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By (user no longer on site) OP
over a year ago
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So people, here is the first instalment in the memoirs of my journey from innocent, naive 20 year old to where I am today, a 40 something bisexual transvestite. I hope you enjoy, please comment/criticise as you see fit. xxx
It all started when I was in my early 20s (some time in the 80’s – I will be no more specific than that!). I had found through my enjoyment of porn that I had a liking for shiny, kinky fetish clothing, high heels, gloves heavy make-up and that sort of thing. At that point my attraction was purely towards women, I had no desire whatsoever for cock, whether in a frock or not. Or so I thought.
I remember that I was looking to buy a car, and so I picked up a copy of a local Free Ad type paper and began to peruse the motor section. As I was doing so I noticed there was a Lonely Hearts section towards the back of the paper, and behind that I saw a Contacts section. I had never come across this sort of thing before, and found the content of the ads highly exciting. Here were people clearly looking for sex, and advertising their intentions in a local paper!
I found I was drawn to one ad in particular, it referred to High Heels, PVC clothing and “No Strings” fun. There was a name in the ad; Deborah. I was dumfounded – a woman in my home town who love wearing the things that excited me, and was clearly up for it! What I had failed to realise was the significance of the two capital letters – “TV” that also appeared in the ad!
I duly wrote to the box number in the ad enclosing my postal order for the Contact service fee, and waited. Just over a week later a reply arrived. Sure enough it was from Deborah, and yes she loved dressing up in kinky gear, was keen on slutty makeup, loved sucking cock, enjoyed getting fucked, and would love to meet – she even gave her phone number and invited me to call. My cock was hard as nails as I read the letter, right up to the last part. This was when she said something like “You should realise that I am a transvestite”. Suddenly I realised what “TV” stood for, and I found my excitement begin to diminish.
There was a photo enclosed with the letter, and as I looked at it I was amazed. Far from the pantomime dame I had visualised when I read the word “transvestite”, I was looking at a slim, leggy, blonde, pvc clad vision. She was looking away from the camera, so face could not be seen, but I was impressed by what could be seen. I was shocked and worried my by reaction to the picture - in my poor inexperienced mind, transvestite meant “bloke” and there was no way I would ever want any fun with a cock, no way at all! So the photo went back in the envelope which was put away with the full intention of throwing it out some time soon (or so I thought).
That evening I had another look at the photo, just to satisfy my curiosity of course. The fact that the photo showed the shiny high heeled boots that I had often fantasised about had nothing to do with it, nothing at all ... and the lovely slinky pvc skirt catching the light in such a sexy was didn’t appeal at all. It was a pure coincidence that I could feel a stirring in my pants as I looked at the shiny corset and long gloves, surely. It must be because I knew that the lovely, sexy, kinky clothing was being worn by a man, and I knew I wasn’t gay. There was no way I would be contacting that weirdo.
So, two days later having wanked myself silly over the photo time and time again, I found myself on the phone to Deborah. I was incredibly nervous, yet excited at the same time. It was wierd hearing the strange voice on the other end of the phone, which although soft and effeminate was still evidently a male voice. We chatted about my likes for fetish imagery, and I stumblingly admitted I had no experience at all with TVs and in all honesty didn’t know why I was calling. I must have sounded like a fool, as I got all tongue tied and making an excuse rang off. After putting the phone down, I knew that there was no way I could ever meet Deborah, not ever. I knew I had to throw the photo away, absolutely had to. Well maybe one last look, and there I was wanking again. Without thinking I was back on the phone to Deborah once more. I remember she laughed and said something like “I knew you would be back, I just hadn’t expected it so quick!” I told her that I was stroking my cock whilst looking at her pic, and I wanted to meet. We agreed I would go to hers the next evening, and I hastily scribbled down the directions she gave me to her flat.
The next day felt like it lasted an age, I told myself numerous times that I wouldn’t go through with the meeting. In fact I was still telling myself that as I tentatively pressed her doorbell. Then, suddenly it was all very real, the door opened but whoever had opened it made sure they remained hidden behind so that they couldn’t be seen from outside. “Come in darling” said the voice I had spoken to on the phone the day before. Almost in a trance I stepped inside, heart pounding, palms sweating and legs trembling. The door closed, and there in front of me was the kinkiest sight I had ever beheld!
Deborah towered above me (or so it seemed) and I gazed awe struck at her. Long wavy blonde hair framed a face that was immaculately, if heavily made up. Blue eyes framed by shimmering silver and blue eye shadow, dark eye liner and long black lashes looked me up and down as deep red glossy lips smiled at me. My own eyes took in the shiny red pvc corset, long black gloves and black pcv mini skirt. As my gaze continued down I saw fishnet clad legs and patent stiletto knee boots. I remember I could hear my heart pounding, and couldn’t seem to speak. “You poor boy, you look terrified” Deborah said to me. She then winked, took me by the hand and led me to the sitting room.
We sat on a sofa, and I recall we made small talk, but for the life of me I can’t remember what was said. I do remember staring at Deborah with a confused feeling inside. I knew I was looking at a man, but I also knew that I was so fantastically aroused. The shiny fetish wear, the beautiful make up, it was all so surreal to me.
Deborah then asked me what I thought of her outfit. Of course she knew the effect it was having, and as I stuttered something about how nice it looked, she leant forward and placed her hand on my thigh. I must have jumped because she chuckled, just like she had done on the phone and told me that I should relax, she would take her hand off if I wanted. Clearly, I didn’t want her to and told her so, and with that I felt her gloved hand stroking my thigh through my chinos (which shows how long ago this all happened!), and it felt heavenly. Her hand drifted up so her fingers were tracing the length on my now straining cock. My lack of resistance was all the sign she needed, before I knew it I was helping her undo my belt, and the trousers were on the floor. Tucking her thumbs into the waist band of my pants she pulled them down, so that they joined the trousers around my ankles. Without a word, Deborah knelt in front of me and placed her lips on the end of my throbbing erection. I looked down at her to see her gazing back at me her mouth resting on my cock, lips slightly parted and the tip of her tongue tickling its tip. I didn’t, couldn’t say a word. She lifted her mouth away from me and said just one word - “Yes?” I continued staring and managed to reply with one word, ”Yes!” With that her wonderful glossy red lips sunk down the full length of my shaft, until I felt myself nudge the back of her throat. I then felt her mouth slowly retrace its path back to the end of my cock, before sliding back down again.
I sat lost in ecstasy as Deborah’s head bobbed up and down, sending waves of pleasure through me, her lips leaving smears along the shaft of my cock. I felt her smooth pvc gloved hands stroking my inner thighs and remember hearing myself moan uncontrollably at the sheer erotic tension. I placed my hands on her shoulders and began to involuntarily rock my hips, pushing my hard cock back and forth, fucking Deborah’s mouth. She gave quiet little moans, which served as an encouragement to me so I continued, loving the feeling of her soft wet mouth pleasuring me. One of her hands was now stroking the underside of my balls, and I felt the unmistakeable twinges that told me I was about to come. I told her I was close, and with that her other hand grabbed my cock and began wanking, as her mouth clamped around my bell end. I warned her again that I was going to come, but her mouth stayed exactly where it was. With a gasp I ejaculated, which caused Deborah to stroke my cock even faster, as she sucked my cock hungrily. It felt to me as if my orgasm lasted forever, but inevitably it subsided, and I became too tender for Deborah to continue. She looked at me and smiled, then did what at that time to me was a very strange thing. She opened her mouth so I could see my spunk then she closed her mouth, winked at me and swallowed, giving a little moan. Having done so, she opened her mouth which was now empty.
She then sat next to me, asking if I had enjoyed myself and telling me how much she had enjoyed my cock. I was shocked to find myself swelling again. Seeing this, Deborah took my hand and gently guided it up her skirt, placing it on her own panty clad erection. It is to my eternal shame that at that moment I froze, suddenly feeling freaked out by what had just happened. I pulled my hand away, and pulling my pants and trousers back up made some excuse about the time. Deborah said something about first timers often getting post orgasmic guilt, and even helped me fasten my belt. Looking back, she was kind and patient, just letting me leave telling me not to worry and thanking me for the visit. Within minutes, I was outside the flat feeling a mixture of shame and wonder and I hurried back to my car. After arriving back home, I got rid of Deborah’s letter and photograph and swore I would never do anything like that again.
With hindsight I know my reaction was awful, I was so rude! Within six months I was once again enjoying sexy tranny fun, and my journey to where I am today was well under way (but that is a whole other story).
I never did see Deborah again, but I look back now with gratitude at my introduction to this weird and wonderful world I find myself in. If by any chance you read this and recognise yourself Deborah, thank you so very much xx |
