Susan's First Challenge

This story follows on from a previous story ("Good Girl Susan"). Although you do not have to read Part 1 - this story works on its own with only limited references to the first part - that initial story explains how Susan first came to submit to a Mistress, whereas this story shows how that submission deepens and solidifies to the point where she cannot easily retreat, even if she wanted to.

It had been over a week since THAT phone call. A long and challenging week indeed as my thoughts dwelt on that initial encounter and tried to make sense of just what had happened and what it implied. And though I'm sure Mistress had no way of knowing whether I had kept my promise not to cum until she told me to, I felt obliged to follow her command. I always keep my promises - I am a good girl after all - but this was more than a point of principle. I knew when she next contacted me she would ask me directly, and for some reason I could just not help but be honest with her - I felt a deep-seated desire to please her that I couldn't figure out. And who knows what she was capable of - after all she had found my phone number from a simple post on Fetlife. And what's more, I wanted to find out where this would all lead to. I wanted to know what it was like to have a strong woman control my orgasms.

But it had been difficult. Mistress had given me permission to touch myself as long as I was thinking of her and her voice. And believe me I had touched myself over and over again. Some days it felt as if I was just waiting for an opportunity to go to the toilet and rub myself right to the brink of orgasm. To get at least some pleasure and to test whether I could control myself and resist the urge to take my orgasm all the way. Needless to say, a lot of pre-cum had been produced and all of it I had licked up and savoured. But now it was over 7 days with no contact at all and I started to think she had just been teasing me, messing with my mind as surely as she had made me mess my pretty pink panties. And I was desperate to cum! How long can you even go with so much edging but without an orgasm of any kind?

On my walk home from the office, listening to some soft music through my earbuds and feeling particularly horny in the late evening sunshine, I finally resolved that if I did not hear from her by the end of the day I would treat myself to a ruined orgasm - that doesn't really count as cumming does it? And besides ...

... the music paused and my left buttock started vibrating as my phone received a call. It could be anyone really - probably my wife wanting to know when I'd be back.

"When did you last cum Susan?" came that low sensuous voice resonating in my ears and through my head, and I had that eerie feeling again as if she were in my mind and talking to me from within. Immediately my chest tightened and my anal muscles involuntarily contracted and I felt a surge of excitement rush through my whole body. I could feel the blood starting to pump into my shaft and slowly engorge my cock.

"Last Wednesday Mistress" I replied, quickly adding "when you told me to Mistress." I didn't want her to think that I had disobeyed her in any way (and maybe I felt a bit guilty that I had been thinking about it). God I wanted to please this woman so much.

"Good girl Susan, good girl! It must have been very hard."

This double entendre made me smile and I wondered if she had meant it that way. Cheekily I decided to play along with it. "Yes Mistress - I've been stiff all week."

And I was rewarded with a chuckle from the disembodied voice inside me that made me feel all gooey and shy. I had pleased her a little bit.

"And have you been touching yourself for me Susan? Have you been thinking about our little talk last week?"

"Yes Mistress - I can't help thinking about you and what you did to me - I'm thinking about it all the time, and ..." I was just blabbering now, my eagerness getting the better of me, and my voice trailed off as I realised this and thought it better to let her talk and to say as little as possible.

There was a pause - too long of a pause really. Oh fuck I thought, have I just messed this up through my own foolishness? Stupid little girl - I'm even calling myself a girl now - what has she done to me - how does she have such power over me?

"I know you want to cum for me Susan don't you. I know how desperate you are now to empty your balls and spurt that hot delicious spunk of yours everywhere."

Was this a question? Should I answer? I hesitated a bit too long - why did I feel that I was getting this all wrong?

"Don't worry my little pet - you will cum soon. But I have a little task for you first."

"Yes Mistress, anything for you Mistress!"

"Check your e-mail." She said curtly.

And with that the call ended and I felt bereft. I had wanted to hear more of that voice. I had hoped she might guide me into masturbating again. But at the same time there was hope - she said I would cum soon. And she had sent an e-mail to me which made my heart skip a beat or two.

I quickly checked my e-mails on my phone, dodging into a side alley so I could read it without feeling overlooked - who knows what it might say? And there it was, simply entitled "Susan's First Challenge". I was too excited to open it immediately - I wanted to savour this - I read and re-read the title as though there were some hidden meaning to it. Did she mean the first of many challenges before I could cum? Or was this just the start of a routine she had planned for me - challenge me and then let me cum?

There was only one way to find out - I clicked on the e-mail:

"Dear Susan!

Congratulations on managing a whole week without cumming. I am very proud of you and I just know you will do your best in everything I ask of you.

I want you to purchase the items below, and then follow the simple instructions I have listed. This should be easy and fun.

Your Mistress."

Those simple words of encouragement lifted my heart and filled me with that feeling of devotion that I had started to recognise within myself every time I thought of her. I scanned down to see what I was to do:

"For this task you will need:

- All-in-one nylon catsuit

- Dildo

- Lubricant

- A small cup

- Your phone camera

1. Position your phone camera so that it will record everything.

2. Put on the catsuit.

4. Fix the dildo to a firm support 18" from the floor and pointing out horizontally.

5. Lubricate the dildo.

6. Place the cup on the ground just in front of the dildo.

7. Ride the dildo until you cum into the cup. Do NOT touch your penis at any point.

8. Eat your cum.

9. Send the recording to the link below.

You must complete this task within 24 hours."

Oh my god! Sure I was going to cum, but how without touching myself at all? And she would have proof of everything from the recording so I couldn't cheat at this. I felt so many emotions in that moment - wonder, joy, fear that I would fail, love for this incredible woman, worry that I would get it wrong, or that I wouldn't be able to cum at all - I had never cum without touching myself - this must be a hands free orgasm and aside from the occasional wet dream when I was younger I had no idea what to do or how it would feel.

Then my thoughts started to coalesce around the practicalities of all this. Where would I get all this from in the next 24 hours? Where would I do this? How do you fix a dildo to a support of some kind? But this part was ok with me - I am quite a practical person and I enjoy figuring out solutions to problems. This was just another problem for me to solve (and to enjoy doing it) albeit the strangest problem I had ever faced before. Throughout this my denied cock was twitching in my panties and I could feel a damp patch that must have been pre-cum. It felt good but reminded me again just how badly I wanted to cum.

It was too late now to try and find anything this evening and my wife would be expecting me home soon, so I decided to go at lunchtime tomorrow. Besides, my wife would be going out with friends tomorrow evening and I would have plenty of time to myself. But I was so distracted that evening thinking about the challenge and just how I could make it work that I could hardly get to sleep.

It was a small and nondescript doorway with a plain sign above reading "ADULT SHOP". I had been into sex shops before (a long time ago before the internet exploded onto the world with its never ending supply of porn) mostly looking for magazines or videos. But it had been decades since then and I wasn't sure what to expect. Probably the same I thought - a grumpy old man behind a glass screen who's seen it all and probably won't even look up.

Wrong!

The world had changed indeed and I was not at all prepared for what I would find. To start with, it was bright and colourful inside, like a sweet shop but with sex toys instead of candy. Everywhere I looked was filled with almost surreal silicone objects that bore no resemblance to any dildo I had ever seen. And there were signs near some stairs saying things like "Clothing Upstairs" and "This way for remote toys". The racks of magazines were absent - replaced with shelves of cock rings, bottles of all kinds, masks, paddles, chains, etc.

And there was a woman! Not browsing, but behind the low counter, reading a book and absentmindedly brushing her long dark hair back with a finger. She looked up when I came in and smiled a genuine smile - "Hey there. Just let me know if you need anything dear."

I grunted a response and rushed upstairs to the clothing. All kinds of outfits awaited me there, from skimpy maid and nurse outfits to gloves and skirts and ... all-in-one bodysuits! There were so many styles though. I picked one at random - plain, black, sheer - mainly because of the picture on the front of a gorgeous lady with a hot body wearing the suit and looking like she would just love me to touch it and feel.

Then I went back down to the main section to find a dildo. But there were so many, and so many different sizes, and I really wasn't sure what would fit inside me and how I could attach it to something.

"Do you need any help sweetheart?" Came a voice from right behind me and I almost jumped out of my skin.

"Err, I'm not sure what size I need ..." I was so nervous that I stumbled over my words and wasn't even sure I should be asking for help from a woman - what would she think of me? How could I describe what I was looking for without telling her what it was for?

"Well do you have much experience with anal play?" She asked so nicely, so matter of fact, like she was asking if I wanted milk with my coffee. And how did she know it was for me to use on myself, for anal play?

"Not really. I'm a beginner really." And then a sudden urge came over me to just tell her everything.

"You see, I have to cum without touching myself, but I've never done that before and ..." I trailed off as her smile widened and I realised that perhaps this was too much information.

"You HAVE to? Have you been told what to do by someone else?" She said in such a sympathetic and understanding voice that I felt a lump in my throat and a sense of humiliation washed over me that I hadn't felt since I was a little boy being told off for something. I felt a tear forming in my eye and I found I couldn't speak. She must have sensed that something was up and so she gently touched my arm with her left hand and said "it's ok sweetheart - you can tell me al about it if you like - I won't judge you for anything. We get all kinds of requests in here and I've really seen it all."

And at this the dam broke and I just started crying openly as all the emotions from this past week tumbled out at once.

"Oh my love - why don't you have a seat and I'll make you a cup of tea!" And with that she guided me with her hand - still on my arm - towards a small door at the back of the shop. "You sit down in there darling and I'll put the kettle on. We're not busy this time of day. You can tell me all about it."

I had stopped blubbering openly but there were tears running down my face and I felt totally exhausted. I sat down on a small sofa in the small staff room, while the woman went back out front (to lock the door I guess) and then returned and put the kettle on.

"What's your name darling? My name's Beth."

"Susan" I said it automatically without thinking and immediately wished I could take it back, but ...

"That's a lovely name honey - I had an Aunt Susan - she passed away though." She hadn't even batted an eyelid at me calling myself Susan - maybe she had seen it all. She must have been in her 40s at least, and was quite large, but very shapely I could now tell as she made the tea and I could look at her without having to look into her eyes. She had enormous breasts, but very pert, and a bum that stuck out. She was wearing a white blouse and a black knee-length skirt with comfortable shoes.

She sat down right next to me and I felt myself almost lift off the small sofa from her weight, before settling down again. It was a small sofa and she was so close to me that I could feel the warmth of her body all the way down my right arm and leg. It felt very reassuring.

"I'm so sorry Beth - I have no idea why I started to cry. I think I'll be ok now - thanks for the tea."

"That's quite alright poppet" - those pet names she kept calling me felt so good - like I was loved and cared for.

"Now tell me what you have to do."

As I explained everything - about Mistress and the phone call and the panties and not being allowed to cum for a week - she listened intently with a look of sympathy and understanding. As I told her about the challenge a broad smile formed on her quite lovely and youthful face.

"Ok - well first things first Susan. You are a very lucky girl." she called me a girl! "You have found a beautiful strong woman who wants to control you and that's amazing."

I felt so reassured by this lovely woman that a lump started to form again in my throat.

"Now this catsuit is just not going to work darling." She said, picking it up from the floor where I had let it fall. "You are going to need a much bigger size. I'll pick one out for you. And the lubricant is easy - we have tonnes of that. The dildo is a bit more tricky though - it's so important to get the right size and you will need one with a wide base so you can tie it onto something."

I really didn't know what to make of this - she was offering to help me, but how?

"It's best not to go for a vibrating one - they can be a bit gimmicky and I don't think it will help get you off. Besides, I'm sure your Mistress would have specified a vibrating one if that's what she had wanted. We have a range that I think will work for you, but we do need to know the size. Wait here sweetheart and I'll be back in a tick."

And with that she left the room and I was left to my thoughts. I really just wanted to get out of here now - it had been embarrassing enough already - but at the same time this lovely woman was so kind and helpful and I just wanted to sit here with her and maybe cuddle her and fall asleep in her lap ... don't be such a silly girl I told myself.

She returned in about 5 minutes with a bag filled with something or other and I couldn't take my eyes off it as she first pulled out a different catsuit.

"This one will fit you perfectly - and it has some lovely flowery patterns on it." It did indeed have some nice patterns, although I wasn't sure why that would be important.

"Your new Mistress will love it if you dress nicely for her - you have to make a special effort to please her."

"Thank you" I managed as I took the catsuit and started to look intently at the size information on the back. As I was doing this she turned the bag upside down onto the floor and shook out what must have been about 5 different dildos, each with a large flanged base, but each a different size. I also noticed some tubes of lubricant and several condoms fell out and spread over the floor.

"It will be far too difficult to guess the right size for you Susan, but I think these are roughly right - you are a big girl after all!" And with this she laughed a real belly laugh and I couldn't help but join in.

"You only have one chance to get this right, so the best thing will be to try them out and make sure. Who knows what trouble you might get into if you aren't able to cum for your Mistress!"

She said this so matter of fact that I didn't quite realise what she meant, but my face must have shown my confusion and she laughed and said "Don't worry sweetheart - we won't let you cum! Then you'd really be in trouble!"

My eyes widened as I started to comprehend what was happening to me and I started to protest: "But ... here? I don't think I can ..."

Beth's face suddenly changed from sweet and soft to firm and just a little angry.

"Now Susan" she chided "you're going to have to let go and trust me if you're ever to please your mistress! No buts - you just do as I say. And I think you should stop talking now and be quiet.

Now these are all display items so there's no need to worry about hygiene." I had not been thinking about hygiene at all.

"I'm a bit of an expert in these matters - I used to milk my ex-husband on a regular basis." I really wasn't sure what she meant by that, but I kept silent as she had commanded and just listened to what she had to say. Besides, this was all having a noticeable effect on my cock, which had started to wake up and was clearly less concerned about it all than my conscious thoughts were.

She picked up the first dildo - about 4 inches long and an inch in diameter - and started to unwrap a condom as she said to me "Now take all your clothes off and fold them neatly in the corner over there."

I rose from the sofa - sad that I was no longer so close to her warm soft curves - and hesitantly started to unbutton my shirt.

"Quickly now Susan, we don't have all day you know."

This triggered me into more decisive action and I quickly stripped and folded everything as best I could. I had completely forgotten about my panties - plain white cotton ones, but they were clearly women's panties - and as my trousers came off, I heard a little giggle from behind me "Ooh you are adorable in those - I can see why she wanted to play with you."

My face blushed red but I didn't say anything - just continued to take off my socks and reaching to pull down the panties I heard a loud "Keep those on Sweetie!"

I pulled them back up and turned round and in front of me I saw a vision of wonder as Beth had rolled up the sleeves of her blouse and stood there with the covered dildo in one hand and what looked like a large glob of lubricant in the other, topped off with the broadest grin on her pretty face. I had a very definite erection and the head of my cock was sticking out above the waistline.

"Well, well, well! We're going to have proceed carefully I think - we don't want you too excited do we!"

With this she dropped he dildo onto the sofa and, with one outstretched hand still holding the lube, she darted out the door again and returned quickly with another small tube.

"Rub some of this around the head. It's desensitising gel." And she handed me the tube.

I unscrewed the cap and squirted a dollop onto my fingers.

"Not too much now - only a bit round the head! Use your finger!"

I rubbed a little onto my left index finger and a sudden intense memory of THAT call with Mistress flooded over me ("Rub it with just one finger Susan!" She had told me) and blood rushed into my cock, already stiff, making it so rock hard that I could feel my heart pumping at the very tip of my penis. I delicately rubbed my finger around the head, smearing the gel all over and within seconds the most intense feelings started to dissipate, though it was still twitching with every beat.