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An Older Woman

A guy remembers his first time with an older woman
It was a hot July and I was working at my father's restaurant. Since it was seasonal, the staff only worked there from May until September. I started working there when I was ten years old, but now that I was eighteen, I was promoted to a more responsible position. The restaurant had a cellar where we stored all the foodstuffs, a main floor that could accommodate 180 people, and an upstairs that could hold 80 people. I was in charge of the cellar.

My father employed waitresses and chefs from London and part of the deal was they had rooms within the restaurant. In fact, there were about eight different bedrooms and I shared one with a friend. One of the regular employees was a married lady named Margaret. I had always liked Margaret and she always called me her favourite boy. She was about five feet four inches tall with lovely blonde hair, big rounded tits, and a trim waist that was exaggerated by her wide belt, which she always wore tight with an above-the-knee blue serge skirt. Her tits looked lovely and full inside her crisp white blouse. She had lovely big blue eyes set in a round face. Her nose had a slight turn up at the end and I always joked about that in a very friendly manner.

She had watched me grow up, but had never allowed this to stop her from putting her arms around me and being very friendly. Little did she know that over the years I had a crush on her and had on many occasions masturbated myself over fantasies about her. But this season I noticed that when I saw her there was a different feeling inside me and I couldn't work near her without getting a hard on. At first she pretended not to notice, but one day when we were having a lunch break together she started asking me personal questions. She knew I had a girlfriend and she asked me if I had had sex with her.

"Of course I have, all the time," I lied.

"Right!" She said as she looked at me as I blushed and as her head kept nodding.

We really did have a good friendly relationship and we always worked together in the upstairs restaurant. She caught me looking at her many times and she even made jokes about it. I was so naive and she obviously knew this and she caught me time after time ogling her ass. She made things harder for me by rubbing herself up against me, even brushing her tits across my arms when we were drying the plates.

One Saturday morning in July my dad told me to go work in the cellar and explained to me what I had to do. I had been down there about an hour when Margaret called my name. I answered and went to meet her. She asked me where all the clean tablecloths were and I told her the last room down to the right, as there were about ten rooms in the basement. She said that she would not go down there on her own, as there was no light.

I put the light on which supplied the room and walked down with her. The tablecloths were on the top shelf and she couldn't reach them so I reached above her head. As I stretched above her, I got the funniest feeling inside me; the small hairs on the back of my neck stood up and my arms were covered in goose bumps. She noticed this and turned around and looked up at me, saying, "l really do have an effect on you, don't I?"

At the same time, she brushed her lovely, small, soft fingers over my arm. By now I was really blushing. I was holding the tablecloths above her head when she said, "What’s this? Are you really pleased to see me?”

Her hands had dropped down and touched my already throbbing cock, she looked up at me and stood on her toes. I lowered my head and gently put my lips on hers. They seemed to be welded together as I dropped the tablecloths and put my arms around her and lifted her off her feet, still kissing her all over her face. Within seconds she had unzipped my pants and had somehow managed to get my cock out. She mentioned that it was dripping with pre-cum.

I couldn't move, I'd never had any female touch me. She kept telling me to relax but I couldn't and within seconds I'd cum. I was so sexually charged. I was shaking and seemed to be transfixed. She told me not to worry and said that I must promise her to go around to her house on our night off. I agreed.

Our night off was Thursday. How I got through the next few days was difficult as all I seemed to do was masturbate. I couldn't stop thinking about her.

I was going to fuck the woman I'd had a crush on for years. I just couldn't wait to get my hands all over her.

I asked one of the chefs about sex. He actually drew me a picture of a pussy as I'd never seen one and told me to work on the clitoris. He told me to tweak the nipples, to suck them and to lick the clit. I felt more at ease. Margaret would now touch my hand, and put her arms across me so that her breast was right in front of my face. She was flirting all the time. On the Wednesday before we were to get together I mentioned that I'd never bought any condoms. She laughed and said that she was on the pill and that everything would be okay.

Thursday arrived and I got in so much trouble during the day because I was making so many mistakes and kept dropping plates. Finally I was at her front door, Margaret opened it and had on a lovely yellow summer dress. She could see that I was nervous and took me into her front room and we sat down on the sofa. She told me that her husband was away on a trip and wouldn't be back till Saturday. We sat talking for what seemed like ages. I could feel my cock really throbbing and leaking pre cum. I just hoped that I could hold on to it but knew that I was good for at least three orgasms as I had jerked myself silly all week, at least three or four times a night.

"Come on then, let's go upstairs," Margaret said.

I'd been waiting impatiently for this moment. When we finally got into the bedroom, she asked me to undress her. The dress undid from the back and I undid the buttons as I kissed her neck. I slid the dress over her shoulders and let it drop to the floor. I was standing behind her and as the dress hit the ground I looked down to see that she was naked. Her ass was exactly how I had imagined it: round, lovely, and with firm cheeks. Her waist was slim and her shoulders square and straight. When she turned around and I saw her breasts, they were amazing. Her nipples were large and prominent.

Both tits were full but firm. She had a flat stomach and tight curly blonde pubic hair. She looked like a model to my naive brain. She told me to take my time as she started to undress me. It felt strange being naked in front of a woman. She put me at my ease by kissing my nipples and biting them till it hurt. We kissed and kissed. She wouldn't let me touch her pussy but I was content to fondle the best tits in the world. I sucked her nipples and tweaked them really hard, pulling them out. They extended a full inch.

She told me to lie down on my back on the bed and she came to my side and knelt over me. She gently took hold of my cock in two hands and told me that I should be proud of the fact that I had such a big cock. She slowly pulled back the foreskin and saw all the pre-cum. She bent over and put my swollen knob in her mouth and nibbled on it, gradually sucking it into her mouth and twirling her magical tongue all the way around the head. I could not bear it and could feel the rush coming from deep within. I told her this and she said she knew and carried on until I filled her mouth full of my seed, which she swallowed.

My erection wasn't impaired at all and I wanted to see her pussy. She turned over and opened her legs as wide as she could. I knelt between her legs and just looked at her glorious pink flesh. She used her fingers to open her lips wide. I could see her pink magic hole. She told me to lick it. It tasted nice and I remembered what I was told and began to suck her clit, I also began to slide my fingers inside her cunt. One, two, three fingers slid in so easily. She told me to slow down and to keep sucking her clit. After a while I noticed her body stiffen and she began to shout faster, faster, fucking faster. Then all of a sudden she shouted out and dug her fingernails in my back, and then she came and I felt her relax.

We both lay there for a while and since I still had a raging hard on she told me the time had come for me to lose my virginity. She said that I would always remember this night because she had passed on her experience to make it special for me. At the time I didn't understand what she meant, but now years later I know she was right. I will always recommend a young man to be seduced by an older woman. She gently guided my cock inside her cunt and began to ride me slowly. I couldn't believe how great it felt. I came within a minute but I asked her not to stop. She kept going as I saw all my juices dripping from her. I turned her on her back and started to pump her quicker, I so wanted her to come. I began to sweat and moan as I could feel that special feeling coming from right inside me. She began to shout, "Fuck me hard Ronnie, fuck me harder, fuck me, oh god I'm coming."

She dug her fingernails in my back and pulled me really hard into her, until I saw the blood rush to her face and knew then that she was spent. Seconds later I came for the third time. Just about every Thursday night we got together whenever her husband was gone, which seemed to be a lot. I never could understand how a man with such a hot, sex crazed wife would be stupid enough to leave her alone.

On one particularly hot night we went out on a real date. To keep up appearances she drove us three towns over to a little club that also served dinner. It was a real hole-in-the wall, but the band was great and so was the food. We danced and chatted until she got up to go to the bathroom. As she walked away from me she looked back over her shoulder and gave me a wicked smile.

I followed her, waiting outside the door. When she came out I pushed her back in. Our summer of fucking had given me a new confidence. Seeing her and feeling her on the dance floor had driven me to a fever pitch. I couldn't wait. I kissed her hard and grabbed at her tits. Her hands were all over me as our tongues battled between our mouths. Not wanting to waste any time I turned her around and bent her over the counter. I reached under her skirt and ripped off her panties before unzipping my pants and taking out my cock.

In no time I was shoving my swollen prick into her hot cunt. I grabbed on her hips and just drove home, over and over, while she held onto the counter for dear life. I was possessed, a fuck machine that she had created. She tried to restrain her cries as we fucked but I was sure the whole club could hear us, even with the music playing. It didn't last long. I unloaded what felt like a gallon of sperm into her hot pussy. When I was done I withdrew and stuffed myself back into my pants. She pulled up her panties and we left the bathroom.

She was right: I've never forgotten her and at the time, I'm sure I did love her that summer. If I saw her today, I would thank her for giving me such a great start.

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