Breaking In Sadie free porn video

"I married a little sissy fag. You like my fingers up your ass, don't you, you fag? You wish it was a man's cock. You want to get fucked, don't you? You want to suck a cock, get it all slippery then have it shoved up your ass, like my greasy fingers. You do, don't you, you little sissy fag? Do you, Hope?" My naked wife was lying next to me on her side. I was lying on my front, my ass up in the air, while she had two fingers stroking in and out of my lubed ass. She was pushing them in and out and humiliating me. She was obsessed with gay men for some reason, often spending hours looking at gay porn and masturbating with her didoes and vibrators. Maryanne discovered gay male porn by accident as a pop-up suddenly appeared when she was searching for more conventional porn one day, and was quickly hooked. We had an OK sex life before, vanilla but I was satisfied; now she was insatiable. "I'm going to fuck you now, to break you in, Hope, then I'll bring home a massive gay man who will really wear you out. You fucking fag, you'll beg him to fuck you, to let him suck his cock. Your little clit will pour with come as he pounds into your sissy fag ass, all smooth and round like a girl's. Mmm..." She caressed my shaven ass with her other hand as she continued to piston her fingers in and out. I was totally hairless from the neck down, and have been on a strict exercise and diet regime for nearly five months now to get the perfect ass and legs, with little upper body development. Maryanne scooted behind me and slowly pressed her strap-on in. "Yes, fucked like this, you fag, feel my cock go in. You can take this eight- inch fine now, you little sissy, feel it, beg me to fuck you." "Yes please, Mark, fuck me with your big cock, oh it feels so good..." I had to call her Mark in bed. Her strap-on pushed into her as she rammed it into me, and stimulated her clit at the same time. She pushed in and out in a deep, hard rhythm, slapping me every so often, bottoming out and pushing against my prostate on each stroke. I was rock hard but knew better than to touch my cock. "Yes, deeper, Mark, fuck my fag ass, yes, harder, faster..." Maryanne really picked up the pace. "Take it now, you fucking fag, take my cock, deep into your sissy ass, yes, ahhh, fuck!" She was already worked up from me going down on her and came hard as she pounded into me mercilessly. Finally she slowed down and pulled out. I quickly turned over and unbuckled the strap-on, eased it off her and gently lapped her sore slit, taking my time until I got to her clit and gave her another orgasm. "My good little sissy, come here..." She pulled me up and we shared an emotional kiss. "You've been a good little fag." She pumped a little lube in her hand and rubbed it on my cock. "Your big-dicked lover takes pity on you, Hope, now come..." It only took a few strokes and I nearly passed out from the intensity of my own orgasm, my first in a few days. I knew immediately to lap up my come from her hands after thanking her. Why do I put up with this? I never knew sex could be so, well, dirty, humiliating, shameful and...great! I'm in a constant state of arousal, nearly as much as Maryanne. It's rejuvenated our marriage, we're like newlyweds, and I've never been happier. I've discovered a serious submissive streak I never knew I had and it's wonderful. We could be eating dinner at a restaurant and she only needs to whisper, "I bet you wish you were naked on your knees in front of that hunk licking his balls," and I'm instantly hard and panting. Or we could be watching TV and she puts her hand down the back of my pants and says, "I can feel your satin panties, fag. Now suck my dick," and I'm erect, on my knees sucking her clit. After 20 years of marriage, it's a miracle that we're so happy together. She's taught me everything she knows about being a woman. I have a great wardrobe and have spent many happy hours in front of a mirror learning the art of transforming myself. We spent many happy days teaching me to walk in heels and the mannerisms and voice to use. Now I'm not really passable but that doesn't stop us going out with me en femme, and as we're in a decent sized city, no one really cares. The gaff usually keeps me from tenting out my panties but sometimes we go out without it, just to embarrass me. Kathy, Maryanne's best friend, knows about all of us and loves giving me tips and suggestions on how to look more feminine. She's my best source for knowing which lip liner and gloss to get, which shades go best with my coloring, and how to apply eyelash thickener without it clumping. There's just so much to learn! Kathy is short and a bit heavy while Maryanne is tall and willowy. I've quizzed Maryanne about her and Kathy and there is a history there but I've only been able to get a few stories about their time together, but Maryanne has more fun role-playing with me. Last night I was on my knees slobbering over 'Mark's' cock which was jutting obscenely out from Maryanne's slit, deep-throating it and then backing off and sucking the head while stroking with both hands. The other end of the strap-on went into her soaking wet pussy and the patterned top was rubbing against her clit. She finished off by holding my face still and fucking my mouth until she slammed into me, groaning as she came. I was wearing stockings and a pink G-string, with a small butt-plug in place, keeping my ass stimulated as I could feel it slipping and sliding inside me. My breast forms were inside a stretchy pink bra, and I was wearing a shoulder-length strawberry-red wig with full makeup. I had been taking care of my nails and they were long and cherry red, both hands and feet. As usual I wasn't wearing any chastity device, as Maryanne preferred to control me herself. My cock was hard and leaking - I hadn't had any release in four days and was experiencing the familiar agony and ecstasy of being continually edged. "Good little fag, now kiss my ass." Maryanne removed the strap-on and went down to her knees at the edge of the bed, bending over so her top half was lying on the bed and her knees were on the floor. She spread her legs apart and I quickly moved in to lick and kiss her perfect ass, licking from the small of her back to her crack and then down. She wiggled her cheeks as a signal and I concentrated on rimming her rosebud, carefully teasing it with the tip of my tongue. I slipped a hand below to delicately part her vaginal lips and use the wetness to coat her clit, which I softly teased and stroked as I tongued her asshole. "Good fag, yes, eat my sweaty ass, yes, like that..." I pushed in harder and basically fucked her ass with my tongue, my hand moving faster on her clit until she came again, pushing back hard against my face. I licked her ass cheeks afterwards as she came down until she pushed me away as she stood up. "That was nice, my little fag. Come and sit down with me." We moved to the divan near the bed. Maryanne slowly stroked my balls and cock while talking to me. "Tomorrow's a big day. Kathy has spent the last month getting Miles ready for you. Remember him? Big, strong Miles, Kathy's hubby? You should see him now, I've seen photos. Been locked up for nearly two weeks, shaved, oiled and perfumed, and Kathy fucks him with her strap-on at least once a day. He even manages to sort of come when he's fucked, something we need to work on, but anyway she's bringing him over tomorrow. Now I know I promised you a big hunk with a massive cock to fuck your brains out but Kathy and I thought it would be even more fun to see the two husbands together. You're much more advanced so you'll need to help him out. If you're a good sissy fag I'll even let you come as much as you want with him. Sound fun?" Well, I can't say I wasn't expecting something like that, but not with Miles. A big brute of a man, always nice to me the few times we've met but definitely not gay and even more definitely not submissive whatsoever. Still, the prospect of being able to come overrode almost anything else. "But Mark, I want to be faithful to you!" Maryanne laughed. "Oh, that's sweet, darling, but I want you to help Kathy train Miles. And he will be your first! Two sissies together. You can nuzzle each other's smooth ass, suck each other's balls, come into each other's mouth. Finally you'll get a real dripping cock into your sweet red lips, feel it pulse and release its salty cream into you. It won't be a real man but another sissy. Kathy and I will love watching it all. You'll help teach him what you know, and finally you'll get to put your own little clit into something soft and warm. I want to watch you fuck Miles, I want to see his face as you fuck him, with Kathy and I laughing and humiliating both of you." Maryanne was stroking me harder and I was ready to come. "No, little Hope, not yet..." She let go before I could finish and played with my butt-plug instead. I was practically crying but I knew better than to beg. "Now, now Hope, don't be sad, I'm sure that your little sissy friend will help you tomorrow. Now get my bath ready, remember you have a lot of chores to do before they get here tomorrow." ***** The next day Maryanne and I spent the morning getting ready - I was freshly shaved, oiled, perfumed, made up and dressed in my best lingerie (complete with breast forms) under a simple summer flowery dress with strappy heels. I had earrings and a choker as well, finished with my lovely dark curly wig. Maryanne went for more of a menacing outfit with painted-on shiny black trousers with a black bustier and open-fingered gloves. Sounds strange but it worked on her, showing off her fantastic figure and with dramatic makeup, she looked perfect. ***** Kathy and Miles arrived early afternoon. Maryanne didn't tell me what to expect so I was a bit shocked. Kathy was, as usual, lovely in an evening dress, making the most of her wonderful breasts. But Miles - well! He stood about six foot four and normally wore jeans and plaid shirts, with his chest hair poking out. Today he was mincing about like the world's largest sissy. He had a frilly top with a very short skirt and the bottom of his ass cheeks on display, framed by pink panties with lacy edges. He was obviously shaved everywhere from the neck down and glowed with a sheen of oil or gel. Pink gloss lipstick, full girly makeup with bright red cheeks, Bobby socks with white lace-up shoes with small heels. Blonde curls cascading down his back, framing his face. Kathy was beaming. "Sadie, curtsey to Maryanne and Hope, just like we practiced!" Miles (now Sadie) performed an awkward but adequate curtsey. Maryanne and I shared a giggle - he was so cute! Was this to be my first 'man'? Delicious... Curiously, Sadie didn't recognize me. Kathy had to tell him. "Sadie, now go kiss Hope but don't mess up her lipstick - at least not yet. Don't you know her? She used to be Henry." Sadie's eyes wide with recognition and even fear as she perhaps thought that I might be her own fate. Ah, she should be so lucky... Sadie was reluctant so I went up to her, looked up (she's so much taller than me) and wrapped my hands behind her head. She slowly moved her head down and I went up on my toes (not easy in heels!) and kissed her gently on the lips, sneaking my tongue in briefly. Sadie's head shot back in alarm. "Sadie, how rude! After all the trouble Hope and Maryanne had to get ready to accommodate us today, you can't even give Hope a proper greeting! Now you two sit down on the couch together and see if Sadie can't behave better. Maryanne, at least I can greet you properly!" "Come here, you vixen..." Maryanne said, and the two women shared a long, passionate soul kiss, their hands squeezing and rubbing asses and breasts. I simply smiled but Sadie seemed distraught. I sat down and patted the seat next to me. Sadie slowly sat down, carefully keeping her knees together, her little skirt framing her on the couch. "Don't be nervous, dear, only us girls here! Don't you look lovely. Where did you get your top?" I kept up a steady stream while continually touching her knees, shoulder and arm. Sadie looked uncomfortable but somehow desperate. I leaned over (and up!) and whispered in her ear, "How long since Kathy allowed you to come?" Sadie smelled of strawberries and fear, an intoxicating combination. "I...uh...nearly two weeks now!" She blushed prettily and I glanced down. Mmm, already starting to tent her skirt. Perfect. "Oh, you poor thing! I've only had a few days. But it's so nice when you do, isn't it? Just gushing over and over, pure ecstasy. Last time she had her strap on deep inside me with my knees up around my ears, on my back, and she stroked me hard. I shot up so far some of it got on my face! Ah, it was fantastic..." Sadie kept blushing and continued to tent out her skirt. I put my hand in her thigh. "I love your legs, they're so smooth. Did you oil them just for me, dear?" I pretended to smooth down her skirt. "This is so sexy. But it seems lumpy...wait, is that for me?" I pulled up the skirt and her pink satin panties were tented out with a good-sized cock with a large wet spot at the end. I ignored it for the moment and reached through the elastic to fondle her balls. Large and smooth. "These must be blue after so long. Do you like me playing with them, Sadie?" She was confused, clearly turned on but mortified that another man was playing with her. Although she was my first, everything felt natural after so long with Maryanne/Mark. Sadie could have easily stopped me but she just looked at me with her wide, made-up eyes, he mouth open, looking startled. I decided to take a leaf out of Maryanne's book. "You love me playing with your big balls, don't you, Sadie? It's my first time touching another man and I love it. Don't you? Feeling another man's hands on your balls, rubbing them. Your cock seems to like it, it's leaking everywhere. Here, taste." I scooped up some of her precum from the head and rubbed it on her lips, then pushed my finger between her full, pink lips. "Lick my finger, pretend it's my cock." Sadie hesitated just for a second then it felt like a vacuum cleaner was sucking my finger off my hand. Clearly hungering for release, she suddenly snapped and turned into an adolescent girl dripping with desire. "Oh, little Sadie likes her own cum, good girl. You're good at sucking, we'll have it put that mouth of yours to good use!" Kathy and Maryanne were transfixed, staring at the two of us. They had their hands in each other's crotch, mouths open, watching our every move. I gave them a Hollywood smile and turned to Sadie. I pulled her head down to me and we shared a passionate kiss, Sadie finally losing all control and ramming her tongue in my mouth. Oh my, I wasn't expecting this, at least not yet! I needed to regain control. I pushed her back. "Not so fast, girl! Slow down! Where's my foreplay?" I took her hand and placed it on my thigh. "At least give me a bit of a rub, big boy!" She looked aghast at being reminded that we were both men. I moved her hand back and forth on my leg, then placed it on my erection. "Your first cock! Feel it, Sadie. Does that turn you on? Do you like it? Lift up my dress..." Sadie seemed to suddenly come to her senses. "No, wait, this is wrong..." and quickly stood up. I wasn't sure what to do but I didn't need to worry because Kathy leapt into action. She quickly stood up and marched over to Sadie. She was at least a full foot shorter than Sadie, more with Sadie's heels, but she reached up and slapped her face, hard. Sadie looked furious and I thought that the evening would turn into a bloodbath but Kathy stared her down. "Is this how you treat our friends? After all I've taught you? So help me God, you'll never come again. I'll get a chastity device and lose the key. You'll never get to touch me again, I'll bring home lovers every night and make you watch. But that would turn you on, wouldn't it?" Kathy suddenly switched personas and became a sex kitten. "Don't you want that pretty girl to touch you, Sadie? It's been so long, hasn't it? You get to eat me out all the time, front and back, but poor Sadie gets no attention, let alone release. Do you really want to deny yourself like that? Look at Hope, she's delicious. Now apologize and pray that she'll take pity on you." I stepped in and fondled Sadie's firm, muscular rear. "Oh darling, I forgive you. Let me worship you. Does this feel nice?" I knelt down behind Sadie and ran my hand up from the back of her thighs to her round globes, and fondled them. God, I was so hard, Maryanne had trained me well. I pulled her pink panties down and Sadie carefully stepped out of them. She lifted her dress over her head and wasted no time in getting my head stuck between those gorgeous buttocks. I started high, at the beginning of her crack, and licked down to her rosebud. I grazed it with my tongue and moved down to her balls then back up. Finally I zeroed in on my target and rimmed her lovely ass. She was very clean, undoubtedly as part of her thorough preparation, and she was moaning and whimpering as I fondled her balls while bathing her hole with my tongue, then sticking it in and out, fucking her ass with my mouth. Sadie was swaying dangerously so Kathy came over again and held her up, arms around her facing each other, while I was still on my knees behind her, face buried in her ass. Kathy gave Sadie a long soul kiss while I continued to assault her rear end. "You love this, don't you, Sissy Sadie? A man licking your ass, fucking you with his tongue. Hope loves it and you do too, don't you, sissy girl? This is what I wanted, you to be a sissy fag, loving it all, embracing your true self! Feel Hope's tongue up inside you - don't deny you love it, I can feel your hard cock. It's dripping wet, yes, taste it. That's it, lick my finger, eat your own cum - mmm, you love cum, maybe Hope will let you taste hers! Yes, suck my finger, pretend it's Hope's cock, while she tongue-fucks your ass, you pretty sissy...yes, spread your legs, let Hope fuck you, a man eating your ass - oh Sadie, bet you didn't imagine this in your wildest fantasies!" Finally Sadie found her voice. "Yes, Mistress, it's wonderful. I feel so feminine, shaved, perfumed and oiled. Hope's so beautiful and she feels so good, I never knew...oh! - yes, oh...such...oh...it's wonderful. It's so dirty, licking me back there, but it's so good..." Kathy let go of Sadie and pulled me away. I could have kept it up for hours, I was deep in my subspace, my enjoyment dependent on Sadie's. Making her happy and excited was my goal. It wasn't a precursor to anything else, it was my only task, and I was profoundly happy to do it! As Sadie said, it was so dirty, forbidden, seemingly unclean that it turned me on even more. Kathy insisted that the four of us move to the bedroom. Maryanne was still on the couch rubbing herself; I could tell that she desperately wanted me to finish her with my mouth but she sighed and stood up, agreeing to the room change. The four of up trooped up the stairs, and I ensured that I swiveled my hips to show off my athletic behind. Kathy was behind me and she fondled me as we walked. Oh, just to be touched was exciting, and I was still hard. I was smiling like the cat who got the cream, and I was certainly expecting to get some cream shortly! We made it to our bedroom and I immediately drew Sadie down on the bed. She was amazing, big and strong yet at the same time soft, gentle and submissive. I took some pity on the poor thing, deciding that she should be allowed some release. Maryanne was definitely very demanding but nothing compared to Kathy. Poor Sadie... I licked and tweaked her nipples to start, while straddling her belly. She was naked by now and I still had on my panties and bra filled with breast forms. I avoided all contact below her waist and concentrated on her torso. "Is that nice, Sadie? Has anyone ever licked and loved your breast like this? I bet you'd love real ones, wouldn't you, honey? Is this nice?" Both nipples stood up nicely under my ministrations. I kept twisting and tweaking with my fingers as I licked her ear. "I love your ears, your earrings are really divine. Mmm, I also love licking your ears, but not as much as your ass. You're my first man, Sadie, so we're in the same boat. Do you want me as your lover? Or should I stop now?" Sadie took my head in her large hands and kissed me gently, her tongue slowly exploring my mouth. "Oh Hope, I love everything you're doing to me, and I want to give you pleasure as well. Don't stop, do whatever you want to me, I want it all. I never knew...well, being with another man could be like this. Gentle, sexy, slow, sensual. I'm so turned on, I'm all yours." Ah, so sweet! Clearly Sadie had been used and abused too long by Kathy. I couldn't see her as a loving partner, only a cruel Mistress. I could be completely wrong of course but it fit my own experiences of her and helped me feel like a Samaritan for poor old Sadie, simply craving a bit of comfort. And cock, of course... I scooted down Sadie's mountainous torso until I was face to face with her meat and two veg. And what a plateful! Hard, dripping man cock was at least 8-9 inches. I wasn't prepared for this - no amount of dildo training will do it. The sight, smell, just the reality of this massive cock, hard and wet, in my face was extremely intimidating. So I went a little lower and licked Sadie's massive balls - slowly and lovingly, then took each one in my mouth for a quick tongue bath. Sadie seemed to be having an out of this world experience - she had her head thrown back, eyes closed, mouth wide open, making little moaning/whimpering noises. Her legs were spread wide and I decided to play with her delightful rosebud while tonguing her balls. I thought that Sadie was hyperventilating so I speeded things up and moved to her large cock. Not only was it long but quite thick. Not Coke- bottle girth but not that far off. I wrapped both hands around the shaft and licked the head like a lollypop. I admired my red nails against her white, hard cock - it turned me on even more, made me feel oh so feminine. I stretch my mouth wide and sucked in the head while pumping the shaft up and down. "Oh, oh, oh...please..." mumbled Sadie. I took that as encouragement and explored the puffy mushroom head with my tongue. She seemed especially enthusiastic when I ran my tongue over the underside, sucking hard. The taste, the smell, my head and mouth crammed down between her legs - all made me giddy with desire. Her pleasure spurred me on, and I tried to look up into her eyes as much as possible. Trouble was that Sadie seemed to be looking into the distance with a fixed grimace most of the time. I wanted to finish quickly to move on so pumped harder and faster, and took as much as I could down my throat without choking. I had practiced with a dildo which helped my gag reflex but I couldn't take the whole thing. I kept pumping and sucking, then moved one hand down to her ass and pushed a finger in, swiveling it around. That did it! I was rewarded with a real gusher. First I felt the shaft sort of twitch then start to spasm, after which my mouth was flooded. Sadie went on and on, not surprising as she was denied release for so long. I swallowed a great deal but by no means all of her creamy seed. It was fine, a bit salty but not unpleasant, and I kept pumping to drain her completely. Finally she slowed and stopped, her hips at rest from their frantic pushing up and back. I licked up what I had spilled and quickly moved up for a kiss. I smiled manically with my lips pressed together and Sadie understood, took me in her massive arms and opened her mouth to receive me. We shared her considerable leavings back and forth in a lovely, exhausted kiss. I was still hard and horny but felt fulfilled. I had made her cum! In my mouth! I was excited at my triumph, satisfied that I had caused this lovely creature to release her load in me. We kissed for ages then I heard applause and looked over my shoulder - the two women were standing at the foot of the bed clapping! Maryanne opened her arms wide and I quickly stood up for a massive hug. "Oh you! Hope, that was magnificent! You were wonderful! Sadie didn't know what hit her! I know it was wonderful for you of course, I could see it on your face. You're now officially a cocksucking sissy fag! Well done, my love!" We kissed long and slow, a soulful exploration allowing her to taste Sadie as well. We broke apart and she immediately took me in for another massive hug. I was so proud! Kathy seemed to be feeling left out so I moved to give her a hug. Predictably she immediately pushed me down and spread her meaty thighs for me to lick her throbbing clit. She was so hot and wet she came quickly, so I stood up and kissed Maryanne again, sharing Kathy's juices. I went back to the bed and stroked Sadie's forehead, adjusting her wig. I kissed her face all over, cheeks, chin and neck. She had tears in her eyes - it was obvious she had been starved of affection as well as sex. I couldn't see her staying with Kathy for long (and subsequent events proved me right). Sadie put her arms around my neck and gently flipped me over. It was time to reciprocate and boy was I ready for her! She kissed me then slowly worked her way down, stopping to lick and gently bite my nipples. Finally she got to the main event. She seemed to need some encouragement. "That's it, Sadie, look at your first cock. Touch it, yes, like that...gently now! Pretend it's your own...but smaller! Put your face right up to it, that's it. Smell it - that's it, smell the sweat and cum, the musty odor. Go ahead, have a taste now, yes, lick the head. Your first cock - you'll remember it, like I did yours! Now take the head in your mouth..." She was hesitant at first but quickly got the hang of it. I guided her through it and even Kathy came over to watch Sadie's first cock sucking. She made up lack of technique with enthusiasm and I was so worked up that I came quickly, all over her face and in her mouth. When I finally finished she moved up and I lapped up what she missed and we kissed the residue away. Finally I looked up and say Maryanne on the carpet, on her back with her legs spread wide, with Kathy between her legs. Maryanne had ahold of Kathy's head and was pounding it into her, Kathy's face mashed into her sopping wet slip. Maryanne was calling Kathy everything she could think of - bitch, whore, slut, whatever she could think of, while pushing her head and face into her crotch. Well, it looked like Kathy couldn't handle Maryanne - not surprising. Maryanne was kind but fair to me, but had a wicked streak a mile long and had no problem taking on and besting Kathy. "One of you come here and fuck this cunt while she licks me!" Kathy demanded. I looked over at Sadie and waved her over - I was too spent and really, the privilege belonged to her. Sadie quickly went over, she couldn't believe it, but Kathy didn't even look up as Sadie smacked her wide ass. Kathy wiggled it in invitation and Sadie, hard already, eased her mighty cock into Kathy's sloppy wet slit from behind. She was merciless, pounding Kathy right from the start, and lasted nearly half an hour. Kathy must have come at least five or six times, and I could tell that Maryanne wasn't far behind. Finally Sadie let loose a mighty growl and grabbed Kathy's hips as he exploded into her. Slamming into her hard and fast, Kathy's face pushed hard into Maryanne's pussy over and over. At least Sadie pulled out with a plop and Kathy lay supine on the carpet. Maryanne wanted dessert so she waved me over - I was to have a really rare treat, being allowed into her with my cock. We even started out in a missionary position but she quickly flipped over to ride me. It was exquisite, a wonderful finish to a magical evening of first for Sadie and me, and I loved coming inside Maryanne. Of course I had to clean her out with my tongue but it was wonderful doing so. ***** A few weeks later we learned that Kathy had become a lesbian bottom slut and lost all interest in Sadie. Poor girl, what was she to do? We offered her shelter at our place and within a week we had fixed her up with a single sissy Maryanne had met. The two of them hit it off immediately and Sadie moved in the following week. We see them quite often but very rarely have sex with them, they're too much into each other for anyone else to get a look-in. Maryanne and me? We're fine, still get together with others but we're rock-solid together. Nothing out of the ordinary to write about, but we did chat to a very interesting threesome the other day at a club - two delightful sissies, Dee and Clair, and their girlfriend Agnes. Maryanne was intensely curious about the three of them and they promised to come over for dinner and drinks soon. Might be fun...