Sissy Fantasy to Nightmare Ch. 02

Hi everyone! It's been a very long time but I wanted to write another chapter of this story. Reading how much everyone enjoyed it last time was awesome. I'd love any more comments on what you'd like next. Also if anyone is up for editing the next I'd appreciate it!

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I woke up the next day with a moan as my pounding headache reminded me of the night before.

I stumbled into the bathroom to shower and get water. I looked into the mirror and realised I was still in the red satin thong from last night. Suddenly it all came back to me and I began to sweat.

I had been dressed as a school girl....

I had given a hot shemale a blowjob...

My fiancés' ex boyfriend caught me, filmed it and made me suck him off...

Fuck.

These were things that maybe in my darkest fantasies I had thought about but I never wanted them to really happen.

I can't believe I'd cheated on Rosie, and it wasn't even with a woman. It was with her ex's cock.

I felt sick as the humiliation rose inside me.

I tried to scrub it all off me in the shower but couldn't remove the image of his 9" cock violating my mouth. And how hard it had made me...

On my phone I saw the usual messages from my best man about how good the night was. But I also saw a message from Richard and the blood drained from my face.

"Loved your performance last night Rosie. I'd love a repeat today as we are in the same hotel." Attached was the video of me as I took the cock in my mouth, bliss on my face and a raging boner clearly visible in my panties under the skirt of my outfit.

I frantically typed a reply "Richard, that was a drunken mistake. You took advantage of me! Please let's forget about it."

He instantly responded "Why is your little dick so hard if you didn't like it?"

"Please, no one can ever see that"

"Then let's talk. What's your room number slut?"

The way he called me a slut began to anger me but I thought if he was willing to talk there was a way out.

"82" I typed. My fingers shook.

Nothing in response. I paced the room as I waited. Then, a knock on the door.

Richard was stood outside, all 6'2" of him looming over me. He immediately pushed his way into the room.

"Look I think we can resolve this like men please? We both know last night was fucked up." I squeaked out as I hurried after him into the room.

He turned and grabbed me, moving his face in close. "It wasn't a mistake, it's what you're meant for. I always knew there was something off with you. I can't believe Rosie is marrying a sissy fag."

"I-I'm not a sissy!" I protested.

"Bullshit, you loved your prissy little outfit. I know you've worn her stuff before. Looks like it would fit you too. Pathetic." He spat the words at me.

I shrank back, feeling totally vulnerable.

Richard continued. "I'm a reasonable man, and one who likes a wager. So I will offer you a way out John... if you can pass a test."

Hope rose in me, this was progress, we could sort it like real men. Then my heart sank when I heard his offer.

"Let's call it the 'Sissy Test'... you are going to dress up again and submit to me. If I can prove you enjoy it, have you begging for my cock then you will become my personal sissy slut.

But, if you make it through without breaking down, cumming or begging me to use you then I'll let you go. I'll delete the videos in front of you and you can carry on with your straight little life."

For some reason I felt my cock swell even as my mind revulsed.

"Richard... we can't do anything again. That's fucked up, I'm not gay and I don't want to suck you off or dress up for you even if I know I'd pass the test!" My voice rose up an octave as I responded.

"Well John... firstly, you don't have a choice. If you don't try the test I'll simply send the video to pretty little Rosie and ruin your life. Secondly, if you're so confident you'll pass then you have nothing to fear. This is your way to freedom..."

I felt torn. I knew he was blackmailing me but I also felt like this was my only chance to win my manhood back. Ironically it was by acting as a sissy. I had to believe I could pass the test.

Richard began to look around the room as I stood there conflicted. This was the room Rosie and I booked for the wedding night so it was the honeymoon suite and all our stuff had been sent in advance.

"What are you looking for?" I asked.

"Your outfit for the test..." he responded.

His eyes lit up when he saw Rosie's bag and he rummaged though it. "Ah ha, perfect" I heard him laugh.

He turned around and my cock stiffened in my jeans. He was holding Rosie's bridal lingerie. It was the stuff of my dreams.

White silk with delicate lace trim across the basque and thong, with matching white thigh high stockings that glistened in the light.

My sissy side collided with my male ego. I wanted to wear that outfit so badly. And I knew I would pass his test.

"Fine. But when I pass you delete everything. And you say you're sick and can't make the wedding tomorrow - yes?" I tried to assert myself.

Richard boomed out a laugh. "Sure thing. But when you lose, and you will then you will be my personal sissy slut. That means I own you. I may not break up your marriage but you will be at my beck and call to serve my sexual needs.

I'm going to film today for collateral. Along with last night if you lose and back out of being my slut I'll post them everywhere and destroy you. If you somehow deny your true nature until I cum then I'll delete them like I said."

I took a deep breath, not allowing myself to think of what happened if I lost, and nodded.

I walked to the bed to begin the test.

The white bridal lingerie was laid out on the bed. It almost glowed with sexual, sensual energy and for a moment I forgot the situation I was in. I would have died to wear Rosie's wedding night outfit under normal circumstances.

But these weren't normal circumstances.

"You know the deal now. If you like you put it on and like what happens next then you are mine. If you don't then that's fine, I'll let you go, delete the videos I have and let you marry Rosie and live a happy straight life." Richard's words filled me with hope, now in the sober light of day I could prove I was a real man.

"Now we begin. Strip and get ready for me in the bathroom Rosie"

I picked up the delicate basque, thong and stockings and the white silk sent shivers up my spine. I carried them into the bathroom and stripped down. As I began to dress my confidence that I'd pass this test of masculinity wavered slightly. The silk caressed my body and it fit like it was made for me. I looked at myself in the mirror and was horrified to see how pathetic I looked. I was clearly a man but the lingerie framed my figure perfectly, you could see a clear bulge in my thong as my cock strained against the silk. I took a deep breath and walked back into the bedroom.

As I opened the door I saw Richard stripped naked in front of the bed with his phone camera facing him and already recording. My stomach sank and I suddenly felt sick.

"Hello everyone, we have something special today for you. You're going to meet Rosie and watch her lose her sissy virginity. Come get on your knees and say hello to everyone Rosie." He spoke into the camera as if it was live and stood up at the end of the bed.

I feel myself walk forwards like a zombie, as if I'm not in control of my body. The garter belt tugging on my sheer thigh high stockings with each step. My confidence weakened again as the perfect silk of the outfit caused blood to rush to my cock.

I sank to my knees in front of my fiancés' naked ex boyfriend, his meaty cock swinging in front of my face.

I turn to face the camera, and reluctantly and quietly say "hello". I know my face is clearly visible in this footage.

Richard kicks me gently, "try again Rosie. You have an audience, tell them what you want."

I felt hot shame burn through me, knowing he needs me to pretend for the camera. "I want Richard's cock to fuck me and show everyone what a real sissy I am." I spit the words out and look up at him. Past his swelling cock I see him nod his head.

"Good girl. Now show everyone what you did to me last night..."

I can't help but add, "he's blackmailing me into this..." to the camera as I try to preserve my masculinity even as I kneel there in lingerie.

The memory of sucking his cock came back to me vividly. I had been very drunk last night and the prospect of doing this sober filled me with disgust.

"You know you like it..." he said as he swung his hard cock to tap the side of my face. I flinched with disgust.

Knowing I have no choice I open my mouth and slowly move forwards until the head of his cock is by my lips. I move the last inch and feel his warm mushroom head enter my mouth. Sober this blowjob is so real. His pre cum is salty and strong, the warmth of his dick feels too masculine on my tongue.

I immediately gag and spit, but he places his hands on my head and guides his cock into my mouth. Slowly almost lovingly he rapes my mouth with his dick. I continue to gag as the salty pre cum leaks into my mouth ever faster.

"Now now Rosie I think you did this better last night. Don't be shy unless you want me to share your real name with our audience."

My face blanched at the thought of it, even worse than them seeing my real face.

I begin to work his cock like I did the night before and how I like it when my Rosie does it. Bathing his shaft and balls with my tongue while I massaged the head with my hands.

I hear him groan and know it's getting better. Part of me hopes if he cums once then he will want to stop afterwards like I do. I try to finish this as quickly as possible and throw myself at his dick. I gag and moan and try and swallow as much as possible in an effort to make him cum, pretending I like it.

"Mmmhhh Rosie you're showing your talents now. I'm getting close and it looks like you are enjoying it too..."

I briefly look down and to my horror I see my cock is trying to make a tent in my wife's white silk panties. There's even a small wet patch. I'd been so focused on him I hadn't realised the effect it had on me. I swallow nervously and look up.

"Don't worry Rosie, a simple boner isn't enough to prove you lose this bet. I know how horny that pretty outfit is making you. We will take some more... definitive to show you're truly a sissy."

I go to start sucking his cock again but he stops me with his hand. "I think it's time to show the audience what I came here for. Get on the bed."

At the head of the bed I saw there was a mirror he had moved there. Even now I couldn't help but watch my lingerie clad body bend and move onto all fours. I imagined how this was meant to go, how it was meant to be my new wife in this outfit, excited to have me fuck her. Not me, here in her place and terrified to take her ex boyfriend's thick cock in my panty wearing ass.

My heart beats faster than ever, all I have to do I show how I'm not enjoying it until the end and this nightmare will be over. So long as I don't enjoy it then I'm still a man, not a sissy. He won't break me I think to myself.

I gasp as I feel Richard's hand pull my thong to one side. My cock now limp from fear still tucked into its satin prison.

Behind my back I could audibly hear him lube his cock and I felt my virgin hole tighten at the thought of what was to come.

He pulls the straps of my basque that were attached to the stockings to move me into the optimal position for him. I had never felt so vulnerable or more like a sissy then in that moment. My lingerie used to manipulate me into the right position for a man to fuck me.

Then I felt it. His warm cock head on my ass.

"Please don't do this Richard, please. I'm begging you not to... you don't want this," my voice nearly breaking from fear as I said the words.

"Oh but Rosie, I do. And the fact you are still trying to hold onto your masculinity makes it all the sweeter to break you."

On the last word I felt his cock push into me and I involuntarily moved forward to avoid it.

"Bad girl" he grunted as he grabbed my shoulders and physically pulled me back onto his cock. His lubed cockhead popped inside me and I whimpered as pain shot through me. I had used dildos before but nothing his size.

"I... I can't take it. Pleaseee stop Richard."

"I'm not Richard, I'm your Daddy now Rosie" he responded as he forced me further back on his cock. I grunted and whimpered as I was impaled by his fat cock and I imagined what Rosie felt like taking it for the first time.

Slowly but surely his cock inches into me until I felt his hips on my ass.

The realisation that he had fully penetrated me broke something inside me as shame overwhelmed me. My sissy side had brought me here. If only I hadn't dressed up I would be safe now. Tears welled up and dropped down my face.

"Mmmm it's ok to cry when you lose your virginity. Your ass is so tight it's milking my cock right now." I could hear him behind me.

He began to ease out before pumping his dick back into me. Each thrust was accompanied by a jolt of pain and more shame as he invaded my ass, I continued to silently cry as he fucked me.

Just a few minutes I thought to myself, you can do this.

"Mmm fuck you look so good Sissy Rosie. That outfit is perfect. Just to think your wife was going to wear this but here you are taking my cock like a good girl.

I know you think you're going to win this bet but I've barely got started."

I closed my eyes and tried to ignore what was happening to me but Richard began to pick up the pace. His thrusting increasing in power and urgency and I now knew what it felt like to be used as a woman. I was helpless as he began to pound me. I realised I had never fucked Rosie like this but he must have. Did she ever think about him when I was trying to pound her with my dick?

To my horror I realised I realised the feelings in my ass were beginning to shift as the feeling of shame and the silk lingerie began to turn me on. My cock was stirring in my panties and I saw that the small wet patch now covered them totally and I was leaking onto the bed.

"Mmm do you like that Sissy Rosie? Tell me what you want sweetheart..."

"Nghhh nooo.. no it's just... just the panties. I don't want your cock." I grunted through waves of pleasure, desperately clinging to the last parts of my male ego. I just needed to last a few more minutes, surely he would cum soon.

"Mmm ok, let's see you handle this then slut," his voice became sterner.

Richard seemed to go to another gear, grabbing my hips forcefully and literally jack hammering his 9" cock into my ass. It almost paralysed me and I gripped the sheets just trying to cling on. Without meaning to a let out a squeal as his cock hit my prostate.

"Oh did Rosie like that?" He asked as he redoubled his efforts. Now consistently hitting the special place inside me and I couldn't help but moan into the bed again. I realised I was getting closer and closer to losing this bet and becoming his permanent slut as pleasure racked through me.

Suddenly a noise interrupted us. I sighed with relief as I realised it was my phone on the bedside table. Maybe I would get a breather. I could see my fiancée's name on the caller ID. I crawled over with his cock still on me to decline the call.

From behind me in a commanding tone Richard ordered me, "answer it slut"

I turned to look at him in panic... "I can't! She will hear you! Please please don't..."

"I don't care slut, do it or I'll send her the video from last night," he responded.

"Pl... please. I'm begging you," I wailed.

"Do it. On speakerphone slut." For added emphasis he shoved his cock a further 2" inside me.

With my heart in my mouth I clicked the accept call button and put it on loudspeaker.

"Hey babe!" Rosie's sunny voice sang through the sex tainted air in the room.

"H-hey sweetheart." I replied, now sweating with fear.

"How was the Stag last night? Did you have fun with the boys? Was Richard nice to you?"

I realised that upon hearing his name Richard's cock swelled in my ass and he began to gently rock in and out of me.

"Errr-m yeah it was great. We went to a strip club, hope that was ok! Rich-hard was fi-ine."

His thrusts making my voice paused and stop with each inward movement.

"Hehe that's ok, so long as you didn't get any secret blowjobs from them baby!" She joked.

I heard Richard snort with laughter behind me.

"I'm glad you got along, I think you should spend more time together, you would be good friends!" Richard was picking up the pace of his fucking and pulled me round the bed so the camera could see me on the phone while he pounded me.

"Uh-huh, y-you are prob-bably right sw-sweetheart." I choked out.

"Are you ok baby? You don't sound good and we need you healthy for the big day!"

"All g-good just a bit hungov-er sorr-rry" I managed to get out

I was desperate for the conversation to end but Rosie started to tell me about her hen party before I could stop her. I had to physically fight the moans and groans of pleasure as Richard used me like a cheap whore.

It was the ultimate emasculation. I was dressed in her wedding night lingerie, on the phone to her while her ex boyfriend fucked my ass. My cock was betraying me and I had never been harder. A constant stream of pre cum leaked from it with each thrust and I began to lose track of time.

Eventually she hung up to go see her mother and I gasp a sigh of relief.

"Good girl sissy, I was hoping you might cum on the phone to her. I know you're getting close. What would she say if she could see you?"

I could only mumble a feeble comment back as I was almost non-verbal and broken.

"You were so confident weren't you? But now you're close to losing it. Don't worry though I'll treat you good as my permanent sissy slut."

I realised he was right and I was almost on the edge of cumming as his cock relentlessly pounded my ass

"Deep down you want me to break you. I'm sure you watch your sissy faggot videos all the time while you jerk that little cock in her panties. I'm just showing you you're true self Rosie..."

I moaned as he began to piledrive me. I've never experienced pleasure like it and I lost control. I groaned and gasped as I tried to hold on but with each thrust I could feel my masculinity leaking away

And then suddenly he stopped, pulling his cock from me and I felt so empty.

"Tell me what you are. This is your choice now. If you ask me to leave I'll go, but if you want my cock you are sealing your fate as my sissy forever." He laid out his ultimatum.

I wanted to fight it. I wanted to tell him to leave. Then I saw myself in the mirror. Rosie's silk white basque was stained with our sweat from sex and I saw my raging erection and cum strained panties. I knew what I was deep down, I couldn't fight it. He had broken me.

"Please fuck me daddy..." I whimpered, knowing I had crossed a line never to go back. "I need it inside me, make me your sissy slut forever."

"Good girl, I knew you'd make the right choice" Richard smiled victoriously.

In a flash he grabbed my ankles and manhandled me into position. His tall athletic frame making mine seem small and feminine.

I uttered an ungodly moan as his cock re-entered me and forced pleasure through my body. "Thank you daddy, thank you for fucking me." I had given in completely as I now committed my ass and mind to being a sissy.

Richard just grunted as he now pounded me with passion and renewed vigour. I felt the pleasure building inside me and I lost myself in it, now moaning and groaning with uninhibited joy as he fucked me like a true slut.

"Da-daddy I'm goin-going to cu-cum," I gasped.

"Beg me for it slut. Tell me what you are!" he instructed.

I could no longer help myself as I gave in to all my deepest, darkest fantasies. "I'm your worthless sissy cum whore Daddy! I'm too pathetic to fuck my girlfriend, I just love to wear her pretty panties and suck your fat cock. I crave being your sissy faggot! Please breed me and break me into the true slut I am daddy!" I was now pleading with him to cum in me.