Had to Improvise Ch. 02

Shocked at this new feeling, I held still and pondered how it all felt. Realizing that it was nothing short of fantastic I again focused in on this new pleasure. I pulled back slightly and then that newly familiar feeling of being pushed back returned. Again I circled the entrance, before tightening the arcs and increasing the pressure again until I pushed passed the entrance once more, this time a little more easily and a little deeper. Rather than pull back out this time I began to twist a little and work in and out first in extremely short strokes but then after each few strokes I would increase the depth of stroke, probing further and further inside eventually feeling a little jolt as each knuckle pushed its way inside the tight passage.

Finally I pressed up against something that had my eyes rolling back into my head as a flood of pleasure rushed through me. I had hit the mother-load of pleasure and wasn't about to stop. With my finger buried to the hilt I began to press, pet, stroke, circle and anything else I could think of to stimulate the newly discovered spot. I looked down and my cock was continually twitching and a steady stream of clear precum was oozing out onto my stomach.

Wave after wave of pleasure was coursing through my body at this point and it was all I could do to resist reaching down and frantically pumping my meat to bring about a quick climax. Instead, I steeled myself and kept probing, anxious to see how far I could take this. My heart was beating out of my chest as I continued to work my prostate, and then it happened...

My hips started to flex involuntarily and then thick, creamy white cum started pouring out without my ever having touched my steely rod. Not wanting the sensations to end I continued my assault on my prostate. The cum continue to surge onto my stomach. It was coming in gentler streams rather than the long shots that I was accustomed to but there wasn't any sign of them waning so I carried on. Eventually the orgasm and ejaculations subsided but I didn't feel the need to stop.

I wasn't immediately falling into the dreaded refractory period and I wasn't losing my erection so I continued what I was doing, only pausing long enough to push a second finger inside along with the first. Since I hadn't lost my lust I did something that I hadn't done since I sent that first email to Steve months before. In my hunger I began to use my unoccupied hand to scoop up the cream that coated my stomach and feed it to myself, devouring every drop that I could, savoring it on my tongue before swallowing it down.

Eventually there was nothing left to savor so naturally my attention started to go back to my still hard cock and the fingers resting against my prostate. I flexed the muscles in my hand, causing my fingers to stroke across my p-spot and once again all of my attention was on pleasuring myself from the inside out. And oh god was there plenty of pleasure to be had.

My nerves were still humming from the previous orgasm and it felt like the next one wasn't far off. It turns out I was wrong once again. I hung in that state, on the brink of orgasm, for what seemed like forever. I was in ecstasy but also anxious with anticipation of my climax. I started wondering if I was going to be able to pull off two in such short succession. I wanted to get everything out of the experience so I focused on all of the sensations that my fingers were bringing deep in my ass, trying new techniques but always returning to those that were most effective, those that sent the strongest pulses of pleasure up through my cock.

The closer I got the harder it became to resist taking my hand and stroking myself, quickly bringing myself to climax and freeing my seed. I gripped the sheets with my right hand while I probed myself with my left, determined to experience another prostate orgasm. I wanted that long, slow, steady release. My patience was rewarded and my manhood started to pulse and twitch freely, all of the sensations coming from within as my seed started pouring out onto my stomach again.

There was less volume the second time but not by much. The orgasm was just as strong though and by the time the climax came to an end I was spent. I slipped my fingers slowly from my ass and immediately missed having them there but at the same time I enjoyed the feeling of being open. Before long, that too was gone. Thoroughly exhausted I lightly traced my fingers across my stomach before sinking into the bed to relax and let my thoughts run free.

Once again, there was the immediate onrush of shame but not at the same level as when I pulled on that thong for the first time. I had come so far since then and after a few minutes of internal debate I was able to convince myself that there was nothing wrong with my interests. What I enjoy in the privacy of my own home is really nobody's business, and boy was I enjoying it! I realize that not only was I going to push aside the feelings of shame and guilt but I was actually going to seriously look into doing some more online shopping.

I went to the usual places that I searched for thongs and panties and began browsing through the complete lingerie selection. After a significant amount of time researching the different pieces and different styles I started to figure out not only what types of lingerie I liked best but also the specific looks that I was interested in. I wanted to start fairly simple, yet sexy so the items that I spent the most time looking at ended up being chemises but only those with a particular kind of fit.

I wanted them short enough to where they would come down just to the middle of my ass, leaving that enticing lower half exposed. Ideally the front would be a little bit longer so you could only barely see the bottom of the front of whatever panties I would be wearing. The materials had to be lace and soft mesh (not fishnet), sexy yet still leaving a bit to the imagination. That was about as far as I went on that first day. I discovered the first style that I liked and how I wanted it to fit but colors were still up for grabs and I didn't really focus a whole lot on other styles at that point. I knew what I like to see but I was getting a little overwhelmed.

Before completely signing off I went to a more racy site to see what they had to offer. Maybe that would steer me in a different direction for next time. I briefly went through the most popular items without filtering at all but what I ended up spending even more time looking at was something entirely different. I found myself following an ad for the Toys for Men section and was in awe of the huge selection. I felt myself falling deeper and deeper into a rabbit hole as I went from one item to the next, following the Recommended Items and Items Frequently Purchased Together with the one in front of me.

I didn't order any lingerie that day but I did end up spending well over $150 on a variety of other items. I had submitted an order containing some cleansing items for myself and for any toys, some anal lube and a set of butt plugs of varying sizes. I made sure to order plugs that had a low profile, curved base that would not only stay comfortably in place but could be discretely left in under my clothes so I could keep them in while I worked or did stuff around the house. And finally, I threw in a vibrating/pulsating prostate massager that came highly recommended. I figured I'd jump all the way in before my mind went to work and squashed the whole shopping spree altogether and possibly prevented me from shopping again anytime soon.

This all stemmed from those two mind-blowing orgasms that I had a short while before, helped along largely by the fingers that I had buried deep inside myself, massaging and milking my prostate. I couldn't wait to give all of my new purchases a whirl but I was sure that the rest of the week and the weekend were going to crawl along while I waited in anticipation of the upcoming delivery.

When I got the notification of a delivery from the ring doorbell I darted from my office to the front door, anxious to open it up and check out what was waiting inside. I tore the tape off and already had the box open by the time I made it back to the bedroom. My cock was straining against the lace of my thong as my heart pounded in my chest in excitement. As I approached the foot of the bed I unbuttoned my jeans and let them fall to the floor as I set the box down and started to reach in and pull out the packages inside.

I continued unpacking until not only the box was empty, but each smaller package was emptied as well. In front of me on the bed lay a small array of toys and accompanying items. Even though it was a fairly small selection I was still in awe, but I didn't let that distract me for too long. I knew exactly what I wanted to do next. I'd been thinking about it since the moment I clicked "Confirm" when ordering late last week.

I put all of the packaging back into the shipping box and then pushed it back into the back of my closet. I headed into the bathroom with a couple things and proceeded to get cleaned up for what was to come. When I was ready I pushed my thong back down to the floor so I could get ready for what was next. I took my time, stroking and caressing as I lubed up the smallest of my new butt plugs, working it all around before reaching back to finish preparing myself.

Not knowing the best way to go about things I just went for it. I spread my feet and bent forward before reaching through to rub and press the slippery tool against my pucker. It wasn't large and I had been working my opening while cleaning and lubricating so it didn't take much before the tip parted my ring enough to slide in slowly against the pressure. Once the widest part passed through it rushed the rest of the way in, the taper pulling the base forward until it nestled up inside my crack.

There was a small twinge of pain as the thickest section passed into my canal but after a couple of breaths it was gone and I could again focus on the task at hand.

I turned my ass toward the mirror to confirm that the plug was nestled completely home. The site of the base crossing over my hole, reaching up between my cheeks and slightly toward my balls was enough to make my heart jump.

Quickly, to prevent myself from going straight to play time, I reached down and pulled my thong back up, wrestling my semi hard cock into place as the back slid between my cheeks. After a few breaths to compose myself I packed up all of my new treats into the gym bag that contained all of my thongs and slid it back into my closet as well. Satisfied that everything was in its place I pulled my pants back on and then headed for my office to make what was sure to be a worthless attempt at getting some actual work done.

It only took one step for me to realize that there was not going to be any productivity for the remainder of the day as long as I had the plug inside. Every step I took sent a shockwave of pleasure through me. The slight fullness combined with the plug barely rubbing against my prostate was almost too much to take. By the time I got across the house and was about to take a seat behind my desk I was sure my pants were soaked from the puddle of precum spreading in my panties.

Every time I moved into a new position so did my new toy, and taking a seat was definitely no exception! Earlier, as I walked it had been barely grazing my prostate. When I sank all of the way down onto my chair the feeling as it pressed into me was even more intense. I just closed my eyes and gasped as the breath was forced out of me. This was better than I had ever hoped for when placing that order last week.

I knew I wasn't going to be getting any more work done that day. My body was humming as I slightly rocked back and forth on the chair so I decided to do some more window shopping instead. I spent a little time online drooling over lingerie, imagining the sexy fabrics against my skin, then moved on to reading various erotic stories. I was drawn to certain types of stories and found myself spending more time searching for the right ones than I was actually reading. Finally, I decided I would just settle in and try to write some of my own.

Once I got going I found the words were just pouring out. I wasn't spending time thinking through what I was typing. I just let the words fall where they would so as not to slow the process down. I didn't know where I wanted to go with the story yet but I knew that I wanted to get to the end. And so I wrote, the keys at times clicking furiously for minutes on end and at others the sounds only came in short bursts. It was never a matter of thinking planning out the story. Rather, the delays were just me hesitating to put it into the right words for the moment.

Hours later I had reached a good stopping point so I decided to wrap up my first story to submit, at least the first part of it. There was going to be a healthy bit of editing of course. I got a quick drink and then jumped back to the beginning to start reading through to fix things and to see if things made sense and if it was something that I would want to read.

I won't go into details now but considering I was the main character in the story, I'll be the first to admit that I was more than a little surprised with how the story unfolded. Also, after reading through I realized that it was pretty long and it should probably be broken up so I decided to submit it as 4 separate chapters with a serious cliffhanger suggesting that there is a fifth in the works. The path that my freshly written story took was something I was sure to think about and wrestle with further but that was going to have to wait.

While reading back what I had just put together I had become incredibly hot and hard. The presence of my new toy had mostly slipped to the back of my mind while I was focused on writing but the pressure and pleasure came rushing back full force. My brain was telling me to head back to the bedroom to play but those thoughts were quickly forgotten as lust overtook me. I wasn't going anywhere right then.

As I pulled the front of my thong down below my balls my straining cock sprung forward, a string of precum hanging from the tip. Immediately I gathered as much of it as I could and rubbed it all around my lips before licking them clean. The taste and slightly creamy texture of the clear coating on my lips was intoxicating. I resumed rocking back and forth on my chair, focusing on working the plug around trying to get as much pleasure out of the small intruder as I could. Cradling my swollen balls in my left hand I gripped my shaft with my right and began to slowly stroke, quickly realizing that there was a pressure built up inside and I was already rapidly approaching the edge.

After only a few more pumps my balls pulled up tight to my body, my ass clenched around the plug and my swollen cock began to flex and pulse in my hand. I barely had enough time to aim but I was able to direct the jets of white cream onto my stomach and chest. Blast after blast were soaking my shirt before they began to weaken, eventually the last of my seed spilled out in a gentle stream, running from my engorged tip and down the back of my hand.

Completely spent and satisfied I relaxed back into the chair. With the front of my shirt soaked and no towel handy, out of necessity more than desire, I licked all of the fluid from the back of my hand. There was no jolt of desire like before but I still enjoyed the taste as the thick cream slid down my throat.

Normally, as my erection subsided thoughts of any kind of sexual activity quickly faded from my mind but this time was different. I wasn't caught up in the heat of the moment anymore which understandably sent my mind in all sorts of directions. Maybe it was the new story sitting on my screen that had my brain still going but I couldn't get certain thoughts out of my head. I couldn't stop imagining myself taking a hard cock into my mouth and swallowing down its seed straight from the source.

The only other time that I had someone else's rod in my mouth had been during a surprising turn of events that happened in the heat of the moment. I had never thought about sucking or even touching anyone before that and hadn't since. As I sat there in front of my computer, wearing a shirt heavy with cum, I realized that it was something that I actually wanted to experience again, and not just while I was caught up in the moment. Rather than rushing to get the taste of cum out of my mouth, I sat and savored it, wondering if I would taste someone else's in the future.

After that first day with the small plug I took to using it every day or two for a little while. I started getting a little more used to it so I could actually work with it in. I would get used to it as long as I was focused on what I was doing and not moving around too much. If I got distracted or had to get up to do something then I would be quickly reminded of its presence. Despite that, I decided I was ready to graduate. I wanted more fullness and deeper penetration so I stepped up to the medium one, and boy was i pleased with the upgrade.

As my experiences with my new toys progressed I made sure to keep in touch with Steve and let him know what I was up to. He was always anxious to hear what I had to say and he ate up the stories that I shared with him. Unfortunately he didn't respond with stories or fantasies of his own but that didn't deter me from continuing to share mine with him. He did, however, often let it be known that he would love to meet up with me, but he wasn't pushy when I resisted due to my current relationship.

In one email he told me that he would be in town and wanted to know if I wanted to meet up, possibly with an additional friend. I became instantly hard when I read it but I still couldn't bring myself to have a physical relationship outside and I told him as much. I did say that I would love to see him and catch up and I asked if there was any chance I could watch. He said he could probably make that work or he could at least put on some sort of display for me.

After a few more email exchanges it became apparent that he probably couldn't find anyone available in my area. Having shared with him the sexy lingerie that I was most drawn to I told him that I had another proposal for him that didn't involve contact on my part but would still be an exciting time. He was to let me know where his hotel was and lay out my outfits for the evening/night. I was going to come to his hotel room, then model the lingerie and sexy costume while he watched. Meanwhile, I was going to get to watch him stroke himself, edging for as long as he could take it while I made my way through the outfits that he brought for me.

We left it at that for awhile, vague plans to get together with no specific date or location and no plan for how I was going to get away. I kept writing and we kept talking, me always trying to see what kind of reaction I could get out of him with my next stories or links to outfits or toys that I wanted, and him always briefly sharing what he did after he read what I shared. I was usually pretty happy with the result. The biggest disappointment for us both was when either of us would take too long to respond.

Despite my varied attempts things continued to deteriorate at home. Finally I took to wearing panties or thongs under my clothes and keeping a plug in even when Jenny was home. I knew nothing was going to happen anymore where she might find out and I liked how it made me feel, the thrill of just wearing them, along with the added thrill of the possibility of getting caught.

The urge to dress up more, and having someone else see me was always in my thoughts. I masturbated daily, sometimes multiple times, and often some variation of the same scene played in my head. I shared with Steve the evolution of what type of stories, videos and pictures that I searched out when I wanted something more than my imagination. Not too far back I had pretty broad tastes in my erotica (hetero, bi, trans, threesome) but the topics that I had become most interested in had started to narrow.