I could handle the rest of the story.

"Then she put the tip of my penis on her anus, she slowly pushed backwards forcing the tip inside her. She grunted and it seemed to hurt her, but she would stop for a moment, and tell me to stay still. She would pant and moan for several seconds. It seemed like when the pain subsided a bit, she would resume pushing back forcing a bit more of me inside her. And then she would pull forward a little bit and then push back a little further. Each time she pushed me a little deeper into her bottom."

Stephen looked at me to gauge my reaction. "It was very hard not to cum, she was so tight back there, and her moans and whimpers were really getting to me. I was only about half way inside her and I thought I would lose it right there; but I was able to fight off the urge to cum."

"Did you enjoy it? Did you enjoy being in her as that way?" I asked.

"I don't know. In a way I did. She was very tight back there; and that really felt good. And I felt so...I don't know, naughty, bad. I knew this was something really 'out there."

Yeah, sometimes being really naughty can be very exciting. I mean, that is a part of your appeal. You are the teenage son of my best friend. It is pretty goddamn wicked to be fucking your best friend's son." I said in full disclosure. "So how do you feel about what you did with Stacy?"

"It was obvious that when I first went in her backside, it hurt her; but it seemed to hurt her in a way that she liked. She kept telling me I was too big, not to push, that it hurt; but she kept pushing back against me, driving me in a little deeper. And every time she would push back, she would tell me to be still and that it hurt; but she liked the fact that it hurt a little bit. She was almost crying when I was about halfway in, but it was not like she wanted me to stop. It was like she was determined to take me back there no matter how bad it hurt. I did not really understand why."

"Stephen, a strange fact about human sexuality is that there is often a very fine line between pain and intense pleasure. And a lot of women are very aroused by having their anus stimulated."

"Do you enjoy it?" Stephen turned this back to trying to learn about my likes and dislikes.

"That is a very personal question, but it is a fair one. I enjoy having my backside touched on occasion, and stimulated. However, I am a pretty small, petite woman and I cannot accommodate even a small penis in my backside. It simply hurts me too much." I wanted to get back to what happened with Stephen, "So Stacey liked being taken back there, huh?"

Stephen nodded his head, and said, "It was strange. Like I said, it obviously hurt her. In fact, at first, I thought it might be hurting her a lot, too much. She acted like it did and had me hold very still for a while at first. But she wanted all of me inside her. And I did not move much at all, but she had an orgasm almost as soon as I got inside her really good. I only stroked in and out a few times before she came. She buried her face in the pillow and just screamed 'oh god, I'm cumming'. I am surprised you did not hear her."

"Stephen, I did hear her." I said shaking my head.

He stopped for a second, and then continued, "Cindy, there is something else."

"What?"

"It turned me on."

"What did?"

"The way she seemed to enjoy me pushing inside her despite the fact that it seemed to hurt her. Every time I would flex my penis, it stretched her anus and she made a sound like it hurt but hurt in a good way. She would let out a little scream, or screech. She would groan and grunt, and she would beg me not to move until she could get used to my size. All I had to do was 'pulse' my penis and she would moan and bury her face in the pillow. She was whimpering every time I just flexed my dick inside her backside."

Stephen paused to see how I was reacting before continuing. His penis was growing as he told me of his first anal experience. He obviously enjoyed reliving it.

"I kept doing it, flexing my penis in her bottom. I think that is what made her have an orgasm, because I wasn't really stroking in and out of her when she came. She really liked the way I could flex my dick and stretch her open repeatedly. And I liked the way she would react, and almost cry into the pillow from being stretched open like that, but she also got more and more excited. And the fact that she liked it turned me on. I really liked having her bury her face in the pillow and cry out and whimper every time I flex my cock, making it a little bigger. When she came, I came inside her backside. She said she loved the fact that I 'came in her ass'."

"Is this sick? Am I sick for having done that?"

God I loved this boy. He was the most genuine and sincere lover I had ever known. "No Stephen, you are not 'sick'. You are completely normal. You became aroused by arousing a woman. There is nothing more normal than that. Now Stacey, she just might be a little sick; but you are normal and healthy." I could not help taking the barb at Stacey in my response.

"I only wish if I was going to do something like that, I would have done it with you. At least the first time." Stephen seemed to sense I was hurt or disappointed at this point.

But I laughed loudly at his last suggestion that he and I should try anal sex. "Well my good man, that is just not going to happen. Your cock is way too big, and my backside is way too tight and small. The geometry just does not work. No sir, if you want to pound someone's backside, you better stay in touch with Stacey."

I hugged him again, and took his partially erect penis in my hand. "So how well did you wash this thing afterwards? You better scrub this cock absolutely raw if you ever want to get it back in my mouth again!"

He shook his head, "I am thinking that maybe I should not have told you about this, huh? I scrubbed it and scrubbed it. I'm kind of freaked out myself."

I then led him by his cock back to the bed. I removed my clothes, and said, "Stephen, will you make love to me? I want to feel you inside me now. I want you to show me that I am still the number one woman in your life."

Stephen's cock grew fully erect under my gentle stroking. I decided I did not want to put his cock, which less than a hour ago had been up Stacey's ass, in my mouth right now. That was just too weird. Tomorrow or the next day, I would get over this irrational repulsion; but for right now, Stephen was going to have to do without me sucking on him. And I would have a latex sheathe between him and me while he was in my pussy this afternoon.

Once fully erect, I encase his penis in its protective condom. I laid back and invited Stephen to mount me, to make love to me. He climbed out top of me, and entered me. For the next 15 minutes he fucked me slowly and lovingly. We necked and he caressed my breasts as he slowly pulled out and slowly pushed into me. I loved the feeling of his thick cock entering and leaving me. I was aroused, but did not want to come, this was about emotion and love.

When he finally came inside me, I was so overcome with emotion that I started to quietly cry. Stephen held me as I sobbed silently in his arms. I had fallen in love with this young man. Yes, I loved Jim, and I always would. I would always be Jim's wife. But I had fallen in love with Stephen as well.

Coming soon - Chapter 8

cindyexposed
cindyexposed
2,343 Followers
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  • COMMENTS
5 Comments
lenmc02091964lenmc02091964almost 5 years ago
Love You Cindy

Your the best Cindy. Love your stories just wish I had known a girl like you in 1974.

ChasteCuckoldChasteCuckoldover 9 years ago
Super hot

Hot story loved it

DaveXX80DaveXX80over 9 years ago
So erotic

Wow. This story took a fun and very hot turn. Loved it!

TigerPaw1010TigerPaw1010over 9 years ago
Oh yea...

Very nice twist of events. Looking forward to Chapter 8.

arrowglassarrowglassover 9 years ago
Soooooooo nicely done!

Such a great ay to handle naughty HOT sex!

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