Anal Teen Folly

Story Info
A teenage virgin dives into sex, anal and all.
4.4k words
4.33
74.6k
34
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

All character are above 18 years of age.

Having just turned 18 the world seemed to have opened up for me...I closed my eyes and took a deep breath feeling the headless rush of being so swept away in what I was seeing and feeling that I almost didn't recognize my own body. My eyes had closed as I'd tried to process all of the sensations coursing through me.

It was an electric jolt that went through me as something warm and wet enveloped me, the heat surged from my groin all over my body and I could barely contain my breath as it jolted out in a ragged pant. Opening my eyes and looking down I saw her sweet lips were wrapped around my cock. Her tongue flickered over the head as she pushed her lips deeper down, the heat becoming almost unbearable. She pushed me backwards so I backed into the bed and with one hand pushed me backwards so I was laying down on my back, with her mouth encasing my cock. One of her hands was tantalizing my balls and the other had a finger circling and playing with my nipple. The sensations were amazing and nothing like what my 18 year old virgin self had experienced before.

I could feel the heat gathering in my balls and doing half a sit up I pulled her shoulders up so her lips came up and met mine, the rough texture of her pubes rubbing against my stiff groin. I may not have been in this situation before but I didn't want to lose a single opportunity as I quickly learnt how to kiss; not the kind of kiss that my Mum gave me on the forehead before I went to school, but a deep thrusting passionate kiss that pulled me away from consciousness on a wave of absorption.

As we kissed my hands moved over her chest feeling the weight of her breasts in each hand. My fingers circled each nipple and I ran my thumb over them, she let out a low groan. The desire to suck on her nipples overcame me and I bent my head down and my tongue ran over the flat of her nipple, reaching the center, my lip nudged it and then my mouth devoured her nipple. My other hand played with the other as she groaned and leant back so I could access her breasts more easily. I could have stayed there all day, happily exploring her chest with my mouth and tongue but there was more that I wanted to do. This may be my only chance and I was determined to take it. I sat up and holding her body close to mine I flipped us round so that she was lying on the bed and I was on top of her. I pressed my tongue into her mouth again, the slight taste of chewing gum reminded me of my urgency as chewing gum was not allowed in my home, just as what I was doing now and planned to do next, would never be allowed.

My tongue traced a trail from her mouth, down her neck and to her other breast, it flickered over it then I sucked on it, hard. She let out a groan, a good noise I hoped. Then between kisses and my tongue I made my way down to her belly button, her flat stomach was a perfect vision and I paused for a moment to take a long look at the perfection of her breasts rising like mountains above me. Then slightly tentatively, I trailed my way down to her groin.

To begin with I met the coarse hair that covered the bony mound in the front of her crotch. It smelt slightly musty and of vanilla soap, a scent that would always bring back this memory to me. Then, with both hands pushing her knees to part her legs I saw for the first time the true, complicated glory of the female anatomy.

I used my thumbs to gently part the flaps of skin that folded around her glory, one layer, two layer, then I saw a tiny little nodule, the size of a pea that stood out at the top of her most intimate areas, leaning forward my tongue gently licked over it. A salty taste, unlike anything Id tasted before, but utterly divine. I bent my head again and licked it again then placing my lips over it, forming a vacuum I began to suckle on it. Her groans became louder, still that deep noise but with my lips over her I felt as if I was at the center point of where these deeper moans came from.

I remained in that place for a few minutes as her legs thrashed round my head and her hands grabbed at my head then let go, only to grab again a few moments later. Her breath turned into ragged panting and I gradually slowed down my suckling motion, not wanting for the experience to finish before I had truly experienced all that I had fantasized and wanked about in the cubicle of the public toilets in the local shopping center. Home didn't give me any peace so any moments of privacy needed to be found outside of the house, I took full advantage.

Making my tongue thick and heavy I licked, using the back of my tongue, from her tiny little bead down past a puckered hole protected by another layer of skin down to a larger gash in her cunt. The aroma coming from there was heavy and dusky, I dipped my tongue in and she shivered with pleasure. I went to her clit again and wiped my tongue down her, dipping my tongue into her vagina as I arrived. Was this my final destination? I wasn't sure. There was more that I had fantasized about but maybe that was just a fantasy reserved for porn stars. Putting that thought to one side I put my hand between my own legs and played with my cock as I explored her with my tongue. Her clit was the most sensitive place and a single flick of her little bud with my tongue would send convulsions through her body. I didn't want her to come yet though.

My cock was rock hard and she let out an audible moan as I moved away from her pussy and went back to her breasts. She pushed her pelvis forward as if to get me to go back down there. I resisted but instead used my finger to flick at her clit, dipping into her vagina to get the juices I needed to keep everything lubricated.

I pressed my mouth against hers and her mouth opened to allow my tongue in as I climbed onto the bed, I pushed her body further up the bed and placed both my knees on the edge of the bed as I lent into her astride legs.

The anticipation of that tight warm wet place was nothing like the actual wonderful reality as my cock nudged at the hole that my finger was pushing in and out of. The start of the entrance resisted me but as the large head of my cock made its way past the start, the juices then lubricated the way. The warmth and moist squeezed around me as she let out a low groan and began pushing her hips towards me then pulling away.

Without even knowing I was doing it I responded by pushing my hips into hers, forcing the large bulk of my well-endowed manhood into her scented being then withdrawing just to push again. She let out high pitched moans each time I pushed in then inhaled as I pulled away. We found a pattern and the heat in my balls was beginning to build as I leant my head down to her chest and began to suckle on her large firm breasts with deep brown areolas. She began to thrust into me, taking charge of the speed, more erratically then both her hands pushed into my back as she whispered, sounding as if she was in pain, "don't stop" I took her cue and matched her speed of thrusts and suckling on her breasts. The heat built and built then a sudden explosion, what felt like a firework going off in my groin and going through my entire body, wiping any thought out of my brain as I burrowed myself even further into her pussy. She let out a shriek and pulled me to her, her body shaking with the orgasm, as I let out an involuntary moan.

We clasped each other for a few minutes as our pulses got back to a more regular speed. I was still on top of her with my flaccid penis inside her. Finally she let out a low chuckle, "I thought you were supposed to be a virgin, church boy" The nickname didn't rankle me as it usually did and putting my hand down to guide my cock out I extracted myself, looking round for tissues or kitchen roll to clear up the thick wet goo that covered my dick. "You need to go to the bathroom for toilet roll" She told me and laughed as I half covered my manhood with my other hand and tiptoed out of the room to the communal bathroom.

I wiped then rinsed myself, using soap to make sure everything was clean. My Mother could smell sin a mile off and we were well within 100 meters of each other even now. Taking a toilet roll off the hook I crept back into her bedroom and found her lying on her bed with her eyes closed, as I came in she opened them and taking the toilet roll she smiled at me, "Ah, thanks Church Boy, You're a real gent".

I wasn't too sure where to look as she mopped herself up and put a clean pair of knickers back on with a large wedge of rolled toilet roll in the crotch. She seemed entirely unselfconscious, but years of social conditioning was hard to shrug off and I, very self-aware, slipped on my white pants and trousers, hesitating to put my top back on, aware that once I was fully dressed that she might decide to kick me out or never see me again, I didn't think I could cope with either of those scenarios. In part because my head was still light from the strength of the orgasm Id had, nothing like the furtive wank sessions I had thinking about the shape of the girls breasts in her Sunday dress who sat across the aisle from my family at church; but also in part that I didn't know if I would be able to go back to a life without sex; without that sweet nectar to taste; without the weighty mountains with the clear mountain tops that needed to be explored. I held my t-shirt in my hands and looked at the floor, unable to meet her gaze.

"You know, Church Boy that was the best sex I've ever had. Are you sure you were a virgin?"

I nodded. I was sure. Very sure.

"Shall we do it again someday?" I froze, my heart betraying me by keeping its beat, just a little more regular than it was.

I shrugged, "Sure".

She suddenly smiled and swiveled so that she was on all 4s with her face close to mine. "You know something I'd like to do?"

I shook my head.

"I've never done anal" Her right eye closed up a little as if she were surveying me for my reaction. She must have been pleased as she smiled a little more and leaning in to whisper in my ear, "I want you to break it!"

My mouth went dry and my head spun as I tried to understand what she was telling me. That she wanted to live out my ultimate fantasy with her. Normal sex had always had the lure of the unknown, the forbidden before marriage, but anal sex is what truly made me hard and I would rub my thick shaft imagining it to be pushing in and out of a dark brown hole, so tight that tiny fissures were left in the muscle as I pushed in and out of the tight forbidden space.

Suddenly there was noise from downstairs, the opening and closing of the front door and the sound of general rummaging. "Shit, my Mums home" She suddenly said. "You need to go" She didn't say the second part as at the idea of being discovered anywhere other than church and in the unescorted company of a girl, a girl with mountainous breasts, my life wouldn't be worth living if my Mother found out. I was soft and dressed by the time Scarlet had even found her knickers. I was fully prepared to dive headfirst from the first floor window if it meant I wasn't found out, I was slightly relieved when Scarlett pulled on my arm telling me to follow her. She crept out to the hallway then pointed to a door that lead out onto the first floor veranda. I knew the house well enough from the outside to know that there would be steps down into the back garden. I kept my head low as I scurried through her garden. Within 10 minutes I was at home and mowing the grass, reliving what I had done with Scarlett in my mind.

Over the next few days I found many reasons to visit the public toilets and wank to the images of Scarlett and I together, the question of whether it was a dream or not always rose to the front of my mind as my mind woke after my ejaculation. I hoped that it wasn't my imagination although I was sure it wasn't as even my imagination couldn't imagine what we had done, and then her final offer of... At this I had to stop thinking and pull my pants up, that hope was too much to touch with thought.

On Monday at school Scarlett smiled knowingly at me and I had to turn away before my group of church friends noticed our interaction. It wasn't until Friday morning, nearly a week since we'd come together, that Scarlett came up to me in Science, "Can you make it to my place? After school? Like before?"

I nodded, "like before".

She smiled, biting her lower lip a little, "Well, maybe a little more than before".

My cheeks flooded red as my member shifted into an upright salute. "Okay" I watched her as she walked off, her uniform barely hiding her phenomenal body.

After school I told my church friends that I had a headache and needed to head home, I walked slowly out of their eye line then, with both shoulders of my back pack on, ran to Scarlett's house. She opened her door in her uniform and we were barely in her bedroom as I began pulling her uniform from her. My trembling hands undid the buttons of her shirt, I pushed it open and gaped at the black lace bra she was wearing, I'd seen something like that in the widow of an underwear shop but no-one in my family ever wore anything like that. I touched her bra then my fingers caressed the breast that pumped over the bra. My face nuzzled against her soft skin and my mouth was searching for her nipple. I pushed her bra down and latched onto her nipple, flicking it and caressing it with my tongue and lips. She threw her head back, pushing her breasts forward for my attention.

My hands pulled at her skirt and she helped me unbutton it as my mouth pressed against her, my tongue probing and exploring this wet orifice. A couple of times our teeth bumped, a strange sensation and she murmured a laugh which disappeared as my hand made its way inside her black knickers and explored her. As my fingers brushed against the tiny bud at the top of her layer covered crease she let out a moan and I concentrated my hand there, occasionally going down to her vagina to pump my fingers in and out and wetting them with juices so they were lubricated and ready to brush over her tiny bud again.

Her breathing changed with each change to my fingers, I nuzzled her neck then made my way back to her breasts, I struggled to keep my fingers in action as I lowered myself down her body. Then I remembered what she had said last time, I had to take a risk, had to see if she was willing to go through with it; I wouldn't have taken such a risk of ruining such a good thing unless it had been my biggest fantasy. I paused my sucking of her breasts and looked up at her, "How's your bottom doing?" It sounded more experienced and dirty than I could have made it even intentionally. She threw her head back to laugh and I noticed her teeth glimmering like a seals slick body.

Looking down to me she gave a tiny smile and a coy nod, "Maybe, you'll need to heat me up some more though" Later that evening, as I lay very satisfied in my thin, hard bed at home, I would run this sentence though my head and decide that this was the best sentence in the universe, "you'll need to heat me up some".

At the time I wondered what it was that I needed to do to "heat her up", my sexual experience was limited to our earlier meeting and furtive wank sessions in the local public toilets.

Never one to avoid a challenge I pushed her back onto her bed and went down on her, parting her secret lips and running my tongue strongly over her most private parts. As I did that I dipped my fingers into her honey pot, with the sweet tasting juice I ran my fingers around the tight brown bud that I hadn't even noticed on my earlier forays. It was tight and beautiful, a couple of stray hairs surrounded it and that gave me a gently flicker in my stomach as I realized that this was the most precious place, possibly un-ventured into before.

As I licked her, her legs moved around me. Picking up her legs and putting her feet on the bed, next to her rear meant I had far better access to all of her secret places. Once I was satisfied that my finger was as lubricated as it could be I gently attempted to ease the tip of my finger into her butt. The tight ring of muscle resisted but after a few attempts the tip made its way in, once that was in I found the rest of my finger could ease its way in, my finger went all the way in, up to my knuckle, then I pulled it out a little then pumped it back in. My finger swirled around the new orifice and I found my dick was as hard as a rock just from feeling the tightness of her around my finger.

I needed to stretch her in preparation for my large, hard member. I wet my next finger and she let out a gentle moan as I eased it in next to my first finger. "You're so tight" I found myself whispering.

"I want you" she whispered back to me, finally I got 4 tightly squeezed fingers into her, the muscles around her sphincter grasped at me, trying to push my fingers out. I resisted.

"Do you have any lube?" I asked realizing that my member was a great deal wider than my 4 fingers squeezed together.

"Dip in me" She replied, "My pussy is wet enough" That was true I thought as I pulled my fingers out of her, they smelt a little funky. My pulsing erection pushed into her pussy, the wetness was exquisite, the sensation of the dark wet warmth was overwhelming but with all the will in the world I couldn't stop myself pumping in and out, feeling my climax coming closer. She seemed to know what I was doing, "Pull out" She hissed, "Pull out"

I followed her instruction and the heat building in my balls slowly subsided with a heavy ache. I threw myself sideways and lay on my back on her bed, "That was close" I muttered, disgruntled at the lack of orgasm that I had been building for, but through my unhappiness I realized that this meant I had a chance of coming in her arse. That thought got my attention and I quickly rolled up onto my elbow, "How you feeling?"

"I want you in my arse" She whispered then rolled herself on top of me, I lay back on my back and allowed her to kiss me as she dipped my dick into her honeypot. Oh it felt good, even better now she was in control, setting the pace and the actions to her own satisfaction.

She positioned her arse over my dick and I could feel my dick being pushed and sculpted as she held its shaft and steered it against her tight anal muscle. She pushed against it but each time my head bent away from the pressure and slipped out of position. "Fuck" The frustration was unbelievable for us both. I needed to get in.

I rolled her over onto her back and pulled her hips to the end of the bed, folding her legs up so I had access. A single dip into her juices and I held my dick firm, the squidgy head pushing past the tight, squeezing ring of muscle. She let out a sharp cry. "Slowly" She muttered and I did my best but the tightness made my head spin and I had to force myself to breathe, panting like a dog, to stay still as she gyrated herself on my pole. Her eyes had gone back into her head and her breathing was deeper, a lower growl seemed to come out with each exhale.

As she gyrated she made her way deeper and deeper onto me and the exquisite tightness tightened the heat that was building in my balls. She put her hand down between her legs and began rubbing her clit in quick circular movements. Her groaning got deeper still and I felt the vibrations of each moan through my sensitive pole.

She changed her rhythm to a round motion and I leant forward to suck at her nipples, her breathing changed again to short shallow bursts then occasionally a long exhale as if she had just remembered that breathing was necessary regardless of the sensations flying through her. Her panting got louder and closer together as my tongue licked her nipples faster and her hand worked harder, "I'm gonna..." She didn't need to finish, as her body began bucking forward and backwards, the heat from my balls rushed into my dick and we came together, rocking together like we were each other's rocking horse; both grunting and groaning as fireworks flew round our bodies.

12