The bitchboy’s First Time


The bitchboy’s First TimeIt had started as a few exchanged messages on PM. Now I knocked on the hotel door – it swung open and there was Mistress – looking fabulous in a leather dress, fitted beautifully to her curves, with the top couple of buttons undone for effect – just glimpses of her fabulous cleavage within. Her hubby the birthday boy was behind her – almost naked – except for a rather fetching pair of lacy red panties – thong style, which were struggling to contain his obvious excitement. “Please come in”, She said, opening the door wider”Thank you, I hope I’m not interrupting anything?””No your timing is perfect – and you look lovely, thank you for coming round to help birthday boy here with his birthday surprise”. “You’re very welcome”, I said as I bobbed a little curtsy for Her. “I’m looking forward to what you have in mind, very much”. I was dressed in my tight pink angora sweater, that does a good job of emphasizing my round breasts and perly nipples. A pearl pendant bounced and swung from my bust as I walked and and black leather pleated leather skirt. Underneath a full set of my favourite lacy lingerie – stockings and suspenders of course! had not taken his eyes off me since I’d walked in, neither had the fellow behind the desk in the lobby when I’d asked directions to the lifts earlier. It’s not that I look particularly good or even passable – but a 6′ tall transvestite in 5″ heels is hard to ignore. I have a lot of ‘head and shoulder’ moments and double takes…Mistress went over to the dressing table where she poured herself a top up to her sparkly wine, bending slightly as she did – Her dress was also the perfect length to show off her fabulous legs, accentuated by elegant heels and lovely expensive looking embroidered lacy stockings with seams. She was quite the vision in black leather!. “Have you got something for me?” She enquired as she returned”Oh yes,of course” I said and I rummaged in my clutch back and took out the key to my chastity. I handed it to her and she fastened it to a necklace around her neck – next to another key. Both disappeared inside her dress – only visible occasionally nestling between her beautiful breasts. “Now then bitchboy”, She said to hubby, “I hope you’re going to enjoy the rest of your birthday present!” I knew they’d been staying in the swanky hotel for a couple of nights, had taken in the sights, had romantic dinners, and he’d been given lots of attention from Mistress, his wife – spoiled in fact. She’d given herself to him and he’d benefited from a considerable amount of bedroom time – they’d made romantic love, and hot sex! He’d been given full access and he’d taken her in all his favourite positions, and most of all she’d given him a lot of oral attention – blowjobs to wake up to, blowjobs before dinner, blowjobs before (and after) sex. Blowjobs were his favourite things ever, and that’s one of the the reasons I was there. Now Kay, please take a seat on the edge of the couch” said Mistress, so I sat down, trying to keep my composure as my plug pushed further into my backside as I sat right on top of it. I followed Her with my eyes as she went over to hubby. My . He was still standing a little nervously – but was clearly showing some excitement through the thin lace of his panties – she ran her middle finger up the length of his good sized cock from his balls to his tip – poking out from the top with a little pretty ribbon just below his glans. He Involuntarily stuck is bum out at this point, I’m not sure how he felt being played with, obviously hard, with me in the room.”I just want you to relax,” she said to him as she positioned herself behind him, hands on his shoulders, and gently maneuvered him towards me, nibbling his ear as she went. He was standing istanbul escort in front of me – his pantied cock right at my eye level. I looked at it and then up at him looking down at me. I hoped I was going to be allowed to give him a suck – I love to suck – to be supervised like this by a gorgeous Mistress would be delightful. My own cock became tight inside it’s little cage at the thought and I could feel the precum building inside – I’d soon be dripping wet!Gently she pressed down on his shoulders and he was then kneeling in front of me, her behind him. “Say hello to Kay. Kay this is bitchboy Chris and he loves blowjobs””Hello Kay” he said as he looked at me – uncertainly”Hello Chris” I responded. “Your so lucky to have such a wonderful wife that gives you so much attention and such special presents. Have you had a good birthday?”Before he could reply Mistress said to him “He has. And now It’s time for a treat! Having had me pleasuring him so many times over the last few days I want him to have to have the full oral experience – I think I want to introduce him to giving so much pleasure as I have. Kay, Please stand up”.I did as I was told – the bulge in my black leather pencil skirt now level with Chris’ face.”Reach up and take off her panties” She whispered into his ear, so I could hear clearlyOh my – he reached under my skirt and found the little thin waist of my panties in amongst the suspenders and other accessories hidden from his sight. I wiggled to help them down to about my knees. “Lift your Skirt please, Kay”I dutifully pulled the hem of my skirt up, revealing my stockings and my little locked sissycock inside it’s cage. “See how she looks after herself for her mistress – smooth and locked away. No chance to play with herself without permission. What do you think of that bitchboy.He looked at my smooth sissycock, the tiny little cage.”It’s so small he said eventually – and does the cage hurt”?”I can’t deny it’s small” I said. “As you can see small cage means small cock inside – I used to be quite big before I was locked away. the cage doesn’t hurt, unless I get turned on and attempt to get hard inside but I always know its there. It’s unforgettable.” It’s true I’m a grower rather than a shower and on the few occasions I’m let out it can still stand up OK. As Chris was about to discover. But in my small cage I look tiny. My lipstick is bigger!”Here, let me” said Mistress as she leaned forward an arm each side of Chris’ head as she lifted her chain from inside her dress. the keys rattled as she leaned forward and placed the key in my lock, turned it and removed the cage from the ring, still tight around my very full sissy balls. The long tube glistened with drippy pre-cum as it emerged from it’s little hole, and there were marks where the bars had been all over the soft dome at the end. His face was right up close now as she pushed him towards me. my cock slowly expanding as it does when released. I felt the urge to rub the pins and needles of returning circulation away, but kept my hands behind me.”Oh look, bitchboy”, She said, gently nudging Chris’ face closer still to my wrinkled sissycock, “I think she might need a little help”… I wondered what she meant.Chris lifted one hand towards me but she stopped him and pushed his face right up against my sissycock – “No – after being locked away for her Mistress for so long I think we can do better than that… Far Better”.He tried to turn away but she pushed his cheek to me again and turned his head, his lips against my limp cock.”Open up bitchboy” she said simply, and he did. And as he did so my sissy cock went between his lips. He gave it a little suck and I felt his teeth and tongue inside wet and warm against my head. It plopped out”Good avcılar escort bichboy” She said as she encouraged him further. So there I was – my sissy cock growing ever bigger harder in Her bitchboys, mouth as she stood behind him guiding his head around my cock. Sucking one moment licking me underneath the next. Running his tongue around the chastity ring which I was never going to be able to remove at my current size – a raging hard on being well underway. Once or twice he lifted his hands towards me – everytime she placed them back behind him as he kneeled. Occasionally she bent down offering me a gimpse of her cleavage, which just helped with my now considerable excitement.After all this time locked I was not far away from cumming. His eyes would occasionally bulge as She reached down behind him – I imagined She was playing with his little hole – unprotected as it was by the skimpy thong panties he had on; I could see his naked cheeks every now and again, the pretty lacy fabric disappearing between them as he bobbed up and down on my fully erect sissycock. She gently pulled him back by the ears.”Take a seat, Kay”, she instructed.I sat back down on the sofa leaning back a little, my sissycock standing right up – his dribble and drool running down it’s length over my full balls, now turning a little purpley as a result of the tight ring still in place. She pushed him between my knees and came and sat beside me, also opening her legs and lifting her dress to reveal her panty-less pussy. “Carry on, bitchboy” She said to Chris, so he did.As we sat together, Mistress playing with her pussylips and clit, her hubby bitchboy Chris bobbing up and down on my by now large erection, it felt wonderful. I didn’t know whether to look at him as I enjoyed his wet mouth lips and tongue on my sissycock or Her as she rubbed ever harder at her clit, starting to moan and groan with pleasure as she watched her husband giving me the oral sex of my life, and quite possibly his too. I have to say for a novice he was very good. “I’d love to help you with that, Mistress” I said to her, I was beginning to moan now too – as I got closer to loosing it altogether. “How so?” she looked over enquiringly.I lifted Chris off my cock for a moment and stood – my erection sticking out obscenely from under my skirt, still hitched around my hips and waist. I took it off and laid down on the carpet, my head between Mistress’ feet. My cock was now raised slightly from my tummy.”Please continue” I said to Chris guiding him between my legs so he could continue on me. I reached up Mistress’ soft stocking clad calves and pulled Her knees down towards me – She understood…. and gently lowered herself onto my face. She had a perfect view of her hubby sucking and slobbering all over me,whilst I started licking her pussy lips, running my tongue all the way to her little arsehole and back again, concentrating on long slow strokes of wetness against her pussylips. This was a welcome distraction from my own growing orgasm – I focussed on pleasuring her as only sissies know how. I worked my tongue to her clit – she leaned forward to improve access as she watched her hubby still sucking and licking my cock like a big engorged lollipop. I could feel his drool running down my arsecrack as I sucked at Her clit; She soon started grinding against my lips and tongue and I could taste her juices start to flow as I licked and sucked away, the musky smell of her pussy overpowering me. Then it was all too much for me. I pulled her down against my mouth as the inevitable happened and I started to cum.When I’ve been locked for a long while a number of things happen, in order…First I start to leak a lot of cum – it just runs out of me…Then the building orgasm hits, and the cum starts to şirinevler escort squirt – one, two three, huge squirts as I benefit from the full bone shaking leg trembling result of a very infrequent full orgasm,In the third phase the pulsing continues to run through my whole body for some minutes as more cum continues to flow, my overfull balls emptying themselves over whatever is in the way. On this occasion it was Chris. He was clearly surprised by the un-announced start of phase one – so in no time he had a very full mouth of my first cum… He’d sat up as the second phase started – phase one cum running over his lips and chin, just in time to be spattered by the phase two squirts. I was involuntarily pulling Mistress tightly over my mouth by this time and I felt her orgasm just at the same time, her juices filling my nose and mouth as I groaned loudly into her, my lipstick lips hard against her pussylips. When your a sissy being Queened, no one hears anything. As my phase three started then continued, Mistress sat up too so I could see the last of my cum running out of my still twitching sissycock, Chris sitting covered with phase one and two cum, and Mistress behind me holding her dress and inspecting my make-up which was now not on my face but smeared all over her pussylips and clit. mixed with all her own creamy juices. sat like that for a moment – then She indicated that Chris should clean his wife up. Still covered in my cum he started licking Mistress, his wife eagerly. I went round to the other end and saw his own good sized cock was still hard inside his panties. I pulled it out and went to work returning the favour. It didn’t take very long. He came in my mouth after just a few licks and sucks. There wasn’t much cum either given the weekend of sex he’d just had. I didn’t spill a drop as I tucked his cock back into his panties whilst he finished cleaning Mistress. “Thank You Chris” I said – I loved what he’d done, from the amazing way he’d given me my first orgasm in months, to depositing his little load into my own mouth. I hope you enjoyed your special Birthday Treat – I think you’re an amazing sissy cock sucker”. I turned to Mistress “And thank you too Mistress for arranging such a wonderful treat for me. I can’t thank you enough.””You’re welcome” she said – and there’re two things left to do”. Once again the keys emerged from between Her breasts under Her dress.She had two softening sissies in front of her, panties in various positions of disarray. She handed me my cage. I slipped the tube into it’s little hole at the end of my now very soft cock and pushed it all the way in, and located the pins in the right place around in the ring. I stood in front of her so she could lock me away safely. she reached into her handbag and produced a lovely gift wrapped box. She handed it to Chris. “Open it please bitchboy” she said smiling sweetly. With trembling hands he opened the wrapping, lovely ribbon, pink sparkly paper all falling to the floor. Inside was a little zipped pouch. He opened it and took out the contents, wrapped in soft pink paper tissue. Out came a lovely pink holy trainer chastity device. He looked at it and turned it in his hands. She leaned forward and unlocked it with the other key on her chain, the one next to mine. “Could you help him with that please Kay”. She said, so I do. I knelt in front of him, his little cock now fully soft and compliant. I slipped his balls and cock through the ring ans straightened it up, puling as much as I could though the ring. I gently moistened the soft pink tip of his cock with my tongue. I could still taste the last of his cum as I slipped the little tube up to meet the ring and held it there whilst Mistress leaned in and locked him in.Inspection she said sweetly – so we both stood in front of her – my cage and his new holy trainer in full view as she sat on the sofa, looking up at us. “Aww that’s so lovely” she cooed appreciatively…. “my new sissy and my new sissybitchboy all locked up!” She paused, “together!”.

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