A Wedding Night Pegging

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first and see just how compatible we are. It's just that I think the idea of the wedding night being such an important thing kind of died out when it stopped being about losing your virginity."

"I suppose you don't think it's appropriate for me to wear a "virginal" white dress either, then?" Naomi had replied, "Seeing as you think that the whole event is just full of played out traditions that are no longer relevant."

"No, no," Jon had answered, "You wear what you've always wanted. But I'm sure you'd look great either way. And I know the wedding night is going to be good, just like all the other great nights we've enjoyed together before and hopefully will for years to come after we're married."

"So, "good but not special" is what we're aiming at," Naomi had laughed.

"All I'm saying is that it would be more special if there was some kind of way that it involved losing your virginity."

And that had been the end of that. That was a few months ago. Tonight was the wedding. And after that, of course, the wedding night. The conversation hadn't really been raised since and Jon had forgotten he'd ever said anything of the sort. Naomi had indeed worn white and she'd looked great in it, as her new husband had known she would. She was normally a casual, jeans and t shirts, no make up, kind of girl, but today she wanted to feel special. With all eyes on her, all her friends who might have expected something a little alternative were surprised to see Naomi's curves squeezed into a very flattering, elegant ivory gown that sparkled in the candle light of the wedding venue.

Jon had certainly been impressed with his beautiful new bride and, whatever comments he might have unthinkingly made a few months earlier, as he twirled her around on the dance floor and gazed into her lively brown eyes, he definitely looked forward to the time when they would be alone together later in the bedroom. It would undoubtedly be something special, loss of virginity or not.

"Don't worry about tonight," his bride had whispered in his ear during the dance, "I've got something that will make it a wedding night to remember."

Now they were up in the bedroom together, Jon feeling almost as much nervous excitement as when it had been their first time together almost five years earlier, Naomi looking a perfect picture of his dream bride in her big white gown with its wide skirts.

"Remember what you said about the wedding night not being as special without it being the first time," Naomi said.

If Jon noticed the naughty smile playing across her lips then he didn't mention it. Instead he blushed a little at being reminded of a conversation that he had since forgotten, a conversation in which he had unthinkingly said something that made it sound like he cared less than his new bride about the wedding and all the stuff that surrounded it.

"Well, don't worry, because I've got the perfect solution," Naomi said.

With that she grabbed her wide white skirt and lifted it up to flash her new husband, giggling to herself as she did so. She only gave Jon a couple of seconds glimpse beneath her skirt, but that was enough for him to see. To see her legs in white lace stockings and garters, yes, but more than that, to also see what was between her legs. If the former made him excited at seeing his casually dressed girlfriend transformed into his sexily dressed wife, it was the latter that really made his jaw drop. You see, Naomi wasn't wearing sexy white lace panties to match her stockings. No, instead she had on a leather harness that fastened kind of like a jock strap but with a metal "o" on the front of her crotch. And through that "o" was pushed a dangling black dildo!

"What the hell?" Jon asked, "Is that what I think it is?"

"Remember when you said that tonight would be special if it could involve some way of losing your virginity? Well, I found a way..."

"Have you been wearing that thing all day?"

"Oh yes," Naomi gave a bigger naughty smirk.

Jon had never given much thought to the idea of a woman with a strapon being an exciting thing for him. As far as he was concerned it was something for lesbians to use so that they could penetrate each other. Nevertheless, the thought that his bride in her elegant white dress had been concealing a strapon dildo throughout, that it had been hanging there as they said their vows, when they kissed for the first time as man and wife, that he might have almost felt it as they held each other through that first dance, did catch his curiosity and get him a little hot under the collar at the naughtiness of it.

"And nobody could see?" he said. Her usual clothing would have made five inches of silicone rod between her legs pretty obvious, but the wide skirts of her princess-ish wedding gown concealed it completely.

"Well, just Anna." Anna was Naomi's maid of honor. "I had to have someone help use the bathroom in this dress, so she had to hold that too while I went. Don't worry, though, this was kind of her idea."

"What?"

"What do you think happens at a bachelorette party? It's all gossip and giving the bride "sexy" presents like lingerie and sex toys. Conversation turned to the wedding night and I mentioned to Anna what you'd said about its importance being all about losing virginity. And she pointed to a dildo and said: "You could always shove that up his ass. I bet he's still a virgin back there." We all laughed a bit and I didn't think any more about it at first. But when I did, it occurred to me that Anna was kind of right."

"How?"

"Well, it would make tonight special to do something completely new. You're right that our wedding night can't involve losing our virginity the traditional way, but losing your anal virginity could be the next best thing. Besides, we're going to be together for the rest of our lives, that's what all this wedding stuff means, don't you think at some point over the years we're going to need to mix it up in the bedroom to keep things fresh?"

Jon had to admit that he could kind of see the point here. They were committing right now to a life spent only with each other and he didn't want to be one of those married couples that gets to middle age and only has disinterested sex once a month. He wanted to know that married life promised years of passionate lovemaking ahead. Maybe opening himself up to new experiences was the way to achieve that. Meanwhile, he had to admit to himself that, all the time she'd been talking, Jon couldn't shake the image of Naomi packing that strapon beneath her wedding dress and the thought was making him horny despite himself.

"When I showed Anna she was thrilled," Naomi was saying. "She said she wished that Andy was up for something like this, she'd wanted for ages to get him into anal play." Andy was Anna's husband, married a few months earlier at a wedding where Naomi had been maid of honor. "Their married sex life seems like it might not be going anywhere fast. Please, let's do this and I can tell Anna what she's missing. Come on, why shouldn't we be the adventurous couple?"

Truthfully Naomi had indeed thought nothing of Anna's joke about nailing her new husband's butt when Anna had first commented during the bachelorette party, but the thought had returned to her again and again in the days that followed. She had been a little put out at first by how her fiancé didn't seem at all excited by the possibilities of their wedding night. Naomi had been looking forward to that first moment of sex as husband and wife as one of the highlights of the whole wedding day. She had already spent hours picking out the perfect bridal lingerie, wanting it all to be just right. And then Jon had said that it wouldn't really be special anyway without the loss of virginity.

A few days after the bachelorette party, Naomi's thoughts had, quite at random, returned to Anna's jokey remark. Only now, in the comfort of her private thoughts, Naomi had begun to turn it over in her mind and begun to wonder whether actually this did provide a way to make Jon's wedding night the special night he'd talked about. A couple of years ago, they'd tried anal with her as the receiving partner. The way they'd both talked about it then it was clear that both Jon and Naomi perceived Naomi giving up this other part of her constituted a second loss of virginity, her anal virginity. Why shouldn't the same hold true for him?

So, she had begun to look online for whether this was normal. Should a bride really be considering penetrating her new husband's ass with a sex toy? And she had found so much stuff about "pegging". Apparently it was far more common and popular than Naomi had realised not only to engage in a little anal play with a man, but to fully strap on a dildo and take your place screwing his ass. Naomi had never thought much about it before but now she had read about pegging the thought of standing over her new husband and penetrating his virgin hole held a definite appeal for her.

As the wedding approached, Naomi had found it harder and harder to get the image of her pegging her new husband out of her head. Whenever she saw his firm ass in tight jeans she just couldn't help imagining strapping on a new toy and thrusting it inside him. By the week of the wedding, she knew that she had to give it a try. If Jon really wanted a special wedding night that was about the loss of virginity, then he was sure going to get one.

The day before the wedding, Naomi's special delivery order had arrived: a black leather harness and a five-inch black silicone dildo. There was no turning back now, she was ready for the wedding night that she had begun to fantasize about. Of course, she didn't have to wear the strapon beneath the wide skirts of her $2000 white wedding dress during the ceremony. There was no requirement, even if she was going to use it on her new husband during their wedding night, to be packing her prosthetic member throughout the wedding day. But it had given her a thrill to feel it and think about it all through the day. When she had stood at the altar and said "I do", simply knowing that the strapon hung there between her legs and nobody else realized was enough to get her wet.

Of course with a dress this grand it was bound to be awkward going to the bathroom and she was inevitably going to need her maid of honor's help. So, she had known from the start that Anna was going to see what she was wearing beneath her virginal ivory skirts. But then, hadn't this been Anna's idea all along? Anna, dressed in her blue pastel satin bridesmaid's dress had gasped and giggled when she'd seen what Naomi was packing beneath her wedding dress, but she had been hugely supportive and encouraging.

"Oh yes," Naomi's maid of honor had said, "Guys are supposed to totally go for anal play once they let their guard down and stop thinking it's unmanly or something. I've been working on Andy for ages, trying to convince him it's a good idea. You know the male G-spot is in the prostate, right? The only way to get there? Up the ass!"

Now, standing in front of her new husband, strapon hanging beneath her wedding dress, and giving him a flash of what was to come, Naomi could only hope that Jon was more open minded than Anna's husband, more willing to experiment. She had explained to him why she wanted to do this, told him that this was his chance to experience a real wedding night, a wedding night that would be their first time, now she just had to wait for how her new husband would respond.

"OK," said Jon, "I guess we can give it a go."

His quietly non-committal seeming answer concealed the excitement that was going on inside him. The more he thought about it, the more he wanted to try it. He couldn't help looking at his beautiful bride in her white dress and hungrily thinking about the hard silicone dildo she had concealed beneath, couldn't help thinking about how it might feel thrusting up inside him, invading parts of him where no previous lover had ever been, making this a real cherry popping wedding night.

Jon's heart was racing as his new bride guided his fingers to where she was laced into her fancy bridal dress. Stumblingly, his fingers unlaced her and slid the elegant gown down her body, leaving Naomi standing in a pool of white satin, lace and taffeta. Standing before him now was his wife in her white wedding lingerie. Even without the special something extra, Naomi looked amazing. He liked how casual and uncaring she often could be about her appearance, but that just made the sight of her smooth legs in white sheer stockings held up with lacy garters just that much more of a treat. Above this she wore just a white satin and lace corset which served to push her curvy body into just the right places, clinging to her waist and pushing up her ample chest.

Despite all this arousing lingerie, it was between her legs from which Jon's gaze could not shift. He was entranced by the sight of his beautiful bride in the hottest white lingerie with this eye-catching black prosthetic just dangling there, daring him to want it. And want it he did, more and more badly the more he hungrily stared at it. He was starting to really feel a need to understand what it would be like for his wife to take his anal virginity on this, their wedding night.

As Naomi pulled Jon in for a kiss, sliding his suit jacket from his shoulders as she did so, he could feel the hardness of her strapon rubbing against his semi-erect cock through the material of his suit pants and it was getting him more and more excited. He got a great view down his new wife's corseted cleavage as Naomi quickly took off his tie and began to unbutton his shirt, kissing him across the chest. Sliding down his body, she took off his belt and dropped his pants around his feet, then his underpants. Jon's cock sprang free and he was there, totally naked, with his new bride kneeling in front of him in her white wedding lingerie and black silicone strapon.

Holding his semi-hardon in his hand, Jon put his other hand on his new bride's head, where she still wore her veil pinned back over her silver tiara. As he pushed Naomi's mouth towards his cock, she stopped him.

"Not tonight, lover," Naomi pushed herself away from her new husband's hand, "This time it's your turn."

As they switched positions, her standing up and pushing him to his knees, her standing over him and holding her prosthetic shaft in her hand, stroking it like it was the real thing, Naomi began to feel the thrill of being the one with the power. Standing over her husband, pointing her strapon at his face as he knelt and looked adoringly up at her, she could see why men loved being in this position so much. Her husband had barely touched her and yet she was wet just with the feeling of power her strapon gave her.

"Come on, hubby, blow me," Naomi giggled.

She hadn't imagined it would feel so good, given the strapon dildo wasn't after all a real flesh and blood part of her, when her new husband willingly and eagerly wrapped his hand around it and started to pull it into his mouth, to slide it between his lips just as she would do with his real cock. But it did. It wasn't just the way that as Jon pushed to suck on her strapon, it rubbed the other end of it against her crotch, stimulating her clit, although that certainly helped. It was also just the feeling of standing over him and watching him submit to swallowing her glistening black hardness.

Of course, once Jon discovered that the jock strap-style harness that held his bride's dildo left an opening between her legs that exposed her pussy, things were taken to another level for Naomi. Now she felt the titillation of watching her eager husband swallowing her strapon all while his finger ran over and inside her wet slit, fingering and sucking her all at once. Naomi began to wonder whether this would all be too much for her. She didn't want to reach her climax before the main event had even happened.

Jon couldn't believe how stiff it made him, simply going down on his bride's black strapon. As his finger explored her wet pussy, he sucked and swallowed on her silicone dildo and thrilled to hear Naomi moaning loudly. Still, his cock sprang to an even harder level of excitement when his beautiful bride withdrew from his mouth and told him to turn around and bend over. This was it. Jon was about to get the wedding night virgin penetration that was usually reserved for the bride, only tonight it was going to be the bride herself, in her sexy bridal lingerie, that was going to be topping him.

As Jon turned away from her, bent face down and presented his fine, toned ass back up at her. Naomi went into her little clutch bag and found the lube she had bought along with the strapon dildo the previous week. Squeezing a healthy amount of the slick, shiny liquid onto the index finger of her right hand, soon Naomi was kneeling on the floor behind her new husband, finger poised between his legs where his cock hung as stiff and erect as she had ever seen it.

"Are you ready for this, babe?" she asked.

"Oh yes, honey, do it," Jon replied, "I want you inside me."

Parting her new husband's legs with her dry hand, Naomi slid the lubed hand between Jon's thighs. Her slick finger traced a line from his balls, along the perineum and into the crack between his cheeks. She began to rub around his tight hole, getting him used to her finger back there and making him nice and lubricated before sliding her finger inside him.

Jon let out a long sigh, almost a sound of relief, as Naomi pushed her finger up into his ass until it was buried most of the way inside him. The exquisite sound her husband made as she fingered his butt was heavenly for Naomi to hear. It was a real turn on to have this kind of power to make him moan and squirm with just a little slide and turn of her finger. As she turned her finger and applied a little pressure downwards, she found the harder fleshy spot of Jon's prostate and began to massage it in tiny concentric circles, making her husband make a noise that mixed surprise and delight like "Oh...oh! Ohhhhh."

Jon hadn't imagined that just one of his new bride's fingers could fill him up so much, nor that it would feel so good rubbing against his prostate. His butt was clenched tight around Naomi's finger but as he got used to the feeling of being filled and fingered he began to relax into it. When she pulled her finger back, he even rose his butt back to meet it, he was getting so used to having part of her inside him.

Fortunately for Jon, his puckered pink hole wasn't left empty for long. Another squeeze of lube all over her fingers and Naomi was pushing back inside him, this time with her middle finger joining her index one. Jon felt stretched out but in an exciting, tantalising way, as his wife pushed two fingers up his ass and used them to push down on his prostate, his stiff erection dribbling pre-cum in a way that Jon could do nothing to stop.

"I want it," said Jon, feeling he might not be able to hold back much longer with Naomi's fingering and prostate play. Now that they'd started down this path, he needed to feel her penetrate him, the wedding night would not be complete without it. "I want your strapon inside me."

"OK, honey. Prepare to have your wedding night cherry popped," Naomi giggled, squeezing lube onto her black silicone shaft and stroking it all over like she was masturbating a real cock.

Jon looked over his shoulder to see his bride, dressed in lacy white stockings and corset, still with two fingers up his butt, kneeling between his legs, rubbing lube all over her black strapon dildo. Just knowing that in moments she would be pushing that thing right up into his tight virgin ass made Jon's heart skip a beat in nervous anticipation. He couldn't remember Naomi ever looking as hot as she did now, completely owning his naked ass.