Wow… what a weekend. I just got back from LA and I’m thinking of moving down there! I haven’t had time to write up my adventures yet (I still have to work a little bit), but I’ll get it to you asap. Let me just say that I had sex with 5 girls down there, and three of them were LESBIANS! I think I have found a new niche of girls for my quest that I had never thought of before! I’ll get to the details when I get back to my computer tonight…
How do I go about fucking a porno star? Can’t be that hard. Porno stars are all over the place down here… two-thirds of all pornos are filmed here in LA (okay, in The Valley). Always wanted to have sex with a porno chick… if anyone knows one that might be willing, send me an email and I’ll get her some good publicity in this blog. I’m up to over 1,000 hits a day right now, and it is getting more all the time…. and I’m guessing that it is a readership that would enjoy porn!
In LA for a few days… came down to have sex with an old friend of mine. I’ve known her for 25 years, went to high school with her and for some reason we never slept together. We were always flirting, always attracted but we always both had other people we didn’t want to cheat on. We finally had our chance last night!
She is a sweetheart and has the classical LA body… nose job, boob job, bleached blond hair, Pilates body, tan all year, etc. She was an actress on a Soap Opera for about ten years and is now a writer for a couple of the daytime dramas.
She came to my hotel (Loews in Santa Monica) yesterday afternoon, and without even saying a hello to each other, we started kissing fondling and stripping each other. It was like we tacitly agreed just to get the sex out of the way before either of us said a word to screw it up! Was a lot of fun, but didn’t last long. She came within about ten minutes of me being inside of her and I was very quick to follow. Then we talked, and laughed and walked on the beach and had dinner and then fucked our brains out for the rest of the night. Can’t believe we didn’t do this 25 years ago! Yes, she is still married, but obviously not that attached.
Have another date tonight with an AshleyMadison chick… met her for coffee this morning and we had a lot of chemistry… very cool chick. I told her about this Quest and she is all into it. She might even be able to score me a friend or two of hers while I am down her. Heck I might just stay down here through the weekend!
I love that women are into this Quest… at least half of the positive email I get is from women who are turned on by the descriptions, if not the Quest itself. Of course nearly all of the negative email comes from other women…
14 down, 86 to go and still loving it!
Screaming Hot Little Cleaning Chick came over again today… Oh my God that girl is something. So young, so innocent, so dirty, so willing to please, so desperate to be loved, so fucking good. What a difference from that young Suicide Girl.
I successfully put off offering to take her to Tahoe for now, but it is just a matter of time… She desperately wants to spend the night… she even told me that she would let me fuck her in the ass if I take her to dinner and let her stay the night… that is the kind of girl she is, and I just know I will end up paying big-time for it someday… hopefully after I fuck her in the ass!
No way I am taking her to dinner in public. (I just refuse to be THAT guy.) But I probably will take her to Tahoe sometime… and maybe lunch in public… I’ll pretend she is my daughter…
She also asked me to teach her to deep throat, and I was happy to oblige… seems to be a skill few girls have, but many want to work on. I pushed her hard, she gagged a lot, and then I fucked her from behind as long as I could, pushing her head into the bed, and staring at her perfect little body…. I just love that view… ass spread wide, head down, tits swaying… a perfect position with the right girl.
I gave her a website to check out that shows you how to deep throat, and told her to practice, practice, practice, then come back and see me!
I love this new shaved pussy trend. 15 years ago it was rare, for me at least, to find a girl that routinely shaved much more than her bikini line, but now almost everyone is shaved to one degree or another.
Been with some who have the landing strip, some who have the triangle and a couple who go totally bald…. all of which I love. I love to lick pussy (probably because my wife was always uncomfortable with it and we humans always seem to want what we don’t have). And licking pussy with no hair is much more fun. More fun on the eyes, on the tongue and on my cock. The only thing I don’t like is the unshaved/whisker look or feel. Don’t do that. Once you start shaving, keep it shaved!
Just my two cents for today.
A Few folks have asked how to get chicks on AshMad or other dating sites.. it can be tough. I don’t know the numbers, but it seems like there are about 100 guys for every hot chick. And some of the “girls” are not girls, but idiot guys with no life and like to Chat. Or they are too ugly or too afraid to actually walk their talk, and will do nothing but waste your time or want to “chatsex” with you. Boring!
I’ve spent a couple months studying what works and what doesn’t and have had some real successes. I’m happy to pass along some of my lessons learned. I’ll write em up whenever I can, and post them. Happy to hear of anything that you have found that works… never too late to learn! I still have 80 something chicks to convince to fuck me!
Here are a couple off the top of my head… I’ll get more detailed when I have time.
1. I never go for the younger girls. I can get them at coffee shops. On AshMad I look for the married, 30-40 MILF who are so bored or frustrated that they will do ANYTHING to you, for whatever desperate reasons they have. Young girls have so many offers that it is nearly impossible to get their attention and they are way too high maintenance.
2. I never go for the single girls… same reason as above. Some of these chicks are looking for sugardaddies, and while I support that, AshMad is not the place for it. There are several good websites where the girls are hotter and easier to deal with if that is you thing.
3. I try to target women from the suburbs. I rarely go for girls from San Francisco or San Jose… I try for those in Concord, Walnut Creek or Petaluma or Sonoma. You want a small town girl that doesn’t have much other opportunity to do this sort of thing and that has something to lose if it becomes public.
Lots more to come…
Suicide Girl was a bit of a bummer. Of course I still had sex with her since I’m a guy think with the little head when I am in bed with a chick, and because I need the numbers for my Quest, but I really should have just kissed her forehead and left soon after I got there. Sad case…. miserable life and she likes to re-live the miserable parts… Guess the SuicideGirl thing is more than skin deep.
I met her at her apartment that she shares with her roommate and her roommate’s unhappy cat. We sat on her bed and I listened to her. Just nodded and said “hmmmm…” a lot. After an hour or so, I just reached out and started to take off her shirt. She hardly flinched and didn’t stop talking. I spent the next half hour half listening to her while I sucked on her sweet little breasts that each had a tattoo and a nipple ring. Never really thought much about nipple rings before, but I have to admit they are kind of sexy.
My body was turned on, my brain was turned off…. my body won, of course. Moved down to her well groomed (a nice surprise) kitty and had my fun there. Clit was pierced too of course, and I am not opposed to that either. She barely noticed I was there. I didn’t even bother with a blowjob, or trying to really get her into it. Just played with her body and tried to tune out her talking and sighs. Finally I just turned her over spread her legs and fucked her from behind lying flat on top of her and pushing her head into the pillow. She shut up for awhile, but started in again as soon as I was done. I split as soon as I could… she seemed resigned to it. She thanked me for spending time with her and said I was a really nice guy.
Strange, sad little girl. Perfect little slutty body, fucked up brain. Maybe just too young somehow. What a difference between her and my little 19 year old cleaning girl… I need another session with her to wash this one out of my brain.
Another one down, but not a very fun one. 87 to go!
God Bless the dudes that started Ashley Madison! They really hit on something, and while there are lots of other sites out there, I’ve never found one that worked as well… and no they don’t pay me! But maybe I should ask them to host this blog….hmmm..
Some of you have emailed or commented that you want some tips on how to use AshMad best… I do have some things to share and I’ll do so when I get a couple minutes… my first priority is to get myself laid, then I’ll help you…
Speaking of which… date tonight with that dark little Suicide Girl. Not sure about this one… she is physically perfect for me, tiny and slutty looking, but I get the feeling that she is going to talk a lot about how miserable her life is. I’ve talked to her on the phone a couple times and texted back and forth a little now. I’m a type A kind of guy and naturally want to get people to figure out how to fix themselves – which almost no one appreciates. I will have to try and hold my tongue, or use it for purposes other than talking. We’ll see. I am prepared for the worst, and will hope for the best.
Still don’t have a third girl for this week… need to stop hanging out with Girl #2 on the weekends so I can catch up… I’m still one girl short for my goal right now.
31 years old, Asain babe married to a somewhat successful sports star here in the Bay Area. (Hope I’m not giving away too much.) He is on the road a lot and cheats on her all the time. She listens to Howard Stern, heard an ad for AshMad and decided to play the same game. Basically she was out for revenge and for a good time, and I was very happy to help on both counts.
About 5′3″, 105 lbs, limber, in great shape, hair too short and kind of angry, but was a lot of fun in bed. Got a hotel in the city (Hyatt Regency, top floor) about 5pm, had a drink in the bar downstairs, went to the room, checked out the view. I stood behind her and fondled her breasts a little, nibbled on her neck, and a few seconds later she was naked and we were in the shower together.
Married girls are so much less inhibited than single girls, and they are usually sexually bored, frustrated or, in her case, out for revenge… with these types I usually start off with the nastiest things, just to see what they are up for… She was up for anything. I had my tongue in her ass before I even kissed her, and she was squealing. Pretty soon I was showing her how to hold her head so she could deep throat me without gagging too much. She gagged anyway and threw up her drink, but it wasn’t too bad and she was determined to get it right… I assume this was the revenge part, because it is rare to find a girl that eager to do something that submissive so quickly.
We fucked for a couple hours, went to dinner, fucked some more, made a real mess of the bathroom and bed, and called it a night just after 11. She had to get home so her husband wouldn’t get suspicious when he called. I went home completely sated. Felt a little sorry for her… her marriage will not end well, and she will probably regret tonight, but I won’t. And I bet she wants to do it again.
Met a Suicide Girls model yesterday in SF. She is one of these typical young, skater, dark, frownie types that hang out in coffee shops with lots of tattoos and piercings… A little like Girl #6 but less happy and has no money. You could see her nipple piercings through her skimpy white t-shirt with no bra. I just love this look. Quickly struck up a conversation and when she asked me what I doing there, I handed her my Quest card and told her the whole story of the 100 Girls in 1 Year. That’s when she told me she had posed for one of the Suicide Girls books/website. She showed me her pic on the website, and the pics of some of her friends, and I figured I was in.
Damn these Suicide Girls are amazing. If you haven’t checked them out, do it quickly www.suicidegirls.com. They just have such a “fuck the world, then fuck me hard” sort of look to them. Kinda sad, but ultra sexy. Very skinny, very dark and slutty all over.
I’m meeting her at her apartment Thursday afternoon. I’m pretty sure sex is a sure thing. That gives me two for the week… need to find one more!
Saw G1’s friend last night… tall drink of MILF… very sweet, nervous, and ready to play. Married chicks are so uninhibited, and lusciously desperate for sexual attention. We started slow with my usual neck kissing and booby fondling, started playing with her nipples, which got very hard (I love that), then started whispering what I was going to do to her… she arched her butt against me and we were off!
I threw her right in the shower (huge, stand up shower), and had my fingers inside her little lips in just a couple minutes. I was inspired to break out my toy collection with this girl, blindfolded her, and then told her to play with herself using the toys.
I always try to make a chick play with herself… some girls are feel inhibited and you have to really encourage them (sometimes I grab their finger with my teeth, then drag it to their clit… then lick their lips while they touch themselves). Getting a chick to do this is always a good idea for a guy… it does a few things.
1. It shows her that you are not afraid of them playing with themselves, as some girls cannot orgasm without using their fingers. I have NO issues with a chickee getting herself off while I am fucking her. Some are too shy to do this, which is ridiculous… the more fun they have the more fun I have.
2. It teaches you what they like and how they like to be touched. Every girl likes something different, and often what one girl likes is a turnoff to another. Getting them to play with themselves shows you what they like, then you can duplicate it and they think you are a genius!
3. Lots of girls think masturbation is “dirty”, so if you can get them to do it, it kind of gets them in the mood for lots of other “dirty” things – kind of heightens the level of play.
She was game, and I enjoyed watching her make herself squirm. I opened her mouth with my hand while she was playing and just held it open…. then slowly put my cock in, just teasing her a little, going gently in and out till I figured she could handle it a bit rougher. From there we went to missionary and I tested her flexibility (excellent… Yoga and Pilates is the greatest thing in the world for sex). We fondled, sucked and played for a couple hours. I teased her ass a lot, but never actually pushed myself in. I came twice, she came once… she tried for another but she was just too tired by the end.
Good girl. Hope she finds more boys to play with… her husband hasn’t had sex with her in two years… marriage sucks (have I mentioned that?). Okay, actually I like marriage, I just don’t like sex combined with marriage.
21 down, 79 to go!
I saw G1 again this morning for some sweet sex play. She loves anal. With the right girl I can get into it, and she is sure the right girl. Lovely little MILF. She isn’t on birth control, so she always blows me, then begs me to fuck her in the ass. (No we don’t use a condom… I do with almost everyone else though, so don’t bug me…). She used to only be able to take me while she was on her back, but we have slowly worked up to doing her tight little ass doggy style. Never met a girl who loves anal as much as she does. She is very small and bendable and so much fun.
She has also acquired another chick for me. Another MILF friend of hers. She showed me pictures the other day… looks tasty. Tall, dark, 43 yo, one kid, still married, but looking to leave her husband and wants some fun. Very common story, I’m finding. She is coming over tonight – I just love fucking two or more girls in the same day… such a turn on!.
G1 is amazing… she actually has hot chicks coming to my house for the sole purpose of fucking me! If I could get 5 or 6 other chicks to do this, my job would be so much easier! I can’t count the number of dud dates or hours I’ve spent trying to woo other chickees. Poor me!
I told her about my Lesbian adventures in LA, and asked her if she new any lesbo couples who might want to have some fun with a guy. She is a well connected chickee in the art world, and surely there are lots of them there right? She likes the idea and promised to scope it out, but wants to join me in playing with one… no problems there!
I decided to go a little more public with my Quest, see if it can help me round up a few more chickees. Believe it or not, some girls are actually into this Quest… never occurred to me… in fact I am starting to get the idea, based on my email, that they are the majority of my readers – which totally turns me on.
So why not try to make it work for me? I’m going to post an ad on Craigslist, talking about my Noble Quest, and asking good looking chickees to help me out. I bet it actually works. I am stunned at how easy it is to get girls in to bed these days… maybe I was just a total dork before, but it seemed like I had to put a whole lot more work into it back in my pre-marriage days. Course I do work out and have a hell of a lot more money now… guess that helps.
Here is the ad, so far.
“40 year old, recently separated, good looking rich guy, seeking to make up for lost time by having sex with 100 girls in the next year. If you have any desires unfulfilled and/or just want to have a one shot afternoon/night/weekend fantasy, I’m your guy – I like doing new things and I can afford them. I’m chronicling the whole adventure in a popular blog online (I will be discreet about WHO you are, but NOT what we do). If you want to be a part of this fun, email me and we will be having sex asap in a nice hotel in SF, on a beach in LA, or at one of my beautiful houses in the north bay or Tahoe. You can check out the blog at 100girlsin1year.blogspot.com. Email me at 100g...@gmail.com”
Alright! I’m 20 chicks into this Quest, and having a blast… most of them have been rocking good fun, only a few duds, and I am looking forward to another 80 in the next ten months.
Is it possible to get addicted to new pussy? I think I have achieved it. I am consumed with being with new girls… not that I don’t still have fun with G#2, but my interest is really only in being with a new body, a new girl, a new mouth, a new ass I even find myself occasionally avoiding being with any of them for a second or third time… (except G2, oh and and the amazing little cleaning chickee… yes I am still seeing her once a week or so. Oh, and G1 on occasion…. oh, and…). Hope this Quest doesn’t spoil me for a real girlfriend! Maybe I’ll be sick of women altogether by the time this Quest ends…
Thank you to all of the wonderful, beautiful, sweet and willing chickees that have helped me out so far.
Black Girl was hot! Wow was that fun.
We spent most of the day together on my buddy’s boat, sailing around the Bay doing the Golden Gate Bridge thing, drinking beer (wine for her), and having fun on a picture perfect day – minus a little smoke and some ash falling on us. She sat on my lap, laughed a lot, got wet, nibbled my fingers, and probably would have gotten more serious if we had been on a bigger boat!
Took her back to my place in San Francisco since my wife is in Chicago for the week. G20 was as eager to get to the sex as I was, and I had her naked from the waist up before we got in the front door. I slid inside her wet little pussy the second the door closed, and then romped around with her for the next three hours.
She had a perfect bubble butt that I devoted at least an hour to… I fucked that perfect ass with my tongue and my cock by the time we were done. For a skinny girl, she had a major set of boobies on her that were perfect for sliding in between. She had a great way of holding her head so that as I fucked her tits, I would slid directly into her mouth on every stroke… very nice move that I’ll have to teach to G2 (who has sort of become my primary girlfriend).
We finished our fun, then watched an unbelievable sunset through the smoke clouds from all the fires here in NorCal. This girl was fun, uncomplicated, out for a good time, and probably up for doing it again soon! She also asked if she could use me as a personal reference for a job she just applied for! Uh… sure…
I didn’t tell her about the Quest, but I might do it next time we talk.. She might be a little pissed at first, but I think she might get off on it.

