Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
I reach back and take out another beer. I open it and take a drink.
"Don't worry I won't ask, I'm just here for the view." I say while getting comfortable and look out over the water.
She lets out a small laugh.
"What the fuck did I do Simon?" She asks.
"I don't know," I reply playing dumb.
"We took a guy back last night," she replies.
"I'm guessing it didn't go so well," I reply.
"I'm not sure," She replies. "It got weird."
"Look you don't have to tell me if you don't want to," I reply.
"No, it's ok...Actually I'd like your opinion on something," she replies.
"Ok," I reply hesitantly.
"So yesterday afternoon, Adam comes back to the villa and says he's met a guy who's open to a three-way," she says.
"Adam's your husband, yeah?" I ask.
"Yeah," she replies.
"And why does a couple of newlyweds want a three way?" I reply. "If you don't mind me asking?"
"I know weird right?" She replies with a brief laugh, followed by a sigh. "We'd been taking about it for ages. But we come from a small gated community in Tennessee and we really didn't want people to find out our business. It's quite a religious area... So, we decided with being away to try to do it here instead," she replies.
"Ok," I reply. "Makes sense."
"Adam said he met the guy by the pool. Will or Bill or something like that. Said he works for a luxury travel company in DC. I said fine and that I would meet him," she replies while taking a drink. "So last night, we met up at the bar. He seemed nice, bit overly sure of himself but he had a hot body and big strong arms so I said, ok."
"If that's the kind of guy you're into why ask me?" I reply.
"Don't get me wrong you're hot, way better looking than Will or Bill or whatever his name is. You were very much my choice but you said no," she replies.
"Fair enough," I reply.
"We get back. Adam fixes us some drinks as I sit down with Will...Bill. Fuck it. I'm just going to call him Bill I think," she says.
I can't help but laugh.
"Ok, Bill it is," I chuckle.
"Adam hands us our drinks and sits so I'm in the middle. We talk a little but soon Bill takes my drink from me and places it down. Then he starts kissing me. I feel his hand on my stomach and then he slides it under my shirt and onto my tits," she says.
"Ok, hot so far...Please continue," I joke.
"He plays with them for a bit, then removes his hand and slides it down onto my thigh. I open my legs and he slides it between them and rubs my pussy. I'm thinking this feels ok and I start to get a little into it," she says.
"Ok," I reply desperately trying not to get hard myself.
"So, I take his dick out and start to jerk him off," she says. "Simon, it was huge. The only way I can describe it, is it's a fucking porno dick!"
She holds her hands out and gestures its size, which looks to be quite big. Maybe ten to twelve inches it's hard to tell.
"He stops kissing me and rubbing my pussy. He grabs me by the back of the head and the next thing his cock is in my mouth...My jaw's actually still aching from it," she says while rubbing her face. "Anyway, I blow him for a bit and Adam hands me a condom. I roll it on as far as it would go and I'll say this his cock was so big the condom only covered about two thirds of it."
"Jesus," I reply.
"Right? I was praying for it not to hurt too much," she replies. "Anyway, I straddle him, take his cock in my hand and try to slide it in. It fucking hurt like hell. But I managed it...Been on top really helped."
I nod along to the story desperately trying not to judge.
"I ride him for a bit and the pain starts to die down and just as it does, he pulls out. He picks me up and places me to the side of him. He climbs down onto his knees, on the floor, tells me to get down on the floor and when I do, he bends me over in front of him. He sticks it back in and fucks the shit out of me," she says. "I mean straight up pounding me."
"I...erm...do...do you think this is an appropriate thing, to be telling a stranger?" I ask, feeling very uncomfortable and almost as equally turned on.
"Yeah, you don't know me. We'll probably never see each other again," she replies.
"That's true," I reply.
"Anyway, it hurt like hell. So, I pushed him off and had him sit back on the sofa so I could ride him again. As I get back on it. Adam moves around behind me and starts tonguing my arsehole which I thought was a little risky to be honest," she says.
"Too right it is. If you lift up a little too far, he's licking cock," I reply.
"That's what I thought too," she replies. "Well, it still hurt so I lift up off his cock to take a break. As I lift up Bill sucks on my tits and rubs my pussy. After a few minutes, once the pain dies down, I'm ready to go again. I reach down to take hold of his cock and it's not there. I'm thinking to myself what the fuck? I reach down further to feel for it and it's pointing straight out away from him. I try to grab it, but I can't move it. I look around to see Adam sucking on Bill's dick!"
"Oh shit!" I reply in shocked manner.
"Yeah, not only that, he's removed the fucking condom too," she replies.
"Did you know he sucks cock," I ask.
"I knew he was bi curious when we met, he said he'd never done anything with a guy before," she replies.
"Were you ok with it?" I ask.
"You know what, not really. But I was going to let it slide as a one off. He sucked him for a bit then points it back up towards me for me to fuck...But I say no and to get another condom. Adam tells me that we'd ran out and that the one he took off was the last one we had. So, I refused," she replies.
"Sensible...you don't know him," I reply.
"You'd think," she replies sarcastically. "So, I join Adam on the floor and we suck Bill's dick together. It was kind of a turn on, I guess. Then Adam pulls the lube out of my purse and asks me to finger his arse while he blew Bill. At this point I'm thinking just go with its Danielle, let him get it out of his system. You know?"
"To be honest I...I'm a little in shock," I reply still stunned.
"Yeah, you're in shock now. Just wait," she replies. "I start to finger Adams arse and he immediately gets into it. He asks for two, then three, then four fingers very quickly. He's pushing back, demanding it harder to the point I'm practically fisting him. Some of my knuckles even slipped inside, I swear. I've seen nothing like it. Then he slides off my hand."
She looks at me with a confused look on her face.
"Do you know what he did?" She asks.
"I think I can make a good guess," I reply.
"Yup, he turns around on all fours, Will...Bill climbs down behind him and sticks his dick straight into Adams arse," she says. "Literally, instantaneously balls deep. He then fucks the shit out of my husband."
"I don't think I want to hear anymore," I reply feeling very uncomfortable.
"But...do you think that's weird?" She asks.
"Well...yeah...you're married," I reply. "Has he ever been with a guy before?"
"I don't know, I was actually going to ask you...Do you think an anal virgin could take a ten- or eleven-inch dick on his first attempt? I'm talking straight in."
"Well speaking from experience...it's not that easy," I reply.
"Experience?" She asks looking confused.
"Yeah," I reply. "I used to be in a relationship with a trans girl."
"Oh shit, really?" She asks sounding surprised.
"Yeah," I reply.
"Wow, didn't have you pegged as the type," she replies.
"Well, it was a long time ago," I reply.
"So, it's not that easy then?" She asks.
"Well put it this way, Hallie struggled taking my cock our first time and I'm nowhere near that size. And as for my first time, I just about managed with some pain, but to be honest Hallie's cock is long, but not girthy," I reply.
"So, do you think it's possible to take a huge cock on first attempt?" She asks again. "I'm talking long and girthy."
"I mean it's possible. I don't know if I should be saying this, but in my opinion, it's likely that he's either, done it before or he's been using toys to prepare. I don't know, I wasn't there...but I know the difference between my first time and my twentieth or even one hundredth time," I reply.
"Oh my God my husband's gay," she says before finishing her drink.
"Another?" I ask.
"Please!" She replies.
I reach back and take a couple more beers out of the box and hand her one. Her hands are shaking.
"Where the hell did you get a box full of beer?" She asks. "There's no store on the island."
"I know a guy," I reply.
"How do you know a guy?" She asks confused. "You've only been here a few days, haven't you?"
"Ok, I know a guy. Who knows my guy," I reply.
"Well, I hope you don't mind me drinking most of them," she replies.
"Hey, I'm only offering two or three. That's all," I reply.
"Yeah, that's what you think," she replies cheekily.
"So gay husband?" I reply moving the conversation on. "Do you really think he's gay?"
"I don't know...I think he's bi at least," she replies with a sigh. "Simon, what the fuck am I going to do?"
"That's one thing I won't tell you...It's your marriage, that's your decision to make," I reply. "Could you live with a man that wants to fuck guys?"
"No, I want to go home and live a normal life," she replies. "Now I'm going home, forever panicking that he's the one fucking the pool boy."
"Best clean your own pool then," I reply.
"You kid. But that's exactly what's going through my head right now," she replies. "You should've seen them. I could have left the room and they wouldn't have noticed."
"Then I guess you're going to have to have a conversation with your husband," I reply.
"I know," she replies. "Do you know what's worse?"
"What's that?" I reply.
"They didn't even use a condom. He came in Adam's arse. So, when we get home, Adam's going to have to go get tested...What do I do if he's caught something?" She asks.
"Pass...I can't answer that for you I'm afraid," I reply.
"We had a huge fight about it just before I left. He wanted to have sex...I said no," she says before bursting out laughing. "He's been walking like he's shit himself all day, but still wanted to have sex. tonight"
I can't help but laugh along with her.
"Fucking hell Simon, why couldn't you have just come back with us?" She asks. "Then all of this wouldn't have happened."
"Do you want to know a secret?" I reply.
"What's that?" She replies.
"Last night, I was on my way to your villa and you guys passed me," I reply.
"Fuck off!" She replies. "You're joking?"
"Nope, afraid not," I reply.
"Fuck!" She replies.
"Yep," I reply.
"That must mean that you wanted to fuck me?" She replies.
"I did," I reply. "At least until I heard you got stretched out by a python and your pussy is as loose as a wizards sleave."
"Fuck you! It's not that bad," she replies nudging me in the ribs.
"True," I reply. "You may tighten up in a year or two...In the meantime, make sure you carry a warning sign around with you...Caution open trench."
"Fuck you!" She shouts while laughing.
She starts playfully hitting me, I grab her wrists and she lunges in. We pause for a second, our faces a matter of inches away from each other. Danielle closes her eyes and makes the first move. She kisses me on the lips. Within seconds she ramps the kiss, into a lustful frenzy and I find myself eagerly reciprocating. Our hands are all over each other. Her hands quickly make their way to unbutton my shorts, my left hand is on her breast and my right hand sliding up her thigh.
A moment later she has my hard cock in her hand. I pull her underwear to the side and I start rubbing her wet pussy. Danielle stops kissing me and moans as I rub her clit. I can feel her stroking my cock faster and faster.
We don't stop, her pussy keeps getting more and more wet. I slide my index and middle fingers inside her and she moans even more. I feel her pussy gush as I finger her. She lies back and pulls me on top of her. I remove my fingers from her and she guides my cock to her pussy as I kiss her again. I can feel the warmth from her pussy against the tip of my cock and I waste no time in thrusting inside of her.
It feels amazing, her pussy is actually pretty tight and extremely wet. I fuck her passionately, but before long the thought of her being married begins to weigh me down. It doesn't take long for the guilt to get the better of me.
"Wait," I say as I try to break our kiss.
"What?" She replies in a flustered tone.
"We shouldn't," I reply as I remove my cock from her pussy.
"Why not?" She replies.
"Because you're married," I reply.
"So, it didn't stop my husband last night," she replies.
"Last night you both had each other's blessing to do what you did," I reply. "If you two are going to have any chance, then this can't happen."
"Please just keep going," she pleads.
"I can't...I'm sorry," I reply, while lifting myself away from her.
Danielle pauses and adjusts her underwear.
"Fuck I'm so wet right now!" She exclaims.
"Hey...don't!" I reply. "I'm already regretting stopping."
"I'm pretty gutted to be fair," she replies. "I was pretty fucking close too."
"Fuck!" I reply in frustration.
I wipe her saliva off my mouth with my hand and I get a whiff of her pussy on my fingers. I can't help but think how good it smells. We quickly tidy ourselves up and I somehow get my cock back in my shorts.
"Another drink?" I ask.
"Sure, why not?" She replies.
I pass her another drink and get myself one at the same time.
"Can I ask you a question?" She asks.
"Sure," I reply.
"You said you used to be in a relationship with a trans girl," she says.
"Yeah," I reply curiously.
"Does that make you bi?" She asks.
"I guess that depends on how you look at it really," I reply. "For me Hallie's a girl, so no I wouldn't consider myself bi but I do understand how others would think I was."
"Would you ever do it again?" Danielle asks.
"With Hallie? No," I reply.
"I meant with any trans girl," she replies.
"I don't know, to be honest," I reply. "What I had with Hallie was special. I was head over heels for her...I guess if I had that again, with another trans girl then probably. But the chances of that are very slim."
"How did you two end up together in the first place?" She asks.
"Oh, you know. Boy meets girl, boy falls in love with girl, boy finds out girl was born a boy...Boy breaks up with girl, boy is miserable without girl, boy realises he wants girl back the end," I reply.
"You didn't know?" She replies.
"Nope," I reply. "Didn't have a clue. In hindsight, not knowing was probably what got us together in the first place."
"What do you mean?" She asks.
"Well, if I'd have known from the start. I would've probably avoided her, or at least be on my guard around her. I would never have gotten to know her the way I did and that's why I fell for her in the first place," I reply.
"What happened for you two to break up?" She replies.
"That's a shorter story, I needed money to stay in uni and buy her a ring. I was working all the time and never saw her. She had a breakdown and started fucking half of the campus," I reply.
"Ah," she replies.
"Yeah," I reply. "And do you want to know the kicker? Until last Sunday, I hadn't seen her in almost six years."
"You saw her recently?" She asks.
"Yeah," I reply.
"And how was that?" She asks.
"A bit of a rollercoaster to be honest," I reply.
"Do you still have feelings for her?" She asks.
"I don't know. I do still have a lot of anger and resentment towards her," I reply. "But what got me most was that, in the end I kind of felt sorry for her."
"Sounds like a yes to me," she says with an uplifted tone.
"Maybe...I mean at times it felt like nothing had happened, we just slipped right back into how we were. I had to keep reminding myself why I was mad at her in the first place. What was worse though is that she's still hot as fuck," I reply.
"Is she why you stopped fucking me?" She asks. "Did you feel like you were cheating on her?"
"Nah...She didn't cross my mind," I reply.
Danielle's, question resonates inside my head. I can't help but think about what happened between me and Becca when she was with Joe. I went through with it then, why couldn't I go through with it with a stranger? Was Hallie part of my decision to stop?
"Do you think you'll get back with her?" She asks.
"No way!" I snap.
"Why not?" She asks in a surprised tone.
"Because when I think of her, all I can picture is all the guys that she was with...It makes me sick," I reply.
"And yet you tell me I should try to work it out with my husband," she replies. "And I was actually in the room for that."
"Well, I saw a video...Two guys one chick," I reply sarcastically. "And once again, your situation's different...He did that with your blessing, you could've stopped him anytime," I reply.
"Oh yeah, what was I going to do? Shout get your dick out of my husband!" She replies.
"How about Adam, take that man's dick out of your arse," I reply.
Danielle starts laughing uncontrollably and I can't help but laugh along with her.
"What are we like?" She asks.
We sit and talk for a few more hours, making a considerable dent in my beer supply. Eventually while both of us are very much intoxicated, we part ways and I head back to my villa while Danielle heads back to her husband. Even with the blue balls, I feel at peace, knowing that turning her down was the right thing to do.
The next time I see Danielle is on Saturday morning. I see her and Adam taking their suitcases to the main desk to check out. She blows me a kiss and waves as they depart the island on the boat to the mainland. She looks amazing in a tiny summer dress that barely covers her breasts or her pert arse and all I can think is you fucking moron Simon you shouldn't have stopped.
With a strange sense of frustration and satisfaction I go about the rest of my holiday with the intent of having as much fun as possible out of it. I fill my days doing all the touristy things I can and in the end I'm sad to leave.
A week later, I return to work. I catch up on my emails and I see one forwarded onto me from the company contact us email address. It from a woman called Danielle asking to discuss an investment opportunity. I email back and receive a reply.
Hi Simon,
I hope you don't mind but I google'd you and thought I'd get in touch.
Adam and I've managed to patch things up, although we're still working some on things. He's promised me his dick sucking days are over. But should I catch him in a three way with the pool boy and the gardener I know where to find you. Although I am still pissed at you for stopping that night, I think about it often. Maybe one day we can finish what we started.
Danielle XXX
I reply back, telling her I'm pleased things are going well for her and I hope the two of them have a good life together. I also add, that stopping that night will always go down as one of my biggest life's regrets and although I'd love to finish what we started I hope her circumstances never allow it to happen.
I stay true to my word and resist the temptation to call Hallie. As the weeks go on, I forget I have her number on my phone and to my relief I hear nothing from her either.
It's just before four thirty in the afternoon, on the last Friday in August. The office is almost entirely deserted, with virtually everyone heading off early ahead of the bank holiday weekend. Unfortunately, I'm not able to knock off early, as I've got a conference call to attend after hours. So, I'm working out of Peter's corner office while he's away.
With the markets about to close following a quiet day of trading, I don't have a whole lot to do and I'm ready for my long weekend. I pour myself a glass of Peter's finest Scotch, that he keeps in his draw. I lean back in the chair, put my feet up and look out over the city.
