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Disclaimer: All sexual encounters described are between people 18 years and older.

*****

Somewhat annoyingly my mobile phone buzzed again; another text message from Michelle. That made four in the last hour and it was not even midday yet. As much as I loved being with her, the knowledge of her leaving for a holiday for three weeks and these continuous messages were staring to be more of a frustration than an enjoyment.

“Still waiting to board the plane. Another fifteen minutes should do it. My husband has gone for a walk…he hates waiting, lol. Ray, I have to confess, after last Friday and the unbelievable feeling of you filling my arse I have been wondering what it might be like to do the same to you? While I am away, and only if you are willing (I know you’re able, lol), could you investigate a way of me experiencing what it is like to be the penetrator rather than the penetrated? An unusual request but we have an unusual relationship. Best git…they are calling our flight. Love you, M.”

It took me a number of reads to properly comprehend what she was asking. I laughed and shook my head in disbelief at her request but I was more than willing to do it, especially with her and for her. I chuckled to myself again, as I sat in my office and thumbed a reply.

“Consider it done and can’t wait. Love U2, R.” I just wished I could have been a fly on the wall to see her expression when she read it.

The prospect of fulfilling her request was thrilling to say the least. Many years earlier I had embarked on a quest to explore myself anally but had only rarely had the guts to share the exploration with anyone else. But more on that soon.

To date, I have had good experiences with online shopping but I had to admit, this was the most outrageous. However, all things considered, the consequences of purchasing such an item far outweighed any reservations I may have had. As small as they were.

Good old Google provided the usual swamp of sex video results interspersed with relevant sex toy providers. I clicked on a few sites and browsed and made notes on a scrap of paper (old school never fails) of brands and designs and prices. The variety of options was quite illuminating to say the least but gradually I started to narrow down the alternatives. Initially I had thought of a strap on dildo that literally strapped on but as my research knowledge grew, I soon discovered there were a number of alternatives that dispensed with an actual harness. From the outset, I knew I wanted something that was going to fulfil Michelle’s request; to be able to penetrate my arse. However, I also desired a device that would stimulate her at the same time…mutual satisfaction seemed a good way to go in my eyes. I wanted to replicate the sex act with as much realism as possible, i.e. give her as complete a feeling of building toward orgasm as I would have fucking her.

Bingo! I found one that fitted Michelle’s brief (not briefs…well not yet) as well as my own. The product description read: ‘Experience the extraordinary closeness with this 7 inch strapless strap on. Suitable for vaginal and anal use, one partner inserts the contoured bulbed end into their body (Michelle), holding the realistic dildo in place and leaving it ready to penetrate their lover. The attached dildo has seven (7) inches of insertable length, with the silicone offering a flesh-like texture and a great feel during use. During play, both partners are stimulated with the toy’s soft, flexible feel and realistic shape and it removes the need for a fussy harness or wires, allowing you and your partner to enjoy simultaneous stimulation.’

A win – win I think you could call it.

At $124.95 (AUD) for the dildo, plus another eight bucks for the water based lube (free delivery was part of the deal) the investment was a small price to pay for what I knew would be an amazing experience for and with Michelle during our up coming three days and two nights alone, together; but that was not until after she returned from being away on her trip. I quickly dismissed the thoughts of her being away and continued to the check out to finalise my purchase. It would take two to three work days to be delivered.

I was something like the proverbial cat on a hot tin roof following the order placement. On the day it arrived I could not get inside quick enough to have a look see. I tore off the postage wrapping, stripped off the plastic shrink-wrap and then slowed myself to carefully open the cardboard box it came in. As I did so, the lube dropped to the floor from the corner of the box. Thankfully the plastic bottle only bounced and did not break open. Finally I saw the new weapon of anal destruction and it was every bit as good to look at as it had on screen. In fact, I thought it looked better…slightly longer and thicker than I had expected for both insertable ends.

“That bodes well.” I said to myself as I took the ‘strapless strap on’ (those were the marketing words displayed on the ataköy anal yapan escort side of the box) out and held it in my hand. It was lighter than I had envisaged which also meant Michelle would have greater control over the way she used the device rather than having to worry about a heavier object slipping. I was well pleased with my purchase but it still needed to pass one last hurdle; a private workout with the purchaser. Let’s face it, I could not give it to my lover without first trying it for myself, now could I?

I had no qualms about fucking myself anally with a dildo of this size as I was well acquainted with such, albeit not for a good many years. The personal exploration of my body really started just after I turned eighteen. A few of us ‘guys’ from high school (we were in our last year) took a day off and we congregated at one guys places to pass the time of day playing cards and drinking beer. By mid afternoon, we were all as drunk as and a number of them had passed out. A few had gone off home and a close friend (at the time anyway) and I kind of got into some sort of deep and meaningful conversation. The booze took control and that was when I had my one and only gay experience. I tried to get his hard cock into my arse, without lube I might add (that would account for the lack of success) and it hurt. However, it did peak my curiosity as to what it would feel like to have something invade that part of my body.

At that time in my life I was a skinny, gangly sort of kid. I was extremely short on confidence, especially with girls, but even with male friends…I did not know who I was, what I was supposed to be; a typical lost sole as I now look back. At the time of that man to man episode, I deliberately let it happen, despite feeling unsure, solely because here was someone taking an interest in ME, actually wanting me sexually…I was still a virgin.

I started high school in the early seventies, and during the January summer holidays, before school started, I had met this wonderful girl at Brighton Baths in Sydney. We hung out for what was an amazing four weeks in January. We talked our heads off and laughed profusely, I was on cloud nine. But, there is always a but, I never kissed her or held her hand…nothing. Why I hear you ask? I was shit scared that if I made a move like that she would take off, run for the hills. I still labour similar feelings even today for time to time in a variety of circumstances but usually sexual. I lack the confidence to pounce, for want of a better way to put it. That fear of taking the first step haunted me through out my high school years but none more so than this first one. I can’t even remember her name but I vaguely remember she had long auburn hair, big brown eyes and seemed to enjoy my company. Suffice to say, once school started we lost touch and she moved away, literally, I think.

I never had a real girl friend during the next six years of high school but I did have a lot of fantasy targets. In particular Jenny. Not only was she the centre of my sexual fantasises but, as I look back, I did have a crush on her. She was about the same age as myself, somewhat buxom even allowing for her teenage years, long dirty blonde hair, deep blue eyes and full, sensual lips. I did get to kiss her passionately a number of times, usually after walking her home from the local watering hole…good old Dutch courage. She had a boyfriend and he was a real arsehole and treated her quite badly. Most of us who knew her could not believe she stuck with him for so long.

As I said, as a consequence of my gay sex one-off, it started me on a path to explore myself anally and fantasise about Jenny as I fucked my arse. I remember visualising that whatever I was using to my arse was actually my cock fucking its way up inside Jenny and she was continually building toward one huge orgasm after huge orgasm. During this period, a married guy in his late twenties (who was also our next door neighbour) showed me his collection of pornographic magazines. I would even sneak into their place while they were at work and steal one or two copies and add them to an ever increasing pile of material I kept hidden in the back shed.

At least once a week, I would get home around midday from school, go and collect my porno pile and spend the next couple of hours in the bathroom. Our shower was over the bath, so I would place a chair at one end where I would place my mags and squat in the bath and rest my arms over the back of the bath while I flicked through each magazine looking for images in all states of dress or undress and sexy positions, that reminded me of Jenny. I would fill an empty bottle (a large coke or shampoo etc) with lukewarm water, smear vaseline onto the opening and around and inside my anal opening, and slowly squeeze the water up inside my arse. The feel and adrenaline rush I got as I felt the water slowly fill my anus was amazing. All of a sudden I would feel a soft ataköy bdsm escort thump in my gut as I reached capacity which I then tried to hold for as long as possible until I just had to expel the fluid and all that came with it. I repeated these enemas numerous times until I was satisfied I was clean, only then would I start to fuck myself with whatever I had available; it varied from cut of broom handles, small Lebanese cucumbers, slender zucchinis and the like. But the rush of the water as it filled me was a highlight.

Once cleansed, I would start fucking myself by squatting over the phallic object and bouncing my hips to impale my arse as I stroked my cock in tandem. Balanced thus, I would start to flick through my hoard of porn mags and select Jenny-like images and place them on the floor. As I stroked my cock the pressure would increase along my back passage and on my internal glands to a point where it would sometimes reach an exquisite pain that I would only barely prevent from falling over into an all out orgasm. Time and time again I would build to the brink and stop myself, my breath deepening and rasping as I picked out more and more Jenny photos until I had found at least one per magazine. It was a simple task once I had completed my search to finally bring myself off and explode in a powerful burst of anal stimulated lust. There were times when I was so horny I would even curl myself up onto my back and would blast my load over my own face, fantasising I was coming all over Jenny or that she was coming all over me.

That was the start of my anal exploitive orgasms which lasted until I was in my mid thirties. After I left high school, the Jenny fixation waned and I turned my attention to any number of looks instead of limiting my fantasies to one particular person.

During a raid on the guy next door’s porn supply one day, I happened across a sex contact newspaper. Call it kismet, but I was drawn to one advertisement in particular, labelled ‘sophisticated lady’. I wrote a reply, this was before internet and email remember, and after about a week her answer arrived and we made arrangements to meet. She was tall, blonde and buxom, and into ‘most things these pages’ as the saying went. I saw her off and on over a period of a year, slowly building a rapport, as well as my personal confidence, in sexual matters. On one occasion, I asked her about enemas and she proudly showed me how she would go about administering it all all that went with it, all she required was for me to tell, in advance, when I desired her assistance. I was deeply curious and driven by personal desire to try so we arranged to meet the following week, when we would have a large chunk of time to fully explore this fantasy of mine, as she called it. Sharon also asked that I do some initial cleansing at home, if possible, just to clear the majority of any waste before landing on her door step.

When I arrived, Sharon was dressed in knee length black boots and a black dog collar and nothing else. She had pieced nipples that stood proudly out from her well rounded breasts. Her navel was also pierced with a small jewellery piece and her pussy was bare.

“All in the name of setting the scene.” She commented as I complimented her outfit, or lack of it.

She directed me to lie down on the massage type table she had set up in a darkened room. She had soft music playing, once again, as part of the mood building process and to help me relax.

“All the better for you to take more of this,” she teased as she showed me the bag full of a warm fluid…two (2) litres in all.

“Shit, is that all for me?” I gulped.

“No shit…well that is the hope after you expel this.” She laughed and helped me place my legs in the stirrups on either side of the bench.

“Can you hold this?” She asked as she walked up along the side of the massage table.

‘Sure.” I replied but unaware of what it was she was talking about.

She took my hand and placed a large black vibrator into my palm. I closed my hand around it firmly, as she instructed.

“Now before I can start I need your help.”

“Anything.” I said, a little warily.

Sharon smiled gently and climbed up onto the table. She swung her thigh up over my shoulder and took up a position with my face directly under her pussy and between her legs as she sat down on my face.

“I need to come.” She said sternly. “It will help me concentrate on fucking your arse. The thought of all this has had me as horny as all get out all morning.”

Her revelation, while surprising, and considering she had her dripping snatch centimetres from my mouth, had me in a position where I could not say no. Immediately I began to tongue her crotch and I loved her sweet taste as I dipped my tongue deep inside.

“Eat me Ray, lick my pussy. ohhh, fuck yes…there, right there,” she directed as I sucked on her massive clit. I took it into my mouth as if it was a small ataköy elit escort cock drawing deep and loud groans from Sharon as I looked up to see her twisting and pulling at her nipples.

“Oh fuck, that feels good,” she hissed as I probed her deeply with my tongue. I dipped the fingers of my free hand into her wet pussy, coating them with her own juices before I spread her cheeks and stuck them in her hot arse. That drew a loud groan from Sharon as she raised up and began pushing her arse back onto my fingers.

I had been sucking on her clit for several minutes, enjoying the taste of her succulent opening when she Maggie moaned heavily, “Oh fuck, I’m near cumming.”

Quickly Sharon jumped off the table and squatted over the vibrator I held in my hand. She clamped her hand around mine as she pushed the thick plastic rod deep inside herself and bounced feverishly. Within seconds her body literally bucked and jerked, like she was doing an imitation dance of Peter Garret. She plunged the vibrator hard into herself repeatedly until finally she dropped my hand and sagged against my chest. I caressed her back as she gradually gathered her senses. She kissed me warmly and thanked me for my help. I laughed a thank you as she made her way back to the foot of the table.

Sharon proceeded explain the process in detail as she gently rubbed another vibrator against my arse and scrotum. She showed me the enema nozzle she had chosen for me, a ribbed tan coloured one, and after she fitted it to the hose, she eased it into my arse. My cock laid twitching on my hip, still standing to attention after her orgasmic warm up.

“I’ll get to this later.” She whispered, patting my rod, as she inserted the hose and slowly opened the valve. The water trickled in, the warmth slowly built in my back passage. She closed it and told me to relax and let the water find its way. While we waited, she gently caressed my cock and softly blew streams of warm breath across my tightened flesh. She stopped just as my penis started to respond fully to her ministrations.

“Don’t want to soil the fun by going too far too soon.” She cooed.

She reopened the valve and gradually, over about half and hour, drained more of the water into me, interspersed with more cock play. I looked and saw, to my surprise, that almost three quarters of the liquid was no longer in the bag but inside me. I was beginning to feel a fullness that tantalised and excited without being overly sexual. As Sharon closed the valve I looked along my body and noticed my tummy was stating to rise as the level of water increased in my rectum and intestinal plumbing. After an hour, Sharon congratulated me; I had taken the bag in totality on my first attempt.

“Not many can achieve that. I am impressed.” She smiled. “Now, just relax and try to resist the urge of your body to expel the water. Try and hold it as long as you can. It will get harder to hold, but try to stop it.”

Her insistence was driven more by her not wanting to clean up a huge mess I assumed. As I laid on the bench, she gently massaged my chest with her rounded breasts and tenderly kissed my mouth. Every time I went to raise my hands to her, she pushed them down and told me to relax and let her be my guide. I closed my eyes, and felt her hard pierced nipples graze across my own, the pressure in my flooded back passage slowly built to a point where I was afraid I would not be able to walk. I felt bloated and heavy, like a blow up punching bag in the form of a penguin.

I lasted another ten minutes, I think but I could not sure. Sharon helped me to slowly roll sidewards off the bench and get to the bathroom which was only a few feet away. Man, what a relief when I finally sat over the bowl and expelled…the sudden rush of fluid leaving my body was one of the most wonderful feelings I had experienced in a long time. I felt heavy one minute then as light as a feather. I sighed deeply with relief that I had made it.

“Well done.” Sharon complimented. “Now, if you want to proceed, resume the position?”

I felt so dreamy at the relief of expelling the two litres of water that I robotically did as she suggested. Once my legs were back in the stirrups Sharon smeared a copious quantity of KY gel around and inside my anal cavity. I had not taken any notice of her as I walked out of the bathroom, I was too consumed with my own feeling of relief and the sudden feeling of weight lose.

“I am going to use this.” She told me, slapping a thick strap on cock against my thighs.

“Oh, okay.” I replied gingerly.

“Don’t worry. You are going to enjoy this, I know! Besides, I have a vibrator inside me and it is making me want to come badly.”

I nodded and mumbled some sort of reply which went unanswered. She stood at the end of the bench, the thick pink cock jutted out from the black harness around her hips. She grabbed the cock and pressed the thick head against my anus and used her hips to increase the pressure.

“Resistance is futile.” Was all I could hear in my head accompanied by flashes of Vogons from the Hitchhikers Guide.

I felt her hand grasp the rubber shaft and reposition it slightly and then, pop, she entered me. I could feel the replica veins move past my sphincter as she slowly pushed the plastic cock fully inside.

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