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She Challenged Me!

"My boyfriend's sister challenged me to a game of strip chess!"

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I advanced my King’s Pawn two ranks, a standard opening. She looked at me briefly. We had never played each other before so neither of us had any idea how good, or bad, a player we were. She matched my move, our pawns looked at each other. I remembered an old computer game, Battle Chess, where the pieces would make threatening motions when face to face. Ruefully, this was an ordinary, although lovely, chess set.

The pieces were wood and carved in phenomenal detail. It also looked old yet in wonderful condition. It didn’t show much use even though it had been set-up for a game every time I saw it in this room. Normally, when I came in here with her brother, we headed for the pool table or the gaming console. This was the first time she invited me in here for a game of any sort.

I thought we were just killing time until her brother got home. I didn’t know her well; I’d only been dating her brother a few months and she’s a year older and was away at Uni until the beginning of this month. I was surprised when she invited me for a game, but I figured it was a good way to get to know her a little. Her brother didn’t talk much about her, but then I don’t talk much about my family either. I’d met his parents a couple of times, but we weren’t serious, more hanging out than anything.

The game progressed and I caught her in a simple fake-mate after only ten moves. I wasn’t sure how focused she was on the game, but I was expecting more for some reason. She had this intense look that I thought meant she would play a tighter game. No worries, as I said we were just killing time, or at least I was killing time. We were the only ones in the house. Their parents were at work, Nathan was running an errand that wasn’t supposed to take too long. Becky set up her pieces for another go, so I followed suit.

She was white this time and opened with the Queen’s Gambit, which I followed mainly to see how she handled it. I’m not some chess guru, but it’s one of those games I do enjoy. I get trounced regularly by my brother so I have managed to learn a few things. He got good at it while recovering from a broken ankle last summer and board games were about all he could do for eight weeks! We don’t play as often as we did last summer, but we do still play — and he almost always kills me at Chess. I beat him at Go and Othello. Like I said, lots of board games, aka ‘bored’ games when you are recuperating. I even busted him watching an episode of The Bachelor once, that’s how bored he was!

This game was much closer than the last, she put me on the defensive several times, but seemed to have trouble finishing. I captured a few of her pieces and finally put her on defense and closed the game out. She played much better defense than offense, but the outcome felt inevitable. I had a pretty good feel for her style of play.

“Let’s make it interesting,” Becky said, not looking at my face.

“How so?”

She looked up with a grin, “Something we do at college, a variant called ‘Strip Chess’ ”

“What?” I was surprised, but not shocked. I’d heard of strip poker and a couple of other games with ‘strip’ dropped in front of them. Often by a guy who thought it was an easy way to see naked girls. I think if someone at an all-guy poker game suggested ‘strip poker’, he would probably get his man-card taken away in public while at least one of the other guys at the table privately thought it would be fun. Just my opinion!

Becky continued, “It’s simple, other than pawns, whenever one of us captures a major piece, you have to discard an article of clothing of the other’s choosing. Are you game?”

I thought for a minute that maybe Becky knew more about me than I knew about her. ‘Are you game?’ is a question between Nathan and me which has become the semi-equivalent of ‘I double-dog-dare you!’ It’s usually for the various videogames we play, but we’ve used it for any number of things. It wasn’t as mindless as maybe with kids, when those words automatically meant someone was about to do something stupid. So I thought about it and said, “Won’t Nate be home soon?”

“So, the idea of one of us being naked in front of the other doesn’t bother you, but getting caught by my brother does? Interesting! I think I forgot to give you a message, Nathan had to go downtown for his errand. He’s going to be a lot longer than expected.”

I laughed, “Forgot? Why do I think that’s not totally accurate?”

She grinned and looked down at the chessboard again, “So, are you game?”

I had a pretty good gauge on her play, so I was confident. I was also wearing a lot more clothing. A tee-shirt with sleeves under a Kobe basketball jersey, shorts, bra, panties, socks, and tennies. I have quite a bit to lose before I would be naked.

As for seeing her sans clothing, that wasn’t a big deal. I’d seen many girls naked in the locker room. While I sometimes compared my body to theirs, it was more a quantitative examination than qualitative. I know I did it a lot as a freshman waiting for certain body parts to change. Thankfully, they did and now I stack-up well against just about anyone, well except for Julie Dryman! I mean she was a D-cup at sixteen! Who could compete with that!

I started setting up the white pieces and saw her smirking as she set up black.

“Since you beat me two games, I should ask for a handicap.”

My turn to smirk, “I don’t think so.”

“Okay, so I’ll give you one anyway.” She took off her tee-shirt. I did my best to cover my surprise and for a moment I thought maybe she had sandbagged me, but her play in that second game, especially the defense wasn’t sandbagging, no freaking way! She fought that losing hand well. Of course, I had to look at her. I hadn’t thought about just how pretty she was.

Becky wasn’t a classic beauty, her brown hair with some auburn highlights hung to her shoulders with soft curls. She was shorter than me, with an oval face that had interesting planes and a sharp nose. It was an expressive face, more than I realized during our games. While she wasn’t as built as Julie Dryman, she was a solid C-cup being supported by a thin bra, her dark aureoles visible through the bra cups. She sat straight up during my brief examination. I didn’t find her overly distracting, but the very idea was a little disconcerting. However, I was committed and I rarely back down from a challenge and Becky was certainly challenging.

I made the first move, and I was surprised when she ignored her pawns and moved out a knight. It was a much more aggressive move than earlier and generally a foolish move for most players. The pawns are used to control the board to allow the stronger pieces to project their power to different parts of the board, usually focused on the board center.

The game wasn’t going the way I expected. I thought she would play more defensively, which seemed to be her strong point. Instead, she was playing a form of blitz chess, trying to get all her pieces rapidly in the game regardless of how dangerous it was.

I captured one of her knights and she stood. “What should I take off?”

I looked and for the first time realized she wasn’t dressed in much. She was barefoot and in shorts. The only other item of clothing was her light green bra. She only had three pieces of clothing and was about to lose one of them. Something in me was tempted to have her take off her bra, but I chickened out and told her to lose the shorts.

She grinned like she knew what I was thinking. She slowly stripped off her shorts. She was wearing a pair of boy shorts matching her bra. A lacey green set that set off her skin tone wonderfully. ‘Wonderfully?’ I almost shook my head at my thoughts. She tossed her shorts over by her top and she sat back down across from me. She sat very upright, her chest thrust out, casting a shadow from the lighting across her side of the board.

We started playing again and her aggressive style took one of my bishops and threatened a rook. I stood waiting for her to decide as she looked me over. What hadn’t dawned on me was that having her select the clothing wasn’t an advantage for me. A while back, during a sleepover, a bunch of us tried to play strip poker. Of course, after each hand, the loser would take off the bare minimum, I mean there were socks, hair ties, and even bras pulled through tops before a single bit of skin was uncovered. In this game, there was no way to take off something innocuous like a shoe or a sock first because the choice wasn’t up to the loser of the chess piece.

She took her time and looked at me up and down. It was a little disconcerting and part of me shivered. I couldn’t quite read her expression. After a short time, she said “Shorts, if you please.”

It was a struggle getting them over my tennis shoes, I had to sit down to remove them. She watched me closely and seem to enjoy my struggles. I could feel my face heat up and I vowed to not lose any more clothing!

I sat back down, and we started again. I almost got her queen, but she sacrificed both a pawn and a rook to keep it safe. She stood again and part of me didn’t want to do it, but that would mean backing down. I had two choices: bra or panties. Both had pluses and minuses. ‘Pluses?’ Again, I was surprised at my own thoughts. What was a plus about seeing another girl’s breasts?

That being the case, I told her, “Panties, please.” The look on her face was one that might have been disappointed, but it flashed by quickly. Then she sat down on the floor and took off those cute panties, then she stretched her legs apart and stroked them while looking at me. I caught myself looking at her legs and more. When she brought up her knees to stand back up, I realized she was trimmed, not shaved. I felt myself heating up again.

“It’s really comfy, you should try it.” She said it while running a hand across her mons. I looked away quickly, embarrassed at being caught looking at her like that. Again, my own thoughts felt weird, ‘looking at her like that?’ Like what? I was trying to figure out where my head was when she sat back down.

The board was a mess, there was nothing coherent, no strategy, no tactical advantages. It was the strangest chessboard I’d ever seen. It was more like a random assortment of pieces than anything else. I waited while she contemplated her next move. I was also looking at the board to try and make some sense of it.

She moved a pawn forward one square. It opened a line to her queen from my bishop. I almost didn’t catch it myself. I studied the board very carefully and suddenly it made sense. It was the only answer to her strategy. I look up at her, she was looking at me as well.

“You aren’t playing to win!”

She gave me a wide smile, “It took you long enough to figure it out. The object to Strip Chess is to get naked, not win the game.”

“But why?”

She stood up and came around the table. Surprisingly, she slid into my lap and before putting her arms around me she unhooked her bra and dropped it on the floor. I had a naked woman in my arms, and I had no freaking idea what to do.

“Nate probably didn’t mention that I’m gay. He also didn’t mention to me how pretty his girlfriend is.” She put her face on my shoulder and kissed my neck.

Instinctively my arms went around her, my hands on her bare skin. If I could think straight, I would add those to a list of things I had never done before. When my hands touched her, I felt almost like a vibration running through her body. I couldn’t say anything at all. I wasn’t sure what I was feeling inside or out, all I felt was a warm body against me and her lips on my neck. I realized the vibration was within me not her. I think I moved my hands a little, feeling her smooth skin when she kissed my neck again.

Part of me was thinking that while I know I liked getting kissed on the neck, it never felt like this. It was like a shock to my body. I ran one hand up her back, her soft warm back. She shifted and straddled me, my hands now on her hips right where her hip folded. Her arms went around my neck and her face was very close to mine as she looked at me. I don’t know what she saw, but time moved in infinite slowness as she came closer. I felt like I had hours to think about what was about to happen. Do you know how slow the clock moves at the end of the school or workday? That was nothing to how slow it was moving right then.

There was an unusual scent flowing between us, one I should have recognized since it was similar to my fingers on some late nights when I would touch myself. She was not only in my lap, but she was excited and I could tell! For some reason as her lips got closer and closer, I pictured her in her bed, the lights out, the door closed and her legs clamped tightly around her hand as she brought herself to one orgasm after another.

I felt wetness on my upper thighs, I assumed it was her, but then noticed I was leaking myself. My off-kilter brain worried about the fabric of the chair for a moment. She stopped just a tiny bit away from me.

“I really, really want to kiss you. But I won’t if you don’t want me to.” Her breath was hot with a slight strawberry scent. I knew she had been drinking an energy drink, I guess it was strawberry-flavored. Again, my warped mind seemed to find lots of time to think about silly things, like the chair and her sweet breath. Something deep inside me said I should be acting differently, maybe even freaking out. I thought about Julie Dryman again. For some reason, I thought if she were sitting on my lap like this how interesting it would be to touch those large breasts of hers. As I thought that, I felt my hands move up over Becky’s stomach and stopping at her breasts. When I cupped them, I felt her react and I also felt her smile. She was too close for me to see it, but I felt her smile and she relaxed slightly. Her lips moved closer and I found myself wanting time to speed back up.

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No, that wasn’t the case, I didn’t want time to speed up, I just wanted to feel those lips on mine. I tilted my head slightly and she closed her eyes. My thumbs rubbed over her nipples and she inhaled sharply. Before she could exhale, those lips touched mine.

I don’t know what I was expecting, kissing Nate and the two other boyfriends before him was okay, but nothing special. I mean I think I expected fireworks on my first kiss, but instead, it was sloppy and strange. Of course, I kept kissing them because it was one of the things you do, boyfriends and girlfriends kiss! I mean as gross as it is, my parents, kiss all the freaking time. Hell, even my grandparents kiss! I did it because everyone did it, but it wasn’t much of anything to me.

This kiss was different. It wasn’t fireworks, but heat. When her lips touched mine I felt almost a blast of warmth fill my whole body. I can’t explain it well, but I never felt anything like it. The closest I could come was that time I got shocked in science class.

Have you ever used one of the goofy-looking Van de Graaf generators in school? You know the static electricity experiments that make your hair stand up. Well, if you had and anyone touched your body with a metal rod, you got a small shock between your hands on the generator and the point where the rod grounded out the static charge. It sort of felt like that, only it wasn’t localized in one or two spots but all over. It also wasn’t small, it felt larger than my whole body!

Our tongues twisted around each other as we went back and forth in that kiss. It was incredibly sloppy, sloppier than any kiss I had before, and yet instead of thinking gross, the slickness added to the sensation and it felt incredible — slipping and sliding as our tongues wrestled. I think it was a tie when the kiss finally broke.

Time was still running slow because I half-expected it to be dark instead of just a few seconds passing. The clock said two PM and I think it was lying! It felt so much later. She got up off my lap and I felt chilled for the first time in forever. She lifted me to my feet and tugged at my Kobe jersey and tee-shirt. They came off together and she reached behind me and unhooked my bra. A tiny part of me questioned what was going on, but that thought got lost quickly. She stepped away and gathered up our clothes, then she took my hand and led me to the stairs.

Several steps up, I reached out and pulled her to me. She was facing away and was one step higher, but our height difference put our heads level. I pressed against her and wrapped my arms around her waist, then I kissed her neck and raked my teeth across her skin. I felt her shiver and moan slightly.

“We need to get upstairs before anyone comes home.”

My brain was starting to re-engage. “Do they know you are gay?”

“Oh yes, but I think they might get weird finding us naked down there. Nate knows too. I am very open with my family.”

I thought about it, “Why is Nate running so late?”

She turned on the stair, looking me in the eye. “I asked him to be scarce. He knew I was going to make a play for you.”

My eyes opened wide and before I could say anything, she put a finger to my mouth.

“Don’t be mad at him. He really likes you, but it was more buddy-buddy than lovey-dovey. I think he felt that way but never really put it in words until we talked. I don’t know if you are in love with my brother and that’s probably something we should talk about — later, much later.” She kissed me again and I pushed against her, we ended up laying on the stairs, her legs around me as we kissed more and more.

Another small part of me felt like I should be annoyed, I mean my boyfriend kind of set me up with his sister, but two things prevented me. One was after thinking for a few seconds, I had to agree. We were never lovey-dovey, as she put it. We were simply hanging out and doing some of the things boyfriends and girlfriends do. There wasn’t much to it. The other thing was how I felt at that moment. Some of the romance books I’ve read over the years were making a little more sense to me now. I was feeling things for Becky, things I never felt for Nate or the others. Was I in love with her? I don’t know, but there is something there I hadn’t felt for anyone else.

We got up and managed to get to her room, even with all the touching and kissing. It felt like the most natural thing in the world. I almost stopped to tell her my secret, that even though I had three boyfriends previously, I was still a virgin. It wasn’t that I was saving myself for marriage, it was more that I never felt the urge to go any further than kissing. My first boyfriend tried to change that but getting your newly sprouted titties grabbed and groped didn’t make me feel like he seemed to think I was supposed to feel.

Yes, it was one of the reasons we broke up. He didn’t just keep trying to push me, he even tried to pass some rumors about how successful he was. I got mad when I heard and told a couple of friends that the reason I didn’t have sex with him was because of his small penis. I sort of felt bad about that when it turned out to be true, according to a girl he dated later. I tried to take it back, but like his rumors about me, it was too late. The other downside was my second boyfriend decided that since I had some ‘standard’ for penis size, he was just the guy to fit that standard.

He was fun for a while, but when it finally dawned on him I wasn’t interested in having sex with him, he found someone who was. I didn’t blame him, but he could have broken up with me first! I think those two are the reason Nate and I were more buddies than lovers. I enjoyed his company, even with the kissing. We got along well, liked some of the same activities, and, best of all, he didn’t push me about sex. While I couldn’t imagine being married to him and having kids, he was a better boyfriend than the other two because he seemed to get part of me.

In her room, we barely made it to the bed. We were hanging half off when she took my nipple in her mouth! Oh, my fucking God! My breasts aren’t big, maybe a bit past an A-Cup. They were enough that I needed a bra when doing any running or anything physical, even dancing. It’s wasn’t that I was in danger of giving myself a concussion (like Julie), but they actually hurt after being tossed around willy-nilly. I also learned the bennies of a sports bra over a regular one after it rubbed my nipples raw on a run.

But none of that prepared me for when she sucked one of my sensitive nubs in her mouth. It was like a live wire right through me. I instantly flooded, at least that’s what it felt like. She not only sucked but bit my nipple lightly, the pressure was fantastic!

She pushed me back as she teased, sucked, and bit my nipple. I ended up flat on her bed with my legs hanging off. She was laying half on me, between my open legs, feasting on my chest. Then she stopped and knelt on the floor to remove my sneakers and socks. It was when she took my big toe in her mouth, I think I had a mini-orgasm.

While it was mid-afternoon, I hadn’t done anything too physical so I knew my feet weren’t a stinky mess. As she took off my shoes and socks, that thought did occur to me, but when she sucked on my big toe, all thoughts seemed to flee. I’m not very ticklish, and I couldn’t see what she was doing, but the feeling was indescribable. I never thought toes could be such a turn-on, but there was no question they are now! She gave my big toe what could only be described as a blow job, another of those things I had never done even though my first two boyfriends seemed to expect it. If having their dicks sucked felt like what Becky was doing to my toe, I understand the desire more than ever!

She then licked and kissed her way up the inside of my leg while her hands both led and followed her mouth. She stretched my legs wide and nibble on the muscle of my inner thigh. From my vantage point, all I could see was the top of her head, but it really didn’t matter, I closed my eyes and threw my head back multiple times.

She then placed another kiss right between my thighs, right on my now soaked panties and she looked up at me. Her face looked … well she looked like a kid on Christmas morning about to open what was going to be the gift they wanted most in the world. She paused, “May I take off your panties?”

All I could do was nod. The power of speech must have still been sitting at the chessboard wondering where the rest of me went.

She smiled again, a real smile, not like the one she gave me over the game. She tugged my very plain cotton panties to one side and kissed me again. Lightning struck as I felt her tongue flick my clit. While I recovered from that, my panties went past my ankles. I might never wear that pair again!

It may sound a bit childish, but I have this little chest in the back of my closet. Over the years I’ve put some special mementos in it. The stub of my first movie ticket, the one where my parents let me go and watch on my own. A snow globe that I broke to see how it worked. The globe was gone, but I had the base and the little town. I remember the mess to this very day! A party favor from the first party I remember going to. I didn’t even know I still had it until it fell from the top shelf of my closet one day and I sat there remembering the look on my best friend’s face as she opened my gift. There were many more items in that chest and each one made me remember some significant occurrence in my life. I think I have at least one new item to add!

Isn’t it weird how your mind works as your body is being overwhelmed with new sensations? Once I was properly naked, Becky pulled me more on the bed and lay next to you, one leg over my thigh, her knee brushing my pussy lightly. Her warm body next to mine as she played again with my breast almost absent-mindedly. She was looking at me intently, more intently than during the chess match. She seemed to be waiting for something, but I had no idea what.

I turned and faced her, slipping one leg between hers. I could feel her wetness on my thigh. I looked at her, thinking how I earlier thought she was pretty and yet hadn’t realized how quickly your point of view can change when you look at the face of a lover, your first lover even if she didn’t know that quite yet. Those planes and angles of her delightfully oval face were gorgeous, her sharp nose had a tiny cute little upturn that begged to be kissed. Her eyes held a sparkle and a hint of mischievousness that almost made me giggle. I did the only thing I could do, I leaned over and kissed her right on her cute nose.

She looked surprised, but her smile told me I was taking the right tone. Yes, we were naked in her bed, but we still didn’t know much about each other. For some reason, I’m sure I have no idea why, but I was intensely curious about her. I wanted to know so much. When did she realize she was a lesbian? What was her first experience like? Was I a lesbian? What …. Those questions got preempted as she rolled me on my back and laid on top of me. She grinned like she knew everything I was thinking. And she kissed me again. I loved her kisses!

My arms went around her as she straddled one of my legs, she pushed her thigh between mine. Then she sat up on her knees and slid up until our pussies were against each other. She lifted one of my legs and held onto it. I thought it was a weird position and not one I remember seeing in one of the few porn movies I will never admit to watching. Then she pushed her pussy tight against mine and rubbed them together. I thought the nipple suck was an 'Oh, my fucking God' moment, it had nothing on this.

We were both wet and hot. The heat just kept building as she — well — as she fucked me. That was the only word that worked. Making love involved emotions that we were in the process of building, at least I was. I hope she was as well. But this was fucking plain and simple.

The look of concentration on her face as she ground herself into me was occasionally broken by her own cries of pleasure. Once in a while, during a particularly intense feeling, she would close her eyes. She would press her mouth to my leg and I could feel some of her spit running down it. Later I might think gross, I mean it was spit, wasn’t it? But right then it felt so freaking sexy! I felt myself grabbing at the bed cover, bunching it in my fists.

I heard a cry and hadn’t seen her mouth move, so I guess it was me. My back arched in orgasm like nothing I had ever felt. Seriously, I could cum those late nights, but there was no comparison. I came really hard and she was right there with me. I felt my midsection spasming like I was doing a bunch of mini-sit-ups and I couldn’t help turning my body away from her as she sort of fell over perpendicular to my legs.

We recovered slowly, she crawled up the bed and snuggled next to me. My arms found their way around her as I held her. I couldn’t help but think about the future. I mean she was home for the summer and would return to school. What was I to her, a summer fling? I still had so many questions, but she answered a few with one sentence.

“You are planning to attend my school in the Fall, right?”

Published 
Written by Brookell
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