It was eight years ago that I first met Lisa. I was in my early 40s and a new dad, while Lisa was in her late 40s, a bit curvy, with stunning blue eyes, straight shoulder-length blonde hair, a warm smile, and a friendly, outgoing personality. She was one of the teachers at my son’s pre-school. Typically, my wife Sara took care of dropping our son Billy off at school and picking him up. As a result, she became friendly with many of the teachers and had common friends with them. One day I went along and she introduced me to some of the other teachers, including Lisa. I was instantly attracted. Due to her outgoing personality, hellos and goodbyes with her were friendly hugs. My wife noticed the attraction and jokingly called her my girlfriend and Lisa jokingly called me her boyfriend (even though she was married and a mom).
The preschool had a day camp that Lisa’s teenage daughter Meghan worked at. Billy liked Meghan and we began to use her as a babysitter. She had her mom’s blonde hair and blue eyes, a slim figure, but a young face. She was 16 and I never thought of her as anything more than a cute kid who was babysitting. Even though I told her she could call me by my first name, Gary, she always called me “Mr. L”.
She babysat for a few years and even after she turned 18, she was still the cute kid who babysat. So no stereotypical fucking the babysitter fantasies existed. On the other hand, fucking the babysitter’s mother was a fantasy. I very much wanted to get between Lisa’s legs.
Meghan had graduated high school and was going to college on the opposite side of the country and Billy moved up from the preschool and started kindergarten at a new school. So Sara and I didn’t see Lisa (or Meghan) much anymore. It was a half-day kindergarten so we occasionally convinced Billy to go visit his pre-school teachers, at which times we saw Lisa briefly.
Three years later I saw them again, at the funeral for Lisa’s dad. Sara got called in for a work emergency so I had to go alone. Upon seeing me, Lisa had the same warm, friendly personality greeting me with a hug in front of her husband, who I had met several times before. She was telling family and friends about how she had my son in her pre-school class, we’d jokingly call each other boyfriend and girlfriend and Meghan used to babysit for me. It was also my first time seeing Meghan since she went off to college and although her figure and breasts developed nicely she still had a youthful face, so I still thought of her as the “cute kid babysitter”
Over the next two years we didn’t see each other at all. In those years, both marriages ended up in divorce. Sara got custody of Billy and I got a small apartment a town over. Then I landed a job 25 minutes away in the same town where Lisa lived. Although we hadn’t seen each other in person, we had kept in touch on Facebook.
Lisa got possession of her family’s two-story home and swimming pool in her settlement. During a recent hot spell, she said that Meghan occasionally stopped by to visit. She also asked if I wanted to come over and use the pool, have dinner and catch-up in person. I immediately said yes and we made plans for the following day, which was a Friday.
I decided to make an excuse at work to leave for the day at lunch and drove across town to her house. When I arrived Lisa was in a pair of shorts and a halter top which showed off her 38C cleavage nicely.
“Gary! You’re early!” she shouted as she smiled and hugged me tightly.
“It’s such a beautiful day I couldn’t resist coming over early for extra pool time with you and Meghan,” I said.
“Meghan’s upstairs online chatting with friends, but I’ll go tell her you’re here,” Lisa said. “It will also give me a chance to change into a bathing suit. Why don’t you go out to the pool house and get yourself changed?”
As I watched her go up the stairs I thought to myself ‘my god, I can’t believe how much sexier she’s gotten with age.’
I took my time going to the pool house. I had just finished stripping and hanging my clothes when I heard a splash in the pool. I stood there naked and looked out the window and watched Lisa swimming. When she got out I saw her red thong bikini. She’s in her late 50s, but has the hot body of a woman 20-30 years younger. Her breasts were simply perfect and her hips were slight narrower than I remembered, but had curves in all the right places. She looked like a goddess.
Even though I’m in my early 50s, I still have a high sex drive and a wild imagination. In a scene straight out of my youthful memories, I started stroking myself like Brad Hamilton in ‘Fast Times at Ridgemont High’ thinking of Lisa as my Phoebe Cates. The only difference being I was standing next to a bench looking out the window the whole time, not sitting in the bathroom.
I had momentarily closed my eyes while stroking, picturing myself with a naked Lisa. In the moment I closed my eyes, I didn’t see Lisa come over the pool house and realized I had forgotten to lock the door.
“Gary, what’s taking so long? Are you read…” she keçiören escort started to say as she opened the door but was unable to finish her sentence as she saw me naked, stroking my thick, semi-hard seven-inch cock.
“Oh my god, I’m so sorry,” she laughed and started to turn away.
“Don’t be,” I said without making an effort to cover up and taking a step toward her.
“Did I have that effect on you?” she asked.
“Yes you did,” I said.
“I’m your boyfriend, remember?” I added with a chuckle. “I’ve lusted after you for years now that we’re in this situation what should we do about it?”
I stepped closer to her as I spoke.
“I’ve never seen someone lust after me like this,” she replied, taking a step closer to me and reaching her hand out. “But it is a beautiful cock.”
“You can touch it if you want,” I said pulling her into an embrace so I could feel her barely covered breasts pressing against my body.
“It would be a shame to put this to waste,” she whispered before reaching down to stroke me while pressing her lips against mine.
I slipped my tongue into her mouth and our tongues danced as I undid her top, tossing it aside and rubbing her breasts.
“Can I taste it?” she asked.
“Only if I can reciprocate,” I replied.
“Then 69 it is,” she said. “Now lie down on that bench.”
I watched in awe as she peeled off the bikini bottom to reveal a nicely trimmed landing strip over her pussy. She walked over, swung a leg over my head and then got on her knees and lowered her pussy onto my face.
I felt her breasts rubbing down my body before she started licking my cock.
I was in heaven tasting her juices, sucking the lips of her labia into my mouth, running my tongue all over them, sliding my tongue between them. But she was doing a number on my cock. The way she was licking and stroking me simultaneously before deep-throating me while teasing my balls with her fingernails was amazing. I can’t describe what she was doing to me or the sensations she was giving me. She was simply the greatest cocksucker I’d ever experienced.
I don’t know how I held off from cumming for so long but I did. I had just slid two fingers inside her and was pumping slowly while licking her clit, causing her to lift her mouth off my cock and moan when we heard a voice.
“Oh my God! Mom! Mr. L! What the hell is going on here?!” Meghan shouted.
“Honey, look at this cock,” Lisa said as she stroked it. “I couldn’t resist when I saw it.”
“Yes it looks great, but haven’t you two heard of safe sex? Let me go get you some condoms.” Meghan said and left.
We continued to 69 for a few more minutes before she climbed off my face.
“That was amazing,” she panted. “Now I need to see you cum for me.”
She pushed me back onto the bench and knelt in front of me.
She was bobbing her head rapidly up and down, deep-throating me while teasing my balls.
“Let me try one more thing,” she said.
She wrapped her breasts around my cock and started sliding them up and down.
“C’mon, you know you want to shoot all over them,” she purred.
She teased the tip with her tongue each time it poked out at the top.
I felt my orgasm building.
“Cum for me,” she panted. “I want to swallow your load.”
“Almost there,” I breathed hard.
“Cum for me,” she panted again while stroking my cock hard and fast slapping it against her breasts.
“I’m back,” Meghan said and walked in wearing a sexy microkini while carrying a box of condoms.
“Oh god,” I groaned as I shot the first rope onto Lisa’s tits before she quickly moved her mouth over my throbbing cock and took the rest of my load in her mouth. I put my hands in her hair and held her head down as I came harder than I have in years.
“How was that?” Lisa asked with a huge smile on her face.
“That was without a doubt the greatest blowjob I’ve ever received,” I sighed.
“The feeling is mutual,” she said. “You are the best pussy eater I’ve ever experienced.”
“Glad to be of service,” I laughed.
As I recovered I got my first good look at Meghan. She was no longer the cute kid of the past. She was an incredibly sexy young woman. Her B-cup breasts and body filled out nicely and her face matured as well.
“You were supposed to wait for me to wrap it,” Meghan said with a mock whine.
“I’m sure you and your mom can get me wrapped and ready for round two,” I laughed.
“What do you say mom? Can we do it?” Meghan asked.
“Yes we can, but once it’s ready I want that cock inside me, it’s been too long since I’ve gotten any,” Lisa said. “You can sample that magnificent tongue of his.”
With that the ladies went to work on my cock. They took turns licking my cock and taking it between their lips. One of them was caressing my balls during this oral assault. I just sat there smiling watching the show. After a few minutes of alternating licking and stroking, Lisa took all of me in her mouth, deep throating me etlik escort for a few strokes before passing me off to Meghan. Meghan took just the head between her lips and ran her tongue all over it for a minute before releasing me from her mouth. Then she moved to my balls and took them in her mouth one at a time while stroking my hardening cock with a firm stroke. She passed me back to her mother.
Lisa licked in circles from the base of my shaft to the head before slowly lowering her mouth down over my entire length, humming as she went. She teased my cock with her tongue while it was in her mouth and then slowly raised her mouth off me. It was back to Meghan who once again took just the tip in her lips and was teasing it with her tongue.
“Let me see you deep-throat him,” Lisa said and pushed Meghan’s head down quickly all the way onto my cock causing her to gag. She pushed Meghan’s head up and down on my cock a couple of times before letting it go.
“Mom! What did you do that for?” Meghan mockingly whined.
“I’m just overanxious to get him ready,” Lisa said.
Lisa grabbed my cock in her hand and stroked it a couple of times.
“He’s ready,” she said with a big grin on her face. “Give me one of those condoms.”
Meghan handed her a condom, which Lisa quickly unwrapped, put between her lips and then lowered her mouth onto my cock, the condom unrolling as she went. She removed her mouth, pinched the tip of the condom and gave me a two quick strokes.
“It’s on good,” she said. “Now Gary, lie back and enjoy.”
She pushed me down and had just began to move into position to ride me when Meghan moved to straddle my face hiding my view of Lisa.
“Let’s see if you’re as good as mom says,” she laughed and placed her hands on my head.
I had just begun to lick when I threw my head back and groaned in pleasure.
“Oh my god, this feels so good,” I heard Lisa moan as I felt her tight pussy enveloping my cock.
It was heavenly as I felt her pussy squeezing my cock as she slowly slid up and down my length.
“Hey! Don’t forget about me!” Meghan cried as she grabbed my head and pushed it back to her bald pussy.
Like I did with her mom, I slowly licked my way up and down her labia, sucking those moist lips into my mouth. She tasted sweeter than her mom and I was loving every drop of her juices.
Lisa had increased the speed of her riding and I thought I heard her panting in pleasure but couldn’t make out what she was saying as Meghan’s knees were covering my ears.
I reached my hands up to squeeze Meghan’s ass, pulling her tighter onto my face as my tongue found her clit to lick and tease. I gently nibbled her labia as I felt Meghan gripping my head tighter. I trailed my tongue down between her lips until I got to her entrance. I pushed my tongue up as far as I could, having trouble focusing as Lisa’s movements on my cock were taking me to new heights of pleasure.
After several more minutes of this I smacked Meghan’s ass and asked her to get off me.
“Meghan, please get off me there’s something I need to do,” I said.
“Okay,” she said with mock disappointment and climbed off my face.
I immediately sat up and moved my face to Lisa’s bouncing tits and started to lick and kiss them while slowly thrusting my hips.
Putting her hands on my shoulders Lisa began panting.
“Mmmmmmmhhhh yes, yes, you feel so good, I’m going to cummmmm,” as her pants turned into moans of pleasure.
“Oh god, I’m close,” I cried.
“Not until I cum again,” she said breathlessly as she continued to ride.
I wrapped my arms around her and started thrusting my hips up harder.
“Mmmmmm yes, you feel so good,” she moaned.
“Stand up,” I said.
She stood up and I quickly got up and faced her and pushed her against a wall.
I lifted one of her legs to give myself access and quickly thrust myself back inside her.
“Oh God” she cried as I started thrusting harder, grabbing onto her ass.
She wrapped her arms around my shoulders and lifted her legs so they were wrapped around my waist.
She was using her hips to pull herself against my cock while I thrust into her, pinning her against the wall.
We were looking into each other’s eyes, panting and moaning.
I felt a tongue on my balls and realized Meghan must’ve gotten on the floor to join in.
“Fuck this feels so good, I’m gonna cum,” I cried as I pushed myself deep and hard into her.
“Oh god, yes, that did it,” Lisa cried as an orgasm racked her body.
We continued to hug and kiss breathing hard as she lowered her legs, putting her feet back on the floor as my condom-covered cock slipped out of her pussy.
“Is it my turn?” Meghan asked. “I felt neglected watching you two go at it.”
“Not yet,” I said while kissing Lisa’s neck and hugging her. “I’ll need some time to recover.”
“Can we make this a regular thing?” Lisa whispered in my ear while running a hand across my chest.
“Let’s talk later,” rus escort I whispered back.
“Who’s up for a swim!” I shouted. “I could use a dip to cool off after all this activity.”
Lisa and Meghan moved to put their swimsuits back on.
“No you don’t,” I said. “After what we just did, we’re skinny dipping.”
The ladies laughed and agreed and the three of us left the pool house for the pool naked.
For the next half-hour we swam, splashed each other, and laughed like good friends.
I had gotten out of the pool and was laying out on a lounge chair sunning myself, admiring how beautiful Lisa and Meghan looked when Lisa came over to me her tits bouncing with each stride. She swung a leg over my face and stood with her pussy inches from my face.
“I can’t let that face get sunburned,” she laughed as she lowered her pussy to my face and grabbed my hair.
I took the cue and started to lick her labia.
“We can let this piece of meat get sunburn either,” Meghan said before taking my cock in her mouth lowering her lips over the entire length.
It wasn’t long before I was rock hard and Meghan ran off to grab a condom.
I continued my oral assault on Lisa’s sweet pussy and had reached my hands up to grab her ass. She squealed in shock as I slid a finger into her ass while sliding my tongue between her lips.
Meghan returned and I felt her sliding the condom onto my cock with a firm grip.
When she started to ride me, slowly at first before picking up speed it felt wonderful. But I was a bit surprised that even though she’s 30 years younger than her mother, her pussy wasn’t as tight as her mom’s.
Meghan had put her hands on my chest and rode me harder and faster shrieking in pleasure. I don’t know how long we were in this position for, but eventually I moved my head from Lisa’s pussy and told her to get off my face.
I propped myself up on my elbows and watched Meghan’s tits bouncing as she rode me for another minute or two before I told her to stand up.
She reluctantly stood up and I quickly got up and moved behind her, pushing her over to a chair.
I bent her over, took my cock in hand and quickly rammed into her from behind. I started with my hands on her hips thrusting into her with short, quick strokes. Then I slid my hands up to her breasts and started pumping into her with long slow strokes.
She started moaning loudly as I quickened my pace and slid my hands back down her hips as I knew I was getting close.
With one final thrust and a groan of pleasure I came hard holding myself deep inside her knowing the condom was doing its job.
I pulled out slowly and Lisa was right there on her knees to slide the condom off and lick me clean.
After that we agreed it was time to head in and start getting ready for dinner. We all walked into the pool house together where Lisa & Meghan picked up their bikinis and went into the house while I toweled off and got dressed.
An hour later we were sitting around the table eating a salad, baked salmon, and steamed asparagus.
Meghan said she had graduated with a BA in business administration and was working for a major company in a nearby city. She also dropped the bombshell on me that she was engaged and due to be married next month.
“You’re engaged?” I said in shock. “And you cheated on your fiancée like that with me? I thought you were better than that.”
“I am Mr. L,” she said. “But I’ve always had a bit of a crush on you and when I saw your cock I couldn’t resist.”
“What’s going to happen next time you see a cute guy’s big cock?” I asked.
“Nothing,” she said. “This was a one-time thing. I love Jake and won’t cheat on him again.”
“Good,” I said.
Then I started to laugh and added “Did my invitation get lost in the mail?”
“No,” she said. “We needed to pare down the guest list and unfortunately you and Sara were among the cuts.”
Lisa remained silent during this conversation as I assumed she had talked to Meghan about her behavior and the events of the afternoon while they prepared dinner.
Lisa told me that she was enjoying the free time her retirement brought but that since the divorce she was lonely at times and still a little heartbroken that she & Ed couldn’t work through things.
I told her I’m glad to hear she’s enjoying retirement and that if she ever gets lonely to stop by the office and we could do lunch. I also empathized with her about the marriage not working as I felt the same way with Sarah, a little heartbroken things didn’t work out. But I have good visitation rights with Billy.
“I don’t think they would approve of you licking my pussy for lunch on your desk,” she laughed.
“Mom!” Meghan shrieked. “I’ve never heard you talk this dirty.”
“Sorry honey,” Lisa said. “Gary knows I’m just joking and flirting.”
“Yes I do,” I laughed. “Besides your mom and I could go out for friendly, fun lunches, keeping our clothes on and hands to ourselves.”
I don’t remember much of the subjects of the rest of the dinner conversation but there were laughs and smiles.
After dinner was cleaned up it was time for Meghan to leave and head back home. We exchanged a friendly hug and peck on the cheek. Meghan and Lisa had their mother-daughter goodbye wishes and hugs.