This is not a raunchy story. I just wanted to share my journey to crossdressing and, once shared, it may encourage me to share some other stories relating to my obsession with nylons.
I’ve always been into nylons and high heeled shoes or knee high boots since I was a child. Never having a sister meant I only got access to tights and stockings once I started dating girls in my teens. I’d always loved the look of nylons on women as they could really make an outfit look good, so when my girlfriends wore them I thought I’d hit the jackpot and couldn’t keep my hands off their legs and bottoms. As time went on, I used to slip on their used tights when they weren’t around and stroke my straining cock through the material. Sometimes, I would lose control and cum in them which was such a sexy feeling.
My wife also wore tights from time to time, so I used to try hers on too along with her knickers. If I was doing laundry whilst she was at work, I used to wear her used black opaque tights for a few hours before rubbing my cock and feeling my cum ooze over them. Then I’d wash them and she was none the wiser. Nowadays she also has a few pairs of knee high boots, so I would team those with the black opaque tights and have an even hornier and sexy wank.
It was another girlfriend (let’s call her ‘M’), however, that had first got me hooked on the combination of tights with high heels or knee high boots. We worked together and is a beautiful, sexy blonde, size 10-12, with size 34B breasts (perfect) and gorgeous legs, made even sexier when clad in nylon. For a while M often wore tights with heels and short skirts or short figure hugging dresses. One day, however, M turned up to work in a pink, ribbed tight-fitting jumper, tight-fitting short black skirt, black opaque tights and the sexiest knee high leather boots. I was smitten and couldn’t keep my eyes off her all day. At lunchtime that day, we went out in my car and I couldn’t resist stroking her legs, even letting my hand slip under her skirt. Eventually, I told her how obsessed I was with the outfit and she took it well, as she went on to buy several other pairs of black knee high boots and would wear them most of the time I saw her, especially when we had to travel for work. Stories of what happened with her, especially when she wore boots and tights, will be saved for other stories.
Anyway, M had really aroused my interest in tights and boots and in addition to trying her tights on, I also took a couple of pairs. I still have a pair of her black opaque tights to this day. As I’ve got older, I’ve craved the feel and look of them and decided a few years ago that I should start my own collection rather than rely on stolen moments with my wife’s lingerie and hosiery. Gradually, I have built up a decent collection, starting with black opaque tights, then moving on to black opaque stockings, followed by some lingerie from ASOS and M&S, then being brave and buying shoes with a 4” heel, two pairs of knee high boots and, more recently, a pair of over-the-knee boots and some different coloured opaque tights. I’ve also added several faux leather short skirts to my collection, along with tight dresses and some tops. I’ve even bought some wet-look underwear from Love Honey. It is all thanks to ‘M’ for reawakening my earlier liking for tights and boots, by wearing them herself. It is surely down to the fact she encouraged by love of them by wearing them regularly when we were together, that I always associate my nylons indulgence with her.
And as a result of dressing in them regularly, it made me realise how I’d like to ‘play’ dressed in nylons and heels or boots, which made me bi-curious, eventually realising I’m actually bisexual. So, it’s thanks to my dear former girlfriend ‘M’ that I am on my current journey having fun dressed in the same way I used to enjoy her. Thank you ‘M’ and to all of you who have read this far, thank you for reading.
