The Day I Lost My Anal Virginity To My Domme's Strap-On

Miss J, Ballbusting

Tuesday, 31st July 2012

A week or so ago Jade had said to me "I'll really get the chance to put you to use as my slave as next week because I have a free house for two weeks, so I could use you in the evenings and have you clean and do my laundry. Would u like that slave?"

Of course, I said "yes, Miss J." She'd told me she wanted me to come over for one or two nights to hoover, mop, wash up and change her cat's litter tray. I leapt at the chance, but Jade brought me back down to earth by saying "I really will have to feel I trust you before I let you in my home. So we'll see."

It seems I did earn Jade's trust, because now here I was on an unfamiliar bus route over to East London. I was feeling especially nervous about this meeting, perhaps because it was on Miss J's turf, or perhaps just because it was a part of suburb I'd never been to before.

Miss J had said that morning, "I want to try the strap-on today, so make sure you are fresh from the shower and use the douche before you leave." Of course I was also fully shaved, as was a standing order. As I neared the address Jade had given me, she messaged me saying, "can you stop somewhere and get me fresh custard with apple crumble or a berry crumble, preferably a berry crumble. I'll make an exception if you're late because of it."

I did as asked and showed up to Miss J's house, her family home. I was only a few minutes late and was let in. There was little conversation or small talk. Miss J got straight into my orders. As it turned out, there weren't a huge amount of chores for me to do. She just wanted her dinner cooked, which was an over-ready pizza, so petty minimal effort was required on my part. While the pizza was cooking, there was a sink of washing up for me to do.

Once the drying dishes were stacked in the drainer, I floated around the kitchen for the final few minutes of the timer counting down to Jade's pizza coming out of the over. I put it on a plate, cut it as instructed and brought it though to Jade's in the living room with a glass of water.

I returned to the kitchen to put Miss J's dessert in the over. Then went back to the living room where I was told to sit in the corner and face the wall while Miss J ate. I vividly remember that the television was on and Jade was watching some of the Olympic coverage, which was taking place in London at the time.

I can't describe how it felt sitting in the corner. It sounds boring, but the anticipation was intense and knowing I was obeying Jade's commands made it exciting. Once Jade had eaten her pizza she was ready for her dessert. I went to the kitchen and microwaved the custard while the crumble spent its final few minutes in the oven. I dished up, took it through to Miss J and returned to my corner and waited.

Eventually I heard just put her bowl down and I was called over. My first task was to suck on her toes, something I willing did. Toes and feet do turn me on, but knowing it was a part of Jade's body excited me, especially since I know I have no right to touch any part of her or do anything to her without her explicit say so. So I was appreciative to get to pleasure her with my mouth and tongue.

After a while Miss J asked me to give her a foot massage. I never felt massively confident doing this, but since this was the third time Miss J had asked, I assumed I must be doing something right. This time my mistress provided her own lotion to make the task easier. Of course, if I wasn't performing the massage correctly, Miss J was quick to tell me and also instructed me on exactly where to focus my attention. I got a few slaps around the face for getting things wrong or not putting in the required efforts, or perhaps just because Miss J enjoyed slapping her slave.

With her feet soft and cared for after my massage, Miss J was now going to put those feet to use to cause me pain. She order me to drop my short and boxer and get on all fours. I knelt in the middle of the living room.

In this vulnerable position, Miss J let rip on my balls. Stood behind me she kicked me hard between the legs. One hard punt, followed by another, I fell to the carpeted floor as Miss J swung her foot into my tender balls for a third time.

Miss J seemed a little annoyed at my inability to take this punishment and told me to lie on my back and bend my legs. In this position Jade could kneel between my legs and keep them apart, there was no way to protect myself. Miss J balled her fist and slammed it into my nuts again and again, while slapping my thighs if I even tried to protect myself by moving my legs. After seven or eight hard punches the urge to protect myself became too great and I curled up in a ball with my testicles safely between my legs.

But Miss J hadn't finished hurting my balls yet. She grabbed my knees and forced my legs open, resuming her position of power between them. She then grabbed the flogger she'd asked me to bring with me. This was the same cat o' nine tails type whip she'd used on my on her previous visit.

She swung the whip against my groin, the tough leather strips stinging my scrotum with a flick that made my balls ache. Although intense, the pain wasn't as bad as Jade's foot or fist. I was able to take several lashes of the whip, this time not squirming and curling up into a defensive position. I rode out the whipping until Miss J was ready to try something that was new for both us.

Miss J was wearing a large t-shirt and a pair of comfy joggers, the type that are perfect for lazing around the house in. Stood in front of me and I still sat on the floor, Miss J dropped her joggers to reveal her cute grey and purple panties. She then picked up the strap-on I had brought.

This is something Miss J had asked me to get. She'd experimented on me with a carrot on our previous meeting, but she want a better experience. I'd bought a "beginners" strap-on kit. It consisted of a harness with velcro fasteners and two dildo, one which seemed big enough - it dwarfed my cock. Plus a much bigger rubber cock. I'd left the larger of the two at home and hadn't told Miss J it existed.

Not daring to stand up around Miss J, I helped my mistress fasten the harness around her slim body while kneeling in front of her while trying to resist groping her shapely ass as I did. With the harness attached, the smaller of the two dildos stuff out in front of Miss J. It was six inches long and at least as thick as my dick. I was in the perfect position to suck on Miss J's strap on, something she quickly demand. I sucked how I imagined I'd suck a real cock, taking as much of the length in my hungry mouth, swirling my tongue around the head and working it as best as I could.

After a while, Miss J pushed me away with a hand to my forehead and told me to get on all-fours. I knew at this point that I was about to be fucked in the ass for the very first time. I knelt in front of Miss J's fire place and felt something cold against my ass hole. It was a squirt of lubricant that Miss J worked in with the tip of the rubber cock. Moments later she pushed the full six inches inside of my ass. It didn't hurt and was actually quite easy to penetrate.

It did however feel incredible. Not the sensation of the dildo inside of me, but the power that Miss J had over me at this point. The exchange of trust and the humiliation of being used in this way. The more Miss J slammed her hips into me as she knelt over me, the more under her control I felt. It felt uncomfortable, but exciting. I also felt helpless as I knew there was no way I could stop this.

Miss J struggled a bit with the angles. I guess it's just a little different to fuck as a man when you're female. She had my lie on my back and hold my knees up over my chest. She once again slid the dildo inside of me and got on a little better fucking me in this position.

Surprisingly, Miss J reached out and began to stroke my hard cock. She timed her tugs with the thrusts in which she pushed all six inches of the dildo inside me, her thighs slammed against my ass cheeks. Her hand felt good on my cock, but the stimulation didn't last long enough. She was careful to stop this reward before it felt too good.

While I was being pegged I became aware that the sport had finished on television and the Olympic theme, an emotive song by Elbow was playing on loop. Years from now, this song will still hold strong, fond memories of the day I was fucked in the ass by Jade on her living room floor.

As my first anal fucking came to an end, Miss J said "you seemed too comfortable. It's very small, you'll have to get a proper strap-on at some point, but will do for now."

After pulling the dildo out of my ass, Miss J said "suck it, clean it off." I did as I was told, perhaps not as enthusiastically as the first time I went down on it, but obey. Thankfully my efforts with the douche seemed to have paid off.

Miss J then want me to serve her by worshiping her pussy, but realised that she didn't want my tongue on her after it had sucked a dildo that had been in my ass. She said, "stay there". So I sat on the living room floor and waited as Miss J went upstairs. She returned with a bottle of mouth wash and made me rinse my mouth out, giving me no other option than to swallow the strong-tasting liquid once I was done.

Jade took her panties off and sat back on the sofa. She snapped, "lick me, gently". I crawled between her legs and began to gently tease her delicious pussy. I slowly licked up and down her slit, worked my tongue inside of her and teased her clit, pushed it deeper and lapped up her sweet juices.

Jade seemed to enjoy making me taste her and knowing that I was consuming her. She grabbed my head with a hand on each side and told me to stick my tongue out. She then guided my tongue over her pussy, essentially making me lick her exactly where she wanted it.

She said, "make you tongue a point". I roller my tongue and she pushed my face into her crotch, forcing my tongue inside of her. "Lick," she ordered, "scoop it out." I tried to collect as much of her juices as I could. She then moved my face away from her wet pussy so she could see my face and ordered, "swallow it". I gulped her juices down and barely got a chance to breath before Miss J pushed my face back into her pussy.

This process was repeated several more time before Miss J said, "lick my ass". I request I wasted no time in fulfilling. I lowered my head in order to push my face between her ass cheeks, my eager tongue stretched out and make contact with her ass hole.

I reached up and grabbed her ass, gently spreading her cheeks with my hands and began to kiss and gently lick her stretch ass hole. The familiar, but not unpleasant, flavour filled my mouth as I enjoyed being used for this humiliating act.

As I licked her ass, Miss J pulled out a purple vibrator and held it against her clit as I continued to lick. The vibrator occasionally made contact with my nose, creating a slightly odd vibrating sensation though my whole head.

After a while Miss J said, "lick my clit again". I did as I was told, my tongue met the vibrating tip of the purple toy on Jade's clit. I licked furiously and she rubbed her wet clit with the vibrator. Sadly, I failed to make Miss J cum for a third time, even with mechanical help. This really wasn't like me, I've never had trouble making a woman orgasm before. I was trying so hard, but just couldn't get Miss J there.

Miss J said, "I'm going to the other room. Get dressed and leave, I don't want to speak to you again today." I responded by saying, "yes Miss J, thank you for allowing me to serve you today, it was an honour. I hope you were pleased with my performance."

She merely left the room and walked through to a room I hadn't been allowed in at the front of the house, presumably a family room. I got dressed, packed our toys in my bag and left with Miss J's juices still smeared over my face.

My balls ached, both from being beaten and from being aroused and teased for the last three hours. Miss J hadn't let me cum. My mistress' scent filled my head all the way home. During the journey Miss J messaged me to say, "I just checked my pot and saw it wasn't washed properly. That's a let down after everything else went well." I would have to make it up to her.


The story continues: Out Of My Comfort Zone & Relentlessly Used