A Unique Relationship: Prologue

 

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. 

————————–

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. I was attempting to hide my growing erection. 

I was about to slide into the bed when Lori said, “Take off your shorts honey. These sheets feel great on your skin.” I looked up and realized she had taken her own advice. Her “robe” was hanging on a hook beside her bed, and she had slithered under the sheets without me knowing, and she was topless. 

I quickly maneuvered off my shorts and slid into the bed trying to hide my erection. 

“Oh Jim, could you get the lights?”

“Sure.” I responded. The only problem was my hard dick. If I stood it straight up and put it in my waistband it would stick out at least an inch. If I put it down a leg it would easily draw attention in my flimsy and short boxers. I was screwed. “I’m gonna go get some water want anything?” If I walked straight out of the room she would only see my backside. Threat avoided. 

Until she answered. “Actually yes I do, but you wouldn’t know where it is. I will come get it.”

She got out of bed and put on her robe facing away from me. All that I saw was her smooth back that tapered into her nice ass and shapely hips. I couldn’t stop oogling at her perfect body.

I began to walk to the kitchen. A few steps out of the room Lori had caught up and she grabbed my hand. “My contacts are out. Don’t let me run into anything.”

We walked to the kitchen. The lights were still off, but the moonlight was coming through the open windows and there was a glow from the display on the freezer. I fetched a cup and gulped down some water while giving my cock an “un-pep” talk. That became difficult when I looked up and saw Lori struggling to get a bottle of wine out of the wine fridge hidden in the cabinet. 

At 5’8 I towered over her, “Need some help?”

“More than you know.” She quickly responded. 

Lori stepped back and let me move to the counter. “Which one do you want?”

Lori moved forward and placed a hand on my back and one on my waist. Good thing I didn’t put my cock in the waistband. “It’s the top right one.” But she was more worried about feeling up my stomach and back. “This is the good stuff.” I wasn’t sure if she was talking about the wine or my body. 

I retrieved the bottle, shut the cabinet and poured Lori another glass of wine. We headed back to the bedroom in her near blind and tipsy state. 

By this time it was 4:00. We talked for another hour or so and I made 4 more wine runs in that time. We had talked about my school, her kids, her job, and my future. 

I returner after the 5th wine run this would be her 7th glass plus whatever she had at dinner. As I sat down Lori asked me another question, “So Jim do you have a girlfriend?”

I knew the question was inevitable. “I did. We broke up 3 weeks ago. I am at the age where I am looking for a wife. Not a girlfriend.”

“Are you a virgin?”

7 glasses of wine on a lightweight like her had loosened up the conversation I guess. “No I’m not.”

“How many girls have you gone all the way with?”

“Two.”

“Tell me about them. Tell me about the sex!” Over the last five glasses of wine she had sat up in bed exposing her breasts. Which I learned during glass 5 had been augmented from a B to a C only a few months ago. (They looked perfect and their was almost no scarring) 

“Well I lost my virginity to a girl I dated for about 2 months. She was a virgin as well. I knew her in High School and really liked her company. She has small boobs, but she had a killer body. She plays soccer, our first time was in my bed. She stayed the night when my family was out of town. We didn’t fuck though. We made love. I thought she was the one.” 

“Then why did y’all break up?”

“She was going to school on a partial scholarship. Academic and athletic though. She got an offer to play for North Carolina. She’s a great soccer player and that’s one of the best schools in womens soccer. We decided to break it off before it got “serious”. We had sex so to me it was serious. We actually kept up a purely sexual relationship until about June, but at that point it wasn’t making love any more. We were just neutralizing our teenage hormones. So we started dating in March, broke up in in mid May and fucked til late June.”

“That’s so sad.” She says as a tear dropped down her face. The wine was making her emotional. “What about the second girl?”

“It was mistake. I knew her from college. She is a waitress at Hooters. I was out with some friends one night. Boys and girls. Someone had invited her. We were going to do a movie marathon together. You know like 5 movies in a row? Well after the second movie we went out to my truck and banged it out. After feeling each other up for 2 movies we were both horny. I hadn’t fucked in a week and she was a slut. With the first girl we had bare sex. She was on the pill and we were in love, but with the second girl I always used a condom. She was on the pill too, but she had been with tons of guys. We said we were dating, but we were just fuck buddies. She was great at that though. She had nice big boobs bleached blonde hair and a perfect. We knew it wasn’t going anywhere. We were both mature enough to see that we were only horny.”

I’m pretty sure Lori was fingering herself or at least playing with her clit. “Why did y’all stop?”

“Like I said it was three weeks ago. I started chasing another girl that was more “wife material”. It was only a matter of time until that slut gave me an STD anyway. I actually have a date with that new girl tomorrow night, well I guess that’s tonight now. Being that it’s 6:00 am.”

We had talked for over three hours. Topics ranging from kids to sex. 

Lori said, “I am going to try and get some sleep before the kids wake up. Thanks for staying tonight Jim. I have enjoyed being with a manly man that is also handsome and caring. They don’t make guys like you anymore.” She slid down into the bed, finally covering her nice tits. 

I fell asleep soon after. I woke up at about 9:00 am to Lori rubbing her ass against my morning wood. I don’t think Lori even knew what she was doing. 

Lori began to stir after I made some loud noises so that she would get off my dick. After only a few minutes Lori’s body jumped, “Jim, I’m so sorry. I didn’t mean to make you feel you up like that.”

“It’s no problem we’re both adults. We can handle some contact.” I said as she turned towards me and started running her hand up and down my rock hard shaft. She seemed to have sobered up over the last few hours and she appeared more sure of her actions. 

“Jim, like I keep saying. We are both adults with no other person in our lives. Are you ok with where this is going?”

“It depends. Are you looking for sex or a relationship?”

“Relationship. I’m only in my early forties. I can still have kids and make a man hard. I want to find a man.”

“Consider him found. Lori do you have any plans next Friday night?”

“No I don’t.”

“Then I will pick you up around 8?”

“Sounds good. What about right now?”

“How about we save it for Friday night? That ok Lori?”

“No, but I’ll make it. What about this other girl that you have a date with tonight?”

“I’m going to give it my all. If things work out then great, but if things work out between you and me then…. I’m yours.”

She replied, “Sounds good Jim.” 

She released her hand from my cloth covered cock and got out of bed. She put on her glasses and walked to her bathroom. Topless. Friday can’t come soon enough.