She kisses him lightly on the kneecap as she slowly pulls the second black, silky nylon stocking up his long, pale leg. Carefully, she smooths the seam along the back of his leg, then the lace tops around his trembling thigh. She crawls backwards to let him stand, taking it all in. He had never done anything like this before, until he met her online.
They met because they shared the same love for beautiful pointy stiletto heels, and little by little he let her know how much he loved the idea of one day wearing stiletto heels himself, looking sexy with a garter belt and nylon stockings; and she loved the idea of one day seeing him like that. So there he was, almost naked except for a t-shirt, with her on her knees in front of him, admiring his nylon-covered legs. She had laid out a few things for him to try on, to test, so to speak.
Among them was a pair of nylon stockings that she was already wearing and that he couldn’t help but caress. There was also a garter belt and of course a pair of amazing stiletto heels that took his breath away. A few seconds later, the nylon stocking was attached to the garter belt, and she laughed excitedly at the look on his face and his growing cock. Last came the stiletto heels … oh, those heels. Even as he entered the room, he could feel his cock twitching at the sight of those stiletto heels. He sat down on her bed and let her fingers slide down his leg, and then she began to pull those heels on his trembling feet. She carefully lifted the four straps, which reached almost to his knees, so as not to catch the thin fabric of the nylon stockings. He stood a little shakily, but couldn’t resist reaching down and touching his legs.
Starting at the extraordinary heel and stroking up to his crotch. He watched her as he realized what he was doing and stopped just before reaching his stiff cock. She looked reassuringly deep into his eyes, took his hand in hers and placed it on his stiff cock, which begged to be released and played with. Quickly she pushed him back so that he was sitting on the edge of the bed, his nylon-clad legs stretched out, not used to having twelve-inch stiletto heels on each foot. Still on her knees, she started along the bottom of his left leg, kissing upward, slowly and gently enough to make him breathe harder. As she slowly took the time to press her soft lips along the sticky PVC of his killer heels, tasting the plastic, his eyes continued to stare at her.
He watched her excitedly as he realized what she was doing, and she stopped just before she got to where his stiff cock was. She had never dressed a young man in drag before, although she had often thought about how sexy a man in nylons could be. Before he came to her, she dressed in a very special and sexy way to please him. Starting with a pair of tattered nylons, a garter belt, and then a pair of heels, but not nearly as high as the ones she had in mind for him. She decided not to wear a bra and a thong. Then she put on her PVC mini dress, which showed off her suspenders, nylons, and breasts beautifully. She made up her face with lots of eyeliner and bright red lipstick, and decided to let her hair hang loose.
She looked in the mirror and saw a dominant woman. Shocked, she wondered if this would be too much for him, knowing that this was all new to him as well. As she thought that, her hands naturally went over her body, feeling the curves under the clammy plastic, and ended up between her legs, feeling how wet she already was. That was reason enough for her to keep the outfit on. When he entered her, she knew immediately that he would have jumped her if she had not used the commanding but reassuring voice to try to stick to her elaborate plan. And when he saw those heels, he was like wax in her hands. Tired of being teased, he grabbed her hair, pulled her face toward him and kissed her roughly.
First he let his tongue explore her mouth and teeth before biting her lips. Then he gradually softened to lips that barely touched, just as her hands had done. She found her way into the clothes he was wearing. He moaned slightly, holding his head back as she lightly felt his hard cock in the palm of one hand, squeezing his balls a little with the other. The hand holding his balls became restless and stroked down his soft nylon legs again, while the other hand continued to jerk his now pre-cum oozing cock, faster and faster and harder. He stopped her, pushing her away with one of his huge stiletto heels as his confidence grew along with his cock. She looked up at him with her big brown eyes and realized that his control was shifting. He sat up, pulled her up and made her stand between his legs, her nylon legs pressed against his crotch so he could feel her full breasts against him.
His hands caressed her nipples, between her legs, and he soon realized that she was not wearing a thong. After this unexpected and pleasurable discovery, he stood up carefully but quickly, towering over her on his stiletto heels. With a quick motion, he had her standing, bent over the bed and thrust his cock deep into her tight, soaking wet pussy, making her scream in pleasure at the force with which he was fucking her. He grabbed her hips and thrust his cock deep into her soaking wet pussy, making her cum fast and hard. He enjoyed the feeling of walking on stiletto heels and feeling his nylon stocking rub against her ass. He felt like he was about to explode in her pussy. When her pussy exploded in another orgasm around his cock, he could no longer hold back and squirted his load of cum deep into her pussy, making her come again. Collapsed on the bed, still aroused, he looked at her as she lay in his arms and said, “We should do this again … very soon”.