Anything Goes

He could feel the tip of her cock pressing against his asshole. His arms and legs bound to the bedposts of their bed. The silky fabric of her nightie, her undies pressing against his erect cock, the smell of her perfume behind his ears, it was all terribly erotic and his cock exhibited his excitement. He couldn't hide it as much as he might want to.

His girlfriend had come home early from a meeting and she was surprised to find him in her panties, her nightgown, her jewelry. He was dressed like her, admiring himself in the full-length mirror. He had not seen her, initially, and so she watched him. She watched him prancing around, practicing walking like a woman, correcting himself and his movements as he went along. His erection was evident, hard to hide and while she was shocked, she found that the more she watched him, the more erotic she found it as well. It was endearing on some level but she also knew that he would need to be punished for this, she would have to teach him a lesson.

When his reflection finally caught hers in the mirror, he dissolved. He couldn't imagine what to say or how to say it, how to explain what he was doing and why. It was all too overwhelming, so he just stood there. His cock bulging through the nightie, his legs stretching the fabric of her thigh-highs, the gold earrings on his earlobes, making him look foolish and girlie. How could she understand, he thought. How could she know how this made him feel, how complete and whole?

He stared at her dumbfounded. He began to take down the straps of the negligee but she told him, in no uncertain terms, to leave it on.

"You want to know what it feels like to be a woman?" she asked. "Well, I will show you. Lie down on the bed, face down, spread your arms and legs. I will not stop until you understand, fully, what it is like to be penetrated, no matter what protests you make. Tying you down will ensure that I can finish what I start."

He slowly made his way to their bed, crawling on the bed until he was centered, then lying down, spreading out his limbs. He then waited. He couldn't admit to himself, much less to her, that this is what he dreamed of, fantasized about, wanted more than anything else in the world.

She took four of his neckties, circled one around each limb, so that he wouldn't be able to slip out of them and anchored him, securely, face down on the bed. No words were exchanged between them. It was eerily silent as she went about her work and as he prepared for what was to come.

He was already hard, and lying on the bed, his cock rubbing against the silky fabric only made him more excited. He couldn't imagine what she was going to do to him. The kinkiest thing they had ever done together involved a feather and a blindfold, so his thoughts of what might happen next were pretty limited.

When he felt her come onto the bed, her weight shifting the mattress, he was anticipatory, to say the least. He was helpless and out of control and excited by the thought of anything goes, to use the words of the illustrious Cole Porter.

He did not, in a million years, expect to feel a cock pressing against his asshole. He thought she might stick a finger up his ass, to mock penetration of some kind but this was a complete and very welcomed surprise. Where did she get this cock? How did she know how to use a strap-on? His mind was whirling, like a dervish but he didn't want to miss a moment of this adventure, so he tried to keep his thoughts to the here and now.

"You want to feel this cock up your ass, do you?" she asked as her body spread itself over his. "You want to be penetrated like a woman? Fucked? You want to know what it feels like to have something come in to your holes? This I can do for you and happily."

She lifted herself off of him, leaving him suddenly feeling insecure and cold. He couldn't imagine what he must look like, in her nightie, thigh-highs and panties. What she must think, it was almost too much to bear, so he tried to shut down his mind and just go with it.

"We should start by lubing you up, making sure you are wet and wide enough to take my cock. After all, that is what you do for me." The cold lubricant hit the crack of his ass, torturously slow. She was enjoying this, taking control, drawing out the good parts, making him wait, patiently. One long squirt from the pump top began to drip down his crack, then another, and another. He'd never felt anything so exciting as the liquid running down his asshole - until she began to rub the cold gel against his ass. His hips reacted, instinctively, as his ass pushed up to meet her hand.

She complied, at first, she began to push her finger into his asshole, gently, pushing pass his sphincter. He had never done this but neither had she and she wanted to be sure not to permanently hurt him. When she saw how his body responded, she was again a little shocked - she hadn't expected such enthusiasm from him as her fingers found their way into his hole.

She left one finger in his asshole as she used the other to just rub his ass, his ass cheeks, his lower back, trying to accustom herself to this area of his body. She was usually much more focused on the front, this was new territory. Almost instinctively and without thinking, she spanked him, her hand landing hard against his left buttock.

He didn't respond as she thought he would, she thought he would protest but instead, he moaned, he liked it! She did it again and then again and again. It seemed to turn him on as nothing she'd EVER done before to him or with him, ever had. His hips were moving in a circular motion, pushing back against her finger and he was moaning, loudly, with an occasional "yes, thank you, yes" tossed in. It was like it wasn't even him, the man she knew and loved. It was as if he had been replaced by this man she didn't know at all, one she needed to learn, to study but she had to admit that she was getting almost as turned on by this scene as he was.

She noticed some reeds that she kept in a tall vase in the corner of their room and she pulled her finger out of his ass and walked over to fetch one. She stood on the side of the bed and whacked it down on his backside. It landed, expertly, across both cheeks, leaving a beautiful, thin, red line. His ass was moving, inviting more, so she began delivering the whacks in pairs, waiting a bit, seeing if he was still up for more, and he was! Many, many more. Before she realized what was happening, his ass was covered in red lines, and she was beginning to cover the tops of his thighs with the same.

But he never cried out, he never objected, his body just took it, whatever she doled out. She began to worry that all of these little welts might become infected, they looked pretty horrible and the more sinister side of her was coming out as well.

"Don't move," she teased him, as she left the room again. He heard her reenter, just as he heard the spray before he felt it. His mind almost went numb when he felt the rubbing alcohol being spread onto his open wounds. He cried out, loudly, this time protesting with all of his might. She thought he might pull the bedposts off the bed but the ties withstood his pain and anger.

"What the fuck are you doing?" he screamed. "Stop it! Please! Stop!"

"I may have finally found your breaking point and that is a good thing for me to know. Whipping, yes. Wetting your welts with rubbing alcohol, no. Got it! I am relieved to know that you actually have limits after what I have just done to you. I was beginning to wonder if 'no' was even in your vocabulary," she said to him in a very calm voice.

"May I ask how long you have been dressing up in my clothes and wearing my perfume and stretching out my panties and my stockings? Has this been something that you only do with my clothes or did it start way back when and I am just late to the party?" she asked him, expecting full disclosure.

He was too embarrassed and too ashamed to answer her, so he stayed quiet, groaning as the alcohol seeped into his skin.

"I asked you a question," she said louder this time, "and I expect a fucking answer!" The reed hit his ass, sending a flash of pain straight through his brain but she received no response from him. She tried the reed again but only groaning came out of his mouth.

"Fine, we will do it your way," she said, menacingly. "I never told you this but I had a fling with another woman just before I met you. She gave me the gift of a strap-on dildo because I missed having a man around and she hoped that having my own cock might allow me to stay in the relationship with her a bit longer. In fact, her plan backfired. It only made me want a real cock that much more, preferably one that was actually attached to a man, a real man. Odd that I picked you next. A man who has a cock but dresses it up in lingerie and lipstick. What a piece of work you are."

"As you can see," she continued. "After I found my alpha male traipsing around our bedroom in my fucking nightgown, I figured I would dig out my old trusty strap-on and let you know what you've been missing. I hope you are as ready for this as you might think you are because if memory serves, this thing has a little vibrator that rubs right up against my clit and once I start riding you, it's likely I won't stop until I cum and cum hard. So, be prepared, I am going to seriously fuck you."