So, where are we now in my sexual adventures? If you have been patient enough to read through from the start of my sexual awakenings, to the cross-dressing dominatrix, and latterly to the self-doubting guy who was pushed outside of his comfort zone; well done! But, I warn you, this is brutally honest territory I’m going over here! Nothing at all sexual, nothing to make an uncomfortable bulge in your underpants. I will be talking about my feelings and emotions, so for those of you looking to crack one out whilst perusing gay or shemale erotica; maybe best if you sit this one out!
I’d had a wonderful time with ‘Babs’, but what she had asked me to do never sat comfortably with me. I’d love to say I was honest and talked it through with her. The reality was, it lay in the background of our meetings for the next couple of weeks like a cancer, growing with a resentment from my side. We continued our meets like previously, but I was expecting another request. And when it arrived, I blew up! She arrived, as usual, one Saturday morning, made herself at home, and requested that we engage in what we had done a few weeks before. I knew this was a slippery slope to a regular and expected thing, so I decided to put my foot down; it would also turn out to be the last I saw of her, although she never gave any indication as we engaged in another session of debauchery!
I had a few more casual encounters over the years in ‘cottages’, but, as my British readers will confirm, they have started to disappear at an alarming rate. As I got older, my hairline receded and my waistline started to expand. As for dressing? ‘Babs’ should have really been a revelation for me, showing what years of wearing women’s clothing and application of make-up could do to make an ordinary man into a half presentable female. I remember applying some make-up, adorning some lingerie, feeling my manhood fill up with blood, and slipping on a floral dress and seeing Fatima Whitbread stare back at them in the mirror! I was never going to be petite and ladylike. I lost that semi in a few seconds looking at a man in a dress in the mirror! The veil had been lifted. What had the thrill of cross-dressing always been for me? It was purely sexual, something naughty that I shouldn’t be doing. I’d always loved the feel of the soft silk and nylon against my skin, but seeing it as poorly portrayed as it was against my manly body, killed off any sexual kick I hoped to get from the experience.
I purged my collection of lingerie, as I had done a few years previously. The difference this time, it felt final; not just a break in play! I wouldn’t wilt and start another collection! And so it was. I never thought about adorning myself in women’s clothing any more. For a few years, I led a totally sexless life. For those of you still to go through this experience, you will awake sometime in your early to mid thirties one morning, and your cock will neither be up nor down! Up to this point in time, your one eyed companion has always arisen a couple of hours before you, waiting for you to greet the day. The only time he hasn’t beaten you out of bed is due to illness or a terrible hangover (sometimes that doesn’t even stop his antics!). When you awake with a semi, sometime in your thirties, believe me, you are on a slippery slope!
I hit my late thirties and all of a sudden my cock raged back into life! I lustfully perused the internet for things other than Facebook, eBay, or i*****l downloads of music. Porn! And God knows, there is plenty of it floating around on the inter-web! Firstly, I looked at normal ‘straight’ porn. No problem. Cracked a few out. Purely coincidentally, I came across some ‘shemale’ porn; there was no going back! The first instance I found Ellery Sweet beating her Scottish beef, I was hooked! There was a new generation of well hung and gorgeous looking babes, who got off on getting others off who came across their sexy posts. What a wonderful world we live in..!
And so it has been. I seek no lover. A friend is always welcome. I admire the sexy transvestite and convincing cross-dresser who gets arousal either by the lingerie itself, or the effect it has on those who see it adorned so beautifully. I am now a 250lb ‘bear’. If I have a particular kink, it would be ‘daddy cock’. I could never turn down an older guy, especially after so many positive experiences in my twenties with those in their senior years in the ‘cottage’. At the time, I felt like I was doing them a favour; in the end, they were passing on their experience to a callow youth, who loved nothing more than to wrap his lips around their experienced members and draw a load from their aging balls!
I hope you have enjoyed my experiences half as much as I did. The book may not be shut yet, but if need be, we can write some more chapters…