A Weekend With Billy Ch. 1

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Billy unwittingly puts on strip show for his hostess.
1.8k words
4.29
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Part 1 of the 5 part series

Updated 10/03/2022
Created 04/23/2002
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I'll never forget the weekend Billy came. He was a friend of a friend, and he had a job interview in London one Monday morning. He needed somewhere to stay on Sunday night. I suggested he come on the Friday and spend the weekend taking in the sights. But the sights he got to see, and the sights I got to see, were not exactly what he'd anticipated.

I'm a normal woman. I love having sex. But I'm also a wicked woman, because I love leering at men. Naked men. Men with erections. Men masturbating. Men coming. Men being spanked. Men pumped and ridden and sucked off and milked by women who are still partially clothed and completely in control. I surf the internet looking for the pictures and videos that leave my panties in ruins and my clitoris spent. Magazines litter my house.

Billy arrived about eight and we had dinner together. Afterwards, I left him in the sitting-room with coffee so that I could load the dishwasher. Although I'd cleared most of the magazines away, I'd deliberately left a few of them strategically placed. Nothing too far out. Shots of hunks in the raw. Nice chests, cute balls, firm asses, the occasional erection. I hoped Billy might flick through them while I was away. I wanted him to know I was okay about sex.

He didn't mention them at the time, but I had a feeling some of them had been moved. And of course, I was subsequently proved right. We chatted for about an hour, and then Billy said he was ready for bed. I showed him to the guest room and told him to make himself at home.

'Feel free to read any of the books or watch TV,' I said.

He thanked me and we said goodnight.

I'd left him plenty to occupy himself with. The latest editions of Penthouse and Men Only. A handful of XXX magazines. Several videos.

I went into the room next to his but didn't switch on the light. I watched him. Yes, I confess it now, wicked woman that I am, my guest room has a two-way mirror. It is vast and cost me a fortune, but it has afforded me numberless hours of pleasure.

I looked at Billy as he settled into his room. He must have been about twenty-two. He was handsome and attractively built, but terribly quiet. Very decent, very proper, endlessly polite. 'A very nice young man,' as my mother would say. Usually the kiss of death as far as I'm concerned. But the thought of seeing this innocent, rather sweet young man disrobing was riveting. I was about thirty-eight at the time, I'd long since seen everything, but nothing beats the frisson of seeing innocence exposed.

And yet men are full of surprises, and Billy was no exception. To my delight, he quickly spotted the magazines, but he merely flicked through Penthouse and Men Only. He quickly abandoned them, and I immediately jumped to the conclusion that he wasn't into porn. How wrong I was! Instead of getting undressed, taking a shower and putting himself to bed as I anticipated, he turned to the hardcore magazines. He selected the 'best' one with evident care and sat on the bed to study it. And yes, he was definitely into it. He looked at each page long and hard, and his hand soon wandered to his crotch. I gasped with joy as he began to fondle himself through his jeans.

Billy continued to pleasure himself for some time, then put down the magazine. He looked at himself in the mirror and stood up. Standing with his feet apart at the foot of the bed, clearly contemplating himself in the mirror, he lifted his T-shirt above his head and tossed it to the floor. He advanced a few steps towards the mirror and stood with his hands on his hips. He turned round and half bent down. He looked under his arm into the mirror, deliciously checking out the contours of his butt. And what contours! Firm and rounded, crammed tightly into his jeans.

He stood up and faced the mirror again. He advanced a few more steps. And then he unzipped his fly and unbuttoned his jeans. He pulled his fly flaps wide open. His penis, already bulging, was nudging against the triangular red pouch of his briefs. Red! Whoever would have believed it? I'd expected some hideously sensible white Y-fronts. But these were no Y-fronts. The pouch was sexily cut.

He turned his back to the mirror and, watching himself over his shoulder, slowly lowered his jeans. Another surprise. Not briefs. A thong! He was wearing a bright red thong! He'd been wearing it on the train down from Manchester! He'd been wearing it when he arrived! He'd been wearing it through dinner and coffee! Sweet Mr. Innocent in a bright red thong! I was stunned.

He fondled his buttocks for a while and then faced the mirror again. He grabbed his penis and balls through the fabric of the pouch. He squeezed and massaged, pinched and stroked. The tip of his penis pulled hard against the pouch, desperate to be released.

Billy pulled the ottoman away from the mirror and turned it short-side on. He sat on the edge facing the mirror and slowly lay down, his feet remaining on the floor. The edge of the ottoman was quite close to the mirror, and I could clearly see the outlines of his penis jutting up inside his pouch. More fondling and kneading ensued, and his prick grew harder and harder.

Suddenly, he stood up and turned his back to the mirror. He straddled the ottoman and sat down on it as if it were a motorbike. He lowered his chest to its padded silk seat. And there he was, prone, gripping the end of the ottoman between his knees, his glorious butt mere inches from my face. He fondled that butt lasciviously. Then he stood up again and, still straddling the ottoman, bent down. I stared at his balls pulled tight in the base of his pouch between his thighs. I feasted my eyes on his naked ass cheeks.

And then came another surprise. Sweet Mr. Innocent grasped both buttocks in the palms of his hands and pulled those buttocks wide apart. The under-strap of his thong was fully exposed. I instantly looked for some hint of anus, and, sure enough, a small area of puckered skin was revealed either side of the under-strap close to the point where it joined the pouch.

Billy pinched and kneaded his buttocks and occasionally massaged himself with the tip of his second finger along the length of the under-strap. He tapped at the fabric that covered his anus then pinched the flesh along his butt cleft quite hard.

I lifted my skirt and slipped my right hand inside my panties. My sex was dripping. I massaged my clitoris with the tip of my second finger, shuddering with the pleasure of it. I slipped my left hand under my blouse and squeezed my breasts through my bra. I pinched my nipples and scratched at them gently through the nylon.

Billy stood up and faced the mirror again. Slowly, he lowered his thong. Inch by inch, his shaft was revealed, until his helmet suddenly sprang free of the pouch and his prick reared up in front of him. Leaving his thong round his thighs, he slowly pulled back his foreskin. His purple helmet glistened.

Staring intently into the mirror, he squeezed his glans and, rapt, watched more pre-cum ooze from the eye. He massaged it into his helmet and squeezed again. A further droplet appeared. He scooped it onto his finger and, deliciously, transferred it to his mouth. He repeated this several times, sucking on his fingertip and swallowing.

He gave his glans one hell of a going-over, pinching it, kneading it, twisting it, cupping it. Then he massaged the cleft and ridges, those most sensitive parts of the penis. He rubbed and tapped and pinched. I looked at his face. His neck and cheeks were flushed. His head was thrown back and his nostrils flared. His face was contorted with pleasure.

He sat down on the ottoman and fully removed his thong. He grabbed his penis in his fist and began to jerk off. Slowly, rhythmically, his hand moved up and down. He seemed to go on for an eternity, pulling away with his right hand, fondling his chest and nipples with his left. I watched, transfixed. His penis was fairly long and wonderfully thick. Sometimes he stopped to fondle his balls, sometimes he jerked off with his thumb and forefinger, but he always returned to his trusty old wrist grip. And it was clear he was a seasoned masturbator. He teased himself, speeding up, slowing down, stopping, starting. Now he returned his attention to his glans, now he returned to his shaft. On and on he went.

And then he stopped and raised his knees to his chest. I was amazed. His anus was fully exposed, dark red and puckered. Slowly, he ran the palm of his left hand up the back of his thigh until it reached his left buttock. He massaged that buttock and then continued his advance.

His middle finger slipped into his butt cleft. He massaged that cleft up and down and circled his anus with his fingertip. Mr. Innocent! Tapping and circling that most secret of parts. Then he spat on his fingertip and returned it to his anus. I caught my breath. Could he really be going to do it? He could.

Slowly, he inched his finger into his anus, millimetre by millimetre until it had fully disappeared. He moved his hand about gently. Then, slowly, he withdrew three-quarters of his finger and, equally slowly, pushed it back in again. The puckered skin round his anus seemed to suck and blow. Again and again he repeated the action, in, out, in, out, gradually increasing the tempo until he was rhythmically fucking his own ass-hole. Briefly, he slipped in a second finger and pulled. His fingers launched into a kind of walking motion. He winced with pleasure. Then he removed one finger and resumed his wanton ass-fuck.

He grabbed his penis in his right fist and, still fucking his ass with his other hand, began to jerk off furiously. I couldn't believe how long he lasted. He seemed to be pulling and pumping away with one hand, and deliciously jabbing away with the other, for an eternity. My fingertip was getting into a frenzy against my clitoris, and I struggled not to moan too loudly.

Finally, Billy stopped. Nothing happened for an instant, and then a great jet of sperm arced out from his penis. It crashed down onto his chest, clinging enticingly to his chest hair. Further spurts pumped out and landed on his stomach. He produced an astonishing amount of semen, his ankles dancing about and his torso shuddering, before he was finally spent. Then he just lay there, all wet and messy, before slowly removing his finger from his ass. Slowly, he got up, clearly shattered, and staggered off into the en suite bathroom.

Well, Mr. Innocent, we know now, I thought.

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