TJ Talks

Although this story has seeds of truth, it is fictional. Everybody characterised is over the age of 18.
TJ

*

My ex-sister-in-law TJ was never going to be mother of the year. She was the kind of woman that had the moral-less mindset of "Why not drink and smoke pot with my teenage son and his friends?", "They're going to do it anyway, they might as well do it at home where they won't get caught or get into other trouble."

I had been divorced from her sister for over a year. During the time I was married to her sister, TJ and I were friendly, we got along well and although there was an occasional flirt or many times dirty or sexy comments, we never did anything that we shouldn't have. It was an unspoken line that we simply never crossed. TJ had been divorced for 7 years and there were many stories from both her and my ex-wife of her exploits as an un-caged and free woman. To say the least, she was very sexual.

Now she is 42 years old, very skinny, almost too skinny and has a trashy aura about her. 5'2" and probably hovering at 100 lbs. She always comes off as tough and wears tight jeans and leather coats. Trying to be a Harley Chick without a dude or a Harley. I've seen her in a bikini, she is as flat chested as any adult woman can be with teabag like boobs and virtually no butt. I never judged, she was simply my friend and sister-in-law and I accepted her for who she was.

She had asked me many times to do menial tasks around her house such as fix her boiler or change a faucet. I was always happy to help out. However, since I divorced her sister she hasn't called. I never gave it much thought, often a divorced couple means divorced in-laws as well.

One day I ran into her at a department store, we were both genuinely happy to see each other and greeted with a tight hug. We talked for what seemed like a few minutes but turned into a half hour. She mentioned that she thought about calling me to help with things around the house like she used to but thought it was out of place and didn't know how I'd respond. I told her that I divorced her sister and there is no reason that she and I can't still be friends. "Feel free to call me anytime." I said as we parted.

A few weeks later I got a call. She told me that her 21 year old son was away for the weekend and she was having trouble opening the damper to her wood stove. It seems her son usually handles the stove but this weekend she was out of heating oil and couldn't wait till Monday. I told her I'd be there after work and I'll help her out.

I was stuck at work a lot longer than expected and texted to keep her informed when I would be swinging by. I didn't get there until 9pm. The place was cold so I quickly got the damper opened and helped her get a roaring fire going. I noticed she was a little bit inebriated, I asked if she was drinking. She said she was doing shots of rum hoping it would give her a better tolerance of the cold until I arrived.

"Did it work?" I asked,

"Not really, before I was just cold, now I'm drunk and cold." she replied with a laugh.

We both did a shot and chased it with beer as we were chatting like we used to in the old days. Before we both knew it we had done 3 or 4 shots in less than an hour. I told her that I was in no condition to drive and asked if I could order a pizza or Chinese food because I haven't had anything to eat since noon. Hoping it would sober me up enough to drive home.

After we ate we still drank and she smoked a joint. We were pretty wasted and it was clear I wasn't driving tonight. It didn't take much for us to get our conversation on whether or not we would scratch the proverbial itch that we had with each other all these years. She said she had no problem going for a round or two with me but wanted to make it a bit of a truth or dare game. She said simply getting naked was too easy. I didn't think she was playing hard to get, we already covered that it was a sure thing so I figured if this is what she wants as some kind of foreplay then so be it.

A short while into the game I realized that she kept calling out Truth with an occasional dare. I on the other hand was calling Dare more often. I just wanted us to get busy as soon as we could. It didn't take long for me to realize that she was going through all this because she wanted to have some kind of confession. Now I was intrigued and tried to formulate my questions so she could get out her deepest secrets.

Throughout the game there were enough dares for us to stay wasted, get naked and do a few naughty things, but the truths were far from what I expected. It turns out that 3 years ago when she started to allow her son and his friends to hang out and party at her house, she would many times end up having sex with 3 of his friends. At first she would do them individually telling them to keep it secret but eventually she learned that they all talked, including letting her son know. She thought she had a problem that she couldn't live through but it turns out her son was manipulating the situations and decided who was next and how the nights would play out until it ended up being a weekly gangbang while he watched. Eventually he decided that he wanted in on his mother's action and by then she was all too willing to oblige.

She admitted that the first time with the first friend was her making it happen. She was intentionally being flirty with this one particular boy named Josh. It went as usual with the boys tapering off and going to sleep in various places in the house as the party died down into the late night. She said that at some point it was just her and Josh still up and she had decided that tonight would be the night that she would live out a careless fantasy that she's had for some time.

She said she was wearing tight Daisy Dukes and a simple white t-shirt with no bra, although she didn't have huge boobs, her nipples were usually rock hard. She made it a point to flaunt her sexuality enough to turn him on. While smoking another joint she caught him staring at her hard nipples. She took advantage of the opportunity to kick things up a notch.

"Are you staring at my boobs Josh?"

"Sorry TJ, I couldn't help it."

"I'm sure you have girls your own age that let you play with their titties."

"No, I don't, actually I'm embarrassed to say that I'm still a virgin."

"Oh, that's too bad. If I was younger I'd be more than happy to help you out with that problem, but I'm too old for you and even if I did, I could get into trouble."

"I don't think you're too old. I think you're hot, I've played with myself thinking about you. As for the age, I would never say a word to anybody. But I'm sure you're not interested anyway."

"You promise you'd never say a word." she said as she moved in close and stroked her hand across his bulging cock through his jeans.

"I really promise, never a word."

She told him that she's heading to the bathroom and she expected him to be waiting naked in her bed by the time she got out. He wasted no time in complying. When she crawled into the bed she reached towards his cock and was a little bit shocked at how big it was and how rock hard it was. She promptly went down on him. Swallowing it deep enough to gag a little bit as she stroked and sucked it. She told me that it was the hardest cock she ever felt. He lay there uncertain what to do so she stayed with the head job but she knew she wanted this nice rod buried deep in her cunt. Unfortunately he started to cum, she decided that rather than stop him she would give him great head. He humped his hips as she worked to keep that knob buried close to her throat as he came. He wriggled in a ticklish manner almost wanting to pull it out but she kept him in place until he finished dumping his load in her throat.

TJ thought the night was over and although she was excited that she just took out a virgin, she was still hoping to get off but without too many words he fell fast asleep. She tried to arouse him by playing with his dick but it appeared the weed got the best of him. She just rolled over and masturbated herself to sleep.

Shortly she was awaken to her leg being moved as she felt that nice cock finding its way to her cunt. Josh woke up and decided to move in on the sleeping TJ. She pretended she was asleep for a few minutes until he got his momentum going but she couldn't stop from moaning and woke up as he pummeled her cunt. It only took about 10 minutes before they both exploded in a simultaneous orgasm and fell asleep with his semi-limp shaft in her cunt.

She said she got up the next morning and he was already gone. She was hoping none of the other boys saw him in her room.

We broke away from the game and confession for a few minutes while we took care of each other. I could hardly believe that I was in a sixty nine with TJ. She came a few times on my face as she cranked my shaft but I wasn't ready to end the highly charged night. I pulled my cock away from her so I wouldn't cum. I wanted to hear more about her past three years.