Special Delivery

"I've never needed toys to get me ready. Never been with a guy bigger than eight inches."

"Okay, yes, work it in and out. If you want to help me get our mutual friend ready for a spelunking adventure in a dangerous tunnel, I'd appreciate it."

"Dangerous?"

"He might get lost in there. It's dark and he doesn't have a light."

"I guess it is pretty close quarters, and very slippery footing." She picked up the joke and ran with it as she turned around to face me.

I stood, and she flopped over on her back, and opened her mouth. "Think you can take a little humming yet?"

I rubbed the head of my cock, and it wasn't too sensitive. "Definitely. Remember to keep working that plug. I want the spelunking adventure to start ASAP."

"I thought I was the impatient one?" She muttered with a smile before guiding the head of my cock toward her mouth.

No, but I'm the one that knows how fast we can really go.

"I want this too. A lot." I looked down at her. "Four years since I've been balls-deep. And after two cums, I'm going to last a long, long time before I paint your colon white."

"Is that a threat, or a promise?"

Both, I thought, but I only smiled to her.

"So you're the strong, long, and silent type, eh?" She dragged me a little closer, gently, by my cock, and fed it down into her throat, and then started to hum.

After two cums in less than two hours, I was slow to grow. Steady though. I could feel my pulse along the tube as I watched Cathy with one hand between her legs pulling and pushing the big butt plug, while her other hand and her mouth worked my member.

In about five minutes, Cathy had to take my cock out of her mouth. She scraped my helmet a bit too hard with her teeth, and I winced and jerked back.

"Sorry."

"No problem." I leered down at her. "I'll figure out how you can make it up to me."

She started kissing the head of my cock, looking up at me with doe eyes. "Does this make it better?"

Blood surged to my cock at her expression. She obviously felt it with her hand. "Ooh, I'd say that was a yes. You like cute, innocent expressions on the ladies that you're about to feet a foot of meat to, sir?"

"Apparently, yes." I grated out as she stared up at me with puppy dog eyes while she licked and tenderly kissed the head of my schlong. More strong pulses down my cock, and it was getting close to full size.

"Poor, innocent me. About to be brutally ass-fucked by a brutish ogre with a cock bigger than my forearm. Nobody can save me." She smiled evilly, and licked the tip of my cock, then tried to stick her tongue in the hole, wriggling it a bit.

I almost fell to my knees. "Oh. Damn. That's good."

Cathy let go of my cock, and it raised up away from her a bit. She lightly swatted it back and forth, and it swung like a pendulum over her face. "Looks about ready to me." She raised her head a bit, and stuck out her tongue. As my cock swung back and forth, she licked it. When it passed over her mouth.

I smiled at her, showing my teeth a bit. "Turn that ass around, it's show time!"

"Oh goodie. I love this movie." She bounced around on the bed, getting back into the doggie position with another high pitched "Arf!" before settling her head on the bed and starting to frig herself with one hand while still pulling the plug in and out past her ass-ring with the other.

I moved up behind her and lubed up my right hand.

She looked back at me, and said in a serious voice. "I'm going to trust you not to hurt me with that thing. Stop if I say stop."

"I will. Don't tell me to fuck you harder until you feel that I'm balls-deep. I might hurt you."

She nodded. "Deal."

Using my left hand, I gently brushed her hand off the plug, and pulled it out, replacing the ass-stretcher with the four fingers of my lubed right hand. I tossed the plug on the floor, and watched it roll like a child's top no longer spinning fast enough to balance.

I shook my head, and picked up the anal lube bottle with my left hand, and spread my fingers a little, squirting a long stream into Cathy's ass past the gap I created.

Cathy's ass grew goosebumps, and she groaned, pushing back at my hand with her ass, but she didn't say anything.

I whispered "relax. You've done anal before. You know if you relax, it's easier."

"Hard to relax. I know how big that log of yours is."

"I understand, but try. Once I get all four fingers in to my knuckles, I'm going in. I'll warn you."

"Thanks." She whispered, looking back at me. I could hear the fear in her voice. All bravado aside, this clearly worried her, at least a bit.

Proves she's not that drunk, and reasonably sane. I thought to myself as I put pressure on my hand trying to press four fingers knuckle-deep into her ass.

Four fingers wide was a good bit wider than my cock, but the hole I was making was a narrow oval. My cock was a tube. I didn't want a repeat of the pussy incident, because compacting the head of my cock a second time in one night would leave me seriously sore the next day.

I moved forward, and swung my cock under her, between her legs, and bounced it off her hand as she frigged herself, then I reached around her, and started tweaking her nipples with my fingers.

She jerked back, hard, against my hand, and gasped "Ung." but my right hand fingers didn't go knuckles deep.

"We're close. Don't rush it." I tweaked her nipples again.

"Okay." She whispered, opening her eyes again, and looking back up at me. "I'm ready when you think I am. Won't push any harder."

I felt her relax, and my right hand fingers slipped in to the knuckles.

"It's time." I whispered.

"Go slow. Please."

"I will. Remember who made us go fast last time."

She smiled. "I remember. I'll be a good girl."

"I'd rather you be a very bad girl, but patient."

I felt her body shake as she chuckled. "Okay." Then she relaxed again.

I backed away from her far enough that I could lube my cock, but not so far that I couldn't keep my right hand knuckles deep in her ass.

The lube was cold, and my cock twitched, growing just a little harder. It was a little undersized after two rounds with Cathy, but hard enough to get the job done.

I leaned forward and flexed my right hand fingers a bit, pouring a long steam of lube past the fingers into the pinkness beyond.

"Pull your cheeks apart a bit. It'll help some. Remember to stay relaxed."

She pretended to talk to herself, but was clearly making a point. "Stay relaxed, he says. I'd be willing to bet he's never taken a cock like this up his ass."

"No, I haven't, but I still need you to relax as much as you can. If it hurts, stop me. Hand against my thigh, or say stop, either way, okay?"

"And don't tell you to go faster until I feel your balls slapping on my pussy lips. Got it." She reached back with both hands, spreading her cheeks.

I leaned forward and kissed her between the shoulder blades. "You're awesome." I whispered. "I won't hurt you."

"I'll be more awesome after you scratch that itch." She whispered back. "Carefully."

I stood back up behind her, and lined my rod up behind my right hand. "Here goes."

She pulled a little harder on her butt cheeks as I pulled my right hand out of her ass, and pushed forward with my cock. It stopped moving when the head was almost all the way in.

"Holy shit." She whispered. If I need to keep my cheeks held apart, frig me, please.

I reached around her and started playing with her clit, as asked. "Push out, like you're trying to use the restroom. The head is almost all the way in."

"I feel like I'm trying to shit a bowling ball already, but I'll try." She complained, her voice strained.

"Does it hurt too much?"

"No. No. Give me a second." She took a breath, slowly, then my frigging hand felt her abdominal muscles move a bit as she did what I asked.

My cock head popped in, and the pressure I was pushing against it let an inch of shaft follow.

"Ohhh. Slow. Slow." Both her hands left her ass cheeks and pressed back against my thighs.

"You got a bonus inch there. Feeling okay? I'll hold still till you want more."

She was starting to hyperventilate again.

"Slow breathing. Relax. Now that the head is in, it's just a matter of time before I scratch that itch of yours."

"Okay." She opened her eyes and looked at me, trapping my gaze for e second before closing her eyes again. Her breathing slowed, and I felt her sphincter relax a little, but I didn't press in. Both of her hands were still on my thighs.

Then she started to rock forward and back, slowly. I stood perfectly still and let her do what she wanted. After two cums, I was good for at least thirty to forty-five minutes in her ass, I was sure.

Just like when we were in the same position in her pussy, I reached over, got the lube bottle, and started dripping it on the edge if the tight hole my cock was jammed into.

I felt myself getting harder and bigger as I watched my cock moving slowly deeper into her ass. She was stretching as I was getting bigger though, so it didn't stop anything.

"You're doing great. That's four inches now."

"Past the head?" She asked between low grunts.

"Nope. An inch past where you started."

"Damn. I'm already close to cumming."

"Good. If you cum, you will be very relaxed after, for a few seconds. Try to remember to push back to me after you cum, and if you push like you're trying to-"

"I got it. Anal experienced." She sounded a little annoyed.

"Sorry." I apologized.

"Is okay. Just don't move. Let me. I got it from here, until you're scratching that itch, then it's all yours."

"Yes, ma'am. Standing still until that itch is scratched, ma'am."

She started moving again, a little forward, and then a little more back. She was making good progress, but would hit the inner sphincter in a few inches.

"Can you feel me getting bigger inside you? You're so hot. Do you have an itch thirteen inches deep? I think I'm gonna scratch it."

She opened her eyes and looked at me again. "I thought you would be smaller this time around."

"I was, to start." I shrugged, and grinned. "You're pretty hot stuff, and it has been four years."

"You better last long enough in my ass to give me an anal orgasm." She threatened, darkly.

"I will. Promise. I'm not cumming any time soon."

"Better not." She closed her eyes and started humming a song I didn't recognize under her breath as she rocked back and forth on my cock.

When I was a little over halfway in, I felt my helmet hit a restriction. "That's your inner sphincter. Seven or so inches in."

"How do we push past it?" She whispered.

"More lube. Lots more lube, patience, and an orgasm would help."

"How are we getting more lube past-"

"Ready to cheat?"

"That again?" She paused. "It won't hurt?"

"Maybe a little, but you're stretched out good right now, I'll pop out, and right back in, easy."

She took her hands off my hips and held her butt cheeks apart. "Do it."

I picked up the lube with my left hand, and grabbed the shaft of my schlong with my right. "Three... Two... One... Now."

"Oh, my God. That is so incredible." Cathy nearly shrieked as I dragged my cock out of her ass.

After the head popped out with a loud pop, I quickly pointed the lube bottle at the gaping pink hole in front of me, and squeezed the bottle hard. A steady stream of lube poured into the depths of Cathy's gaping ass.

"Ooh. More cold. Cold is good. Cold means more fucking. Deeper fucking." She sounded like she was dreaming.

Before her ass could tighten back down, I pressed my cock head into the gap, and pushed. It was tight, but my helmet made it through without stopping.

I kept pressing forward to the sound of farting as my meaty member displaced the air that had filled the place it had momentarily vacated. After a couple seconds, I felt the second sphincter again.

"All yours, Cathy. You're doing great. Are you close to cumming? This would be a good time.

"Yes. Can you go in and out some, but not pull all the way out? It feels absolutely incredible as you pull back. When I cum, push in and I'll try to relax and get Dick Peterson past the sphincter.

I grinned. "Your wish is my command. Five of so inches of back and forth till you start squealing, then I push forward and try to get us past the inner sphincter?"

"Yeah. Exactly. Please."

I didn't wait for more instructions. If I could make her cum, I would almost certainly get past that lubed inner sphincter. It wasn't as tight as the outer one.

As I drew back, there was a long continuous moan from Cathy. "OoOoOhOhOoOo"

When I pushed forward, I felt her pushing back. I carefully didn't hit the inner sphincter too hard, but I did nudge against it, pressing it. Testing it. It released partway even before she had orgasmed.

Easy Peasy. I thought to myself. Just need to make her cum.

I was in absolutely no danger of cumming, but watching the ring of flesh drag out around my cock on every backstroke was amazing. The feel of my cockhead dragging against the inner walls of her rectum was a sensation I'd missed for far too long. I felt myself getting harder. Longer. Thicker.

Good thing I'm already inside, or this would be a problem.

I kept slowly plowing back and forth in Cathy's ass. Five inches. Bump the inner sphincter. Five inches, bump the outer sphincter with the back of my helmet. Rinse. Repeat.

Cathy was panting and madly frigging herself, one hand on her clit and the other hand jamming three fingers in and out of her sopping, dripping cunt. Her butt-cheek-holding duties clearly forgotten. I didn't mind. I was in like Flynn, and the end was in sight.

Well, I wasn't in like Flynn. Cathy wasn't under-aged like Flynn's girls had been. Dirty bastard.

Lucky dirty bastard.

Stay on target, Keith. Stay on target. Daydream after you paint her colon white.

Cathy suddenly let out a deep groan and both her hands stopped frigging and started gripping the sheets as she pushed her mouth into the bed and started moaning incoherent words.

I felt her abdominal muscles start to contract and shake. Her anal walls grabbed my cock and started trying to push me out. I didn't try to move, only resisted being pushed out. Stroking might hurt her during an orgasm. I rode out the storm, reveling in the peristaltic muscle action trying to push my cock out of her ass. The almost mindless pleasure noises Cathy was yelling into the mattress were stroking my ego to no end. I was only seven inches in, and she was already having a loss-of-control orgasm.

She wasn't lying when she said she likes anal. Can't wait to see what full length strokes do for her.

Slowly, her orgasm died down. Cathy was silent, panting. Hands clenching and unclenching the bedsheets.

"Cathy. Time to get past the sphincter." I said, quietly."

"You do it. Too tired."

I shrugged. Tired meant relaxed. She certainly felt a lot looser, but that wouldn't last long.

I pushed forward, slowly, inching my way deeper into her ass until I found the inner sphincter with my helmet. I pushed, slowly, feeling it give way. The pressure continued to raise against my cockhead, but I felt the ring of muscle dragging past.

Thinking calm thoughts, I managed to avoid thrusting.

Suddenly my cockhead popped past the inner sphincter and gripped the shaft of my cock.

"You have to be all the way in now." Cathy whispered, eyes closed.

"See for yourself. Reach back and feel where my hips are." I grinned, not knowing exactly what her reaction would be, but imagining several possibilities. All of which were going to stroke my ego.

Her right hand reached back and found my cock next to her ass. Then her fingers started following it back. "God damn you. You still have almost six inches outside me."

"Not that much. Four or so. But we're past the inner sphincter. I'll need you to lay on your right side now. I can get the rest of the way in, easier, that way."

"You want me to move with that anaconda in my gut?"

"I'll help." I carefully supported her weight and kept myself from pushing deeper as I lowered her to her side on the mattress, and put her left leg over my shoulder, pulling her hips to the edge of the bed.

"I feel like I have to take a gigantic shit." She complained.

"That will pass again once we start moving. I'm going to start pushing the rest of the way in, slowly."

"The rest of the way." She blew out a lungful of air. "Please. I want it."

I leaned forward and kissed her cute little button nose. "So do I. Get ready."

The inner sphincter was looser around my shaft, but I still didn't want to move too fast, and pressed in, slowly, carefully, as I dripped lube around the outer sphincter. The sensation of my cock head going around the curve in her intestines was amazing, as always.

Suddenly, Cathy perked up. "Are you all-in yet?" The tone was a little childish. Her eyes opened and looked at me, and I could see the sparkle of mischief.

"About two inches left."

A second or two later, Cathy asked again. "Are you all-in yet?" in the same high, chirping voice.

I suddenly realized what she was doing. "Young lady, I'll be all-in when I'm all-in. If you don't relax and be a good girl, I'm going to stop this car and paddle your bottom."

"I'd settle for just the bottom-paddling, if that's okay with you." She smirked at me.

"I'm almost all-in now. It's hard to paddle you when you are on your side. You want to try cowgirl or doggie again? I can give you a good paddling in those positions."

"Mmmm. Ride 'em cowgirl. After you get all-in."

I wanted to just jam the last two inches of cock into her and start slamming, but she wasn't ready for that yet. I slowly, steadily forced my head deeper and deeper until my hips touched her ass cheeks. Then I kept pushing another inch.

Cathy's hand tickled my cock where it entered her ass, then felt back another half inch till she found where my cock root ended. "There's still almost an inch outside. Fix it, sir."

I stared down at her. "I'll see what I can do, ma'am." I lowered her left leg off my shoulder, and pushed it up, her knee against her perky little breast. "Do the same with your other leg. Hold your legs against your chest, and I'll get that last inch for you."

"Thank you." She whispered as she wrapped her arms around her knees, holding them against her chest.

I looked down at where her ass surrounded my cock, and dripped a few more drops of lube on the stretched muscle. "I need to pull you a little towards the edge of the mattress."

"Do it. Do it." She repeated in a dreamy voice. "This is so incredible."

I pulled her about three inches closer to me, her ass was hanging about an inch off the edge of the bed. I started to push again, carefully, slowly, and after another three minutes, I managed to get practically my whole cock inside.

"There we go, young lady. I'm all in."

"Yee-haw. Ride'em time." She smiled and opened her eyes, letting go of her knees and slowly straightening her legs.

I slowly, I raised myself onto the mattress, and held her firmly as I rolled to my back with her still fully impaled on my cock.

When I stopped moving, I was on my back. She was sitting upright, facing away from me, with her feet on the floor between my legs.

"This is gonna be so damn good." She looked back over her shoulder at me. "You ready to ride, horsie?"

"Sure thing." I grinned back at her. "Stay in the saddle. You know how to post, right?"

She stuck her tongue out at me. "I've got your post, right here." She leaned a little forward, and pointed at my cock, then sat back down. "Ooh. Damn. That's good."