The Making of an Angel Pt. 01

This is part biography and part reminiscing. I've changed names to protect people's identities and skewed some of the locations to make it difficult for people to be identified.

All persons are over the age of 18 at the time of what happened. I wish I was still 18... I would have had my surgery much earlier!

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My name is Angel Lawrence and I'm a 48 year old shemale. I'm sat here writing this feeling pleasure radiating from my pouting, swollen boi-pussy as it gently rubs against my satin panties whilst another man's semen soaks into the gusset from my gaping anus. My breasts are sore from being tormented by my lovers and I've got a stomach full of lovely cum. I pause to run my hand down my sheer 5 denier John Lewis barely black stockings and admire my ankle chain. It says "slut" and my ruby red toenails look stunning under the gauze of the stockings.

This is my story...

I always enjoyed the look of hosiery on women's legs. I would steal my sisters' tights and loved the feeling on them in my hand. I would hold the gusset up to my nose and inhale the scent of their quim before sliding the tights on up my legs and masturbating while wearing them. I was very careful not to get caught and would steal pairs that were to be thrown out. I used to longingly look at the underwear section of the Grattan catalogue and feel dirty but also excited.

I started to date girls and watch porn. My favourite porn was where the girl would be wearing barely black stockings and heels. I loved the look of a completely smooth pussy but best of all was when the girl took cock in her arse. I always preferred the look of a cock being pushed into a slut's bum. It looked so tidy and neat. No labia or other disgusting hairy, worn out pieces of flesh! I always encouraged my girlfriend to wear stockings, heels and suspenders. Often she would leave them at my house. As soon as she had left I'd put them on and luxuriate in the feeling of sheer nylon on my legs and tight panties holding my cock in place. I have quite small feet and my girlfriend was the same shoe size. Once dressed in her lingerie I would practice walking in her shoes before putting on my favourite porn film "packing 2 pistols" where various slutty harlots took huge cocks into their gaping arseholes while wearing stockings and heels. I would rub myself through the panties and masturbate while wishing it was me being fucked by the studs in the film. I didn't consider myself gay and had never had anything up my bum. I was careful not to get any cum on my girlfriend's lingerie and always made sure I put it back as she'd left it until one fateful day...

My girlfriend had decided to surprise me! Unfortunately the surprise wasn't quite what she was planning. I'd since decided to up my game and see what it felt like to have a cock inside me. I had no idea about douching or where to get a dildo from plus I was terrified of anything that big. I'd settled for a household candle in a condom. I'd just finished dress up and was getting to my favourite part of the film where the peroxide harlot gets double penetrated. As I was working my wax boyfriend into my incredibly tight virgin arsehole the bedroom door opened and my girlfriend strode in.

"What. The. Fuck?????" She screamed at me. "Are those my clothes?? You disgusting faggot!"

Bizarrely, as well as being horrified I found the abuse incredibly arousing. What I didn't find arousing what the demands to take her (my) lingerie off and the threats to tell everyone as she slammed the door and left.

After this I decided that I'd be a good boy. No more of this dressing up! I knuckled down and tried to straighten myself out. Time moved on. I moved out from my parents. Met someone else and got married. Then the internet arrived...

I developed a massive appetite for porn. Sluts, Milfs, Skanks. I loved them all until one fateful day. I was on my favourite porn site when I accidentally clicked on a banner with a beautiful amazonesque woman on it. The link opened. Holy hell! "She" had a cock! A big, beautiful fat cock. Hard and veiny with a perfect head on it. I found myself licking my lips and wondered what that cock would feel like in my mouth or even somewhere else...

I spent every available minute on the web looking at shemale porn. I found myself immersed in a world of hormones, tucking and douching. It was like opening Pandora's box. I hung around on the fringes and looked and learnt. The more I saw the more I remembered the delicious feeling of stockings on my legs. Suitably emboldened by these memories I paid a visit to our local sex shop in the nearest large city. I was visibly shaking as I went in through the door. There were posters and huge rubber cocks everywhere together with handcuffs and films. I suppose I was quite naive in that I'd never been in a sex shop before. More shocking was that a woman worked there! She was old enough to be my mother. Oh god! I felt myself start to go beet red.

"Can I help you?" She called.

"I'm looking to buy some lingerie" I stammered.

"Over there love" she replied.

I looked and was like a kid in a sweet shop. There were stockings and basques g-strings, crotchless knickers. You name it. It was there. I stood open mouthed feeling my cock harden in my jeans.

"What size?" a voice asked.

I jumped. The woman had come from behind the counter without me hearing her. She was close enough I could smell her perfume.

"Sorry?" I said.

"The lingerie. What size is your girlfriend?" She replied.

Shit. I hadn't thought about that.

"Um, ah, about my size..." I replied getting even more erect and even redder.

"Is it for your girlfriend or you?" She asked.

Oh my god! Here I was being outed by a woman old enough to be my mother. My hard-on was solid and the embarrassment was actually turning me on. I took a deep breath.

"It's for me" I said...

To be continued