Cinderalla

"White or red?" I felt utterly classy, having both.

"White, please." I shook the Chardonnay box to make sure it wasn't empty, then turned the handle and half-filled her glass, figuring that was how they did it, half a glass being like pinky-up. I got myself a can of beer.

"Would you like to see my room?" I asked her. We went into my bedroom and she set her purse on the dresser without noticing that it was not heaped up with dirty clothes -- she must have thought it's always like this. My bed looked nice, I thought.

Weeks of torture were building up to this night, and I felt a little bit of stage fright. She, on the other hand, seemed cool as could be. She stepped up to me and I kissed her, appreciating the privacy of my own place. And boom, the magic worked. It was amazing, like two puzzle-pieces fitting together. No hurry, no sneaky, no pressure. I ran my hands over her body and said, "We need to get you out of this beautiful dress before we mess it up."

She reached back and unzipped it, then shrugged it off. It fell lightly to the floor around her feet, leaving her standing like a Greek statue in her bra and panties. The bra was cut low, with lace and lacy straps, and her panties were kind of a boyish cut, lavender, lacy, dainty. "Wow," I said. "I don't know what to say." She smiled regally and reached back to unsnap her bra, which she shuffled off and set on the dresser-top. She turned back to me, her arms at her sides, while my eyeballs sprung out like that wolf in the Tex Avery cartoon, taking in every millimeter of her body. Finally she hooked her thumbs into her panties and neatly slipped them off, folded them, and set them on the dresser.

"Well," she said. "This is me. I am really glad this night has finally come. I mean, sorry Randy's in the hospital and everything, but, anyway, fuck him, he's having a good time. Now we will." She kicked off her shoes and nudged them with her toe so her were side-by-side, tucked out of the way under the dresser.

"You are amazing," I said. "I couldn't have imagined how beautiful you would look like, uh, like this. Just incredible."

"Now you," she said.

"Oh yeah." I said. "Well, this won't be quite as exciting."

"For you, maybe," she said.

I unbuttoned my shirt. Normally I only wear this shirt to job interviews or to court but it had done the job at Jacksons. I tossed it on the dresser. It was still good to wear again, I'd hang it up later. I untied my shoes, then kicked them off. I stood up straight, in the interest of transparency and not seeming embarrassed, and undid my good jeans. I scooted them down and tossed them on top of the shirt. I was standing there in my underwear and Pam was looking at me with a mixture of admiration and impatience.

"Not bad," she said. "But you skipped a step."

I did not have a hard-on yet, so it was a little less embarrassing for me to push my underwear to my ankles and kick them off toward the dresser. Then I stood up straight and, like her, I said, "Okay, well, this is me."

"Oh my god," she said. "I did not expect that."

"Expect what?"

She put a hand over her mouth and pointed at my crotch with the other one. "That," she said. "I didn't -- why didn't you tell me?"

"Tell you what?"

"Uh, sweetheart, did you mention to me that you were part horse?"

"Huh? Oh, that, sorry," I said. "I didn't think of it. I mean, it's just me, I'm always like this."

"Yeah, okay," she said, stepping up and taking my penis in her hand. "I don't know what to say. I can't even get my fingers around it."

"Well it's not hard yet, either," I added.

"Yeah, okay," she said. "We will have to see what we can do with this. You just caught me by surprise is all." And she giggled a little.

We lay in the bed and cuddled. I wanted to savor every second. I kissed her and then worked my mouth down to her breasts. I put my face between them while she lay on her side, and said, "I think I will just live here forever." I could not hear if she laughed, as my ears were covered with fine heavy flesh. I sucked her nipples and twisted them and she moaned beautifully.

"I love that," she said.

"Me too."

I put a hand on her pussy and stroked it while I sucked her beautiful tits, and her moaning became more pronounced. "Oh," she said, "You're gonna do it." And in a few seconds she began convulsing and vocalizing through an orgasm.

"Wow," she said, laughing. "And we haven't even started yet."

"We haven't?"

"Oh, no," she said, reaching down and stroking by cock, which was beginning to harden. "We have to get this big boy into the game at some point."

I fingered her to another orgasm and then she wanted to turn her attention to me. She stroked my cock until it was hard, looking down at it. Then she slipped down and put her lips on it.

"I don't know if this will fit in my mouth," she said.

"It's okay if it doesn't," I said, trying to be nice. I was thinking: honestly, it's okay if it does, too. In fact that would be better. But I did not mention that.

She got the head of my cock inside her mouth and used her tongue on it. Then she tried to go down the shaft but suddenly lifted her head and said, "I can't do it. My mouth doesn't open that wide."

"That's fine," I said, pulling her head back toward mine for a kiss. "It's not about me tonight. This can be about you."

That seemed to have been the right thing to say, and she kissed me. She continued to stroke my cock while we kissed, and I pinched and teased her nipples. I played with her pussy until she seemed to be getting close to another orgasm, but she pushed my hand back and said, "Let's try it."

"Let's try what?" I asked.

"Fuck me."

Hey I'm not dumb, I can tell when a girl drops a hint. "Okay," I said. She got on her back with her legs spread, her dark patch glistening. I rolled on top of her, took my cock in my hand, and lined us up.

"Go slow," she said, "Please."

I wouldn't know any other way, actually, they always want me to go slow. I tightened my hips to give a little push and heard Pam moan slightly. I could feel her trying to relax, she shifted her legs a little and reached down with one hand to tug at her pubic area. "Okay," she said again, "Slow slow slow."

I pushed and felt a little progress, maybe an inch. But that's an important inch, some women cannot get that far. "Oh my fucking god," she said. "What have I gotten myself into this time?"

I let my hips push and she took a little more of me. "Stop," she said. "Wait. Hold it right there, uh huh. Now back out a little and start again." I pulled back until just the head was inside her vagina and pushed, and this time it went a little farther. She made a gurgling sound.

"Is that okay?" I asked her.

"We'll see," she said. "Try that again, back out a little and then push, but slow." When I began pushing, she said, again, "Slow." I might have gotten two inches of my length into her this time. "Okay," she said, "I think we're doing it. Do that again, back and then push. Slowly." I backed out so only my tip was inside her, and then pushed but this time I went in increments, pushing a little, pulling back a little, pushing farther, pulling back, see-sawing back and forth into her pussy. "Oh my fucking god," she said, and she threw her arms around my back. "Slow. Slow." She tried to move her hips to meet me but she was pretty well impaled and couldn't really move. We might have gotten to three inches.

"Let's try again," she said. "I want to see if I can handle that thing." I lifted my butt to pull out to the tip and then pressed into her insistently, straight ahead, breaking new ground, going farther than the last thrust, by maybe an inch. She was groaning and muttering, "Slow. Slow. Go slow." I decided now to shift gears and fuck her with those four inches, so I pulled back and then pressed into her, pulled, pushed, working up a slow but powerful rhythm. Her arms held me like steel cables, hanging on for dear life, as I fucked her with the first four inches of my cock. There were tears in her eyes and she was moaning, "Oh my god oh my god, slow. Slow. Oh my god, what have I gotten myself into?" On the other hand, if felt good to me.

"Okay," she said after about a minute. "We tried. You need to pull that thing out of me, slowly. Yes, that's it. Slow. Holy shit." I rolled off her. She looked at me and started laughing, her eyes still teary. "Well," she said, "That was amazing, but if we kept going you were going to kill me with that thing."

"I'm sorry," I said.

We lay side by side in my bed for a while, both of us contemplating the levels of discomfort we were imposing on the other. This was disappointing for her, I was sure, after all this time of hoping and planning for this moment, flirting with me and teasing me, building the anticipation. Talking to her husband about me. And now, rather than being "too much of a good thing," I was simply an impossible match. I felt I had been cheated by nature, I would never fit in anywhere, and she probably felt that I should have said something ahead of time, but I just didn't think of it. After all the build-up, it looked like this was the end of the line for this relationship.

After a while she said, "Actually, I hope this doesn't gross you out, but you could make a fantasy of mine come true, if you're up for it."

"Oh? What is it?"

"I don't know how you feel about anal sex," she said. "Lots of guys think it's gross. But I have always wanted a chance to take a truly big dick up my butt."

Well, that one stopped me. I lay there with my jaw hanging open. "How in the world would that work?" I finally said. "Your, uh, your asshole is a lot smaller than your pussy. I'm going to split you in half."

She laughed. "Oh no, the anal sphincters can stretch a lot. They can handle something big, you just have to be a little careful at first."

She was smiling at me, obviously amused by my confusion and surprise. "Have you ever tried it before?" I asked her.

"Tried what? Anal sex? Of course. I went to a Catholic boarding school. Butt-fucking was our birth control, plus we could still tell the nuns we were virgins. I got damn good at it."

"Wow," I said. "That has never occurred to me. I figured it would just hurt."

"Oh yeah," Pam said, "Most girls don't like it even with a small penis. You have to know how to relax the muscles in the right way, and then size is not an issue."

"And this is something you would want to do?"

"Oh yeah," she said with a devilish grin. "I had a lot of guys in high school, well not a lot, you know, but enough to know. They all fucked me in the ass with their little peckers and it was good but not good enough. I always hoped I would run across somebody, uh, somebody like you, a big one, that can really reach in there."

"For real, huh?" I was beginning to buy it.

"Absolutely," she said. "Tonight might be a first for both of us. You game?"

"Sure," I said. "It's not an issue with me. You're the one who needs to be on-board with it."

"Oh, I am, most definitely," she said. She picked up her silver purse. "Look, I want to clean up for this. Give me a couple minutes, okay?"

"Sure."

She headed to the bathroom then stuck her head out again. "Hey, do you have any lube?"

"No, I don't," I said.

"No problem, I brought some." She disappeared into the bathroom. I lay on the bed with my head on some pillows, waiting, wondering how much stuff she had in that silver purse. She might have a gun in there, or a taxi in case she needed a ride home. Could be anything or everything.

"Okay, better," she said, returning. "I don't want this to be messy but sometimes you just don't know."

"Okay," I said. I had never thought about that before. I realized there could be shit involved.

"Did you say you have never done anal sex before?" she asked me.

"Yeah," I said. "I never seriously thought it was possible. And nobody ever brought it up."

She laughed. "Sure, I get that." She climbed into the bed. "Well I brought it up, and I am looking forward to it." I lay beside her and she rolled toward me. "First thing we gotta do," she said, "Is get this big guy in the mood." She took my half-hard cock in both hands and began stroking it, tugging on it, running her fingertips over my balls. "See? He's feeling better already." She went down to kiss my penis, licking it, sucking the tip. It did feel wonderful. All the time she kept her hands going, coaxing me with pleasure.

"Okay," she said. "This is going to be good." She took a little pump-bottle of lube out of her purse and squirted some into her hand and began rubbing it all over my cock. "Now," she said, "I am going to roll over and you are going to put your dick in my asshole. It should be pretty straightforward. I might ask you to slow down at some point. That doesn't mean we give up, it only means I need to adjust to you. Got it?"

She rolled onto her stomach and put a pillow under her hips. "All right, big boy, let's see what happens."

I got between her legs, took my cock in both hands, and aimed it at her butthole. I had not noticed before how beautiful and vulnerable it appeared, just a wrinkle between her cheeks that tucked up inside her body. I rubbed the head of my cock on it for a second to spread some lube around, and then put it where I thought it should be and pushed with my hips.

"Oof!" she said. "Hold on, that's a lot. Hold it right there. Don't move."

I held still with the head of my cock, like a baseball without seams, pressed against her cute little pucker. She wiggled her hips a little, and reached back to pull her cheeks wider apart. Then she began pushing back at me. "Don't move," she said, "Let me do this." I had my arms straight, in push-up position, and I watched, hypnotized, as she moved her hips so slightly, side to side, pushing back, and after a few seconds I could feel and see the ball of the head of my cock disappear inside her.

"Oh my god," she said, looking back at me with a big smile. "I didn't know what I was getting into here."

"We don't have to do this," I said. I could picture taking her to the emergency room, trying to explain what had happened.

"Oh, no, we are doing this," she said. "This is on my fucking bucket list. Okay, here I go again." And she pushed back harder.

Now I felt sensations that I had never felt before. An asshole does not feel like a pussy. It is not a long snug self-lubricating passageway, there are points where it squeezes you and parts where it doesn't. Also the texture is different, it is smooth in a unique way, and there is a sense of vulnerability that makes the experience especially intimate. Pam kept pressing back on me while I hovered above her, up on my arms, and I watched my cock sink into her, half an inch at a time. She went very slowly, pausing sometimes, biting her lip, her eyes closed, turning her head to look back and smile at me occasionally. She seemed to be having fun.

She took the whole thing. This was something I had never experienced in my life, having my entire cock inside another person. It was unbelievable, and I gave a little push at the end to make sure she got it all. The feeling at the base of my cock was amazing, and new to me, her asshole gripping me, tugging at me whenever one of us moved. She looked back at me and said, "See, that's what I'm talking about." She pulled her hips forward and shoved back at me, a kind of test run, and then said, "Fuck me."

It was an intensely emotional moment for me. I had had girlfriends who refused to even try sex with me, and I had had ones who made me stop after I got the tip inside them. I had had two girlfriends in my life who would have sex with me, both of them somewhat older ladies, where I was able to get five or six inches into them for a few minutes but it hurt them and they did not like it, and also it was not very satisfying for me. None of them had ever had an orgasm, and I usually did not, either, especially when they made me pull out. "You're going to kill me with that thing" was a line I had heard, believe it or not, more than a few times.

I pulled back and then pushed my cock forward into Pam's willing asshole, going my full length. "Arrggghhh," she said, happily. "If you don't mind, I am going to use my hand down there, is that okay? One thing about this is that it does nothing for the clit."

"Do what you like," I said, feeling kind of stupid. I didn't see why it would be up to me, well I figured she was just being polite. She reached her hand down under her tummy. Every once in a while I could feel her fingers moving when my balls touched them. Otherwise I was unaware of her touching herself.

"Ah, give it to me," she moaned. "Fuck me. This is amazing." I reared back and slammed my length into her, pushing her forward on the bed. "Again!" she said. "Do that again." I rammed it into her and she said, "Oh my fucking god," and I rammed it again, and she said, "Here I come, get ready."

Suddenly bam, she tensed up, her back arched back, her head came up, and a sound like gurgling laughter came from her lips. "Oh oh oh oh," she said. "Oh my god, don't stop, don't stop, oh my god." I could feel her convulsing around my cock, and it was a terrific feeling. There was not only intense physical pleasure but I felt a profound sense of accomplishment and of connection with her. Her seizure slowed and stopped and she fell like a limp rag on the bed. I moved more slowly in her, and after a minute or so she began wagging her butt at me again, fucking back at me, and I began pumping my cock deep into her asshole in a hard, insistent rhythm, with long deliberate strokes, and she came again.

We had to reapply lube a couple of times, but she kept wanting more. We had been fucking for about half an hour and I couldn't count her orgasms before she said, "You know what, you are just about wearing me out here. This has been worth every second I waited for it. Now let's get you off."

This was good timing, because I was already feeling that I might not be able to stop myself the next time she came. Each orgasm had been more arousing for me, and I felt I was ready to go. She began rocking her hips back at me, stroking my shaft with the inside of her asshole, taking me deep, and I let my hips flex in a pleasurable way, I let go of my control and let my own orgasm build inside me. I stroked into her slowly, and soon we came to the point where I could not hold back any longer. The cum flooded up into my cock, which began pulsing and pumping as semen shot out into Pam's guts. She was shouting "Yes! Yes! Yes!" and I kept banging her until I had shot every drop. Then she collapsed onto her belly and I collapsed on top of her.

I kissed her ear, my cock slowly shrinking inside her. After minute or so she said, "We should go wash up before we make a mess." I got off her and we hurried to the shower and cleaned up. There was no shit but it was good to clean up anyway. She scrubbed me and I scrubbed her and we hugged and kissed in the shower.

As we were drying off, I asked her, "Are you going to stay?"

She said, "I thought about it, but I think I should probably be home in case he calls or anything."

"Yeah, sure," I said. "Do you think he suspects we have something going on?"

"Oh, sure," she said. "I tell him everything."

"So you really are honest with him, huh?"

"Yes," she said.

"You're going to tell him about this?"

"I'll tell him some of it," she said.