This was about four years ago. I was dating a woman, Cindy, I met on line who was an alcoholic and also used drugs on occasion. And yet she could appear perfectly normal otherwise. Cindy was a nursing assistant at a large nursing home who worked evening shift. I knew the only reason she dated me was to squeeze money and gifts from me. She was living paycheck to paycheck barely able to buy her cheap wines and vodka. She was a skinny little thing and not too attractive, but she gave great blowjobs and swallowed, so I dated her until I could find a better piece of ass.
We generally went out to eat, then a club, then my place for sex. I never set foot in her apartment, and didn't want to as it was in a grimy complex on the edge some bad sections of the city. Anyway, it wasn't until about our tenth date that Cindy mentioned she had a 9-year old daughter whose name is Sara. She mentioned it very casually in reference to her 4th grade teacher that was giving Cindy a hard time because Sara's grades were so low. The father was evidently out of the picture.
I was shocked because she had never mentioned Sara before and, after asking some questions it was apparent that Sara was living very independently since her mother regularly slept through a hangover when Sara was getting ready for school, or she was working when Sara returned from school and had to eat supper, do homework and go to sleep. Cindy didn't seem to think there was anything wrong with it and I contained my surprise and concern out of curiosity to meet Sara.
That evening, after I fucked Cindy and she finished me off with a nice blowjob again, I gave her a fat wad of cash to help pay her rent and bills. I knew she would use them to buy alcohol and probably drugs, but I wanted to tighten the relationship dependency a bit in case her daughter Sara was attractive to me. I don't consider myself a pedophile, just a sex fiend that enjoys sex across the board.
The next time we got together it was a Saturday and I suggested a matinee at the mall because I was busy that evening. I also offered that she could take Sara along. She agreed and said Sara could shop while we watched the movie. That's not what I had in mind but I went along with it.
Sara was a cute, thin girl with long dark blond hair, big brown eyes and a wide mouth and sumptuous lips. Her mother didn't bother to introduce us so I reached out my hand and introduced myself. Sara shyly shook my hand and giggled when I teased her that she was even prettier than her mother. A few times along the way to the mall I attempted to engage Sara in conversation but she only shyly provided one-word answers. Cindy provided the more complete responses for her. There didn't seem to be much of a bond between the two of them.
When we arrived at the movie I lightly asked Cindy how much money she was going to allow Sara to spend. Cindy said Sara didn't have any money to buy clothes. I was taken aback as Cindy was essentially having her daughter shop around but couldn't buy anything. I quickly gave Sara four twenties and told her to buy whatever she needed. Sara was obviously quite delighted and Cindy was appreciative as well.
I wanted to be cool about my approach so the next time Cindy and I got together I didn't mention Sara. We ate out, went for some drinks at a club, went back to my place to have sex, and then I dropped her off at her apartment fairly drunk. The next date, however, I made my move. I asked Cindy how it was going with Sara's teacher and when Cindy said not well I offered to help by tutoring Sara once or twice a week after I got off work, or I could help pay for other tutors for her. Cindy was thrilled as she knew it would get the school off her back.
The first time I went over to meet with Sara I was quickly impressed with the cause of the poor grades. Sara wasn't too bright. She seemed to be a happy enough kid, but there wasn't too much brain category. I thought it was likely that Cindy was drunk a lot and/or on drugs when she was pregnant. However, job one was not educating Sara, it was gaining her trust. So I spent most of my time making her giggle and laugh by teasing her and telling funny stories about when I was a kid. I didn't waist an opportunity to tell her how cute she was. She savored the attention.
After several tutoring sessions we did actually make progress with her subjects, mostly math which required serious remedial help. Most importantly, however, I had Sara's complete trust. I had Cindy's complete trust, too. I beefed up my gift giving by taking Cindy out to get a new used car, which she desperately needed, and I put down $2,000 as the down payment. At this point I could come and go in and out of her apartment to be with Sara at will. I took Sara out shopping a couple of times and bought her a lot of clothes and an iPod.
More and more I began talking about sexual matters with Sara. The response from her was usually blushing giggles. At various times I told her she was no longer a little girl but was quickly becoming a young woman. I told her that it wasn't at all unusual for girls her age to begin having fun and exciting sexual experiences. I feigned surprise that, given her obvious sex appeal, she had never even kissed a boy before, much less had oral sex. At this time, suspecting that she didn't even know what I meant by oral sex, I explained what oral sex was in great detail. She appeared shocked that I would be so frank, her big eyes wide open and darting around nervously, and her wide mouth slightly parted. I was having so much fun filling her largely empty head with sexual images. When we went clothes shopping I encouraged her to buy sexy, revealing clothing to attract the handsome guys.
"You want to have fun at some point, don't you?" I teased. And, "Oh yeah, that'll get the boys to have some fun with you."
I also started bringing movies over which would be Sara's reward for finishing her homework and doing extra lessons. At first the movies were rated PG, but then I moved on into R-rated flicks with heavy sex scenes, mostly comedies. Several times following the movie I mater-of-factly said things like, "Now make sure when you start having fun with intercourse that you put a condom on the guys or go on the pill so you don't get yourself pregnant. Of course you don't need to worry about that until you have your first period. Up until that time you can have as much fun as you want and not have to worry about getting pregnant. But after your first period you need to be more careful."
Another time I said, "Sara, remember, when you decide to go beyond having fun with just oral sex and you start enjoying intercourse with guys, please remember to either go on the birth control pill or make sure to put a condom on the guy's penis each time. Not every other time, every time. OK?"
After her typical blush, and quick giggle and nod of the head, I continued, "Of course that's after your first period. Up until that time you can have a blast having intercourse with as many guys as you want without any concern about getting pregnant. Just remember, after you get your first period and if you're not on the pill and you or the guy don't have a condom, you need to stick to oral sex. Which is not the end of world, you know. You can give a guy a super fantastic orgasm swallowing his sperm, and he can give you a super fantastic orgasm licking your vagina without needing to slide his penis up into your vagina each time you have sex. Right?"
At another time when we were shopping I took her over to the panty section and said, "Look, Sara, do you need new panties?"
She shrugged her shoulders and with a slight blush said she didn't know. That's when I leaned over a said with a smile, "Sara, the reason there are so many nice panties here is so that girls can please guys. Skimpy, colorful, lacy panties turn guys on. Come on, let's get you some sexy panties for the fellas."
Sara giggled and blushed and laughed a few times as we walked around choosing just the right panties for us to buy. A couple times I held up tiny thongs and said to Sara's embarrassed amusement, "Here you go, Sara, go try these on and give everyone in the store a sexy fashion show. You'll have the guys here lining up to take you out on a fun date."
On the way home I said, "Now remember, about those panties, always wash yourself down there and put on a fresh pair before going on a date or if you think there's a chance you'll be able to enjoy some sex. The guys will really appreciate it."
That's when progress was made as she responded, "But I don't even go on dates." She meant this as just a factual statement but I pretended it was a complaint. I said, "Yeah, that's too bad because you could start having a really good time. You don't want really nice panties to go to waste. I'll see what I could do about it. I know a couple of older boys I might be able to introduce you to. I'll help you out, don't worry." She didn't respond and had a slightly worried look on her face so I quickly changed to the subject.
It was about two weeks later that I arranged for Sara to have her first sexual experience. I have a friend who's a real sleaze. He has a 17-year-old son, Alex, who's also a real sleaze. Tall, lanky, a bit goth and enjoying a steady diet of porn that his dad completely allows, I thought he'd be the perfect guy for Sara. I told him I'd pay him well to tutor Sara from time to time. When he laughed and said he sucked at schoolwork, I said with a wink, "Well, do the best you can to teach her math, and if you want to teach her other things you're welcome to it." When he hesitated over her age I responded, "Hell, she seems to swallow her food OK, and she has a nice wide mouth." Alex grinned broadly and agreed to the job.
"Sara," I said, "when was the last time you took a shower?" She responded that she just took one that morning. "Good, because remember I said I'd help you out in the guy category? Well, there's a great guy coming over today to give you a math tutoring lesson. I think he'll be perfect for you." Sara was stunned. She didn't say anything in response. "Go make sure your bedroom is tidy," I said. A nervous somewhat scared look came over Sara's innocent face as she stood up and left for her bedroom.
About fifteen minutes later a know came at the door and I let Alex in. Alex was clearly excited to meet her so I immediately walked him down the hall to Sara's bedroom. I looked over at Alex and gave him a long wink and an nod before entering her room. Sara was sitting at her desk. She was wearing blue jeans and a loose white blouse that was neatly tucked into her pants. Her feet were bare and she had dark pink nail polish on her toes. Sara stood up nervously when we walked in. I introduced them both, "Well, I hope you two really get along." Then I chuckled playfully and said, "Have fun, and try to learn something, too." I walked out and shut the door behind me.
Less than an hour later the door opened and Alex came walking out and headed for the door.
"All done already?" I asked. Alex nodded with a mischievous smile. He had a satisfied look on his face. I said quietly, "Now you didn't go all the way, did you?" He responded with a shake of the head. I continued, "Did she swallow?" He said as I handed him two twenties, "Every drop, Man. I gave her some gum to chew." Then we both chuckled and he headed out the door.
I knocked on Sara's door and walked in. She was sitting on her bed chewing the gum. Her blouse was untucked and the top three buttons were unbuttoned. Her hair was a little disheveled. She had a pensive look on her face and she looked at me with a blank, wide-eyed stare.
"Well," I exclaimed, "I guess you two hit it off. As Alex was heading out the door he said he really liked you and would like to come back soon." After a short pause I said with a self-satisfied laugh, "See, I told you I'd help you out. Now come on, I got a great movie to watch. She only said very quietly, "OK, I'll be right there." I heard her go into the bathroom but the toilet didn't flush. When she came into the den her blouse was buttoned up and tucked in again.
The next time I came over I played it cool. We went out to eat dinner and I helped her with her homework and left. That weekend I went out and fucked her mother Cindy again on Saturday evening. Her mother expressed appreciation again to me for helping with Sara's grades. She was obviously unaware about Sara's additional tutor experience so I gave Alex a call the next day to set up another lesson.
It was the following Tuesday that Alex came over. I decided not to tell Sara so she was pretty surprised when he walked in. I said, "Sara, why don't you go tidy up your room and get ready. Alex will be right there." Alex gave her a broad smile and a nod but didn't say anything. Sara didn't say anything either. Her face was wide-eyed, nervous and apprehensive, but she got up and walked briskly away to her room.
I got up close to Alex and said quietly, "Did you lick her pussy last time?" He shook his head and I continued, "Well, look, she should have a good time too, you know. Don't you know how to give a girl a good orgasm?"
Alex shot back, "Hell yeah I do."
"Well then," I said sternly, "don't just cum and leave this time. She needs to have an orgasm, too. Otherwise she'll stop wanting to see you. OK?"
"Yeah, yeah, OK man. OK."
I smiled and motioned towards the hallway and as he started down I said, "And take your time. Tell her how much she turns you on and be sure to kiss her a lot." He head bobbed up and down as he took off excitedly down the hall.
A little over an hour later Alex left Sara's bedroom and walked towards the door. He had the same satisfied smile on his face.
I handed him two twenties and asked, "Did you give her a good orgasm?" He nodded very assuredly. "You didn't fuck her, did you?" He shook his head. "Did she swallow again?"
He said as he took the twenties, "Every drop, man. Much better this time." Then he said with a chuckle, "Really nice pussy," and he left.
As I walked down the hall I noticed her door open and the bathroom door was shut. I went into her room. The cover on her bed was all ruffled up and I felt around for wetness but didn't find any. I straightened out her bedspread and laid down to wait for her. When at last I heard the bathroom door open I sat up. She was a little surprised to see me. Her lips seemed a bit swollen and she had obviously just brushed her hair. She folded her arms and stood there with a look of expectation that I would ask her something. She was chewing gum.
"Well you certainly impressed Alex. He said he really enjoys the tutoring lessons." I winked at her when I said the word "lessons." "How about you, do you enjoy them, too?" I noticed she was breathing a little heavily. Her wide-eyed expressionless look didn't change as she slowly looked down at the floor. I didn't give her a chance to answer. I laughed and said, "Well, I told you I'd help you to have a good time. Good thing we bought you those pretty panties. Now come on, let's have some ice cream and watch a TV show."
I knew I would invite Alex over a few more times, but I thought as we watched the TV show that evening that some variety was in order. As we sat there my mind was racing on to other sexual experiences I could set up for little Sara.
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