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Girlfriend's Son's Friends at Her Pool

IslandMan

TMF Expert
Joined
Sep 22, 2002
Messages
531
Points
18
Girlfriend's Son's Friends at Her Pool

This happened one summer afternoon 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 all also 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, neither did her kids. There was no answer. So I opened the door and walked in and called out her name. Nothing. Their yellow Lab greeted me, and I saw one of her cats, but no one answered.

So I walked out onto her back porch. Her 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 tan lines on her back. She always had a great tan during the summer. I had a good view of her gorgeous long legs and wonderful ass. Her feet were at the end of the chaise lounge with her soles facing up - in my mind, just begging to be tickled - but I did NOT expect what happened next!

I saw three of Mark's buddies, Dan, Matt, and Casey, on the other side of the pool. That explained the cars. All three were looking over at Lisa, and they were whispering to each other and laughing, but I couldn't hear anything they said as the music from a small boom box was still playing. 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. This was getting interesting.

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 exposed sole. Same reaction. Then they slowly tickled both of her soft arches and her feet moved a bit more and her toes scrunched up. I knew her feet were very ticklish, having tickled them on many occasions myself. And I had often fantasized about tickling her feet when she was asleep. Actually I had fantasized about a lot of things... but I digress.

As I continued to watch, 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 above the top of the chaise lounge, as his friends started really tickling the soles of her sensitive, now very defenseless, feet.

She woke up startled and already laughing with the soles of both of her feet being tickled... and I mean tickled. She tried to sit up but Dan was holding her wrists tightly. Matt and Casey had both of her feet in the air, one under each of their arms, and were really going to town tickling the bottoms of her feet with their free hands. They were laughing as they attacked her soft ticklish soles as she laughed and struggled to no avail. Dan laughed as well while the other two boys raked their fingernails over the bottoms of her sensitive feet. Lisa was trying to tell them to stop in between her screams of laughter, “OHHH NO... NO...AHHH.. HAHAHAHA.... PLEASE.... HEEHEEEE HAAHAA... STOPPPP....NOOOOOO!!” Casey was scrabbling his fingers over the creamy pale arch of her foot and Matt seemed to be focusing right under her toes as she laughed and squirmed and pleaded with them to stop tickling her defenseless feet. After a couple of minutes, they stopped briefly but did not release their grips.

Then I heard Matt tell Lisa that her son, Mark, had told them he overheard her talking to one of her girlfriends about how much her boyfriend liked to tickle her feet and how she really liked it! I was shocked. But to be honest, I was also pretty hard by that time. And 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 with moisturizer were delivered regularly... with a little tickling. Tickling had become part of our foreplay and I even tickled her feet when we had sex. Sometimes I would hold her feet up in front of me and tickle the soles while I thrust into her, and sometimes I would reach down and tickle them when we were doing it doggie style. Her feet had become much softer and more sensitive since we started dating, particularly the soles! I had even tickled and worshiped her feet while she masturbated for me on her bed a few times and even once on the stairs going up to her third floor bedroom! She told me that was SO hot !!

Lisa seemed shocked. They hadn't released their grips on her ankles, but now they were just rubbing her feet. Lisa, trying to look back at them, pleaded, “STOP IT! That's different! Now please let me go!!”

This was was getting me painfully hard !!!

Matt responded with, “C'mon Lisa, you know you like it!”, and he and Casey started scrabbling their fingers over the creamy pale arches of her helpless feet again. She burst into laughter and 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, “Which foot is more ticklish?”, as it looked like he was now using his fingertips under her long toes and then saying, “Uh oh... looks like you're really ticklish here!!” Lisa was going ballistic. Then I heard Matt say, “Cootchie cootchie coooooo!” as he wildly scrabbled his fingers on the arch of her foot. I knew I liked that boy!

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 laughed and stared at her cute pale ass cheeks which were now exposed as they relentlessly tickled the bottoms of her sexy feet. I was harder than Chinese arithmetic !!

I thought they stopped tickling for a minute to let Lisa catch her breath, I was wrong. 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 really tickling the bottoms of her feet again. Lisa was lost in laughter again.

With that, Dan pulled her wrists 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. It happened so fast, Lisa wasn't prepared for what happened. 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 was staring at my topless, incredibly ticklish girlfriend, captive, both of her feet being tickled, with her pale bare breasts exposed with her dark brown nipples pointing straight up toward the sky. 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. They had started really tickling the sensitive soles of her feet again, and had her feet up in the air with her legs spread farther apart now. With all her thrashing about, Lisa's bikini bottom was also pulled very tightly and was beginning to creep in between her lips down there, if you know what I mean! She was a sight to behold, topless, and now her sweet pink pussy lips were beginning to be exposed... it was was an incredibly hot scene, but it only lasted for a 15 seconds or so. The boys were tickling her feet and Lisa was laughing and bouncing around and squirming again with her hips now bucking up off the chair 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 quite stiff by the way. All three boys let go of her at the same time. She grabbed her bikini top and tried to cover up her breasts while getting up off the chaise lounge. She also pulled at her bikini bottom and was shaking while slowly walking away from them as she said, “It is time for you boys to leave now!”

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

She looked a mess... her hair was all over the place, she was breathing very hard and she was sweating. 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 put her bikini top back on. Then she poured herself a glass of iced tea and sat down, taking in more than a few deep breaths and 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!”

Minutes later, I was massaging Lisa's feet. As I slowly began to tickle the soft sensitive bottoms of her feet, she told me what had happened at the pool with Mark's friends. I took my time teasing her, reaching up and tickling her pussy through her bikini bottom. Then I stopped tickling her feet long enough to take her bikini bottom off and told her to tell me what happened in detail. She even started stroking her pussy herself as she thoroughly repeated the story as I massaged and lightly tickled her feet, telling me exactly how each of them tickled her feet and what they did. After that, I stopped tickling her feet and moved up to remove her bikini top. As I went around the side of the bed to do that, I undressed myself. Lisa took me into her mouth and sucked on my painfully hard cock. Minutes after that, I was inside her hot wet sweet pussy and tickling her feet again as they were up in the air. 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. After the initial shock and my reassurance that I would have intervened soon, she asked me if watching her get her feet tickled like that turned me on. I insisted on going down on her and asked her to tell me the story again as I licked and tickled and teased her beautiful pink pussy and tickled her feet a little more... before I really started to work on her clit.

A lot of intimate conversation took place after that, as well as more sexual activity... as I'm sure you can imagine. We finally went out to dinner about 7 o'clock !!!

Boy do I miss her.
 
Last edited:
Lisa_esque.jpg

These aren't Lisa's feet, but they look very close. She had 9½'s, very soft (I massaged & moisturized them often) and always kept her toenails painted.
 
WOW that's a wild story! You're a better sport than me, I could never share my wife or girlfriend like that. It must have been an AMAZING sight.
 
Thanks, CG!

We dated for less than two years. She had only come out of a 20+ year marriage less than two months before we met. It was an emotional rollercoaster.

But for me... that's the one that got away.
 
Absolutely wonderful story, and you've given me a new metaphor: "Harder than Chinese arithmetic." Masterful. Thanks a lot.
 
Wonderfully told story. Amazing turn of events. Thanks for sharing.
 
I loved that story. Barely legal guys tickling a MILF, one of my favorite fantasies. Thanks.
 
L
TOO BAD THE KIDS WEREN'T ON THE BALL AND HAD TIED HER TOP BEFORE THEY TURNED HER OVER. THEY COULD'VE GOTTEN HER SIDES AND PITS BEFORE THEY LET HER GO. (Sorry for the caps. I didn't realize the caps lock was on until I wrote the whole reply and I was too lazy to re-write it). :p
 
nice story ... I'd be hot & ready too if I had watched my wife/girlfriend getting that kind of attention....
 
You should have walked out and encouraged them to tie her down to the chaise, maybe toss 'em some rope. ;) Then pour a drink, pull up a chair, and relieve your "hard time."
 
I am sure I have read this somewhere else... Or I read it before and I did not comment....

Anyway, it is amazing.
 
Truly awesome story. Too bad you and she didn't last. And too bad you don't have some pics of her actual feet to share.
 
Thanks everyone for the kind words!

Truth is, I still think about her every day.

:sadcry:
 
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