Now Or Never
Add: 8 July 2016 / 00:00
He was nervous as he drove to the mall. He had to remind himself that nobody knew what was really going on, and that men purchased lingerie all the time for the wives and girlfriends. Except his purchases wouldn’t be for his wife, who had unceremoniously left him two years earlier with little explanation. He had revealed a few of his fetishes and kinks to her, which she had given off the impression that she was okay with at the time, but that had all been a façade. Apparently she wasn’t as okay about it as she was letting on. Her loss, he tried to tell himself, thinking it better that she had left him so he could find someone who embraced his feminine side and his fetishes. That was yet to happen, but he knew that he or she was out there. He found a parking space and made the trek across the parking lot, trying to calm his nerves. What if the shop assistant knew that the lingerie wasn’t for a woman? What if people knew that it was for him? What if I see someone from work? He thought, stopping just shy of the automatic doors. Be brave, he told himself, now or never. It surprised him that no one gave him a second look when he entered the lingerie store, though why that should be he didn’t know. Men purchased lingerie and underwear all the time, how should he be any different? He had a quick look around, spotting several nice bras and corsets on the display mannequins. He had a clear idea in his mind of what he wanted, and with some help from the young and pretty store assistant, he found what he was after. He then went upstairs to the shoe store and purchased some sexy red heels. He found that he couldn’t get home fast enough. Short of breaking the speed limits and several road rules, he pulled up in his driveway and made a dash for the front door, locking it behind him, unplugging the phone and running to his bedroom. He threw off his clothes with gusto, removing them quickly and throwing them on a pile in the center of the bed. He picked up the bag of lingerie and removed everything, picking up the red lacy underwear he had brought. Now or never, he thought as he held them up. As he put them on, he found that he had an erection, and once the panties were fully on, his cock strained against the fabric in a way that was tight and pleasurable for him. A little see-through lacy camisole was next, which he slipped over his head and pulled it down, covering his torso. As he looked at his reflection, he felt as if grew ten times harder in his lacy panties. He was straining to masturbate and explode all over the sexy, lacy lingerie, but not just yet. The experience, nor the look was complete. Not just yet. The next item he put on was a pair of nude silk thigh high stockings with lace around the top. These sat very comfortably around his thighs, and he liked the way they looked and felt on his skin. The last item left for him to put on were the red heels. He opened the shoe box and stared at them, admiring the shiny redness of the leather, the intoxicating new shoe smell, the pointy heel and the fact that they were so distinctly feminine, so sexy and commanding. He had worn heels a few times before and had sort of mastered walking in them. He wanted to work up to stilettos, which he thought the epitome of girly, sissy sexiness. The shoes he had purchased were only slightly higher than a kitten heel. All in good time, he reminded himself. He had time to acquire different types of heels and make his way through the selection until he was confident in wearing all heeled shoes. He sat down on the edge of the bed and gently slipped the heels onto his feet. He admired the way they looked on his stocking clad feet. He gently stood and looked in the full length mirror, mounted to the wall opposite the bed. His erection was visible and protruding against the lacy fabric of the panties. True, what he was wearing he would not deem a ‘full outfit’ but he reminded himself that he could work up to that. All in good time, he told himself once more. This was just the beginning stage. This was merely the first level of his cross dressing, lingerie fetish. The next few levels included bras, garter belts, suspenders, corsets, even higher heels than the ones he was wearing, wigs and makeup perhaps, and, he hoped a willing male or female partner who embraced his feminine side as much as he did. That was the dream for him. He walked back and forth in front of the mirror, liking the way he looked in his girly getup. He then walked a few laps around his bedroom, getting used to the feel of the heels and trying to control his footsteps. He had a new admiration for women now, never realizing before that heels could be this uncomfortable or painful even. The more he wore them though, he would get used to the feel and come to love them. He just knew it. Now or never, he thought as he learned to walk in the heels. He made sure the curtains around the house were pulled shut. He didn’t want people seeing him just yet, he wasn’t that comfortable. He had to get used to it himself before he let other people get used to it and see him. He then walked around the house in his lingerie and heels, liking the sexy click, clack sound of the shoes on the wood floors in the hallway and living room. The front door was locked and the phone was off the hook, which meant he had some time on his hands and that no one would disturb him. He tried to settle down and get on with his afternoon as normal, doing the housework dressed up, but as time went on he could no longer ignore the rampant erection in his lacy panties. He had to masturbate, the urge was strong, now or never, but he managed to suppress that urge just enough and take some sexy selfies of himself dressed in the girly, sexy lingerie. These would be for future reference - a few secret snaps of him dressed up. He decided to name this collection of secret, sexy, selfies ‘the wank bank.’ They would always be there for him to refer to whenever he wanted to masturbate or perhaps to use as a guide for his next lingerie purchases. After taking the snaps, he lay down on his bed and rubbed himself through the material of his lacy red panties, loving the way it felt against his cock. He slipped his cock out the side of the panties and was soon jacking it vigorously, loving the friction from the panties against the base of his cock. With his right hand he was jacking off, with his left hand he fondled his balls through the fabric, imagining that it was another man’s touch on him. He had been with another man only once, back in college. This was before the cross dressing and the lingerie fetish of his, when he was still exploring his sexuality. It was a guy from one of his classes that he was quite friendly with, Eric was his name. One night they had been drinking together in Eric’s dorm and out of nowhere, Eric leaned over and kissed him. It had been odd at first but not unpleasant. Soon Eric was blowing him, sucking him as if his life depended on it. They then switched around and he blown Eric. The relationship never progressed past oral sex, and soon after completing college, he met his wife Ruth, married her and lived somewhat happily ever after. He was imagining Eric fondling and jacking him now, admiring the sexy lingerie he had put on and the effort he had gone too. He imagined Eric’s warm mouth engulfing the head of his cock and then eventually his whole length. He groaned when he thought of this. It was so hot to him. He imagined Eric liking his feminine side and commending his talents for being able to pick out sexy lingerie. It was all too much for him, he was building up fast. The feel of the silky stockings, the heels, the lacy panties and the sexy camisole, imagining Eric sucking him. With one loud groan he came, several large spurts covering his lace clad torso and running across the material. He breathed out deeply and relaxed on the bed as he went flaccid. He would definitely be doing this again.