For The Win

As I prepare for my third date with J, I feel a bit of nervous energy hit me. It's been over 2 months since I last saw her because she's been traveling across Asia coupled with the fact that she lives in another province that's a flight away. Even though we have kept in contact daily, I wonder how seeing each other in person again after such a long time will feel. Will I live up to her memory of me? I guess only time will tell.

After taking my time to carefully cut my hair, shave, shower and lotion up, I catch myself starring at the wall blankly caught in a daze remembering the amazing time we had on our first 2 dates. Our first kiss at the arcade, followed by us leaving early to fuck in the car behind a closed autobody shop. She's incredible! Smart, funny, driven. Her body...so tight, her passion...so invigorating, her pussy...so fucking wet with desire. Not to mention that I added to that wetness by making her squirt for the first, second and third times in her life...it's kind of my specialty.

I head to the closet to pick out my outfit for the night. I end up settling on a nice pair of jeans that hugs my ass just right. She always tells me how nice it is so I figure I should tease her with it. The shirt and overcoat only add to the style.

Ensuring to pack the gifts I got her, I race around the house packing everything up and jumping in my car. After parking, I arrive at her door with a knock. When she answers, for a moment we stand there taking in each other. She looks as amazing as I remembered. Nice looser fitting jeans with a top that's nice and tight revealing her fantastic tits.

"Hi bb." She jumps into my arms and I grab her and hold her tight, kissing her tenderly on the lips before pulling out the bunch of flowers from behind my back. "Awe...I love them."

"Come in for a second. I still have a few more things to do before we leave," she says, then takes my hand, leading me inside. As I sit and wait on the couch, all I can think is I have every reason to get up, grab her, and bring her straight to bed, but I'll wait. We have a great night planned, and I'm trying my best to be on my best behavior...at least for now. She's finally ready and we head out the door, chatting the whole way to the car.

"So we're playing pool first and then what's happening after?" She asks.

"It really depends on who wins! We do have a bet after all."

We are both very competitive people, going as far as to make a friendly bet on our first date -- which I won. And ever since, she's been trying to find ways to even the score but to no avail. I'm now 2-0 with her now owing me a few sexual favors as my winnings. The second time I won at an online game, she immediately bet me again, double or nothing proving that she doesn't know when to quit...which I kind of like. And now the moment of truth is here and trust me, I intend on taking it all when I win.

Once we arrive at the hall, we get a table and order some drinks. I can see the focus and determination in her eyes. She wants to win! Our beers arrive as I was breaking the first rack and from her first shot I was getting the idea I might be in for a dog fight. It makes sense considering the bets on the table. If she wins, I have to allow her to peg me which isn't happening because my virgin bootyhole has taken up a life of celibacy. If I win; excuse me...when I win, she will have to accompany me to a sex club which will be her first time.

After some time and many drinks deep, she is 1 shot ahead of me with 2 shots remaining to win and it's her shot. She did tell me she "wasn't bad" but clearly she hustled me but I don't plan on losing because my eye is on the prize. Although she clearly has an easier angle available on this shot, she proceeds to select the one that gives me a perfect view down her blouse as she bends over to address the cue ball she looks up to catch me watching her. She winks at me and slams her ball into the targeted pocket.

"You do realize that this is for the win right?" She flashes a coy smile and walks around the table to get setup for what could potentially be her final shot.

"Don't remind me? You hustler! Best 2 out of 3 right? I ask.

"Nope! Those weren't the rules! One game, double or nothing!"

Her shot puts her back to me as I stand behind her patiently and nervously waiting for a chance to play my remaining balls. She bends over to address her shot but then backs up till her ass makes contact with my leg and wiggled just enough to let me know she knows exactly what she is doing.

"Can you please backup sir? I'm trying to win here"

I back away as requested. She strokes her cue stick smoothly but misses the shot.

"I missed my shot; I can't imagine why." Sitting there sipping my beer I see her heading toward me with that mischievous smile on her face. She presses her body to mine, her breasts pushing against my chest. Looking up with serious bedroom eyes she says, "Guess that makes things a bit more interesting doesn't it? Don't blow it or you won't be watching me BLOW it at the club tonight."

"Did you miss on purpose? Fuck! Don't do that...now my cock is as hard as this pool cue."

As she looks down to see the growth in my pants, I take a breath to compose myself, I start to imagine the night we are going to have if I win and that thought alone awakens my inner shark. Now it's on...I must win! I address the first ball and sink it. With 1 ball and the 8 ball left I'm on my way. Shot, in the hole. Here I am with the bet on the line, and before playing the ball I look up at her and say "I hope you're ready to go to your first sex club." With a devilish smile she replies "If you sink this, you can have anything you want but your shot will have to wait until I come back from the lady's room...don't shoot until I'm back."

As she's walking away, I'm imagining her naked. She turns me on so much. From the corner of my eye I see a few glances being thrown my way from the four guys playing two tables over. One of the guys gives me the nod of acknowledgement and I return it with a smile and a nod back. A few moments later she returns, walking straight towards me and now all 5 of us are watching her.

She kisses me on the lips "Can you hold these for me?" She places something in my hand and closes my fist around it...her panties. As she's about to walk away I grab her and pull her into me. Her ass now pressed against my hard cock. I whisper, "Were they too wet to continue wearing?" As I position her ass on my cock she grabs my hand that's firmly grabbing her waist.

"I believe you're perfectly lined up now" I say as I push my cock against her. Before I could go any further she backs away. "You have a shot to make sir, don't get too ahead of yourself."

I quickly compose myself and lean over the table, setting up my shot. My eye looking down the shaft of the pool cue like a sniper looking down the barrel of their gun. While I focus on the hole I see her behind it. The crotch of her pants in perfect alignment. I take aim, shoot....Game over!

"Guess that's better luck next time J. You are now 0-3 in challenging me, I think we should keep doing this because I love winning"

"Did you win or did I let you win? I guess you'll never know who the winner TRULY is." She says while putting on her jacket. "Lead the way...winner." She grabs the rest of her beer and swallows it down.

"Before we go I have something for you. Go to the washroom and put this in." I hand her a small bag.

She laughs as she looks in the bag to see a few different size butt plugs "Seriously?! OK I'll do it because I'm not a sore loser."

After a few minutes she comes back with a smile. "It's surprisingly soft. I feel so full" She laughs again while we start heading to the car.

J has never visited a sex club before, and although she's keen on experiencing it there are rules of engagement one should follow to ensure this is not the first AND last time we attend one. I've always had a thought that she was into voyeurism and watching others have sex based on her sharing stories and pictures of a couple that lives next door to her. They love to be naked and fuck for the world to see and her bedroom window is in a perfect position to watch.

We arrive and approached the club together. As we enter, we are met by the front desk attendant who proceeds to take down our details as we are required to join as members to get in. The attendant then reads us the rules of the club and hands us a key to the lockers.

"Enjoy your night beauties." The attendant says.

"Shall we just get a drink at the bar first, loosen up a little?"

She nods enthusiastically "Yeah, I'm going to need one or two." She laughs jokingly and nervously.

We make our way to the bar and both have a few Tequila shots to get rid of any inhibitions we may have and after we head upstairs to change out of our clothes and into some towels. The club is a bathhouse spa type deal complete with a pool, sauna, hot tub, a dungeon and multiple open or semi-private play areas. After changing we visit the play areas and find a seat. A quick glance to our left is met with a couple enjoying each other. I instantly look at J to gauge her reaction as she watches him drive his cock into her willing pussy. It seems clear she's intrigued by what she is seeing so I take the opportunity to slip my hand between her legs and find my way under her towel. I begin to rub her inner thigh and lean in for a kiss on her neck from behind. As my hand reaches higher, I can feel her start to lean into it.

"Mm fuck bb, I need you right now", she moans into my ear. Not needing to be told twice, I take her by the hand and we walk over to a little area further into the club where there is a small bed, perfect for us two. I lay her down and start kissing intensely, our hands exploring our bodies. Rubbing my hands up and down her thighs, then forcing her legs open I start to make my way down.

"I've been waiting for this all night"

I dive deep into her pussy running my tongue along her pussy lips before parting them and exposing her clit with my mouth. She moans in delight as I continue to eat her pussy and enter two fingers inside her. At this point a very small gathering of people stand around the bed we were on. A couple sitting watching us along with two other females. At this point J has noticed too. I'm watching her looking at how excited some of our 'viewers' are. I stop eating her and move back up to kiss her up to her neck. "You OK with them watching?"

"I don't care just FUCK ME!"

After giving me the permission to continue I knew I wanted to honor her request and give these people something to watch.

I lay down on the bed and positioning J over top of me rubbing my dick along her slit a few times before letting her sit down on it. She slides onto it slowly. The male of the couple in front of us is watching intently while reaching down to his partners pussy. It was clear they weren't leaving until we finished.

One thing I remember from our first 2 encounters is that J loves to fuck me nice and deep. She starts slow at first grinding on my cock while her hands are on my chest. She then leans slightly back and begins to pick up pace, playing with her hard nipples at the same time.

"Oh yes, fucking ride him just like that girl" the female of the couple says with excitement.

J seems only happy to oblige as she starts to go faster, harder and deeper. It starts to become evident that she is close to cumming so I grab her hips and ass and help her to grind.

"FUCK......" She yells out and drops down on top of me shaking a bit with aftershocks. Another thing I know is that once J cums, she can continue to have multiple orgasms in a row so I decide to switch positions cause it's my turn to really let go. I position her on all fours and spread her legs nice and wide. Before fucking her I bend down and run my tongue across her wet pussy tasting her cum. The butt plug she inserted still very much intact.

As I enter her pussy, I can feel her pushing back into me, seemingly ready to take all I have to offer. "Fuck me hard!!!" She pants.

"Mmmm, I love when you say that" I slam my cock inside her and start to give her a hard and deep pounding as she moans with every thrust. J is varying between playing with her nipples and rubbing her clit wanting to cum again and again.

As she's cumming I can't take it anymore and I have to blow my load. I grunt "Uhhhhhh...." As I fill her up with my cum, nice and deep. As I finish, I snap back into reality and notice the couple is now fucking right beside us. By the grunts and moans I knew we helped to peak their enjoyment of each other.

I lay down beside J to cuddle and now watch them do their thing for a bit. "How do you feel hun" I ask.

"Great bb, better than great." She says while kissing my arms that hold her from behind.

"You like watching them?" gauging her interest in continuing to watch.

"Yeah they are hot. He's actually very cute. I didn't think there was going to be so many attractive people."

"Mmm, so you think he's attractive?"

Just then she gets up, her naked body on display, and inches over to the couple. The female is currently sitting on the edge of our bed and blowing her partner whose standing and enjoying himself.

"Do you mind if I jump in?" J shockingly asks the girl.

"After that show you both put on, it's the least we can do."

J grabs his cock while looking at me with that familiar devilish smile. "Since you didn't blow it earlier, I guess it's time for me to live up to my end up of bargain" then she places his hard cock in her mouth.

She begins to rub her hands along his erection from the top to the base of the shaft, with the second hand massaging her own tits and nipples. While she's enjoying it I watch in delight as the female is now massaging Js body. From her shoulders, down her back to her breasts then down to her waist and thighs. The female gently spreads Js legs to get space to touch her cum filled pussy. Seeing this is like a dream come true. The view of his female and Js magic mouth on his cock quickly built up to the point where I knew he wouldn't last much longer. J seemed to know it to. Timing it just right she gestures for his partner to take his cock in her mouth and finish him off.

She navigates away from them towards me "Let's get out of here, I want more of you...alone." She says while grabbing my cock and leading me to the changing room. We get dressed and head out, discussing the experience the whole way back to her place. We get inside and she tells me to go to the shower. Without delay I listen to her wishes.

"Now sit down" She demands.

"HUH?! You want me to sit down in the shower?"

"Yes! Just do it! I want you to eat my pussy!"

I sit down as directed and she positions her feet on either side of my body. She turns on the shower, nice and warm then proceeds to use both hands to pull her lips apart, and starts to pee. I watch it gush out splashing against my chest and stomach. Her pee has no smell to it, and not even a hint of gold in the clear stream. She must have drank plenty of water in preparation for this.

Laughing she's says "You wanted this! You did win it fair and square the first time we met so enjoy."

I actually did tell her that I wanted it and it's been a running joke since that day but I never thought she'd go through with it.

"You are too much!" I say laughing.

Once she finishes, I grab her ass nice and tight and pull her down to sit on my now rock hard cock. At this point she has removed the plug so I know exactly what I want to do. I ease her down nice and slow as if I'm posturing to put it in her willing pussy. She gasps when I instead slide my cock inside her ass. I feel her asshole stretch as I slowly enter her centimetres at a time.

"Fuck bb, be gentle with my tiny bootyhole" She says jokingly but in a blissfully sensual way.

I fuck her slowly ensuring she feels every stroke and once I feel her open up I start to pick up the pace. Faster, and deeper while the shower is raining down on us and I'm suck on her hard nipples.

"FUCKKKKK!" She screams as she cums and I shoot my load deep inside her.

What a night! One I'll never forget!