This story contains scenes of a sexual nature between a young girl and older man. If this is not
to your taste, or is illegal where you live, or you find it morally
offensive, then read no further and leave now!!
The story is purely imaginary and bears no resemblance to any living person
or persons as far as I know, much as you or I might wish!
(feedback/constructive critisism is most welcome)
Brett c/- lexin10@gmail. com
ORPHAN ANNIE
Chapter #1- "Discovering the net"
“No mate, just not into the “singles bar” shit. Yeah, yes of course there are some damn hot girls but too young Ken, not my age and I am not going to feel that humiliation of rejection when they ‘flick” me off. Fuck they make me feel like an old pervert Ken, they’re not interested in someone old enough to be their father or grandfather God forbid. That’s right. Yes, no, no mate you are on your own sorry. Yep see ya and hey, good luck okay?”
I put the phone down having decided my fate for the evening and probably the entire weekend. Ken my single friend from work and some 8yrs younger then me at 40, had pestered me into the night life scene about two months ago and I had gone along with great expectations at first but now just wanted no more of it.
At 48 my life had become mundane.
I had finally broken away from my ex live-in lady and her two snooty nosed teenage boys. Quite frankly the lot of them had taken over some six years earlier making my life a frustrating daily grind to a point I no longer wanted to come home in the evenings and volunteered regularly for the overtime available at work.
Sandra was not a bad women, it was just that I never fell in love. Her sexual appetite was second to none from my past, a lady that liked to be a perfect slut in the bedroom in contradiction to her daily real estate life of glamour and public appearances.
It was sad when she left for both of us but I believe she felt the same and the boys could not get out quick enough, away from my strict old-fashioned curfews and such.
Me and the boys (Peter 18 & Jeff 14), had never bonded and they continually compared me to their ”great” father now overseas in an embassy posting.
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Not that he ever called them but he did remember birthdays and Christmas, spoiling them with the latest electronic gadgets and computers.
It was one of the boy’s laptop computers that first drew my attention to the sites I now use in my loneliness.
It had been left on the kitchen table late one night when I came home and as I touched it to close, the screen lit up on a site Peter was obviously a member of, teenfriendfinder. com. I used the in built mouse to have a look over the page and then saw some affiliate sites listed and clicked on two others before finding the first one that curiosity had me join.
It was a typical lonely-hearts site and one with free viewing of profiles. I was soon to chat with a couple of woman close to my age who urged me to sign-up officially rather then as a guest. Their their sexy photo displays and seducing words very convincing that first night online.
"silly_fuddy_ duddy" was my new id, more a sarcastic shot at myself such was my humor
I did not add a photo and left it alone without thinking too much about it. The mistake I made was putting my work email as a contact and was surprised the next morning receiving two flirts. That afternoon I bought my own laptop under the guise of taking work home.
The following weeks saw me online "role-plying" with women most nights after dinner, surprised at how easy i found it to tell and be part of a sexy story with a complete stranger, very proud of the compliments the all seemed to give me once orgasm had peeked, that is those that did not turn out to be the "Cum & go" ladies who sometimes just rudely signed off without another word.
Once home each day I would sneak into my den and surf around as a whole new world opened up to me and by “child and error” soon become adapt at using the sites and chat-rooms before a conversation might progress more privately to yahoo messenger.
It did not take me long before I had full profiles listed on as many as 5 other sites and each night it was a real rush to check and see who wanted to chat or communicate. Some very attractive and some hopelessly big and out of my ball- park always got my sympathy.
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I would always give their pics a vote of 18 out of 18 just for being brave enough to show.
Now alone with Sandra and the boys gone, these sites soon became my “best friend”
So here I was on a warm Friday night happy in my depression to be with my new “safe” friends and giving Ken’s plans the flick once more.
Dinner over, I sat in front of the bright screen in the darkness of my office with a bourbon and coke for company as I methodically visited each site for news. Further depression took hold as nothing new had come in and I had exhausted my time, about 3 hours, with others, becoming bored in their typical banter and lame role-playing. Same old lines without any imagination, “fuck me hard big boy yes, put your big cock in my sloppy wet pussy” and so on. It was just not working for me and even the one time I went on cam with a lady, I found it hard to get hard and cum and so deserted that idea quickly to avoid further possible embarrassments.
After making a coffee and with a new determination, I surfed some more and found a new site, agematch. com.
“Interesting lets have a little look here” I thought and proceeded to search profiles. Many of the woman or girls I should say stated they wanted to be with ‘older” men. I had not seen so many seemly willing sexy young women expressing this fantasy so I quickly knocked up a profile as a standard member without a pic and entered the free chat room. There was only about 30 members chatting and the men out numbered the females four to one. Some ladies looking for younger bucks and just the two younger girls seeking older males and getting plenty of attention as the room bombarded in a not so respectful fashion.
I looked at the 26yr old’s profile and let it be, she was a plumb young lady with a pretty face but of no interest to me. The other profile took my eye as I first seen her photo and read her details below.
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Such a young innocent face with beautiful pale porcelain skin with a tentative half smile with secret sad looking deep green eyes that looked back at me and told me there was something familiar here. I read on;
“Orphan Annie”
18 yrs Sydney East
Shy at first looking for fun older man maybe more
The rest of the information very simple and short;
Age: 18yrs
Sexual orientation: Experimental
Status: Single
Height: 5’3” (160cm)
Weight: 112lbs (52. 0kg)
Body type: Petite
Education: Some High School
Hair color: Black
Eye color: Brown
Bra size: Prefer not to say
Drinking: Yes
Smoking: Yes
Drugs: Sometimes
About you: I am a girl!!
Ideal match: A nice older man 30-70 willing to see inside and beyond appearances.
I looked at her picture again. Just a bust shot displaying cheap looking costume chains and necklaces with colored beads about her slim neck. It was an image more like from the 80’s, a little scratchy but never the less very pretty and something very familiar.
“Do I know you girl? God there is something about you I am sure. ” I said leaving the profile on the task bar and returning to the chat room.
“Damn, she is gone!” her last comment some minutes ago read;
"fuck off ya fucking perverted sicko pedophiles. ”
She had gotten into a verbal brawl with two other men, one 44yr old from the UK and another 32 yr old from the US, both had tag-teamed satisfying their own humor with degrading text and abuses. I felt very sorry for her.
Not so shy after all with her replied rhetoric making me laugh at her witty comments albeit, full of foul language.
“So your are a feisty little girl then Annie. Good for you young lady. ” I mused then called up her profile and posted a quick wink before sending a short email;
Hey Annie,
Saw you in the room and wanted to say hello but it looks like some assholes chased you away before I could “buzz” you.
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I do not know if we are a match in anyway but would love a chance to chat sometime, maybe offer a shoulder to unload on if you like. Got a good heart and compassionate mind about sums me up in brief but I am sure there is more to tell ~smiles~
Take care Annie and be safe.
Regards
Lex ( silly_fuddy_duddy. )
Shrugging my shoulders I pressed send finding the whole process entertaining and got up and went to the kitchen to make another coffe with a bathroom stop-over before returning to surf some more.
The screen task bar was flashing “Private chat request” and I immediately opened the box accepting.
“Hi Annie”
“Hey. . thanks yeah?”
“lol. . for what?”
“idn. . just for sending I guess”
“you’re very welcome honey”
“Please, don’t call me honey. . no offense. .
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just does not sit well okay?”
“Yup, no problems”
The opening conversation went with small talk before Annie asked about me in rapid fire questions of who are you? Where do you live? Married? Got kids” Where do you work? Etc to which I told her;
“Call me Lex (never give my real name on these sites,sorry but I was a virgin chatter till recently and this is my real name. . lol)) I live in Parramatta, never married, no kids, work in sales for an import company. Let me see, own my own home, quiet comfortable financially, happy in myself, um, just looking about to see who is out here in this cyber space thingy, oh, and very new to the net lol, be kind. ”I posted a quick brief
“Cool, at least you are in Sydney. I knewLex once many years ago. So why did you join this site and how come there is no picture?”
“I haven’t had time to post my ugly face, lol, and the site I only just came across. I don’t know, maybe just experimental to see what happens I guess. ” I replied sparked by her reference to us living relatively close.
“I C, so you have a fantasy of being with a younger girl huh? Just won’t admit it? ~winks~ she flirted back
“Um, now maybe, never really thought about it before though I have to admit going to singles bar in search of anyone, lol, only to get slapped in the face so the whole thing scares me a little. ”
“Come on Lex, you can tell me, A bit of tight young pussy would make any man want right?” she shocked me
“Okay. Lol, You got me Annie. I don’t think too many men would baulk at such a scenario. Lol. ”I typed, the conversation quickly causing my cock to swell in my track pants.
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“That’s better old man, I would have been disappointed if you said otherwise. ~winks~
“May I ask about you Annie? What is the Annie story?” I sent politely and with respect.
“Not sure if I am ready for that yet, sorry, suffice to say I am here because I have always had a fantasy for older men. Do you think that is weird?”
“I understand, maybe after you know me a little better when some trust is there huh? Um, no not weird, just different I guess. No different to someone being gay or having a particular fetish. That is my take and something I never really thought about. ”
“Thanks Lex, you are nice”
“Awe shucks. You are welcome. ~smiles~”
“Lol and funny. ”
I was pleased to sense her likable attitude and pushed a little further.
“Okay, can you tell me then how this liking for older men came about then? Oh, and what is a preferred age?” I asked a little selfishly.
“Okay cool. Yeah um, first the age does not matter so long as they are at least 18 years older then me and well, I’m not really sure why, I just think older men are not as competitive and a lot less complicated. II seems like they, well most, can be just nice, as if age makes them content and knowing, more understanding if you like. Oh and it helps if they have a “reliable” cock of course.
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Lol. You still get the fuckwit assholes of course and as for how?Something I developed as a young kid, I am sure of that. I’ll tell you this much nosy Lex ~grins~ I never really had a mom or dad and was pretty well left on my own at home, told to get out of the house so they could ”entertain” as they fucking called it. I just found myself over next door a hell of a lot. A really nice man he was. I think he felt sorry for me roaming the streets at that age 7 and 8 and always made sure I had lunch there with him, kept me fed and even had me clean up, bath and all. No there was never any drama’s sexually, he was just a fucking real nice man and I always felt safe with him. Mom and dad could care less ~shrugs~
There it was that familiar stirring of knowing more again. I quickly looked at her picture again but nothing came.
“Wow, thank you Annie. Easy to understand that, I don’t suppose you might…”
“Hey, bugger, sorry have to run Lex nice talking. ” Her post interrupted.
“Oh okay, love to again Annie bye, take care. ”
“Sure I’ll be back in about an hour if you are still on okay. Bye!” And she was gone.
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I re-read the scrip a couple of times racking my brain as I compared similar events in my life.
Before I met Sandra I was living alone over in Ringwood and next door in a rented property was this little 5yr old girl who I befriended on weekends. I felt very sorry for her but not for her “druggie” parents. I had discovered during that short period, a deep-seated paternal instinct that had eluded me through life not having bared any children of my own. It was me that reported the lack of parental care to the Department of Children's Welfare only to see the place raided a few weeks later and the parents arrested for supply. Apparently one room in the house was set up with elaborate hydroponics and a street value of over $100,000 worth of dope discovered almost at maturity. I never saw little Kristen Reynard again and often wondered what had happened. I did find out she had become a ward of the state and was in foster care. That would make Kirsten about 18 or 18 now.
Closing my laptop I went into the lounge to see if a cricket match could distract my interest.
I fell asleep with the aided affects of the small amount of alcohol consumed, waking with a start about two hours later. The humid night left my t-shirt wet and sticking to my back so I decided to shower and shake some of the cobwebs aside.
Her pretty image blurred my vision as I let the steamy hot jets shower hard to my face amazed to discover my cock stir half full before washing, rinsing in the sudden chill of cold and stepping out to dry.
A middle age physic reflecting back from the vanity mirror had me take a closer look before dressing and an anxious want to investigate my new site for a sign from my new young friend.
“Not bad for an “old man” Annie” I caught myself chuckling.
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I proudly kept fit running at least once a week and golfing on weekends when the weather suited. I was bigger of course then my more intense football days about one or maybe two stone heavier but a solid look never the less. Thick thighs and muscular calves a testament to my youth. A little hairy for today’s society with a thick mat of grey over my chest, matching my receding temples, gone was any resemblance to the thick brown hair of the past. The only drawback I felt sucking in my stomach was the inevitable small pot that age could not counter. The habit of “grooming” my genitalia still with me from my time with Sandra who had convinced me to try, something I found very sexual now. I was not well endowed by any means but happy enough with my average 5 inches of manhood albeit it now dangling at a soft 3 inches, something Sandra often teased me about in an affectionate manner and had often fallen asleep with it in her hands after an evening of hard sex. There were never really any complaints form former lovers on sexual grounds.
I pulled on some silky feeling boxers and skipped downstairs to the den.
Annie’s box was alight as soon as I opened;
“Lex, you there? (7:12pm)
“Buzz” (7:12pm)
“Buzz” (7:26pm)
“Please come back Lex” (7:48pm)
“Buzz” (7:49pm)
“Buzz” (8:10pm)
“I am staying on line Lex. If you come back buzz me” (8:21pm)
My heart Jumped, flattered that she had waited and tried to reach me. “What time is it? Fuck! 9:07pm. All registered in the rush as I took up my seat in front of the glowing screen, excited like an adolescent kid as I quickly posted in haste spelling her name incorrectly in the haste.
“Annnie?Are you there?
“Oops Annie sorry. Be there Please.
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So Sorry. This “old man” had a “nanny nap” lol”
I corrected as fast. Then waited watching for the screen to show me a sign.
“So you are an old “fuddy duddy” then Lex? How are you?
“Oh great you are still there. So sorry Annie, I fell asleep had a shower and just came back in. Yes, real well thank you, could stay up all night now. lol”
“hmmm, and just what would staying “up” infer huh Lex? Are we that virile then? ~winks~
“Haha very funny Annie. This “old man” might surprise some just the same. lol”
“Maybe you could surprise me Lex? I could do with some nice “attention” right now. What do you say? Are you up for it old man? ~sniggers~”
“Cheeky girl, be careful what you ask for. I might just take you up on it!”
“Okay Lex, do you ever role play here on these sights?’
“I’d be telling lies if I said no Annie. What have you got in mind?” I replied. Now I was getting excited. Just thinking of playing with some one so young was a huge turn on. I was already hard in my shorts waiting for her reply.
“Well if you promise not to be angry I’d like to age play, have you ever done that Lex?”
My mind raced in excited ignorance.
“Um, you may have to explain Annie. I’ll just say I have done some pretty way out there roles for woman so nothing would surprise and I will tell you, I judge no body on these sites, no matter what kink or fetish they request. ” I posted back politely so keen to know what she had in mind.
“That’s good Lex. I want to play young, very young. I want to be 12 or 18 and you are my next-door neighbor. Is that okay?”
“Oh hell Annie, you want me to play a pedophile? I don’t know about that. ” I was surprised and a little disappointed.
“No, yes, well kind of but not a predator Lex. I don’t know let me explain more. You have been next-door for as long as I remember and we are just the best of friends. I am always running across to your place. My parents like and trust you as a good family friend. Um, I just want to try this Lex.
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It really turns me on to think of my little bald slit all wet for my handsome “second uncle” neighbor. I am at that curious age, innocent but wanting to know things and I manage to get you to help me, show me about my body, discover it. Oh and yours of course. Have you never thought what it would be like Lex?”
Why was my cock so damn hard?
“No really Annie but I am game I guess. I’d like to try this. My god you know how to stir an interest” lol
I felt a mix of shame and intense erotic arousal as a picture quickly formed in my mind of a young girl naked before me in all her adolescent glory. Small budding breast and hairless or light fuzzed covered pussy all wrapped in smooth unblemished skin.
“Oh cool Lex let me set it up and see where it goes okay? Remember, no judgments made at this end or at yours okay and it will be great fun, you’ll see…. ”
My brain exhausted some 3 hours later from the constant wish to be equally creative and imaginative as this young woman as I read her next post. My cock remaining hard during the whole episode and now squished about in socking pre-cum on my boxers
“Wow Lex that, this is awesome don’t you think? End chapter one? We can continue this love story? ~smiles and hugs~”
“Man Annie, you are so good at this. I don’t think any play has ever been so good and I like the romance aspect. To think a man my age could be so lucky. . haha” Such a bad/good little girl you are ~hugs~”
We had traveled a path in a world I had never thought about, sexually extremely arousing and romantically very satisfying. We had managed to keep the story clean and respectful even though the content was wild and at times crude.
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It was in fantasy only and something to dream about.
“Thank you Lex, thank you for sharing my fantasy so articulate and warmly. I really believed your words. It was like it was so real to me and my God, I am so, so wet here. I came about 3 times. How about my handsome old next door neighbor Lex? Did little Annie make his nice cock blow?”
It was such a first time experience to me. Chatting so erotically and intimately with this pretty looking young 18 year old girl was a huge turn on. Now as she typed back telling me more personally how our story had affected her was even bigger. To think of her playing herself to orgasm within my words made my already hard cock jerk more. Being bold in a new license of open honesty with this girl I posted back;
“Christ Annie how could I? I needed both hands on the keyboard to keep up. Lol I will tell you however that I sit here now in my boxers hard as a rock with my cock swimming in pre-cum dribble. You are one hot girl Annie, thank you and yes, we must continue soon, chapter two that is, tomorrow night?”
“Please yes, I will be online tomorrow Lex. I can not wait but first do me a favor please?”
“What?”
“I want you to cum for me now before I have to go. I want to imagine you jerking your cock Lex. You painted such a lovely story and description of your character.
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I know it is you whom you describe Lex and I want you to make your self cum for me. I love it. ”
Again her words made me so excited.
“Oh man Annie, I wish it were true, that you were here. I do not think it will take long honey. I have needed to burst all this time. Lol” I replied keenly.
“Wonderful Lex, you are so sweet. I really would love to be there with you right now, watching you. Imagine that Lex, look at my profile pic and jerk your thick cock for me. Imagine I am sitting across from you naked, my legs spread and my fingers shiny wet digging into my young tight pussy. (I am you know ~winks~) Do it Lex, fuck your cock for me and tell me when you cum. God I am so hot thinking about you. ”
I did as she asked quickly standing to drop my shorts, my cock swaying about as if searching for a prey. Her profile open as I began to jerk my fat blood swelled cock.
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”
“Okay Annie. I am doing as you say, imagining your pretty face looking at me, like in our story. Little Annie so excited as I show her how I cum as she sits naked in the bath. My God this is hot!!”
I exploded, turning my self away from the desk to shoot two long thick strings on the carpet before another 4 or 5 pumped free.
“Cuming here Lex…”(12:04am)
Her post was two minutes ago I realized after I used some tissues to clean up.
“Oh fuck Annie I came harder then I can remember honey it was awesome”(12:06 am)
“Annie?” (12:09am)
“Coming back baby?” (12:17am)
“Okay, good night Annie. I am hoping you just fell asleep?” (12:32am)
I reluctantly shut down the computer not quite sure if she in fact did just crash or whether like many times before, the ladies just disappeared after they got their kicks. I picked up my sodden boxers and headed naked upstairs to bed. Not bothering to dress I crawled between the cool sheets and found sleep remarkably quick.
Continue to Chapter #2 "The Role-play"
Brett © 2009
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