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  • — My Cheating Heart —
    Straight Female / 32

    I met my first boyfriend when I was 14. Jack was tall (6'2") and very handsome. We started going steady and I lost my virginity to him. Jack (not his real name), was on the football team and I was on the track team, so we were both very athletic. We grew to have a very active and satisfying sex life. After high school we both went to the same university together. It was a foregone conclusion that we would marry and we did a month after graduation. I was working at a nurse at a local hospital while Jack got his MBA. After he finished school he got a great job, but our love life really started to suffer. He worked long hours and had to entertain clients, so he often came home drunk and passed out. When we did have sex, it was quick and uninspired, and Jack would quickly fall asleep afterwards.

    I was getting really frustrated with our life, so I booked us a vacation to St, Martin for our fifth anniversary. It is a beautiful island and we enjoyed swimming in the water that first day. That night while we were out walking Jack found a casino and wanted to play some blackjack. Gambling and smoky casinos are not my thing, so I went back to the resort. He came home a little later and I had put on my sexiest lingerie for him. We did have sex but again, it seemed like a quickie. Jack did get me off with his tongue, but as soon as he came he passed out.

    The next evening, we went out to a local restaurant that had live music and great food. The place was packed. The tables were picnic style tables. After a while an attractive older man with white hair and an incredible smile, asked if he could sit at our table. He introduced himself as Sean. We had a great evening laughing, drinking, and talking with our new friend. Jack had a bit too much to drink, so when we got back to the room, he couldn't perform. I was sexually frustrated and ended up masturbating while fantasizing about Sean.

    The next morning, we were supposed to go scuba diving, but Jack was too hungover to get out of bed, so I went by myself. As I was stashing the gear on the boat, I heard a familiar voice behind me. There was Sean grinning at me. I instantly blushed because of my fantasy session the night before. He was wearing board shorts, a long-sleeved shirt, and a straw hat. I was taken again by how handsome he was. We ended up getting paired together for our dives. When it was time to get ready, he stood and pulled off his shirt. I could only gawk. He had a slim but very muscular body, and true six-pack abs. He had a better body as a 55-year-old man than Jack did when he played football! Then he took off the board shorts and he was just wearing skin shorts, which did nothing to hide his impressive package. He put on a 3mm wetsuit and I asked if I should have brought one. He told me that he went diving often, and he wore it to keep his body temperature up and the fire corral from stinging him. Then he added that he liked how I looked in my swimsuit and winked. I felt myself get instantly wet. The diving was beautiful, and Sean was an excellent diver. After the dive, we sat at the bar and had a couple of Caribs. I completely lost track of time, and realized that it was nearly 3 O'clock and I had a date with Jack for a romantic dinner cruise at 6.

    I rushed home and got myself ready, but Jack wasn't back yet. At 5 I finally got through to him. I could tell that he was at the casino and already drunk. I reminded him of our dinner date to celebrate our anniversary. He told me he was having a good night and he'd be back in a few minutes. At 5:30, Jack stumbled through the door, bragging about all the money he had won, and told me he would be ready in a minute. He didn't even realized how upset I was. I never heard the shower and went to the bedroom to find him passed out on the bed. I was furious and hurt so I changed out of my expensive dinner dressed, took off my sexy lingerie, and pulled a sundress on.

    I was walking down the beach with tears streaming down my face, when I heard Sean's unmistakable deep voice behind me asking if I was alright. I quickly tried to compose myself and told him I was fine. I could tell by the look on his face that he didn't believe me, but he didn't say anything. I really didn't want company, but he started walking with me. Within minutes he had me smiling and laughing, and I had all but forgotten about the ruined evening.

    He mentioned how beautiful the sunset was and I looked over to see the most stunning red sunset I'd ever seen, reflected off the ocean. He told me that on the islands they believe it is good luck to kiss during a blood-red sunset. He put his right hand around my neck and pulled me in for a kiss like it was the most natural thing ever. And wow, what a kiss it was! It was the best kiss I'd ever experienced. His left arm snaked around me and he pulled me in to him. I felt his hardness, and it took my breath away. We could have kissed for ten seconds or ten minutes, I'm not sure. I had completely lost track of time and everything around us faded away. It was just him, me, and that incredible kiss. When we finally broke the kiss, I looked into his eyes and said, "Take me home and make love to me". He grabbed my hand and headed to his bungalow. As we stepped in the door, he gently pushed me against the wall and started kissing me again, even more passionately this time. The thought crossed my mind that I had never been truly kissed before. I was so drenched that I could feel my juices dripping down my leg.

    When we broke the kiss, he stepped back, regarded me for a second, and in one quick move, pulled my dress off over my head. I stood there naked in front of him, feeling very self-conscious because I had gained 15 pounds from my high school days. But the look on his face was one of lust and adoration. He told me I had a beautiful, womanly body. I started removing his shirt, and fumbled with the snap on his shorts. As soon as I pulled them down, the most beautiful cock I've ever seen sprung out in front of my face. I wasted no time sucking it into my mouth, noting how big and very hard it was. He was at least two inches longer than Jack and much bigger around. Sean pulled me up and pushed me back on to his bed. He crawled up and kissed me, and I could feel the tip of his cock teasing my pussy lips. Slowly, he pushed his shaft into me until I was filled like I'd never been filled before. Now I've never been one of the lucky woman that can have an orgasm through penetration, but it felt heavenly! As he fucked me slow but very deep, he was kissing me with those amazing lips. I started to feel very good, and when he kissed down the side of my neck, I exploded! And the orgasm wouldn't stop! It felt like I had an orgasm with each stroke of his cock. I was in another world.

    I don't know how long he fucked me that way, but after a time he was pumping into me harder. Then I felt him grow impossibly large, and I felt the warmth as he released deep inside. The naughtiness of it sent me over the edge and I had another orgasm. He slowly pulled out and started to kiss down my body. I told him my pussy was too sensitive for him to go down on, but he ignored me. He brushed his lips across my breasts and I was on fire again. He kissed all the way down my belly, saying things like, "I love your curves" and "Your body is divine". Then he got to my pussy. He teased gently and got me so horny I couldn't stand it. He performed fellatio for almost an hour like a master, taking right to the edge of orgasm and then backing off slightly. Then as he circled my clit, he pushed two curved fingers deep inside me. As he pulled them across my G-spot, I had the biggest orgasm of my entire life and gushed everywhere for the first time ever.

    After cuddling for a while he got us some ice-water. I wanted to return the favor. I had never really enjoyed giving Jack a blowjob. It was reserved only for special occasions and I only did it because he liked it. I also never liked the taste or smell of his cum and wouldn't swallow it. Instead, I'd let it drip out of my mouth over his cock. But all I could think was that I really needed to worship Sean's beautiful cock. And worship it I did for almost an hour! When he did cum in my mouth, I began to swallow all of it and was going to suck him dry, but he had other ideas. He pulled me up, flipped me over and plunged that huge cock deep inside my cum-drenched pussy. Then he fucked me with purpose, and again I found myself in heaven. I soon felt him release deep inside me again, and that pushed me over the edge as I had yet another orgasm. It was the best sex of my whole life, before or since.

    After we had made love, he told me to put on my dress he was taking me out. We went to a local Reggae bar where he seemed to know everybody. We had a great island meal and we danced and I fell in love with him right there. After one song the band called him up on stage. They started playing "One Love", and he sung it with perfect tune! I wondered if there was anything this beautiful man couldn't do.

    After dinner I was planning to head to my room, but he asked me to stay the night. I slept so soundly that night wrapped in his warm embrace. I woke to the smell of coffee and bacon and we had a leisurely breakfast on his patio overlooking the sea. Then Sean took me again from behind as I looked out over the turquoise waters of the Caribbean. Again, I had an earth-shattering orgasm when I felt him explode inside me.

    When I did get back to the room, Jack was just waking up. He had no idea that I had been gone all night or that I had another man's cum leaking out of my sore but satisfied pussy. He apologized profusely, but I had made up my mind that I was done with him. I re-booked my return flight for the next morning. That evening I went over to Sean's and made love to him one last time and I said goodbye to him. I never saw him again.

    When I got home I moved out of our house and filed for divorce from Jack immediately.


    Five years later I'm married to a great guy and I have a toddler son. My husband is an unselfish lover, and our sex life is good, but I still think of that one night of perfect pleasure and passion with Sean and wonder what happened to him. If you are out there Sean, thank you for giving me the courage to leave Jack and find love.

    #38202 — Comments (5) — Nov 28, 2017 at 4:14 PM — That's Juicy! (20) Remove This.
  • 1
    That's a great story and reminds me of my own. I was in a marriage with a controlling, abusive man and didn't realize it until we went on vacation. He spent the whole time drunk out of his mind. We went on a party boat one evening and he was just acting like a drunken ass. The captain of the boat saw what was happening and took pity on me. He let me stay in the wheelhouse with him. He was much older but very handsome. As the evening wore on and the band started playing, we ended up fucking right there in the wheelhouse. It was the best sex of my life.

    The difference with your story, is that I stayed on the island, divorced my jack-ass of a husband, and married the boat captain. That happened almost 20 years ago and we are still together and he is the love of my life. I found myself sad reading that you never saw Sean again. Older men are truly the best.
    19 days ago
  • 2
    That is one very hot story...and well told. I'm with the person that wrote the first comment. It was sad that you said goodbye to the man that opened your eyes, showed you more pleasure than you'd ever had, and that you said you fell in love with. Why did you go home?
    18 days ago
  • 3
    I've been married for three years now and have recently slept with another older man.
    My husband's and my sex life has been adequate but not sensational to say the least.

    When a man fifteen years older than us and a member of the group we go out with started making suggestive comments I kind of melted.

    He made remarks about certain types of lingerie that really turns him on and I reciprocated. I bought and began wearing them when I'd know he was going to be there when we went out. My husband questioned the sudden change in my lingerie tastes and I lied. I said I was wearing them for him.

    It was the second time we went to a party at my lover to be's house when he took me. I'd been flirting with the guys in our group and though there was a little touchy feely going on I always went home to have my wet panties satisfied by my husband. This case wasn't different, at least not from the start.

    He was all over me, and I actually struggled for awhile trying to keep my legs together. He went down on me, sliding my panties down while I squealed in excitement. He was massive compared to my husband and pushed in almost violently. I had multiple orgasms!

    My husband wanted to make love to me to that night, but I was too sore. I made excuses and settled on orally satisfying my husband. I can't say no now.
    17 days ago
  • 4
    I'd only known one man until recently, my husband. I was hanging new blinds on Saturday at the office and my boss helped from behind. With both of us on a step ladder I could feel his growing presence from behind.

    I had on a short comfortable sundress that had risen considerably in the back from both his obvious excitement and my uncomfortable reaction of stepping down the ladder one rung and firmly into through his jeans erection.

    After a considerable amount of school kid bumping and grinding my wet panties were too much of an invitation for his fluttering tongue and hard blunt penis.

    We came up with projects to feed our Saturday morning love fests. It's so satisfying! I love him cumloads he leaves deep inside of me. I'll never leave my husband but but knowing my lover's seed is in me has caused a bit of a conundrum? My husband and I haven't been able to have a baby, his low sperm count is the problem. It's been a few months and I've missed ovulating at the right times but eventually it's going to happen. My husband has no clue, but when my lover is deep inside of me I feel no guilt until I'm sleeping with my husband, my true love.
    15 days ago
  • 5
    I went to a family wedding last Saturday, my husband was out of town on business. It was a short distance away and everyone stayed at the hotel where the reception was held.

    The problem is that I had too much to drink and woke up the next morning in different panties that I'd worn with my dress. The panties weren't mine and were full of sperm that had leaked out of me. I have no idea how I got into these panties nor how many men I'd been with. I also have multiple hickies all over the place!?
    15 days ago




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