Mr. Big Ch. 02

Slowly I pulled back. "Oh Jesus, that -- that's so -- so intense!" She was almost talking in a whisper now, and I guessed all of her attention was on that big hunk of meat filling her pussy. I jiggled my hips a little, moving my cock maybe an inch in either direction, and she let out a long squeal.

"Fuck! That's -- that's so strong, and right on -- oh yes, right there, right there!"

So then the jiggle became a wiggle as the movement got longer and gradually faster. Maybe two inches each way, then three. Her knees fell back toward the picnic table as she seemed to want to open even wider for me. Four inches in and out, five, then six, until I was almost hitting bottom.

Kristy had stopped trying to speak. She just kept making these kinda guttural "Uh! Uh! Uh!" noises in her throat. The pitch rose as the thrusts got deeper and harder. Just before I was pounding my entire length into her at a strong fucking rhythm, the gasps and moans turned into something more like a scream. Her cute little body started writhing around on the table, her head moving rapidly from side to side. About then, I slipped my thumb onto her clit; and it was like an electric shock had just gone through her. The lucky girl was receiving almost twelve inches of thick, hard cock, thrust energetically up her juicy and oh-so-tight little cunt. She came again before lucky Shawn, who was watching his girlfriend get seriously fucked, got to fill an orgasmically-moaning Loretta up with his own spunk. And I was just seconds behind them all.

"Fuck. That was -- that was -- fucking unreal!" Kristy panted as I slowly withdrew.

"You'd better believe it, girl," Loretta smiled back, separating from a grinning Shawn. "When he gets it all the way in, deeper than I thought anyone could go, it just blows all my fuses. Having said that, your boyfriend is pretty damn good. He doesn't have Tommy's dimensions, but he sure can use what he has. We're on our way to Scottsdale, but if you'd like to lend him to me on the way back, I'd be very grateful. Probably grateful enough to eat your cute little pussy 'til you scream like that again."

We exchanged phone numbers, kissed -- it seems odd that I'd shoved all of my length into Kristy but hadn't actually kissed her -- and then we went our separate ways. I guessed that Loretta would make her own arrangements for a liaison with this fun young couple for the return journey.

Around two hours after we'd left Kristy and Shawn, we stopped at a motel. It was the last night before we got to Justine's place, and I sensed that Loretta had planned something special. The bathroom of our room wasn't big enough for us to shower together, as we usually did, so I went first. Loretta seemed to spend quite a while in there before coming out in her robe.

Like I said, we usually got room service, but that night Loretta suggested we eat in the diner next door to the motel. She dried her hair, and then just pulled on a tight-fitting dress with no underwear. Not many women her age would look as good as she did, dressed like that. The material molded to her sexy curves, and her nipples stood out in the horniest way. All through dinner, she teased me, sucking on the straw of her cocktail while making very suggestive eye contact. She kept squirming around in her seat, making her tits jiggle under her tight dress and her nipples stand out even more. And then, when we'd paid the check and were finishing our coffee, she reached down and rubbed the front of my pants. I was already half-hard, watching her little show, but I soon get even harder.

"OK, big boy -- very, very big boy," she said in a sultry voice, before licking her lips in a completely slutty way. "Why don't you take me back to your room and see if you can fit this huge creature in my ass?"

At first, I thought she was joking. I mean, Loretta's cunt -- as she insisted on calling it -- was tight enough for me, although nothing like as tight as those belonging to other girls I'd tried to fuck -- or, indeed, Kirsty's. Her ass was, I guessed, probably much tighter than even Donna's little snatch.

"Sure, Loretta," I replied with a smile. "And when it doesn't fit, I guess I'll just have to fuck your juicy little cunt until you scream." I guessed that she was just trying to sound slutty to get both of us really fired-up.

"Tommy, honey -- we're gonna make it fit." She fixed me with a look that told me she was serious.

With that, she got up and wiggled her way out of the restaurant, with me following closely behind, watching the way the tight fabric of her dress hugged that nicely-rounded ass -- and wondering what would happen if I tried to slide my cock between its cheeks.

Back in the room, Loretta went to the dressing table opposite the bed and pulled a bottle of lube out of the drawer, placing it on the surface beside her. Then she just hiked up her dress and bent over, resting on her forearms, spreading her legs, pushing her ass out and looking into the mirror. "Think you know what to do, kid?" she asked, looking at my reflection as I moved in behind her.

In her ass was a plug, different again to the second one she'd been wearing earlier. I took hold of the end, and realized it was vibrating. That might explain why Loretta had been fidgeting so much over dinner. The lips of her pussy were pretty wet -- I tested with a finger and tasted it to be sure it was woman-juice and not lube -- and she sighed. Then I tugged a little on the plug. She gasped. I pulled harder. She moaned. I pulled even harder, and she cried out as a plug maybe five inches long and really thick opened up her tight ring and slid out of her ass. This definitely wasn't the one she'd worn when I -- and then Shawn -- had fucked her earlier.

"I needed to work up to that one," she said, answering my unvoiced question. "If I'd stuck with the smaller ones, I would've still been too tight. With that monster -- well, we'll see, won't we? Use lots of lube. Keep going unless I say 'stop'. If I don't say 'stop', then whatever other noises I'm making, you keep going. Got it?"

"Sure, Loretta. It's your ass. I'll do exactly as you say."

I squirted a load of lube into my hand, slathered it over my dick, then stuck two well-lubed fingers into the vacant hole to add a little extra inside -- which I guessed might be needed soon. She moaned again. It felt seriously tight to me, but this is what she'd demanded, and who was I to argue?

I lined up my cock head with the slightly-open hole and started to push. She kinda grunted, my dick bent under the pressure and then slid up along her ass crack.

"Hold it in place. You're gonna have to push hard to get it in. Can you do that, boy?"

OK, she was goading me. Two could play at that game.

"Sure can, slut. Hold tight. I'm gonna force that tight ass wide open. Then we'll see who's moaning and screaming."

"Promises, promises. I bet you -- AH!"

I'd lined up my cock head for attempt number two, gripped it in both hands to try to stop it sliding off or bending, and pushed hard with my hips. This forced her hard up against the dressing table, and honestly, the pressure on the head of my dick wasn't exactly pleasant. It felt like I'd lined it up with the keyhole in a door and was trying to drive it in.

Then at last, slowly, excruciatingly slowly, her ring started to open. And that's when the noises really started. "OH! Ohmygod. Ohmygod! OH! OH! OHMYFUCKINGGOD! OH SHIT! OH -- OH -- OH FUUUUCK! NNNNNN!" In the mirror, I could see her face, screwed up with concentration and what I guessed was also quite a lot of pain. But fuck, she'd quite literally asked for this, and she hadn't said 'stop'. This didn't feel great for either of us, but it still seemed to be what she wanted, so I kept shoving hard.

Most of what she said for the next half-minute was unintelligible. There seemed to be a mix of moans, squeals, high-pitched whining noises, gasps and little shrieks. Then I felt my cock-head finally pop inside that unbelievably-tight ring, and for the first time since we started, it didn't feel like my dick was being driven back inside my body. Loretta let out a loud gasp, sucking in a very deep breath like she had suddenly surfaced from under water.

"Fu -- fuck, Tommy. That's -- that's -- ohmygod -- that's so -- so fucking HUGE -- inside my -- my asshole," she panted. I could see in the mirror that her face was red and there were long streaks of eye makeup down her cheeks. Her breathing was ragged and her mouth was open wide like she was struggling to breathe.

"You asked for it, slut," I replied. To be honest, it felt very weird for me. The grip of her ass on my dick was bordering on pain, and the sensations going in were definitely not a turn-on. I just hoped that, once I'd managed to stretch her enough to get some in-out action started, it would feel better for both of us. "What do you want now, you filthy anal whore?"

I guessed that the dirty talk would help get her into the zone she wanted, and maybe, if she talked back dirty to me, I could get there myself. As it was, I felt the only way I would come was if I pulled back out -- hoping her super-tight ring didn't tear the head of my dick off -- and shove it inside her cunt.

"Please -- please -- rub my -- rub my clit!" Her voice was close to sobbing. I guessed that her little fantasy might be turning into a nightmare. We'd done a lot of dirty things together, but Loretta wasn't into pain, and neither was I -- either receiving or inflicting. Pulling out right now was gonna hurt us both, so this little experiment could easily become a fucking disaster, in every sense.

So I rubbed her clit, like she asked. I was surprised to find just how wet she still was. Her juices were running down her thighs. I guess that could have been a mixture of anal lube and pussy juice; there was so much of it I couldn't be sure. Anyway, after maybe a minute of stroking that clit, occasionally letting my fingers stray back to just lightly finger-fuck her, she started to push her hips back toward me. I took this as a signal that her ass had now relaxed enough for me to start tentatively fucking it, so I started to move with her -- a little in, a little out, barely an inch either way.

The noises coming out of her mouth were still a mixture of gasps and little cries, but it seemed that there were more gasps of pleasure and fewer cries of pain. Gradually, very, very slowly, my cock sank deeper into that oh-so-tight tube. I still can't say I was getting a lot of pleasure out of it -- it felt a bit like someone had applied an XS condom to my XXXL dick -- but I could feel her relaxing a little as we moved together, me thrusting gently forward, she pushing back to meet me and fuck herself on something never intended for the hole it was now stretching so far out of shape.

I guess that after maybe five minutes, we were finally moving in what might be called a normal fucking action. If, instead of presenting her ass to me, she'd done her usual trick of lying back and spreading her legs, saying something like "go on, kid, show me what you've got! Fuck my horny MILF cunt with that fucking huge cock," -- you know, something a little subtle like that -- by now I'd be pounding her, balls deep, and she'd be shrieking in her first, or maybe second, orgasm. But no. I was surprised to see that maybe as much as a third of my cock was now riding the shuttle service in and out of her dirty MILF asshole, and she seemed to be enjoying it. In fact, "fuck my slutty MILF whore asshole," was one of the many things she was moaning, rather hoarsely, as I did exactly that.

And actually, it finally started feeling good to me. There's snug, there's sexily tight, and then there's the human vise. As her ass had adjusted, we'd now moved down into the 'sexily tight' zone, and I was gradually increasing the length of my stroke. I picked up the tube of lubricant and dribbled some more onto my dick at the end of the back-stroke, and then pushed a little deeper than before. She cried out. "Oh fuck, Tommy, that's -- that's deep!"

"Actually, you anal slut, that's less than half my length. How'd you like me to shove the rest all the way in?"

I felt her asshole give a little pulse -- I guessed either from excitement or terror. "Oh fuck, Tommy, no! Please -- please be gentle. I mean it. I'm -- I'm beginning to like -- the feel of that fucking great cock -- in -- in my ass, but -- but please, not too deep. Please, I'm begging you. Keep it slow. I can't -- I can't take -- much more -- it's so -- so -- fucking BIG!" I looked at the reflection of her face in the mirror. She actually looked scared.

I leaned in close, still slowly rubbing her clit, cupping one of her nice, full tits in my other hand and squeezing the nipple quite hard. She gave a little squeal.

"You wanted it, Loretta. You wanted to be a fucking anal whore. You wanted a thick, twelve-inch cock up your tight little ass -- right up your tight ass. You virtually begged me for it. So how does it feel, Loretta, now that your ass is full of a huge dick? Now that you're a total dirty anal slut?"

"Oh my fucking GAAAWWD!" Loretta almost shrieked, because, as I was speaking, I pushed in a little deeper. Fuck, I was finally beginning to enjoy this game!

I still kept edging a little deeper on each thrust -- maybe eight or nine inches in -- and Loretta kept moaning and gasping while we repeated a lot of obscenities, until she just screamed "OH FUUUUUCK!" and her asshole started squeezing me hard, pulsing like a strong hand, gripping and releasing, until I couldn't take it anymore. I'm not sure which of us made the most noise. Loretta seemed to be sobbing, I was moaning like crazy, and the whole world seemed to spin.

It took quite a while for my dick to soften sufficiently to pull it out without hurting either of us, and to allow Loretta to run to the bathroom, with a large wad of tissues pressed between her ass cheeks. By the time she'd finally emerged, I'd mixed her a Margarita from the contents of the mini-bar -- the only mini-bar we found on our journey with Margarita mix and tequila -- and tidied away our 'stuff'.

"Tommy, if I ever suggest doing anal with you again, will you please just say 'no'? That was an amazing experience, and one I don't regret, but I think it may take a week for my ass to get back into its normal shape."

I put my arms around her and kissed her. Loretta and me, we didn't often get 'romantic'. We both knew that we were together to fuck, and the primary reason for this was the adventure and challenge that my cock -- and my youthful, fit body -- provided to her, and that her juicy, willing and ever-open cunt provided to me. But right now, I wanted her to know that I cared about her. She'd been kind to me, even if that was initially because she lusted after my body. She was the first woman -- and with the exception of Kristy, the only woman -- I'd ever fucked, and she'd taught me a great deal about sex. I loved the feeling of her tits against my skin, her head resting against my chest.

When she looked up at me, I saw that she was crying.

"Hey Loretta, what's up, baby?"

"Oh, Tommy, this has all been so magical; getting to know you..."

"Getting to know my cock, you mean," I replied, trying to lighten the mood a little.

"Sure, that." She smiled. "But it's been such fun. We've been so good together, so -- so into each other."

"Loretta, I think it's mostly been me into you. Deeply into you." I was very immature back then, and really didn't understand emotions.

"Tommy, please stop being frivolous. I need to say something important. These last few months have meant a lot to me. It's been way outside my normal behavior, and that's been kinda scary and kinda thrilling at the same time. We have just a little while left before we have to go our separate ways, and I feel sad that our fun time together is coming to an end. I needed to -- to do what we did tonight, because... Well, because... See, it's a bit like when I first seduced you. I saw that amazingly strong, sexy body, and I wanted it. Then, when I saw the size of your cock, I knew I just had to have it and damn the consequences. I've done everything I possibly could with you over these weeks because I knew this was just a mad adventure, a once-in-a-lifetime experience. When I go back to Chuck in a few days, I'm not sure what will happen. I have to pretend that we're back to normal, but 'normal' won't ever be quite the same for me after you. I just needed you to know that."

"Hey, Loretta, you're amazing," I smiled at her. Then I bent down and kissed her; a long, soft, sensuous and romantic kiss. She put her arms around my shoulders and kinda melted against me. When we finally separated, I continued. "You've done so much for me. Fuck, I mean -- I was a virgin until I met you, until we -- until that session in your back yard. You've taught me so much. You've given me so much confidence, and I don't think I'll ever find someone as great in bed as you."

"Or across the hood of a car, or up against a tree, or under a shower, or bent over a desk..." she grinned back.

"All of those places. Fuck, we've been great together, haven't we? I have no idea how many times we've come over the past few weeks, but it must have been nearly a hundred. I think you enjoyed them all."

"Yeah, except possibly the last one. Jesus Christ, when you got in deep, I almost fainted. The climax was really strong, like nothing I'd felt before; even more than when you first got all of that monster into my cunt and hit all those places no man has gone before. But it sure as hell hurt when you were forcing your way in, and when my asshole started pulsing around your cock, I thought I was going into cramps. Still, it's another thing to cross off the bucket list. Only I think I'm going to need those anal plugs for a few days, just to stop stuff leaking out while my asshole shrinks back."