I would occasionally babysit for the couple across the street. Just into their forties they had two kids in elementary school. They lived in a very nice house with pool and all, and they drove very nice cars.
They got divorced one summer. I had just turned 19 and was attending a community college only a few minutes from my house. I still would babysit for my neighbor, Lori, from time to time, because the money was easy and plentiful.
Lori is in her early forties, but she doesn't look a day over 25. Pale skin and 34B breasts (I have snuck a look at her bra while babysitting a while back) compliment her toned ass and flat stomach. One August night she became mine.
At age 19 I was 6'4" 190 pounds. Almost washboard abs and large toned muscles every where else. I walked over to Lori's house one night to watch her kids. Now at ages 12 and 10 I really didn't think that they needed a babysitter, but I didn't mind getting paid to play video games and watch sports with them.
I knocked on the door and Lori answered, "Hey Jim! I'll be ready shortly." She looked absolutely stunning. In her black dress that hugged her toned body and showed off her nice legs. "The kids are in the media room."
"Ok."
I walked towards where the kids were. Lori looked damn hot. Her breasts looked larger than usual too. I said my hellos to the boys set down my laptop and went into the kitchen. A few minutes later Lori emerged now wearing black pantyhose along with her black dress and high heels. Her hair was usually some shade of a dark red, but since the divorce she had colored it a dark sandy blonde, and it reached down the middle of her shoulder blades. Her usually pale skin now had a nice tan to it. Being August I assumed it was a natural tan from her summer time in the pool.
"Alright Jim, you are ok with staying the night?"
"Of course. Tomorrow is Saturday so it's no big deal."
"Thanks a lot. I will have your money for you in the morning. Wish me luck on my date."
"You look great. He is a lucky guy."
She flashed me a seductive smile and was out the door. I looked out the window and saw her new Mercedes roaring down the street. What a MILF.
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The rest of the night was fairly uneventful. Video games, pizza, and a movie before the kids went to bed. I was off the clock by 11:00. I made myself a place on the couch and fell asleep watching Sportscenter.
I awoke when I heard a door open. I looked at my phone, it was 3:00 am. I got up and walked through the house in only my boxers. I went into the kitchen and was surprised to see Lori there.
"Lori?"
"Oh! Jim you startled me."
"Why are you home already?"
"My date didn't go as planned. One of my friends set me up with him. He is a slob. Hairy everywhere and overweight."She stopped and gave my body a once over. Being startled out of bed I was only wearing my boxers. She eyed my defined stomach and toned arms.
"Well that is too bad. I'm sorry. Give me five minutes and I'll head home."
"No, no. It's three o'clock in the morning. Stay."
"Umm, ok. I would probably scare my parents anyway setting off the alarm at this hour."
Lori turned towards a cabinet and said, "Would you like a drink? I have some wine, scotch, and some beer in the garage fridge."
"I actually don't drink."
"I usually don't either. It's all of my ex's left over stuff." She sighed with an obvious look of regret on her face. "I really miss having a man around. My boys aren't old enough to be men of the house yet. I hope they will grow up fine without a strong male presence."
"Why won't they see their dad?"
"He ran off with some blonde 25 year old. Took all of our savings. Millions. Once they tracked him down he had blown most of it on some house and cars in California. I got only 2 million of that put into my savings and a 200,000 settlement. Child support is 5,000 a month and he has to put 1,000 a month into each of their college funds. I guess I came out good in the end, but he's the one with the hot new wife while I'm here dating obese hairy men."
She began to cry. Leaning against the kitchen counter she began to sob into her hands. I really didn't know what to do.
I walked over and placed a hand on her shoulder. Gently enough as to not show affection, but strong enough to show that I was here for her. "He lost you too. You're kind and caring. Plus he won't get to see his own kids until who knows when."
She stood straight up and reached her arms around me, pulling me into a hug. I wrapped my arms around her neck and our bodies pressed together. We stood like that for maybe 20 minutes. She would sniffle from time to time, but after a while she began to compose herself. I surprisingly didn't get hard with her hands on my bare skin and my cock pressed against her flat tummy.
We removed ourselves from the embrace and we faced towards each other. She took one of my hands in each of hers and placed a kiss on my cheek. "Thanks for being here for me Jim. It's nice to talk to another adult. My kids aren't old enough to understand this, and no matter how stupid my ex-husband is I will not bad mouth him in front of his kids. He can make himself look like an ass on his own."
She walked over and fetched a tissue. She ran it across her face cleaning up her makeup that had run down her face.
Lori said, "Well I am a mess. Where were you sleeping?"
"On the couch."
"That's not very comfortable. Why don't you come sleep in my bed."
"I couldn't."
"Please Jim. I insist, we are both adults here. The bed is plenty big for two people."
Both of us being adults is exactly what I was worried about. "Ok, since you insist." Can't say no when teenage hormones are in the mix.
"Pour me a glass of wine and meet me in my room. I will go change."
She exited the room. Rubbing her freshly manicured nails across my hard stomach, sending a jolt into my flaccid penis.
I did as I was told and entered her room with a glass of wine. I sat down on a chair in the corner of her room waiting for Lori to exit the bathroom. I had also cleaned up my prior sleeping location and put on a shirt and some shorts.
My eyes wandered across Lori's room. Neutral colored walls and random decorative features on the furniture and walls. However, her bed was not all that big. Probably a queen sized mattress. Plenty big for one person or two lovers, but not for a single woman and her 19 year old babysitter.
In mid thought Lori emerged from the bathroom. She had removed her makeup and now wore a robe.
This wasn't the big fluffy hotel robe. No this was a pink "covering" that didn't cover all that much. It went down to just past her round ass. The material was more or less see through. The tie was around her up near her naval, but open up top all the way down to just before her belly button. It showed off her flawless neck into her chest, and the insides of her breasts, along with some of her flat belly below her breasts. After the tie the "robe" parted showing off her black lace panties.
I handed her the wine as she walked past me. She took the wine saying, "Thank you sweetie." Continuing to her side of the bed I got a good look at her panty clad ass as she pulled back the sheets. "Get in the bed Jim. I won't bite."
I got up from the chair and walked to my side of the bed. I took off my shirt but left on my shorts.