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Winter Break with Son's Friends at the Gym
Published on Sunday, July 31, 2016

This story was submitted by IslandMan.

To read his 1st story, go to Girlfriend's Son's Friends at Her Pool.

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This is sort of a continuation of the story about my girlfriend's son's friends tickling her at her pool a few summers ago.

Matt, Dan, and Casey were all back from college on winter break. They were hanging out at Dan's house having a few beers, talking about their experiences at college, who they were dating, and what kind of mischief they could get into over the winter break. As they drank more, Casey brought up their experience of tickling Lisa at her pool, how hot and ticklish she was, what great nipples she has, and that he hoped they could do it again this coming summer!  Casey immediately asked if anyone had told Lisa's son, Mark, what they had done. Matt and Dan immediately replied that they had shared nothing with Mark about what happened. They all agreed that it should remain their secret – top secret - and they would share it with no one!  Dan then insisted that he should get to do some tickling the next time, because last time all he got to do was hold her wrists!  Matt immediately countered with the fact that Dan got to look at her breasts and nipples much longer than he and Casey.  Dan then argued that Matt and Casey had a better view of her pussy lips sneaking out around her bikini bottom crotch.  Matt said that he might have an angle where they wouldn't have to wait until the summer to tickle Lisa again. He said to give him a day to work out the details!

It turned out that Matt was dating a girl, Megan, who was now working at the gym that Lisa went to in the mornings. She had mentioned this fact to Lisa's son Mark while he was with Matt, when they ran into her at the pizza shop a few days before. Megan was talking about the fact that Lisa always went in to use one of the tanning beds after she worked out. She laughed about Lisa always falling asleep and Megan would have to go into the room and wake Lisa up. Lisa apparently was a very heavy sleeper and even the sound of the tanning bed shutting down didn't wake her. Megan said that it wasn't uncommon for people to fall asleep on the tanning beds with the music blaring and the eye protectors blocking out all light.  Matt asked her how she got into the room and Megan explained that the doors to the tanning bed rooms no longer had locks, in case of a medical emergency.

So... after Matt, Dan, and Casey had their discussion about getting the chance to tickle Lisa again, Matt decided to have a conversation with Megan and offer her some incentive to cooperate in his plan. Megan agreed to help, but she wanted $150 in cash. Matt told her that shouldn't be a problem but that he would have to talk to the other guys.

Matt shared the details of his plan and the costs involved that evening with Dan and Casey. They both quickly agreed to split the cost evenly and the three of them set to mapping out the timeline and specifics.

Megan had shared with Matt that she was the only employee who came in until 8 AM, and that Lisa came in every Monday morning and that she was usually out of there well before 7 AM.  She also stated that on Mondays there were generally fewer people in the gym and using the tanning beds as well. Given the fact that their winter breaks were relatively short, the boys decided to execute their plan that coming Monday morning!

Each of the three young men made up a story about staying at one of the others houses that Sunday night, so their parents wouldn't be suspicious.  They met at 5 AM in the smaller parking lot / delivery area behind the building which housed the gym. The gym opened at 5:30 AM and Megan arrived about 5:15, unlocked the employees' entrance and escorted them in. Matt had the 'supplies' he thought they needed in a brown paper bag with him. Megan first showed them the tanning bed room that she would direct Lisa to use. Then Megan took them to the office, which was a perfect place for them to hide, but have a clear view of the gym, because the front side of the office had a huge one-way mirror facing out. Each of the boys then gave Megan $50 and she promptly went out to the front desk and sat down to count her money.

Sure enough, a little before 5:50 AM, Lisa came in through the front door and waved to Megan who was behind the desk in front of the office window. The boys were hardly able to contain themselves!

Lisa spent a little time on the treadmill, then the elliptical, then the universal gym, doing many repetitions with lighter weights at all the stations. The boys were whispering to each other about how good she looked, how tight her ass looked, what a great dark tan she had and wondering about her tan lines!  It then occurred to Matt that she might not actually wear anything when she uses the tanning bed, but he didn't say anything to Dan or Casey.

About 6:30 AM, Lisa approached the desk and asked Megan which tanning bed she should use. Megan told her to use bed #5, since that was in the back corner of the building and farthest away from the gym floor.  Megan was also happy that there were only four other people in the gym and no one else was using the tanning beds that morning. She also made sure that the music was turned up, playing louder than normal throughout the gym. Megan told Lisa that she would turn on the tanning bed in 2 minutes and that she'd see her in about 25 minutes.

Lisa walked around the corner and went directly back to tanning bed room #5, went in and closed the door. Megan told the boys to wait at least 10 minutes and to be very quiet when they opened the door to peek in to make sure that Lisa was soundly asleep. Dan set the timer on his watch for 10 minutes.  Megan assured them that Lisa always wore eye protection and always fell asleep, and that she had also turned up the music on the tanning beds.  Megan told the boys that it was all up to them now and if they got caught, she had no knowledge of what was taking place, and that they must have sneaked in the back door which she had left unlocked. Then she went back out to the front desk and sat down.

The boys were so excited they could hardly contain themselves, all of them sporting hard-ons by now. Fifteen minutes seemed like an eternity!

Finally Dan's watch beeped. He turned it off immediately and the three of them looked out through the one-way mirror. All was quiet. Megan was sitting at the desk reading. Four people - three women and one man - were all focused on their workout routines, and the bonus was it looked like all four of them had MP3 players with earbuds. Perfect!

Matt opened the bag and took out a large black blindfold and three pairs of sunglasses for them. He showed them the 'blindfold' and told the them he wanted to make sure Lisa wasn't able to see anything, and that when they started tickling her, she would undoubtedly thrash around and the eye protection goggles would undoubtedly fall off. They all agreed that was smart thinking.

They quietly walked back the hall, happy to hear the loud music from the gym also emanating from the tanning beds.

Matt very quietly open the door just a little. All three of them could see the glow from the tanning bed, and Lisa's feet visible at the end closest to the door. Matt crouched down to see if she was moving at all and make sure she was asleep - it was then he realized that she was naked!  He put his finger to his lips and then leaned over and whispered to Dan and Casey the good news. Dan was worried about Lisa's nudity, but his hormones were raging and he chose not to say anything.  Casey then crouched down to confirm Matt's assessment. "God her nipples look good!" he whispered to Dan when he got back up.

Moving slowly and quietly, the three young men stationed themselves as they had discussed. Casey was above her head and would be responsible for holding her arms. Matt was next to him and he would be tying the blindfold over her eyes around her head, while Dan at the bottom end of a tanning bed held her ankles if she woke up while that was happening. Matt had told the other two that he would very gently put the blindfold on her and really try not to wake her up.

They put their plan in action. Matt and Dan slowly and quietly lifted the top of the tanning bed up away from Lisa's nude body. She didn't move. Dan was in place to grab her ankles if she startled and he had a wonderful view of her smooth shaved pussy lips and the dark landing strip of hair just above them. Casey was in the corner at the top of the tanning bed as Matt started to slide the blindfold underneath Lisa's neck so that he could tie it over her eyes without lifting her head. He was really glad it was such a big piece of fabric. He had actually purchased a very small black tablecloth to use as a blindfold!  It was on - mission accomplished!  There was no way that Lisa could see anything. It took tremendous restraint and focus on Matt's part not to take more time staring at her wonderfully naked body, so now he stepped back for a minute to examine their prize.

Dan pointed to his watch and they realized it was time to start the tickling!  Matt took his place next to Dan and they both started to very slowly and gently tickle the bottoms of Lisa's soft sensitive feet. She didn't respond at all. They smiled knowing that she was sound asleep. With that knowledge, Casey reached down and lightly touched her nipples. They were soft and warm, having been just inches from the tanning bed lights moments before. Matt, having seen what Casey had just done, reached up with one hand and ran a finger over her warm smooth pussy lips. Dan watched all of this but remain focused on tickling the sole of Lisa's right foot, and as he got just under her toes, she started to move her feet a little bit and crunch up her toes. Matt returned his focus to tickling her left foot, slowly gliding his fingernails up and down the creamy pale arch.

Lisa was a really sound sleeper and was hardly responding to the tickling. She still hadn't moved her arms at all which were still down by her sides. Casey had nothing else to do, so he reached down with both hands and played with her dark brown nipples, which were now starting to get hard. Dan had also reached out to tease her pussy lips a little, and when he did, they parted slightly. It startled Dan a bit, so he went back to tickling the bottom of her right foot. Matt noticed what had happened, and he reached up and teased her pussy a bit more, moving one finger very slowly up and down in between those lips.

Dan and Matt weren't sure whether it was Casey playing with her nipples or Matt tickling her pussy - but Lisa seemed to be getting a little wet down there. The bright lights from the tanning bed definitely highlighted the moisture forming in between her very sweet, slightly parted pussy lips.  Casey was now gently pinching her dark brown nipples and pulling them up in the air a bit.  Dan reached up and actually put the tip of his finger into her pussy and wiggled it around just a little bit!  Lisa actually let out a very soft little moan. It kinda' surprised Dan, so he went to tickling the bottom of her right foot. Matt looked over at Dan as he was scrabbling his fingernails over the bottom of Lisa's left foot and whispered, "Kitchee kitchee kooooo".  Lisa's feet were now moving back and forth a bit more with her toes occasionally scrunching up.  Both Dan and Matt were both tickling her feet bit harder while Casey alternated between playing with her nipples hand reaching down to tickle her smooth tanned tummy.  Lisa now had a smile on her face and slowly moved her head from side to side.  They also noticed her pussy was officially as Matt whispered to Dan that he was going to tease her clit. Matt then ran a finger up and down inside the entire length of her sweet wet pussy lips and then showed his wet finger to Dan. Dan smiled and then asked Matt what they would do if she woke up. Matt really hadn't thought that far ahead and he asked them how much time they had.

Dan looked at his watch and then motioned to the other two. The three boys had a very quick, very quiet meeting next to the tanning bed while watching Lisa's sweet naked body beside them.  The three of them decided to get the hell out of there before Lisa woke up. Matt hadn't planned any exit strategy and was glad to have the opportunity for a clean escape! He gently removed the little table cloth / blindfold without disturbing the eye protecting goggles. Then Matt reached down and teased both of her dark brown nipples, which were now quite stiff. At the same time, Casey went to the lower end of the tanning bed and started tickling both of the soft sensitive soles of Lisa's feet as he stared at her smooth sweet wet pussy. Dan reached down and ran his finger between those wet smoothly shaved lips, then brought it up and put it in his mouth.  Then Matt did the same.  Lisa moaned a bit louder and moved her feet back and forth, as Casey was really tickling them, and her lips parted as her smile widened. They stopped touching her and Matt waved his hand back and forth just above the eye protection goggles. Nothing - no movement - Lisa still seemed like she was sound asleep!

The three boys spent a minute just staring at Lisa's nude body before they lowered the top of the tanning bed and quietly sneaked out of tanning bed room #5.  All three of them jumped into the car and as soon as they were out of the parking lot began screaming, laughing, and high-fiving each other!  On the way back to Matt's house, they talked about whether they could each afford another $50 before winter break was over! They also agreed to spend more time at Lisa's pool this coming summer!

Immediately after the boys closed the door to tanning bed room #5 - Lisa reached up and removed the eye protection goggles. With a big smile on her face, she reached down and began to play with her already wet pussy. She closed her eyes and imagined the boys tickling her and teasing her and having their way with her. She imagined them holding her legs apart, tickling her feet, while one of them licked her juicy pussy. It didn't take long for the orgasm to overtake her. As she rubbed her clit and arched her back, with visions of the three boys tickling her and pinching her nipples - the juices flowed from her sweet pussy as she climaxed.  Hard.

As Lisa laid there in the glowing aftermath of a wonderfully strong orgasm, she began to think about ways that she could discreetly offer her ticklish body to her son's three friends again! As she thought about it, she reached up and started to play with her hard dark brown nipples, wondering how much time she had left until the tanning bed shut off.


This story was submitted by IslandMan.

To read this author's next story, go to "The Nude Beach Incident".

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

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