Timmy #11: Restaurant Fuck & More

Restaurant Fuck and More

The Rest of Sunday

It’s been a while since I updated my life in full. I’ve been stuck in the past, reliving that hotel experience with my sister every time I open my journal. It’s time to move on from that. I don’t know how much longer I’ll be writing in this—I was going to stop altogether, but interesting things have happened in the past four weeks.

A quick recap of my time with Diana in the hotel involves one thing: sex. Diana had plans, but she didn’t want to leave the room any more than I did after that first time. I had my sister in the shower, her facing the wall and me behind her, holding onto her hips while I pulled her pussy onto my cock as I pumped my meat between the soft shell of her silky clam. Water splashed all around us, droplets on my sister’s skin, her hair soaked and swinging, her butt smacked wetly against my hips—the tight jiggle of her ass sending my balls into overdrive. When I came, I didn’t pull out, filling her pink box full of my seed once again. It wasn’t until later she told me she was on birth control and had been since she decided that she wanted her brother, me, between her legs.

I learned during that shower that water does not make for easy penetration—it’s wet, but it isn’t slippery—but my sister’s little cunny dripped with so much cream that a couple of slides through her lips was all it took before my knob popped into her pink slot and down the Slip N’ Slide I went.

The only time we managed to leave the hotel room was to go to dinner. We went to a fancy restaurant, and we had dressed up, my sister looking about twenty-five years old in her red cocktail dress slit down the left side, the halter top wrapping around her neck, and leaving her shoulders bare, most of her cleavage open for viewing. Eighteen or not, men’s eyes were on her. Before our meal arrived, my sister went to the restroom, and a minute later, a young waitress asked me if I was Diana’s brother and that my sister needed my assistance. It turned out that the waitress was one of Lana’s cousins, the daughter of the uncle that she was fucking, and my sister was in the staff’s locker room.

“You have five minutes,” the waitress said; Cindy was her name, I think.

My sister stood in the locker room, sideways to me, one high-heeled foot on the ground, and the one closest to me posted on a bench where employees could sit. Diana was toying with the straps around her ankle while the slit portion of her dress was thrown over the back of her ass to the right, leaving the profile of her smooth body naked from her waist down. Diana wasn’t wearing panties, and her smooth, tan skin hardened my prick on the spot.

She didn’t say a word as I walked behind her, pulled her dress to the side and completely off her ass, and caressed her ass cheeks and pussy lips with my hands. I bent low, licking her, kissing her, tonguing her crack and pucker, and then she reminded me that we didn’t have much time. My cock came out, and I stuffed her pussy full of meat, my sister uttering soft fuck sounds as I slowly worked my prick through her juicy twat. Once I was inside her, I fucked her hard, making her titties shake. She lost her balance and had to straddle the bench. I followed her pussy, sat down behind her, and made her lay her tits and stomach flat on the bench. She had to bend her knees and ride the bench like a jockey in a race, her leg muscles straining as she fucked herself back onto my cock. I gave her a fucking, leaving her breathless. By the time we walked back to our table, there wasn’t a person in the restaurant who couldn’t tell that I had just ridden this stunning young woman to a leg-shaking orgasm.

“Fucking wrestlers,” Diana said as she tried to fix her hair. Her lack of panties meant that she had to sit in my cum for the rest of our dinner. Once in her Civic, she made me lick her clean several times.

That night we made love, and the following morning we fucked against the floor-to-ceiling windows, then we went home after checkout.

Present Day

The wrestling season has started. That means long practices, weekday dual meets, and weekend tournaments, and our star senior is out with a broken collarbone. Poor Roy, but I couldn’t feel bad about it, even if my sister was pissed that I was the guy responsible for his injury.

On the Monday following our night at the hotel, I asked her why she had chosen me to have a relationship, her own brother, when she could have any guy she wanted. It’s not like you woke up one morning and decided that you wanted to become romantically involved with a family member. It took a while for her to answer, but she did answer me.

“Roy,” Diana said. “It happened while I was dating him. One night, he was tired of kissing me and wanted more. He didn’t want to listen to me when I told him no.” She put her hand on my shoulder. “Don’t interrupt me. We struggled. I managed to grab my phone, but I couldn’t dial anyone. I accidentally hit the video record button.” Diana frowned. “To get him off me before he could undo my jeans, I bit him on the neck hard enough to draw blood”—I’ve seen those scars on his neck—“the pain was enough to bring him back to reality.”

“Why didn’t you tell me,” I asked, “or call the police?”

“Tell you, why? What the fuck could you do? And don’t suggest one of those stupid scenarios where you come to my rescue by beating him up. That’s a pathetic boy’s daydream; you’re not a boy, are you? Men who think like that stay single for a long time, and they spend their lives jerking off to rescue fantasies. Besides, I had a video of him trying to rape me. I had what intelligent people call leverage.”

I kept quiet, but let’s be honest, every man wants to be the hero, I sure did.

“I took the attempted rape video to his family, with a few friends of mine to watch my back. And his parents paid me to keep quiet about it, but I told them that I was keeping the video and that if I ever heard of Roy trying something like that again, I was going to the police.”

“How much did they pay you?”

“One-hundred and fifty-thousand,” Diana said, laughing. “And I get that same amount once again when we graduate. Roy’s grandfather left him a small trust, so I’m sure it came from there.”

I stared at my sister, wide-eyed and stunned. We came from wealthy families, but damn, that was a lot of money for a high school girl. This writing does no justice to how everything happened. I’m paraphrasing because it’s almost too hard to believe sometimes.

“The money is in my closet,” Diana said. “Something happened that night. What Roy had tried to do to me had turned me on, but only after it was over. I don’t understand it. I was so fucking wet from thinking about it that I masturbated in the shower and then in my room when I got home, but I never thought of Roy. I touched myself to the idea of being forced by some faceless person that I trusted. Someone I knew would never hurt me. Someone I loved.” Diana shook her head. “I talked to Lana about it, wondering if I was sick, and she told me that she fucks her uncle, and that’s when my faceless lover became you for the first time.”

I still had nothing to say.

“I thought my brother would never hurt me, and I’ve always thought you were sexy”—she smiled at me—”but you were an asshole—that’s not fair—we didn’t get along for some reason. But, I trust you to take care of me, so why not go after you? I don’t know, but maybe that night fucked me up, or maybe it awoke something in me that was always there, but here we are, and I like being where we are.”

I didn’t know what to say. Sometimes there are no words, so I kissed my sister, and made love to her in her bedroom, followed by tying her hands behind her back—on her command—and blindfolding her. I fucked her from behind until she came on my cock, and then I turned her over and covered her tits with my jizz.

The next day, during practice, I dropped Roy on his collarbone while doing what we called the Fireman’s Sprint—that’s sprinting while we hold a teammate in a fireman’s carry position across our shoulders. I don’t know what I thought would happen, maybe a dislocated shoulder at most, a bruised ego, but I broke Roy’s collarbone. When I dropped to the mat to check on him, I whispered, “For Diana,” and he didn’t say a word.

Diana was pissed when she found out, and she was right to be: it was a little boy’s revenge, but she still fucked the hell out of me that night, riding my dick until it ached and then sucking my cock until I had no more nut to bust. Then she masturbated for me with her legs spread wide until she couldn’t come anymore. She did it right in her room, with Abbey and Mom in the house. Diana didn’t even care that they were home. She locked her door, and away we went. Fuck, she had been aggressive with me.