I Dressed My Boyfriend in Women's Clothes

I had always been the one in control in our relationship. It’s not that my boyfriend was totally submissive or anything, but more that I just had a more dominant streak. If I suggested something, we usually did it and we often used to joke about how I wore the pants out of the two of us! But whenever we said this, I used to think that what would really be interesting would be if I actually dressed my boyfriend in women’s clothes - I wear the pants, he wears the dresses. Sometimes, I suspected that he imagined it too, but I knew he would never say anything first. He would wait for my lead.

One night, on a quiet evening at home, I decided I was going to go for it. I knew him well enough to know that the best way to go about this was to come straight out with it. He’d be surprised but he’d do as I asked. “I’ve always wanted to dress you up in women’s clothes,” I said. His head whipped round, his eyes wide. I quickly added, “let’s face it, you’ve definitely got the legs for it,” with a reassuring smile. Looking uncertain but intrigued, he replied, “ok”.

Taking his hand, I led him up to the bedroom. I started to undress him, to unpeel the layers of his male clothes and to look at him naked, to think of how I would feminise him with this new look. The best place to start of course, I thought, is lingerie. I walked over to my lingerie draw and pulled out a silky, black basque with matching silk panties. Looking over at him, I smiled as I then reached for a pair of my smoothest black stockings, “and we’ll need these of course.”

His eyes were fixed on the underwear as I walked back to him, never having worn anything like it before in his life but anticipation building in him. “This will give you the shape you need to look like a woman,” I said, fitting the basque around him. I walked around to the back and pulled on the lace to nip in the waist, tying it up and running my hands over his feminine curves. I then picked up the panties, slowly sliding them up his thighs. He shuddered slightly at the light, soft touch of the silk against his skin. “Sit down on the bed,” I instructed him. I carefully, placed a stocking at the end of his foot and gently slid it onto his leg, smoothing it against his skin as I moved upwards. I took the suspenders at the top and clicked the stocking into place. His face flushed, I knew he had enjoyed the delicate touch of the nylon and so was extra indulgent when putting the second one on him. I caressed his leg as I moved up to the top of his thigh, complementing him on his long, slim and feminine legs.

And what better way to show off a great pair of legs than with some sexy heels. My size wasn’t too much smaller than his and I knew just the pair that would fit. Killer heels, with a metal stiletto but with a dainty strap around the back of the heel. “You’re going to have to learn how to walk in these fuck me heels,” I said, winking at him. He half smiled back at me. There were still some nerves, I could see them in his face. I knelt down and lovingly placed my favourite pair of heels on him, gliding them on easily over his stockinged feet.

“Stand up and let me look at you,” I said to him. As he raised himself up, I saw a totally different figure. The shape was lean with a curve around the hips and as he turned around for me it made his behind more shapely too. To complete the look, he needed the icing on the cake of womanhood - make up. Sitting him down on the bed again, I got my make up and started to get to work on him. Full dark, smoky eyes and red lips with a hint of gloss, his face was beautiful and seductive. How can I not share my long, black haired wig with him to complete the look? I’d worn it many times when dressing up for him. Now I realised that when he’d run his fingers through it he was yearning to wear it himself.

“Now,” I said gently taking his hand in mine, “come see how beautiful you are my sweetheart.” I took him over to the mirror and let him take in the vision that was before him. He had never been so resplendent, so enticing. His hands hovered over his figure, wanting to touch the soft fabrics on his skin. He hesitated, so I did it for him. Running my hands all over him, down to his thighs and between his legs. I had dressed my boyfriend in women’s clothes and now I was going to enjoy deflowering him!

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