Sinnndy's Dates an Older Man

Hi, my name is Sinnndy. Some of you have read stories about my sexcapades, but I haven’t told you information about myself. I am 18 years old, 5-3 just under 100 pounds, 34B-24-34, shoulder length brown hair, and I have been told I am very attractive and that I have a great ass.

Don’t let the fact that I’m only 18 let you think I’m inexperienced, because that’s just not true. I have probably tried more different and kinky things than even my mother has. I was born and grew up in a northern suburb of Chicago. I love it here, and plan to never leave.

I have great parents, I love them both, and I have a great brother, 5 years older than me. He lives in Chicago. We were brought up in a nudist household, when no one else was around; we would walk around the house naked, that’s why I am not ashamed of my body. America is way too uptight about nudity. During the summertime, I lay out in my backyard nude. I know the neighborhood boys, and men, love me.

I first started touching myself when I was 11. I had older cousins that I was close to, and we talked mostly about sex. So I tried masturbation, and of course, I loved it. At 12, I gave my first blow job to a friend of my brothers, who was about 18. I lost my virginity at 14, to a friend of my fathers. I wanted to have sex with someone much older and experienced, and I was glad it turned out to be Jim.

I was now hooked on sex. I wanted to try everything. I really liked older boys; they were much better than guys my age were were, so usually my brothers friends would take care of my needs.

By the time I was 16, I had probably had sex with over 25 guys, most of them were at least 5 years older, but some were in their 40’s. I started hanging out in a bar where a lot of lawyers, doctors and other professionals went. When I decided to dress up, I looked old enough to be in a bar. I would go there with my cousins, since I was 18, one of them got me a fake ID, just in case, and it looked just like me.

On occasion, I would make dates with some of the men there. Guys like that know how to take care of women, They take us to nice restaurants, and wine and dine us. While mostly not as energetic as younger guys in bed, they know how to please women.

One night, a very good-looking man came up to our table, and started talking to us. His name was Michael; he was about 45, brown hair, with gray temples, very good looking, and a doctor. I was there with two of my female cousins, but he seemed to pay more attention to me. We talked about a variety of subjects, from his occupation, to what we did for a living. I had to lie, and said I was going to college, studying business. What really piqued his interest, was when I started talking about sports. My dad brought me up as a tomboy. My brother wasn’t much of an athlete, dad could tell at an early age that he wasn’t, but could tell that I had his athletic genes. So my dad would take me to baseball, football, basketball and hockey games, and we would watch everything on TV. So I am a big time jock, I now play softball at least 5 times a week during the summer.

So when I started talking about the Bears, and sounding like I knew what I was talking about, and I did, Michael started paying more attention to me. He was divorced about 3 years ago, and had 2 kids. He and his ex-wife just didn’t have anything in common. She hated sports, and hated the fact that because of his job, he was never home. He was lucky to have sex once a month, and when they did have sex, it was with the lights off, missionary position, and when he came, it was over. She wouldn’t give him head, and didn’t want him to see her naked.

We had a nice evening, and Michael asked me out on the following Friday. I said yes of course, and told him to pick me up at my cousin’s apartment. I went shopping for a new dress during the week. I wanted something sexy, but also elegant. I found a real nice black number, very short, I have great legs, but it had a nice touch of elegance. I went to the salon to get a manicure and a pedicure. I got myself all dolled up. I looked hot in that dress, and of course, I never wear panties. I am an exhibitionist; I really get off flashing waiters and patrons.

I went over to my cousin’s apartment at 6:30, and had a couple of beers. Michael picked me up at 7:30 sharp. He looked great, and smelled nice too. He is about 5-10, 175 pounds. He looked like he takes great care of his body, and I would find out later that he really did. He drove a very hot Mercedes, and took me to a very fancy Italian restaurant, very dark and romantic. The conversation and wine was flowing nicely. He even ordered dinner for me. The food was wonderful, and I wasn’t feeling any pain from the wine. The waiter paid extra special attention to us, especially since I had been flashing my shaved pussy at him all night.

When dinner was finished, Michael came right out, and asked if I wanted to go back to his place with him. That’s what I like about older men, straight to the point. I was pretty horny at the time, so I said, “yes, that would be nice.” As he held the door open for me, he grabbed me, and pulled me close to him, and kissed me. It was a wonderful, sweet passionate kiss, our tongues swirling in each other’s mouths. Another thing I like about older men, is that they know when and how to take charge. We finally broke off the kiss, and got into the car.

As we headed for his house, I started running my hand up his leg, coming close to his penis, but not touching it, teasing him. I finally started to lightly rub his penis through his pants. He was doing a great job of driving, considering what was happening. At a stop light, I unzipped his pants, and he scooted up, so I could pull them, and his underwear down. The light turned green, and I started licking his cock head. He was already hard, and had a nice thick cock. It was probably about 7” long. I was really teasing him, licking his pee hole, circling his head, completely avoiding his shaft, and driving him crazy. I could tell by his soft moaning. I then surprised him by swallowing his whole cock in one fast swoop. I then started to bob my head up and down, sucking and licking his shaft at the same time.

Because I was driving him crazy with my oral talents, he pulled over to the side of the road. It didn’t take too long, he was a true gentleman, warning me that he was about to cum, trying to pull away from me, his ex-wife never swallowed his cum, but I wasn’t hearing any of that. I took him deep in my throat, and could hear him moaning, and then felt my gooey dessert sliding down my hungry throat. It was yummy. We were pretty close to his place now. He thanked me for the best blowjob he had ever had. I told him that was only the beginning. He had a strange smile on his face, and I found out later just what that meant.

He had a beautiful house, it wasn’t huge, his ex got the family house, but it was a three-bedroom place, with a nice basement, and a Jacuzzi in the backyard. He opened a bottle of wine, just what I needed, more wine. It was a nice mellow Chardonnay. He put on some soft music, and sat next to me on the couch. He was really close to me, pulled me to him, our lips met in another passionate kiss. He was a great kisser. He started lightly moving his hands on my body. I was really wet. He would fondle my breasts, run his hands down to my ass, he was really good.

He lifted me up, while we were still kissing, and carried me to his bedroom. He helped me undress, and then took off his clothes. He wasn’t muscle bound, but I could see he was in great shape. He lifted me up again, and placed me on the bed, kissing me deeply.

He worked his tongue around, and then in my ear, I love having my ears licked. He then started kissing and licking his way to my neck. He was very deliberate, and passionate. I was used to wham, bam, thank you ma’am. This was a nice change.

He kissed his way down to my breasts, mmmmmm that felt great. He licked, and teased my nipples, occasionally lightly nipping them with his teeth. He then worked his way downwards, licking my sides, and licking my belly button. I was so horny. He then licked downward, blowing lightly on my pussy, but he didn’t lick it, he kept going downwards to my thighs, licking and kissing his way down my legs. I was really glad I shaved that night. He was now down licking my ankles, and then kissing my feet. When he popped my big toe in his mouth, I almost came. It was the first time I had ever had a man suck my toes, and I loved it. He put all of my toes in his mouth, and then repeated the process on my other foot and toes. I really wanted him to fuck me right then and there, but he had other plans.

He licked and kissed his way back up my legs, and then was lightly blowing on my pussy. I raised my hips to meet him, but he pulled away. He wanted to let me know that he was in charge. He then surprised me, by lightly licking my pussy lips. He knew how to please and tease a woman. He paid attention to just my pussy, completely avoiding my clit, which made me crazy. He darted his tongue in and out of my pussy, it felt wonderful. He finally started licking my clit, I was in heaven. He slid two fingers in my pussy, fucking me with them, while his magic tongue licked my clit in circular motions. I was really close, thrashing about on his bed, his strong hands keeping me from bouncing off of the bed, he then sucked my clit into his mouth, and that did it. I had never felt anything so wonderful. It was my first orgasm, and it felt great. I had to push his face away, I couldn’t take any more. He moved his body up, and slowly slid his penis into my now extremely wet pussy.

He filled me with strong, slow strokes. Pulling his cock almost completely out, and then slowly sliding it in. This man knew how to fuck, and drive me crazy at the same time. He then took my legs, and placed them on his shoulders. He then picked up the pace, slamming into me like a wild bronco. I love being fucked hard like this. He was close to cumming, and asked me if he should pull out. I told him that I was on the pill, and wanted his cum deep inside of me. He moaned that he was cumming, and I could feel his creamy liquid filling me up deep inside. He collapsed on top of me, kissing me. I felt really great; it was a wonderful session. His penis finally slid out of me, and we cuddled in bed for a while, and fell asleep.

I was awakened in the middle of the night, by a wonderful feeling. I was on my stomach, and felt a wet tongue lapping at my pussy. I love being woken up this way, it felt wonderful. He was licking me all over. He surprised me by kissing my ass cheeks, and then licking around my asshole. I could tell he was waiting to see my reaction, it was the first time any man had paid attention to my butt, so when I lifted my ass up to meet his tongue, he had his answer. He then licked my asshole, my god I loved it. He darted his tongue in and out of my dark hole. I started playing with my pussy, rubbing my clit, loving this new feeling.

I was really wet now, he just slid his cock in my pussy, fucking me really hard. I loved it, he was the best lover I had ever had, doing things to me that no boy would think about trying. He slowed down the pace, but was still slamming his meat into me. I felt him slowly sliding a wet finger into my ass, it was really uncomfortable and it hurt a little. He told me to relax, and enjoy the feelings. I relaxed, and started enjoying it. He then slid another finger inside my ass, and still was fucking me good. He was sliding his fingers in and out of my ass. I reached between his legs, and rubbed his balls with my fingers. I could tell by his moan that he liked that.

He pulled his cock out of my pussy, and before I had a chance to complain, I felt his big head at the door of my ass. I tried to pull away, telling him, “no, please not in my ass. I’m not ready for that, your cock is too big.” He told me to relax, and enjoy it, that I would thank him later for initiating me into the world of anal sex. I pleaded with him not to do his, but the head of his cock popped into my ass. The pain was unbearable, and I tried to get away from him.

How could he be so gentle, and then do this to me. I was screaming at him to please stop, tears rolling down my face. He calmly told me to relax, like I did when he first put his finger in my ass. He still had just his head inside of me, and so I figured that I would try to make the best of this bad situation. I concentrated on relaxing my sphincter, and to my surprise, the pain subsided, and I felt a pleasurable feeling that I never knew existed. I then said, “fuck me Michael, fuck my ass.”

He started to slowly move inside my ass, in and out, maybe 4” in my ass, as I got used to feeling him inside me. My fingers were working overtime on my pussy. He then pulled almost all the way out, and slid his entire length in me, staying there for a couple of seconds, letting me get used to his whole cock in my ass. I started begging him fuck me, fuck my ass, please. He then started to fuck my ass like it was a pussy, pistoning in and out of my ass. I loved it, it was one of the greatest feelings I had ever had. He kept up a nice hard pace for a couple of minutes, and announced that he was cumming. He grunted, and I felt his warm load filling my bowels. It was great. He stopped pumping, leaving his dripping cock in my ass, kissing my neck and licking my ears. We moved into a spoon position, his cock still in my ass, and fell asleep.

I woke up a couple of hours later, and decided that it was my turn to wake him up. I pulled back the covers, and started licking his shaft like it was a lollipop. It had a musky taste to it, I figured that it was from being in my ass, but I liked it. He finally woke up with a big smile, as I continued to lick up and down on his shaft, not missing a spot on either side of it. I worked my tongue down to his balls, licking them, teasing them, lightly biting on the hairs on his balls. I then popped one in my mouth, gently sucking and licking it. I then popped the other one in my mouth, sucking on it. He was the one now thrashing about on the bed, moaning loudly, his fingers running through my hair. Lightly pushing my head down in his crotch. I released his testicle, and started licking up and down on his very hard shaft. I pulled my mouth away, and started to climb on his chest, lowering my pussy onto his rod. I was in control now, slowly bouncing up and down on his cock, one hand on chest, the other reaching around my back, fondling his balls. He really liked having his balls played with while I was riding him.

He grabbed me around the waist, and rolled me onto my back, his dick still deep inside me. He put my legs around his shoulders, and started fucking me hard, I loved this position, he really got deep inside of me. He then pulled his cock out, placed saliva on it, and placed it at my asshole. I was ready and willing this time. His head popped in, and he then slid his cock deep inside of my ass. He wasn’t gentle this time, and I didn’t want him to be. I wanted him to fuck my ass hard. With my legs around his neck, he really penetrated me deep, fast hard strokes in and out of my ass, his balls slamming against my ass cheeks. I was in heaven, sex would never be the same for me, I was now an anal whore. He was really picking up steam, and I could tell by the look on his face, that he was getting close. I told him I wanted his load down my throat. He asked me if I was sure, and I said, “yes, please fuck my face.” He pulled out of my ass, and started fucking my face. I loved the taste of my ass on his cock, I knew it was so dirty, but I couldn’t help myself. He was grunting and groaning, so I did something I had never done before, I licked my finger, and slid it into his asshole. When I did that, he grunted, and starting filling my mouth up with his love juice, which I greedily gobbled up.

We took a shower together, soaping up each other’s bodies, and he fucked me in the shower one more time. It was quick and nice. He then drove me back to my cousin’s place. He kissed me good bye, and asked me out for the following weekend. We went out a couple of times after that, the sex was good, but I wanted to try more new things. There were a lot of guys out there that I wanted to fuck. I wasn’t ready for a relationship, and told Michael that. He understood, and we went our separate ways.

I still saw him in that bar every now and then. He met a nice lady, closer to his age, but still younger. He told me she was pretty wild in bed, not as wild as I was, but really a great person. I told him that I was happy for him. They got married this past May. I went to the wedding, and met a hot hot doctor, but that’s another story for another day.

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