A Weekend With Billy Ch. 5

'In…in…in…all the way,' I said. 'I can feel your ass against my knuckles. Oh, darling, how warm you feel! Shall I try to find your G-spot?'

I squeezed my finger against Billy's prostate gland. Squeeze, squeeze, squeeze. Pre-cum coursed out of his prick.

'Oh, look!' I said. 'Wetter and wetter! You like that, darling, don't you?'

And with my free hand, I massaged the pre-cum into his stomach.

Finally, I removed my finger from his asshole and picked up the dildo.

'Oh, darling!' I said. 'I need to be inside you. I need to be inside you.'

I coated the dildo in lubricant in front of Billy's face, then moved it down to his butt-hole.

'Oh, please! Now! Let me in. Let me IN!' I said.

I nudged the tip of the dildo against Billy's asshole. A sharp intake of breath from Billy. Slowly, slowly, slowly, I pushed the tip of the dildo into Billy anus. I paused.

'Oh, Billy!' I said. 'I love the sight of my prick just entering your cunt. But I want to be in you. I want to be IN you.'

Gently, I pushed the dildo further up his ass. Further and further. All the way.

Billy moaned.

Slowly, I pulled the dildo back out till just the tip was engulfed, then pushed it all the way back in again. Deeply but gently, slowly but rhythmically, I fucked Billy's ass.

'Oh yes! Oh yes!' I moaned. 'Your cunt feels so tight. You're so tight.'

I must have gone on fucking his ass like that for about five minutes. And all the while I kept talking to him.

'I'm fucking you, Billy. I'm fucking you, Billy. Just like you fuck me in your head. I'm filling your cunt with my prick, Billy. Do you like that? Is that what you'd like to do to me? Is it? Like that? And like that?'

When I'd finally done with him, I left his anus impaled on the dildo and asked Polly and Angela to spin him round on his back so that his head was facing the audience.

I looked down into Billy's eyes.

'Do you know what you're going to do now?' I asked him.

He shook his head.

I got Angela and Polly to lift his butt off the desk until his prick was hanging above his head.

'Do you know what you're going to do now?' I asked again. 'You're going to come in your mouth. You're going to make yourself come in your own mouth. You're going to jerk off and shoot your load into your mouth. Now do it!'

Billy remained motionless.

I moved round to the other side of the desk and gave each buttock the hardest spank I could muster.

Billy grabbed his prick in his right hand. I retraced my steps round the desk and knelt beside him, our faces inches apart. I looked up at his hand on his dick. He began to jerk off.

It was an amazing sight - the dildo still sticking up from between his ass cheeks, his balls hanging down, his glistening erect penis in his hand. Gently, he squeezed his glans. His eyelet opened, and a thin strand of pre-cum slowly dropped towards his mouth. He squeezed again. Slowly, the pre-cum descended until it finally entered his mouth and pooled on his waiting tongue.

Billy closed his mouth and tasted. Swallowed. Milked some more pre-cum onto his tongue. Tasted and swallowed again and again. I was mesmerised at the sight of it, knowing how excited Billy must be feeling to produce such a quantity of fluid.

Then Billy started to jerk off slowly. I looked up at his foreskin moving back and forth across his glans. Sometimes he pumped his shaft, sometimes he squeezed his helmet, sometimes he rubbed and pinched the ridges of his glans. But he always returned to his finger-and-thumb grip and fucked his foreskin with his helmet.

He masturbated for a good five minutes, and then suddenly began pumping furiously. This went on for a further two minutes or so, and then he began grunting uncontrollably. Almost immediately, a jet of semen coursed down into his mouth. Another followed. Another, and another.

Billy's aim was pretty good. Most of his spurts hit their target, so that I wondered if he'd done this a few times before. Even so, one spurt hit his nose, one his chin, and one landed on his right cheek.

When he was finally spent, I removed the dildo from his asshole, Polly and Angela lowering him back down to the desk.

I told him to stand up and open his mouth.

He did so, staggering a little at first.

I looked at the semen inside his mouth.

'Good,' I said. 'Now rinse your mouth with it.'

Billy swished the semen about in his mouth. The sound it made was out of this world.

'Now show me again,' I said.

He opened his mouth. The semen, mixed with his saliva, bubbled and frothed.

'Now swallow it down,' I commanded.

He obeyed. A beautiful gulping sound reached my ears.

We stood and feasted our eyes on the aftermath - the sperm on Billy's nose and cheek and chin, his post-tumescent cock still glistening and sticky, his ass cheeks still red from his spanking.

I turned to Angela.

'Could you give me your g-string?' I asked.

'Sure,' she said, not batting an eyelid.

She deftly removed her g-string under her dress without revealing anything. She stepped out of it and handed it to me. I made Billy step into it and then pulled it up. It was tiny - no more than a sling for his prick. He looked surreal.

I took off my suspender belt and stockings and got Billy into them.

'Do you know what I'm going to do now?' I asked.

Billy shook his head.

I retrieved the cane that, unknown to him, I'd hidden under the desk before the performance began.

'I'm going to cane you,' I said.

Billy's eyes widened, but he was silent for a moment.

'I guess I deserve it,' he finally said.

'Of course you deserve it. Now bend over my desk.'

Billy complied.

He looked fantastic, his red ass cheeks framed by the suspender belt, the suspenders and the stocking tops below. The red g-string was the icing on the cake.

I picked up the bottle of baby oil and squirted a liberal quantity on his butt cheeks. With gentle caresses I massaged it in.

'This will make you even more sensitive,' I observed.

Then I whispered something into Billy's ear. He nodded.

I raised the cane, waiting for a moment, then brought it down sharply.

SWISH-CRACK!

'Argh!' Billy cried, as a livid red welt appeared across his buttocks.

SWISH-CRACK!

'Argh!'

Another welt.

SWISH-CRACK!

'I'm sorry. I'm sorry. I won't do it again. I won't strip you with my eyes again.'

SWISH-CRACK!

'Please.'

SWISH-CRACK!

'Arrrrrrgggghhhhh!'

Five red stripes decorated his ass. I paused and looked at them for ten seconds or so. Then I raised the cane and brought it down still harder than before.

SWISH-CRACK!

'Blue! Blue!'

It was hardly more than a whisper, but I heard it. It was the 'safe' word I'd whispered into Billy's ear before striping his ass.

I wasn't surprised. I'd warned him how painful it would be in the garden after lunch. I was annoyed that he'd insisted so stubbornly and felt like giving him another stripe by way of punishment. But a safe word is a safe word and trust is trust, so of course I resisted the temptation.

I looked once more at the six welts across his butt. Silly Billy!

'Have you learnt your lesson?' I asked.

'Yes. Yes.'

I believed him.

'Okay. You can stand up now.'

Billy raised himself up and faced me. His eyes were watering slightly, but he shook my hand.

I put on my skirt and blouse then picked up Billy's suit pants.

'Polly,' I said, 'could you take off your miniskirt? You can wear these.'

She stepped out of her miniskirt and handed it to me. Then she put on the pants.

I easily got Billy into the miniskirt. He was truly like putty in my hands.

'You can stay like that for the rest of the day,' I said. 'Maybe we'll strip you with our eyes from time to time. Contemplate your hot sticky prick in its tiny red sling. Dream of those dark red stripes across you well-oiled ass.'

Polly and Angela laughed.

And with that, we all lined up in front of the audience and took a bow. They went wild, clapping and cheering and baying. When we took our second bow, Billy gamely turned his back to the audience and raised his skirt. We had one last glimpse of those six stripes. They were livid.

The following Thursday, Billy phoned me. He'd got the job. He'd be moving down to London in about a month.

'Where are you going to live?' I asked.

'I don't know yet.'

'Why don't you stay with me while you're looking?'

'That's really kind of you. Are you sure it's okay?'

'Oh yes. It'll be fun.'

'You can be certain of that,' Billy laughed.

'How's that ass of yours?'

'It's getting there.'

'I did warn you.'

'I know you did. But I really wanted to try it. Actually, I'm glad I did.'

I hoped Billy would be staying with me for a very long time.