Special Delivery

byOneShotBob©

"You better. I've come this far, I'm going all the way." She licked my cock helmet and my hips jerked. "Heh. That's funny."

"What, the bad cum pun or that you can make my hips jerk at will by licking me?"

She slapped my hip. "The hip jerking." Then she licked me lightly again, and my hips jerked.

"You're asking for a long, hard fucking, young lady." I threatened.

"From what I've seen, I'm definitely getting a long, hard fucking, even if you only last a couple minutes. I think I want more 'mouthwash.'"

"You don't-"

"No, I'm not afraid any more. I want it, but I also know I'll need to be relaxed, or it might hurt more. The tequila is to help me relax now, not to help me be brave."

"Okay, just making sure." I waited until I heard the bottle open, a swallow, and the bottle closing sound, and then I started working my fingers in her pussy again as I licked her clit.

"Damn, you're ready again already?" She licked my helmet and my hips jerked.

"No, still too sensitive. But I want to get you ready."

I felt her twisting under me, and heard her rummaging in the box. A small hand holding a bugger butt plug and a tube of lube appeared. "This too, I think?"

"Probably a good idea." I agreed, then I had to ask. "Are you going to need to, ah, use the restroom before-"

"No, Shelley said you were big. I've been eating only protein shakes and smoothies for the last couple days, and three enemas this morning."

"Oh."

"Too much information?"

"No, not really." I shrugged. "I'm just surprised you changed your diet."

"I didn't, not really. I normally drink most of my calories in smoothies and protein drinks anyway. I just made sure to stay away from anything bulky. I'm glad I did. I think you can reach last week's food with that thing."

I laughed, knowing she was kidding this time, then I pumped my four fingers into her pussy again a few times before withdrawing them.

I pushed the bigger butt plug in to replace my fingers. It was only about an inch and a half at its thickest point, so it went in easily after my fingers came out.

"Err, that's not."

Then I turned on the switch at the end of the plug, and the vibrator started.

"Oh. Damn. Yeah, that's good for a bit."

I laughed. "Just for a bit. I need to work on your butt. That plug is a good bit bigger than the first, even if it's nowhere near as big as me. But it'll keep you from closing down all the way while I open up the other end a bit."

"Hmmm." She mumbled happily as she twisted her hips. "Okay."

She licked the end of my cock, and my hips jerked, again. She giggled.

"I'll get you for that." I mock threatened.

"I am eagerly awaiting my chastisement." She licked me again. I was waiting for it, and barely jerked.

I raised my head and shoulders off the bed far enough to see the bottle. It was nearly three quarters full.

"What?"

"Checking the bottle. It's no fun to fuck someone who's completely sloshed."

"It's a half-pint. I could drink the whole thing."

"And be completely sloshed. Stop at half, please. I don't want you puking on the bed. Especially now that I know you haven't eaten any real food for-"

"I'll be fine. I don't like being too drunk when I'm having sex either. If you go too fast, I want to feel the pain, so I can make you stop. That thing could actually damage me, I think."

"Okay, we agree, but if the bottle goes below half-way, we stop. If you want to finish it after, that's fine, but you won't be biking anywhere tonight if you do."

"Oh, you'll take my keys?"

My voice got a little sharper and louder. "I'm serious. I think this might work out, and I've already almost lost one person to an accident."

"Oh. Sorry, I was kidding about the keys, and I guess I can see where you're coming from."

I took a moment to calm myself down. "Sorry. Sore spot. Killed the moment a bit."

A tongue rasped around the most sensitive bit of my cock head, right at the edge of the helmet. My hips spasmed. "Damn!"

There was laughter from the other end of the bed. "Get to work, sir. You have things to do before you can see if your package can fit in my shrink-wrap tube."

"Yes, ma'am." I replied as I lowly tugged the small vibrator loose. I looked at it and found no stains, and it smelled like musky strawberries. Satisfied, I set it on the floor.

Before things could tighten back up, I stuck a pussy-wet finger into her anus, then worked another in next to it.

"Oof. Give a girl a minute to get ready before you add more fingers, please."

"That's all the fingers for now." I replied smoothly as I dribbled oil directly on top of my two fingers, so the oil would flow down the crack where the two fingers were net to each other, and flow directly into her ass through the little gap in her sphincter between my two fingers.

She shook her butt and clenched her ass on my fingers. "That's cold."

"It'll get warmer quickly. It's pretty hot down here." I slowly pushed my two fingers in as I drizzled more oil on them in a steady stream. She'd need a good bit of oil in her if I was going to fit everything inside.

"Oooh. Damn, that's good." More ass-clenching on my fingers.

I stopped drizzling oil after I guessed a few tablespoons were inside her ass, then I started sawing the fingers back and forth slowly.

"Uh. Uh. Damn that's good. It's been so long, and a vibrator just isn't the same."

It's only been a year for you. Four for me.

"So you really do like anal?"

"I do. I hope that thing of yours will fit."

"It will."

I made a promise to myself. Even if it takes six hours, I'm getting balls deep in this ass, and she's going to like it.

"Another finger, please." Cathy gasped.

"It still seems a bit tight. You sure?"

"Yes. Finger. Now."

This might be easier than I thought.

I added a third finger, and more lube before starting to slowly drag the fingers back and forth as I felt her stretch out.

Suddenly, a tongue rasped against my cock again, and I jerked. My hand jerked as well pushing hard into her ass, burying all three fingers well past the second joint.

"Ow. That was fast." She complained.

"You keep licking me before I'm ready, I'll keep jerking around."

"Oh. Sorry."

"It didn't hurt me. If you want to lick me, feel free, but not on the head, unless you want me doing that again. When it starts to get hard again, you can go back to the head. It won't be long before I'm hard, with what I'm doing down here." I pulled and pushed the fingers in her ass a couple times to illustrate.

Two hands grabbed my shaft and I felt her start corn-cobbing my cock, nibbling and licking on the tube but avoiding the head.

"Mm mm. Much better." I thanked her, then got back to ass-stretching.

It didn't take long before three fingers moved fairly easily, but I didn't want to rush things. Three deep fingers would be plenty big enough to fit the second butt plug, which was quite well-lubed by the pussy it had been sheathed in for several minutes.

I pushed the three fingers into her ass and held them there. Then I used my other hand to grip the very slippery end of the plug in the other hole.

"Going to move the plug from one hole to the other. You ready?"

"Yes. Please. Do it."

I pulled a little on the plug, then let it settle back in.

"Mm mm. Nice."

"You like that?"

"I do. A little more of that would be good."

I pulled on the plug, and then sawed my three fingers back and forth in her ass.

"Oooh. Better. Please. More."

I spent the next minute randomly pulling and pushing the plug and my fingers in her pussy and ass, respectively.

"Stop. Move that thing to my ass. You're starting to get hard, and I want to start fucking."

"Did you get more into that bottle?" I asked.

"No, I'm just tired of playing around. I want the real thing."

"You can't handle the real thing yet."

"I bet I can."

"You can barely fit the head in your mouth when I'm hard. I bet you can put your hand in your mouth if you try."

I felt one of her hands come off my cock, and the licking and nibbling stopped.

"Well, yes, but I still-"

"Aren't ready. Please. Trust me. I want you to enjoy this."

"If I can fit my hand in my cunt, will you fuck me?"

"That's actually the test I use. A woman's hand is wider but thinner than my cock. If your hand will fit, including the thumb, my cock probably will, or it will at least be close enough for me to cheat."

"Cheat?" She'd picked up on that. "How do you cheat to stick a dick in a pussy?"

"I'll show you, if we need to. After you can get your hand in your pussy."

Her hand reached down to where I was sawing the vibrating plug back and forth, and tapped on it with two fingers. "Get that thing in my ass. I have work to do."

I couldn't help but laugh.

"What's funny? This is serious fucking business, mister. Literally."

We both started laughing.

"We're going to be punished for our sins, you know." I choked out between chuckles and intakes of breath.

"I know. I'm going be resigned to an eternity of bad jokes, some day." She paused. "But for now, move that thing."

I popped the vibrating plug out of her sopping wet hole, and she immediately pushed three fingers in, then managed a fourth. "Give me a minute." She started sawing her hand back and forth.

I pushed hard with my three fingers in her ass, spread my fingers a little to stretch things out a bit more, and then withdrew the fingers and pushed the plug into the gape before it could close again.

"Ugh. That feels good. So good. I can't wait for the real thing."

I pulled away, and rolled to the edge of the bed. "I'm just going to watch if you want to get yourself ready."

Her eyes were closed and her other hand moved down behind her, to her ass. She started wiggling the butt pug in and out just a little bit while she corkscrewed her other and in her pussy, trying to lever it wider. "Okay. If you want me to lick your cock while I do this, I'll move on the bed a bit."

"Nah, I think I'll watch, and stroke a little to get ready." I looked in the box. "There's a bigger plug in there. Do you want it?"

"No. Dang. Kids. These. Days. When I was a sexy young woman, we did things with our hands, not toys."

I busted out laughing.

She opened one eye and looked at me, then smiled back. "Don't bother me. I'm busy."

I started slowly stroking my rod, getting it ready. The head was back to near-normal sensitivity, and I was back up to about eleven inches length.

Watching a good-looking young woman doing her best to jam her hand into her pussy while pulling and pushing on a substantial plug in her butt was doing wonders for my cock-growing efforts. The euphoric look on her face was helping. A lot.

I found the bottle, and it was half-empty. I'd been so into jamming her pussy and ass with plug and fingers I hadn't heard her open it. I made sure it was tight, and slid it between the mattress and box spring. She was so worked up she didn't notice.

I damn well do not want tonight ending with my cock half-buried in the ass of a good-looking woman puking in my bed.

It worried me that she'd drunk so much in a short time, but it was a half pint, and we had been going at it for about an hour since her first drink. She'd also spilled some and used some on my dick. Her words weren't slurred. I was probably worrying too much.

Still, I was going to be putting a lot in her ass, and Shelley had complained that it was uncomfortable if she'd recently eaten a meal, even if there wasn't anything in her ass to stop my cock. I certainly wasn't going to tell Cathy that, but I didn't want her puking either.

"I'll be back in a minute, Cathy. I need to get something for you."

"Okay." She grunted. "Hurry up. I think I'm almost there."

The twirling hand was noticeably deeper into her pussy, but not yet up to her knuckles.

"I'll hurry." I promised.

And hurry, I did. Bathrobe. A quick pater down the stairs. Jar of peanut butter. And then I ran back up the stairs with what I hoped would prevent puking.

"Okay, got something for you."

"Is it almost a cubit long, with a fat head?" Her eyes opened, and she looked at me with my bathrobe and jar of peanut butter. "Huh"

"I saw that you drank more. You said you haven't been eating much. One spoonful of peanut butter."

"Awww. Mom. Do I have to?" She complained.

"If you eat your peanut butter, you get a big sausage for dessert." I shrugged my bathrobe off, and my cock jutted out almost straight away from my body, bouncing to a stop a few inches from her face.

She started laughing, and her hands stopped moving. "Sure. That's a good idea anyway. Once we really get rocking, I guess I might get sickish without anything in my stomach."

"You keep going with those hands young lady, so you don't shrink back down. I'll feed you the peanut butter." I opened the jar, and scooped out a couple fingers worth, then smeared it thickly on my cock head.

"Damn. That's definitely the best way to serve peanut butter that I've ever heard of." She jutted her head towards me and opened her mouth like a baby bird, as her hand returned to grinding into her snatch, trying to widen it enough for my cock.

I held the helmet barely out of reach. "Careful, it's fully erect, you can't put it all the way in your mouth without hurting me with your teeth."

She nodded, and held her mouth open again, but said nothing.

I fed her peanut butter. Carefully. Fortunately she didn't seem too drunk to bite or try to jam me in her mouth. A couple minutes and she had licked at least two tablespoons off my cock. Plenty to coat her stomach with oil, which would hopefully keep her from puking when I started really jamming it to her ass.

Mission successful.

"So, how is the hand job progressing?" I asked, looking for myself.

"Think I'm ready."

She had all four finger knuckles in, but not her thumb. I was skeptical. "Maybe. Let's find out?"

"Definitely. You're the one that knows how to use that thing. What position is best for me?"

"Doggie. I won't touch your hips until you give me the all clear. You can push your hands back against my thighs and make me stop if I go to fast."

"My hands will go that far back?"

"Yes. With your fingers outstretched. Once I'm a couple inches in, it will get easier." I noticed she had pulled her hand out of her pussy. "Don't stop with your hand. When you're stretched out like that, it closes up fast."

"Voice of experience?" She mumbled into the mattress as she kept twirling her four fingers up to her knuckles in her pussy while she struggled to get into doggie position with one hand. It took her about ten seconds. I didn't help, it was fun to watch.

When she was in the doggie position, I answered her. "Yes. Thirty seconds is the difference between me fitting and me really having to work for it, and causing you more pain than I'd like."

"A little pain is fine."

"A little pain is going to happen." I promised. "But you tell me if it's too much, I'll stop and we can get that bigger plug to make it happen."

"It'll fit. I know it will."

"That's the tequila talking. But you might be right. Ready to find out?"

"Yes!" She wriggled her ass at me. The butt plug was visibly vibrating back and forth as I watched.

"Arch your stomach down more."

"If I do that, my hand won't reach."

"We don't need your hand there now, but you better play with your clit while I get started."

I reached over with my foot and dragged the box of toys next to me, and quickly leaned over, lifting it and putting it on the chair. I'd need the lube bottle.

It took me about five seconds to put slather my cock with a bunch of lube.

I did a double-take into the box. "Wait. Condom"

"Nope. I'm on the pill. Stuff me, sir. I'm shrinking."

I laughed. "Yes, Ma'am. One good stuffing coming up. Remember, one hand behind you on my thigh- push back on my thigh or tell me to stop, and I stop."

I lined up behind her, and checked her tightness with four fingers. They fit up to my second joint, held flat.

This might actually work. She's got bigger hands than I thought.

"Fingers?" Cathy complained.

"Just checking before the real thing."

"Now. I want that cock." She demanded, and it wasn't a joking voice.

"Yes, ma'am."

I pressed my purple helmet against her slot and worked it back and forth, to feel for the hole. When I was centered, I started to slowly push.

I felt my cock head shrinking from the pressure as it started slowly working into the cunt-channel.

Cathy started panting, and in a strained voice complained. "Damn, is that your fist, or a baseball bat?"

"I warned you."

"Stop. Let me stretch a bit. Is the head in?"

"About half of the head is in."

"Damn. Okay. Let me do this. Don't move."

"I'll stay still."

Cathy slowly started to rock back and forth, moving only the tiniest bit. I carefully leaned over without moving my hips and picked up the lube tube, and started dripping a drop at a time at the top of my cock head, so it would work around her sorely stretched pussy. It was painfully tight, and I knew from experience that the lube would be squeezed off. Fresh lube was needed right at the entrance, or the fucking would be over before it began.

And I'm fucking this woman, even if she tries to go too fast.

I shook my head, and corrected myself.

Unless she says stop.

"You. Said. You. Could. Cheat?" She said between micro-thrusts." Looking back at me from the mattress where she had her head pressed against her right ear.

"Do you want me to, or do you want to do it yourself? You're making progress. At least a quarter inch more so far. A half-inch or so to finish getting the head in."

"Cheat. Please." She gasped.

"Yes, Ma'am. Stay very still. This will hurt me more than it hurts you."

"Wait. What?"

"I'm going to squeeze my cockhead so it's a good bit smaller with my fist, and pop it inside before the blood goes back into it. It hurts, but it works."

"Do. It." She was still micro-thrusting.

I pulled away, put my fist on my cock head, took a deep breath, and squeezed carefully, pushing the blood out. It was not pleasant, and my whole cock started to throb. But after about three seconds, I was small enough that I should fit. I held my cock with one hand, and used the other to squirt a healthy stream of lube into the still-gaping pussy in front of me. Then I pushed forward, my hand against her pussy, and still confining my cock.

"Ready?"

"Yes."

I pushed forward, hard, at the same time as I let go of my cock. I was barely fast enough to get the whole cock head in, and maybe a half inch past that.

"Whoa. Whoa. Stop. Wait." Cathy squeaked, but it sounded more like surprise than pain. Her fingers pushed against my thigh.

"Operation package-in-box is now officially a go." I joked. Then in a more serious tone. "Tell me when you want more. You're past the worst part."

My cock head still hurt. I didn't really want to move for a minute anyway. "Remember, frig yourself. You really need all the lube you can get."

She nodded and I felt the entrance of her cunt start to vibrate a little as she started furiously frigging herself. "Did you have to jam it so far in with one thrust?"

In a patient voice I corrected her. "That was just the head and maybe a half inch past that. We should be able to get at least another six to eight inches in you."

She stopped moving. "You're shitting me."

"Nope. Keep frigging. Tell me when you want more."

The frantic frigging continued, and her breathing got ragged.

"Breathe slower. Hyperventilating is bad. Concentrate on relaxing."

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byOneShotBob© 6 comments/ 98795 views/ 97 favorites

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