Summer that Changed Everything

All characters are 18 or older. All past descriptions was when the character was 18 or older.

I never thought my summer would turn out like it did. In ways this summer changed everything for me... in ways I never would have expected.

It all started soon after school ended and summer was just beginning. I was 19 and back from my first year of college. Back to small town America. Back to my parent's house. Back to being basic. Back to how things had always been for me, or so I thought.

But oh how things were going to change!

A little about me. My name is Jacob and I'm quiet, usually shy until I know someone, and pretty average. I grew up in a typical home with my mom and dad. We went to church every Sunday and Wednesday. I basically lived a sheltered life. I went to school and came home, occasionally hanging with friends. In high school, I had good grades and a couple of close friends, but nothing in the relationship department. I tried, I really did. But girls just did not seem interested. I think I was too basic. I wasn't the jock, I wasn't the one with the ripped body, or the excessive flirt like others. I could blend into the crowd and no girl took notice. So that left me a virgin going into college, something I hoped would change.

However, it did not. Nothing changed at all in the relationship department in college. Again, I tried, but nothing happened. So that left me excessively horny all the time and left me beating off in my dorm room daily. Just like when I was back home, each day I could be found with my hand on my dick until I came. Luckily all the rooms in the dorm hall I was assigned were single rooms, so that left me with a lot of privacy. This was good for me, since I was horny all the time and jacked off at least twice every day. Honestly, sometimes it was even more. What else was I to do? I just couldn't help myself. I'd see a beautiful girl or a professor and I couldn't take my mind off of them until I was done beating off in my room. Frequently I found myself rushing into my dorm after class, locking the door, quickly stripping all my clothes off, and furiously beating off to whoever I had just saw. Then as soon as I came I would clean up and just lay there naked until I was ready to get dressed.

This became a regular habit for me. I enjoyed jacking off and knew I did it a lot, but what else was I to do. It gave me relief and it felt good. When school was nearing the end of semester I soon realized things with my masturbation sessions would change once I was back in my parents' house. My midday sessions or anytime I wanted would definitely end with mom not working and being home. Honestly, I'm a bit noisy when I jack off so I knew things would change. I'd have to result to jacking off in the shower or really late at night or anytime I actually had the house to myself.

I didn't realize though that mom had other plans for me being home during the day. When I got home from college she informed me that she had gotten me a summer job. I was fine with working, the idea of making money thrilled me, especially when I learned the pay for I'd be getting. Just the idea of working every day didn't thrill me much, but I had no choice. Mom had agreed and thought I'd be thrilled. I didn't like to disappoint my parents so I didn't show any of my reservations with the job.

The job would last all summer. An older lady, who had started attending our church during the fall when I was away, had a lot of plans around her house and needed a summer worker. Her name was Hattie Lee or Ms. Hattie as mom called her. I hadn't ever met her, but mom said she was friendly and was glad of the help. She had been asking around the church for a good, reliable young man who could help do a lot of the updates she had in mind that summer. The job would also entail yard work and work on her pool. She had moved in last year to our town and really wanted to update the place. Mom had volunteered me and said I'd be perfect for the job. I couldn't object with mom. Ms. Hattie's husband had died of cancer a few years before she moved here mom said so she had no one to help. As much as I didn't want to work every day, and not be around the house for any chance I may have to jack off without any interruptions when mom would go out, I felt good about the job and helping Ms. Hattie out. I felt bad that she was alone and had no one.

On the first day on the job I showed up a couple minutes before I was suppose to be there at 9:00. I hadn't been to her house before so I made sure I had time to figure out where it was exactly. Her house was on Shady Drive, on the other side of town from where we lived. I found it with no difficulty. As I walked up to the front door, my nerves hit me. I didn't know quite what to expect as far as Ms. Hattie's looks. I knew she was older so I expected a much older person than who greeted me at the door. I could tell she was older, but not bad at all. She sure didn't show her age like so many do. She was sweet, with a gentle nature about her. She was polite and welcoming. I could tell she was grateful for the help and my presence. For someone who is generally shy, I felt instantly at ease around her.

After the general greeting at the door, she welcomed me inside. She asked if I wanted anything to drink, but I said no. She showed me around the inside of the house describing what she wanted to do in each room. She had made a list she gave me too luckily because there was no way I could remember it all. None of the supplies had been bought or picked up yet, so I'd have to do that too. Most of the tasks involved moving furniture around or painting the walls/baseboards, or switching out things like light fixtures, faucets, knobs, etc to update the house. Then outside she wanted to really get the pool cleaned daily and kept in check, along with keeping the lawn mowed and replacing all the landscaping. It would definitely keep me busy, especially since I hadn't done hardly any of this work before. I felt I could do it though and she seemed to know what she was doing, just needed someone to do it. I was definitely good with my hands (or hand lol) so I knew I could get it all done.

Ms. Hattie told me she liked to spend time at the pool each day if I wanted to do the pool first thing every morning. The order I did the rest of the work was totally up to me. I was to work from 9:00-5:30 each day, with lunch and drinks provided. She told me I could come and go in the house as needed to use the restroom or to get more drinks. She was going to cook lunch each day. She told me she usually went out for a walk in the later afternoon, about the time I'd be finishing up for the day. She said I could just let myself out and leave on time when she was gone and she would see me the next day. I'd be working Monday- Friday each week. She was so nice, welcoming, and explained things so well so I was excited to get started.

After she explained everything she asked if I had any questions. I didn't and thanked her for the job. I headed outside and started cleaning the pool. It was already filled for the season, but did need cleaned. In the outside shed I found the chemicals too and luckily they had instructions of how to check them. I checked and adjusted the levels. After the pool I then got the mower out and mowed the yard. This took a bit of time. It hadn't been done this season yet and it was already mid May. After mowing I then weedeated. Soon I saw Ms. Hattie on the back porch, I stopped the weed eater and she said lunch was ready.

Lunch with her wasn't awkward. She had fixed blt's that day. She asked me about college- what I was studying and stuff like that. It wasn't hard to talk to her. She was just so nice and kind. It was honestly like I had known her for years. As we were both finishing up lunch she asked me what I planned to do next. I told her I thought I'd go ahead and start removing all the old plants that were dead around the house. She said that sounded great and she liked the idea of the landscaping being done before it got so hot in June and July. She said the inside jobs would be better then. I told her I better get started and she told me that she would check in on me later on.

I started working outside. The owners before Ms. Hattie definitely loved landscaping. There were so many shrubs and bushes around, along with flowers too. They went around the whole house and then scattered amongst the fence line and around the pool too. All were dead or not something she wanted anymore. A lot of the smaller trees needed trimmed too as they were starting to brush up against the house and windows. I figured this work would take a couple days at least. Ms. Hattie had all the tools I needed in the shed so it was easy to get busy. After about an hour and a half, I was getting hot and went inside to get some water and use the restroom. As I was going inside Ms. Hattie was coming out, wrapped in a towel. She asked if everything was okay and I told her of course and that I was just getting some water. She told me to help myself and she would be in the pool if I needed anything.

After coming back outside I went back to work. I noticed a large vine growing along the side of the house. I got the ladder to start removing it. It came off easily but stretched all up the side of the house, even to the upstairs. When I was climbing up the ladder I noticed I had a good view of the pool. The water looked so good. It made me proud of my work earlier this morning cause it didn't look that clear when I got here. As I was removing some vine I noticed what or who I hadn't noticed earlier cause she must have been in the part of the pool I couldn't see around the other side of the house. Ms. Hattie was getting out of the pool. Her back to me, so she couldn't see me looking. I didn't look long but was surprised at what I saw. She looked so good to be approaching 60 as I had learned earlier at lunch. I couldn't believe how good she looked in her light blue bikini. I also didn't expect her to be in a bikini. I didn't stare long and went right back to work. She soon went into the house wrapped in a towel.

I finished up with the vine and then finished removing the plants on the same side of the house. It was getting close to time for the work day to end. The day really seemed to fly by. I wanted to give myself plenty of time to clean up. I got all the removed plants loaded up in old trash cans I found in the shed and a couple of wheelbarrows. I'd get rid of them in the morning. As I was closing up the shed I noticed Ms. Hattie coming across the lawn, looking as if she was about to leave.

"Wow, Jacob it already looks so much better," she said, "you certainly have gotten a lot accomplished in just a day."

"Thank you. I'm glad you like it." I replied.

"Well I'm headed out to the store. I'll see you tomorrow morning."

"See you in the morning"

I glanced at her as she was walking away. Then headed to grabbed the ladder to put beside the shed. I looked at my watch and it was time for me to go. I had paced myself good that day and was proud of the work I got done.

When I got home, Mom was finishing up supper and dad had just gotten home from work himself. I cleaned up in the bathroom and was ready for supper. After the hard work today, I was definitely hungry. As we ate my parents asked me about the day. They were glad of the work I had done and said a summer job would be good for me. After supper I went to my room and finished unpacking the last few boxes from my dorm. I then read a little and then decided to go for a run. It was about nine when I got back and my parents were watching tv in the living room. They asked me about my run then I excused myself to go shower.

At our house there are two bathrooms with showers. One attached to my parent's room and then one to mine. I could tell exhaustion was setting in from working outside all day. As I stripped down to get into the shower I made sure to lock the bathroom door. My parents were already in bed but I'd rather be careful than risk getting caught. Instantly it's like my dick knew what I was about to do. Growing up in this house it had become a nightly ritual for me to stroke off in the shower. In the shower I could make a little noise and not be heard, plus less of a risk of getting caught than beating off in my bed.

As I got in under the warm stream, my dick was already semi hard. I let the water run over me for a bit. It felt good after the work I did today. As my dick started to grow even more under the warm water, probably in anticipation, I wrapped my hand around it and started to tug it to get it to its max. I'm not exactly big, not that I've had a girl tell me or anything, but from I've read online I was a little more than average at 7 inches at my hardest. I wasn't thick though. As my dick was hard in my hand I started to think about what I'd jack to that night, well really to who I'd stroke off to. Suddenly Ms. Hattie came to my mind. Why her? I tried to shake her out of my mind and think about someone else. I couldn't think about my boss, who was so much older than me.

Maybe Rachel from my English class this past semester. I started tugging but she wasn't doing the trick. Maybe Mia from Chem Lab. She was so beautiful and I had beat off way too many times to count in my dorm at school thinking about her. But tonight she wasn't doing the trick either. I'd always thought she was so amazing looking and she was the one who I thought of most of the time this past semester as I whacked off. But even she wasn't doing it for me. My dick was starting to go soft and then Ms. Hattie came to mind again. Could I honestly be turned on by such an older woman who happened to be my boss? My dick was springing back to life in my hand. I guess I could be. It was just jacking. What could it hurt?

I suddenly started jacking wildly like I always seemed to thinking of Ms. Hattie in the dress she was wearing when I had first arrived this morning. Man was thinking of her turning me on! I kept stroking up and down on my dick. I wasn't going to last long I knew. I was then thinking of her face and hearing her talking to me when suddenly, without much warning, I busted my load all over the shower wall and my hand. A longer than normal for me moan escaped my mouth when I did.

My load was huge. How could thinking of such an older lady make me cum so much more than normal? My hand was covered and the wall too with several big globs of my white cum and then streams of it and some clear cum hanging. I seriously hadn't cummed like that in awhile and didn't expect it either.

I was about to wash my hand off when I squeezed the head of my dick to get the last gob out. It felt so good and I could feel my dick start to come back to life. I didn't expect to be in the mood still. I can get hard again pretty fast but this was different. It's like I was ready to jack again. I gave my dick a few tugs with my cum covered hand. I thought the feeling would go away but it didn't. The idea of doing something I hadn't done in quite sometime came to my mind- to use my cum as lube and jack again. I always get so messy when I do that. But my dick did feel so good in my hand.

I quickly covered my dick in my cum and got more off the shower wall on my hand. Suddenly Ms. Hattie in her bathing suit came to my mind. Her getting out of the pool. Her butt in full display. I was stroking fast already at that point. Thinking of her butt. What I wouldn't give to touch it? To touch it while I was jacking would be a dream. To rub my dick on her butt, I couldn't imagine. I was really getting into my stroking. My dick was covered in my cum. I got more from the wall to use on it and resumed my stroking. I already felt myself getting close. What I wouldn't give to see Ms. Hattie without the bikini bottoms. I bet her butt was amazing naked, even if it was older. Suddenly I felt myself about to burst and after a couple more strokes I erupted again. This time my load went straight up and landed on my chest and stomach.

I was out of breath. I was covered in cum. That was intense. I didn't think I'd be stroking off to my new boss when I met her that morning but thinking of her gave me two intense back to back orgasms. My dick started losing its hardness so I washed away the cum from my body using the removable shower head. I made sure to clean the walls off too. I sure had a lot of cum going down the drain at that point.

I quickly took my shower after cleaning up and got out. I put on my pajama bottoms and read a little more. I always sleep in pajama bottoms and no shirt. After reading I got into bed. I was laying with my hands behind my head thinking about what jobs I'd do the next day at work when suddenly I thought of Ms. Hattie again. No way could I be turned on again so soon. Especially after blowing two huge loads in the shower not that long. But I felt my dick start to rise.

I hate going to bed hard and horny so I eased down my pajama pants while staying under the covers. I couldn't get too into my jacking this time but the door was locked and I knew my parents were asleep, so I started stroking. Slowly but again I could tell real quick I wasn't going to last. Usually I last longer, especially after two loads being emptied not that long ago. But thinking of Ms. Hattie sure had an effect on me. An effect I never could have imagined. This time I imagined her watching me stroke. Her just sitting there in a bra and panties, white I imagined, as I stroked off. She would just sit and watch. I didn't last but a couple minutes thinking of this until I came all over my stomach. I was out of breath. What an effect thinking of her had on me!

I quickly got up and went into my bathroom to clean up with toilet paper and flush away the evidence. After this I put my pajama pants back on and fell asleep quickly.

*the action will get more intense! This is my first story and had to build the story line. This will be a longer series with lots of entries.