“There is no fucking way. Why does every guy want that? I knew you were going to make that the wager. There is no fucking way I am ever going to let anyone fuck my ass. Look at me I’m tiny and my little butthole is even tinier. One of my boyfriends before you tried it. He got like zero of his little dick in me and there was just no fucking way. Furthermore, I’ve never told you this because I didn’t want it to go to your head, but you have the biggest cock I’ve ever seen, let alone fucked. Shit, that thing splits my pussy open and I’ve had a baby! You are out of your mind.”

“Damn girl. There’s no reason to get all crazy. If you don’t want to try it that’s ok. I have initiated many neophytes into the pleasures of anal sex though. Lots of lube, slow going, communication and you might be surprised at the pleasures to be found. But really, it’s up to you.”

“Ok. It’s just really scary and I’m not going to do it.”

Three weeks pass

“It won’t hurt?”

“What won’t hurt.”

“Anal sex.”

“Oh. Well, it may be uncomfortable but if it is done correctly any pain will be minimized. Probably less than the first time you ever had sex.”

“If the guy who popped my cherry had a dick like yours, I would’ve screamed bloody murder.”

“Well look at you now! You ride me like a rented mule!”

“Lie back stud, I need to mount up.”

Looking into my eyes, she took my hard, thick cock and nestled it into her folds, right at the entrance to her first gate. Then she lowered herself down slowly engulfing the entire length with her tiny pussy.

“God, I love your cock. It fills me completely. Fuck, that was good. You’re the only guy who has ever got me to orgasm with his dick.”

“So glad you enjoyed your ride Baby girl.”

Three more weeks pass

“OK, I’ll try it.”

“Try what?”

“Anal sex. But you must promise me.”

“Promise you what?”

“First it won’t hurt…too much. Second, if I say stop you will immediately. And third, you’ll be super gentle.”

“Ok, I can make those promises. But I have a question for you. First, do you trust me?

She nodded.

“I’m going to take my time and the foreplay will be very long and enjoyable if you are willing to let yourself fall into the sensations that your rear has waiting for you.”

She smiled, shyly, and nodded.

“Lay back, spread your legs for me. Bring your knees up toward your chest. Expose yourself.”

She did and her moist pussy was exposed, her clit peeked from between her upper lips and her tiny butt hole stared back at me.

“Your pussy is beautiful, and so smooth. I can see your wetness glistening from your lips. You’re turned on by this…exposing yourself so wantonly, aren’t you?”

She nodded, biting her lower lip in the cute way she did.

“And look at your tiny little butt hole. Thank you for saving it for me. Go ahead and squeeze it for me. That’s it. Now hold it closed tightly. And release it now. Good girl.”

“Oh god, I am so turned on. This is so hot and so naughty and nasty. I can’t believe how much I want this.”

“I’m going to inhale you now and then I am going to taste and eat you.”

I lowered my head to her center and placing my nose just outside her soaking pussy; I inhaled deeply.

“Your sex smells of the sea and the forest.”

I lowered my nose to her small starfish and inhaled deeply, once, twice, and then again. My cock stiffened as her musky odor flooded my brain with her pheromones.

“Your ass smells clean with a hint of soap and a deep underlying earth tone”

Without warning my tongue began a journey from her asshole up to her clit and back again.

“OOOOOH my, that’s ummmmm...”

This time I allowed my tongue to flick and lick her butthole, spreading her ass cheeks wide.

“Your ass tastes like garden soil, ready to be plowed and planted.”

I summoned more saliva and wet her tiny hole while my tongue began to massage her hole.

“Oh, that feels strange, good but strange. I’ve never felt anything like this.”

She began to move her ass in small circles as my tongue began to plow into her waiting butt hole. I took my time and began to devour her virginal hole, alternatively licking and penetrating her slowly loosening starfish. Her body began to undulate and move under my ministrations.

“Fuck. You’re eating my ass. Don’t stop, please don’t stop, I love this.”

I drove my face into her ass and began to piston my tongue in and out feeling her sphincter begin to relax. I pulled back slightly and wet my thumb. Running my tongue up to her dripping cunt I allowed my thumb to circle her nether hole and slowly inserted it as my tongue found her clit.

“Ooooh, that feels nice. And your tongue, fuck yes.”

Using my thumb I pushed against the walls of her sphincter, allowing her muscle to relax and contract against my intrusion. When I felt her loosen a little, I replaced my thumb with my wet finger, slowly inserting the entire length in her anus.

“That’s deep. I don’t…oh my clit…”

I sucked her clit as my finger probed her inner passage, smiling to myself knowing how much longer and thicker my cock is over my finger. Taking my time I slowly withdrew and inserted my finger repeatedly.

“Oh, my ass. You’re fucking my ass. It feels strange, good but different. And sucking my clit. I might cum. Oh, I am going to cum if you don’t stop.”

I slowly withdrew my single finger and grabbed the lube to coat two fingers, keeping the pressure on her clit. She began to rock against my mouth, her moaning music to my ears. I positioned two fingers at her relaxing little hole and began to push, listening to her breath intake as my fingers pushed past her resistance.

“Oh my, be gentle, be gentle. It’s so thick and wide. I can’t, oh, oh, oh, yesss.” She whispered as my fingers slowly made their way into her anal canal.

I continued to suck her engorged clitoris and began to move my fingers in and out, slowly at first and then faster. I wanted her to orgasm while I fucked her ass digitally, the pressure on her clit expanding her orgasm to include her entire mons. As she began to arch her back and her moans shifted into a long, deep keen. I thrust my fingers into her previously untouched ass and wiggled.

“Nooooo, cummmming, fuuuuck, fuuck, fuck meeee.”

Her orgasm exploded into the world; her breath went ragged as she was gripped in the throes of bliss. I stopped the pressure on her clit, removing my mouth, allowing my fingers to remain as the muscles in her anal passage clenched and relaxed spasmodically. When I felt her relax, I slowly withdrew those two fingers and reached for the lube. She looked at me with amazement and a little confusion.

“That was amazing. I’ve never cum like that. I had no idea”

“Good, I’m glad you enjoyed your foreplay. Are you ready for your first ass fucking?

“What! Oh my god.”

Looking down she saw my raging erection as I slowly dripped the lube on my cock and began to stroke my long thick member.

“Fuck, please, you’re so thick, be gentle.”

“Don’t worry, baby girl, you are going to love this.”

I placed the head of my cock at her entrance and began to rub it all over her little hole. I was well-lubed and added more as I continued to massage her waiting hole.

“Look at me. Keep your eyes on mine. I want to watch you as you give your ass to me for the first time. Do you feel the pressure of my cock in your hole? I want you to squeeze down and release. As you release just relax.”

“Ok, like this…ooooh, your cock, it just, I don’t know what, it just kinda slipped in a little.”

“That’s right and now I want you to force it out, push that little bit of cock out of your ass as hard as you can.”

“Oh FUCK. Your cock is in my ass. It’s in my ass. I can’t believe this. How much cock is in?”

Laughing, “Just the head baby and now push it out again.”

I felt her pressure against my cock head and when she relaxed, I pushed another two or three inches in. Her eyes widened and her mouth opened soundlessly. I held myself still to allow her small passage to adjust and accommodate my intrusion.

“Ok baby, one more time, push it out hard.”

As she bore down on my penetrating penis, I allowed myself to begin to withdraw until I felt her relax. At that moment I slid the entire thick 9” intruder into her formerly virginal ass. Her eyes snapped open in shock and a loud moan escaped her lips.

“Oh. My. Fucking. God. My Ass! Your cock!”

“That’s right, baby. You’ve got my cock in your ass. All of it. Just look at me and let yourself get used to this feeling.”

I felt her inner muscles rippling against my cock as she began to relax. I began to withdraw and as I did, I smeared my thick tool with more lube before I began to re-enter her anal passage. Slowly I began to see-saw in and out, never too deep, never too fast, just slow and easy. Her moans and sighs were music to my ears.

“Are you ready now?”

“Ready for what? Is there something else?”

“Oh yes, I’m waiting for you to ask. I’m waiting for you to decide you are ready.”

“Ready? Ask for what?”

I slid my cock deep into her anus and laid atop her, my lips at her ears.

“Ask me to fuck your ass. Ask me to take you to places you don’t know exist. Ask me, no beg me to show you the secrets your tiny precious hole must tell you.”

She whispered, “Fuck my ass, please.”

“What? I didn’t hear you.”

“Fuck, you fucker. Use your massive cock on me. Fuck my ass. DO IT.”

Her orgasms that night were otherworldly. She screamed, begged for more and when I rolled her over and penetrated her like a stallion with his heated mare she orgasmed like a runaway train.

Three more weeks pass

She had mounted me, my cock deep in her strong, sweet pussy. She looked down at me and raised off my cock. Grasping me in her hand, she moved my cock to her little asshole.

As she impaled herself on my member, she smiled and said, “My turn.”