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LINKS
HOT LINKS     |
18/01/2010
I don’t know if you read “Kinky Girlfriend” on here… I posted it a couple of days back. This isn’t like a lot of the stories on here. It’s not a “I saw this blonde and she tore my clothes off and we had sex” kind of story. So this story may not be to your liking. But it IS a true story.
Hey… I’m 50 year old. In all that time I’m bound to have had a few interesting things happen to me, right? So read on or skip it or whatever that’s up to you. But keep in mind this story is 100% true (or as close as I can remember seeing as it happened 10 years ago).
This isn’t really “Kinky girlfriend 2” either - because this is about a different girlfriend. I promised Kinky I’d never tell anyone her real name and that’s a promise I have kept so we will just call her Kinky. Very sadly, after a wonderful affair which lasted for a couple of the most enjoyable and exciting years of my life, she and I parted. Something about her husband holding a power tool to his head and getting all suicidal. Let’s just say things got very messy for a while and she left me.
I was feeling amazingly sad. Damn I loved her so much… I even get a bit misty about it now. I really went into a dark place. I’m not a “woe is me” kind of guy but I never figured there’d be anybody remotely like Kinky in my life again and that’s a depressing thought. Some day I may post a few more stories about Kinky and me… but it’s a bit painful and I’d rather look on the bright side of things.
Anyway in my depression, one night I saw those commercials about all the cool beautiful fun people you can meet if you call this local number for $$$ per minute. Not the phone sex lines. This was more like an old school party line where you can talk live to people from your city. So what the hell… I called it.
No, I didn’t meet any cool people. Most were lonely old hags with horrible smokers voices... which is to be expected because at the time I was in my early 40’s and lonely too. I wasn’t exactly a beautiful 20 year old stud - no idea why I expected the female half of this pathetic experience would be anything different. But there were a few young ladies on the line. After an hour or so I did get an invite to a party if I brought beer.
I showed up with a case of beer and a Pizza. HOLY was I out of place. Everyone was in their early 20’s. The girl who invited me called herself Tia. She looked like an ugly crack whore. Picture Courtney Love but much younger and even more strung out. She had a baby that didn’t cry or even move much… the whole scene was dirty, ugly and very nasty. Drugs. Booze. Drunk people. Vomiting. Not good. Now if I was making this up I’d tell you how there were beautiful people there and we all got naked and had wild sex but nothing could be further from the truth.
The only ray of sunshine at the party was Tia’s friend Amanda, although I didn’t know her name at the time. I also later found out it was Amanda’s place. She was renting a rundown old shack in a very bad part of town. How Amanda and Tia were friends I was never clear on but Tia was having a party at Amanda’s place and the party got out of control. Poor Amanda was just beside herself trying to keep people from butting cigarettes out on her sofa and puking on her carpet and stuff like that.
Tia never left the phone – she was still on the chat line busy inviting (read conning) more 40ish guys to bring beer and Pizza to the party. Anyway I got the hell out of there (and took my beer). I was there just long enough to fall madly in lust with poor frantic Amanda. Then I felt like a dirty old man for the rest of the night and drank my beer alone.
A couple of days later I was looking for my keys and it took me forever to find them. Briefly I wondered if I had lost them at the party. But that was a stupid thought. How had I made it home in my CAR without my keys? Still… that gave me an idea.
I drove over to the house where the party had been
held and knocked on the door. Yep… beautiful Amanda answered the door. I told her that I thought I had lost wallet at the party and I wondered if she might have found it. That’s when I found out that her name was Amanda, this was her place… and she had a certain spunky innocence and just the nicest laugh. She invited me in and we shared a beer while searching under the sofa pillows and stuff.
I said I could leave her my number if she found the wallet. She joked and told me she would probably not call if she found my wallet because she was so broke she needed the money. Then it wasn’t a joke anymore… she was going to get kicked out of her place if she couldn’t come up with a couple of hundred bucks for rent in a few days. Now a nice guy would have just handed her the cash. But while I’m not a total jerk, I’m not that nice either. The whole situation gave me another somewhat impure idea!
As I was leaving, I told Amanda that I was going on a business trip in a few days and I’d love some company. I invited her to come along and I told her I had a feeling her luck was about to change. I told her we could stop in at a casino and I’d give her a few bucks and stake her for a bit of gambling. If she won she got to keep it and if she lost she wasn’t out anything. I lied and said I had a “system” and I could help her turn a few bucks into a few hundred bucks easy. Hey, I’d say more or less anything to spend a bit more time with Amanda.
She was just innocent enough to believe that stupid story and she agreed to come along. 2 days later we headed off. Now a bit about Amanda. She really was stunning. Medium length blonde hair, blue eyes, 5’6” tall, 36D, 110lbs. Basically way out of my league! I mean I’m not a bad looking guy. I’m 6’2” tall and not out of shape. I hit the gym 3x a week and I run but hell… I was 40 and had a few extra pounds that just refuse to come off. And she was what… 25ish? Less? I have trouble telling women’s ages. But she was broke and really out of options. Ok, I’m not a 20ish stud but one thing I have that they don’t have – a decent bank account.
On the way we listened to music and joked around. It was a very pleasant trip. At one point we passed a trucker and I dared her to flash him. “No way! Are you nuts!” She said. I said “I double dare you and I’ll give you $20 if you do it.” You should have seen the look on her face. She turned red and I could swear she was even sweating a bit. She thought about it for a second or two then she turned her back to me and gave him a blindingly fast flash that I doubt he even noticed. She turned crimson red and closed her eyes and said “OH MY GOD”.
I handed her $20 and with a huge smile she took it and giggled and laughed for about 10 minutes. She told me how she had such a strict upbringing and how she would never do anything like that… but that it was so fun. I got the idea that she was hinting she wanted to do it again. I was willing to just let it drop. But she went on and on.
So I said “feel brave enough for another dare?” and she said “mmmm… maybe. What is it?”
I said “Unbutton your pants and let me see your panties. You do it and I will give you another $20.”
She didn’t think about it very long… she unbuttoned her pants, slid them down a bit and I could just barely see the top of her panties.
I handed her another $20 and I made sure she could see my wallet was stuffed with a couple of hundred bucks.
As she went to button them up again, I said “tell you what… take them off till we get to the outskirts of the town and it’s worth $50.”
She was very reluctant… laughing and giggling and said “no way!”. But she didn’t button up her pants either.
After about 10 minutes she turned a shade of red and said “don’t look” and the next thing I knew she was taking off her jeans. She had the cutest little butt and those jeans were really tight. She had to do a lot of bending and twisting to get them off and she forgot to take off her shoes first. By the time she did get them off we were both laughing our heads off and she started to relax a bit.
I handed over the $50 I owed. This was getting a bit expensive.
So we drove along and she said “That’s it? Just sit here in my panties?” Was that a hint? She wanted another dare? More likely she wanted another $50.
I said… “well I’ve got another dare for you. If you are brave enough.”.
She said “What is it????”
I said “For this dare you have to agree to do it BEFORE you hear the dare or no dice. But it’s worth another $50 to you if you do it.” You could tell she was thinking I wanted sex and to tell you the truth, a blow job had crossed my mind… but that would be too fast and too soon and I figured she’d probably get out at the next stop.
She said “I’m not a hooker!”
And I said “Oh you goof. It’s not that. You don’t have to touch me at all. And I guarantee you will like it.”
So after some reluctance she said “ok. I’ll do it.”
This chance wasn’t going to come along every day. Ok… sure I sound like a dirty pervert but you are on a porn site reading this so fuck off for judging me – you would do the same thing.
I said “Your dare is to take off your panties and finger yourself until we get to town – but NOT cum. If you do that I’ll give you $50.”
She just turned purple and said “NO WAY!”
I said “I thought you were too chicken… Make it $100. And when we get to the Casino I’ll show you how you can at least double that on the Black Jack table”. Like I knew how to do that…
“What do you want me to do? So just finger myself?” she asked.
“Just do whatever you like. Whatever makes you feel good. But not too good – you don’t get to cum” I replied.
So slowly she started fingering herself through her panties. Kinda granny panties I’d have to say. So I reminded her “the panties too… they have to go”.
Now she turned really redder if that was possible. But I pulled out five twenties and said “hey… it’s a dare.”
Without another word the panties came off. I noticed that she shaved like the young girls do these days… I’m used to a bit of a bush. But ya… this was nice. She started slowly stroking her pussy.
She said “This is so dirty. I can NOT believe I’m doing this!”
I said “oh come on. You do this all the time anyway and we are getting to be good friends. What’s the big deal?”
She said “NO! I don’t do this all the time! I’ve only done it a couple of times and I felt so guilty about it!”
Then something started tugging around in the back of my head. I said “Umm… Amanda… how old are you?” Remember I said I’m not that good about telling ages? Well I really can’t. Perhaps I’m just stupid but past age 17 I just can’t tell till they hit about 30 or so.
Amanda said “Old enough! I’m not a kid.” Then I got this sick feeling. I grabbed her purse from the tangle of jeans and panties. Over her sharp protests I searched the purse and found a driver’s license. Bit of quick math. She was 19 years old. I was Soooooo relieved.
OMG that was close. I was a dirty old man and I was going to hell for sure but probably not to jail. Actually I live in Canada and at the time my Province had a legal age of consent of just 14 (It’s 16 now) so I would probably have been ok… but still. That’s young. The legal drinking age is 19 and you could go into a Casino at 19… so the trip would be ok. But she was SO YOUNG and I was SO OLD.
I did my apologies to Amanda and said I was just worried that she was under age and I was going to go to jail. She laughed a bit… then I said “What about our dare? You don’t have to do it if you don’t want to. Your not a virgin or something are you?”
She looked down and seemed a bit surprised to see she was nude from the waist down.
She replied “no I’m not a virgin. I’ve had a boyfriend. But sex doesn’t feel good and I don’t get orgasms…. Well sometimes when I’m by myself. But I feel too guilty when I do it so I don’t do it very often. It’s against the church and God.”
I don’t really believe in God but it seemed pointless to argue from that angle. I said “Amanda… Did you know that the clitoris only has one function. You don’t pee out of it. The only thing it does is bring you pleasure. It doesn’t do anything else at all. And God put it there, right? So obviously he wants you to have pleasure or it wouldn’t be there.”
She was really red now and covered up her crotch with her hands and put her purse on her lap. But you could see the gears turning in her head.
Thinking back to her house I said “Hey Amanda… how come you are living on your own so young?”
“Bad situation at home. I moved out. Dropped out of school. I’m trying to get on welfare or find a job or whatever.”
I asked a few more questions. She said something about her dad being in jail but then she clammed up and said “NONE OF YOUR BUSINESS.”
Ok. More alarm bells. She acted a bit like my last girlfriend Kinky who had been abused as a kid. This was turning a bit weird. But I was a bit too turned on to really care all that much.
I still had tiny bit of decency left so I said “Hey… let’s forget the dare. Put your pants back on. It’s ok.”
She asked “Do I still get the money?”
I replied “What… for not doing a dare? I don’t think so.”
She said “No way! I’m not letting you off. I said I’d do it and I’m going to do it.”
So she closed her eyes, turned up the music and laid back. She started by lightly stroking her pussy and then a bit more firmly. After about 5 minutes she was sliding a finger into her pussy, getting it wet, then swirling it around her clit. By 10 minutes, her breathing increased and she was arching her back.
I reached over and held her wrist. “Slow down girl. We are still a long way away.”
She pouted a bit but she did slow down. Playing with her clit and dipping a finger in and out. This continued for another 20 minutes and I could see she was getting frustrated.
I said “Hey Amanda… you have done really well. You can cum if you want to. But then I don’t have to give you the money. ” but she said “no a dare’s a dare” and she slowed down even more.
At the end she has a little puddle on the seat. I was very glad I’d gone for the leather package with the stain protector! By the time we got there she was just about frantic and dripping wet. It was sad and hilarious both.
When we reached the edge of the city, I pulled over and she pulled on her pants looking flushed and a bit frustrated. Or Horny. Or embarrassed. Or something. If I can’t read ages how am I supposed to read expressions? But I paid up and her mood improved quite a bit.
When we got in to town I had to pop in and see a customer. I left Amanda at the Casino with her money and told her to try and make it last as long as possible. I told her I’d be back in an hour and show her how to play Blackjack then she would make some serious cash.
I hurried through my meeting. When I got back to the Casino I found Amanda still planted at the slot machine I had left her at. How she managed to stretch that money in a Casino for an hour was beyond me. Those places are money pits for suckers.
I noticed that Amanda had at least 3 empty drink glasses beside her. Seems every guy in the place was sending drinks over plus the free ones they hand out anyway and she seemed a bit loopy to say the least. Then the slot machine went a bit nuts. Lights started blinking and it said she had won about $10.
I was busy looking around for a good blackjack table and didn’t notice what she was doing. She hit the “Double or Nothing” button. And WON. You could keep hitting this button as long as you liked and she just kept slapping it. By the time I turned my head back and saw what she about to hit the thing again for what must have been the 6th or 7th time. I said “STOP!” and I hit the CASH OUT button. Out came a credit slip for $640.
Amanda was really mad and told me she could have kept on doubling her money. I pointed out that the other half of that button said OR NOTHING. Rule 1: “Do not gamble what you can not afford to lose!” I told her it was time to get going. Her luck couldn’t hold forever. And judging by the slowly growing group of young studs circling like sharks I figured mine would run out sooner or later too - she’d run off with one of them.
Under protest she headed for the cashier wicket.
We had a really nice dinner that night. Amanda insisted on treating me from her winnings which actually made me a bit uncomfortable. I’m a bit old school that way. I was going to be driving so I went light on the wine but Amanda drank for the both of us.
When we hit the road we were just out of town and Amanda, flush with cash, full from a good meal and half drunk on wine was in a really good mood. She leaned over and kissed me on the cheek and thanked me for a really fun trip.
Then she said “I had so much fun with the dares and the dinner and the wine and winning! But how about you? Are YOU brave enough for a dare?”
I said “Ummm… well nobody wants to see a naked old man and remember I’m driving.”
She said “Well the dare is really simple. You just sit there and don’t say a thing for an hour and I’ll give you back all the money you gave me. But I’m keeping my winnings! “
I said “mmm… seems simple enough. I know it’s a trick. But ok. Let’s do it.”
And with that she slowly started stroking my crotch. HOLY CRAP.
It didn’t take very long and I was swollen and uncomfortable. She undid my belt and zipper and unbuttoned my pants to let the bulge in my underwear have a bit of breathing room. She continued to lightly tease and stroke my cock through my underwear. By this time the tip of my cock was poking out from the rubber band of my underwear and I’d had about all I could take. I lifted my ass and without a word she slid my pants and underwear down.
She used her finger tips to lightly massage my balls and my cock. She took the moisture from my pre-cum and worked it all around the head of my cock. Then she took her hand, spit into it, and used it to slowly slide up and down the shaft.
This slow easy motion was so distracting… but I was on a long wide open stretch of perfectly straight flat road (well my whole province is like that). This exquisitely wonderful torture lasted for what seemed like a day or two. She would speed up then slow down. Lucky I had cruise control or I’m sure I’d have attracted the attention of the RCMP patrol car we passed.
I don’t know how I managed it but I held my tongue and my cum for the whole hour. Barely. But talk about blue balls! I was dying for some relief and when I was allowed to talk again I said so.
She said “Well now you know how I felt!”
I said “Want to do something about it?” She looked very shy and said “ya.”
So we pulled off on a side road and parked behind a small grove of trees. I went over to the passenger side and got in. I slid on a condom from the glove compartment. I had my little snip-snip a few years earlier so there was no chance of kids. And I didn’t really think Amanda would have any diseases but you never know. The main reason was that I was worried I wouldn’t last very long and I always find with a condom I last longer.
Amanda stripped down totally naked this time. What beautiful breasts she had. Very large full perky breasts that you would swear were fake if you saw them on a porn or something. But I discovered very quickly that they were totally natural. She then followed me into the car. With almost no warning she sat down firmly on my rock hard cock.
She was so tight! She started to rock back and forth, moaning, her breasts brushing my nose, as her nipples became erect. After a few seconds she started moved slowly up and down, sliding my cock all the way out of her pussy then pushing it back in and down the full length. Her head was nearly hitting the roof of the car with each up stroke.
After about 30 seconds I released my load. Embarrassing to say the least! The condom was no help at all. But hey… you try getting a 1 hour hand job from a hot 19 year old blonde and see how long you last when she sits on your cock!
She smiled and got off. I said “Hey… wait a second. I’m so sorry!”
She said “For what?”
I said “Come on. Polite is one thing but I only lasted 30 seconds. That’s pathetic. It's ok to be mad.”
She said “That’s about how long my boyfriend lasts and he’s not even half as fun as you are.”
I thought back to when I was 20 something... ya... I didn't last too long back then either. “Well I last a lot longer than that! Give me a few minutes here.”
So we lay there holding each other. I lightly stroked her pussy and fingered her while we lay talking and kissing and cuddling. She was playing with my balls and lightly stroking my limp cock.
She told me how she always wanted to have a nice place to stay and how she wanted to go to school. She told me how her dad got into drugs and how she was sure he was going after her little sister. Not exactly sexy bed time talk but somehow I didn't mind. Her voice was so beautiful and her eyes sparkled in the starlight. Caution... do NOT fall for her I told myself.
She told me that she had called the cops on her dad and they broke up a drug deal he was working on. She had sent her own father to jail to save her little sister. Then her mother tossed her out of the house. She had wanted to finish school but the last couple of years were nuts. She only had part of her grade 12 and she wanted to go on to nursing school but she could barely afford to eat. Tia was cleaning up in comparison because welfare paid her a lot more because of the baby... all of which went to feed Tia's drug and booze addiction.
While we were talking honestly, I told her how young she made me feel. How it was a bit creepy being so old compared to her. She just laughed that perfect laugh of hers and said she didn’t give a shit and she wasn’t going to look at MY driver’s license so to “just fuckin drop it.”
As things went along I noticed that while she was quite wet to start with, but after 10 or 15 min she was down right soaking. I could start to feel a bit of a tingle too. And slowly my cock rose to attention. Not bad for an old guy! The talk slowly ended and the kissing took up in earnest. Deep and passionate.
Then Amanda and I made love properly. I made sure to finger her clit every now and again at first and I could tell she was having some small orgasms. I took her from behind. We even moved outside the car and did it over the still warm hood. She shuddered and moaned and groaned. Then she let out a few strange little yelps. I felt her vaginal muscles contract around my cock again and again. The contractions told me she was having a very deep and intense orgasm.
It did seem like a long time but it was probably only about half an hour of actual intercourse. When we were finished she started to cry and I held her. I asked “What’s wrong pretty lady?”
She said “What the fuck was THAT?”
I said… “umm… well women can have at least 3 kinds of orgasms. Clitoral, vaginal and G-Spot. I’d say you had one of each.”
Then she started to cry. Damn. I hate that. But I had to ask “Why are you crying?”
“It’s nothing. I’m just so happy and sad and tired. I feel all mixed up inside. I know this is wrong and I know it’s against the church but it feels so perfect. You showed me how to make money for rent and you have been so nice to me. “
I answered “ummm… Amanda I have not been nice to you at all. You are young and broke and I took advantage of you and your situation. And you can NOT make your rent money in a Casino – that was a total fluke. It would never happen again.”
I continued “But I’m going to make this up to you. I’ve got one last dare for you.”
She said “Sure but I’m just too tired for anything like… like THAT”.
I said “oh this one is the hardest one of all. I dare you to go back to school. If you do that and get good marks, I’ll find you a nice place. I'll pay your rent and give you some spending money too.” Hell... I make good money. This was really nothing. And maybe I was falling for this kid just a little bit.
She said “You would do that? And what do I have to do?”
I replied “Not much. Get good marks. Do your homework. Stay away from Tia and her friends. And...
She said "and???"
I said "... Maybe go on a few trips with me like this one. But only if you want.”
She said “Oh I thought that would be part of it. And if I'm extra extra good and we have a lot of fun... we are going to talk about a car. Deal?”
I didn't hesitate a moment. I said "DEAL".
Amanda and I had an amazing relationship. Yes, I paid her bills and we slept together a few times a week. She earned her car the very next weekened. Ohhhh how she earned it.
Over the years we took a few wonderful trips to Vegas and had a blast in the Casino's... never any luck there. But I felt like I'd won a gigantic jackpot every night with beautiful Amanda in my bed.
We even went on a cruise to the Bahama’s once.
Ever been on a cruise? They seat you with another couple for dinner. Everything was going well until one night when the other couple said something about my daughter. Amanda piped up and said “oh no. He’s not my father – he’s my Sugar Daddy!” Well the other couple asked to be seated somewhere else the next night.
So ya… This kind of thing has been going on since men lived in caves but I guess the world’s not really ready for this it to be so public. It's a hell of a lot of fun. It kept me young. There's even a name for it now. It’s called an “arrangement”. There’s even a web site now to set up this exact kind of relationship. Us old farts are called “Sugar Daddies” and the young girls are called Sugar Babies and for a couple of grand a month you can get a hot young thing around your arm. Google it.
But it’s so much more than that. Ok… there’s the financial side and I’m not stupid enough to think Amanda would have been with me without that. But we did develop an intense bond. We became good close dear friends.
We have long since parted company. I needed someone I could introduce at the company banquet without whispers and stares. Someone who didn’t say “who” when I said I liked listening to “The Who”. And she needed someone she could take to keggers. But I kept to my deal and I’m so glad I did. I’m proud to report that Amanda did get her high school diploma with a solid B average then went on to Nursing College and became an RN.
Amanda is married now and has a kid of her own. A cute little 3 year old with a devilish grin and a wonderful little giggle. I'm also married to a wonderful woman who has no idea I'm such a dirty old pervert.
I never fell in love with Amanda like I did with Kinky. I don’t think she fell in love with me either. But late at night… who do I think about now? Not my wife. Not even Kinky… it’s usually Amanda. When she can’t sleep she still calls me up now and again. We chat like old friends and the years melt away and I’m sitting there watching her finger herself in the car all over again. Maybe I should call her up with another dare or two…
--Smirky
Hey… I’m 50 year old. In all that time I’m bound to have had a few interesting things happen to me, right? So read on or skip it or whatever that’s up to you. But keep in mind this story is 100% true (or as close as I can remember seeing as it happened 10 years ago).
This isn’t really “Kinky girlfriend 2” either - because this is about a different girlfriend. I promised Kinky I’d never tell anyone her real name and that’s a promise I have kept so we will just call her Kinky. Very sadly, after a wonderful affair which lasted for a couple of the most enjoyable and exciting years of my life, she and I parted. Something about her husband holding a power tool to his head and getting all suicidal. Let’s just say things got very messy for a while and she left me.
I was feeling amazingly sad. Damn I loved her so much… I even get a bit misty about it now. I really went into a dark place. I’m not a “woe is me” kind of guy but I never figured there’d be anybody remotely like Kinky in my life again and that’s a depressing thought. Some day I may post a few more stories about Kinky and me… but it’s a bit painful and I’d rather look on the bright side of things.
Anyway in my depression, one night I saw those commercials about all the cool beautiful fun people you can meet if you call this local number for $$$ per minute. Not the phone sex lines. This was more like an old school party line where you can talk live to people from your city. So what the hell… I called it.
No, I didn’t meet any cool people. Most were lonely old hags with horrible smokers voices... which is to be expected because at the time I was in my early 40’s and lonely too. I wasn’t exactly a beautiful 20 year old stud - no idea why I expected the female half of this pathetic experience would be anything different. But there were a few young ladies on the line. After an hour or so I did get an invite to a party if I brought beer.
I showed up with a case of beer and a Pizza. HOLY was I out of place. Everyone was in their early 20’s. The girl who invited me called herself Tia. She looked like an ugly crack whore. Picture Courtney Love but much younger and even more strung out. She had a baby that didn’t cry or even move much… the whole scene was dirty, ugly and very nasty. Drugs. Booze. Drunk people. Vomiting. Not good. Now if I was making this up I’d tell you how there were beautiful people there and we all got naked and had wild sex but nothing could be further from the truth.
The only ray of sunshine at the party was Tia’s friend Amanda, although I didn’t know her name at the time. I also later found out it was Amanda’s place. She was renting a rundown old shack in a very bad part of town. How Amanda and Tia were friends I was never clear on but Tia was having a party at Amanda’s place and the party got out of control. Poor Amanda was just beside herself trying to keep people from butting cigarettes out on her sofa and puking on her carpet and stuff like that.
Tia never left the phone – she was still on the chat line busy inviting (read conning) more 40ish guys to bring beer and Pizza to the party. Anyway I got the hell out of there (and took my beer). I was there just long enough to fall madly in lust with poor frantic Amanda. Then I felt like a dirty old man for the rest of the night and drank my beer alone.
A couple of days later I was looking for my keys and it took me forever to find them. Briefly I wondered if I had lost them at the party. But that was a stupid thought. How had I made it home in my CAR without my keys? Still… that gave me an idea.
I drove over to the house where the party had been
held and knocked on the door. Yep… beautiful Amanda answered the door. I told her that I thought I had lost wallet at the party and I wondered if she might have found it. That’s when I found out that her name was Amanda, this was her place… and she had a certain spunky innocence and just the nicest laugh. She invited me in and we shared a beer while searching under the sofa pillows and stuff.
I said I could leave her my number if she found the wallet. She joked and told me she would probably not call if she found my wallet because she was so broke she needed the money. Then it wasn’t a joke anymore… she was going to get kicked out of her place if she couldn’t come up with a couple of hundred bucks for rent in a few days. Now a nice guy would have just handed her the cash. But while I’m not a total jerk, I’m not that nice either. The whole situation gave me another somewhat impure idea!
As I was leaving, I told Amanda that I was going on a business trip in a few days and I’d love some company. I invited her to come along and I told her I had a feeling her luck was about to change. I told her we could stop in at a casino and I’d give her a few bucks and stake her for a bit of gambling. If she won she got to keep it and if she lost she wasn’t out anything. I lied and said I had a “system” and I could help her turn a few bucks into a few hundred bucks easy. Hey, I’d say more or less anything to spend a bit more time with Amanda.
She was just innocent enough to believe that stupid story and she agreed to come along. 2 days later we headed off. Now a bit about Amanda. She really was stunning. Medium length blonde hair, blue eyes, 5’6” tall, 36D, 110lbs. Basically way out of my league! I mean I’m not a bad looking guy. I’m 6’2” tall and not out of shape. I hit the gym 3x a week and I run but hell… I was 40 and had a few extra pounds that just refuse to come off. And she was what… 25ish? Less? I have trouble telling women’s ages. But she was broke and really out of options. Ok, I’m not a 20ish stud but one thing I have that they don’t have – a decent bank account.
On the way we listened to music and joked around. It was a very pleasant trip. At one point we passed a trucker and I dared her to flash him. “No way! Are you nuts!” She said. I said “I double dare you and I’ll give you $20 if you do it.” You should have seen the look on her face. She turned red and I could swear she was even sweating a bit. She thought about it for a second or two then she turned her back to me and gave him a blindingly fast flash that I doubt he even noticed. She turned crimson red and closed her eyes and said “OH MY GOD”.
I handed her $20 and with a huge smile she took it and giggled and laughed for about 10 minutes. She told me how she had such a strict upbringing and how she would never do anything like that… but that it was so fun. I got the idea that she was hinting she wanted to do it again. I was willing to just let it drop. But she went on and on.
So I said “feel brave enough for another dare?” and she said “mmmm… maybe. What is it?”
I said “Unbutton your pants and let me see your panties. You do it and I will give you another $20.”
She didn’t think about it very long… she unbuttoned her pants, slid them down a bit and I could just barely see the top of her panties.
I handed her another $20 and I made sure she could see my wallet was stuffed with a couple of hundred bucks.
As she went to button them up again, I said “tell you what… take them off till we get to the outskirts of the town and it’s worth $50.”
She was very reluctant… laughing and giggling and said “no way!”. But she didn’t button up her pants either.
After about 10 minutes she turned a shade of red and said “don’t look” and the next thing I knew she was taking off her jeans. She had the cutest little butt and those jeans were really tight. She had to do a lot of bending and twisting to get them off and she forgot to take off her shoes first. By the time she did get them off we were both laughing our heads off and she started to relax a bit.
I handed over the $50 I owed. This was getting a bit expensive.
So we drove along and she said “That’s it? Just sit here in my panties?” Was that a hint? She wanted another dare? More likely she wanted another $50.
I said… “well I’ve got another dare for you. If you are brave enough.”.
She said “What is it????”
I said “For this dare you have to agree to do it BEFORE you hear the dare or no dice. But it’s worth another $50 to you if you do it.” You could tell she was thinking I wanted sex and to tell you the truth, a blow job had crossed my mind… but that would be too fast and too soon and I figured she’d probably get out at the next stop.
She said “I’m not a hooker!”
And I said “Oh you goof. It’s not that. You don’t have to touch me at all. And I guarantee you will like it.”
So after some reluctance she said “ok. I’ll do it.”
This chance wasn’t going to come along every day. Ok… sure I sound like a dirty pervert but you are on a porn site reading this so fuck off for judging me – you would do the same thing.
I said “Your dare is to take off your panties and finger yourself until we get to town – but NOT cum. If you do that I’ll give you $50.”
She just turned purple and said “NO WAY!”
I said “I thought you were too chicken… Make it $100. And when we get to the Casino I’ll show you how you can at least double that on the Black Jack table”. Like I knew how to do that…
“What do you want me to do? So just finger myself?” she asked.
“Just do whatever you like. Whatever makes you feel good. But not too good – you don’t get to cum” I replied.
So slowly she started fingering herself through her panties. Kinda granny panties I’d have to say. So I reminded her “the panties too… they have to go”.
Now she turned really redder if that was possible. But I pulled out five twenties and said “hey… it’s a dare.”
Without another word the panties came off. I noticed that she shaved like the young girls do these days… I’m used to a bit of a bush. But ya… this was nice. She started slowly stroking her pussy.
She said “This is so dirty. I can NOT believe I’m doing this!”
I said “oh come on. You do this all the time anyway and we are getting to be good friends. What’s the big deal?”
She said “NO! I don’t do this all the time! I’ve only done it a couple of times and I felt so guilty about it!”
Then something started tugging around in the back of my head. I said “Umm… Amanda… how old are you?” Remember I said I’m not that good about telling ages? Well I really can’t. Perhaps I’m just stupid but past age 17 I just can’t tell till they hit about 30 or so.
Amanda said “Old enough! I’m not a kid.” Then I got this sick feeling. I grabbed her purse from the tangle of jeans and panties. Over her sharp protests I searched the purse and found a driver’s license. Bit of quick math. She was 19 years old. I was Soooooo relieved.
OMG that was close. I was a dirty old man and I was going to hell for sure but probably not to jail. Actually I live in Canada and at the time my Province had a legal age of consent of just 14 (It’s 16 now) so I would probably have been ok… but still. That’s young. The legal drinking age is 19 and you could go into a Casino at 19… so the trip would be ok. But she was SO YOUNG and I was SO OLD.
I did my apologies to Amanda and said I was just worried that she was under age and I was going to go to jail. She laughed a bit… then I said “What about our dare? You don’t have to do it if you don’t want to. Your not a virgin or something are you?”
She looked down and seemed a bit surprised to see she was nude from the waist down.
She replied “no I’m not a virgin. I’ve had a boyfriend. But sex doesn’t feel good and I don’t get orgasms…. Well sometimes when I’m by myself. But I feel too guilty when I do it so I don’t do it very often. It’s against the church and God.”
I don’t really believe in God but it seemed pointless to argue from that angle. I said “Amanda… Did you know that the clitoris only has one function. You don’t pee out of it. The only thing it does is bring you pleasure. It doesn’t do anything else at all. And God put it there, right? So obviously he wants you to have pleasure or it wouldn’t be there.”
She was really red now and covered up her crotch with her hands and put her purse on her lap. But you could see the gears turning in her head.
Thinking back to her house I said “Hey Amanda… how come you are living on your own so young?”
“Bad situation at home. I moved out. Dropped out of school. I’m trying to get on welfare or find a job or whatever.”
I asked a few more questions. She said something about her dad being in jail but then she clammed up and said “NONE OF YOUR BUSINESS.”
Ok. More alarm bells. She acted a bit like my last girlfriend Kinky who had been abused as a kid. This was turning a bit weird. But I was a bit too turned on to really care all that much.
I still had tiny bit of decency left so I said “Hey… let’s forget the dare. Put your pants back on. It’s ok.”
She asked “Do I still get the money?”
I replied “What… for not doing a dare? I don’t think so.”
She said “No way! I’m not letting you off. I said I’d do it and I’m going to do it.”
So she closed her eyes, turned up the music and laid back. She started by lightly stroking her pussy and then a bit more firmly. After about 5 minutes she was sliding a finger into her pussy, getting it wet, then swirling it around her clit. By 10 minutes, her breathing increased and she was arching her back.
I reached over and held her wrist. “Slow down girl. We are still a long way away.”
She pouted a bit but she did slow down. Playing with her clit and dipping a finger in and out. This continued for another 20 minutes and I could see she was getting frustrated.
I said “Hey Amanda… you have done really well. You can cum if you want to. But then I don’t have to give you the money. ” but she said “no a dare’s a dare” and she slowed down even more.
At the end she has a little puddle on the seat. I was very glad I’d gone for the leather package with the stain protector! By the time we got there she was just about frantic and dripping wet. It was sad and hilarious both.
When we reached the edge of the city, I pulled over and she pulled on her pants looking flushed and a bit frustrated. Or Horny. Or embarrassed. Or something. If I can’t read ages how am I supposed to read expressions? But I paid up and her mood improved quite a bit.
When we got in to town I had to pop in and see a customer. I left Amanda at the Casino with her money and told her to try and make it last as long as possible. I told her I’d be back in an hour and show her how to play Blackjack then she would make some serious cash.
I hurried through my meeting. When I got back to the Casino I found Amanda still planted at the slot machine I had left her at. How she managed to stretch that money in a Casino for an hour was beyond me. Those places are money pits for suckers.
I noticed that Amanda had at least 3 empty drink glasses beside her. Seems every guy in the place was sending drinks over plus the free ones they hand out anyway and she seemed a bit loopy to say the least. Then the slot machine went a bit nuts. Lights started blinking and it said she had won about $10.
I was busy looking around for a good blackjack table and didn’t notice what she was doing. She hit the “Double or Nothing” button. And WON. You could keep hitting this button as long as you liked and she just kept slapping it. By the time I turned my head back and saw what she about to hit the thing again for what must have been the 6th or 7th time. I said “STOP!” and I hit the CASH OUT button. Out came a credit slip for $640.
Amanda was really mad and told me she could have kept on doubling her money. I pointed out that the other half of that button said OR NOTHING. Rule 1: “Do not gamble what you can not afford to lose!” I told her it was time to get going. Her luck couldn’t hold forever. And judging by the slowly growing group of young studs circling like sharks I figured mine would run out sooner or later too - she’d run off with one of them.
Under protest she headed for the cashier wicket.
We had a really nice dinner that night. Amanda insisted on treating me from her winnings which actually made me a bit uncomfortable. I’m a bit old school that way. I was going to be driving so I went light on the wine but Amanda drank for the both of us.
When we hit the road we were just out of town and Amanda, flush with cash, full from a good meal and half drunk on wine was in a really good mood. She leaned over and kissed me on the cheek and thanked me for a really fun trip.
Then she said “I had so much fun with the dares and the dinner and the wine and winning! But how about you? Are YOU brave enough for a dare?”
I said “Ummm… well nobody wants to see a naked old man and remember I’m driving.”
She said “Well the dare is really simple. You just sit there and don’t say a thing for an hour and I’ll give you back all the money you gave me. But I’m keeping my winnings! “
I said “mmm… seems simple enough. I know it’s a trick. But ok. Let’s do it.”
And with that she slowly started stroking my crotch. HOLY CRAP.
It didn’t take very long and I was swollen and uncomfortable. She undid my belt and zipper and unbuttoned my pants to let the bulge in my underwear have a bit of breathing room. She continued to lightly tease and stroke my cock through my underwear. By this time the tip of my cock was poking out from the rubber band of my underwear and I’d had about all I could take. I lifted my ass and without a word she slid my pants and underwear down.
She used her finger tips to lightly massage my balls and my cock. She took the moisture from my pre-cum and worked it all around the head of my cock. Then she took her hand, spit into it, and used it to slowly slide up and down the shaft.
This slow easy motion was so distracting… but I was on a long wide open stretch of perfectly straight flat road (well my whole province is like that). This exquisitely wonderful torture lasted for what seemed like a day or two. She would speed up then slow down. Lucky I had cruise control or I’m sure I’d have attracted the attention of the RCMP patrol car we passed.
I don’t know how I managed it but I held my tongue and my cum for the whole hour. Barely. But talk about blue balls! I was dying for some relief and when I was allowed to talk again I said so.
She said “Well now you know how I felt!”
I said “Want to do something about it?” She looked very shy and said “ya.”
So we pulled off on a side road and parked behind a small grove of trees. I went over to the passenger side and got in. I slid on a condom from the glove compartment. I had my little snip-snip a few years earlier so there was no chance of kids. And I didn’t really think Amanda would have any diseases but you never know. The main reason was that I was worried I wouldn’t last very long and I always find with a condom I last longer.
Amanda stripped down totally naked this time. What beautiful breasts she had. Very large full perky breasts that you would swear were fake if you saw them on a porn or something. But I discovered very quickly that they were totally natural. She then followed me into the car. With almost no warning she sat down firmly on my rock hard cock.
She was so tight! She started to rock back and forth, moaning, her breasts brushing my nose, as her nipples became erect. After a few seconds she started moved slowly up and down, sliding my cock all the way out of her pussy then pushing it back in and down the full length. Her head was nearly hitting the roof of the car with each up stroke.
After about 30 seconds I released my load. Embarrassing to say the least! The condom was no help at all. But hey… you try getting a 1 hour hand job from a hot 19 year old blonde and see how long you last when she sits on your cock!
She smiled and got off. I said “Hey… wait a second. I’m so sorry!”
She said “For what?”
I said “Come on. Polite is one thing but I only lasted 30 seconds. That’s pathetic. It's ok to be mad.”
She said “That’s about how long my boyfriend lasts and he’s not even half as fun as you are.”
I thought back to when I was 20 something... ya... I didn't last too long back then either. “Well I last a lot longer than that! Give me a few minutes here.”
So we lay there holding each other. I lightly stroked her pussy and fingered her while we lay talking and kissing and cuddling. She was playing with my balls and lightly stroking my limp cock.
She told me how she always wanted to have a nice place to stay and how she wanted to go to school. She told me how her dad got into drugs and how she was sure he was going after her little sister. Not exactly sexy bed time talk but somehow I didn't mind. Her voice was so beautiful and her eyes sparkled in the starlight. Caution... do NOT fall for her I told myself.
She told me that she had called the cops on her dad and they broke up a drug deal he was working on. She had sent her own father to jail to save her little sister. Then her mother tossed her out of the house. She had wanted to finish school but the last couple of years were nuts. She only had part of her grade 12 and she wanted to go on to nursing school but she could barely afford to eat. Tia was cleaning up in comparison because welfare paid her a lot more because of the baby... all of which went to feed Tia's drug and booze addiction.
While we were talking honestly, I told her how young she made me feel. How it was a bit creepy being so old compared to her. She just laughed that perfect laugh of hers and said she didn’t give a shit and she wasn’t going to look at MY driver’s license so to “just fuckin drop it.”
As things went along I noticed that while she was quite wet to start with, but after 10 or 15 min she was down right soaking. I could start to feel a bit of a tingle too. And slowly my cock rose to attention. Not bad for an old guy! The talk slowly ended and the kissing took up in earnest. Deep and passionate.
Then Amanda and I made love properly. I made sure to finger her clit every now and again at first and I could tell she was having some small orgasms. I took her from behind. We even moved outside the car and did it over the still warm hood. She shuddered and moaned and groaned. Then she let out a few strange little yelps. I felt her vaginal muscles contract around my cock again and again. The contractions told me she was having a very deep and intense orgasm.
It did seem like a long time but it was probably only about half an hour of actual intercourse. When we were finished she started to cry and I held her. I asked “What’s wrong pretty lady?”
She said “What the fuck was THAT?”
I said… “umm… well women can have at least 3 kinds of orgasms. Clitoral, vaginal and G-Spot. I’d say you had one of each.”
Then she started to cry. Damn. I hate that. But I had to ask “Why are you crying?”
“It’s nothing. I’m just so happy and sad and tired. I feel all mixed up inside. I know this is wrong and I know it’s against the church but it feels so perfect. You showed me how to make money for rent and you have been so nice to me. “
I answered “ummm… Amanda I have not been nice to you at all. You are young and broke and I took advantage of you and your situation. And you can NOT make your rent money in a Casino – that was a total fluke. It would never happen again.”
I continued “But I’m going to make this up to you. I’ve got one last dare for you.”
She said “Sure but I’m just too tired for anything like… like THAT”.
I said “oh this one is the hardest one of all. I dare you to go back to school. If you do that and get good marks, I’ll find you a nice place. I'll pay your rent and give you some spending money too.” Hell... I make good money. This was really nothing. And maybe I was falling for this kid just a little bit.
She said “You would do that? And what do I have to do?”
I replied “Not much. Get good marks. Do your homework. Stay away from Tia and her friends. And...
She said "and???"
I said "... Maybe go on a few trips with me like this one. But only if you want.”
She said “Oh I thought that would be part of it. And if I'm extra extra good and we have a lot of fun... we are going to talk about a car. Deal?”
I didn't hesitate a moment. I said "DEAL".
Amanda and I had an amazing relationship. Yes, I paid her bills and we slept together a few times a week. She earned her car the very next weekened. Ohhhh how she earned it.
Over the years we took a few wonderful trips to Vegas and had a blast in the Casino's... never any luck there. But I felt like I'd won a gigantic jackpot every night with beautiful Amanda in my bed.
We even went on a cruise to the Bahama’s once.
Ever been on a cruise? They seat you with another couple for dinner. Everything was going well until one night when the other couple said something about my daughter. Amanda piped up and said “oh no. He’s not my father – he’s my Sugar Daddy!” Well the other couple asked to be seated somewhere else the next night.
So ya… This kind of thing has been going on since men lived in caves but I guess the world’s not really ready for this it to be so public. It's a hell of a lot of fun. It kept me young. There's even a name for it now. It’s called an “arrangement”. There’s even a web site now to set up this exact kind of relationship. Us old farts are called “Sugar Daddies” and the young girls are called Sugar Babies and for a couple of grand a month you can get a hot young thing around your arm. Google it.
But it’s so much more than that. Ok… there’s the financial side and I’m not stupid enough to think Amanda would have been with me without that. But we did develop an intense bond. We became good close dear friends.
We have long since parted company. I needed someone I could introduce at the company banquet without whispers and stares. Someone who didn’t say “who” when I said I liked listening to “The Who”. And she needed someone she could take to keggers. But I kept to my deal and I’m so glad I did. I’m proud to report that Amanda did get her high school diploma with a solid B average then went on to Nursing College and became an RN.
Amanda is married now and has a kid of her own. A cute little 3 year old with a devilish grin and a wonderful little giggle. I'm also married to a wonderful woman who has no idea I'm such a dirty old pervert.
I never fell in love with Amanda like I did with Kinky. I don’t think she fell in love with me either. But late at night… who do I think about now? Not my wife. Not even Kinky… it’s usually Amanda. When she can’t sleep she still calls me up now and again. We chat like old friends and the years melt away and I’m sitting there watching her finger herself in the car all over again. Maybe I should call her up with another dare or two…
--Smirky
Poster:
Smirky
