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Introduction:

A very surprising evening
I will preface the following story with this bit of knowledge: Everything below is the truth. With this comes several potential issues that some readers may not like. 1. The dialogue - the reality of it is this; we were young and it was the first time something like this happened for either of us. The dialogue is awkward due to the fact that it really was that awkward. 2. I have stuck to the story as it actually happened and have relived it as I wrote it. This can also result in a longer story than it could have been, but again, I wrote it as it occurred without embellishment. And lastly, 3. If something didn't happen, then I didn't add it in. Everything written is what happened for better or worse. If this is well received, I may write more in the same fashion which chronicle our other encounters or I may write about different ones. But I promise this; they are factual and accurate. I hope you enjoy.


I can't really say what started it as it has been so many years, but I will do my best to recall everything accurately. I do remember that prior to that night, Cindy never really wanted anything to do with me. Cindy and Jennifer (Jen) were my step sisters. I was 16 at the time and Cindy was 14 followed by Jen who was a late blooming 10 year old. 10 and flat on all sides. Cindy on the other hand had developed quite nicely but I honestly never gave it a second thought. I got along with Jen real well because we enjoyed the same types of music and movies but Cindy and I just kind of accepted each other as a step-sibling and nothing more. We had different groups of friends with none in common so the only time we ever saw each other was at the house. We grew up in a small town of less than 1500 people before anyone even knew what the Internet was and home PC's were not even heard of. Because of this, we were all fairly naive regarding sexuality. Everything I knew came from a copy of Penthouse Letters a cousin had given the year before.

One night the three of us were home alone, which happened a lot since our parents always went to the next county to go dancing. We lived in a dry county so all the bars and clubs were at least forty minutes away. Since they always stayed until closing time they wouldn't be home until at least two or three in the morning.

It was on one of these evenings that Jen suggested we turn all the lights off in the house and play "hide & seek". Cindy and I couldn't come up with any better ideas so figured, what the hell, why not? This wasn't the first time we had done this so it started off fairly routine with two hiding and one seeking. The house was rather large so at times it would take five minutes to hunt down the "hiders". On my second or third time seeking, I ended up in the bathroom. This was an interior room with no windows so it was pitch black. As I was seeking, I had my hands out in front of me when all of a sudden I felt something I had never felt before, a breast. While blindly feeling around, my left hand had basically perfectly cupped Cindy's right breast. It was then I noticed that not only where they bigger than I realized, but that she wasn't wearing a bra. How the hell did I miss that? I froze. My mouth was dry and my mind went blank. I can't say how Cindy reacted as I was unable to see her but it did take about five seconds before she took a step back and spoke in a quiet voice, "Uh... I guess I'm it". With this, she left the room. I stood there for a few seconds before continuing on, looking for Jen. I finally found her and it was then Cindy's turn to seek.

I don't know why but I found myself going back to the same spot I found her in and standing in the same place she stood. Cindy did the countdown and started looking for us. It didn't take long and I heard her come in the bathroom. I could almost feel her hesitate as her hand touched my chest. Again, in her quiet voice she said "Now your it again". After Cindy found Jen, I was again the seeker. My heart was beating so hard I thought for sure anyone could hear it. I did the usual countdown and slowly, quietly, made my way to the bathroom again. I didn't really think she would be again, but I just had to know. With a parched throat and a shaking hand I entered the bathroom and turned to the corner she was in previously. I raised my hand at the same level and slowly moved forward. Then it happened. Again. My hand lightly grazed her left side and I slid it slightly over, just enough to cover her breast again. This time I moved my right hand up as well to cup her left breast. I ever so lightly rubbed them through her cotton T-shirt for another five seconds or so and was rewarded with a slight intake of breath on her part. Then she again took a small step back and left the room. I was on cloud nine. To me, this was the greatest night of my life. Not only had I touched a breast (Twice!), but she didn't scream and run, but actually seemed to enjoy it.

As it turned out, that was the last round of the game. Jen decided that she was tired and was going to go to bed and asked Cindy if she wanted too as well. Cindy paused for just a moment and said "Yeah, I'm getting tired myself". I was disappointed but not even that would take away the amazing feeling I had. I resigned myself to just spend the rest of the evening in my room reading and thinking about what had happened. I was quite startled when there was a soft knock on my door almost an hour later. I opened it up and there was Cindy. I was stood there for a moment before stepping back into the room and she entered. It was then I noticed she was dressed for bed. Which meant she was wearing nothing but her T-shirt and panties. No shorts, and I already knew she wasn't wearing anything under the T-shirt.

"What are you doing?" she asked.

"Nothing, just reading" I replied.

"What are you reading?" she asked hesitantly.

"A book by Raymond Fiest. It's pretty good so far".

She had never shown interest in anything else I had ever done so I was at a loss as to what I should say or do. We stood there for a few seconds and she turned as if she were about to leave so I thought I had to say something fast or she would leave and I would never have this opportunity again.

"So did you want to hang out and do something?" I said. Wow, how lame I thought to myself.

She turned to me and said "Sure, like what?".

I replied "I don't know, we could just hang out in hear. I could rub your shoulders or something". Yeah, I know. Super lame. I had no experience with girls at all so I thought I was floundering really bad. That popped into my head because I was just trying to think of anything that would allow me to touch her again. She seemed to think about it for just a moment and imagine my surprise when she said "Yeah, that sounds good".

"OK, well, go ahead and lay on the bed and I'll rub your shoulders for you." She crawled onto the bed and I caught a glimpse of her powder blue panties for the first time. They were the silky kind, not cotton and I damn near had a seizure when I saw them. I mean, this was real, not a movie or one of the stories from Penthouse Letters.

Cindy was about 5'2" and her body was amazing. She was firm in all the right places and her breasts were about the size of medium oranges. I never paid attention to her cup size before when I saw her bras laying around her room. I made a mental note to find out later however and the tag on her bra indicated she was a size B.

She lay there with her arms folded under her head with her forehead resting on her forearms facing down. I realized I had nothing to use for her massage and told her to hold one second while I grabbed something. I prayed she wouldn't change her mind while I ran to the bathroom real quick and grabbed a towel and a bottle of mineral oil. I got back to my room and thankfully, she was still there.

I started to sit next to her but quickly realized how awkward it would be so I straddled her, kneeling over her rear end. I pulled her shirt halfway up her back, enough to gain access to her back but not enough to scare her off. This also exposed her entire ass to me and allowed me to see her in nothing but the panties. Up until this point I was to nervous to really think about it all but now I was starting to really enjoy the moment and really wanted to see how far I could go. I put a little of the mineral oil on my hands, rubbed them together to make sure it was warm and started rubbing her back. I couldn't believe my luck. She just lay there and enjoyed the massage. As I progressed up and down her back she just lay there and enjoyed it (I assume). I started slowly and with each stoke up and down her back moved my hands to each side a little more until I was rubbing her back and her sides. As I rubbed her sides I could feel the slight curve of her breasts that were pressed into the bed. At this point her shirt was still on and since it was only halfway up her back, this meant it was halfway up her front as well, blocking full access to these breasts I so desperately wanted to see and feel. This had been going on for about five minutes already and since she had not protested so far I figured why not go for broke. Praying my voice didn't sound as nervous as I really was, I simply said "I need you to take your shirt off, it's getting in the way." I held my breath and after the longest ten second pause of my young life she lifted herself up just an inch or so on her elbows. I took this to mean "Go ahead" and wasn't disappointed. She didn't say anything when I took the bottom of her shirt and pulled it up. Once it was up as far as it could go she lay back down and held her arms out straight so I could pull it over her head and arms. Once again she folder her arms together and placed her head on them. I sat back and admired her ass and back. Holy shit! How did I get this lucky?

Once again I started on her back except this time I immediately moved to her sides. With the mineral oil on my hands I was able to get the first inch or so of her skin that was facing the bed. I was moving up and down her sides steadily and after another three minutes or so (yes, I was watching the clock, I didn't want to take to long between "making a move" and bore her into leaving) I simply said, "Prop yourself up on your elbows so I can reach the front a little better.". Again there was another long pause where I thought I had blown it but once again, she did as I asked. She propped herself up on her elbows with her head just hanging forward. I started on her back again knowing that her breasts were just one small motion away, hanging there for me to caress. My mouth was getting dry and my shorts were getting very tight for space but there was no way I was doing anything to lose the moment. A couple of more passes up and down her back and I moved back to her sides. Another minute or so of this and I did something I had never thought I would do; I slowly reached around on both sides at the same time and gently ran my hands over her breasts.

Time slowed and everything got very surreal. I couldn't believe this was happening but it was. I kept rubbing her sides and breasts for another two or three minutes (I had quit watching the clock by now) and took the next step. "OK, your back is done, go ahead and roll over." She didn't say anything for a moment said "It's to bright in here to roll over." My heart stopped, I was sure I had blown it but then she said something that confirmed she wanted this as much as I did, she said "Can you turn the overhead light off and just leave on a desk light or something?" Could I? Hell yes I could! I would have broken my chair to use as a small torch if that would have made her happy. Without trying to appear desperate, I got up and turned on the desk lamp and then turned off the overhead lights. I turned around just in time to see her roll over.

I almost lost it on the spot. There, on my bed, was my step-sister with nothing but a pair of powder blue panties on and my God did she look stunning. She was laying there with one arm off to the side and the other laying across her eyes to block what little light was in the room. I walked around the bed and admired her from every angle. Her chest was glorious and her nipples were bigger than I thought they would be. They were about the size of half dollar coins and a soft pale pink color. I was just wearing a pair of workout shorts and a t-shirt so I ditched the t-shirt. I didn't work out but I was active so I looked fairly decent without it. I realized I was staring at her for quite a while and moved back to the bed. This time I straddled her and was supporting myself right over her hips.

Again I warmed up some mineral oil and started rubbing her. I started with her stomach and moved my way straight up to her breasts, neck, and shoulders. I was, of course, spending a lot of time on her breasts but she seemed very pleased by it so I didn't stop and she didn't complain. As I went lower on her stomach I started turning my hand sideways with my thumb facing down. Each pass and I would spread my thumb out a little more. I was on the third pass that I felt pubic hair! The night kept getting better and better! How much better could it get? Since she was not stopping me so far, and seemed to be enjoying it, I was going for broke. After five or so more passes my thumb was far enough down to lightly brush up against the uppermost part of her pussy lips. A few more times of this and I slowly pulled down each side of her panties about an inch and continued for another minute or so. Since she didn't say anything the first time I lowered her panties slipped my fingers under the sides again, planning on sliding them down another inch or so. This time however when I started to move them down, she lifted her ass off the bed, allowing me to pull them all the way off.

There before me, bathed in the light of my desk lamp was my step-sister in all of her naked glory. I got my first view of a real girl and she was a beautiful sight to behold. Her body was just amazing. I knew it was good from what I could see when she wore tight jeans and t-shirts but this was something totally different. This was just pure beauty in its natural form. Her young breasts were flawless and firm, her stomach was flat from all of the sports she played and then there was the most perfect pussy ever. It was covered with a small patch of hair that was naturally only about three fingers wide and was extremely soft to the touch. It was one of those pussies that looks great naturally without having to trim it.

As I tossed her panties on the floor, instead of closing her legs back together as they had been during the massage, she left them spread wide for me. I slowly started to use one hand to massage her lower abdomen and the other to massage her pussy. I started lightly stroking her with just my thumb and made sure I used soft circular motions on her clitoris. I had never done anything like this before but I had read way to many issues of Penthouse Letters to not know what would make her feel good. It didn't take long for her to get wet and then I started slipping my thumb up in between her pussy lips and slowly working to get her as turned on as possible.

I moment after this the worst thing (Later to be the best thing) happened, I got a leg cramp. Dammit! I tried to tough it out but that wasn't happening. Instead, I got up to work it out real quick and this time, I laid down next to her instead. I lay on my left side and propped my head up with my left arm, and used my right hand to keep rubbing her. I would alternate between rubbing her pussy and moving up to rub her breasts. I kept this up for another couple of minutes and then pushed my luck a little further. I used my hand to knead her right breast, the one closest to me, for about twenty seconds to make sure her nipples were nice and hard, then licked my lips and slowly leaned over and kissed it. I paused only a second before doing it again and then moved my hand back to her pussy and took her nipple in my mouth and started to gently suck on it. She responded in the last way I expected. She started to move her hips in a rocking motion and moved her right hand to the back of my head and held it where it was.

By now she was extremely wet so I progressed from simply rubbing her pussy to actually, carefully, inserting my middle finger. I did it slowly so I wouldn't hurt her and started to slowly slip it in and out while using my thumb to rub her clit. Her breathing started getting very fast and shallow. I couldn't see her face but could tell from the sounds that she was getting close to her first orgasm. It hit just a moment later and damn did it hit hard. She put both hands on my head and pulled me into her chest and arched her back so that her hips came off the bed while at the same time clamping her knees together, trapping my hand between her legs. I kept my finger buried inside of her and kept working her clit with my thumb while she struggled to stay quite and shook for close to a minute.

Once it passed she fell back to the bed and her hands fell beside her. I lay there next to her, my hand resting on her pussy and propped up next to her just stared at her. She lay there for five minutes with her eyes closed coming down off of her high and then quietly fell asleep with a small smile on her face. I stared at her for another five minutes and softly ran my hand over her body. I got up and walked around her, admiring her from every angle. I realized that it was late and didn't want to run the risk of getting caught so I gently put her panties back on her and sat her up so I could drop her shirt back on her as well. She was still sound asleep so I opened up both of our bedroom doors and carried her from my bed to hers. She shared a bed with Jen so I was nervous about her waking up but luckily that didn't happen. I again returned to my room, closed my door, lay down, and fell asleep with feeling more relaxed and excited as I had ever been.

The next morning I awoke to the sound of people moving around the house so after going to the bathroom, I went to the kitchen for breakfast. Everyone was up and about getting ready for the day and the house was its usual controlled chaos. I grabbed a bowl of cereal and sat at the table and a moment later Cindy sat down across from me with her omelet. We didn't make eye contact at all until everyone else drifted out of the room and then she looked right at me. I looked up at her and she broke out in a beautiful smile and said quietly "Thanks for last night, I owe you one."
147 comments

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