It's So Easy

By Joseph Hammond

Published on Mar 21, 2019

Transgender

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It's So Easy

You will of course guess what I am but let's say I don't care, I can live with myself and enjoy it too! However there is one episode that stands out in my early life and I'll tell you about it now...and maybe have a wank after - hopefully you will be joining me?

Well it was like this, as a young teen for some time I'd been fooling around with myself, lying in front of a mirror while fondling my prick, then I graduated to sex toys...that was real fun, twisting my body to watch as the object slid into me, then the feeling as I edged it up...and up...oh lovely! And I only had to close my eyes to imagine it was a boy's hard cock...hear him pant as he did it to me...which set me thinking...how would I look in something sort of - fetching...I had long slender legs and a trim body, perhaps some stockings? The next step required some thought - how to get hold of some stockings, too risky trying to search my Mums or sister's stuff...

In the end the solution was simple, I made an easy purchase of a pair of sexy looking items by taking them to the automated checkout of a larger store and once home hurried to my room. Not waiting to undress completely I stepped out of my pants then carefully examined what I'd got, obviously they would need to be put on with care so sitting on the edge of the bed I eased first one and then the other up each leg. Wow! Naked from the waist down I revolved before the mirror, boy was I sexy but mind you I've always thought that a half naked boy - from the waist down that is - is far sexier than one totally naked, wouldn't you agree? I stood there admiring the view, enjoying the sight of the erection jutting between my milky thighs and elegantly stockinged legs so of course I began to wank. Then there was the sound of our front door and mum's urgent voice...panic...there was a family meeting over at uncle Spiros place...exciting news involving us and the solicitor had made a house call. I dithered, no time to shed the stockings without damaging them, I thought so simply putting on my shoes and trousers I raced down to mum.

At uncle Spiro's I could sense their impatience to be started, in addition to assembled family there was the solicitor, a dapper, nattily dressed youngish man who noting our arrival he began his announcement. The essence of it was there'd been a death in the family with uncle Spiro being the principal beneficiary but there being residual assets flowing to mum and myself. Good news and worth the recent panic, I thought. Suddenly I became aware of the solicitor's gaze, it was fixed upon my ankle and my heart sank.....I hadn't bothered to remove those nylons I'd been trying on and just my luck, they were visible where normally my socks should have been. I froze and avoided eye contact while tucking my feet under the chair. A short time later the meeting broke up and I noticed my mum and the solicitor having a chat, occasionally mum would glance my way and I became uneasy - had he told her what I was wearing? Then, breaking off, mum came over to me "Dear, Mr. Lovejoy here says he'd like to show you around his office...I had told him about your school project and he thinks he can help out, says he'll drop you off back home after - what do you think?". I was confused, however it seemed best to go along with the suggestion so putting a bold face on it, I agreed.

The trip to Mr. Lovejoy's office was a brief one during which he casually asked me a few questions before pulling into a parking bay beneath a commercial block, then leaving the car I watched as he keyed open a door and beckoned me inside. "This is our after hours entrance, it's quicker than using the front door and also more private" He smiled gently as he said that and with a hand on my back ushered me in. Following his lead we progressed through a couple of corridors to an open area, thickly carpeted and lined with plush looking couches "This is our waiting room, clients can relax here which is why we made it as comfy as possible" He paused there and stood eyeing me before asking "How old did you say you were, 14 was it?" I nodded and he resumed "Well, you are a very attractive looking boy - hope you don't mind me saying that?" I blushed and stammered "No, no that's alright...." He had drawn closer meanwhile and as my breathing quickened, I had a funny lump in my throat. I felt hands at my waist and then, a rustling as my pants fell around my ankles. I was mortified, there I stood naked from the waist down save for those black lace stockings. I heard him catch his breath "Wow, what a lovely, lovely sight...." He just stood there and suddenly it hit me, he liked what he saw and then to add to my confusion, I found that I liked having him there admiring me and there it was, my prick stirred and began to rise.

The voice was soothing "There, let me just feel, you like this don't you?" His hand was stroking my prick, God he did it beautifully, much better than any of the boys I let do things with me so when he unzipped himself I simply reached in and did the same for him. Silence for a minute and then I glanced up at him, he smiled back at me knowingly and we stood like that just enjoying each other, for me it was extra exciting, I'd never played with a grown man's prick before and told him so. He expressed amazement "What, don't tell me - no one has tried to get off with you before??" I did however mention that there were other boys...that I did things with, or rather that did things to me and I noticed I had his full attention "What sort of things is it, that you do? I told him that we sort of fooled around just like we were then and that after a while and if I was in the mood and feeling sexy enough, I might let one, or even two of them, do other things. "What other things?" "Well, mostly I suck them a little, not enough to cum though and then..." Here I hesitated before continuing "If I'm really randy, I let them you know, come in.....yes, well, they can fuck me..."

As I finished I looked up at him sheepishly to see his reaction, it came swiftly "Will, will you, suck me for a bit, please....." Well of course he felt huge in my mouth and there was that same slightly salty taste....rather nice but then he suddenly withdrew and with a croaky voice announced "OK, let's see how we go...." next thing he'd picked me up and laid me on one of the couches, saying to wait there while he got something. On return I noticed a small jar in his hand, Vaseline. Seated on the couch beside me his fingers got busy removing the rest of my clothes, then he sat back, his hands roaming my body. Do you know about a boys nipples? Well, if someone knows what they are doing they can make you feel really sexy....that was the first time that I really wished I had a girl's tits, something he could really get his hands on as it was I never realized my prick could get so hard. Finally, after feeling me up to his satisfaction, Mr. Lovejoy took the top off the Vaseline and dipped in a finger, I knew what was to come and lifted my hips with my legs wide apart so when it arrived, his finger slid in to a welcome - and I was ready!

There's nothing like it, watching someone lubricate their prick knowing where it will be going and what it will be doing! I'd never had one that size in me before and I wasn't nervous, just excited. So when he got on the couch and knelt between my legs I was ready. Carefully he raised my legs to position my knees next to my chin "Ready then my lovely?" He asked, I nodded, gulping with excitement and reached for his prick to position it at my hole. He leaned forward and pressed against me, still with moth hands on my legs. I relaxed as I had learnt to do with the boys and then, wow, there was a stretching...it hurt....but...it was moving up, slowly, so slowly it moved up still hurting but then, past the difficult bit, God, he was up inside me. A pause for breath and then the lovemaking began...slow languid thrusts, he'd obviously found an attractive boy and fully intended to enjoy him, yes as he later confirmed, he wanted to take his time! One good thing about the position we were doing it in was that I was able to watch...it was so sexy being able to see his prick going in and out. Too soon though it seemed, his breathing became strangled grunts, he shuddered, moaned and then came. Silence for a while and then suddenly, he kissed me!

Much later, he drove me home, he'd had lots of fun that afternoon, so he told me and asked if I would be interested in....more of the same another time, like in a few days. I pretended to hesitate and mumbled "If you like, then". I was actually quite apprehensive as well as turned on at the thought of being fucked by a group of men. Well, that seemed to start things up again, he pulled over the car and we both got down to business wanking each other. "God, we are a right couple of queers" he said. I wasn't fussed whether I was or not but then I had a thought, well there was a way to find out - I had these thoughts about fucking mum and was pretty certain I could get her to agree. How would it be if he got to have her too - while I watched, of course? I came then and there at the thought.

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