Small Silicon – part three

Today’s task was similar to Thursday and Friday’s task however today I was instructed to penetrate for only 10 minutes. The Domme was toying with me.

i jumped in the bath and squatted down as if I was a bird sitting on its perch. I rolled a condom down over the toy and squeezed a large amount of lubricant onto it’s tip. I slowly lowered myself onto the toy and let the weight of my body do the work in regards to sliding it it. The short time frame meant I could hold this position for the duration of the task without my legs getting. particularly fatigued.

I slid onto the toy as far as physics would allow and pushed hard on my ass to expel it during the Howard movements. I bounced up and down on the toy, whilst pushing hard which made the sensation of being penetrated particularly interesting.

Ten minutes really wasn’t very long and before I knew it, the timer went off unexpectedly. Usually by this time I’d be just getting warmed up and my ass only beginning to relax which made me quite frustrated. For this reason, ten minutes is more frustrating than 20.

I wanted more – wider, longer, deeper. This will have to wait.

Small Silicone (cont.)

Todays task was identical to yesterday’s except only for 20 minutes. I had a feeling The Domme new yesterday’s task was frustrating given the size of the you and its general lack of girth.

I chose to complete today’s task on the bed, with two towels underneath my lower body. I slipped on a pair of latex gloves and rolled a small condom over the toy. To make things interesting I decided to lubricate my ass instead of applying directly to the toy. I rubbed the toy up against my ass to evenly distribute the lubricant and began to push slowly inside. The tip of the toy was only slightly larger than the shaft so it was easy to tell when it had made it past my sphincter muscles. I lubricated the shaft of the toy while it was partially sticking out, then twisted it while pushing deeply. The toy was buried in my ass – a very frustrating feeling given it was slightly too short and nowhere near wide enough to be overly fulfilling.

I was determined to complete the task as specified so continued to penetrate myself with the toy, applying lubricant every few minutes. I still liked this toy and it made me extremely horny to know I was only using it because The Domme knew it was frustrating for me.

I pounded away at my throbbing and dripping wet asshole until the timer ran out – comfortable that I had done the task justice.

I expect more from this toy in the future.

Small Silicone

Today’s task was simply to fuck myself continuously with a medium sized, smooth black silicone dildo. This dildo was a great warm up toy when used with the strap-on harness, but would be made much more frustrating today given the 30 minute time frame I was to continue to task for.

It was chilly today so I grabbed a towel and sat in front of the heater. I stretched a condom over the toy and lubricated it heavily. I placed the toy upright on the towel and began to lower myself onto it as if I was straddling a cock. I loved to be fucked like this however it was hard work as it’s mostly the legs that have to do all the work. I slid all the way down onto the toy and tightened my ass muscles as hard as possible. I could feel my ass pushing against the toy. I bounced up and down on the toy, and watched as my cock harness bound cock and balls slapped back and forth with my movements.

I continued this for around 15 minutes, when my leg muscles became too sore from the repeated positioning of my body. Under the assumption I wasn’t to have any breaks, I rolled onto my back, lubricated the toy again, and slid it straight back up my ass. I continued this for the amount of time remaining.

It wasn’t a huge toy in length, nor girth, which was very frustrating for me as I liked a challenge. I was certain this toy was chosen specifically for this fact. The Domme wanted to frustrate and annoy me, which had been accomplished.

I left for work with my heart racing and my ass begging for more, however I felt comfortable in knowing that I had completed the task as requested.

Black and Ribbed

Today I was to penetrate myself with my black ribbed, large silicone dildo. This was one of The Domme’s favorites and was mostly used in a strap on harness whilst fucking me from behind. I was to penetrate myself with the toy for 20 minutes with no breaks and absolutely no penile stimulation.

I decided to complete this task whilst lying in the bath – this was I had absolutely no limits regarding how much lubricant I could use and also made clean up a little easier. I slipped a large latex condom over the toy and squeezed a generous amount of lubricant into my gloved hand. I then grabbed the toy by the shaft and lubricated it well. I applied more lubricant directly onto the opening of my ass (it was cold!) and also a little more on the toy itself.

I began to slide to toy inside – it was large for this time of morning however pretty soon my muscles relaxed and allowed me to push all the way inside, up to it’s flared base. The flared base provided great amounts of grip and meant I could bang away as hard as my hands could move.

I was lying on my back fucking myself with the toy, then found I couldn’t quite get enough leverage in the current position – my bath wasn’t very wide so it was difficult to get my arms down the side of my body. I got up onto my feet and squatted to allow full access again. I slowly slid the toy back into my ass, one rib at a time – the hard, ribbed texture kept the toy in place even without using my hands. I continued to fuck myself – pulling it all the way, re-lubricating, then sliding slowly but firmly back in with every few dozen strokes.

My 20 minute timer sounded it was time to clean up. I had made a slippery mess – as usual.

Getting (Very) Messy – Part 1

Today I was instructed to “Get Messy”. The Domme gave me a budget of $40 and was told to purchase a number of food items which I would then use to explore my sense of temperature, textures and flavours – by playing with my food in the bath.

I went to the shops and with my $40 in hand brought a few fun items:

• 12 eggs
• A large tub of Mango Yoghurt (1kg)
• A large tub of Blueberry Yoghurt (1kg)
• A Chocolate Cake (500g)
• A Custard Filled Danish (700g)
• A dark chocolate dessert (250g)
• 1L of “double thick” chocolate custard
• 2Kg of vanilla custard

Three was quite a bit of food there – I was surprised I managed so much for the budget that I had. I look forward to the day when the budget is $100.

I arrived home after my purchase and immediately removed my clothes. I placed each item in the microwave for 60 seconds to bring them to room temperature. I sat in the bath and looked at the items I had laid out on the floor. This would be a messy afternoon indeed.

I picked up an egg and felt it in my hands. It was still cold as I was unable to heat this in the microwave (eggs burst in the microwave). Without hesitation I cracked the egg over my head. The shell broke with a loud “crack” and the egg began to slide down the side of my head and down onto my chest. It was cold but it was a very pleasurable sensation. I grabbed the dark chocolate dessert and opened it. I laid myself down in the bath and closed my eyes, and opened my mouth wide. I held the dessert above my head and began to pour it over my head – it was very thick and I could already smell the dark chocolate and sugar within the tasty treat. The entire contents of the dessert landing in the middle of my face, some landing in my mouth but mostly on my nose and in my eyes. I held my eyes shut while I swallowed the amount that had made it into my mouth. It was very sweet and still a little cold, however some parts were warmer than others. I threw the cartoon down and rubber my face which was covered in thick, dark chocolate dessert. It tasted great!

I grabbed the chocolate cake – unwrapped it, and began stuffing it into my mouth as if I was being force fed continuously – I had eaten maybe 1/3 of the cake and then I buried my face in it, rubbing it all over my head and into my eyes. I felt bits of the cake fall onto my body and into the bath. The cake was a little dry, so I decided to dial things up a notch and grabbed the tub of Mango yoghurt. I pulled the wrapped off and dumped the entire 1kg contents over my head while looking up with my mouth open – I swallowed as much of the yoghurt as I could before the carton was empty. The yoghurt was very cold and by this stage I was very messy and my body was covered in chocolate cake, and Mango yoghurt. I repeated the process with the Blueberry yoghurt, by first pouring the entire contents into my mouth, until it overflowed onto my warm body. I had made a lot of mess and began to rub my hands over my yoghurt and chocolate covered body. I rubbed the mess into my chest and my legs, careful to avoid stimulating my cock as this was forbidden.

I cracked a few more eggs over my head in quick succession, and sat still while the insides of each trickled down my back and the side of my face. I picked up the Danish. I took it out of its packaging, and dropped it upside down, on my chest. I began to rub it into my chest and kept pushing harder until it began to split up into multiple messy pieces. I grabbed handfuls of the mess and shoved them straight into my mouth, swallowing mouthful after mouthful as if this were my last meal. I grabbed the container of chocolate custard and opened it. Again, I laid down in the bath so I was perfectly horizontal and poured the contents directly above my head – it was warm and heavy, and I could smell and taste the chocolate as it left the container, and dropped onto my face. It was heavy – like a slippery chocolate blanket – it slid slowly down past my face and around the sides of my head. It was delicious.

I was still lying down and cracked the remaining eggs over my forehead whilst the contents tricked down the front of my face. I held an egg in my mouth and slowly cracked it with my teeth until it broke open. I felt the yolk and egg whites slide into my mouth, which I, without hesitation, swallowed in its entirety.

I had just one item left – 2kg of warm, room temperature vanilla custard. I opened the container and began to pour it over my head. My entire head and face was covered in the thick yellowy-white substance and I could feel it sliding down the middle of my back. I consumed as much of the substance as gravity would allow, while it overflowed from my mouth and down onto my chest. I continued to pour the custard over my entire body – 2L is a lot – it truly felt like it was an unlimited quantity. I watched as it slowly covered every area of my skin, while large portions of it slid off my body. The container was now empty, and the bath contained nothing but my warm, horny, naked body and about 7 litres of thick, slimy, yellow liquid, with random swirls of chocolate distributed amongst it. I rolled around in the mess and cupped quantities of it up with my hands, and dribbled it slowly over my face.

I had run out of items, and as a result, I turned the taps on. The bath began to fill with warm, milky water which was a wonderful feeling. It took some time to clean the mess I had made, but ultimately, it was $40 very well spent. After all, how often do you get to play with your food like this?

I look forward to playing with The Domme in a future visit.

First eleven

Today I was instructed to penetrate myself with the Njoy Eleven – and eleven inch long giant made from cold, hard steel. It had been quite some time since playing with this toy and as a result it stretched my ass painfully wide. This toy had the unusual ability to make me climax from anal stimulation however, this was forbidden. I awoke as per the 7:30am schedule time and positioned myself on the bed with two pillows underneath my lower body to bring my ass a little higher and make access easier.

I was told to get messy so I chose the thickest lubricant I owned – Glide. This lubricant came in a huge 2L bottle and I had plenty left for this task. I liberally applied lubricant to the toy and spread it around with my hand as if I was stroking some monster robotic cock. I applied another larger amount to the small head (‘small’ in this case was still more than 1.5 inches wide) to initially help the toy slide inside.

I began to push the toy, slowly past my first sphincter muscle – it was uncomfortable but I knew within a few minutes the pain would turn to pleasure. The small end of this toy is a wide, bulbous head much like the larger end. I continued to slowly push the toy deeper inside my ass, making a few mm’s of progress with each stroke. All of a sudden my anal muscles relaxed and the head of toy slipped all the way inside. It was a wonderful feeling that I hadn’t experienced in some time. I slowly pulled the toy out and then jammed it straight back up my ass with one violent motion. I felt like I was being fucked by The Domme – an event which I missed dearly.

I buried the toy inside as far as it would go, pushing it past each ridge on its surface then began to swirl and twist it enthusiastically. I continued to push and pull on the toy which was very intense. I had to make sure there was no climax so slowed down when I felt the urge.

My fifteen minute timer had run out which felt like just a few minutes. I had used quite a large quantity of lubricant and as a result had made a mess – so much so the lubricant had soaked through the two layers of towel I bad placed underneath me.

I cleaned up the mess, and prepared for work. I was certain id be thinking about this all day.

Week 4 – Day 21 – Friday, 17th December 2010

Today’s task was very simple, and a result of still having a sore ass from Wednesday’s butt plug effort.

• You will lubricate your cock.
• You will give yourself a hand-job for 10 minutes.
• You will not orgasm, climax, or have any breaks.
• You will wear your black lacy panties to work, and leave them on throughout the duration of the day.

I awoke this morning and skipped my daily exercise. I had a very busy work day ahead of me so needed an extra hour of sleep. I hated myself for not getting out of bed on time but sometimes it was worth it to be well rested.

I grabbed a latex glove from my bedside table, and a huge bottle of lubricant. I slipped on the glove and generously applied lubricant along the shaft of my cock. I grabbed my pulsating, hard cock and squeezed it tightly. I hadn’t played with my cock for many weeks (six perhaps?) so it felt great to finally get some stimulation with The Domme’s consent.

I started to pull on my cock slowly and firmly. I wrapped my entire hand around my cock and began thrusting towards it. It was very wet and slippery which made me extremely sensitive. I reached the point of climax several times, however wasn’t permitted an orgasm, which was very frustrating but inline with The Domme’s instructions. I continued on slowly, the whole time thinking about the frustrating tasks The Domme would have me doing over the weekend (as mentioned in an earlier post, The Domme was coming to visit).

I passed the five minute mark and had to stop. After six weeks of no orgasms and no stimulation (in combination with the lubricant) I was extra sensitive and would have had an orgasm if I’d continued. I jumped in the shower and washed the lubricant off my now very hard, purple cock. I began stroking it in the shower as I was determined to complete my 10 minute hand-job. It was much less frustrating and more pleasurable in the shower as I had a lot more control over my level of arousal. I continued to wash myself with my left hand, while pulling on my cock with my right. I completed my 10 minute task, however was disappointed that I couldn’t do it without breaks. The Domme would be disappointed, however still pleased with the fact that I did not orgasm.

I finished my shower and dried myself in front of the heater. I laid out my clothes for the morning which included the black lacy panties I had been instructed to purchase weeks earlier. I slipped on the panties. I felt incredibly sexy, staring at myself in the mirror and the short black laces attached to the side, purely form over function. My cock was still quite hard, which made the panties uncomfortable, however I knew my erection would subside as the morning continued on.

I put on a pair of suit pants to go over my sexy new underwear. I felt very wrong, but that was the attraction! I’d be wearing my black panties at work throughout the day, meeting people, shaking their hands, all the while knowing I had a pair of Pleasure State black panties on just one layer beneath my suit. I put on the rest of my suit and continued in with my day, starting with breakfast.

Today would be interesting.

Take care,
Jordan – xo.

Task frustration level – 6/10
General frustration level – 8/10