Steve and Gloria Write a Story

The next part came when Gloria removed her fingers and pushed the little stubby strap-on dick into his ass. And it turned out she was right. It felt good as it slid right in without any pain.

"How're we doing, Steve?"

"That actually feels pretty good. Is that all there is to it?"

"Umm, not quite. Hold on a minute."

Steve felt the little dick slide out f his ass and after half a minute had passed he felt something else tapping against his ass cheek."

"Alright, Steve, go ahead and spread those cheeks wide for me."

As soon as he'd done so, he felt the something begin to push into his ass and this time it was not going. Steve cried out at the pain and started to pull away.

"Hold on Steve. You've got to learn to relax," Gloria said as she pulled her fake dick back from his ass. He could feel more lube being added, then the pressure was back. "This is just about the size of Ronnie's dick. When you've taken this, taking him won't be such a big deal. Now, relax those muscles and I'm going to push in a little. You let me know when to stop and when to go on."

Steve felt the fake cock begin to enter him. He tried to relax, but when it seemed like to head was about all the way in the pain began to build. "Hold on a second," he said, and Gloria immediately stopped pushing, but did not pull out. When the pain had subsided, Steve said, "Go ahead," and Gloria slowly pushed another inch into his ass. Again Steve told her to stop, and she immediately went still. It wasn't that it hurt so much now as that it felt strange and stretchy. It felt like something much bigger than any normal sized dick was stretching him apart and Steve wanted time to experience that strangeness. When he had gotten used to it he said, "Okay, go on," and Gloria resumed her slow entry until he could feel her belly against his ass.

"Congratulations, Steve. You've taken it all. How's it feel."

"Frankly, it feels like I need to take a shit. But beyond that, it just feels kind of kinky."

"Yeah, some people say that 90% of sex is in your head. I'm not sure that my clit and nipples would agree, but my ass could probably go with that. If you start with the idea that butt fucking is exciting, it is exciting. I love butt fucking. It's kinky, it's dirty, forbidden, whatever, and that makes it exciting. I swear that once I got used to it some of the orgasms I've had with a dick in my ass are even more powerful than the ones I've had with it in my pussy. And you guys have a prostate that helps you get off with a finger or a dick up your ass, which makes it even easier for you once you get the hang of it."

"Ah, Gloria, that's all very interesting, but right now all I'm feeling is stretched and, like I said, kind of like I need to poop. Would you either do something or take your dick out of me."

"Well, I'll give you a few pokes just for fun, but I don't want you to come. I'll want all of that for later tonight." She pulled her dick out and pushed it in a few times, and Steve had to admit that it felt much more interesting that way. Then she pulled out with a pop.

"Oh, don't move for a minute," she said as she ran into the bathroom and back to the bedroom.

"Okay, now you can get up."

When Steve was on his feet, Gloria showed him a picture on her phone. His fingers were still spreading his cheeks, and his asshole was gaping so wide it looked like you could drive a train up it.. Steve looked down to see what she had really shoved up his ass and was surprised to see that, like she said, it was just a fake cock a little smaller than his own.

"Very nice," he said, "but would you please delete that before it accidentally finds its way onto the Internet."

"Sure, Steve, we're into privacy too. That was just for you to enjoy. And congratulations on losing your anal cherry. I'll call Ronnie to come on up and join us, and we can clean up our toys and get a shower."

"Okay, that's the end of Part One. That we were already there first and after our shower I had us change into those terrycloth robes that the ship provides, and Ronnie was waiting for us when we came into the living room from the bedroom -- obviously that won't fit with your opening, so I think we should use mine. Except I liked the part where you wanted to know what he looked like, so we should work that in. And I liked the margaritas. We can have them waiting there in the living room when we get there; Ronnie must have ordered them while we were in the shower. The rest of your story I like just fine. How about mine? Anything you can't live with?"

"You're really in control a lot here. Is that the way you see it?"

"Honestly, Steve, at the expense of bruising your fragile male ego, isn't that the truth most of the time. Short of rape or extreme inebriation, or maybe the giddiness induced by raging teenage hormones, unless you add poverty to the equation, weren't we brought up on "The woman gets to choose." When a man wants me, that gives me power and yes, I use it. If it makes you feel any better, at the wine tasting it was you who turned me on enough to make me want you to want me. I love to play, but I'm rich enough, and experienced enough, and invested enough in my relationship with Ronnie, that I get to play by my rules, and that means the guy I'm attracted to has to play by my rules if he wants to play at all. I hope that isn't going to turn you off."

"No it hasn't turned me off. I've always been attracted to intelligent women who knew what they wanted and were determined to get it. Maybe that's what attracted me to older women when I was younger."

"Steve, you've made a point of not talking about Sandra very much. A personal question, if you don't mind. She's older than you, isn't she?"

"Yes, she is, by 10 years. You remember my English Lit teacher in my story?"

"Yes. And I'll pry no further except to ask you to assure me that you haven't been walking her to the point of exhaustion each day so that you could have your evenings free. I'd feel badly about that."

"Oh, no fears there. Sandra is the one who's pushing herself. There's a big difference between 65 and 75, even a spry 75. And while she knows she can't do as much as she'd like, Sandra wants to do it all before she can't do it at all. There's a cliche about the candle burning brightest before it goes out. It's sad but its true. Anyway, what Sandra wants to see, I make sure, as much as possible, she sees, even if at the end of the day she can barely eat supper before heading for bed."

"Thanks, Steve. Now, is there anything else in my section of the story that concerns you."

"Yeah, is my big reaction to getting my ass stuffed really going to be that I'll feel like I need to take a dump?"

Gloria laughed at that one. "It might be, Steve. Like I said, 90% will be mental. If you go in thinking that it is going to be exciting, it's going to excite you, and that excitement will overcome, or enhance, the physical details. Ronnie's as sensitive a lover as you portray yourself in your story, so he's going to do everything he can to make this enjoyable for you. In the end, no pun intended, it really comes down to you. It's possible you might come out of the experience just wanting nothing more than to find the nearest toilet. If I were to bet, I think that the real Steve, you, not our fictional one, if he goes through with our proposal, will find the experience more interesting than enjoyable, and you'll go back to your usual orbit with your curiosity satisfied, rather than becoming a raving faggot. But if this were to turn you into a well-adjusted bi-sexual, that wouldn't be such a bad thing either, would it?."

"Yeah, well, I know all about the arguments on that. But let's not get ahead of ourselves. You've already had the pleasure of taking Steve's cherry. Let's see how Ronnie goes about buggering him."

Gloria made a few of notes on the first and last pages of her next stack of papers, then started dictating to her phone.

No sooner had Gloria said 'Ronnie's turn,' than Ronnie himself said "Yes it is, old boy. That was really inspiring, watching you and Gloria. Now I'm even harder than before you sucked me off. Makes me regret that your missus isn't here for me to return the favor. But she's not, and a deal's a deal. You're here, I'm here, so like they say in your home town, laissez les bon temps rouler. How about kneeling at the foot of the bed for me. Gloria, how about you scoot on down so that Steve can lick your cunt some more if he's of a mind to."

Steve and Gloria arranged themselves as directed, giving Steve a great view of his cum leaking out of Gloria's inflamed pussy before he planted his face firmly in it. Remembering Gloria's instructions about spreading his ass cheeks, Steve reached back and pulled them firmly apart.

Ronnie took one look at his red rosebud and said, "Ah, I can see that Gloria has had her way with you. She told me you were an anal virgin. With Gloria around, it's been years since I had a real anal virgin. Ah well, still this will be you first real cock, won't it Steve?"

"Yes, Ronnie, so extra lube if you don't mind. And what is it they always say, 'Please, sir, be gentle with me.'"

Apparently Ronnie was not holding Gloria's earlier buggering against Steve, as he was indeed generous with the lube, slathering it around Steve's asshole and fingering it deep inside. After toweling off his hands, he grasped Steve firmly by the hips and started pressing his engorged cock into his anus.. When he felt Steve tense up and try to pull forward Ronnie said, "No, Steve, just stay still and try to relax. If you can't talk with your mouth in Gloria's cunt, just give a little pat on your left cheek to tell me to stop, and another on your right cheek to tell me when to go on. You think you can do that?"

Steve nodded his head, which got an interesting reaction from Gloria, and patted both his ass cheeks at once to say that he understood. Ronnie waited, as promised, then when Steve's right hand patted his cheek resumed pushing forward. He could feel Steve's anal sphincter stretching around his cockhead, and then he felt it pop through. Steve let out a little yelp and furiously patted his left cheek.

Ronnie stopped pushing and said, "Ah, you're doing great Steve. That was the toughest part. We'll give it a rest until you're ready." After a minute, Steve patted his right cheek and Ronnie said, "Right Steve, now here's what I want you to do. Just push back until you've got yourself speared all the way on my cock. Once you've got me balls deep we can get on with some real fucking."

Steve continued to push back until he could feel Ronnie's pubic hairs rubbing against his ass. He felt even more full than he had when Gloria had pegged him earlier. His feelings were a sense of wonder that he had finally satisfied his curiosity to be fucked by another man, excitement at the idea of what the whole tableau must look like to a fly on the wall, or a guy shooting a porno, and, sadly, a need to use the bathroom. He tried to focus on the excitement, and started licking Gloria's pussy as a means of taking his mind off the need to empty his bowels.

"You can let go of your ass cheeks now Steve," Ronnie said. "I need for you to help hold yourself in place while I'm fucking you."

As soon as Steve had braced himself on the bed with his hands, Ronnie started fucking in earnest. Steve, with more control over his upper body at least, was able to do a better job of licking and sucking Gloria, and soon the room was a mixture of grunts, groans, sighs and slurping. Amidst all these noises, Steve noticed himself getting hard; maybe, he figured, his prostate was getting into the act as well.

Ronnie had endurance. Steve figured he had been being fucked for a good five minutes before Ronnie's grasp on Steve's hips tightened and his strokes became shorter, more urgent, and even deeper than before. Ronnie snarled, "I'm gonna cum," then a shout emptied his balls into Steve's ass at the same time that Gloria cried out her latest orgasm.

Then, just the relative silence of people gasping as they caught their breath.

When Ronnie pulled out of his ass, Steve could feel cum running down his thigh, an experience he had missed when Gloria pegged him. But Steve hadn't come with the others, and what really had Steve's attention was his raging hard on. He took his face from between Gloria's thighs and flopped onto the bed, turning over as he went.

He said, "Would someone help me with this, please?"

Gloria took one look and said, "That's mine, lover. I told you you could have all my holes. Let's start with my ass. And Steve, I like it rough, so don't you dare be gentle with me."

Gloria put her papers down, turned off her phone and topped off their wine again. "So, how does it play, lover?"

Steve said, "It plays pretty well as an erotic fantasy. Do you really think it would play half that well in real life?"

"I guess there's only one way to find out. It's not even 11 yet. The night's young and tomorrow we have a whole day at sea, so I doubt that Sandra will go down early. I could call Ronnie to be up here in an hour, and we could find out now. Or you could think about it all day tomorrow while we're at sea and make your decision in Barcelona. But this story has made me horny as hell Steve, and in about an hour I'm going to be getting royally fucked. Whether by you or Ronnie is your call."

The next day, Steve and Sandra slept in and spent most of the rest of the day lounging in the Rooftop Garden. For Sandra, the last few days ashore had been exhausting, and she was glad to take it easy. As for Steve, it had been a long night, and his ass was sore.