I was on holiday and by a strange coincidence just happened to be staying in the same hotel as the Online Mistress. What a fortunate turn of events I thought, to be staying in the same place as her. Naturally I couldn’t take my eyes off her and found myself peering through my sunglasses at her at every opportunity. Whenever she appeared my heart would be racing. I would study what she wore and admire how immaculate and fashionable she looked. I loved her shoes, dresses hats and anything else she wore.
As I lay on my sun bed during the day I would find myself daydreaming of her. I would feel a tingling in my loins and find myself adjusting my position to conceal the fact. As the tingling grew and didn’t abate, this would become unbearable and I would find myself slinking off to my room to lie naked on my bed, pumping away at my cock until I squirted out a tribute to her. After a clean up I would be able to return to the poolside feeling temporarily appeased, but the cure didn’t last and soon I’d be thinking of the Online Mistress again.
I had vainly tried to get her attention, by smiling pleasantly when we passed or holding doors open for her, but I either received a haughty look or total disregard in return. There were other girls around the pool and staying in the hotel, but of course I didn’t notice them for I was far too concerned with the Online Mistress.
One day on the beach, I did receive one scrap of acknowledgement in the form of a faint smile when I hopped up and assisted her with an umbrella which was proving difficult to set up. I just happened to be nearby and noticed that she and her friends had arrived at the same spot. Of course I took this blatant non-rebuffal as nothing more than an indication that she had changed her opinion of me overnight, and now considered me a viable male. With this misplaced thought flying around my mind I spent the rest of the day happily imagining courting the Online Mistress and receiving the same faint smile, which from her seemed to indicate approval.
Perhaps she does have some regard for me after all? I began to think as the afternoon wore on. Perhaps I had spent just a little too long in the sun that day, because by the time I went back to the hotel I was beginning to think that I had a chance with her. No, it was impossible, a little voice kept saying, but I kept seeing that faint smile. She doesn’t smile like that at just anyone, I thought. I think she’s just begun to notice me and thinks I’m alright! came my startling revelation. Of course why else didn’t she shove me away or rebuff me? I was elated at the thought of this, then suddenly a problem occurred to me.
The problem was how could I capitalize on such good fortune? I couldn’t spend the rest of my holiday just doing good deeds. Then the realization dawned on me that I would have to attempt to approach her and see if she was receptive to the idea of us getting together. Why not? I thought, I’m as good as any other male! But as the realization dawned so did an awful feeling of dread. What if she didn’t appreciate one of her slaves trying it on with her? There was always the chance she would be put out, and then I’d be for it. I consoled myself that she would probably take it as a compliment anyway, and not be too outraged by such impertinence. Anyway, my cock was up now, for days I had been dreaming about her, I knew I just had to try else I would have no peace at all!
So it was I prepared meticulously. Scrubbed, shaved, put on my best aftershave and clothes, polished my shoes furiously and prepared to attempt to court the Online Mistress. I must admit, I felt a little like the male Black Widow spider, who risks being eaten when he attempts to mate with the female. I went out for dinner, and decided the best time to catch her would be at the pool side bar later in the evening, when they had returned from their evening meal. Hopefully this would place her in a more agreeable mood? I took up position at a table where I could watch TV and took a single large brandy. I would certainly need that.
Some time later the clopping of high heels and some laughter signalled the arrival of the Online Mistress and her friends. She wore a tight fitting blue dress with short skirt, stocking and high heels. My heart leapt when I saw her and my determination to see my quest through was redoubled.
They went to the bar and I observed her glance around to see who was about tonight. I thought I noticed another faint smile when she looked at me, or was it a suppressed grin? Difficult to tell in the fading light. I took a large gulp of brandy, and tried to think about how to approach her? I couldn’t just bowl up with her friends there, it would be quite rude and I’d probably be laughed out of the bar. I would have to be patient and wait for an opportunity to speak to her alone.
An hour later, after I had long since finished my brandy, and when it seemed that the Online Mistress’ friends were busily engaged in talking to some other guests, and she herself was simply listening to the conversation, I deemed it about the best opportunity I would get. I needed another brandy anyway as I was feeling quite anxious. Putting on an air of confidence, I strolled over to the bar next to where the Online Mistress sat.
“Good evening, Mistress, might I buy you a drink?” I asked politely. The Online Mistress regarded me haughtily for a moment and seemed on the point of telling me to get lost, but then with an air of amusement, accepted my offer. “Very well, slave.” she replied, to my surprise. She insisted that I buy her friends one too, and I had no choice but to agree.
As she sipped her drink warily she eyed me over the top of her glass.
“That’s a nice dress you’re wearing.” I remarked.
“Hmm.” she replied impatiently. “Did you want something slave, or did you just come over here to irritate me?”
“Um, well, no not to irritate you, Mistress. No, quite the contrary. Well, you see, I was sort of th-thinking, you know. Erm, well that is, I-I find you very attractive, and I-I was wondering whether you would like to go out for dinner with me one night?” I eventually managed to blubber out.
The Online Mistress regarded me with a look that suggested suppressed laughter, and covered her mouth. I thought I heard a faint titter. Fighting down the urge to burst out laughing she forced herself to put on a serious air.
“You want to take ME out to dinner?!” she repeated incredulously.
“Um, y-yes mistress. I do.” I replied.
“What as if we’re kind of….equals?!” she said, as incredulously as before.
“Well, yes Mistress. You see I realize you are a superior female and all that, of course I do. It would be foolish to regard matters otherwise, but surely you feel the need for some male company from time to time?” I suggested.
“The problem for you though, Stephen dear, is that I don’t regard you as a man at all. You are a mere plaything with which I amuse myself when I’m bored. You seem to forget that I have seen photographs of you naked, and you look so pathetic and sexually inadequate that you really do have no hope at all in that direction.” was the Mistress’ cutting reply.
Fighting down a wave of humiliation, as several people nearby had caught wind of our discussion, I attempted to pacify the Mistress.
“Please Mistress, not so loud.” I pleaded, glancing nervously about.
“How dare you tell me to be quiet!” she said slapping my face to remind me to whom I was speaking.
“I’m sorry, Mistress, I didn’t mean to suggest that.” I replied, feeling a hot glow on my cheek.
“Look Stephen,” she said, “before I would even consider going out with you, you have a major obstacle to overcome.”
“What’s that?” I asked.
“That is, a real penis is at least 8″ in length and thick too. Your withered little worm is barely 3″.” she informed me.
I felt utterly humiliated at having my penis described thus, and in the hearing of her friends and the barmaid too, but I just had to persist in spite of this.
“But Mistress, you don’t seem to understand.” I began, “I just find you so irresistible, everything about you is perfect, I’m not interested in any other women, just you, you see. I would consider it a great honour if you’d consent to giving me a chance to prove to you that I’m up to the job of, well, being your companion?”
The Online Mistress took a deep intake of breath, then explained.
“I think stephen it is you who doesn’t seem to understand. To me, you are pathetic. You’re not a man at all, you dress in women’s clothes and underwear, you’re weak and easy to push around, and instead of a canon between your legs you just have a tiny little pea shooter. You simply don’t have the first idea of how to treat a woman such as myself.”
“I’m only weak and easy to push around to you Mistress, not to anyone else.” I replied. “It’s because I have far too much respect for you to disagree with you.”
“And I have my doubts as to whether you could actually satisfy a woman with that ridiculously inadequate pin-prick of yours.” she went on.
“No, i can, Mistress.” I replied.
“Also,” continued the Online Mistress, “the sort of relationship you are talking about suggests us being equals, a sort of 50-50 give and take kind of relationship, and that we certainly are not. You are nothing more than a mere slave to me, to serve my every whim, and that really is how I prefer you. The thought of you running around free, having your own thoughts and opinions, expressing yourself freely, etc. quite frankly turns me right off. You were born to be a slave, stephen, to a superior goddess such as myself, and that is how you will remain, and you’ll be thankful enough for that! And if I experience any more of your backchat or futile attempts to chat me up just so you can vent your lust, I shall begin devising the most evil tortures for you to endure. Do I make myself clear, slave?”
“But…I..Um…” I bleated, but as the truth of what the Mistress said sunk in I found myself compelled to agree with her, though not out of choice. “Yes, Mistress.” I finally admitted utterly crestfallen.
“Yes, slave.” she affirmed. “And the last word in this matter has been spoken, but there is another matter I wish to discuss with you. That is the pathetic size of your manhood.”
“Please Mistress,” I said “there’s not much I can do, it’s what nature gave me.”
“You haven’t even tried, have you? You realize having such a small cock throws dirt on my name?” she challenged.
“Well, I’m sorry you feel that way about it Mistress, but I could try enlargement or something?” I suggested.
With a look of mock sympathy she said “Oh, I think it would be a lost cause in your case, Stephen. No, you were meant to be puny. Now get another round of drinks before I forget where I am and thrash you.”
I obediently complied, and this brought Mistress’ friends over who had been chatting at the other end of the bar.
“How are you two getting on?” asked one named Marsha. I was about to reply “oh, fine.” when the Mistress said “We’re discussing Stephen’s small penis problem, Marsha. He’s in such a state, he just doesn’t know what to do.”
Giggling, Marsha said “Oh, poor thing.” in mock sympathy, and sticking up her little finger said “Is it about that big?”
I didn’t know where to look, and when Mistress put her finger half way up Marsha’s little finger and said (quite seriously) “I’d say, more that big.” they both fell into fits of laughter. I felt quite humiliated, and uncomfortable as her other friend Fiona, joined us.
“How terrible,” said Fiona, “You must be totally incapable of satisfying a female partner.”
And there were more peels of laughter.
“It isn’t that small.” I replied, defensively.
“Nonsense!” said Mistress, taking out her mobile phone “I have photos of it, and you can judge for yourselves.”
Soon Mistress had located some of the photos I had sent her during my lessons, and I stood aghast for some time as she showed them to her two friends who giggled and cackled merrily.
“Oh, you do need help!” said Marsha.
“Look at his shrivelled nuts too!” said Fiona.
“Really Stephen,” said Mistress “I’d forgotten how totally pathetic you really are!”
Fighting back a tear of humiliation, I offered “Yes, but what if I managed to increase in size, would you give me a chance then?”
The ladies fell about laughing. The Online Mistress was the first to regain her composure.
“Look boy, even if you did manage to increase by say 50%, 50% of nothing is still nothing!” she said.
“Oh please Mistress, look if you would only take me seriously for say just an evening, and let me prove to you that I am capable of fulfilling your needs…” I pleaded.
I was cut short by another slap around the face, and cackles of laughter.
“How dare you suggest you might even be up to the job of fulfilling My needs. I shall be the judge of that, remember your place slave!”
“I-I’m very sorry Mistress,” I apologized, “it’s just that, well, I-I can’t stop thinking about you.”
“Oh, I think the poor slave’s in love with you?” suggested Marsha.
“Is he indeed.” replied the Online Mistress, quite unimpressed, “We shall see.”
I was ordered to buy another round of drinks, and kneel at Mistress’ feet while she flicked peanuts up into the air which I was supposed to try and catch in my mouth. If I missed one she would plant her pointed shoe into my groin quite forcefully to the mirth of Marsha and Fiona. The evening wore on and it got quite late. The ladies were in high spirits with the drinks they’d had, when Mistress suddenly had an idea.
“You know what I think we should do?” she announced, then whispered to her friends, who soon began to cackle evilly. they finished their drinks and advanced upon me menacingly. Marsha and Fiona each grasped one of my arms and with the Online Mistress leading the way, I was virtually frog-marched out of the bar, and up the stairs.
“Which room are you in slave?” asked Mistress.
“Um, number 17 Mistress.” I replied, rather nervously, wondering what they were up to?
They marched me up to my room, and Mistress fumbled in my pocket for my key. She opened the door and I was shoved inside. The three of them stood around me menacingly.
“Right, get your clothes off, stephen!” ordered Mistress.
“B-but…Mistress…please…” I replied bashfully, but with a single motion of her hand, signalled Marsha and Fiona to strip me. I clucked and shrieked but to no avail, as I was seized and had my trousers undone and unceremoniously yanked down, my shirt pulled over my head, and my boxer shorts almost ripped of. I soon stood in the corner of the room red-faced, covering my privates.
“Please ladies, look I think you’ve all had enough to drink tonight and this has gone far enough…” I said.
“Now first of all, I’m going to give you the opportunity to show what you can do with that pathetic little cock of yours.” said Mistress. “Lie on the bed!”
I lay down nervously feeling red-faced and humiliated at lying naked before three fully clothed females.
“Now take your cock in your hand and start pumping, I want you to show us what you can do with it.” she said.
Obediently I began to rub my cock. It rapidly became stiff and rigid as I pumped away. I felt very nervous. What if I felt I was about to cum? Was I supposed to? What if I came too quickly? Evidently Mistress wanted to see something to impress her, and this was my big chance! If I could pull off a good performance, maybe she would reconsider my advances?
I continued pumping. It wasn’t easy with the girls there giggling, sniggering and making rude comments. I also felt under extreme pressure as I so wanted to impress the Online Mistress. This and the girls distracted me and I found it hard to concentrate, especially with them all looking at me. I felt so humiliated. At least it stopped me ejaculating prematurely which had been my other fear. I rolled over on to my side and continued pumping. “Pump it hard slave, as if you’re fucking someone, not tickling yourself to death!” shouted Mistress. Thus spurred on I began to thrust my pelvis into my fist and my engorged head protruded, dark red through my fist. I began to gasp, and a look of tension appeared on my face. At this point my humiliation intensified as I became keenly aware of my nakedness, and degrading position. I felt a orgasm rising within me and determined that I must put on a good show for the Mistress, despite the mocking of her friends. I began to gasp and stutter, my muscles all tensed, my eyes felt as though they were about to bulge out, and my countenance looked as if I were in great distress, but I was almost in ecstasy.
The moment arrived and I rolled on to my back again groaning and pumping my cock furiously. I tried to really go wild, hoping to impress the Mistress as she sat watching showing no emotion. Suddenly there was a shriek of surprise followed by cackling, and a moment later I felt a wet, warm splash hit my shoulder and chest. It must have been my seed jetting into the air as I came. I squeezed every last drop out, and carried on after the orgasm had subsided, but this didn’t fool the Mistress. “All right you can stop now!” she called throwing a loo roll at me which landed in my groin and brought my ardour to an abrupt halt. I cleaned myself up, and awaited the verdict.
“What an over-acted performance.” suggested Marsha.
“But he did almost hit the lampshade with his spurt?” proposed Fiona.
“Probably the result of days of pent up frustration.” sneered Marsha.
“Like popping the cork of a Champaign bottle.” said Fiona.
The online Mistress said nothing.
“W-Was that Ok Mistress?” I asked.
Completely ignoring me, the Online Mistress went onto the balcony and untied the washing line which was strung up at one end. Dumping my clothes that were drying on it on the floor, she instructed Marsha and Fiona to restrain me while she tied the clothes line very tightly around my now flaccid cock. Not wishing to waste her favourite implements of torture the Mistress clipped the clothes pegs to my nipples and scrotum.
“No, no please what are you doing?!” I shrieked.
Marsha’s hand was slapped over my mouth to silence me, while the Mistress finished tying the rope.
“Right, hold him tightly girls!” she said “Here goes!”
The girls held me while the Online Mistress pulled hard on the rope. I let out a stifled shriek as burning pain suddenly erupted in my cock. “Noooo!” I wailed.
Mistress wrapped the rope around her wrist several times and with a gleeful look in the eye tugged lustily on the rope.
“Come on, let’s stretch that feeble little dick of yours slave. By god you’ll thank me for this one day!” she called.
I was being pulled in two directions with my cock in the middle. I struggled and shrieked, but all to no avail. I was terrified she would pull it off. Looking down the end had turned blue and it felt as though it was on fire.
“I won’t have any slave of mine walking round with a tiny cock.” she affirmed.
This treatment carried on for twenty minutes, after which Mistress suddenly let go and we all tumbled back onto the bed. I began to nurse my poor stretched cock, but was ordered to get up, stop acting like a baby and make some tea for them, while they sat on my bed and discussed their next move.
I had barely served tea, when I was seized again. This time Mistress threw the rope over a clothes hook attached to the wall and began to yank hard on it again. Marsha and Fiona sat cackling loudly while I danced on the end to the rope, beseeching the Mistress to have mercy. Mistress tugged away as hard as she could and the more I pleaded the more she stretched. The other ladies intervened when in order to relieve the agony of my burning cock I tried to grip the rope to stop it pulling.
“One more exercise for you before we depart tonight, stephen.” called the Mistress as she went out onto the balcony again. She looked over, as if sizing it up, then picked up a large carved stone ornament in the shape of a lion. Motioning for the girls to bring me out to her, Mistress took the end of the rope and tied it to the ornamental lion. It looked quite heavy, a few kilograms and I struggled to no avail to try and break free. The girls held me firmly against the balcony edge, Marsha’s hand still clamped firmly over my mouth, while Mistress placed the lion on the balcony wall. All at once I saw what she was going to do and tried to shriek and plead her not to, but my protests were muffled by Marsha’s hand.
Mistress stood in front of me, looking magnificent in her stunning blue dress. “So, you think you’re up to going out with me do you, stephen?” she said, and tickled my balls with her finger nail. I struggled frantically, but to no avail. “Well, you’ll need a much, much bigger cock than the one you’ve got now. Are you sure you still want to go out with me?” she said very slowly pushing the ornamental lion to the edge of the wall. I was frantic with fright! And terrified of what would happen if she pushed the lion off the wall, and it fell toward the ground before jerking to a halt, as it was attached to the rope around my cock. I tried to plead with her but my cried were muffled. My ears were filled with the giggling of her friends. All I could do was stare pleadingly at the Online Mistress as she slowly, inexorably slid the lion across the wall toward the edge. “Nooo! Nooo! Nooo!” I tried to scream. Would she really do it? Surely even the Mistress wouldn’t be that cruel? Would she? The lion now teetered on the bring of the wall. Tears of terror ran down my cheeks as I wondered whether the force of the fall would rip my cock off.
Mistress kept it teetering on the edge for some time and knocked it over a couple of times enjoying my jumps of abject terror as she did so. She even pushed it off and caught it one time, I was panic-stricken. At last she picked it up, and said “Oh, did diddums really think I was going to let this nasty weight drop and hurt your poor little willy?”
I relaxed somewhat as the danger subsided, and the girls released their iron grip on me. Gasping for breath I said “Oh, please Mistress, I wish you wouldn’t do things like that! I was terrified.”
“Yes, you did look a little worried.” she agreed with a look of satisfaction. “Anyway, it’s far too late and way past our bedtime, say goodnight girls we can humiliate stephen some more in the morning.”
I received a peck on the cheek from Marsha and Fiona who went back inside leaving the Mistress and I on the balcony. “I’ve decided to treat you to one single, small peck on my cheek for your troubles tonight stephen.” said the Online Mistress, baring her cheek toward me.
“Oh, thank you Mistress!” I exclaimed, feeling that my tortures throughout the evening were more than compensated for now. I eagerly stepped forward to kiss the Mistress on her cheek, when she suddenly flung the ornamental lion she was still holding, up into the air and over the edge of the balcony. “What?!…Nooo!” I shrieked, too late. Mistress was already moving past me when after a short, silent pause I felt the rope go taught, and a searing burning pain erupted in my cock as the full weight of the stone lion was transmitted up the rope to the base of my cock. It felt as though an elephant had stepped on it and I felt something snap in my cock.
“AAAAAAAAAAAAAAAAAAAARRRGGHH!!” I couldn’t help crying out into the night. The final tortured howl of a hapless slave.
As the Mistress passed through my apartment on her way out she paused to listen to my scream, and nodded to herself in satisfaction that the evening had finished on a satisfactory note. i.e. a scream of agony, which all the resort should have heard. Now there was no doubt the Online Mistress was abroad tonight.
By the time I had recovered my wits and summoned up the courage to look down to see if my cock was still attached, the Mistress was long gone. I was relieved to note I still had a cock, and quickly hauled up the ornamental lion, and unfastened the excruciatingly tight rope from around my poor red, raw, stretched cock. Staggering back inside I had to find some ice to bath my bruised cock in. I lay on the bed, still naked, fretting and gasping as I tended to my poor penis. I think a tendon must have snapped as it felt tender and sore, a black bruise appeared on it and it began to swell. I sobbed gently as I moved it from side to side, limp and lifeless. I suddenly realized that ironically, it did look longer than it had been at the beginning of the evening. Not surprising after all it had been through. I lay back gasping with my bell-end throbbing even when bathed in ice cubes. When I thought of the online Mistress it began to swell, and as a consequence it hurt mightily. I groaned in pain again. It was some time before I was able to relax and settle down. Eventually I drifted off into a disturbed slumber, full of awful cackling harpies, and dreadful cock tortures.
The following morning I awoke, and gingerly inspected my tender cock. It was swollen and bruised and getting an erection still caused a lot of pain. I wouldn’t be playing with it for some time, I realized. The Online Mistress had rendered me well and truly hors de combat. I had certainly strained something, and had to spend the morning resting it on a pillow, until I felt able to walk normally again. I began to reflect upon whether it had been wise to presume to try it on with the Online Mistress? I had naively sought to go out with her, and this had been my reward. Well, She coud do what she wanted with me, but at least I had tried, I thought.
Later on, I staggered down to the pool side, braving taunts and jeers from Marsha and Fiona, and their constant “little finger” signs at me. I spent a good deal of time bathing in the cool pool water as this was the only way to relieve the inflamed burning swelling on my cock. It had swollen twice it’s normal size, albeit with bruising and inflammation. Mistress assured me it would feel twice as good when I next came. Unfortunately I had to wait until I arrived home for that pleasure, as the swelling took a week to subside. But Mistress was right, there was a tender tingle whenever I got an erection, and came which lasted for some months to follow. It serves me right, I thought, I was a fool to have ever believed I could get away with trying to chat up the Online Mistress!
Here ends this sorry tale for the time being. I do hope you enjoy it Mistress. I really enjoyed writing it, although it did take a bit longer than I intended, so profuse apologies for keeping you waiting. I just hope it was worth it. As always, I look forward to your comments, and next task.
Yours most gratefully,