Oh, No! Oh, Yes

A few years ago, I was away on business when this incident happened. It started a string of events that I couldn't have imagined. My wife and I will occasionally send each other some naughty pics and messages while one of us is gone. Sometimes funny, sometimes super naughty, whatever the mood might be. On this one particular night, I was in my hotel room lying naked on my bed, with my hard cock in my hand when I snapped a picture and prepared to send it to my wife. I attached the picture to my email and lazily began to type in her address. The auto-fill function on my email completed her address for me after typing in the first few letters and I clicked send. That's when my heart sank. I realized I was looking at an email that was just sent to my wife's older sister. Their names are very similar and begin with the same letter and I hadn't even realized at the time the wrong address was added. Oh no.

My wife and her sister are both in their mid-40s and my sister-in-law is also very attractive like my wife. We are very friendly with each other, but not to this extent of course. I instantly panicked while sitting there, not knowing what to do. I decided the best thing was to email her again and apologize for sending her the picture that showed me from the waist down holding my rock hard cock in my hand. I did my best to explain that this was meant for my wife and I had accidentally sent this to her. I'm sure it sounded like a bunch of B.S., but I immediately sent the 2nd email anyway trying to explain.

About 40 minutes later I see a response from my wife's sister in my inbox. My heart sank again and I was afraid to open it to read what it might say. I took a deep breath and clicked on it.

Her response:

"hahahaha... no worries. My sister is a lucky girl if she gets to play with that all the time. Thanks for the free show!"

Needless to say, it was a huge relief to read her response and realize that she was very cool about the situation. I emailed her back and thanked her for understanding and made a comment that now she knows how perverted her sister and I are. I also mentioned that I was glad I didn't accidentally send her the short video I made on my last trip. (I realized at this point I was provoking the situation a little bit).

Her response:

"A video?? Wow... I can only imagine. Well, if you did "accidentally" send that to me, I promise I won't view it!"

Damn. Should I do it? Will she think I'm even more of a perv if I follow up on it? Being that I had a few drinks in me, I thought what the hell. I found the video and attached it. It was about a 1 minute video of me sitting on a chair and stroking my hard cock. At the end, I shot 3 or 4 long ropes of cum all over my chest and stomach. Needless to say, it was very graphic. Again, my heart raced a little bit, but I clicked send.

Her response:

"Wow! Is all I can say. I must admit you made me a little wet watching this."

I couldn't believe I was having this conversation with my wife's sister. Unbelievable.

I emailed her back and said I was glad she liked the video and now I have something to think about next time I played. I told her knowing that she's seen me cum was a huge turn-on.

Over the course of the next few days we emailed each other back and forth about a dozen more times. I won't bore you with all the details but where we left off was that I told her I would love to secretly masturbate for her in person the next time the situation presented itself. She brought up that in about a month our families would be getting together at their parents cabin for the holiday. "That might be a fun time" is what she said.

Fast forward a month and our families had all arrived the large cabin. It was my family, my in-laws and their parents. We'd be there for 5 days.

When we first saw each other we gave a coy smile and polite hug as we always do. There was so much sexual tension in the air I was afraid everyone else would notice. The long weekend began and my mind constantly raced as to when or if this was going to happen. I didn't want to be too persistent but I was constantly aware of every situation to see if any time presented itself as the right time. It was tough. There were so many people in the house that there was hardly a moment any of us were alone.

On the second night, my wife's sister and I found ourselves alone in the kitchen making some drinks to take outside to the bonfire. We knew it wouldn't be long before we were no longer alone so I quickly told her that I was a little embarrassed seeing her in person knowing she's seen 'all of me'. To my surprise she told me not to be embarrassed and that over the past month she's thought about it a few times while she was alone. Wow, did she really masturbate thinking about me? My mind raced with these thoughts. I told her what a turn on that was and that I was going to need some relief soon.

"Oh really?" she said.

I instantly came up with a plan in my head and told her in the next 30 minutes or so I was going to excuse myself from the bonfire to use a particular restroom and get some 'quick relief'. I told her if she 'accidentally' walked in on me, she might catch me cumming again. She looked at me with a coy smile and returned to the group outside.

We joined the rest of the family around the fire and drank and had some laughs for a little bit. About thirty minutes later I decided to make the move. I casually got up from my chair and told my wife I was going to use the restroom and get another drink. She gave me her wine glass and asked for a refill on my way back. Her sister gave me a quick look, but I was unable to tell if she was going to follow through or not.

I went to the bathroom next to our room where we were sleeping. It was a bit out of the way of the back door and kitchen where the group was. Upon entering the bathroom, I quickly unzipped my jeans and pulled my cock out. I began stroking it and getting hard, hoping my sister-in-law would show up. I was nervous but excited at the same time. I couldn't waste time if she did show up, so my plan was to be fully hard and ready to go.

Then it happened. I heard a faint knock on the door. I opened the door just slightly and saw that it was indeed her standing there. I opened the door and she had the biggest smile on her face. She didn't want to come in and shut the door because we needed to be on the lookout for family members. She stood in the doorway and simply said, "Do it, I want to see." And for the first time in person, I slid back down my underwear and exposed my hard cock for her to see. I started stroking hard and fast for her. She just stood there staring at my cock as I stroked for her. This went on for about 30 seconds or so and she said, "Hurry, cum for me."

Being extremely turned on by the situation it was easier than I thought, considering the pressure of her telling me to hurry. I turned slightly to face the sink and started cumming all over. She stood there and watched me cum and it was such a huge turn-on. This entire episode probably last a minute but it was amazing. I stood there in from her, cum dripping down the shaft of my cock and all over my hand and just soaked in the moment. As I began to clean up, she surprised me again and reached out and cupped by balls and gave them a little squeeze and said 'thank you' and walked away.

She returned to the group and a few minutes later I joined them all with re-fills in hand. Nobody suspected a thing.

Over the new few days, we would secretly flirt with each other verbally when we found ourselves alone for a second. it was a fun game of cat and mouse trying to avoid getting caught by our family members. I would tell her that I just masturbated in the shower thinking about her ass and things like that. I kept reminding her how much I enjoyed looking at her ass and how I wanted to feel how wet she gets. We had a great time teasing each other back and forth.

On the second to last day of our vacation, we were all getting ready to go out for the day. My wife's parents were on the complete opposite side of the cabin with their own bathroom. My wife and I were in our own room right next to her sister and her husband. We shared a bathroom in the same hallway in between both rooms. This morning was our last but most exciting encounter of the weekend. My sister-in-law was the first in the shower that morning and when she got out she went to her room to finish getting ready. As soon as the bathroom was empty it was my wife's turn to take a shower. The men, of course, would go last. My sister-in-law's husband was outside on the back porch having coffee. I started thinking this may be our last good chance.

I heard my wife shut the bathroom door and eventually turn the shower on. My sis-in-law's door was shut, but not all the way. I opened it ever so slightly and told her it was me. I opened it a little more and she was standing there wearing her towel and looking great with her wet hair. I said, "wanna watch again?" She looked at me and smiled and asked where her husband was. I told her he was comfortable on the back porch and we probably had a couple of minutes of privacy. We didn't want to go into one of the rooms because we couldn't see if someone was coming or not. Believe it or not we went out into the hallway, because it allowed us to see her husband out in the back and hear my wife in the shower at the same time. So there she was standing in front of me with wet hair and her body wrapped in a towel and I was in a pair of shorts and a t-shirt. More comfortable this time, I lowered my shorts and underwear exposing my cock to her again. I could tell she was enjoying the show and she kept staring at my cock while occasionally looking out to make sure her husband hadn't moved.

I asked her if would show me her body and with no hesitation, she opened up her towel, showing me her beautiful tits (about a C cup I guessed) and a nicely manicured bush. Her dark brown bush was so sexy, I couldn't believe she was showing it to me. It was so hot. I told her how much I loved seeing her pussy and tits. After a second or two she closed up her towel a little bit and continued to watch. I then proceeded to ask if she would show me her ass and she slowly turned around and removed the towel again exposing her sexy round ass with some adorable tan lines across her cheeks. I stroked for a few more seconds with my eyes locked in on her butt. I reached out and cupped one of her cheeks and she arched her back a little bit to my surprise and stuck her butt out more.

"Do you like?" she asked.

I just confirmed to her how much I loved it. I kept stroking faster and scooted closer to her ass until the tip of my cock was actually touching one of her ass cheeks.

"Are you going to cum on my ass?" she whispered to me.

"Yes babe. I want to cum all over your sexy ass" I said to her.

"Mmmm, I like that," she said. "You better hurry, we're running out of time."

I wasn't sure if I was overstepping my boundaries or not, but I decided to grab both of her ass cheeks and spread them apart. There we were, standing in the hallway of this cabin, my wife in the shower a few feet away, her husband on the back porch and her parents in their room getting ready for the day... and my sister-in-law was standing in front of me slightly bent over, letting me spread her ass cheeks apart. Unbelievable. I grabbed my hard cock again and began stroking faster and faster. The tip of my cock was slightly pushing against the crack of her ass and very close to her asshole. My hand stroked my shaft and would slap against her cheeks at the same time.

"Cum for me baby" is all she said and a second later I was ready. I pushed forward a little harder and guided the tip of my cock against her ass just slightly. She pushed back letting me know it was okay. I began cumming and felt my cock pulsating and pumping cum in between her ass cheeks. It was amazing. Hearing her soft moans while I came was something I will always remember. I stroked slower and slower while her entire ass crack filled with cum. When my orgasm subsided, I took a step back and admired her beautiful ass, soaking wet. It began running down her leg and she cleaned some up with her towel and said I better go get cleaned up. And with that, she wrapped herself up and walked into her room and shut the door.

I returned to my room and a few minutes later the shower stopped. My wife came into the room and said "Your turn!"

We all got ready and had a great rest of the trip. Nobody ever suspected a thing. My wife's sister and I had a few more fun encounters at later times, but I'll save that for another story.

I'm so glad that email was sent to her.