"Waiting" on Fantasy

"Are you ready for this Mish?"

"Not really but it's too late to back out now."

I stood in a dark alley before a metal door shaking with both anxiety and the cold, waiting for the door slot to open and for the night to begin. I wouldn't admit it to my friend Simone but secretly I hoped we would be turned away so I could stop trembling so much and I could slink off home, pretending to be disappointed all the while.

Slink may have even been the wrong term to use in this case though. Perhaps clatter, clop, click or even stumble may have been more appropriate in these shoes.

I still couldn't believe that I was wearing inch high, stiletto heels. In fact, quickly glancing over my outfit tonight, I could believe that I was wearing any of it especially the short black dress, which was not only backless but figure hugging.

How did I get myself into this position!

__________________________________________________

It had only been earlier that same evening that my beautiful best friend and roommate came home early after one of her typical nightclub escapades bursting with excitement.

"David! David!" she called from the doorway breaking my introspective silence within our little apartment as the door slammed open. I was slumped on the sofa, beer in hand and feeling pretty relaxed already for this early in the night.

"You won't believe my news." Simone stated as she races into the longue room and bounced onto the coach beside me. I didn't even look up from my movie as I responded in rather a less enthusiastic tone than she may have hoped.

"What's his name this time?"

"No, no it's not a boy it a chance for us to make some good, no great money!"

That got my attention. I had looking for a job for almost a year and without money soon I would not only have to move out but return home to live with my parents.

That was something I dreaded even more than moving away from Simone. I sat up and turned my attention to her.

There she was - Simone, my beautiful best friend. I had always wanted it to be more that 'best friends' but unfortunately I just never seemed to find the right way or method to change our relationship.

It killed me when she came home disheveled from clubbing, looking drop dead gorgeous with her long jet black hair, pale blue eyes, large pert breasts and dress out of place, and she just wanted to talk. I had become a good listener but must say I did often become distracted staring at those long legs and tits she never seemed to cover fully. To top it off she was nice too.

Caring, thoughtful and kind it's just not fair. A beautiful girl who was this nice and hot but threated you like a brother is a special form of hell I believe.

"So what do you mean great money?" I asked skeptically, drawing my eyes away drunkenly from her cleavage.

"Tonight I was sitting there with Alice (another of Simone's smoking friends that treats me like a little brother) and this guy approached us in an expensive suit. We thought he was either trying to hit on us or buy us a drink but he wasn't. He gave us these two red tokens and said we could make thousands of dollars as waitresses for one nights work!"

Simone stopped to take a quick breath before continuing with her eyes wide with amazement.

"My friend Jenny said that one of her friends was asked and made $5000 in one night just waiting on a bunch of rich guys."

"So how does this help me?" I asked taking one of the token from her and inspecting it. It read 'Sirens' and had an image of a beautiful redhead blowing a kiss with today's date etched below it.

"Well Alice can't do it tonight as she had to meet her boyfriend for his birthday and I know you've worked as a waiter and behind a bar before so I thought you could do it..." Simone looked at me expectantly.

"Ok but wouldn't they be expecting another hot girl to go with you instead of a short skinny bloke? I mean they weren't handing out these tokens and the address to other blokes were they?" I asked raising an eyebrow.

"No only me and my friend. Supposedly they only ever choose the most beautiful girls so I don't know why they gave me one?"

"Yeah – because you're so ugly," I laughed I said as she playfully punched my arm.

There was an expectant pause as I watched her building herself up to say something.

It was quite cute really.

Simone moved her hand to my leg and leaned forward, "Remember last month at our housewarming party when you got really smashed while we were playing that game and we had to swap clothes in the closet?" she said raising her eyebrows suggestively.

"Vaguely," I said trying to move away from her touch, uncomfortable where this was heading. I did remember trying to see and feel as much of her as we changed in the confined space that was for sure.

"Remember how hot you looked once I placed that blond wig on you and how you liked the feeling so much you left my clothes the rest of the night." she reminded me shuffling forward on the sofa towards me as I found myself inching backwards.

"Yes, I was just joking around and..."

"And remember," Simone interrupted, "how one of our new neighbors arrived late and tried to pick you up and started rubbing your thigh on the coach?"

"Yes I couldn't get away," I stammered getting up from the sofa

"And remember when I dragged you away from him into the bedroom you had a massive erection." Simone smiled lifting herself from the coach too.

"It must have been the way the way the dress rubbed against my crutch," I muttered.

"Any way you looked beautiful David. I mean you really looked like a girl. If you had padded out the bra you were wearing..." she said pushing me up against the wall and squeezing my chest

"Oh, ok, thanks... I think," I stammered. She had her body pressed to mine and the feeling of her ample chest squashed against me was very distracting.

"Could you dress up for me now David? I would really like it." Simone eyes held my own with an intense gaze. I felt her hand move down my chest to my stomach and then stop teasingly just under the top of my pants.

"I, I, I guess so, I mean if you re...really want me too," I stuttered

"Great I'll go to my room and find something for you to wear."

Simone slowly peeled off me and moved towards her room, looking over her shoulder as she entered and giving me a naughty little smile when she caught me watching her ass.

I stood there for a minute in a daze. I did remember that night. David had enjoyed how he had felt in the dress and had marveled how sexy he looked when he caught himself in the bathroom mirror. He kept catching his friends at the party checking him out and the most surprising revelation to him was that he found he liked it. He really liked it! He had always had a rather feminine body. He was short, skinny and almost hairless.

He even seemed to have female curves with his hips curving into his small muscular waste. He was toned had long lean legs, no protruding voice box and feminine facial features. He had often be mistaken for a girl with short hair with guys trying to char him up or even pinching his ass before he became angry with them and set them straight. Given all that David always fancied he still had a good sized penis but granted he hadn't a lot of others to compare to.

"David, I'm ready," Simone called from the other room.

I went in and there she had laid out the same dress I had worn that party a month earlier. There was also the same long blond wig and next to it was a pair of black lacy, and might I say, skimpy undies. There as also a black lacy bra and what looked like large breast shaped silicone bags to fill them. Black suspenders and red high heels shoes completed the outfit.

"Let's go to my bathroom first."

Simone led me into the bathroom and promptly told me to undress.

"What? Down to my jocks?" I asked concerned.

"No. All the way!" she said seductively.

Shit! This was really turning her on and judging by the big tent in my pants it was having the same effect on me. Here was a girl who had barely kissed him on the check and was now asking him to get naked for her and he was hesitating. Well there was no better time to show off his member than while its at its biggest. So I stripped off my clothes while she watched me with a cheeky smile. When I removed my jocks I was at full attention.

"That will have to come off!" she said with a slight frown.

"What!" I said, covering myself up protectively, "you're not touching my penis."

"Not your willy silly! You're pubic hair." Simone laughed, "In fact, all your hair from your eyebrows down and even those I'll need to use my tweezers on."

She then proceeded to wax, shave and prune me. Luckily I wasn't a hairy man. In fact, other than my pubic hair and under arms, she struggled to find any other hair to remove. I did enjoy her searching in areas I never though you could even grow hair though. Shaving my balls was probably the only really nervous moment he had. She then thinned out my eyebrows and began to apply nail polish and make up.

Through it all I just reveled in her touch and attention.

Once she was satisfied she led me back into the room and had me sit on the bed. She then drew out a little jar of adhesive and applied it to my chest and then stuck the silicone breasts to my chest carefully. When she was pleased with the way they looked she asked me to gently feel them. Shit I thought, they felt like the real thing with nipples and everything.

"When did you get these?" I asked.

"After that night you looked so hot in my dress I ordered them for you just in case.

They will stay on for days unless you use the right solvent to take them off."

"I'm going to need another beer," I said admiring my new cleavage.

Simone smiled and obliged disappearing into the other room before bringing me back a beer and bourbon. I started with the spirits, which was bloody strong, and then sucked down the beer quickly. Simone then kneeled in front of me while I sat on the bed and she started to help me into my lacy undies. She drew them up my calves and thighs but found a roadblock in the form of my massive boner.

"I can't have you looking like a woman with an erect penis now can I!" she purred looking up at me with those amazing pale blue eyes.

Simone kept my eyes locked with hers as she gripped the base of my penis with one hand and then ever so slowly parted her full red lips and opened her mouth to bring out her little tongue to lick my engorged penis from base to tip.

"Fuck!" I moaned throwing my head back in pleasure.

"So you like that?" she teased

"Yes," I said empathetically nodding.

"Well then you'll love this!" she smiled and opened her mouth to take me into fully into her.

The heat and moisture of her mouth was breathtaking but the way she moved her tongue around the head of my penis was incredible. She then pushed her lips slowly down my shaft and then up it again. She repeated the process over and over again pushing it deeper and deeper into her mouth and throat each time.

All the time keeping her incredible smoking eyes locked on mine. It was sensational. The girl I had lusted after for years, the girl who was my best friend was giving me the best blowjob I had ever had.

I watched as my saliva sheathed cock disappeared in and out of sweet mouth. More and more of it disappeared past her red lips until I felt the tip of my rock hard rod ram into the back of her throat. I couldn't believe the feeling. My balls were pushed right up to her chin and she held me there, as if it was a personal challenge to see how long she could maintain the depth of my insertion before she quickly withdrew me with a sudden gasp.

"You are a goddess," I cried and she began to gently stroke my saturated appendage while licked my freshly shaved scrotum.

"And you are a naughty little girl letting me lick your dirty little hole aren't you!"

Simone said between sucks and licks.

"Yes I am!" I replied caught up in the moment. Wait a minute. Did she say 'hole'?!

Suddenly I felt the tip of her wicked tongue dart in to touch my untouched anus. Shit! I involuntarily clenched my cheeks together and pulled back. Simone still had my cock in hand though keeping me both hard and close.

"Just trust me," she whispered pulling me back, "Now bring your legs up and spread them."

I did as she asked slowly still unsure where this way going. This time she slowly brought her tongue to my ass and lapped at it before probing deeper with the tip.

Fuck it felt so good, so naughty, so evil. After a while I found myself pushing back on her face to help her get further into my ass. Suddenly she stopped and moved over to her bedside draw to retrieve something.

"Please don't stop," I begged.

She giggled and said "I'm not finished yet Michelle."

"Michelle?!" I asked.

"It's what I thought I would call you when you're looking like such a hot little girl."

She laughed taking my penis in hand again and began to take me in her mouth again.

"Fuck! Call me what you want if it means you'll do this to me!" I gasped, throwing myself back on the bed.

Simone began to work her magic on my cock again before asking me to shuffle back again and bring my feet up on the bed to bend my legs.

I then heard a little pop of a tube opening and a squish off something being squeezed out from down below my eye line where Simone knelt. She continued to work my penis in and out of her mouth before she turned her attention back to my eager asshole. It felt amazing with her tongue stretching my ass as she gently kept me erect.

It felt so good but then she withdrew her tongue and replaced it with one of her fingers. I felt her lubricated finger slowly slip into my ass bit by bit and she moved her mouth back up to my swollen member.

"Yes," I moaned, and began thrusting slowly into her mouth. She murmured in approval.

Simone then began thrusting her finger in and out of my ass in time with my own building momentum. I loved it. I felt her finger go all the way to her knuckle and her touch and pod my prostrate. I almost came then and there! She then took out her finger and took me out of her mouth before I felt her re-enter my ass with not one finger this time but two!

She continued to thrust in and out of my ass while rotating her mouth between my balls and cock. I felt overwhelmed with pleasure and knew I needed to ejaculate soon or I would burst!

Once again she took her fingers from by stretched ass, applied more lubricant and then I felt her insert what felt like her whole hand but turned out to be all four of here fingers. I felt my ass stretch and squeeze back on her fingers before I relaxed when she took my penis back in her mouth and she began pushing her fingers in and out further each thrust. Before long I had four of her fingers stretching and fucking my ass up to her knuckles as I fucked her mouth with uncontrolled rhythm.

"This is amazing," I yelled and felt myself on the verge of exploding.

"I'm coming!" I warned just seconds before spurting stream after stream of hot cum into her luscious mouth. She didn't pull away but took it all into her mouth. Once I was finished I watched as she pulled her fingers first out of my stretched anus and then her amazing mouth back from my shrinking rod. I saw some of my sperm drip from her lips to the floor.

Simone looked up to catch my eyes with a lustful hunger while she moved up from the floor, slid on top of me and kissed me passionately with a mouth full of seamen. The salty taste rocked my senses as her seamen saturated tongue swirled around my own. I thought I should have been revolted but I was strangely aroused sucking my salty cum down my throat desperately. What was happening to me?

"Thank you," was all that I could force out after our passion slowly abated.

Simone giggled and then went back to lick me clean before finally placing my now very satisfied penis into my lacey G-string panties.

Simone proceeded to complete dressing me while I lay back exhausted, letting her take complete control. She first put on the bra over my new 'breasts', then pulled on my back thigh high suspenders and then made me stand to pull my dress on, securely hooked my wig on and did my hair. After touching up my make up she led me to her full-length mirror and asked me to look.

"My God!" I gasped.

There, looking back at me was a bloody smoky hot blond. I had to move around just to make sure it really was me. Fuck! I even had a figure and those fake tits were sensational. My legs were long and toned. My ass was lifted and pert but it was my face that I couldn't believe. Simone was an artist. I thought I was a good-looking bloke with perhaps a little too feminine features but as a girl my face was beautiful. I had long eyelashes that framed my brown eyes and my lips were round and full. My long blond hair was bounced upon my shoulders and hung down my back. I was a knock out blond!

"What do you think?" Simone asked, a wry smile fixed on her face.

"I'm gorgeous," I replied, "I can't believe how hot I am as a blond!"

"I know David! As Michelle you are a super model! Shit you even have female curves and your legs and tits are better than mine!" Simone pouted over my shoulder as she admired me in the mirror.

"I wouldn't go that far!" I teased turning around and wrapping her up in another kiss.

"Don't do that, you'll ruin your make up for tonight!" she said disapprovingly.

"Tonight? Oh that waitress gig," I said, "You can't seriously think that I could go out in public looking like this?" I said turning back to the mirror.

"Of course you can," Simone said, "there is no way anyone would know you're a guy."

Looking back to my reflection in the mirror it was hard to argue. The alcohol and moment obviously got to me because whatever common sense I had completely slipped.

"What do I have to do?"

Simone had me practice walking in the stiletto high heels and talking in a feminine voice. Both were more difficult that I imagined. Just walking without falling over was tough enough but then add trying to look natural and stay poised was nigh impossible.

I gained a lot of respect for women within 5 minutes of feeling like I had been walking on a tight rope why trying to appear alluring and carrying a tray of glasses in one hand. After all my efforts we would need to buy more glasses tomorrow that was for sure. Simone took a great deal of mirth from my early attempts and actually did very well to disguise her bursts of laughter from me with well placed coughs and encouragement.

After what seemed like the 50th time practicing walking back and forth to Simone did she seem pleased. I would walk towards Simone and ask her if she would like a drink before walking away again slightly swaying my hips only to then return from the kitchen with a loaded tray of drinks and place a glass in front of her. I gave her a wink and a smile and then left. Simone even began acting like a guy sometimes pinching Davis butt or making grabs at her to try and throw her off.

"Do I get a pass mark cutie?" I asked in a suggestive soft voice that I had been trying to perfect over the past hour.

Simone giggled and said "I don't know about the guys we're waiting on tonight but I would definitely like you serving me!"

Simone looked at her phone to check the time and quickly moved to stand.

"Ok we need to move now David, I mean Michelle! I need to give you a quick crash course on topping up your makeup if we get separated and then we'll need to go. I'll get you the matching handbag for your dress and one of my little make up kits to go in it."

After a few minutes and practicing applying and reapplying lipstick, foundation, eyeliner and mascara I was more confused than educated but Simone assured me that as long as I could make sure my lipstick was fresh the rest was a bonus. While the coloration was almost spot on, she did make sure I placed foundation around my chest to ensure my 'breasts' matched my own skin color.