Growing up my family and a few other neighbors became really good friends. We’d be invited to various parties and celebrations at each other’s houses.
The Sheffields lived across the street. The oldest daughter, Mary, babysat for me when I was a kid. I had a bit of a crush on her older brother Matt who was ten years older than me.
The Sheffields were in their late fifties when I graduated high school. They were always nice like all the other neighbors. Mr. Sheffield was fifty nine. I thought Mrs. Sheffield was still pretty even though she was older. I never thought about it much but even as a younger teenager I thought Mr. Sheffield was handsome. An older version of Matt really.
Right after I graduated high school the Sheffields had a pool party my family was invited to. I wore a one piece because I didn’t feel comfortable wearing a bikini around family or family friends.
My mom would have scolded me anyway. One time she saw me wearing a bikini I bought to wear to the beach with my friends and told me I looked like Pamela Anderson as if that was a bad thing.
I had developed early so by the time I was eighteen I was a full C cup on a five foot two inch frame at one hundred and fifteen pounds. I’m Mexican on my mother’s side and those latina curves definitely kicked in early.
I would get noticed by guys but I never dated guys my age. I didn’t want to be bothered with drama that a lot of peers went through with boys. My very Catholic mother always told me sex before marriage was a sin but I never bought into that.
I was a theater and choir geek in school and wasn’t part of the popular crowd anyway. Though doing local community theater is how I initially met and fucked older guys.
Also I had a friend who was a goth chick who dated a couple older guys. She was a nice girl but a bit bad too. She was the first to tell me how awesome it is to be tied up and fucked.
I always found older guys attractive and thought guys in their thirties and forties were the hottest. I wouldn’t say I dated them because it was only fucking around. Luckily I never confused sex with love so I never got too duped by an older guy.
The summer after high school I found out even older guys could be hot and amazing lovers.
At the pool party, Mr. Sheffield asked me about graduating and my plans for college. The usual stuff grownups ask high school graduates. As we were talking, I noticed his eyes looking down at my body. I didn’t think too much of it and felt flattered.
“Sandy, Alanya Escort if you ever get bored during the summer you can come over and use the pool. Bring a friend over,” Mr. Sheffield offered.
“Oh thank you. That’s really nice of you to offer,” my naive eighteen year old self had said.
“I’m home Mondays so you can come right on over. Let yourself in the back through the fence.”
The first couple weeks of summer I didn’t think about it. Then one Monday I was home bored with nothing to do. So I decided to take Mr. Sheffield up on his offer. At first I was going to put on a one piece but then decided to wear a bikini. My parents would be home from work after five and I’d be long home by then.
I grabbed a towel and went over to go use the pool. I was out there maybe ten minutes swimming around when Mr. Sheffield came out.
“Hi, Sandy, glad to see you,” Mr. Sheffield said.
“Hi. Thanks again.”
“You want some lemonade?”
“Sure, that’ll be nice,” I said. He turned to go get the drinks. Still drying myself off, Mr. Sheffield came out with the drinks. Seeing me in my bikini, Mr. Sheffield couldn’t hide how flustered I got him. I acted like I didn’t notice but secretly I liked how I was obviously affecting him.
Eventually I said my goodbyes and didn’t think much of his reaction. However when I went back the following Monday I thought I’d tease Mr. Sheffield. I did the whole “I need someone to rub sunscreen on my back” bit. As his hands rubbed my back, I quite enjoyed his touch. It turned me on and I was fantasizing if he would touch other places on me. He didn’t and though nothing happened there was an unspoken thing definitely happening between us.
The next Monday I got bolder. I laid on his lounger on my stomach and asked if he could untie the string to my bikini. I didn’t want to get tan lines of course. I don’t know what I was thinking but I wasn’t a clueless virgin to not realize that it would lead to something bigger.
His hands began massaging my back and definitely was taking more time than needed to put sunscreen on. I moaned and I was embarrassed but it was a natural response I couldn’t help. He worked his hands down my back and eventually was massaging and squeezing my ass. His hands even dipped inside my bikini bottoms. Again I moaned.
“I want to worship your ass,” Mr. Sheffield said, surprising me. He started kissing and licking my ass cheeks and then pulled my bottoms down. Spreading my ass cheeks, Alanya Escort Bayan he tongued my asshole.
My internal monologue was debating whether I should say something or just lay there and let him do his thing. Also I thought about how hot it was and how it was turning me on. I loved ass play and at that point I’ve had anal sex a few times.
I let myself enjoy it and moaned my appreciation.
Mr. Sheffield paused what he was doing, “I want to eat your pussy. You don’t have to do anything to me.”
Taking my hand, he helped me up from the chair and led me into the house. As soon as we were inside, he kissed me so passionately. I had been with older guys but didn’t realize a man of 59 could be so passionate. He was a great kisser.
Since my top had been untied earlier, I was topless. He led me to the sofa in the living room where we kissed again and then he went to take care of my breasts. The way he sucked, licked and nibbled on my nipples was out of this world.
Then he went on to take my bikini bottoms off. And his mouth was on my pussy. If eating pussy was an Olympic sport, he’d be the Michael Phelps equivalent. I loved how he sucked on my clit. He was the first man to make my legs shake when I came. He was relentless too. I started losing count how many orgasms I had.
I wanted him to feel good too even if I couldn’t be at the same level as him reciprocating with my skill.
“I want to suck your cock,” I screamed, pulling him away from my pussy. We kissed and tasting myself all over his mouth was hot. He sat on the couch and I gave him the most enthusiastic blow job I’d ever given in my life to that point. He had a nice cock too. It was a good seven inches and I tried my best to take as much of him into my mouth. I also made sure to pay attention to his balls.
For all my efforts I was finally rewarded with a big load of his cum. I loved the taste and it made me feel good I could make him come after he had made me come so many times.
Afterward we kissed again and had big grins on our faces. Mr. Sheffield’s name was Mike and that’s what I started calling him when we were alone together.
Mike loved orally pleasing a woman. He said it was a fetish for him. I would feel so sexy when he would tell me to ride his face. So many mind blowing, leg shaking orgasms he gave me.
I would sometimes feel guilty because Mrs. Sheffield was a nice lady. He told me they hadn’t had sex in years and she only let him go down on Escort Alanya her a handful of times in all the years they were married. That absolutely blew my mind because I don’t know why you would be married to him and not be expecting that every night. Seemed to be a waste of a man’s talent to not be used.
He had cheated a few times over the course of his marriage. At the time we started our affair. He was seeing a couple. Mike would eat out and fuck the woman while the guy watched. He was getting tired of the guy always being there and wished the guy would take a walk sometimes. Not long after we started our thing, he broke it off with them.
Mike had a vasectomy so even though I was on birth control it eased my mind to know that wasn’t a big of a concern. He never pushed to have sex though. The first few times we were together it was just oral.
One day I was over there and we were in his guest bedroom where we normally did our thing. I was coming down from an orgasm but I felt an overwhelming need to have him inside me.
“Mike, fuck me,” he looked up at me, “I want to be close to you.” We had sex missionary style. My legs wrapped around him and my arms held him tight. We kissed throughout and I kept telling him how I needed him. One of the most sensual times I had with a man. It was the first time I felt like I was making love and not just fucking a man. When he came, he came hard and long. I loved watching his face at that moment.
I had long been shaving my pussy but that summer I got my first Brazilian wax. Mike loved how smooth it made my pussy. I made sure to make appointments right before I was to see him.
He also got to fuck my ass as well that summer. Even when he fucked my ass, I was able to come without any clit stimulation many times. We also tried some bondage which of course was amazing. We also fucked in the pool a few times.
I never felt embarrassed to tell him any of my desires and I was open to hear his. I can’t say it was true love but I did grow to care about him deeply. I went away to college but still would find time to be with him at least once when I was home.
The year I graduated college he and his wife retired down to Florida. I missed him but it was for the best. Our relationship had run its course. He was forty one years older than me and I was starting my life and he was winding down. Plus he was married so this was to come to an end sometime.
Into my 20’s I would hook up with older guys. Sometimes with men in their fifties and early sixties. Much older men kind of became a fetish of mine. When I was between relationships, I would sometimes make an older gentlemen’s day by propositioning him. I never was turned down.
Still Mr. Sheffield holds a special place in my heart.