My New Pretty Sissy-boi James

I met James at a subway station downtown one hot summer evening going home from work.

'Can you spare change for a cup of coffee?' The lovely, petite youth standing with his back to the tiled wall begged.

I stopped and stared at him, he was beautiful, his slim hairless arms ended in nice soft hands. He wore tight black jeans that hugged his hips and showed off his thin legs.

Amongst that milling crowd, those eyes held me: those wide, innocent looking dark blue eyes with long eyelashes and pursed red lips.

'Hey you're staring at me mister!' He snapped.

'Can you spare any change, or are you just looking?'

I offered him five bucks for coffee and a phone card.

'Here,' I told him. 'How old are you' I asked eagerly, as he looked very young and beautiful to me.

'Nineteen' he answered. I breathed a sigh of pleasure.

'If you want to earn some good money, just phone me...'

I handed him a business card, with my home number on it, and then walked away, smiling and smacking my lips. I figured, rightfully as it turned out, that I'd hear from him.

Then, last night he phoned.

'What do I need to do to earn this money?' he asked anxiously.

'Just pose for some photographs for my private collection; however I want you to dress; in whatever position I ask of you. And I'll pay you one hundred dollars an hour.'

'Pardon?' He'd asked, in a quiet voice.

So, I repeated myself.

There was a long silence, in which he must have thought long and hard about my proposition.

'Okay,' he answered finally, 'I'll do that for you. I need the money.'

'A-ha,' I thought, 'good boy' and gave him an appointment.

And, he's due here, soon. I thought to myself excitedly. I had not felt this way about a boy in ages.

The front room is ready -- it's to be the ''studio', where he'll pose for me, in pictures I'm sure my friends will like.

After all, they share their private pictures with me; it'll be good to return the favor.

There's the doorbell now...

I walked down the short hall to the front door; already I was very excited at the prospect of seeing him again.

I had it in mind that he wouldn't show, as he sounded so hesitant on the phone.

But then, he'd said he needed the money.

'Who is it?' I called out.

'It's James, you met me at the subway station,' he answered.

I smiled as I opened the door: and he looked just as I recalled; slight of build, dark longish hair, with wide guileless eyes. Perfect boy I need for this.

'Come in,' I told him, standing aside, so he has to walk close by me -- very close, noting his unease, with pleasure.

He turned to me, as I closed the door.

'When do I get paid?' He asked.

'When you've earned it in an hour, my young friend,' I assured him in a serious tone of voice, slowly looking him up and down.

To judge by his slim build, he'd easily fit into the stuff I'd chosen for him to wear.

'Do you want a drink?' I asked.

'What have you got?' He responded, as he followed me through to the kitchen.

'Whiskey, vodka, wine: red or white?'

'Er... Vodka.'

'Sure,' I reply, 'with cola, or straight up?'

'Cola, please?'

'Sure, okay,' I answered him, then said, 'you go through to the sitting room. We'll have our drinks there.'

Following my gesture he goes into the room, as I pour myself a straight whiskey; and for him, a triple vodka and cola.

Then I took the drinks to the room, where he sits on the sofa, opposite the plasma TV obviously still quite nervous.

I sip at my drink, passing him his as I do.

'Get that drink down you,' I tell him, sitting in the armchair next to the TV so I can look at him, as his soft-blue, oh-so appealing eyes are held by the images on the screen and the film I'd left on, to gauge his interest: in it, two dudes are rough-housing a blond teen, who looks like a slightly older James.

One muscular tanned dude has already undressed the slim white teen; the other dude is now holding him by the head, pulling him towards the bulge in his jeans.

My young guest seems quite interested, chugging down his drink, entranced and wide-eyed, watching every move on the big screen.

'Are they really hurting him?' He asks me breathlessly.

And, I can't help but smile -- this is so much better than I'd hoped.

'Not yet,' I told him.

'But they will,' I added, noting the fixed expression he wears, as he stares intently at the screen.

'Will you too'...? This question lies unfinished. But, I can hear his interest in his excited voice.

'Perhaps I might...' I tell James suggestively, 'If you're real good, at being real bad, for me.'

'May I have another drink?' He asked, looking at me.

'Sure,' I answered, standing and taking the empty glass from him.

And, when I return to the room, with another drink for him, it's plain by the bulge in his tight black jeans that he's aroused by what he's watching.

On the screen the young naked blond has been shoved onto his back, his knees pushed towards his chest; one man over him, his cock embedded deep in his boy-cunt, as the other man straddles his neck and face fucks him.

'Here,' I say, offering him his second drink and sitting to his left on the sofa, with my own desires growing by the second.

I want James now; he is so cute and sexy.

'You're so pretty,' I say to him, stroking his face and adding, 'You're going to look so-nice in what you'll wear, for me...'

'And, will you?...' he asks again hesitatingly.

Again he had to ask to ask what he now wants more and more from me, as he watches the teen on the screen enjoy the dudes fucking him non-stop.

But, he's apprehensive -- and it shows.

He shrinks back just a little, as I lean in toward him, taking his face in my hands: and I kiss him. Kiss his soft, luscious, warm, moist lips.

I feel him tense, as I open his lips with my tongue, and I place my right hand directly on the bulge in his jeans.

He opened his mouth, with flickering eyes, as we touched tongues lightly and continued kissing, and I held him tightly close to me.

He sighs with pleasure and then kisses me back.

Reaching up with my left hand, I caress his cheek softly and we kiss some more, as I continue to stroke his hard cock bulge with my right hand.

He sighs some more, he wants it badly now and I can feel it. He has been watching the screen intently as the teen gets fucked: boy-pussy and mouth.

I go for his nipples caressing them with my left hand, he raises his shirt so I can nibble, lick and suckle them as the dudes had done on screen a while back to the blond. Fast learner, I thought to myself.

Now my right hand starts to fondle his plump girlish ass. He is falling apart, as all his inhibitions leave him as he succumbs to his lustful desires.

Sitting back, I push young James down to the carpet, where he sprawled there, shocked.

'What?' He exclaimed.

'It's time for you to get ready,' I told him; as I sit forward a little, my hands on my knees.

'Get up,' I snapped.

He does as told, to stand before me, shaking.

'Go in the front room,' I instruct, 'you'll find some pretty things on the table that I want you to wear now. And fix your hair.'

He leaves the room, pausing in the doorway, to look back longingly at me, a moment before walking out of the room.

It's obvious he has doubts, but the money and lust override these and he leaves, his lower lip trembling sweetly, as a single tear trickles down his cute face. Damn I missed that photo op.

On his return I smile as he stands before me, trembling a little, my little pretty sissy boy, ready to pose for me, dressed in a pink short nighty, self-support black fine stockings and black lace panties. His hair nicely done up in a cute ponytail.

He has applied the lipstick carefully and it looks good on his quivering lips. The eye shadow too, makes his eyes prettier, and the rouge on his cheeks, he must have made up before. He is so beautifully fem now.

'You look beautiful doll' I compliment him on his make up and he smiles eagerly for me.

I rise, towering over the teen and take from my pocket the last article he is to wear for me: a two-inch wide, dark brown studded dog-collar which I place lovingly around his neck, while he bows his head in submission and I give him a kiss on his rosy cheek.

'Now you're ready babe,' I tell the youth, pleased with his obedience to all I have asked of him, so far.

I clip a leash on the collar and pull him with me, as I walk back into the front room and then I stand there before him, my hands on his shoulders as I stare down at him, as he looks at his pretty stocking-clad feet in high heel sandals.

The room curtains are closed and the room is lit by two standard lamps and this moment is mine. The moment I was waiting for and desired so much.

Lifting his chin, so that he looks up, I lean down and enter his mouth with my eager tongue once more, seeking to possess him, as I glide my right and up his nylon-clad left leg, toward the bare flesh above; and he moans softly against my lips.

And I stand back -- to look at him, my lovely new sissy boy, ready and eager to pose for me and please me.

'Now stand still my love while I get my camera,' I tell the teen.

Retrieving my digital camera from the sideboard, I look to the clock and realize that I only have a half hour left, or my pleasure will cost more than I'd expected.

'Now, dance for me,' I direct, turning on the stereo and as the sound of Dire Straights fills the room, he begins to sway: and I take picture after picture. He moves very sexily, he glides as if dreaming. He is ravishing! I drool in anticipation of what comes next in my program.

Yet, I'm aware of the time moving on.

So placing the camera down on the table; and picking up a tube of man lube, I walk toward him and slide my right hand fingers beneath the collar and lead the sissy boy across the room to an armchair by the window.

'Sit down I order him,' kneeling before him and parting his legs.

He obeys and watches me mesmerized, as I slide the nightie's hem slowly up his legs, to reveal his cute small erection bulge tenting out the front of the black sheer lace nylon panties.

I ease over my hungry wet lips over his taut buttocks; then down his legs and then lean forward to engulf his small cock in my mouth. He shakes with unbridled lust.

He grips my shoulders, closing his eyes, moaning with pleasure as I swirl my tongue round his cock-head, then begin a slow sucking action, causing him to writhe beneath me and moan uncontrollably with pleasure.

As I pleasure him, I undo my belt and the buttons on my trousers.

Then I stand, leaving him panting and wide-eyed, as I finish undressing and he stares in disbelief at my fully erect manhood and massive dark hairy balls.

I smear my cock with the lube, and then insert two lubed fingers into him, one by one, opening his boy hole, ready for my use. Ready

for his first pleasuring.

'Please..?' He pleads. It's a question of need, or something else? I don't care -- I want him, real bad now. He is so fuckin hot.

Grasping his ankles I open his legs wide and push his knees toward his shoulders, making his arms loop around them and holding his boy pussy wide open for his first fuck, as I lie down on him, holding my hard erect, pre-cum dribbling, eight Inches of man cock against his tight, puckered but well lubed, virgin pussy hole.

His little cock and small nuts are pressed against my belly, as I use my right hand to ease myself into him, my left hand behind his head pulling his face to me.

As his boi hole slowly widens to accommodate me, I kiss him, holding him tight as I begin to thrust back and forth working my way deeply into him.

'Please... please... oh...yes...yes...I want more...' he keeps saying now in encouragement. But, his needs aren't important to me, mine are now.

Then supporting my weight on my arms, I look down at the young teen, lipstick smeared across his mouth, dressed as my very own private sissy-slut.

He wraps his legs round my thighs, and he pushes his boi cunt toward me, as I fuck him. His hole grips my cock tightly. His pussy is so good. I slide in and out now, faster and deeper all the time. He is panting with lust and so am I. He is mine. James is my sissy-boy now and he loves it. He shows it all over.

His head turns from side to side, thrashing as he wraps his slender arms tightly round my neck, pulling me toward him, until finally I can feel the tremor in my thighs announcing my oncoming climax.

I push deep into him exciting his G spot now, as he kisses me fervently, his own need to climax obvious. I had forgotten the joy of pleasing a virgin boy for the first time.

As I pump my man seed deep inside him, I find instant relief and incredible pleasure. He releases his own creamy load over his smooth, hairless belly groaning loudly in ecstasy. I soon ease out of his tight embrace. It's over. My needs and his are totally fulfilled in this brief passionate moment of bliss and lust.

I stand looking down at him, lying there, legs splayed open, my cum trickling out of his distended boi hole and I look at the clock.

'Fifty minutes, James.' I tell him smiling. 'You were wonderful'. 'And so were you sir.' he smiled back gratefully.

'Now for the next ten minutes, you can finger your cunt with our sperm while I take a few more pics, okay?'

James looked at me, with a blank look on his face.

'Just wank your hole with our cum.' I explain.

The teen does as he's told, as I get my camera and begin to take the pictures I want, as James slides one, two and then three cum-filled fingers in and out of himself, a glazed look on his face as he vainly tries to bring himself to climax again with his fingers, as I had just done him with my 8 inch man tool. He is such a good sissy boy for me.

'Well, you've earned you money now,' I assured him, with a smile. I watched him undress, dress in his street clothes and paid him.

'Want to come back for more' I asked throwing him some more bait. 'Just give me a ring next week and I'll pay you for two hours work.'

'O yes sir, thank you', he says eagerly.

'Here, wear this collar so you remember' and I put the dog collar on his slim long neck giving him one last kiss for the day. He shuddered.

He smiles gratefully. 'I do need the money sir'

'We all do James' I answer as I open the door and pat his cute butt one last time.

Now to view and send these pictures out to my friends, they will enjoy them, and send me more of theirs. This is going to be one heck of a good summer.

Can't wait for next week!