A Weeend with Billy

I told Billy to go upstairs and take a shower, but not get dressed. I went up to my own room and took a shower myself. What with the fun we'd had in the garden and the spanking I'd so recently administered, my sex was sopping, and I easily brought myself to a climax before getting myself clean.

I put on a tiny black bra and matching g-string, then took a white blouse and microscopic green miniskirt from the closet. I carried them into Billy's room.

Billy, freshly showered, was sitting on the bed, a towel around his waist. I put my skirt and blouse on the ottoman and brazenly bent over Billy's suitcase. I found a couple of clean thongs, one black, one purple, and a white tanga. I choose the purple thong, along with a pair of white cotton chinos, white short-sleeved shirt and white socks.

I took them over to Billy, stood him up, removed his towel, and began to dress him. Even in its flaccid state, his penis was a delight to behold. I got him to step into the thong and pulled it up, boldly adjusting his penis inside the pouch. Then I put on his white cotton socks. They looked sexy with only the thong for company. Sadly, I got him into his chinos. I was about to pick up his shirt when I noticed something. His chinos had no pockets at the back and, being designed for summer, were unlined. The cotton was generously thin, so that the waistband of his thong showed vaguely through. To a careful eye, it was a dead give-away.

I told him I had a top that would really suit him and returned to my bedroom, hoping that he wouldn't catch a glimpse of his butt in the mirror. Luckily, he sat down on the bed as I left the room. I fetched a white singlet that had belonged to an ex-boyfriend. It was tight and short and Billy, being muscular, had the body for it. I returned with it and slipped it over his head. It didn't quite reach his belly-button.

'Wow! This is cool,' he said.

Little did he know!

Finally, I put my blouse and skirt on in front of him and we went downstairs.

We went into the kitchen. I asked Billy to fill the kettle for some coffee. And yes, as he leaned over the sink, the seat of his trousers was drawn tight across his butt, so that the waistband and the little triangle at the top of the under-strap were both enticingly visible.

'I want to buy you some underwear,' I said.

He straightened up.

'Underwear? Why?'

'Because I love the way you're going to look in it.'

Billy laughed.

'I know a brilliant shop,' I said. 'I'll take you there.'

'Fine.'

We took the Tube into town and stepped out into blinding sunlight. 'Thank God!' I thought and fell behind Billy for a moment - and sure enough, the purple waistband was vaguely visible. I took his hand and walked beside him, proud as Punch. After we'd been walking for a minute or so, a woman suddenly rushed past us, stopped, turned to face us, grinned broadly, then rushed off on her way again.

'What the hell's she got to grin about?' Billy asked.

'I can't imagine,' I lied.

I led Billy to a place I know very well. A small store. Downstairs is a women's lingerie boutique, but upstairs, accessed via a separate entrance, specialises in men's underwear. Several men were furtively flicking through the racks, pretending to be more interested in the boxers than the thongs. To my delight, the assistant was a young woman. She can't have been more than about twenty.

I got straight down to business. I knew what I was looking for. First I found some skin-tight, black cotton-and-lycra trunks with very, very, very short legs. Next a dark blue full-backed tanga. A bright yellow three-quarter-backed tanga. A mid green half-backed tanga. A bright red quarter-backed tanga. This I particularly liked, as the back panel was exactly the same size as the pouch, only flat! A dubious turquoise silk thong and - finally - a tiny, tiny red nylon g-string with plain black elastic waistband and under-strap. All of which I bundled into Billy's embarrassed hands.

I thrust him to the pay station, where he coyly deposited the underwear on the counter. The assistant scrutinised each item separately, checking they were all the same size and slowly removing the price tags.

'Just about one of everything,' she finally laughed.

'Ah! Just a minute! That reminds me,' I said, and rushed back to the racks of underwear. I returned to the counter with a lovely little blue and white striped thong.

The assistant raised her eyebrows in interrogation.

'This will be great for spankings,' I explained.

Billy turned crimson.

'Yeah, right,' he said, trying to make it seem like a joke.

I paid and we left the store.

'Why so many?' Billy asked as we descended the stairs.

'You'll see,' I mysteriously replied.

'I'd like to ask you a favour,' I said, as we sat over lunch in my kitchen about an hour later. 'A very big favour, in fact.'

'What is it?' Billy asked.

'It's one of the reasons for all the underwear,' I replied. 'I want you to strip for some friends of mine. Women, of course. In my living room. This afternoon. And not just strip. Give yourself an erection. Show us your butt hole. Shove your finger up it, if you dare. Jerk off. Come. Right in front of us. And enjoy yourself doing it. Can you do that?'

'Well…'

'Oh, and I want to video your performance. If you don't mind. All right?'

Billy was speechless.

'Please!' I begged.

'All right, then,' he said very quietly.

I phoned six friends of mine and invited them round. I told them I had a surprise for them. I knew what they'd be thinking. They'd be thinking I'd invested in another raunchy video which I was desperate to share with them. Some guy stripping and giving himself an erection. Possibly a guy being paddled and caned. They'd been through it so many times before. They'd never guess they were going to see a live show.

Once I'd made all the phone calls, I took Billy upstairs to get dressed. I removed his trousers and thong, but left the singlet and socks in place. I knelt beside him with the bag of new underwear on the floor in front of me. His beautiful prick was inches from my face. First, I got him into the tiny red g-string, then the thong. Next came the quarter-backed, half-backed, three-quarter-backed and full-backed tangas. Finally, the skin-tight trunks. Seven items of underwear, not counting the singlet! The dance of the seven veils came to mind.

'I think we'll have you in your underwear from the start,' I said, 'but come with me for the finishing touch.'

I led Billy to my bedroom. He stared in amazement at the framed magazine photos on the walls - a big round ass, anus exposed, balls and prick hanging down underneath; a guy in a shower with the beginnings of an erection; a close-up of a fully-erect prick; a guy mid jerk-off. Then he noticed the piece de resistance on the back of the door. A life-sized poster or a guy at the moment of climax - head thrown back, nostrils flaring, dick firmly grasped, a stream of semen shooting up from the tip.

I rummaged about in my wardrobe and found an ex-boyfriend's cowboy hat. I planted it firmly on Billy's head. He looked ravishing.

Billy was in the kitchen when the women arrived. I sat them down in the lounge and we talked about this and that. As planned, Billy came in after about five minutes with a tray of coffee. The women fell silent, eyes riveted on his crutch. He took the tray round to each of them in turn.

Judy was the first to speak. 'Is this guy really standing here in his underwear?' she asked.

'And a cowboy hat,' Angela chipped in.

'Not for long,' I replied. 'Meet Billy. Billy's going to entertain us this afternoon. If you don't object, that is.'

The women were too stunned to reply at first, but they eventually murmured their various 'no-nos' and 'not-at-alls'.

Half an hour later, I made Billy, still naked and messy, sit and watch the video with us. His video. The video I'd made of his performance. And what a performance! …Billy stands in his underwear and cowboy hat, dance music playing in the background. He massages his chest and stomach through his singlet. He slips his left hand under his singlet and lifts it up to his chest, exposing his stomach. With his right hand, he massages his stomach, then slowly removes the singlet, which he tosses to the floor. He massages and pinches his nipples. He turns his back to us and fondles his ample butt through his trunks.

He walks right up to Angela and places her hands on his waist. Angela obligingly removes his trunks, revealing the full-backed tanga underneath. Billy fondles himself back and front, squeezing and pinching and stroking through the fabric. He goes up to Judy, who removes the first tanga. She is surprised to discover a second one underneath. Billy turns round to show off his three-quarter back, then struts around the room. He walks up to Helen, who briskly pulls down the second tanga. The third is revealed, and everyone laughs and complains. They laugh and complain even more when the fourth comes into view.

Billy turns round and the room falls silent. The quarter-backed tanga looks fantastic, pulling tightly against his ass. Most of his swelling butt cheeks are deliciously exposed, together with the top of his cleavage. Billy faces us and fondles his prick through the fabric. A tell-tale bulge appears. He goes up to Polly, who makes to remove the tanga, but is checked. Billy turns round, straddles Polly's lap and bends down. His ass is inches from her nose. She places one palm on each buttock and kneads. Billy stands up and turns round again. He straddles her left leg and begins to squat down. He presses his bulge against her left knee-cap and brazenly fucks her knee.

He stands up, the bulge now more prominent, and walks up to Judy. He presses the bulge against her nose. She giggles and squeals in excitement, and grasps his buttocks in her hands. Billy goes up to Jennifer, straddles her lap and pushes his bulge between her breasts. He squeezes her breasts through her T-shirt and thrusts between them with his bulge. He goes up to Angela and raises her up. He bends her over her chair and lifts up her miniskirt.

The tiny black back of her panties is revealed. Billy places his hands on Angela hips, thrusts forward, and fucks her butt cleft with his bulge. Again and again he thrusts, forcing the thin fabric of her panties between her cheeks. Slowly, lasciviously, he rubs his bulge up and down her butt cleft and prods firmly where the fabric nestles against her anus. Angela groans with pleasure.

Billy returns to Polly, turns his back on her, straddles her legs and bends down once more. This time Polly goes wild. She grabs Billy's waistband and yanks it up his back. The tiny triangle that purports to cover his rear disappears between his ass cheeks. And now Polly is lapping away at his ass and darting her tongue into his butt cleft. Billy gasps with pleasure for thirty seconds or so, then stands up. He deftly retrieves the tanga back from between his butt cheeks and restores it to its rightful position. It is clearly damp.

He moves over to Jean and places her hands on his waistband. Jean, a colleague of mine more than old enough to be Billy's mother, surprises him by pulling him over her lap and proceeding to spank him very hard. Her hand rains down on the tiny triangle of fabric and the naked acres of his buttocks, which rapidly turn pink. Billy wriggles about, but Jean continues to spank him for about a minute. Forcefully, she makes him stand up and yanks down his tanga, revealing the silk thong beneath. She forces him, tanga round his ankles, back over her lap and spanks his bare buttocks even more wildly. The other women whoop in appreciation. Billy's ass is now dark red.

Finally released, Billy moves to the centre of the room. He grasps the waistband of his thong. The women stare in anticipation. Billy lowers his thong, and sure enough, there is the tiny red g-string. The women groan, but their disappointment is short-lived. Billy has produced a prodigious amount of pre-cum, and the nylon around the tip of his penis is soaked.

He thrusts his hips back and forth, his penis straining against his pouch. He goes up to each of the women in turn and jabs his pouch against their noses. They giggle and wipe away the pre-cum with the backs of their hands. He returns to the centre of the room and turns his back to us. He plants his feet wide apart and bends down. Compared with his reddened buttocks, the skin inside his bum cleft is very white, and compared with that, the thin elastic under-strap is very black indeed.

'Look at his anus!' Judy gasps.

And sure enough, on either side of the barely-there under-strap, the dark red puckered flesh of his anus is revealed. Jean stands up and walks up to him. Billy, clearly wondering what's likely to happen next, makes to stand up too, but Jean won't let him. She yanks his waistband far up his back so that the under-strap tickles and massages his butt cleft and pulls into his hole. Billy snorts. Jean digs her thumbs into his ass cheeks very close to his anus and pulls them wide apart. His asshole clearly opens before our eyes. Jean calls on Angela to help her.

'Pull his waistband up,' she says.

Angela does so.

'As far it will stretch, front and back,' Jean adds.

Angela does as she's told. Billy's prick and balls are pulled cruelly against his body, and the under-strap of his g-string cuts sharply into his hole. Of course I zoom in very close, and the image on the TV screen is truly awesome. Jean releases and reapplies the pressure on her thumbs and Billy's anus closes and opens rhythmically like a fish mouth, devouring the under-strap.

When Billy is finally released, he stands in the centre of the room. Slowly, he lowers his g-string. His hard shaft is gradually revealed. Finally, his penis jerks free. The women cheer. Billy's glans is glistening with pre-cum. He squeezes the head of his penis and yet more pre-cum weeps from the tip. It is fascinating to watch. Billy milks more and more of the stuff and massages it into his glans and shaft. When his penis is incredibly hard and glistening, he squeezes more pre-cum onto his fingertips and brazenly laps it up. He walks up to each of the women in turn and thrusts his rock hard penis under their noses. The scent of sex is in the air.

Billy strikes a number of poses for us. He gets down on all fours and lowers his chest to the floor, his knees wide apart. We see his anus and balls between his legs. He pushes his hard shaft down and we see that too, the helmet purple and glistening. He pulls his butt cheeks wide apart and opens his anus slightly.

He gets up and raises Jean, Angela and Judy from the sofa. He lies on the sofa on his back and slowly masturbates. After a couple of minutes he lies on his side and masturbates some more. Then he lies on his stomach and massages his ass. He kneads and strokes and pinches. When he sits up again, we notice a little pool of pre-cum on the sofa. Fortunately, it is leather, and Jean wipes it up with a tissue.

Billy sits and allows his erection to subside somewhat. This is extremely enjoyable to watch, because it takes a considerable time. He then gets up, and rather to our surprise walks up to the television. He stands with his back to us, feet wide apart. We crouch low to get the best possible view of his prick and balls below his buttocks. He presses his prick against the TV screen and moves it about. It is soon very hard again, but forced to point straight down. The screen becomes smeared with pre-cum.

Again he walks up to each of the women, and wipes his bursting, soaking helmet against their cheeks. He kneads and pinches his helmet, tapping and pinching the ridges and cleft. His neck and cheeks are flushed and his breathing is deep and slow. He fondles and pleasures his shaven balls.

Finally, he lies on the floor and masturbates in earnest. He calls Polly to his side and gets her to suck on the fingers of his left hand. She does so with evident pleasure as she watches him jerk off. Saliva drools from her mouth and runs down his fingers.

Billy gets Polly to kneel behind his head. He raises his knees to his shoulders and gets Polly to hold them there. His anus is fully revealed. Still pulling his rod with his right hand, he lowers his left hand to his ass. He extends his middle finger and taps at his sphincter with it. He moans with pleasure. With all the women crowding round in disbelief, he slowly inserts his finger into his anus. Slowly, oh so slowly, it advances, and his sphincter stretches and sucks. Finally, he has inserted his finger right up to the knuckle.

He leaves it there and continues to masturbate. Then he begins to fuck his anus rhythmically with his finger. He does this for a minute, and the women get down on the floor and take it in turns to get the closest possible view. Then, still fucking his anus, Billy begins to jerk off more quickly. Faster and faster he masturbates until his back is arched with ecstasy. He moans with pleasure. Uuh! Uuh! Mm! Nn! Nn! Mm! Mm! And then, with a glorious grunt, he comes. Prodigiously. His semen gushes out in jet after jet. The first hits him right in the face, just under his nose. The next hits his neck. The next his chest. And so on, down to his stomach. Finally, the last few drops trickle down his glans and shaft and nestle in his pubic hair.

He lies back down on the floor and slowly removes his finger from his anus. We watch mesmerised as his erection slowly subsides until his penis flops wetly against his thigh. To our unutterable delight, he licks the semen from under his nose and gallantly swallows it down. He asks for a tissue, but we won't give him one…

I stopped the video. Everyone looked at Billy to see how he had taken his exposure. The guy was semi-erect! He'd enjoyed every damn minute of it! And what a gloriously messy picture he presented, drying semen still adorning his neck and chest, his stomach and pubic hair, his thigh.

'Well!' said Jean. 'You are a wicked boy! I've never seen such lascivious depravity. Masturbating to completion in front of, what, seven women! Brazenly probing your anus! And allowing yourself to be videoed doing it! Unbelievable! You must be soundly spanked, my boy!

I quickly inserted a new tape in the video camera and pressed 'record'.

Jean pulled Billy up from his chair. She found the quarter-backed tanga on the floor. It was evidently her favourite. She made him step into it and pulled it up around his waist. She sat on a dining chair.

'Now get yourself across my knees,' she said.

Billy looked at the sperm on his chest and stomach.

'Never mind that,' barked Jean. 'Just get yourself over my knees.'

Billy lowered himself into position.

Jean gently stroked his buttocks for a moment as we all stared at the tiny triangle of fabric that barely covered his crack. Indeed, an ample cleavage was revealed. Jean raised her hand and paused. She waited a good ten seconds and then brought her hand down with a resounding smack. She paused again, then smacked again, equally hard. She spanked him slowly like this about twelve times, then spanked him at least twenty times very hard and very fast. She rested for a few seconds, then administered another twenty fast smacks. Billy's buttocks wriggled and writhed, already bright pink. Now she spanked the bare parts of his buttocks, now the tiny triangle of fabric, now the backs of his thighs. The sound was deafening. Billy gasped and gasped. Finally, Jean was exhausted.

'Get up,' she barked.

He did so. Jean got up too and walked over to one of the armchairs. She turned it round.

'Now bend over the back of this,' she bawled.

Billy hesitated.

'Do you dare to hesitate?' Jean asked, and spanked him hard again as he stood there.

Billy walked over to the armchair and bent over it.

'Angela!' barked Jean. 'Spank him long and spank him hard.'