Just bear in mind that some people got into this lifestyle accidentally. I certainly had no intention of getting into anything kinky with Jeremy. I was several years older than he, and he had the pick of the most beautiful girls imaginable. Yes, I fantasised about bedding him, but it was pure accident that we got together.

I run weekly tennis parties during the summer months. Not because I'm a great tennis fan, but I do enjoy having young athletic men around. On this particular Saturday afternoon Jeremy had just finished a game with me. He ran around the net, caught his shorts in the iron-rail, and ripped them across the front. And Jeremy wasn't wearing anything underneath. I caught a flash of his genitals. He clutched his groin and cringed. We were a few hundred yards from the house and the changing rooms. And he had to pass half a dozen pretty girls to get there. Acting instinctively I quickly wrapped a tennis skirt about his waist. It was one of those pleated skirts, white cotton with a side button. He was so glad to be covered it took a few seconds for it to sink in that he was now wearing a skirt. A very short skirt! And I thought he looked really cute! His tanned thighs were even more appealing somehow than when he was wearing shorts.

'Stand right next to me.' I said, 'With a bit of luck nobody will notice it's a skirt. And at least you're decent!'

Grimacing with embarrassment he had no choice but to walk slowly alongside me. I held his arm tight. And as our thighs brushed against each other, as I realised how helpless and scared he was I became quite excited. Instead of taking him to the changing rooms I steered him to my bedroom which could be entered via a couple of steps and the balcony.

Wanting to remain very much -in-charge I said, 'Give me your shorts, I'll try and mend them.'

He reluctantly removed the shredded and torn shorts with a face that glowed with humiliation. 'Couldn't you just get me my jeans?' He asked, not quite masking his irritation.

Stung by his tone I answered, 'I was only trying to help. I'm not going into the men's room. I'll call Steven.'

'NO!' He cried. 'Don't.' I smiled to myself, Steven had a wicked sense of humor, and seeing Jeremy wearing a skirt would delight him no end.

I raised an eyebrow, 'I could tell them you've gone home. You could stay here until its safe to retrieve your pants?'

He nodded. I left him alone, in his first skirt, in my bedroom. I quickly called off the rest of the games pleading a headache. Half an hour later I was back with Jeremy. He was seated on my bed, the short white pleated skirt lying neatly high on his thighs. When he saw my stare he tugged the hem of the skirt - just like a woman!

'Are they gone?' He asked fearfully. It belatedly occurred to me that he was truly frightened, men are such babies. 'Jenny is getting dressed, she won't be long.' I lied.

He sighed. 'I feel so stupid.'

'I think you look cute and sexy.' I whispered thickly. He recognized the heat in my words and stared. I saw him frown. 'You could at least thank me for keeping quiet.' I said before he could reply, 'Have you any idea how tempting it was?'

He blinked. 'What do you mean?'

I moved close, 'I could have dined out on this incident for weeks. Jeremy wearing a skirt. Jeremy in my bedroom hiding his blushes. It would make such a wonderful conversation piece!'

I saw his eyes calculating. What I'd said was true, and was still true. Without actually saying it - I'd told him I could describe his shame any time I wanted.

He smiled weakly. 'Thanks Ilene, I owe you one.'

'Then pay me.' I said deliberately. I was too excited to be subtle. I saw him swallow. His eyes ran over my body. I flipped open the buttons of my blouse. His eyes went wide at the sight of my satin bra. I'm a little overweight but I have really good breasts. I unbuttoned my skirt and allowed it to fall to the floor. Knowing he had nowhere to run I slipped my arm about his waist and kissed him. My hand sneaked under his skirt. And found him rock-hard! Tumbling him back onto my bed I slid on top of him. I found to my surprise I enjoyed being in control. As I kissed him I shoved the skirt upwards and guided his erection inside me. I began to jerk my hips. Making love to him as though I was the man, and he was the woman! As he gasped beneath me I stared down and whispered, 'You're wearing a skirt and you're being fucked!' And before he could reply I covered his mouth with mine.

It was very good sex, the best I'd had in years. I fell asleep exhausted, and when I awoke - Jeremy was gone.

I sent him invitations to my next two tennis parties - but he didn't even bother to reply. Angered by this I bought a really cute tennis dress, not a skirt, but a proper sleeveless tennis dress. White nylon with a V-neck, and a tiny hip-hugging skirt it would look saucy on even the most demure female. I posted it to him with my next invitation!

Jeremy 'phoned me the next day. He sounded wary. 'I got your invitation. And the er, dress?'

'Jeremy, darling. You've been avoiding me. Now that must stop. Be here tomorrow, I haven't invited anyone else. We can have our own private tennis party.'

He didn't answer for an age. 'I don't think that's such a good idea.' He eventually replied. But I sensed his fear. And it aroused me.

'OK Jeremy, I'll have a dinner party instead. I do so like a good gossip.' And I hung-up the 'phone.

It rang almost immediately. 'Ilene.' He whispered fearfully, 'Of course I'll come.'

I laughed softly into the 'phone, 'And you'll bring your new dress?'

Now the silence was deafening. And I wondered if I'd gone too far.

'My dress?' He finally asked faintly.

'Your dress.' I replied. And I hung-up and went shopping!

He was on time. Very pale and wearing a silk shirt, jeans and trainers. He looked adorable. And he was holding the box I'd sent him his dress in! I pulled him inside and kissed him. He shivered in my embrace. 'Why don't you slip into your new dress while I pour us both a drink. I can't wait to see you in your first skirt.'

He cringed like a beaten puppy! The blood simply drained from his face. I saw his eyes bright with unshed tears. Poor Jeremy, he had no idea what to do, or what to say.

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