That Moment

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A sissy begins her journey.
3.7k words
4.74
17.4k
36

Part 1 of the 3 part series

Updated 06/11/2023
Created 07/03/2022
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It's a bit of a cliché to say you remember it like it was yesterday. In this case it's also true.

I had gone swimming. An outdoor pool had opened near where I lived and I wanted to check it out. Running was my preferred exercise but, I wanted that cool water. A perfect blue sky overhead, boiling hot day, what could be better.

I'd done a couple of lengths of the pool when I stopped to catch my breath. Standing in the chest high water, I leaned back against the side of the pool and looked to my left.

For the first time in my life I looked at a man and without conscious thought three words flashed through my mind, 'He is gorgeous.' And he was.

He was sitting on the edge of the pool, in the corner, lying back on his elbows face to the sky. He was handsome enough but, it was his body that caused my heart to race, my mouth to literally water. Broad shoulders, well defined muscular arms and chest muscles. He had that 'V' shape. His stomach muscles stood out proudly as my eyes traced them down to the bulge in the black cycling shorts he wore. He didn't miss leg day in the gym either, his thighs were huge and sexy as hell. I couldn't take my eyes of him.

I had never considered that a man could be attractive before, not once in my life but, I was nineteen and hadn't much experience with girls yet either. Girls. Whose swaying hips, and jiggling breasts always caused me to look at them. I liked the way they looked, the clothes they wore, how they smelled. Merely looking at one had never caused my heart to race however, or my cock to go instantly hard. Like it was now.

I had to tear my eyes away from this guy before someone saw me drooling. My cheeks absolutely flaming, I slowly swam away, confusion reigning. When I got to the other end of the pool, I had to stand facing away from all that gorgeousness behind me until my heart stopped thundering and my cock went soft.

As soon as it did, I left. Shorts straight on over my wet trunks, everything else stuffed in my bag. I walked out without looking at him. Now, looking back, I wish I'd had sex with him. I'd have spent hours on my knees, his no doubt beautiful cock in my mouth as I worshipped all that lovely maleness. But, I wasn't capable of that then. I didn't have a clue what I really was.

When I got to my apartment I went right to my bedroom, ripped off all of my clothes and masturbated. I tried not to think about what it meant. The fact that I was picturing another man's body in my mind as I pleasured myself. Imagining myself running my soft hands over those gorgeous muscles. Down that firm chest, tracing his abs and then onto his cock. Which would be big and hard. That's as far as I got before I came.

I spent the next couple of days telling myself I wasn't gay. That it was a one off. These things happen. Yeah, right.

I decided to visit an adult store. It would, after all, have magazines with every kind of sex in them. I'd be able to look and whatever aroused me, well that would be that. It wasn't too far away and the parking lot in front was deserted when I pulled in. Taking a deep breath, I went for it. Out of the car and through the door before I could chicken out.

It was bigger than I thought. A counter in the far left behind which stood a bored looking guy in his mid twenties. Racks of magazines were everywhere, videos, DVD's, both still had a place here. Sex toys too. I wasn't prepared for that. Dildo's of all kind and sizes lined the walls along with lingerie and high heels. On the right was what I was looking for. A beaded curtain hung in a gap in the wall. Above it, in neon pink letters, the word 'GAY'.

Shit! Suddenly, I couldn't do it. I couldn't openly proclaim myself as a homosexual. Couldn't let this other guy see me that way. Even if he was, obviously, someone who must have seen lots of men walk through those beads. I pretended to browse the magazines. Looking at all the hot women, scantily clad, posing suggestively a thought sprung into my head. 'Aren't women lucky that they can openly display their bodies, wear sexy revealing clothes, sway their hips. Desire to be taken by men and not hide it if they want the right man to know it.' Yes, lucky indeed.

The guy's voice stopped my train of thought before I could take it to it's logical conclusion.

'Can I help you buddy?' Startled, I look at him and away, quickly. 'No, no, it's okay for now. Just looking.'

'Okay' he replied. 'But it's ten to one and we shut at one for an hour. So if you don't want to have to come back, you should make your choice.'

Biting my lower lip I managed a nod. My eyes flicked across to the curtain and it's neon sign. In doing so I gave myself away. The guy behind the counter's head dipped imperceptibly as if my traitorous eyes had only confirmed what he already knew. Pointing, he simply said, 'the gay porn is over there.' I think he knew the whole time. Like a special radar porn shop assistants must develop.

Cheeks burning like the sun, I gave in and walked to the beaded curtain and entered.

Magazines, of mostly men, were everywhere. And dildos, lots more dildos. Well, this will put my mind at rest, I thought. No more of the am I or aren't of the last two days. I'll either like what I see or not.

The muscle men having sex together? No.

Hairy men together? No.

Muscle men and slim, younger guys? MMM, no.

And on and on it went. Nothing.

Until, I saw the picture. He was wearing lacy top stockings and high heels. A pink basque and nothing else. His hair was long and blonde, his nails were pink to match his underwear as was his lipstick. A large powerful man had bent him over, legs spread so his little cock and balls could be seen limply dangling underneath his smooth buttocks. The man was in the process of inserting a huge nine inch, rock hard cock between those buttocks. The Sissy was looking back at the man adoringly.

I grabbed the magazine as my cock went hard and heart began to thud in my chest.

Opening it, I could see more sissy men and their lovers. On their knees sucking, on their backs, legs spread with a man's cock inside them. I was so engrossed I didn't even hear him come in.

'That's one o'clock, I've locked the door but, you can take your time, I'll let you out once you're through.'

'Thank you' I replied without looking. Did he see me looking at sissy porn? He must have, he knew what went were and I was right in front of that section. Sighing, I decided to get it over with. At least there was only that one guy here. Only he would know, apart from me. I grabbed three magazines and headed for the counter.

'So, three sissy mags' he stated as I lay them on the counter. I blushed again, managing a nod. He spread them out as he reached for a bag to place them in. He was smiling at me, brown eyes twinkling. 'Yes' I replied. He has pretty eyes, I thought. Shit, again. It was like I'd taken the cork out of something and now whatever was inside was running out. In this case it was any last thought that I might be strait.

'Anything else I can get you. We have some sexy lingerie, heels, make-up. All stuff your boyfriend will love to see you in.'

'I don't have a boyfriend' I answered quickly. How did he know I was the sissy? I could have been buying the mags because I was attracted to sissies? Porn shop worker radar again I supposed.

I did want some lingerie though. I couldn't deny it. I was momentarily pondering why lingerie had suddenly become so interesting when he replied.

'No boyfriend, eh' he mused. His eyes raking over me. 'Can't see that continuing for long.' He opened a drawer, pulling out a messy bundle of what I could only assume was ladies underwear. It lay in a big tangle between us on the counter as he continued. 'You can try these on for size, see which ones you prefer before you buy any.'

I don't think I've been as embarrassed so many times in one day. Cheeks on fire again I struggled to form a response. Who was this guy anyway to just assume I'd go along with his every suggestion. To, matter-of-factly, just talk to me like I was a sissy boy and that I would be okay with it.

But now he'd pushed the lingerie into my arms. 'The changing room is over there,' he pointed. 'What size shoe are you?'

'Eight' I mumbled, turning away. The changing room had a bar with three hooks hanging from it, a square, knee high red leather stool and the obligatory huge mirror. I sat on the stool to sort out the underwear, anticipation made me hurry. My fingers pulling and prizing the tangle apart in seconds. There was a lacy, silky body, full in the front but tapering to a thong at the back. As soon as I saw it, I knew I wanted to wear it. I stripped down, tossing my clothes into the corner. Pulling the silky lingerie up my legs, fixing the front so it held my little cock in as much as possible, settling the thong between my ass cheeks and pulling the straps over my slim shoulders was one of the most erotic feelings I'll ever have. I loved it. I turned this way and that in the mirror, trying to see myself from every angle. Before I knew it I was on tip toes with my back arched admiring how my backside looked. It felt amazing. Every movement caused the thong to rub against me, sending little thrills racing through my body.

When I saw the black lacy top stay up stockings lying on the floor, I knew they were next. Sitting, I crossed my legs. The sheer nylon smoothly caressing my legs made me wiggle a bit on the stool. It looked gorgeous, the lace against my thigh strangely satisfying. Uncrossing and re-crossing my legs, I was just pulling on the second one when the guy from the counter opened the curtain. I froze. My arms automatically covering as much of my body as I could. 'I thought you might like to try these' he said. He was holding out a pair of three inch, black glossy heels. 'Finish fixing your stockings first' he went on, looking at my legs. The whole while just standing there, heels in hand, eyes roving all over me.

I didn't want to move my arms away from my body. Didn't want this guy to see my little hard on bulging out of my silky lingerie. Leaning forward, I managed to pull the stocking up and rather primly fixed the lacy top of it in line with the other one.

I took the shoes with my right hand and placed them on the floor. Slipping my feet in, I knew right away they fit. I also knew I would love them once I stood up. I just didn't want to stand up and let my tormentor (That's kind how I was thinking at that point) see me.

He was nothing if not persistent. 'Well, lets see how them shoes fit you baby' rolled off his tongue as he grinned down at me. He'd just called me baby. I wasn't outraged, not even a little. I was still embarrassed to let him see me though. He could sense my hesitation, that was clear. Holding out his hand, his voice was soft. 'It won't be so bad once you stand up, get a good look at yourself in those heels. Don't worry about me, you're not the first sissy I've seen and for what it's worth I already think you look great in that lingerie. Don't think I'm judging you in a bad way, far from it.' He had me at that point. I wanted him to like me, in my outfit. I knew that, I could feel it. I wanted this man, whose name I didn't know to look at me and enjoy what he was seeing.

I took his hand, uncrossed my legs and stood. The heels did feel fabulous. I took a couple of steps in the cramped stall, turned looked at my rear end in the mirror and liked what I saw. Without realizing it my right hand had slipped onto my hip. I could feel my left wrist trembling as it struggled not to go completely limp. For a few seconds I forgot about the guy standing just behind me as I marveled in my sissyness. 'You look beautiful baby.' The words took me by surprise almost as much as my reaction to them. I turned to face him, able to look at him directly for the first time in a while. 'You like this,' I asked. My hips swaying as I turned full circle for him. 'I do baby' he replied. Being called baby was growing on me, a lot. He pointed at my stockings. 'Think you need to pull those up at the back though, they're not quite right'

He was correct, my stockings had slipped. I pulled them up, one at a time. Better but, not perfect. 'Let me help baby. Just stand and I'll fix them for you.' Before I could reply he was behind me. I could see his face over my shoulder as he slipped his hands up my right leg adjusting the stocking top as he went. He kept his eyes on mine as he moved to my left leg, his hands brushing by buttocks along the way. 'There you go honey. Perfect.' Without warning he pulled on my thong. A small gasp escaped my lips as the feeling burned through me. 'Just needed a little fixing' he whispered in my ear. 'How is that front doing.' His hands moved round me, pulling the front of my bodysuit. Long, strong fingers brushed my little, rock hard cock causing me to moan again. A little wet patch was developing there now. My eyes half closed as a big hand caressed my bum cheeks. His other hand was on my chest holding me to him as he kissed the side of my neck.

'You're so fucking sexy baby,' he breathed into my ear as his hand went between my bum cheeks, his thumb probing for my hole. I was completely gone now. Left wrist limp, my bum pressed against him while he played with me. I certainly felt sexy. I also had an almost irresistible urge to bend over. I couldn't help it. I started to go over as he played with my ass and balls. The feeling of his hands sending waves of pleasure through me. 'Not yet' he told me, pulling me back up. He turned me to face him, his hands on my waist. It felt like the most natural thing in the world to put my arms around his neck and kiss him. His tongue probed mine as our lips met and another moan of pure pleasure was dragged out of me. Big hands roamed my body, touching where they pleased.

'Crouch down baby' he said, his hands on my shoulders, easing my down. I went down willingly. The kissing and touching had pushed me over the edge. I wanted him so bad now. I crouched in my heels, my cock throbbing in my lingerie, my back arched so that my backside stuck out. The thong of the bodysuit was driving me wild, my hips were bucking a little as I looked up at him. He gazed down at me as his hands unbuckled his belt, pulling down his zip so I could see the bulge in his briefs. I didn't have to wait long to see his actual cock. He pulled his briefs down and there it was, my new object of desire. At least seven inches uncut, it was thick, veiny, with big round balls sitting high and tight to it. He pulled his foreskin back so I could see his shiny smooth head. My mouth literally watered.

'Open wide baby' he instructed, 'and stick your tongue out.' I obeyed instantly. My eyes locked on his as he placed the head of his cock on my tongue. 'Lick it,' he was smiling as he said it. It was a smile of triumph, of control. I didn't care. I licked my first cock, running my saliva around his beautifully smooth bell end. Within moments he had pushed it into my mouth. 'Hold still' he told me as he fucked my mouth. Slowly he pumped his hips, the first three inches of his cock sliding between my, now very eager, lips. It tasted salty but, not horribly so and after a minute or two I decided I liked it. My lover was moaning occasionally as he fucked my mouth but, it didn't stop him from talking. Or more accurately, from calling me a 'cocksucker', a 'sissy faggot' or a 'sexy little sissy bitch.' I loved it.

He pulled his cock from my mouth and presented his balls to me. I knew what to do and didn't hesitate to start sucking on them, trying to get his big balls in my mouth. I could really get the manly musky smell of him now and it was driving me crazy. I went to work on his cock, Sucking the end of it with my wet lips while I played with his balls. He loved that. 'That's it baby suck my dick' he kept repeating, his hand now on the back of my head. I thought for a moment that he was going to come in my mouth and although I liked the taste of his pre-cum I wasn't sure if I was ready for that. I needn't have worried.

'Up you get honey' he commanded me while pulling on my arms. He spun me round. Put your foot on the stool I was told and I complied, my left foot resting on the red leather a second after he said it. He pulled the thong aside, kissing and biting the back of my neck. I could feel his urgency. He slipped a hand between my cheeks and I moaned out loud. It felt so good to have him touch me. My back arched instinctively as I presented my bum to him. He was lubing me up, strong fingers working a large load of lube into my hole. It was driving me crazy.

'Pull you ass cheeks apart' he said.

I reached around myself and pulled them apart, as instructed.

'You want my cock in your ass, baby?'

'Yes honey' I replied, realizing even in my excited state, how girly and weak I sounded.

'Are you my faggot?' was accompanied by a spank to my right buttock. God he was driving me mad.

'Yes' I replied, louder.

'Yes what?'

'Yes honey, I am your sissy faggot and I want your cock in me. I want you to fuck me.' My voice was getting louder, higher, my bum was grinding into him as much as I could get it to.

He pressed the tip of his cock against my hole. Rubbing it up and down and then slowly, he inserted his manhood into me. It did hurt but, not enough for me to want him to stop and he did it slow enough that I did no more than utter a little girly cry of surprise. He was in me now. He made me reach down and cup his balls as he very gently pumped his cock in and out of me in short movements. 'That's my balls against your hole faggot,' he informed me once or twice as he incrementally increased the pace. 'Didn't want to hurt this fine ass of your baby but, now I think you're ready.' And so saying he began to slide the full length of his cock in and out of me. I was ready for it, wanted it, loved the feel of his cock stretching me while his balls banged against me. He spanked me again, several times, and I though I was going to lose my mind. I think I had been making little squeals and 'oh fucks' or 'oh god, oh god' for a few minutes before I realized I was doing it.

His big right hand reached round me and began to rub my little cock. 'Oh fuck' I all but screamed. He kept doing it, bring me close to climax. 'Fuck me' I was shouting now, my bum going backwards to meet his cock. he increased the pace and force of his thrusting while his hand kept rubbing me. With a long high pitched moan, I came, my little dick still inside my lovely bodysuit.

'That's it sissy boy' he said as I began to bend over. I couldn't stay even half upright now. 'I had both knees on the stool, my ass in the air while he hammered his cock into it. My mind was dazed. I just kept repeating, 'I'm a faggot, I'm being fucked' to myself as if I was only now just realizing. The picture of the sissy in the magazine came into my mind. His little limp cock hanging down while a real, manly man, fucked him in the ass with a big hard cock. I must look like that now. I smiled.

My new lover humped me for another minute or two before he came. Grunting and thrusting like a wild animal at my ass while his balls emptied into me. He leaned over me, breathing heavily, his cock still in me. I waited patiently, submissively, for what came next. He was in charge, after all.

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5 Comments
DinatagailDinatagailover 1 year ago

That story made my little dicklette bust a load. Kisses baby.

OttoDidactusOttoDidactusalmost 2 years ago

It never fails to amaze me, at my advanced stage of life, that these lovely stories of first initiation make me long for having learned earlier lessons and experienced earlier joys the way you described. I can only wish you all the delights of the discoveries you made and will continue to make.

AnonymousAnonymousalmost 2 years ago

I wish i was him and used like that. very hot. jessica carlisle

Dani_does_DallasDani_does_Dallasalmost 2 years ago

This is a great first story, really well done, I hope you continue

EmmaCDnzEmmaCDnzalmost 2 years ago

Love this story and the beginnings... I cant wait to see where this develops

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