Involuntary Sissy Pt. 03

It is forever two steps forward, one step back with my boyfriend.

Our first date had seemed so promising. He was charming and kind and was able to give me total control in the bedroom once we'd overcome his objections to wearing lingerie. The crumbling of his resistance to me pegging him was as beautiful as any act of love I have ever known.

Love crystallised for me then, and I know that one day he will be overwhelmed by it too. He needed a lot of help on our second date, though. It was only when I turned up at his office with the suggestion that I show his colleagues my photograph of him in silk that he let me be intimate with him again.

That was at lunchtime today, when I ended our tryst in the ladies' lavatories with high hopes for the future. I took the keys to his flat and did a little shopping while he stayed at work. I left him sitting meekly in his knickers, waiting to sneak back to his desk without being seen.

He had always been at his most devoted when wearing feminine clothing so when I let myself into his flat my first task would be to refresh his wardrobe. Some replacement underwear and a fancy dress costume would be a good start, I thought.

In the event, I did not have the chance. Not long after I arrived there was a rattling at the front door and voices as he and a woman came in, presumably with the aid of a spare set of keys.

I had been going to welcome him home, but the woman's presence put me on edge. I waited in his bedroom. There was a large gap between his bed and the floor and I shuffled myself into it as they began a search of his flat.

"There's no one here," the woman said, the bottom of her legs visible to me from my hiding place. They were good legs, from ankle to shin. She wore black fishnet tights and patent heels with ankle straps. I wondered if he liked that.

He entered the room and thanked her for helping him with his stalker. It took a moment for me to realise he was referring to me. Stalker? I almost snorted with irritation. What game was he playing?

She asked how he knew me. "Did you go on a date? Did you sleep with her?"

He was interestingly evasive. We had been on a date, he admitted.

She had forthright tone when she spoke. He would have to change his locks, she said, as he had been stupid enough to let me have his keys. She helped him to ring around for a locksmith but the best they could get was an appointment the next morning.

He asked her to stay the night, and it was here that I picked up something useful. There was a pause. "You'll have to sleep on the sofa," she said. "I'm serious. We can't keep doing this. We agreed to move on."

The room went quiet. I looked at their legs brushing against one another. Were they kissing?

"That's enough," she said finally, emphatically. "You're on the sofa."

So that was why he was denying our love. He still had feelings for this woman.

I had a lot of time to ruminate on my next move as I lay under that bed. It wasn't until she slipped beneath the duvet and I heard her breathing deepen that I dared to emerge. I looked at her and recognised her instantly from his Facebook photos as Marie, a pretty barista I had suspected of being a past girlfriend. As I slipped out of the flat with the clothes I'd failed to distribute I resolved to get to know her better. I'm sure we could be the best of friends.

***

It took almost no effort to find the coffee shop where she worked and I was there two days later, striking up conversation. It turned out that we had a lot of shared interests, which had been easy enough to learn about from her social media profile. She was especially keen on the idea of salsa dancing, although she was an absolute beginner, she said.

"Oh, me too," I said. "Although I've never been brave enough to go to a class on my own."

I returned to the shop the next day armed with a pair of reservations for a class. They cost a little bit of money but I told her airily that I had seen an advertisement for a free taster session. Would she like to come?

We went. It was a blast. We had drinks afterwards and I steered the conversation to ex-boyfriends.

She was reticent at first but after a round of pisco sours (listed as a favourite on her online profile) she listened intently as I recalled an ex who was ever hopeful of taking me back to bed. She told me that she had the same problem and was hoping it would just fizzle out. "Well, if it doesn't, come and ask me what I did," I said.

I declined to elaborate. I needed to plant a seed and hope to intrigue her.

When we parted she asked: "Same time next week?"

***

My longing for my boyfriend only increased as time passed, but my patience was just about still intact a few weeks later when I invited Marie round to my place for dinner. She brought a bottle of wine and so did I. The digestifs were probably the key to it, though. She'd had another encounter with him, she confided, and he had given her his puppyish look as he suggested that they go back to his place. "He's great company," she said. "But I can't spend time with him without him wanting to go to bed together. What did you do, when your guy kept asking?"

So I told her a story.

"I put him in knickers," I said. We both laughed. "I said that it would be the sexiest thing he could do for me."

I told her that my first plan had been to make our sex kinkier than he would enjoy. I imagined making him wear all sorts of fetish gear, but the clothing doesn't come cheap and it dawned on me that I could achieve the same effect with my own clothes.

"I told him that we could only have sex if he indulged me with a little role play," I said. "Once he was naked I gave him the girliest knickers I owned. They were white satin with a pattern of large pink roses, you know, and a little bow and frill around the waist. He was mortified."

Still, I told her, it wasn't enough to put him off. "He pulled on the knickers, so I kept going in the hope that he would refuse and I could flounce off. That way, if he ever suggested sex again I could put him off by insisting on the role play."

"Did he do it?" Marie asked. "Did it make him stop?"

I listed clothes my imaginary ex-boyfriend was forced to wear. There were fishnet stockings, a gold micro-miniskirt, a white satin blouse and finally the silk scarf I used to tie my hair. "I could tell he hated it, but his desire pushed him on. When I ran out of clothes options I told him to masturbate."

Marie giggled and told me to go on.

"It was quite a sight. As he stood there stroking himself I made him tell me how much he loved dressing like a girl. He pleaded with me not to have to say it, but he did as I asked. I told him that I always knew he was a sissy and it carried on like that till he finished. I teased him about it for a while afterwards, too. I didn't touch him that night and he's never asked me for sex since."

Marie found this hilarious and said that she would never have the courage to do something like that. I told her she could do it easily, and that I would help her if she liked. "I don't know," she said. I poured her another drink.

Not long afterwards she excused herself to go to the bathroom. As the door closed I took her mobile phone, entered the passcode I'd seen her type numerous times and found the text messages they exchanged. I got a vague sense of her style and sent him a message: "Feeling a little tipsy. X"

Once the message was sent I deleted it from her phone and returned the device to the table. It buzzed as she sat back down. She glanced at it and rolled her eyes. "Guess who it is?" she asked, then read aloud: "'I'm at home watching a film if you want to drop by. Kiss.'"

"Come on," I said. "We're getting a taxi. I'll coach you on the way."

One part of my plan that I was nervous about having to explain was why I had a miniature earpiece for Marie to wear. I was going to say that I had bought it to help me with giving a presentation, which sounded vaguely plausible, but I still worried that I seemed overprepared. It turned out not to matter. Whether it was the drink or the excitement of our mission she just accepted it as just another part of an already outrageous idea. She put it in her ear unquestioningly and immediately turned her interest to the bag of clothes I had put together.

"Alright," I said as the taxi drew up. "I won't be able to hear you at first, but leave the door on the latch and I'll let myself in after ten minutes. Then I'll be able to give you ideas through your earpiece. Till then, all you have to do is flirt with him and tell him you've got a surprise that you can show him in the bedroom."

"Do you really think this is a good idea?" she asked as we drew near. I fished a small bottle of brandy from my jacket pocket and took a swig before passing it to her.

"I'll be with you all the way," I said, paying the taxi driver and getting out. "I promise I won't let you down."

Marie was better at her part than I could have hoped. By the time I was through the front door they were in his bedroom and, I could tell from the men's clothing strewn about the hallway, he was at least partially naked. Their voices were too muffled to hear from any distance because the bedroom door was only slightly ajar, so I stationed myself by it and peered through the gap.

He was unclothed, but questioning why she wanted a role play. I whispered my first instruction into Marie's earpiece. "I want to feel like I know you properly."

She repeated the line verbatim.

"I want you to trust me completely so I can place my trust in you. It's a fantasy we're going to explore together."

She took a long golden silk scarf from the bag and playfully passed it around his neck, tying it into a big bow.

"That's a good start," she told him as I prompted her. "You're looking the part already."

She rewarded him with a kiss. He started to stiffen and whispered something about his affection for her.

"Good," she said. "Now, you're to do the rest."

She handed him the knickers. They were bright pink satin on the front with a see-through mesh panel on the bottom. He hesitated. He asked whether someone had put her up to this.

I gave Marie her next line. "This is a mistake, isn't it? I don't think we should be doing this at all."

She turned and marched toward the door, a look of relief on her face. He pleaded with her to wait. She put her hand on the door handle and glanced back to see him putting his feet hurriedly into the knickers. She paused as they went on. He looked at the bag containing the rest of the ensemble.

Once a man has volunteered to put on one item of feminine clothing there is little reason for him to object to another, but the dress I had chosen escalated matters to a new level. It was a fairytale princess ballgown, a vision of polyester satin as pink and lustrous as his knickers.

The blush disappeared from his cheeks as pulled it from the bag and his faced paled.

He stuttered something, an expletive perhaps. "You're not ready for this?" Marie asked. "It's alright. You can put your clothes back on. I'll go and get them."

She walked out and gestured for me to follow her into the sitting room. "I can't do this anymore," she said. "What if he wears it? It's too much."

I gave her the brandy bottle, to calm her nerves. She had only a brief sip.

"No more," she said. I noticed that she was starting to slur her words. "I've had enough."

"Okay," I told her. "Do one more thing and I'll take care of the rest."

She listened and nodded, pleased to be handing over responsibility.

We marched quickly back to the bedroom door and Marie went through. I chanced a peep through the open doorway and saw him standing awkwardly in the dress, the zip at the back unfastened but otherwise ready. Marie approached him unsteadily and reached for the bow of the scarf round his neck. She fumbled but fulfilled my instruction to turn it into a blindfold for him.

I smiled reassuringly and whispered as she passed me: "Good job. Have a lie down on the sofa in the next room and I'll tell you if I need you."

I watched her go and heard her sigh as she slumped into the sofa, fit to pass out.

I closed the bedroom door behind me. My love and I were together again at last.

I bent down to reach beneath his skirts and ran my hand up the inside of his thigh till I was cupping him. I gave him a playful rub through his knickers before lowering the waistband. His cock bobbed excitedly while I found my tube of lubricant. I moistened my hand and began a slow manipulation, twisting and sliding over the head to tease out a series of long groans that rose in pitch to delicate sighs.

I stopped to apply more lubricant, but this time I squeezed it onto his hand, which I guided to take up where I had left off. I zipped up his dress as he stroked himself before leaning close to his ear. It is hard to tell one person's whispers apart from another's, but in any case I kept my message concise: "Keep your eyes closed."

I gently lowered his blindfold before whispering: "Closed. Till I tell you. And I want you to tell me how much you love it."

I settled on the bed and got out my mobile device to record the scene. He stroked at first at the slow pace I had set for him, but his hand began to move faster and faster. He blurted out that he loved it as his skirts swished about his hips. His chest heaved against the tight bust.

I had to raise my voice above a whisper when his groans became too loud and frequent. "Do you want to come in your pretty dress?"

He panted that he did. He was close now. I wanted to take over but it would spoil the recording. I settled for reaching out to fondle his balls with the soft lining of the skirt.

"Are you going to come in your dress, princess? Yes?" I asked.

He repeated "yes". I moved his spare hand so he could take over my fondling, then ran my fingertip along the underside of his knickers, pressing the fabric against the contours of his bottom.

I wondered when he would recognise my voice. I sat back and spoke again as his head tilted backwards in what I recognised as the precursor to his orgasm.

"Such a pliant sissy," I jeered. "Come for me, my little pansy. Give yourself to me."

He opened his eyes, startled and bewildered. They shone in terror while his mouth formed an O. Short, uncontrolled grunts rose from his throat. His hand fell away but his body betrayed him. He looked into the camera as he came onto the floor. His eyes creased and his chin lifted in a look of surrender and disgust.

"It's a shame that Marie wasn't here to see it," I said as he tried to understand how this could have happened to him. "But this video is the next best thing."

I put the device away and beckoned him over. "Let's see how you'll persuade me not to show it to her."

I lay on the bed and used the scarf still tied round his neck to draw his head between my legs. Shattered, he crawled into place. I flipped my skirt over his shoulders so that it caressed the back of his head as he began to bob. He was doing such a good job that I almost wanted to keep my end of the bargain, but I knew that sooner or later Marie, at the very least, would have to know the truth.

Whether his colleagues, friends or family had to know was up to him. I had a feeling he would follow my wishes from now on, all the way to the altar.