Straight Male / 50
I came from a broken home and no real guidance. I lived with neighbors and grand parents off and on through most of my teen years. I lived with good people and bad, but I some how managed not to go down the wrong road. I lied about my age to get a job at a movie theater because you had to be 17yo and I was only 16 at the time.
My Boss was an older lady named Mary, and she was 49yo I heard her telling another employee one day. Mary was nice but she didn't take any shit. Most of the people that worked there were teenagers except one guy that was gay. We didn't really know what being gay was back then, but everyone liked Dave regardless.
As I said Mary was 49yo. She was short, most likely 5'2" and always wore high heels to work. She was curvy but not bad at all. What Mary did have was a "Rack" how she carried those Breasts around was beyond me. She always wore make up and many a Movie goer took notice of Mary when she was out in the lobby.
Anyway with most of the employees being teenagers attendance was always a problem. When you are that age the idea of parties and having fun beats out going to work anytime! I was told I may not get many hours when I started, but we had so many kids not showing up for work Mary was always calling me into work even when I was supposed to be off.
One night after the theater was closed and I was sweeping the theater Mary came in and sat down in a chair near the door to the lobby. Row after row I had my little broom and dustpan sweeping up the popcorn until I got to the row she was sitting in.
When I was done I just pulled the seat down and sat next to Mary without a thought. I was tired it was way after midnight and I was ready to go home. Back in the day we had to wear those stupid little bowties and Mary reached over and unclipped mine without a thought.
For the next 30min Mary asked me all kinds of questions about my personal life. The reason she asked was the fact me and the gay guy Dave were the only two employees she could count on showing up for work. Since Dave was older he obviously understood responsibility but she wanted to know more about me. So I told her pretty much everything in the time we talked. No girlfriends and I was living with people that had family problems of their own. It was just better me being there at work than it was anywhere else.
Now the theater was as old school as the bowties we wore. Two levels with a balcony and a huge lobby upstairs with cushioned wingback chairs and sofas. Things had got a bit bad where I was staying and one night after we closed I asked Mary if I could spend the night in the theater. At first Mary said no way she could let me stay, but she would give me money for a motel and I thanked her but said no. As we were leaving Mary told me to follow her home and I could sleep at her house if I wanted?
I didn't notice the mileage but Mary lived in the middle of nowhere it seemed. We got to her house about 1:30am and there wasn't anything around her house that resembled another home for quite a distance. We walked inside and the house was fixed very nicely. Mary led me to the kitchen and opened the Fridge and had two beers in her hand. She sat them on the table and told me to open them while she got us something to eat. Mary had cold cuts and we each made a sandwich and talked for a bit.
We each had another beer and finished our sandwiches. The beer had soaked in before the food had a chance and I was feeling really tired suddenly. I think Mary saw that I was done and showed me where the bedroom was and flopped on the bed and was asleep in no time.
The next morning I woke up and went out to my car to get my toiletries so I could get cleaned up a bit. Without thinking I opened the bathroom door to see Mary standing there basically with her bra and panties on doing her makeup and hair. So embarrassed I went back outside and lit up and cigarette until Mary came outside a short time later. She asked for a cigarette, I didn't even know she smoked. Mary was smiling and asked me if it was the first time I had seen a woman only partially dressed. I suddenly thought about those large breasts that were spilling over the top of her bra just before leaving so quickly.
I had to think about it for a moment, and after some thought I guess it was the first time really. We finished our cigarettes and went back inside her house. Got a shower and brushed my teeth and Mary had some breakfast ready on the table when I came out. We had a nice talk as I enjoyed a meal that didn't come out of a box for once. Mary got up and I realized how short she looked without her heels on and I almost started to laugh.
The day was going by and Mary had things to do before going to work that night. I gave Mary a hug that lingered a bit too long maybe, but she didn't seem to mind. I kissed her cheek and she raised up on her toes to kiss me on the lips. I made a joke now about her being short and she said she could remedy that as she turned and walked back to her house. I went back to where I was staying and nobody questioned where I had been all night. I went to my room and hung out until it was time to leave for work.
That night we were busy, all three shows were packed. Other than seeing Mary before we opened the doors we didn't have any conversation. After closing I was upstairs with Dave cleaning up and he would be leaving before me. He had another full time job and had to be up early, so I usually was the last to leave besides Mary since she had to lock the doors at night.
I was just stacking cases of Candy that had come in during the day in the storage room when suddenly I felt hands around my waist. I quickly turned and there was Mary behind me. Before I could say anything she put her red lips to mine and kissed me. I could taste the color on her lips as her tongue slipped into my mouth. I don't know how long it took me to react but at some point I followed her lead. The kiss stirred me almost at once and the blood pumped into my cock and within moments I was rock hard.
Mary must have sensed my excitement, the next thing I felt was her hand rubbing my hardness up and down. I kissed her harder and my breathing quickened. My hands found their way to her ample breasts and I nervously squeezed them in unison. Mary's voice was subdued with my mouth on her own, but I knew she liked what I was doing to her breasts.
Finally she pulled away and took a small step back, her breasts heaved with every breath she took. Mary's face and neck was flushed with excitement. She then made a comment about the remedy for her being short and I followed her gaze down to the heels she was wearing now.
She led me out of the storage room into the lobby with chairs and sofas. Mary began to unzip my pants and when her warm hand wrapped around my cock the room began to spin it seemed. I was so hard when she let my cock go for an instant it slapped against my stomach. Mary kneeled in front of me and took my cock into her hot mouth a moment
later. I had to put my hands on her shoulders to keep from falling over, the pleasure was overwhelming. Within a few seconds my cock began to throb and twitch as Mary's mouth slid back and forth over my shaft. A sensation of pleasure washed over me and I began to ejaculate. Mary made a sound of sorts, her right hand clawed at my waist as my hot cum jetted into her Mouth. I remember hearing my voice as if I were shouting, my head thrown back as the release took me away. Mary's nails dug into my waist as she tried to swallow my cum as it pumped into her mouth.
Thankfully there was a sofa behind me and I collapsed onto it a moment later. Mary had quickly kneeled up between my legs and I watched her painted lips go to work on cleaning the cum from my cock. I was so mad because only after a few moments I could feel that "hardness" begin to abate. Mary noticed it too but she didn't seem to mind, she worked her mouth until every drop of cum was gone. She leaned forward and kissed me, her tongue blasting it's way into my mouth instantly. The taste of my cum was in her mouth and I reached outwards and squeezed her ample breasts very hard and she moaned with pleasure.
Mary stood up and reached under her skirt and pulled her panties down. She took my hand and guided it between her legs that were slightly apart now. Mary was soaking wet and she guided my fingers into her wetness. I didn't know exactly what to do, I had never done this to a woman before. Mary took my wrist and I moved my fingers within her wetness. Her eyes were shut tightly and she moaned with pleasure as I felt more wetness coating my fingers inside of her.
I had Mary lay on the sofa and I pushed her skirt up above her waist. I put three fingers inside of Mary and she took hold of my arm in a death drip. I don't know how many times Mary came but each time she dug her heels into the cushions and climaxed again. I leaned over and kissed Mary as she lay there trying to catch her breath, I could still taste myself when her tongue slithered into my mouth again. My began to feel the hardness returning to my cock a few minutes after our mouths joined. I stripped and Mary pulled me down onto her and into her a moment later.
My cock entered her wetness and the heat from her loins would make me cum again rather quickly. Mary dug her heels into the backs of my legs and her red nails clawed at my back as she arched her hips upwards and came all over my cock that was buried inside of her.
I followed her home that night and we showered together. I soaped her breasts and made her cum in the shower without touching her below the waist. That would be later in her bed, and she would show me how to please a woman and how to take my time doing so. Mary got me a cock ring so I wouldn't cum so quickly and showed me things that she liked to do as well.
We were lovers for almost two years before it ended. Mary told me she was going to resign and take some time off and do something else. She said it was time that I got on with my life and I needed to move on and be with people my own age. I didn't want to move on, I was in love with Mary. Obviously when you are a teenager your mind doesn't see the big picture and I was devastated. Ashamed to admit this but I stalked her for a while. I would go at night and park my car down the road and walk to her house. I was sure there was another guy, probably older and he was the reason Mary wanted to part ways with me. The times I did go I never saw another vehicle in the driveway besides Mary's car.
My Boss was an older lady named Mary, and she was 49yo I heard her telling another employee one day. Mary was nice but she didn't take any shit. Most of the people that worked there were teenagers except one guy that was gay. We didn't really know what being gay was back then, but everyone liked Dave regardless.
As I said Mary was 49yo. She was short, most likely 5'2" and always wore high heels to work. She was curvy but not bad at all. What Mary did have was a "Rack" how she carried those Breasts around was beyond me. She always wore make up and many a Movie goer took notice of Mary when she was out in the lobby.
Anyway with most of the employees being teenagers attendance was always a problem. When you are that age the idea of parties and having fun beats out going to work anytime! I was told I may not get many hours when I started, but we had so many kids not showing up for work Mary was always calling me into work even when I was supposed to be off.
One night after the theater was closed and I was sweeping the theater Mary came in and sat down in a chair near the door to the lobby. Row after row I had my little broom and dustpan sweeping up the popcorn until I got to the row she was sitting in.
When I was done I just pulled the seat down and sat next to Mary without a thought. I was tired it was way after midnight and I was ready to go home. Back in the day we had to wear those stupid little bowties and Mary reached over and unclipped mine without a thought.
For the next 30min Mary asked me all kinds of questions about my personal life. The reason she asked was the fact me and the gay guy Dave were the only two employees she could count on showing up for work. Since Dave was older he obviously understood responsibility but she wanted to know more about me. So I told her pretty much everything in the time we talked. No girlfriends and I was living with people that had family problems of their own. It was just better me being there at work than it was anywhere else.
Now the theater was as old school as the bowties we wore. Two levels with a balcony and a huge lobby upstairs with cushioned wingback chairs and sofas. Things had got a bit bad where I was staying and one night after we closed I asked Mary if I could spend the night in the theater. At first Mary said no way she could let me stay, but she would give me money for a motel and I thanked her but said no. As we were leaving Mary told me to follow her home and I could sleep at her house if I wanted?
I didn't notice the mileage but Mary lived in the middle of nowhere it seemed. We got to her house about 1:30am and there wasn't anything around her house that resembled another home for quite a distance. We walked inside and the house was fixed very nicely. Mary led me to the kitchen and opened the Fridge and had two beers in her hand. She sat them on the table and told me to open them while she got us something to eat. Mary had cold cuts and we each made a sandwich and talked for a bit.
We each had another beer and finished our sandwiches. The beer had soaked in before the food had a chance and I was feeling really tired suddenly. I think Mary saw that I was done and showed me where the bedroom was and flopped on the bed and was asleep in no time.
The next morning I woke up and went out to my car to get my toiletries so I could get cleaned up a bit. Without thinking I opened the bathroom door to see Mary standing there basically with her bra and panties on doing her makeup and hair. So embarrassed I went back outside and lit up and cigarette until Mary came outside a short time later. She asked for a cigarette, I didn't even know she smoked. Mary was smiling and asked me if it was the first time I had seen a woman only partially dressed. I suddenly thought about those large breasts that were spilling over the top of her bra just before leaving so quickly.
I had to think about it for a moment, and after some thought I guess it was the first time really. We finished our cigarettes and went back inside her house. Got a shower and brushed my teeth and Mary had some breakfast ready on the table when I came out. We had a nice talk as I enjoyed a meal that didn't come out of a box for once. Mary got up and I realized how short she looked without her heels on and I almost started to laugh.
The day was going by and Mary had things to do before going to work that night. I gave Mary a hug that lingered a bit too long maybe, but she didn't seem to mind. I kissed her cheek and she raised up on her toes to kiss me on the lips. I made a joke now about her being short and she said she could remedy that as she turned and walked back to her house. I went back to where I was staying and nobody questioned where I had been all night. I went to my room and hung out until it was time to leave for work.
That night we were busy, all three shows were packed. Other than seeing Mary before we opened the doors we didn't have any conversation. After closing I was upstairs with Dave cleaning up and he would be leaving before me. He had another full time job and had to be up early, so I usually was the last to leave besides Mary since she had to lock the doors at night.
I was just stacking cases of Candy that had come in during the day in the storage room when suddenly I felt hands around my waist. I quickly turned and there was Mary behind me. Before I could say anything she put her red lips to mine and kissed me. I could taste the color on her lips as her tongue slipped into my mouth. I don't know how long it took me to react but at some point I followed her lead. The kiss stirred me almost at once and the blood pumped into my cock and within moments I was rock hard.
Mary must have sensed my excitement, the next thing I felt was her hand rubbing my hardness up and down. I kissed her harder and my breathing quickened. My hands found their way to her ample breasts and I nervously squeezed them in unison. Mary's voice was subdued with my mouth on her own, but I knew she liked what I was doing to her breasts.
Finally she pulled away and took a small step back, her breasts heaved with every breath she took. Mary's face and neck was flushed with excitement. She then made a comment about the remedy for her being short and I followed her gaze down to the heels she was wearing now.
She led me out of the storage room into the lobby with chairs and sofas. Mary began to unzip my pants and when her warm hand wrapped around my cock the room began to spin it seemed. I was so hard when she let my cock go for an instant it slapped against my stomach. Mary kneeled in front of me and took my cock into her hot mouth a moment
later. I had to put my hands on her shoulders to keep from falling over, the pleasure was overwhelming. Within a few seconds my cock began to throb and twitch as Mary's mouth slid back and forth over my shaft. A sensation of pleasure washed over me and I began to ejaculate. Mary made a sound of sorts, her right hand clawed at my waist as my hot cum jetted into her Mouth. I remember hearing my voice as if I were shouting, my head thrown back as the release took me away. Mary's nails dug into my waist as she tried to swallow my cum as it pumped into her mouth.
Thankfully there was a sofa behind me and I collapsed onto it a moment later. Mary had quickly kneeled up between my legs and I watched her painted lips go to work on cleaning the cum from my cock. I was so mad because only after a few moments I could feel that "hardness" begin to abate. Mary noticed it too but she didn't seem to mind, she worked her mouth until every drop of cum was gone. She leaned forward and kissed me, her tongue blasting it's way into my mouth instantly. The taste of my cum was in her mouth and I reached outwards and squeezed her ample breasts very hard and she moaned with pleasure.
Mary stood up and reached under her skirt and pulled her panties down. She took my hand and guided it between her legs that were slightly apart now. Mary was soaking wet and she guided my fingers into her wetness. I didn't know exactly what to do, I had never done this to a woman before. Mary took my wrist and I moved my fingers within her wetness. Her eyes were shut tightly and she moaned with pleasure as I felt more wetness coating my fingers inside of her.
I had Mary lay on the sofa and I pushed her skirt up above her waist. I put three fingers inside of Mary and she took hold of my arm in a death drip. I don't know how many times Mary came but each time she dug her heels into the cushions and climaxed again. I leaned over and kissed Mary as she lay there trying to catch her breath, I could still taste myself when her tongue slithered into my mouth again. My began to feel the hardness returning to my cock a few minutes after our mouths joined. I stripped and Mary pulled me down onto her and into her a moment later.
My cock entered her wetness and the heat from her loins would make me cum again rather quickly. Mary dug her heels into the backs of my legs and her red nails clawed at my back as she arched her hips upwards and came all over my cock that was buried inside of her.
I followed her home that night and we showered together. I soaped her breasts and made her cum in the shower without touching her below the waist. That would be later in her bed, and she would show me how to please a woman and how to take my time doing so. Mary got me a cock ring so I wouldn't cum so quickly and showed me things that she liked to do as well.
We were lovers for almost two years before it ended. Mary told me she was going to resign and take some time off and do something else. She said it was time that I got on with my life and I needed to move on and be with people my own age. I didn't want to move on, I was in love with Mary. Obviously when you are a teenager your mind doesn't see the big picture and I was devastated. Ashamed to admit this but I stalked her for a while. I would go at night and park my car down the road and walk to her house. I was sure there was another guy, probably older and he was the reason Mary wanted to part ways with me. The times I did go I never saw another vehicle in the driveway besides Mary's car.
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