First experience as the lawn boy

[BareBones]

I lost my draft so I'll keep it brief. I had a summer job at 16, around 40 years ago. In addition, I cut lawns on the side. One day I was finishing up the last job of the day and it was during a heat wave. This house had a swimming pool so I decided to cool off before riding my bike home. I had to wear light sweatpants and a long sleeve shirt because of poison ivy at one of the homes. This home is the new one. The other 4 or 5 I did the prior summer too.
I decided to strip down naked, jump in, cool off, get out before anyone gets home. Problem is, someone was already home. I remember being in the pool for maybe 5 minutes? I swam underwater from deep end to shallow then stood up with my back to the house. I then hear "nice job. Now what do you think you're doing in my pool" or something like that. I turn around to a nice looking lady in a tight shirt and daisy dukes. She's the home owner, Mrs James. I immediately grab my dick. I'm average size, but very tall and athletic built. She orders me out and to walk to her. She's by the edge of the patio, probably 15 or 20 feet from the pool. As I'm walking to her, she says no, hands down. I start looking for my clothes and plan to run away but she tells me she already put them in the wash. I must have been in the water for longer than I thought. I stop for a sec, take a breath and drop my hand. She says again to walk to her. I do, average dick wiggling around. I remember wondering why is she smiling at me. She grabs a camera from the table and starts taking pictures of me! And a few close ups of her holding my dick which immediately sprouts to a 6 inch boner. At that point she goes back into the house with the camera then returns a few minutes later with car keys and purse. She has a small towel that she hangs on my penis and while gripping it again, says she's going out for a few hours and that her daughter will be home soon to put my stuff in the dryer. I wrap the towel around me and it barely covers me. My whole leg is exposed. She leaves and then it hits me. Daughter? Damn.

I'm recalling this from many years ago. I've been reading stories here anonymously for a while now and finally have the balls to write up my first story, which shall be continued

[hightab]

welcome to the site.

What happened next ?
Did anything happen with her daughter ?

[NickTwisp]

As a teenager I used to cut lawns in our neighborhood. Two of them had backyard pools. One particularly hot day, after the homeowner paid me, she asked if I would like to take a swim. Replying that I could go home and get my swimsuit, she said, "Oh, it's just me here right now, just strip to your underwear and go in."

I decided to do it, stripping to my blue boxer-briefs, and jumped in. I felt weird swimming there in my underpants but it was refreshing. No one else arrived during the time I swam there, fortunately. Next time I did her lawn I took a swimsuit along in a bag. I changed in her garage, worried that her daughter might walk in there since it attached to the house. That did not happen.

Definitely continue your story. Several of my high school buddies whom I have mentioned in posts here occasionally view this forum but are not registered.

[Bitsnbobs]

What happened to the photos, did you get to see them? Did anyone else see them?

[BareBones]

Nothing happened with the photos. I think she was mad and protecting herself by taking the pictures.
Here are more details.
I'm now alone in the yard locked out of the house with the towel. I'm thinking that maybe a babysitter or husband is coming home soon with the daughter. I have no clue so I now go oug front to maybe grab my bike and ride home nude. No way. Car pulls up. Lady gets out. Yells at me to get in the back yard. I of course listen. I'm covered up front but not my ass. I'm now sitting out back again. She comes out and introduces herself. She's Mrs James' friend. Turns out the daughter is coming home so she is going to help me get out of there. Clothes are now in the dryer. At least 30 minutes more of humiliation for me.
The friend is a few years older and a little taller and thicker. Big tits barely covered by a tube top, tight sarong around her waist. Thinking back, she was built like Mimi Rogers from that massage movie.
I remember being terrified that I was going to get in trouble. She sensed it and reassured me that no one was going to find out. Knowing me, I was probably feeling better looking at her breasts, which she probably also sensed. Anyway, clothes dried, I got dressed in front of her but she turned around. I think she only saw my butt. She gave me her phone number because she needed help with yardwork. She was impressed with my work? And her husband was injured or something.
I asked where Mr James was. She said there is no Mr James. She's Ms. James, a single mom. Oh. So we left. She said she was looking forward to my call and hoped I could start soon.
I don't remember the friend's name so let's call her Mrs Rogers.
I hope my story telling is okay. I'm regurgitating all of this from memories from decades ago.
To be continued...

[BareBones]

This is long, be warned, but I'm writing as I'm recalling details from many years ago. I'm finding that I thankfully remember A LOT of details

I called the next day and Mrs Rogers wanted me to clean up the yard as she was having guests over. I went the next afternoon after work and knocked on the door. She answered opening the door slightly but enough that I could see she was covering herself with a towel. She said the mower is out back in the shed. I mowed the front first then made my way to the back and started mowing again. She came out with a bottle of wine and sat on the patio. I think she had a book or magazine. I finished up the job and put the mower away. She walked over thanking me with some water. She seemed a little tipsy, stumbling just a little bit. She was wearing shorts with a button down blouse cut like a halter top. I remember this clearly, how it barely covered her breasts and how they jiggled as she walked. I then asked her to check me for tics since i had to go through some tall grass to pull some weeds. This is where my strange summer got even stranger, and I learned how drunk people can get super crazy.
She went inside and came out with a towel, a basket with soap and shampoo and another glass of wine.
She asks me to take off whatever I don't want to get wet. I took off my shirt, sneakers and socks leaving my shorts on. She sits me down on a plastic chair, leans my head down and washes my hair with the soap and garden hose.
She's now checking my scalp from in front of me, her chest just a few inches from my face. I'm not sure exactly how this happened but she lost her balance. I held her up by holding under the shirt with one hand kind of on her ribs and the other under her armpit. Once she was steady I put my hands down but she said no, hold her. This time I put both hands on her ribs under the shirt and pressing against her braless breasts. She didn't seem to notice or maybe didn't care. She kept checking my head. Somehow, maybe she shifted or something, but I had even more breast under my hands. I didn't move them but just held two big breasts steady. Now my dick is obviously fully erect and I started shaking with nerves. This lasted only a couple of minutes before she finished up and said to stand up, she now needs to check my legs. She wanted to sit with me standing in front of her.

My heart is pounding now because she's going to definitely notice my boner, but I listened and stood up. I remember her saying something funny, like "wow, is that just from holding me up?" She was now smiling and sipping more wine as she pulled down my shorts and underwear. She grabbed the soap and hose again, wetting me from the waist down, me naked. Now she stood behind me with the soap and washed my backside and legs. Then she reached around the front and washed my penis, balls, under the balls, groin, pubes etc. She was pretty drunk because I could feel her pressed up against my back holding herself up. She came around me again, sat down and rinsed the soap off.

Now her face is by my penis, leaning in and actually checking for ticks, running her fingers on my legs. She then told me to hold her steady so I thought screw it, and grabbed her breasts from the sides. She didn't say anything. Her focus then shifted to my pubes. She grabbed my penis with one hand and moved it around as she checked me. At this point, with me holding her breasts and her hand holding my dick, I start feeling a little tingle, then a big tingle, then, to my horror and pleasure, I ejaculate. More specific, I'm now squeezing those breasts as I ejaculate on her! I don't know if she said anything but she let me finish, squeezing out the last of it. She told me to help her get inside. We get in the house and I start apologizing. I thought I was in big trouble.
She then said "no, I'm the one that can get in trouble". We go to the landry room. She is facing the sink, back to me, and she takes off the cum covered blouse. Then to my surprise as I'm about to leave, she orders me to hold her steady, she has to wash the cum out before it stains. I hold her arms from behind. She said "no, underneath. I can't wash if you're holding my arms". I think she called me stupid too. So she raises her arms a little. I see massive side breasts, so I grab them. She leans over just far enough to press her behind against my semi hard dick which quickly becomes hard again. Now to my surprise again, she orders me to squeeze her breasts. I was just holding them. She also unsnapped the skirt so I'm now rubbing up against her bikini bottom covered ass. She put the blouse to the side but still faced away and grinded against me.
She then turned around and faced me, hands over her nipples. She smiled as she removed her hands. This was the first time I saw them completely bare. Wow. She then drops to her knees. "I need to clean you" she said (or something like that). She grabs my penis, rock hard, and licks the tip, then puts it in her mouth. This was my first blowjob! Needless to say, I came in her mouth a few minutes in. I didn't know why but she kept it in her mouth after I came for a minute or so.
She takes me out now finally and declares that she has to pee and is now slurring her speech so bad. The bottle of wine was now empty. She drank the whole thing. She tried standing up and fell into me. I caught her and helped her fet to the bathroom. I held her as she pulled down the bikini bottom. I got a good look at her bush. I try to leave her now but she made me wait. No, I wasn't turned on by the noise of her piss hitting the water. She finished, wiped and tried standing up. She didn't bother putting on the bikini as I helped her to the bedroom. I get her on the bed and she says I better ho, her husband will be home soon. I run to the backyard and grab my clothes when i realize that I left her on her back. My friends and I always knew that if one of us passed out drunk, to move us to our side. So I ran back to the bedroom just in case and yes, she's out cold on her back. I gave the breasts a few more squeezes, moved her to her side and got out of there. I rode my bike as fast as I could back home. I saw a message on the answering machine and thinking it was a friend, I hit play. It was a girl asking for me! It was the daughter and now I made the connection. Kelly James was two years ahead of me in school but we knew each other from sports. She was on the girls basketball team and I was on the boy's team. Anyway, I'll continue this story hopefully soon. And if you're wondering, this came back to me since I had a nude experience recently after a few years of nothing happening.