Written by M & A
14 Aug 2009
A cross dressers dream come true
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6 minute read
From a young age I'd enjoyed dressing in womens sexy underwear, I stopped when I met and moved in with my first serious girlfriend. It wasn't a question of, don't want to mess this relationship up, more a case of my sexual appetite was already being very well taken care of so didn't feel the need. Anyway she didn't know and I wasn't going to tell her.
Imagine my surprise when on arriving home one day to our bedsit flat there was a black wrap-around dress laying across the bed. It was a bit formal for our usual outings so I asked, "What's that for?". "You", she replied. She went on to explain that she'd entered me for a charity fund raiser and put it rather bluntly that as she'd paid a deposit there was no point my arguing with her.
I really didn't want to be seen dressed, I felt guilty about my fetish. "We'll practice this evening after tea", she said. "But I er, don't have any underwear and stuff" I stammered. My heart was pounding when she started pulling her sexy underwear out of her drawer and said, "Some of these will fit you". I thought I'd died and gone to Heaven.
After tea I stripped naked, she sat me down at the foot of the bed and held up various items for my appraisal. I stood up to put on the white lacy suspender belt, she did it up from behind, then she came round to my front and knelt in front of me, I placed a hand on her shoulder to steady myself as I slipped my foot into a tan stocking as she held it open for me, then the other. As she rolled them up my legs I said with an air of defiance, "You'll have to attach the suspenders, I don't know how", I lied. All was going well until next I stepped into her navy waist slip (with white lace trim), she was getting up from her kneeling postition in front of me and as I pulled the sexy slip up my stockinged legs my swelling cock gave the game away, I pulled the slip into position, turned it so the seam was at the back and she touched my cock through the still cold material, "What's this?" she demanded. "Well I er, all this is a bit of a turn on", I blushed. "We'll sort that out later", she said matter of factly. Her bra didn't fit, although I loved trying it on, having her behind me helping as the sexy shoulder straps caressed my naked and tingling skin, my cock now straining into the slip, we compromised on a bra and I wore her stretchy, shiny blue satiny feel halter neck bikini top. We used some tights for the padding to the bra, which only made me even more horny. She helped me into the dress, and tied the waist straps behind my back. "Now you can put these on", she said as she held out a pair of very lacy, white, crotchless knickers. (a present from her previous boyfriend). Christ, they felt good, the lace ever so gently caressing my cock and balls.
Realising that I wasn't putting up any resitance at all, her tone changed and she smiled as she patted the bed where she wanted me to sit for her to practice her make-up technique on me, a little founation, some of her eye shadow, mascara and her dark (nearly red) pink lipstick. When she'd applied the lipstick she told me to pull my lips in to even it out and to close my lips on some tissue to remove the excess. "You look great, just one more thing though", and out came a shoulder length blonde wig, "I borrowed it from the organisers of the fund raiser", she said. She brushed it out and helped me put it on, I could feel the fine hear tickling my neck as it fell loosely to my shoulders. Finally she said, "There, take a look at yourself". We only had a small mirror so I couldn't see all of me but my make-up was nice and sexy, more importantly I was making the right impression on her. Throughout all of this the thought that this was turning her on hadn't crossed my mind at all, now I realised that she was horny, very horny. We kissed, gently at first then tongues, being careful not to mess my lipstick up. I wanted to savour this, this was my ultimate dream come true.
She ran a hand up my stockinged leg, under my skirt and slip and stroked my thigh, he fingers finding their way under the suspender straps and caressing my legs just inside my stockings, then in turn she caressed "my breasts", I thought I was going to cum and didn't want to. I did what I could to slow things down but soon realised I was wasting my time. She stood up to take her jeans off, then her panties, never taking her eyes off me. "Just stay still", she said as she climbed back onto the bed, my cock was out and proud as she straddled me, I reached under her sweat shirt and cupped her (36B) breasts as she eased my cock past her lips and deep into her pussy. We moved down the bed a little so I was lying flat, "Open your legs", she said as she lay on top of me, as i did so she closed hers so we were in the missionary position with her on top and my cock was still deep inside her! I'm sure I heard her say something like, "Just enjoy this like a good girl", as she started pumping me. I wrapped my stocking clad legs around her, caressing her and pulled her down on to my clit and let her feel my nails on her back. I could feel myself getting close when at the same time she arched her back and panted her way into her orgasm. I, full of emotion released my cum deep into her, "Fuck me, please fuck me", I begged and we both came long and deep, I released a gutteral groan as she settled deep on to my cock with her soaking pussy leaking cum (hers and mine) onto my crotchless knickers and balls, we kissed again and I whispered, "Thank you", as we held on tightly to each other.
As we parted we held each others hand and for the rest of the evening the subject of me getting undressed or changed didn't crop up, we just cuddled and caressed. What a night!