With my sister’s help I got a girlfriend, a very nice loving girlfriend.
Fbailey story number 345
With My Sister's Help
My sister Tina is older than I am and is now a very popular senior in high school. She is nineteen years old, a tall well built blonde, and a cheerleader.
I on the other hand just turned sixteen and became a freshman in high school. I’m a nerd, a computer geek, and not very popular. I like to play chess and other games that do not require much effort.
Tina was determined to make me popular before she graduated in June so she got started right away in September.
At first she made sure that all of her friends knew who I was, then she had them saying hi to me in the hallways, and eventually they were asking me to help them with their computers. The jocks just wanted faster computers to play their games quicker or the codes to give them unlimited lives and ammunition. They really didn’t give a shit about learning anything about their computer and would usually leave me alone until I finished. I always made sure to check out their files to see what was going on, what they liked to do, and what files they kept. I almost always found something on their machine that I wanted. In my backpack I carried hard drives that I could plug right into their USB ports and copy their entire hard drive if I wanted too. I also carried blank CD’s, DVD’s, and a few Flash Dives.
Mostly I took programs that I thought that I could use, sometimes I would copy a game too. However, I made it a practice to copy all of their JPG’s to a file to look at later.
I could not believe some of the pictures that I found. Those jocks would take pictures of themselves naked to send to girls on the Internet I figured. In reply the girls would send pictures of themselves to them. At home I would sort them out keeping the pictures of the girls in a folder with that guy’s name on it.
The more computers that I worked on the more I saw the same girls popping up again and again. Then I started seeing some of those girls in school. Wow! In no time at all I was able to put a name to the face and body in those pictures. Then at home I started making folders of those girls and copying their pictures to that folder. Many pictures were duplicated because the girls sent the same pictures to everyone.
When the captain of the football team needed my help I hit the mother load. He had nude and partially nude pictures of all the cheerleaders including my sister Tina. Those pictures were taken in his bedroom on his bed because I recognized the furniture, the bedspread, and the carpet in almost every picture. He had a series of pictures fucking them all. They were dressed, undressing, and then fully naked, they were on his bed, his big cock was entering their willing pussy, and then his cum was dripping out of them. It was the same scene with different girls. He even named the files properly with the girl’s full name, date, and sequence number. According to the dates my sister was one of the first girls that he had fucked.
After that I planned a way to get my sister to help me with my sexual problem. My sexual problem was that I wasn’t getting any, I had never gotten any, and the future looked just as promising.
Eventually I just said, “Tina I need your help.”
Tina replied, “With what?”
I said, “Sex! I’m a virgin and I don’t want to be.”
Tina laughed and said, “What do expect from me?”
I replied, “I just want you to help me find a girl that might be willing.”
Tina laughed again and said, “You want me to find you a slut to fuck?”
I said, “Absolutely not. I want a nice girl, a virgin like me, and one that could become my girlfriend.”
Tina said, “It would be a lot easier to set you up with some of my loose friends.”
I said, “Easy isn’t exactly what I have in mind but I could use some instruction so that I don’t fumble around and look stupid the first time.”
Then it finally came, “Why should I help you?”
That was when I handed her six pictures of her naked that I had printed out. She looked at them, knew where I had gotten them, and threatened to tell the captain of the football team to kill me.
Once again I asked her to help me. She smiled and told me to undress so that she could see what she had to work with. I then had to jerk off in front of her. Twice! She liked the fact that I could do it twice that quickly.
Surprisingly my sister Tina then undressed so that I could see her naked. She then explained her breasts to me and let me touch them. She told me what she liked and how hard to squeeze them. Tina liked her nipples pinched and twisted a little bit but not too hard unless she was in the middle of her orgasm, then I could pinch and twist them as hard as I wanted too. She let me kiss her a few times, kiss her neck, and then kiss and suck her nipples. Tina let me look at her pussy as she explained to me about her pubic hair, her pubic mound, her outer lips, her vagina, and her clit. I got to feel, pull, and open her parts. I got to probe her hole with my fingers and rub her clit until I gave her two orgasms. Tina really enjoyed that and told me that if I fingered her every night that she would help me find a nice, willing, girlfriend. Deal!
That night after her shower but before bed, Tina came into my bedroom so that I could rub her clit until she had three really good orgasms. She covered her face with my pillow whenever she felt the urge to cry out. Afterwards she let me sit on her stomach and slip my cock between her tits as she held them together. I was literally jerking off in her tits. She didn’t consider that sex because I wasn’t putting it inside her body. Tit fucking Tina was the best thing yet and I could hardly wait to put it inside a girl.
Two days later Tina brought a girl home with her. Brie was the younger sister of the football captain, she was really cute, and she was also a virgin. Brie was fifteen years old and still in the eighth grade. Tina had been talking to her about me and apparently Brie was willing to let me fuck her. Great!
Wait a minute, why was she so willing?
Well Brie was really pretty but she didn’t quite fit in with the ‘in crowd’ at her school because she was known as ‘little miss goody two shoes.’ Tina had comforted her in her time of need and suggested that I would be willing to help her out. She convinced Brie that I was the perfect boy for her and the perfect boyfriend too. If she wanted sex I was her man. Tina told her that I was looking for a girlfriend. She said that if she gave me sex that I could probably be talked into taking her to her school dances and to other things, where she could be seen with a high school boy and be the envy of all of the other girls.
Yes, I would take her to her school dances and even go with her to parties. I would be proud to be seen with a girl that was that pretty and willing to let me have sex with her.
Tina told Brie to go up my bedroom, lock the door, and to make sure that she was done by the time our parents came home. Brie would then go into Tina’s room for Mom to find her there when she came home. The plan was simple enough.
We went to my bedroom and locked the door then I helped Brie unbutton her blouse and take it off. She had known about this get together for a whole day so she had dressed especially for me to undress her. Brie was very sure of herself and smiled as I checked out her nice little boobs in that sexy little bra. I then reached for the snap and zipper of her jeans. She sucked in her tummy to help me get them down over her hips and all the way to the floor. As I started working on the snap my face got close to her breasts where I smelled some lilac perfume. It was faint but very sexy and feminine. As I leaned down further pushing her jeans down my head came closer to her pussy and I could smell the same lilac perfume there along with a very pleasant odor coming from her pussy. It was even nicer than the odor from my sister’s pussy. I was rock hard by then.
Brie stepped out of her jeans and stood there waiting for me to continue. I was in no hurry. I pulled Brie to me and kissed her softly and gently on the lips before I nuzzled my face into her neck and nibbled on her earlobe. She liked that. I reached behind her unhooked the two hooks on her bra like an expert, thanks to my sister letting me unhook her bra a few times. I pulled the bra off and smelled it before tossing it and leaning down to suck a hard little nipple into my mouth. After sucking on both of them for a moment I knelt down in front of Brie and hooked one finger from each hand in her waistband and pulled her panties down her hips revealing a very nice patch of pussy fur. I nuzzled my nose into it and inhaled deeply. She gently ran her fingers through my hair and held my face to her crotch. I kept my face right there as I lowered her panties to the floor and she stepped out of them. I then kissed her pussy and stood up holding her panties. I looked around and then I put her panties in a basket that was up on my top shelf. She knew that she was not getting them back and just smiled.
I undressed and took her to my bed putting her in the middle with her head on my pillow. I admired her body for a moment and then I touched every inch of it with my hands, front and back, and then her insides. I slipped a finger into her pussy and found her hymen. Tina had told me about them and said that I needed to break it with my cock and not my finger, so I was careful. Tina had told me to tickle her clit until she had at least one good orgasm, then lick her pussy until she had a second one. Only then could I slip my cock into her after asking her permission. Once I got just the head inside I was to stop again and ask permission. It was to be her idea all the way. Then once I had the entire length inside her and rested for a moment I was to start fucking her slowly. After that I could just let nature take its course.
It went like clockwork. Brie loved the clit stimulation and said that it was much better than she could ever give herself. She loved the fact that I was willing to go down on her. None of her girlfriends had ever had a boy do that to them, although many of her girlfriends had done that with another girl. That thought excited me. It was Brie that actually told me to stick it in her. After the head was resting at her hymen it was she that forced her hips up in the air and forced my cock inside her. Brie didn’t wait for anything she just wrapped her legs around me, kicked my ass cheeks with her heels, and forced me in all the way. God she wanted it more than I did. Well there was no longer a need to go slow and gentle so I just started thrusting into her with a need unlike any other that I had before. It was fast and furious and it didn’t last very long but I cum soon.
Brie said that my sister had told her that every cock that went in her pussy had to go into her mouth afterwards for a tongue bath. She rolled me over and sucked me clean. She also sucked me hard and got on top. She really was as horny as I was. I got to watch her titties bounce as she fucked herself on my cock. She was a possessed animal in heat. She was out of control as her orgasm struck her and she cried out.
Shortly after she collapsed on my chest there was a light tapping on my door and Tina asking me if everything was okay. Yes, it was more than okay. When Brie recovers she once again sucked my cock into her mouth. That time it did not get hard.
We heard a car pull into our driveway, Brie looked out my window and saw my mother get out of her car. Brie just casually picked up her bra, blouse, and blue jeans then unlocked my door and left. I quickly got dressed and went down the stairs. Mom passed me on her way up.
A few minutes later Tina and Brie came down the stairs laughing. Mom had caught Brie buttoning her blouse up and had accused them of making out together. Just to be a wise ass, Tina said that they had been. Surprisingly, Mom said that it was okay as long as I didn’t catch them doing it. That caught Tina off guard but it also gave Brie a reason to come over more often.
Tina had her own car so I went with her when she took Brie home. Tina said that we would be dropping Brie off at school every morning and picking her up after school every night. I was to be a gentleman and open Brie’s door, help her out, and give her a nice long kiss every morning, so that everyone in school knew that she was dating an older boy.
Meanwhile we were in the backseat, I was playing with her tits, and she was playing with my cock. We kissed a lot and then we were at her house. I almost got out without putting my cock away. She laughed and then I walked her to the door and kissed her goodbye.
On the way home I sat in the front with my sister. We talked about me loosing my virginity and how excited Brie had been afterwards. Tina then asked me if I would mind if she made out with Brie sometime. I asked her if I could watch. Tina suggested a threesome. I asked if I would get to fuck her too. Tina smiled and said that after what Brie had said about my love making skills that she would like to find out for herself just how good I really was. I told Tina that I owed it all to her instructions. She told me to come to her bedroom later after Mom and Dad went to bed. Okay! She also told me that she had to give Brie a pair of panties to wear home since I kept hers. I laughed.
At home Mom wanted a talk with Tina and took her up to her bedroom. I snuck up the stairs and listened outside Mom’s bedroom door as they talked. I heard most of it but afterwards Tina came to my bedroom and told me about their conversation. Mom was bisexual and liked girls as much as she liked men. Dad loved the fact that Mom was always willing to help him out with a threesome with another woman. That way they could both have sex with her. Mom only told her so that it would be easier for them to go to a motel for a night every now and then. Mom knew that Tina would understand. Tina said that on those nights that she would invite a girlfriend over to stay with her. Mom warned her about me but Tina said that she could control me. She told Mom that we just might have our own threesome with Brie. Mom liked that idea herself and asked Tina if she might join Brie and her sometime. Wow Mom wants to eat my sister and my girlfriend as much as I do. Cool!
The next day we picked Brie up early and drove to her school. I got out, helped her out of the car, and then I proceeded to kiss her for a full minute before handing her, her purse and her backpack. Then I gave her another shorter kiss and held onto one of her breasts as I did so, allowing the other students to see me do it. I got in the front seat with my sister and we left.
I was in heaven all day long, especially knowing that Brie would be spending the entire weekend with me. Mom and Dad were going to a motel to pick up women to share.
After school Brie was waiting for us with some of her girlfriends. I recognized one of the girls from Brie’s brother’s computer. He had fucked her. Anyway I greeted her with a single yellow rose that my sister had picked up for me and gave her a sweet little kiss right in front of her friends. Brie introduced me as her boyfriend and asked if I would take her to the dance that evening in the gym. Of course I would. She said goodbye and I let the other girls see my hand run down her ass and between her legs as she got in the car.
Brie told us how popular she was, how much she liked having me for a boyfriend, and how horny she was. She removed her panties, pulled out my cock, and sat on me as my sister made her way through traffic. When I cum in her she clamped her legs together and sucked me clean. I got hard but Tina said that we would have to wait until we got home.
At home Tina gave Brie a douche while I watched. She told Brie about our mother and father sharing girls that they picked up. Then Tina asked Brie if she could join us in bed. Brie said yes, then Tina let her give her a douche. Tina explained that nice clean girls were better to eat. Brie said that she already knew that and blushed. She told us that her girlfriend Stacy and her had done it a few times and that once her girlfriend tasted funny. It was the girl that I had recognized.
I told Brie about the pictures that I had found on her brother’s computer and took the girls into my bedroom to look at Stacy. Brie could hardly believe that Stacy had let four high school football players gangbang her virginity away. She had not believed Stacy when she had told her but the pictures proved it. She recognized her brother’s bedroom and him in the pictures, then three of his friends as they took turns fucking Stacy. The file dates confirmed the approximate time that Stacy had said that she lost her virginity and the fact that her brother had fucked and then gang banged a fourteen-year-old virgin.
Right after that Tina put Brie on the bed and started working on her lower half while I worked on her top half. After a while Tina traded places with Brie and I got to work on her top half for a while. After the girls were happy I got to cum in Brie. Then we took a shower and got ready for the dance. Tina loaned Brie some of her clothes and I got a quick lesson in slow dancing.
Tina dropped us off at Brie’s school and told us when she would return. If we needed her before that we could call.
Stacy was waiting for us when we arrived. She didn’t have a date so Brie invited her to hang out with us. I kissed Brie a few times and a teacher chaperone told me to stop. I didn’t but I was more careful about it. I also touched Brie’s boobs and butt often. When we slow danced I pulled Brie’s ass closer forcing my cock to harden between us. Brie whispered that I should take a few liberties with Stacy too. Once I was sure that she meant it I asked Stacy to slow dance too. I gave her a little kiss and ran my hands down her body. Stacy was not wearing a bra, she was wearing panties, and I could cup the bottom half of her ass cheeks in my hands under her miniskirt. I pulled her into my erection and she giggled. Then she ground her pelvis into me trying to jerk me off as we danced. I danced her into a corner were I could fondle her ass and cup her breasts in piece. I then reached inside her panties, into her moist slit, and rubbed her clit until she had an orgasm. Then we returned to Brie and I told her what I had done to Stacy.
Brie then told Stacy that she had seen the pictures that her brother had taken during her virgin gangbang and she apologized for not believing her. Stacy said that that was the only time that she ever had sex. It had not been a pleasant experience and not one that she wanted to repeat. Then Brie asked Stacy if she would like to spend the night with us in a threesome. Stacy liked the idea and asked her mother if she could spend the night with a girlfriend. It was okay with her. She hadn’t even asked which girlfriend.
The girls got me into the restroom where there were other girls but no teachers so we could make out all that we wanted too. The other girls didn’t seem to care because all of the stalls had doors on them. So Brie and I had a great time, Stacy and I had a great time, and then the girls had a great time too. I watched Brie and Stacy finger each other’s pussies and then suck their fingers clean.
Brie took me into one of the stalls where she had me pull my pants and underwear down, sit on the toilet, and for her to sit on my hard cock. I needed the relief and she just wanted to get fucked in her school, in the girl’s bathroom, and with other girls in there knowing what she was doing. They sure knew what she was doing too unless they were deaf. Brie kept telling me to shove it in harder, deeper, and to make her cum. I rather enjoyed fucking her in there like that too.
When the three of us came out of the girl’s restroom a teacher was standing there and escorted us outside where we waited for my sister to come and get us. Meanwhile the girls laughed their asses off for getting caught by the principle like that. They figured that they hadn’t heard the end of it yet and were just going to see what happened on Monday. Until then we were together and we were going to have a great time in a three-way…unless Tina wanted to make it a four-way. That way Tina could sleep with Stacy that night.
Tina came by as quickly as she could to take us home. She was pleased to see Stacy with us and Brie told Stacy that Tina had seen the pictures too. On the way home we filled Tina in on what had happened. She laughed because she remembered that Principle giving her a hard time once too.
At home Brie suggested that the girls all douche but Stacy wanted to eat my cum out of Brie just the way she was. Tina wanted to try Stacy in her natural state too. I didn’t care because I was just going to sit back and watch, that is until Stacy asked me if I was going to take pictures of them making out. Brie was all in favor of it and even Tina said that it was okay, especially knowing that I already had copies of her pictures from Brie’s brother’s computer.
So I observed one the best three-girl lovemaking sessions that ever existed. I took hundreds of pictures of them all, them close-up, and parts of them really close-up. I got still pictures and video too. In that two hours they exhausted themselves and one another with so many orgasms that they practically passed out. When they were done I was able to slip my cock into their pussies and into someone else’s mouth. In the end I figured that Stacy needed me the most, after all it had been about two years since she had lost her virginity in that gangbang and I was just what she needed. Brie was pleased that I showed Stacy what a nice guy could do for her. We all wanted to sleep together so we headed in to sleep in Mom and Dad’s king-size bed.
Saturday we didn’t even bother to get dressed. We walked around all day long in the nude playing with each other, kissing, and making love whenever we wanted too. Brie was very good about letting me fuck Stacy but kept reminding Stacy that I belonged to her.
Sunday was more of the same until Mom and Dad came home. I ran to my bedroom and the three girls ran to Tina’s bedroom. I got dressed and came out in time to see Tina invite Mom in for a little fun. They didn’t come down for another hour. Brie told me that I should have been there with my camera. She said that my mother was really good in bed. She also told me that on Tuesday Dad was going to be at work late and that Mom would be joining us in bed when she got home.