This is a print version of story Meeting my match ( Part 1 of 3 ) by louise1234_06 from

Meeting my match ( Part 1 of 3 )

I couldn’t believe I was doing this, as I stood by her front door I struggle to find breath on a surprisingly clear day. It had started some months ago, in an internet chat-room, boy those things can be dangerous. I had spoke to Mary almost every night, soon chats turned to sex then to fantasies. The difference was she only lived in the next town so when she asked to meet I jumped at the idea, she was so sexy in her pictures. Admittedly Mary was 41 and I was 26, but still. She stood at 5ft10, long straight red hair, a body most twenty one year old girls would be jealous of. She was stunning.

Mary had decided it was time to meet, and her place would be best. We had done all the talking that there was to be done, in her words this would be ‘playtime’.

I knocked on the door and within no time Mary opened up, I don’t know what I was expecting but because we had talked so much about bondage I expected her to be in a latex outfit, but she was in a business suit, still smart and sexy, just not that I expected. She welcomed me in, looked around outside then closed the door. Then putting me on edge she locked it, removed the key and placed it on a shelf.

“Don’t want to be interrupted do we?” she asked. “No Mary” I stammered, slightly in awe and embarrassment. “Mistress!” she pointed out was what we agreed.

She walked down the hallway chatting about something or other, I watched her peach like ass moving. Then she turned to face me, grabbed the sides of my face and started kissing. It took no time for her tongue to part my lips and start searching me. It felt so good, goose pimples worked up my back, and my cock started to harden in my jeans. Then she stopped.

“Upstairs, first door on the left, get changed into what’s on the bed, understand slave?” She had spoken like this in the chat-room but her voice made it a little frightening. “Well? get a move on” she said smacking my ass.

I didn’t need telling again, I was off and up the stairs while she vanished into the kitchen. This house was like any other, I opened the door which she had told me to, and found, well a bedroom, what else did you expect, on the bed was a pile of clothes. Sitting next to them I saw what she had chosen.

Ok this was strange, black stockings, a black thong, lacy Basque, long elbow length gloves, knee high boots which looked like they would fit and a strange toy with a note. Before jumping to conclusions I looked around for other clothes, but these were the only ones. I took off all my clothes and began changing into these women’s underwear. God I looked silly, I picked up the toy and was about to open the envelope when Mary walked in.

“I got your…” she said before fully entering the room. “MY GOD, they are not for you” she said shocked.

I almost died, I blushed and looked towards the floor. She threw the pile of men’s clothes on a chair and walked over to me, lifting my chin and looking in my eyes.

“You’re a filthy pervert, you never mentioned dressing up in chat” she scowled. “I’m sorry but…”

Slap she hit me, hard.

“Fine we’ll play your way”

With that she grabbed me and threw me back, she was very strong, maybe it was anger, maybe it was part of her game. I was frightened, not at being hurt, but losing her as a friend. Once on my back she grabbed my arms and I hadn’t seen them but a pair of leather cuffs awaited my wrists, and like a professional policewoman I was bound before I knew it. Next she kneeled between my legs, very close to kneeling on my crotch, quickly to save pain I spread my legs. Mary grabbed one leg and then the other and tied them to long lengths of rope attached to the headboard by my wrists. Before I could figure out what my stupid actions had gotten me into I was tied to the bed with my legs spread and in the air.

“I knew there was more to you my boy” she said smearing the toy with some kind of lubricant. “We haven’t spoken about you dressing up, but you took the bait you’re a pervert”

She got back between my legs and I felt the thong being pulled to one side and some gel being spread on my virgin asshole. The toy I learnt later was a butt plug, about 5’’ long and 3’’ at its widest point. Without any kind of pleasure she slipped the thin bit in, smiled at me then f***ed the rest. As I went to call out in pain a rubber ball with straps landed in my mouth, turning the screams into just a muffled cry. She adjusted the straps around my head and went back between my legs. This was more like it, she pulled my limp cock from the lacy thong, slowly she rubbed me until my cock was hard enough to break ice. Her hands were so good, and the plug was rubbing my prostrate begging me to get hard for Mary. Once hard she looked down and nodded in agreement before placing a 5 ring gates of hell on my cock. One ring behind the balls and 4 rings all going down in size working up my cock. Then a strap separated my balls, making them two hard round objects either side of the strap.

Mary got up and left the room, closing the door behind her. Well it was supposed to be a midday call, have sex and go home, but as my tied body looked out of the window I saw night drawing in. Then to my horror car headlights reflecting into the room, someone had just pulled up on the driveway and I remembered Mary was married…

What the hell was I going to do? Mary had always been honest with me and I knew what I was getting into, I don’t know what this man, her husband was like but what the hell would he think. Here lay on his marital bed was a young guy, probably young enough to be his son. I had chosen to come see and fuck a married woman, if only I knew this was going to happen.

As the engine outside died down and the headlights stopped illuminating the whitewashed ceiling I rested my head back, my bonds were too tight to fight, there was no getting out of this. I hoped, prayed that this guy would just find it funny after that maybe he’d let me go home. The worst thing that could happen is he could put me in hospital.

I heard the front door open and could hear voices, Mary’s soft voice was easy to recognise, and unfortunately I could hear a guy’s voice. I was scared to death now, but somehow I couldn’t stop myself being erect, because of the gates of hell cock rings on my 8’’ cock was throbbing. The head was purple and looked solid, not its normal hard spongy touch. It hurt like hell and if I could have got my hands free I would have taken it off and just allowed my cock to go soft. Being only 26 I couldn’t believe I wanted to be soft, I’d spent far too much time playing with myself to want a soft cock!

Before leaving me for the last time Mary had slipped inside my virgin anus a 5’’ long butt plug, when she had roughly slipped it past my resistant muscles it hurt like hell, but even now that didn’t feel half as bad.

Time passed, I lay there tied down and dressed as some kind of slut, my own punishment for my own stupidity I guess. There were no clocks in the room so I had no concept of time, I think at some point I even fell asl**p. Mary had known from our many chats that I was a single guy, parents lived miles away and I was currently between jobs, which was ok as I lived off my parent’s money. So who would know I was missing, I could be gone days and nobody would know. If my mates tried to get hold of me they’d just think I was on one of drinking weekends. My god, I could be here days.

As it went I had been tied to the bed for close on eight hours. Fear had stopped me wanting to carry out normal duties and that fear was about to increase tenfold. I had been asl**p and I awoke a little groggy when the stairs creaked, there were footsteps approaching. I hoped it was Mary and she would release me from this ridiculous game she was playing. The door creaked open.

With the blindfold on I was desperate to see who it was, I wanted to hear a voice, anything, but instead the bed felt like someone was sat next to me. I moved my head as if looking around, pointless considering. Then it happened. The tip of my cock was poking through the waist-band of the black thong I had stupidly put on, it was in pure pain having being so damn hard. I felt just the tip of a tongue licking over the pee hole of my cock, warm and wet, making my poor defenceless cock throb wildly from its touch. The tongue slid gracefully over the rings that confined my imprisoned cock. Then a hand got hold of my balls, only this wasn’t Mary’s hand, not that I had yet had the pleasure of feeling that, these were big hands.

The hand squeezed lightly, pulling them down and away from my body. It felt like I was being cut in half as the ball spreader f***ed the two globes further apart. I had a horrible feeling that when I heard a gasp the sound seemed like it was male, there was nothing I could do or say but lie there like a toy for a man’s pleasure.

I’d never considered myself gay, or even bi. I’d watch porn like everyone else and seeing two guys did nothing for me. But as I got older I thought about it, only a little, but as soon as I started getting to know women properly the thoughts left my head, and there was no way I wanted them back. But I wanted to get off, I needed to cum and at this moment in time I didn’t care by whom. I wanted this rough large hand to just pump my cock until I was milked. My back was arching as the hand rubbed, trying desperately to increase friction, oh how I needed that hot rush to leave my balls.

Then the persons second hand came into play and started pulling and pushing at my butt plug, twisting it. All the time it rubbed over my prostrate turning me on, making me wriggle underneath my unknown captor. I had heard stories about men apparently having a G spot but it must have been old wives tales, if you could turn a guy on that much why the hell put that spot up a hole that’s only supposed to be used for getting rid of rubbish. But this guy moved the plug about until he heard me gasp from beneath the ball gag that was forcing my mouth open. With that he had found the spot ensuring that the tip of the plug kept running back and forth over the gland he fucked me with the toy for about five minutes, still I hadn’t heard anyone speak, it was spooky, I was being pleasured in ways I didn’t know by someone I couldn’t see, who was the same sex.

At this moment of time I didn’t care, all I knew was the constant rubbing of this so called G spot was causing the cum deposits in my balls to grow and grow with no release. The 5 cock rings that encircled my cock were not letting anything escape. If it was turning this guy on and that’s all he wanted to do then go for it, hell as long as I could cum I didn’t care.

Just as the soft silicon surfaces of the plug were giving me immense pleasure the rules of the game changed, the small plug plopped out leaving me feeling empty.

“Don’t worry you wont be empty for long” a rough voice said.

The weight on the bed next to me shifted and I felt the mattress between my legs being pushed down, this was not good news. Suddenly realising what he meant I panicked, my breathing increased and I was snorting through my nose because of the gag. My god he wasn’t was he?

I felt what I could only guess was the head of a cock sliding up and down my anus, mixing his pre-cum with the lubricant that had eased the plug in earlier that day. My god no please, that’s what I wanted to scream but I couldn’t. Slowly the cock pressed harder and harder toward my virgin hole, I didn’t want this. I tried to tighten my muscles as some kind of defence but it was useless they had been so relaxed from the plug that it was no more that a tight pussy for this man to enjoy. Then with a burning sensation something hard pushed inside me, it was about twice the width of the plug and judging the feel of his cock, it must be ten inches long. As my ass began burning he stopped just two inches inside me, he was incredibly hard, I had no idea at the time but his cock was already big, but had been made a lot harder by the single cock ring at the base of his cock.

As my ass got used to his girth I lay back flat, giving myself to this strange before I was hurt, I guess I had to be thankfully he didn’t f***e the entire length straight in me. As he allowed me to get used to it he went back to using a fingertip on my cock, tracing his short nail up and down the underside of it through the fabric of the thong. Surprisingly to me there wasn’t any sign of pre-cum, in reality my stomach should have been sticky with the stuff by now. Without warning another three inches f***ed my ass to part as I felt the thick head working its way deeper into me. Sapping my strength, sapping my will. With 5’’ in me he rocked back and forth obviously enjoying the tight velvet like ass that gripped his cock. The tip of his monster began rubbing that dam gland again. Now feelings were getting strange, I didn’t want a cock in me, it hurt, but now there was a tingling of pleasure shooting through me, don’t stop.

This time the wait was shorter, he was getting excited and showed it by the way the whole 10’’ was quickly buried inside me. The he started fucking me, pulling his cock out to the tip very very slowly before ramming the b**st back in me hard, back slowly he went again, each time surging forward spearing me on his meaty thick cock. Back and forth it rubbed over my prostrate building the cum in my balls, the cum that had nowhere to go.

The fucking, the ****, whatever the hell it was, lasted for about twenty minutes. My body had given up on me a long time ago, but my mind had gone now, I wanted this to happen, I needed to be fucked while dressed like a bitch. If I could get the gag out I would have begged to feel his cum, but there was no way that was possible. My ass had given up all signals of fighting back, or signs of pain, it was now pleasure, it might have taken some time to get to that point but I didn’t want to stop. The gag was in tight but I didn’t need to beg him to cum, without warning I felt his cock swell as he slowed down his strokes. His cock was pulled back, the tip at the entrance of my hole, all the way out. Then in one powerful stroke it slid down my anal passage right up to the hilt. Then it came, a flood of boiling cum filled me inside, it felt like the power of the orgasm shot through to fill my stomach. My god I wanted to join him, but instead I lay there like some dirty toy being used by a stranger, and I wanted it!!!

A few grunts later and a few shorter spurts of cum later I felt the cock reluctantly leaving me, leaving me empty again. My senses suddenly came back, shit what had he done, ****d me. When they untie me I was going to be mad, this bloke and Mary, she had tricked me it was her fault.

The weight on the bed between my legs vanished with a huff and a puff, all it left was the thick hot cum sliding down my insides, soaking the bed under my ass cheeks. I tried holding it in but to no avail, most of it was leaving me rapidly. I lay there in a surreal world, still in darkness, still wondering what had happened and how I got into that position. The guy left the room and again I was alone. Knowing that nobody could see me I allowed my body to relax and even found myself wriggling in the pool of cum that had congealed under my ass cheeks. It had been only ten minutes and I was relaxed, almost dreaming of it happening again when I heard a little clap, single slow claps and a weight on the bed next to me again.

“You seemed to enjoy that,” Mary said pulling the blindfold off.

She was still beautiful, her red hair framing her face, her red lips full. The last time I had seen her she was in a plain boring business suit, now she sat next to me in a PVC thong, a push up bra, stockings and knee length boots. Her gauntlet gloves worked up and down my Basque before slipping over my tortured cock and down to my ass. A smooth finger began slipping in and out of my used ass.

“You’ve been a good boy” she said smiling, I just wanted to call her a bitch but the finger felt so good massaging my sore anus.

Mary leant to one side almost making me look over into the corner of the room. There it was set up on a tripod, a bl**dy camera. If this gag hadn’t been in my mouth and me so tied down I would have hit her.

“Now I can see in your eyes you’re mad, but through our chats you have been subconsciously submitting to me boy, you know it. If I said jump you said how high” he voice was soft and level, she had no feelings for what she had just put me through. “I tell you what we will do,” she continued. “I will leave you tied up for the whole weekend, don’t worry WE will feed you and help you to the toilet, if after this weekend you want to leave then you may do so, however I will keep all the videos, if you chose to serve us both as our sissy slave then you get the tapes and your world becomes a lot bigger and meaningful”.

I couldn’t reply, I couldn’t move, I tried to demand she release me using my eyes but that was pointless as the blindfold slipped back down.

All I could do was lie there full of cum wondering what my weekend would bring, how would they make me serve them, the moment I was untied I was off to the police, or was I?

When the ordeal was over it was almost midnight I hadn’t realised but it had all been captured on videotape and Mary, or Mistress as I was to call her offered me a deal. Stay the weekend and leave Monday with the video and serve them as their sissy slut or leave now and they keep the video tapes, if anything was ever said about them the video would be sent to all my friends, f****y and workmates, not a hard choice, I wasn’t happy but I had to stay….

I’m not sure if Friday night I fell asl**p crying to myself under the blindfold, I just don’t know how I could have been so stupid to fall for tricks such as these but I had and I had chosen to see the weekend through as a sexual play toy for Mistress Mary and her husband, either way I awoke the following morning. Although I couldn’t see the sun because she had put the blindfold back on last night I could feel its warmth through the windows and knew that the first of my three nights were over. My anus still hurt from the pounding her husband’s 10’’ cock gave me last night, the cum that had freely dripped from my ass was now all over my cheeks, I was in some kind of mess.

My sense awoke when I heard the bedroom door open, I had half hoped that Mistress and her husband were staying in bed after last night’s fun and games, but on the other hand I didn’t want to be left here to rot. The footsteps on the floor were light and sounded as if they moved gracefully over the floor, but each step brought the person closer to me. Slowly and carefully my blindfold was raised and I was shocked at what I saw leaning over me.

Stood there naked and in all her glory was a young girl I had never seen before, she was no more than 21 years old. Her blonde hair was long and beautifully looked after, her eyes as blue as the sea. She was stunning, but who was she and what was she doing here. I moved my neck about trying to free it of the aches that had come from sl**ping in a restrained position, I looked the girl up and down, her skin was pale but a perfect complexion, which was easy to see as she was completely naked all but for a leather collar which seemed to be a little too tight around her pretty neck. Her pussy had been completely shaven allowing me to see every inch of her sexual beauty.

“Who are you?” I asked with a dry throat.

She ignored me, only smiling with those sexy lips as she pulled the blanket from me to reveal the sissy underwear I had been wearing. Where the thong had slipped back into position over my anus it had the remnants of dried cum from Mistress Mary’s husband. The young girl smiled and climbed on the bed next to me, turning she stayed to one side but her ass and pussy lips were in plain view for me to see. Now like most men I like to wake with a hard-on, and the feeling was good, having a sight like this inches from your face on a Saturday morning was almost enough to let me forget about last night. But as my shaft got thicker and began to harden I was bluntly reminded of last night as the cock ring behind my balls and at the base of my shaft took effect. My cock was too far gone to go soft now, it kept hardening, sending the bl**d rushing up my shaft, past the rings into a place where it would stay for some time. Last night when I had hardened wearing the rings it had been painful but this morning it was painful but also a pleasurable feeling. I hadn’t come so any kind of contact against my cock was a welcome pleasure.

Just as the young girl was about to do something I once again asked her what she was doing here, she turned as if to say something then stopped quickly as Mary walked into the doorway. The young girl caught Mary’s eyes and immediately dropped her head as if in shame.

“Boy you can speak to her all you wish but she knows not to answer you, if she does she knows her punishment, just let her do her job, you might enjoy it” Mary barked before leaving and heading downstairs.

The girl didn’t bother to look back at me again, she just began to do her work. I could feel her long finger nails pulling at the cum soaked thong, pulling it once again to one side to show my anus off, its humiliating having a strange but beautiful young girl staring straight down at your recently fucked hole. As she leant forward a little more her erect left nipple made contact with the tip of my cock, she lowered her head even more, rubbing my cock head teasingly with her nipple, was this her job to frustrate me, if so it was working. Then her actual job started, the younger girls tongue flicked out and began licking my asshole, I have to admit it felt good, like I say I woke a little sore but this was just the kind of medicine needed. She had been licking around my ass for some time, her tongue occasionally passing over my anus, all the time torturing my cock. It was now obvious that her job was to clean me of last night’s cum. When the exterior was cleaned her tongue began to move into my ass and it was heaven, if you’ve never had a skilful tongue enter you there before you have to try it. Not only was her nipple rubbing my cock but also as she licked I used what movement I had to wriggle about, trying desperately to rub my cock more in the hope of cumming. It was no good I wasn’t going to cum, not with this dam harness on.

Mistress Mary entered the room again and looked at the young girl’s handy work, once she was happy she sat on the bed on the other side of me and rested a small toilet bag between my spread legs.

“Slut you may suck his cock while I work” she said to the girl, “but do not make him cum, if you do you’ll be in trouble”. Mistress leant forward and placed the ball gag back in my mouth before I could complain.

Immediately the girl began using that experienced tongue on my shaft and balls, circling the head of my cock before moving down to my balls. Taking each one in her mouth she sucked and pulled on the swollen balls, again it was painful but I didn’t want it to stop. Then she would leave a trail of saliva as she licked all the way back up my angry throbbing cock before engulfing it down her throat, as I was in her mouth her tongue continued to rub up and down my shaft from inside, it was heaven but torture because I knew I wouldn’t be able to cum in her mouth, or maybe cum all weekend.

As my cock was being pleasured I felt some cream being spread over my asshole, I didn’t want to be fucked again so it came as a surprised when I felt something sliding up and down between my cheeks, then it dawned on me, Mistress was shaving me. After five minuets Mistress was done, she sat up and looked at her handy work.

“Hmm much better, if you’re going to serve as a sissy for us I don’t want to see hair” she stated.

Mistress adjusted her position and pulled the young girl off my cock by her hair.

“Go sit in the chair and entertain yourself” she commanded.

The girl got up and walked to the chair as ordered, both Mistress and I sat and watched the naked beauty as she sat in the chair and lifted her legs until they were hanging over each arm, her shaven pussy clearly on show for us both to see. Her fingers got busy, one hand immediately went to the nipple that had been rubbing my cock, and slowly she pinched it and pulled it, allowing a few light groans to escape her mouth. Her other hand slipped down to her glistening pussy and slowly she rubbed her clit.

Mistress had soon seen enough and went back to the pubic hair around my groin, no, this was wrong I had to stop her, she couldn’t shave there. But I was in no position to fight and I knew it, instead I lay back, turning my head to one side and watched the young blonde masturbating. Mistress went to work and before I knew it I was clean shaven, hairless like I had been as a boy, but now I was her boy, her toy, her slave?

Using a finger to beckon the now soaked young girl over Mistress Mary just used her eyes to instruct the girl to get on all fours over my chest, her tits swung teasingly close to my cock that was now begging to be allowed to cum. Mistress in the meantime had slipped on a realistic looking 9’’ thick black strap-on, no sooner had she put it in place and she was behind the girl, without mercy she plunged it deep and hard into the girls shaven pussy, the whole bed shook but the girl took it. For ten minutes the two of them fucked over me, Mistress would pull the cock out right to the tip then drive it straight back into her young victim, pull it out and drive it back in. I tried to keep count but I think the young girl came about four times, and each time Mistress pulled the cock from her the juices from the sweet young girl dripped onto my chest making a sticky yet sexy mess, the aroma of sexual activities was turning me on, let alone watching this big black cock abusing her.

Soon they were finished and the young girl left the room, walking slightly funny, out of breath and red faced. Me I was still lay there, trussed up, gag in mouth, a tight thong rubbing on my abused cock. Mistress stood straight and removed the cock from around her waist. Once off she wiped it over my face and around my nose, leaving the young girls scent on me.

“Were all going out now my boy except for you, but tonight you might get to cum, if you behave, understand”

I just nodded and with my answer Mistress left the room, only stopping to slide a video into the recorder. She closed the door and left, before I heard her heading downstairs the video started, this was going to be interesting, Dominant men fucking TV’s, I had no choice I had to watch.

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