When it Finally Goes Right

Most I'm sure would agree that whenever you try something for the first time, sexual or otherwise, it can feel different or even uncomfortable and you are faced with two choices: either give up or continue on learning as you go until it all falls into place.

Anna and I decided to give pegging a try, if you don't know what this is look it up or just keep reading, and while this was at my suggestion I have had the good fortune to be blessed with a partner who is both broad minded and happy to experiment with new things.

After a bit of research on the subject and the acquisition of what we thought were suitable toys we started experimenting. As expected it was a little uncomfortable and uncoordinated at first but nonetheless there were some very pleasurable moments that convinced us to keep trying.

In these early attempts there had been no domination play no real acknowledgement of the whole role reversal thing we were just trying to work it all out. Then something seemed to click and it went from clumsy and awkward to ecstatically hot. This is not about the first time we tried it but it is about the first time it seemed to go oh so right.

The image of a woman wearing a strapon is anything but subtle, it makes what is about to happen very very clear, and while it doesn't in anyway change their physical characteristics it makes them seem somehow taller and undeniably more confident. While some may consider the appearance confronting, intimidating or even fearful it to me appears extremely sexual.

Anna works most evenings and doesn't get home until around midnight a time when she will often find that I'm still awake, if somewhat tired. I try to wait up for her simply to re-establish contact after being apart for nearly 24 hours. This particular evening I was sitting in bed with my iPad, reading Quora as it happens. On entering the room she made a beeline for me taking up a position sitting on the side of the bed we embraced and kissed and asked each other how our respective days had been. A not unusual occurrence to be sure.

As she stood up I slid down the bed to get into position for something I genuinely look forward to, even after being together for thirty five years, watching her get undressed. It is for me one of my life's simple pleasures and is the 'prequel' to another, drifting off to sleep pressed firmly against her bare skin. This evening however was different. Before returning to her side of the bed she reached into our 'toy draw' and removed a white, mesh drawstring bag and casually dropped it on the foot of our bed before continuing on to dispose of the days clothing.

As I stared at the bag I could see through the mesh the unmistakable rich blue colour of our feeldoe. Glancing back at my now rapidly disrobing wife she said nothing but her playful smile told me everything I needed to know. My night was taking a sudden, and unexpected, turn and I was now much more awake than I had been mere seconds before.

With her final piece of clothing dropped to the floor she kicked the pile of now discarded garments to one side before returning to the end of the bed and the previously deposited bag. After releasing the string on the neck of the bag she upturned it allowing it's contents to fall onto our bed the weight of the feeldoe causing it to bounce ever so slightly as it landed.

Reaching down she picked up the harness, a utilitarian affair of leather, steel and nylon, shaking out the bundle of straps before holding it in front of her thighs to orient it in the same manner as one would for an ordinary pair of shorts. Then bending forward she guided one foot and then the other through the harnesses straps before looking squarely at me as she slowly and deliberately brought the harness up her legs and over her hips tightening the top straps just enough to prevent it from falling back to the floor.

At this point I was completely mesmerised by what was unfolding before my eyes. If ever a woman wanted her partner's complete and undivided attention this was it and as I watched on she reached down for the remaining two items the feeldoe and a bottle of lubricant. A quick squirt from the lubricant's bottle saw a small amount of it's contents deposited on the feeldoe's bulb before with a snap of its cap it was returned to its place on the bed. With her free hand she started to spread the clear gel across the entire bulb before sliding the shaft of the feeldoe through the steel ring at the centre of the harness.

She paused briefly and looked up at me probably to make sure she still had my attention, I can assure you she certainly did, before looking down again and moving the harness to the side allowing me a very clear view of the feeldoe's bulb as it slid up and disappeared from view inside of her. The next few moments were spent carefully adjusting the harness straps to make sure that everything was centred followed by a final coordinated tug on the upper and lower straps to keep it all firmly in place.

Of course by this time my anticipation levels are through the roof and she's just standing there looking at me while I'm expecting her to come towards me at any moment. Then she turns and walks away to the bathroom. I must admit I'm a little confused at this point until she returned with a towel which she tossed at me. I knew what was expected so I sat up, laid the towel across the bed and resumed my former position waiting ever more expectantly for her next move.

Then with an impish smile on her face she stepped towards me while dropping her left arm and, starting at my ankle, running her fingers slowly up the inside of my leg before lightly brushing over the head of my cock then once again turning and inexplicably heading back to the bathroom and commencing to brush her hair.

Watching my wife's reflection in the mirror as she brushed her hair has always been a source of viewing pleasure for me with her upraised arms lifting her breasts which move seductively with each pass of the brush through her brown shoulder length hair. While this was a sight I'd witnessed countless times before it was still as captivating as the first time I experienced it. This time perhaps more so with the straps of the harness pressing against the cheeks of her arse as they crossed diagonally from her hips before disappearing between her thighs.

All throughout this she kept her gaze fixed on my reflection this left no doubt in my mind that I was being toyed with. Something that was further confirmed when she returned the hair brush to its place on the vanity and turned and walked back towards me stopping to pick up her earlier discarded clothes and placing them in the laundry basket. Laying there watching as she completed more mundane tasks I became almost hypnotised by the feeldoe as it swayed rhythmically with each step she took. The intensity of the visuals were not lost on her either as she occasionally glanced in my direction as if gauging my readiness by how hard my cock was getting.

While I was fully conscious of the teasing I was being subjected to I was more than happy to lay quietly knowing the time when I would play my part in this was surely not that far off.

Then almost without warning she stopped, once more positioned at the end of the bed and picked up the bottle of lubricant from its resting place. With her gaze fixed on the feeldoe and a hand cupped under it to steady it she carefully ran a line of the crystal clear lubricant from the tip of the feeldoe along the top of its shaft stopping just short of the harness. The sudden snap of the bottle cap as it was closed pierced the stillness of the moment before it was once more dropped to the bed.

Now she was staring directly at me the impish smile was gone replaced with look that said your body's mine and I'm going to do you. Without taking her eyes off me she grabbed the shaft of the feeldoe close to the harness with her right hand. Then with an overhand grip she started working the lubricant around the shaft with a twisting forwards and backwards movement she had often used on me. When she reached the head of the shaft she ran the palm of her hand across its tip coating it with lube before continuing to work back towards the harness.

For a brief moment she stood still and I could see the feeldoe now looking as though it had just been polished, the light glistening off of its now well coated surface. Then without breaking her gaze leant forward placing her right knee on the bed and in a voice that was both sensual and commanding said simply "Roll over.".

I rolled over laying flat on my stomach and without the need for further instruction spread my legs awaiting her approach. As I laid there I could feel her getting into position between my legs followed by her placing a hand on the back of each of my legs and slowly moving them up towards my arse. Once there she started massaging and squeezing the cheeks of my arse.

I now found myself in a unique situation, on the one hand the anticipation of what was to happen was intense while Anna's hands working on my arse was truly pleasurable which resulted in several soft moans of pleasure escaping from my lips. So engrossed was I by these mixed feelings that I didn't notice that Anna had removed her hand from my right butt cheek but I certainly noticed the sting of it returning there palm first and hard. This 'attention getter' was followed by a request delivered in the same sensual and commanding tone she had used earlier. "Get your arse up."

As I raised myself, first one leg and then the other, Anna kept her hand in the very spot where it had landed on my arse. It was almost as if she was trying to keep the intensity of the slap from escaping. Once I'd positioned my arse at what I thought was a good height Anna started to slide her hand across towards the centre then down along my crack pressing with her middle finger as hard as she could causinging me to flinch slightly as it crossed my hole.

On reaching my balls she paused briefly to give them a gentle squeeze before her hand slid further down wrapping her fingers around my cock which was dangling between my legs. I felt her pull on it, almost as if she was just holding onto it and allowing it to take the weight of her arm. Then she began to squeeze again and this time there was nothing gentle about it. As her grip on my cock tightened in a soft voice she said "I love how hard I've gotten you without even touching you but I guess this means it's too late to get the cage on your cock now." Being worked up and constrained would not have been a new experience for me but I was certainly glad it was not the case this evening.

Her hand released its vice like grip on my cock and within mere moments I heard the familiar snap of the lube bottle being closed. Then I felt the cool sensation of a finger drawing circles of lube around my arsehole this in itself is a sensation like no other but then that same finger in a single movement pushed its way in then began probing its way around spreading the lubricant as it went before retreating.

I soon felt what I knew to be the feeldoe's tip brushing against random places on my arse as it swung in its harness before coming to rest at the top of my crack telling me that Anna was getting herself into position. She then placed her hands on my hips pulling my arse higher. She stopped pulling me up, I waited expectantly then without warning my left cheek suffered the same type of stinging blow that had struck my right cheek a few moments earlier. "Spread your cheeks" she said and I dutifully reached back with both arms placing a hand on either cheek and separated them as ordered.

There I was, face down, arse in the air and cheeks spread. It doesn't get much more prone than this. Then I realise the feeldoe's movements are no longer random in fact it's not moving at all. I can now feel its tip centred on it's target and exerting an ever so slight pressure.

In the following moments my anticipation continued to grow, seconds seemed like minutes as I waited in silence. "You're ready for this." Anna said in a low sensual voice. I was ready, I'd been waiting for this since she dropped it on the bed. I started my response of "Oh yeah I'm ready" but it was turned into a long deep moan as I felt the head as it pushed its way into me sending a shock wave throughout my body. The sensations didn't stop there and neither did Anna.

Unlike our earlier times she didn't stop or even slowdown but continued to push her way in sending incredible sensations throughout my body. It seemed that as she pushed deeper into me different parts of my body felt it. First in my balls, then my cock started to throb followed by a feeling deep in the pit of my stomach before engulfing the rest of my body in wave after wave of intense feelings.

These feelings grew to such a level that as I felt the leather of Anna's harness against the cheeks of my arse I collapsed onto the bed. As I lay there collecting my thoughts I felt Anna, who was now laying on top of me with the harness still pressed against me, kissing me in a line up my left shoulder before gently biting me. I then felt her warm breath on my neck as she whispered into my ear "I'm sorry but when I said You're ready for this.'' what made you think I was asking a question?"

After pausing for a moment she pushed harder against me, forcing the feeldoe into me as far as it was going to go holding it there briefly soliciting and involuntary moan from me before relaxing and slowly pulling back.

For the next few moments I lay there face down, arms by my side and palms facing up as Anna moved slowly and methodically in and out of me. Each time she withdrew she would stop with just the head of the feeldoe remains in me, pausing for a moment before once more sliding back into me each time sending a fresh wave of intense feelings throughout my body and ending each stroke by pushing as hard as she could manage into me.

After a few minutes of Anna's slow determined movements my mind was racing. I had no idea what it was I was feeling. Was it pleasure, was it pain or was it some kind of sensory overload? I didn't have the presence of mind to work that out all I knew was that I wanted it and I didn't want her to stop.

Then she did.

Once again I felt her warm breath on the back of my neck as she placed as much of her weight as she could squarely on the feeldoe. "It sounded like you were enjoying that weren't you?" All I could muster in response was a low moaning "uh huh". "Well" she replied "my plan for this evening was to pound your arse not worship it so unless you want a few more ripe red handprints as souvenirs of this evening get back up now!"

I pushed myself back up lifting Anna as I went until I was back on all fours with now Anna kneeling behind me and the feeldoe still firmly in me. I then felt a slap on my right hip followed closely by one on my left and without repositioning her hands Anna began to tighten her grip on my flesh. She then moved as before slowly pushing the feeldoe into me pushing herself into me as she pulled hard on my hips as if to ensure she'd reach 'maximum depth' before just as slowly withdrawing until only the head of the feeldoe remained in me.

After a short pause and without further warning she pulled me hard towards her while she thrust towards me driving the feeldoe rapidly into me stopping only when her harness slammed into my arse. She then tightened her grip on my hips before giving one more hard thrust, as if to prove her intentions, before slowly withdrawing once more. After a pause of mere moments she again thrust forward into me, this time withdrawing almost instantly before again slamming the feeldoe back into me.

In no time at all Anna had built up a rhythm and with this I found myself completely at her mercy. My mind was a haze of intense feelings from the sharpness of her fingernails as she maintained her vice like grip on my hips to the feeldoe as it repeatedly buried itself deep within me with feeling the leather and studs of her harness as it's forward motion was stopped by it's impact my arse. I had completely lost control and while I had managed to keep my arse in the air my arms had collapsed from under me and I was now in some contorted downward facing dog position as if I was a participant in some perverse yoga class.

Through all this I heard Anna's voice telling me repeatedly "Play with yourself". Truth is I couldn't, I was completely lost in an ocean of sensations that was flooding every inch of my being. I tried to comply with her request. I even managed to get a hand on my cock for a few strokes before it fell back to the bed almost as though paralyzed.

I'm still unsure as to how long Anna kept up her pace but as she began to slow she loosened her grip on my hips and then pulled me to one side causing us both to collapse onto the bed. As we laid there on our sides I could tell by her breathing she needed a break and as she reached around to grab my cock I felt her now damp skin on my back as she pressed against me the sweat telling me she'd worked hard. As we laid there my mind slowly began to clear and I could feel her squeezing my cock in unison with the feeldoe which she was now moving ever so slowly. While the movements were slow and gentle there seemed to be a reassurance that this was simply marking time, that things were not over yet.

"Do you have any idea how much of a turn on the sounds you make when I'm doing this to you are?" she said. The sounds I made were completely involuntary they just happened. "So you enjoyed that huh?" "Oh fuck yeah" was the only response I could manage. "There were times I wasn't sure if you were enjoying it I thought I may have been hurting you". "Oh yeah I was enjoying it" I replied.

For the next few moments we laid there in silence as Anna's breathing slowly returned to a normal rate while she continued slowly moving in and out of me. "Ready for more" she said in a hushed tone. "Hmmm yeah. That's if you're asking." I said. Her response of "I don't think I am." Was accompanied by her arching her back which once more drove the feeldoe as deep into me as it would go. Now with one hand on my hip and the other on my shoulder she again began slowly moving in and out of me.

I had now found myself on the receiving side of one of my favourite positions. This was a fact not lost on Anna as she quipped "I can see why you like doing me in this position." and she was right. It was an ideal position to wake her up with and now I was feeling it from the other side, or should that be the other end?

As with me when waking her up she started slow but soon was back to her earlier tenacious thrusting and I was soon again lost in a haze of intense feelings. This time there was no commands to play with myself instead Anna slid her hand off my hip and grabbed my cock but this seemed to throw her rhythm off so it she would return her hand to its previous position. After what was a few minutes, though I'm not quite sure, she slowed to a halt and said "You need to get on your back." Before sliding out of me.

I dutifully rolled onto my back placing a leg either side of Anna who was now sting on the bed with her legs spread. As she reached for a nearby pillow she said "Lift your arse up." Before sliding the pillow under my lower back. She then arched back briefly as she reached for the bottle of lube on the bed behind her. I was in the perfect position to enjoy, if only briefly, the visuals of her stretching backwards lifting her breasts up as their skin tightened. I then watched as she applied a fresh coating lube to the feeldoe before applying the excess to my cock with slow tight movements, ensuring it was still good and hard. With a final wipe of her hand on my chest to remove the last of the lube she inched herself towards me before stopping and reaching down placing a hand under each of my ankles.