I’m sharing an experience that I had a few years ago over the summer that led to many other things. One that I most likely will never forget, not because of what we did, but because she was way older than me. I live in a nice upper middle class neighborhood, a gated in street with decent and big sized houses. Okay well to tell you a little about myself, I was 18 at the time, 5’11, body toned and fit, 8inches long, and 2inches thick. Anyway, it was a normal hot summer day, just sitting around the house playing Black Ops, staying cool. It was the summer I was going to leave for school. My dad had walked in my room and let me know that Ms. Barbra called and asked if I could cut her grass soon because it was getting pretty long again. I had cut her grass on a number of occasions, so this wasn’t the first time. Now Ms. Barbra was cute for her age. I would say she was about 50-55 at the time, she had red hair, she lived by herself, had big boobs (at least DD’s), wore glasses, about 5’5, and 150lbs. I never thought about her sexually until I cut her grass that day.

I said okay and called her back asking when would be a good time for me to come down to her house and when will she be there, she asked would Saturday work for me? And I said around what time because I kind of had plans. She said would 5ish work, because she didn’t want me out there cutting grass in the middle of the day since it was so hot. I replied that I kind of had plans with some friends to go out later on (which I didn’t, this was really going to be date time for my girlfriend and I). We discussed possible days and times and she said she was having some company over on Sunday and needed it to be done on Saturday. So she threw out the idea that if I was really going to be in a rush I could just freshen up at her place in her guest room, I gave it some thought and said okay. I guess she felt bad about possibly cutting into my plans.

So I get down to her house on Saturday and put my change of clothes in her house. I go out back and get her lawnmower and start cutting the grass. I was cutting for about 13 minutes before I had to pee. I knock on her back door and ask if I could use the bathroom, she leads me to it. And as she leads me, I can’t help but notice how good her legs are shaped in her shorts, how big her boobs really were, and how sexy and perfect her feet are. As I get to the bath room and close the door, I could feel a hard growing. I pee, wash my hands and relax myself so I can go back out there. I go out and she asks me if I wanted anything to drink, I said water. She reaches down into her dish washing machine and as she reaches down I sneak in a couple more peeks of her. And before you know it my hard is growing again, she handed me the water and she notices, she glanced down for a few seconds at it but didn’t say anything. She kind of gave me a weird look. And I noticed she bit her bottom lip a little. I didn’t respond, I didn’t want to think anything, or didn’t want to look at her. I was so embarrassed because I had on basketball shorts and boxers underneath. So my hard couldn’t hide even if I wanted it to. I go outside and finish the front and back in about 25 minutes. The whole time I was kind of nervous and scared she would tell my parents or one of the other neighbors about what she seen or what happened.

I walk back and lightly knock on her back door to let her know that I’m finished with the front and back. She thanked me and everything, saying how she really appreciated it because she really needed it done because she was going to have guest over the next day. I shyly replied you’re welcome because I wasn't trying to talk, I was just wanting to hurry up and be done. She says “We better not waste too much more time, don’t want you to be late”. I go and grab my bag, she leads me to the guest room and says if I needed anything just let her know. She had the soap, and towels already laid out in the bathroom. I shower and dry off, put my clothes on and walk out to her kitchen area. I told her that I left the towels in the bathroom hanging up, she just kind of looked at me and didn't say anything. I could tell something was on her mind though, so I just gave an awkward smile and she said “you know, sometimes a woman’s curiosity can get the best of her” I chuckled and said “oh okay, what do you mean by that?” She took a deep breath and said she didn't know if it was okay to talk about it with me, but I assured her that it was fine and that whatever it was, was going to be safe with me. I started getting the idea that she could possibly be talking about my hard that she seen in my shorts earlier. Yeah I was only 18, but I wasn't dumb, I've had my fair share of girls. I know how the game goes.

I’m going with the flow of the convo, and she asks “what was going through your head earlier” I said, “earlier? I was just cutting the grass earlier” she says “I’m talking about when you were getting your drink”. I paused for a couple seconds and said “ohhhhhh you noticed” and put my head down in embarrassment and apologized. She said there’s no need to apologize it’s a normal thing and sometimes that just happens. I go on to tell her what I was thinking about, how she looks really good for her age and how she has a really nice shape, a perfect one. She smiles and says thank you and starts to blush. She wanted to know more of what I was thinking, I start cheesing pretty hard and scratching my head and just laughed. She said that it was a pretty big thing down there, I laughed and said “its okay I guess”. From there on I knew what could possibly happen, either I get some head, sex, or a handjob. She was really upfront and didn’t bite her tongue with any of it, I guess she was really curious about how it looked. I would have never thought she would be openly blunt about my dick.

She then ask if she could see it, but only if we keep it between us. I said “I won’t tell, if you don’t”. Her smile grew from ear to ear. I then smile at her to let her know it was okay for her to reach and feel. We were both standing up, and she reaches and rubs my penis and balls through my pants, it felt real good so I was hard in no time! I’m standing there watching her rub and caress my balls through my jeans, as she was taking it all in. I was literally hard as a rock and she could definitely tell, she looked a k** in a candy store! Lol. She had then unzipped my pants and pulled them down, releasing my dick standing at attend hut looking at her under my boxer briefs. She said “WOW, that’s a big cock”, I just chuckled. She pulled my dick out and gave it some slow hard tugs pulling it towards her. It felt soooo good, her hands were really soft and she knew exactly where to touch and caress it. She had my nuts in her hand jiggling them in and out of her fingers and pulling on them a little. Nothing major or painful but pleasurable. I was like “that feels really good”, she smiled and told me to have a seat and that she’ll be back.

She comes back from out of her room with a bottle of oil. She rubs some in her hands and starts back at jacking me off and giving me one of the best handjobs that I have received to this day. Up and down her hands go sliding on my dick, one hand she’s stroking me off and in the other she’s massaging my nuts, It all felt AMAZING. I then reach and grabbed and rubbed her boobs, I figured why not? Since she is all on my dick. She stops and takes her shirt off and undo’s her bra, and when she dropped that bra. I was blown away at how big and juicy her boobs were, with some big hard nipples. I started to rub them and lightly pull on her nipples. They were so soft and warm, it felt like baby skin. I pull her close to me so I can suck on them. I just had to smother and put my face in between her perfect boobs. I started licking around her areolas and softly biting over her breast, making my way to her nipples. I was sucking on her nipples like there was some milk in there for me, as I’m rubbing and kissing on her boobs she starts jacking me off again this time speeding up the process and combining it with caressing my balls.

I let her know how good it felt, and she just smiled back at me. Now she’s really going to work with jackin me off, not fast but sliding her hand up and down at a steady speed, one hand rubbing every inch of my dick and the other cuffing my balls, I thought I was in heaven it felt so good. This went on for about 7 miutes, and then I was started to get that feeling, of soon cuming. I let her know that I was about to cum. She didn’t stop, she kept at that steady pace of up and down. As I started to cum she leaned in closer to me and pulled my head in closer. Completely smothering my face in her boobs as I was breathing hard and softly moaning. Shooting load after load into her hand. She did not stop jackin it either, she made sure she drained all of me. I shot so much that it started to run down my balls. She made sure she got the last drop out too, as I was all drained, breathing hard catching my breath she slowly stroked and pulled on my dick. Mixing the oil and all of my cum together. That felt good too, this lady really knew how to stroke a dick. After the mood dies down, she smiles and says “thank you for that, I always wanted to do something like this, trust me you have no idea”. I laughed and said “you’re welcome, and guess one of these days I could possibly find out”. She said with a smile “yeah one of these days maybe”. After that I went to clean up and get ready to leave, on the way out she gives me a hug and a big kiss on the cheek. And said see you next time.

There’s more to come if I ever feel like typing it out, but this lady is the truth! I’m glad I met her. And I still cut her grass and help her out to this day whenever she needs anything ;)