A Pleasurable Vacation

Hi it's Bree here again. I've been having A LOT of fun lately with my new toys, sometimes too much as my poor pussy will attest some mornings! To tell you a bit about myself I'm 24 years old, 5'3" and fairly petite, with blue eyes and brown hair I keep fairly short because I like to think it suits my pixyish-looks. I'm really enjoying being single now, having been in relationships fairly constantly for the last 5 years. Having the time to discover myself and what I really want from this life has been somewhat of a revelation, some "me-time" if you like.

Not too long after the events that inspired my first story here on Literotica I decided to take some time off that was owed me from work and get away for a holiday by myself. I booked small apartment in a holiday town up north to enjoy a bit of sun and relaxation. Arriving in the town after a warm 6 hour drive, I was pleasantly surprised to find a lovely single bedroom apartment on the second floor that overlooked the pool. Throwing my bags down I headed for the shower to freshen up and revive myself.

Padding out of the shower naked I set my bags on the bed and began to unpack. Putting everything away I got to the bottom of my suitcase where my toys were tucked away, stored in a pillow-case. I'd brought all of my toys knowing I would be away for a week or more, sure that in that time I would find a need for each. Laying them out on the bed sent a delicious tingle to my pussy - knowing the pleasure they were soon going to be giving me. I had an 8 inch red vibrator, a slim 12 inch double dildo and a 12 inch beast of a dildo with balls and a suction cup base. Putting them away in the bedside drawer I threw on a bikini and headed out to the pool for some rays.

Languorously soaking up the sun after a swim, my mind drifted to the toys in my room and I began to think of the ways that I would pleasure myself with them that evening. As the sun dried my skin my pussy dampened my swimsuit, the more elaborate the fantasies in my head became. I deciding to retire to my room before my dripping pussy and erect nipples gave away my aroused state to the other bathers around the pool.

Shedding my bikini as I entered my apartment I enjoyed the sense of freedom I felt from being naked - not something I have always felt comfortable with. I headed to my bedroom where I decided to indulge myself and smoke a joint. Lying on the bed with a pleasant buzz on from the pot I could feel my blood coursing through my body, nerve endings tingling, with the sensation centring on a fantastic throbbing/pulsing in my pussy. Cupping my smooth mound in my hand I part my sticky lips with my middle finger, dragging it slowly up my pussy till it rubs over my juicy clit, sending a jolt of pleasure through my body.

The effects of the pot seem to be multiplying the intensity of the sensations I am feeling. I lie back on the bed with my arms at my sides and take a few deep breaths, not moving. My pussy seems to be pulsing with a life of its own, my clit throbbing with every beat of my heart. As I lie there I can feel my pussy juices starting to run down between my ass checks, making them slippery, as I clench and unclench my pelvic floor muscles.

Getting onto my hands and knees on the bed I position myself so my ass is facing the full-wall mirrors that hide the wardrobe at the end of the bedroom. Staring at the lascivious image of this I tilt my pelvis back and watch as my sticky pussy lips slow part to reveal my hungry pussy within.

Reaching a hand beneath me I run two fingers through my pussy and up to rub my tightly crinkled asshole, already sticky with my juices. I slowly run one finger around and around its entrance then apply pressure and force it to slide in to the first knuckle. A wave of pleasure rushes through me from the nerves in my tightly clenched hole, to be slowly replaced with a desire to feel something larger slide into my ass.

I reach down to the bedside draws and removed the lube and the double dildo. At 1 1/4 inches in diameter it's not huge but it certainly fills my ass nicely! Lubing up half its length I resume my previous position on the bed, looking over my shoulder at my soon-to-be fucked ass. My left hand gripping the jelly cock stretches over my back and rubs the veined shaft back and forth through the crack of my ass and over my parted pussy. My right hand between my legs grabs the toy by the head and positions it at my quivering hole.

My eyes closed to concentrate on the sensations I slowly press forward with my left hand, slow deep breaths to relax my as yet unyielding ass. With a long exhale I feel my ass begin to relent and the head of my rubbery toy begins to open up my tight hole. With a satisfied groan I feel it slip home, my sphincter gripping the back of the large head and its smaller shaft behind.

"Ahhhhhh........" I sigh with pleasure as my asshole begins to pulse and grip the intruder being forced into it.

Holding it there for a few breaths I let my body adjust to the feeling of fullness and concentrate on the throbbing pleasure that my ass is giving me. Slowly I begin to push further, till a few inches later the head meets more resistance, something inside of me only slowly expanding to accommodate the girth of the dildo. I begin to twist it around, turning the shaft in full circles, the veins on its shaft setting off fireworks of pleasure as they rake the nerve-endings within my ass.

Pushing again I can feel the head slowly parting the resistance deep inside me and with a sigh it seems to pass through this constriction and another couple of inches slides easily into my hungry ass. I lift myself up onto an elbow and look back over my shoulder at the view in the mirror - Ass cheeks spread, my pussy glistening with moisture and about six inches of dildo protruding from my ass.

"Mphmm... GOD!" I groan at the wanton picture this presents in the mirror. The pleasure from stuffing my ass full of cock pushing me ever closer to orgasm.

Easing the dildo back out, till I feel my ass gripping just the head, I pull it free with a pop and squirt lube deep into my still gaping ass. As I slip it back into my ass the sensation of the head scraping the nerves of my sphincter makes me groan with lust. Pulling it free I force the head in and out of my ass a few times, bucking from the pleasure of every entry and withdrawal.

Deciding for some serious penetration I push further, taking more and more of its length. As I pass 8 or more inches I feel it twisting in my grip, bending inside me as if turning a corner within my body. Easing it deeper still I find myself holding no more than the head, with near on 11 inches of dildo spearing me to my core. With a groan I begin to pump it back and forwards in my ass, long deep strokes that I can feel penetrating me so incredibly deeply.

With my left hand fucking my ass hard, I reach my right between my legs and start frigging my erect clit, bring me closer and closer to an enormous orgasm. Laying flat on the bed I close my legs, trapping my right hand between my thighs, maintaining the pressure on my clit but not moving my fingers.

"Oh...Fuck...Fuck...Fuck!" I grunt out as my left hand brutally fucks my ass deeply with every thrust, the pleasure of anal penetration getting me so close...!

I imagine myself spread on the bed like this pleasuring myself, the door opening and a stranger walking in, his cock now being the object filling my ass to it limit, slamming me into the mattress with every thrust. With this fantasy in my mind I feel my body stiffen and with a final thrust into my ass a massive orgasm rips through me. Bucking and grinding onto the hand trapped between my legs, my asshole clenching furiously at the long intruder within it, I scream out into the pillow as wave after wave of pleasure wracks my body.

"Ahhh! Yes...Yes...YES!" I cry.

With slowly diminishing pulses my orgasm subsides, my hand slowly pulling free the dildo from my now burning ass, a final groan of pleasure escaping my lips as the head pops free of my ass. With a long drawn-out sigh I roll over, completely satisfied and with a huge grin on my face I just cannot subdue I fall into a blissful sleep.

An hour later, much revived, I headed out to dinner to a lovely seafood restaurant that had been recommended to me. After a wonderful meal and with a glass of white wine in my hand I could not help smiling at the thought of what I had been doing to myself earlier in the afternoon. It had almost been with sluttish abandon that I had furiously brought myself off and I could not help a blush rising to my cheeks in response.

Ordering another glass of wine I had to laugh at myself for my somewhat prudish concerns -- not really in keeping with the newly confident and self sufficient Bree I was trying to become. As I savoured the wine, with my ass still tingling deliciously, I found a smile had again appeared on my face.

Awaking the next morning I threw a short sun dress over my nakedness and walked out on to my balcony to take in the view. The beach off through the trees in the distance, a warm breeze blowing and a few early morning sun bathers gathered around the pool below me. Standing there with just a short dress covering my naked pussy, almost flashing the swimmers below, gave me a delicious thrill.

I began to imagine myself sitting out here in the sun, riding one of my toys and bringing myself to orgasm, while casually watching everyone go about their morning, completely oblivious to my activity. With rising arousal levels I head back inside my room and remove my dress, standing in front of the windows with nothing but the thin lace curtains concealing me from everyone below.

With flushed cheeks I decide to act out this fantasy -- or as much of it as I dare! I go to my bed and open the drawer containing my toys, looking at each in turn and deciding which I feel like using. With a shudder of raw lust my hand closes around the massive shaft of my 12 inch monster dildo and pulls it from the draw, along with the bottle of lube and a towel from my bed.

Placing them on the small dining table in my room I drag the table closer to the balcony windows. I stand in front of the windows, the table's smooth Formica surface reaching to nearly mid-thigh behind me. The sun filtering through the fine curtains warms my naked body, possibly visible to the people I can see below me.

With the pulsing of desire increasing between my thighs I turn back to the table and pick up my thick dildo. With a swipe of my fingers through my pussy I moisten the suction base of this big beast and stick it firmly to the corner of the table, twisting it so the big head is pointed towards the windows. Picking up the lube I squeeze a large amount onto my palm and spread it to both hands. Needing both hands to fit round its fat girth I grip the shaft and stroke it up and down, coating its full length liberally in lube.

Turning to again face the window I take a small step back till I feel the cool slippery cock nudging against my ass cheeks. Rising up onto tip-toes I tilt my hips back a little and lean forward, rubbing the fat head back and forth over my hungry slit. With one hand against the window my other reaches down to position the big cock at my pussy entrance, then slowly I start lowering my body down. The tapered head begins to force it way into my pussy, widening my hole to its limit as I near the thickest part of the helmet on this huge cock. Easing off by raising my weight again I take a few deep breaths and lower myself on to its girth again.

"Oh...Ahhh!" I cry as I try to force myself to take its massive size.

I thrust my pelvis back and forth trying to find an easier angle of entry, slowly engulfing more and more of the near-soda can-width head. With a slippery rush my pussy swallows the head, drawing from me a gasp of pleasure mix with relief, as my fully stretched hole settles round the smaller diameter of the shaft on my fat rubber cock.

"Oh GOD!" I groan at the sensation of such massive penetration, every nerve ending in my pussy thrumming with pleasure.

The dildo now securely lodged in my dripping pussy I place both hands against the window and look at the view outside. Not 20 feet outside my window are maybe a dozen people around the pool, needing only to look up at my window to see my shadowy figure through the thin curtain, surely? The feeling of exposure is incredible! My pussy floods with moisture as I stand there impaled on my massive toy, the thought of catching someone's eye, the look on their face as they see what I'm doing causes a shudder to run through me.

With my forearms now on the window, bracing my weight, I begin to ride up and down my big cock, spreading my feet further apart as I swallow inch after inch of fat rubber cock. Rocking my pelvis up and down I can feel the huge head of the dildo moving within my body, like a fist thrusting its way towards my cervix. As I get a good rhythm going I look down between my legs, watching my gapping pussy swallow 8 or 9 inches of this beast with every thrust. With every upstroke my juices are milked out of me, running down the shaft they drip onto the table.

Lowering myself further I feel the head reach my cervix, with nearly 2 inches of shaft still to go I am determined to take the whole cock. Somewhat uncomfortably I keep applying pressure and with slow deliberate breaths I feel my vagina elongating and taking more of the dildo. With each exhalation I feel my pussy creeping down the remaining shaft, till at last I feel the balls rubbing against my ass cheeks.

Now fully impaled on my 12 inch cock I raise my head to look outside, my eyes settling on a rather attractive guy laying by the pool, his head turned my way but dark glasses hiding his eyes. Not sure if he's looking, or if he can see me, I begin to put on a show for him. I begin to plunge up and down on the huge cock below me, lifting up onto my toes to ride as high up the shaft as I can then throwing my weight back down to spear myself deeply.

With increasing need I ride faster and faster, relentlessly slamming the big rubber cock into my body as I stand exposed before my bedroom window. The act of pleasuring myself in full view of those below gives me an incredibly erotic kick, bringing my orgasm ever closer.

Locking my eyes on the handsome man by the pool I concentrate on the sensations coursing through my body. My pussy gripping hard to the fat shaft, its veined texture sending my body into spasms of pleasure as they ripple within me.

With a final thrust, my full weight forcing every inch of the huge cock inside my abused slit, an orgasm rips through me. The intensity of it shocking me as my body bucks, with wave after wave of pleasure crashing through me.

"OH MY FUCKING GOD!!!!" I scream as my legs give way beneath me and my pussy grips hard, almost cramping round the huge cock within me.

With my hands and sweat-beaded forehead resting against the window, my weight seems to be wholly supported by the massive cock between my legs, its balls digging into my ass with the pressure. With shaky legs I lift my weight up, with inch after inch of fat dildo slowly withdrawing from tightly stretched hole, until I am standing fully upright with just the dildo head still within me.

I can feel my pussy gripping the back of the fat head, struggling to let it go. I'm forced to go up onto my tip-toes to lift my body off the remaining dildo beneath me and with a juicy pop the head finally come free. Turning back I look down at my massive pleasure toy, glistening with my moisture, juices pooled around it base. A shudder of lust runs through me at the sight of it and I leave it stuck to the table.

Heading to the bathroom I grab a towel and wipe dry my sticky thighs and dripping pussy. Putting on a bikini I head outside and dive into the pool to cool off, floating gently at the side of the pool letting my body calm down and relax after such an intense session. Pulling myself from the pool I spread myself on a sun-lounger and soak up some sun, my pussy still swollen and puffy from abuse, I sunbath surrounded by the people I had just put on a show for.

The handsome man in the sunglasses was still there, his head turned towards me and a small smile on his face, and is that a noticeable bulge in his shorts! I smiled to myself, turned my head away and thought of how much more fun this holiday was going to be...