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Double or Nothing Ch. 04

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To the reader: I hope you can tell by now that I love writing stories like this. I never intended this simple brother-sister one to turn into a saga, but your comments and private feedback have encouraged me to let it keep coming to me. It surprises me every time. Writing is the first joy, and your feedback is the second. Don’t let any author try to tell you otherwise. Thank you. – Brandie

Emily was my best friend in high school. She had gone off to college in New York while I went to a small school in North Carolina. Today was one of those rare chances for the two of us to catch up, since I had the day off and her summer internship had just ended.

We were sitting around a table on the deck at my parents’ house, under a big green umbrella, sipping some sangria that Emily had brought. My parents were both at work. My little brother, Jordan, was home, but he left us girls alone. In idle moments I wondered if he would want to play our game after Emily left. I had been enjoying our little game and it had been a few days now since the last time.

Emily had on a bright yellow summer dress with a tiny print. It had little strings on the shoulders and was ruffled across the breast, made to be worn with no bra. Unlike my small chest, hers filled out the dress properly.

I had on what I called boy-shorts: soft flannel things cut like oversized boxer shorts. They were pink, and above them I wore a loose white tank tee, also with no bra underneath. It was baggy enough that it revealed nothing about my chest, as I wanted it.

Along with the wine, Emily had also brought a copy of Penthouse magazine that she had “borrowed” from her younger brother.

We looked and giggled together and sometimes gasped at the girls who were splayed so obscenely across the well-used pages. But looking at “wide open beavers” – or “WOBs” as Kurt Vonnegut called them – had only so much interest for two college girls. Emily turned to the “letters” section and, reading to herself for a second, wiggled in her chair and grinned, “oh, listen to this!”

She proceeded to read me a story about a man who had been working as a nude model when the gorgeous, 36-24-36 blonde who was drawing him set down her pencils and had sex with him three different ways. Although I’d seen a boy start to get hard again not long after having one orgasm, it sure seemed to me that three in a row was a bit much.

“I never dreamt this would happen to me,” indeed!

Although we both laughed, I felt a familiar warmth start to grow in my middle.

I grabbed the magazine from Emily and read the next letter to her. It was from a woman who really enjoyed sharing the magazine with her husband, and who took inspiration from the photos of some of the girls to let her husband enjoy her anally for the first time. I remember she described the feeling as “not unfamiliar,” and I wasn’t sure I wanted to know what that meant. In fact, I squirmed a little thinking about having a penis in there. I mean, I knew some people did that, but, ouch.

With a few glasses of sangria in me, and the pleasure of being with Emily, I was becoming nicely relaxed. The raunchy discussion of sex between us, even if it was just other peoples’ crazy fantasies, kept a pleasant tension growing in my belly.

It was Emily’s turn, and she read a story about a young man masturbating alone in his room, describing in some detail the way he touched his penis and cupped his balls to give himself pleasure. Then came a tap on his door and, too quickly, his mother had walked in with a stack of clean laundry. Confronted with his obvious predicament, she had frozen on the spot. Meanwhile, the sight of a woman observing his private business had pushed him over the top, and he described how he coated himself with “buckets of goo” right there in front of his mom.

“Buckets of goo.” Honestly, who thinks of these phrases?

But you know, of course, what that story had brought to my mind. My own little brother, 19-year-old Jordan. This summer, I had discovered that he liked letting me watch him masturbate. And I discovered that I liked watching it, too. In fact, just a few days ago, we had each pulled off our bottoms and pleasured ourselves in our turn, right here on the deck.

Unaware of my thoughts, Emily let out a “whew” and made a show of wiping her brow as she passed the magazine back to me. There was one letter left.

“I’ve never seen a boy do that,” she said, “but I just know my brother does it. What else would he be doing with this stuff?” She gestured at the magazine. I blushed as I fumbled to pick it up.

“Whoa, what are you blushing for? Don’t tell me… Have you … you know … ever watched a guy doing that?” I avoided her eyes. Seeing me hesitate, she rushed on. “You have! Oh, no, girl, you have to tell me all about it. My God, ataşehir sarışın escort that’s so nasty! Really? Who was it? What was it like?”

I was embarrassed to the limit. I gave her a weak smile and held up one finger and stood, making like I had to go to the bathroom.

“I want to hear everything when you get back,” she called after me.

I did not have to pee. Instead, I went quickly down into the family room, where my brother, Jordan, was alone playing bumper pool on the little table down there. I noticed that two windows high up on the wall of the converted basement were open.

“Jesus, Jordan! Were you listening? Could you hear us?” I asked in a low tone, unable to hold back a smile.

He laughed gently. “Yep. I heard. I know why you’re here and the answer is ‘no.'”

“Oh Jordan, come on. I think she would love it. Why not? You know I do!”

“Really? I think she’d just think I’m a loser.”

“I think you’ve got it all wrong. You need to trust me on this.” He looked at me and raised his chin in a way that said “I’m listening.”

“Just let me ask her, please? And you can listen and see what she says.” I gestured toward the open window. “I’m telling you, she’ll love it.” And I added, even more softly, “and then she’ll owe you one.” I could not resist a wink.

My little brother moved away from the bumper pool table and set down his cue. I thought I detected a bulge in his crotch. He just shrugged, saying nothing. “Wait here!” I whispered, and practically flew back up and out to the deck.

I sat down across from Emily, doing my best to suppress a smile.

“So, Emily,” I said slowly.

She leaned forward to hear my story. “No, wait,” she interrupted quickly. “Tell me it wasn’t Bill Kelly, isn’t he the one you … you know…?” She meant the boy whose cum I had swallowed the summer after graduating from high school.

“No,” I assured her. “Better.” This got an appreciative “ooh” out of her and she clapped her hands.

“What if,” I began, still dragging it out slowly, “what if you could actually watch a guy do it for you right now, live?” Her eyes went big and round, and her mouth was following suit, as the realization came to her.

“Jordan!? No!” and she leaned forward so far she nearly came out of her chair. “Oh my God, I mean yes! Are you serious? He…” and she made a gesture with her hand simulating a guy stroking himself. “Oh my God!” she repeated.

“Do you want to? I’m sure he would if you want.”

“Girl, what are we waiting for?” I had expected I could eventually talk her into watching him. I was a bit surprised, however, at her eagerness. I guess I was not the only girl who liked watching a man showing his most private touch for me.

She stood up and gave me a “get moving” gesture. I led her down to the family room where my little brother was setting up another game of bumper pool. He looked at me and blushed when Emily and I came in. He avoided looking at her.

“Well, bro, she said ‘yes.’ In fact, I think what she said was ‘hell yes.'” Emily gasped and slapped me lightly on the arm.

He kept his eyes on me and said, “Well, you know the deal. I’m not the only one who loses my pants.” Crap. I hadn’t thought of this. My secret was out. Emily was staring at me now with her jaw open and it was my turn to blush. “In fact,” he went on, “since I’m … since there’s two of you, I think someone should get naked. All the way.”

Emily and I stumbled on each other’s hurried denials. “Oh no. No way.”

“Ok, fine,” he said, and pretended to go back to his game.

To my surprise, it was Emily who wouldn’t let go. “We’ll make it fair. We’ll … we’ll play a hand of Hearts, and the loser has to strip.” Hearts was a game that Emily and I and our friends had played a million times over the years. “Jordan plays too, but his score doesn’t matter, just me and you.”

I really, really didn’t want to show my chest to my brother, any more than I wanted to be naked with him where Emily could see us. But her compromise seemed only fair, and the sangria and my desire were out-voting me. So with a slight feeling of dread at where this might lead – what I might have to do – I gave in and grabbed a deck of cards from the game closet. We sat on the floor around the coffee table and my kid brother removed the two of clubs and dealt out the 51 remaining cards.

I picked up my cards and sorted them. I looked worriedly at the Ace, King and ten of Diamonds; that could be trouble. But there was not much else in my hand. No high Spades, and just two low Hearts. The rest I could find a way to get rid of.

Emily, to Jordan’s left, played first. We played a few tricks without breaking the ice, and finally Emily was the first to take a Heart. Nice. ataşehir şişman escort I relaxed a bit thinking that I was one card closer to keeping my clothing on my little breasts.

When Emily took the second heart, a nagging doubt rose in my mind. By the time she had collected five of them, I was sure.

She’s shooting the moon, damn it, I thought, biting my tongue to avoid table talk with my brother. Shooting the moon: a truly appropriate name under the circumstances, I thought with a wry smile. If she took all the “bad” tricks, she would win. It was risky, sure, but sometimes the only way out if you had a lot of high cards. It failed often enough, and when it did it failed spectacularly, leaving that player with most, but not all, of the unwanted cards.

Emily must have a very bad hand. She was playing all-or-nothing with her modesty. And mine.

“Little brother,” I willed him to read my thoughts, “do something! You’ve got to protect me. Take one before it’s too late. Too late for me. Don’t make me be the one who has to undress.” But I respected the rules and said nothing.

She led out the high Spades, trying to draw the Queen. Jordan must have had it. He ducked the Ace and the King. With that, Emily gave an exasperated sigh and led a low Club with a gesture of surrender. She had failed and she already had five hearts against her. I smiled triumphantly, imagining her shame as she dropped the cute summer dress in front of us. My brother was going to love watching that.

I had to take the Club trick with only the five. I pushed a low Spade at my brother, and he smiled broadly at me before playing the Queen. Emily dropped another high Heart on the trick, now desperately trying to get rid of her winners. But the first bridge had been crossed; my brother had taken one for me, preventing Emily from getting them all. It was 14 points for him, but as Emily had pointed out, that didn’t matter. He would be stripping for us no matter who won the game. This was between Emily and me. And he was on my side.

Alas, brother led a Diamond, and my ten was good. I was stuck in the lead with few cards left and the knot in my belly grew as, one by one, I collected the remaining Hearts. At the end of the game, Jordan had 14 points, and Emily 5. I didn’t bother re-counting the 7 Hearts in my pile. I had lost. I would have to strip naked in front of Emily and my brother together.

Jordan stayed quiet as Emily gloated. “Come on, girl, take it off! You’re holding up the show.” I was tense, reluctant, and I felt heat spreading unwanted from my breasts to my cheeks.

We all stood, with Emily smoothing her summer dress and taking a seat in the overstuffed chair near the sofa. I looked at my brother with a nervous smile. “Turn around a sec, ok?” I asked him. He gave me his own reassuring smile and turned to face away from me, folding his arms. I turned as well, and stepped out of my boy-shorts and stopped. The top or the panties next? It didn’t matter in the end. I chose the top and removed it, and noticed Emily watching me, a hand covering her mouth. “What are you looking at?” I demanded in mock anger.

This was it. It was hard – harder than peeling off my pants on the deck for Jordan to see. I had never undressed in front of my best friend. She would see me do it now, with my brother right there in the room.

And worse, if it could be, the handfuls on my chest had never been seen by a male.

Emily reached out suddenly and yanked my panties past my knees. I felt my bareness right through me. I bent at the knees, ladylike as I could; freeing my panties, I folded and set them with the rest of my clothes. I quickly dropped onto the couch, trying my best to crawl into the corner of it and disappear. Looking at my brother standing there, his back to me, I reminded myself this was going to be worth what I was feeling right now. I was going to get another boy show, and to share it with my best friend. But my naked body was paying the price of admission for her. I vowed not to let her forget it. I drew my bare knees to my chest.

“Ok, go ahead. You can turn around now,” my voice quivered as I said it. He turned his head and found me. My hands moved involuntarily to cover my boobs.

He turned the rest of his body then, and seeing me covering myself, he cocked his head and gave me a half-hearted scowl. He peeled off his shirt, and then in one motion pushed his denim cut-offs and white briefs together to the floor. Emily let out a little “oh my God” as he straightened back up. He was hard. She whispered to me “it’s so… nice!” A whisper, but loud enough that I knew my brother could hear it.

He took himself in his hand while still standing and, returning her appreciation, he pointed himself straight at Emily. It ataşehir sınırsız escort might have been the first time he had looked directly at her. He touched himself slowly up from the base of his shaft, letting his hand slide all the way past his swollen tip. His erection bounced free and he settled himself on the corner of the sofa across from me.

The cushions shifted with his weight. Without thinking, I moved my hands down from my breasts to help me adjust on the couch. Once I settled, I quickly returned them.

“It’s ok, you know,” he said gently, subtly massaging himself as he spoke. “I think they’re really pretty if you ask me.” My own kid brother telling me, naked me, that my breasts were pretty. An odd sort of gratitude washed over me and a tingle ran over my skin.

“She has beautiful breasts,” Emily responded firmly. “I can see you don’t mind looking,” she added, giggling as she nodded at his rigid member.

“Hmmmm,” he breathed, taking just one finger and rubbing the tip of it up and down the length of his penis. He had one leg bent and resting along the back of the couch, his foot a mere inches from mine. The other leg was stretched out with his foot resting down on the floor, pointed nearly at Emily. His testicles rested softly on the cushion beneath him. As he continued to touch himself lightly like that, my eyes were locked on his body, and Emily ceased to exist. My hands fell forgotten to my sides. I let one bent leg rock back and forth against the other, sending pleasant sensations coursing through me.

My brother took so much time pleasing himself, gently, slowly, lazily. He would seem to reach a plateau where his toes would stretch apart and he would breathe out a soft little moan, then remove his hand completely and draw in a gasp and start all over again. The sweet agony of want was driving me crazy; I don’t know how he lasted so long.

At last, he could postpone it no more. He tilted his head way back on the arm of the sofa and pointed his penis higher in the air than he ever had before. He gripped himself in his thumb-and-two-fingers way and his movements became quick and uneven. “Oh fuuuu…” he breathed, and then he shot stream after thick white stream of himself up in the air, looping ropes of his climax, to land on his stomach and ribs. I sensed real wetness arrive at the tops of my thighs and my nipples were so taut and sensitive just then that I’m sure they would have burst from a touch. I loved watching his seed squirting up from the fat tip of his dick.

If I thought he had pumped out a large volume of liquid before, I had seen nothing yet. Clearly, this new escalation of our secret masturbation game had brought him to a new level of climax.

He looked down at himself and quickly brought his arms in to his sides and leveled his belly. It dawned on me: he had draped so much of his fluid on his belly that if he so much as moved right now, he would drip sperm onto the fabric of the couch, and that would be a bit of a problem.

I jumped up without thinking, to get a hand towel, and in the same motion I grabbed my top, dragging it with me. As I moved, I saw Emily, remembered Emily, from the corner of my eye. She was quickly pulling down the hem of her dress and pretending to brush something from her knee. She looked up at me sheepishly, cheeks speckled red, and shrugged. I wondered if Jordan… Had she…?

There wasn’t time to finish the thought. I imagined him soiling the couch any second. I moved quickly to the downstairs powder room, pulling my top over my head as I went. It barely came down over my privates, but it was something. I grabbed a hand towel and wetted it with warm water.

When I got back, Jordan still lay there nude, his penis thick now but not hard, still awkwardly using his arms to stop his orgasm from staining the cushions. Without thinking, I reached down and began wiping his cum from the arm nearest me, so that he could free it to clean himself the rest of the way. I inspected my work and saw that there was a good bit of the stuff on his hand, the hand that he had used so slowly to produce this condition.

While Emily sat silent and still, I took my brother’s hand in the wet towel and gently cleaned his thumb and fingers. It rushed through me hard without warning that this was a deeply, unexpectedly intimate way of touching him, hand to hand, separating his fingers, taking care of his semen for him.

It had been an unstated rule that we did not touch during these games, my brother and me. Watching each other was one thing.

That barrier held solid for me, meaningful and important to me, and I hurried to finish his hand and release the raw touch; yet, as I wiped his mess from my brother’s hand one finger at a time with the cloth, something light and electric seized my heart. My bare sex felt the air burning between us.

And then a movement near his belly drew my eye, while Emily sat there yet, silent and still.

Oh God, little bro. Oh, Jesus God, not now.

Lying on the sofa right after his hot climax, bared there before Emily and me, with his hand being cleaned by me and the wet towel, my kid brother, Jordan, was hard.

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