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It has been awhile but I am back with an update. In this story, I will recount my two most recent experiences, the second one happened earlier today and I am still a bit unnerved by it. For those that don’t know, I am a middle aged dude (49), married with a family. Over the past couple of years, I have developed a secret, submissive sissy fetish. My first real encounter was about a year ago and that, along with my other activities, have been detailed in these stories. I have occasionally updated my profile page with some new pics and short vids to show that I am real. Anyway, I hope you enjoy my story.

The first experience I want to recount took place in early October. As I have mentioned previously, I get to travel to Miami for work on a pretty regular basis. This has afforded me an opportunity to get some extracurricular playtime. I still try to utilize Reddit (Floridar4r) but the subreddit is not nearly as active as in Chicago. So, I also use Doublelist to find hook-up partners. I have a couple of listings that I can post when I am down there. My standard one is that I am a submissive, married dude, staying near the airport and looking to serve. I always forget to edit this listing as I end up with a bunch of responses of which airport? Fyi – the Miami airport. I travelled down on a Tuesday morning and put my post up just as I landed.

As usual, I got a mix of messages from various flakes but I also got a few from some real dudes looking to hook-up. As I was going through the messages, I came across one that was very familiar. As I checked his e-mail message, sure enough, it was the dude from my story “A Doubleheader with Doublelist.” This is a black dude, about 6’3” and 225 pounds. I would guess that he is a couple of years older than me and he was pretty cool during the last go around. I responded to his message and reminded him that we had hooked-up a few months ago. He was happy to come over again. Just like last time, he wanted me naked on the bed with the hotel door left ajar. Laying there for him to come-up really heightened the experience as you just don’t know who might walk in. I laid there, naked, waiting in anticipation and then I heard the door open and then shut completely. Laying in the bed, you cannot see the door as the wall of the bathroom blocks the view. My breath stopped as I waited and a moment later he appeared from the doorway. It was a little unnerving since we had hooked up before. While I still don’t know his name, the familiarity made it seem a little weird. Does that make sense?

Anyway, he came into the room, saw me, smiled and immediately started undressing. He was only wearing a t-shirt, shorts, and flip flops. After undressing, he laid down next to me, smiled and said “Good to see you again” as he began to caress my chest and legs. My hand immediately went down to his groin and started fondling his hardening cock. I remembered that he wasn’t especially large, probably around six inches but his dick was really curved upward. As he continued to harden, I started nibbling my way down from his chest to his nether region. I started kissing his dick and balls as I continued to gently caress the shaft. I then crawled between his legs and took his dick into my mouth. Again, not being overly long, he would not be hard to deepthroat. Unfortunately, the curve of his erection made it a little challenging as his dick was pointing in the opposite direction of my throat. I was able to adjust my position to take him all the way in. He groaned in appreciation as he slapped and rubbed my ass. After a few minutes of cock sucking, he pushed my head further down. Knowing what he wanted, I adjusted my position and lowered my head below his balls as he lifted his ass up. I stuck my tongue out and started licking his asshole and he groaned loudly. After a little bit of licking, he grabbed the back of my head and shoved my mouth against his hole. I started really going to town on his back door, kissing, slobbering, licking, and slurping his ass. While this was happening, I continued to stroke his cock.

After a few minutes of ass worship, he pulled my up to him and asked me to start sucking on his nipple. I did so. He then asked me to stick a couple of fingers into his ass. I complied. While I sucked on his nipple and finger fucked him, he started stroking his cock. He then started talking dirty to me. “Do you like eating my ass? How did it taste? Keep sucking my nipple! Oh yes! I am going to come!” With that, he shot his load all over his stomach. I can’t lie, I was disappointed. This is the second time I had been with this dude and neither time did I get a chance to swallow his load. After he came, I removed my fingers from his ass and he quickly got up and went into the bathroom to clean-up. I continued to lay in bed and we traded small talk as I heard the water running from the sink. A few moments later, he reappeared and got dressed. He thanked me and said his goodbyes and left. While the experience was pretty hot, I was left disappointed but before I could really start thinking about it, I was in for one more bit of awkwardness. He forgot his sunglasses in my room. I sent him an e-mail and he also sent me one. A few minutes later, he was back at my door and I opened and handed him his sunglasses. It was an odd feeling. I don’t know your name but my fingers were just inside your ass, here’s your sunglasses and have a good night…

I did not have any additional encounters on that trip nor did I want any. I was left feeling confused about what I was doing. Was this what I really wanted? Was this still a turn-on? Getting back to Chicago, I would think about this periodically but I was not able to come to any conclusions as both work and family got really busy. Over the next month, my libido really dropped as I had to concentrate on work as well as on things at home. During that month, I really started thinking about ditching this “hobby.” While sex remains a non-starter with my wife, we have become much closer emotionally over the past several months and I was really feeling guilty about my prior activities and thought many times about giving it up. However, as is usually the case, it wasn’t long before I was going back down the rabbit hole. The first thing I did as I was feeling a little randy was to purchase a few new items from Amazon. First, I bought a new wig. The style is very short, kind of pixie. I knew I wouldn’t have to be worried about getting hair in my mouth anymore. I also purchased another pair of thong panties as the previous pair I had purchased were just too big. Lastly, I also purchased thigh high stockings. After getting a chance to try on my new things, my desire to suck a cock was as strong as ever and I reached out to my BBC, Paul.

Paul and I would trade messages, periodically. They would be short notes, usually with subreddit recommendations but we would also talk about getting together. Again, being as busy as I was, I was never able to suggest a day. Well, yesterday afternoon I found out that my schedule today had suddenly opened up. I was supposed to have a couple of meetings with some customers from out of town but their travel plans changed and my calendar suddenly was wide open. I texted Paul to see if he wanted to get together today and he immediately jumped at the chance. My cock started hardening, thinking that someone finds me desirable as a submissive sissy. I was able to get my gurly stuff from the hiding place in my basement into my trunk without anyone noticing and I headed over to his place this morning.

Despite us hooking up several times, we still don’t really know each other. We communicate by Kik and I need to message him when I get to his apartment building. He then comes down and escorts me up. I arrived today and, as usual, he let me lock myself into his bathroom to transform into a sissy. I undressed out of my suit, hung up and/or folded my clothes as neatly as I could after I got naked and I proceeded to get dressed. I started by inserting my butt plug which really felt good in my ass. I then put on my Calvin Klein thong panties and bra. I then put on my thigh highs and marveled at my legs for a moment. Damn! I have sexy legs. I just wish I could shave without arousing any suspicions at home. I then put on a dress, a simple blue cotton dress with long sleeves (again to hide the hair). I then put on my new wig. Wow, it was really cute! I brushed it out a little bit but it really framed my head/face nicely. Feeling really good, I started putting on make-up. I can still count on one hand how many times I have done make-up but I was able to do a decent job in very short order. A little primer, followed by a light layer of foundation really made me look different. I added a little blush and then applied some mascara. Oops! Still learning with the mascara as I got some underneath my eye and on my nose. I cleaned that up, finished applying the mascara and I was really liking how I was looking. Next up was eye shadow. My experience with eye shadow has been a disaster as I have not been able to blend colors. I just said, fuck it, picked a color that matched my lipstick and applied it to my eyelids. After a couple of minutes I stood back and looked at myself in the mirror. Not bad! I was no supermodel but I thought I looked pretty sexy. Mental note, keep it simple with the eye shadow. I then applied some lipstick and to finish my look off, I gave myself a couple of squirts of perfume that I had picked up at the d**g store. I put on my high heels and walked out of the bathroom.

Sitting naked on his couch, Paul’s eyes widened when he saw me and a big smile grew on his face. “Wow!” “Do you like?” I asked. “You bet, I love your new wig” he responded. I then crawled down between his legs and started caressing his cock. It was already rock hard. God, it felt so good in my hands. I leaned down and kissed the tip. He groaned, “It has been so long, I thought you had given this up.” “No chance” I responded as I opened my lips to let his massive dick into my mouth. Paul’s cock his huge, well over eight inches and incredibly girthy. I have a hard time keeping my teeth off of his shaft when I deepthroat him. I continued to suck his dick while I caressed his balls in one hand and stroked his thigh with the other. Slowly, I took more and more into my mouth until I had the entire massive dick into my throat. Wow, I had forgotten how good that felt. His cock smelled great, felt great, and tasted great. I was back in sissy heaven.

Once I got his cock drenched with my spit, I would occasionally drop down and suck his balls as I continued to stroke his shaft. I would also stroke him with just the head of his dick in my mouth. I would then go back and deepthroat him again. After going through this routine a couple of times, he stood up, grabbed the back of my head and started throat fucking me. I was gagging as I tried to keep my teeth off of his mammoth shaft. I really like having his cock forced into my throat, what a feeling of submission! Paul then sat back down and I was ready to really go to town as he would usually like me to start stroking and sucking really fast. Today, he told me to just gently kiss and suck his cock. Mmmmm, I started swooning as I slowly nibbled, licked, suckled and kissed his beautiful piece of meat. He whispered “your mouth is incredible, this is so much better than edging.” I just looked up into his eyes and smiled.

This was going great, I couldn’t wait to have him shoot into my mouth but all of a sudden, things took a turn. Paul whispered to me “do you think about getting fucked?” “All the time” I huskily responded as I continued to worship him. “Do you want me to fuck you now?” Wait, what? Fuck me, here? Now? I don’t want to be fucked, I wanted to taste his cum. So, how do I respond? “If you want to, I am willing to give it a try.” What the fuck am I thinking??? Paul got up and pulled me onto the couch. I was on all fours with my knees on the couch and my forearms on the back of the couch with my ass wriggling. He went to get some lube and came back and started squirting lube on his dick as he pulled down my panties. “What is this? A butt plug?” I blushed. He pulled out the plug and squirted some lube onto my ass. I kept thinking that I can’t believe I am doing this. I shouldn’t be doing this, right? All the time, my ass was shaking back in forth in anticipation of his huge cock. A moment later, I felt the tip against my hole. My god, how is this going to feel. I have been playing with some larger butt plugs but it has been a few weeks and I am pretty patient about getting them in. Paul was less than patient as he pushed his huge cock against my hole. Please don’t hurt me, I silently prayed. He continued to push and then…he was inside me! My god, he is big! I groaned out loud. Paul asked “Are you alright?” I nodded and he started to pull back out and push in again. Hmmmm, it felt so good. It only got a bit uncomfortable when he pushed all the way in. I don’t think I was in the best position to accommodate his full length but I didn’t say anything as he started to fuck me. I squeezed one of my nipples as I pushed back against him each time he would thrust. Jeez, here I am dressed as a sissy, in a wig, make-up, and dress, getting fucked by a bbc on his couch. Unbelievable! It didn’t take him long. “I am going to cum, okay?” What do you mean, okay? “Is it alright if I come inside you?” Clearly, not thinking, I responded “Please give it to me!” He then grunted and shot his load inside my ass. I was just bred. What did I think about that? Well, my cock is rock hard as I type this so I guess I don’t have to really ask myself.

It was a quick come down as Paul went into the bathroom to clean-up and offered me the use of his shower. I thanked him as he gave me a towel and wash cloth. I went into the bathroom, sat on the toilet to allow anything left to leak out. I then removed my make-up, took a quick shower, and got dressed. I got out of the bathroom and told Paul that I took myself by surprise that I let him cum inside me. Did I need to have any health concerns? Paul assured me that he was clean and that he would not put anyone in a position to risk their well being. I hope so, I thought, because I would love to do this again. Until next time…

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Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry. Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...

3 years ago
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The Ostler and the Lady Chapter Four Thoroughbred

Seeing the twin horse-driven polished box-like carriage heading up the main drive, Jack Wetherly knew exactly what it contained. His heart gave a heave, knowing that this was his new challenge, arriving with two long-coated men sitting upfront. Excitedly, he called to Alf, his boss and mentor.Alf came hobbling out of the stable. Jack couldn’t help thinking how much slower on his feet the older man had become. He was due to retire soon and that was why Jack had been appointed. But this new...

Historical
2 years ago
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Lunchtime Munchtime

As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...

1 year ago
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A Reply to Black Bred

Dear Noel, Thank you so much for your letter. Emma and I really enjoyed it and we were so glad to hear your own wife Sandra has recently had ‘good news’ of her own. We both found your story 'Black Bred' a real turn on and it inspired us to relate our own recent adventure. From my writing you might have already guessed that Emma is pregnant too. She is expecting what will be her first next month and remains thrilled and excited by what is to come. You will of course, be delighted to know that...

Interracial
2 years ago
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Wartime

Elizabeth Fleming told me some of this story in the years before she died, aged eighty, in 2010. The more graphic scenes are mine but the emotions and surrounding history are hers. She was my Great Aunt, great in so many ways for she was the third family member I ever revealed my sexuality to, the first two being my parents. I had known since girlhood that she shared a cottage in Hampshire with her friend, Portia, but had never known their relationship was more than sisterly. When I told her...

Lesbian
2 years ago
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Daytime friends nightime lovers

She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½ feet. Dark red… it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the crystals were so thick it turned everything pastel. Breaking it apart just enough to smoke easy, she arranged the weed in...

3 years ago
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Daytime friends nightime lovers

Introduction: While a few details have been tweaked, this story is as close as I can remember it Prologue She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½, feet. Dark red&hellip, it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the...

4 years ago
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Sandy and RandyChapter 2 Daytime Funtime

After the close call and excitement, in more ways than one, of that first night together, Sandy decided they better cool it a bit so Mom wouldn’t get suspicious. Mom also went back on day shift, 8am – 8pm, so bedtime was less private, but days were not such a problem. Randy tried to act normal around Mom and of course, around Sandy, but he did have some issues like being quieter and more protective. Mom just thought he was getting older and closer to starting into puberty, especially now...

3 years ago
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FaceTime with Ann Next Door

I never FaceTime. I'm not a adolescent girl. I don't need to see your face when a simple text will do. Call me an old bastard, get-off-my-lawn type, but that's the way it is. (By the way, I'm not that old).So when that mechanical beeping emanates from my phone that someone wants to FaceTime me, it's definitely out of the ordinary. Especially when it's 10:30 on a Tuesday night. I got to my phone and it said "Ann FaceTime video."Well, this was different. Ann Next Door and I been fooling around on...

1 year ago
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Halftime Stranger

It was a warm October night and I was at a college football game with a few buddies. Throughout the first half of the game, I looked to my right and there was this hot sexy bald guy 3 sections to my right. He had huge arms and was wearing a black wife-beater and jeans. We kept looking at each other and at each time, he would show that bright smile of his.At halftime, I went to the restroom and used one of the stalls, luckily I was the only one in the bathroom. As I opened the stall, he was...

2 years ago
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Summertime In Colorado

Summertime In Colorado I absolutely love summertime. The hotter it is the less the girls wear. Instead of long jeans they wear short shorts. Instead of full blouses they wear skimpy tops. Coats are strictly out of the question too. Bikinis are popular even if it is just the top half with a micro mini skirt. Like I said I absolutely love summertime. Girls of all ages are wonderful to look at. Touching them might be a different story but looking at them is still legal. The problem...

3 years ago
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Summertime Blues

Summertime Blues Author's Note: This is an old story of mine which I self-edited using the great suggestions I been receiving. I will go back and edit it more. I want to see how well I could implement the suggestions which I got. Also, I want to give a thanks to all the people who had help me in my writing. It was a bright sunny Saturday afternoon in July yet it was raining in Joe's mind. This was for Joe was having a run of the mill bad day so he headed to the bar for a drink. He...

2 years ago
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FaceTime surprise

I have a new job working away and I bought an iPad to keep in touch with the wife, it’s great seeing her when away I miss her so much so it’s great when I’m bored in my room. Jane and I for years have spoke about sharing? But she never comes through, it must be 4 years now we have had the same conversation about it and it’s always the same answer maybe! Jane is great in the sack she knows how to please, I keep telling her she needs to give it out cos it’s going to waste on me as I only last...

4 years ago
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Showtime for Teri

Showtime for Teri By Teri Franken Chapter 1 My name is Teri and I am 28 years old. I have been a closet sissy for as long as I can remember. My parents knew that I was not your typical child and they let me live how I wanted to and did not judge me, they just loved me unconditionally. I grew up loving everything that a little boy typically doesn't like, such as dresses and dolls. My parents were concerned that I would be a target for bullies, so I was home schooled, took my GED...

3 years ago
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Eagle in the Sunset 2019Chapter 29 Summertime for Us All

October 17th, 1995, 7:30 AM PT, Metro Plaza Hotel, Los Angeles, CA Miriam had been tossing and turning all night; she spent time just sitting in the chair in the corner of the room to try and let Baruch sleep. She was so upset she was oblivious to the fact that Baruch couldn’t sleep either, which was not in her nature. She was usually fully aware of what was going on with her husband. They thought together almost telepathically, and yesterday had been one of the first times in decades when...

3 years ago
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Timeless Beauty

TIMELESS BEAUTY BY PAUL G. JUTRAS Sam walked in the dorm house, looked at the lock and then in the dorm mistress's room. The plus size woman was dress in a black blouse and flats, black with white palm tree design jacket and skirt with dark brown nylons. She new there was only a half hour before she made her rounds and called lights out. Upstairs, roommates Chris and Alex waited on their beds. Like their friend Sam, both guys were petite and lovely looking. Being transsexuals who...

2 years ago
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Younger Than Springtime

The door was open. I had no reason to have it closed. We were all in this together. So I was sitting in the large chair as my nurse prepared to access my port to begin the first liter of Cisplatin. The cancer center had been busy today and I glanced out the doorway as several people passed by. Then I noticed a woman pausing as one of the nurses escorted her somewhere.It was Katherine. I recognized her at once even though it had been so many years ago. Then I heard her laugh as her companion...

College Sex
3 years ago
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Master of All Timelines

Your name is Edward Richardson. You're 20 and you've been fascinated by history ever since you're 11. You're also good at making inventions as well. As you're growing up, you usually found that at various points in history of each country, things always turned ugly at many points. And you wanted to change that. You decided to use your intelligence you create the device called the T.O.S, abbreviated for Timeline Opener and Stopper, that can make you travel back in time and alter the histories...

Mind Control
3 years ago
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First Time Sex With My Longtime Bestie

Hi everyone Akshay here, age 23 from Chennai. I’m a reader of ISS for the past 5 years, and it’s high time I shared my experience. This happened a couple of months back. It was with my longtime bestie. Her name is Vaishali. We know each other for around 6 years, starting from our college days. She lives half an hour away from my place. I’m pretty familiar with her parents. We got to know each other from our college days as we were from the same department. She had a sexy shape, which gave me a...

2 years ago
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I was a wartime TV for the US Army

‘I was a Wartime Transvestite for Uncle Sam!               TJ Ryder                                            Chapter 1           Reform School Romance!     I couldn’t believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II.    I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another old geezer in an assisted care center who if he ever had...

4 years ago
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Wartime France

The funeral was a gloomy affair as funerals go. I am somewhat irreverent and remember clearly my twin brother and I giggling all through my Uncle’s funeral because his widow had the price ticket still dangling from the back of her hat. John and I shared a sense of mischief and humour. At our Grandfather’s funeral, we’d been unable to look at each other during the hymn ‘Praise my soul the king of heaven,’ because John had written an alternative verse that was utterly filthy and we both knew what...

Lesbian
2 years ago
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Wartime Passion

A few years ago, my wife was having a midlife crisis while I was away serving in Iraq. She was both lonely and horny. She had been without me for nearly 8 months and I still had four more months to go on my tour of duty. Char is an attractive 40 year old woman, 5'8" tall with blonde hair and green eyes. She keeps herself in great shape and still has a body to prove it, 36-30-36. Our sex life is absolutely wonderful when I am there, and I would not change a thing. She is a Hottie and we are...

1 year ago
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I was a wartime TV for the US Army

  'I was a Wartime Transvestite for Uncle Sam!              TJ Ryder                                          Chapter 1          Reform School Romance!    I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being hisfavorite grand nephew was an old diary from World War II.   I mean I thought we got along pretty darn good, and its not like he had any money or anything, just another oldgeezer in an assisted care center who if he ever had anythinghad...

Crossdressing
4 years ago
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Summertime Fun0

Summertime Fun After my divorce I got my daughter every other weekend and for the entire summer. Now that she was fourteen and developing quite nicely I was enjoying her even more. I also indulged her desire for sexy revealing clothing, since her mother wouldn’t. Holly was pleased that I had purchased a summer home alone the beach. We used to go to the ocean when we were still a family. Another thing that I did to piss my wife off after the divorce. It was a very nice place and I...

1 year ago
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Summertime Chapter One

Summertime: Chapter 1 By Tommie Summertime, and the living was easy. I had just graduated college and I was home for the summer. My parents were on vacation and I had the house to myself. I had settled into a relaxed routine. Up late, lazy breakfast, a little bit of work on the computer to keep my hand in for the programmer's job I was starting in the fall. Then, as often as not, a lazy afternoon reading in the back yard before soccer training in the evening. Soccer had paid my...

2 years ago
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TimeLine chapter 1

Like Billy Pilgrim, John and Amy have become unstuck in time. Unlike Billy Pilgrim, theirs is a fate more akin to eternal recurrence. Fate, for sure, had intended more for them. The timeline was diverted and the two were paying the price: Amy for her stubborn obstinance; John for his arrogance. For her stubborn behavior, Amy was dealt a hand similar to that of Sisyphus. She was placed upon life's treadmill: forever struggling to make ends meet; forever struggling to find her way...

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