Chapter 1

I was so close to not seeing her at all.

It was getting pretty dark, I was driving and the fucking draw-string on the disgusting orange boardshorts I was wearing was too tight and had knotted. I had bought the ugly shorts two months ago - My relationship of eleven years had ended. And ended badly. I was feeling pretty shit about myself so I decided to take some time off work and just lose myself. Run away from my problems and become ‘Holiday Jake’. I didn’t even pack, just headed for the border. I picked up some new t-shirts and shorts on the road. Loud and fun. As far from my usual conservative dockers and button down as I could get.

Sizing is always a bit of a challenge and most of the things I found were a bit on the snug side, but that didn’t matter. I was going to swim every day. Lose weight, build a bit of muscle. Yeah right - So this is how I found myself , six weeks later, back over the boarder, ten pounds heavier, on a dark backroad leaving some beach town outside San Diego, going home two weeks early, wearing tight shorts and fucking with my draw string. I kept glancing down at the knot then up at the road. Down and back. As I looked up for the how-ever-manyth-time and I got a quick glimpse of tanned legs and blonde hair on the side of the road. A second later and I would have missed her.

Just to be clear I was in the middle of nowhere. The last thing I thought I’d see in the brake lights of the car was a young woman jogging up, wearing a big back-pack.

I wound down the passenger window to the most SoCal girl you can imagine. I think now, in retrospect, it was the pure confidence and cool that made her seem that way. It helped that she did also look like a pro surfer that also occasionally modelled. She gave a bright, sunny smile with impossibly white teeth and impossibly blue eyes. “Any chance of a ride?”.

“Um, sure.” My tee-shirt and shorts suddenly seemed even more ill fitting. I popped the trunk, jumped up and ran around to help her with her bag.

Ten minutes later I was driving down a dark road with a beautiful young lady who had already adjusted the air, radio and the seat and was now just staring at me curiously. It would have been annoying, but there was just something about her that made it charming instead. And not because she was pretty. In fact, generally it would add to my annoyance. I would think this person was being entitled because of their good looks. With her it wasn’t like that.

I had also found out her name was Kaylee and told her mine was Jake, apart from that we hadn't talked much. And now she just watched me. Curiously. Finally she broke the silence with “Soooo, what’s your story?”. It took me by surprise, “Who, what, oh, um. Nothing really. What do you mean?” I sounded like I had the brain of a four year old.

“Like who are you? Wife or husband? Kids? Where are you from? What do you do?” She gave me a grin. “Or what are you doing peeling out of town in the middle of the night?”. I shrugged. “Just decided to end my holiday early.”
“Ah, you are on holiday, I see. And when were you due back?”
As not a big talker and a little shy I was finding this very awkward, but her comfortable tone compelled me to keep answering. “I, um, guess I’m due back in about two weeks.”
“What?! Why would you want to cut your holiday short by two weeks?”
I don’t know what was wrong with me. I’m no great judge of such things, but I thought I was probably about fifteen years older than her, but I was the one mumbling like a teenager. “Um, I guess I just wasn't having that much fun.”

She looked at me then for a long, uncomfortable moment. Her eyes were sympathetic. It felt like she understood a whole lot more than I was saying. Finally she said, “Tell me from the start.”

And I did. I must have sounded so pathetic. I told her about the one relationship I had been in. Seventeen years. She was way out of league so I did my best to make up the gap. I worked hard, earned good money, but after the first couple years she was distant. I think she wanted me to be better than I was. Better looking, more charismatic, fitter. I think the only place I performed for her was financially. I’m pretty sure she had affairs.
At the point I told her that she gently put her hand on my arm and I looked at her. “You ‘think’ she had affairs?” I responded with another shrug. “I Guess I know. I mean I do know. I just spent so much time trying to fool myself. I, um, I spose I couldn’t have coped otherwise. But now that I think about it, I probably did more cover for her than she did. Particularly in my own head.”
“Anyway, we went on living our together but separate lives when, about three months ago, she ended it. I think she met someone.”

She squeezed my arm in empathy then patted it. “Well, going home has just become unacceptable. You have two more weeks to make this a holiday to remember. Oh, and forget too,” She drummed her hands on the dashboard. “Here is the plan. The next motel we see, we stop at for the night. On me.” I started to protest, but she cut me off. “No way man, you just told me how you’ve been taken advantage of. Anyway, get somewhere to stay tonight, then tomorrow morning we spend some time cruising around, maybe head a little further north, until we find somewhere I approve of. We’ll find you some accommodation, then you can drop me at the nearest greyhound station. I’ll get out of your hair and let you get on with having an awesome holiday!”

It was another half an hour before we found somewhere with vacancy. She ran inside and came back with a single key. “Sorry, last one. It’s a twin, so we don’t have to share a bed or anything.” I later found out this was a total lie. She just didn't have enough money for two rooms. She was willing to give up her last dime to make a stranger feel better.

The room was clean and modern and as promised there were two single beds. As we walked in she ran and threw herself on one of the beds and stretched out. She was in a short pair of cut-offs and a blue tee-that now rode up to reveal a taught and muscled belly. I found myself staring and quickly looked away. The last thing this beautiful young lady wanted was some gross, fat, middle aged guy staring at her.

She seemed not to have noticed because when I looked back she had rolled over onto her side and was looking at me with her bright, sunny smile. “You have first shower, you’ve been doing all the driving after all.”

I grabbed my bag and retreated to the bathroom. I showered quickly and got dressed in a fresh pair of ill fitting shorts and shirt. I was almost sick with how self conscious I felt, then would berate myself for even thinking Kaylee would care enough to think I was gross, which would not make me feel even worse. Man, I certainly had low self esteem.

I packed up my stuff and cleaned up, making sure everything was at least as good as I found it. Kaylee was lying on her stomach watching TV.
“All yours” I chimed as I walked out. “Great," she said as jumped to her feet and grabbed her bag. “I can’t wait to wash the road off” and she disappeared into the bathroom.

She was in there for quite a while. I would occasionally hear snippets of singing, but eventually the shower stopped and after a while the door opened. I looked up and Kaylee was standing there in a pair of blue cotton underpants with one arm held across both boobs. She saw me look away and by how hot my face felt I knew I had turned brick red. She laughed, not unkindly, and said, “Don’t be such a prude. Do you have a tee-shirt I can borrow?”

“Ah, um, sure” I grabbed my bag and started to rummage through it. “I have a new one somewhere that I haven’t worn. It, um, didn’t fit.” As I tried to get to the bottom of the bag, she wandered over and grabbed a folded shirt from on top “That's okay, this one will do”. She held it up to her face and sniffed it “I like how you smell”. As she pulled it over her head I got a glimpse of two perfect, and surprisingly large breasts.

After that we both settled into our respective beds, turned out the lights and went to sleep. Well, in theory. I laid there awake. My brain oscillating between attraction for this cool, confident, beautiful girls and self loathing. I must have laid there an hour before I heard “Psst. Are you still awake?”
I rolled onto my side to face her, “Yeah”. Her lamp flared on. In the soft warm light her hair looked golden. She was incredible. “I can’t stop thinking about how she was with you.”
“I guess we were just different. I think I was too weak with her and it really eroded my sense of self. But, I don’t think that was good for her either. Just oil and water that stayed together too long. Maybe just forced a bit at the start then got trapped, both of afraid we couldn’t cope without the other. It ended in her feeling resentful and me with very low self esteem. The two fit well together in a sad kind of way.”

We were quiet for a while, then I said, “anyway, that's in the past. Tell me about you. How did you end up hitching on a dark road late at night?”

“Ha, my story is for another time.” We both fell silent again, facing each other. Her eyes bright in the lamplight. Slowly a devilish grin crossed her face. “I know what will help us sleep” She kicked her covers off, “You show me what you used to do with,” she yanked her shirt off, “your wife and I can give pointers” She slid her underpants off revealing a small patch of dark pubic hair. “If you need any, that is.”

I was shocked. I just sat there on the side of my bed. “Come on.” She said, “We would be doing each other a favor. There’s nothing like a quickie to help get to sleep. Now show me what you would do.”

I found my words, “well, she didn’t really…”, but Kaylee cut me off. “I said show me not tell me!”
“But…” she cut me off again. “Show!”

It was her radiant smile that did it. There was no malice in it, she may have been doing this out of sympathy, but I couldn’t even see that. I jumped up and ran into the bathroom, reemerging a second later with the complimentary tube of moisturizer.

“Oh, kinky” she smiled as I walked over. I sat down at the bottom of the bed, next to her feet. “I don’t think you’re going to be able to do much from down there. And are a little overdressed.”

“You said like I used to do with my wife.” I squeezed some moisturizer into my hand, rubbed them together a moment then gently took her foot in my palms and began kneading. Starting with her feet, I worked my way up her tanned legs. The little moans of pleasure she gave and I massaged her were like breaths of air across my naked brain. It tingled right down my spine. The thought that I was able to bring any kind of pleasure to this goddess was so unbelievable arousing. I could feel myself stiffening inch by inch. Her skin was smooth and blemish free. I worked her calves, then asked her to turn over as I reached her well muscled thighs and butt. She was stunning. It was a difficult balance to find the right pressure to release the muscles but not dig in and pinch, but I could feel her well muscled body give way under my kneading palms and and thumbs.

I worked my way to her shoulders, working every knot of tension out, running my hands down her arms to her hands. As I leaned forward I did the most impulsive thing I have ever done in my life. I kissed her neck. I know it’s not very impulsive given the circumstance, but for me it was huge. And led to everything that followed. She gave a soft “Mmmm.” So I continued.

From her neck I started working my way down the curve of her back. She let out a moan at that point that almost broke me. I could feel myself throbbing inside my shorts, but more than that, it seemed to pulsate right through my body. I continued kissing down the back of her thigh, then gently turned her over and continued up her inner thigh. Again she moaned. I could smell her warmth and her spice. As I started with my tongue she moaned “Holy fuck”. She reached down and caressed my hair. Her breathing became slower deeper, with an occasional hitch as I continued, slowly increasing speed, introducing a finger, just to play in the shallows. I knew I was good at this bit and took pride in it. I could sense her reaching climax and knew this is where it would end, as it often did with my wife. But, as Kaylee’s panting seemed to reach a crescendo, she gently closed her legs and still panting said, “Come on” and patted the bed next I hesitated and she looked down at me. “Oh, shit, you’re still dressed? Get those off and get up here.”

I did as she said. I took off my pants and undies. As I went to lie down next to her she said. “Shirt too.” I slid it over my head and lied down. She had watched my eyes the whole time, smiling warmly. “Alright” she said as she slid a thigh across my stomach and hopped up to straddle me. It wasn’t until her bum was over my pelvis that her eyes opened very wide. She lifted her bum up and peered down over my gut between us to my crotch. “Holy fuck!”

She repositioned herself. I was physically pulsing, throbbing up and down. I didn’t quite know what was going on but I was extremely grateful for how kind she was being. As she genuinely seemed to be turned on. We finally met and she began to ease herself down onto me. Her giant blue eyes were huge and a pink flush had crept into her cheeks.

“Now I see why you spent so long preheating the oven.” she said as she slowly moved down my shaft. She didn’t quite reach my pelvis before she started to move back up. She pressed her forehead against mine as she slid up and down, slowly finding her rhythm.

Her breathing became deeper and she rode. She kissed my neck and my face. She reached a steady rhythm I hoped would never end, but her breathing became a pant and she stared into my eyes. I knew she was close. I grabbed her waist and rolled her over. Her eyes widened and she let out a deep, involuntary moan. I gave one deep thrust and her back arched, the second she let out another deep moan. I could feel the pressure building and on the third we both climaxed.

Afterwards we laid side by side in the narrow bed. Kaylee looked up at me. “Well I feel like I just had the best massage of my life followed by the biggest orgasm of my life so I don't really have any pointers”. She put her arm around my fat stomach. I gently took her hand. “Please don’t. I’m pretty self conscious of my stomach and, well, how fat I am in general.” She wiggled her hand free and patted my belly. “Dude, without this extra padding you would have been too big for me. If you lost it I’d have to put on extra padding.” Her blue eyes found mine. She gave one of her dazzling, toothy grins, both of us aware of the implication that this was not going to be a one time thing.

* Thanks for reading. I’m aware there wasn’t much in the way of weight gain in this one (maybe a little foreboding at the end), but just wait for chapter 2. If you liked it please let me know*