Chapter 1: First Encounter I came across Hailey online, her profile indicated that she was interested in exploring her submissive side. We chatted for a while and I soon became convinced that she was genuine and an ideal candidate for training. I set her some rules and some challenges, and she eagerly accepted. Dress code is important to me, so Hailey could wear bra and panties, but never a thong, and stockings or bare legs, but never tights. I then sent her to a shop in London’s Soho with a shopping list including crops, leather restraints, vibrators, nipple clamps, gags and then suggested she use her imagination to select some surprise items. It was time to meet, as I walked up to her front door I was as horny as I had ever been. She opened the door, and I got my first look at her in the flesh. Hailey was tall about 5’ 10”, long ash blonde hair in a ponytail, white tee shirt, dark grey pleated skirt, and neat black shoes. I was glad to see she wore nothing on her legs. Hailey had given her age as 34, but she looked younger. Her figure was slender, but her breasts were full, and I could see she was not wearing a bra, her nipples were large and firm. I was pleased to see she had skillfully applied her makeup, eye shadow, mascara, and dark red lipstick. “Good Hailey, you have dressed to please, and you have. Now let’s go upstairs,” I murmured into her ear. She turned and began to climb the stairs, I bent to lift the hem of her skirt, and was surprised to see bare cheeks and the string of a thong. “Oh, dear! That is bad, now I will have to punish you,” I told her, relishing the idea. In the bedroom across the bed, Hailey had laid out her purchases from the Soho Sex Shop. I investigated and saw that in addition to my list of essentials she had purchased a pink remote-control vibrating egg, a selection of black rubber cock rings, and a see-through textured cock sleeve. First, I selected a ball gag and put it into her mouth, gently but firmly tying it at the back of her head. I had Hailey lay on the bed on her tummy and lifted her skirt to better see the offending thong, it was made of black leather and had obviously been bought on her recent sex toy buying trip. Clearly, she was testing me too. Down came the thong, pulling away from the crack of her bum. I peeled it down but left it just above her knees, that was to remind Hailey what had been the cause of her punishment. I ran my thumb from the small of her back, between the cheeks of her arse, and then between her pussy lips – she was satisfyingly wet. I spanked her bare bum, each buttock in turn, fast and hard, enjoying the fast-developing blush of red. When I got her to her feet, I could see tears in her eyes, but her nipples were still hard, and her cunt was very wet indeed. I ordered her to undress and revelled in her naked magnificence. I tied her wrists and removed the ball gag. Kneeling she knew to take my cock in her mouth and to cradle my balls and cock in her fingers. I let her fondle and caress my penis, and suck and lick. This was so I could assess her cock sucking skills – not too bad, but I thought she needed a bit of schooling. So, then I sat her on the edge of the bed and pushed her back with legs wide apart. I loved her shaven pussy and its neatly trimmed Brazilian, quite the cutest cunt I had possessed in a long time. My turn now to kneel and to lick, and to flick my tongue over her clit, and even to spread her pussy lips with my fingers. I set to and began to explore and probe the folds of her vagina, fucking her with my tongue. Mouth hard up against her vagina, my tongue going in and out, as deep as I could reach, fucking her with my mouth until I was rewarded with Hailey moaning and squirming under my oral onslaught. She orgasmed, and that was my cue to stand and to turn Hailey around, so her arse was presented to me. I positioned her legs and pushed her head down onto the bed, so her pussy was just at the right height. I rubbed my penis against her labia, spreading her pussy lips apart with my erection, teasing her arse with the tip of cock, and finally pushing my penis into her wet and willing vagina. I could feel her vaginal muscles gripping the shaft of my cock, holding me inside her cunt. With my hands gripping her waist I pulled Hailey back and forth along my cock, deep slow strokes of the length of my cock – delicious! Of course, this was going to be just about my climax, so I sped up, fucking hard and fast, enjoying the feelings building up in my cock and balls. As I neared my orgasm, I slapped several times at Hailey’s still red bum, until I came with a long burst of sperm, followed by several smaller bursts, until I was spent. Only after I had showered and dressed did I release Hailey from her wrist ties. Chapter 2: Remote Controlled The next day I telephoned Hailey and ordered her to insert the remote-control vibrating egg into her pussy. When she was ready, I opened the app on my smartphone and gave her a gentle continuous vibration, judging by the sounds she making I surmised that Hailey was enjoying the sensation. Experimenting I tried out the various settings, a little faster, then I tried a bit slower, interspersed with gentle and then powerful pulses. Hailey was breathing hard and I could tell that it was all going very well. That evening I had a surprise for her. We were going to a smart restaurant and she was to dress appropriately. “Oh! And be sure not to wear any knickers,” I said, adding. “And don’t forget to put the vibrating egg in your handbag.” She had brushed her hair up and looked a picture dressed in a light blue floral summer dress with a plunging neckline. The dress showed her beautiful cleavage to great effect. Once seated and after we had ordered, I leaned over the table and ordered her to visit the Ladies and insert the vibrating egg. On her return, I dialed in a slow pulsing vibration, glad that I could not hear the buzz of a motor above the hubbub of the busy restaurant. As Hailey ate and talked, I teased her pussy with bursts of harder and faster vibrations, it was fun watching her try to keep her composure as the vibrating egg stimulated and excited her vagina. Later having paid the bill, we walked to my car, I kept the vibrations going and Hailey held onto my arm as if her life depended on it. “For Gods, sake take me somewhere where we can fuck before I go mad,” she pleaded with me. As I drove to a nearby ‘lovers’ lane’, Hailey undid the belt of my trousers and released my cock, rubbing and squeezing and playing with my cock head. No sooner had I parked than Hailey went down on me, taking my cock in her mouth, and she began sucking and licking me frantically. Of course, I kept up the fast vibrating and pulsing rhythm deep in her pussy the whole time. I told her to get out of the car and lean over the bonnet so I could lift her dress up. First, I removed the now silent egg and replaced it with my cock. Within seconds Hailey was orgasming, flooding my cock with cum, knowing she had climaxed I could concentrate once again on my own pleasure. Pounding in and out of her cunt, I soon ejaculated, breathing hard, but satisfied. We played and experimented with the vibrating egg a lot, sometimes in public, and even once on a crowded train. But the best time was when I inserted the pink egg and then tied Hailey’s legs together, and then her arms behind her back before putting on the ball gag and gently laying her on the bed. I knew by now just how to start the journey to Hailey’s orgasm, slow pulses growing harder and faster. I soon had Hailey squirming and rolling and gyrating in time to the vibrations in her vagina, and I could see her pussy lips were getting swollen and wet, as I pushed the settings to maximum and was treated to watching her full body orgasm, contained and restrained by the cords. I let the vibrations leak away, and ease for a while, and then began again. Her second orgasm was not so strong, but it did last for quite a while. Finally, I released her from bondage and took out the egg, she needed to recover, but eventually, we had a nice vanilla fuck. Chapter 3: Cock Sucking Practice I was acquainted with Tony, the owner of a nearby sex shop, who had recently created three adjoining video booths, each with cock and ball-sized holes cut in the walls. Each Gloryhole booth had a TV on the wall, a keypad to select a porn video of choice, and a couple of chairs, oh! yes, and a strong deadbolt on the door. This was a concept that was common in America, less so over here, but word soon got around that Tony’s backroom was, for a suitable fee, the place to see a choice of porn videos and maybe get a blowjob at the same time. Because I had felt that Hailey’s cock sucking technique needed some improvement and since practice makes perfect, I had arranged for her to take a two-hour session in the middle booth on a Friday evening. I had made it clear to her that she was to service all cocks presented at the Gloryholes, taking cum on her face or on her tits. While Hailey undressed, I selected and played a ‘Gloryhole Visits’ video which featured two teenage girls hard at work sucking cocks in a similar booth somewhere in America and then settled down in one of the chairs to watch it with Hailey. Hailey watched the two girls getting facials, and tit cum, and one girl even turning around and pressing her cunt up to the Gloryhole for a fuck. I could see that Hailey was getting turned on by the video scenes, mesmerized she was rubbing her nipples and her cunt as cock after cock shot sperm on the girls. After a while, I undid my belt, unzipped my jeans, and pulled her onto my erection as we waited for her first customer. Her cunt felt wet and warm as my tumescent cock penetrated her vagina, still staring at the screen Hailey began to rock back and forth on my cock, god that felt so good. Just then we heard two knocks on the wall, and we were off with customer number one. Hailey knocked back twice and instantly a rock-hard cock complete with a pair of balls pushed through the Gloryhole. Hailey sat on the chair, legs wide apart took the cock in her hands, and began an exploratory rubbing. Soon she was bending to take the cock helmet into her mouth and gave this cock all the attention it needed to explode in her mouth. Releasing the cock Hailey turned to me and let the cum dribble from her open mouth onto her tits. Two more knocks, this time from the other booth, she turned repositioned the chair, and answered with two knocks of her own. Customer number two was only semi-hard, so Hailey squeezed and played with his testicles for a few moments before starting to wank a by-now erect cock. Again, she leaned in and took the penis into her mouth, continuing to stroke its shaft she licked and sucked. Then when she could feel he was close she made him cum with a flying arc of jizz covering her cheek and neck. Cock number two quickly disappeared. All was quiet, so Hailey came back to me and I let her cunt slowly envelop my still hard cock and we watched some more of the video. Hailey rocked back and forth as cock after cock was sucked and wanked to a climax on the screen. Until, finally, there were two sharp raps for Hailey to answer. This time her customer was a well-hung black man with a tight ball sack. She wasted no time slurping his dark brown cock into her mouth and gave him a blowjob to remember. In no time the big brown gleaming cock was spurting cum over her face, and hair, and tits. I complemented Hailey on her technique, just as customer number four gingerly tapped on the wall, eager for more she quickly echoed his knocks and fell on the average size prick proffered through the Gloryhole. By now she was so excited that she gave the cock a hard and rough rubbing, squeezing its glans and shaft demanding a cum facial. As she wanked that cock, she was also frantically rubbing her own pussy lips and clit and had barely taken the cock into her mouth before he came with an audible sigh. As the cock withdrew Hailey turned to me and opened her mouth, so that I could see the cum dribble out onto her breast, she rubbed the cum into her nipples and used it as lube on her puffy pussy lips. Without prompting Hailey returned to my chair and sat on me so that my cock could easily slide into her slippery cunt. Feet on the floor she rode my rock-hard cock up and down, up so that only the tip of my penis was held in her pussy and then down balls deep. I reached around for her tits and squeezed her nipples between finger and thumb as she continued to bounce on my boner. The up and down rhythm made my balls twitch, and I would gladly have ejaculated then and there, but once again there were two knocks on the wall. Dutifully Hailey stood and let my cock fall from her cunt to attend to another big black cock, but then again perhaps it was the previous one back for some more cock sucking who knows. Anyway, Hailey obliged, cooing over and then caressing his big black balls, stoking the heavy shaft against her cheek with her other hand. Eager to continue she took that ebony dick into her mouth and began a sexy, drooling, pumping blowjob that had my cock straining with anticipation. Somehow the black stud kept control, making Hailey work for it, and she did until finally she pulled that cock from her mouth and took the first arc of cum on her face, wanking it hard there were more shots of cum that hit her chin, her tits, and face. Even when he was spent she kept on rubbing and pulling on his balls, holding on so he couldn’t withdraw his cock, I swear I even heard him whimper as she kept on rubbing his sensitive helmet. Finally, stud could take it no more and pulled his cock and balls from her grip – that must have hurt! “Kneel on the chair,” I ordered, and she did with her tits hanging over the seatback, and her pussy at just the right height for me to fuck. By now I was ready and was soon pumping sperm into her eager little cunt, I gave her arse a big slap as my cock slipped out of her cunt. “Get dressed, it’s time to go,” I said, “Oh! And leave the cum on your face.” With Hailey presentable, we left the cubicle only to find her ‘customers’ waiting and clapping as we walked through to the shop, Hailey was red with embarrassment, and yes there was only one black cock. to be continued .....