Captain's Choices

Chapter 1 - The Beginning

Your name is Captain, well that is what you prefer to be called, and this is your story, your life has been a crazy rollercoaster living a double life and most people on the surface think, You're just this normal guy who doesn't know much but if only they knew how wrong they really were.

After having a fallout with your ex, You never truly dated anyone but there is one girl You have been talking to for a while, today is your date with her and to tell you the truth you are a nervous mess right now, you may have agreed to this date but do you think this will go far or just fizzle out.

It all started when you met her online on a social media site, it started off casual and day by day it grew, you two instantly clicked. You told her about the break up she sympathized with you, she told you her stories and you listened to her being the great guy you are. The usual stuff.

As the days passed you were definitely sure you were attracted to this girl and wanted more, so you decided to test the waters as you were horny. When you are horny you do crazy shit, One night you decide to send her a text

"Thinking of you, wish you were here.. Would have loved to cuddle with you!" LAME!!, you thought to yourself not expecting a reply but to your surprise you get a call from her. "Okay maybe that wasn't the brightest idea" you tell yourself

"Just cuddle? Nothing more?" She says in a slightly seductive tone as soon as hear her speak you feel a twitch in between your legs.

"Hmm, alright maybe more.." you tell her slightly excited from hearing her speak.

"Why don't you tell me? what would you do if you were here?" she says as you both start getting in the mood.

"Firstly I would kiss you and then have you pinned against the windows, for anyone passing to see us." you say, as you start getting even more aroused than before, "Then, I would bite your neck, and pull your top down revealing your tits for anyone to see, ANYONE" to see. "I would put my hand down your legs and rub your clit as we make out, standing in front of the window".

"Hmmm that's pretty hot, you'd really want people to see us?" She responds. You smirk as you as say "Oh fuck yes, I wouldn't mind it in fact I would love to kiss you, while someone walks past watching us, you say. "And what if he or she decides to stop and watch?" she questions you again, "Then we would let them, and put on a show" you say "Maybe, I'd rub your pussy and bring my fingers to your mouth so you can taste yourself when anyone lucky enough shows up to watch us.

"Kinky!", she exclaims and her breathing definitely seems heightened, "Looks like I am not the only one who is turned on", you remark and suddenly the call cuts off.

Surprised and a little concerned whether you did something running, you sit there thinking, and you get a text,

"Hey? I have an idea" as your about to reply you get a video call from her, you swipe and attend it to see her sitting on her bed with a sexy smile on as you watch her, " want to know what my idea is?", she asks as she moves closer to the window in her room. "The curtains blocking the view, would you really want to open the curtains?", she asks teasing you.

Surprised by her move, "You're bluffing aren't you?" you ask.

She bites her lower lip, and slowly starts pulling her top off exposing her bra straps, for the first time in a while you are watching a girl undress who is not a porn-star or your ex gf.

She pulls her bra straps as she slowly starts removing the bra, exposing are curvy, well rounded tits, they weren't as big as your favorite porn stars, but they were definitely well shaped. She removes her bra completely, exposing those tits but she had the areolas and nipples covered by her hand. That was more than enough to cause a bulge in your pants.

"Still think I am bluffing?" she asks you. You are not sure what to say, She pulls the curtains, and stands exposing her boobs to the world pressing against the glass, she turns the camera around to let you see that there indeed is a street where anyone passing by could see her naked.

"See, I was not bluffing" she says, as she still stands against the window. "Is this how you wanted me pinned down?" she asks you, before you could say anything, you notice her bringing her fingers closer to her mouth.

"Are you tasting yourself??" you ask as you pull your own pants down. Releasing your semi hard cock out, she sees this, "does this answer your question?", she asks this time showing you her fingers entering her pussy and being covered with her pussy juices.

"Its really unfortunate you're not here, i would love that cock of yours pressing up against me as you have me pinned here, she starts thrusting her fingers inside her pussy as she watches your cock throbbing, "hmmmmm, mmmm ohhhh" she moans as she stands in front of the glass window watching your cock, "Oh God ! Oh God!" She moans as she starts speeding up "Fuck fuck fuck" she cusses as her pussy starts dripping making fleshy sounds.

You start imagining you being there and instead of her fingers its your cock thats thrusting in and out.. suddenly she strips completely.. and tells you that she has another surprise. "You know my vibrator died a week ago and i I haven't gotten a release", she says all this talk made me really horny.. realizing she's trying to control herself you ask her " Don't stop what you started " .. she smirks and says I wasn't planning to.

You watch her searching through the drawers as she bends over looking for something, while giving you a better view.

"Youre gonna love this", she says as she shows you her surprise a pretty big dildo.

"Surprise!", she exclaims now im gonna pretend this is you fucking me as she says that the image that caused your break up, your ex being fucked by someone else pops in your head.

Instead of getting upset or angry over it your cock starts twitching and getting even harder than before she starts to fuck herself with her dildo slowly at first, then starts to fuck herself pounding away the dildo in her pussy you nonchalantly start jerking off to the scene as you imagine her getting fucked in front of you, she starts moaning loudly as she keeps going " harder harder harder fuck me fuck me fuckkk" she keeps groaning as you hear her moan you start to rub your shaft faster and faster both increasing the tempo.. "Fuck fuck yes" you moan along with her as you now imagine her being fucked by you, she looks at you through the screen as you focus your gaze on her pussy leaking its pussy juices.

Out of nowhere she decides to pull her right boob to her mouth causing you to jerk off even faster you both dont utter a single word as the video call is filled with your moans, seems like you both are reaching the climax at the same time, as you keep jerking off you hear her say "what would you do if the person watching us wanted to do more than just watch" she gives a devilish grin, would you let him join in? She says in between moans grunting loudly what if hes bigger than you? Or fuck me while i suck off our guest ! She tells you moaning ..You dont utter a word instead your cock starts betraying you as it starts lubing you by leaking more precum than before..

"Fuck babe im gonna cum" she screams loudly as her dildo starts ramming her "fuck me fuck me fuck me" she keeps begging for more as she fucks herself with the dildo.. watching her make things this steamy you reach your own edge as you approach your climax as well.

You truly wish you were there with her fucking her.. as you both start breathing heavy she turns the camera towards her pussy and asshole. As you are still shocked at her questions you watch her pussy and asshole twich open and close rapidly and her pussy starts leaking overflowing with her own juices this send you over the edge and you too end up shooting your cum all over the place, both of you just lay there in silence collecting your breath she then starts by saying you see i wasn't bluffing she laughs and says now i definitely want to meet you. You cannot deny this was the hardest you have cum in a long time and you want to meet her too you decide not to bring up the questions she asked right before cumming, you tell her that was really amazing and that you want to do it again and again. She agrees with you and both of you wish each other goodnight.

You lay there on the bed with your hand covered in your own cum, and some of which is flowing down your shaft on to your balls, you look down holding your own cock and you watch as the tip of your cock still leaks cum and twitches in your hand as it starts softening.

You close your eyes thinking of what just happened, you were trying to test waters and it seems like you did the right thing because this turned out way better than you had hoped, as you start smiling thinking of your "Phone fuck", the image of your ex laying down on her back getting fucked in front of you with her legs locked around a strangers hips as he pounds her flashes in your mind.

With your tip still leaking cum in your hand you feel strange as the cock that was softening starts to feel a bit stiff again! "Okay I need to stop thinking about that" you mutter to yourself as you get up to clean yourself up.

You try take a shower thinking about the phone sex you had and you inevitably start getting hard again as the shower drips on you start stroking your cock, recalling the events that just happened. Watching that pussy get pounded by that dildo which you instead wished was your cock you start imagining it again "Oh yes" you grunt as you start stroking yourself trying your best to quickly rub one out as this is the first time you have been this horny in a while.

You vividly remember her moans as you keep jerking your tip which feels really sensitive but you keep going anyway "oh god, fuck" you exclaim as you keep it going, you feel your balls churning again preparing another fresh load to shoot out.

As you keep jerking, you think about what she said at the end, you think to yourself, what you would actually do if a passerby actually decided to stop and join you, as you think about this question, the image of a guy coming towards you two as you are fucking the living daylights out of her, your pace increases as you feel tension building in between the region under your balls and above your asshole.

You imagine this dude coming towards your window, as you watch her looking at him, you keep stroking more as you imagine her saying "Look we have someone coming towards us" with her tits slamming against the glass window.

To your own surprise, she opens the window and the guy comes up to you two stand with your cock ramming her pussy as she bends over the stranger dude unzips his pants and reveals a huge cock, even bigger than your own.

Suddenly she grabs his dick in her hand and starts stroking this random stranger in front of you, you cannot believe your imagining something like this, with a girl that you are actually attracted to, why does it feel so fucking hot imagining a stranger joining us, you think to yourself. You are snapped back to reality as you feel the churning sensation in your balls increase and you feel like you are about to explode again, you cannot believe this is happening again right after cumming hard just a while ago.

You start stroking intensely as you imagine her bending forward to suck the strangers dick before you could think of anything your cock starts shooting cum again you grunt "Gahhhh", as strands of cum, fly out of your cock and stick to the wall in front of you as you cum hard yet again twice in a row. This is fucking nuts you tell yourself, as you clean yourself off, washing all that sticky cum off of your tip, eventually reaching your bed you fall asleep.

You agreed to meet at the nearby restaurant for the date which is convenient. But I am getting ahead of myself aren't I? The girl you have been talking to is older than you and you do admit she is quite a hot chick, you have seen her over the phone but you are still nervous to talk to her in person. As you are thinking about your "date" you notice a waitress looking at you giving you smile.

{ this is my first story so hope you guys like it, im open to all suggestions do let me know what you would like to see ill try to update this as often as i can, let me know if theres any themes you'd want to be added. Commissions welcome too . This is the end of the first chapter}