Timmy #10: Losing Our Virginities

The First Time

Saturday, in the Hotel

The hotel loomed above us, a pretty building of white and peach stone with a circular parking lot and a several-storied parking garage behind it. Diana parked in the garage. She led the way to the hotel’s entrance as I walked behind her, both of her bags held in my left hand, and my bag was in my right, held in front of my tented jeans. Each uncomfortable step I took made me grit my teeth behind the flat line of my lips. My eyes searched everywhere for anyone who might notice my crotch’s predicament.

We walked into the lobby, and Diana headed straight to the front desk. I stood near her in line, and she smiled as I held my bag in front of me. She shook her head. I shook mine. She shook her head again, tugged at her lower lip with her teeth, and jerked her head to the side several times.

I shook my head.

She removed her sunglasses and widened her eyes at me, leaning her head forward.

Sighing, I moved the bag. Even though I was in jeans, only a person missing the benefit of sight would miss seeing how excited I was to be in the hotel. My cheeks reddened, and Diana patted one of them before moving up to the counter to talk to the desk clerk.

I looked around the marble lobby. Shiny fixtures, pretty furniture, high ceilings, and fancy TVs didn’t hold my attention. Some people looked at me; some noticed my situation, some didn’t. One, an older woman, laughed. I realized that standing next to my sister as I was, we looked like a pair of eighteen-year-olds getting away from home for a sex-filled weekend ... which we were.

In the elevator, I asked, “How did you book this?”

“I didn’t,” Diana said. “Lana did, with her uncle. They left us keys at the front desk.” And then she handed me mine, but since my hands were full, she slid the key into my pocket for me. “Still hard? Good.”

“I don’t want to wait until tonight,” I said.

“Too bad,” Diana teased.

“I’m not going to.”

“No?” she asked, shaking her head at me.

“No.”

My sister laughed, saying, “I’m giving you my mouth, little brother, so you better enjoy it.”

I didn’t say anything. The doors clicked open to the sound of a bell, and we walked onto the twenty-first floor and down the hallway. My feet echoed off the carpet, my sister’s glided, her long legs carrying her quickly through the halls. I watched her dress swish around her thighs, my aching more and more with each of my steps.

I wanted her so damn much; I imagined myself not waiting for the room. I imagined myself dropping the bags, grabbing her from behind, and pushing her against the hallway wall. My sister would struggle, but I’d lift her dress above her hips, free my cock with one hand as I held her in place with the other, and then I’d push my knob through her silky lips and into her virgin body—right to her core, and she’d thank me for it.

Fuck, I clenched my ass as a spurt of pre-cum entered my jeans.

We stopped at our room. Diana swiped her card in the mag-lock, and in we went. I dropped the bags as soon as I crossed the threshold. My sister had run ahead of me, admiring our large room with its king-sized bed, plenty of walking space, a TV, a sofa, a table, and chairs. Everything was in red, white, and gold, pretty colors for a pretty room. The far wall was one giant window set flush within thick metal panes; their sheer white curtains were open and swept to the side, letting the daylight fill our room.

My sister walked to the window, threw up her hands, and spun. “Look at this room!” She smiled as she saw me walking toward her. “Timmy, no-no-no, my mouth, remember? You get my mouth.”

I picked her up and pushed my lips to hers, my forward momentum pushing her against the floor-to-ceiling windows.

“Umm, wait,” Diana moaned. “Tonight, oh fuck, can’t you wait?”

“No.” Lust and need hardened my voice. I slid my hands down the backs of her tapered thighs and then up and under her dress, cupping her bare ass cheeks sticking out of the French cut panties she wore. Her firm hills filled my fingers, and I squeezed her meat hard.

“You fucker,” Diana said, kissing me back, her tongue everywhere. “What if I say no?”

“Don’t say no.”

“What if—”

I slowed down and kissed my sister deep, taking my time as I ran my tongue over hers, tasting her as I rolled my body against her like an oiled, exotic dancer. Diana moaned, then sighed, her voice drifting away as she closed her eyes and let me make love to her mouth.

“You disobedient fucker,” Diana whispered when I broke the kiss. “If you’re going to force me, then you better make love to me the way you just kissed me, okay?”

“Okay,” I said, lifting my sister by her ass and carrying her to the bed.

Diana bounced when I dropped her onto the comforter. She crawled backward, an anxious smile on her face as I pulled off my shirt and pushed off my shoes. I leaned down to remove my socks. My sister didn’t bother undressing. She sat on her butt on the bed, legs extended, knees slightly bent, her hands on her thighs, and her eyes on me.

“My cock hurts,” I said as I unbuttoned my jeans, the zipper following.

“My fault?” Diana asked, pouting apologetically. “Oh, my poor little brother.”

I shimmied my jeans down my legs, my prick so hard that it turned my skin-tight, cum-stained boxer-briefs into a divining rod pointing straight between my sister’s legs. Diana purred as I pushed my briefs down my thighs, and she laughed as my dick sprung up, big and hard, surprising me with its size. My member looked angry, veined, and harder than granite.

“I’m not kidding,” Diana whispered. “You better take it easy on me. I mean it.”

I laughed, my heart swelling with ego, my shoulders rising with pride.

“Nerd,” Diana laughed.

“I’m just hoping I don’t come before I’m inside of you,” I said and crawled onto the bed.

“We can take care of that.”

Diana surged forward, catching me off balance. I almost backed off the bed, but my sister gripped my cock in her gentle fingers and engulfed my prick with her warm mouth before I could decide what to do.

“Fuck,” I gasped, trying to pull away as my balls tingled and my orgasm surged to life.

I was too close to coming, and the warmth of my sister’s tongue against the underside of my shaft was too intense to fight. She went down as far as she could, gagging with about a quarter left of me to take. I clenched my jaw, grabbed my sister by her head, and came while trying to push her from my prick.

“Fuck, oh fuck,” I moaned. My hips jerked, forcing my cock further into my sister’s throat. She pulled off, gasping and breathing hard as my cum splashed against her chin, throat, and chest above her neckline.

“Oh well,” Diana said, laughing. “I guess we’re waiting until tonight.” She looked at me with big, apologetic eyes that were impossible to believe by her smug grin and laughing lips. “Can you get a towel for me, little brother?” She pouted. “You made a mess on me.”

I glared at her, but I walked to the restroom. I grabbed a hand towel, turned on the warm water, and washed my cock. Fuck, but my prick wasn’t going down. That’s right; my erection never left me, staying hard for my sister, who sat so pleased with herself in the next room.

When I exited the bathroom, my sister’s laughter died away slowly as I went to her. Her surprise and resignation sent a thrill pulsing through my shaft. I held the cloth in my right hand and tilted her chin up with my left, and I wiped my cum from her chin, neck, and chest.

“We’re not through,” I said and bent down to slide my tongue across her lips. “Brace yourself.”

Diana laughed, and so did I, having heard that line in a Milfhunter porno once, right before Mason Storm looks into the camera and says, “He’s tearing up my pussy,” a couple of times. I had no intention of tearing up my sister’s pussy, but if my sister ever told me that I was tearing up her pussy, I’d come right after.

I undressed my sister, starting with her knee-high leather boots. I’d have loved to let her wear them, but this was our first time, and my naked body sliding over hers felt like the right way to do this. One boot and then the other, then her socks, and held onto her right ankle and licked the smooth sole of her foot—the scent and taste of her lotion clinging to her skin.

“Ah,” Diana gasped as my tongue ran the length of her sole.

She shivered and tried to pull away from my tongue, but I held on, remembering how sensitive her feet seemed to be. I licked her again. She dropped her head back and clawed at the bedspread. Goosebumps sprouted across her leg when I took her big toe into my mouth, and she shook her head as I sucked on the little piggy. From there, I kissed my way up her legs, pushing her thighs apart and her dress up and over her hips. I ran my nose along the seam of her lavender panties, stopping to tickle her slit with side-to-side motions of my head.

“Mmm,” Diana whispered, humping her soft pussy against me, her thick and heavy scent filling my lungs as I breathed her in.

I removed her panties, the crotch creamy and wet, and I tossed them to the side. Her bare muffin waited for me, glistening and shiny with her cummy juices as if she had poured oil across her skin.

“So fucking sexy,” I said as I ran my hands up the insides of her thighs, bracketing her pussy with my thumbs and forefingers. “I can’t believe we’re doing this.”

“I’m can,” Diana said. “But I planned it, so...” and she shrugged, her cheeks blushing pink.

“And now you’re letting me in right here.” I kissed my sister’s muff, tasting her sweet, sticky honey from earlier. The flavor of her cunny warmed my mouth and throat as I licked it up. Diana whimpered, bucking her hips and feeding me her snatch with snake-like motions of her hips. I licked her slit from top to bottom and then back to the top, taking her clit into my mouth and sucking the rubbery nub with gentle, inward motions of my lips and tongue.