Double or Nothing Ch. 09

It didn’t take Jordan long to figure out that Emily and I had been making out together, and maybe even a little bit more. Emily did her best to be attentive to his needs so that our fooling around together wouldn’t make him jealous.

That seemed to be working out fine, because what Jordan began to display wasn’t jealousy at all, but instead an intense curiosity about what we had done together, and what it was like.

Emily, who of course had been totally intimate with him now, wanted to let him watch us make out. “I guarantee it’ll get him to play with himself for you,” she tried to encourage me.

But I was still painfully shy even about letting my kid brother look at my little breasts, or about letting him watch me masturbate. It had been a big step for me just to be able to pull my pants down in front of him, as he always wanted me to do when I watched him.

So, my answer was “no.”

This didn’t stop Emily and me from sneaking off together whenever we had the chance, to explore this new side of our sexuality. We would go into my bedroom if Jordan was around, and I would always lock the door just in case.

After just kissing and cuddling in my bed the first time, Emily had then brought me off with her hand in the shower. The next time we snuck off, we kissed and petted each other for a while, until eventually I got up the courage to take the next step. I was determined to return the favor for her, only this time, I wanted to help her along with my mouth.

I pulled back from our embrace and touched a finger to her pretty young lips. “Let me,” was all that I said. I helped her out of her sweater, and took a few moments to stroke her pale shoulders before my hands moved to her bra. I helped her out of that, too, and cupping her breasts in my hands I leaned in and kissed each one, right on the nipple. Her little points became firm against my lips as she cradled my head in her hands.

I stroked the curve of her waist and then trailed my fingers inside the tops of her jeans. I unfastened them and nudged her to lift up off the bed so I could pull them down. Tugging at the hems, I took them all the way off of her long slender legs. I kissed my way back up her calves and her thighs and then stopped, my face hovering just above her pink cotton panties.

I was so close I could smell her desire. I touched her there, softly, with two fingers, through the thin fabric, and she let out a soft moan. I was vaguely aware of the nice feeling of her fingers in my hair. I brought my head down and kissed her through the cotton, working up my confidence to actually taste the real thing.

She moved to pull down her own panties, but I gently replaced her hands with my own. Slowly, teasingly, I inched them down past the beautiful curve of her hips, and before taking them all the way off, I used a hand to smooth her sparse pubic hair away from her special place and, looking up at her with a smile, I bent down and kissed her there softly.

I was intoxicated with her. I let my tongue peek out and touch her, tasting her for the first time. It was salty and rich with her natural aroma, and she moved herself against me as my tongue grew more bold. At the same time, I peeled her pink panties the rest of the way off.

I savored my first taste of a woman then, taking my time and giving plenty of attention to her engorged little button. I had to stop every so often to pull one of her little curly hairs out of my teeth, but I didn’t mind.

As for Emily, she became wetter and wetter as I explored her with my tongue. I stroked her soft curves with my hands as I pleasured her with my mouth, and she showed her gratitude by rocking her hips and grinding her beautiful sex against my face.

There was no doubt of her orgasm, when it came. Her whole body clenched as she cried out “yes” and “Oh my God, yes,” and I was especially proud of those cries. My face was soaked with her moisture by the time her climax subsided, and I could still smell her as I withdrew my head from her thighs and stroked her glistening lips with my fingers.

I had done it. I had given oral sex to a girl.

Over the next several days, Jordan and Emily continued to press me to let him watch the two of us girls doing anything with each other, and I continued to resist until, one day, my dad happened to leave one of his ties on the dining room table.

Emily and I had been in the kitchen, putting away our lunch dishes, when she picked up the tie and ran the length of the silk through her fingers. She nodded suggestively toward Jordan, who was sitting alone on the love seat in the living room. I thought I knew what she had in mind.

I stood in the doorway as she straddled Jordan, tying the tie across his eyes like a blindfold. She kissed him and stroked the front of his pants once before taking a place on the couch and gesturing for me to join her.

I knew what she wanted and, with Jordan blindfolded that way, I was just bold enough to do it. I moved to the sofa beside her and sat down, and resting my hands on her soft little shoulders, the two of us started to kiss.

From the very first moment, we could tell that this was getting Jordan excited, and almost immediately he began rubbing himself through his jeans. That in turn encouraged us, and we explored each other’s mouths for a while.

As the two of us girls traded kisses, Jordan gradually opened his pants and pulled them down past his knees. He brought his hand to his shaft and began slowly giving himself pleasure as Emily and I continued just softly kissing each other.

My hands went to Emily’s face, brushing her hair back from her forehead as, again and again, our lips softly touched and released.

This time it was Emily who started undressing me first and then treated me to long strokes of her fingers on my skin. I lay back and watched my brother remove the rest of his own clothing and return to his slow gentle touching.

Emily brought her tongue to my clit for a while before finally letting me undress her too. She hesitated then, unsure what to do next, so I stretched out on the couch and guided her above me so that we could simultaneously pleasure each other with our mouths.

Her beautiful bottom presented a lovely sight for me, spread out right there above my face. I leaned up and tongued the whole length of her sweet opening before settling in on her sensitive place, my nose nestling between her tight little hole and the puffy wet base of her lips.

We each came, then, letting Jordan hear the soft cries of our pleasure, and as the two of us girls untangled ourselves, I could tell that he was getting close to showing us his own release.

On an impulse, I nudged her toward him, and she climbed up onto his lap on the love seat and, drawing his hand away from himself, she impaled herself on his hard penis.

Once again, I had a perfect view of her little brown jewel as his thick member parted her lips. I used a hand to roll one of my engorged nipples between finger and thumb, and let the other one move down to answer the need that was growing inside me again.

Emily sat still on Jordan’s lap for a moment, and they shared a long, passionate kiss. As I touched myself, I wondered if my brother could taste my own juices on Emily’s lips. I was rising inevitably toward another orgasm as Emily started moving herself up and down again on Jordan’s erection.

His hands roamed over her body and she shuddered, throwing her head back as she had one more climax. I cried out myself as the strong waves of my own orgasm gripped me, and I watched Jordan’s manhood pulse again and again as he filled Emily with semen, some of which flowed back out of her as she continued to ride him.

I stood, then, and caressed Emily’s bare back as she lay collapsed on top of my brother, letting my hand come teasingly close to her cute little anus, so close yet not touching my own little brother inside her.

Planting a kiss on her delicate shoulder, I gathered my clothes and headed up for a shower.

As the summer drew near its end, I confessed to Emily that the one regret I had was not having a penis inside me at all during the entire three month period. It was then that she suggested her plan, and with a few adjustments at my suggestion, I finally agreed that it was something I would at least try.

It began with borrowing not one but two ties from my father’s wardrobe. With them in hand, we lured Jordan into my bedroom and, as we had done once before, we secured one of the ties around his head as a blindfold.

Then Emily had him stand while she undressed him completely. Once he was naked, she made him lie down on his back on my bed, and used the other tie to bind his hands together, drawing them above his head and finally securing the loose ends of the tie to one of the spindles at the head of my bed.

She and I stood, then, kissing and undressing each other. Jordan, meanwhile, had become fully hard listening to our feminine passion, but with his hands tied above his head, he could do nothing about it.

Once the two of us girls were both naked, Emily could not resist the sight Jordan presented, and she knelt beside him on my bed and started stroking his engorged penis. I stood near her, kissing her back and her shoulders, letting my breasts brush lightly against her warm skin. I reached down between her legs and, slipping one finger into her wetness, I massaged near her clit with two others.

My own desire by this time was an insistent ache in my loins, and I used my free hand to make sure that I was ready for what I was about to do.

Emily bent down and took Jordan’s penis in her mouth, getting him very slick and wet in the process. Her butt was now sticking up in the air, and soon my attentions had brought her to orgasm. All of this was getting Jordan very close, too, so we stopped, and Emily climbed off of the bed, leaving him tied, and blindfolded, and hard.

I kissed Emily once more for luck, and then I carefully climbed onto the bed, straddling my brother’s nude body, with my ass towards his head and my face towards his feet. We had agreed that this position further reduced the chance that Jordan would ever realize that it was me.