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Being Sarah

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Please note, this is a story about a male-to-female crossdresser. It includes themes of bisexuality, dominance/submission, embarrassing erections, anal play, cunnilingus and cum-eating. If you like that, awesome. If you don't maybe it's time to check another post. You can't say I haven't warned you ;)

****

There are many difficult decisions I've had to make in my life. Deciding whether to confide in someone that I liked to crossdress was definitely one of them. In fact, "difficult" was an understatement, "agonizing" would be a more appropriate term. Especially when, in my case, the potential recipient of my little secret was someone as unpredictable and dangerous as my friend Abbey.

As I sat next to her, the rational part of my brain told me that it would be a stupid idea to open up to her. She was too impulsive. Too reckless. Too oblivious to the consequences of her actions. Part of me knew that she wouldn't be able to keep her mouth shut. Another part of me half-suspected that she'd use the information against me if I ever got on the wrong side of her.

However, I couldn't deny that part of me actually did want to tell her. My hidden self absolutely craved recognition. Added to that, I guess I wanted to prove to Abbey how interesting, unique and different I was. The latter was a stupid motive, but the desire to impress a beautiful, flirtatious and sexually-liberated young woman is one only the strongest men can resist. And back when I was eighteen, I definitely wasn't a strong man.

****

Half an hour before, I sat alone in the seniors' common room at my high school. It was a hot day and I was dressed simply in a T-shirt and shorts. I was trying to work through a set of physics problems that were due in the next week, but I was getting distracted. As the sun had come out, so had the skimpy sun dresses. Out of the corner of my eye I couldn't help but stare at all the beautiful, smooth, female flesh on display. I was counting down the minutes until I could go home, creep into my room, and jerk my dick until I'd drained every last drop of cum from my balls.

My level of distraction reached breaking point when I saw Abbey walk up to me. Almost the second she entered my vision, my breath caught in my throat. God damn she looked gorgeous--even more so than usual.

Abbey was five-foot-six with long blonde hair, and the most wickedly beautiful face. It was the kind of face that suggests the owner is always up to mischief--which, in Abbey's case, was usually true. Her crystalline blue eyes sparkled as she strode towards me, and that big, beautiful smile of hers drilled its way directly to the pleasure centers of my brain. I could barely handle the visual stimulation as she pouted her full, soft lips in my direction.

Abbey was never one to downplay her glamor, but as she walked towards me in a low-cut top and an eye-wateringly short skirt, I felt I could be finally be entering heaven, or perhaps blue-ball hell. Her legs passed over each other, one after the next. Long, toned and shimmering with a silky, youthful sheen: they were a veritable work of art. The slight outward curve of her hamstrings and the elegant contours of her calves simply reduced me to jelly. I could worship those legs all fucking day long. Her hips curved inwards towards her slim, taught waist-- and her torso was topped off with a set of naturally firm, round breasts. I was agog. My train of thought completely lost.

"Hi gorgeous," she said, smiling and pulling out the chair beside me. "Whatcha doing?"

"Just some physics problems," I replied, as she sat herself down next to me.

"Got time for a chat?" she said, fluttering her eyelashes.

"For you Abbey, I suppose," I said back, with a smile. "Do I even dare ask how your weekend was?"

She bit her lip and smiled with her eyes.

"Well I had quite the weekend," she enthused.

"On Friday, I went to that new club in town, you know the one near the marketplace?"

I nodded.

"Well I went there with Maria and I met this absolutely gorgeous guy."

She took a deep breath, looked at the ceiling, and fanned herself with her hand.

"He was a Commando in the Royal Marines. He had a body to die for. He led me to the toilets and he fucked me right there. My God, I came so fucking hard. It made me horny for the entire weekend. I can still feel him inside me now."

"So did you see him again?" I asked.

"Alas, no," she sighed. "He was only in town for a day, so on Saturday I called up Jack, my ex, because I absolutely needed some more dick. I suggested we go skinny dipping, so we went walking to the lake, but I couldn't wait that long and his hands were all over me, so we just did it by the side of a farmer's field. I got my new dress all muddy, but it was worth it."

"Then on Sunday you went to confession, and ended up fucking the priest?" I asked.

She laughed.

"No, on Sunday I just started chatting with guys online. There was this guy who had a foot fetish. He was begging me to show him my feet... so I did. Then he kept asking if he could come over and lick them. He was a hedge fund guy and lived in America, but he said he'd pay to fly over here. It was so weird. It was awesome teasing him though. I got him to jerk off his tiny, and I mean tiny, dick on camera. I laughed so fucking hard!"

She sighed, before continuing, "I love just it when guys have little kinks, you can have so much fun with them."

She paused for a second, then her eyes focused on me with a wicked glint.

"I bet you've got some kinks John... It's always the smart guys like you who have dirty little secrets."

I laughed. "Maybe," I said, off-hand.

Abbey's eyes widened. "Oh you have got some haven't you. Oh come on John, tell me!"

Oh crap, why hadn't I just said "no". I took a deep breath. "Maybe another day Abbey," I replied.

"So you admit it!" she exclaimed, gleefully. "I can't wait, you have to tell me now!"

She pressed her bare leg against mine. The sensation of her soft, delicious skin sent a surge of arousal through me. Every instinct in my male body told me to prepare for breeding. I could feel my face flush and my dick begin to engorge. Shit, shit, shit. But the torment didn't stop there. She leaned towards me, pressing her firm, round tits against my arm. Jesus Christ.

"Tell me John, you know you want to... and it's only fair... I tell you everything."

I couldn't fault her on that point. As my dick stiffened uncomfortably in my shorts, I looked around the room. There was nobody within earshot--but even so.

"Look," she said, "it's not as if I'm going to be shocked, it's me for fuck's sake."

I breathed heavily, not knowing what to say. Part of me desperately wanted to tell her. Part of me knew that telling her would be a very risky choice. The weight of the decision caused beads of sweat to appear at my temples.

"Tell me, John," she demanded. "I bet it's good."

Wracked with indecision, I opened my mouth, then closed it again. The words teetered for a second on the tip of my tongue, before being forcibly gulped back down my throat. But Abbey's sparkling blue eyes were still boring into me, coaxing my secret back up from the depths.

"I..." I stammered, my voice losing all of its depth.

"Yes?" she said, with a wicked grin on her face.

"I... err... I like dressing as a girl."

Abbey's eyes widened. Her jaw dropped in utter glee. Then she started to laugh.

"Oh my God. You little sissy bitch!" she squealed in excitement.

Her mouth hung open and she scanned me up and down. "Now I know why you grow your hair so long."

My face started to burn deep red. She was right though. I did indeed let my mousy blonde hair grow long so I could look more like a girl when I wanted to. I'd told everyone I was going for the rock-star look, and since I played the guitar most people had believed me.

"So do you dress up often?"

"Yeah... every now and again."

"Does that turn you you?"

I gulped. This was another thing that it was really too risky to reveal.

"Yeah... kinda."

I squirmed in my seat as Abbey laughed at me.

"You've got to show me," she yelped. "I bet you'd make such a cute girl!"

And with those words, deep below my red-faced, squirming exterior, part of me glowed with pride.

****

Before I get too far ahead of myself, it's probably worth me giving you a little insight into my life--both now and back when all this occurred.

I've always had a pretty broad sexuality. I'm male, currently in my early-twenties and bisexual; and yes, I have been to bed with both men and woman. I've got a penchant for dominance and submission, again on both sides of the equation. Since I turned 18, I've been the Dom and I've been the sub, I've been spanked and been the spanker, I've teased and been the tease victim.

And I like to crossdress. I guess you can say there is a lot of stuff that turns me on.

I don't exactly identify as transsexual: I have no intention of undergoing any treatment to actually become a girl, and I do not believe I am a woman born into a man's body. For me it's a little more complex: I've always thought of myself as having two parts, perhaps even two similar but distinct personalities, one male and one female. Whilst the male personality generally comes to the fore, my alter-ego, Sarah, likes to come out and flirt every so often. And she likes being a girl with a dick, although she'd love the chance to be a girl with pussy on occasion too. I've often wished that I could change my body at the flick of a switch. Click--now I'm a girl. Click--now I'm a guy again. Click-- now I've got a pussy. Click--now I've got a dick.

For as long as I can remember, going back to when I was very young, a certain portion of my dreams and fantasies involved me being Sarah. I stress that I don't mean all of my fantasies, in fact, not even the majority, but a substantial portion: let's say around 30%. Some were romantic, such as being swept away by a boy; some were just about going about my life as a girl; some were downright sexual, especially by the time I'd grown up.

I guess I started as many guys do: I slipped into my sister's clothes when the house was empty--and felt that rush of excitement you get when you feel the delicious silky, feminine fabric against your skin. I shimmied into her slutty skirts, pulled her sexy stockings up my legs, and experimented with her make-up. I got away with it too: she was so untidy she never knew where half her stuff was to begin with.

After some amateurish first attempts at feminizing myself, I began to read online about how to do it properly. I wanted to be as passable as possible, and as sexy as possible. Sarah was shy, but she wasn't a wallflower. Beneath her bashfulness she wanted to flirt and be desired.

I soon graduated from pilfering my sister's clothes and make-up to buying my own. I needed outfits that fitted me better, and foundation that better blended with my own skin tone. I didn't want to risk ordering online as sometimes my parents "accidentally" open my packages and mail. So I simply went into town with my measurements and told the shop assistants I was on an errand for a friend.

As time passed, little tips and tricks became second nature. I learned to use eyeliner to make my eyes look bigger. I learned to give myself a feminine hourglass figure with a thick belt around my waist. I learned to hide my Adam's apple using contouring make-up, wearing high collared tops, or wearing a slutty collar. Sarah loved that last one especially.

I guess it helped that I'd never had a particularly masculine appearance. My face was oval shaped, my skin was clear, and I was slow to get facial hair. Even now it is nothing but slightly wispy, but when I was eighteen I was pretty much entirely hair-free. I am, and was, pretty skinny, which helps too, as body fat distributions can be a give-away to gender. Over many years I even grew my hair long. This was much to the derision of some of my male friends, but surprisingly, many girls liked it, even when I was my masculine self. Maybe some girls really did buy into my "rock-star" excuse.

I got better and better until one day I looked in the mirror and was impressed that not only did I actually look like a girl, but I actually looked cute. Almost instantly I was consumed with excitement. As I winked and flirted with myself in the mirror, my dick got hard in my filthy little knickers. I couldn't help but run to my bed, tie my ankles together, jam a dildo in my mouth and masturbate until my dick was sore--fantasizing about being a cock-sucking slave girl. I writhed and moaned in ecstasy, then spurted multiple loads of cum all over my sheets.

I'd experienced difficulties at first wearing heels, but with practice I got to the point where it was second nature. I could walk in them, dance in them, sway my hips in them. The most difficult part was sounding like a girl. I tried so many different voices, most of which sounded utterly ridiculous - until I read a tip that cross-dressers should try a different accent and see whether that worked. I searched YouTube for videos of girls with different regional accents and tried to mimic them. Eventually, I found one that I could I could do: a Scottish accent that was both realistic and feminine. From that moment Sarah became Scottish.

Searching maps, I came across the small town of Burtisland in Fife. With a population of around six thousand I guessed that virtually nobody I'd meet would be from there. I did my research and it became my cover story if I needed it. Sarah's childhood summers were spent on the beach and at the annual summer fairground. She attended Burntisland Primary School, before moving on to Balwearie High School. That, of course, all happened before her family had moved to England last year, but she could still wax lyrical about the ancient Parish Church and Rossend Castle, two of the town's most important historic sites.

Despite the cover story, I didn't think more than letting Sarah play around the house when my parents were out and my sister was off at university. She tied herself up, she spanked herself, she sucked her dildo cock. Sure, she fantasized about going out, being a little minx, teasing guys and having a dick plunged deep into her slutty ass--but it always seemed too risky to do it for real.

And then came the incident with Abbey.

Abbey never ceased to amaze me. We'd known each other since we started primary school. My miniature self had thought she was cute even then, but boy how she'd developed. We'd never had classes together until recently as she had always been in the school year above me. However, despite her being pretty smart, she had done very badly in her final exams--so she had decided to stay back a year and resit. At nineteen she was the oldest girl in the school.

I have no doubt in my mind that the reason for her poor academic performance was her over-active sex life. Whenever she should have been studying, she was sucking, or fucking or engaging in some other act of decadent sexual depravity. I've never met anyone before or since who had a such a high sex drive--and she had no shortage hard, willing cocks to indulge her cravings. In the last few of years of high school, she had gone from cute to gorgeous. As I described earlier: flowing blonde hair, tight toned body, and long tanned legs. Mix that in with her utterly compulsive flirtatiousness, it is difficult to see how things could have worked out much differently. Sex was written in her stars.

I was no stranger to her affections--not that I'd succumbed. I didn't really doubt that she would have fucked me if I were willing: she'd suggested we "go and have some fun" more than once--but I was too scared that I wouldn't meet her standards. I knew from her stories that she took a dim view of guys who didn't know how to please her and I was a virgin--at least of sorts. I'd never had sex with a girl. My only proper sexual experiences involved being fucked by a guy, and I wasn't sure that provided me with the training I needed to satisfy her.

Nevertheless, between classes she'd come up to my desk, play with my hair, tell me I was cute, then proceed to regale me with stories of her sordid sex life.

She'd fucked two of our teachers. One simply because she thought he was hot. One because she wanted a better grade. She'd told me about her back-alley sex, her favorite way to give blow jobs, and how one should properly take a cock in the ass. She told me about her dildos. She told me about her handcuffs. She told me about her experiences with other girls.

I never tired of listening to her. It opened my eyes--and gave me a lot of images to masturbate to in the privacy of my own room.

I was a moderately popular kid, but my friends were the really popular ones. I was the smart one, but just funny enough to get away with it without rubbing people up the wrong way. As a guy who circled in the popular crowd, I was on good terms with the popular (read: attractive) girls--of which Abbey was definitely one.

However, our friendship extended a deeper than just associating in the same circles. I was also one of the few people she could open up to. Although I wasn't particularly sexually experienced, I was stridently liberal minded. I was genuinely interested in what she had to say--and listened to her without casting judgment or mockery. With me she had the perfect audience--and I think she liked the intellectual fire power I could bring to an argument if someone tried to make out that her lifestyle as morally wrong.

Despite that, I wouldn't say I entirely trusted her, for as I mentioned, Abbey was dangerous. She liked to tease boys. She liked to get them hard in awkward places. She liked to make people squirm. She liked to make people go red. She liked to rate guys by their sexual prowess and dick size -- and she wasn't afraid of revealing who didn't measure up--all said with a wicked grin on her face.

I can't say that I didn't jack myself off furiously to the thought of her humiliating me - and there was a fair chance she'd have delighted in doing just that If I'd asked - but my rational mind did not think that was best for my prestige or my future. As such, I'd played my cards incredibly close to my chest for a long time--but as you already know, I couldn't hold out forever.

****

So let's get back to the meat of the story.

The moment of pride induced when Abbey said that she thought I would make "a cute girl" was short lived. The next thing she said overwhelmed everything.

"I'm going to tell Maria!" she exclaimed. Instantly my regret chip fired.

"What? No. Abbey!" I seethed under my breath.

"Come on, Maria won't mind. She's seen everything."

Maria was Abbey's partner in crime, perhaps even her protege. They went out on the hunt together at weekends and they made quite a pairing. Abbey was about my height, but Maria was one of the tallest girls in school. She was also very pretty. She had been a bit of an ugly ducking when we first met six years ago--but she would definitely win the award for 'most improved' since then. She had pale creamy skin, thick, dark-brown hair, a light smattering of cute freckles, and a long lean body capped with generous round breasts. Maria had been the subject of a number of my fantasies too.

"Abbey, please don't. I only told you because I trusted you'd keep it quiet," I begged, pathetically. My mind was going insane with worry, but my submissive side caused my dick to twitch involuntarily in my pants.

"I promise I won't tell anyone else, but I have to tell her."

She got up from her seat.

I grabbed her wrist.

"Abbey, NO!"

"Let go or I'll shout it to the whole room," She looked at me sternly, like I'd committed a crime.

I squirmed in my seat and let her go.

I watched her skirt bounce against her firm little ass as she skipped away.

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