She’s No Tomboy Anymore
Fbailey story number 408
She’s No Tomboy Anymore
I watched Teresa grow up. My wife and I have lived next door to her parents since before she was conceived. Her mother is a tall, thin, sexy woman of about thirty-five. We have a daughter that age that lives in California but no grandchildren yet.
Teresa wasn’t always a tomboy. She stared out life as a very pretty little girl in dresses that hated to get dirty. Then about age ten or eleven she became a tomboy. I guess its because there are not very many girls in the neighborhood and none her age. I have seen her beat the boys at wrestling, football, and even basketball.
Then she stared to develop about age twelve and she hated it. She used to complain to my wife and I that her boobs were starting to get in her way when she played with the boys. Besides they just wanted to touch them all the time anyway. She complained about her periods too. She got cramps, she got irritable, and she hated those damn thick pads between her legs.
One day I listened to her complaining and suggested tampons to her. She had no idea what I was talking about so I went in the house and brought one back out to her. My wife hadn’t had a period in about a year but had a few boxes of tampons on hand just in case.
Teresa wasn’t sure what to do with it so I told her to ask her mother. She came back without the tampon and was she ever upset. It seems that her mother doesn’t use tampons because there are some side effects from using them and she told Teresa to never use them either. However, she really hated those damn pads. She begged me to give her another one and to tell her how to use it. I wished that my wife hadn’t taken off for a week to see her mother.
I took Teresa in the house and up to the master bathroom. I got out the open box of tampons and took out the instruction sheet for her to look at. She pushed me out of the bathroom and then tried to get one in her pussy. She kept talking to me through the door. She got more and more frustrated. Finally Teresa just opened the door and came out bottomless. She had removed her shoes, blue jeans, and her panties. Before me stood the most adorable fourteen-year-old girl that I had ever seen. Her pussy had a light coating of peach fuzz on it and there was some blood smeared around.
I took her back into the bathroom, sat her on the toilet, and proceeded to wash her pussy with a warm soapy washcloth. She liked that and so did I. In fact I liked it a lot more than I should have. I then proceeded to try and shove that tampon into her pussy. I then wished that my wife still used the kind that had the cardboard applicator. After a minute of struggling I inserted my index finger up into her vagina. Her hymen was broken and there was no reason for that tampon not to go up into her. Meanwhile she seemed to really enjoy having my finger in her pussy. I told her that she just had to relax so that the tampon would go in. Then I started masturbating my fourteen-year-old neighbor. She tensed up but eventually she relaxed and went along with the feeling that was growing between her legs. Soon that little girl was wiggling around on my fingertip as if it were the only thing in the world. She had the best orgasm of her life because she told me so. She masturbated every night but she never felt that good doing it herself. I slipped that tampon up into her easily leaving the blue string hanging out of her. I took the washcloth and washed her pussy off again. Then she wanted to know what to do if she had to pee. I told her to take it out, pee, and then put it back in if it wasn’t too bloody, otherwise put a new one in. Then I gave her the open box.
Teresa smiled at me, pulled the string, and removed the tampon. She kept her legs open and peed into the toilet while I watched her. I always enjoyed watching my wife pee but watching Teresa pee was even more exciting to watch. She wiped with a couple of sheets of toilet paper, and then tried to get that tampon back in. She couldn’t seem to get it in but I did.
She couldn’t get the hang of inserting a tampon and she couldn’t get caught with a box of them either so for the next three days Teresa came to my house to pee, to get her tampon changed, and give me the best time of my life.
Teresa changed from a tomboy to a sexy little lady overnight. She started wearing the tiny miniskirts and sexy blouses that her mother had bought her in hopes of her wearing someday. She would spend most of the day on my front porch with me and several times a day we would go into the house to pee or change her tampon. She always removed her skirt and panties like she did that very first time but the second day when she wore a dress she also removed it, only she wasn’t wearing a bra. Teresa stood before me completely nude. She had beautiful little breasts that were quite good size for her body. They were perfectly formed and had the cutest pink nipples and matching areolas. As I masturbated her I noticed how hard her nipples got and without thinking I slipped my mouth over one as I fingered her clit. She wrapped her hands around my head and held me tightly until I felt her tremor and relax from her orgasm. She said that she loved the way I made her feel. She loved my finger fucking, masturbating her, and now sucking on her breasts.
She then asked me to fuck her. I told her that I just couldn’t do that no matter how much I really wanted too. She begged me but I refused. Then she asked me if I would fuck her if she let Teddy fuck her first. I knew Teddy, he was not a nice kid and I had seen him bully the boys and feel the girls up for years. I told her to stay away from Teddy. She said that she would if I fucked her.
She had me trapped between a rock and a hard place. I sure as hell didn’t want that little asshole Teddy fucking her. So reluctantly I gave in. We went up to my bedroom as always but instead of going into my bathroom we walked to my bed. Teresa undressed while I placed a big bath towel on top of my bed and then I had Teresa lay in the middle of it. I undressed and gave her what I thought was her first look at a man’s cock. Apparently she had seen her father’s cock on several occasions. It seems as if he has been showing it to her for the last few months now. I would question his motives if I weren’t about to do the same thing that he wants to do her. I pulled the plug and fingered her to two orgasms to lubricate her insides. I kissed her gently on her lips and I stimulated her nipples with my tongue. When I felt that she was ready I slipped the head of my cock into her and paused. She didn’t seen the least bit uncomfortable so I slipped in a little more and little more until I was all the way inside her. She seemed to be enjoying the feeling as much as I was so I started fucking her slowly. She really did like it so I went a little faster. She told me that my cock gave her the best feeling yet and she proceeded to have two orgasms to prove it. When I could not stand it any more I let my cum flood her cavity. It was without a doubt the fuck of a lifetime.
Teresa got up and sat on the toilet to pee and let a big gob of our cum drop into the toilet. She washed up and slipped a fresh tampon in all by herself. She thanked me for opening her up enough to get it in and she thanked me for the sex. It had been even better than she had thought it would be. She also told me that she would never have let that disgusting Teddy fuck her. I had to smile.
Early the next day Teresa brought her mother over to me. My heart raced but I tried to keep my cool. Teresa looked at her mother and said, “Tell him.”
Sylvia was a very good-looking lady and that day was no exception. She had on a white sundress and was standing in such a way that the sun shined through that dress allowing me to admire the shape of her legs and the gap under her pussy. It was strapless and just held up by her beautiful breasts. The length was quite short and well above her knees. I was impressed.
Teresa hit her mother in the side and repeated, “Tell him.”
Sylvia twitched nervously and finally said, “Teresa caught me just as I was going to let that kid Teddy fuck me. We were both naked and he had his hands on my breasts when Teresa caught me. Teddy grabbed his clothes and ran for his life leaving me there to face the music alone.”
She paused to catch her breath and gather her thoughts before she continued, “My husband doesn’t satisfy me anymore. Not in years actually. I have turned into the frustrated suburban housewife that my mother is. He only wants sex once or month or even less lately. I’m tired of masturbating all of the time with no real release in sight. Out of sheer need I let that little bastard Teddy seduce in. I bet he is telling everyone that he saw me naked and that I let him feel my breasts. I’m so embarrassed.”
She was turning a nice shade of pink as she continued, “Teresa told me that I should let you fuck me. In fact she ordered me to let you fuck me or she would tell my husband what I had done today.”
I smiled at Teresa and asked, “Is this what you really want?”
Teresa smiled back at me and said, “I think it will be for the best. Afterwards I’ll have another talk with her. You take her up stairs and I’ll find that little fucker and set him straight.”
I reached out my hand and Sylvia took it. I got up out of my chair, opened the door, and led her through the house and up to my bedroom. I turned Sylvia around but found that her dress did not have a zipper, it had a stretch top. So I slipped my fingers into the top of her dress and started slipping it down over her breasts exposing them. I looked over her shoulder at them and then cupped them in my hands as she melted into my arms. She said that she hadn’t been held like that in years. I couldn’t imagine why. After a few moments I lowered her dress down even further. I avoided catching her panties on the way down. I pushed that elastic to her ankles and watched her step out of it. My face was resting against her thigh, my ear was tickling her buttocks, and I could smell her sweet perfume. I knelt down so that I could press my nose into her panty-covered butt crack and reach around to stroke her public mound. She cooed softly then she had an orgasm and I had hardly even touched her. She was in desperate need of attention. I then lowered her panties to her ankles and she steeped out of them. I then turned her around to face me. Her public hair was neatly trimmed and slightly darker that the hair on her head, it needed to see more sunlight. I pressed my nose into her pussy rubbing my nose against her clit giving her another orgasm. The smell of her sweet perfume was mixed with her womanly odor.
I stood up and took her over to my bed, I pulled the covers back, and then I helped her onto my bed. I then undressed and climbed in next to her. She lay there on her back as I explored her body with my hands, my feet, and my lips. She liked having her nipples played with, pinched lightly, and sucked on. She cooed and had she another orgasm just from my nipple stimulation. This woman was in serious need of release.
I felt the heat radiating from her crotch, I cupped it, and then I fingered it. I finger fucked her hole and then I attacked her clit gently giving her a string of orgasms. My finger got bolder and more aggressive as I went on and her orgasms increased in intensity and duration, until it was just one long endless pleasure for her.
When she had a sexual overload and passed out I kissed her on the lips gently and just lay next to her.
Teresa came in and whispered to me. No, I hadn’t fucked her yet but I had certainly given her pleasure. Teresa told me that she caught up with Teddy and convinced him to keep his big fucking mouth shut or she would cut his balls off and feed them to him. He believed her too because she had sat on him, pulled his pants down and had a hold of his balls with one hand at the time. She also had a butcher knife in her other hand. She told me that he pissed himself too. She was pretty sure that he wouldn’t tell anyone what he had done to her mother. I just smiled.
Sylvia opened her eyes and looked at her daughter, she smiled, and then she said, “Thank you for taking care of Teddy and thank you for making me come here. I have never had a another lover like him in my life.”
Teresa giggled and said, “Me neither.”
Sylvia looked her daughter and asked, “What did you just say?”
Teresa climbed onto the bed and kissed her mother right on the lips, she grabbed a hold of her cheeks, and said, "I said that I have not had another lover like him in my life either. I gave him my virginity yesterday.”
Sylvia asked, “Is there anything else I should know?”
Teresa smiled and said, “I like tampons better than pads, I like being a girl now, and he masturbates me better than I can do myself.”
Sylvia said, “I already know about his masturbation technique. I can’t believe how good he is. I lost track of how many orgasms he gave me. I can’t wait to feel his cock inside me either.”
With that remark Teresa moved off the bed taking the covers with her. I rolled over onto Sylvia and worked my way down between her legs inserting my cock into her pussy. I heard her coo and I felt her orgasm. She was without a doubt the most sensitive woman that I had ever made love too. Fucking into her was wonderful. She responded to every probe, every touch, and to every kiss. She was constantly exploding with orgasms. When I finally released my load inside her she gave one last coo, closed her eyes, and fell asleep exhausted.
I got out of bed, put on a robe, and took Teresa down to the kitchen for lunch. We had a great time talking about what she had done to Teddy and how much she appreciated me taking care of her mother’s needs. She said that life at home should be better now.
As we finished washing and drying the dishes Sylvia came in. She was wearing one of my white dress shirts and it was not buttoned. She looked radiant. She said, “I want to thank you both. I really needed that and now I really need a shower. Would one of you care to join me?”
I looked at Teresa and she looked at me. Then she took my hand and she took her mother’s hand and led us both up to my bathroom. Sylvia asked me if I had a douche bag and then proceeded to teach her daughter how to use one, especially after her period ended or before a hot date where she wanted her pussy to be nice and clean. I watched Sylvia wash herself out and then help Teresa wash herself out too. Sylvia took me into the shower and washed herself completely from head to toe with my help. She got out and sent Teresa in to wash me off.
We dried off and I watched Sylvia use my wife’s hairdryer, her perfume, and put on one of her neglig? too.
Then Sylvia asked if she could watch me make love to her daughter.
She’s No Tomboy Anymore