Massage in a Bottle
“Tonight, I’m gonna have myself a real good time,” I thought as the download started. My favorite game just received a bunch of new levels, skins, and weapons. I couldn’t wait to try these out. Right now I was sitting naked on my chair as I just came out of the shower. I was idly toying with my dick and fiddling with my sparse pubic hairs, as I checked if the download would indeed start and not stop at 2% like last time. The progress bar was going at it steadily and was at 7% already, so I figured it would go now.
I got up from my chair to get a clean pair of boxers, and I could hear myself groan. My muscles were sore from practice this afternoon. I ran track in school and at thirteen, I was the youngest of four members of my team to make it to the state semifinals.. My mom was really proud of this, and wouldn’t let an opportunity go to waste to talk endlessly about it. I’d be lying if I said that I wasn’t proud of my achievement. I knew I had a real talent for running, but I didn’t want to brag about it. Just recently I took an interest in girls, and in Monica DeWitt in particular. She used to date Brad Johnsson but broke up because he bragged about his football skills all the time. We were in the same class, and after she saw me winning, we started talking. So, I knew better than to brag and be all studly about it.
I was pulling up my boxers and feeling bummed about my aching muscles when there was a knock on my door.
“Just a sec!” I said.
I pulled up my boxers, adjusted my junk, slapped on a t-shirt, and walked to my door. When I opened it, I saw my older sister Ashley standing there with a big bottle in her hand. I couldn’t make out what it was exactly, but I could see it wasn’t a big bottle of champagne to celebrate my victory.
“Hi, Jacob. Mind if I come in for a moment?”
“Of course not,” I said, and stepped aside to let Ashley in.
She walked over to my desk and put the big bottle on it. She checked my screen and a smile appeared.
“Downloading the newest update?”
“Yeah. I heard it’s awesome.”
“You know there are naked chicks in this update, don’t you?” she smiled.
“Uhm. No?” I tried.
“Don’t worry. I won’t tell mom or dad.”
“Thanks,” I said.
My sister and I got along quite well, largely because of our small age difference. Ashley was just 10 months older than me. We weren’t the best of friends, but we each accepted the other. Ashley was a pretty girl. Even I could see that, and I was her brother. She was in the popular cliques at school, where I was a little bit of a nerd. I liked math and computers, which obviously weren’t the subjects the popular kids were into. But I didn’t care about fitting in or cliques at all. I had a few close friends, no one picked on me, and I could do what I liked to do. Why would I worry about what other people think or expect? But our differences at school were not reflected at home. We helped each other out where we could. And, besides the usual bickering a brother and sister always have, we respected each other. We talked about pretty much everything with each other too. Just recently Ashley told me that she had a major crush on Brandon Green, the basketball captain at our school. We talked about ideas to help her get close to him.
Ashley sat wiggling in my chair and looked at me, as I put on a pair of shorts. Not that walking around in underwear was a really big deal in our house, but I felt a bit more comfortable with pants on in front of my sister. I could see she was a bit nervous, as she kept fiddling with a button on her shirt. She laughed at my moan as I bent over to step into my shorts.
“A bit sore, Jacob?” she asked.
“Yeah. I guess I trained a bit too hard,” I said while pulling up my pants and sat down on my bed, facing Ashley.
“Ehh… About that…” Ashley stammered and continued fiddling with her blouse.
Now I was curious. I had no idea where this was going, but considering her being so nervous, it must be important or something awkward.
“What is it? Don’t be shy.” I thought back to about half a year ago, when she helped me out big time after I had my first wet dream. I was extremely embarrassed about it and didn’t know who to turn to. At first, she laughed a bit when I told her, but after seeing the despair in my eyes, she helped me with my stained underwear. She showed me how to quickly clean it, dry it, and then put it in the hamper as if nothing had happened. “I mean… I’ve told you about my wet dream. Talking about not being shy…” I trailed off
I could see Ashley’s eyes light up when I said that. We hadn’t talked about it after it happened, but I was positive she remembered.
“Yeah. That was a bit awkward, wasn’t it? But I’m still glad you trust me enough to come to me with it,” she smiled.
“I do. I didn’t want to go to mom or dad with it. They’d be acting all too understanding and probably have ‘the talk’ with me after that. So, yeah. Thanks for that. Now. What’s up?”
“I have a bit of a weird question,” she started while taking the big bottle in her hand. “Do you remember us talking about Brandon the other day?”
“Of course. Made any progress?”
“Not really,” Ashley said and looked a bit down.
“Oh…” I responded, not sure what to say to that.
“But I think I may have found a solution. I discovered this website online…”
“You know that a lot of bad stuff starts with that sentence, don’t you?” I interrupted her.
She started laughing and I could see her relax a bit now. I looked at the bottle, and saw that it wasn’t an ordinary bottle, but couldn’t quite place it either.
“I overheard Brandon talking with his best friend. He said they could really use a massage after the intense training schedule their new coach uses. I started thinking and figured that maybe I could be that person and get my hands all over his body. Well… maybe not ALL over, but you know what I mean.”
I couldn’t help but smile when she said that. In my head, I saw my sister sliding her hand under the white towel covering Brandon’s privates.
“I see. But you don’t know how to give a proper sports massage?”
“No. I don’t. So I started googling how to give a massage when I stumbled on this website. It’s called massageinabottle.com,” she said and held up the bottle for me to see.
As I saw earlier, the bottle was big. But as she held it in front of me, I noticed that it wasn’t a bottle. It was just a bottle-shaped package. Ashley twisted the top half and lifted it off, revealing a few separate packages.
“It’s a complete set to start and learn how to give a proper massage. Considering the current COVID19 situation, almost every hands-on training is canceled. At least the affordable ones are.”
“I see,” I said. “But is it possible to learn this from a book?”
“I don’t think so. That’s why I think this is the best option. In the package, there is a book, a link to the private youtube channel, different types of massage oil, and three webcams. These cams need to be placed inside the room, so the instructor can watch what I’m doing and give me pointers.”
“And that’s what my question is about,” she started.
“You need help setting everything up,” I completed her sentence.
“No. Well… Yes. I do. But that’s not what my question is about.” She cleared her throat and continued. “It’s obvious you could use a massage with all the running you do, so…” she paused. “Would you mind being my guinea pig?”
I honestly didn’t see that one coming. I wouldn’t mind a massage to relieve the ache on my muscles. But I wasn’t sure if she was any good at it. And having a webcam on me wasn’t exactly relaxing either. But the muscle ache would probably be way less. And maybe my running would improve even more… During my contemplations, I noticed the tense expression on my sister’s face.
“Okay. I guess,” Was my not-too-enthusiastic response.
“Really? Thank you, Jacob!” Ashley said and came over to hug me. “I wouldn’t know anyone else who would do this with me.”
“Well, if it doesn’t kill you…” I said, a bit sarcastic.
“Don’t worry, little brother. This is one of the best in the business. And I’ve got an awesome discount on this package because I’m the first one using the webcams. If I promised to help them with the setup, create a manual, and a good review, I’d get the course practically for free. And if I’d like to, they’ll even train me with all the other techniques they offer.”
“There’s more than one? What different types are there?” I asked, not knowing what other types than sports massages there could be.
“Well, there’s a Swedish massage, Hot Stone, Deep tissue, Shiatsu, Trigger Point, Thai…” she said smiling at me.
“I see. That’s a lot. Well, I think you caught a great deal, sis! And they’ve got a funny name,” I giggled. “Are they named after the song by The Police or the bottles people on deserted islands throw in the water?”
“I don’t know. I’ll ask her during our next session. Oh, Jacob. I’m so glad you’ll help me out!”
The smile on my sister’s face was priceless. I wasn’t entirely sure how this all would work out, but I was glad I made her happy. Ashley had already talked to our parents, and she was allowed to use the empty bedroom on the far end of our home as her studio. Ashley knew that I had different plans for the evening, so we decided on installing everything the next morning. Our parents would be out all day and considering it was a Saturday, we’d be having the entire day to make it all work. Later that night, while I was wanking away behind my computer, the idea of being massaged had landed in my head and I had to admit to myself that I was looking forward to it.
The next morning, we were working in Ashley’s new salon. I was currently setting up the cameras. The manual they wrote, was very poorly written. If I wasn’t this good with gadgets, I never would’ve figured it out. I made a few notes on how to improve the manual, so I could write a new and improved one later. Besides their manual, I was very impressed by their hardware. They had auto-rotating cameras with autofocus. I didn’t know for sure just yet, but it seemed that with the right software, these cameras could automatically find the subject pointed out by the operator, and follow it through the room. I placed two cameras on the shelves around the table and hung one on the wall, close to the ceiling. This way, the entire room was visible for the cameras. I grabbed my old PC monitor and placed it inside the room, near the table, so Ashley and I could watch the trainer too.
In the meantime, Ashley was setting up the room. She stuck a big piece of foil against the window, making it non-transparent. If someone was in here, and the curtains weren’t closed yet, then the neighbors wouldn’t see anything more than a silhouette. After that was done, she put up a big, fluffy curtain, so it would be nice and cozy in the room. I helped her carry in a screen, so you could change in the room, and still have a bit of privacy. Our dad helped her yesterday with hauling in the massage table she bought on eBay, so by noon, we were pretty much done.
“I’ll go and start writing the manual, okay?” I said to Ashley.
“Okay. Great. I’ll put some posters on the wall and find a place for all the accessories like oil bottles, the incense burner and sticks, the stones, the towels. You know.”
“You sure take this stuff seriously, Ashley. It looks almost like a real massage salon.”
“Thanks. Mom already asked if I could do her too, and so did my friend Laura. But first I want to learn how to do it properly. And they understood,” she said.
“And you don’t mind that with me?” I asked with fake indignation.
“Haha. No, I don’t,” she said and smiled at me. Then, more seriously: “Of course I do. But you have a smaller body, which means it’s easier for me to learn. And besides, I won’t charge you and you’ll still have a decent massage so your running will improve.”
“You’re right. I’m just teasing.”
“Okay. In about half an hour my first course begins. At first, it’s just the theory and a lot of technicalities. That’ll take about an hour. So if you can come over here in, let’s say ninety minutes, that’ll be great!”
“Sure. No problem,” I said.
Then a thought occurred to me. I just realized that with some massages, the person being massaged is naked and only has a towel draped over the private parts. If this was necessary, I’d do that because I’d promised to help. But I wasn’t too keen about this. And I also didn’t know what Ashley expected of me.
I cleared my throat. “Eh … what do you want me to wear?” I asked.
She thought for a moment. “I think you can wear a t-shirt and your underwear. But I’ll check for you. You can change in here. So just come on in and we’ll see, okay?”
“Thanks. I’ll be in my room writing.”
“Great. And Jacob?” she asked.
“Thanks again! You’re the best brother a girl can have,” she said and smiled at me.
I went back to my room and started working on the manual. I had to admit to myself that I was looking forward to the massage. My muscles were still aching and if a massage could relieve that pain, that would be great.
As I was finishing the last part of the manual, there was a light knock on my door.
“Jacob?” I heard my sister say. “Are you ready? We can start now.”
Ashley was ten minutes early, but I didn’t mind. I got up from my chair and opened the door.
“Sure. Let’s do this,” I said and walked with my sister to her massage salon.
When I entered the room, I saw a woman, probably in her mid-forties, smiling at me from the screen. I didn’t expect this to be honest. I figured it would be some eerie, spiritual touchy-feely-vibe kind of guy. But she seemed nice and could just as well have been my mom.
“Hello Jacob,” she said to me, still smiling. “I’m Jennifer and I’m teaching your sister the proper massage techniques.”
“Hello, Jennifer. Nice to meet you,” I responded, immediately feeling at ease.
“I’m going to explain the setup of this course to you too, so you’ll know what’s going on and what to expect. The cameras you set up so perfectly, are fully automated. My son is pretty handy with this stuff and wrote the software for this course. The camera will automatically detect the person lying on the table and knows what’s needed to be in the frame. You’re always able to see what I see in these small pictures at the side of the screen,” she said and pointed to the left side of the screen.
“Okay. That’s pretty awesome,” I said, genuinely impressed by the automatic cameras.
“Unfortunately my son isn’t as good in writing manuals as he is with writing software. So, I want to thank you for helping me out with that. I really appreciate it.”
“No problem, Jennifer. You’re helping us out, so returning the favor is the least we can do.”
“That’s great. But still a big thank you, she smiled. “Now. In some of our lessons, the person on the table will be naked. Of course, there will be a towel covering everything, so no one has to see anything. But in the event of the towel dropping or any other unfortunate event, there’s an automatic blurring system build in. That way, you’ll never be naked on camera.”
“Ehh… Okay?” I responded, not too sure what she meant.
“Here. Let me demonstrate,” Jennifer said.
She surprised me by lifting her tank top. The moment her breasts came into view, they were immediately blurred.
“See?” She said, still holding up her top.
“Ehhh… I see. That’s a cool feature,” I said, blushing furiously.
“Thank you, Jacob,” she said and pulled her top back down and I noticed the blur automatically disappeared. “One last thing. To correctly point out to your sister how things work, and to show some techniques, I’ve asked Sam to help me. This way, I can show some things in real life. Do you mind if there is another person present?”
“No. I don’t think so. You mean over at your place, don’t you?” I asked, not too keen on having some old dude joining us in these lessons.
“That’s correct. Sam?” she called.
I could hear a door open and the camera automatically switched. What I saw on the screen surprised me. Instead of an old hairy guy, a beautiful young girl walked in. She had shoulder-length brown, almost black hair, and a lovely face. I guessed she was around twelve years old and she was wearing a fluffy white bathrobe.
“Jacob, this is Samantha. She’s my daughter and helps me out with this course,” Jennifer said.
I must’ve looked stupid because my mouth was open and I didn’t say a word.
“Hi, Jacob,” Samantha said sweetly to me.
“Ehh… Hi!” I managed to get out of my throat. ”I was expecting a man, so I’m sorry I look surprised.”
The three of them started laughing. I looked over at Ashley who gave me a questioning look. I figured she wanted to know if I was still game. I was. Jennifer was a very nice and open person, and Samantha was really easy on the eyes. So I figured nothing was stopping us from advancing on.
“How do we start, Jennifer?” I asked in the camera, answering Ashley’s unspoken question.
“Do you mind undressing down to your underwear and lay face down on the table?” she asked me.
I’d already made up my mind about this. She was nice, and Ashley saw me in my underwear lots of times when we were younger. And besides, when we went swimming in our backyard, she’d see me in my swimming trunks, which didn’t differ too much from this.
“No. I don’t mind.”
“Great! Jennifer said. Sam, will you disrobe too, and get on the table please?” Jennifer asked her daughter.
I stood up and started unbuttoning my pants. On the monitor, I saw Samantha untying the knot on her robe. The moment it came undone, she let the robe slide from her shoulders, causing it to fall on the floor. I had dropped my pants and was just starting to pull up my t-shirt when Samantha stood back up with the robe in her hand. I was looking at a gorgeous girl in a skimpy white bikini and I immediately felt a stir in my underwear. I quickly took off my shirt and laid down on the massage table, so no one could see me getting hard. I turned my head toward the monitor as Ashley placed a towel over my butt and looked at the screen too.
Samantha laid down on the table, and Jennifer draped a towel over her butt too. As Jennifer did this, Samantha untied the back of her bikini, slid the top away from under her body, and dropped it under the table. The way she was lying, she could be completely naked. If I hadn’t seen her wearing a bikini bottom, I’d swear she was naked.
“Okay, Ashley. Take the appropriate oil, and lube up your hands. Make sure they are warm, so you won’t shock Jacob. Are you ready, Jacob?”
“Yes. I am,” I responded, smiling at her.
“Good. Start at his feet and work your way up, Ashley. Just as we talked about earlier.”
I kept my eyes glued to the screen and saw Jennifer starting to massage Samantha. I felt Ashley’s hands working on my lower legs, and was feeling more and more relaxed. She gently massaged the tension out of my calves. After a while, she moved higher and was working on my upper leg muscles.
“You need to make sure you get the gripping points of the muscles too,” I heard Jennifer say and I opened my eyes to see what she meant by that. Jennifer had her hands under the towel and judging by her arms and the position of her hands, she was touching the underside of Samantha’s butt and had her hand between her legs several times.
I felt Ashley’s hands move up closer and under the towel. She touched the underside of my boxers and at that moment, the towel dropped to the floor.
“Sorry,” she said and began to pick it up.
“Give it to me,” I said and placed the towel near my head on the table. “It’s not like I’m naked, and this way it’s easier for you.”
I didn’t know why I did this. The shyness I felt earlier was gone. I guess the way Ashley did her thing and the way Jennifer and Samantha were doing things, caused me to feel less bashful. Ashley reached the top of my legs and started working near my butt. She pushed the fabric of my boxers upward a bit and did her magic on my upper leg muscles. Her hand went between my legs a few times, and the third time she did this, her fingers accidentally brushed against my sack. I didn’t know if she realized what she just touched because she kept going at it as if nothing happened. But I sure as hell knew. My boner had gone down, and I wasn’t sporting a full mast yet, but I did chub up a bit after this contact.
“Okay, Ashley. We move to the upper body now,” Jennifer said.
Ashley’s hands did their magic on my shoulders. And despite this being a sports massage, it was very relaxing for me. I had closed my eyes, and way too soon I heard Jennifer talk again.
“It’s time for the front. Turn over please, Jacob.”
I turned over and lay on my back. I didn’t feel the need for the towel, as I was totally at ease with the situation and I was still wearing my boxers. Besides, it was way easier for Ashley this way. So I left the towel lying there beside my head. Ashley started working on my shoulders and arms, and as she did this, I glanced at the screen. Samantha had turned over too, of course. I noticed the blurring system did its work. Apparently, Samantha had left her bikini top off, and was now lying topless on her back as her mother massaged her. Judging by the way Jennifer reacted, this wasn’t the first time for them.
After Ashley was done with my arms, she moved down to my calves again. As she worked her way up and came closer to my boxers, I suddenly wished I did put the towel back. Her hands were massaging my upper leg muscles again, and her hands came closer and closer to my crotch. The topless girl on the monitor didn’t help either. The moment her fingers brushed my sack again, she noticed it. I could see her blush, and I wished I could vanish into thin air. I was sporting a full-on boner and had no way to hide it from my sister. Almost four inches of hard meat can’t disappear in a tight piece of underwear. She looked me in the eyes and I could see she didn’t know what to do.
“Do you want to stop?” she whispered.
“No. It’s… Just keep going and try to ignore it,” I whispered back.
I tried hard to make my boner go down, but none of the tricks I knew worked. Ashley kept going at my other leg as if nothing had happened. I did see her glancing at my boner a few times. And I couldn’t blame her. It was practically in her face this way.
“Ah! I see the usual had happened,” I heard Jennifer say.
I looked over at the screen and saw Jennifer smiling.
“Don’t worry, Jacob. This is a fact of life. Nothing to worry, or to be ashamed of. With another person’s hand so close to your groin, erections are bound to happen. This is something Ashley has to learn to deal with too. Don’t worry about it. Okay, Ashley…” she continued.
Now it was my turn to blush. It was bad enough I had one, but pointing it out so blatantly wasn’t cool. This meant Samantha knew I had a hard-on too. But after a few moments, I realized Jennifer was right. It is a normal and healthy reaction to all the touching. I just don’t want everyone to see it. Ah, well. Maybe I’ll get used to it and it’ll happen less frequently. Or maybe we’ll both get used to it and find a way to work around it.
After a short while, Jennifer and Ashley were done talking and Jennifer said that I could sit up straight. I saw Samantha sitting up too, and she was still topless. She was clearly a lot less shy about her body than me. She smiled at me, and my heart did a backflip.
“So, we’re done. You can get dressed now, Jacob. Thank you for helping your sister out. See you next time?”
“Of course,” I said. “Ashley did a great job! I can feel my muscles are way more relaxed now.”
“Great,” Jennifer answered. “Next week, we’ll do the Swedish massage. In the meantime, please keep practicing you two. It’ll benefit you both. And the more practice, the better. You can’t practice too much!”
“Will do,” Ashley said. “And thank you for this first lesson. It was really helpful!”
“You’re welcome. See you both next week,” Jennifer said, clicked on a button and the screen went black.
“You okay?” Ashley asked.
“Yeah. Don’t worry. It was a bit awkward, but I guess Jennifer is right. Consider it a compliment,” I said, trying to lighten the mood.
Ashley smiled at me and hugged me tightly. I was extremely aware that I was hugging my sister in my underwear. This morning I would’ve found this awkward, but now I found it soothing. I liked it.
“Thanks again, Jacob. I’ll clean up in here. You can go shower and wash the oil off your body.”
“No problemmo. Glad to help,” I responded and picked up my clothes.
“Same time tomorrow?” Ashley asked.
“Sure!” I said, trying to sound not too excited.
The next morning, I was sitting in my room blasting away at some alien army on my computer, when there was a knock at my door.
“Jacob?” I heard Ashley say.
“Come in,” I responded without taking my eyes from my monitor.
Ashley walked into my room, and in the corner of my eyes i could make out she was wearing a red tank top and some loose-fitting, grey sweat shorts. She was carrying a towel and smiled at me the moment she saw me. When I was concentrating, the tip of my tongue stuck out of the corner of my mouth. She always teased me with that, but now she just smiled.
“Almost done,” I said as my health bar was diminishing quickly.
“Take your time. I’m early.”
At that moment I was shot with a rocket and my screen went red. This boss battle was hard and I was a bit annoyed that I couldn’t pull it off. I sighed and slid my chair back, turned around, and looked at Ashley.
“What time is it?” I asked. I knew when I was gaming, I quickly lost track of time.
“Ten thirty. Mom and dad are in the study for the online church service, so I figured we could do a session now. And maybe we can do another one this evening. Jennifer said you can’t practice too much,” Ashley said and smiled at me.
“Great! I can do my regular practice run this afternoon, and then you can massage me again. I’m being spoiled,” I laughed.
“Come on, then. I’m glad you enjoy it. That makes it easier for both of us,” Ashley laughed.
We walked over to the massage room and when I entered, I noticed Ashley already turned on some background music. I was dressed in my usual chilling outfit, which consisted of a loose-fitting t-shirt and sweatpants. I wasn’t sure what to do now, so I just stood there as Ashley walked in.
“Listen, Jacob,” Ashley said seriously while looking me in the eyes. “I’d understand if after what happened yesterday you want to keep your clothes on.”
“Ehh… It was a bit awkward, yes,” I said, feeling myself blush again. “But I thought about it, and Jennifer is right. It’s not like I want to have sex with you or something. I just get… You know…”
“Yeah. I know. I didn’t know what to do either. I just didn’t expect it. That’s all. So we’re cool?”
“I guess. It’s not like I want you to see it. But I want these massages too. So, if ‘it’ happens, it happens,” I said, emphasizing the first it, and trying to sound as casual as I could.
“Cool. I did some thinking too, and if it makes you feel more comfortable, I wouldn’t mind stripping down to my underwear too,” she said with a slight blush on her face.
“But then I’ll be hard the entire time!” I blurted out. “Ehh… I mean…”
Ashley gave me a questioning look. She clearly didn’t catch on to what I meant.
“A beautiful girl in her underwear usually doesn’t help in the boner department,” I giggled.
That lid up Ashley’s face considerably. She started smiling and a deep red blush spread across her face. She started fiddling with the towel in her hand and looked shyly at the ground.
“You think I’m beautiful?” She softly asked.
I didn’t expect this at all. My sister was insecure about her looks? Heck! Even I could see she looked amazing, and I was her brother. Brothers aren’t supposed to see that in their sisters.
“Well, duh!” I said as normally as I could. “You are pretty hot. All my friends say so!”
“All your friends?” Ashley asked with a sly smile.
“Well… I think you’re not too bad either. I mean… In your bikini at the pool and stuff, you look pretty good to me,” I softly added.
Ashley started laughing and hugged me tightly.
“So. What do we do?” she asked. “Want me to join you?”
“Ehm. Okay then. If you can ignore my ehh,” I cleared my throat. “Boner, that is.”
“Don’t worry. Like I said, I just didn’t expect it last time,” Ashley said and started lowering her pants.
I quickly lifted my shirt and lowered my pants, so I was dressed only in my orange Bjorn Borg boxers. As I stood back up straight, I saw Ashley was ready too. And I wasn’t lying. She stood before me in her green panties and black bra and I let my eyes roam over her body, not caring if I got hard or not.
She was a bit skinny, but not as much as me. I couldn’t count her ribs for example. At least not as much as you could with me when I inhaled deeply. She had a tight belly, and I noticed two small gaps between her skin and the waistband of her panties. These gaps were on both sides of her stomach between her hip bone and her belly. I couldn’t see anything, but I found this extremely sexy. I let my eyes roam over her breasts and they were sexy as hell too. They were about the size of half a lemon, and she wore a black bra with a lot of lace. It wasn’t see-through or anything, but I was pretty sure I could see her stiff nipples poking through the fabric of her bra. Ashley had a dark skin complexion, raven-black hair, and brown eyes, just like me. Our Italian roots were probably to blame for that.
This all happened in a few moments, and after my eyes roamed high enough to get to her eyes, I could see her checking me out too. I didn’t get a full-on boner yet, so I let Ashley check me out until she snapped out of it.
“You’re not too bad either, Jacob,” Ashley said and smiled. “Lay down on the table so we can get started. We don’t want to make it an all-day job, do we?”
I laid down on the table and relaxed as Ashley started working her way up my legs again. As she reached my upper leg muscles, her hand went into the leg of my boxers, and her fingers rubbed right at the underside of my butt cheek. I had to hold back a gasp because this was a bit unexpected. But I didn’t see a reason why I should stop her, so I didn’t say anything. She moved her fingers forward and they moved over my skin, toward the inside of my legs. As she went further, I could feel myself getting hard in a microsecond. I didn’t know where this would end. And this was, as a later learned, an extremely erogenous zone for me.
Her fingers stopped just shy of my ballsack and they found the gripping point of my leg muscle and started working on that. As she was kneading away, she accidentally touched my ballsack a few times. I was feeling hornier by the minute, but didn’t want to let on because I figured that Ashley didn’t do this intentionally.
“You don’t mind me doing it like this, do you? Without the fabric of your boxers in the way, I can feel your muscles better,” Ashley said.
“N… No. I don’t mind,” I said, as her finger brushed my sack again.
After she was done with my other leg and touched my sack a few times more, she moved to my shoulders and arms. This gave my boner the time to deflate before I had to turn over. When I did turn over, Ashley gave my arms and shoulders another rub-down and then started at my lower legs again.
“How am I doing?” She asked.
“Great! I can really feel a difference in the muscles you did already,” I said.
And this was true. Her hands were amazing and I did feel awesome. When her hands went near my crotch again, I could feel the growth in my pants, before she was even close to my dick. Her hands went higher and higher, and as I looked at Ashley, she had a very concentrated look on her face and her eyes were glued to my groin. Maybe she wanted me to be hard?
Her hands went inside the leg of my boxers again, searching for that gripping point, I guess. But she went way too high and her fingers were touching my pubes. Luckily my dick was pointing straight up toward my belly button, so she didn’t touch that accidentally.
“Oops. Too high,” she said, but I wasn’t quite sure if she actually meant it.
Her hands moved down a bit and worked on that gripping point. She was close to my sack a few times but didn’t touch it. I guess because she could see better what she was doing this way. All this time, my dick was hard as a rock. I couldn’t help it. But I wasn’t ashamed of it either. And considering how Ashley reacted around it, neither did she. Her eyes practically never left my dick.
“Doesn’t it hurt?” Ashley asked as she was finishing up.
“What? My boner?” I said, sitting up straight.
“Yeah. I mean… It’s been hard for quite some time now.”
“Well. Yeah. After a while it does. It hurts a little bit, but now it’s going down and then it’s quickly gone.”
“I’m sorry for hurting you,” Ashley said. “If you want, I can avoid that area.”
“Nah. It’s fine. Don’t worry. After I jerk off in the shower I…. Ehh” I started blushing furiously as I realized I talked before thinking again.
I saw a sparkle in Ashley’s eyes as she realized what I was about to say.
”I mean…” I couldn’t think of a quick way out of this, so I decided to just keep talking. “The upside is that my muscles are feeling way better this way,” I said while pulling up my pants, still blushing.
Ashley just smiled and gave me a tight hug. Considering I was still shirtless, and she was in her underwear, this meant I could feel her bra-covered breast pressing against my bare chest. My boner popped back up immediately.
“Tonight at around seven?” Ashley asked, breaking our hug.
“Sure! Thanks again,” I said, casually adjusting my boner so it wouldn’t tent my sweats.
The evening session was pretty much a copy of what we did in the morning. We were both in our underwear and Ashley slid her hands in the legs of my boxers to massage the muscles there. And it seemed to me that her ‘accidental’ brushes against my ballsack increased, but I wasn’t completely sure yet. Other than that, it was a copy of the morning session. In fact, every session during the week was basically the same. Ashley had improved considerably on her massage techniques, and I liked it a lot. During each session, I was as stiff as I could get. Ashley’s eyes were almost constantly fixed on it, and I didn’t mind that one bit. I liked what we were doing a lot, so I didn’t bring it up and neither did Ashley.
Saturday morning I was gaming again when Ashley came into my room. After I was done with the level, I pressed ‘save’, and turned over to my bed where Ashley was sitting. I could see she was struggling with something.
“What up?” I asked.
“Ehm… Today’s practical lesson is about the Swedish massage,” she trailed off.
“I know. What about it?”
“Well. It involves long strokes from shoulder to ankle, and from ankle to shoulder.”
“Okay?” I responded, not sure where she was getting at.
“Ehm. I know I’m asking a lot, but it would be way easier when there isn’t anything in the way of these strokes…”
“Do you want me to be naked!?” I asked, not sure if I understood correctly.
“Well, Uhm, yes?” She said a bit uncomfortable. “But you’ll be covered by a towel and I’ll turn around when you turn over. And I’ll only move the towel out of the way on the parts I need to work on. And I won’t be looking. And the blurring system on the cameras will prevent them from seeing you. And…” she blabbered.
It was obvious that Ashley had thought about it a lot already. And I realized that it took her a lot of courage to ask me this. But completely naked? Okay, there will be a towel hiding the family jewels. But, naked?
On the other hand… Up until now, Ashley had been very professional about it all and perhaps the massage would be better this way. And we’d both make sure that the towel stays in place because I don’t want to show my penis to Ashley, and I was confident that Ashley wouldn’t want to see my junk either. But… naked?
This all happened in a few moments inside my head.
”You’ll promise you won’t look?” I asked.
”Cross my heart!” Ashley said seriously and I saw the load being lifted from her shoulders.
”Okay then,” I softly said, not looking my sister in her eyes.
”Oh, Jacob. You’re the best!” Ashley said and gave me a really tight hug. ”I’ll go and set everything up. I’ll make sure there’s a towel ready for you behind the screen, and that the cameras are working so you won’t have to worry about that.”
”Great, ” I said, trying to sound as brave as I could.
Ashley left my room and I was left to my thoughts. I wasn’t shy at all about my body. In the showers after running practice, I wasn’t the smallest boy in the room and my muscles, despite that I was on the thin side, were getting there too. So I knew I had nothing to be ashamed of. And maybe this was just a line I needed to cross. I knew that nudity was a part of most massages, but I was really nervous about actually doing this.
When I walked into the massage room, it was already nice and warm. Ashley was talking to Jennifer and they both smiled at me when I walked up to the monitor.
“Hello, Jacob. Nice to join us again,” Jennifer said. “Are you ready for the Swedish massage session?”
“Yes. I think I am. I’m curious if it is as nice as the sports massage.”
“Oh. Don’t worry! This is way more relaxing! It’s a complete top to bottom massage, which most people find extremely relaxing. Ashley told me she talked with you about your clothing?”
“Yeah. Yeah, she did. And honestly, I’m not too keen to do this, but Ashley told me it’s an essential part of this massage, and that my privates are covered by a towel the entire time. So I agreed to do it.”
“Thank you, Jacob. This means a lot to us. And learning to cope with naked people and their objections to it, is also a part of the training material. She can now bring that theory into practice. Did she also mention that the last half of this session is with the hot stones?”
“No. I didn’t,” Ashley said quickly. “I was too concerned about the underwear bit, that I completely forgot it. I’m sorry.”
“No problem, Ashley,” Jennifer said. “In a nutshell, you can say that a hot stone massage is the same as a Swedish massage. But instead of your two hands, you use stones, or one hand and a stone.”
“I see,” I said. “I don’t see a problem.”
“There isn’t one. We just want to make you feel as comfortable as we can, because you’ll probably be nervous about this one. By telling you what to expect, maybe you can be a little bit more relaxed about it,” Jennifer said.
I don’t know what it was about this woman. All nervousness I felt walking in, was gone by now. She had a natural way of putting people, and me in particular, at ease. By now, I wasn’t worried about taking off my clothes anymore. I just knew this was going to be okay now. Totally weird and I couldn’t explain it, but it didn’t bother me either.
“Thank you, Jennifer. I’ll just have to see how it goes then, I guess,” I smiled.
“Of course. Ah. There’s Sam. Can you get yourself ready too, Jacob? Then we’re all set and ready to go,” Jennifer said and I walked over to the screen.
Ashley already put down two towels, so I could decide for myself what to do. I undressed quickly but hesitated slightly when it was time to pull down my boxers. I looked over my shoulder and no one could see me, so off they went. Next, I wrapped the big towel around my waist and tied a knot at the front, so it wouldn’t come off. As I walked toward the table, I saw on the monitor that Sam had joined us too, and was standing beside the table smiling at me. She was completely naked, but the blurring system did its work. Obviously, she had a different relationship than I had with my mother. I’d never let my mom, or my dad for that matter, see me naked like this. Seeing Jennifer and Sam acting the way they did, this wasn’t even remotely an issue to them. I even wished that I was brought up a bit more liberal on this issue. But I wished even more that I was in the room with Samantha. She looked amazing AND was naked. I liked looking at naked girls a lot lately.
I untied the knot in the towel, laid down on the massage table, and tried to maneuver the towel in such a way that I was nicely covered. But it immediately became obvious why Ashley had put the smaller towel behind the screen too. This towel was way too big and too fluffy. Using this just wasn’t going to work. I was trying to switch the big towel with the little one, but if I wanted to do it right, I had to get up and probably expose myself.
“Ashley,” I whispered, so I couldn’t be heard by Jennifer.
“What?” She whispered back.
“Can you quickly switch these towels?”
“Are you sure?”
“Yeah. It’s just my butt. Just… Don’t make a big deal out of it, please.”
Ashley smiled and quickly swapped the towels. Jennifer was talking to Samantha and didn’t see, or didn’t let on that she saw the swap.
“That’s a nice butt, bro,” Ashley whispered.
I looked over my shoulder at her, assuming she was making fun of me. But she looked serious and had a slight blush on her face.
“Thanks. I guess?” I whispered back.
Was she just complimenting me on my body? She looked sincere, but I didn’t expect that. It was basically her birthright and task as a big sister to mock me.
“Okay. Are you guys ready?” Jennifer asked.
And that was the start of an even better massage session than the sports massage. Ashley started at my shoulders and worked her way down. She pulled down the towel a little bit, so she could reach my lower back unobstructed. After that, she gently put it back where it was before.
During the first part of the session, Jennifer pointed out a few things to Ashley by using Samantha as an example. Apparently, the blurring system wasn’t programmed for butts. Because Samantha’s butt was nicely on display to me when Jennifer showed some techniques to Ashley down there. A bit later during the session when Jennifer showed some shoulder techniques, I couldn’t clearly see Sam’s boobs, but still liked what I saw. I mean, I knew they were there and despite the blurring, I could make out where her nipples were and I could see where the slopes of her small breasts were. It looked magnificent to me.
Next up were the long strokes from top to bottom. Ashley started on my left-hand side. She exposed the better part of my butt cheek, and after that, she stroked me from my shoulder to my toes in one, long stroke. This, of course, meant that her hands rubbed my butt too. It wasn’t supposed to be erotic, but to me it was. Sure, it was also very relaxing. But each time she rubbed me there, I had to suppress a small moan. I guess Ashley sensed it too, because each time she got there, she seemed to linger a little bit longer.
All too soon it was time to turn on my back. Ashley turned her back to me, which I found both comforting and professional. I was hard as a board, and the last thing I wanted was to fully expose my boner to my sister. I grabbed the towel before I turned over, and quickly laid it back in place. Seeing what I was doing and not having to twist your arms unnaturally, made it a lot easier. I was lying on my back before I knew it and informed Ashley we could continue.
The front massage was even better, especially when she did her long strokes again. When she started it, I helped her out by adjusting the towel. It was trapped between my legs, and I laid it down over my dick in such a way that only my dick and balls were hidden, but everything besides that was visible. Even my pubes, which I noticed when Ashley’s fingers touched them, but by then it was too late and too awkward to do something about it. Ashley saw me blush the first time she touched me there but just smiled a warm ‘don’t worry’ type smile at me. I had to admit that I was getting hornier by the minute with her hands so close to my dick. I knew she wasn’t going to touch anything, but the idea that she might as well could, was extremely arousing to me.
I had to turn over one more time, so she could work with the stones. It was the same struggle I had before, and a slight cough was enough for Ashley to turn around and adjust the towel. I didn’t like the stones as much as her hands. But Ashley had to learn that too, so I let her work with it.
After almost one and a half-hour of massaging, we were done. Ashley turned around again and I awkwardly sat back up. I could see on the monitor that the blurring worked. If it hadn’t, everyone would’ve seen my boner, so I was very grateful it worked. I got up, held the small towel in front of me, and quickly walked behind the screen to get dressed.
After Ashley got her instructions for the coming week, and her promise to join the online theory session on Wednesday, we said our goodbyes to Jennifer and Samantha. I helped my sister clean the room and felt completely relaxed.
“You’re getting really good at this, you know?” I said to her.
“You think so?”
“I know so,” I laughed. “And thank you for being so understanding about my shyness and stuff.”
“I guess I’d feel the same, Jacob. One thing I learned so far, is that people will eventually lose that shyness. The only way for me to deal with it is to let them have their privacy, and allow them to determine their own pace.”
“I guess you’re right. I mean, you just touched my butt a lot. This morning I was nervous about taking off my underwear, and now I don’t care that you touch my butt. Or see it.”
“Thanks. And it’s a fine butt to look at,” she giggled.
I didn’t know how to respond to that, so I started giggling too.
“I’m glad this is working out for you,” she said a bit more seriously. “This week we’ll have to practice the Swedish massage a lot and if you didn’t want to do it anymore, I would have had a problem. So it’s in my interest too to let you have your space.”
“Well. It’s working out great. So, see you at seven?”
“Great. At around four, I’m giving mom her first massage. I’m a bit nervous about that, so I’m glad I can work on you again after that. That’s way more familiar to me now, and you’ve got a much nicer body. See you later, Jacob,” she said blushing and smiled again. She did that a lot lately.
After my massage, I took a shower and went downstairs to vegetate on the couch all day. It was awful weather outside, and I could afford it to skip one practice at the weekends. I decided that today was the day. The massage made me completely relaxed, and after I jerked off in the shower, my horniness was down a notch too. I was sitting on the couch in my sweatpants and a t-shirt. I didn’t bother with underwear, as I liked the freedom of going commando in sweats a lot.
I started thinking about being massaged again this evening, and how much I liked Ashley’s hands roam over my body. How I liked her compliments about my butt and her fingers fiddling with my pubes. I was feeling myself get stiff and horny all over again. I was all alone in the living room, so my tented sweats wouldn’t be noticed. I tried focusing on the current episode of ‘Stranger Things’ I was currently bingeing as I heard a noise in the hallway.
“You’re amazing, Ashley. Honestly!” I heard my mom say.
“I don’t think I’m THAT good,” Ashley modestly replied.
“Yes. You are. And just to think you haven’t even followed all the lessons yet! I’ll tell your dad that he needs to try it too. Oh. Hi, Jacob,” my mom said, walking into the living room noticing me.
“Hi, mom. How was it?” I asked.
“I was just saying to Ashley how good she is at doing this! She told me you’re a great help and that she couldn’t do it without you. It melts my heart hearing my kids get along so well,” she said with a huge smile on her face.
“Ah. Well. She’s doing all the hard work,” I responded. “I’m just lying there.”
“No matter. You’re a great help. So, keep it up you two,” she said to both of us and headed to the kitchen.
“What are you watching?” Ashley asked.
“Stranger Things. You’ve seen it?”
“Yeah. I did. It’s pretty awesome,” she said and sat down next to me on the couch.
We watched the show together until we ate dinner. During the show, my mind wandered to my sister’s massaging fingers and Samantha’s boobs a few times. It was a good thing I was holding a pillow to hide my tenting erection.
After we ate dinner, our mom sent us upstairs, so Ashley could practice some more. Of course, I didn’t mind and we walked to the massage room together. It was a bit hot in there because Ashley had turned up the heat. Mom complained a bit about it being cold, and she figured that too hot was better than too cold. I noticed Ashley looked a bit nervous as she got her oil and towels ready. She started lighting up some incense sticks, as I moved behind the screen to undress.
I walked over to the table holding the small towel in front of me and laid face-down on the table. I pulled the towel away from under my body and laid it down beside my head. I’d already made up my mind that from this session on, I’d be lying there with my butt exposed. I guess Ashley was right and that your inhibitions fade a bit after a few sessions. I glanced over at Ashley, and she was pulling down her pants and was pulling up her shirt.
“You don’t have to do that, you know?” I said to her as she looked over.
“You don’t mind me seeing your ass anymore?” she asked eying my butt, avoiding my question, and took off her shirt completely.
“Nah. It’s okay. It’s just a butt I figured. An amazing butt, for that matter,” I giggled. “You see it in bits anyways during the session, so why not make it easier?”
“I’m glad you trust me enough to feel that way, Jacob. And I know that I don’t have to strip down to my undies. But I like the connection it creates when I do.”
“It’s not that I mind…” I softly said. “I mean. You look amazing.”
I couldn’t dare to look her in the eyes when I said this. This didn’t just slip out. I meant to say this to her. Ashley didn’t say anything, but I saw movement in the corner of my eyes. I looked at her, and I saw her taking off her bra and drop it on her other clothes. When she removed her hands, I looked at my first ever, real-life boobs. My eyes must’ve been huge and my mouth was open as I drank in the sight. I was right about the size I guessed, when I saw her in her bra the first time. They were about the size of half a lemon. I noticed the pointy, hard nipples, and small areolas. Ashley snapped her fingers, which made me break out of my trance.
“Up here, little bro,” she pointed at her eyes laughing but seemed a little shy.
“Uhm…” was all I managed to get out of my throat.
“Well,” Ashley started, “Since you’re being so open, I decided to add something to our session too. As I just said, being undressed adds a whole new level to it. So I want to try it this way. You don’t mind, do you?”
“No,” I squeaked. I cleared my throat and said: “No. Of course not! I think it does too. I’ve just never seen breasts before, so that’s why I stared. I’m sorry. But your breasts look amazing!”
“Thanks, Jacob. That’s sweet. Let’s just get going, shall we?”
And off we went. It appeared to me that Ashley put even more effort into it than before. She did my neck and shoulders first, which was extremely relaxing. She was standing in front of me, and the way I was lying, I could see from her navel to her legs. She was wearing black hipster-style panties with a lot of lace on it. I couldn’t make out anything in her groin area, but I liked checking out her long, tanned legs. By now Ashley had reached my lower back, and as she stretched out over me, I could feel her bare nipples lightly touching my shoulder blades. I didn’t know if she did this on purpose, but damn! This was hot.
She walked over to my feet and started working her way up from there. As she reached my upper leg muscles, she searched for that gripping point again. Since my boxers weren’t in the way now, she found it immediately. She was rubbing away on my left leg, and her right hand slipped between my legs to grab hold of my muscle there. This meant that she accidentally touched my balls again. I wasn’t sure if she knew it or did it intentionally, but it was an incredible feeling. She didn’t back away either. In fact, it seemed she was rubbing it deliberately, practically toying with my balls and all the while pretending to be massaging my muscles.
I couldn’t hold back a moan as she was doing this. I didn’t want to be too obvious about it and tried camouflaging it with a cough. The same thing happened on my right leg and I had to hide a moan there too.
“You okay, Jacob?” Ashley asked softly.
“Yeah. What you’re doing feels great!” I answered with a bit of a hoarse voice.
Ashley stopped toying with my balls and her hands went higher. She held my butt with both hands and started massaging my butt muscles. I didn’t know yet how amazing that could feel. She even slid her slippery fingers between my cheeks to get a good grip. She was inches away from my anus, and I was wondering if she’d go there too.
“With her slippery fingers, this could get interesting,” I thought to myself and giggled internally.
Next up were these amazing long strokes over my entire body. I just loved this. And I was glad that there were no clothes or towels in the way. It was just hands and fingers everywhere. Every now and then, I felt Ashley’s nipples brush some part of my body, and feeling her hands all over my back, got me pretty worked up.
“Time to do your front,” Ashley said and I saw her turn her back to me.
I knew I had a difficult decision to make. Ashley was showing off her tits, I was showing off my butt and would I dare to show my bare boner to my sister? I was horny as fuck because of all the touching and bare flesh. But nevertheless, I chickened out. I turned onto my back, took the towel, and stuffed it between my legs like this morning. I made sure my balls and boner were covered, and everything else was accessible for my sister.
“I’m ready,” I said to Ashley.
She turned around and looked at me. I forced my eyes on her face instead of her boobs, and I wasn’t sure, but there was a hint of disappointment on her face. She looked me in the eyes, smiled, and started working on my upper body muscles. Now that I was lying on my back and I could see the upper half of my sister’s body, I couldn’t take my eyes away from her boobs. She was standing at my head, working toward my groin, which meant she was bent over and her boobs were inches away from my face. I was fighting an internal struggle, whether to kiss her nipple or to pretend that this was the most normal thing in the world. I chickened out once again and decided to leave her boobs alone.
All too soon Ashley moved back down to my feet and did her magic down there. Because of the towel between my legs, she couldn’t touch my balls, which a part of me regretted deeply. After she was done with my muscles and it was time for the long strokes, Ashley hesitated.
“Do you know what a happy ending is, Jacob?” she suddenly asked.
“Uhm. It’s when a book or movie makes you feel good after it’s over?” I tried.
I didn’t have a clue back then what she meant. I never heard about the happy ending Ashley was referring to. I almost fell off the table because of what Ashley did next. Her hand slowly slid under the towel and her slippery hand gripped my straining boner firmly.
“You’re right. It’s meant to make you feel good. But it’s not always a book or a movie,” she softly said and slowly started to stroke me.
I heard myself moan as her fist was sliding up and down my dick. I managed to look at her face and she was looking concentrated at my dick. I looked too and it was still mostly covered by the towel. I opened my legs to release the towel and the moment I did this, Ashley’s other hand took the towel and dropped it on the floor.
There I was. Butt naked, lying on my back on a massage table, with my topless sister jerking me off. She gripped my dick firmly and because of all the oil on her hand, it felt like nothing I ever felt before.
“Ohh… Ashley… This is… Ahhh,” I moaned.
“Sshh, little brother. Just let me take care of you,” she said, her eyes still focused on my dick.
She obviously wasn’t an expert. But her slippery hands and her naked breast made up for that big time. And because I was already worked up, my orgasm approached all too quickly. The familiar tingling in my balls was starting, and usually, I’d hold the jerking back a little as this happens. But since I wasn’t in control, the tingling kept spreading and the spreading was way faster than when I jerk myself. Ashley didn’t speed up or slow down, she just kept going. I reached the point of no return quicker than ever before, but it took longer for my orgasm to take off. It was a weird sensation.
“AHHHH… MMNG…” I groaned.
It took another second or two for my sperm to blast out of my dick. Four blasts of my still watery sperm landed on my chest. The first one even hit me on the chin. Considering this was my second cum of the day and still be able to shoot this much and this far, was a big compliment to Ashley.
“Wow,” Ashley whispered.
I could only smile as I laid there panting in the afterglow of my best orgasm ever. Ashley looked at her hand and wiped the few drops of sperm on it in the towel. I was lying there, completely exposed with globs of sperm on my body but felt absolutely no shame or shyness. I was still hard but felt satisfied nonetheless. Ashley looked me in the eyes and I could see she was a bit uncertain.
“I know what they mean about happy endings now,” I giggled.
The uncertainty washed from Ashley’s face and she started giggling too.
“I wasn’t sure if you’d let me do this,” she softly said.
“Why did you do this? Is this in the book too? Because if it is, it’s my favorite chapter!”
“There is something in the book about full body-to-body massages and couples massages, where penis techniques are mentioned. But I wanted to do this to you from the moment I saw your erection in your underwear. I don’t know why, but I just had to see and touch it. Is that weird?”
“Nah. I don’t think so. I wanted to kiss your nipples too a couple of minutes ago,” I confessed.
“You did? Why didn’t you do it?”
“I wasn’t sure how you’d react. So I chickened out,” I said and took the towel to wipe the cum off my body.
“I wouldn’t have minded it,” Ashley shyly said and looked at the ground.
I dropped the towel on the ground and sat up straight. This time I didn’t hesitate, and softly kissed both Ashley’s nipples, extracting a moan from her.
“Ashley?” e heard our dad say as he softly knocked on the door.
We were both startled by this unexpected intrusion. Thank god she locked the door and our parents were decent enough to respect the privacy of a massage salon.
“Your mom said that I should ask you for a massage,” our dad said.
“Just a second, dad. I’m almost finished with Jacob. He just needs to get his stuff, and then I’ll be ready,” Ashley said with a surprising calmness in her voice.
I got up from the table, put on my clothes, grabbed the towels we used, and put them in the hamper. Ashley quickly put her clothes on too and before we knew it, the room was as if nothing out of the ordinary had happened. Because of the surprise and fear of being busted, my erection was gone, so we were good to go. Ashley gave me a quick kiss on my cheek.
“Thank you, Jacob. I liked it a lot,” she whispered in my ear.
I blushed and didn’t have an answer, so I kissed her too, only I chose the lips. We broke our kiss and Ashley opened the door. I looked at our dad and smiled at him.
“Mom’s right. She’s an excellent masseuse,” I said to my dad and gave Ashley a wink.
“Well. I hope she’ll give me a massage because I’m really curious by now,” he smiled.
“Come on in, dad. Get ready to be amazed,” I heard Ashley say as I went to my room to digest all that had happened.
I was still sleeping when I heard a light knock on my bedroom door.
“Grmbl…” I responded.
Ashley opened my door and walked into my room. She was wearing her bathrobe and I noticed she hadn’t done her hair and make-up yet.
“Mom and dad will be gone until about two. They’re going to the Parkers to attend the online church meeting there, and they’ll be staying for lunch too,” Ashley said and sat on the edge of my bed.
“What time is it?” I asked, still a bit sleepy.
“Almost nine. I figured you’d be up for another session, so I decided to wake you.”
I was instantly awake.
“You want to do it again?” I asked.
Last night I figured that maybe this had just been a one-time event, and didn’t expect a second session. I was still green as grass with this stuff and obviously misjudged it.
“Of course I do! I had a lot of fun yesterday. And I need the practice, remember? And because we’ve got a lot of time on our hand now, I’d like to try the full body-to-body massage too. If you don’t mind that is.”
“I don’t know what it is, but it sounds like fun,” I said, not sure how that would work, but the name did sound kinda fun.
“Great! Let’s go then,” Ashley said and as she stood up, she yanked the blanket from my body.
“Hey!!” I squeaked, immediately covering my dick with my hands.
I sleep in the nude, and covering myself was a natural response to sisters exposing you. I immediately realized Ashley had seen it all already, but I wasn’t giving in easily.
“Come on, Jacob. Don’t be a prude. I’ve had it in my hand, for Christ’s sake,” she laughed. “Come on, I already turned the heating on.”
Ashley waited for me at the door as I contemplated my options. I could be all shy and grab my boxers, or I could pretend I didn’t care anymore and just walk over to the room in the buff. I decided to act all cool and just go naked. So, I got up and walked past my sister to the massage room.
“Nice butt, bro,” I heard Ashley giggle behind me.
“Yeah, yeah. Stop treating me like a piece of meat, will ya?” I laughed.
When I opened the door to the salon, I felt the warmth spreading over me. I walked over to the table and laid down on my belly, waiting for Ashley to start. She walked over in front of me, dropped her bathrobe, and hung it on the hook on the wall. I almost couldn’t believe my eyes. Ashley was wearing a white thong and nothing else. It must be in our genes because her ass looked fabulous too. Especially in that thong. I was instantly hard as a rock.
The first part of the session was pretty much the same as yesterday. Every now and then, I felt her nipples brush my skin. And she was toying with my balls more openly now. Because I spread my legs a bit wider, she had much better access to it. And now I didn’t feel the need to suppress my moans.
“You like this?” She whispered with her mouth inches away from my ear and her nipples brushing my back, as she gently kept toying with my balls.
“Ohhh, yesss. Mmhhh,” I purred.
“Good. Time to turn to your back.”
I rolled on my back and let my eyes roam over my sister’s body. I noticed she did the same and had her eyes fixed on my rock-hard boner. She stood at my head and started massaging my upper body again. This time when one of her nipples came close to my mouth, I sucked it in and lapped my tongue over it. Ashley continued massaging me, but I could hear her moan as I paid attention to her nipples. Eventually, she had to move, because she couldn’t reach the rest of my body. But up until today, she never gave this much attention to my upper body.
She was working on my upper legs again and kept toying with my balls every chance she could get away with. Her long strokes missed my dick by a hair each time her hands came near it. It was driving me nuts, and I could feel my dick leaking stuff. I was so horned up, that a bit of cum was already coming out. I later learned it was precum, but up until then I never had this. My big sister was driving me nuts. In a good way.
And then, all of a sudden, and when I didn’t expect it anymore, she started massaging over my dick. She wasn’t stroking me, but her oily hands moved over my dick, the same way as over the rest of my body. At this point, I couldn’t stop moaning.
“Do you want a happy ending?” Ashley teasingly asked.
“Ohhh… Yes please,” I moaned.
At that moment her hand closed around my dick and started moving up and down on it. With her thumb, she rubbed the cum all over my glans, which was an even better feeling, and the other hand played with my balls. Her jerking hand kept alternating between a firm and a loose grip, which caused a build-up when it was firmer, and it went down a bit with the looser grip. I never thought of this before, but in my private jerk-off sessions, I’d definitely try this too.
I kept moaning constantly and each time I was close to cumming, Ashley squeezed my balls. Not to the point that it hurt, but enough for the tingling sensation between my balls and my anus to die down a bit. But as she kept increasing the speed of her fist, the inevitable was going to happen. The tingling spread from between my legs to my balls. And from my balls to my lower abdomen, until…
“Ahhh! I’m cumming, Ashley!” I groaned.
“OH, yes! Shoot, Jacob! Cum for me,” I heard Ashley say in the background.
My ears were beeping and my vision blurred. As the first spurt left my dick, Ashley’s finger slipped over my anus. I didn’t know if she did it intentionally, but it had an awesome effect on me. I came so hard, I almost screamed. All the time I heard Ashley moan as she kept milking my dick. She let go of my cock and moved toward my head. Before I knew it, she kissed me hard on my mouth and slipped her tongue between my lips. It was my first French kiss, but I figured out the mechanics of it quickly. Ashley moaned in my mouth while we were Frenching. Out of the corner of my eye, I saw her hand inside her thong. We kissed like this for a few minutes, before she broke the kiss.
“I’m sorry, Jacob. But this was so hot!” she said a bit apologetic.
“Huh?” I asked a bit confused. “What do you mean?”
“I shouldn’t be molesting you like this. It isn’t exactly professional, is it?”
“I don’t care. To me, it’s the best feeling in the world,” I honestly said.
“I don’t know why I find your dick so appealing,” she said, eyeing it and licking her lips.
“Don’t you want Brandon’s dick in your hand? Isn’t that what started all this?”
“Fuck Brandon!” she said and kissed me again.
After this kiss, she took a towel and cleaned the cum from my body. I was still as stiff as I could ever be, especially after Ashley cleaned my dick. She stood straight and looked me in my eyes with a look I never saw before.
“Let’s try the body-to-body massage,” Ashley said and started peeling off her thong.
I just had to look. Slowly her thong slid down her thighs, exposing more and more of her vagina. She had a small stripe of pubic hair, which looked great on her. Of course, this was the first pussy I ever saw in my life that wasn’t a drawing, and I didn’t know what to think of it. There wasn’t much to look at, so I decided I liked her tits better. After my sister was completely naked, she took the oil and started spreading it over her upper body.
“There,” she said after she was done.
I had a vague sense of what this type of massage was, and as she climbed on the table with me, I realized I was right.
“Relax, little brother. Enjoy this session,” she said with an odd tone in her voice.
Ashley started at around my knees and pressed her boobs against my body. She slowly moved her body upward, so her whole upper body rubbed against mine. When she was stretched out completely, she kissed me deeply. I felt the heat of her pussy against my hip and my hard dick was trapped between our slippery bodies. She moved her body down, all the time her boobs and upper body pressed against me. She reached my dick and pressed her boobs together, trapping my dick between them, and moved up and down a bit, mimicking a hand job. This wouldn’t get me off but was wildly erotic. This went on for a couple of minutes and I was horny as hell again after all this contact.
Ashley moved her body up again, and I could feel her shift a bit. She kissed me deeply again. At that moment, I couldn’t resist anymore and my hands grabbed her butt. She spread her legs and now I felt the heat of her pussy directly on my dick. Her hips started moving and she was grinding herself against my pole. My dick was already slippery, but the wetness of my sister’s pussy increased it even more.
Ashley was panting heavily and so was I, but she kept on grinding. If she kept going like this, I was sure I’d cum again in a few minutes. But she suddenly stopped moving and broke the kiss. She looked me deep in my eyes and moved her hips a bit further up my body.
“I don’t wanna wait any longer,” she groaned and reached between our bodies, took my cock in her hand, and pressed my dickhead against her warm, wet opening.
My heart skipped a beat or two, as I realized what we were about to do. Ashley had a very focused look on her face, as she started moving her body down again. At that moment I felt the tip of my dick enter my sister. I started moaning the moment I entered her.
“Fuck me, little brother. Fuck me!” Ashley said, moving down even further.
My thirteen-year-old virgin dick slowly entered my fourteen-year-old sister’s pussy. She didn’t stop once and just kept impaling herself on my dick.
“Ohhh… Jacob! You’re almost completely ins… ahh. I fee… grrmph,” Ashley said a little out of breath.
I couldn’t think straight anymore either. As the last part of my dick entered my sister, I had to do some math and think about dead kittens and stuff because my entire groin area was tingling. This was a lot better than her hand and way better than I ever imagined.
The moment our pubes merged, we both froze. This was it. We were officially no longer virgins. We looked each other deep in the eyes, and without using words we both knew what the other meant. I couldn’t explain it, but it felt magical at the time. Ashley nodded lightly and started moving her body up, making my dick beginning to slide out. She must’ve felt she was running out of dick because right before I would slip out, she moved back down again.
As she did this, the look on her face changed. Her focused look had made room for a more dreamy look as if she wasn’t quite with me anymore. My hands were still on her hips as she picked up the up and down pace. I saw her oil-covered tits jiggling in front of my face, and couldn’t resist. I moved both my hands from her hips to her boobs and started massaging the slick globes. Her nipples were extremely stiff and poking in the palm of my hand. It was a nice distraction from the feeling on my dick. I was feeling close to cumming, but massaging my sister’s tits, got the edge off a little bit.
“Hmmm. Ohhh, Jacob!” Ashley kept moaning.
As I felt sparks started flying between my balls and anus, I knew I wasn’t going to last much longer. I involuntarily started matching my sister’s rhythm, by lifting my ass from the table and practically slamming our groins together. By now Ashley was panting heavily and as I looked up at her eyes, I saw them cross and she clamped her lips together, so just a small stripe was visible.
My sister froze completely and her hands gripped my shoulders so firmly, it almost hurt. And that’s when I felt her pussy sharply contracting around my dick. Her mouth opened and she tilted her head back, so she looked at the ceiling.
“AHH… YESSS!!” she moaned.
I was approaching the point of no return and had no intention to stop fucking my big sister. So I kept slamming my hips against hers as she obviously came, and I kept massaging her tits. The contractions around my dick slowed down a bit, and Ashley looked down at me, still panting heavily. I could see the tip of her tongue in the corner of her mouth, so I figured she was concentrating hard too. I didn’t care. I needed to cum. There was only one thing in the world that mattered to me now, and that was filling up my big sister with my cum.
This thought scared me a little bit but excited me terribly at the same time. I kept slamming my groin against Ashley’s and all the time feeling the tension build up more. I was way past the point where I thought the build-up would end and I would cum. I’ve never felt this much on the edge of cumming before. I wasn’t thinking anymore, just sliding my cock in and out of my sister’s pussy.
And that’s when it happened. I saw bright sparks in front of my eyes and heard that beep in my ears again as I slid my cock deep inside for the last time. During this last upward motion, I felt my balls emptying themselves and by the time I was all the way in, the first spurt came out.
“HHHHH…” was all that left my mouth.
“Ahh! I feel it…” Ashley moaned. “AHHH!!”
I was still balls-deep inside my sister and emptying my balls, as I felt her pussy contracting again. This feeling prolonged my own cum even more. My balls were still contracting, but there just was no cum left anymore. I collapsed back on the table, and as I felt the contractions on Ashley’s pussy fade, she laid herself down on me. We laid there sweating, panting, and still slick from all the oil. Ashley started stroking my hair and my hands started caressing her back. If this was the way sex worked, I wanted it every minute of every day. I felt so at ease and so connected with my sister at this moment, that I wanted this to last forever.
“You’re amazing, Jacob,” Ashley whispered in my ear.
“YOU are amazing, Ashley,” I responded.
Not the most intriguing dialogue, but I was already glad that something came out of my mouth. Ashley started kissing me again, but this time it wasn’t enough to keep me hard. I guess two cums within thirty minutes, is too much. Even for a thirteen-year-old boy. As I slowly slid out, Ashley stopped kissing me and looked me in the eyes.
“And we haven’t even reached our final lessons,” she giggled.
“Wow. You’re right! I can’t wait,” I said and started laughing.
“Well. No matter what’s in these lessons, we’re doing this a lot more,” Ashley said seriously.
“Definitely!” I said. “I do think we need to wash the oil off our bodies, don’t you think?”
“Wanna shower together?” Ashley asked with a sly smile.
“Sure!” I responded enthusiastically.
And off we went to take a shower.
About three-hundred miles away, a young girl sat panting in front of a computer screen. Her big brothers hard dick was still balls-deep inside her, slowly deflating after he just fired his sperm into his sister once again.
“Sam? Will you come down, please? Brunch is ready.”
“I’m coming, mom! Just a sec.” she responded casually.
“Is Blake in there with you?”
“Yes. He is. We’re fine-tuning the software for the afternoon session.”
“Great! Will you both come down, so we can have brunch together?”
“Sure. We just have to save this and then we’ll come down.”
“This is awesome stuff, Blake. We have to help mom get more customers,” the girl softly said and started giggling.
“Don’t worry. I’m almost done with the new website. That’ll probably get us a lot of new customers,” Blake said as he slipped out of his sister and stood up.
With his dick so close in front of her face, she couldn’t resist. She took the soft cock in her mouth and licked it clean, as she did so often.
“Ahh. Stop it, Sam. We need to go downstairs, or our mom will be suspicious,” Blake said stepping back and started putting on his clothes. “Don’t forget to re-enable the blur option.”
“Don’t worry.” Samantha said, checked the ‘enable blur’ icon, and turned off the computer. “We’ve got to start recording this stuff,” she mumbled to herself.
Here you go, kids. A sweet, short little story. I focussed on keeping it short, and I think I managed. I know massaging it’s a chewed-out subject with these kinds of stories. But I just couldn’t resist. I also realize that this isn’t my best story. I miss the story arc and character development to be honest. But my goal was to keep it short and it came out easily. I also wanted to make a small reference to the current COVID situation, which resulted in this setup. Maybe if you read this story in a few years, you might wonder what the fuss was about. Or maybe not. We don’t know. I just knew I had fun writing it.
Amissis mihi locus