tagToys & MasturbationAnal Discovery

Anal Discovery

byAnalAnnie19©

Looking back I guess I was very sexually reserved as a young person. But by 18 I was beginning to feel more relaxed about have sexual desires and fantasies.

I didn't start masturbating until I was 19 but it soon became a very regular thing. I would often think about touching myself during the day and I thought I was terribly sexually liberated because I knew I was going to act on it that night.

I thought people would be astonished to know that I touched myself sexually. I now know that I was doing nothing out of the ordinary, but at the time I thought I was a real wild one.

I was still living at home and I would masturbate most nights, usually in bed before going to sleep. At the time I thought what I was doing was about as outrageous as sexual behaviour got.

Then, as now, I prefer to have my knees up and legs spread wide when masturbating, partly because of the easy access to my clitoris and vagina but also because of the heightened sense of brazen sexuality of being naked and having your legs wide open.

But although alone in my room I was never quite 100% sure that I wouldn't be interrupted by a family member so I'd usually masturbate on my back with my legs slightly apart and my pajamas still on.

Usually by the time I would climax I'd have one hand working my clitoris fairly quickly while using the other to work one or two fingers in and out of my vagina.

On one occasion which I remember very vividly it was fairly late and everyone else was long in bed. On a whim I deliberately took my pajama pants completely off in a mood of heightened freedom before even getting under the sheets.

At this point the light was still on and it felt great to stand there with my bottom and pubic hair exposed. I took the time to enjoy my nakedness and carefully fold the pajama pants and placed them in the dresser drawer.

Instead of just flicking back the sheets and getting in I leant across the bed with my legs slightly apart and pushed out my bottom before drawing back the covers. I had this sense of exposing my labia, my nakedness to the world even though the only thing behind me was the wall.

I found it so arousing that I looked around the room for things to pick up. I bent over keeping my legs straight and apart to pick up this and that. Each time I bent over I felt a sexual focus between my legs rising.

I imagined I was being watched and stood in front of the mirror. I had planned to leave my pajama top on because if someone came in while I was under the sheets they wouldn't see my naked bottom half but would be able to see my naked torso.

But I was caught in the moment and watched myself in the mirror as I unbuttoned the top and let it fall to the ground, exposing my breasts. Seeing myself naked like this, fondling my breasts, nipples erect was surprisingly sexual. It was like I had leap into a new realm of sexual deviancy.

It was not like being naked after getting out of the shower or something. There I was standing fully exposed looking at my breasts and pubic mound and seeing my naked self in a purely sexual way.

I was thinking of men looking at me like this, seeing and being aroused by my naked body. "Come on and fuck me," I whispered quietly to men in general.

Saying the words 'fuck me' was liberating. There I was, supposed to be wholesome and innocent but touching breasts and wanting to be fucked. The idea immediately shifted my focus to my vulva. I wanted to touch myself more intimately; I wanted my fingers inside me!

I turned off the light and got into bed. I had a much greater feeling of raw sexuality compared to my usual masturbation sessions when my hands were down my pajamas.

While often intense, masturbating with my pajamas on gave a sense of discretion, privacy and reservation.

There was something immensely erotic about being naked for the sole purpose of wanton sexual gratification. Once I got into bed I was surprised how physically sexy it felt to have my naked bottom and hard nipples against the cool sheets. I spread my legs wider than usual but still flat on the bed.

I started by fondling of breasts and nipples then down to my labia and clitoris. My sexual arousal came on much more quickly and insistently than ever before – I was already so wet! I soon found myself at the usual end game of right hand quickly rubbing my clitoris with two fingers of my left hand in my vagina.

I could feel the sexual energy rising, magnified by my nakedness and lusted after the orgasm I knew would come. I couldn't help but lift my left knee up to get my fingers further inside me as lust overtook my usual sense of refrain.

It felt great as another layer of restraint fell away and I was more deeply penetrated by my fingers. But I also felt exposed with that never quite complete sense of privacy that you have in the family home. Wondering if someone is going to barge in and see one leg up in the air.

But I couldn't let the sexual pleasure to subside so I rolled onto my right side so my knee could be hard up against my ribs without being up in the air. But while my right hand still had great access to my clitoris it was hard for my left to get at my vagina.

I didn't consciously think about it but I just arched my back and switched to fingering myself from behind which felt different and was further liberating as another layer of inhibition peeled away.

However, the shift in position had slightly slowed the rush toward orgasm and while I was still totally consumed by this sexual act I also felt like I could take my time to enjoy it.

I took the time to smear my whole genital are with the copious amount of fluid I had produced before reinserting my fingers. The sopping wetness was in itself highly erotic.

Soon both my hands were wet, my labia, my clitoris and really my whole genital area were slippery and wet and my vagina kept producing more. I took it as a confirmation from my body of the intensity of the pleasure I was feeling. I thought to myself, "Yes this is as good as I thought it was. Look how wet I am getting."

My breathing was shallow and quick and I started to quiver and my hips began to relexitively grind against my hands. I was completely unconscious of anything in the world except my body and the orgasm looming.

The wetness egged me on and as I continued to masturbate I would take my fingers out and rub it over myself. I hadn't masturbated from behind with anything like this intensity before, nor in such a state of lust. So the first time I touched my anus it wasn't intentional.

It sent a jolt of pleasure that took me completely by surprise. Academically I knew that some people engaged in anal sex but it never occurred to me that pleasure from this source would apply to me.

I quickly slid my fingers back into my vagina and went on fingering myself but the next time I took them out I was immediately drawn to my ass.

I thought I would just brush my fingers against my sphincter as I had done before – just give myself a little tickle to see if it actually felt good. But it felt great and I found my fingers lingering and probing.

As my finger probed at my sphincter I was suddenly struck by the thought that putting a finger in my ass would be the ultimate act of letting go and of complete and utter nakedness and exposure.

The earlier moment that I had taken off my pajamas came back to me. Just that spur of the moment decision to take my pants off gave me a sense of erotic taboo then which came back with redoubled intensity.

I wanted my finger in my ass and I decided to do it. The fingers working my clitoris stopped. My breathing stopped. I gently eased my finger in and every millimeter of penetration was pure pleasure.

Once my finger was in to the first knuckle I could feel the clamping tightness.

The physical feelings were intense but were magnified by my sense of outrageous, brazen willingness to do whatever felt good. I felt I had totally let go and utterly surrendered all inhibitions to my sexual desire.

I had never felt anything like it, I couldn't believe the level of sexual gratification it gave me. It was a near orgasmic level of pleasure and I wanted more, more, more.

Then I realised I was feeling this level of intensity when I wasn't even moving. With an uncontrolled jolt I arched my back pushed the finger further into my ass. I began to rub my clitoris in a frenzy and my whole body began to shudder.

I pumped the finger inside me with fast but tiny in and out motions. All I had was half a finger in my ass and although I was moving it quickly the distance it was going in and out was minimal. But I had never felt so much like I was being fucked in my life.

In seconds I felt an orgasm rise and then overwhelm me in long, slow, intense wave after wave of unashamed pure pleasure.

After a minute or two to get my bearings I slipped my finger out and had this abstract sense that I should feel guilty or dirty. Instead I had an unexpected and slightly nervous but also liberating giggle to myself.

I had just discovered a whole new world of pleasure in sex and my mind boggled at the future joys I would experience.

I had often thought with lustful excitement what it would be like to have a penis inside my vagina. I couldn't begin to fathom the ecstasy that being fucked in the ass would bring.

Discovery 2

Once I had discovered the pleasure of fingering my ass it became a common part of my masturbation.

I wouldn't necessarily put my finger in my ass every time I masturbated, and sometimes I didn't touch my ass at all, but more often than not I would at least be rubbing my ass crack by the time I came.

I always got a thrill of sexual anticipation when I realised I'd be home alone for the night. If by some fluke my siblings all planned to be out on the same night as my parents I'd be a little short of breath every time I thought about it – even if it was a week in the future.

As soon as the last one walked out the door I'd be at the window to watch them get in the car and drive off. No sooner than they were around the corner my hand would be down my pants to get at my usually already wet pussy.

I would still go to my room, usually at a half run with my hand never leaving my crotch. I always wanted to be completely naked and my legs wide open to feel maximum sexual freedom. And I just couldn't bring myself to do that in any room except my own with the door firmly closed.

Then one day events conspired to give me an opportunity to go to the next step in exploring my anal sexuality.

A couple who were friends of my parents were paying a visit and talking about their much anticipated dream holiday to explore Europe for a month. I was sort of half joining in the conversation but not really tuned in until they mentioned that their daughter wouldn't be able to house sit for them because she was now living interstate.

They were having trouble figuring out what to do about watering the plants and looking after the cat in their absence. We lived about an hours drive away so it wasn't really an option for one of us to go up there every day.

I had plenty of leave owing from work, some old friends living reasonably near to their house and I was behind on the study I was doing part time. Three pretty good excuses for me to volunteer.

The implications of having all that time alone to explore my ass in freedom meant I had to clamp my legs closed to keep control of myself. Despite feeling short of breath and my heart racing I managed to sound fairly casual when I said, "I could look after your place for you if you like." I rattled off all my excuses and to my utter delight all concerned thought it was a great idea.

I came very quickly in bed that night – having been wet for most of the day. Then I masturbated every morning and night for about a week in a state of ecstatic anticipation.

Eventually (about three very long weeks later) I was in their garage bidding them farewell. I watched them turn the corner, waited for the roller door to close then dashed through a door they had from the garage to the kitchen.

I shut the door behind me and leaned against it. I was in a fairly cosy corner of the kitchen behind a bench and in no time I had my jeans and panties around my ankles. With my bare ass against the cool door I used my right hand to rub my clit and my left to reach up under my top and fondle my breasts. I raced to orgasm in about 60 seconds flat.

Once I'd come I felt very exposed standing there in someone else's house with my pants around my ankles and my pussy and fingers wet. It felt like such a brazen thing to do and I felt like a deviant but that made me feel cheeky and sexy rather than uncomfortable. But I did quickly composed myself and pull up my pants to get a sense of normality back.

It was late afternoon when they left so by the time I'd unpacked, fed the cat, rang my parents to say I'd arrived safely and went out to get something for dinner I decided to take a shower and settle in for a private night alone in front of the TV.

When I got out of the shower I automatically started getting dressed but as I looked at myself in the mirror standing there with just my panties and a bra on I thought, "I don't have to wear clothes here."

It was such a liberating idea. "I can do anything I want in any room of the house," I thought. That was a sexy idea but it was thrilling to know that I actually would be doing anything I wanted.

I looked at myself and rubbed my breasts through my bra then put one hand down the front of my panties and fondled my labia and clit.

I decided I wasn't gong to put anything else on for the rest of the night. I was going to stroll about the place in my underwear. It was such a powerfully liberating feeling that my nipples hardened and I felt my stomach muscles tighten as my pussy began to gently pulse.

I had a momentary concern, "What the fuck am I gong to do if someone knocks on the door?" But I thought, "Well it's hardly a crime to walk around in your underwear." Still, I grabbed my dressing gown and decided to put in near the front door so it would be handy just in case.

As I walked out of the bathroom I was so excited that I went straight downstairs and threw the dressing gown on the ground near the front door. Once that was done I felt safe to do whatever I liked.

I took my time as a strolled around feeling freer than I ever had before. I grabbed a magazine and put it in the middle of the kitchen table. Then with my legs straight and slightly apart and my ass pointing out I bent over the table to flip through it.


If felt great with my ass in the air like that. I thought of the view that someone watching me from behind would have and as I kept my left elbow on the table I used my right hand to reach behind and grab my panties and pull them up my butt crack. They were just a plain cotton pair and I didn't give a damn if they got stretched out of shape. The pressure against my asshole felt fantastic and I decided to leave them that way.

I walked to the lounge and with every step the panties jammed in my crack rubbed at my ass and pussy. I felt so wantonly, outrageously sexual and I had an amused thought at the shock the owners would be feeling if they knew what I was doing in their house.

I sat on the couch and took off my bra. My nipples were hard and my tits felt so, so naked and so, so good in the big empty lounge. I felt as naked and exposed as if I were starkers in a supermarket.

I lifted my right leg over the arm rest. I leaned back and shifted my ass close to the edge of the couch. I put my left foot on the coffee table and let my knee drop so my legs were now wide open, this time thinking of what someone in front of me would be seeing.

That really threw me over the edge. It was one thing to be in just my underwear in this big house all by myself. It was another thing to have my panties jammed up tight in my ass crack, strutting around and feeling sexy. And it was yet another thing to have my tits exposed and nipples hard. But once my legs were spread wide like that I had shifted from sensuality to raw sexuality. Psychologically it was like shifting from playing with myself to fucking myself.

I could feel my vagina and clit tingling even though I wasn't touching them. It felt so good I didn't want to break the spell and I just sat there rubbing my tits and playing with my nipples.

I kept at this for about 10 or 15 minutes – just enjoying my breasts and nipples – and eventually I was just quickly flicking the tip of my ring finger of each hand across each nipple. Eventually I rose to a near orgasmic ecstasy – just from rubbing at my nipples!

The whole time I didn't touch my vagina or clit but just left my legs spread wide with my panties up my ass crack and tight against my pussy. Despite not touching myself between my legs I felt that having my legs wide open like that gave an enormous focus on my vagina and clit. My hips began to hump minutely, more as a reflex than a conscious decision.

I had always enjoyed touching my breasts and nipples in particular but I had never got so close to orgasm from them alone. I could feel my juices oozing out and wondered at how wet my panties would be when I finally took them off.

I found it so intensely erotic to have my legs open in such a provocatively sexual pose and not hidden away under the sheets in my own room but outrageously exposed in these neither private nor intimate surroundings. It was erotically like masturbating in public but without the practical downside of actually being in public.

Eventually the joy from my nipples peaked out and it was time to move on. I knew if I touched my clit I'd come in a flash but I just wanted this to go on and on. I decided I'd just work on my ass as I had with my nipples and leave my vagina and clit alone.

I put both feet on the ground and leant forward thinking to just lift my ass up enough to take of my panties. As I did so I looked at my crotch to see if any wetness from my vagina was showing through. I had a double take when I saw that they were not only wet they were actually glistening where my juices had completely soaked through. I left them on and put my hand between my legs. It came away wet and I suddenly realised the amount of juice that had come out of me.

I decided to go upstairs to take off my panties and finger my ass sitting on a towel to soak up my flowing juices.

On the way I walked past a mirror in the hall and looked at myself and I thought about fingering my ass in front of a mirror. I'd never done that before, with my ass or vagina, and the idea of watching my finger go in and out of my ass really turned me on.

There wasn't a mirror in my room (I was using a spare room upstairs next to the master bedroom) but I knew there was a full size one in the main bedroom. I thought it would be another level of cheekiness to actually masturbate my asshole while in their room. And, caught in the moment I decided to do it.

I got a couple of towels from my room and took off my soaking panties while I was there. Now it was time to get serious and I wanted to be totally naked. I was desperate to get down to business and start fingering my ass. I was also fascinated to see what it would look like to watch my finger going in and out of my asshole.

But when I walked into their room I thought about what people would think if they knew I was about to masturbate not just in the house of our family friends, not just in their own bedroom but that I would be putting my finger into my asshole.

A part of me knew I was doing something wrong and I also knew I wouldn't have done it if I wasn't so worked up and horny. But another, stronger part of me reveled in the outrageous deviance of the act. This strong sense of sexual perversion fed on itself and I wanted to be as wanton and reckless as possible.

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byAnalAnnie19© 113 comments/ 553561 views/ 200 favorites

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