tagTransgender & CrossdressersSissy Fantasy to Nightmare

Sissy Fantasy to Nightmare


My first ever story here so I would appreciate any feedback. Hope you enjoy it!


Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me.

"Morning sleepy head," she greeted me with a smile. "No time to waste if you're getting ready for the stag."

It was just 3 days until our wedding and the pre-ceremony traditions were happening today.

Rosie rolled out of bed and I watched her seductively walk to the bathroom for a hot shower. She was dressed in an ivory silk chemise and boyshorts trimmed with lace. Her taste in lingerie was impeccable and some thing I loved (and indulged) about her.

We'd met 2 years earlier during a leaving party for someone at work. She'd been getting a drink at the bar next to me, we'd started talking after she accidentally got my drinks order and before we knew it were making out on the dance floor before heading to her house. It had been a whirlwind romance.

I would have got up to join her in the shower but in anticipation of the wedding we had put ourselves on a two week sex ban to make sure our first night together as a married couple was amazing.

Rosie didn't take long and soon she was drying her perfect body in front of me. 5'8" with a perky ass and perfect c cup tits, her long golden hair fell across her tanned body. I still couldn't believe she was mine, or that she'd agreed to marry me. I definitely considered myself the luckiest man in the world.

"Have a good time with the boys tonight, just let yourself go. I will be with my girls doing the same. And please be nice to Richard, he's excited about joining in," she instructed me as she quickly got dressed to go.

Ah yes, Richard - her ex. They were still good friends and she'd asked me to invite him on the stag as a favour. He seemed nice enough but I wasn't best pleased about it given their history.

"Of course, he will be just like any one of the guys, I promise," I answered.

With a quick kiss to say goodbye she headed put the door and I was alone in bed.

Despite our self imposed celibacy I opened up my iPad to browse some porn and logged into my favourite site. As I logged into my favourite site the web page loaded with videos of men in lingerie spitroasting each other or shemales feminizing and fucking them.

An early girlfriend of mine asked me to wear her panties one night and I was hooked. It felt so sexy and naughty. Over time it had slowly become more and more serious as I moved from just panties into full outfits, surfing tumblr and watching hypno videos, it just escalated. Even when we had broken up I'd bought a small collection for myself. I couldn't stop; it felt too good and touched something submissive deep inside me.

Rosie has no idea about this. We have a lively sex life, which I loved, but I knew this was too far. Luckily we are similar I'm size so I can wear her lingerie without arousing too much suspicion. It's one the many reasons I bought her such expensive underwear, especially anything in silk or satin.

With reluctance I closed the site and got up to shower. Walking into the bathroom I check my reflection I see a handsome, lean body looking back at me. My cock, still firm from my surfing this morning hangs 6" long. I'd always been reasonably proud of it and certainly never had any complaints but knowing I had to meet the guys in an hour I stopped checking myself out and jumped into the shower.


As I walked into the hotel bar I saw all 5 of them already sat with pints. Punchy for 10.30am but very much in character with my friends on a day like today.

They were mainly uni friends, plus Richard of course, and all jumped up to give me a hug to greet me.

"James buddy your pint is all ready for you," said John, my best friend and best man.

I noticed immediately that they were all dressed in school uniforms, like we would have worn in high school. Seeing the dubious look on my face Jack speaks up.

"Ah yeah, that will all be explained a bit later. Don't worry, it's going to be great."

We started with a hefty breakfast all catching up and having a great laugh. Before heading out for a round mini pub golf, just 5 holes to warm us up.

At the first pub Richard came up to thank me for inviting him. While Rosie and I are similarly sized he definitely wasn't. At 6'2" and built he loomed over as he shook my hand and bought me a pint, a nice gesture I thought.

With the mini golf done we headed back to the hotel to get ready for our night out. Everyone in the group seemed to be acting a bit weird as we re entered the hotel, suppressing their laughter. I was deeply suspicious about what was to come.

"Well," John started, "As you may have noticed we are all in uniform. As part of tonight's activities you need to be dressed to match. Your outfit is upstairs in my room so I'll show you up and we'll meet back down here in 30."

In the lift of the way up John gave me a pat on the shoulder, "Don't be nervous! It's going to be a great night." He clearly sensed my anxiety on this development.

"Your outfit for the night is laid on the bed. We thought it would be a good look for you! Plus it will be even more appropriate for where we are heading later. I'll wait out here for you."

I swiped the key card and walked into the dimly lit bedroom. Then I saw it on the bed, my heart jumped into my mouth and I broke into a sweat.

On the bed was a school girl outfit, from tip to toe. Blonde wig, white shirt, plaid shirt, black heels. But with it was a set of red silk lingerie, half cup bra, suspender belt, thong and white stockings.

I stopped and stared. Did they know about my habits? Panicking I thought about leaving. Then I heard John laughing through the door, "You're gonna look great mate! The guys had this planned for ages!"

I felt reassured this wasn't a trap but was deeply concerned about wearing it. It was the outfit of my dreams but I knew I'd have a hard time not having an erection all night. Especially given the silk lingerie, it got me hard just looking at it. It was delicate, with small bow details and a deep, slutty red. I'd have died to buy it for Rosie (and me) if I'd have seen it in a store.

"Hurry up we don't have all night!" I heard through the door.

I stripped and began to dress. I won't lie, it felt incredible. Pulling the stockings and lingerie on awoke the familiar feelings in me, the utter naughtiness and submissiveness of wearing something so delicate and beautiful. The silk was unbelievable, the way it cradled my body was electric and my cock immediately responded. Clipping my stockings to the suspender belt I could see it tenting my thong and skirt.

I caught my reflection in the mirror as I finally slipped the wig on and gasped. I looked just like the women from my favourite site. Feminized like a whore and ready for a fucking. The effects of two weeks without cumming meant I had rarely felt hornier and here I was, dressed like the slut of my dreams.

I waited for my erection to subside before tentatively opening the door. When John saw me he burst out laughing and doubled over, clearly thinking it was hilarious whilst I mostly tried not to get hard again.

"Amazing, you almost look hot! The guys will lose their shit over this. Best idea we've ever had."

Walking to the lift and down the elevator I was acutely aware of the feeling of the outfit and how the heels made me walk.

Needless to say there was a similar reaction from the rest of the guys when they saw me. I was greeted with catcalls and whistling, Jack actually slapped my ass. Richard bellowed out a laugh, almost a little too loud for comfort given he's fucked my fiancée before.

"Alright, alright, very good. Now are you going to explain where we are going?" I tried to quiet them down.

"I thought it would be obvious," said John, "we are going to The Schoolhouse."

Suddenly it all made sense. The Schoolhouse is a strip club we had sometimes gone to on the weekend from uni so it would be a trip down memory lane.

Without discussion John led us out to the street to get a cab.

In public I was suddenly very conscious of how I looked. Particularly the way the heels made my ass perk up as I felt the thong running between my cheeks. It was heavenly. To everyone else this was a funny stag trick, but unbeknownst to them I was dressed in my greatest fantasy costume and desperate not to show it.


The club was the same way it had always been dark, smellier than you want with sticky floors. It was also a bit of a labyrinth of rooms with doors leading off a windy corridor where guys would go for a private dance.

We were all pretty buzzed from the boozing during the day and John insisted that as the stag I should be getting a special dance. I was taken by the hand of a sexy Latina woman and guided through the building, walking past room after room until we reached a free one for us to go inside.

She sat me down in the chair in the middle of the room, "I like your outfit, very pretty, I have something similar at home," she smirked. In my mind's eye I pictured her in it, accentuating her sexy body.

Having done shots in the cab and after the day I was pretty loose and incredibly horny. As she slowly danced, grinding her lithe body on me I couldn't help but have my cock grow and strain against the silk panties and skirt. It became unavoidably clear this was happening to her.

"I see you're having a good time..." She whispered in my ear.

The combination of what I was wearing, her movement and pent up sexual frustration meant I couldn't do anything other than groan in agreement.

Her ass grazed my cock, and it noticeably twitched in its satin prison. She did it again and I couldn't help but groan again.

"Wow, someone's a horny boy. Although given your outfit maybe that should be horny girl."

My cock twitched at that.

"Interesting... you're not one of those guys who gets off on dressing up like a girl are you?"

"No, no," I stammered, "My fiancée and I are on a sex ban to build tension for the wedding night that's all!"

She seemed convinced by my argument. But continued to tease my cock over the next 15 minutes.

She finished the dance on her knees between my legs with her hands gently resting on my stocking-clad thighs. As looked up at me from there and softly asked, "Maybe you'd like a treat to finish?"

She eased up my skirt and pulled my rock hard cock out of my panties.

Despite my overwhelming sex drive I knew I wasn't comfortable getting a blowjob from this sexy stripper.

"Please, much as I would like nothing more than this right now I can't," I told her in a strained voice, though my cock told a very different story.

"Ok babe, whatever you say - I get it." With that she gently tucked my cock away again. "But as penance you have to do some shots with me," as she pulled a bottle out from below the table and laughed.

Three tequilas later I tottered out of the room in my heels. The alcohol had definitely set in and I swayed as I headed back to the room the guys were in.

This place was a total maze and I wasn't sure I was heading in the right direction. After going round in a circle I was convinced I had found the right door so pushed it open and walked in.

It was immediately clear I was wrong. The room was dimly lit and the walls were all mirrors making for dizzying reflections. Instead of it holding my friends there was just a single woman in the corner, fixing her stockings after a performance I guess had just ended.

"Sorry, my bad wrong room," I said, slightly slurring my words as she turned to see me at the door.

"No problem honey," she replied.

Then I saw it. Hanging between her dark brown thighs.

A thick cock.

Maybe 7" long and gently swaying as she turned. I was mesmerized by it. I'd watched a lot of shemale porn but had never imagined I'd meet one in real life. Especially not when I was dressed like a naughty school girl.

She couldn't help but notice where my attention was focused. "I see you've met my best friend," her voice thick and seductive, "Like what you see?"

I couldn't speak but the alcohol in my veins meant I didn't want to leave either.

"It's ok sweetheart, maybe you're nervous. Why don't you come in and have a seat?"

My legs automatically carried me forward, without my brain even asking them. My eyes were firmly fixed on the meaty cock.

"Have you ever met a woman like me before?" She whispered softly. I just shook my head.

"Would you like to feel it?"

I knew this was a dangerous path. But I was so horny I couldn't help myself. Even as my head told me not to, shouting at me to turn and leave, I stayed. I'd fantasized about it for so long, maybe this would be my only chance.

Sensing my nervousness she took charge of the situation.

"Kneel," she instructed.

I knelt before this ebony goddess and looked up and down her statuesque body, firm and toned, finishing with her cock resting inches from my face.

She lowered her voice even further, "I've met girls like you before. Nervous to try it in case you like it too much. Desperate for a taste, but scared of what it means. It's ok, give in to it."

"Besides, look at your cock; it clearly wants you to."

I glanced down to see my dick firmly pressing against my panties under the skirt. Worse, there was a very obvious wet patch where it had begun to leak heavily.

It was too much. The clothes, the booze, the hot woman with a cock in front of me, years of fantasy all triggered something inside of me as I leaned forward and gently took the head of her hardening dick in my mouth.

"Good girl, that's the right choice" she whispered, almost to herself.

It was spongy and warm, tasted like sex and sweet on the tongue. It wasn't what I imagined in my constant jerk off sessions. It overwhelmed my senses and I had never been hornier, beginning to bob my head up and down on it, slowly working more and more of it in my mouth.

"Are you sure this is your first time? You're a natural cock sucker. You look like you are enjoying yourself," I heard her say above me.

I hated to admit it to myself but I was. I was finally living my hottest fantasy. My stockinged legs underneath me quivering as I licked and tongued her hard dick.

I couldn't believe that just five minutes earlier I had turned down getting a blowjob from a sexy stripper and now here I was, on my knees and giving one. Not just giving it, but loving it.

It felt like the sissy hypno videos I'd seen all came together and before long I was desperately worshipping it. Licking her balls and trying to gag on her hardness. I lost myself in it. It was all the hotter knowing my best friends were just doors away from us in the club.

I heard her breathing quicken as my mouth did and I knew she'd be close.

She twitched, as if distracted by something, but then she urged me on, "Nearly there baby, good girl. Make me cum like real sluts do."

I couldn't help it, I went into a frenzy, suddenly nothing was more important than tasting her hot seed. She moaned louder and louder, then suddenly her cock spasmed in my mouth and I tasted her. It spurted two or three times and I coughed a little but drank it down until just the tip of her cock was in my mouth. This was the most powerfully erotic moment of my life, on my knees before a shemale goddess, dressed like a wanton slut with the taste of her cum lingering in my mouth.

"Wow" she said breathlessly "what a performance."

*clap* *clap* *clap* "Yes it was, very impressive," I heard a deep voice say from behind me.

I jumped and twisted round to see Richard stood behind me, a smug look on his face.

My stomach dropped as I felt like the floor fall away from under me and the blood rushed to my ears.

Behind him I saw the door I'd come through ajar and realised he must have seen me as he walked by. That's why she had been distracted; it was when he came in the room behind me.

I started to stammer some kind of response but he cut me off firmly, "No need to explain yourself John. Why doesn't your lovely friend leave us alone to chat now?"

The authority in his voice meant that without another word she picked up her things and left. Richard followed her to the door and quietly locked it behind her before coming to sit on the chair in front of me.

I felt sick, as my hottest fantasy had quickly turned into my worst nightmare. I had been caught sucking cock by my fiancée's ex boyfriend!

He leaned in a spoke to me quietly.

"John I'm not going to lie, that was incredibly hot to watch. I had no idea my replacement for Rosie was such a whore."

I started to protest but he shushed me again, leaning in further. "Shhhh, shhh, it's ok, your secret is safe with me."

"You and I share some tastes, I actually spent a lot of time in Thailand on business and I have to confess I love shemales too. So taboo and sexy when the girl has something extra."

Hope rose in me, he understood! He even sympathized. Maybe we could just get up and leave now. In my mind's eye I pictured Richard in my situation, his muscular body servicing a hot tranny, him worshipping her like I had, maybe he liked wearing lingerie too.

I tentatively asked, "So you have sucked them too?"

He leaned in very close and whispered in my ear.

"Actually John that's where we differ. Unlike the sissy faggot you are, I get off on fucking them and making them my bitch. Not sucking cock like a pathetic slut."

My stomach dropped again and I tried to move further away but he pulled me close and carried on.

"I especially love the girly, pretty ones with nice taste in lingerie like you" he menacingly pinched my neck, "So if you want to keep hold of Rosie you'll be a good girl for me tonight."

I panicked as the enormity of what was happening hit me. I couldn't let this happen. A random stripper was one thing, but this man knew my fiancée and me!

"You can't prove anything," I told him in a desperate effort to salvage the situation.

In response he simply pulled out his phone and started playing a video that clearly showed me gagging on the stripper's cock as she came in my mouth. What made it worse was that I hadn't seen him filming because my eyes are closed in ecstasy as it happened and my dick is clearly standing proud. I looked like a total whore; there was no denying it.

"So back to our discussion. As you're already on your knees I'd like a repeat performance please, I'm sure you'll perform even better on your second time."

"Go ahead take it out."

Knowing I had no way I slowly moved my hands to his belt and undid them. I could already feel the heat coming from his crotch. I unzipped the fly and reached in. There was a part of me desperately hoping his cock would be small to make this easier.

I was going to be very disappointed. As I pulled it from his briefs I could tell it was huge and when I fell out in front of me I gasped.

It must have been 9 inches at least and so thick. I had horrible images of this fucking Rosie and what it would do to her.

Richard smirked as he saw the look of shock on my face, "You look like Rosie did the first time she pulled it out too. Don't worry, you will get used to it just like she did. Now suck."

In a moment of deep humiliation I did what I had to and slowly took a cock that had fucked my future wife in my mouth. I have never felt so pathetic in my life. How had I got here? These were just harmless fantasies, now horribly playing out.

I glanced up and saw Richard's face grinning, "You've got a pretty mouth. Keep working it. Say thank you to me for letting you taste it."

"Please Richard, don't do this," I begged him.

"Look John, you can either say thank you or I text Rosie and all your friends this video. Maybe I even just bring in the rest of the guys here? What do you think they'd say if they could see their best buddy here with my cock in his mouth?"

Report Story

byAnon729© 17 comments/ 58569 views/ 46 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: