Deflowering him gently

I shouldn't have done it.

I used to feel guilty about it, but perhaps putting my boyfriend in lingerie was the best thing I ever did for him.

Alec and I were what others thought were sweethearts, feeling our way through young love, earnest and unworldly. We were hand-holding, first-kiss-at-the-prom lovers with sheltered pasts and open futures.

And so it might have carried on, wholesome courting leading to a path familiar from our own upbringings, but curiosity drove a wedge between us.

He was emphatically not a curious type, never more clearly expressed than his wish to preserve his chastity till his wedding night. I thought this cute, then quaint, but I always thought he would bend in his will.

We were allowed, by him, to do other things short of sex: fumblings that went nowhere or, latterly, simmered to a frustrating anti-climax as he excused himself.

We would kiss and fondle. We would undress one another, stroke each other's backs, fall asleep in an embrace, his desire protruding gingerly into the folds of my nightie.

I was curious. My friends, in person and especially online, became my vicarious sex life. I harvested their crop of gossip. I reaped them, the stories of first-date sex, comfortable sex, bad sex, getting-the-spark-back sex, break-up sex, make-up sex, sex that dared not speak its name and sex that did so freely.

The consensus, among those who knew, was that we had to get over the hump.

The closest we had come to sex was on his birthday, when I managed to get him naked from the waist down and rubbed myself against him. We were almost there, only the thin fabric of my knickers between us. I held him as I caressed his cock against the satin, convinced that now was the moment. I pushed the knickers down and he rolled away, apologising as he retreated to the bathroom to purge himself.

The apology did nothing to disperse my feelings. I lay in bed, busying myself as he was doing a locked door away. As I tried to wish away my resentment I realised that there was something there to build upon. Something about my knickers.

I was prepared when he next had to excuse himself, no more than a few days later. I pressed a pair of my briefs into his hand and told him that he could take them with him to the bathroom. He said nothing but as I listened at the door I could hear the ruffle and rub as he stroked.

I avoided his advances for the next two weeks, enough to find encouragement in some of the kinkier online forums. Enough, also, to give an edge of hunger.

It was a Friday night when I deemed him ready. After dinner I told him to go to our bedroom and strip down to his underpants. I made him wait.

I appeared in the doorway with a present for him, a small gift in pink tissue paper. He carefully prised the taped ends open to find a pair of black satin knickers, unshowy in their cut but with scalloped edges to the leg holes and a sheer panel at the rear. He stared uneasily at them draped across his thighs. "These are for you," I said. "I'm going back downstairs. Call me when you've put them on."

It took him two goes. When I first returned I found him still in his underpants, primed to make excuses about not wanting to do it.

I told him it was fine and to call me again if he changed his mind. It took him five minutes to summon me back.

"Oh, that's much better, darling," I said. "You look so cute."

He did. The confidence of his bulging knickers was entirely at odds with the apprehension in his downcast face.

I sat next to him and allowed him a kiss while I fondled his bottom. I hadn't wrapped his next present. I produced a matching black camisole from beneath his pillow and helped him put it on, kissing him more ardently as I did so. It was little different from a man's vest, just with stretch satin instead of cotton and thinner straps.

"Doesn't that feel nice?" I asked as I caressed his nipples through the fabric. "Doesn't that look nice, Alice?"

I kissed him again before he could murmur his answer. "It was a rhetorical question, Alice," I said. "You know what that means do you, Alice? It means you don't have to answer."

I used my most patronising tone as I laid a hand on the front of his knickers.

"You're a good listener, Alice. That's one of the many things you're good at. You're good at doing what you're told, aren't you?"

I wanted a reply this time. "You can answer that one, Alice."

He looked at me, confused as I rubbed my palm in a gentle circle.

"Is Alice good at doing what she's told?"

He nodded meekly.

I helped him to lie back on the bedclothes.

"If Alec were here, none of this would be happening," I said, risking a mention of his name as I placed my legs either side of his thighs. "But Alice wants this. She wants it so, so much."

I traced the outline of his cock with my fingertips, pressing the soft material against the head. I stroked, my palm gliding backwards towards his closely wrapped balls, then smoothly forwards onto and over his tip.

He sighed. He was slipping dreamily into the character I had made for him, the pliant Alice, playful and susceptible to her desires.

I developed a slow rhythm for his cock. With my other hand I pushed his face sideways, the better to kiss him between his gasps.

"Good girl," I whispered. "Such a good girl. Looking so pretty for me. Do you want me to go faster, Alice?"

He cooed his assent, as if I needed it. I had him now.

The knickers struggled to contain him as I persisted in my attentions. I let the tip protrude from the frilly waistband at first, then slid my hand inside to release it from its silken restraints.

I rose on my knees over him while I continued to stroke. If he had been wondering whether I was going to stroke him against my own knickers, he was disabused as he felt the wet sensation of my skin against his, then suddenly around him.

"Oh Alice, my darling girl."

His eyes widened at the shock of it, a sensation like none we'd known. With just the head of his cock inside me we were one. I lowered myself slowly into our new embrace.

I felt like dropping the roleplay but I needed to know he wouldn't try to break away.

"I can't wait to see you in a dress, Alice," I said, bringing his mind back to his uninvited persona. "I wonder what dresses you like."

I propped my hands on his chest, soft beneath me, bracing my arms while I found my rhythm. I rocked myself back and forth and him in and out.

I nurtured his confusion as I went, describing dresses from my wardrobe as if they were his. Would Alice choose the prom dress, fuchsia pink and boned at the bodice? Or the witch fancy dress costume? Perhaps we could buy her something.

"Something cute and girly, hmm?" I said, panting as he was. "Or something else?"

I dipped to give him encouraging kisses the pleasure building within me.

It was close now. I was close. I leaned away again, perched on his hips and gripping his thighs tightly with my hands. "Oh Alice," I said, distracted, almost using his real name. I was leaning back now, exploring ways to pull him deeper.

"A cute dress just isn't you, is it? You need something... trashy."

I was on a plateau of pleasure and could feel another one rising. He groaned quietly, as if despite himself.

I let out my first big cry as a convulsion ran through me, squeezing us together deep inside.

I laughed at the joy of it, and the anticipation of the next one, so close.

"A silly dress, a naughty one, one to show what you really are."

Here it came again, a fireburst of nervous energy.

"You know what you really are, Alice?"

He shifted his torso, arms taut as he gripped the bedclothes in bunches. He was fighting an urge too powerful to resist.

I felt my spasm beginning again, subsiding, resurging.

His eyes, screwed tight for so long, sprang open as his mouth formed an O.

"You're a slut, Alice," I said, a last verbal effort before I squealed my climax. I felt my own pulses echoed by his. He cried out, either an "oh" or a "no" or a mixture of both. I kept at him still, wringing the pleasure from both of us, grinding till I was light-headed.

I fell slowly forward to lie on top of him, a dead weight on his silky chest, faint but fulfilled.

He would need me to tell him what to think, but I needed a moment. Just a moment to recover.

There were tears in his eyes when I looked at him again. I cupped his cheek. "Go to the bathroom now, Alice. When you come back, you can be Alec again."

We talked on his return, about how good it had felt to be Alice and his knowledge that the persona couldn't fully take away his compromise. I told him that we had sacrificed nothing but our ignorance. We weren't part of an Old Testament story, we were human beings being human. Alice was just a catalyst for his self-expression.

He didn't know, he said.

I wondered aloud if we would ever see Alice again.

He thought not.

How little he knew.

But that is another story