Experiment with my Sister (Inc, Bro, Sis) Sometimes it amazes me how a little thing can turn into something memorable. You can go around looking to be lucky, but nothing happens. Yet again, something small can lead you to rewards that you never expected in your wildest dreams. This is about how my luck changed one day. I am an average guy who just earned my high school diploma and hanging around at home, enjoying the hot Arizona sun, till the autumn session started at the nearby community collage. My father has his own business and doing reasonably well and my mother works as branch manager for a regional bank. My only sibling, my sister, Samantha, who I call Sam is year and an half older than me and attends the same community collage that I am planning to attend and works as part time waitress, hoping to save up enough to move out of the house. Sam is not centerfold material, but has a very sexy athletic body packed in her 5’5’’ frame, highlighted by big perky breasts, tight long legs, and an awesome round ass. She has dark hair and brown eyes inheriting our mother’s Hispanic genes. If you saw her once, you may forget her face, but not her awesome breasts and her ass. In any case, I cannot think of many men who would kick her out of their beds. Sam and I had a great relationship. Yes, we had our little fights, but in spite of that we got along really well. In fact, Sam often told me that I was ‘cool’ for a guy my age. Our relationship even got closer, when I caught her smoking pot in the backyard and didn’t tell parents about it. Then she also became my smoking buddy. When parents weren’t home, she would often rollup a joint and shared it with me. I wasn’t much into pot, but I always kept her company and had a puff or two. One particular morning, I had just finished my breakfast after our parent left home to work and was getting ready to mow the lawn when Sam came home after working the night shift at the chain restaurant where she worked. Knowing that she likes to hit the bed soon as getting home and not wanting to disturb her with the sound of the lawn mower, I warned her of my intentions and she decided to take dip in the swimming pool till I finished my yard work. Usually, I also jump in the pool after yard work in the hot sun and therefore I normally mow the lawn in my swimming trunks. When I came downstairs after changing, I went straight to the kitchen to have a glass of water before going out to bake myself in the sun. Sam was already in the kitchen, standing by the sink wearing her two piece bikini swim suit. Instead of walking into the kitchen, I stood by the doorway and admired her awesome ass, her nice olive thighs and her sexy figure that drove me insane at times. Part of me wanted to lean behind her and enjoy the warmth and softness of her body, but I knew that was wrong. Instead, I found the center of her bikini stuck between her ass cheeks and decided to walk in and grab the bikini from two ends and get it out of her crack, which I did in one swift move. “Hey, what FUCK are you doing?” she turned her head around and yelled. It was very unlike Sam who would initiate similar horseplay at times. Her annoyance to my play and tone of voice had me taking few steps back immediately. “He Sam, chill out… I was only playing. You damn bikini was stuck in your ass and I only got it out of there. It wasn’t like I was going to stick something in your ass, you know” I said, defending my action and walked out mow the lawn. After I finished my work, I jumped in the pool for dip. I found Sam seated in the shade after a dip in the pool, waving a joint at me as I approached her. She looked calm and appeared to have gotten over the earlier incident. “What the hell was wrong with you earlier Sam” I inquired as she took a puff. “I am just tired of all the guys looking and treating my ass as a sex toy, Josh, I wasn’t angry with you, it just that…” Sam stopped in the middle of her sentence. She glimpsed at me then looked away. “Just what?” I asked wanting her finish what she had in mind. “I don’t know… It is like all these macho men are gay or something…. They want to stick their things in assholes, more than anywhere else…That’s why I am angry. It wasn’t what you did” She said looking at me as I could explain action of all men. “Sam…sounds to me like someone wants to stick it in your butt and is that why you are angry? I don’t think all men are responsible for that” “Well then, tell me Josh, have you ever stuck you thing in your girlfriends butt?” she asked, taking another puff from the joint. I had often fantasized ass fucking my girlfriend Kathy, but I never had the courage to try. I had played around her asshole, but never even came close to inserting a finger, much less my cock. “Hamm...Yes” I lied with a straight face. “That’s what I just said Josh. Brad is the same way, now he wants to try it in there” she said, passing the joint to me. “Why don’t you try then? Who knows, you might like it” I said smirking to hear her reaction. “Are you crazy? His thing is like a large cucumber. You think I am going to let him stick it in my ass?” she said looking at me, and then glazed her eyes over the wet crotch of my swimming trunks. “Sam! If you try and don’t like it or if it hurts, you can always ask him to stop, right? So, there is no harm in trying, right, Where is your sense of adventure” I pressed on looking at her cloudy eyes. “No fucking way I am going to experiment with him. You don’t know Brad. If I let him get close enough, he is going to get his thing all the way to my intestines. There is no turning back or stopping him. In fact, I am afraid to turn my back to him these days, because that’s what he wants now, since one of his friends did it with his girlfriend and bragged about it“ “Well then, get a dildo and workout your rear till you can handle him” I said thinking of suggesting alternate method to work her up to Brad. “Yah, Right. Who is going to one of those stores to buy one? You or me?” she laughed. I knew she was right and I know that I don’t have the guts to walk into an adult store and purchase something like a dildo. With parents at home, mail order is out of the question. I thought I had enough of this conversation since my cock was beginning to get stiff just by listening to Sam and therefore got off my chair, looked down to meet her eyes and said; “You can always have mine to practice you know” somewhat jokingly. “I can probably handle yours Josh” she said with a smile “But, I can’t as long as it is attached to my brother’s body...” Sam replied playfully and looked up to meet my crouch, stopping there momentarily. We have played around with words before and I knew Sam was just kidding. She may not have intended to insult my manhood, but I dropped few words to let her know my displeasure before heading into the house to cool off. Knowing that Sam normally slept after her nightshift, I decided to watch TV in the den for little while, before heading out to hang with some buddies. But for my surprise, Sam came down stairs after her shower looking for me and stunned me by asking; “Hey Josh, I thought I’ll accept your offer to experiment with your thing.” She Stuttered. Sam was visibly high after the joint and I knew she was making references to our earlier conversation to allow her to experiment with my cock in her ass. “What do you want to experiment with me now Sam?” I asked looking to see if she was serious. I didn’t expect Sam to ask me to be the one to expand her horizons. Sam looked very appealing in her nightgown that hid nothing beneath. I couldn’t deny that I wasn’t excited seeing her in her nightdress after the conversation that we had, but her words were lest expected. “It’s not having sex if we just experiment, right” Sam mumbled. “I don’t think so. It is just like you experimenting with a dildo, I guess” I said trying to hide my excitement. “Well then, it’s now or never. So, let’s try to experiment with your thing. You can get it up and stick it to me SLOWLEY, but you have to stop if I ask you to, okay” I just couldn’t believe my sister Sam asking me to stick my cock in her asshole. By the look on her face, she appeared to be still high, but serious. How could I refuse a wonderful sisterly gift like that? “Are you sure you want to try this Sam?” “Well, you better start before I change my mind Josh. I thought about it couple of times and decided to give it a go. I would rather experiment with you than Brad, but…remember, when I say stop you have to stop. And I won’t touch you and you cannot touch me anymore than you absolutely have to. Do you promise and agree?” She said with a nervous smile and looked with her still gloomy eyes. “Ok, Sam. I’ll help you. But I hope you know that I cannot just stick it in there. If I do that, it is going to hurt you like a son of bitch. For your sake, I have to prime it first to make sure it doesn’t hurt you” Even though I wasn’t an expert in ass fucking , I knew enough to know that I just couldn’t penetrate her asshole, without first lubricating it to prevent discomfort. From the same time, it occurred to me that I may or may not get another chance to mess with her ass and wanted to make sure that I get her permission to play with as I wished. “What do you mean Josh? What do you have to do?” She enquired. ‘Not much. I may insert a finger, massage your buns, lubricate and stuff before even sticking it in a little. So, what that means is that I have to touch you more than you may want me to. Are you okay with that?” “If I became doubtful that you are doing anything more than you need to, that’s it, ok. You got that? Now tell me what to do then” Sam stuttered again. Her face displayed no emotions and her body swayed and eyes looked unfocused. Never the less, I was thrilled that Sam was still willing to give a go at it. More so, since she was letting me on the driver’s seat. I really didn’t care how far she let me go or when she would ask me to stop, but just the thought having full access to her ass excited me. My cock got hard instantly as it knew what it had on the plate. “Hmm… why don’t you kneel on the couch, so that I could get you ready” I ordered. Sam obliged without saying another word. Once she settled on the couch, she lifted up her nightgown up over her hips exposing her round thighs and glorious ass. I got a glimpse of a brown triangle of hair before her nightgown fell back down again. I was already near heaven. I would have gladly settled for the opportunity to jerk-off to the sight, but I had much more waiting me. Without wasting anytime, I quickly kneeled on the floor by her and raised her nightgown to bring her awesome buns back my eyesight. I ran my hands over her smooth, silky ass cheeks, and bent to kiss them. I rubbed my hands all over her back for a few minutes, and she wiggled her rear. Sam lowered her head to the backrest, placing her head on it. Her eyes kept shutting. I ran my tongue ever so slowly over her inner thighs, while holding and massaging her buns with my hands. I continued to kiss and lick her thighs, slowly moving up towards her crack. My hands tenderly parted her cheeks, kissing her ass checks gently making her shiver. I wanted to take much time as possible to make Sam enjoy her first ever ass fuck and I wanted make sure she was ready before I made any attempt to stick my cock in her. I resumed kissing and licking her ass checks up to her back. On the downward move, I left one hand on her back to caress it while wrapping my left around her front. Then I buried my nose between her ass cheek, slowly started to lick up and down, sticking my tongue bit more inside with every upward stroke. At the same time, I caressed her stomach with my left, sensing and feeling tightening of her of muscles with every movement of my tongue. I felt that she enjoyed it as much as I did and wanted find out how far she would let me go. I resolved to start by lowering my left hand down her stomach to her clit, but did not want to touch it yet, so I continued rubbing over her pubic area. Sam didn’t balk. Perhaps she was too doped to protest or she paid more attention to my tongue that parted her rosebud. After a minute or so, I leaned forward and pressed my tongue deeper into her anus. She tightened her bottom and gasped. While my tongue was bust there my hands were free to roam over her body. Sam reached back, ass still in the air, and grabbed her butt, spreading it out and clenching her nails into her soft, plump flesh, giving my tongue grater access to her brown bud. Getting little bolder, I lowered my left index finger o her clit while settling my palms of my hand over her pubic. I could tell that she was really into it with my tongue teasing her ass bud and my finger massaging her clit at the same time. I heard her moan as she moved her hips slowly to get the most out of my tongue and the finger. Having gotten through the first level of the experiment to our mutual satisfaction, I decided to move on to the next level. I looked at Sam, waiting for me kneeling on the couch with spread out legs and naked ass still in the air. The sight carried me to another level of stimulation that stirred up me even more. I lubed up a finger with saliva and lubed outskirts of her rectum. I worked more on her bum, bit by bit easing further down in-between, up and down, squeezing firmly, watching her beautiful anal opening clasp and relax as I came closer and closer to it. At one point I stopped massaging and just rested my fingertips on the inside of her cheeks. She whimpered and lowered her hips, pushing her anus against my finger. I knew then, this experiment would have positive results. I lowered my upper body, gently relaxing over hers, while still keeping my finger moving inside of her anus, I used the other hand to massage her clit, without making any contacts with her pussy hole. Again, she started to move her hips, moaning softly to my delight. But when I moved my hand to her pussy, she panicked. “What are you doing now Josh? We agreed not to go there” “I need something to lube you Sam” I lied, but she understood the need for a lubricant to get her ass ready and stopped her protest in obliging. I can felt the warmth radiating out from her shaven pussy as I slowly press my index finer between her smooth lips, discharging her wetness. I was surprised at how wet she already was, and the more I wiggle my finger, the more her juices start flowing out until she was so wet, it started to run down not just my hand but her inner thigh as well. So, I moved my fingers between her sopping wet pussy lips and switched hand to lube her ass with it. By the third time I switched hands; her anus was ready and was able to stick in two of my fingers without any apparent discomfort to her. In fact, I thought Sam rather enjoyed the moment with fingers stuck in each hole, moving her hips rhythmically and letting out a soft moan. I wanted to get her used to the feeling and introduce my steal hard member with a purple head. I stopped action long enough to dropped my pants to the floor. Then I quickly returned to Sam’s ass, moved forward and let my hard cock rest between her smooth thighs, touching her left inner thigh. By look of Sam waiting patiently, I thought that she was ready to reach the final phase of the experiment. “Sam, would you like to move to the floor and try the experiment in doggie style?” I asked. Perhaps she was too doped or too horny declined. Without any hesitation, she got down on her hands and knees on the floor. What an awesome sight, seeing my sister Sam on her fours waiting for my cock to enter her elegant ass. I took a moment to get lube my cock with saliva and kneeled behind her, making my cock to bounce between her thighs as I parted her cheeks and rest at her pussy. She jumped in fear that I was trying to enter her pussy. “I need lubricant on my thing Sam” I gave her a lame excuse to comfort her and slid my cock between her slit immediately. Man, she was hot and dripping wet. I let it brush between her folds, absorbing her nectar for a while. Not wanting to upset Sam, I gripped my cock with my right hand, and placed it by brown bud and then slowly eased it up to her anus. I pushed slightly forward and met with some resistance. I held her ass cheeks apart; I took a deep breath and tried to work my cock back and forth at her back door slowly. Within a short time, I had my head in, but stopped the forward thrust when Sam murmured “Hold it Josh, give me a sec”. Then she slowly started to rock her ass swallowing little bit more of my cock with the each move, sending hot vibrations through my whole body. Knowing the third phase was in full swing without only little discomfort to Sam, I begin to fuck her ass with slow short strokes, in and out, pressing my cock into your ass. It was totally hot. Sam’s ass hole was slippery with my pre-cum and smooth. It felt spectacular and I was in heaven, fucking the virgin ass of my big sister Sam. With each of Sam’s breaths I could feel her anal muscles give slightly, and then relaxed enough to let in more of my aching cock slid in. I could feel my cum starting to rise in my shaft. I wrapped my right around her waist and started rub her clit with my index finger in circular motion while sliding my cock in and out of her anus. Within few moments, I felt her ass muscles tightening around my cock. Sam rode my cock, while I massaged her clit vigorously. I entered my fingers into her slit and this time she did not question my motive, instead she led out a loud moan. I pumped faster and faster, deeper and deeper, and suddenly felt the end of my cock swell up to bursting point. I felt my own body tense up and then I came, four or five hot jets of it in her lovely tight asshole. The sensation of my hot cum and the finger that boogied in her hot pussy made Sam reached her own climax and she exposed her delight with several loud moans. As she moaned, she shook her hips violently making my cock rock. I was exhausted. Sam appeared as she enjoyed the experiment when she collapsed on the carpet, leaving her ass that was still stuffed with my cock in the air to me to keep fucking, as I remained hard. This time, my hot cum in her ass made it more slippery and pleasurable. I pumped harder, each stoke now making her moan again. She reached and started to finger her own pussy this time, since I had both hands gripping her ass. I kept fucking. She kept fingering her own pussy. Again, I felt my balls tighten. Knowing that I was ready to shoot my second load, I wondered how her pussy would feel around my cock. I also knew it would be once in a million shot that I would get to come close to her again like this. I quickly withdrew my cock from her anus, causing my hot cum to drip down. Then in one swift move, I held my cock and inserted in her hot, inviting pussy, and then held her from her hips to assure that she could not cause my cock to dismount. “You are not going to do that, are you Josh” she asked softly. Her voice wasn’t that convincing I thought. I didn’t answer, instead started to pump in and out till my cock disappeared in her juicy pussy, and increased my pace. To my utter surprise, Sam started to wiggle her butt, giving me more pleasure than I bargain for, causing me to unload once more, this time, deep inside her love cannel. Second later, I clasped on the carpet next to Sam. “Would you experiment with me one more time before I try with Brad, Josh?” Sam asked, giving me a quick kiss on the cheek. “Anytime! I think we should do this few times before you take on Brad”