Ever wonder what happened to your high school sweetheart? You know, your earliest crush. The girl you first loved and lusted after? Maybe things didn’t work out between you, maybe you never even had a chance with her – but you must admit, you’re curious about how her life turned out. Has she done well for herself? Is she married? Kids? Or maybe she’s a career girl, still single, still waiting for the right man to come along.

She was hot, wasn’t she? Although she dumped your ass, you can’t help wondering if, given your financial success, you might stand a second chance with her.

Well, I thought that. I thought I had a second chance with my ex fiancée. Heather had kicked me to the curb age 19, and five years later I’d tried to win her back. I’d lost her to another guy while at college in Albany NY and the circumstances had devastated me. Heather wasn’t just my girlfriend, she’d been my first love and soul mate. I didn’t take the breakup well. This is the story of what happened.

I’m Tim, and Heather and I are both from Syracuse. She was a gorgeous brunette from a liberal ****** who were friends of my mother and father. She was slightly plump with medium length hair and freckles. She had a cute cat that she doted over. Although she worried about her weight, those curves made Heather so much sexier to me. I’d been in love with her since High School, and finally plucked up the courage to ask her for a date when we both started college in Albany. And, even though we only dated a few months, I had persuaded her to wear my engagement ring.

However, just weeks after accepting my band of loyalty, Heather had abruptly ended our relationship and started dating a black basketball player named Du’Shawn. To make matters worse, Du’Shawn was a notorious bully. He’d intimidated me while Heather and I were dating. Twice he’d stopped me in the school corridor with Heather present, and tried to persuade me to fight. Of course, I was no match for the black man physically, being rather slight and short myself. He’d tapped my face, asking me if I “wanted my ass kicked”, daring me to retaliate, but I kept my hands firmly at my sides. Once, he knocked my books out of my hands and gave me a hard kick to my backside when I bent down to retrieve them. Heather was sympathetic to my plight, urging me to file a report to the Principal and referring to Du'Shawn as “that asshole”.

Christ! It still riles me to recall what happened then. I loved Heather with all my heart. I couldn’t believe it when, just weeks after accepting my ring, Heather was exclusively dating “that asshole” as she put it. It ruined me, I tell you.

“I’m sorry Timmy, really, but I’m not ready for an exclusive relationship yet” Heather had said to me over a hurried coffee, as tears welled in my eyes. “We’re both too young for a full time commitment, we both need our freedom. We have our entire lives ahead of us.”

But just fucking days afterwards, the bitch who’d told me she “wanted her freedom” was the exclusive property of Du’Shawn! She started followed him around everywhere, I’d see them walking down the corridors of college, Heather hanging onto Du'Shawn’s muscular arm and staring doe-eyed up at him like a lovesick slut. She even had a new way of walking with him, she wiggled her ass sexily like a fucking bitch on heat . For me, it was such a mental slap in the face, I went crazy! Honestly, I felt such a fool.

Once, I swear man, once I walked into the cafeteria to see Heather sitting on his lap as he chatted on his cellphone. I freaked, man. I couldn’t believe that my Heather was openly sat with her ass on her black lover’s lap in heels with her tight skirt riding high, in front of about 30 other students, feeding Dushawn pieces of a fucking Hershey bar if you please. Feeding him while he chatted on his cell, his big paw round her waist. The sight ruined me. I couldn’t comprehend how she could actually date the same guy who had bullied me and kicked my ass. She’d just discarded me just like that fucking Hershey wrapper.

I’d never slept with Heather, but looking back it seems she broke off our engagement after succumbing to the big black man’s advances and letting Du’Shawn fuck her. I guess she’d simply chosen the stronger, more attractive male over her weaker boyfriend. She’d “traded up” as attractive girls often do.

As I said, I didn’t take it well. I became bitter, a bit unhinged. I was obsessed with how badly she had treated me. I contacted Heather on numerous occasions after the split. I just couldn’t let it lie. I must have tried talking to her six or seven times, waiting for her and stopping her in the street, trying to win her back. I texted her constantly.

I made things worse for myself by, after a few drinks, visiting her liberal parents to try to win them over. I told her mom that Du’Shawn was a dangerous bully who had threatened to beat me up and was probably involved in the drugs trade. I didn’t hold back my tears, and naively I felt that Heather’s mom would support me. However, to my shock she told me she approved of her ********'s decision.

“Heather’s made her choice Timmy” she said, after I’d opened my heart to her "Why shouldn't she date a black man?.

“Why are you objecting to my ********’s dating preferences?” Heather’s mom said. “Don’t you know how racist that sounds?”

For a while Heather didn’t tell Du’Shawn about my pestering but eventually she had enough and told her new boyfriend that I was “stalking her”. As a result he beat me up pretty badly. He confronted me outside my apartment one day and didn’t hold back.

He beat me pretty bad, but it was what he said to me while beating me that convinced me to leave town and move to the big city. Du’Shawn told me he’d got Heather all juiced up then refused to give the slut more cock until she ditched me

“Took her all of five minutes, then she was back on my pole” he growled

It couldn’t be true, I thought…could it?

”I was fucking yo bitch five minutes after she ditched yo ass, hows about dat? Du’Shawn yelled as he kicked me.

There’s a thin line between love and hate, they say, and in the end, when I knew for sure she wasn’t coming back, I hated Heather with a passion, Right before leaving town on the late Amtrak for NC .I sneaked outside her house intending to pour sugar in the bitch’s gas tank. Unfortunately it was locked. Then, Heather’s evil cat then sidled up to see what I was doing. I launched a kick on its backside, making it yowl in pain. Just for a moment, I felt good.

Part Two

Well, almost five years on, I’d managed to put the events in Albany pretty much out of my mind. I’d moved to NYC and, while not exactly successful, had a lower grade accountancy job and an Inwood co-op. I was making ends meet, the property had doubled in value and I had savings. Problem is, I couldn’t get laid. I just couldn’t find the right girl. My wallet and ego needed long recovery times from my high-stress dates. To be honest I spent most evenings on the computer, smoking weed and watching porn. I really needed a woman.

During my first year in NYC I had taken a job on the male stripping scene, mostly working bachelorettes and gay events. The work was crappy but at the time I really needed the money. I found some of the scene downright nasty, especially the bachelorette events. Those hot girls could be mean to strippers. I don’t have a massive cock, and on more than one occasion the unveiling of my package was met with hoots of derision from those mean bitches. I quit as soon as I got a day job.

The NYC dating scene is so ruthless that you must use any advantage you can. I’d kept a picture of myself on my dating profile back from my stripping days, dressed as a “hot waiter” at an event, bare-chested but for a bow tie. I also had a video of me at a bachelorette dancing to “You Can Leave Your Hat On” – stripping naked from a sailor suit. It’s a good video, I had a decent body back then, before I put on weight.

The only flaw in the video was at the end, after I’m naked and the music is finished. One of the girls clearly yells “Pull your pants back on honey!" and a number of other girls screech with laughter.

Anyway one day I was browsing Facebook and there she was. “People you may Know – Heather Aston”. It was my ex, all right. I couldn’t mistake her. That smiling, cute face in a tight sweater. Her relationship status said “It’s complicated”

I was immediately curious and clicked on her profile, but most posts were private. Seeing Heather’s profile brought memories flooding back. She hadn’t really done anything bad, I reasoned, apart from falling for the wrong man. Should I send her a friend request?

I had to make a decision. Would a quick mail hurt? Should I test the water?

Before I had time to reconsider, I put in a friend request and added a message. The message read: “Hiya Heather, guess who? I’m sorry for acting like an asshole in the past, but I’ve moved on now, gentler and more chilled. Joined the rat race I suppose. I have a place in NYC and work by Wall St. It would be great to catch up sometime, but no worries if not. Hope you’re doing OK, Tim xx

There then followed an anxious few days, and I’d almost given up on a reply when I saw the red message notification on my Facebook.

“Hi , good to hear from you, sorry for the delay, I don’t use FB that much” Heather wrote. “I feel guilty about that time, I know I treated you mean. I was so messed up in the head . I hope you can forgive me, Heather xx.”

In our subsequent messages Heather told me she’d “gotten involved with a bad crowd” and had dropped out of college. But now she was getting her life back on track, she said, and was looking for work, possibly in NYC. If I was ever in Albany, she said, I should look her up. As far as I could tell she lived alone, and there was no sign of Du’Shawn or any man on the scene.

“What’s that picture?” Heather asked me in a FB message “Is that you, that sexy hot waiter?”

“Err…could be” I said.

“You look fantastic” she replied. “You always were a good dancer Timmy”

A week later, on a whim, I sent Heather the video of me stripping. She sent back lots of smiley faces

“That’s brilliant, maybe I should have you come up and perform for me” she said, adding a smiley.

“LOL” I replied. “Maybe I will sometime”

“Seriously, if you are ever up here, look me up” Heather said. “It would be good to have some company and catch up on old times. To be honest I could use a drink. I haven’t been out for weeks”

I had no plans to go to Albany but I reasoned, I could easily invent an excuse. I told her I would be taking the Amtrak to Syracuse next month to visit my ****** and could hop out for a night in in Albany on the way. It would be fun to get together, I said. We arranged to meet on a Friday night in the middle of September.

I quit work early, took a shower and jumped on an Amtrak heading upstate. As an afterthought, I threw my sailor suit, into my case. I'd strip for the bitch if that's what it took to get laid, I reasoned. On Heather’s recommendation I’d checked into the Best Western for the night. I hired a car at Rensselaer. The hotel was cheap, in a rough part of town, with a couple of dodgy-looking nightclubs on the street opposite We’d arranged to meet in Olive Garden, and I arrived early after another wash and shave.

When Heather arrived she was fatter than I remember, almost plump, but she still had the same eyes, smile, and dimples I’d fallen in love with. She was wearing very tight jeans, a polka dot blouse and high heels. In a second all the memories came rushing back to me. Heather had been the love of my life. I was somewhat shocked to see her this way. She had a few tattoos, including a couple of symbols on her wrists. But still, she was very beautiful.

Well, Heather and I had a great meal and shared a bottle of wine, then another. She told me that she had only been together with Du’Shawn for about six months after we split, and had had a succession of crappy boyfriends. Heather then asked me about my stripping. I'd made it sound more glamorous than it was, and after my fourth glass of wine I mentioned that I actually had that sailor suit in the trunk of my hire car.

“You never know, this might be my lucky night!” Heather said and laughed

Before we knew it the restaurant was closing, and we were both reluctant to go home. I was going to invite her to my hotel bar, but she had another suggestion.

“I know, we can grab a nightcap in the Black Star Lounge” Heather said. “It’s right beside your hotel. It’s a decent place and they play great music.”

We took my car, and five minutes later we were walking into the joint. The place was about half full, mostly black guys and women of all races There was a long stage jutting out into the middle of a seated area, a dance floor and a DJ booth.. All the black men looked tough, I though, and some were wearing what looked like gang insignia. I was the only white guy in the place, I suddenly noted.

Isn’t his a bit rough babe? I murmured to Heather as we strolled in.

It’s OK we can get in the VIP Area” Heather said. “It’s this way, follow me”

I followed Heather’s hot, jeans-clad ass across the club. She nodded to a bouncer sat on a stool and we walked through some plush curtains into a discreet private area, and sat at a table. There were four black guys there in that small room, and a couple of women, drinking champagne and smoking reefer.

“So, Timmy, you think you’re a gentle guy really?” Heather said

“Yes, I think I got more of a hold of my temper these days”

Then I started feeling a little uncomfortable. I noticed that the black guys were all staring at me. Two were now sat very close to me, closer than before. They had moved their chairs closer to our table, uncomfortably close. One of them was staring me, right in the face.

“Really” Heather asked.

“Did you have a hold of your temper when you killed Bart?” Heather asked

At first I simply didn’t understand. Who the fuck was Bart? I didn’t know how to respond. What had she just said? Did I hear her right

‘Don’t try to deny it” she said. “I saw you running away after you fucking kicked Bart to death”.

Then, all of a sudden I remembered. Bart was her fucking cat of course. .

Fuck me! I could hardly comprehend it. The mangy feline hadn’t been in the best of health. I knew that as I’d previously spent a fortune on its meds. But no way the fucker could have actually died? Could it? Shit, she had loved that cat. She must hate my guts, I thought.

Then I realized that the black man staring me in the face was Du’Shawn.

Suddenly I was terrified.

Heather then just stood up and walked about six feet away from me, behind the black men.

“I can forgive a lot of things Timmy” she said. “But not killing fucking my cat. “You fractured her fibula and she had to be put down” she said. “How could you stoop so fucking low”

Heather was seething

“Go on guys. I’ve been waiting for this” Heather said icily “Give him what he deserves”.

I was then set upon by the men. My arms were held down and I was and slapped, again and again, across my face. Then they started kicking and punching me. My arm was pushed up behind my back, causing terrible pain if I resisted. They continued to beat me as Heather looked on. ‘Yeah, pummel him Du’Shawn” my ex fiancee said. “Make him feel pain, like Bart felt”

Then eventually a guy who I later learned was called Flip grabbed hold of my jaw and held it in his fist

“We want PIN codes, want every dollar from every bank card, bitch, and we went your online banking” he said. “You gonna stay here while we drain ya cash”

They made me write down the pin codes for each of my cards, which Flip then pocketed along with my wallet.

Heather just looked down at me, her arms folded, just staring at me. She looked angry.

“House keys” Du’Shawn said and I handed them over. He tossed them to Flip

Take da Mustang” Du’Shawn said and Flip vanished,

Horrified I realized that Flip was heading out to drain my credit and then take anything of value from my apartment. My spare cash was there, right on the dresser at home, a couple of grand. I’d be left with nothing.

Then, I saw that Heather was showing the black guys something on her phone. They were cracking up with laughter. Then I heard the music. It was “You can Leave Your Hat On”.

Suddenly I realize she was showing them my strip video.

“That’s fucking hilarious” Du’Shawn said

“Is he serious?” said one of the girls who were with the black men.

“Listen, she tells’ him to put his pants back on” Heather said.

Put your pants back on, Honey!!!

They clearly all heard it. The entire room all burst into laughter. She kept rewinding it.

Put your pants back on, Honey!!!


Put your pants back on, Honey!!!

Then the curtains to the VIP area opened and big, bald black man strode in. “You guys needin’ drinks? he said

“Hey Big D, you be needin a pole dancer? DuShawn smirked.

I stared at him in horror

“White boy here’s a stripper, we need to hold him a few hours while Flip checks his crib. How bout we get him out on the pole? Make him strut like a bitch for us”

“You said you’d dance for me Timmy” Heather said

"That right white boy?" Big D said

“He’s got a costume in his car” Heather said, standing arrogantly in her tight jeans and black heels and staring at me.

One guy fetched my costume. Then I was forced to changed into it. Heather vanished for a moment and returned with some pink "fuck me" heels she’d procured from somewhere

”Put these on” she said. Heather took out her lipstick and put some red gloss on me. “Pout” she said, laughing. The evil whore was *****. To finish off my look, Heather put a pink collar around my neck. "If only Bart could see you now" she said.

Then, the music stopped and the DJ made an announcement. “Ladies and Gentlemen, coming up, all the way from the Big Apple, give it up for Tiny Tim!”

“I was pushed onto the catwalk, to the braying laughs of the women present and the guffaws of the men. I had no option but to start prancing round that stripper’s pole to some god-awful hip hip music in my sailor suit and bitch heels.

“Yeah, dance like a bitch” one girl cried

“We wanna see what yo packin” another shouted.

“Tiny Tim!” another cried.

"Strut your stuff white boy"

So there I was, stripping and humiliated, wearing makeup and dancing for the hot bitches of the state capital whilst my bank accounts were being drained and my apartment robbed. Those whores took plenty of photos, of course, videos too. Maybe they were even live streaming .

Right at the end of my strip, the part where I remove my hat from my crotch, Heather did something terrible. As I revealed my penis, the girls in the audience were shrieking with laughter. Heather was sitting at a table a couple of rows back, and we caught each other’s eyes. Staring into my eyes, Heather raised her left hand and deliberately folded all her fingers into a fist except her pinkie finger - which she then proceeded to wiggle about in the air, at the same time fixing me with a scornful look. It was excruciating

“Awwwwww” Heather mouthed at me.

Well, that’s not the worst of what happened at the club that night. I as forced to stay there for the entire time it took Flip to drive down to NYC and empty my apartment. It was hell. I’m sure they were all high on drugs.

I didn’t get out until 6am, when I was thrown from the club onto the street wearing just a G-string and high heels. I had to make the two-block walk to the hotel dressed in that manner and then request a new room key from the intern at reception. Luckily I had a spare car key and my gas tank was full.

I put on some clothes, got in my car, and drove back to NYC. The first thing I did when I got home was unfriend Heather.


[Inspired in part by the writings of “Weak White Wimp” on Literotica]
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