Warning and disclaimer:
This story deals primarily with female domination, forced feminisation, and strong transsexual themes. If this sounds like the kind of material that might offend you then, STOP READING NOW. THIS IS FOR ADULTS ONLY!

All constructive comments a little criticism if needed and possibly even warm applause where fitting, is as always welcomed. E-mail: sararever@hotmail.com

 

Emma - Taken By Surprise                 by: Sara Rêver Éviellé

 

I had never had a good relationship with my sister Lisa, maybe because it seemed that my parents always favoured her, or maybe it was with her being one year older I had always been bossed around by her. Or even maybe it was because she was so pretty and clever, that even from an early age she had won some beauty competitions and had been the centre of attention of family and friends.

By the time we reached senior school, she was one of the most popular students, with both classmates and teachers alike. Lisa excelled at Maths, Chemistry and English and was also a good athlete, she was a perfect student. These attributes when combined with her beauty, long flowing blonde hair, and perfect body, Lisa was most also very popular with boys in particular. More recently she had become the girlfriend of Mike Richards, who was one of the most eligible young men in town.

Mike was the only son of a wealthy family who owns and run a chain of shops throughout the north of England. Mike is only a two years older than me, but already has his own penthouse flat and a really flash TVR sports car.

All of this attention and ego stroking from friends, family and Mike, made Lisa a real bitch to me. I was painfully shy and extremely introverted, and Lisa constantly teased me, saying that I was a wimp, that I would never get a date, and that I was probably gay.

In the pain and confusion of my adolescence, I discovered cross-dressing as a form of release. I cannot recall exactly how it started, but it seemed to help me, by imitating my perfect and remarkable sister, then maybe I would be as popular as she was, who knows? But I saved up my pocket money and started to buy make-up in contrast to my few friends who spent their money on more typical boyish things and I became wrapped up in my own, secure and safe little fantasy world.

I didn't think I was gay because I was still very much attracted to girls, but I really found it very difficult to get a girlfriend, and dressing seemed to help me be, closer to them somehow.

By the time I was eighteen, I was really quite adept at applying my makeup, so good that I could probably pass for a girl. I had even grown my hair quite long and kept it in a fashionable ponytail, so that when I let it down and brushed it out, I was pleased to see, the sister of Lisa's staring back at me from the mirror.

By this time Lisa had also left for college, which gave me the opportunity to 'borrow' some of her clothes that she had left behind and happy to find that they fitted me nicely. Up until this time my few female clothes had been obtained by stealing from clotheslines or shop lifting from the local Mall. I had found it quite easy to get bra's, panties, nylons and the like this way, it seemed that nobody suspected a boy of stealing lingerie and dresses!

During my teens, I spent hours locked away in my bedroom, dressed in silky panties and nylon stockings masturbating furiously. My sexual fantasies ran riot from being seduced by a man, to being the playful girlfriend of a lesbian. These dreams that got me off were a lot better than the two real-life sexual experiences I had.

These both involved a chubby, near sighted neighbour's daughter. The first incident ended in premature ejaculation and the second with me vomiting in her lap after too much to drink. Both of these events made me feel insecure and nervous with girls, and I found that I was much happier when I could simply satisfy myself.

One spring afternoon when I was eighteen, a rare event happened, I was finally going to be alone in the house for a few days. Over the years this had only happened once or twice and I couldn't wait to get dressed up and spend some time relaxed looking and feeling like a girl. My parents had just left for a vacation, and Lisa wasn't due back from college for another two days.

So I got my makeup and applied it to perfection, just like those fashion models in the magazines. I wore quite thick mascara and eyeliner, and subtly blended two or three shades of eye shadow such that my eyes looked wide and sexy. My lips were coated in glistening scarlet lipstick, which gave me a Marilyn Monroe like pout. I then painted my toenails and fingernails in a scarlet nail varnish, which matched my lipstick simply the smell of the varnish, was enough to stimulate me.

When everything was dry, I then went into Lisa's room and chose a pair of her satin panties and a soft satin and lace trimmed bra, a pair of tan nylon stockings and a suspender belt. Then I found a pretty floral summer dress that I recalled her wearing two summers ago, and the final touch was to be a pair of 3" stiletto heeled sandals.

As I was rummaging through her stuff, I surprised to find a vibrator, it was wrapped up in an underskirt at the back of the drawer. It was flesh coloured and shaped like a real erect cock, quite realistic. I picked it up and held it up to my nose, and I could detect the faint aroma of my sister juices on it, the smell excited me, and the thought of Lisa using it thrilled me even more, so I took it with me back to my room.

I took my time putting on the clothes savouring every moment, when I was done I stood and admired myself in the mirror. Once again the girl who I envied so much was staring back at me, it was Lisa, or at least her sister 'Emma', I had given my alter ego the name when I first started dressing. I was pleased with my metamorphosis it was like a chrysalis turning into a butterfly, so much so, that my cock began to swell and I had to start to masturbate straight away.

I lay down on my bed and stroked my cock and probed my asshole with a finger, something which I had just started to discover gave me heightened stimulation.

Soon I was writhing in ecstasy, with my panties soaked in pre-cum. I reached for Lisa's vibrator and closed my eyes and began to suck on it, imagining it was real, but soon that was no longer enough, and I so I placed the tip of it against my anus and began to slowly ease it into it. It hurt at first but after the head had penetrated me the rest of the shaft pushed in with far less discomfort.

I was so caught up in my excitement, that I didn't hear the front door open and close, until, finally and suddenly I heard footsteps coming up the stairs and the sound of two voices. It was Lisa! And her boyfriend Mike, back from college early. I froze too scared to even move, or breathe!

I could here their voices getting louder, Lisa was giggling, then horror of horrors, I saw my doorknob turning, and in barged Lisa, with Mike right behind her!

My brain froze and I flushed all over in a boiling hot glow of mortified embarrassment, this was my worst nightmare. Why oh why hadn't I locked my bedroom door?

At first Lisa appeared to do a double take, probably amazed that there was a girl in my room, then she gasped as she suddenly realised that the girl was no girl, it was her brother.

"Richard! Oh my god! What the hell?" she screamed in amazement, there was a moment's silence, which seemed to last forever before she added.

"What are you doing? Is that my dress?"

My brain suddenly clicked back in and I attempted to remove her vibrator from my ass, cover myself, and hide the vibrator under the duvet all in one movement, and failed to disguise any of it, successfully.

Mike just stared at me in silent amazement, at least partially at the fact that I resembled a fairly attractive girl, albeit with a hard cock under my panties and dress.

"Oh boy!" Lisa said, "wait until I tell Mom and Dad knew about this?" I was totally flustered I didn't know what to do. My eyes darted back and forth between Lisa and Mike.

Mother was a very righteous woman, and my father was extremely conservative, if either one of them knew about my cross-dressing, I felt sure they would never understand. They had even refused to let Lisa bring Mike back to the house when they weren't in, in a vain effort to prevent her having sex with him.

"Please, Lisa!" I stammered, "this is embarrassing enough being caught by you two! Please don't tell Mom and Dad as well! I'll owe you big time, I promise!"

Lisa walked slowly over to the bed and looked me over more closely, whilst I tried to cover myself with the duvet. My skirt was all over the place and I saw Mike smile as he saw my stocking tops, peeking through a gap in the duvet. Lisa tormented me by stroking my hair, I saw a smile come over her face and then she began to speak again.

"Okay here's the deal, I won't tell Mom and Dad that they have a pervert for a son, and you don't tell them that I brought Mike home with me, deal?"

My sister, for the first time in my life, sounded almost fair and reasonable in her demands for my compliance.

"Okay, Lisa!" I said, "it's a deal, no problem, I owe you!"

"Damn right you do!" her normal tone was back, "so, I think you're going to start paying right now! Get out from under there and stand up so we can get a good look at you."

I protested, for a minute, but Lisa pulled the duvet away, leaving me humiliated and exposed. Lisa then grabbed my arm and pulled me up of the bed and onto my high heels. I made sure my dress covered me and stood silently before them, wobbling nervously on my heels.

Even though I had always resented my sister, at this moment with her looking at me dressed as I was I found that it was a relief that I had finally been discovered. I had always hated having to hide my true self from the world, how I wished that I could wear anything I wanted too and to be accepted. Lisa was one of the most beautiful girls you could wish to meet, and I guess I had always been kind of jealous of her.

Lisa said, "Now, lift up your dress so we can see you in your underwear."

"I can't this is too embarrassing, I'm sorry for this Lisa, don't make it worse for me!" I pleaded.

"Just do as I say, little brother!" was her simply reply to my pathetic remonstrations.

My time for protesting was over, so I did as I was told, and reached down and grabbed hold of the hem of my skirt with my painted fingers and lifted it up to my waist. Mike's eyes widened and Lisa giggled as she looked at the head of my cock poking over the top of my panties.

"Well, well" she said, "don't you look nice. Don't you agree, Mike?"

"I have got to say that he looks pretty cute, I could quite fancy him!" he ridiculed.

"Just how long has this been going on?" she asked.

"Just today, this is my first time!" I tried to lie.

"Don't give me that, you're makeup is far too good for it to be your first attempt! I bet you have been doing this for ages! You pervert!" Lisa lifted the back of my skirt and slapped my bottom.

"I am so sorry Lisa, please try to understand, I'm not a pervert or a queer, I just like to pretend to be a girl sometimes, that's all! I don't know why?" this time I was trying to justify myself.

"So what do you call yourself, you don't look much like Richard any more?" she teased.

"Emma!" I said as I looked away, trying to avoid her eyes that seemed to be boring into me.

"Emma, how cute! Well Emma if you want to be a girl that means you're going to have to act like one too, so you're going to have to prove to me and Mike how sincere and sorry you are!"

I wondered what she meant as I dropped my skirt back down and smoothed it down, to cover my exposed stocking tops.

"What do you want?" I asked.

"I want you to suck Mikes cock, that's what I want. If you want to be a girl so much, you need to find out what it's like to satisfy a man!" I was shocked at her demand.

"I can't, I just can't do that, please Lisa, I wont!" I protested.

"You will, or Mom and Dad and all your friends will find out about your disgusting habit!" I guessed her threat to be real.

Lisa grabbed my arm and pushed me down onto my knees in front of Mike so that my face was right in front of his crotch.

"Unzip him!" she commanded.

I demurely took hold of his zipper, and slowly pulled it down, as I bit my lip and looked up at him, looking for some compassion, but it was in vain, he was not even looking at me.

"Take it out!" I heard Lisa say as my mind tied to block out what was happening.

At this stage it was as though somebody else had taken over my body and brain, and I was just running on instinct alone. I reached inside his jeans and found his stiffening cock under his boxers. I struggled with the boxers and managed to pull them down so that I could release his now stiff cock.

When it sprang out in front of me, I realised that I like the way it looked. The shaft was long and thick, and the large purplish head looked swollen and almost pulsating. Mike was quite big at least seven inches, and I could feel his heat from it on my lips.

"Go on Emma! Suck it!" Lisa demanded.

It was now someone else controlling my body took over and I decided that person decided they would give Mike the best blowjob possible, just like all those girls in the porn videos I had seen. I gripped his shaft in my hand and gently ran my tongue over the head. I ran it down the length of his shaft and briefly suckled his balls. I then returned my attentions to his head itself, and began taking it in out of my mouth.

Slowly I took bigger and bigger mouthfuls and continued pumping his hot shaft as I did so. It took some work, but soon my lips were gliding down three to four inches of his thick cock, and I could feel Mike begin to rock back and forth.

I pulled back once more and licked his sensitised glan, and heard him moan in delight, I thought he was about to cum, when Lisa grabbed my hair and pulled me off him.

"Okay, okay!" she said, "just relax, unless you want him to cum all over you!"

She sounded a little upset or resentful of my competence for getting Mike to the point of orgasm!

"Mike put on a rubber, I want you inside me, I want you to show this girl just what its like to get screwed!" this time she was making demands upon Mike.

I struggled up onto my feet and sat back onto my bed, and watched in incredulity as Lisa unzipped her skirt and let it fall to the floor.

Her long legs looked even longer presented, as they were perched upon her stiletto heels and white lace thong panties. She then pulled of her short cut halter-top and released her bra-less breasts. It was incredible, for years I had catching Lisa in a state of undress and now here she was before virtually naked.

Mike by this time had also stripped down to just his boxers, and was taking a condom out from a packet. His cock stood out in front of him like that notorious Greek statue that all tourists seem to come back with, to amuse their friends.

Lisa took the condom from him and unravelled it over his cock, then bent down with her bum toward him and grabbed her ankles. Mike then pulled her panties to one side and guided his erection into my sister's sweet pussy. I then watched with my own erection aching under my dress as he grabbed her hips and proceeded to pump himself in and out of her whilst she moaned and squealed in satisfaction.

It seemed to go on forever, Mike grunting and pumping whilst Lisa moaned and squealed, until eventually, she apparently climaxed, as her screams suddenly got faster then equally suddenly died away. Lisa then staggered forward and pulled herself off the weapon that impaled her.

After seeing her stand upright, I could easily see her panties were soaked in her own juices.

"Emma, get over here you and finish him off!" she ordered me.

Once more I got to my feet and went over to Mike, "What do you want me to do?" I asked meekly.

"He hasn't cum yet so make him cum!" Lisa said as she stepped back into her skirt, so I got down onto my knees once more.

"Take his condom off first!" she instructed. I gingerly began to peel the gossamer rubber off his erection, until finally it slid off the end.

As I took him back into my mouth, I began to stroke my own cock with my free hand, as I feasted on Mike's. Meanwhile Lisa had finished dressing and had mysteriously left the room, I didn't really care because I was too busy concentrating on satisfying Mike.

Soon Mike started to moan loudly, and I also quickly reached the brink of no return, and with most of his cock still in my mouth, I felt my balls tense up. I was then hit with the most incredible orgasm I had ever had, my semen came shooting out in hot spurts, drenching both my belly, and panties.

Seconds later, I felt Mike tense up too, and then the first hot stream of his semen hit the back of my throat. I swallowed as fast as I could, but his tanks were obviously full and try as I might I couldn't gulp down the huge amount of his cum and I had to pull his cock out of my mouth.

Mike kept cuming, with spurts of sticky white cum shooting all over my face, coating my chin, nose, and cheeks. Then I heard a familiar click and whirring, and I looked up, and there was Lisa with our digital camera in her hand. She had just taken a picture of me with my face coated in huge globs of Mikes cum!

"Just a little something to remember this day by!" she said smiling as clicked off several more pictures, whilst I shamefacedly licked the last drops of Mikes cum from his rapidly shrinking cock.

My mind was in a whirl I was confused and frightened at how agreeable I had been, although I had believed that I had no choice, in obeying my sister's orders, I had almost too readily chosen too obey rather than 'fight'. Was it simply coercion that had made me satisfy Mike, or had I really wanted to do it?

"Go and clean that cum of your face and make yourself pretty again!" I heard Lisa's voice blending with the other perplexing voices that were echoing through my head.

I looked at myself in the bathroom mirror and was disgusted at what I saw, gone was the innocent girl, now I saw a slut with smeared makeup and streaks of glistening cum across her face. I ran some warm soapy water and scooped up handful's to wash my defiled face clean, it was a relief to wash away the gluey semen.

 

I dried my face a re-examined it, I was now saddened to see the boy in me looking back, in stark contrast to the feminine clothes he was wearing. I felt shame and sorrow now!

I went back into my bedroom, relieved to find that Lisa and Mike had left, I sat at my table and picked up the small mirror I used for applying my make-up. Then looked into case, which contained the vast array of cosmetics that I had collected over the preceding months and set about repairing my damaged looks!

It was approximately ten minutes later that the familiar feminine face of Emma returned. Her eyes blue and wide framed by long black lashes and eyeliner, her cheeks glowing with soft rouge and her lips glistening with bright red lipstick. I brushed my hair and teased it back into the style, which pleased, for a boy I made a damned pretty girl!

Almost right on queue I heard the bedroom door open and Lisa walk in, this time Mike was not with her. She had changed and was now wearing a simple pair of jeans and a cropped top T-shirt, which displayed her small but pert breasts off to perfection. The clothes she wore were very plain yet she still looked feminine and sexy, an ability, which I presumed she took for, granted.

 

She seemed far more at ease with me know and sat along side me, her denim clad legs brushing against my nylon clad ones.

"Mike was very impressed by your cock sucking abilities!" her words shocked and shamed me, "he claims that you must have the same natural gift for it as I have!" she laughed and stroked my hair, in a strangely friendly manner.

"So what are we going to do with you?" she asked, I didn't answer, as I believed she didn't want one.

"You know, I think I could prefer having a sister to a brother! He really was such a poor specimen, yet you are quite the reverse. You are an absolute doll! I suspect that once all the boys in town get to know you, you will be most popular, most popular indeed!" This was strange Lisa was being almost friendly to me now!

"Please! Lisa, don't tell anyone about this, I don't think I could stand it if everyone knew!" I found myself pleading once again.

"But, sweetie, don't you want to go out and meet boys, a pretty thing like you shouldn't be cooped up here in your bedroom. Besides, nobody would know who you were they would believe that you were just a new girl in town!"

"I really don't think I'm ready for any of that yet, Lisa." I attempted to show her my innocence, but inside, I relished the opportunity to go out and, just be one of the girls.

But Lisa, didn't give in, "Don't you want to find out, what it's like to be a girl? What happened earlier with Mike, was just the start, you can have so much more fun, are you curious?"

"Yes of course, I am kind of curious, but I'm a boy, how can I ever experience what its like to be a girl, like that?" she was starting to confuse me gain.

"My darling, little sister, its so easy, what would you say if I could make it happen for you?"

"I would say you were crazy! Or a magician!"

Lisa stood up and saying nothing she began to unbutton her 501's, one by one she released the buttons until her fly was completely open. I watched then as she reached into the opening with her long and elegant fingers and pulled out an erection!

"What the? I don't understand!" I cried out, as I looked away in horror.

Lisa took hold of my chin in her other hand and pulled my face back around to take another look. I was relieved this time to realise that it was just a phallus, a dildo! Relieved, what was I thinking?

Lisa was now unbuckling her belt and seconds later her jeans were falling to the ground, and she was stepping out of them, and she was not wearing any panties. She had a beautiful pussy it was her fine blonde pubic hairs had been delicately trimmed so that a narrow strip lined her prominent lips. I desperatley wanted to touch it, to place my hands on her firm bottom and pull her into my face, but I was helpless with apprehension and mistrust, what did she want me to do?

The dildo that had been poking out of her jeans was now clearly visible it was at least a foot-long and gripped tightly in Lisa's left hand. I guessed that she must have been tucked away down her thigh, it looked so lifelike other than for its length, and then I saw that it was double headed.

I watched open-mouthed as Lisa began to stroke her pussy with the palm of her right hand her long red nails sliding up and down her crack, then first one finger than another began to work slowly inside her protruding lips. For a few minutes she masturbated herself, inches from my nose, I could smell her arousal and she her juices starting to wet her fingers.

Lisa then began to guide one end of the phallus into her pussy, I could see her pussy lips clearly encircling the thick pink dildo, slowly swallowing it inside. She kept on easing it in until she had about half the length inside the remainder was protruding from her vagina like a barbers pole.

"Wouldn't you like to feel this inside you, Emma? Wouldn't you like to find out just what its like to be screwed like a girl?" Lisa teased her voice now had a fierce rasp to it!

She bent down and kissed me on the lips, then stood up again and pulled of her T-shirt, her breasts with erect nipples hung just above my head. I was silent I tried to speak but my throat was dry and words just wouldn't come out!

"Get up and go and bend down over the bed, theirs a good girl!" Lisa was starting to give me instructions once again and just as before I co-operated without attempting any form of serious protest.

I stood wobbling on my heels with my arms outstretched on the bed with my ass in the air. I felt Lisa raising my dress up and over my back, I could hardly believe what was happening, I was in a daze. I then sensed her move away.

I turned my head to look what she was up to, I saw her with a tube of KY jelly, squeezing a blob of it onto her fingers then rubbing it onto the head of the phallus. She then squeezed out another blob and came back over to me.

"Take off your panties, Emma!" this time it was more of a request than an instruction.

"Please Lisa, don't do this, I'm so, so sorry!" I whimpered.

"Quiet, just do as your told, and take off your pretty panties and show my your pussy!" it was an order this time.

I reached back and hooked my fingers into the elasticated waist and eased them down over my hips and wiggled them down my thighs, until they dropped to the floor.

"Step out of them and spread your legs wider!" I did as I was told, then felt the cold KY on my anus, as Lisa smeared it on, "Now then my darling sister, just relax and enjoy!"

At first as she pushed the head onto me, it made me stagger forward, as my anus resisted her probing, but Lisa grabbed my hips and pulled me back onto it. I then felt pain as my anus was stretched wide to forcibly accept the head of the phallus which Lisa was jabbing into me.

I moaned in the discomfort and ignominy, "Ah! No please, please don't, stop your hurting me!"

"Then don't fight it, darling just accept it, relax you muscles! Then it won't hurt so much." Lisa was now trying to soothe me.

I dug my chin into my chest and looked back between my legs, I saw my stocking clad knees straining against the force that wanted to make them buckle, and let me crumble down onto the bed.

The pain did not diminish and the more she pushed the more intense it became, further and further the monster was shoved into me stretching me to the point where I swore that it must be splitting me. For the first time I understood what it must be like for a girl to be penetrated by a rock hard penis.

Lisa pushed harder into me, and I concentrated on trying to relax my sphincter. Finally I felt her flesh against mine, and presumed that she must have the entire length within me.

"Now jerk yourself off, you pervert!" she demanded, "take hold of that pitiful clit of yours and make yourself cum!"

I thrust one hand back between my legs and took hold of my raging cock I had never felt it quite so hard or so hot. Lisa began to withdraw the dildo as I started to rub myself, then she rammed it back deep back inside.

I moaned once again, a feeble, "Ugh!" Lisa was now pumping the hard rubberised phallus in and out of my aching ass, as fast as she could, whilst I masturbated myself.

I heard Lisa beginning to groan, she was obviously now starting to get pleasure from the dildo herself, "Ah! Yes, yes! Nice!" she murmured.

Now I realised that the pain I had been enduring, was being replaced my waves of pleasure, and almost immediately I began to orgasm, and sperm began to ooze down over my hand.

Lisa carried on mercilessly, pumping the dildo the full length in and out of my anus. I was now wracked with a strange sense of ecstasy, as my cock continued to ooze.

"Oh, oh! Oh, Agghhh! Yes! Yes! Yes!" Lisa cried as finally slowed to a halt, and a climax overtook her body.

Then I heard another voice, "Yes! Yes! Harder! Harder! Yes! Agghhh!" and realised that it was my own.

She cried out once more as she bucked for a last time before she pulled off the dildo and collapsed onto the bed.

I meanwhile was left impaled with the phallus, some six inches or so sticking out of my bottom. I reached back behind me and grabbed a hold, it was wet and slimy from my sister juices and I struggled to grip it firmly. It took my several more attempts to grab it tight, to ease it at last free from my aching hole, and dropped it to the floor, then fell forward onto the bed, in a state of semi-consciousness.

I closed my tear filled eyes, and we lay motionless and silent for a few minutes recovering from the physically draining experience. After a few minutes I felt a hand on my face, gently caressing it, I opened my mascara stained eyes. Lisa hand was touching me gently her fingers playing with my hair, she was smiling.

"Well Emma?" she asked, "do you feel more like a real girl now?"

"It hurt, Lisa!" I whispered.

"It does the first time, but I also heard you moaning in pleasure too!" she replied reassuringly.

"It was good too, in a way, I suppose!" I was surprised to hear myself say.

We lay together listlessly for several more minutes, holding hands, I was now only feeling warmth and love from her, a stark contrast to earlier. I assume I drifted off to sleep for I did not hear Lisa get up and leave.

 

It was Lisa that woke me, with the words, "Wake up Emma! Its time to get up and clean yourself up!"

I opened my blurry eyes, and rolled over and sat up, as I put some weight on my ass I found it to be still sore. Lisa was stood by the bed wearing a short denim skirt, black lace tights and black high heeled boots, and a blue turtle neck sweater. She had obviously showered and washed her hair as it was still slightly damp, and her makeup look fresh and expertly applied as usual.

"Hi Lisa?" I said, in a low tone as I rubbed my eyes and yawned. Lisa shocked me into full consciousness by slapping me across the face.

"Its seven o'clock now and Mike is picking us up at eight so get yourself washed and prettified were going out!"

The slap and her words jolted me, "Out?" I queried hardly believing what she had said.

"Yes, out! Now hurry!"

 

 

The End - for now

=========================

This is a possibly just one off story involving Emma, which may only generate a sequel if I get encouraging feedback, its up to you?

 

 

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The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.