“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.