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 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.
