That was this summer. I had very long relationship and last year i got ridden of it. So I sex occasionally wit various girls till then. One night this September I was very very tired of everything. Job went finally better and some private investing also, but I had being working for 14 hours a day at time. It was About 1 am in the morning and was just went of from long shower and about to lay down on my bad.The voice from the other side of cell phone was very pleasant, some kind of baby talking voice. Voice said" Annnn' what what do want from me now?...LOL.. i said "who is this?&... Continue»
I was away on business for 3 days a while back and when this happens, my wife and I
will occasionally send each other some naughty pics of each other. On this one night, I
was in my hotel room lying naked on my bed, with my hard cock in my hand when I
snapped a picture of cock 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 s****r. Their names are very similar and begin with the same letter and I hadn’t
even realized at the time the wrong name was added. Oh no.
My wife and her s****r are both in their mid-30’s and my s****r in law is also very
attractive like my wife. We are very friendly with each other, but not to this extent and
never really sexually. I instantly panicked while sitting there, not knowing what to do. I
decided the best thing to do was email her again and apologize for sending her the
picture that showed me from the waist down holding my hard cock in my hand. I briefly
explained to her this was meant for my wife and I had somehow accidentally sent it to
her. I’m sure it sounded like a bunch of crap, but I immediately sent the 2nd email to
her trying my best to explain.
About 40 minutes later I get a response from my wife’s s****r in my inbox. My heart
sank again when I saw the email and I was afraid to even open it to read what it might
say. I took a deep breath and clicked on it.
My s****r in law’s response:
“hahaha… no worries. My s****r is a lucky girl if she gets to play with that all the time.
Thanks for the free show!”
It was such a 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 s****r and I are while I’m away on business. I
also mentioned that I was glad I didn’t accidentally send her the short video I made on
my last business trip. (I realized at this point I was provoking the situation a little bit).
This is where it got interesting.
My s****r in law’s response:
“A video?? Wow… I can only imagine. Well, if you ‘accidentally’ send that to me I
promise I won’t view it, wink wink!”
Damn. Should I do it? Will she think I’m even more of a perv if I follow up on it? (if that’s
possible.) Being that I had a few drinks in me, I thought what the hell. I found the video,
attached the short video of me masturbating and clicked send. It was about a 3-minute
video of me sitting on a chair and masturbating. 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.
My s****r in law’s 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 s****r. Unbelievable.
I emailed her back and said I was glad she liked the video and now I have something
to think about the 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 large cabin for the holiday. “That might be a fun time” is what
Fast forward a month later and our families were together all staying in the same
house, along with my in-laws (it was a huge cabin). We would be there for 5 days.
When we first saw each other we gave a coy smile and a 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 there was hardly a moment any of us were alone.
On the second night, my wife’s s****r 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 told her that I was a little embarrassed seeing her in person
knowing she’s seen ‘all of me’. To my surprise she said, don’t 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 I turn on that was and that I thought I was going to need some relief very soon.
“Oh really?” she said. I instantly came up with a plan in my head and told her that in
about 30 minutes I was going to excuse myself from the bonfire outside to use the
restroom and go to a particular bathroom for some ‘quick relief’. I said, “If you
‘accidentally’ walked in on me you might catch me cumming again”. She looked at me
and gave me that coy smile and returned to the group outside.
We joined the rest of the f****y around the fire and drank and had some laughs for a
bit. About thirty minutes later I decided to make the move. I casually got up from my
chair and told my wife I needed to use the restroom and I’d be right back. She gave
me her empty wine glass and asked for a refill on my way back out. Her s****r 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 rooms where were sl**ping. 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 it
hard, hoping that my s****r 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 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 that would
just be bad and we needed to be on the ‘lookout’ for f****y members. She stood in the
doorway and simply said, “Do it, I want to see”. And for the first time in person, I slid
my boxers down and exposed my hard cock for her to see. I started jacking off hard
and fast for her. She just stood their staring my cock as I stroked for her. This went on
for about a minute 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 turn on. This entire episode probably lasted a
minute but it was still great. I stood there in front of 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 my 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 next 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 f****y members. I would tell her that I just jacked off 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 and 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 of the
day. My wife’s parents were on the complete opposite side of the cabin with their own
bathroom, etc… My wife and I were in our own room right next to her s****r and her
husband’s bedroom. We didn’t have our own bathroom room but we all just ended up
using the same one that was near our rooms. This morning was our last but most
exciting encounter of the weekend. My s****r 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 would go last
as we didn’t need as much time to get ready. My s****r in law’s husband was outside
on the back porch reading the paper and having some coffee. I started thinking this
may be our last good chance.
I came out of my room and heard the bathroom door shut and the shower turn on. My
s****r in law kept the door cracked and I slipped my head and saw her wearing only a
towel while she put on some makeup. I said, “wanna watch?” 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 secretly see her husband out
the back window and listen to 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
some gym shorts and a t-shirt. More comfortable this time, I lowered my shorts and
boxers 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
I asked her to 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, and I could believe she was showing it to me. It was
so hot. I told her how much I loved seeing her pussy and tits and she closed up her
towel and continued to watch. I asked her to let me see her ass and once again she
turned her back to me and lifted up the towel exposing her sexy round ass with some
adorable tan lines across her cheeks. I reached out and cupped one of her cheeks
and she arched her back a bit and stuck her butt out a bit more for me. “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 her ass cheek.
“Are you going to cum on my ass?” she whispered to me? We started whispering dirty
things to each other. “Yes babe. I want to cum in your sexy ass”… “mmmm, I like that”
she said. “You better hurry, we’re running out of time” she responded.
I wasn’t sure if was about to overstep 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, her husband on the back porch and her parents in
their room getting cleaned up and my s****r in law with her ass peeking out from under
her towel, letting me spread her cheeks apart. I grabbed my hard cock and wedged
the tip in between her cheeks and began stroking faster and faster. The tip of my cock
was slightly pushing against her asshole as my hand stroked my shaft and would slap
against her cheeks at the same time. I will never forget that image of me masturbating
my cock while it was wedged in between her cheeks. “Cum for me baby” is all she
said and a second later when I was about to cum, I pushed forward a little harder and
guided the tip of my cock into her ass. She pushed back a little letting me know she
wanted me in her. I began cumming and felt my cock pulsating and pumping cum in
between her cheeks. When my orgasm subsided, I took a step back and saw my
s****r in law’s beautiful ass crack dripping with my cum. 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 her self 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 time the rest of the trip. Nobody ever suspected a
thing. My wife’s s****r and I had a few more fun encounters at later times, but I’ll save
that for another story. We agreed never to have sex, but these secret masturbation
games we played were so much fun. I’m so glad that email was sent to her.