Waitress Takes More Than the Tip

Hi, friends - something different this week, a heterosexual (!) story I wrote a few years back. Let me know what you think!

Jen and I were the last ones to finish our side work on what had been a beyond-busy night waiting tables at the restaurant. It had been a hell of a night in every sense of the phrase, the worst of which occurred when our busboy dropped an entire tray of food then cut himself cleaning it up and had to be rushed to the emergency room. 

Still, as deep in the weeds as we'd been, I was grateful to be working with Jen. I could always get a lift from the sight of her perky tits in her uniform-standard oxford shirt; her round, luscious ass flexing as she ran to and from the kitchen. 

Side by side, vacuuming crab shell and corn kernels off the carpet, we looked worse for wear in just about every place but our nice, fat pockets. She shut off the vacuum, rested her elbow on the handle and looked at me through half-lidded eyes, her fair blonde hair falling across her face. 

“Let’s get drunk,” she said. I said that sounded like a great idea. 

Four vodka and sodas later the stress of the night was a distant memory. As big of a crush as I had on Jen, we’d never really hung out before. Mainly because I had a girlfriend and she had a boyfriend. Both of whom, we realized after we ordered a fifth round, were out of town. That was pretty interesting. 

Plus Jen and her boyfriend were having problems. I tried to be understanding.

“The sex is lousy,” she said bluntly. “He…oh, I shouldn’t say this,” she said, and threw back one of the shots we’d ordered. “Fuck it,” she said, looking at me straight on. “His cock is too small.”

“That’s unfortunate,” I said, clenching my teeth to show dismay, but also maybe trying not to smile. My cock was starting to shift in my pants. Jen chewed on her stirrer, looked up at me. 

“I’m guessing you don’t have that problem,” she said. I sat back in my chair. I shook my head.

“Nope, I don’t,” I said.

“I had a feeling. I mean, it’s not like those tight uniform pants hide a whole lot.”

“Oh jeez,” I said, genuinely embarrassed. “Guess I should go up a size.”

“No you shouldn’t,” she said, grinning. 

I had never cheated on my girlfriend before and from what I could tell she and her boyfriend were monogamous, too. And so we found ourselves in an unspoken moral quandary. We coped by getting drunker, too drunk to do anything but stumble back to her place three blocks away, where I promptly passed out on the couch. 

***

When I woke she was in the kitchen making coffee. She wore a pair of boy's boxer shorts and a roomy t-shirt - her boyfriend's, I assumed. Her hair was wet and I guessed she'd just got out of the shower. 

"Morning," she said, and handed me a steaming mug. I sat up. My head throbbed.

"Fuck," I said, rubbing my temples.

"Tell me about it," she said, sitting on the chair across from me. "Guess we overdid it a bit last night." 

"Yeah. Probably a good thing we passed out, though. Otherwise we might have a lot more to regret," I said.

"Yeah," she said, smirking over her coffee. "I told you way too much about my boyfriend troubles."

"Well, the fact is that I'm having the same problems. My girlfriend and I haven't fucked in over a month."

"Damn," she said. "I can't understand why people aren't as horny as I am, sometimes. There are so many things I want to try and I feel like I'll never get a chance. Especially not with him."

"Like what?" I said, unable to resist pushing the conversation to where it wanted to go. "What would you want to try, if you could try anything?" She shifted in her seat.

"Oh, god," she said, glancing up at the ceiling. "Okay. The one thing I am most curious about is anal." As soon as she said it my cock started to rise. I thought of that gorgeous ass bent over, my cock sliding in and out of her asshole. I was only wearing my boxer briefs and I was glad for the blanket draped over my lap. "I've tried to get him to do it. He says it's too dirty."

"That's too bad. I love anal."

"Really?" she said. I noticed her nipples were erect under the shirt. 

"Yeah. I'm pretty good at it, too." The room was so quiet. I sipped my coffee. She did the same.

"Have you ever cheated on your girlfriend?" she said.

"No. What about you?"

"No," she said. "But if I did cheat on him, I'd want to do that. The one thing he won't do for me." She adjusted herself, setting her feet on the floor and spreading her legs so that I could almost see up the legs of her boyfriend's boxer shorts. 

"And if you did do that - get fucked in the ass, I mean," I said, "it almost wouldn't be like cheating, right? Cause it's sort of not real sex."

"I guess so," she said. "There's no chance I could get pregnant, at least," she said, and chuckled.

I nodded. "You wouldn't even have to use a condom. I mean, hypothetically speaking."

"Right," she said. Her face was getting flushed. She squirmed a little in her seat. I thought about her cunt, which was probably starting to throb and get juicy. I imagined that juice dripping down toward her asshole. "This conversation is making me horny."

"Me too," I said.

"Let me see," she said, looking toward my lap. Hesitantly, I pulled off the blanket. I told myself I would just do this, just let her see. It wasn't really cheating. It didn't have to go any further.

I spread my legs and let her see my throbbing hard on, like a steel pipe wrapped in the fabric of my black boxer briefs.

Her eyes go wide. "Fuck," she said. "It's bigger than I thought."

"Yeah," I said. Proudly, I guess.

"Could someone even take that in their ass?" she said.

"Oh yeah. My ex did all the time. The thing is, you have to work up to it." As I talked I casually tweaked my boner through my boxers. She watched this intently as she moved her hand up her thighs and pressed her fingers into her crotch. I imagined her juicy cunt lips against the fabric of her boyfriend's boxer shorts.

"How do you work up to it?" she said.

"Well," I said, rubbing my palm up and down my cloth-clad boner, "First you lick it. Has anyone ever done that to you?"

"Sort of," she said. I saw her finger flick toward the top of her pussy, near her clit. Her body shivered a little when she did that.

"What's that mean?" I said, chuckling.

"My boyfriend barely licks my pussy." I thought that was pretty unfortunate. "But I've had guys run their tongues over my asshole. Nobody's ever, like, focused on it though."

"I love licking ass," I said. "I'd have you get on all fours. First I'd lick up and down your smooth thighs. Run my tongue down the small of your back and down your crack."

"Yeah?" she said, rubbing herself a little harder.

"Yeah. I'd go to your pussy next. Flick my tongue against your clit. Get your pussy nice and throbbing and wet. But I'd just flick it, just run my tongue around your pussy lips really lightly. I'd do the same around your asshole."

She nodded. She was really getting flushed.

"I'd work up to it, so that when I'd finally spear my tongue in your asshole you would moan really loud. I'd press my tongue into it nice and firm and deep." Now I watched her fingers travel lower, underneath her pussy to where her asshole was surely clenching and relaxing as she imagined my tongue pressing into it.

"I bet that would feel amazing," she said.

"Are you touching your asshole right now?" I said. She nodded. Her finger dug a little deeper into herself. I had my hand pretty firmly wrapped around my cock. I felt like I could cum just from that.

"I want to see your cock," she said.

"Only if I can see your asshole," I said.

"Okay," she said. She slid her hand underneath the boxers now. I swear I could hear the moist sound of her palm rubbing across her juicy pussy as she directed her fingers down to her asshole. 

I guessed I had to go first. I lifted the waistband of my boxer briefs and pulled them over my huge hard cock. It rose up into the air and just kind of swung there. She gasped a little, pressed her fingers deeper. "Goddamn. It's so big." I stroked it for her. Truth was I could barely stroke cause I was so close to cumming. There was precum collecting at the tip.

"Your turn," I said. She took a deep breath then slid off the boxer shorts. Her pussy gleamed in the soft morning light. She was so wet and she was shaved smooth. She pulled her knees up to her chest and her pussy lips parted a little as she did. Then I could see it - her tight, pink asshole. 

"That looks delicious," I said. She grinned a little half-grin, rubbing her pussy lightly with her fingers. With her other hand she played with her asshole.

"What would you do after you licked it?" she said.

"I'd get my finger nice and wet, and then I'd slowly press it inside," I said, tweaking the thick head of my cock, cupping my heavy, cum-filled nuts in my palm.

"Like this?" she said, and brought her index finger to her mouth. She slid it between her luscious lips, sucking it into her mouth and wetting it with her tongue. The she brought it to her asshole. I held tight onto my cock as she pressed it into her. Her eyes widened and her face slackened with ecstasy. "Oh my god," she groaned, sliding her finger in past the second knuckle.

"Feels good, doesn't it?"

"Uh huh," she said, nodding, looking right into my eyes.

"I'd finger you for a while, next. Real slow and gentle." She did as I suggested, pushing her finger back in, sliding it out again, back in. Goddamn I was horny for her ass. It was impossible not to imagine my cock in there too. But I was still hesitant. There was still the feeling that what we were doing wasn't cheating, exactly. That as long as we didn't touch, it would be okay. 

"I'd suck and lick on your tits, too," I said. 

"Yeah?" she said. With her finger still pumping inside her asshole she used her other hand to lift off the t shirt. There were the tits I'd admired for months - firm and round with hard pink nipples. She ran her hand over them, cupping them, tweaking her nipples, still fingering her asshole. "I feel like I could cum just from this," she said.

"Me too," I said, laughing. I took off my shirt. Now we were totally naked and masturbating in front of each other.

"The next step would be to slide a second finger into you. Get you really relaxed and ready for my cock."

"I don't know if I could take that much," she said. As if to test this theory she brought two fingers to her mouth and got them wet. I wondered how the finger that just been in her asshole tasted. She brought the two wet fingers to her hole and pushed. I watched as her asshole swallowed up the tips. She paused there, her face some mixture of pleasure and agony.

"I'd go slowly," I said. "Giving your asshole lots of time to adjust to it." She nodded, looking right into my eyes, and slid them in another inch. "Once you get used to it, it feels good." She nodded, her fingers going deeper. "Then you just want more and more."

"Fuck. You're so right," she said. "It feels amazing." She pumped her hole with her fingers, her other hand fingering her clit.

"That's when you'd be ready for my cock," I said. I stood up. Her eyes got wide, I guess from seeing my cock hanging there, long and fat as a baby's arm.

"I still don't know if I'd be ready for that," she said.

"We'd have to use a lot of lube," I said.

She let those words sit for a moment. It was me pushing the boundaries, I guess, seeing how far we could go without actually going there. "There's some in the nightstand in the bedroom," she said. I ran to the bedroom and found it in the back of the nightstand drawer, sealed, unused. I held it in my hand. I told myself I could just use it to jack off, because that's all we were doing, right? 

She'd changed her position on the chair and now she was on all fours. Fuck. Her perfect, creamy ass was raised high up in the air and she had three fingers pumping inside her asshole. 

"Damn that looks good," I said. I cracked open the lube. "Here," I said, and I poured the lube down her crack where it streamed over her asshole. As she fingered herself the lube went inside and her three fingers went deeper. 

"Fuck I want a cock in me so bad," she said, looking over her shoulder at me. I poured some lube in my hand and got my cock slick. How easy would it be to just get in position and slide it in? How good would it feel to have that warm, tight asshole gripping my cock?

"We can't though, right?" I said.

"We shouldn't," she said, her fingers as deep inside her as they could possibly be. I was harder than I'd been in months, maybe years.

"What about just the tip?" she said.

"It wouldn't be a bad idea. Just to see if you could take it," I said.

"Yeah," she said. She took out her fingers and pulled her ass cheeks apart, letting me see her asshole which was a deep red now, gaping, opening and closing like it was hungry. "Just the tip."

"Right," I said. I walked over to her and kneeled in front of the chair. I could smell her more clearly now, a fresh softness laced with something muskier - the smell of her pussy and asshole. I lined my thick cock up with her hole and the tip made contact. It was the first amount of actual contact we'd had and it was red-hot and intoxicating. Holding her legs, I slowly pushed inside. Her breath was coming hot and fast. The tip of my cock flattened then popped inside. She took in a sharp breath, I let out mine. Fuck. Maybe I knew it then, feeling her tight virgin asshole grip my cock - it took it so easily. I was going to fuck her ass until I came, wasn't I? It seemed inevitable. But I couldn't. I shouldn't.

"Oh my god," I said, looking in her eyes. "Feels amazing."

"Uh huh," she said, nodding. We stayed like that, not moving, just the tip of me inside her. She pulsed her asshole around my cock and I felt it grip me even tighter, like it was trying to draw me in. Then my cock pulsed and swelled - she moaned when she felt that. 

"I feel like I want more," she said.

"We shouldn't though."

"Maybe just another inch," she said. 

"Okay," I said. I pushed inside. Her asshole gripped each millimeter of my bare cock as it disappeared in her asshole. Goddamn it felt good. But I forced myself to stop, and when I did she threw her head back and gasped. 

"Fuck!" she said. She came forward and grabbed my ass. She was trying to pull me in deeper but I held steady. "Please," she said. "Just slide it in all the way. Just to see if I can take the whole thing." I did as instructed, pushing deeper and deeper, the thick root of my cock stretching her wider and wider until my cock had disappeared in her and my balls were pressed against her ass. "Oh my god," she moaned deeply.

"You're taking it," I said.

"It's so fucking big," she said. After a moment her breath slowed a bit and her asshole relaxed around my cock. She kept her hands on my ass, still trying to pull me in deeper, as deep as possible. So I pushed deeper. I would've stuffed my whole body inside her if I could've.

"Should I pull out now?" I said.

"No, don't. Just stay inside me."

"Fuck you feel so good," I said. 

"Feels amazing," she said, and started to finger her clit again. "Stay in me, I want to cum like this."

"Okay," I said. Her nipples got harder as she fingered her pussy, her whole upper body got flushed. Every time her pussy would contract her asshole would tighten, too, and it would grip my cock, like she was milking it with her asshole. 

Her wet pussy squelched against her hand as she fingered and flicked it. I couldn't help myself, I had to have a taste of those tits. I leaned forward and as I did my cock pulled out just a bit. I wrapped my arm around her delicate back and pulled her upper body toward me, directing one of her delicious tits to my mouth. I swirled her firm nipple in my mouth, sucked down on it hard, nibbled it a little. As I did I pressed my cock back inside her asshole all the way. She moaned. I went at her other tit, and now it was like my hips took on a life of their own. I pulled out a little, pushed back in.

"God yes," she said. I looked up at her. "Fuck me," she said.

"I'm fucking you," I said, pulling out a little further, pushing back in a little deeper. "I'm fucking you in the ass, Jen."

"Fuck Anthony. I need it. Fuck my ass. Fuck it hard." I knew this wasn't going to last long. I pulled out almost all the way - "just the tip" yet again, but not for long - and then slammed the entire length of my thick meat inside her. She called out. I think I did too but my mind was so flooded with lust that it was hard to say. 

"Fuck my ass till you cum," she said, still furiously fingering her clit. Her pussy was red, engorged, her clit firm and swelled. I looked in her eyes and she was right there with me.

"I'm gonna cum," she said.

"Me too," I said.

"Shoot it in me," she said. Our faces were so close. I leaned forward and she leaned forward and as I felt her whole body start to quiver, her moans getting long and low, my lips met hers. I shoved my tongue in her mouth and she shoved hers into mine. Her asshole spasmed around my cock as she came, her orgasm rocking her body, our moans muffled by each other's mouths. One more thrust and I held it deep, emptying what felt like a gallon of cum deep into her guts, a place her boyfriend's seed had never been. It was the best orgasm I'd ever had.

And yeah, the aftermath was a little awkward. She took a shower. I thought of splitting but I didn't, and that was interesting because by the time she got out of the shower I was hard again. I didn't try to hide it. She saw it in my boxer briefs, then came over to feel it. 

"One more time," she said, dropping her towel. Who was I to argue?