Taboo
2003-09-16

Cindy and I were together again the very next afternoon, and it was virtually a repeat of our second fling, except that, if anything, Cindy was even more adventurous and had even stronger orgasm after orgasm. We experimented with various positions and Cindy really liked taking my pole up her pussy when we fucked doggy-style. She was tremendously turned on by the attention that I paid to her asshole, so I decided to work our love making in that direction. I visited a nearby porn shop and located a copy of a film I had seen previously. It had a part that I remembered as being particularly informative in that area. I also purchased a couple of other tapes that I thought might just add some spice to future episodes with Cindy. She seemed willing and eager to learn, and I was eager to teach. A day or so later, Cindy had made an appearance at my door after the school bus had dropped her off, and I showed her the films I had acquired. “These are especially for you, Cindy,” I explained. “You are as natural a lover as I have ever encountered and perhaps we can discover some neat ideas from these films to enjoy together. ”“Oh, Mike, how neat you are. Like you’re always thinking of ways to make me tingle and get wet. Just thinking about watching these movies with you had made my panties get soaked. See…?” She hiked her skirt up to show me that her little cotton panties were showing where her pussy had leaked out juices. “Of course, I was already wet when I got here. In fact, I could feel myself getting wet on the bus on the way home, thinking about being with you,” she boasted.

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  I chose the film that I wanted her to see first, and put it in the VCR and turned it on. The preliminaries in the film were pretty typical. A pretty young girl was waiting at home for a TV repairman. One look at the girl and the repairman had other ideas than fixing her set. He wanted to get hold of her delightful set of tits. Cindy and I took advantage of the warm-ups to shed our clothes. We were sitting on the couch, kissing and touching as the repairman and the girl began to get real hot. The girl was giving the guy a great head job and he was eating her pussy and fingering her asshole. The camera was paying particular attention to the workout her anus was getting, and Cindy was very interested in what the repairman was doing and how is customer was reacting. “Look, Mike, he is fingering her asshole the way that you do mine sometimes,” Cindy observed. “See, she is really enjoying what he is doing. ”The repairman adjusted his position so that he could rim the girl’s anus. Soon, his tongue was probing deep into her shit-hole. The guy was dipping his finger into her cunt while he tongued the girl’s ass. She had lost some of her concentration on sucking the repairman’s big tool, and was close to cumming from the workout her asshole and pussy were getting.

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   Her eyes glazed over and she began to cum, shrieking and reaching down to press the repairman’s face into her buns. Cindy’s eyes were glued to the screen as her hands were caressing my cock and balls, but almost absent-mindedly. She stroked her hand up and down the length of my prick and played with the hole in the head with her index finger. My cock was hard and I was very turned on. “Look at the way that girl is coming, Mike,” she said curiously. “She is so excited and horny. Don’t you think so? Just look at the expression on her face.

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Do I look like that when I come, Mike?“Even more beautiful, Cindy, but, yes that is the kind of expression you have on your face, too. ” I replied. “Man, she like really digs what he is doing to her asshole,” she said. My hand had wandered, seemingly without direction, but very purposely into her crotch. By this time I had a finger in her dripping pussy and another playing with the outside of her asshole. Her reaction seemed positive, so I stuck the anus finger into her cunt to get it wet and then slid it into her anus. I had fingered her asshole before, but this time Cindy seemed to be very interested in the feeling. “Wow, Mike, that feels neat.

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   Will you stick your finger in me a little bit deeper?” Cindy asked. About that time she gasped, “Look, Mike, it looks like he is going to fuck her doggie-style. ” The repairman had rolled the girl onto her knees and she was on all fours. I knew what was coming next, having seen the movie previously, but I was anxious to see and hear Cindy’s reaction. “Oh, he is fucking her that way, Mike. I like it when we do that,” she said. I merely gave an affirmative grunt and continued to work my hand into her pussy and asshole. My fingers were buried deep in both openings and I could feel one with other through the membrane of skin that separated the two holes. For a second time, Cindy gasped. “My god, look. He is going to fuck her in the ass, Mike. ” Indeed, the repairman had pulled his large member from his customer’s pussy and was pushing into her asshole. These were experienced actors and the girl has obviously taken a large number of cocks up her rectum. By contrast, Cindy’s tight young ass was squeezing down on the finger that I was using to probe her shithole. “He is putting his cock into her ass!” she exclaimed.

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  I was not sure how she was taking to this idea. From her tone of voice, she was predominantly startled by the activity on the TV screen. I could tell from the actions of her hips in reaction to my probing fingers that she was turned on and interested in what I was doing, but perhaps not by what the repairman was doing to his newfound friend. “Look at her, Mike,” Cindy cried. “She likes it. Look how completely horny she is for his cock. It’s going inside her ass and she loves it. Look how she is grinding back on his dick. ”“Can we do that, Mike? I mean is my asshole big enough for your big cock? Look at them, Mike, they are really going at it…it’s like she can’t get enough of that guy’s cock. Your finger sure feels good in my ass, I’ll bet your cock will feel even better. ”I simply could not believe this girl. She was the most wanton female I had ever encountered. Not only was she willing and eager to experiment and try anything, she was incredibly relaxed and open about discussing her feelings. But, those thoughts were frankly more retrospective. My immediate reaction was to assure Cindy that her anus would accommodate my cock and that I would try hard to make her feel as good about anal sex as she obviously felt about pussy fucking.

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  “I’ll go slowly, Cindy. It may hurt a bit at first and if it does, just say so and I will back out,” I instructed. “Just roll over on your tummy and I will show you how to really enjoy this. ”Cindy rolled over and I reached for a tube of KY jelly that I had strategically positioned for just such an occasion. I squirted out a generous gob of the stuff and applied it liberally to the inside and outside of Cindy’s cute ass and butt. I ran my finger deep into her shit-hole and rotated it to further relax the sphincter. She looked back over her shoulder at what I was doing, then looked up at me and smiled. “That feels great, babe,” she said. Following my gestures, Cindy raised up onto her knees, which left her backside pointing up towards me. I knelt behind her and spread some of the remaining jelly on the head and shaft of my dick. I slid my prick into her pussy and gave her several hard strokes and felt her cunt start to spasm in the preliminaries of a giant orgasm. As tempting as it was to continue this to its logical conclusion, I eventually withdrew and aimed the head of my cock towards the opening of her bowels.

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I grabbed my cock in my hand and guided it home to her anus. As I started to poke it in, I could feel Cindy tense up. Her spine arched a bit and I could see that she was clinching her fists.

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   I had barely begun, so I could tell that she feared the fear (with apologies to FDR) rather than the actual act. “Relax honey, I’ll be careful,” I assured her. “You will soon find out that this is just another way that men and women can enjoy each other. ”“I know, Mike, and I trust you…it’s just kinda new and scary. ” But, she did relax enough for me to get the head of my prick past her tensed-up sphincter and into her chute. I paused to let her (and her asshole) adjust to the experience, then I began to thrust forward. Cindy let out a low, animal-like groan after my dick had slid in a couple of inches. I paused again and said, “If this is hurting you, Cindy, I will stop. Do you want me to pull my cock out of your ass?”“No, Mike, I want to feel you in my ass. Don’t stop now,” she insisted. I did pull my dick back a bit – maybe an inch – and then started to push forward again. In a few moments I had about half of my organ planted in her asshole. Again I paused when Cindy took a very deep breath. Her hands were clinched into tight fists and her knuckles were white. “Maybe that is far enough, Cindy,” I quizzed.

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  “Nooo…it hurts a little, but it hurt a little when you fucked my cunt the first time,” she almost screamed. “Give me more of your wonderful cock. Fill my ass, Mike. Don’t you dare stop now. ”So, I resumed the penetration and in no time I was buried full to the root of my member in this beautiful girl’s very tight shithole. “Oh, God, I feel like there is an entire telephone pole stuffed up my ass. It feels really strange, but in a very good way. ”“Your ass is so tight, Cindy. It is squeezing my cock like it is in a vise. ”Gradually, I began to withdraw my spear until only the tip remained, then slowly reentered and let it fall until my balls were once again flopping against Cindy’s juicy pussy. Then out until just a couple of inches remained and then deep into her bowels. Slowly, at first, and very gently, then gradually, I began to pump her with increased force. I braced my knees and placed my hands on either side of her hips and before long I was fucking her quite hard. Cindy instinctively reached back between her legs and pulled at her clitoris with one hand while she braced herself with the other. “Oh, that feels so great, Mike.

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   You are really fucking my ass. Keep it up. Give me all of your wonderful cock. I can feel my pussy, Mike, it is flowing like a river. ”I reached under and felt her cunt. She was right, it was producing huge quantities of her delicious juice. I put my finger into her cunt and then drew it to my mouth to suck off her nectar, then repeated that several times. “Fuck me, Mike. Fuck my hot asshole,” Cindy cried. “Please fuck me hard. I am cumming and cumming. ”“Hang on, Cindy,” I replied. “There is going to be some cum flowing into your bowels very soon. Your ass is gripping me so very hard. Good grief, it feels like you’re going to squeeze it right off.

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  ”It was true, too. Cindy’s up-until-now virgin ass was tightly clinging to my cock as I pounded it furiously into her again and again. I could feel the stirring in my groin that signaled my orgasm, and it welled up deep in my guts. Then, like a cannon, my cock erupted deep in Cindy’s bowels and began shooting my jism in her cavity. Again and again I spurted into her ass and she howled out her pleasure at the top of her lungs. She was pulling at her snatch and bucking back on my cock as the explosions continued. Only after they had subsided and my penis began to lose its turgidity and retreat out of her anus, did Cindy’s orgasm begin to wane. Cindy literally fell flat then curled into a fetal position as I settled in behind her like two spoons in a silver drawer. Her breathing, and mine, returned to normal over a few moments. Not a word was spoken for several minutes as we enjoyed the warmth and closeness of our snuggling. Finally, Cindy broke the silence. “What a neat experience. Imagine in just a few days you have helped me become a real woman, Mike. You have shown me how to feel so comfortable about everything…you’re a master! I can hardly wait to know what’s next!”.