The Octopie Creampuss

I spent most of my thirties single and getting laid as often as possible. A good handful of one night stands and several 'repeaters' were sprinkled around a number of regular 'friends with benefits' types long before that term had been popularized. As a result, I was able to enjoy a decade of almost nonstop sex with as much variety as I could find.

It wasn't that I couldn't imagine marriage and children, I just hadn't found the right one. I don't mean to suggest that none of the women I met would not have been suitable long-term partners. Indeed, I might have enjoyed a lifelong union with two or three of the incredible women that were part of my history in those days but the simple truth was, I was just too picky or didn't really know what I was after.

I was always self-aware of my own indecisiveness about settling down. I always thought I would get married and start a family but I didn't want that at the expense of maintaining a healthy and evolving sexual lifestyle. I didn't want to find myself in a sexless marriage or with a partner who didn't share my passion of exploring new sexual experiences.

As a result, I arrived at the conclusion that if I was ever to find the woman of my dreams I would need to do as much research as I could find. I set out to sleep with women of different backgrounds and varied sexual histories. As much as I wanted to explore the variety of the physical female form, I craved the knowledge of their turn-ons and their desires. In short, I wanted to be taught what a woman wants and needs. I wanted to understand what they really craved and how far their sexual boundaries might be expanded.

The way I saw it, my experiment would be a success if I achieved one of two goals. The prime objective was to find a partner who shared my life interests and had a healthy appetite for sex. Barring that, I would also have considered it a success if I was able to satisfy each and every one of my sexual curiosities before settling down with someone who at least liked sex even if they were less adventurous than myself.

The firmest conclusion derived from my personal sexual investigation is without question, that a woman who freely communicates her needs and desires without censor, is the partner one must choose if they aspire to a truly fulfilling sexual relationship. Finding these types of women allowed me to cross many items off my list. My interests had little to do with less sexually inexperienced partners back then but that would come to be a powerful interest of mine much later in life. Sure, it is fun to teach and share new firsts with a relative newbie but I was seeking learning for my own needs. I actively sought out women whose experiences were much more vast than my own. I worked hard to find sexually confident women who would actively test my boundaries and force me to question assumptions of what I had defined as normal or appropriate.

Ultimately, I feel that I've achieved both objectives but were it not for the breadth of my experimentation I do not believe I would have evolved into the sexual partner I now am. By the time I finally bit the bullet and married at the relatively late age of 41 I truly felt that I had scratched every itch and was in a position to commit to another without ever regretting that I hadn't explored as much as I had needed to be sexually fulfilled.

Those years allowed me to watch and later participate in sex with multiple women at the same time. Lesbian sex and threesomes have always been two areas of extreme interest to me. I learned the excitement of consensual sex with power imbalances both as a dominant and as a submissive. Masturbation went to a whole new level when done with another and the introduction to the wide world of sex toys led to many situations I hadn't really considered. In short, I was able to live out almost every fantasy I had ever relied on while jerking off multiple times daily since that first time I learned the wonderous secret of making myself cum. But alas, this story is not actually about me so for the telling of this tale it is only necessary that I share my experience with Fiona.

As I climbed into the octopus costume I thought back to our sparsely shared history. At 5'5, Fiona still has the hard body of a woman who had raced up and down a soccer pitch for most of her life. Her smallish breasts perfectly suit her personality and that hard ass never failed to grab the attention of every customer that had the pleasure of her service. The freckles and blonde ponytail were just icing on the cake.

Our relationship had only developed because of my love for tuna and Scott's Diner had the best in town. I was 27 and probably averaged 4 lunches a week at Scott's. As I came to be a regular, Fiona came to be my regular waitress. I've always been a generous tipper which probably had something to do with the extra attention she came to provide my table but I'd like to think there was a certain spark between us despite her tender age of 19 and the reality that we moved in much different worlds. In fact, were it not for a chance meeting one night I very much doubt our relationship would have ever ventured beyond friendly customer service.

The 8 year difference in age wasn't necessarily disqualifying on its own though I'd normally always connected with women closer to my own age. The issue at that time was my quest for experience. Though criminally attractive Fiona just wasn't what I was looking for in my life back when we first met.

I was done with the bar scene in those days but being single meant frequent nights of eating out. It was one of those nights when I had shared dinner with friends and later found myself staying behind to finish the night alone with two or more fingers of scotch. There was an acoustic guitarist playing some great music which prompted me to stay longer than I normally might all by myself. I'd just considered calling it a night when I noticed a familiar ponytail coming out of the restroom. Instantly, my cock began to ache as it stiffened to full length. My heart had begun to race and I needed another shot to quench the sudden dryness in my mouth.

Probably because I was staring for far too long Fiona happened to notice me sitting alone at the bar and came straight over. At this point I was quite drunk. To be truthful, despite my consumption I was keenly aware that Fiona had consumed her fair share as well. Sober, I would have shared a friendly exchange and made sure that she found her way back to her table, back to the group of friends her own age.

If I had acted on what I knew to be the proper move, this story would not be worth telling. But whether it was the booze or the throbbing erection clouding my conscience, I couldn't find a way to resist the temptation. And so, as my young perky waitress engaged in shameless flirtation I flirted right back with all of the loaded sexual innuendo of a common player looking for a cheap bar pick up.

When I announced that I was heading out for a quick smoke a part of me hoped she would follow despite knowing that she was not a smoker. Without hesitation, Fiona grabbed my hand and together we stumbled out the back door. Any pretense of resisting the temptation of this young beauty had been long ago abandoned and when she manoeuvered us between two cars at the back of the lot I was definitely all in.

To this day and despite the scotch, I can still imagine that feeling of pushing my hand into her jeans. I didn't bother to pop the button or undue the zipper. I just had to discover her. I had to explore that tight young body. She was wearing panties but that did nothing to slow my advance. I pushed further against the tightness of her jeans cupping my hand around the matted curve of her pubic bone. Her slippery clit was noticeably erect. I curled my middle finger which slid effortlessly between her soaking pussy lips.

The moment I entered Fiona I felt her hips lower forcing my digit as deeply as I could reach. I still remember the warmth and texture of her insides and the desperate clench of her vaginal walls. Another finger joined in my invasion as we gripped each other tightly and continued to makeout with the passion of youthful lovers. I savoured her wonderous flavour as I paused to smell and lick my fingers while she watched. The lust of her expression mirrored my own.

What I thought was to happen next (in my mind), would have made for an amazing sexual tale. Unfortunately, just as I had gone back down to resume my fingering of this 19 year old sex pot the back door swung open and the chorus of voices alerted Fiona to the presence of her friends on their way home for the night. With a gentle pull at my wrist and a kind kiss on the cheek Fiona was off and my chance to ravish this freckle faced beauty came to an abrupt end.

For the sake of getting to the real story I won't waste time describing my conflicting emotions or the conversation that followed several days later. Suffice it to say that we agreed that a fun drunken night should be left at just that -- no harm, no foul. I think we both believed that would be it. I certainly did and I meant it. Great girl with a great personality and I continued to look forward to the brief moments we shared at lunch. But humans are human and alcohol has its known effects and she had become the regular inspiration of my always frequent masturbation sessions. In fact, I'd even begun to fantasize about her while I had sex with others.

So yeah, I eventually fucked Fiona. It wasn't often and usually nothing more than a drunken roll in some place of convenience. It was never a regular thing and often years between meetings but those daliances as vanilla as they now seem, remain some of my goto jerkoff fantasies when I really need to cum hard.

Fast forward 20 years and I'm climbing into an octopus costume with this girl I had fantasized about on so many countless occasions. Fiona had called out of the blue and as it happened, I was without plans that night. Truthfully, I likely would have cancelled whatever I was doing the minute I heard her voice. Unlike the distant past when we had last met up, I was now armed with a world of experience and had often fantasized about introducing Fiona to some sexual experiences I was pretty confident she had not yet discovered.

The octopus costume obviously had eight tentacles which were filled with our arms and legs. With Fiona in front and I in the back, the costume offered just the amount of room to fit the two of us pressed tightly together. Though our limbs were obviously stuffed into separate compartments there was no material separating the rest of our bodies. The head of the beast was made of a rigid material and allowed either of us to speak through a dark mesh opening. Knowing her as I do now, I wonder if the story of a needing a last minute replacement for her two person octopus was pure bullshit. Knowing her as I now do, I wonder if she purposely sewed the costume on the small side to force us so closely together.

Admittedly cheeky, I suggested that the costume would be far too hot for us to be fully clothed and Fiona agreed without hesitation. So with me in my boxer shorts and and she in just bra and panties, we trapsed about her apartment trying to perfect our ability to walk in unison. Unsurprisingly, the minute we climbed into the octo-suit my hard cock was pressed firmly against the cheeks of Fiona's ass. We hadn't even left her apartment and my hands had snuck around inside the costume to tweak her hardened nipples as I made sure that my ever present erection made clear my desires for her. It sounds like so many Halloween costume stories I know, but this is exactly how it happened and I promised Fiona that I would retell this adventure with every element of the tale completely unvarnished.

I was so incredibly horny at that moment that I proposed skipping the party all together and proceeding immediately to bed. With every thrust of her ass back into my groin I knew that Fiona equally shared my passion. My hands took advantage of the fact that Fiona was in no position to escape. Like an overly eager teenager I tried every move to persuade her to ditch the costume and get right to the fucking.

Fiona had persuaded me to hold off until after the party and though I suggested I would, I had neither the ability nor the intention of keeping my hands to myself. I was looking forward to being trapped together in a Halloween costume that practically begged me to molest her for the entire night. I fully intended to do as I wished with her body and indeed I did just that. And while I did not hesitate to roam and explore at will, I did so with the express intent of teasing and frustrating Fiona for as long as she could stand it.

The reality is that much of what I did with and to her that night would on its own make for an intensely erotic story but unbeknownst to Fiona I was about to expose her to a sexual experience that she would never have seen coming. However, in order to get to the big reveal I've decided to include the lead up to the real highlight of the evening.

As we cabbed to the party it occurred to me that we could have the benefit of total anonymity. Though the crowd was mostly comprised of coworkers from Fiona's business firm none would be able to identify us in the octopus costume. I suggested and Fiona agreed that we should try to get through the night without anyone knowing who we were. Fiona agreed and suggested that between muffling her voice and the noise of the loud crowd, they just might be able to pull it off.

Upon entering the crowded Halloween party I was certain that we could blend in as complete strangers. The music was way too loud and most of the crowd was well on the way to a good and proper drunkfest. Many of the costumes were incredibly elaborate and few of the partygoers were easy to identify according to Fiona. Our first stop was directly to the free bar where we asked for drinks with staws which was the only way we could drink without removing the octopus head and revealing our identity.

As soon as we had grabbed some drinks and shuffled our way over to a corner to people watch, I began taking advantage of the situation Fiona had created. My 'arm tentacles' were left to hang at our sides so that my hands were free to roam inside the costume. We weren't in the house five minutes before I fished my cock out the seam of my boxers and began dry humping Fiona's panty covered ass. Though I knew that Fiona was every bit as horny as I was, it was equally clear that she was nervous about anyone being able to figure out what was really going on inside the tentacled sea beast. But Fiona couldn't stop my insistent thrusting and I wasn't about to let her in any event. Likely in an attempt to control the situation Fiona started moving about the room but with my hands firmly on her hips I was able to continue rubbing my cock up against her ass in coordinated rhythm with our steps. The more she tried to tone it down, the more urgent I became.

Fiona's next move was to walk up to a random partygoer who was dressed as a naughty nurse. While the two women engaged in small talk my hands slid up under her bra and began to massage her breasts and perky nipples. From within the confines of the costume I could sense Fiona's nervous excitement and both of us were now keenly aware that she was completely at my mercy.

Angling my cock lower I pushed the head of my cock with as much force as I could. In my mind, either the thin silk of her panties would tear or it would be pushed inside her by a desparate cock that was not to be denied.

"Hey, careful where you're pointing that thing!"

I didn't respond nor did I relent. I could feel the tip of my cock pressed hard against the tight ring of her anus. Backdoor sex was not something Fiona and I had tried or ever discussed -- yet, but without question that moment had to have made it clear that if given the opportunity, I was very much for it.

With her only measure of protection being the thin fabric or her panties Fiona was completely helpless to frustrate my advances. Precum had begun to pour from the head of my cock providing a lubricant to my thrusts. Between the two of us, Fiona's panties were now dripping wet which made the protection of her panty barrier even more vulnerable.

Though I really wouldn't have fucked her ass for the first time in a crowded public setting such as this, I did manage to push the tip of my cock between the clenched ring of her anus enough to make her think about the act. For minutes I would just hold in place with full force and threatening that if she didn't continue to clench I would push the whole head inside her. Then, when someone came by to make small talk I would back off momentarily leaving her to wonder when the next assault on her ass would begin, which it inevitably did.

Several more rounds of drinks coupled with a number of shots and both Fiona and I were both well on our way to a great buzz. Not many words were spoken between us but I was confident that she was just as horny as I. At one point she suggested finding a room or even somewhere out back to get on with the deed but I was having way too much fun manipulating a situation that she had created even though she could not have possibly anticipated all that she was to experience that special Halloween night.

To claim that I had some mastery of patience would be completely untrue. I would have loved nothing more than to lock ourselves in a room and ravish each others' bodies all night long but this was to be a special night on so many levels. And despite my almost unbearable need to cum I kept reminding myself to follow through with the plan that had begun to develop in my mind from the very moment Fiona had called to invite me to spend an evening together trapped in an octopus costume.

Unable to wait any longer, I decided it was time to move plans to the next step. Manoeuvering us into the middle of the main room and surrounded by others I asked Fiona to hold my drink. This had the effect of immobilizing the use of her arms while mine snaked into the costume to lower her panties to mid-thigh. Before Fiona could respond to my latest move I pressed my cock firm between the cheeks of her very slick ass. The head of my cock was knocking at the back door but in truth, this was nothing but a threatening tease. I felt her ass clench hard but it didn't matter because that's not where I was heading. I reached down and angled my cock lower. A moment to confirm I was on target and one hard thrust had me balls deep in Fiona's tight wet pussy.

Lest it appear as though I was taking advantage of Fiona let me be clear, I was. Having said this, Fiona was very much a willing participant despite having next to zero control over what was happening between us. Whether the alcohol had lowered her inhibitions or Fiona just simply couldn't continue to deny her own needs, it became obvious that her discomfort with sex in this public setting had been all but abandoned. As my hands groped her breasts and rubbed her rigid clitoris, Fiona's hips began to thrust back forcing my cock to the very bottom of her pussy.

As it became obvious just how desperate Fiona was for relief I knew it was time to increase her sexual frustration. By design, I needed to have her craving an orgasm with such need that she would continue to let me direct our engagement in anyway I desired. To be certain, both of us desired much more and for certain, I was intent that we would both ultimately realize our needs. But it was going to be at my time of choosing, in the manner I decided and only once my full plan had played out.

I managed to deny myself and hold off for almost three full hours. During that time I had used my cock and my hands not for myself but to tease and torment Fiona to the extreme. Each time I felt her responding as I rubbed her clit furiously, I would pause to deny her climax. As her thrusts became more urgent than my own, I would pull back leaving only the head of my cock between the blonde matted curls of her lips.