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Here I was again. Same situation, same problem. Exacerbated by the fact that this time, the difference was around twelve years instead of three.

It wasn’t that I couldn’t be trusted. The problem, at least for me, is that I can.

Let me explain.

I hadn’t had a boyfriend for a while. The last boyfriend I had was actually quite a bit older than me. He’d said he was forty, when he asked me out. Turned out he was 48. Not a bad age, exactly, except that I’m 30. A ‘young’ 30, although I wince at the term. And to put it mildly, he couldn’t keep up with me, in bed or out of it. The memory that springs to mind is the two of us climbing a set of stairs outside a mall, with me trying (a bit impatiently) to subtly slow down and him puffing along behind me. He kept asking me to marry him, actually. The funny thing is that despite his age, he really wasn’t ready. That much was obvious. I’ll leave out the gruesome details of our sex life, because basically they consist of him trying to convince me that I really wanted to sleep with him, which I didn’t, and, the two times I reluctantly went along with his clumsy seductions, that I had enjoyed it. Mhm. No, I don’t think so.

So, to put it in simple terms, I don’t consider myself particularly age-ist. I just want someone who isn’t going to slow me down. And I don’t want to think about retirement plans! I know I’m not eighteen, but I do feel like I’m just getting started on the rest of my life. Which means that if a guy is looking for a trophy wife to settle down with on a farm in the back of nowhere, he’s got the wrong girl. Woman. Well, whatever.

On with our tale.

I’m relatively new in town. I’ve been living in this city for just over two years. The first year I was here, I was too caught up in recovering from the most major and most disastrous relationship of my life. Believe me when I say that I shocked myself by having absolutely no interest in men at all for quite some time. I’m not the type to sit home with my multiple cats and multiple cheesy movies every night. Well, I don’t even like cats, I admit it. I’m more of a dog person, although I have been known to pet a kitty now and again. Point being, I haven’t been my usual social self until recently. Now I’m getting back to normal, or as close to it as I ever do get.

Rachel is one of the few people I consider a friend here. Which means seducing her baby brother is probably not a really good idea. I’m trying to avoid it, but he keeps sort of popping up, all hopeful puppy eyes and gangly legs. I can tell by the way he looks at me when he thinks I’m not paying attention that he has a little crush. It’s sweet. Well, sweet and dangerous. He’s at a hard age. I don’t want to hurt him.

It’s nice to have someone a little bit in lust with you, but it’s kind of tough when it’d be really wrong to encourage him. I’ll be honest. I’m lonely, he’s awfully cute, and I’m tempted. But I won’t do anything stupid. I’d like to think I’m not that careless of a person.

I was thinking, tonight, when he messaged me on Facebook, that I shouldn’t even talk to him. But the evil interweb intervened, as it does. Someone sent me another tacky app, ‘Sexy Date’ I think it was. Well, I know the girl who sent it, and she probably just thought it was funny. But I vaguely skimmed the friends that appeared on the list, wishing one of them really was a sexable date. My wifi crashed just then. So, bearing in mind the scientific repercussions of Murphy’s Law, of course the app sent messages to all my friends because of the page error. Oops.

He was practically burbling with excitement. ‘So, I’m your top Sexy Date, huh?’ Uh oh. Screwed by proxy, in this case, via bad bandwidth.

‘Oh um well… sorry! Actually it was a page error. I wouldn’t have sent that to you! You’re practically jailbait, ya know!’

Quickly, I put up a status message informing all and sundry that any ‘Sexy Date’ messages they received from me were due to an error.

‘Damn,’ he typed back. ‘People keep telling me that!’

I thought back to his parents’ barbeque on Independence Day. How he’d half-heartedly tried to convince me he was twenty-two. How, for a second, I’d believed him, because with his height and shoulders, he easily could be. But then I looked at his face and saw that slight babyishness around the chin, and decidedly hollered back, ‘You are not!’ It was all very relaxed and casual. At some point we all wound up singing old Simon and Garfunkel songs. I think I was the only one who knew most of the words. I love singing, and I’m not terrible at it. I was belting out lyrics with the group, and he was sort of staring without staring, if you know what I mean. Hey, not my fault I have a chest. I didn’t invent it. I don’t flaunt it… much. He ducked inside halfway through, and I felt unreasonably guilty. Le sigh.

Last time I had a little mutual crush on my best friend’s little brother, back in my hometown, he and I were both in our twenties. Well, he still is. I somehow thought it was important to be honest and tell my friend. She was horrified. ‘He’s my baby BROTHER!’ she hissed. ‘Yeah,’ I pointed out. ‘But he is twenty-one, not a child.’ My twenty-fifth birthday would be just before his twenty-second. It didn’t seem to make much of a difference to her. I never did anything about that one, either. I remember hanging around their house all summer that year, and my friend’s brother making a point of casually appearing in a tight undershirt whenever I showed up. Oh, it was kind of nice.

I knew my friend, and her family, which I consider to by my extended family, were too important to me for me to mess up that relationship for a little fling with Studly Jr. over there. Her mom actually encouraged us to date, dropping heavy hints when she saw us together. But once I saw past the Ben Affleck looks (I swear, not exaggerating: probably better-looking) to his less-than-enormous brain, my crush was over. When it comes to gray matter, size does. He’s married now, to a very nice if not very bright girl. He has a little pot belly. And he still casts lingering looks in my direction if I’m around, although he’d never do anything about it now. I’m really glad I never went further than some flirtation with that. His laugh is really kind of dopey. I know that sounds mean, and I’m not trying to be. Just saying that because it was the one thing that first clued me into his non-genius-type status. Augh. I’m not as snotty as that makes me sound. I’m happy for him. He’s got kids and all.

But back to Rachel’s brother, whose name I won’t mention to protect the semi-innocent. No one’s that angelic in their teens! We can call him Gabe.

I saw him on the bus the other day. Trust me to find a way of making catching a bus look crazed. It was late, and it was the last bus. I was a bit distracted, thinking about the movie I had just seen, and the bus nearly passed without stopping. I waved my hands and ran after it, and it skidded to a stop a bit farther down. Nice when the bus driver recognizes you. He’s too grumpy to admit it, but he does, and it was really nice of him to stop. I flung myself aboard, grabbing the waistband of my cute new skirt. Damn thing was far too stretchy and almost stretched itself into a pile of fabric on the floor.

‘Hey, young lady.’

I looked around in bewilderment, catching my breath. ‘Oh, hi.’

‘What are you doing out so late?’ His tone was mock-stern.

‘Oh, uh… just coming back from seeing a movie with a friend.’

I could see the wheels a-turning. Date, he was thinking. Well, no. Actually, it had been an evening trying to cheer up my stressed-out friend Lara. I had treated her to dinner and a movie, and she is sort of ex-gay, except on alternate Wednesdays, but we really are just friends. So no, not a date. I’m kidding about the Wednesdays. She does get ‘that look’ in her eyes every so often when I’m wearing something sexy, but she’s trying out straight as a lifestyle, and I’m very supportive of
that.

I have to admit I was a little bit pleased to see him. There’s always a shortage of available, good-looking guys. I have to keep reminding myself that he’s actually NOT available. Not unless I were his age. Ha! I wouldn’t go back to being a teenager for anything. Besides, most guys didn’t look twice at me when I was that age. Goofy, frizzy, frumpy and braces, plus some chub. Ouch. Nope, wouldn’t switch.

What is it with this ‘older woman’ thing? Shouldn’t guys his age be attracted to the dazzling young twits flitting by? Things! I meant young things. They’re rather sweet, really. I just don’t have the patience for them anymore. I don’t think I’d have the patience for myself, either, if my younger self somehow appeared on this city bus and sat down next to me. It’s easier dealing with people my own age, or older. Which should mean that I’m not as pleased to see him as I actually am.

Is it really so wrong that I’m thinking unprintable thoughts about my friend’s little brother? Yes! YES it is. I shake an imaginary finger at myself, in my head. Bad girl! Very bad.

Gabe got up and sort of hovered, shifting with the bus’s motion.

I patted the seat next to me, trying very hard to be virtuous and succeeding in lying only to myself. ‘Want to sit?’ I wasn’t going to do anything. Really. Not on a city bus, anyway.

He looked at the scruffy bus seat regretfully. ‘Nope. Gotta get off next stop.’

I smiled. ‘See ya around.’

Gaah.

Damn.

I smiled anyway, thinking things that should get me at least a slap on the wrist, all the way home. Good thing my trusty plastic pal was ready and waiting, as it always is.

It’s hard doing the right thing. I hope he stays away from me. He should be falling in love for the first time, not being enthusiastically corrupted. Double damn. I swear I’m trying. But couldn’t hurt him since he doesn’t know… that I’m seeing his face, among other things, at the most inappropriate moments.

Good luck, Gabe. Find yourself a girlfriend at your high school, or in your theater group. Someone who has the right to play all the naughty games she wants with you. I’m taking my piece off the board.

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Guy Line

"Okay, then, guys, here are the rules. As each of you loses the game, you get to be next to do what I want you to do with me. As you come into my bedroom, you must strip and show me your cock, hopefully already hard seeing my naked body there waiting to be fucked," Lisa giggled. "Hmm, I may ask you what you like or I may just tell you to continue what the previous guy started. That again depends on me." She continued with the rules as we stared on, "Steve gets to be first obviously,...

2 years ago
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Cut OffChapter 3

When I started telling Melly about the embryonic village just east of Branson I saw her eyes glitter. She became more and more excited. As her excitement grew my mood fell. I did my best to hide it. I felt that I owed her a chance at her own family. For the next month we taught her how to drive the semi and filled it full of bio diesel, as well as a home starter-kit. When she finally left, full of hope and ambition, my life crashed to the floor. I looked around and decided that I didn't...

3 years ago
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I Love Florida Man

This Story is one of my fictitious Stories, But really Awesum..!!!EnjoyIt was a rainy day like any other in Florida when we met. Having stopped by his house not knowing he would be the one who was home, we stopped to have my car fixed. Jesse – my current friend who knew the home owner as she had dated his brother and wanted to sleep with him as she did everyone else recommended we stop by to get help.We ran to the door to get out of the rain, we knocked and waited as the front door opened and a...

2 years ago
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The Traveling WizardsChapter 4

Sunlight shining through her eyelids woke Celeste early this morning. Sitting up in bed, she looked out the glassed in doors overlooking the Twin's Yard. The Twin's Yard was a courtyard positioned between two arms of the castle the guestrooms and Offspring's Hall. It was a modest courtyard containing a simple pond in on corner. A large weeping willow grew on the bank away from the stone walls, forming a shadowed hideaway beneath its branches. Opposite the pond was Celeste's pride and joy....

4 years ago
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How I Got My Wife To Be Shared For The First Time

After I tried for 3 years to talked my wife into being shared I finally made it happen. It took a calculated risk but in the end I got my wife to except it. I had asked my wife on a number of occasions about her fucking another man but I was rejected each and every time I had asked. I knew I needed a different approach.I was going through the personal add site in my area when I came across an add that said, “I want to massage your wife for free.” It had gotten my curiosity up as I decided to...

Wife Lovers
1 year ago
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My Virgin And Hot Cousin

Hi friends, this is Rohan from suburbs of Mumbai. I’m a regular reader of ISS. This is my favoret sex stories site. I like INCEST column the most. This is my first story on ISS. My real incident that happened with me at my home itself. I’ll tell the story in 2 parts. I’m average looking guy with 5’8” height. Wheatish skin tone. My cock is of 6 inches long.The incident occurred with me in my summer vacations after my 12th exams 2 years ago.Before going straight to the story, let me tell you...

3 years ago
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Indian Mom And Son Love 8211 Lustful And Romantic

This story is fictional, and is about a forbidden relationship between a Mom and her son. In a lower middle class family, Rajan (41) is a Bus driver working with the state transport corporation, he does night shifts on a regular route between Tuticorin to Chennai. He is home every alternate days and leaves at night for work, he seldom ends up with day off because the allowances and overtime always interested him rather than resting at home. Rajan’s wife Kalyani (40), a typical house wife took...

Incest
2 years ago
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HOLY DAYS and Christman with Her

user]NikMature[/user]C had expressed wanting to attend temple, I declined the invite .Ifelt during the festival of lights I would be an intrusion.So she invited the lil neighbor boy, they left all dressed and were gone for a few hours, I thought nothing of it, until C came home, I heard muffled talking with lil shit and then she came in. Have I got something to tell you , it was confession time over coffee after, he told her that He was very aroused listening and catching peeks through the...

2 years ago
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College Town Part 3 Drunk and Young

Samantha's parents were out of town and she was throwing a party with a lot of her classmates from high school. The party was heating up and most of the crowd was already drunk from the kegs that her friends' brother had brought. Samantha was already extremely drunk as she joined the guests in the crowded kitchen to take shots. “Just one more!” Samantha said, raising her index finger, referring to the number of shots she intended to take, stumbling while she said it. Her friends Jess...

3 years ago
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what do they wantPart 1

My husband likes me to dress in sheer revealing tops, go braless in the house and wear short micro mini skirts with no panty or just sheer and even crotchless panty.I never had suck clothing articles and the feel of the material was in itself arousing against my nipples especially. I am a Filipina and have very large nipples even when not aroused. My husband loves them and has even had me go to public places such as grocery stores, parks, malls, etc with no bra and clingy stretched cotton...

3 years ago
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My Boss Is a Shemale

I slowly put my tongue on it. It’s so hard and solid. I feel like I could break my skull on it. I can feel her breathing and shiver as I slowly put the head in my mouth, so warm. I alternate between suck the head and licking the shaft, even giving some attention to the balls. I had a really bad week. Actually, bad would be an understatement, shitty would be more appropriate. Problems after problems had punctuated my Days. I managed to get a new job as an assistant executive at an...

2 years ago
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Five Times Fourth Time

This is the fourth of five accounts I’d like to share with you about my experiences between 2008 and 2016. This account takes place between 2011 and 2012. As with my previous entries, these events really happened. However, this account covers almost a year, so I’ve combined some of the experiences in order to avoid repetition and keep the story to a reasonable length. The traffic was worse than usual, and it was already dark by the time I arrived at her house. I unlocked the door, dropped my...

2 years ago
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nightmares and dreams0

I NEVER WANTED TO BE GAY THE IDEA OF IT MADE ME SICK BUT FATE HAD OTHER PLANS > PART ONE - MICHAEL AND BARRY For me all i ever wanted was to meet someone and fall in love get married and have children. So i guess before i get to that i should start at the very begining. As a small kid i was top of my class and liked by all , i did what most kids did but when i reached the age of 8 one of my friends insisted on both of us getting naked even though i never knew why , i did not...

3 years ago
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Shellys spit Brandons Cock and my mou

I'm not sure if this blog post will be everyone's cup of tea, but I'm going to share an eye-opening experience that I had a weeks ago. Maybe some of you enjoy this "flavor" of kink. I'd never been in to the Sub/Dom scene -- it wasn't like I wasn't aware of it, I just never had much exposure to it. Then I hooked up with Shelly and Mark, a mature couple I met on a swingers website. She was 57, tall, slim, with graying brunette hair, glasses -- she was attractive and hovered between MILF and GILF....

1 year ago
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Juicys Wish

My cock is hard again from watching him fuck her. I climb on her, she’s face up, I kiss her passionately Her manhunt had eventually found a compatible guy for Juicy. Muscular, tall, nice smile thirty seven and a smooth body. They have been chatting on the text and he is polite, his grammar is good, she’s keen almost fallen for him and she looks forward to his daily contact. I’ve seen him and he looks good, after all I will be sharing my soulmate, the love of my life with him. I have...

Sex With Stranger
2 years ago
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The Derelict Station

The landscape flashed by. The box car wasn't that comfortable, but it did accommodate his bike for he knew from past experience that a bike in a passengers section of a train didn't mix. 'Should reach my destination around lunch time', he muttered. 'The map said that the old rain line, now converted into a cycle track should take two and a bit hour to do the entire circle. The rail line doesn't do the circle but it picks up a bike track that does the return'. A quick gander at his watch...

2 years ago
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The Knight and the Acolyte Book 7 Illusory PassionChapter 3 The Piratersquos Claws

Thanks to b0b for beta reading this! Warlock Faoril – The Golden Hunger, The Nimborgoth Shock paralyzed my actions as the pirate captain, Thyrna, pressed my face into the shaved, spicy folds of her pussy, smearing it on my flesh as she held a fistful of my short, light-brown hair. Pain flared across my scalp as she humped against me. She lay on her bed’s edge. I knelt on the deck of her cabin while her ship rocked and creaked about us. It was dim, sunlight streaming through small portholes,...

4 years ago
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The pastorrsquos family 17

Sunday morning and I wake up to William shaking the bed trying towake me and Luke. I acted like I was asleep while Luke asked him what wasup. William said any chance I can wake him and take him in the shower withme. Luke said he had a hard night last night, so I guess we will just lethim rest up. Remember, tonight is his call on what happens. William saysthat shit could get out of hand if he wants to be mean. Luke said Mattie isa good k**, he just wants fun. I peeked out of one eye and say...

2 years ago
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Damn I love college

Damn I love college   Well I’m in my second semester of college now, its fun but some of the classes stink.    I mean, come on.   I’m majoring in science, why do I have to take a music class?   Anyways, my name is Thomas Parker, construction worker turned college boy.    This year I get the joy of taking a couple classes that any sane person wouldn’t touch with a 10 foot pole; Biology, Music appreciation (oh joy), Psychology (great now I can figure out how messed up I am in the...

First Time
3 years ago
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College life 31 the final chapter of the first se

To start my Sunday here in December, I headed down to do some laundry andhave it done before finals began here on Thursday with Wednesday being`dead day'. I was nice and threw in Kris's towels along with mine eventhough he still had a lot of laundry left. While doing laundry, I didcarry my laptop down and studied for some tests. I got a call from Dadwanting us to meet at his house for an early Christmas. I told him Tuesdaynight would be best for me. He agreed and gave me directions....

2 years ago
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Oops I must be dreaming

Ann... graces daughter...20 and hot Me...64 and semi retired... The house a 5 bedroom place 4 up stairs one down...2 1/2 bathrooms 1 up 1 1/2 down .... In the summer, it is usually pleasant not hot really and a mild wind seems to blow all the time but this year was different, call it climate change or just bad luck but this year was hot...smothering hot and humid but no rain. I'm known as Jr and being 64 well it has its advantages and drawbacks ...being a part time...

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