That Moment Ch. 02

....I remained on all fours. The man behind me, his semi-erect cock still in me, moaned one more time, a low growl of masculine satisfaction. 'Fuck', he exclaimed, grinding himself against my buttocks, his strong hands on my waist. I stayed still, waiting to see where he would go next. I didn't wait for long. His hands ran up my body, reaching my slim shoulders as he climbed right on top of me. Kissing my neck, my ear, he breathed his satisfaction over me and then his wet tongue went in to my ear as his right hand reached under me and cupped my little cock and balls. I whimpered, a little moan of acceptance, of pure pleasure. Grasping my chin, he turned my head to face him. I was taking all of his weight now, on all fours with his cock still stretching my hole. Now I was staring into the eyes of the first man to fuck me. His pretty eyes. I shifted position a little, involuntarily moving my ass from side to side. A big grin lit up his face.

'You enjoy that baby?

'Yes' I replied, smiling back. 'It was lovely'. His smile widened.

'Thought you would, minute I laid eyes on you, Didn't know you'd be a sissy but, I knew you'd like my cock.' And then he kissed me. Long and deep our tongue's slowly entwined. A little bit of me wanted to ask him how he knew so easily when I hadn't even been sure myself but, I was enjoying being kissed by this man so much I didn't want to break it off. Besides, you never really know what another person sees when they look at you.

We kissed for a couple of minutes more and then he stopped. 'Need to open the shop in a little while baby, we'll have to break this off.' I heard a small voice say 'Okay honey' and didn't question for a second just how girlish and feminine my own voice was in that moment. He slid back, withdrawing his cock from me. It was a strange feeling, a short quick pain, and there was this realization that a man was now staring down at someone he'd just fucked, ass still the air. That someone was me. How did he view me now. Was I his bitch, an anonymous faggot he'd used, a sissy slut just there for him to fuck, did he even think of me as a man. Did I even think of myself as a 'man' at that moment? Things to think about later.

Reaching behind myself I adjusted the thong of my bodysuit nicely between my bum cheeks before spinning round to sit, facing him. Crossing my legs I looked up at him as he pulled his tight boxer shorts up and settled his cock and balls in snugly. I didn't want to move, to get dressed or otherwise do anything that would spoil this, my first sexual encounter with a man.

He was watching me in return and that was the first time I became aware of how even just simple things like fixing my thong or crossing my legs made me feel so sexy, so feminine but, how they also affected the man watching me do them.

He made his appreciation obvious. 'If I had the time, I'd stick my dick back in your mouth and let you suck me off.'

I bit my bottom lip, like I was thinking about it. 'If we had the time, I'd let you.' This got me a laugh. 'You're quite relaxed, for a sissy whose just been fucked for the first time, not nervous at all are you?

I shook my head. 'I was nervous and very embarrassed, which I think you know'. He laughed again and pulled me up to stand in front of him. 'You suit the color in your cheeks baby. It was sexy as hell seeing you pretending you weren't a sissy. When I handed you the underwear, your face might have went red but your eyes lit up and you pushed your hip out. I don't even think you were aware you were doing it.'

'Look at you now' he continued. 'Standing in front of me in your stockings and heels and not even being conscious of it.' 'I know' I replied, my left wrist all flappy as I waved my hands about. 'What's the point of me being self-conscious now after the humping you just gave me. Some lingerie is the least of the things I could be embarrassed about. I mean, twenty minutes ago I had your balls in my mouth, right?' I slid a hip out, my hand resting on it. My other wrist as limp as a girls, I was teasing him and he knew it.

He spun me round by the hand and slapped my rump. 'Keep the underwear on, just put your boy clothes over the top. You can bring it back tomorrow..' His lips were right by my ear as he said it, his eyes holding mine in the mirror. 'I'll be sure to' I replied, hips wiggling. He laughed as he walked away and I quickly got dressed. Pulling my jeans on over my stockings was fine but, the feeling of just having the thong of my bodysuit between my cheeks was simply divine. I spent a moment or two pulling my jeans tighter to see what my bum looked like. (How good would a satin or silk skirt feel?)

I positively swayed as I walked out to the front counter of the shop. My new lover watched me come. A thoughtful look on his face. 'I have your magazines ready to go baby, you want anything else before you go?'

You bet I did. 'Those two dildo's' I said, pointing. 'That big bottle of lube, that maid outfit, those stockings, those panties in all the different colors, that brunette wig..'

On I went. We filled four bags before I finished and then I realized I didn't even know his name. I was a bit hesitant, the shyness creeping in a little. It was also making me feel girly, I don't know why. I mean, we'd just had sex, during which he made me feel plenty girly and now just asking him his name was giving me issues. So I just blurted it out. 'What's your name?' This got me another smile. I was beginning to like his smile. 'Rob' he said without hesitation. Rob, I thought playing it over in my mind. It suits him I decided. I don't know why but his dark hair, pretty brown eyes and easy smile had me thinking Rob suited him. It's unexplainable, maybe a guy can only start thinking like that once another man has fucked him senseless.

'Well Rob I'm...' I began. 'No no', he interrupted. 'Don't tell me your boy name, I don't want to know it.' He stepped round the counter, slipped his arms round my waist and pulled me in tight. My own arms went round his neck and we kissed. I pressed myself into him like I was trying to merge into his body. His kissing was so hot and the matter of fact way he just took charge of me, even hotter. He broke off and I just stared up into those lovely eyes. 'Come back tomorrow and tell me your girl name. Yeah, same time.'

' I don't have a girl name ' I protested.

'You will by tomorrow' he replied, murmuring in my ear. 'Get yourself all dolled up tonight, get a little make up on, some perfume. Slide one of those dildo's you bought up your sexy ass and ride it. By the time you come, you'll know what to call yourself.' His right hand had crept round to my bum and he was giving me a good squeeze as he said all this. I though I was going to faint, I was so turned on. 'Oh god, ohh okay' I stammered. A quick peck on my cheek and a little slap on my bum and he said, 'you'll have to go baby, need to open the shop.' 'Yes dear' I replied. Picking up my bags, I positively wiggled my way out of that shop and all the way to the car. Rob watched me go, his eyes locked onto my ass so hard I could feel them.

I had to compose myself before I could drive. I just sat there for a couple of minutes with the words 'I'm gay, I'm gay, I'm gay' running through my head and worse 'I'm a sissy, a girly sissy who has just acted like a girl with a man. I let him fuck me. I sucked his cock.' I had gone there to but some magazines, to help me sort through my feelings after my reaction to the guy at the pool. I had wanted to end the indecision. Well I had certainly done that. And I had loved it. Rob was sexy in his own right and as far as I could tell, a pretty experienced lover. I knew that the more time I spent with him the less awkward I would become and being girly in response to him would become more natural. I wanted it. I pictured myself sitting cross legged, in a skirt, next to Rob. On a couch, making out. Feeling those lovely lips on mine, those man hands possessing me, touching me, controlling me. I damn well nearly crashed the car.

In control of myself again, I started to think about my purchases and how nice it was going to be trying on the clothes I'd bought. It wasn't enough. I let the turn to my apartment go by and continued on to the local mall. This wasn't going to be easy. I still had my lingerie on and hadn't even though about whether it could be seen under my -shirt. I wanted to buy make-up, perfume, maybe a purse and I definitely wanted some hair removal products. I checked myself over in the car. It didn't look like my underwear could be seen, I'd just have to go with it. I was very self-conscious of my thong as I walked. It was an amazing feeling but, it made me want to wiggle my bum a little as I walked and I wasn't ready for people to see that.

A little traitorous voice in my head pointed out I'd been happy to wiggle for Rob and I thought, well yes, that was true and I'd be happy to move my bum in any direction he wanted but I didn't want the whole mall seeing me wiggle, not yet.

In the end it was less stressful than I thought. I kind of took the easy way out and told the girls behind the counter I had a sister turning sixteen and I wanted to get her some girly presents. They were more than happy to help. I don't think they all believed me and one or two did seem to be sizing me up when we picked the lipstick colors and the fashionable black purse but, I 'manfully' saw it through and returned to my apartment with my make-up, jewelry, and everything else I'd decided I'd need to enhance my girliness.

I could barely contain my excitement as I opened up all my new girly attire. Just holding one of the slutty party girl dresses next to myself, running my hands over it's silky smooth material gave me a hard on. I couldn't wait to try it on. Same with the matching bustier and panty set, black with glittery blue sparkly bits all over it. First things first though. Bath time. Time to lose the hair. I'm not a very hairy person, particularly my face which didn't require shaving very often but, I wanted to lose the lot. It took me a while but I got there and what a feeling those smooth legs gave me as I rubbed them together, so sexy.

I couldn't wait to get my panties and bustier on and dried myself in record time. Bustier on first, standing naked in front of the mirror. It had a little zip at the back but, I got the hang of it quickly enough. I thought it looked great and I spun round and round in it, seeing myself from every angle. Then the panties, another first. My wrists were trembling as they went up my smooth legs. I tucked my little cock away and adjusted the nearly full panty at the back. Now I really was turned on. I slipped into my heels and just couldn't stop looking at my own backside. I started dancing, my hips and ass swaying from side to side while looking over my shoulder in the mirror. Rob will love these, I thought. At once, I had the urge to bend over and shake my ass. So I did. I imagined him standing there behind me, his big cock hard and lubed up as he watched me sexy ass gyrate. Imagined him grabbing my hips, spanking me. Pulling my panties aside...

I couldn't wait any longer. I tore open the packaging from one of the dildo's. A lifelike vein covered eight inches and stuck it straight into my mouth. My ass gyrating, my lips going up and down on that dildo like my life depended on it, my sissy cock leaking. This is amazing, I thought, wishing the dildo was a real cock attached to a man. I was getting more and more excited and knew I'd have to ride the dildo, just like Rob told me to before I would be able to settle down. One thing I had to do first though. Lipstick. Bright pink first I decided, a real girly color. Applying it was easy and by the time I'd put some lip gloss on over the top I was in love, with lipstick. I pouted into the mirror, loving how sissy I looked and felt. I wondered what it would be like to kiss Rob with this on, what it would be like to giver him a blow job.

Whipping of my panties, I got on the bed. On all fours with my bum facing the mirror, a huge load of lube in my hand. Rubbing it onto my still achy hole was enough to have my cock leaking and I moaned like a girl as I pushed a finger in. The dildo was big and I wanted it to go easy. Just like the way Rob had taken me earlier. I got two fingers in, lube dripping everywhere and the achy feeling in my hole was fading fast in the face of my rising horniness. Rubbing the last of the lube onto the dildo's shaft, I positioned it under my hole. I was really horny now.

The head of the dildo was big and by the time it was half way in me I was gasping with the pain. I wanted it in me though, all of it, and I kept on easing it in a little bit at a time. I was moaning like a bitch I realized, as it finally slid all the way in. (I came to realize, that like all horny bitches, I would go that extra mile to get a cock in me).

I sat there for a bit, panting. The dildo right up my hole. Only the fake balls sticking out. Glancing back at the mirror, I grabbed those fake balls and raised myself up a little. Oh, yes!. It still hurt a tiny bit but, oh my god! I got into a rhythm, sliding up and down that glorious rubber shaft. Oh, fucking yes. I kept my eyes on my ass, watching that dildo slide in and out of me. Oh yes, Oh yes, Oh God, Oh fuck! I was loving it. My ecstatic cries degenerated into little girly moans and yelps. I began to imagine Rob was fucking me, pounding his cock into me, his big balls slapping my sissy ass. I came. I gave a high pitched squeal and my semen sprayed all over my bed.

I rode the dildo for a few more seconds until all I could do was fall forward onto my elbows. Face down, ass in the air, dildo buried balls deep in me. Much as I'd been earlier in the day when a real man had taken me for the first time. As I lay there, chest heaving, hips quivering, I did ponder the questions I had asked myself that afternoon. What am I now? Can I still call myself a man. Do I feel like a man? An image from earlier in the day entered my mind. Rob spanking me, calling me a faggot, a sissy, a bitch. How I'd loved that. He was right, I thought. I am a sissy faggot, not a man, not really. I'm a gay, girly, cock sucking sissy. Not a girl, but girly.

I needed a girly name now, to define my inferior status in the eyes of Rob and the other guys. That's how I'd think of them now. Guys. They were and I wasn't. They were real men and as I was finding out, I wasn't. I didn't care.

I pictured a girl I once knew, in school. She wore her sexuality openly. Short skirts, tight tops, nails done, lips permanently glossy. She'd fucked her way through high school without a care in the world. Lisa, her name was Lisa and now, so was mine.