Stockings and Heels

Shelia kisses Gavin lightly on the knee cap as she slowly pulls up the second black silky stocking up his long pale leg. Gently she straightens outs the seam along the back of his leg and then levels out the lacy tops around his quivering thigh. Shelia crawls backwards to allow Gavin to stand and take everything in.

Gavin had never done anything like this before, until he met Shelia online. They met due them sharing a love in 'pretty pointy Goth shoes' and gradually he let her know how much he loved the idea of wearing heels and looking sexy in stockings; and she loved the idea too. So this is how he ended near naked apart from pants and a t-shirt with Shelia on her knees in front of him admiring his legs coated in silk.

Shelia had laid out some bits for him to try on, to test the water so to speak. Including the stockings already on; that he couldn't help but caress, there was a suspender belt, and of course some amazing high heels that took his breath away. Seconds later the stocking were clipped to the suspender belt with Shelia grinning madly at the look on his face and his growing bulge. Lastly came the shoes... oh those shoes. Even when Gavin entered the room he felt his cock twitching from just the sight of them. He sat on her bed and allowed her to run her fingers up and down his leg and then she started to put those shoes on his shaking feet. She carefully did up the four straps that nearly reached to his knees so not to snag the thin material on the stockings. Gavin stood up wobbly but could not resist reaching down and touching his legs, starting at the extraordinary heel and stroking up towards his groin. He looked at Shelia as he realised what he was doing and stopped just before he got to where the bulge began. Shelia looked deep in his eyes reassuringly and took his hand in hers and placed them on his hot cock that was begging to be released and played with. Quickly Shelia pushed him so he was sat on the edge of the bed with his legs sprawled out not used to have an extra 5 inches on each foot. Still on her knees she starts down the bottom of his left leg and kisses upwards, slowly and softly enough for Gavin to start to breathe more heavily. As she slowly takes her time pressing her soft lips along the sticky PVC of his killer heels, tasting the plastic, Gavin eyes do not stop staring at her.

Shelia had never dressed up a boy before in women's clothes, even though she had often thought how sexy a man in stockings is. Before Gavin had arrived at hers she dressed herself up especially to please him. Starting off with stocking and suspenders and then some heels, but no where near as good as the ones she had in mind for Gavin. She then gowned her PVC mini dress that showed off her suspenders and breasts beautifully. Made up her face with lots of eyeliner and bright red lipstick and let her hair down. Shelia looked in the mirror and saw a dominatrix staring back. Shocked she wondered if it would be too much for Gavin as she knew it was all new to him too. As she thought this her hands were wondering her body, feeling her curves under the clammy plastic and reaching between her legs, to find no knickers, feeling how wet she was already. This made up the decision to keep the outfit. When Gavin arrived if it wasn't for the commanding yet comforting voice she had put on to try to keep to her worked out plan he would have pounced her, and when he saw those shoes he was putty in Shelia's hands.

Gavin fed up of being teased grab Shelia by the hair and pulled her face to his level and kissed her roughly at first allowing his tongue to search her mouth and teeth to bite her lips, then gradually he softened to lips barely touching as Shelia's hands had found there way into the little clothes he had on. Gavin let out a little moan and tilted his head back as Shelia lightly felt his hard cock in the palm of one hand and with the other cradled his balls squeezing ever so slightly. The hand holding his balls grew restless and went back to feeling his ever so soft legs while the other hand continued to jerk off his now oozing with pre-cum cock, getting faster and firmer. Gavin stopped Shelia by pushing her away with one of his glorious heels, as his confidence had grown along with his cock. Shelia looks up at Gavin with her big brown eyes realising the control was shifting. Still sat down Gavin pulled Shelia from her knees and got her to stand in between his legs pushed against his groin so he could feel her curves against him, unzipping her dress a little way he allowed his hands to explore her body, down her spine, over her nipples, between her legs quickly realising she had no knickers on. With this unexpected and pleasurable find Gavin stood up carefully but quickly to tower over Shelia. With a swift motion he had her stood up and bent over the bed and his cock deep inside her tight wet cunt, causing her to scream in pleasure at the forcefulness. Gavin grabbed her hips and thrust deeply into Shelia's soaked pussy making her cum fast and hard without stopping again and again. Loving the feeling of being in heels and feeling his stocking rub against Shelia's ass Gavin felt himself about to explode inside her. As Shelia's cunt exploded in yet another orgasm around his cock he couldn't hold on and fired his load deep inside her causing her to cum yet again.

Slumped on the bed still in drag, Gavin turned to Shelia who was curled up in his arms and said "we should do this again... very soon."