December 1 – 15 2000 Post Archive :: I Want a New Girlfriend

December 1 – 15 2000 Post Archive :: I Want a New Girlfriend

Thursday December 14, 2000

Old News / Forums

Ask Jack (11:33PM EST)Jack
Been awhile since I did some relationship advice so I decided to whip out a letter from the inbox.

From: Rave 4 Life
Subject: Hey Jack (giving you some props)
Great website. I have to give you mad props for it. I’m an interracial child :). I am Half white and half Asian. Throughout my life i’ve hanged around different crowds of people and seen how each are treated. I have to say Asians have been treated and stereotyped so much. Since i am percieved as Asian by whites and by some Asians as non-Asian. People are unsure if i am Asian or not.. You can usually tell but if i where sunglasses, a hat, or in a dark room (like a dance club) people sometimes can’t tell if i’m white or not. Being “white” i have had more success than being asian when around a girl. I read that post about that kid eric and i can relate. I am only attracted to white girls also (usually and was true up until Sophomore year in HS), there are a few girls i like who are from south america (latinos). I have also never had a true girlfriend.. (someone i called a girlfriend.) I just wanted to wish eric the best of luck and wanna know how he’s doing.

What a nice guy…. I forget who Eric was, but yeah I hope you’re doing good to. That sucks about the Asian thing, and the lack of a girlfriend. Asians are almost as stereotyped as blacks. People think all Asians are super good at math and karate.

Two reasons for my bad luck – one i am asian (well i feel like this is one of the reasons) and two because i am shy. I need some help to overcome my shyness… (i’m not sure if it is because i’m shy but it seems like i never have any thing to say to her this even happens when i with a group of my friends friends or people i don’t really know.)

Yeah shyness is tough dude, it’s just something you have to work at. It’s not one day you’re going to wake up and be the center of attention. Try learning some jokes or something, or even as gay as it sounds, join one of those after school clubs. It sounds like you’re in a slump or something. Maybe you should just get a hooker….. They will do wonders to your self esteem.

This began to happen ever since i entered High School… i always remember up until that point i used to make friends easily and was even popular (through my eyes), people used to follow me around because i was funny and fun to be with. I only hang around the people i know and it is hard for me to get new friends… This year i only sit with the people i’ve known for a few years and when they are not their i go to the library so i don’t have to sit by my self at lunch. Any info would be helpful, i don’t want to be quiet anymore.

You sound like a pretty smart dude, smarter than most of the birdbrains that write in to me. Find a girl that has some common interests and start talking with her. Or just be a total jerk to every girl you meet and you’re guaranteed pussy.


P.S. This props msg has has changed to a help msg… lol (reply back please)

Comments For Jack Can Be Posted Here

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How Paranoid Are You? (7:47PM EST)Jack
I just got this link sent to me. Semen Test: Is She Cheating? From what I’ve read they check out your panties and boxers and see if there any semen present. If there is they can do a DNA check and all this other shit to see if your girlfriend or boyfriend is cheating on you. They even give step by step instructions on how to collect the sample. So fellas, if you start to notice your boxers full of little holes, she’s on to you.

Old News / Forums

Posted Some New Stuff (7:11PM EST)Jack
Put some new stuff in the Sex Tips section. Things about women’s fantasies and crap like that. Found an awesome new site the other day. It’s called Inner Filth. Not only is it a bad ass domain, they made me a button!! Check them out and visit often.

Old News / Forums

This Was Pretty Funny (6:26PM EST)Jack
I received this is my inbox today. Some douche bag with an anonymous email address sent this to me. For the record I would never hit a girl, espcially a pregnant one.

From: Anonymous
nice to know the real reason why you’re ex doesn’t want you anymore. wait till this gets out.

“Jack Sullivan, Man Sentenced for Beating Pregnant Former Girlfriend, Boston Herald, September 10, 1999, at 14, available in 1999 WL 3407650.”


ok, moron. if only you knew how to read… the “14” is a citation, indicating where you can find the case info. not your age. you’re dumber than i thought.

Boy 14 seems like so long ago….. If I was 14 last year that would make me 15 this year? Seems a far way off from the 22 years I’m carrying around now. 14 was a good age I guess….. We used to get into R rated movies for the children’s price, shit I never got carded for smokes when I was that age. I always just told them they were for my mom. Stupid clerks always bought it to. My biggest goal back then was getting up a chicks shirt, and the worst thing I had to worry about was getting caught smoking pot in the bathroom. Now I’ve got insurance, finals, and a fuckin job!

Old News / Forums

Fuck (5:57PM EST)Jack
How come no more hot girls take pictures of themselves any more? I used to get at least one picture a week, and now they’re barely coming in. Kind of a let down if you ask me. Don’t despair people I’ll still continue to write my stories and share my advice. I’ll do it till the day I die baby.

So what do you people want today? Porn or Advice? You can choose for yourself I guess. I hope some of you guys and/or girls get something out of this site. I love doing it, and it’s great to know that people like the shit I do. I want more women to contribute though!! Bless us with your knowledge, or just fuck off and show us your tits!

Wednesday December 13, 2000

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Forum News (10:56PM EST)Jack
I’ve recently noticed that the message boards are starting to pick up. There’s plenty of cool members, and tons of interesting stuff to talk about. But I’ve got a proposition for other webmasters. How about I make my message boards a community system. If you have a website and you want to have a high quality message, email me and I can set it up. We could make this great place to exchange ideas and shit like that. And you get to be a moderater!

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Ways To Be The Hit of The Party (7:44PM EST)Jack
With Christmas right around the corner it’s now party time. In the next month you’ll probably be going to more parties than during the rest of the year. And even when Christmas is over, there’s New Years right around the corner. So if you’re looking to score at your company or friend’s party here some tips you need to know.

Don’t Be Shy
Have you ever seen the little nerd from accounting pick up the hottest girl at the end of the night? Of course not. To get a girl’s attention, or anybodies for that matter, you have to overcome your shyness. Nobody was born Don Juan and you’re going to need some practice to home your social skills. Try talking to people who look shyer than you. There’s no need for some long drawn out opening line, just be yourself. I can’t tell you how many times a simple ‘Hi, my name is….’ has worked out for me.

Look Good
During the regular week you may wear jeans and you’re wife beater… That shit aint going to fly if you want a classy girl. I’m definitely not what you would call, ‘in style.’ I need girls to pick out my clothes for me so I don’t look like Urkle. But I do know that a girl isn’t going to take home Biker Joe, is Don GQ is at the party.

It’s Not What You Say
At a party it’s not what you’re talking about, but how you’re saying it. If you’re shy then you’re going to have to work on your banter. Basically banter is just small talk before the eventual conclusion of sex. Think up some witty things and see what works. If you notice that your joke about the president and Monica Lewinsky is bombing, don’t use it. If the joke about Elian and Janet Reno is a hit, file it for later use.

Go To As Many Parties As You Can
The only way to become the hit of the party is to go to as many parties as you can. Make yourself known, and make yourself available. Make friends with the people who run the parties and shit like that. It’s all about connections baby, and without those you’re going to be going nowhere….. fast.

Old News / Forums

Some Times On a Slow Day (6:55PM EST)Jack
I’ll go through the referral logs and see what web sites have linked me.

Angry-Kids – got your usual assortment of rants and other shit. They do have some games and mp3s which is kind of cool.

Shock Comics – fucking funny ass site with tons of shockwave stuff. Every time I go there, something new grabs my attention.

Electralux – I love Violet! I love her so much and I want her to have my kids. Well I at least want her to pose naked in every position for me.

Shoot the Stupid – this girl runs a pretty sweet site. Plus she wrote some good stuff on her hand.

chaste – this site showed up in my referral logs, but I can’t find a link to me anywhere. I checked it out pretty quick and it’s totally fucked up. First picture I saw was some dude with a metal thing on his dick. Fucking weird people.

Slashdot – another one of those phantom referals…. Awesome site with tons of technology info.

Troma – you remember the Toxic Avenger right? Well there’s a website now….

Psycho Ex – I think the name says it all.

There’s a ton of other, but I don’t feel like putting them up right now. I’m more concerned about watching Serra’s naked body on the webcam. If you’re a CHICK and you want to be on my webcam portal, just drop me a line.

Old News / Forums

Hump Day (6:24PM EST)Jack
It’s the middle of the week and you know what that means…. free porn! Of course that shit happens every day, so what’s the big deal. Today I’ll give you some special stuff to get you through the long winter night. Of course if it’s cold where you are, you could try some streching. It’ll loosen you up and make you healthier too.

Remember how I was talking about my new line of insta-girlfriends? They are the ones where you don’t have to waste all that time getting to know her and making her happy and shit…. Well I made a brochure. The Insta-Girlfriend will love you, and give you your space.

A week from today I will be a free man…. No more early morning trudging through the snow to get to class, and no more late nights studying for finals. I’m going to take advantage of this time off and have me some fucking fun….

Tuesday December 12, 2000

Old News / Forums

IWANG To Cut Staff (7:15PM EST) New York Times

SPRINGFIELD, Mass. (Reuters) – I Want a New Girlfriend Inc., a relationship and E/N website, said on Tuesday it will cut 25 percent of its workforce and take a fourth quarter charge of $10 million to $12 million for a restructuring.

The move follows IWANG’s earnings warning last week that it expected a fourth-quarter pro forma loss of $18 million, or 50 cents a share, far wider than the 33-cents-a-share loss analysts had expected, according to investment research firm First Call/Thomson Financial.

The staff cuts announced on Tuesday, which amount to about 180 full-time positions, will reduce costs by about $45 million in 2001, the company said, adding it expects to achieve profitability in the fourth quarter of next year.

Shares of the Springfield, Mass.-based company lost more than half their value on Friday, a day after it issued the warning and said that Chief Executive Jack Sullivan was resigning. Sullivan was to remain at IWANG as executive vice president of market development, the company said at the time.

He was replaced by Tyler Durden on an interim basis until the company finds a permanent replacement.

IWANG stock rose 21/32 to $3-31/32 on the Nasdaq on Tuesday. The shares are well below their 52-week high of $139-1/4, reached shortly after the company went public earlier this year.

It joins a litany of other dot-com companies that went public in the past 18 months and have now seen their fortunes change dramatically as the dot-coms have fallen out of favor with investors.

In explaining the moves, President Marla Singer said in a statement: “We have realigned the organization to leverage (our) core assets and exit 2000 with a stronger business model that produces that consistent growth and profitability our shareholders expect.”

As part of the reorganization, IWANG will split into two divisions — Lesbian Porn and Relationship Advice. Both units will have independent profit and loss accountability, including separate sales, marketing and engineering departments.

Help me run this website, click here.

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Dumping Your Girlfriend (6:52PM EST)Jack
Every one has been in that position where they are just sick of the person they are dating. Of breaking up isn’t the easiest thing in the world to do. Normally if you’re doing the dumping, your soon to be ex is going to whine and do everything to get you to stay…. And if you’re the one being dumped, you’ll going to make damn sure that you don’t lose your one and only……

I think many people break up for the wrong reasons…. In the past I’ve dumped girls because I would think, “Wow if I can get this girl in the sack, I wonder if I could score some other hot chick….” Not the best reasoning, and it never really worked out in my favor. I’d usually dump some hot piece of ass, and then end up not getting laid for a few months.

It can work out in other ways too though. Has any one else noticed that when it rains it pours?? It seems like whenever I’m in a relationship, I get more ass from different girls. I was going out with a great girl and we were hitting it off great, but the temptation was way to much for me. How could I, as an 18 year old kid turn down unattached poontang. I’d have these spurts where the poon rained down, and then all of a sudden I’d get a dry spell worse than the Mojave desert.

As a college student I’m not really looking for anything to hot and heavy. I like sexual adventures on my college campus and I like going out drinking. Not to complex, and I need a girl that will let me do that shit. Any takers?

Old News / Forums

Quick Links (6:45PM) Jack

Payback Productions – I Love Bacon – Bad Ass Mofo – Electronic Whore –

– Club Sandra – Stile Project – X-Entertainment – Dot Cult –

Old News / Forums

I Hate Winter (6:08PM EST)Jack
Christmas is like two weeks away and I can’t fucking wait until it’s over. I’m what you would call a last minute shopper. You’ll find me on December 24 cruising the mall looking for that a for everyone on my list. I’m really starting to hate winter too. I have this thing called Raynard’s disease or something like that. Basically it means my blood circulation sucks a fat dick. So in the winter time I’m constantly cold and always uncomfortable. I really need to move my ass down to Florida.

Oh yeah to top this wonderful day off, the power was out for a couple hours this morning. Not to big a deal, unless your clothes are in the middle of the dryer cycle. Luckily it came back on and I didn’t have to go in to work all sopping wet. Other than that, it was another non eventful day in the life of Jack. I plan on partying like a rock star this weekend, so I should have some good drunk stories for you.

I think every office needs a girl like this…. You know come in grab some coffee, a donut, and blow job. I think sex on the job is vastly being underused. Morale would go up, profits would explode, and dot com companies would prosper again. Hey if they got saunas and other shit like that, why don’t they bring some hookers??

Speaking of hookers, I’ve never really had a hooker experience. Most guys can tell some story about how their dads brought them to the local whore house so they could become a man. Or maybe how they are their buddies took the bus to the city and came back to there homes men. I have no stories like that. The closest I came to a hooker was when I was walking from AIC to the package store. Some fat black lady with about 2 teeth came up to me and asked of I wanted a blow job for 5 bucks. I looked into my wallet and saw that all I had was five dollars for the six pack I was going to buy. So I kinda weighed out the advantages and disadvantages….. and well the six pack won over the blow job. If she was hotter I probably would have taken the blow job. But living here in Western MA, I’ve never even seen a hot hooker. I have to be content with farmers daughters they chew on hay all day long…….

Monday December 11, 2000

Old News / Forums

Piss Off Your Ex-Girlfriend (7:37PM EST)Jack
I love getting emails from guys whose girlfriends have cheated, dumped, or basically fucked them over. Of course these girls are too stupid to remember that they had some naked pictures of them taken before…….

From: Some Guy
Subject: My ex is a whore
Hey Jack here you go, post this bitch on your site.

– Ex Girlfriend 1 – Ex Girlfriend 2 – Ex Girlfriend 3 –

Very nice my man! If you have an ex-girlfriend you’d like to showcase on this site, give me an email. If you’re a girl and would like to be on the site you can email me too.

Old News / Forums

I Came To Bring The Pain (5:14PM EST)Jack
It’s another Monday and that means another day of school. Of course it means one less day that I have until Christmas break. Over the weekend I went to an awesome wedding. I drank some beers and kissed a lot of girls. It was a pretty good time I’d say. Both the bride and her girlfriend got a little messy later on and started to indulge in some fun before whisking off in their limo. They made such a pretty couple….

Going to the wedding made me think about marriage, and how fucked up it is…. I don’t think I’ve ever going to get married. Every relationship I’ve been in has been worse than the last, and I don’t see myself finding the one at the school I’m going to now. Then there is next year where I’ll be so busy with school, work, my kid, and everything else that I’ll barely find time to jerk off… Let alone try and make a girl feel special. You know those insta-meals, I need an insta-girlfriend. I wont have to waste time getting to know her, or taking her out to dinners and crap like that. The insta-girlfriend will come with all her vital stats written right on the box.

Name: Cassandra
Height: 5’7 (I’m tall)
Weight: 120
Bust: 36C
Interests: Giving head, cooking, cleaning, hand-jobs, making sure I’m happy.
Turn-ons: Farting, belching, smelly socks, threesomes with Victoria Secret models.
Turn-offs: Soap operas, a dirty house, actually, nothing turns her off. She’s always horny!

There we go…. That’s all I need to make me a happy man. Plus all her other minor details would be right there on an index card for me to periodically glance at. Shit I’m going to start marketing that crap……

Quick Links:American Jackass – The Campus Rag – Daign – Dgnr8 –

Chimptopia – Stile Project Top 50 – Mac’s Ramblings – Amateur Porn –

Sunday December 10, 2000

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What’s Up Sluts (2:13PM EST)Jack
For the last couple of hours I’ve been been chilling working off my hangover. Any one know any quick tips to feeling better? The only thing I’ve been able to do is smoke some butts and watch Beverly Hills 90210. They had back to back episodes and they were both classics. It was the one where that ugly chick Donna gets drunk at the prom and they catch her and bla bla bla….

What’s funny is that I had a similar experience happen at my prom. We were all hanging out at my friend’s house taking pictures and waiting for the limo to arrive. Me and this girl go around to the back of the house take a couple rips off the boule and drink some champagne. Everything was fine until it came time to get in the limo and go to the prom. The chick that I was smoking with could barely fucking walk and we had to carry her to the limo. We knew there was no way she was going to make it to the prom….. When we got there we had to tell the limo dude just to drop her off at her house, sucked to be her on that night……

The prom pretty much blew goats for me. There’s a whole story behind how I ended up taking the wrong girl, but I wont bore you with the details. It all comes down to how I didn’t get laid on prom night. Nothing really exciting there.

From: Rick
Subject: a crazy story that happened to me tonight……
Hey man, I’ve been coming to your site for a while, I think it’s pretty

With that, let me relate a story that happened to me:

I met this girl on ICQ, but she lived in the same town as me. So I thought
that was pretty cool. She had a little website with pictures of her, and she was pretty good looking I thought. It said she played basketball and
snowboarded. Combining the pictures with that info, I was picturing a hot little sport chick. We messaged and shit for a few days, and she seemed really cool. Then, she said that I could call her, so I did. We talked on the phone for a while, and it was even cooler. We had alot in common and I had fun talking with her. I wanted to meet, but she wouldn’t (yeah, can you see this coming a mile away yet?). I was confused. I would say “aw come on, we’ve both seen pics of eachother, you said I was cute, I think you are cute, we have fun on the phone, what could go wrong?” But still, she said she didn’t want to meet in person yet.

So, at this point, I am like “what the fuck”. Well, she calls me from one of
her friends house tonight, and we get to talking. It was fun as usual, so I
wanted to go down to her friends house. She said no way in hell. So, her
friends gets on the phone and tells me the address, and I proceed to go down there, and this girl did NOT want me to go. Yeah, I bet you can guess why…

Well, I show up. And guess what… THIS AINT THE FUCKING GIRL IN THE
PICTURES. Oh no, this girl is much, much ‘bigger’, or wider I should say.
She did resemble the girl in a pics a little bit, but YOU COULD TELL THE
FUCKING DIFFERENCE. The girl in the pics was cute and NOT FAT, this girl was quite large in person. So, when I saw her, she knew her game was up, and I felt like the worlds biggest dumbass (which I was). I fucking fell for it man, the fucking “fat girl, cute pictures, internet predator” scheme, hook, line, motherfucking sinker, pole and boat.

That’s when you should have hooked up with her friend!

I tried not to be a fucking asshole. I mean, I could understand why she
didn’t want to meet in person. I didn’t need to hurt this girl more than she obviously has been hurt in the past. But, she did fucking trick my ass, and I looked like a stupid ass. I stayed and talked to her for a little while, doing my best to run ‘damage control’, but fuck, all I could do was duck when that shit hit the fan.

So, near as I can figure, I am stuck with a few things 1. A girl who was
cool on the phone, but was running some sort of scheme and fucking with me in a way. 2. A girl I am completley not attracted to physically, just what she was afraid of. 3. I feel slighted and like a colossal dumbass. 4. She seems to feel like ‘the game is up’ and that I will not want to associate with her now that I know the ‘truth’, and now her attitude is totally changed. 5. This whole thing is such a fucking shitball I wish it had never happened.

Cut your losses and bail dude! I’ve tried being just friends with a girl that I’m not attracted to, and it never works out. Some night she’ll put the moves on you, and you either have to jump on the grenade and fuck her, or just crush her self esteem. It’s better to get out right now and forget it ever happened.

So anyways, that’s what happened to me tonight. I guess it could have been worse, but fuck, I mean come on, I can’t believe it happened to me.

Shit like that has happened to everyone. I think every girl can find at least one picture where they look semi-doable. There was only one time that I saw a picture that actually looked like the girl I met in person. You’re only real plan is to meet as many girls as possible and hopefully find the one decent chick out of the bunch.

49 Other Sweet PornSites

Saturday December 9, 2000

Old News / Forums

Some More Useless Shit (6:32PM EST)Jack
Also in the last couple of days I’ve gone through the mountains of mail that I’ve got from this site. What I’m in the process of doing is weeding through it all and posting the best emails for each section over there.

In other news….. I’m probably the horniest mother fucker on the planet. Getting laid a few days ago just made me remember what it’s like to have hot monkey sex again. Now that I’ve gotten a taste of it, I want it all the time. I want a girl to seduce me. I want her to run her fingers through my hair. And most of all I want her to undo my fly with her teeth. I want it all the time and I want it now. I’m sick of looking at beautiful girls I’ll never have. I want the real thing, and I’m not going to stop until I’ve found some model to worship me. Any one want to apply for the job?

Old News / Forums

Some Things To Tell You About (6:22PM EST)Jack
As you may or may not have noticed, updates have been pretty lacking in the last couple of days. Basically was switched over to a new server and I’ve been busy with a lot of other stuff. One thing to let everyone know, if you’ve sent me any emails in the last couple of days, I haven’t received them. The old address isn’t letting me collect any emails, so try this one So what’s new with everyone? Shit’s been pretty chill over here but it’s about to heat up. I’ll let you know more details as I come across them.

Thursday December 7, 2000

Old News / Forums

Ask Jack (8:01PM EST)Jack
I added a new section to the message boards. It’s called Ask Jack and it’s where you post any questions of comments for me. I promise I’ll check it out and respond to anything you post in there. It takes like two seconds to register and the forums are pretty fun.

These chicks are pretty fun too!

Old News / Forums

So Ready For This Weekend (6:30PM EST)Jack
I am so happy the weekend is only a day away. I don’t think I could handle another day or two of school, I’d go fucking crazy. I’m going to drink like a fish and blow off some of the steam I’ve been collecting for the last week. If you don’t see an update on Saturday you’ll know I ran off with a hooker to the Bahamas.

Speaking of places that are warm, it’s fucking freezing where I live. Sometimes I wish I lived in a nice warm climate where the girls wore as little as possible. Kind of like if chicks in Florida wore the same shit as those African people, but with out the saggy tits. Now that’s my heaven.

I emailed some chick a couple of days ago, and for some reason she actually dug me. We had decided to make plans to get something to eat for lunch and maybe hang out for a little while after that. I had no idea what was about to happen to me though.

We went to this chill little restaurant and ordered our food. I put on my best Jack charming skills and flirted like mad. Luckily for me she couldn’t keep her hands off me. Every time I reached for a French fry she would ‘accidentally’ bump into my hand. When the appetizers were cleared her foot was so far up my pants I could barely control myself.

It turns out that our little nymph had been in a bad relationship before and was looking to just get some revenge on her ex-boyfriend. I had told her how I had made a web page to get back at my ex. She loved the idea but said she something else in mind….. As she said that her hand rested right on my crotch. She undid the buttons to my fly and started to pull down my zipper…. That’s when my hand went up and I yelled out, “Check please!”

On the way to her SUV I could barely control myself. She kept fondling me and kept wanting me to do her right there in public. Now I’m an exhibitionist, but doing in the parking lot of a major restaurant, isn’t really my idea of erotic. But shit, the back of the SUV will work fine for me!

As we climbed into the back seat it only took her a second before her shirt was off, and she was already pulling down my pants. Before I knew it her face was right where it should be and she was doing her duty!! I could tell this chick knew what she was doing, and enjoyed every minute of it.

After a little while she climbed on top of me and rode me for what seemed like forever. I was hypnotized by the way her titties just bounced up and down in perfect symmetry. Before long a crowd had started to gather, and was intent on watching the show. This seemed to turn her on and just made her enjoy it more. After we had both gotten our cookies, she hopped into the driver’s seat, and pulled out of the parking lot. Did I mention she was still topless?

Old News / Forums

Web Cam Girls (12:38AM EST) Jack
I’ve been reading the funniest web site on the net for the last couple of days, and I can’t get enough of it. What happens when you put a some humor, web cam girls, and biting commentary on a site, you get His site “reviews” all the web cam girls that whore themselves out on the internet. Although sometimes, getting a little personal, his shit is dead on the mark. Check it out and show him some support.

Old News / Forums

Information From The Women (12:08AM EST)Jack
It seems like this week is never going to end. College finals coming up in another week, and then it’s vacation time. The love life is picking up a little bit finally and things are starting to fall into place. Now if I could just hit the gym and put on some muscle things would be perfect. I’ll just have to be content with the beer gut for now I think.


From: Sara
Subject: Relationship Pussy vs. One Night Stand Pussy
As a chick, I think I can offer a different perspective on this topic…
First of all, boys, if you’re in a relationship, don’t even *try* for
one-night stuff. Definitely *not* cool! But ladies… If you’re not
making it fun (read: last e-mail Jack received on this topic), he’s gonna
try to get out! Normally, I’m much more tactful, but anonymity is
comforting… There’s no way to be “ladylike” about these issues, so I’m
just going to tell it like it is… I really am an ultra-feminine chick!

As for me and my boyfriend… We’ve known each other for over a year now, but only introduced the physical side of things six months ago. Normally, you think things would taper down after a month or so… Not us! 🙂 We keep things new and exciting all of the time! My nightstand has a cabinet dubbed “The Cabinet of Sin.” It’s full of toys and magazines and AstroGlide and tons of fun stuff!

We try different positions, places, everything! We go to the mountains, to the beach, to the golf course, to construction sites… We do it every
which way. (As a side note… Girls… TRY ANAL!!! I promise it’s worth
it! Use lots of lube and grit your teeth for the first minute. Once you
get into the groove of things, there are few better feelings! I PROMISE!!!) We even went on NetMeeting on the computer together (NEVER alone!) and found a hot couple from Europe who watched us. We had that camera hitting every angle! 🙂

And while the “FM” (fuck me) moods are great, it only makes the “ML” (make love) moods that much better! If we get the FMs out of the way, both of us actually enjoy and look forward to the sensuality and intimacy of MLs.

A tip for the gals: After six months, he still gets regular “waha-wahas”
and I still swallow! 😉 What a lucky man! 🙂

As long as you’re with a cool chick, relationship stuff is DEFINITELY
better! 🙂

If you’re not with a chick click here.

Tuesday December 5, 2000

Old News / Forums

The Dumping Story Part Deux (11:56PM EST)Jack
If you scroll down a little bit you can read part one of this dumping story. Basically this guy likes his guitar better than his girlfriend, and the last thing he wrote was the she stormed out of his apartment.

2 days passed since Sunday, and still no contact. I decide it has to end. I lock myself in my bedroom, choose the right album, and proceed the perilous task of getting myself prepared to rip someones heart out.

I myself prefer some White Zombie, or Nine Inch Nails. It used to backfire when I was into goth chicks……

I had to work at 4:30, so i decide if i am at her house at 3:30, i cant be there too long, which is a good thing. I need a fast escape. I drive to her house, with my favourite all time band ‘Faith No More’ cranking in the car. This is a good choice of music, because it reminds myself of single life. I rock up to her house, and guess what? Nobody’s home. I knew i couldn’t ring in advance to see if she was home. What would i say? “oh, your home, ill be there to dump you in 15 minutes”. So i am dissapointed and i drive to work.

It’s 10:30pm and im playing pinball on my break at work. All of a sudden, she is standing next to me. Smiling. Like nothing has happened. Remember, only 2 days ago i told her that my bass is more important than she is. So we chat for a few minutes, i decide i don’t want to break up with her at this moment. She convieniently suggests i come to her house after i finish at 1am. I agree to do so.

You fell into the trap. Girls are notorious about delaying our dump… I can’t remember how many times I’ve been close to dumping a girl and then she busts out some sort of memory…. Or promises no strings attached sex…..

The next few hours just fly passed, and i skull a couple of beers to gain a bit of ‘dutch-courage’. I drive to her house, and she is standing on the porch waiting for me. I take her out to my car, where i pour my heart out, and gradualy tell her that its over. She makes me look her in the eye and tell her that i dont love her. I say “I dont love you”, and she shuts her eyes, and turns to go inside. We both fight back the tears. Its now 4am, and i am glad i did it. She will be crying now. I just broke her heart. I’m so sorry.

What a sad, sad, sad story. I can almost hear the women across the country bawling their eyes out. The whole ‘I don’t love you’ was a great touch. At least she didn’t whine and beg like most other girls.

Girl’s That You Can Really Love

Old News / Forums

Some New Faces (11:09PM EST)Jack
I added some new faces to Jack’s Girlfriends page. Check it out and if you want be one of my online hoes, just send me an email. Some people have emailed me recently saying that I don’t know what the hell I’m talking about on this website. Well here’s an email that proves that I am an all knowing god.

From: Adam
Subject: Revelation
Hey Jack
Ive been a fan of yer site for a while now…you and I think alike. Anyways heres my scenario…I have been in a relationship with this chick for 10 months now and the relationship pussy is the way to go. I get it anytime i want and who can complain bout that right? Well i remember a few weeks ago you analyzed Realtionship Pussy vs. One Night Stand pussy and i totally disagreed with your synopsis…that is until this past weekend. I went to the bahamas with one of my bros and we met some braods there. Well after a night of hot tubbin and partying i ended up going back to this chicks room. Man o man i fucking forgot how awesome one night stand pussy is! It was new and wild and 10x better then my everyday pussy at home. I banged that hoe 10 ways from sundown then went home to my chick. I had sex with her when i
got back and it was boring. Now i gotta break up with her LOL!
Peace out

Dude don’t break relationship pussy!! Although one night stand pussy is awesome, unless you’re getting it non-stop, there’s no reason to fuck up a good thing. Stay with the chick you’ve got, but try and make relationship pussy more exciting. Spice it up in the bedroom…..

If that’s not the way for you, screw it…. Dump the bitch and hit the strip clubs like it’s going out of style!

Old News / Forums

I’m So Totally Fucked (10:44PM EST)Jack
Finals are coming in up in a couple of weeks, and they couldn’t come any sooner. I can’t wait to take a much needed month off from the daily grind of college. It’s also that time of the year when I’ll be submitting myself to college applications. I’ve only done two so far, and that’s probably all that I’ll do. I think Westfield State and Umass are going to be my choices for next year.

Umass would be an awesome school to go to, but I’m not sure if I’ll be able to juggle the party scene and classes. I tried it once when I first went to college and my GPA was something like 1.0 at the end of the semester. Of course I’m a little older and wiser, so maybe I can try it again.

The thing I’m looking forward to the most is living in a dorm. I loved it the last time, and now it’s just going to be even better. Girls will be everywhere and I’ll show everyone the Jack charm that I used to have. Nothing is going to stop me now.

So it’s about 11:00 and I’m waiting for this girl to come online. If you read a few days ago you’ll know that I put myself out on a limb by telling this friend of mine that I had feelings for her. She responded with a comment that I had never heard before, and I had no idea on how to react…. Well she’s supposed to come online so we can discuss it… I fucking hate discussing things. I’m no good at it, and I’d rather just crack jokes and make witty comments. When it comes to serious stuff I’m just no good. I’ll let you know how it goes though.

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Old News / Forums

Ask Jack (12:19PM EST)Jack
Hey peeps I’m back for another episode of Ask Jack. This is the place where I comment on all your fucked up relationships, and try and figure why the hell I’m not in one.

From: Jenn
I am 26 years old from Denver, a single girl everywhere I go. The thing that bothers me about being single is just that, I am 5’10, green eyes, brown/blonde hair I consider myself to be attractive. And yes I want to meet “THE ONE” and share my hopes and dreams with that person. I just hate being single. It’s a waste of time if you ask me. The only thing i like about being single is that I can go home and be by myself if I want but how fun can that be! It really gets to me when I am with my friends or my family because I ALWAYS feel like the 3rd wheel if ya know what I mean. What does not help me is that all my friends are guys, so when we go out, I am sure people think that I am taken. Anyways, is this normal or am I just freaking out here?!?! Are there any single guys left in Denver????? help me out here!

You’re at the point in your life where you’re looking for the guy to have babies with. I’m sure you’re attractive, but I bet you have the baby vibes protruding from you. Just kick back and relax, and I’m positive you’ll meet some guys.

From: Kyle
Subject: Cheap Dates
Get yourself a cheap ass map of the sky (I’m sure you can find tons of them online), read up on it a little bit, at least until you think you’ve got enough constellations up your sleeve to get her interested in finding out what you’ve really got up your sleeve 😉 Get a couple of blankets and Find a nice dark place (free from light pollution so you can actually see the stars, for those of you who live in the sticks this shouldn’t be a problem), a nice open field will do. Take her there and impress her with your astrologer’s wit and astronomer’s intellect. Cost of date: $0.00

Good call dude! Chicks go all googly for stars and will love it if you can point out the constellations. Bring a bottle of wine and make it a fun night for all involved.

From: Wes
I am in exactly the same situation you are. In fact are similarities sans the kid are quite unusual. I recently graduated college and moved to a place where I know no one. I can’t network through friends to meet girls. I have a good job and my own apartment. However the only way I will end up meeting anyone is to go to the bars by myself. It’s a drag but when you have no other option what do you do? I get extremely restless knowing its Friday night and I’m staying in watching movies or playing on the internet. The real trick to meeting girls in bars is courage. I see losers all the time that literally talk to every girl in sight. I figure if I could do that, I’d be set. I’m pretty a decent looking guy and with odds like that I can’t lose. But I’m still a long way away from that phase and unless I change it will continue to lonely Fridays for me. I can’t seem to find your email so I thought I’d drop you a line in this format. I guess I just wanted you to know that there are people like you out there.

Courage is the total babe pick up line. All you have to do is not be afraid to hear the word no. At a bar you have a limited amount of time to pick up a chick. So this is what I do.

1. Find out in the first 10 minutes if she’s interested: Say you’re talking with a chick at the bar and you spend a good hour just talking with her. At the end of the night she takes off with all her girlfriends, and leaves you there with your dick flapping in the wind. In the first ten minutes you have to see if she’s interested. If she’s not, say you have to go to the bathroom, and move on the next girl.

2. Have some sort of game plan. I know it sucks, but as a guy, you have to do it. Girls have it easier here, as they can just sit back and talk to the guy they want to, but we have to have some sort of plan. If you’re funny try and make her laugh, remember you always have to play up your strengths.

3. If that doesn’t work for you, try looking at porn.

Monday December 4, 2000

Old News / Forums

Interracial Dating (8:01PM EST)Jack

From: Lisa
Subject: Interracial dating
Hi. I’ve been in an interracial relationship for about 4 months now.

More power to you sistah!!

It is so hard because I know my parents wouldn’t approve.

Oops, my bad, I bet you’re white. Or at least have white parents.

I’m away at school and he’s at home still (it’s only about an hour)so it is easy to hide it from them. The thing is I don’t want to hide it from them. I’m almost 20 now and when I was a freshman in high school I had a black boyfriend (i’m white by the way)

I knew it………

and they went crazy. They forced me to stop seeing him and I guess it didnt’t seem that bad because I was only 14 and the relationship obviously wasn’t that serious. But now I see how wrong it is for them to think that way. My boyfriend understands that some people are like that and he’s used to it, but I don’t. I’ll be going home for a month for x-mas and I have to tell my parents about him because it’s killing me that I can’t share the person I love with my family. I just don’t know how to approach the subject.

Why are your parents so dead set against you going out with a black dude? I can see how some ‘rents are kinda thrown off by it, but they seem totally out of control. Especially since you’re college, and you’re not really a kid anymore.

Once we do talk about it I’m going to explain to them that I’m an adult and can make my own decisions. I’ve never done anything to dissappoint them so why should this upset them? It’s also hard to talk about it with them because I never talk about boyfriend relationships with them. I know they are going to tell me to stop seeing him but I can’t. Now that I’ve told you my whole life story, if you have any advice I’d appreciate it!

Right on sistah!! You go on and made sure that you’re little rebellious outbreak you’re having right makes your parents do whatever you’re little heart wants.


Old News / Forums

Free Porn (6:55PM EST)Jack

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Old News / Forums

Today is the Day of Web Cam Tits (3:56PM EST)Jack
The guy over at Jeremiad emailed me a couple of days ago about getting a spot on one of the webcam portals. He sent this long email about most portals don’t feature boring guys. Since I’m a boring guy myself I could understand how he felt. But since I want more chicks on the cams then guys, I didn’t want to just give him a spot. So I asked him to take some pictures of his girlfriend, or just some girls tits and email them to me. Most of the time I never hear from them again, but I just received this email couple minutes ago.

From: Nate
Subject: Re: so I was thinking…..
i hooked it up today im taking this film to the one hour in a bit… my friend kelly holding an I want a new girlfriend sign my web cam kinda cought some of it… so heres the web cam pic and ill get you the real pic tonight or tomorrow igor

Fucking sweet is all I have to say. It’s another girl that will join the pages of Jack’s Women. Keep them coming cause I just love this shit. Also check him out on Portal Number 4.

Old News / Forums

I Love Web Cams!! (1:10PM EST)Jack
There’s so much you can do with your handy web camera. You can stay in touch with family, friends, far away loves…… Or you can put on strip show for every one to see!! This right here brightened up my night last night.

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Sunday December 3, 2000

Old News / Forums

Why The Past Should Stay In The Past (11:21PM EST)Jack

From: Anonymous
Subject: why the past should stay where it is…..
jack, so i went out tonight with a friend to talk over some coffee. all was good until i look over at a guy that just sat down at the table across from us. i feel the gag reflex coming on as i realize it is this guy i used to date back in junior year of high school.

Oy Vey!! I hate it when that happens. It’s just like you’re finally cool with them out of your life and then all of a sudden they show up again.

i like to call him psycho. now psycho started off really cool at the beginning of our relationship. he was about 3 years older than me, but he knew how to have fun. on our first date we went to play lazertag at the mall. he helped me to realize that a lot of the things i was doing were fucked up and i needed to stop. the first month was one of the best times in my life. that is where it ends. he started doing some wierd ass shit after that. for instance we were riding in his car one night, and the song ride the lightning, by metallica come on the radio. im down with metallica, so it was all good when he started telling me how it was about prison and the electic chair. but then he pulled out a gun from under the front seat and started waiving it around in the air, going about 60 on a back road.

Riiiiiiiight….. I think that’s when it’s time to get the hell out and not look back.

at this point i am contemplating whether it would be better to jump out of the car and break a few limbs or to risk getting shot. after sitting for about a minute in complete shock, staring at the guy who used to give me the warm fuzzies, he pointed it at my head. he said some lame ass line from a clint eastwood movie and pulled the trigger. well it was a fake fucking toy gun. a 20 year old guy is riding around with a toy gun under his front seat. fucking weird. unfortunately i was pretty stupid back then, and could only think about how in love i was. so i stayed with the fucking psycho. then one night he was like yeah can you guess what is in my trunk?

Now that’s a pick up line if I’ve ever heard one before……

something told me that i really did not want to know and i made up some lame excuse about having to be home soon. weird ass mother fuckers. thats what i get for living in a back woods town i guess.

Old News / Forums

I’m Bored (10:41PM EST)Jack
Sundays are usually pretty boring for me. I have the whole day off from work so I spend most of my time looking at porn or watching chicks strip on the web cams. I think I need a new hobby or something.

One thing I do love is when girls take their clothes off and write my name on their bodies. If you want to be a part of this ever growing list just email me. It’s very easy and you’ll even get some hits off of it.

I found a new site to check out though and it’s pretty damn cool. It comes from across the pond and it’s called God Shave the Queen. There’s everything from jokes, cams, and tons of other stuff. Check it out and let him know Jack sent you.

I just recieved this email and I hope it’s the first of many. I guess you could call it an online soap opera. Here’s the first installment.



I’ve been seeing this girl for three and a half months, which seems to be a common ‘pull the plug’ time for guys. What I love about this girl, is if i take her out, she gets all dressed up, and every guy wants her. But she has eyes for only me.

You may think has eyes for only you, but get real if she’s really hot she’ll always be checking out the competition.

Then i get drunk and fuck her until she hurts. So it seems like a good situation? Yes!? NO! It seems as if everything she has to say, is un-interesting. She talks gossip, and how some girl i’ve never met is cheating on some guy i’ve never met. I need earplugs to filter the bullshit.

HA HA HA HA! I’ve been in that spot before. You just gotta ask yourself.. Is the sex worth listening to the bull shit that spews out of her mouth??

Anyway, yesterday, she’s telling me how much she loves me, and how we will always be together, and all that shit that guys dread to hear, but is a good ego-stroker. Today, she arrives at my house and i took advantage of the fact that she was in a foul mood. I rose the ‘you have nothing interesting to say’ argument. It got ugly, so i picked up my bass. I was playing away whilst we argued about various things. Then she says ‘you give your bass more attention than you give me’, and i tell her ‘my bass doesn’t feed me bullshit’, and she gets up, leaves the room, gets in her car and drives off. So now, im hoping she hates me, so i can break things off smoothly. I don’t want to hurt this girl. She honestly loves me. But i can’t help feeling empty about things. I’ll update my story tomorrow.

She wont hate you, that’s the fucked up thing. Sure she’s probably crying to her girlfriends telling them what an asshole you are, but deep down she loves you more than ever. She’s just going to try harder to get your love and make things right. Dude you better email me tomorrow I want to make this a daily thing!

Old News / Forums

Responses (1:34PM EST)Jack
Here’s some good email I’ve gotten in the last few days.

From: Kathleen
Subject: Girl knowing how you felt
well, that certainly is an odd thing to say, but here’s how I interpret
1. she knows you like her
2. she is still willing to hang out with you
3. she made a smart-ass comment about how long it took you to bring up how you felt

so since she hasn’t stopped hanging out with you or run away screaming, then I’m quite sure that she is interested in pursuing somethign with you… but the key thing is she wants you to take control and set a date or whatnot.


Either yesterday or the day before I wrote about telling this girl that I liked her, and she gave me some weird remark. You’re right she hasn’t stopped hanging out with me, but should I really take control? I feel like just dropping back and now hopefully just being buds again. I don’t want to be some 3rd grade relationship right now, I just want some one that either likes me, or thinks they like me. I don’t need little mind games, but of course most girls play them so I like I’m out of luck.

From: Dammy
Subject: Hey about that post…….
The one you made when the girl said “I knew how you felt, and was wondering how long it would take for you to say it…..” Same thing happened to me. We started as friends, it grew to more and as time went on, I fell in love with her.

Finally I told her, and bingo, that was her answer. Then a day later I asked if we can go out and stuff, and she basically said no. I was her friend, and nothing more.

If you happen to get something out of it other then just staying friends, let me know.

Sadly I don’t really see anything happening between us, but no fear people, I’ll survive. There are plenty of fish in sea, all I have to do it drop some bait.

Old News / Forums

Couple Of Quick Things (1:21PM EST)Jack
Just a couple of quick things before I get to the updates. Recently I’ve started to get a lot of emails from people who are looking for relationship advice. Now, don’t get me wrong, cause I love getting your tales of woe, but I’m just not able to give out advice to each person that emails me. I like to pick out stories that will interest other readers, and maybe help them out also. If you really have a question to be answered, check out the message boards. There’s plenty on smart people that can definitely help you out there. You can still email me all your shit cause I do love to read it.

The almighty pussy….. That right there is what causes us to do things we would never thought of doing before. We lose all control of natural thought processes and start to think with our little heads. Girls know this and will use this to their advantage any chance they get. This is their one asset in life that they can use to get what they want. They can use it to get raises, promotions, and even become celebrities. Monica Lewinsky used her mouth, but that’s a whole other story. Personally I’ve done some fucked up things for pussy. I’ve blown off friends, skipped work, even emptied back accounts….. There really is no limit to what I’ll do to get a piece. When I was seventeen and scoring like Wayne Gretzky, there was no problem getting pussy. Things were so much easier back then. There were simple steps to follow to almost guarantee it. Now that I’m 22 the pussy has disappeared. To me it’s like the prey and I’m hunter, but there’s none in my sights. Maybe I’m looking in the wrong spots, or maybe I just keep frightening them away when I get near. Either way it’s going to be a long hard road ahead……

Saturday December 2, 2000

Old News / Forums

New Cam Additions (7:23PM EST)Jack
Added a couple new cam additions to web cam portal 4. It looks like I’m going to have to add a couple of new pages to keep up with the demand for spaces. I’m looking for chicks to fill up the spots, but if your a guy with a website I like I’ll think about it. Now it’s time for everyone’s favorite section……..

Viewer Mail

From: Claudia James
Subject: hello
hehe, hey i think you’re really REALLY cute.I’m 22 years old and have done amateur erotic vids. (how old were you again?).

22 and all man baby!!

Anyway, If you shout out my name on your site. (Claudia James is coming soon!) then i’d be happy to send you a free vid, and i do live close by you so i think we could arrange some free head too! hehe.

anyway, see what you can do.

Well I’m a sucker for free head so here’s your little plug baby. I’ll expect you waiting at my door tomorrow morning on your knees.

Claudia James Is Coming Soon!

Old News / Forums

So Much Stuff To Do, So Little Time (7:15PM EST)Jack
Today has not been a good day for the Jack man. First off I’ve decided not try and get girls anymore. I hate to sound like a whiny little bitch, but today was the last straw.

I’ve been hanging out with cool chick for awhile, just as buddies… So I finally get up the courage to tell her how I feel about her. So as I bare my heart and soul to this girl, what does she do? She has the balls to say ‘I knew how you felt, and was wondering how long it would take for you to say it…..’ What the fuck kind of answer is that? I would like any advice from the ladies on that one. Most of the time if you say something like that and the girl’s not interested, then she’ll tell you. And if she is interested than she’ll give you a hug and shag you rotten. I’m confused if the girl knows what’s going on but doesn’t act either way…..

So I’m stuck. She still likes hanging out with me, but knows how I feel and I have no clue about what she’s thinking. Totally in need of help from the ladies that come here. Help a dumb ass out!

Old News / Forums

Viewer Mail (1:02AM EST)Jack
From: Mike
Subject: Bartender
Jack i hope you dont mind playing bartender for a bit.

Nope, been a bartender for years so I’ve got plenty of experience.

Its easier to talk about problems to someone you dont know or in this case never meet. Plus i check out the site all the time and respect your advice. Im a freshman in college. Ive been seeing this girl for about a month now and i really care about her. She is everything i want in a girlfriend and she says that she really cares about me too. But to start at the beginning, the first time we met we hooked up and we hooked up the next night too. She had a b/f at the time but broke up with him for me.

It’s not really a good idea to go out with this type of chick. She obviously was cheating on her boyfriend with you. What makes you think that she wont do the exact same thing to you if she gets the chance. Keep this girl around if you’re getting laid but don’t stress over her.

Here is the thing though. Now we dont spend time together as much as we would like. We are both involved on campus and are busy in other activities. When we are together though we dont do anything. We sit in the same room and kiss once in a while. She says she wants to take things slowly.

She wants to take things slowly, but hooked up with you the first night you guys hung out? Not a good sign if you ask me. Sounds like she may have something going on the side……

Im okay with that but im not sure its going anywhere. The only time we touch or act like there is something between us is when we are alone.

Bad sign. If there’s no PDA then something is definitely wrong. Most girls complain that we don’t show enough affection and make them feel loved. If she’s the one not showing the affection you’re in trouble.

As soon as people are around she acts like there is nothing going on. I mean if we are sitting together and someone comes in the room she jumps across the place. I dont know what to do casue she is a great girl and i know shes not a prude or anything but things are getting retarded
between us and i dont know how to even try and fix things. That is kind of a brief over view otherwise this would be way to damn long for you to read. anyway, hit me back, or if you dont have time, i think just writing this out and thinking about it helped a bit. ttyl man

Three words for you….. Not Worth It. She’s playing you like a piano and hitting all the wrong keys. Cut your loses right now because the longer you let this go on, the more attached you’re going to get. It’s only been a month and it times to let the fish go back to the sea.

Old News / Forums

Fucking Windows (12:37AM EST)Jack
I just spent the last hour and a half reinstalling windows on my computer. My little piece of shit pentium II kept crashing tonight and wouldn’t even let me log on. I think I fixed most of the shit, but we’ll see what happens in the next day or two.

So what’s up folks? Is everyone still as bitter about dating as I am? I think I must have done something wrong and now am paying the price for it. Maybe all that time cheating on girls is catching up, because I’ve never had this amount of a dry spell before. I think I just need to get out of this slump and I’ll be back to normal. That might be the toughest part though. It’s tough to build up self confidence when you don’t feel it, and with out confidence the only action I’ll be getting is my hand.

One thing that has brightened my spirits is this website. There’s so much shit on that site that I can’t even begin to list it all. Check out the Fat Project and the personals that they do. If you’re bored or just looking for funny stuff make sure you visit them.

This picture cheered me up today. It’s from Serra over at Fuh-Q. Besides having a funny domain name it’s a site with some great content. Plus there’s more pictures of her beautiful breasts that I just to suck on. I could nibble on those nipples all night long if she let me. But I can only dream. It’s been so long since I tasted tits that I almost forget what it’s like. I almost feel bad for the next girl I get in bed with. I think the foreplay with last about two seconds before I pump my shit into her wet cootchie. Then that will be over in about a minute because….. Well we all know why. Well that’s enough of my whining. Check out Serra’s Site and you can also her on Webcam 3.

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