Winner Take Nothing

PUBLIC BETA

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

It was full dark when I got the docking routine done. Zoe was a superb bosun. We drove back to her place in comfortable silence. It had been a perfect day. We were feeling extra close. And we didn't want to break the spell.

She didn't invite me in. And I didn't ask. There would be a lot of time for that in our future.

Thus, the days rolled on. We spent all of our time together. And she eventually moved in.

It wasn't anything sexual. It was just that she needed a place and I had three bedrooms. So I offered and she accepted.

At that point there was no need to draw up rules. I slept in the downstairs bedroom and she slept in the one upstairs in the dormer. We shared a bathroom but living with Zoe was more like living with a guy. She didn't use all of the paraphernalia. Basically it was just a toothbrush.

I mean - she used makeup. But she kept that in her room. And at work she kept her luxuriously thick auburn hair in a long easy to maintain ponytail. Around the house she just let it loose down to the middle of her back.

We had a comfortable life together, sharing the household duties and generally enjoying each other's company. We would hang out in various places during the workweek and sail on the weekends.

It was an idyllic life. Until a couple of months after she moved in.

That Friday morning I asked her what time she wanted to leave for the boat. She said utterly casually, with no hint of anything sinister in her voice, "I can't go sailing this weekend. I have a date."

THAT statement dropped on me like a cartoon safe.

I said, "Excuse me - did I hear you right? Did you say that you had a date?"

She said absentmindedly, "Yes Anthony Piccardi asked me to go into the City with him. He has tickets for Wicked for tonight."

My head exploded. Okay, we had never talked about it. But I just assumed we were exclusive. Admittedly I hadn't tried to seal any deals. But I knew her situation. And given the cataclysmic ending to her last relationship I didn't want to put any pressure on her.

Then Piccardi just waltzes in and sweeps her off to New York for a weekend of fun and fucking. Unbelievable!!???

I was trying to keep my voice under control. But I probably sounded like I was choking to death. I said, "How long has THAT been going on?"

She said, conversationally, "Well he has been asking me out since I arrived. I don't find him that attractive. So I kept turning him down. But I really want to see that show. I'm not sure what HE has in mind but if it's anything other than dinner and a play he's going to be disappointed."

Okay!! I had to say it!!

I said, trying to make my voice NOT sound as frantic as I felt, "That guy is the biggest pussy hound on campus. He has had sex with half the staff and large portions of the student body. If he takes you to the City, he is going to expect a lot more than a good night kiss."

She said laughingly, "Oh, he'll get a LOT more than that. I'm just not going to give him the whole meal at the first sitting. I don't fuck ANYBODY on a first date."

Then she walked off toward her room chuckling at the sheer nerve of me thinking that she would put out for anybody.

I was left sitting there with my eyes bugged out like Wile E. Coyote, when he suddenly realizes that he has just run off the cliff.

I thought, "MY GOD she is totally oblivious!! She has no idea what she just did to me!"

I didn't know what to do next. I had never said one word to her about how I felt. How DID I feel??? I knew for sure that I didn't want her sharing herself with any other man. But I hadn't told her anything to the contrary. I had treated her like a pal. What was I going to do???!!"

I could rush upstairs and declare my undying love. But that would be the single wimpiest thing I could think of. Sniveling is just so unmanly in a situation like this.

So I sat there with my heart in my throat as she rattled around preparing to go out on her date. She was actually humming some Australian ditty like it was no big deal.

But it sure-as-fuck was a big deal for me.

I saw it all in a blinding flash of insight. I had a healthy 29-year-old woman living with me. And I had not made a single move on her.

Okay!! I was aware of her failed relationship and I was trying to respect her grief. But seriously!! Two months of walking around here wearing nothing but a long t-shirt and panties and I hadn't tried to molest her???!!

Instead of seeing me as her gallant knight-errant, she probably thought I was queer!!

She came downstairs at that point. I was sitting on the sofa trying to look cool. There was nothing I could do now. That is - without sounding like an insecure weenie.

But my nonchalant attitude was a total act. Underneath I was a seething cauldron of undistilled jealousy.

And she knocked me out.

I had never seen her dressed to kill. My rough-and-ready Aussie boat buddy was wearing a classic little black dress. It was tight enough around her body to show off her narrow waist compact hips and jutting ass. And it was short enough to display her magnificent legs. There was a scooped front with some pearls. Plus, a hint of surprisingly ample cleavage.

But the part that almost stroked me out was the face.

She normally doesn't wear much makeup. So I had no idea what a beauty she could turn herself into. But she was going into the City so she was firing for effect. She had done those gorgeous eyes. And their impact alone would have been sufficient to pea-green kill me.

But her lips are world-class and she had brought them to the forefront. They are so sexy that even without lipstick they are practically labial. Now - outlined and colored like they were - all I could think of was them contorted in passion as Piccardi entered her.

And to top off my misery she was wearing some kind of exotic perfume that provoked thoughts of wildly beating drums, fervently dancing flames and debauched jungle rituals.

She looked at me with deep affection, did a little turn on her four inch heels and said surprisingly tentatively, "How do I look?"

HOLY SHIT!! It was like she was asking a girlfriend.

I was speechless, sitting there with my mouth working like a recently boated tuna-fish. I think she saw the apocalyptic suffering in my eyes. Because she rushed over to me looking very concerned. She said anxiously, "Jonathon, what's wrong?"

I should have told her!! I absolutely should have told her THEN!! But my stupid pride wouldn't let me. I know it's a cop-out. But the dynamic was all wrong. It's a guy thing. I just couldn't wimp-out in front of Piccardi.

So I got it together and told her the absolutely lamest thing imaginable, "Well I was just disappointed that we are not going sailing this weekend."

She smiled lovingly at me and actually ran an affectionate hand down the side of my face. She said. "There are still a lot of weekends left. We just need to plan better."

I thought, "PLAN BETTER!! FUCK YOU AND THE LAWYER YOU RODE INTO TOWN ON!!"

This catastrophe wasn't caused by bad planning. It was a total communication FUCK-UP. I had made a bunch of stupid assumptions. I had gotten it all wrong. And now I was forced to sit there while that jackal made-off with the love of my life.

It wasn't her fault. She obviously had needs and I had treated her like she was my roommate. Well she WAS my roommate, but that was just temporary - until I had worked my way into her affections - and her panties.

How fucking stupid could THAT be???!! This wasn't a fucking Jane Austen novel.

At that point the doorbell rang. She rushed over to open the door. And there in all of his greasy glory stood Anthony Piccardi.

Okay, he was younger, better looking and a little bigger than I was. And he had money. But who's counting.

He was an absolute nobody on campus, an Assistant Registrar. But his family was rich - probably from prostitution, loan sharking and drugs. But it spent just like everybody else's.

He gave me his usual condescending sneer and said, "Jonathan my man! How're they hanging?"

Okay, James Bond he wasn't.

I was definitely NOT going to fold. I said dryly, "Great dude. How're they hanging with you?"

He grabbed Zoe around the waist, gave her a leer and said something subtle like, "They'll be hanging a whole lot better after this evening's over."

Then he turned and whisked her out of sight. She blew me a kiss as she was unceremoniously yanked onto the porch.

I got up and closed the door. As I did it I saw the douchebag helping her into his Corvette. The glow from his smirk outshone the streetlights.

There are moments in your life that you will remember forever. This was one of them.

I was actually surprised that I wasn't dead on the spot. Every system in my body was at the red-line, blood pressure, heart rate, and I was about to shit myself while I yakked on the living room carpet.

I wandered over to our couch and sat down with my head in my hands. How could I endure the eternity between now and when she got home?

I was going to straighten out this catastrophic misunderstanding as soon as she got back. And it would be in no uncertain terms.

It is one thing to be surprised by the kind of pre-emptive strike that would have made December 7th, 1941 seem like a nice quiet Sunday on Oahu. But it is another to let it happen twice. I was going to make sure that this farce ended the minute she arrived home.

Zoe was a grown-up woman and she had every right to accept an offer to do something fun. I hear that Wicked is a great show - not that I could afford to take her to it. All the same, if she went anywhere with Piccardi again - after I had made it clear how I felt about her. THEN we would know exactly where we were at. And we would go our separate ways.

I couldn't concentrate as the clock ticked. I paced and tried to read. That was a laugh. I never touched the TV. I just sat there staring off into space - locked in a maelstrom of emotion. The clock ticked some more. It was getting close to midnight.

They had been gone for over six hours when a cheerful text came in. It said, "Staying in the City. Don't wait up." It had a kiss emoji.

Oh how fucking wonderful!! They were getting a fucking room!!

I thought I was suffering before. I wasn't even in the foothills. It was like my heart was a trailer park and Zoe was the tornado.

Somewhat justifiably to my pain crazed reckoning - all of that agony transitioned to rage.

Anger is a primal instinct. It protects you - motivates you to fight.

But anger is also mindless. So, it is practically guaranteed that the next thing you do will be the stupidest thing imaginable.

I spent a mostly sleepless night staring at the ceiling plotting my revenge.

If I wasn't a pussy, I would have just toughed it out until we had our little talk. Instead, I chose to, "Give the slut a dose of her own medicine. Show her how it felt."

Every subsequent happening stemmed from that single bad choice.

I even realized that I was being infantile. My rational brain told me that it was asinine to try to exact retribution from Zoe. She was just acting like any other normal attractive woman - even if her taste in men was a little tacky.

The fact was. She didn't have a clue about how I felt about her. And the poor girl must have been as horny as I was.

Nonetheless, my lizard brain told me that I had been totally humiliated. I could see it in Piccardi's eyes.

You don't have to point out how childish THAT idea was. Zoe had done nothing to disrespect me except go out on a date with the douchebag.

Okay - the choice of date sucked. But he was also the only man who had actually asked her out. That included me.

Even so... I still felt like I had to get my pride back.

So at 8:30 AM sharp I picked up the phone. And I called Alice Whithers. She is the Dean's secretary.

She is more commonly known as "Alice the Bod." That was because she has the biggest pair of tits in Nassau County - and a booty that would drive J-Lo and any Kardashian wild with envy.

And Alice had already let it be known that she would meet me any time and any place.

I had never THOUGHT about taking her up on that offer. In my estimation she was dumber than a box of dildos. And I was pretty sure that I would get better conversation from Buster.

But if my Zoe could spend a sweaty night in a Manhattan hotel with that manslut. I could endure Alice for 24 hours.

She was delighted. I said, "Alice, I've been thinking about you. And I was wondering if you would like to sail down to Port Jefferson and party? Come back Sunday night?"

Port Jefferson is the place where the Ferry from Connecticut docks. And it has the kind of funky atmosphere that a girl like Alice would love.

She squealed with joy and said, "What time will you pick me up?" So much for playing coy.

I said, "How about in an hour? Bring something for overnight."

Okay - the fat was now well-and-truly in the fire. And I was already beginning to doubt my decisions. But I picked her up anyway. She lived in a cheap apartment complex north of town. I knocked on her door and she answered like she had been waiting on the other side.

She was wearing a slightly too tight t-shirt over her monsters - double D at least and maybe a letter further up the alphabet like "M" or "Z".

Her shorts were practically pornographic

She threw her arms around my neck, smashed those huge pillows into my chest, grabbed my thigh between her legs and gave me a kiss that included a lot of tongue.

That was exactly ten seconds into the date. God only knew what the next 23 hours, 59 minutes and 50 seconds would hold.

I un-pried her and said, "Wow!! That was hot!! Are you ready?"

I wasn't lying, It WAS hot.

She giggled and said, "Ready for anything big boy." The meaning of that statement was clear.

The little voice that lives in my head - and who I think might be my mom - smacked her forehead and said. "Oh my God!! This is SUCH a bad idea!!"

But I am gallant to a fault. So I manhandled Alice and a roller bag off to the boat. Zoe in contrast, travels with a cloth backpack.

Alice prattled all the way about things she had read on the internet. That was her version of "being informed." It was the usual celebrity hokum that I can't stand.

We got out on the Sound and Alice went into the cabin to change into a bathing suit.

I use that term advisedly because she came out in something that involved two small squares over her jutting nipples and a strategically placed triangle. That was all held in place by strings that looked like dental floss - which the swaying of her massive tits was threatening to break.

It was exhibitionism at its finest. She said gaily, "Can I get some sun?"

I said, "Sure - just spread out a blanket forward."

I thought, "Thank God I won't have to talk to her."

She made her way gingerly along the side of the cabin and up to the foredeck spread a towel and lay down on it. Then she took off what might be laughingly considered her top.

Lying on her back all I could see was her thick mop of curly blond hair with two huge heavily nippled mountains rising behind it and her feet widely spread. I assumed that was Alice's normal horizontal posture.

We had good wind and I was supplementing it with the engines. So we were doing close to 12 knots. That made the normal four-hour trip closer to three.

I got a call about two o'clock. I was just rounding Old Field Point and heading down the narrow peninsula toward the entrance to Port Jefferson harbor. A cheery Aussie voice said, "I'm home, where are you?"

I said just as cheerily, "I'm on the boat, like I said I would be. I'll be home tomorrow."

At that point Alice, who does not have a subtle bone in her body, loudly inquired, "Who's that Jonathon?" She had come back from the foredeck and was strapping those massive titties back down in preparation for arriving at our destination.

There was a long pause on the other end of the line. Then she said in a strangled voice, "Is that a woman with you?"

I said intentionally blithe, "Yeah - I didn't want to go out by myself and Alice Whithers volunteered to come along. We are just going to party it up in Port Jeff and then come back as soon as possible tomorrow."

Zoe knew that I was with the female equivalent of her date last night.

I realized what I was doing. In fact, I had planned it that way. The thing of it was though; instead of giving me great pleasure, like I thought it would - it just killed me.

You could have heard a pin drop on the other end of the line. Then Zoe said in a broken-hearted tone, "Well enjoy yourself" and I could hear the beginning of a little sob as she cut the call.

We docked at the public slips at the bottom of Port Jefferson harbor and walked up the main street to the several dance clubs nearby. It was evening now and things were just starting to heat up.

Alice was back to t-shirt and Daisy Dukes. To say the least, the local predator community was interested.

I had thought I felt rotten yesterday. NOW I was devastated. Alice was totally oblivious - of course. I ordered us a pitcher and we sat down at the table. She immediately started jiving in her seat.

She looked at me quizzically. I said, "I don't dance."

She was trying to pull me out on the floor when some guy who looked like he worked the Bridgeport ferry came over and asked her. She looked at me and I said, "By all means."

For the next three and a half hours Alice drank and dry-humped her partners. A group of about four roughnecks were pouring drinks down her. I was watching her get drunker and sluttier as the evening wore on.

As I sat there I felt nothing but emptiness. Zoe had gone on a date. I had escalated. I didn't think this was the end of the match. And I was not looking forward to the return volley.

Meantime Alice had disappeared. I had no interest in who she might be with. But I felt responsible. So I went looking for her.

The voice in my head - who might be my mom - shook her head in disgust and said, "You are such a fucking over-principled, over-bred dumbass."

I eventually heard Alice rather than saw her.

There was a rhythmic wet, slapping noise and a choking Ughhh-Ughhh-Ughhh-Mmmmmph-Mmmmmph-Mmmmmph coming from the far side of the parking lot.

I walked toward a beaten up Chevy van - while staying in the shadows.

There was Alice on her hands and knees with her massive butt sticking up in the air. She was taking it from the back from some invisible dude who was inside the van. While she deep throated a guy who was standing on the cement in front of the open doors.

The other two dudes were impatiently waiting their turn.

It would be a vast understatement to say that she looked and sounded like she was having the time of her life. The guy she was sucking let out a low grunt and an Unhhhh and I could see his butt muscles flex. Alice's throat rippled enthusiastically.

Then she dropped his cock and began a frenzy of frantic moaning. It was a play by play that I could hear from where I was standing. She was wailing, "That's it baby - so good - fuck me - fuck me - HARDER - Oh Jesus I'm cumming." The last was a feral howl.

I am no hero. But I had brought her. So I had to do something. I was not going to take on four burly dock-hands to protect Alice's highly questionable virtue. But I COULD dial 911 from the bar's ancient payphone and report a ruckus in the parking lot.

I was standing in the shadows as the cruiser rolled up. Alice was just finishing up the second pair as the flashing blue and red lights appeared. The guys scattered leaving her lying face first in the back of the van.

She had the presence of mind to pull her shorts back on, grab her t-shirt and head for the bar - giant melons flapping as she ran.