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#Mature #Teen

Low self esteem

1.7k words | 6 | 4.67 | 👁️
Bob in Tulsa

47 year-old single never married mom with low self-esteem who blames her 14-year-old daughter for a lot of her own mistakes.

I met Brenda, she was one of those girls who had the sad puppy dog eyes, but could smile on queue, but you could tell it was fake. I started chatting with her. She was probably about a six on a scale of one to 10 on looks. She was 47. I’m quite a bit older than she is. Like 15 years older. But most people say I look a little bit younger than that. We developed a friendship. We built some trust. And one night she said, why are you even bothering to be with me? I said what do you mean? I mean, I’m fat and I’m ugly. I said no, you’re not. What makes you think that?

Basically at her age, she’s looking at her life and thinking I haven’t done a damn thing and she recently she got into alcohol for her depression. Well, alcohol is a depressant so she became even more depressed while she was drinking to feel happier. I can see tears coming down her eyes at this point, and I said you look like you could use a hug and with that, she just melted into my arms and started sobbing. I could feel her very large mature breast up against my chest, and I loved it and I held her close. I said I think you’re very beautiful. She pulled back and looked at me and it was an instant communication for I need a kiss. And the kiss was very long and very passionate.

I knew she found validation in herself by how many men would see her as attractive. I didn’t want to disappoint her, so I said I think you’re very sexy. I will say she gives the most amazingly perfect blow jobs. She dropped to her knees without even me asking and pulled down my shorts and started stroking my cock and then devoured it. The sounds that she made with her mouth as she suck on my cock or porn star like. And and oh yes, she could deep throat with the best of them. There was no gag reflex. It wasn’t long before I was shooting my load right into the back of her throat. Then and only then after she showed me the cum on her tongue and then showed me that she would gladly swallow my gift to her was a real genuine smile.

Brenda said I guess I won’t be seeing you again because usually that’s all guys want and I said no that’s not necessarily true. I’m thinking in my head I want your pussy and your ass also. I said let’s go out and have something to eat. We went to red Robin and had some of their hamburgers and then back to my place. Where we picked up right where we left off and yeah, I took some Viagra. I wanted to keep up with this little bitch. Her pussy was magnificent. Her Clit must’ve been about a full inch long and about a quarter inch wide and I stroked and licked it to full hardness and then I sucked it. She came so incredibly hard. Her legs started shaking. And then I slipped a couple of fingers inside of her and started on orgasm number two. I was pushing upwards with my finger toward the G spot and sucking that clit for all I was worth and she arched her back, pushing her pussy into my face and had a full body orgasm with her entire body, shaking and squirting right in my face, and I loved it. She said it was her first time she ever had a squirting orgasm, and she felt so embarrassed because she thought she pissed on me. I said oh no. If it felt that good, it was an orgasm.

She got on her knees with her head down and my cock, found her beautiful pussy, and I started pounding that little bitch hard God she was a good fuck I loved it when she called me, daddy I later found out. She always liked older men because older men could buy her alcohol when she was under aged and she traded sex for it starting around age 10. I was on the verge of coming and I wanted to make this last so I pulled out and I said I need to for you to ride me. She got on cowboy style, and I gave her a Hitachi magic wand to put on her clit. She rode me and I could feel the vibration through her clit all the way into my cock and she started coming hard, and I started coming also and exploded into her. I’ve had a vasectomy, so no need to worry about that. She was still having a few periods, but strange things have happened.

We laid there together in bed and I said please spend the night that’s when she told me about her 14-year-old daughter that she had to get home to. I didn’t know she had a daughter until then. I said oh really what’s her name? She said her name was Emily. I was a little shocked and surprised because most moms brag about their kids, but she never mentioned the kid until now. I said I’d like to meet her. She said usually I don’t let my daughter meet the guys I fuck but you seem like a nice person. Do you think that we can actually have something real in long-term ? I said, of course we can.

A week past by slowly, but I had a date with her on Friday night, but this date was gonna be more of a kid friendly date so I can meet Emily. Emily was a knockout. Long blonde hair. She had her mother’s boobs and they didn’t sag one bit. Very nice ass and legs that would not stop. I may be old, but I got a hardon just looking at her.

The date went really well, and Emily seemed to like me which was good. I dropped them off at their house and I was invited in. I didn’t think sex was going to be on the menu since Emily was present but mom asked me to spend the night and I said of course. Mom slipped Emily a little sleeping pill. I don’t know exactly what it was, but I know that I had to carry her to bed. And of course, I didn’t mind doing that at all. She was about 5 foot Nothing probably weighed about 100 pounds of that 30% was probably her tits. I’m just joking on that a little bit. And while I was tucking her in, I felt her up and gave her a kiss. I pushed my tongue into her mouth, and she automatically pushed her tongue into my mouth, even though she was asleep.

I went to Brenda’s bedroom and Brenda was already underneath The covers completely naked waiting on me and she said oh Bob I need you to fuck me again. But first I want you to give me a squirting orgasm like you did the other day. I’m not about to say no to that. When I got between her legs, I noticed that she had shaved her pussy. It was not shaved a week ago. And it was very smooth and I loved it. She said I wanted my daddy to have a smooth pussy to eat and fuck. I said thank you so much. I started kissing her neck down her chest sucking on her beautiful nipples kissed down her belly. She spread her legs wide and then I started kissing up her thighs from her knees up to her pussy, teasing her a little bit and I could tell that she wanted me too attack that pussy I started sucking her clit and finger fucking her hard and it wasn’t long before she was squirting, and shaking, and trying to talk but only gibberish came out of her mouth, that was fucking amazing! I took her doggy style and then finished off with her legs over my shoulders in the missionary position as I plowed my cock into her pussy deep. As we lay together, kissing and making small talk, I found out that she didn’t really want to have Emily, but she didn’t have a heart to have an abortion.

she said I’m stuck with her now, he said she can be a pain in the ass. I said most teenagers are like that. Brenda said she needs a man to take control and teach her what it’s like to be submissive. She didn’t know if Emily was still a virgin or not probably not. Then Brenda looked at me and said. Do you think you could teach her? I said exactly what do you mean? I was hoping she would say fuck the shit out of that little girl and she did. She said I need a man to teach her what sex is. How good it can be and how to behave with a man. I said would you be OK with me fuck her? She said, of course, is my idea.

I said I would have to think about that. There was no thinking about it of course I’m gonna fuck that bitch, but I wanted her to think that I was mulling it over a little bit, leading her to believe that I might have a moral core. Which by the way I don’t. I said yes, when can we start? She said how about next Friday night. We can come to your place and spend the weekend with you and you could have your way with both of us. I said would she be agreeable or would I have to rape her? Brenda look at me and smiled and said either way is fine with me, but I hope you have to rape her cause I like to see a little bitch cry a little bit. I said not a problem. And that will be part two.

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Comments (6)

  • TellMore: Hoping to read part two

    Reply↴ • uid:ln4ps42
  • BiBoy: You played this perfectly, complimenting the slut with low self esteem and setting yourself up to fuck, preferably to rape, her daughter! Agree with Jay, don't hold back!!

    Reply↴ • uid:8n9x2i3m9i
  • Never enough: Yes you bad mommy : Yes you baby doll you aggressive slut fuck call me when you read this one baby lol just got this same offer in real life omg So excited,,,,,

    Reply↴ • uid:7pqjf5vt0i
  • Unknown: Part 2 of u teacher the daughter and lesson

    Reply↴ • uid:5wwnzuerm9i
  • Jay: Don't go easy on the daughter, give it to her nice and hard.

    Reply↴ • uid:1e3g2d6ok7qa
  • Roughest48: Fuck yes. Nothing better then a mother giving away the daughter to be raped and helping you rape her in all her holes

    Reply↴ • uid:y14l0qxddfx