Susan's First Challenge

Not really knowing what to do with the rest, I just stood there looking sheepishly at Beth with my hands out with the remains of the gel mixed with my pre-cum on the index finger. The twitching head of my cock was sticking out of the white panties, a clear delicate thread of pre-cum hanging down about a foot or so, my balls sticking out of the sides.

"Do not move!" She said as she pulled out her phone with her free hand and quickly took a picture. "Beautiful Susan! You look fucking gorgeous like that!"

A wave of devotion spread across my whole body and I actually felt proud of myself, even though I felt completely humiliated like this in front of a complete stranger, and despite the fact that she now had very incriminating evidence to use against me should she wish.

"Right! On your knees Susan." There was now a stern but amused look on her face and she was clearly enjoying this. I obliged - there was no longer any room for questions or protest - just do exactly what she says.

"Shuffle forward so your arms and chest are resting on the sofa." I duly shuffled.

"Bum out! Higher! I want you to present yourself to me Susan. I want you to give me your arse!"

I arched my back and pushed my bottom out as far as I could. The tip of my cock was oozing pre-cum onto the very edge of the sofa but I couldn't feel anything there now - just the pulsing of my heart within my shaft and my balls tightening and retracting.

I felt my panties being pulled firmly to once side and a wet coldness right in the crack of my bum as Beth smeared lubricant around my anus - it was a great feeling to be touched there for the first time by a woman.

"We'll start with a smaller size and go up from there. We need to find one short enough that it doesn't hurt too much when it's all the way in, but wide enough that it really pushes the sides when it goes in and out."

And then I felt a firm pressure on my anus that both spread out and entered in as she slid the dildo into my arse in one slow continuous movement. I gasped out loud as I felt the stretch and wondered if I could take this.

"Good girl Susan, good girl!"

Oh my God! Did she just use the exact same words as Mistress? Could this all have been some kind of plan all along? No - surely not.

"That went in quite easily - can you feel the tip inside you?"

"I don't think so - I can feel it stretching me but ..." I didn't really have the words to describe what I was feeling "... it feels really good Mistress." Oh Fuck! Had I just called her Mistress?

Suddenly my head was pulled right back by my hair and I heard her whisper loudly right in my ear.

"I am not your Mistress Susan. You have a Mistress already remember?"

And with that she pushed my head forward again, tousled my hair and said "But you can call me Auntie Beth."

That combination of pain from my hair being pulled back, fear from having done something wrong, and then warmth and love from that simple gesture of my hair being ruffled, deepened my desire to please this woman.

"I think you need a thicker one Susan." And with that I felt my arse explode as she quickly pulled the dildo straight out with a plop!

"Fuck!" I screamed, part surprise, part pain, but mainly pleasure.

SLAP! My right buttock stung with fire at the hard smack.

"No swearing!"

SLAP! My left buttock now stung as much as the right.

"And don't speak unless I ask you a direct question!"

Tears started to fill my eyes as I bit my lip from the sharp pain and the growing soreness on my buttocks.

Some rustling behind me. I knew the next dildo would be coming soon and it would be bigger.

"This one is a bit longer but it's much wider and it has a slight bend which should help us get to the prostate."

Again the pressure in the centre of my anus, but this time it spread more slowly out - and kept on spreading until I thought my hole would actually split. More tears came, now running down my face and dripping onto the sofa. But my cock was still rigid and the feeling of such pain and pleasure at the same time was making me giddy.

And then the pressure was no longer spreading but pushing inwards and as the dildo rubbed tightly against the walls of my anus I felt a level of pleasure I had never felt before - a slow continuous intense hit from the innumerable nerve endings all round the inside of my anus and I wondered just why that part of my body needed so many pleasure-sensors. I moaned loudly but formed no words.

"There we go sweetheart - this one might be the right one for you. That feels nice and tight doesn't it?" I moaned in agreement.

"Now let's see if we can reach your prostate."

And the pleasure-sensors reignited as she rotated the dildo inside me. I could feel the tip now inside as the bend in the dildo made the tip rub against the anal walls deep inside me as Beth rotated it. And then without warning it ran over my prostate and a jolt of electricity coursed through me, up my spine and along my perineum, up the base of my shaft and then stopped at my numb head. My sphincter contracted and my cock twitched and rubbed against the front of the sofa, smearing more pre-cum.

"Mmmmm!" I moaned loudly.

"Bingo!" She cried "Houston, we have lift off! Now tell me when the feeling is most intense." With this she moved the tip of the dildo around and I squirmed as jolt after jolt rushed through me and my cock started flailing up and down - thank god for the desensitising gel or I would be squirting cum everywhere!

"There! Auntie Beth. There!" I shouted, half crying as she stopped moving the dildo and just applied a firm pressure. I felt like I wanted to pee and I thought for a moment that I would wet myself rather than cum but then the pressure eased a bit and I just felt the tip resting on my prostate.

"Ok. This is definitely the right one for you. Now, with the tip on your prostate the dildo is not quite fully in, but that's good because it means you can still move it in and out. The trick to a hands free orgasm is to find the right spot ..." and with that she reapplied the pressure and I felt another jolt "... and then rub the dildo around it. It will feel like you are going to wet yourself but you won't - that's just the prostate gland getting ready to squirt your spunk out. With practice it should take less than 5 minutes to empty, but since you're a beginner it will take longer. And you probably won't get it all out in one go - you'll have to pause and then go again. I reckon you could get at least three loads after a week of denial."

All this information at once was confusing me but I tried to focus on what she was saying and take in as much as possible.

And at that my arse exploded again as she started to pull the dildo out, and out, and plop! My sphincter contracted swiftly but I felt completely empty inside - such a strange feeling of pure physical longing for a missing part. And now the soreness in my buttocks returned and the realisation that I could not cum yet, and an involuntary sob escaped me and the tears started running down my face again.

I felt one warm hand on my buttock and one on my head as Beth ran her fingers through my hair and gently rubbed my bottom.

"There there Susan. You've been such a good girl for me haven't you. You've been very brave haven't you."

I nodded vigorously but couldn't speak through my tears and the sobs that now racked my body.

"It's going to be ok sweetheart you'll see. We've found your dildo at least. Now why don't you get dressed and then come through to the shop."

"Yes Auntie Beth. Thank you Auntie Beth."

She gathered up the other dildos and condoms and headed back out the door, turning round to see me standing up, my panties stained with pre-cum and my erection starting to fade inside them. Tears lingered on my face and I must have looked dejected as her face changed back into a soft caring visage.

"Smile Susan!" And she took another photo with her camera.

I put my clothes back on and made my way into the shop. Beth had unlocked the door and a young couple had entered and were browsing the BDSM section, giggling like school children. Beth was behind the counter and had a small black bag in her hand.

"That will be £99 my love." She said as I approached the counter. "And I'll need your contact details for the guarantee." She pointed to a notepad and pen and without thinking I wrote down my name and phone number. "Your address and e-mail too darling." I wrote these down as well and she swiftly took away the pad and placed it under the counter. I suddenly remembered the photos she had taken and I was gripped by a sense of dread!

Beth leaned forward and whispered to me "It's ok Susan - I'm very discrete!" And as she placed her hand on mind she added "And I'll need a copy of that video too!"

As I left the shop, bag of goodies in hand, mind all over the place, arse empty, buttocks sore, wet panties and a semi erection (will that ever go away?), I looked at my watch and realised that my lunch hour had actually taken two hours and now I would have to stay at the office later to catch up on work. I messaged my wife to let her know (to be honest I would rather she was already out of the house when I got back) and headed back to the office.

It was nearly 8pm when I finally got home and sat down exhausted on the sofa with a beer to think through my challenge. I could fix the dildo to the dining table leg - I had some cable ties that should work for that. I also had a small tripod that would hold my phone for the recording. I was pretty much set, and hopefully it wouldn't take too long - besides I really wanted to cum at last.

My phone pinged and I checked the message to see whether it was my wife - didn't want her coming back early!

And up popped an image of me from earlier that day - standing with my hands out wearing nothing but my white cotton panties, the head of my cock sticking out and dripping, with a surprised look on my tear-stained face! It was from "Auntie Beth"! And a caption: "Good luck tonight lovely Susan. Don't forget to send me a copy of the video! What time do you have to complete your challenge by?"

And with those last few words a chill ran down my spine - what time had Mistress set my challenge? It was on my way home from work yesterday - around 6pm. FUCK! I was already 2 hours over the 24 hour time limit! Had I somehow thought maybe she meant by the end of the day? What was I thinking? Maybe she did mean by the end of the day? Maybe the time limit had only been advisory? Yeah right - wishful thinking! Oh Fuck! What should I do?

Well I have to send her the video - that's non-negotiable - maybe I could apologise profusely and explain what had happened?

I decided to set up the tripod and phone first so I could get a good side view with the table leg on the left of the frame. That was the easy part. I got a cup and some cable ties and placed them near the table. I thought the best thing was to record everything from start to finish, so hesitatingly and with a long deep breath I pressed record.

"Thank you for my challenge Mistress." I said directly into the camera (she already had my face in a recording from that first FaceTime call so I was not so worried about showing myself to the camera).

"I hope you enjoy this."

Then I slowly undressed myself - shirt and vest first, then my trousers and socks and finally my (now dried) pre-cum soaked panties. Already my cock was starting to rise as I was completely naked and starting to think about cumming at last.

I took the nylon bodysuit out of its packaging (first showing the pack to the camera) and started to put my legs in while still standing, hopping about trying to get the foot on properly and then falling on my arse - probably easier while sitting I thought. It took a while but eventually it was all the way on. And then I realised the first problem - no holes for my cock to stick out of, or for the dildo to enter. I grabbed the front and ripped it a little and then worked my now hard cock out of the small hole. The nylon felt fabulous against my skin and the slightest movement made me remember that I was totally encased in nylon. I enlarged the hole toward the rear until I felt that there would be enough room for the dildo.

Taking the cable ties, I positioned the dildo against the table leg about 18" from the floor. The cable ties worked really well with the dildo's large flanged base and soon it was held firm against the leg, pointing straight out like some kind of weird black growth. I made sure the slight bend in the dildo was pointing downward since I figured that had the best chance of hitting my prostate. Finally I squeezed out a handful of lube and rubbed it first on the dildo and then all around my anus. It felt cold but it didn't feel half as good as when Auntie Beth had lubed me up earlier.

Ok I thought - here we go. I got down on all fours with my arse toward the dildo and started to slowly reverse until I could feel the cold tip touching my buttock. I squirmed my arse around a little until I felt it nestle in the crack just above my opening - too high I wondered? I recalled what Auntie had said about "presenting" my bottom to her, and I arched my back like before and pushed my bottom up and out until I felt the tip nuzzle my sphincter. It felt nice resting there and I paused for a moment, taking in a deep breath and preparing myself for what I was about to do to myself. I felt a flush of shame that I had so quickly and so easily gotten to this point. I was really going through with this! My cock was sticking out almost horizontally and just the weight of it hanging there in free space felt delicious - I put my head down and looked back toward it, still tacky from all the pre-cum of the day, bobbing slightly up and down, feeling each movement. Fuck this looked hot! I hoped the camera was catching it well.

And then I pushed slowly backward and felt that stretching burning sensation as the dildo tried to find its way in. It hurt quite a lot but I knew I had to persist and that once it was in it would feel much better. So I pushed back a little harder and felt that incredible inward rubbing sensation inside my anus as the largest part of the silicone object passed in. I had started to perspire somewhat with the strain and so I paused again, hoping that my anal muscles would settle around it. The burning sensation eased a little and I moved back even more and suddenly felt that now-familiar jolt as the bent tip ran across my prostate - oh my god that felt good!

I decided to experiment with moving in different directions and varying speeds until I started to get into a rhythm of pushing back and forth while swaying side to side. It was mesmerising! The slow rimming of my prostate by the dildo head was sending sparks all through my groin and then through my whole body and my legs began to shake. I felt the need to pee and even though Auntie Beth had told me to expect this, it was unnerving and I paused a while to regroup.

I bent my head down to get a good look at myself from below and was shocked to see a long line of pre-cum trickling from the head of my rigid cock, all the way down to the rim of the cup. It was almost like watching a POV porn film and I shivered with excitement.

I reached back and moved the cup further back so that the cum would fall into it, and relished the thought of touching my penis - just a little light rubbing of the head and I'm sure I would spurt everywhere. But no - Mistress had been extremely clear on that rule - no touching!

I started to move again, this time watching myself from below, transfixed by the sight of my rigid dick bobbing up and down with every jolt of pleasure that ran from my prostate straight into the base of my cock, my anal muscles contracting and sending waves of pleasure all the way up my shaft. The only sensation missing was contact with the sensitive head! Instead I felt a powerful yearning to be touched there - please! What would I agree to do if someone would just touch me there right now?

And then I saw a bead of milky cum pop out of the tip - and another one pushing that out, and then a sudden stream of cum running out steadily and flowing down to drip into, onto, all around the cup. But I couldn't control it and I couldn't feel it - I was drooling cum everywhere but not spurting and with no orgasm! The head of my swinging cock was still crying out for touch and my sphincter was contracting and I could feel a firm pressure inside the shaft but no screaming orgasm!

I moaned loudly and it came out more as a cry for help. Maybe I hadn't done it properly - maybe I need to fuck myself more forcefully in order to cum properly. I still felt so incredibly horny and desperate for relief and I moved back and forth so vigorously that the dildo popped out and when I moved back again it rode up my bum crack smearing lube everywhere. I found the tip again with my anus and pushed myself firmly and quickly backward into it again - Arrgh! Ouch! The dildo stretched me wide and filled me again but the desire for an orgasm overrode any pain now. I remembered that Auntie said I could probably get three loads out having been denied for so long and I started thrusting myself back again and again I saw more cum flow out and pushed myself all the way back on the dildo - my arse cheeks now firmly either side of the table leg, gripping it as I squeezed my anal muscles and more cum flowed out and still my sensitive head cried out for touch and was left bereft.

I was shaking almost uncontrollably now and had to pause and try to aim the cum flow at the cup, not entirely successfully.

The river slowed and my penis stopped bobbing and, my head resting on the floor I took in this image of myself. Spent and exhausted, but still desperate to orgasm!

How ridiculous I look!

How cruel she is!

How wonderful it is to do this for her!

I slowly moved forward and felt a sublime pleasure as the thick dildo slid out for the last time.

And now, I pondered, the last humiliation. I sat back on my haunches and picked up the messy cup, cum slopped all around and inside. I placed it to my lips and that sweet sour salty smell of spunk filled my nostrils. It didn't flow out of the cup as easily as it had flowed out of my cock and I had to lick all round the inside of the cup to get it out. I felt a surge of disgust, and then a thrill of transgression and even savoured the last few drops.

I reached across and turned off the recording. I should send it immediately I thought - I'm already almost three hours late. Clicking on the link in the e-mail that Mistress had sent with the challenge took me to a drop box folder simply titled "Susan's Challenge #1". I uploaded the video - there was no way to add a comment or anything to explain why it was late - and gulped as I considered what could happen to that video. While I had the phone, I also sent the video to Auntie Beth - all I could manage was a smiley emoji.

I had some cleaning up to do.