Cycling Weekends with Sis

This is the second story I published on Literotica. It dropped on 8/31/13 and immediately started getting comments. Back then, Literotica published comments as soon as they were submitted. I was stunned at how many comments the story got, all of which were very positive. The story quickly reached 15 comments, far more than what my first story "Heather and Michael", and new comments kept trickling in. After the success of this story, I began to think I might be able to get good at writing incest stories.

I took this and all my other stories down in January 2023. I'm republishing it now as it was originally published with the exception of this intro.

"Time to get ready, Julie." The bike rally was due to start in ten minutes, so my sister and I needed to get into position. My friends Ben, Patrick, Connor and Evan also got on their bikes. There were twelve loud pops as we snapped our cycling shoes into our pedals.

We rolled over to the pack for the forty-mile ride and I placed us at the back. It was a lovely day for a bike ride: a pretty blue sky with a few clouds, a mild breeze, a little on the cool side, but it wouldn't be too hot later.

"Are you sure you want to do this?" I asked. "You've never ridden anything close to this far."

When we had signed up for the rally, there was to be a twenty-four mile ride. I had thought that would be a challenging but doable ride for my sister. Yesterday morning, I got an email from the rally organizers that emergency roadwork had forced the cancellation of that distance. The choices were ten, forty or sixty-six miles.

Julie looked at the pack behind us. The people lined up for the ten-mile ride were mostly families.

"Josh, I'm not doing the kiddie ride again."

A year ago, I had convinced Julie to go to her first bike rally and she had hated it. She had weighed 165, which was a lot of weight for her 5'1" frame. Her bike had been an entry-level bike. Her clothing and gear had marked her as a newbie, more likely to quit than to ride another bike rally. My friends had each given her a once-over and then ignored her. She had felt pathetic when she hadn't been able to keep up with twelve-year-olds. Now, Julie weighed 110 with toned, firm legs. She had a much nicer bike. Her clothing was similar to everyone else's in the pack. She looked like she belonged.

She didn't blend in in one way - she was a woman. I looked ahead of us and could make out three other woman in the large group; biking was very much a man's sport. With light blue eyes and blond hair that came down to a little beyond her collar, Julie looked like what I would imagine Tinker Bell would look if she were human and let her hair down. Julie again looked like she had looked when she had been a cheerleader in high school, a thin little thing with big tits, a short beanpole with two cantaloupes.

"It's okay. I'll stick with you the whole time and we'll take lots of breaks. Don't push yourself too hard. On a scale of one to ten where one is no exertion and ten is an all-out sprint, I want you to ride at four or five."

A trumpeter played the national anthem and then a guy with a bullhorn sent out the riders for the sixty-six mile ride. Our pack moved up to the start line. After giving the first pack a five-minute head start, the guy with the bullhorn sent us out.

* * * *

Patrick and Evan stayed with us until they were warmed up, then they took off. Ben and Connor rode with us to the first rest stop, which was at twelve miles. Julie and I averaged 13.9 miles per hour, which I thought was a good pace for her. If Julie wasn't with us, Ben, Connor and I would have averaged over twenty miles per hour.

"How are you doing, Julie?"

"Okay. A little sore, but no big deal. I like the new bike. I'm going to make all forty miles."

Her attitude had changed so much since she started training with me. Over a year ago, she had come depressed to my apartment, feeling fat and ugly. Her weight had undermined her self-confidence. Without self-confidence, she hadn't been assertive at work and instead had been shy and passive. Co-workers had regularly dumped grunt work on her. She had been hating work and life in general. Now, she was confident again; she was once again outgoing and finding the joy in life.

As I tended to our bikes and refilled the bottles on them, Julie and my friends hit the snack table. After I was done, I walked over. The snack table had bananas cut in two with their peels on. There were also lots of different types of homemade cookies. I grabbed a banana and a yummy-looking lemon bar. Julie and my friends had gotten similar refreshments and were chatting a little ways from the snack table. I joined them.

Ben and Connor towered over Julie and me. I was short and thin like Julie, standing 5'6" with light brown hair and brown eyes. Ben and Connor were both at least 6'3". They could kick my ass on flat sections, but I was faster if there were big climbs.

"Your bike is a lot nicer than one you had a year ago," said Ben to Julie. "How much did it set you back?"

Not a topic I wanted brought up.

"I didn't buy it. Josh bought it for me a few days ago."

"How much did it set you back, Josh? Twelve hundred? Fifteen hundred?" asked Ben.

"It wasn't too bad. You guys ready to get going?"

"Joshua, could I speak to you for a moment?" asked Julie. She grabbed my elbow and steered me away from my friends.

"You spent how much on my bike?" she asked in an angry tone.

"Thirteen hundred."

"You shouldn't have spent so much money on me. My old bike was fine. How much did you spend on it?" I had bought her a used, entry-level bike a year ago when I convinced her to start training with me.

"Two fifty."

"Son of a bitch. I had no idea. Why didn't you tell me bikes were so expensive?"

I shrugged.

"I'm serious. Can we take this new bike back?"

"I'm thinking of taking it back, but so I can trade it up for an $1800 bike. I hadn't anticipated you'd be willing to ride so far so soon."

Julie crossed her arms. "That's bullshit, Josh. No way can I pay you back for an $1800 bike." Julie's job at a mortgage processor didn't pay well and she hadn't made much of a dent into her student loans the two years she had been working.

I crossed my arms too. "I have plenty of money, Julie." I was an engineer at an engineering firm. I had gotten good raises all four years there and made good money. In the next year or two, I would probably be made a manager. I spent a lot on biking, but not much on anything else. My student loans were all paid off. "There's nothing I could spend my money on which would bring me more pleasure."

We stared at each other. Eventually, she looked away.

She looked back at me and asked, "How much did your bike cost?"

"Five grand."

"That's crazy."

"Connor's crankshaft - the part the pedals screw into - his crankshaft alone cost three grand."

Julie shook her head. "That's nuts. How can so many people afford bikes that cost so much? They look like bikes you can buy at Walmart for a hundred." She paused for a bit. "My new bike is a lot better than my old bike. Thanks for buying it for me. Would an $1800 bike be that much better than this one?"

"Over one mile, it'd be a little better. Over forty miles, it'd be tremendously better."

"Okay." She went back to my friends and resumed talking to them.

We had had a similar confrontation a year ago. When she had come to me depressed, I had suggested she start training with me. Dieting and going to the gym hadn't worked out for her and she hadn't been able to keep up either. I had been tired of her complaining about her weight. Her first excuse for not training with me had been that she wouldn't be able to keep with me. I was an avid biker and regularly did hundred mile rides. I had told her I would push her to ride as fast as she could, but would go no faster. She had countered that she didn't have money for a bike. I had said I would buy her a cheap one. We had gone back and forth until she finally realized that I wasn't going to take no for an answer.

* * * *

Three miles beyond the first rest stop, we came to a steep incline. I knew Julie couldn't do such a hard climb without exhausting herself.

"Pull over, Julie. We're going to walk the bikes up the hill."

I turned to my two friends. "You guys go on. We'll meet you at the finish line."

"No, it's-" said Ben.

"Get out of here, guys," I said firmly.

They shrugged and took off. When I had been in high school, I could never have told guys like my friends to do anything. They would have laughed at me. In high school, everyone had called me "Little Joshie". I had hated it. HATED IT. High school had been hell for me. With my shirt off and long pants on, I looked like a 98-pound weakling. Everything below my waist though was solid muscle.

I took Julie's bike and we walked up the hill.

"Thanks for sending them off. They're nice guys, but I don't want them wasting their time with a poor rider like me."

"You're not a poor rider. You just aren't as good as my friends. I can tell they'd like to go out with you. I expect to get texts from them soon asking for your phone number."

"I don't want to go out with anyone right now."

I wrinkled my brow. How could she have worked so hard on getting into shape and not want to take advantage of it? I asked myself.

"Why?"

"I met them last year, right?"

"Right."

"And they ignored me. I want a guy who likes me and sees my body as bonus, not some guy who wants to date my body and sees me as a bonus."

I was disappointed. One of the reasons I had convinced her to come to this rally was to set her up with one of my friends.

* * * *

"What should I eat?" asked Julie.

We were at the second rest stop, twenty-five miles into the ride.

"You did fine picking out foods at the first rest stop. Pick out something similar here."

When we had started training, Julie's weight hadn't changed much. It hadn't been until I had convinced her to let me make her dinner and a sack lunch every night that she lost weight. Until then, she had eaten fast food for almost every meal and fast food portions were terrible for someone of her size. When she wasn't exercising, Julie should have eaten 1500 calories a day. She had been frequently eating a Bacon Ultimate Cheeseburger, fries and a Diet Coke for lunch or dinner. That had been 1360 calories for one meal. Once I had gotten her eating homemade meals that were the right size for her body, the pounds had melted away. Now, she often asked me what she should eat whenever we were away from home.

It was a lot more pleasant cooking for her and me; cooking for only me sucked. After work, we rode bikes either outside or on trainers in our apartment and then I made us dinner while we chatted about our days. When she had graduated from college, she had gotten a studio apartment in the same complex where I had a studio, about ten miles from where we had grown up. Once I had taken over cooking for her, she had said it was pointless for her to have a kitchen. She had suggested that we get a two-bedroom apartment together to reduce the amount of rent we paid. When I had agreed, she had gone to the management and arranged everything. We lived mostly happily together with fewer fights than when we were kids. Julie liked to joke she was training me to be a good husband.

"How are you feeling now?"

"I'm feeling it now, but I can finish the ride."

"I think you hit peak benefit of the ride around twenty miles. Every additional mile is less and less of a benefit, and it will make you sorer when we're done. Why don't we call a SAG wagon and get a ride to the finish?"

"I'm still getting a benefit for each mile?"

"Yes."

"Then we'll keep going."

* * * *

I was so proud of Julie when we crossed the finish line. She had rode steadily the whole way without complaining, though she had to be hurting now. We rode over to the lunch area and my four friends were waiting for us at a table.

"Get a protein bar and some chocolate milk. I'll join you shortly." I put our bikes on the roof rack on my Subaru, locked them down and walked over to my friends.

Julie looked bad. She was definitely in pain. She was walking around awkwardly with little winces. My friends and I looked sweaty but not tired. For us, it had been the first ride of the season and we hadn't pushed ourselves.

"How are you doing, Julie?"

"My legs are on fire. My feet hurt. Everything else is sore. You warned me I would hurt, but I hadn't thought it would be this bad."

"Walk around and see if you feel better." I knew she wouldn't. Her body had produced an excessive amount of lactate and she would be in pain until it was processed.

My friends tried to engage Julie in conversation, but she didn't respond. Pain has a way of making you not talkative. I finished my protein bar and chocolate milk. I didn't see any point in sticking around with Julie in such pain.

"Guys, we have a motel room and I'm going to take Julie there for a nap. Could you stick around and join us for dinner at five?"

They all agreed to stick around. I gave them the name of the Italian restaurant that I had planned to eat at. With that, I took Julie's arm and gently walked her over to the Subaru.

To convince her to do another bike rally, I had found a rally at a tourist trap town three hours from our place. I knew Julie had wanted to visit it, so I had suggested we drive out Friday night, get a motel room for two nights, do the ride and spend the rest of Saturday exploring the town. I had offered to pay for the motel room, as it didn't cost anymore for two than one. It had taken quite a bit of wheedling, but I had gotten her to agree. Now I was glad that I had gotten the motel room, as Julie needed a place to crash.

As soon as we got in the room, Julie collapsed on the bed closest to the door. I went into the bathroom and got some ibuprofen out of my toiletries bag. I filled a glass with water and went back to Julie.

"Here. Take this."

She leaned up a little bit to take the ibuprofen then sprawled back on the bed. I went out, got the bikes off the Subaru and brought them into the room. Julie hadn't moved.

"I'm going to take a shower. Are you going to be okay?"

She grunted something that I took to be a yes. I took a shower and came out in my shorts. While I was in the bathroom, Julie had stripped off her biking jersey and shorts, pulled back the bed covers and was now lying on top of the sheets in a dark gray sports bra and gray panties. Her panties were soaked with sweat and hugged her cute little ass. She wasn't moving.

I want back into the bathroom and found the baby oil I kept in my toiletries bag to masturbate with when I traveled on business. I came back out and approached Julie.

"I'm going to give you a massage, okay?"

She gave a weak grunt. I rubbed my hands together, poured some baby oil on them and began kneading her calves. I had never given Julie a massage before and hadn't planned to give her one after the rally. With her in so much pain, I felt like I had to do something. My ministrations provoked some groans. Her calves were very stiff and I worked quite some time on them to get them relaxed. Julie was getting bikers' legs - narrow at the ankle and knee with large, muscular calves. She had some muscle definition, but nothing close to mine.

My dick had gotten a little stiff when I had seen Julie lying on the bed mostly naked. Now that I was fondling her body, I was rock hard. I loved massaging a firm body. I hadn't massaged a body this nice since I had broken up with Kim and that had been four years ago. God, I missed Kim. Since we broke up, I hadn't dated a girl that could hold a candle to her.

I got Julie's feet relaxed and then worked up her body. She laid there unmoving and occasionally moaned. When I got to her lower back, I was hugely tempted to slide a hand into her panties. Her ass looked fantastic and was only inches away. Would she have had the energy to protest? Sick thoughts for a brother to think about his sister.

After an hour, I had finished her backside. "Turn over, Julie." She weakly moved and eventually flipped herself over. "Julie, you're going to be very relaxed when I'm done. Go to sleep and have a nice nap. When you wake up, text me and I'll come back."

I spent thirty more minutes massaging her front, starting with her feet and working up. As I kneaded her muscles, Julie got more and more relaxed. When I got to her upper chest, I was tempted to slip my hand into her bra. Her tits looked so big on her and again I wondered if she would have the energy to protest. I pushed the sick thoughts out of mind and continued.

When I finished, she was well on her way to dreamland. I finished dressing; got my wallet, cell phone and keys; and slipped out of the room. Across the street from the motel was an upscale burger place. I didn't want to go far, so I hiked over there. I had a double cheeseburger with bacon and barbecue sauce. It was ridiculously far off my diet. However, I knew I wouldn't be riding hard again for over 48 hours so it was okay. There was something about eating something forbidden that made it extra delicious. I couldn't remember enjoying a meal more.

I checked my cell phone while I was eating and sure enough, I had texts from all four guys asking about Julie's availability. I texted them back that Julie had said she wasn't interested in dating right now.

I played a game on my phone until I got a text from Julie - "Up. Taking shower". I headed back to the room and Julie was still in the bathroom when I walked in. She came out wrapped in a towel.

"I'll get some clothes and change in the bathroom," she said.

"No, change out here. I'll turn away." I wanted to get out as soon as possible to explore the town. The massage and nap had taken up a lot of the time that I had planned to spend exploring.

I turned around and faced the other side of the room. I could hear Julie rummaging around in her suitcase. I could hear her doing something, but I couldn't tell what. What was taking her so long?

There was a mirror on the wall in our room and I couldn't resist looking in it to see what was taking her so long. She was bent over the bed topless, holding up different shorts to the T-shirt she had gotten at the rally to see which matched better. I tried hard to not suck in my breath. Her tits were beautiful. They were pear-shaped and pert with no sagging. Her nipples were relatively large and light brown. In college, some of my Engineering friends had joked about a "Standard British Handful" for measuring tit size and she seemed like a 2 or 2.5.

I had never seen tits that nice. Oh, I had at strip clubs, but they didn't count as I could never touch those and they were probably fake too. These were all natural. Not that I would ever be able to touch Julie's.

Julie had gotten a few bras out and she was testing to see if they would show through the T-shirt. The T-shirt was white with a red and blue design on it. She decided a light blue bra that matched her panties would show through, but a light peach one wouldn't.

She looked up and caught me looking at her in the mirror.

"Sorry," I said, feeling very embarrassed. I looked away from the mirror and stared at the far wall.

"It's okay. I shouldn't have taken so long."

In few moments, she said, "Ready." I turned around. She looked great.

"How do you feel?"

"Sore, but much better. Where did you learn to massage like that?"

"Kim. She loved massages. We took three massage classes together."

"Damn, she was a lucky girl. I've had boyfriends give me massages, but nothing close to that good."

"She loved a massage after a hard workout. She would moan and groan the whole time I worked her body. When I was done, she would be like 'Do whatever you want with me'." I smiled at the happy memories. "Oh, that was TMI."