Cycling Weekends with Sis

"So you were drifting apart?"

"Yeah. I went to Florida for Spring Break, but the passion was gone. We tried, but she was a different person that I didn't have much in common with. She broke up with me a few weeks later. She began dating someone she trained. They got married two years ago."

"You haven't been serious with anyone since, right?"

"Yeah."

"Why not?"

I sighed. "Things have gone pretty well with the girls I have dated until I get them naked. The girls I have dated haven't been fit and their flabby bodies turned me off. Kim spoiled me for women I can date."

I was working down her arms now. Since I had reset myself, I had been doing better at giving a good massage while talking. Julie and I had done some weight lifting during the winter. I had done mostly legs, but Julie had done exercises for her whole body. I squeezed and kneaded the firm arm muscles she had developed and enjoyed how they felt in my hands.

"Why don't you date someone who's fit?"

"Cause every guy wants to date a girl who's fit. A 5'6" guy doesn't have a chance. I keep hoping to find a cute aerobics instructor who wants to marry a good provider, but no luck so far."

"Am I fit? How does my body compare with Kim's?"

I took a deep breath. I felt uncomfortable where this discussion was going.

"Flip over."

Julie turned over, exposing her marvelous tits to my sight. They looked even better this close. I shook my head and moved to her feet to re-start the massage.

"Your body is better and worse than Kim's"

"Huh?"

"Kim had been a triathlete for a few years before I got her naked. Her whole body was firm muscle with almost no fat."

"So she had a lot better body than me?"

"In ways not. She had no tits and no hips. She kept her hair short in a pageboy cut and had a masculine-looking face. Most people assumed she was a guy when they met her. Nobody would think that of you."

I looked up and Julie gave me a smile. I finished her thighs and was ready to work on her upper body. Her beautiful tits were right in front of me. I told myself to stay away from them. I worked on the muscles of her upper chest.

"So you think I have a sexier body than she does?"

"Definitely. Nobody stared at Kim's body like how my friends stare at yours."

I had tried hard to resist touching her tits, but I couldn't do it. I dropped my hands down to them. I hoped she thought it was all a part of the massage. They felt wonderful, so soft and yet so firm. I was afraid she would scream or something, but instead she had a small smile on her face. My dick was like steel, the hardest it ever felt.

I did one more pass over her tits and moved on to her shoulders. My heart was hammering in my chest. I felt like I had dodged a bullet. I kept massaging her body. Julie didn't say anything more and kept the same contented smile on her face.

"Done!" I said as I finished. "Are you going to take a nap now?"

"Yes." She got under the sheets. "Josh would you nap with me?"

I normally didn't nap after a ride, but how could I refuse a beautiful, almost naked woman?

"Sure."

She slid over and I got under the sheets. She took my hand like she had when we slept together before. I laid there for a while, trying to understand what it all meant. I gave it up and drifted off to sleep.

* * * *

After we woke up, Julie took a shower. She came out of the bathroom in only tiger stripe panties. She once again pulled out a number of shorts and compared them to the rally shirt to see which one looked best with it. I stared at her wonderful body.

Once she was dressed, we got into the Subaru to go to the festival. Once we were seated, Julie leaned over and gave me a kiss on the cheek.

"Thanks so much for the massage, Josh. I never suspected my big brother had magic fingers."

I felt my cheeks get hot. "Um, it wasn't a big deal. I enjoyed doing it." I had particularly enjoyed palming her tits.

I put the Subaru into drive and headed us towards the parking for the festival.

"How is a sensual massage different than the massages you have given me?"

"With a Swedish massage, you are trying to get stiff muscles to relax, so it is all about manipulating muscles. With a sensual massage, you are trying to stimulate the senses for pleasure and to create erotic energy. It is a lot less formal and I do whatever I think will stimulate my partner."

"Would...would you give me a sensual massage tonight? I'm really curious as to what it would be like."

"You would have to take all your clothes off."

Julie was quiet for a bit. "I guess that would be fine. You have seen me mostly naked, so seeing me all the way naked this once will be okay."

I was surprised when Julie agreed to get naked for me. I was going to see all of her wonderful ass. And her pussy too. I was back to being rock hard. I knew I shouldn't be excited about seeing my sister nude, but I was.

We arrived at the festival. We got out of the Subaru and walked around. Most of the festival was a line of booths with items for sale, mainly craft items.

I texted Ben and Connor where we were and they came over. They seemed the most interested in Julie of my friends and I thought they would treat Julie well if she dated them. I hoped some chemistry would develop between Julie and one of them, but I knew I couldn't push it.

The four of us wandered around the booths and had a good time checking out the wares. The glassblower was my favorite and I spent a lot of time watching her work. Some of my friends found us as we perused including (sadly) Chuck. Chuck stayed glued to Julie's side.

My favorite part of the festival was a track they had barricaded off with hay bales. Go-carts with Formula One-type bodies put on top were raced around the track in various heats by tween kids. It looked like a blast. I wished I could have done that when I was their age.

* * * *

Some of my friends had gone home after the ride, but the rest met at the Italian restaurant at five. There were nine of us, so we had to wait a bit for a table for six to be pulled next to a table for four.

Connor, Julie and I walked down one side of the combined table. Connor pulled out the next to last chair for Julie to sit in. Ben sat down opposite of her while Connor sat down to her left. I pulled out the last chair to sit to Julie's right and...Chuck sat down in it before I could.

"Chuck, Josh was going to sit there," said Julie.

"Well, he should have sat down quicker."

Chuck was such an asshole. I walked around the table and sat down diagonally from him so I wouldn't be tempted to punch his lights out. Though, it might have improved his looks.

Julie stared at Chuck for a while as he talked to her like nothing unusual had happened. Julie eventually stood up, walked around to the empty chair next to me and sat down. We had a pleasant dinner with Julie dominating the conversation at our end of the table. Whenever Chuck tried to talk to her, she pretended not to hear him.

Once we had finished eating, I got up to empty my bladder. When I came back, Chuck was sitting in my chair. Julie was standing, facing him and looked livid.

"Hell yes, I'm loyal to my brother!" said Julie loud enough for most of the restaurant to hear. "Where were you when I needed someone to push me to exercise? To eat right? Where were you when I needed a friend?" She faced the whole table. "Where were any of you?"

All of my friends suddenly developed an intense interest in the little sauce splotches left on their plates. I put my arm around Julie and asked, "Everything okay?"

"Yes. Chuck here is going to back to his seat now. Isn't that right, Chuck?"

Chuck sat there as if he had no intention of moving. Where was a bouncer when you needed one? Finally, Chuck sighed and slowly stood up as if the weight of the world was on his shoulders; as if moving out of someone else's seat where he wasn't wanted was the noblest sacrifice.

After the confrontation with Chuck, the mood was ruined. The conversations were flat. After ten minutes, I said it was time for Julie and I to go back to the motel and we wished everyone good-bye.

* * * *

It was a quiet drive to the motel. I guessed that Julie was upset from dealing with Chuck. I had other things on my mind. The feel of my sister's tits when I had massaged them and the little smile she had given me. Her awkward request for a sensual massage. Her agreeing to get naked.

What did she want from the sensual massage? What did I want from the sensual massage? I didn't know. I did know that whenever I had finished giving a woman a sensual massage, she had been hot, horny and ready to fuck.

* * * *

Some part of me hoped Julie would chicken out on getting naked. When we got into the room, I watched to see what she would do. She quickly stripped as if it was no big deal and laid down naked on the bed. I stripped down to my jockeys. I knew pre-cum would eventually leak out while I massaged Julie and I didn't want any to drip on her.

I went to the bathroom, got a plastic cup, filled it with hot water, and put the bottle of oil into it. I also grabbed a condom from my toiletry bag. Would I need it? Was I sick to hope that I might need it? It was my little sister out there, but she was also a hot, sexy woman.

I walked towards the bed. I hid the condom while I approached the bed, set it on the floor and put the plastic cup on top of it. I didn't want Julie to see it.

As I rubbed my hands together to warm them, my eyes were drawn to Julie's ass. Her cheeks were firm from the biking, but had some padding on them. They looked oh so squeezable. I would be squeezing them later; I had to prepare her first.

Once my hands were warm, I ran a finger along the top of each shoulder. I moved my hands down each shoulder blade, trying to touch Julie as lightly as possible.

"God, that feels good," said Julie.

I continued moving my hands slowly down her body. Sometimes I would make a long, slow stroke down her skin. Other times, I moved my hands in circles or other patterns. I tried to be unpredictable with how I moved my hands.

"You are making me feel all tingly."

I slowly worked my way down her back and on to her ass. I resisted the urge to cup and squeeze her cheeks. Instead, I spent a lot of time stroking all that soft, smooth skin.

"Josh, you really do have magic fingers. They are making me feel great."

I continued the strokes down her body and eventually reached her feet. I had her flip over and started again on her front. Her nipples were hard. This time, I openly ran my hands over her tits and she sucked in her breath when I did. I moved my hands around her tits in circles, and then resumed working my way down her body.

"I so wish one of my boyfriends had done something like this for me. I just love this."

I gradually reached her crotch. Her pussy hairs were a light brown and neatly trimmed. As I moved my head close to her pussy, I could smell the scent of arousal. I continued working down her body.

When I got to the end of her legs again, I had her turn back over on to her stomach. I moved up to the top of the bed and sat down above her head. I put oil on my hands and worked her arms. She seemed to respond best to light touches, so I rubbed her skin lightly.

I bent down and nibbled on her neck. Julie moaned. I kept working my way down the top half of her body as I continued to nibble her neck or her earlobes. She moaned the whole time. When her top half was done, I moved to between her legs. I ran my hands over her wonderful ass, cupping and squeezing. I moved down to her thighs, concentrating on her inner thigh. I could smell that she was very aroused.

"I am seeing now how Kim would be willing to let you do anything to her after a massage like this."

I had her flip over. Once she was lying on her back, I straddled her just below her crotch. As I ran my oily hands over her shoulders, arms and tits, I ground my crotch into hers. Her eyes were closed and she was concentrating on the pleasure I was giving her. Once I was done with her upper body, I knelt next to her as I ran my hands down to her crotch. I slipped a finger of my right hand between her pussy lips as I massaged a tit with my left hand.

I had been concerned she would protest me touching her sex, but all she did was groan. I continued running my finger along her pussy lips, bringing fluid up to her clit. As I rubbed her upper body with my left hand, I applied gentle pressure to her clit, sometimes using a circular motion and sometimes a figure eight. Julie was breathing hard now. She had a look of sensual pleasure on her face.

I moved further down her body so that I could slide a finger of my right hand inside her while I massaged her clit with my left. I massaged her G-spot. That quickly brought her to buck her body on the bed. She gave a small scream as an orgasm swept over her. I moved my hands away from her, the massage finished.

Julie laid there panting for a bit, and then said, "So, is this where I let you do whatever you want with me?"

I shook my head. "I only want to do what you want me to do."

"Josh, come here."

She grabbed my arm and pulled on it to guide me to move my mouth to hers. She kissed me softly on the lips.

"I told you earlier that I was figuring out how to make myself happy. Make my happiness complete, Josh. Make love to me."

I kissed her, gently at first, savoring the feeling of her lips on mine. She opened her mouth and I slipped my tongue inside. We kissed passionately for a while. I broke off the kiss, stood up, and took off my jockeys.

I took the condom out from under the cup and began to open it.

"Don't do that," said Julie. "I want to feel you in me, not something plastic." I tossed the condom aside.

"Come back here, sweetie," Julie said with a smile. I moved to between her legs. I guided my dick into her pussy and her legs hooked behind mine to pull me all the way in. I easily slid into her. She was so wet, so warm and so wonderfully tight.

"This is what I want, Josh. To feel you in me."

We kissed for a while. Being with Julie was like some wonderful, crazy dream and I was enjoying that it had come true. I broke the kiss off with a smile, pulled away from her and started pumping in and out of her. I was raised up on my arms, looking at her beautiful face and body.

I have only a five-inch dick, but the way Julie moaned and cooed, I felt like I had a full nine inches. I was so stimulated from the massage that I knew that I would not last long at all. To slow things down, I arched my back to bring my mouth to her tit.

"Suck on them, Josh. They're yours to enjoy."

I slowed my pace to feast on her magnificent breasts, sucking on one and then the other. Her nipples felt wonderful in my mouth. Once I had sated that desire, I straightened out and resumed thrusting in and out of her.

"Julie, you feel so great. I am not going to last long."

"Just fuck me, Josh. Don't worry about it."

I picked up the pace, fucking her harder. She pushed herself at me in perfect rhythm, grunting with every thrust. I loved watching her tits bounce up and down as I slammed in and out of her. I felt so lucky to be fucking a girl this beautiful.

I felt my cum boiling out of my balls. I rammed one last time and unloaded into her. Surge after surge shot out as waves of pleasure swept over me.

When I finished cumming, I bent down and kissed Julie. I kissed her softly, to show her how wonderful I thought she was. She pushed me over so that we were side to side. I slid out of her. We kissed languidly, taking our time now that the first rush of passion was over. I ran one hand over her body, feeling her smooth, slightly oiled skin.

"Julie, that was wonderful. I hadn't intended the massage to end this way, but I am glad it did."

"I hadn't intended the massage end this way either. You made me feel so great, so horny that there was no way I wanted to stop."

We kissed again. I stroked her side, palmed her tit, cupped her ass; exploring all of the wonders her body had to offer. Julie played with the hairs on my chest, tweaked my nipples, and rubbed my stomach.

After a while, she dropped her hand to my dick and leisurely stroked it. Her hand felt wonderful as it slid up and down. I was soon hard.

"Now it is time for me to do what I want to you," said Julie.

She rolled me on to my back. I slid back into the center of the bed as she straddled my waist. She positioned herself so her pussy lips were on top of my dick as it lay against my stomach, then leaned forward so she could lean on her hands. She slid her pussy lips up and down my shaft. I loved how her body felt against mine. She soon had me panting.

Julie brought up her right knee so she was on one knee. She grabbed my dick and slowly slid the head up and down her slit.

"Do you know what I want to do to you?"

"No idea."

"I want to fuck you. I want to fuck you until you cum inside of me again. And do you know why I want to do that to you?"

I could tell she felt what she was saying was important, but I didn't know what she expected me to say.

"No clue."

"Cause I love you, Josh. I love you for all the wonderful things you have done for me. For pushing me to be the person I am now."

She guided my dick into her pussy and let herself down until I was fully impaled inside her.

"I have always loved you, Julie. I loved you in high school and I love you now."

She smiled. "You feel so right inside of me." With her hands on my chest, Julie slowly unfolded her legs to raise herself straight off of me and then folded them again to sink slowly back down. I groaned as my dick slid into and out of her tight pussy.

"Josh, you are the right size for me to do this."

She continued slowly raising herself up and down while I alternately massaged her tits and teased her nipples. I was in heaven.

"God, I love doing this," said Julie, "but my legs are too tired to keep doing it."

"Let me help you then," I said as I reached down and cupped her soft, firm ass. I lifted her up and then pushed her down on me while pushing up with my crotch to pound my dick inside of her.

"Yes, Josh, just like that."

Lift, down, lift, down - we soon established an easy rhythm. I watched as her large tits wobbled back and forth in front of me. I could see drips of sweat run down from her head to her chest. Her eyes closed, she was breathing hard. I hoped she was close because I wouldn't last much longer.

Julie threw her head back and cried, "Oh god! Oh god!" I took that as a sign she was having another orgasm. I pulled her ass down hard one last time and came inside of her. I closed my eyes and felt the waves of pleasure roll over my body.

We held that position for a while, and then Julie collapsed on top of me. I guided her to the side so she was lying along my side with her head on my chest and my arm down her back. We laid there for a while, silently enjoying the bliss. I ran my fingers through her beautiful blond hair as I thought. It was all out in the open now - I loved Julie and Julie loved me. I knew that our lives would be different from now on, but how we would have to work out.

Julie raised her head off my chest, looked at me and asked, "When we get back to the apartment, are you moving into my bedroom or am I moving into yours?"

Some typos were removed in 2024.