Shemale
2008-09-26

This is a fictional story exploring my life long fetish for cross dressing and how I imagine being caught by a woman who surprisingly understands this desire and need. The story contains adult material of a sexual nature. If you do not like this topic then thanks for reading thus far, otherwise, hope you enjoy. I would love to hear your feedback. The first part of this story is very dialogue based to help set the scene and shape the second half of the story (the naughty bit!) *A little about me to set the scene, I'm early thirties and a professional guy who lives alone in a rented top floor apartment (this has some relevance later on!), I look after myself and keep myself in shape. However, my fetish (we all have them, even if we don't admit it), is I adore women's clothing, shoes and dressing up to change myself into Ellie. Work had been mad and I'd felt like I'd spent more time at the office of late, this led to the apartment being a mess with me just leaving stuff all over the place and I totally forgot Lily Jones my land lady was due for a visit to check out the place. Lily is an amazing lady, I've know her now for close to three years and on a social level we get on with each other quite well, letting the business side of me renting an apartment take care of itself. Today this was all going to change as the phone rang . . . "Hi", as I picked up the phone, "It's me Lily, just wanted to check your in, it's the three month check over time again", "Lily, sorry I totally forgot, can you give me an hour?" Thinking to myself, I got some major tidying to do in an hour! "Sure sweetie, it's 1pm just now, I'll be over about 3 that'll let me get another errand out of the way first" "Ok, that's great, see you then". Some breathing space I thought, so I quickly tidied up the place, making it look more presentable, the magazines etc all just got put into piles to make everything look organised. No need for the desk area, Lily knows I work from home and won't expect that be tidy! Into the bedroom, I just looked, lingerie, heels and a couple of dresses where over the chairs, as a quick fix, I folded everything onto one chair and put a large towel over it, Lily never spent any time in the bedroom, just gave it a once over in the past! Ok, the place looked not too bad now, at least it was tidy and presentable, even if it did hide a few 'secrets'. 2:30pm and it was a real hot day, so I decided to jump in and have a quick shower so I was nice and fresh and didn't look like I had been running round for the last couple of hours. A nice cool shower and I was all sorted! After showering I slipped on a lovely black stretchy PVC pouch thong under some black shorts and t-shirt, I just could not resist slipping on some nice underwear, maybe it was the hot summer weather, any excuse really! 3pm arrived and the buzzer went, letting Lily through the security door, I could hear the familiar click of her heels coming up the concrete stairs, I left the door open and greeted her as she arrived, some small talk about how we were doing etc followed and I offered her a drink, having a glass of cold wine already poured for myself.

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"Got some nice cold wine there I see?", Lily said with a smile "Sure have, fancy a glass?" "Yeah why not, I just had to drop the car off for some repairs and will be getting a cab home so would love a glass!" I could not help noticing Lily's new hair colour, a deep red and she had it bobbed to her shoulders now.

She was wearing a lovely white summer dress and strappy heels, which really showed off her tall slim figure, she was the same height as me in the 3" heels she was wearing so I guess she must be 5'8" bare foot and has long slender legs with a perky firm butt. I'd say her figure would be 34c-24-32. I poured her a large glass of wine and sat down on the sofa which faces the large window and catches all the sun. "I forgot how much sun you get in this apartment, it's lovely isn't it?" "Oh yes, especially with a glass of wine!" Lily giggled and said cheers as she took a drink, "Oh I needed this, it's been one of those days today" "Tough day then?" "Just lots to do, mind if I sit down for 18 minutes before we check the flat?" "Not a problem at all Lily, I'm finished for the day, so take your time!" My eyes glanced her over, checking her out, even though she was a little older she was still very hot and desirable. Her makeup was perfect as usual, the dark red lipstick matched her hair toning perfectly. "I love your new hair style it really does suit you Lily!" "Thank you sweetie, I just fancied a change and went for this bold colour" This made us relax a bit and sip the wine, taking in the afternoon sun, I could actually feel myself starting to sink a little into the couch as I relaxed more. Once we finished our wine, Lily mentioned we better check over the apartment. "Feel free, you know where everything is!" "Lazy, lazy" with a tut tut in her voice "but yeah enjoy your wine and I'll have a look around" After about 18 minutes, Lily returned to the living room and said, "everything looks perfect to me!" Lily stood with her hands behind her back over the sofa, and I could not help but notice her cleavage and the wonderful shape of figure. "Fancy another drink before you head off?" "Yeah go for it, we can discuss something while we drink" Ah hell I thought, here we go, rent increase! It had been about a year since the last one! I poured some wine and Lily was still standing with her hands behind her, as I motioned for her that the drinks where ready, she smiled and we headed for the couch, I slipped past so I could put the glasses down on the table, Lily still had her cleavage on show and I tried not to make it obvious I was staring! As I sat down I said "fancy a seat?" "Yeah, but first I need to ask you something?" "Sure, whats' up?" "Well, this is going to be awkward, but when I was in the bedroom, I hung your towel over the radiator so it dried better!" "Oh!" as my face turned crimson red "erm, you did?" From behind her back she produced my black silky dress, "This is lovely, new girl friend?" "Eh, er, no still single, it's mine!" Somehow Lily standing there with my dress in her hands was an amazing turn on and I could feel my crotch twitch in its little thong enclosure! "Please don't tell anyone?" I semi pleaded with a need of privacy in my voice "Do not worry about that sweetie, what you do in your own time is your business, and the size 18 high heels gave it away, sorry I noticed them as I was checking the wall vent under the dresser!" "Guess the secrets out between us now then!!" "Guess so sweetie! I think it's kinda cute actually a man who can explore herself!" she smiled a very wicked smile as she said 'herself'. Lily, stood drinking and then sat down beside me, putting her hand on my thigh, which made me twitch and my body shudder a little both with excitement and nerves! "Sweetie, I couldn't help notice your shaved legs and your always shaved smooth and very presentable, guess I know why now. The legs are no just for your cycling!" "Yeah the cycling is a good excuse for the smooth legs" I could feel my embarrassment subside a little, but this was uneasy ground for me. Just then the conversation took a drastic change as Lily asked. "So are you Gay?" "No, I like women" I spluttered out "Are you sure?" "To be honest I've thought what it would be like to be with another dressed up 'girl' " "mmmm, ok, I can understand that sweetie" Lily sat round to face me, "I've a secret too, not like yours, but I'll share it with you" "When I was born I was both a girl and a boy, the doctors and my parents decided I was too be a boy, and guess they got that wrong! I'm everything female except I don't have a pussy, I've the same as you sweetie, a nice long squirting clitty!!" "Oh fuck!" was I all I could manage Lily looked me in the eye "shocked?" "Yes, I mean your so hot and sexy!" "Thank you sweetie, but now you know why I am single!" "Pass me the dress Lily, please" "Why?" "I want to show you how I look, see what you think?" "Oh yes I would love that!" I took the dress and said "back in 10" as I headed to the bedroom, I quickly had my shorts & t-shirt off and the dress slid over my perfectly shaved body, I slipped on some 4" spike heeled black court shoes and put in my black haired short bobbed wig with some pale red lipstick and a quick flick of eye liner. I was too nervous for a complete makeup job and my hand where shaking too much anyways! Ok, here goes I thought to myself, no one has seen me dressed up before apart from a couple of pictures I had taken, gulping down the last of my wine, I was ready.

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I slinked through to the living room and gave a little twirl on my heels, the dress swirling round with me and my hair fluttering. "Wow sweetie, very sexy!! I love your look, nice hair style!" "Thank you Lily, but I need another wine now!" "Me too!" Lily replied I took her glass and got us a refill, my mind racing and my nerves starting to settle a little, this was actually happening, I was being a girl in front of another person, a sexy lady at that too, a mixture of adrenaline and feeling horny ran trough me as I thought about what was under Lily's skirt!! "So I can't call you by your male name anymore, I guess?" "No, I'm Ellie now!" "Indeed you are, but honey, your nerves showed a little, come here and let me fix your makeup for you Ellie" I walked over to Lily and sat down beside her, as she touched my lipstick up with a napkin and straightened out my lips, "that's better sweetie". Any tension I was feeling was gone as Lily kissed me softly of the lips and stroked her fingernails gently down my face, my hand on her smooth firm thigh was at the bottom of her white summer dress as I kissed her back. The feeling of kissing with both our lips painted in lipstick was amazing and they almost felt like we were stuck to one another, our kiss got more passionate and before long I could feel Lily's tongue in my mouth as we started to French kiss, her had slid up my thigh inside my dress, her fingernails just touching the top of my thigh.

My hand followed up Lily's thigh, slowly teasing her, but I did not stop, I had to find her clitty and pleasure her, I wanted this adorable woman with heated passion. Breaking the kiss, "Are you sure Ellie?", Lily whispered to me, "Yes, very sure Lily" Lily stood up and without showing me, pulled down her French cut knickers, I noticed they had an insert in them that had a 'body shaper' is the best way to describe it, giving her a very female form. "I just need to use the bathroom, these shapers can be a bit hot in summer" "Ok honey, be quick!" With that Lily's heels clicked off to the bathroom as she had a quick freshen up and when she returned she stood in front of me, her waist level with my face as I sat, putting down the last of my wine, I stared up at her, smiled and lifted her skirt. As her skirt lifted I held my breath, and stared, there was the most beautiful shaved, smooth uncut 18 inch cock with a beautiful huge and looking very full pair of balls! I run my hand along the length of the shaft slowly and pulled back her foreskin, pre-cum flowed out the tip and I did what I felt natural, leant forth and licked her clitty-head clean!! "mmm . . . wow Lily . . you taste fucking amazing!" "Why thank you girl friend, I'm glad you enjoy it Ellie, I want you too!" My right hand cupped her full heavy warm balls, feeling the smoothness of the skin and gently squeezed them as my mouth slid over your clitty-head, gently blowing my warm breath around her head and shaft as my lips closed and I sucked her smooth velvet purple head into my mouth, flicking my tongue over her pulsing sex, feeling her slide deeper inside my mouth. I massaged her balls a little tighter and rubbed the base of her clitty with my index finger just stopping at her tight little rosebud pussy. I could feel Lily's hips start to move in time with my mouth as I sucked as much of her in my mouth as I could, getting about three quarters of the length of her in my mouth, her clitty-head pulsed on my throat as her heavy cum filled balls twitched in my hand.

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I bobbed my head as a fast I could, letting Lily fuck my mouth my lips wrapped round her long thick clitty cock sucking her as deep and hard as I could. "Ellie, I'm gonna cum!! Fuck don't stop!!!" I dropped to my knees on the floor, grabbed her shaft and started to wank her clitty cock as fast as I could girating my hand on the shaft as I suck her head, massaging her balls with my other hand. As I felt her balls tighten I took her cock head out my mouth and wanked Lily as hard as possible over my face. "Fuck yes , fuck YES FUCK . . . ohhh sweetie" Lily screamed The pulsing reached a point where Lily's body shook with an intense orgasm and I felt the cum rise from her balls past my hand on her shaft and then pulsing out of her clitty cock head all over my face and into my open mouth, three massive quick huge squirts sprayed my fast covering my cheeks, lips, eyes, hair, you name it!! Lily was still quivering when I felt a several smaller squirts land right in my mouth, at this I wrapped my mouth around her cock and suck everything out her girly clitty cock, squeezing her balls for every drop. Lily collapsed beside me as I used my index fingers to collect all her cum from my face and drink it down, it tasted so amazing and warm. Once I had clean myself up best I could I leant over and kissed her. "Thank you Lily, I know now I love girly cum!!" "By fuck girl you suck an awesome clitty!!" We lay for a while, sipping wine and cuddling, "Want to stay the night Lily?" "I sure would girlfriend we have a lot to explore!" I giggled and said, "Well I'm not a cum virgin anymore" "But yes you are, unless you've felt it squirt elsewhere . . . . " I stood up, slapped my ass and said "No this is yours too . .