I was twenty-five at the time of this story. I was married at the time to my high school sweetheart. We got married right after high school graduation because I was pregnant. I hadn’t started to show yet, but I soon would.
At first, everything was great. My husband’s family owned a company, and of course, he went to work at the family business. He was a loving husband and doted on me during my pregnancy. He was very attentive and gave me everything I asked for.
It was the same way for about the first five years after our son was born. Dave spent a lot of time with our son, Steve.
The next couple of years, Dave seemed to be in a world of his own. He started working twelve to fifteen-hour days. Steve and I hardly ever saw him, and our sex life was pretty much non-existent. We may have made love once a month in the past three months, but it wasn’t satisfying. He was always too tired.
We hadn’t taken a vacation in over two years. When some of my girlfriends asked me to go to the Caribbean for two weeks, I jumped at the chance. Dave didn’t have a problem with it, and I had a friend who would babysit my son, so I was off to the Caribbean for two weeks with six of my friends.
Tina, the friend who planned the trip, came to my house the day before we were to leave. She said, “I know how conservative you are when it comes to how you dress, so I’m taking you shopping for clothes for our trip. “
Everything she had me try on was way too revealing, I thought. Tina had been to the Caribbean before and knew how the locals were, so I didn’t argue.
I was all packed and ready to go when Tina stopped by the next day to pick me up. I dropped Steve off at my friend’s house, then off to the airport. It was my first time on an airplane, and I was a bundle of nerves, but I made it through ok.
When our plane landed, Tina hustled us all to the bungalow we would be sharing and then told us we needed to change because we were all going to the bar that was close by. We changed, and Tina held up a little cloth bag and told all of us to put our wedding rings into it.
When I asked why we were taking our rings off, Tammy spoke and said we were doing that so nobody at the bar would know we were married. I had a problem with that. I told them I was married and wasn’t looking to hook up with anyone. Tina told me that none of them were looking to hook up, but that if we didn’t take the rings off, none of the men would talk to us.
Tammy told me that we could just flirt with the guys and that nothing had to happen. If a guy started to come on too strong, I could just tell him I was married.
All the other ladies had put their rings in the bag, but I still hadn’t yet. They all started encouraging me to take it off. They said none of them would have fun if they had one friend with them who was married.
I reluctantly took off my ring. Tina quickly grabbed it and tossed it into the bag. Then she told us that nobody would be getting their rings back until we boarded the plane to go home. She then told us to go change into one of the outfits we brought, and then we would all go to the bar.
I changed into a short skirt that was too short for my liking, and a halter top that was a size too small, but I didn’t say anything. I didn’t want to ruin anyone’s fun.
As soon as we got to the bar, this man, who was the sexiest man I had ever seen, he was about six feet tall and looked to be about two hundred pounds with dark hair, a mustache, and a goatee, came over to our table and started talking to us. He introduced himself as Greg. He wasn’t obnoxious. He just wanted to buy us drinks and wanted one of us to dance with him.
When we all turned down the dance, he told us he would buy us all a round of drinks anyway. Then he asked if he could join us, and before we had a chance to answer him, he just sat down at our table.
He flagged down a waitress and told them to take our order and put it on his bill. All my friends ordered mixed drinks, and I just ordered a ginger ale since I’m not much of a drinker.
He sat at our table the whole night. And he kept telling us about all the places he’d been and all the things he’d seen. He said he was from the USA and he’d be going back in a week or so.
Tina told him that we were there on a kind of girls’ getaway and we’d be there for two weeks and that this was our first day there. She also said that she was the only one of us who had been there before.
At the end of the night, the bartender blew a loud whistle and yelled, “Last call!” And Greg told us to order whatever drink we wanted, and he would take care of it. The ladies all ordered shots. I was just going to have another ginger ale, but they talked me into having a shot.
After we left the bar, Greg asked if he could walk us to our bungalow. We let him since it was dark, and we figured nobody would mess with us if he was with us. When we got to our bungalow, he asked me if he could talk to me in private.
After the ladies went inside, Greg asked me if I would have dinner with him the next night. I told him I barely knew him. He told me that’s why we should have dinner together, to get to know each other better.
I politely told him no, and he gave me a big smile and told me maybe he could change my mind before I left to go home.
When I went inside and told all my girlfriends what Greg wanted, they all thought I was nuts for turning him down. I reminded them that I was a married woman.
Becky, one of the ladies, said, “You could have fooled us.”
They all knew my situation, and Tina said, “Becky!”
She said, “Hey, it’s true. What’s the harm in having a little fun? Besides, you’ll probably never see Greg again.”
Becky then added, “And what happens in the Caribbean, stays in the Caribbean.”
I told her, “That’s Vegas, Becky. What happens in Vegas stays in Vegas.”
Becky said, “That can apply to anywhere.”
The next night, when we all went to the bar, Greg was there. He came up to our table and insisted on buying us our first round. My girlfriends ordered mixed drinks, and I just ordered a ginger ale.
We all just sat around making small talk. A couple of the ladies got up and danced with some guys. After about an hour, I heard the Limbo song start playing.
Greg got up and yelled, “Ok! It’s Limbo time!”
They had a Limbo stick already in place, and a line had formed when Greg came over and asked if any of us wanted to play. All of my friends turned him down, but Tammy said to me, “Go ahead, Sarah. I bet you can beat everyone.”
The rest of the girls were encouraging me to play. I kept putting them off, but they just wouldn’t let up. Greg finally said, “I’ll tell you what, beautiful (that’s what he had been calling me instead of my name), if you play and win, I’ll pay for all of your drinks the rest of the time you are here. Until you go back home.”
I asked him, “And if I lose?”
Greg said, “If you lose, you have dinner with me every night until you leave.”
Tina remembered how good I was at Limbo and told me, “Come on, girl, you can do this.”
Tammy spoke up and said, “Yeah, then we’ll save a bunch on drinks.”
Greg could see I wasn’t convinced, and he added, “If you lose, I promise the dinners will be two people getting to know each other, no hanky panky.”
I finally relented and told them, ok. It took almost two hours before it was down to just me and Greg as the only two participants. The Limbo bar was down almost as low as it could go.
Greg didn’t have any trouble getting under the Limbo bar. I was nervous when it was my turn. I had never gone that low before. I was halfway under the bar when I got a cramp in my leg and fell on my back and lost the game.
All the girls groaned. Greg called the bartender over and told him, “Even though she lost, I’m going to pay for whatever these ladies drink tonight.”
At the end of the night, half the girls were drunk and the other half that wasn’t had to help them to our bungalow.
After the ladies had all gone inside, I waited outside to talk to Greg. He told me, “Listen, beautiful, I shouldn’t have made that bet with you, so let’s just forget about it.”
I told him, “Oh, no. A bet’s a bet, and I lost.”
He told me, “Ok, but if you don’t want to have dinner with me after tomorrow, you don’t have to.”
Then he bowed and said, “Until tomorrow, beautiful.”
Then he walked away. I went inside the bungalow, and Tammy asked, “So, are you going to have dinner with him after tomorrow night?”
I was only half listening, and I said, “Huh, what? Oh, I don’t know.”
Then I said, “I’m tired, I’m going to bed.”
I don’t remember anything until the next morning. Tina was shaking me awake, telling me, “Come on, wake up. We want to go shopping.”
I got up and had a quick shower and got dressed. We were going to be walking everywhere we went that day. The first thing we did was have breakfast at a little cafe. After breakfast, we did some shopping and bought souvenirs for our friends and family.
We mostly checked out the shops within walking distance of our bungalow. It must have been a big tourist area because every shop had samples of food for people to try. We tried all of them and I loved them all.
We made sure to get back to our bungalow with plenty of time for me to get ready for my dinner with Greg. All the girls helped me. After my shower, Tina and Tammy did my hair and nails while the other girls helped with everything else.
My nails, hair, and makeup were perfect. I just had to decide what to wear. Tina talked me into wearing a red dress with spaghetti straps that matched my purse.
When Greg rang the doorbell of our bungalow, I answered it, and he just stood there dumbfounded. I said, “Greg, are you ok?”
When he finally spoke, he said, “I know I promised we were just going to dinner as friends, but I must say, you have got to be the most gorgeous creature God ever put on this earth.”
I just blushed, and before I could say another word, he said, “I know. I promise, that’s the last time I’ll mention it.”
Then he offered me his arm, which I gladly accepted. As we started to walk down the sidewalk, I asked him, “Where is your car?”
He told me, “I didn’t drive. I just live three blocks away.”
I asked, “Wait, we’re having dinner at your bungalow?”
He said, “Yes, unless you’re uncomfortable being alone with me.”
Well, I certainly wasn’t, so I said, “I would love to have dinner with you in your bungalow.”
I could smell something cooking even before Greg opened the door to his bungalow. I asked him, “What smells so good?”
Greg told me, “Well, I cooked you a real authentic Caribbean meal.”
I told him, “It smells delicious.”
He told me, “Wait until you taste it, beautiful.”
He quickly apologized and said, “I’m sorry, but I can’t help it.”
I said, “That’s ok.”
For a second, I thought he was going to kiss me. To tell the truth, I wouldn’t have minded if he did. Greg opened the door to his bungalow, and I walked inside. There was a candlelit table for two in a dining area. He pulled out my chair to sit down, then he lifted the lid from both the dinner plates on the table and said, “Enjoy.”
When I saw the glasses of wine on the table, I told him, “I’m sorry, Greg. But I don’t think I should drink any alcohol tonight.”
He gave me a big smile and said, “I guess it’s a good thing this is sparkling grape juice.”
I smiled back and tasted it, and said, “Mmmm, delicious.”
He told me, “Wait until you taste the food.”
Greg told me exactly what it was we were eating, and I couldn’t have told you what he said it was two seconds later, but I didn’t care; it tasted delicious.
We made small talk as we ate. He asked me, “You know I didn’t ask you if you were married or had a boyfriend before I asked you to dinner. I assumed you weren’t married since I didn’t see a ring, but I mean, you could have someone. I don’t want to cause you any problems back home if you have someone waiting for you.”
My response was the first time I lied to Greg. I told him, “I’m not married and I don’t have a boyfriend. It’s just me back home.”
Once we were done eating, Greg got up and turned on some light Caribbean music and turned it down low. He extended his hand to me and asked, “Would you like to dance, beautiful?”
As I took his hand and he helped me out of my chair, I told him, “Well, I do have two left feet.”
He told me, “That’s ok. I’ll lead.”
It wasn’t as bad as I thought it was going to be. I think I only stepped on his feet about half a dozen times. And we were both barefoot since we kicked off our sandals as soon as we entered the bungalow. But he never complained.
When the music stopped, Greg kissed me. After the kiss, he apologized, “Oh, Sarah! I’m so sorry. I broke my promise. I guess you’ll be wanting to leave now.”
Then he turned to walk away from me. I grabbed his hand and pulled him to me. I asked him, “What makes you think I didn’t want you to kiss me?”
He just stood there speechless, so I kissed him. It was the most passionate kiss I’ve ever had. When we broke the kiss, he asked, “I thought we were just going to be having dinner as friends?”
I smiled and said, “You said that. I didn’t.”
Still holding hands, he led me to his bedroom. It had a huge bed, as soon as we were inside, he became more aggressive, not that I minded.
He slid my spaghetti straps off my shoulders and planted a kiss on the top of each of my shoulders, and then reached back and undid the clasp on my bra, letting it fall to the floor.
He then said, “From now on, I don’t want you wearing a bra and panties, especially when you come and have dinner with me.”
I asked him, “What makes you think I will be having dinner with you after tonight? You said I didn’t have to if I didn’t want to.”
He smiled at me and said, “You’ll be wanting more, I promise.”
My dress was now in a pile on the floor at my feet. Along with my bra. He kissed down my neck to my tits, that are 34DD, about cantaloupe sized.
Greg kissed my tits and as soon as he kissed my nipples they became erect. He moved down my body slowly, licking and kissing. Tonguing my belly button. He then used his teeth to pull my panties down. All of my clothes, except for my stockings, were now in a pile at my feet. Greg looked up at me and said, “Step out of your clothes, my pet.”
I put my hands on his shoulder to steady myself, then I stepped out of my clothes. I was standing almost completely naked in front of a man whom I had known for less than two days.
Greg then kissed me again and slowly walked me backwards until I touched the bed. He said, “Up on the bed, beautiful.”
I told him, “I have a name, you know. But I love it when you call me beautiful.”
As I turned my back to him to crawl up on the bed he gave my ass a little love slap. I turned around and smiled and said, “Hey!”
Then I got up on the bed and turned over onto my back. I propped myself up with my forearms. Greg then unbuttoned his Hawaiian shirt and took it off. My God, his chest was so sexy! Next, he took off his shorts. He wasn’t wearing any underwear and he was rock hard and he had the biggest cock I had ever seen. It was as big around as a soda can and had to be twelve inches long.
He told me, “Give me a foot.”
I lifted up my right leg, and he slowly rolled down my stocking, kissing and licking my skin every time it was exposed. After he had the one stocking off, he told me, “Give me the other foot.”
I lifted up my right leg, and he did the same with that stocking. He then leaned over me, supporting himself with one hand, and with his other hand, he reached into the nightstand beside the bed and got a condom out of the drawer. He handed me the condom to open. I was nervous and all thumbs; I kept dropping it, and I couldn’t get it open. He took it from me and used his teeth to rip it open
He smiled at me and asked, “Do you think you can manage to put it on?”
I took the condom from the wrapper and put it on the head of his cock and slid it down. I could tell from the wrapper that it was a Magnum-size condom, but it was still a tight fit. It only went about three quarters of the way onto his cock and the way his cock was straining against it I thought it would break at any moment.
Once I had the condom on him, Greg told me, “Lie flat on your back, beautiful.”
Greg then lifted my feet up and rested them on his shoulders and he used a hand to guide the head of his cock to my pussy. I gasped and he asked, “Are you ok? Have you changed your mind?”
I might have been a little too eager, but I said, “God no! It’s just that I have never been fucked with a cock as big as yours, that’s all.”
He leaned in and kissed me and said, “I promise. I’ll be gentle.”
I was wet enough that the head of his cock slid right in without any trouble. Once he had the head in me, he moved both hands to my wrists, pinning my arms to the bed. Not that I was going to resist. Once Greg started to push his cock into me I knew it was going to be a tight fit.
When he was about halfway in me, I was biting my lip to keep from crying out. Greg must have noticed because he asked me, “Do you want me to stop?”
I viciously shook my head no. He asked me, “Do you want me to pull out?”
Again, I viciously shook my head no. He asked me, “So you want me to keep going?”
I smiled at him and nodded my head yes. He kept his hands on my wrists pinning my arms to the bed and he kissed me as he slowly slid his cock in until he was balls deep.
Once he was balls deep in me, Greg stopped and asked me, “Do you need a minute?”
I told him, in a strained voice, “Please…just…Fuck…me.”
Greg didn’t say a word, he pulled his cock out of me all but the head and then leaned in and kissed me and held the kiss as he slowly pushed back into me again balls deep. He did this over and over again. Each time he slid his monster cock into my hungry pussy he went a little harder and faster.
Once I started moaning he broke the kiss and raised up off of me and said, “Look into my eyes as I fuck you, beautiful.”
I did as he said. I just wanted to wrap my arms around his neck and pull his face to my tits and have him suck on them but he still had a hold of my wrists pinning my arms to the bed. I had never been in a position where I couldn’t move my arms, but for some reason, I liked it.
Greg just kept fucking me over and over again. Each time he shoved his monster cock in me it was harder and faster than the last. I just kept staring into his eyes. He told me, “Cum for me, beautiful.”
I started moaning, “Oh, God! Oh, God! Greg…I’m…going…to…cum!”
It’s like he didn’t hear me, he just kept fucking me over and over and over. When I came, I squirted, something I had never done before. It was also the most intense orgasm I had ever had up until that point. I don’t know if it was because I squirted or if that is why I squirted.
I had read that some men don’t like it when women squirt. I could feel Greg cuming although I knew he wasn’t cuming in me. Once both of our orgasms were over, he rolled off of me and lay beside me on the bed. As we both recovered, I said, “I’m sorry about the squirting. Had I known, I would have warned you. I have never squirted before in my life.”
Greg wasn’t phased by my squirting one bit. He told me, “That’s ok, beautiful. I don’t mind.”
Once we had both recovered, Greg said, “Why don’t we both get quick showers and head down to the bar and join your friends?”
I was disappointed and asked, “Wait, is that it? Were done?”
He gave me a smile as he turned to kiss me and said, “No, beautiful. But I think we should save something for another day, don’t you?”
He then kissed me and said, “You can take a shower first if you want.”
I took my shower and then, while he was taking his, I called Tina and asked, “Are you all at the bar?”
Tina said, “Yes, why?”
I said, “Greg said we should join the rest of you for drinks. We should be there soon.”
Tina asked, “So, how’d dinner go?”
I told her, “I’ll tell you all about it later.”
I started to get dressed while Greg was taking his shower, but I couldn’t find my bra or panties. I waited until he was done in the shower to ask him where they were, so I was still naked when he came out of the bathroom.
When he came out, I asked him, “Greg, where are my bra and panties?”
He smiled and said, “Don’t you remember? I said I don’t want you wearing them anymore.”
I couldn’t believe what I was hearing. Surely he only meant when I came over to have dinner with him, not all the time.
I told him, “But you meant, just when I come to have dinner with you, right? Not all the time?”
He started to dress and said, “No. I mean, all the time.”
I blushed and told him, “But, Greg. I can’t go around for the next ten days without wearing a bra and panties.”
He asked me, “And why not?”
I blushed and stammered and said, “W-well, I-I mean t-t-hat’s just not me.”
I continued to look around the bungalow for them, and once Greg was dressed, he came up behind me and put his hands on my waist, pulled me back into him, kissed my neck, and said, “Don’t waste your time looking for them. I threw them away while you were in the shower.”
I turned around to face him and I asked, “Greg, where are my bra and my panties, for God’s sake! What have you done with them!”
He said, “Hey, come on. Live a little. This is the Caribbean. Nobody knows you here. Have some fun.”
Well, I couldn’t be mad at him, so I wrapped my arms around his neck and kissed him on the lips and told him, “I guess I’d better get dressed. Tina and the rest of the girls are waiting at the bar.”
I looked at myself in the full-length mirror in Greg’s bungalow, and a person would have to be blind not to know I wasn’t wearing a bra. And sure enough, as soon as I got to the bar and saw my girlfriends Tammy saw that I didn’t have a bra on (anyone could tell from the way my nipples were erect that I was braless) and asked, “Did you forget something at Greg’s place?”
I knew exactly what she meant, and I told her, “I’ll explain later.”
I guess the other ladies saw and heard us talking because none of them questioned me about it. Greg again told the bartender, “Drinks for the ladies are on me tonight.”
Then all my friends ordered drinks, and I ordered my usual ginger ale. Tina came up to me and said, “I didn’t think we’d see you until in the morning.”
I told her, with a big sigh, “Yeah. Neither did I.”
Tammy asked, “Is everything ok with you and Greg?”
I told her, “Yes. Look, I’ll tell you all everything that happened, but later. Ok?”
Tina said, “Ok. You better.”
I made sure not to show any affection to Greg when we were out in public. I really didn’t need my husband, Dave, to see pictures of me posted on one of the lady’s Facebook pages of me with another guy. Whenever Greg tried to kiss me or touch me, I was able to avoid it. I told him, “I don’t feel comfortable expressing affection in public.”
He seemed ok with it and didn’t push it. We all mostly sat at the table and drank and talked. Sometimes one of the ladies would get up and dance with one of the guys at the bar. I didn’t know if they didn’t realize their husbands might see them on Facebook or if they just didn’t care.
Half the ladies left the bar drunk again that night, and Greg and the sober ladies and I had to help them back to the bungalow. After we got everyone inside, I walked back outside with Greg, and he asked me, “So, see you for dinner tomorrow night?”
I said, “Of course, unless you don’t want to see me.”
He took my hand and said, “Of course I do. Don’t you know that? I just wanted to make sure.”
I asked him, “You’re going to come get me, right?”
He bowed and kissed my hand and said, “Until tomorrow night, beautiful.”
As soon as I went back into the bungalow, the girls who weren’t passed out drunk were all asking me questions about my dinner date with Greg. I answered them all truthfully. Plus, I told them things they didn’t even ask about. I was surprised that none of them mentioned my husband, Dave, back home. I’m glad they didn’t.
All of them told me how happy they were for me and wished they were in my shoes. I slept like a baby that night, dreaming of what Greg had in store for me on our second dinner date.
Greg was at my bungalow the next night at six P.M. He was wearing khaki shorts and a Hawaiian button-up shirt like last time. I had on a dress with spaghetti straps again, so it would be easy to slip out of. We walked to Greg’s bungalow hand in hand. As soon as we were inside his bungalow and had the door closed, I was kissing him.
When we broke the kiss, I told him, “I don’t smell anything cooking.”
He said, “Well, I’m only hungry for one thing, and I thought you might feel the same way.”
Then he took my hand and led me to his bedroom, just like he did the night before. When we got to his room, he quickly undressed. He then slipped my dress off my shoulders, and when he saw I had on a bra and panties, he told me, “I thought I said, no panties or bra from now on?”
I had totally forgotten. I was so used to wearing them. He smiled and said, “That’s ok, it’s easy to fix.”
With my dress in a pile on the floor at my feet, he removed my bra and panties. We had both kicked off our sandals as soon as we walked into his bungalow. I was now standing there naked in front of him, except for my stockings, and then he sat down on the bed and took my hand, pulling me to him and said, “Bend over my knees.”
I laughed and asked him, “What?”
He smiled and said, “You disobeyed me by wearing a bra and panties, and you need to be punished.”
At first I thought he was joking but he pulled me down onto his lap and over his knees and started to spank my bare ass with his hand. He wasn’t spanking me hard, and the truth was, I enjoyed it. Even when he spanked me harder and it started to sting, it was a real turn-on. Everytime he spanked my ass I could feel his hard cock press into my belly. My husband, Dave, would have never done anything like that.
After he was done spanking me, he helped me up off his lap and told me, “Get on your knees.”
I knew what he wanted and I wrapped my hand around his cock and licked the head of it tasting his precum. Then I sucked on the head. I waited for him to put a hand on the back of my head and slide his cock balls deep down my throat, which I wouldn’t have minded one bit. But he didn’t. He just let me suck it at my own pace. I sucked him in long slow strokes, taking him as deep as I could until I gagged and choked. When I knew he was about to cum I stopped and he said, “Don’t stop. I was about to cum.”
I told him, “I know. But I don’t want you cuming until you are deep in me and I can feel you shoot your cum in me.”
He asked, “Wait, you don’t want to use protection?”
I told him, “No, I’m on the pill, and I know I am disease-free, and I’ll believe you if you tell me you are.”
Greg helped me to my feet and said, “Yes, I’m disease-free. But wait. If you aren’t seeing anyone, why are you on the pill?”
I thought fast and said, “Because it does wonders for my complexion.”
He said, “Ok, we don’t have to use protection if you don’t want to. Now get up on the bed on all fours.”
I quickly got up on the bed and assumed the position. I was surprised when instead of getting on the bed behind me Greg knelt down and started eating my ass. My God! The feeling was amazing. I had never had anything done to my ass before. My husband, Dave, wasn’t interested in it all. He wouldn’t kiss it, lick it, spank it, or fuck it, nothing.
I felt Greg shove his tongue deep in my hole. He flicked his tongue in and out of my ass so fast. I pushed my ass back onto his face as he licked me. God, the pleasure was unbelievable.
I reached back and played with my pussy as he ate my ass. Greg pushed my hand away and said, “No, no, beautiful. I’ll take care of that.”
Well, I wasn’t going to argue.
Greg spread my ass cheeks wide and licked me from my pussy up to my asshole. He did this slowly about six times, sliding his tongue in both holes each time he did it.
I just moaned, “Oh, Greg.”
Then he asked me, “Are you ready for me to fuck your ass, beautiful?”
I just moaned my answer.
I would have loved for Greg to have taken more time eating my ass, but I also wanted to feel his bare cock inside me and fill me up with his cum. He told me, “Put your hands on the headboard and keep them there.”
It was a wooden headboard, and I did what he told me. Then he got off the bed. I waited for what seemed like an eternity before he came back. I asked him, “Where did you go?”
He smiled and said, “I had to get something for us.”
He held up a bottle and said, “This here is body oil. It heats up as it reacts with our body heat. And it’s a good lube too.”
Dave and I had only used regular lube, nothing special. As I looked back, I saw Greg pour some of the oil into his hand and apply it to his cock. It glistened as if it were a God’s cock. I really wanted him to fuck my virgin ass. I knew it would hurt since he was so big, even with the lube.
After he was done lubing up his cock, Greg rubbed some on my ass cheeks and then put the tip of the bottle in my asshole and squirted some in me. Then he fingered my asshole. My asshole was so tight even his finger hurt. I gasped and said, “Ow, ow, ow,”
He asked me, “Are you ok?”
I told him, “Yes, it’s just that’s always just been an exit.”
He asked me, “So, you’re an anal virgin then? Well, we don’t have to do anal.”
I told him, “What, no, no. I really want to do it.”
He asked, “Are you sure? I mean, I’m pretty big. My cock will hurt a lot worse than my finger.”
I told him, “I’m sure.”
I had always wanted to try anal and I knew this would be my only chance. I mean, Dave wasn’t interested. And I didn’t have anyone back home that could fuck my ass without Dave finding out. He told me, “Well, I’ll add a little more of the oil before we start.”
A little more. I felt him put the tip of the bottle in my ass and squirt more in. When he set the bottle on the nightstand beside me I could see it was almost empty and it looked full before he poured some in his hands to lube up his cock and it looked to be a quart sized bottle. But hey, I wasn’t going to complain. I have been told by others that the more lube you use if you are tight the better.
He gave me a minute for the oil to get deep in me, then he asked me again, “Are you sure you want to do this?”
I gave a big sigh and said, “Fuck my ass, or I’m out of here.”
He didn’t say a word, he just gave my ass a hard slap with his hand. I just looked straight ahead to prepare myself for the pain I knew was coming. I felt one of his big hands on my ass cheeks as he spread them. I looked back over my shoulder to see what he was doing. He gave my ass another hard slap with his hand and told me, “Eyes front until I tell you different.”
I quickly looked straight ahead. I could feel the tip of Greg’s cock at my virgin hole. He tried to be gentle, but we both knew being gentle wasn’t going to work. The oil had run down into my pussy and I could feel it working. Without any warning I felt Greg give a quick hard thrust with his hips and the head of his cock was in my asshole. I let out a scream and buried my face in one of the bed pillows.
Greg reached up and grabbed a handful of hair on the back of my head and pulled my face up off the pillow. He told me, “Keep your head up.”
I asked him, “But, what about the neighbors?”
He said, “Who cares about the neighbors? I don’t. Do you?”
He didn’t wait for me to respond. He just kept a hold of my hair and then placed his other hand on my hand on the headboard so that both of his hands were on top of mine and then slowly shoved his huge cock in me until I could feel his balls touching my ass. I could feel tears streaming down my face, and God, the pain!
As he fucked my ass I cried, “Oh God! Oh God, Greg, it hurt so bad! I’ve never felt any pain like this, oh, God!”
The former statement wasn’t exactly true. It was a toss-up between childbirth and this. I didn’t use any medication when I gave birth to Steve, I had him the natural way.
After about a half a dozen slow strokes, Greg’s cock started to feel good in my asshole. I begged him, “Yes, Greg! Faster, harder, deeper!”
He was happy to oblige me and did as I begged. I could feel my orgasm building. I wondered if I would squirt again or if it was just a one-time thing. I would soon find out.
As my orgasm continued to build I could feel Greg grunting every time he rammed his cock into my ass. He rammed me so hard I thought for sure it was going to shake the headboard off the bed.
I held out as long as I could before cuming. I loved the pleasure I was getting from Greg’s cock deep in my ass and I didn’t want that pleasure to end.
When I couldn’t hold out anymore, I just let go. I think that orgasm was even more pleasurable than my last. And yes, I did squirt again. And it was a lot more than last time.
I think when I started squirting, Greg must have pulled his cock from my asshole because when I turned around to look at him his face was covered with my cum.
I couldn’t help but laugh, “Oh, Greg! I’m so sorry.”
He just laughed and said, “It’s your mess, how about you clean it up?”
I didn’t hesitate. I turned around and kissed him, then licked his face clean. Then we just play on our backs in each other’s arms. I asked him, “Do you mind if we don’t go to the bar tonight? I would just rather stay here overnight.”
Greg said, “Sure, I don’t mind. But you want to tell me why you don’t want to go to the bar?”
I told him, “Well, I’m sore. And I’m pretty sure I’ll be walking funny and my girlfriends will put two and two together and know what we did.”
Greg got up off the bed and asked, “Do you regret doing it?”
I quickly got up off the bed and told him, “No, I don’t regret anything we’ve done. In fact, I loved it.”
He said, “I’m sorry I hurt you. But first time anal is always painful with someone as big as me.”
I reassured him that it was ok and that the next time we did it, it wouldn’t hurt as badly or maybe not at all.
He smiled and pulled me to him and kissed me and said, “I think we should still take a shower even though we aren’t going to the bar. Then I’ll cook another authentic Caribbean meal. And you can rest up.”
I agreed and said, “Let’s take one together.”
We walked into the bathroom and Greg turned on the shower and adjusted the temperature, then we both got in and lathered each other up and washed one another.
Then Greg took the shower head from its cradle and rinsed the soap off both of us. Then he kissed me, kissed down my neck to my tits, kissed and licked them. He sucked on my nipples making them rock hard. Then he motorboated them.
He turned me around so my back was to him, then whispered in my ear, “Bend over, beautiful.”
I started to go to my knees but he gave me a love slap with his hand on my ass and said, “No, no. Stay on your feet. Bend at the waist and grab your ankles.”
I did what he instructed me to do. At first I thought he was going to fuck my asshole again. I wouldn’t have tried to stop him if he did. I felt Greg spread my ass cheeks and to my surprise I felt his tongue on my asshole. The warmth of his tongue felt amazing. As he ate my asshole he slowly slid a finger into my pussy.
He told me, “See, I told you I would take care of it.”
I just moaned. Greg Just kept fucking my ass and fingering my pussy. I didn’t know if he wanted me to cum again, but if he kept that up I surely would. As he licked my asshole he told me, “I can’t wait to fuck this again tomorrow night.”
I let out a gasp. He said, “You want me to fuck your ass again, don’t you?”
Before I could answer, Greg said, “It won’t be as bad tomorrow now that I took your cherry tonight.”
He brought me to the brink of cuming then suddenly stopped. He planted a kiss on my ass and told me, “Ok, time to get out and dry off.”
I couldn’t believe he left me hanging like that. He got out of the shower and quickly dried off. I did the same and followed him to the bedroom. He then went to the kitchen without bothering to get dressed so I didn’t get dressed either. He got all the pans and utensils out that he needed to fix dinner. Then he got out the food he was going to need.
I asked him, “Is there anything I can do to help?”
He told me, “No, just sit there and look beautiful.”
I blushed. As he started preparing dinner, I saw him cutting up what I assumed were vegetables, but I had never seen anything like them, and asked him what they were.
He told me what they were called and where they came from, but again, like last time, I couldn’t tell you what he said. Their names were so elaborate. We sat and ate dinner naked. He said, “I’ve been thinking, beautiful. Why didn’t you stay here with me the rest of the time you are here?”
I was surprised and said, “What?!”
He said, “I don’t mean for you to spend all your time with me. Just spend your nights here.”
I told him, “Well, I’ll have to talk to my friends about it. Can you wait until tomorrow after I speak to them?”
He looked into my eyes and smiled and said, “Of course, beautiful.”
After we ate, we went back to Greg’s room and watched some TV. He was behind me, and I was nestled in his arms. I had almost dozed off when I felt his cock at my pussy. I turned my head to look back at him and said, “Ummmm, twice in one night. What a treat.”
He didn’t anwer me, he just slowly slid his cock in me and fucked me as he reached around and squeezed my tits and played with my nipples.
As he slid his cock into my pussy balls deep he kissed the back of my neck and said, “I love your pussy, beautiful.”
I moaned, “Mmmm.”
He fucked me in long show strokes until we both came. Then we fell asleep with his cock buried in my pussy. I don’t remember anything until I woke up the next morning.
When I woke up and realized Greg wasn’t still inside me, I reached over and felt his side of the bed. When I didn’t feel him, I turned my head and opened my eyes to find that he wasn’t there.
I went to the bathroom and he wasn’t there, so I took my dress off the back of the bathroom door where I had hung it and slipped it on. Minus my bra and panties.
I thought I smelled food cooking, so I made my way to the kitchen. When I got to the kitchen, I found Greg already dressed and fixing breakfast. It wasn’t anything fancy like dinner, just bacon, eggs, toast, and orange juice.
He gave me a big smile when he saw me and said, “Good morning, sleepy head. Breakfast is all ready.”
There were two plates of food and two glasses of orange juice sitting on the table. I was starving, so I sat down and we began eating.
Greg said, “How about first thing after we eat, we stop by your bungalow and talk to your friends about what we discussed last night?”
I asked him, “You mean about me staying with you the rest of the time we’re here?”
He said, “Well, yes. Unless you’ve changed your mind.”
I told him, “No, no. I haven’t changed my mind. But don’t you think we should get a shower first?”
Greg said, “I’ve already had a shower. I’ve been up for a while. I thought maybe you could take a shower at your place when you pick up your things, if you decide to stay here with me.”
I told him, “Yeah, ok, sure.”
After we finished eating, we walked to my bungalow. I was still a little sore from the anal sex Greg and I had the night before. But I wasn’t walking as badly as I would have been if I had gone to the bar last night. I was hoping none of my girlfriends would notice.
I was about to open the door to the bungalow when Tina opened it from the other side. She gave me a big smile and said, “Hey, girlfriend! Come in and tell us all about last night!”
She must not have seen Greg at first because she shut up real quick, and she blushed. Then she stepped back into the bungalow and said, “Well, please. Come in.”
Greg and I walked inside, and all the ladies were in the front room. And I said, “Ladies, we need to talk.”
Tammy asked, “Do you want Greg to leave?”
I told her, “No, he knows what I want to talk to you guys about.”
Tammy said, “Well, come on. Let’s all sit.”
We all sat down, and I said, “Greg has asked me to move in with him for the rest of my stay here.”
When none of the ladies said anything, I said, “I would just be moving my things to his place and sleeping there. I’ll still be spending my days with all of you.”
They all seemed relieved when I said that. Then I said, “But only if you all are ok with it.”
They all said they were ok with it. I said, “Well, I didn’t get a chance to take a shower this morning, so I’m going to take one here.”
As I started to the bathroom after I got clean clothes and other stuff, I said, “Please, be nice to Greg, ok?”
Tina said, “Hey, don’t worry. We will.”
I could only imagine what they talked about while I was in the shower. I would find out later, after we got back home. I knew it was all just in fun, but I was so embarrassed.
Tina said that Greg told them, “I was serious when I told her she was the most beautiful woman I have ever seen. And why isn’t she married or seeing someone?”
Tammy said, “She keeps saying she just hasn’t met the right man.”
Tina said that he told them, “I have never been with a woman as sexually adventurous as Sarah. She doesn’t say no to anything I want to do.”
Tina asked him, “Like what?”
At first, Greg was reluctant to tell them. He said, “I… don’t know if Sarah would want me to say.”
Tina said, “Oh, come on! Sure, she would. All of us ladies have known each other since we were five years old. There are no secrets between us.”
Greg said, “Well, ok. I mean. If you’re sure.”
They all assured him I would be ok with it. He said, “A lot of women don’t like having their ass spanked, but Sarah seems to like it…a lot. And anal sex, once she got over the pain of me taking her cherry she seemed to love it.”
Then they said he added, “I told her, I don’t want her wearing a bra or panties the rest of her stay here. She agreed.”
Tina said, “But when she left here last night, she was wearing a bra and panties.”
Tammy told me he said, “Yeah, and I bent her over my knee and spanked her ass for wearing them and she liked it.”
Tina then said he told them, “She loved it when I rimmed her asshole.”
When I came out of my room fully dressed except for a bra and panties, of course, I asked, “So, did everyone behave themselves while I took my shower?”
Tina just gave me a big smile and said, “Of course.”
The ladies had all eaten breakfast by the time we had gotten to the bungalow, so Greg suggested we go walk around and see the sights.
He showed us things we hadn’t seen before. It seemed everyone knew him. He was like a local celebrity. We bought some more souvenirs for friends and family. There was a young boy taking people’s pictures, and Greg said, “Should we get ours taken together?”
I tried to protest, but Greg insisted. He told me, “A little memento to remember your trip.”
Tina said, “Oh, I think Sarah has plenty of momentos to remember her trip already.”
I just blushed. We were out all day. Greg paid for whatever we ate or drank. He bought me a few things. He would have bought me half the items in the stores we went to if I had let him.
When we got back to my bungalow, Greg insisted on carrying my suitcase back to his place. I knew how heavy it was, and I wasn’t about to argue. He picked it up like it was as light as a feather.
When we got back to his place the door was barely closed before I was on my knees pulling his cock out of his shorts. Greg looked down at me and took both my hands in his and said, “Look at me.”
When I looked up at him, he said, “Slow down, beautiful. We have plenty of time.”
He then pulled me to my feet, and we shared a passionate kiss. Then he picked me up and carried me to his bedroom like a groom would carry his new bride across the threshold of their new home.
He tossed me onto the bed and quickly took his clothes off. He then slipped the straps off my dress off my shoulders and pulled my dress down and off. We were now both naked, looking at each other.
Greg kissed me and said, “How about we try a different position tonight, beautiful?”
I told him, “Hey, I’m up for anything.”
He said, “How about you on top?”
Then he laid on his back on the bed, his cock already rock hard. I asked him, “Can we use the body oil again? I loved it.”
He told me, “Well, there’s not much left. But there should be enough left for one more time.”
He was about to open the bottle and lube up his cock, but I took the bottle away from him and said, “Let me.”
I poured about half of what was left in the bottle right onto the tip of his cock and let it run down to his balls. Then I slowly used both hands to coat his cock. Going all the way to his balls and back up to the tip of his cock. Greg moaned, “Your hands are amazing, beautiful.”
Once I had his cock lubed up good I raised up onto my knees and used my hand to guide the head of his cock to my pussy and slowly lowered myself it. He wasn’t a tight fit anymore, but he still felt amazing inside me. Greg grabbed my ass to lift me off of him, but I slapped his hands away and told him, “Uh uh, baby. This time it’s all me. You just lie back and enjoy it.”
I started off riding him slowly. I placed my hands, palms down, on his chest as I sped up. We were both really getting into it, moaning and groaning. I started pinching his nipples between my fingers, and he loved it. He begged me, “Mmmmm, yes! Your fingers feel so fucking good, beautiful! Pinch them harder, as hard as you like, I don’t mind!”
I didn’t want to hurt him too badly. But it was a big turn-on to have a man beg me to hurt him. But I did like he asked and pinched them harder. Even though I told him I would be doing all the work, Greg started thrusting up into me, but I didn’t mind. I continued rocking back and forth on his cock. I arched my back and leaned back until the back of my head touched his feet.
I cried out, “Oh God! Oh God! Baby, I’m going to cum!”
I asked him, “You’re going to clean all your cum from my pussy once we both cum, aren’t you?!”
By this time I think I was rocking on his cock as fast as I could and he was thrusting up into me as fast and as hard as he could. He cried out, “Yes, yes, beautiful! Whatever you want, I’ll do it!”
I think I came a split second before Greg did. As we both went into convulsions, I lay flat on my back so my back was resting on his legs. And of course, I squirted again. Once our orgasms had subsided, I lifted myself up and straddled Greg’s face, sitting on him, putting a knee on either side of his head. I slowly lowered myself onto his face, covering both his mouth and nose. I told him, “Look at me, Greg.”
When he looked into my eyes, I smiled and said, “Eat up, baby.”
I could feel his tongue go deep into my pussy flicking in and out to get his own cum out of my pussy that he had just deposited there. His tongue was so long and he was going so deep, I thought for sure I would cum again.
I must have sat on his face for a good two or three minutes. I could tell from the look on his face that he needed air. He could have easily tossed me off his face anytime he wanted. I guess he didn’t because he wanted to make me happy. It was such a turn-on to have a guy do anything to make me happy that I just sat on his face for a few more seconds before lifting myself up.
When I finally lifted myself up off his face, Greg immediately started gasping and taking in big gulps of air. I laughed and asked, “Are you ok?”
He gave me a smile and said, “I’m great. I loved that.”
Needless to say, the rest of my time in the Caribbean didn’t go as planned. I only saw my girlfriends once or twice after that until it was time to go home. Greg and I shared a whirlwind romance. We made love morning, noon, and night. We couldn’t get enough of one another. When we weren’t at his bungalow, Greg was taking me on hot air balloon rides where we made love in the basket. I would bend over at my waist and look over the side of the basket which at first made me nauseous until I felt him slide his cock into one of my holes from behind.
We went paragliding. When we went snorkeling, we would find secluded spots where we could have sex under the water, only coming up when we needed air. Greg had a friend who had a small eight-passenger plane, and we had sex in it. I guess you could say I am a member of the mile-high club now.
Sometimes we would have dinner out and we would get a table in a dark corner and I would suck Greg’s cock under the table. Greg paid a waiter once to look the other way when I did.
It was like a romantic honeymoon, only we weren’t married.
But all good things have to come to an end, and before I knew it, the time had come for me and my girlfriends to go home. Greg insisted on driving us all to the airport. I took a minute alone with Greg to say goodbye.
As we shared one last kiss, I told him, “I left a letter for you on the desk back at your bungalow. I want you to read it.”
I put in the letter how I thought my time with him was amazing and the most fun I had ever had in my entire life. I apologized for lying to him when I said I didn’t have a husband. I explained how long I had been with him and why we got married, and how my life had been, and how he and my husband were the only two men I had ever been with.
I made sure to tell him he didn’t have to worry about me getting pregnant because I was telling the truth when I said I was on the pill. I didn’t have to worry about Greg finding me when we got back home, since he didn’t know my last name or my phone number. At least I didn’t think I had to worry…
