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Introduction:

One boy, four girls, and a whole lot of fun.
Fbailey story number 420


Sister, Girlfriend, And Fuck Buddies


Veronica was sixteen years old, she could drive a car, and she had a job as a cashier at the local drug store. In other words she was a responsible adult…so Mom and Dad left her in charge of me for the weekend while they went off somewhere.

The first thing Veronica did was call all of her girlfriends and tell them to come over Friday night around dark. Then she told me to take some food, drinks, and movies to my bedroom and stay there. At fifteen, I didn’t like to be told what to do by my parents let alone my sister.

Obviously, I decided to resist.

I knew every inch of our house inside and outside. I knew how to slip in most of the windows and which of the windows that I could see into from the ground, trees, or on the roofs. I even got out Dads two ladders and set them up outside Veronica’s bedroom. Then I ran around inside the house fastening the drapes back in those cute little cloth straps that Mom likes so much. I opened the see through curtains, raised the blinds, and even used Windex to clean the glass itself. I cracked a few windows open an inch or two so that I might hear them too. My camera batteries were fully charged, the SD card was empty, and I had cleaned the lens.

That Friday night I was outside as the girls started arriving. Veronica headed them down into the family room. Perfect! I could lie on the grass and look in the windows. Veronica knows that we have shrubs and bushes all around the house, keeping people from looking in the windows. However, I know how to crawl in between the house and the bushes to look in the windows. I noticed that no one had bothered to close the drapes.

I looked as the girls built a nest of sleeping bags, blankets, and pillows on the floor. Then Veronica pulled a case of wine out of the closet. I wondered where to hell she had gotten that and then I quickly decided that I really didn’t care. In fact I was hoping that they would all get drunk and that I would get some great pictures.

It didn’t take that bunch of girls very long to start drinking and playing Truth or Dare. Her three girlfriends were Sally, age sixteen, a cheerleader, and a blonde that always wore her hair in a ponytail. Tessa was a fifteen-year-old from down the street that both my sister and I had known forever. She was cute and had brown hair almost to her waist. Then there was Scary Sherry, age seventeen, and every boy’s nightmare. Sherry was mean to everyone including the teachers. Her hair was jet-black, all of her clothes were black, and her nose was pierced.

Their game started out simple enough. They were building up their courage and the wine was helping. The truths revealed that only Tessa was a virgin, that they all liked to drink, and that they had all smoked pot. As they continued I found out that they had all made out with another girl and that they had enjoyed it. The ones that had let boys fuck them had liked that too but not as much. It seems that the boys just used them as a fuck toy and cast them aside. Tessa said that she wanted a nice boy…like me. My sister laughed at her and said that she would regret telling her that. I learned bra sizes, boyfriend’s names, and heard about them loosing their virginities.

My sister said that she lost her virginity to a boy when she was only thirteen years old. According to her he was twenty-one years old and had given her a ride home after she finished soccer practice. She was supposed to get a ride home from a friend but he had offered to take her home. Then he didn’t take her home at all, he took her to his place. He kept kissing her and feeling her breasts until she started enjoying it. Then he started feeling her pussy against her will, but then she started enjoying that too. Eventually he was fingering her pussy, giving her orgasms, and telling her how much he wanted to fuck her. Before she knew it he had her clothes off and he was lying on top of her. When he forced himself between her legs she opened them up for him. Soon he shoved his massive cock into her virgin pussy causing her to cry out in pain. He clamped his hand over her mouth and kept fucking into her until she stopped screaming. He had raped her and he had cum inside her. Afterwards he made her get dressed and walk home. She cleaned the skin from his back out from under her fingernails as she walked home. She had cut him up and he was bleeding from the attack. She too had bleed from the attack. Her pussy had been sore for days afterwards. She never went back to soccer practice and she never saw him again. I never knew that my sister had been raped and that that was how she had lost her virginity.

As the night worn on they drank heavily and Truths turned to Dares. Then it was decided that all of the girls would do whatever was said. I watched as they all got naked, as they kissed all of the other girls, and as they fingered the other girl’s pussies. Then it was my sister that Dared everyone to suck my cock. I panicked and rushed up to my bedroom. I just barely got in my shower when my sister barged in and told me to follow her down into the family room where the girls were. I had gotten my clothes off with the dirt and grass stains on them at least. First I had to give her some shit about coming into my room unannounced and then coming into my bathroom while I was in the shower. She apologized and told me that I could do the same to her sometime. When I looked out at her she was still naked so I asked her what she was up too. She told me that she and the other girls had been drinking and that they were all feeling pretty good. She said that they had dared one another to get naked and then she told me that I didn’t need to get dressed either. I smiled and dried myself off a little, and then I followed my naked sister out of my room.

I followed her into the family room where the other three girls were sitting on the floor naked. It was much better than sneaking peeks at them through the window.

Veronica sat down in the circle with the other girls then said, “Each of us girls have to suck your cock for ten seconds. It’s a Dare.”

Scary Sherry said, “Don’t you dare cum in our mouths though.”

Tessa said, “Because you have to cum in my pussy. They ‘dared’ me to give you my virginity.”

Sally said, “Afterwards you get to fuck all of us including your sister.”

I looked at Veronica and asked, “For real?”

Veronica replied, “Yes, little brother we figured that it was high time that you and Tessa loose your virginity.”

I said, “I meant about fucking you.”

Veronica smiled an said, “Yes, Scary Sherry ‘dared’ me to let you fuck me. It seems that incest is just about the only thing that I haven’t done sexually.”

Scary Sherry added, “Actually the ‘dare’ was that she let you fuck her every single day until she graduates from high school.”

I looked at my sister and said, “For real?”

Veronica scowled at me and said, “Yes. Any hole. Anytime. Anywhere. Are you satisfied?”

Tessa said, “He will be after this weekend. I’ll see to that. I’m part of the dare too. I’ll be your girlfriend and you can fuck me every single day until I graduate. Any hole. Anytime. Anywhere.”

I looked at Sally and Sherry and said, “So far these ‘dares’ seem to include all four of you girls.”

Sally and Scary Sherry said in unison, “Okay. You can fuck us every single day until we graduate. Any hole. Anytime. Anywhere.”

I had to laugh at the way they said it. Their hearts certainly were not in it. I looked over at Veronica and she was smiling from ear to ear. I knew right then that my sister had taken care of my sex life for the next several years. I certainly appreciated having Tessa as my girlfriend. I had known Tessa my whole life and she was my own age. I was looking forward to loosing my virginity with her. Then I thought that I should loose all of my virginities to her so I walked over to Tessa and stuck my cock in her face. She smiled at me as she took it in her hands, kissed the shinny pre-cum head, and then sucked it into her mouth. Ten seconds later I fed it into my sister’s mouth, then Sally’s mouth, followed by Scary Sherry’s mouth.

When I pulled my cock out of Scary Sherry’s mouth Tessa was on her back with her legs up and open inviting me in. I looked at her in a whole new way. I had always liked her and wondered what it would be like to make love to her but this was different. She was offering herself to me like a sacrifice, her body was fully exposed to my gaze, and it was completely at my disposal. I knew that I could do anything and everything to her and that she would let me.

I had often wondered about trying to get into some girl’s bra or panties to cop a feel with her just barely allowing me access. I had often thought about trying to get a girl to uncross her legs so that I could get my tongue or even my finger into her pussy.

Then I looked down at Tessa again. Here was my dream girl fully open and available to me. It was so much more pleasant than anything that I had ever dreamed about.

I got down on my knees near her crotch, smiled up at her, and then licked her pussy. My tongue slipped into her moist slit and I tasted my first girl, my girlfriend. My tongue touched her clit and she moaned out sweetly as if she never wanted me to stop. I didn’t want to stop. I spent a long while licking Tessa’s pussy and her asshole before I kissed her bellybutton and then her little breasts. I then touched the head of my cock to her vaginal opening as I sucked on her nipples. After I had enough of her nipples I moved my mouth to her mouth and my cock into her pussy. For the next few minutes I fucked my tongue and my cock into her orifices enjoying both immensely. Tessa was actively fucking back at me. I was pleased that she wanted it as much as I did and not just because it was a dare. I could feel the cum raising in my balls and somehow I thought that Tessa could feel it too. All of a sudden I thrust into her hard and shot a gob into her as she gripped me in her limbs and shook as if she was shivering from the cold. I realized that she was having an orgasm and that we were cumming together. It felt wonderful. I fired into her over and over again as she to had more than one orgasm. We were both spent and sweaty when I rolled off her.

Veronica allowed us to bask in our afterglow before sending the two of us to my room to take a shower. Tessa and I stood under the nice warm spray and kissed. She thanked me for taking her as my girlfriend. I told her that I had wanted to ask her myself but that I was too scared to ask her. We were both glad that my sister had put us together. I ran my hands over every inch of her body trying to memorize it. She was doing the same thing to me. Eventually we joined the other girls in the family room. We were holding hands as we went in.

Veronica reminded me that I had three more girls to fuck before the night was over. I looked at them all while still holding Tessa’s hand. Sally was the typical blonde cheerleader with her hair back in a ponytail. She was what most boys would want and I could have her. Most people considered my sister a slut but she was also very sexy and the thought of fucking my own sister was very intriguing. I also knew that I would be fucking her every single day until she graduated from high school, maybe even longer. Then there was Scary Sherry. Her jet-black hair was straight and shinny, her pierced nose was sort of cute but not really, and then there was her pussy. It was quite puffy, the black hairs were trimmed short, and her outer pussy lips stuck out prominently. I could see her inner pussy lips hanging out even further and her swollen clit at the top of her slit. She might be scary but she was also sexy as hell. I was looking at the three of them and wondering who I would fuck next.

Scary Sherry took my hand and said, “I don’t want an audience.” Then she took me off toward my bedroom. She pushed me in and locked my door, and then she led me over to my bed. When she got on top of it, it was not in the completely submissive way that Tessa had. She looked scary or possibly just scared. Either way she pulled me on top of her and mashed her lips to mine. Soon she was pushing me down to her pussy so that I could lick it for her. She had the sweetest taste yet. Well I had only tasted two girls but she was still the sweetest. Like Tessa I enjoyed her pussy and that protruding clit for a good while before moving up to her hard nipples and resting the head of my cock at her pussy entrance. After I finished with her nipples I moved up to her mouth and again inserted my cock and my tongue into her two orifices. My tongue went in easily but my cock didn’t. I had hit an obstruction. Her hymen was still intact. It was an obstacle that I could over come. Of course at the time I didn’t know what I had hit. All I knew was that Sherry told me to press harder and I did. Something snapped and my cock slipped halfway in. Sherry let out a soft scream and clung to my body tightly. As I fucked into her tight tunnel Sherry confessed to me that she had been a virgin and threatened to kill me if I ever told anyone that I had taken her virginity. She was scary enough to do it, so of course I told her that her secret was safe with me. Knowing that I had gotten her virginity excited me. Knowing that I had broken her cherry excited me even more. Tessa had already broken her hymen before I got to her and in my mind that made Sherry even more of a virgin. I liked knowing that. I also wondered why Sherry had given it to me but I wasn’t about to ask her.

Pushing my cock into her was the best feeling ever. She was tight, like one of those surgical gloves that we have to put on in science class. The difference between her and Tessa was incredible. Sherry’s body was much firmer, her breasts were too, and that ass of hers was spectacular. She held onto me for quite a while until she got used to the intrusion, then she relaxed and told me to go slow. I got into a nice slow motion and she seemed to enjoy it. She even started to moan a little and breathe a little harder. I could tell that she was going to have an orgasm. I didn’t think that girls had orgasms when their cherry got broke, but I could feel my cock rubbing against her large clit as I pushed in and pulled out of her. That was when I made sure to rub it extra hard. My thoughts were to give her several orgasms that she would remember forever along with the fact that she had given me her cherry.

I was making love to Sherry and she was no longer scary plus making love to her was even nicer than making love to Tessa. I kissed her every time that I felt an orgasm erupt in her. I could feel her pussy contract around my cock. I could hear her breathing become shallow and I could hear a deep hoarse sound coming from deep in her throat. On her fourth orgasm I stated thrusting into her and filling her with cum. Sherry just held on for dear life. As we lay there side by side Sherry said, “Please don’t tell anyone about me being a virgin. I think I love you. That was the most painful and the most pleasant thing I have ever experienced. Thank you.”

I asked, “Does this mean that I can do it again?”

Sherry laughed and said, “Not right now but as we all agreed: Any hole. Anytime. Anywhere.” Then Sherry kissed me and took me into the bathroom for another shower.

When we entered the family room, Tessa smiled at me and winked. My sister smiled too as did Sally. My sister said, “Two down and two to go. Are you saving the best for last?”

I smiled at my lovely sister and said, “Maybe.” I was positive that she was no virgin. I had actually listened at her bedroom door on a few occasions when one of her many male friends were in there with her fucking her brains out. I knew when she orgasmed too because she always cried out “Oh my God” three times and then went dead silent. Soon after that I would hear the toilet flush. That was my cue to get out of there.

Once I had found her computer on and she had entered her password. I managed to find her diary and copy it to my flash drive before she knew it. Then I had spent several hours reading it. I had no idea that my sister Veronica was such a slut. She had made a list of every boy in her high school by grade and she was fucking her way through them. At that time Veronica had fucked seventy-three of them. I was on that list…

An hour later I let Tessa suck me hard and then I fucked Sally right there in front of everyone like I had Tessa. Sally wanted it doggy style with her big tits swinging as I pounded her from behind. I entered her easily, grabbed a hold of her blonde ponytail, and then held on for the ride of my life. For a moment there I thought that I had joined the rodeo and entered the bucking bronco contest. Sally was thrashing around wildly and I had a hard time staying with her. Soon I had split her ponytail and was holding on with both hands while thrusting into her violently. She was nothing like my first two fucks. In fact Sally could be called, ‘The fuck of a lifetime.’ She was a ride worth taking. When I started cumming in her it was me that cried out, “Oh my God” three times. Sally just waited until I had finished and turned around to lick my cock clean. Sally said, “I love to suck my juices off a guy’s cock.”

When Sally was done with me Tessa took me to get a drink and a bite to eat while my sister flipped Sally over and licked her clean. I had to smile knowing that my sister was sucking my cum out of Sally.

Tessa said, “Only one more to go. Are you up to it?”

I replied, “I’m sure I will be in a while, especially if you help me get hard again.”

Then Tessa asked, “What was it like fucking Scary?”

I said, “She tasted really sweet down there and she was tight too. Actually she was just as nice to make love to as you were. Sally on the other hand was not at all what I had expected.”

Tessa said, “I know, that is what I expected you to get from Scary.”

I replied, “Not at all, Sherry was just as nice as you were, I swear.”

Tessa then asked, “What do you think about your sister?”

I replied, “I don’t know. In a way the incest thing is a real turn on. I like the thought of fucking my own sister. Hell, I like the thought of fucking my mother too. Then when I think that a hundred guys have already fucked her I get worried about catching some disease.”

Tessa said, “A hundred. Oh my God!”

I treaded water by saying, “I don’t know but I think it is a high number. Then again after fucking Sally I can’t help but wonder how many men she has let fuck her.”

Tessa said, “Why don’t we just ask them.”

I followed her from the kitchen back down to the family room.

Tessa said, “Hey guys I have another ‘truth.’ How many different cocks have fucked you? I’ll go first. One!” Then she kissed me and took a hold of my cock.”

Sherry looked at me with anger in her eyes. I shook my head no signaling her that it was not my idea.

Sally said, “Twenty-eight, no twenty-nine now.”

Veronica said, “Eight-two with one more to add later.”

Everyone looked at my sister as if she had exploded. No one even looked toward Sherry.

However, Sherry said, “Promise not to laugh.” Everyone nodded their heads. “One. His. I too was a virgin until tonight.”

Tessa squeezed my cock harder as it started to raise.

Not a word was said until Veronica asked, “Is that for me little brother?”

I then asked, “Is it okay?”

Veronica asked, “Why wouldn’t it be. After all it was my ‘dare’ initially.”

Tessa said, “I think he wants to know if he will get some sexually transmitted disease from you and pass it on to the rest of us.”

The other girls looked at my sister.

Veronica said, “That’s a fair question. Mom was concerned too so she took me to a doctor last week. I’m clean. No STD, HIV, or AIDS here.” Then she patted her pussy. “I don’t have chlamydia or a yeast infection either. I’m clean. I swear. Now fuck me.”

I felt Tessa pushing on my ass to send me in Veronica’s direction.

Veronica leaned back and opened her legs up me. She said, “I’m wet. I’m always wet. Just stick it in me.”

I did as requested and shoved my cock into my sister’s pussy. I shoved it in hard. She really was very wet and it slipped right in with no hesitation at all. My pelvic bone smashed into her love mound with an urgency that neither one of us realized.

Veronica said, “You’re number eighty-three. I’ll never forget you.”

I laughed and said, “I’m your brother. How could you ever forget me?”

She too laughed and said, “No stupid. I will never forget that you were number eighty-three.”

Puzzled I asked, “What’s so special about being number eighty-three?”

She thrust her hips up at me hard in an effort to throw me off her. Then she said, “It’s my birth year you jerk.”

I slammed down into her just as hard as I could and said, “Should you be calling the guy fucking you a jerk?”

Veronica said, “Yes! Because when I get them mad they fuck me like they never fucked anyone else. I like it rough, the rougher the better. Come on little brother you can do better than that. I’m not Tessa, you can fuck me a lot harder.”

I had become an expert at jerking off but real fucking was a lot different. Instead of my hand doing all the work, my hips and arms were getting a workout. Also, fucking my forth girl in one night was sure taking its toll. It seemed to be taking forever too. Veronica was so wet that I had to do something to make more feeling so I told her to cross her ankles. That closed things up around my cock for sure and gave me the friction that I so desperately needed to cum. “Thar she blows!”

That night I took Tessa and Sherry to bed with me while Veronica took Sally to bed with her. As I lay there between the two girls I could feel their bare breasts against my ribcage.

Tessa asked, “Am I going to be your girlfriend?”

I replied, “Can I have two girlfriends?”

Sherry said, “I’m not sure that that would work out very well.”

I said, “Well when this day started out we were all virgins and you both gave your cherries to me. I would really like it if the three of us could be good friends. Like in a threesome.”

Sherry said, “In all of the threesome movies that my mother has in her collection the two women in the threesome make love too.”

Tessa asked Sherry, “Have you ever made out with another girl?”

Sherry said, “Only once when I was eleven in Bible Camp.”

Tessa started laughing and said, “Me too. Honest to God, I was eleven years old and in my Church Bible Camp. She was my Cabin Monitor. I had to lick her pussy in the shower every night and then she would piss on me.”

Sherry asked, “She never licked your pussy?”

Tessa said, “No.”

Sherry said, “At least I got my pussy licked. There were two of us girls in that cabin that hadn’t started our periods yet, so we were forced to sixty-nine every night while the rest of our cabin watched. They called it the ‘floor show’.”

I decided to get in on the conversation, “Well from my standpoint I have tasted both of your pussies and I liked them both. Sherry I do have to admit that your pussy is delicious.”

Sherry said, “I always lick my own fingers after I masturbate.”

Tessa said, “So do I.”

I got up and moved to the bottom of the bed taking the covers with me. I then raised their knees and opened them so that I could get in near their pussies. I licked Sherries pussy, swirled it around in my mouth, and them swallowed. I licked her again and moved up to stick my tongue in Sherry’s mouth. Then I liked her again and stuck my tongue into Tessa’s mouth. After that I licked Tessa’s pussy and tasted it myself, then I fed it to Tessa, and finally to Sherry.

That got the ball rolling. Sherry came down near me and licked Tessa’s pussy directly. After a couple of licks she turned around and pressed her pussy into Tessa’s face. I watched as my two girlfriends made love. It was special and it was so beautiful to watch. They didn’t stop until they had each received an orgasm. Then both girls stuck their tongues in my mouth.

I got back in between them and we three fell asleep.

The next morning at breakfast Sherry said, “Last night Tessa and I made love. If we share a boyfriend we should share one another. We need to include you two girls now.”

My sister said, “Not a problem. Sally and I made love last night too.”

Sally added, “We have done it a few times before but usually just to entertain the guys around us. However, last night was for our own benefit and we both enjoyed it.”

Veronica added, “Yeah, three times each.” Then she laughed.

I knew right then that my harem of four girls was going to work out well.


The End
Sister, Girlfriend, And Fuck Buddies
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