Sissy 101 Intro to Sissy Sluts
- 3 years ago
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2 Stood-up Sissy Sluts. (failed Threesome) free porn video
Just over a year ago, I went to meet up with a guy who had been asking me if I'd be up for a threesome for ages. When the day finally came, I was really excited, especially as it was another sissy who would be joining us. I had all my things in a rucksack, clothes, wig, lingerie and some extras besides and went into town to meet up with the guy (let's call him dickhead) and the other gurl in a quiet little pub. When I got there, it wasn't hard to spot the other sissy (let's call her Lucy, coz that was her name). I spotted the waif-thin, androgynous-looking guy stood at the bar, waiting nervously with a bag and half a lager. He was about five-six with sandy blonde hair that would have been equally pretty on a guy or a girl, all spikes and angles. I introduced myself and we went to a quiet little corner of the pub to wait for dickhead. Two and a half hours later, we were both kinda drunk and attempting to play a game of pool. Dickhead had not shown up and wasn't answering calls or texts so eventually, we gave it up. Lucy told me she was really disappointed and that she had all her sissy stuff in the bag at her feet. Curious, I asked what she had in the bag and we giggled and blushed as we shared what each of us had brought with us. She said she had some lacy red underwear (matching bra and panties as well as some stockings, suspenders, heels, her favourite little black dress and wig. She even let slip she was wearing a chastity cage as well as already being plugged. I told her I too was locked up in chastity and we casually discussed which cage we were in and other stuff like which we found most comfortable for long term wear and other related stuff. She said the cage she was wearing was a little pink one and I replied that I had a pink one too, although I wasn't wearing it and was in a stainless steel one. "C'mon, let's have a look then," she said as she strode off to the toilets. Trying to seem casual, although nobody even gave a second glance, I followed her into the men's room. From inside a cubicle, she swung the door open and flashed me her tiny little cock-cage, and it was admirably small indeed. I saw that she was totally hairless and her skin was so smooth and pink, I must admit I was more than a little jealous. Pulling up her skinny jeans she came out of the cubicle and I hurried inside then quickly pulled down my pants and showed her my shiny metal cock-cage. She giggled and riskily flashed me her bum, pulling her cheeks apart to show off the red jewelled plug in her hole. When we heard the door creaking we both hurriedly zipped up and went back out to finish our game of pool, the same game we had begun nearly two hours ago. "It's his loss" Lucy pouted as I was attempting to pot the black ball, which I completely missed as an idea struck me. "We could always go back to my place" I suggested, adding that it would be a shame not to get dressed up as we both had our stuff and had been obviously up for some fun. "Taxi?" she asked. "Now?" I replied. Grabbing our bags we left the pub, leaving the black ball still un-potted.
In the back of the taxi, talking in whispers, she asked: "So what you wanna do?". In reply, I tried my best to seem casual and said we should just get dressed up and then take it from there. Outside my flat, I paid the taxi driver, leaving a big tip because I was in such a fluster, then let her into the flat, locking the door behind us. We dumped our bags on the floor and collapsed onto the sofa, giggling like a pair of school girls. Eventually, I got up and went to get a bottle of wine for us to share, not that we needed any more alcohol, but it seemed like such a good idea at the time. We drank and chatted and cursed D***** (dickhead) then I decided I needed to shower and told Lucy she was welcome to use the shower too. With a little wobble, she picked up her bag and headed off to the bathroom. Five minutes or so later, I heard her calling me and I went to see what was up. I politely stood outside the bathroom door and asked what was up. "come in, I'm decent, I need a hand with something" came her reply. So, I stepped into the steamy bathroom to find Lucy peeking out from behind the shower curtain, water dripping from her sandy blonde hair. " I need a favour, but it's kinda embarrassing," she said. "will you help me shaving, I just can't reach certain, um, places?" she continued, holding out her razor. Nodding dumbly, I took it then asked her exactly which places she couldn't reach. Without a moments thought, she pulled back the shower curtain and I stared at her body. Damn! she was the perfect amount of skinny and petite. Looking her up and down I saw patches of shaving foam clinging to her body, on her shoulders, the base of her spine, between her cheeks. "These places," she said, pointing to the patches of foam. "ok, turn around then, and keep still," I said, moving next to the shower cubicle. With exaggerated care, I shaved her (she really did NOT need to shave a thing). Moving downwards to the tops of her ass cheeks, I told her she would have to lean forward so I could get between her cheeks. Lucy reached back, spreading her ass with both hands and bent over, exposing herself fully to me. She had removed the butt plug which rested on the lip of the shower. Trying not to burst, smiling like a cat that got the cream, I made every last inch of her as smooth as a baby's bottom. She rinsed off and of course, during helping her I had gotten soaked myself. "Jump in," she said, adding "you're already wet". And I was. Loving the innuendo, I stripped off and stepped into the shower. "You have to help me shave now," I told her, and after washing each other with shower gel, she proceeded to make my entire body (from the neck down) smoother than it had ever been before. After some messing around and more than a little splashing, we got out and hurried to the front room wrapped in towels to sit in front of the fire. Lucy reached into her bag and handed me some moisturizer, saying I do her and then she'll do me. I sat behind her while she knelt and removed the towel. I rubbed the lotion into her body from the neck to the tips of her toes, and everywhere in between. Then we swapped and she returned the favour. As she ran her hands over my body I could feel her little pink cock-cage gently bumping against me. I stood up and announced it was time to get dressed up as it would be a shame to have all these girly clothes and not put them to use. Lucy agreed and stood up, her cage coming to face height in front of me. I stared and possibly licked my lips as one single drop of pre-cum made its way out, hanging in that way only pre-cum can. "You're dripping" I whispered and she looked down at her cage as I stuck out my tongue and let the sticky droplet fall onto it. Swallowing and tasting her, I forced myself to stand and put on some sissy clothes, otherwise, I'd have licked her body from head to toe and neither of us would have managed to get dressed. With urgency, I started to get dressed.
Five to possibly twenty minutes later we were both dressed like sluts, her in a tiny little black dress, red underwear, stockings and suspenders topped off with ridiculously high heels. I was in a light blue matching bra and panty set with flesh coloured hold-ups, a navy tank top and short, short, shorts. I looked nice but she looked hotter than most real girls ever did. After we put on our wigs, mine two-tone blonde and brunette and her black one hanging to just above her exposed shoulders. Again the conversation moved to being stood up by dickhead. "We should take a few photos and send them to him, show him just what he's missing out on," Lucy said with a wicked smirk. Even though he didn't deserve a thing, I used her phone to take a few snaps and she did the same to me. Then, with my webcam set on a timer, I took a couple of the two of us together, trying our hardest to look as provocative and slutty as possible. Then with a press of the keyboard, I sent the pics to his profile. Satisfied, we got on the sofa and had another glass of wine before the conversation turned to sex toys. Lucy reached into her bag and took out two toys, one a pink vibe about 5 inches and a slim flesh coloured dildo not much bigger. I got my big bag of tricks from the bedroom and her eyes went wide as I showed her my collection. The smallest I had was bigger than the biggest she had and she giggled, putting a hand to her mouth saying "You're a slut". I casually nodded as if it was a compliment, which to me it actually was, and then asked if she saw anything she liked. Without hesitation, she grabbed a suction cup dildo, 8 inches and pleasantly thick. "This one, but I don't know if I could possibly take it," she said, her tiny hands clasped around the thick toy. "One way to find out," I said, looking expectantly and judging her reaction. Lucy nodded at me and handed me her pink vibe, adding "start with this and see how it goes". She turned her ass round to face me, on all fours, arching her back. Her tiny panties barely covered her caged clitty and I hooked a finger around and pulled them aside. Using my hands to spread her ass cheeks, I stuck my tongue out and began to lap at her little fuck hole. I could have spent hours with my face between her cheeks, my wet tongue exploring and probing her tight little boi pussy. Lucy was moaning quietly while I licked away, then let out a gasp as I introduced her pink toy to her hole. As I slid it in and out I put my tongue on it, keeping it nicely wet as I teased her ass. When I eventually removed my face from her ass I saw her little caged clitty was now oozing with pre-cum. It had formed a tiny little puddle on the leather sofa and I took a second to show her the mess she had made, pushing her face towards it. Obediently she lapped it all up and came up with a strand of cum on her shiny lips. I took my chance and leaned in, licking it from her lower lip and her tongue flicked out to meet mine. As we kissed, she lay back, pulling me down on top of her and parting her legs. I was licking and kissing my way down her neck, taking her little puffy pink nipples in my mouth, sucking, licking and taking each one gently between my teeth until they stood proud and erect from her chest, swollen and red. I looked up at her as I moved my head down further while she took her nipples between thumb and finger, tweaking and rolling them. When I reached her caged clitty I removed her panties (I do love gurly panties but sometimes they just hinder rather than help things). Pulling her hips towards the edge of the sofa, I pushed a cushion underneath her ass, propping it up in front of me. Kneeling between her spread legs, I reached for the dildo she had chosen and slowly, deliberately, covered it with lube. Lucy's eyes never left the thick toy in my hand and I could see she was a little nervous. As I rubbed some lube between her cheeks with my fingers I told her that I wouldn't do anything she was not fully comfortable with, which seemed to settle her nerves. I asked if she wanted to try the toy, waggling it in front of her face. Almost too softly to hear, she whispered "fuck me" with unabashed lust in her tone. "Slowly" she quickly added and I laughed. "In a few minutes you'll be begging me to put it in" I smirked and she snorted saying " I don't beg, well, I don't beg other sissies". She begged, oh how she begged.
I used the fat head of the dildo to relax her tight little pussy, pushing it ever so gently and just as she seemed about to let it sink in, pulling it back out. Teasing her fuck-hole with patience I didn't even know I possessed. It was totally worth it to watch the look on her face changing and to see her tight little boi pussy almost sucking the toy into her body. I watched intently and when I glanced up at her face, she mouthed the word "please" under her breath. "oh you can do better than that" I laughed as I pulled the toy back before the hungry little hole could engulf it. Pouting at me, she said "please put it in me" in a much clearer voice. Ignoring her request I told her that the dildo was making her gape a little and she replied "really, I wanna see", then handed me her phone. I took the hint and told her to spread her cheeks with both hands to exaggerate the gape. Without actually inserting the dildo, I started to record on her phone, alternating between her fuck-hole and face, capturing her panting and gasping, begging and pleading, all her dignity thrown straight out of the window. After making her gape a few more times, leaning over to touch tongues and stare into her eyes, she let out a sigh of frustration and pulled me onto her. Pressed against her she whispered in my ear, "for fuck's sake, I need you to fuck my ass, right now". I couldn't resist making her add "please" to it before I said I would do it. She held her ankle up, exposing her pink little hole to me, and I watched the big dildo slowly sink into it. "oh god" was all she could manage when her ass pulled the toy even deeper. I wasn't pushing it at all at this point, just resting a finger against the base of the toy. I even let go of the dildo completely and watched with a stupid grin on my face as it slipped in deeper. Lucy had closed her eyes now, gasping and moaning quietly, but she opened them again when I let go of the toy. "Fuck me" she urged, "fuck me like a slut". Which is what I did.
I eventually climbed on top of her, kneeling with my ass over her face and my own face looking down at her ass. I didn't have to tell her to lick me while I fucked her, she grabbed my ass cheeks and pulled me down onto her wet tongue. I squirmed and wiggled while her tongue licked at my own fuck-hole before she plunged it inside me, snaking it as far in as it would go. I had begun moaning with pleasure myself and urged her to keep licking my ass, calling her a dirty little anal whore and lots more besides. When I knelt up to get a toy for myself, I saw my clitty had been dripping onto her face and neck as if I had actually just emptied my balls on her face. She used a finger to taste me, while her other handheld the dildo in her ass, thrusting with more intensity than I had dared. With a toy of my own in hand, I stood and watched her cum covered face as she slowly started to really fuck herself. "somebody likes my big dildo" I laughed and she laughed in reply adding "I fucking love it".
I pointed out that she could stick the suction cup to the laminated floor and ride it if she wanted. "fuck yeah" was all she said, sticking the toy to the floor and lowering herself onto it. Without another word, she took the full 8 inches, balls deep, grunting in satisfaction. I lay on the sofa in front of her, handing her my dildo and spreading my legs in her face. With a little shift of position, she had her face back between my cheeks and I could look down to watch as her hungry tongue teased my ass. "Lucy, fuck me" I half-whispered, half growled at her. The dildo looked stupidly large in her tiny grasp(it was 9 inches if I remember correctly, but it looked huge). Taking it with two hands, she inserted it as I moaned like a whore. She gently pushed the whole length inside me until the balls at the base were pressed against my skin. "Greedy slut" she gasped and I couldn't argue with it, I was so desperate for it at this point. I stared down as Lucy bounced herself up and down on the dildo, using her hands to thrust in and out of my ass, a look of concentration etched on her still-dripping-with-pre-cum covered face. I didn't bother to tell her she'd missed quite a bit of it, I'd lick it off myself when I had the chance but right then I was struggling not to explode all over her. My cage bobbed about as she took the hint and fucked me proper. When I couldn't hold it any longer, I blurted that I was gonna cum, then gasped "I'm cumming!". The moment she heard me say it, her mouth was beneath my chastity cage, tongue out to catch my cum, which squirted twice then dribbled and oozed with each thrust of the dildo. She made certain that every last drop had been milked from my clitty and opened her mouth to show me my cum. I should have known a sissy would know exactly what to do with a mouthful of spunk, swallowing it without letting me see first would have been a wasted opportunity and sissy sluts don't let those moments pass unnoticed easily.
In the back of the taxi, talking in whispers, she asked: "So what you wanna do?". In reply, I tried my best to seem casual and said we should just get dressed up and then take it from there. Outside my flat, I paid the taxi driver, leaving a big tip because I was in such a fluster, then let her into the flat, locking the door behind us. We dumped our bags on the floor and collapsed onto the sofa, giggling like a pair of school girls. Eventually, I got up and went to get a bottle of wine for us to share, not that we needed any more alcohol, but it seemed like such a good idea at the time. We drank and chatted and cursed D***** (dickhead) then I decided I needed to shower and told Lucy she was welcome to use the shower too. With a little wobble, she picked up her bag and headed off to the bathroom. Five minutes or so later, I heard her calling me and I went to see what was up. I politely stood outside the bathroom door and asked what was up. "come in, I'm decent, I need a hand with something" came her reply. So, I stepped into the steamy bathroom to find Lucy peeking out from behind the shower curtain, water dripping from her sandy blonde hair. " I need a favour, but it's kinda embarrassing," she said. "will you help me shaving, I just can't reach certain, um, places?" she continued, holding out her razor. Nodding dumbly, I took it then asked her exactly which places she couldn't reach. Without a moments thought, she pulled back the shower curtain and I stared at her body. Damn! she was the perfect amount of skinny and petite. Looking her up and down I saw patches of shaving foam clinging to her body, on her shoulders, the base of her spine, between her cheeks. "These places," she said, pointing to the patches of foam. "ok, turn around then, and keep still," I said, moving next to the shower cubicle. With exaggerated care, I shaved her (she really did NOT need to shave a thing). Moving downwards to the tops of her ass cheeks, I told her she would have to lean forward so I could get between her cheeks. Lucy reached back, spreading her ass with both hands and bent over, exposing herself fully to me. She had removed the butt plug which rested on the lip of the shower. Trying not to burst, smiling like a cat that got the cream, I made every last inch of her as smooth as a baby's bottom. She rinsed off and of course, during helping her I had gotten soaked myself. "Jump in," she said, adding "you're already wet". And I was. Loving the innuendo, I stripped off and stepped into the shower. "You have to help me shave now," I told her, and after washing each other with shower gel, she proceeded to make my entire body (from the neck down) smoother than it had ever been before. After some messing around and more than a little splashing, we got out and hurried to the front room wrapped in towels to sit in front of the fire. Lucy reached into her bag and handed me some moisturizer, saying I do her and then she'll do me. I sat behind her while she knelt and removed the towel. I rubbed the lotion into her body from the neck to the tips of her toes, and everywhere in between. Then we swapped and she returned the favour. As she ran her hands over my body I could feel her little pink cock-cage gently bumping against me. I stood up and announced it was time to get dressed up as it would be a shame to have all these girly clothes and not put them to use. Lucy agreed and stood up, her cage coming to face height in front of me. I stared and possibly licked my lips as one single drop of pre-cum made its way out, hanging in that way only pre-cum can. "You're dripping" I whispered and she looked down at her cage as I stuck out my tongue and let the sticky droplet fall onto it. Swallowing and tasting her, I forced myself to stand and put on some sissy clothes, otherwise, I'd have licked her body from head to toe and neither of us would have managed to get dressed. With urgency, I started to get dressed.
Five to possibly twenty minutes later we were both dressed like sluts, her in a tiny little black dress, red underwear, stockings and suspenders topped off with ridiculously high heels. I was in a light blue matching bra and panty set with flesh coloured hold-ups, a navy tank top and short, short, shorts. I looked nice but she looked hotter than most real girls ever did. After we put on our wigs, mine two-tone blonde and brunette and her black one hanging to just above her exposed shoulders. Again the conversation moved to being stood up by dickhead. "We should take a few photos and send them to him, show him just what he's missing out on," Lucy said with a wicked smirk. Even though he didn't deserve a thing, I used her phone to take a few snaps and she did the same to me. Then, with my webcam set on a timer, I took a couple of the two of us together, trying our hardest to look as provocative and slutty as possible. Then with a press of the keyboard, I sent the pics to his profile. Satisfied, we got on the sofa and had another glass of wine before the conversation turned to sex toys. Lucy reached into her bag and took out two toys, one a pink vibe about 5 inches and a slim flesh coloured dildo not much bigger. I got my big bag of tricks from the bedroom and her eyes went wide as I showed her my collection. The smallest I had was bigger than the biggest she had and she giggled, putting a hand to her mouth saying "You're a slut". I casually nodded as if it was a compliment, which to me it actually was, and then asked if she saw anything she liked. Without hesitation, she grabbed a suction cup dildo, 8 inches and pleasantly thick. "This one, but I don't know if I could possibly take it," she said, her tiny hands clasped around the thick toy. "One way to find out," I said, looking expectantly and judging her reaction. Lucy nodded at me and handed me her pink vibe, adding "start with this and see how it goes". She turned her ass round to face me, on all fours, arching her back. Her tiny panties barely covered her caged clitty and I hooked a finger around and pulled them aside. Using my hands to spread her ass cheeks, I stuck my tongue out and began to lap at her little fuck hole. I could have spent hours with my face between her cheeks, my wet tongue exploring and probing her tight little boi pussy. Lucy was moaning quietly while I licked away, then let out a gasp as I introduced her pink toy to her hole. As I slid it in and out I put my tongue on it, keeping it nicely wet as I teased her ass. When I eventually removed my face from her ass I saw her little caged clitty was now oozing with pre-cum. It had formed a tiny little puddle on the leather sofa and I took a second to show her the mess she had made, pushing her face towards it. Obediently she lapped it all up and came up with a strand of cum on her shiny lips. I took my chance and leaned in, licking it from her lower lip and her tongue flicked out to meet mine. As we kissed, she lay back, pulling me down on top of her and parting her legs. I was licking and kissing my way down her neck, taking her little puffy pink nipples in my mouth, sucking, licking and taking each one gently between my teeth until they stood proud and erect from her chest, swollen and red. I looked up at her as I moved my head down further while she took her nipples between thumb and finger, tweaking and rolling them. When I reached her caged clitty I removed her panties (I do love gurly panties but sometimes they just hinder rather than help things). Pulling her hips towards the edge of the sofa, I pushed a cushion underneath her ass, propping it up in front of me. Kneeling between her spread legs, I reached for the dildo she had chosen and slowly, deliberately, covered it with lube. Lucy's eyes never left the thick toy in my hand and I could see she was a little nervous. As I rubbed some lube between her cheeks with my fingers I told her that I wouldn't do anything she was not fully comfortable with, which seemed to settle her nerves. I asked if she wanted to try the toy, waggling it in front of her face. Almost too softly to hear, she whispered "fuck me" with unabashed lust in her tone. "Slowly" she quickly added and I laughed. "In a few minutes you'll be begging me to put it in" I smirked and she snorted saying " I don't beg, well, I don't beg other sissies". She begged, oh how she begged.
I used the fat head of the dildo to relax her tight little pussy, pushing it ever so gently and just as she seemed about to let it sink in, pulling it back out. Teasing her fuck-hole with patience I didn't even know I possessed. It was totally worth it to watch the look on her face changing and to see her tight little boi pussy almost sucking the toy into her body. I watched intently and when I glanced up at her face, she mouthed the word "please" under her breath. "oh you can do better than that" I laughed as I pulled the toy back before the hungry little hole could engulf it. Pouting at me, she said "please put it in me" in a much clearer voice. Ignoring her request I told her that the dildo was making her gape a little and she replied "really, I wanna see", then handed me her phone. I took the hint and told her to spread her cheeks with both hands to exaggerate the gape. Without actually inserting the dildo, I started to record on her phone, alternating between her fuck-hole and face, capturing her panting and gasping, begging and pleading, all her dignity thrown straight out of the window. After making her gape a few more times, leaning over to touch tongues and stare into her eyes, she let out a sigh of frustration and pulled me onto her. Pressed against her she whispered in my ear, "for fuck's sake, I need you to fuck my ass, right now". I couldn't resist making her add "please" to it before I said I would do it. She held her ankle up, exposing her pink little hole to me, and I watched the big dildo slowly sink into it. "oh god" was all she could manage when her ass pulled the toy even deeper. I wasn't pushing it at all at this point, just resting a finger against the base of the toy. I even let go of the dildo completely and watched with a stupid grin on my face as it slipped in deeper. Lucy had closed her eyes now, gasping and moaning quietly, but she opened them again when I let go of the toy. "Fuck me" she urged, "fuck me like a slut". Which is what I did.
I eventually climbed on top of her, kneeling with my ass over her face and my own face looking down at her ass. I didn't have to tell her to lick me while I fucked her, she grabbed my ass cheeks and pulled me down onto her wet tongue. I squirmed and wiggled while her tongue licked at my own fuck-hole before she plunged it inside me, snaking it as far in as it would go. I had begun moaning with pleasure myself and urged her to keep licking my ass, calling her a dirty little anal whore and lots more besides. When I knelt up to get a toy for myself, I saw my clitty had been dripping onto her face and neck as if I had actually just emptied my balls on her face. She used a finger to taste me, while her other handheld the dildo in her ass, thrusting with more intensity than I had dared. With a toy of my own in hand, I stood and watched her cum covered face as she slowly started to really fuck herself. "somebody likes my big dildo" I laughed and she laughed in reply adding "I fucking love it".
I pointed out that she could stick the suction cup to the laminated floor and ride it if she wanted. "fuck yeah" was all she said, sticking the toy to the floor and lowering herself onto it. Without another word, she took the full 8 inches, balls deep, grunting in satisfaction. I lay on the sofa in front of her, handing her my dildo and spreading my legs in her face. With a little shift of position, she had her face back between my cheeks and I could look down to watch as her hungry tongue teased my ass. "Lucy, fuck me" I half-whispered, half growled at her. The dildo looked stupidly large in her tiny grasp(it was 9 inches if I remember correctly, but it looked huge). Taking it with two hands, she inserted it as I moaned like a whore. She gently pushed the whole length inside me until the balls at the base were pressed against my skin. "Greedy slut" she gasped and I couldn't argue with it, I was so desperate for it at this point. I stared down as Lucy bounced herself up and down on the dildo, using her hands to thrust in and out of my ass, a look of concentration etched on her still-dripping-with-pre-cum covered face. I didn't bother to tell her she'd missed quite a bit of it, I'd lick it off myself when I had the chance but right then I was struggling not to explode all over her. My cage bobbed about as she took the hint and fucked me proper. When I couldn't hold it any longer, I blurted that I was gonna cum, then gasped "I'm cumming!". The moment she heard me say it, her mouth was beneath my chastity cage, tongue out to catch my cum, which squirted twice then dribbled and oozed with each thrust of the dildo. She made certain that every last drop had been milked from my clitty and opened her mouth to show me my cum. I should have known a sissy would know exactly what to do with a mouthful of spunk, swallowing it without letting me see first would have been a wasted opportunity and sissy sluts don't let those moments pass unnoticed easily.
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