Involuntary Sissy Pt. 02

All the clichés about love have started to come true for me. They seem to be taking longer for the object of my desire, but I know that given time he will wake up to the truth.

When I met my boyfriend I had no intention of making it last. Ever since my first experiments with humiliating my lovers I found that I wanted to be rid of them after a while. The ones who seemed to like it bored me and the ones who didn't took too much energy to maintain.

My boyfriend, as I call him, was particularly reluctant to let me dress him up in girly nightwear let alone introduce him to pegging. In the end, though, I got my way.

I told him that wearing the satin didn't make him a sissy, only wanting to would do that, and distracted him orally long enough to let me get the silky floral shorts on him. The matching camisole took a little more persuasion but once on it had a pacifying effect.

I mocked him for being so feminine as I took his anal virginity and afterwards took a photo for posterity. I have treasured it ever since.

When he left the next morning, finally convincing me to return his clothes after some accomplished oral sex on his part, I told him that I'd be seeing him soon. It's something I always say to see the look on their faces, and his was nothing short of ashen.

This time, though, I realised that I wanted it to be true.

I tried a conventional approach first, messaging him through social media and ringing him at work. When I eventually got through he told me that he was sorry, but he did not wish to see me again. The tease.

I waited outside his office but rather than confront him in such a busy space I decided to follow him home. It was a lovely ground floor flat with nice big windows that I could gaze through from my car. When I rang his mobile phone, the number of which he helpfully gave out on his office voicemail message, I could see him checking his screen before ignoring the call. He looked so cute when he frowned. He looked cute doing anything.

If a conventional approach would not work, more unorthodox methods would have to come into play. I bought him a lovely pair of knickers in the same floral pattern as the nightwear he wore for me and sent them to his office with a number to call. It wasn't my usual phone, but a pay-as-you-go one I bought for the purpose. He was my special project and it had occurred to me while watching him at home that it was like being a secret agent. Having a "burner" phone seemed only fitting, and given his wilfulness it made sense to have deniability.

You can imagine how disappointed I was when he didn't ring. I decided to resume my vigil outside his flat. When he returned home there was a parcel waiting for him, which he opened in plain view in his sitting room. He held up the stretchy floral mini-dress, in as close a pattern as I could find to his knickers, before throwing it across the room. He was on his phone for the rest of the evening, gesticulating angrily as he spoke to whoever it was. I wondered if it was a woman. Who was she? What did she have that I did not? He should have been calling me.

As I sat in the car I browsed the internet for private investigators who might be able to let me gain better access to his life. I realised that I had a trump card that might prove irresistible. The photo of him looking demure in his girly outfit, so precious to me, would remind him of the love we shared.

Before I drove back home I posted a job on a freelancing website popular with coders, offering a reward to anyone up to the challenge of a bit of corporate website hacking.

It was lunchtime the next day when I saw him again, in the lobby of his office building.

"Hi," I said, with a big smile. I had dressed in a way that I hoped would be distracting for him. Lots of the women in his social media posts had their hair up and wore hooped earrings and pale pink lipstick, so I had done the same. I reasoned that it would also do my chances no harm to wear a fitted blouse and pencil skirt.

He told his colleagues that he would catch them up and took me aside. I cocked my head to one side as he told me that I needed to stay away from him and made various unconvincing threats.

As he wittered on I took out my phone and brought up his profile page on his company's website. I asked him how often he thought people looked at the page and showed it to him on my screen. "I'm sure we can clear this up," I said as the sight of him as a freshly fucked sissy sank in. "We should talk somewhere private, don't you think?"

I said that the company's IT department could probably sort it out in a few hours with only a handful of his colleagues seeing him like that, but I could offer a more discreet solution.

Dazed, he agreed, looking towards the exit.

"No, let's go into your office," I said. "Go over to the reception desk now and get me a visitor's pass. Are you listening to me? I'm not in a mood to repeat myself."

He did as he was told and took me up in the lift. He mentioned a conference room, but I said that if it had glass walls he might prefer the seclusion of a lavatory. "Did you keep the knickers I sent you?" I asked. He looked mortified. I pressed him. He admitted he had not.

"It's alright, I have another pair for you. Go in there and put them on." I followed him into the ladies' room and waited by his chosen cubicle for him to oblige me. "I don't imagine you kept the dress, either," I said, throwing one at him in the same manner as he had thrown my gift across the room.

He didn't need any further instructions. He pulled the shiny lycra dress over his head and his arms into its sleeves. I smiled as he tried to tug the hem lower than the tops of his thighs.

As he completed his look I admired the décor of the bathroom, which was quite distinctive. It made an excellent background for another photo.

I joined him in the cubicle and locked the door. "Your profile page will automatically revert to normal in a few minutes," I said. "But we're not in any rush, are we?"

I ran my hand between his legs, feeling the tautness of the silk. With one hand I cupped his chest, running a thumb over his nipple. The other stroked across the front of his knickers, my palm pressed gently against the shaft of his cock while my fingertips scratched the head.

The intense blush I remembered so fondly from our first encounter had returned in earnest and I couldn't resist stealing a kiss.

He was just starting to protest when we heard the sound of a door opening and the clicking of heels across tiles. I widened my eyes theatrically as I broke off the kiss but my hands continued busily.

When he moved his hands in what looked like an attempt to push me away I wagged a finger at him. "I'm in charge," I whispered.

He bit his lip - coquettishly, I thought - as he suppressed a moan. The woman in the next cubicle was admirably quick, but even so I had teased a spot of precum onto the front of his knickers by the time the door banged behind her.

I tutted as I pulled the knickers down to his thighs, then sat him on the loo seat. "Hold it steady for me," I told him. I held his gaze lovingly as I lowered myself onto him.

No sooner had I set a rhythm than the door wafted open once more. It was tempting to carry on regardless, but I liked the desperation in his eyes as he silently pleaded with me not to let us get caught. I switched to a circular grinding motion, slow enough to be quiet but deeply pleasurable for me. I sighed softly into his ear, causing him to flinch, then sighed again.

I don't think that our neighbour heard anything before she left but by now I was beginning not to care.

"I see the way you look at me," I said once we were alone again. "I know how much you need me." I introduced thrusts as I continued my circular pattern, small at first then increasingly powerful. "We are going to be such sweethearts."

I felt a rush of anticipation and I wanted more shame. "No one here needs to know about your dressing up fetish," I said. "It can just be our little secret. Hmm?"

I was gasping a little now. "Yes? Darling? Yes?"

He squeezed his eyes tightly and with a sob he tensed inside me. The sensation pushed me over the edge. I let my head tip backwards in abandon as my body went into spasm. Even as I recovered my composure I could feel him pulsing still. His crestfallen look as he failed to keep control set me off once again. I folded my arms around his neck and pulled his face tightly into my chest where he belonged.

"Well darling," I said as I edged him out of me. "Let's get this thing off."

I peeled the dress upwards but gave a tut as he tried to shuffle out of his knickers. "Those stay on. Pull them back up."

He balefully complied.

I checked the pockets of his trousers before I handed them back and confiscated his house keys and some cash from his wallet. "I want to see you wearing your knickers when you get home," I told him, jingling the keys? I cupped his cheeks for a lingering kiss. "Don't be late."