• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Fantasy to Reality

Fantasy to Reality

I faded in and out of consciousness.

My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I searched for something that would rekindle them. A flash erupted inside me as a sudden noise infused with my thoughts, time seemed to slow as I separated the noise from the sea of consciousness, It was the sound of a door opening and closing. I eliminated all other thoughts and focused on sound, footsteps, walking closer towards me, the footsteps echoed which told me the room was empty and the floor was hard. The pit of my stomach turned and I felt suddenly excited, the feeling spread upwards and my mind began to fill with arousal. I heard a rustling noise, much closer this time, I felt my eyes slowly open very slightly to tiny slits, everything was blurry. Another sound filled my mind, a chain rustling, a key opening a lock, then it hit me, I was in the chains! I couldn't feel them but I somehow knew. I strained my eyes open just a fraction further and another wave of arousal filled me - amidst the blurriness and confusing light I could see something pointing towards me, it was the head of an erect cock. The blurring room disappeared and I saw only the cock, through the small gaps in my eyes the thick head came into focus, it was inches from my face, I studied the round pink flesh and I became even more aroused, I yearned to kiss it. As if by command it moved towards me and the numbness subsided from my mouth, I could feel the saliva soaking my tongue and my soft lips felt almost throbbing.

I was desperate to have the cock fill my mouth, to completely fill me. Finally the head touched softly against my lips, sending my mind into a frenzy and my eyes snapped shut to control the disorder. The soft flesh of the head ran across my bottom lip, causing them to tremble with pleasure. The cock slowly pressed into my mouth, my lips hungrily wrapped around the thick head, everything was automatic, I knew what I was required to do, I knew what I was desperate to do. A pang of dismay filled me as the cock pulled out of my mouth and my eyes strained halfway open, I could only partly see this beautiful cock, it was the only thing that mattered in the world. A red mark on the top of the head caught me eye, lipstick? I tried to lean forward to the cock but I couldn't control my body, a slight twinge ran down my arm, I could finally feel something there. I tried desperately to move it, I wanted grab the thick shaft and pleasure it with all my energy. Again I heard the noise of a chain and by focusing intently I realised my arm was tied behind my back with a chain, both arms actually. My arousal spread down my body and I could, albeit only slightly feel my legs, the floor felt cold, I was kneeling. Again I felt the head of the cock softly against my lips, my body twitched with desperate desire for the cock, desperate arousal. This time the chains clanged some more, I was slowly regaining feeling in my body. My body twitched more and I realised my ankles were tied together, I felt the the air on the top of my feet but I could feel shoes, I tried to move them, was I wearing high heels? Catching me by surprise the cock forced its way into my mouth, I felt the thick veiny shaft with my lips as my mouth spread wide, straining to take it all in.

I felt a surge of arousal around my crotch and my nipples began to tingle in intense pleasure as the cock pressed even deeper into my mouth. My chest felt unusually heavy as numbness continued to trickle away and I could sense something other than just my pecs. Time seemed to slow down as the taste of the juicy cock began to soak into my saliva whilst my neck tickled along with the top of my back, long hair?

The cock had only been inside my mouth for a few seconds but the pleasure grew almost too much to bear, I became dizzy with incredible arousal and numbness slowly returned to my arms and legs, my eyes closed and my mind drifted into unconscious blackness.

--------------------

--------------------

Two Weeks Earlier...

--------------------

--------------------

I sat at my large, mahogany desk and glanced at the clock, it was 8pm and I was still finishing paperwork. I started this job the same year that I married my wife Hannah, just over 5 years ago. It was well-paid but rather tedious and I didn't get to spend as much time with her as I wanted to which frustrated us both. The calendar caught my eye, only a week until my 25th birthday and I started to think about what I was going to suggest for 'birthday sex' as we called it. About a year into our marriage I had confessed to some small roleplay fantasies, namely gender swapping. I said I would like to pretend that I was the wife and Hannah the husband and maybe experiment with a strapon or cross dressing etc, she wasn't really comfortable with it so I dropped the idea and passed it off as a small thing. The truth however was that I had been slowly becoming more and more addicted to the idea of gender-swapping, secretly I considered myself bi-curious and spent considerable amounts of time on the internet masturbating to all sorts of pornography. Deep down I have always been sexually submissive and my fantasies started off as simply being dominated by women, to cuckolding, which then developed to the idea of being 'forced' by a woman to dress up like a slut and suck a cock, the ultimate act of submission. These were however fantasies, and I was happy with my wife.

I glanced at the clock once more, 8:45pm, just wasted 45 minutes fantasising, this was getting too often an occurrence!

I arrived home just after 10pm and saw a Bentley parked outside the house, it was Carl's. Carl was a friend of Hannah, some hot-shot surgeon who owned his own practice at just 35 years old.

"Hello gorgeous!" I called as I entered the house and walked into the living room.

"Hi," came the reply, her greeting much less enthusiastic than mine, she was busy chatting to Carl with a half-empty wine glass in her hand. Hannah was just as pretty as the day we met, long blonde hair, deep blue eyes and soft features. Her body was even better than the day we met, she was a bit of a gym freak and had an amazingly toned body, a quite large but firm ass with long slender legs and D-cup breasts. She was a very girly-girl, currently wearing a pink low cut frilly top with short denim shorts, nails painted pink and a good amount of jewellery. I often found myself fantasising about being dressed up as girly as her and made to please another man, more specifically, the man who had been frequenting these recent ones was Carl. (Despite these fantasies I didn't like Carl, he spent too much time with my wife which naturally caused animosity towards him. I was fully aware that I never wanted to act out fantasies like these).

Carl was, annoyingly, in fantastic shape for someone with such a difficult job, he was around 6"2 with short, smartly cut hair, strong features and some 'designer stubble'. He was currently wearing a tightly fitting t-shirt which showed off his large chest and tight waist which most likely hid some washboard abs. He managed to maintain a gentlemanly yet dominant aura which shone through no matter what company he kept or what clothes he wore. I sat on the chair opposite and felt like the third wheel for the rest of the evening.

Later that night after Carl left I started kissing Hannah's neck, attempting to initiate sex, she pulled away from my advances;

"I have a big surprise for your birthday," she said in her sexy voice as she stared into my eyes seductively, "I'm saving you for then."

---

Much to my annoyance I was away on business for the week approaching my birthday. The night before the big day I spent hours and hours staring at sissy porn on the internet (using my work laptop) but not touching myself, truly looking forward to what Hannah had in store, I had my fantasies but told myself that I would love to try anal, her ass, not mine! It got to around 11pm and an email popped up from Hannah, I opened it excitedly, she always sent me dirty pictures of her when I was away on business:

A few weeks ago I was using your Macbook to book a gym class when I stumbled across something interesting on your laptop...

My heart pounded in my chest, I had gigabytes of videos, pictures and stories all depicting my very secret fantasies. However I had them in an encrypted folder and kept some 'regular' porn in a more obvious location as a decoy, "she can't have found the secret folder, I always close it and make sure it's password protected, oh please tell me I didn't forget," I said to myself. "A few weeks ago?" Came my second thought, why is she just bringing this up now?"

"...I found your porn stash."

This second line hit my like a blow to the face, my stomach turned and I started to sweat, desperately hoping that she didn't find the actual folder. Strangely my penis was semi-erect, bulging slightly in my jeans, I quickly dismissed it and read on.

"...I wish you would tell me that you watch porn, however It has opened my eyes and given me some ideas about your birthday present, I am sure you will enjoy it!

See you tomorrow

xxx"

I hardly slept that night, full with a mix of conflicting emotions; excitement and fear. I tried to subdue all thoughts of my real fantasies coming true, constantly telling myself that I hope it was just anal.

---

My birthday came and I arrived home and knocked on the door, I had to concentrate on not letting my hands shake, I was that nervous. What answered the door took my breath away; Hannah was standing there, hand on hip, looking the most sexy I have ever seen her. she was wearing frilly black lingerie with tiny underwear and huge black high heels. After what felt like minutes of staring her deep provocative eyes met mine and without saying a word, she grabbed my tie and began to lead me upstairs. My mind was racing, "she hasn't found the real stuff, it's just going to be normal sex, maybe anal." During the ascent I watched her amazing ass move from side to side as she stepped, I was transfixed on her amazing body, ignoring a pang of disappointment. She stopped just outside the bedroom door and turned to face me, pressing her breasts against my chest and whispered in my ear:

"You're going to love this."

We entered the room and I stopped dead in my tracks, I felt the wind completely knocked out of me. On the bed lay some lingerie, pink and frilly, some pink high heels and long white socks. My mind raced and panicked, "they could be for her to wear," I thought, but the heels looked too big. My stomach knotted further:

"Put them on." Hannah demanded, her voice had changed from a provocative whisper to a firm order. "I've seen all of the weird porn you watch and now it's your birthday, I told you it would be a special treat, you get to re-enact one of the videos."

I just stood there, frozen with no idea what to do or say, I fought a battle with deep sexual urges, my sense told me to just deny it and claim the porn wasn't mine but they were overcome by my desire to wear the lingerie and be a sissy. She might even have a strapon waiting somewhere for me to suck, pretending to be a sissy. Hannah looked at the massive bulge in my trousers and knew I was very aroused.

"What are you waiting for, sissy? Put them on and come downstairs, I'll be waiting..."

My stomach knotted with pleasure when she called me a sissy, I heard the door close and moved towards the bed, transfixed with the lingerie. I had never felt such arousal, excitement and fear all rolled into one, it was an incredible feeling. I was on autopilot now, doing as my deep fantasy has always wanted to do. I stripped naked and put on the frilly panties, they barely contained my now bulging erection, my hands were shaking as I put on the sexy pink top and slid the long, soft socks just above my knees. Finally I slipped on the heels, a perfect fit. Standing up wasn't as difficult as I had expected in the big heels, my balance was very good and I was able to walk without any problems, a born sissy. My heart raced even faster as I left the bedroom and walked downstairs, very happy with myself that I didn't fall down. I turned the corner to enter the living room and stopped instantly, fear tore through my body as I saw Hannah sitting on the sofa alongside Carl. They both burst out laughing:

"Oh my god, I cannot believe how much of a sissy you look!" She said between her hysterical fits of laughter.

"I didn't think he would do it, you were right!" Came Carl's response, also amidst loud laugher.

I stood bolt still, my cheeks burned red with embarrassment as my mind erupted with humiliation, my cock twitched even harder. I couldn't find any response so I just stared at the ground, wanting it to engulf me. Carl moved towards Hannah and put his arm around her, I stared in disbelief, "she said re-enact one of my videos," I thought, my stomach pitted even harder but the humiliation only increased my arousal.

"Happy birthday, sissy!" Han erupted with more laughter as she said it. Her hand was resting on Carl's thigh. "I think you can now guess which video we are going to re-enact...get on your knees!"

The sheer dominance in her voice made me automatically obey, I sank to my knees, still unable to fully process what was happening.

"For the past few weeks, Carl has been fucking me." Hannah said bluntly, I stared in disbelief as she turned and kissed him passionately, her hand sliding higher up his thigh. their tongues ran across each other and after what felt like ages she looked back towards me and continued; "I always knew there was something wrong with you, you have been dreaming about being a sissy bitch for years, I have seen the date on some of the videos. I deserve a stud like Carl, not a sissy like you."

Her words hit me hard, this wasn't a one-time treat, it was real. Yet despite my inner dismay and humiliation I felt more aroused than ever, having her talk to me like this and call me a sissy. When she kissed Carl I expected to get up and punch him or something, instead I just watched like an obedient sissy, it was nearly overwhelming.

She began to kiss Carl passionately again, tearing off his t-shirt revealing his perfect upper body and causing me to stare in awe. She ran her hands down to his underwear and pulled them down revealing his huge erect penis. My eyes went wide and I saw Hannah smile her sexy smile, his cock was huge! 8 inches long and very thick, perfectly formed. They stopped kissing and they both looked across to me, Carl had a cocky yet dominant grin and I felt utterly subservient to them both.

"Crawl over here sissy," She ordered. "You are going to worship the cock that has been fucking your wife for weeks."

I obeyed and instantly and began to crawl towards him transfixed on that perfect cock, it was even more beautiful than I had ever imagined and I was more aroused than I could ever imagine, I felt like I could just explode right there and then. Carl's grin remained arousingly cocky and dominant as he opened his legs allowing his large balls to droop between them with that fantastic cock pointing towards the ceiling. He had no hair on his balls and the rest was trimmed very neatly, a perfect sight as I noticed myself salivating profusely, my pink panties stretched to accommodate my ever increasing erection. I crawled between his legs feeling like a slut and finally planted a kiss in the middle of his thick shaft, much to their amusement. Hannah said something but I didn't hear it, I was truly focused on worshipping this cock. I planted several more soft kisses up and down the shaft and caught myself letting out a high-pitched moan which encouraged more humiliating laughter. My lips drifted down to where the base of his cock met the balls and I kissed that area delicately, feeling the cock rest against the entirety of my face, I continued down and worshipped the soft, wrinkly balls planting kisses on every part. From here I let my tongue touch the soft skin and let out a long lick from the base all the way to the tip, it seemed to take forever due to its size. I spread my tongue wide and licked the whole cock time and time again, feeling the bulging veins and soft thick skin, it glistened with my saliva looking both amazingly daunting and insatiably arousing. I quickly realised why Hannah had been fucking Carl now, this was way better than my cock, he is way better than me. I proceeded to run my tongue around the wide head, giving extra attention to the frenulum by darting my tongue around it, alternating between light flicks and heavy licks. I felt his legs and body twitch as I did alongside some moaning, they were kissing passionately obviously enjoying my subservience. After what seemed like an eternity of bliss I felt a hand gripping my hair and pulling my head away, I looked up to see them both staring down at me.

"How much do you love being a sissy?" Hannah asked, her tone demeaning yet authoritative.

I answered without thinking, "I love being a sissy, I was born to be a sissy."

"How much do you love my cock?" Carl asked.

I turned my head to Carl, "I love your cock, I love worshipping your cock, my job is to be a sissy and worship your cock." They both laughed at my utter submission and humiliation.

Hannah continued, "I think we both know that our marriage cannot continue after this, I need a real man, not a sissy cock worshipper." My heart sank and my stomach knotted but I knew this was true, I was a sissy, not a husband.

Carl glanced at Hannah and winked; "To be honest you look ridiculous with that outfit, why would I let some male sissy suck my cock for a second longer when your sexy wife can do it?" Hannah smiled at Carl's comment and immediately leaned down to wrap her lips around his cock, I immediately became very jealous as she worked it deep into her mouth, Carl leaned back and moaned with pleasure. I heard loud slurping and she moaned like a whore as he approached orgasm. I stared in utter desire, desire to able to worship him like my wife could, I desperately wanted to be sexy. Carl looked down at me, breathing heavily as she continued to slam his cock into her throat.

"Tell me how much you want to be a sexy slut like your wife." He said before quickly moving his head backwards and looking at the ceiling as Hannah deepthroated him once more.

"I would give my life to be a sexy slut," I begged, this filled me despair that I could never really be one.

Finally Carl began to moan loudly and his hips thrust up a he came into my wife's mouth, she held her mouth around his cock for about a minute as it became filled with this stud's cum. I wished more than anything to be able to taste a stud's cum like that. Eventually Hannah lifted her head and looked towards me, her mouth filled with cum, knowing how much I desired to be in her position. She grinned and played with the cum in her mouth, teasing me before swallowing melodramatically.

Again Carl looked down to me and my bulging cock sticking out of the panties, his tone was now calm but commanding. "What would you say If I told you I can turn you into a slut?"

I answered instantly and automatically, "I would give anything and everything, I want to be a slut to worship cocks all day and night." This was truthful and genuine, I had fantasised about it for years.

Transfixed with Carl, I finally noticed Hannah had left the room at some point. Before I could wonder where she went I felt a sharp prick in the back of my neck.

"Happy birthday, slut," she whispered into my ear as the world went black.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Fantasy to Reality

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 33 milliseconds