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Girlfriend's Son's Friends at Her Pool
Published on Sunday, July 31, 2016

This story was submitted by IslandMan.

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This happened one summer afternoon a few years ago when I stopped by my girlfriend's home.

Lisa had a 19 year old son, Mark, her youngest, who was going into his freshman year in college. He and his friends were done with high school, but they were all still into skateboarding.  They spent a lot of at that house, they liked the fact that they could fly around, doing jumps on their skateboards, without worrying about traffic.  They also all loved the pool that Lisa and her ex-husband had put in the backyard behind their garage years ago.  It was an older rural home, but it was where she wanted to stay, where her two sons grew up, etc.  The pool had a nice private setting behind the garage, with a huge thick hedge on one side that ran the length of the property and a eight foot wooden privacy fence on the other side, front and back as well.

It was a Saturday afternoon and I had told her that I'd be down around 6 PM to take her to dinner, etc.  I usually run late, so after I finished my round of golf, I decided to shower and go straight to her house, to be early for a change.  I wound up getting there much earlier than I had told her, it was only about 3:30.  There were a couple of other cars in her driveway that I didn't recognize, so I parked up across the street in the bank parking lot.

I crossed the street and walked toward her driveway.  I went onto her back porch and knocked on the back door. (Lisa never used the front door and neither did her kids.)  There was no answer.  So I opened the door and walked in and called out her name.  Nothing.  Their dog greeted me, and I saw one of her cats, but no one answered.

So I walked out onto her back porch.  Lisa's car was there and the two other cars I mentioned.

As I walked toward her one car garage (which was always full of other stuff), I heard music coming from back by the pool.  It wasn't that loud, but I could hear it clearly as I got closer.  So I walked into the garage to go out the back door of the garage to the pool, which is what everyone did.  As I got closer to the back door, I could see Lisa stretched out, face down, on one of the chaise lounges sunning herself.  She looked quite relaxed, wasn't moving, and I guessed she was asleep.  She was wearing a bikini, with the top untied so she didn't get lines on her back. She always had a great tan during the summer.

I also saw three of Mark's buddies, Dan, Matt, and Casey, on the other side of the pool.  They were all looking over at Lisa , and they were whispering to each other.  It seemed like they were up to something, so I didn't open the door, I stayed out of sight and continued to watch through the door window.

Within a couple of minutes, all three of them walked, more like crept, slowly around the pool to where Lisa was laying.

When they got to her, Matt reached down and lightly tickled the bottom of her left foot. Her foot moved a little, but she really didn't stir.  Then Casey reached down and tickled her other sole. Same reaction. I was now enthralled.

Then Dan moved to the top of the chaise lounge and nodded his head, at which point in time, both Matt and Casey crouched down and started tickling the bottoms of both of Lisa's feet.  They started slowly as her feet began to twitch and move a bit.  Then all at once they grabbed her ankles, each wrapping one of their arms around her slender ankles.  At the same time, Dan grabbed her wrists, holding them together under the chaise lounge, as his friends started really tickling her sensitive feet.

She woke up startled and already laughing with both of her feet being tickled... and I mean tickled.  The boys were laughing and asking her which foot was more ticklish, as she laughed and struggled to no avail.  As Lisa laughed and pleaded with them to stop tickling her feet, they stopped briefly but did not release their grips.  Then I heard Matt tell Lisa that her son, Mark, told them he overheard her talking to one of her girlfriends about how much her boyfriend liked to tickle her feet !!    I was shocked.  But to be honest, I was also pretty hard by that time.  I knew that having her feet tickled turned her on now.  No one had ever paid any attention to her feet before me, and I made sure that foot massages were delivered regularly... with a little tickling.

As they tickled her sensitive feet, Lisa pleaded, “That's different! Now please let me go!!”

Matt responded with, “C'mon Lisa, you know you like it!”, and started scrabbling his fingers over the creamy pale arch of her helpless foot.  She burst into laughter again.  She squirmed on her stomach as both boys tickled the soft soles of her feet.  As she continued pleading and struggling, her bikini bottom was riding up and showing more and more of her delicious ass.  Casey now taunted her, asking again, “You still didn't tell us... which foot is more ticklish?”, as he now was using his fingertips under her toes.  Lisa was going ballistic.

The tan lines on her ass were now more than clearly visible, her bikini bottom had ridden up and was now more like a thong.  Matt pointed that out to Casey and they both stared at her wiggling bottom as they relentlessly tickled the bottoms of her defenseless feet.  By then I was harder than Chinese arithmetic !!

I thought they stopped tickling for a minute to let Lisa catch her breath, but that's when I heard Dan say, “Let's turn her over!”

Immediately Lisa objected, saying that Mark would be home any minute.  Matt quickly responded with, “No way!  Mark went to that skateboarding competition in York and it won't be over until at least 6 o'clock!”, and then both he and Casey started tickling her feet again.

With that, Dan took her wrists out from under the chaise lounge, pulling them together toward him, stretching her out even more.  As if on queue, Matt and Casey took her ankles out from under their arms, grabbing each ankle with both hands, and flipped her onto her back.  They may not have intended to do it, but her bikini top fell onto the cement below her chair and Lisa was now topless, on her back, with her arms being stretched up above her head!   I almost came in my pants.

Matt and Casey had already firmly wrapped an arm around each of her ankles again, so they were kind of facing away from her, and they had started really tickling her feet.  Lisa was laughing and bucking and squirming again when they heard Dan yell, “Wait! Wait! STOP!!”  It took a few seconds for everything to settle down.

It was like time stood still.  Everybody stopped.  Lisa realized that she was topless about the same time Matt and Casey did.  Dan was the lucky one who had more time to gaze at her beautiful breasts and perfect dark brown nipples, which were hard by the way.  All three boys let go of her at the same time.  Lisa grabbed her bikini top and tried to cover up, slowly getting up.  She was shaking and slowly walking away from them as she said, “It is time for you boys to leave now!”  The boys stood, dumbfounded, watching her walk away.

I quickly and quietly ran back out the front door of the garage, fast enough that I was just walking up the driveway when Lisa came out of the garage.

I asked her if everything was OK, saying that I thought I heard her laughing as I was walking up the street, and that I heard other voices.  I told her that I had parked over in the bank parking lot because of the other two cars in her driveway.  She took my hand and we went into the house.  As I was standing in the kitchen, Lisa immediately put her top back on.  Then she poured herself a glass of iced tea and sat down, taking a few deep breaths and big gulps.  She shook her head and said that the other two cars were from Mark's friends, three of them, and they'd been at the pool.  Then I saw the two cars pull past the kitchen window and out of the driveway.

She walked over and locked the kitchen door.  She said she wanted to tell me what happened, but that we should go upstairs first.  I said OK and again asked her if everything was alright.  She said, “You'll get the whole story as soon as we're in bed!”

Ten minutes later, I was the one tickling Lisa's feet, but this time, they were up in the air and she was naked.  We only lasted a few minutes until we both exploded.  The first time.  As I was inside her for the second time that afternoon, I confessed to her that I had witnessed the whole event.  A lot of intimate conversation took place after that... as I'm sure you can imagine.   We finally went out to dinner about 7 o'clock !!!

Boy do I miss her.

This story was submitted by IslandMan.

You're encouraged to post your comments here in our chat forum's story section.

To read his next story, go to Winter Break with Son's Friends at the Gym.

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