My sister lost a bet and I turned out to be the big winner.
Fbailey story number 614
She Lost A Bet
It was a very worm summer day. It was the kind of day when you cannot take enough clothes off. Our house is usually cool throughout the day because of the shade trees and the constant breeze. That however was not what it was like that day. There was no breeze and the sun was overhead heating the house like an oven.
I was wearing my tight swim trunks and my sister Alice was in her skimpiest bikini. She had really matured over the winter and she was looking amazing. Her breasts had grown, her waist had slimmed, and her hips had filled out. She resembled Mom more and more each day. She was fifteen years old and I was fourteen.
She had called some of her girlfriends up and asked them to come over. Only two showed up but they were her prettiest girlfriend and if I may say the sexiest ones too. They arrived in T-shirts and shorts but quickly stripped them off to reveal their skimpy bikinis too.
I was surrounded by three of the sexiest girls that I knew. They disappeared up into Alice’s bedroom but came down shortly afterwards. I was out in the backyard sitting under a big shade tree trying to stay cool and read. It was Dad’s latest Playboy magazine and believe it or not, he actually lets me read it. Mom isn’t so pleased about it but she tolerates it.
Angie came dragging Alice out to me. Alice had both of her hands covering her breasts. She was not wearing her top.
Angie said, “Show him.”
Angie said, “You lost the bet, now show your brother your boobs.”
Again Alice refused. About that time Gina slipped up behind my sister, reached out, and pulled Alice’s bikini bottom down to her ankles.
Alice stood there in shock. She could not believe that one of her girlfriends had done that to her. I was treated to her beautifully trimmed brown bush. It was in the shape of a double heart. The inside was a small bare heart-shaped spot just above her slit and the outside was a furry heart-shape. I had never seen anything that nice in Playboy. It all took place in slow motion in my head. I saw Alice moving her hands down from her covered breasts to her exposed pussy. Her breasts then became my prime focus. They were just as nice as the Centerfold that I had been admiring. Somewhere in all of this Alice left one hand on her half-exposed pussy and tried to cover both breasts with the other hand. Obviously that did not work out very well. In an effort to get away Alice turned, tripped in her bikini bottom, and fell right in my lap. Her arms went flying above her head. All I had to do was reach out and grab both of her wrists in my one hand and then place my other hand on her belly to hold her down, keep her exposed, and admire her for a couple of seconds longer.
Alice said, “Let me up, please.”
I replied, “I can’t. I’m in love with your body. It is the most beautiful thing that I have ever seen and I have seen all of Dad’s Playboy magazines for years.”
Alice calmed down and asked, “Do you really think so?”
I replied, “You bet.”
Angie laughed and said, “That was the bet that she had lost.”
Gina said, “We told her that you would say so.”
I had to smile because it had just occurred to me that Alice had been set up. Gina knew very well that I was in love with my sister’s body. We had often discussed it at length. Gina was also in love with my sister’s body but she had actually seen it on several occasions. She always jumped at a chance to go shopping with my sister in hopes of seeing her naked in the changing room. Gina was even hoping to get Alice and I in bed with her sometime. She was willing to give me her virginity in exchange for a chance to have sex with my sister. Angie had just been duped into helping unknowingly.
As Alice lay there on my lap I loosened my grip on her wrists and she put an arm around me and her other arm down to her side.
Alice asked, “How long do you want to look at me?”
I replied, “Until I get so hard that I will have to go up to my bedroom to jerk off.”
Alice asked, “Can I watch? Can we watch? Can you do it right here?”
I smiled and said, “As long as you stay naked I will.”
Alice smiled at me and asked, “Would three naked girls make you squirt more?”
Gina was already removing her bikini top when Angie said, “This was not part of the original bet.”
Gina said, “I don’t think he will care if a tampon string is hanging out of you bloody hole.”
Angie said, “But it is embarrassing to me.”
Alice asked, “What if you just removed your top?”
I asked, “What if you tucked the string up into your pussy lips just a little way?”
Angie turned around, bent over slightly, and played around in her bikini bottom. Soon she dropped them and turned around to face me before removing her bikini top. Meanwhile, Gina had removed her top and was stand close to me naked. Angie came closer too and my sister scotched away from me but stayed on the grass and opened her legs up wide. Gina opened up her stance to expose her pussy more. Angie just looked down at me with her knees clamped tightly together.
I lifted my butt up and pulled my trunks off. I grabbed my cock in one hand and reached out to touch my sister’s nipples with my index finger. I reached for Gina’s nipples and she leaned in for me. Angie did too when I reached for her nipples. I was stroking it pretty well by then.
I reached out to touch Alice’s pussy. She let me run a finger up her slit to touch her clit and down her slit to slip my finger just inside her a little bit. Gina stepped closer and squatted down for me to do the same to her pussy. When I reached for Angie she hesitated but she kept looking at my cock as she too squatted down for me. I stroked my cock and I fingered her slit, I rubbed her clit as I tightened the grip on my cock, and then I fingered Angie’s hole poking at her tampon as I shot squirt after squirt into the air. The first two shots hit my sister but the rest landed in the grass until I was finally dribbling down my hand.
Alice said, “That was simply incredible, can you do it again?”
Gina said, “I had an orgasm when you fingered me.”
Angie said, “I’m still having one, please don’t stop fingering me. I get so horny when it is my time of the month. I always though that it was dirty and no boy would want me then.”
I said, “I don’t think it is dirty, I think that it is normal, and I would give anything to make love to you right now.”
Alice said, “Anything! How about…”
Angie cut her off by saying, “Hey this is my body if anybody gets his ‘anything’ it will be me.”
I grabbed a hold of her string and started to pull as I said, “Make a wish.”
Angie said, “I wish that you would fuck me.”
I smiled, pushed her back onto the grass, and then I slipped my virgin cock into her. I said, “Wish granted.”
Angie asked, “Do I get two more wishes?”
I replied, “Yes, of course.”
Angie kissed me and said, “My two girlfriends are virgin too. Will you fuck them?”
I replied, “Yes, I will.”
With my cock nestled lovingly inside her bloody hole it didn’t really care what the lubricating fluid was. To my cock that warm wet tunnel of love was everything in the world to me right then. Angie would forever be my first fuck but I could not help but anticipate fucking my sister, the girl that I had dreamed of fucking since I first started to masturbate. My mind seemed to wonder from Angie to Alice as I fucked into the girl below me with all the passion that I could muster. The ground was not forgiving as I pounded her pelvis, flattening her ass out with every stroke, and enjoying the feeling of her love muscles squeezing my cock. The sensations that were flowing through my body were not new but the feelings were. It seemed like a long time that we made love to one another before we climaxed together.
Angie kissed me holding me tight to her as she whispered, “Thank you for making me a woman. If you will have me, I would be proud to be your girlfriend.”
I whispered back, “I would like that…but…would you mind if I fucked your girlfriends?”
Angie said, “Not at all. In fact you can invite them or any girl for that matter to join us in bed anytime that you want too.”
I whispered, “Only girls?”
She replied, “I really like girls but they seem to want a boy in bed with them, otherwise they think that they might become lesbians. I know of a lot of pretty girls that would join you and I in bed, including the two behind you.”
When I rolled off from Angie my sister was right there with a soapy washcloth and a towel to clean us up with. Gina even had a fresh tampon to insert into Angie’s freshly fucked hole. I was washed first and I enjoyed my sister’s hands on my cock and balls as she cleaned me up. Then I got to watch her as she ever lovingly cleaned Angie up. Angie did not have to do a thing other than spread her thighs and lift her butt slightly. Once she was clean it was Gina that slipped the tampon into Angie. It was not the kind with the applicator though, because Mom used the smaller ones to hide in her purse. I watched the tip of Gina’s finger slip into my girlfriend’s pussy. She wiggled it around much more than I figured it should. It finally dawned on me that Gina was feeling her up. I knew right then that she would join us in bed just as easily as she wanted to share me with my sister. As aggressive as Gina was I couldn’t help but wonder why she had not taken Angie to bed all ready.
When I was rested I crawled over to where Gina had been sitting. I gentle pushed on her shoulders and she lay back on the grass. She opened up her legs and welcomed me in between them. She even held my cock and aimed it at her virgin hole. With her feet behind me she pulled me into her. I thought that her aggressiveness was perfect so I rolled us both over and let her lead. Gina smiled as she lowered her breasts into my face to give me something to do as her hips bounced up and down like an out of control elevator. I could then feel her crushing my pubic bone with her own and my ass flattening out on the grass as Angie’s had earlier. I smiled as I clinched one of her nipples between my teeth gently and waited for her to sit upright ripping it from my mouth. She giggled and offered me the other one to latch onto. Soon I was holding onto her ass, kissing her, and shooting gobs of cum up into her. I hugged her for a few minutes before I allowed her to roll off from me. Angie was right there with the warm wet washcloth and cleaning my cock but not before she sucked the head into her mouth and drained the last couple of drops from it. Then I smiled as Angie licked my cum from Gina’s pussy before washing her up. I knew that both of those girls were fulfilling a fantasy right then. I looked over at my sister and she looked jealous that Angie wasn’t sucking on her pussy. I knew that she would be soon enough.
We rested and we talked about what a beautiful day it was to loose our virginities. Alice crawled over to me and asked, “Can you do me doggy style?”
I replied that I would be honored too and watched as she crawled over top of Gina into a sixty-nine. I crawled up behind her. Angie came in real close behind me and watched me fuck my sister for the first time, in a front row seat. Alice then leaned down into Gina’s pussy as I slipped my cock into her. I had never thought of my sister as a lesbian but I could hardly think of her as anything else as she sucked on that pussy.
Angie said, “I wish I was Gina right now.”
Alice stopped long enough to say, “It would have been you if you weren’t on the rag. Maybe in a few days we can all do this again.”
Angie went around me and slipped her hand down between my sister and I. She then felt my cock slipping into my sister. I didn’t know it at the time but she was getting her finger wet so that she could stick it in my sister’s butt. I could feel her finger rubbing along my cock through the thin membrane that separated her two holes. Fucking my sister third was exactly what my cock had needed. I had all the time in the world now and I took it. Alice was the tightest of the three girls even without Angie’s finger in her ass. Alice was also the one that lived in the same house with me so I knew that I would be fucking her more often that the other two girls. As for Angie, she showed no signs of jealousy. She seemed to like girls as much as I did. I could even envision myself marrying her someday. Like Dad always said, “Son, if you find the right girl don’t let her get away. I didn’t let your mother get away.”
The only problem was that I had three girls and I didn’t want any of them to get away. My sister would always be my sister, my girlfriend would become my wife someday, and that only left Gina. I remembered the conversations that Gina and I had about getting my sister in bed and thought that maybe I would not loose her either. Watching Alice eat Gina’s pussy I was pretty sure that she and Gina could become lovers. Maybe everything would work out for the best in the long run.
I filled my sister’s pussy with cum and was pushed off by Gina so that she could latch her lips onto Alice’s pussy lips. Meanwhile, Angie kissed me and whispered, “I like watching you fuck the another girls especially your sister. I found that to be very erotic, you know, the incest thing and all.”
I whispered back, “I can hardly wait until your period ends so that I can watch you three girls in action.”
Angie said, “Maybe tomorrow. I’m near the end.”
That night Mom asked, “So how was your day?”
I was drinking a glass of milk at the time and some came shooting out of my nose.
Mom laughed and said, “That good huh?”
Alice said, “Better that that. He lost his virginity and gained a girlfriend at the same time.”
Mom looked at me as I was cleaning up the mess that I had made with my T-shirt and said, “Well he does have a nice chest, he isn’t bad looking, and maybe I’ll have less cum to get out of his sheets.” She paused and said, “Then again I just might have more cum if they make love in his bed.” She looked me straight in the eyes and asked, “Can I ask who the lucky girl is?”
Again Alice chimed in with, “Angie is his main girlfriend, Gina is his number two girlfriend, and I am his number three girlfriend.”
Mom just looked at Alice.
Alice added, “Well he took all of our virginities but he gave his to Angie.”
Mom blushed and asked, “You let your brother fuck you? After all the fighting you two did this past winter.”
Alice smiled and said, “What can I say? I lost a bet.”
Mom smiled and said, “I lost a few of them myself.”
I knew that Alice wanted to tell Mom the details but she let it go. It was sufficient that Mom knew that we were having sex together and that it didn’t seem to bother her one bit. That of course led me to believe that there was more to Mom than met the eye.
That night after I had gotten in bed my door opened and Mom came in. She turned on the light and asked, “Are you wear anything?”
I replied, “No.”
Mom then reached out into the hallway and pulled my sister into my bedroom. Mom then removed Alice’s nightie and pushed her toward my bed. As she closed my door she laughed and said, “Have fun. I will.”
Shortly after that I heard Mom and Dad giggling as they ran past my bedroom door, down the stairs, and out through the back door slamming it as they went. Alice and I peeked out my bedroom window. Mom dragged Dad out to the shade tree where Alice and I had lost our virginities. They were butt naked and giggling like school children.
Mom pulled Dad in between her legs and waved at us in the window.
Alice said, “Apparently we weren’t the first to make love out there on a hot day.”
I asked, “Should we join them?”
Alice pulled me back to bed and said, “No, she won honest and fair. I lost again, but at least I got you and a bed this time.”
We made love often that night taking a nap in between each time. Gina and Angie were there early and climbed in with us. It was going to be another hot day.