Siss the Bride Ch. 03

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Trouble in paradise for Ophelia and Patrick.
4.6k words
4.52
41.2k
39

Part 3 of the 3 part series

Updated 06/07/2023
Created 06/20/2015
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Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfect tool to keep you there; and also, naturally, I do love him.

However, the other thing I've built this new life on is sex: I'm a walking fetish! (which I do love by the way, both in sexual and non-sexual situations). However, the problem is that I am as dependant on gratification as I am my brother – gratification is one of the other great masters of life, relentlessly buttfucking humanity in the brain. So, there was one little incident, a few stupid mistakes, that nearly jeopardised what I have.

It started, as some of my best stories do, with me on all fours. Malcolm, the hunky, bombastic Australian with the body of a movie star and the sexual stamina of a High School Footballer, had his cock in my cherry-red lipped mouth. His head was just pushing open the tightness at the back of my throat, guiding the rest of his member onto my ever-lapping tongue. Meanwhile, my big brother was casually thrusting his own massive cock into my accommodating sissy ass – he was taking his time, teasing me, slow in pace, and only hitting my sweet spot every once in a while. He was doing this on purpose, he was an excellent lover and knew exactly how to please me if he wanted to get me off – teasing me just extended the pleasure. So there was me, fully naked apart from my stockings and heels, in the garden (did I forget to mention that? We'd just been fucking in the pool when Malcolm and Katherine arrived), being fucked torturously slowly by the two greatest cocks I have ever had the repeated pleasure of servicing. As per my brother's promise, Katherine had started coming to watch these little fuck sessions and, as per her promise, this time she had her camera next to her filming the entire thing. She had her hands down the front of her denim short-shorts and I could hear her as she narrated a story of my degradation for the camera.

"Look at this desperate, faggy, slut." She was saying, in a lusty drawl. She was putting on the 'domme' voice which would undoubtedly turn on admirer and fellow sissy alike "two cocks in her and you can tell she still wants more – how naughty! She should be glad her husband has been kind to share her with his friend, how selfish can a bitch be? Such a greedy cumslut, she'd probably hump, fuck, and suck her own brother if it meant she'd get a hot, sticky, load of cum: everywhere, in her mouth, her hair, her eyes. She has such good skin, right people? The secret is lots and lots of cum."

I like Katherine. She was actually really kind to me when we went out together, she really made me one of the girls, especially with all the clothes she gave me and helped me buy – my own style was very much influence by this blonde punk-princess, though being a princess she was of a higher class than the punk-whore. I mean, she was glad a guy could embrace his feminine side! But she also recognised that as soon as sex was explicitly involved, that embrace is one of submission, and she swung in the other direction. She did everything she could to make me out as a submissive sissy fag, neither man nor girl, just a slut to be used. Which is why, after her little story, I saw her whisper something to the camera out the corner of my eye. I might have wondered what she was up to, but I assumed it was a cue for me to play up the slut act, so I moaned loud onto Malcolm's cock, and tilted my head as I bobbed my head forwards, savouring the taste of the dick on my tongue, which I rubbed along the veined ridge. My brother also picked up his pace at that point, but just as I was getting into it, he stopped suddenly. For a split second I thought he had cummed, but the lack of wetness splattering my insides soon proved that wasn't the case. Then, provoking a disappointed moan from me, he slipped out. I flexed my gaping hole, a signal begging for his re-entry, but he just walked round to my front and rubbed his pre-cum on my cheek as I continued to suck. I got the hint. I grabbed his dick, and moved my mouth from Malcolm to him. He thrust his dick into my mouth in one fluid motion, but at the same time, something entered me in a slick, rubbery thrust. It was like oil in my ass, it was deeply erotic in that it was something new and unknown – but of course, I knew exactly what it was. I pulled my mouth away and looked over my shoulder; sure enough, Katherine was there, fucking my ass with a massive black strap-on.

My brother grabbed my hair and twisted my head round to face the two men. He had both his, and Malcolm's cock in his hand, right next to each other. I looked up at them, innocence and lustful hunger once more mingling in my eyes. This was new, and exciting. Malcolm, who I always thought of as the most straight-laced guy ever, did not seem phased by his dick in contact with his best friend's monster cock, or that both would soon be in the mouth of the cross-dressing brother of said best friend. Oh, and his girlfriend was fucking the brother in the ass with the same dildo he had come to know. I opened my mouth wide and wrapped it round the two cocks – holy fuck, it was like trying to fit in a mega lollipop in all at once. The width forced my mouth even wider than I had it, and now air could rush through. I was breathing hard through my nose, and the taste combined with the sheer mass had me salivating uncontrollably. All the while, Katherine was ripping into my ass, forcing me forwards as she tried to get as much pleasure as possible from the toy as it rubbed against her clit. My own sissy 'clit' was getting ever harder, but still managed to be the smallest 'cock' around. Katherine slapped my ass, and Patrick tugged my hair so I started to choke on the cocks – even Malcolm had his hand at the back of my head. They were all narrating this degradation.

"Hey Katherine" The Aussie accent chimed to his girlfriend "how's this bitch enjoying Lucian?"

"Well she's moaning good enough" Kate grunted "but I think we should introduce her to The Duke next time."

"Woah, Kate, hold up" Patrick said "As her husband, I don't think she should – I don't want her knowing there are dicks bigger than mine!"

"I told you, don't call me Kate! Do that again, I'll use the Duke to cuckold you and make you both my sissy bitches. You all know I would!"

I was feeling really good about all this (even the idea of my brother becoming a fellow sister, because I'd still be the sub!) and was just getting into the swing of things when I felt 'Lucian' stop moving while buried as deep as possible in my ass. My brother and Malcolm backed away, and my brother knelt down quickly and kissed me hard before turning me onto my back. That is when I saw one of the most unappealing sights a gay guy can see in his life – a fully aroused, dripping wet, pussy. Just not my cup of tea I'm afraid, and I probably won't be very good at describing what came next but I sure can try.

Katherine had unstrapped herself from 'Lucian', but had left him deep inside me. After I had been turned to look at her, she produced a small piece of string and tied it tightly around my shaven balls, making them go numb. I was still rock solid, a full 6 inches pointing straight upwards, and now Katherine had her pussy poised over it – I looked away, focusing on the two cocks which were still hovering over my face. I knew instinctively what was going on next: I reached out both my hands and grabbed the two dicks, started stroking them slowly, rubbing my thumbs over the heads. Something warm, and wet, wrapped itself around my dick. Gay is gay, and attraction is attraction, but when I can't see what's down there, it just feels the same as my brother's mouth. Either from her own arousal, or what she called the 'mediocre girl-cock', Katherine had slipped straight down to my base and was working the pool with long, haughty moans. It sent a wave of pleasure down my little dick, that swiftly turned to a pulse of pain when it reached my tied up balls. I continued to focus on the cocks, on working the shafts with my hands, with the messy load due to cover my face, but Katherine was getting very distracting in her excitement.

"ugh, you little fag, you'd better thank me for this. Your silly little dick doesn't get the pleasure of being in a hole very often, you should be grateful for what you get." Somewhere, something inside of me reacted to this in a way I thought I never would:

"Yes mistress" I replied obediently. She laughed.

"Aww, Ophelia, that's so cute!" which made me smile, before she continued in her dome voice "but you're gonna prove your submission by letting me enjoy your cock as much as possible." And she continued to grind her pussy on my dick, hitting my head against her clit. I had lost all control, even the two dicks in my hands seemed to be pumping themselves – time sped up and soon enough Malcolm was shooting ropes of cum over my face. It splashed in my hair, and some dropped onto my tongue; seeing her boyfriend cum must have really helped Katherine because she tightened on my dick, and let out the loudest scream. The neighbours, if they hadn't heard us before, definitely heard that. She was flopping on top of me, cumming, and I could only feel an extreme throbbing where my dick was getting desperate to spew. This in turn obviously got my brother going, for another burst of cum hit me square in the eye while I was distracted by Katherine. The strapon was pressed against my prostate, and all this sexual activity around me made me the horniest I have ever been in my life (which is saying a lot). I absolutely needed to cum, but my brother had set down the absolute rule I am not allowed to do it myself unless he asks me to show him. For some reason, no matter what, I stuck to that rule.

Which is why I was very confused when Katherine slipped off my still-throbbing dick, and fetched the video camera to take the last shot – I still smiled my cummy smile for our fans, but I was slightly put out. My brother got me a cookie and dried my face off (a favourite treat of mine) and they all went and got dressed.

"Umm, honey?" I asked, causing all three to turn around. Patrick and Katherine, forever the closest friends, wore the same expression of pretend innocence. Malcolm looked a little more abashed. "that was really lovely, but do you want me to do a show for you now?"

"Oh that!" my husband laughed, light hearted but still scary and unknown "No, Katherine was telling me about this excellent thing called orgasm denial. Should make you ever hornier and hornier, always desperate for the next opportunity to cum" as he said this, Katherine came over, untied my balls, winked and gave me a kiss on the forehead. It was part of a great game obviously, and this was her in caring mode, but I was shocked. They'd all got their orgasm, where the fuck was mine?

In this confused state I got up and followed them into the house, and went up to my room to get changed into some clothes. It was difficult getting the panties back on, what with my still raging boner, but I dressed up diligently just the same, I always liked to look pretty. As I was pulling up my red pleated mini-skirt I heard a car pull out of the drive. That must be Katherine and Malcolm going home, I thought. Then, as I was buttoning up my blouse, I heard my door creak open. That must be my brother, I thought. I was wrong both times.

Malcolm stood leaning against my doorframe, hands in his pockets, and a sad smile on his face. He was clearly admiring me. He stepped forward into my room, I sat back on my bed.

"Sorry about all that Ophelia" he sighed "Katherine never does that stuff with me and, well, you're special to her. She gets to try things out, you're exciting."

"It's okay, I know she means well" I looked back at him, half-smiling, before adding "god it's fucking painful though!"

"It bloody well looks it! But, you know... the two of them have just gone out to dinner together – I said I'm not hungry. I'm sure they wouldn't notice if..."

"If what?" I said, already perking up despite an underlying guilt somewhere in my gut.

"Well, if I fucked you into a cummy oblivion to be frank about it" He responded, smiling fully. I bit my lip, looked up at him, and nodded my head.

It felt so wrong, betraying my husband like this, but my heart nor my brain was in charge at that moment, I was being led by the fully charged lust of my dick. I got up from my bed, and kissed Malcolm on the lips, not a romantic kiss at all. A wet, sexual kiss that served its purpose: Malcolm, despite having just cum all over me, was near-instantly hard. He grabbed me by both arms and swivelled me round him, thrusting me against the wall and kissing me hard, his tongue crawling down my throat, causing me to gag in surprise. I pulled away from the kiss, both our saliva bridging between us, and turned around. I put my hands on the wall, I arched my back and emphasised my ass and panties, clearly visible beneath the skirt. Malcolm simply slid the panties aside to reveal my hole and fucked me fully clothed. His cock fell into my gaping hole (still sore from 'Lucian') and caused me to fall against the wall. I grunted my satisfaction. He thrust in, slowly, patiently, not wanting to cum until he knew he had it right – and when he had it right, he knew. He hit my prostate and I wailed like a little baby. He put his hand on my cock, to my delighted surprise, and started stroking me very lightly and slowly – then he thrusted again, hit my prostate, and I came buckets. My cum hit the wall, my dick feeling a glorious release mingled with a tingling pain. Some of it splashed back, onto my legs and feet, and as the shockwaves of pleasure passed through me, Malcolm also started to cum, filling my ass with his seed. I felt so incredibly dirty, but that kind of sexual gratification was incredible. Maybe my brother was right about orgasm denial, but I didn't take note of that at that moment. I just knew that I wanted more of that. First things first, my sissy instinct cut in and I dropped to me knees and started licking the wall clean, drinking my own cum and moaning my thanks to Malcolm: he took a few pictures and a short video. Then, after that, he kissed me and helped me clean up. Since that, I started seeing him when my brother was at work.

In the morning, I swallowed my brother's cum lovingly and happily, as I always had done and hoped to always continue to; at midday, Malcolm would fuck me in the ass so hard that I would cum everywhere – sometimes he used his hands if I need help, I normally don't; and then, obviously, at night my brother fucks me with a string tied tightly round my balls. After he cums in me (which I still enjoyed) he'd tell me that I wasn't allowed to cum until he said, that he was saving it for some special event that was coming up. Now, I have no idea what he thought was 'coming up', the only thing I knew was 'coming up' was Malcolm 'cumming up' my ass. Luckily, I was less frustrated than I could have been because of all Malcolm's help, but the fact I had to attempt to go to sleep with an uncomfortable boner. That mild inconvenience alone gave me the will to continue the affair.

However, that stupidity, arrogance and stubbornness is what led to it all going sour. Naturally, one day, my brother caught me cheating on him. I was dressed in his favourite PVC outfit of mine, as a proper thank you to Malcolm for helping me evade my orgasm denial. It was comprised of a very tight waisted corset, elbow-length gloves, and thigh-high socks. All jet black shiny PVC. When I wore that, I didn't wear anything else, and sex was always at its sluttiest. Malcolm was sitting on the sofa, and I was straddling him, spread-legged, bouncing up and down and slapping my bare ass onto his lap. He was biting along my back and calling me his secret beautiful sissy slut – he was starting to get as good at fucking me as my brother, he'd started to know all my little kinks that my brother knew from a lifetime of being in the room next to me and the many men I'd bring home. And also from marrying me, that put him at an advantage too. Even so, Malcolm was fucking me really well – though I was doing most of the work, he just had to sit and keep hold of my cock so I could pleasure us both – and I had my eyes closed in ecstasy. I was moaning and bouncing when I hear Malcolm say 'shit' from underneath me. I assumed that was another grunt of pleasure and I went into overdrive, milking his cock with my ass, desperate to get that cumload that would send me over the edge. The truth was far from it.

"Get out" I heard my brother whisper hoarsely. My eyes shot open. Shit. He was ashen faced, appalled, and actually looking a bit hurt. Looking back, I gotta say, his pale face underneath his tangled black hair; the spark of anger that glinted at the back of his sad silver eyes. It was pretty fucking hot. However, at that moment I only felt the deepest shame. What was I doing, playing around like this, this was my brother I was hurting. I couldn't do this to him, of all people! After I'd married him it seemed to love him like I did was the most natural thing in the world, but by fucking Malcolm I'd gone back on that. "Get out" he repeated, a little sterner. I jumped off Malcolm and quickly put on some red silky panties, but ran outside in due haste – Malcolm followed, zipping up his trousers.

"It'll be okay, Ophelia" Malcolm cooed, trying his very best to calm me down as I was obviously in a panicky state, breathing quick and shallow. "He's mad now, but it will blow over and – "

"No, fuck off!" I wailed, breathing heavily, scared "I've messed it up, I've lost everything. I'm nothing now!" and I pushed him back, hard. Taking the opportunity of him being stunned, I ran. I ran for god knows where, towards town, even at that time of day. I tottered slightly in my heels, but heels were the only type of shoes I was allowed to wear so it wasn't too different when it came to running. I started taking back alleys to avoid people, in case my cock was still showing through my panties. I hadn't cum, so it could have still been throbbing. I made my way to this alley, near a gay bar I used to frequent. In fact, I took my older brother there once on my 21st birthday. He got hit on by so many guys, that I had to swoop in on the dance floor to save him – I'd even worked in a cheeky grind now that I thought about it. I was really drunk, they did good cocktails at this place – it's where my husband first had his favourite drink of amaretto on ice. Well, ex-husband now, I thought.

I sat on the dirty alley floor and considered my position. The PVC squeaked as I sat down. I was no longer really a man, I couldn't very well go back to a normal human life and job. I hadn't exactly made any irreversible changes, to be fair, but I had essentially killed off my former self. I had basically made myself into a fuck toy – and if I was honest that was the life I enjoyed. So, for a sissy fucktoy like me with no master in sight, there were two options. One, pornography, which let's face it is too difficult to get into (even if I do have amateur experience). The other, street prostitution. Random hook ups, plenty of different cum, money for sex. That last thing struck me as pretty fair a deal – money and sex! Considering I would pretty happily do it for free. It was an easy job too, suck a cock here, open my ass there – and as long as my ass remained as good as it was, no one would ask questions about the front. But still, the idea terrified me, it was nothing to the fantasy of returning to my brother's arms.

The day had grown dark, and quiet. It was night now, definitely night. I still definitely needed to cum, I was still horny from Malcolm fucking me, even if my boner had receded. That thought, the PVC tight against me like a second skin, and the silky smoothness on my dick started to get me hard again. Yet, I still didn't stroke it; I resolved that I only deserved to cum if a client made me cum. I could self-impose some punishments, it would just make me more industrious. As I thought this, I heard the noise of a car drifting down the road, the first I'd heard. I crawled out the alley and stood up in the blaze of the headlights – in this part of town, how I was dressed wouldn't matter. The car stopped, I was prepared to meet my first client. I shielded my eyes against the light as the car door slammed, and a man climbed out, a black silhouette approaching quickly. He grabbed me round the waist, and forced me back into the alley. My eyes adjusted, and who else should I see but my brother?

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