BigJohn
10-20-2009, 03:41 AM
Having posted one story and felt it was received well I figured I would post my first time with an older lady. I'm 25 now, but back when I was 19 I was the PM manager at a convenience store.
I had worked at the store through high school and then went away for my freshman year of college. The next summer I came back and got my job back. My bosses name was Julie. She was 36 years old, 5'3" tall, and probably around 140 lbs. She wasn't fat, but carried a little weight in her ass and thighs. She had short black hair and about a c cup. She kind of looked like Cathrine Zeta Jones if you shrunk her down and gave her a bigger ass.
My shift was always 2-11 4 nights a week. I never worked Sundays, but had to go in on Sunday nights to stock the freezer for the breakfast restaurant that ran during the week. An older lady worked in the restaurant and had trouble with the boxes. Every Sunday I would take enough out of the walk in freezer so she didn't have to labor to hard on Monday morning.
On this particular Sunday I had just come from the gym. I'm not in the best shape, but I like to run 5K's and half marathons. You don't have to be in great shape for those. I showered at the gym and just threw on a pair of gym shorts without underwear and a gray tank. I kept a pullover at the store for the freezer. A 19 year old male has a pretty easy time getting a hard on in mesh gym shorts. Just as a precursor.
I went to the store, moved all the food, and decided to mess around on the internet. I sat at the only chair at the desk and before I knew it the door flew open and Julie walked in. I had only seen her outside of work and in a non uniform twice. Nothing like this. She was wearing a tiny gray skirt made from sweat pants material and a blue tank top. She had no bra on and heir hair was down. We exchanged why we were there. She decided to come in on Sunday to do the books for Saturday and Sunday. We chit chat for a while and go about our business. I stood up at one point to change the channel on the TV above the desk in the office and at the same time she bent over in front of me to get something from a file cabinet. My cock rubbed right on her ass cheeks and immediately jumped. She lunged forward and said sorry. I turned 7 different shades of red and tried to hide what was now becoming a hard on. I just sat in the chair hoping she would break the silence or leave so I could get up and leave without her seeing my hard on. She giggled and said it's okay hon you're a young man and I'm a sexy lady. I laughed a little and then she asked me if she could use the chair. I stood up hunched over to try and hide it, but she noticed. She giggled again and joked that I should just go "rub one out" in the bathroom. I told her I was sorry and would leave. Here is where it gets foggy for me. It just sort of happened in a minute. I went to take off the pullover and while I was doing it my cock had really made a tent in my shorts. She turned and asked how long it had been for me. I was shocked. At this point I had slept with 7 women, but none in the 6 weeks since I had been home from college. I hadn't had the time or privacy to jerk off either. With that she turned and asked if I wanted to jerk off in front of her. I had no idea what to say. She pulled her tank top off and said c'mon, just picture me. Her tits were nice. Not saggy, but not super firm. I did the only thing I could think of and pulled my cock out of the bottom leg of my shorts and started to stroke it. She was talking to me the whole time. what she said makes me laugh now. It was straight out of a porn. "stroke that cock." "I bet you want to fuck me?" After a few minutes I said I needed a paper towel and she just got down on her knees and told me to spray her. I got it everywhere. Her face, hair, tits, neck, and skirt. As I stroked my now limpening cock I noticed she was trying to lick every drop of cum off herself. My cock started to get hard again. I just kept stroking. She then slid a pair of white cotton panties off and started to play with herself. I had never seen a woman masturbate in front of me before. Even when I was 19 my biggest turn on was having sex while the girl still had her dress or skirt on. My first girlfriend and I had sex like that all the time since we were young and it had to be quick. Her pussy looked like something out of a retro porn. It was very hair and I couldn't even see the lips. I don't know what came over me but I went over, stood her up, and bent her over. She stopped me and asked if I had a condom. I didn't. Then I remembered where we were. I told her to hold on, but she grabbed my hand and took me to the condom aisle. She opened a package and put it on my cock for me. She got on all fours and I fucked her right there in the condom/medicine aisle of the convenience store we worked at. Luckily I had jerked off or else I would have lasted under 30 seconds. After switching between doggy style and missionary for a while she asked if I was ready to cum. I was close and just started to pound harder and harder. When she could see I was almost ready she got up and pulled the condom off so I could spray her again. The same thing happened. All over her and she cleaned it up. She was standing there in just a tiny gray skirt and me in a tank top and we both laughed so hard. She told me that she had been into younger guys for a long time and love watching guys masturbate. I told her I had only been with girls my age and the sex was always pretty plain. We cleaned up the floor and got dressed in the office. I left, she finished her paperwork. We never had sex again, but I jerked off for her 3 more times in the 5 weeks left that summer. She would cum just from watching me jerk off. Every time I shot it right on her. One time she even lef me finish in her mouth.
I never went back to work there during the summers again. We saw each other a few times since but nothing ever happens. She got married and had a few kids. From that point on until I was 22 my sex life was very vanilla. I slept with a large number of girls, but it was almost always missionary, but if the girl was wearing a skirt I always made her leave it on.
I had worked at the store through high school and then went away for my freshman year of college. The next summer I came back and got my job back. My bosses name was Julie. She was 36 years old, 5'3" tall, and probably around 140 lbs. She wasn't fat, but carried a little weight in her ass and thighs. She had short black hair and about a c cup. She kind of looked like Cathrine Zeta Jones if you shrunk her down and gave her a bigger ass.
My shift was always 2-11 4 nights a week. I never worked Sundays, but had to go in on Sunday nights to stock the freezer for the breakfast restaurant that ran during the week. An older lady worked in the restaurant and had trouble with the boxes. Every Sunday I would take enough out of the walk in freezer so she didn't have to labor to hard on Monday morning.
On this particular Sunday I had just come from the gym. I'm not in the best shape, but I like to run 5K's and half marathons. You don't have to be in great shape for those. I showered at the gym and just threw on a pair of gym shorts without underwear and a gray tank. I kept a pullover at the store for the freezer. A 19 year old male has a pretty easy time getting a hard on in mesh gym shorts. Just as a precursor.
I went to the store, moved all the food, and decided to mess around on the internet. I sat at the only chair at the desk and before I knew it the door flew open and Julie walked in. I had only seen her outside of work and in a non uniform twice. Nothing like this. She was wearing a tiny gray skirt made from sweat pants material and a blue tank top. She had no bra on and heir hair was down. We exchanged why we were there. She decided to come in on Sunday to do the books for Saturday and Sunday. We chit chat for a while and go about our business. I stood up at one point to change the channel on the TV above the desk in the office and at the same time she bent over in front of me to get something from a file cabinet. My cock rubbed right on her ass cheeks and immediately jumped. She lunged forward and said sorry. I turned 7 different shades of red and tried to hide what was now becoming a hard on. I just sat in the chair hoping she would break the silence or leave so I could get up and leave without her seeing my hard on. She giggled and said it's okay hon you're a young man and I'm a sexy lady. I laughed a little and then she asked me if she could use the chair. I stood up hunched over to try and hide it, but she noticed. She giggled again and joked that I should just go "rub one out" in the bathroom. I told her I was sorry and would leave. Here is where it gets foggy for me. It just sort of happened in a minute. I went to take off the pullover and while I was doing it my cock had really made a tent in my shorts. She turned and asked how long it had been for me. I was shocked. At this point I had slept with 7 women, but none in the 6 weeks since I had been home from college. I hadn't had the time or privacy to jerk off either. With that she turned and asked if I wanted to jerk off in front of her. I had no idea what to say. She pulled her tank top off and said c'mon, just picture me. Her tits were nice. Not saggy, but not super firm. I did the only thing I could think of and pulled my cock out of the bottom leg of my shorts and started to stroke it. She was talking to me the whole time. what she said makes me laugh now. It was straight out of a porn. "stroke that cock." "I bet you want to fuck me?" After a few minutes I said I needed a paper towel and she just got down on her knees and told me to spray her. I got it everywhere. Her face, hair, tits, neck, and skirt. As I stroked my now limpening cock I noticed she was trying to lick every drop of cum off herself. My cock started to get hard again. I just kept stroking. She then slid a pair of white cotton panties off and started to play with herself. I had never seen a woman masturbate in front of me before. Even when I was 19 my biggest turn on was having sex while the girl still had her dress or skirt on. My first girlfriend and I had sex like that all the time since we were young and it had to be quick. Her pussy looked like something out of a retro porn. It was very hair and I couldn't even see the lips. I don't know what came over me but I went over, stood her up, and bent her over. She stopped me and asked if I had a condom. I didn't. Then I remembered where we were. I told her to hold on, but she grabbed my hand and took me to the condom aisle. She opened a package and put it on my cock for me. She got on all fours and I fucked her right there in the condom/medicine aisle of the convenience store we worked at. Luckily I had jerked off or else I would have lasted under 30 seconds. After switching between doggy style and missionary for a while she asked if I was ready to cum. I was close and just started to pound harder and harder. When she could see I was almost ready she got up and pulled the condom off so I could spray her again. The same thing happened. All over her and she cleaned it up. She was standing there in just a tiny gray skirt and me in a tank top and we both laughed so hard. She told me that she had been into younger guys for a long time and love watching guys masturbate. I told her I had only been with girls my age and the sex was always pretty plain. We cleaned up the floor and got dressed in the office. I left, she finished her paperwork. We never had sex again, but I jerked off for her 3 more times in the 5 weeks left that summer. She would cum just from watching me jerk off. Every time I shot it right on her. One time she even lef me finish in her mouth.
I never went back to work there during the summers again. We saw each other a few times since but nothing ever happens. She got married and had a few kids. From that point on until I was 22 my sex life was very vanilla. I slept with a large number of girls, but it was almost always missionary, but if the girl was wearing a skirt I always made her leave it on.