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By (user no longer on site) OP
over a year ago
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This is the (true-ish) tale of the next step on my long journey to where I find myself today, please comment – feedback both good and bad is equally welcome.
Suzie let me keep the negligee and heels, which I took home and added to my collection. When alone at home I spent many a happy hour dressing up and mincing around, each session finishing with me pleasuring myself, and sometimes tasting the results. During this time I took the opportunity to buy myself a little black and white maids dress, all silky and frilly.
About a month later I found myself calling on Suzie again, standing at her front door with stockings and a basque under my outer clothes, new dress and heels in a bag I was holding. The door opened and I was invited in. Suzie was dressed differently this time, a leather mini skirt and tight leopard print top. Still the same red hair, but slightly more extravagant make up – sparkly dark lined eyes and deep red glossy lips. My heart skipped a beat when I saw her, she looked delicious.
We sat again on her sofa and talked, but my attention was distracted to the porn videp playing on Suzie’s TV. The film was showing a young guy being feminised by an older TGirl. Make up was being applied and then the guy was dressed in undies, and a wig put on his head, transforming “him” into “her”. The newly transformed girl was then made to suck her mistress before being roughly fucked. I found myself highly aroused by the scenes. Suzie asked me if I had liked what I had seen, and I confirmed that I had indeed.
I was told to strip to my girly undies, and I duly obeyed under Suzie’s watchful eye. Once down to my basque and stockings I was taken by the hand and led to Suzie’s room where she made me sit at a her dressing table. “You look so lovely in your lovely lingerie,” Suzie said “I feel we need to enhance the effect don’t you?” I didn’t know what she meant initially, but soon realised when she started to fuss about applying foundation and powder to my face. “I cant wait to see how pretty you are going to look” she purred as she busied herself with her make up brushes and sponges. She continued applying various colours to my eyes, cheeks and lips as I sat motionless, loving the attention. All the time she was telling me how much my current situation was like the opening scenes of the video we had just seen. Last of all she stuck a pair of false eyeleshes in place, took a step back and pronounced the job done. I tried to look at myself in the mirror, but Suzie told me not to, and I of course obeyed, feeling totally in awe of this gorgeous lady who was lavishing such attention on me.
It was then that Suzie asked me what I had brought in my bag, so I showed her my maid’s dress. “Oh how wonderful, another step along the road,” she said. I was told to put it on, and she helped me into the dress, fastening it for me and smoothing the lace trimmed skirt into place, brushing my swollen cock through the fabric as she did. I was then helped into the heels, and stood before Suzie as she looked me up and down. I could not help but notice the clearly visible lump which had appeared in the front of her leather skirt. “One last thing needed I think” said Suzie, opening her wardrobe door. She produced a wig, a blonde straight bob, and placed it firmly on my head, teasing the stray hairs into place. “Oh you really are my girly sissy slut now” she pronounced with the sexiest smile on her beautiful (if slightly over made-up!) face.
Suzie now allowed me to look in the full length mirror inside her wardrobe door. I was astounded, the peron looking back at me was totally unrecognisable. A pretty, if slightly slutty blonde maid stared coyly back at me. Butterflies fluttered in my stomach and I felt on the verge of tears. “I cant believe it,” I gasped “Thank you. Thank you so much” I managed to stutter. I was allowed to stand for several minutes admiring myself, stroking the soft material of my dress, running my hands over my stockings, posing and pouting at myself. I felt wonderful.
Suzie then picked up my bag and asked “Oh my goodness what is this?” as she held up my vibrator. I blushed and looked at the floor, saying nothing. “This looks like a sex toy, you naughty girl” Suzie continued. “Yes it is” I confirmed. “What do you use that for, as if I didn’t know” demanded Suzie, with mock sternness. I stuttered a little and said “I use it on myself when I dress up” Although feeling embarrassed, my cock was throbbing in my panties. “And how exactly do you use it?” I blushed and told her that I liked to push it in my bum when I was masturbating. “Show me” she demanded, passing me the toy.
With that I lay on my back her bed with my knees raised, turned the vibrator on, and started to play the tip over my pantie clad hard on. I closed my eyes and relished the feeling of the vibrations as they stimulated my shaft. I then ran it down over my balls before nestling the hard plastic tip between my cheeks, on the outside of my knickers. My other hand was now inside my pants slowly easing my foreskin back. I lay like this for a while running my fingers over the exposed tip of my penis. When I could wait no longer, I eased my panties down, leaving them draped around one ankle (for some reason I have always like to leave my panties in that position when I pleasure myself). I then lubed the vibrator and my eager hole before pushing the entire length inside me. I pushed the dildo in and out of my arse feeling the vibrations sending waves of sensation through me, letting out little gasps and whimpers. I felt another hand take a gentle but firm hold of my cock and opened my eyes to see Suzie slowly stroking my straining erection. “You horny little slut” she whispered as she used her spare hand to remove the vibrator from me. She then gave a wicked grin and told me that my little toy was all well and good, but she had something much better. With that she held up a flesh coloured, cock shaped dildo, about 2 to 3 inches longer and noticeably wider than mine.
I knew exactly what was going to happen next and must have looked a little anxious because Suzie leant forward, gave me a peck on my freshly painted lips and said gently “Trust me”. She then put the dildo in my mouth and made me suck it, all the while telling me how much she had enjoyed my slutty cock sucking mouth the last time I had visited. I was made to turn around and kneel on the bed in an all fours position, and the plastic cock was removed from my mouth. I then felt my cheeks parted and a coolness as more lube was applied to my rear end. And then, inevitably i felt something hard placed against my sensitive hole. This was followed by a strange stretching, burning sensation which second by second became more intense until it was almost unbearable. I was about to ask Suzie to stop when she told me to relax, breathe and push back as if I was trying to go to the toilet. I did as advised, and the feeling lessened. I then felt a feeling as if I had relaxed, and the pain stopped to be replace by a slight pressure inside and a tingling, excited sensation that felt as if it was coming from right inside the base of my cock. I could also feel movement, and a sliding sensation from the rim of my anus that told me the dildo was still entering.
As I became used to this new experience, and relaxed I found that the whole experience was intensely pleasurable both physically, and probably most intensely, emotionally. The feeling of submitting in the most intimate way possible was mind blowing and I recall feeling as if my cock was going to burst. Placing my hand around my rigid shaft I realised I had never felt it so hard. Suzie told me that I had now taken the whole thing, and congratulated me. It was such a thrill to know I had all of that larger, intimidating cock inside me. The strange tingling sensation had by now spread to the pit of my stomach and along the whole length of my cock. I was moaning and gasping and crying out with the sheer pleasure of it all.
Suzie made me turn kneel next to her bed and told me to hold the dildo in myself, which I did. I was stunned to find only about an inch of its 8 inch length protruding. Suzie sat on the edge of the bed, and positioned herself so that her own cock, which was by now sticking out from under her mini skirt, was inches in front of my face. “Suck it, slut” she commanded, and without further bidding I slid my red lips down the length of her tranny cock. Taking the base of the shaft in my fingers I wanked her furiously as my wet lips slid over its engorged head. My other hand kept the pressure on the dildo which was still filling me. I thrilled at the sight of the red lipstick smudges I was leaving and also at the glimpses of the hair from my blonde wig at the edges of my vision. “Yes, that’s it, my cock sucking maid, keep it up” was the encouragement I received as I lost myself in the joy of the moment. All too soon I felt a hand on the back of my head forcing me forward, as Suzie’s hips began to buck. Her cock swelled in my mouth and twitched as I felt the same warmth on my tongue and the same salty bitter taste as before. I was moaning at the sheer horniness of it, allowing both my arse and mouth to be filled, allowing my face to be fucked, and taking someone else’s cum in my mouth. I was moaning like a whore, and Suzie was telling me how filthy I was and what a slutty cock sucker I was. I swallowed greedily, looking into Suzie’s beautifully made-up eyes as I did so.
I released my grip on the dildo which slid out from between my cheeks with a plop and was then made to stand facing the mirror again. Once again I felt the thrill of looking at the mirror and being turned on by the person looking back, a thrill that has never gone away, even now. I stood, gazing at myself as Suzie stood behind me, reached in front and grabbed my still hard cock. I was made to watch the reflection, as she vigorously stroked me, whispering in my ear what a pretty thing I was, and recounting to me that I had just taken an 8 inch dildo and a mouth full of cum. This was all too much for me and my knees nearly gave way as I shot spurts of cum out in front of me. I swear the first nearly hit the mirror which was about 5 feet away such was the force of my ejaculation (although maybe my memory is exaggerating the reality!).
We collapsed on the bed, and spent some time cuddling, caressing and talking. My relative youth at the time allowed me another erection which I put to good use in Suzie’s expert mouth, coming a second time that night. Suzie, with her characteristic generosity allowed me to keep the wig. The memory of that night is still precious - the very first time I dressed fully, the first teetering steps (in heels one size too small!) on a journey, a long and wild journey that has been at times agony, at times ecstasy, but an adventure nonetheless |
