Alison Has a Bad Month

This is my first story about Alison. If readers like it, I may write more. Please let me know! Thanks, JB

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It had been a bad month. First, I caught my partner cheating on me, and I kicked him out. Boy, was I glad we had never married. He had simply moved in with me, so one day I had the locks changed, and put his things on the sidewalk. You don't cheat on Alison Sullivan. He should have known better.

That was the beginning of the month. The second week of it my father died. He was not that old, only 50 years old, but he dropped dead of a heart attack. My mother had died 10 years earlier, in her mid thirties, of breast cancer. So now at the tender age of 25 years old, I was on my own, except for my sister.

So I went to Aruba to get away from it all. Different people grieve differently and I thought a beach holiday might work for me. I flew down here from New York, but apparently my suitcase did not. They finally found it, and it is in Turkey. How that happened is beyond me, but it's just not my time for good luck right now. It will be delivered to my hotel here in Aruba, most likely the day before I leave.

So here I am, checked into an upscale beachfront hotel, with only the clothes and underwear I traveled in. Not wanting to spend my first day buying clothes in what passes for a city in Aruba, I went to the hotel store, where I found a blouse, a skirt, and a bikini. The store does not have a dressing room, but it has a return policy, so I could have tried on the clothes in my room.

I did not want to do that, which would have entailed the making of multiple round trips to the store from my room until I got everything right. So I tried on everything in the store. It's a good thing I did, too, since nothing fit right the first time. Apparently I am not the size I thought I was, at least for the clothes on sale in that store.

I was repeatedly reduced to a bra and panties in the store. Since all the walls are glass, I was a bit exposed that way, but by this time I was so exasperated I did not care. And it is a beachfront resort, so I figured how different are a bra and panties than a two-piece bathing suit? Of course one big difference is that both my bra and panties are transparent. I happened to wear that set for the trip, and now that's all I have. So the careful voyeur could see all of me.

Anyway I just did not have the energy to care. I was still mourning the death of my father. His death brought up my mother's death too, and I was an emotional basket case.

Then came the bathing suit. You really need to get naked to try on a bathing suit, so this was a limit case. I tried on a bikini, stripping naked and then quickly putting on the bottoms, which happily fit perfectly. But the top did not, and my boobs were spilling out of it, even my nipples were easily exposed in the top. So I tried on the top in a bigger size, and it was a perfect fit. But I was topless in the store for a while, while searching for the right size.

Being topless also did not seem like a big deal to me, because I was looking forward to sunbathing topless on the beach, later that same afternoon. Seeing my boobs through a store window did not seem that different just then to seeing them on the beach.

The store would not sell the swimsuit parts separately, and I was in no mental shape to argue, so I ended up buying two sizes of the same swimsuit, in order to get the top and bottom that fit. Given my emotionally fragile state, it was the right thing to do.

Upon leaving the store, I bumped into a man who had been loitering outside the store. I excused myself, and he said, "No problem. I hope you do not mind. I enjoyed watching you choose your bathing suit just now. You have beautiful breasts."

This was of course not my first choice for a first interaction with a man in Aruba, and I was taken aback. The man was big and muscular, good looking, and he had a mellifluous voice which set me at ease. I did not know how to reply to such a remark, so I just said, "Thank you. Maybe I'll go topless on the beach, then."

He said, "I hope you do. I'll try to find you. My name is Mark, by the way."

"I'm Alison. That's Alison with one ell. Alison Sullivan is my full name. I'm pleased to meet you," I said. Then I wondered why I gave him my last name. I guess it was in case he wanted to look me up. I liked the way he looked, and I already knew he liked my boobs. Hey, that's a start for a lonely woman who is in mourning, right?

Besides, I was up for some casual sex in Aruba. I thought it might help in terms of all my problems.

My luck was turning, and he invited me to dinner that evening, right there on the spot. I accepted, and he told me he would pick me up at my room at 7pm. I told him I was in room 812, and that was that.

I took my purchases to my room, stripped naked, applied suntan cream all over my body, and then put my bikini on. I headed out for the beach: it was vacation time. I donned my sunglasses and got a mattress with a shade umbrella, and lay down and opened my novel. The weather was perfect, the water inviting, and the sun warm on my skin. This was just what a girl needed.

Nobody was topless on the beach, to my surprise; I guess that's the downside of going to an island that used to be Dutch, and not French. So I kept my top on too, at least when I lay on my back. When I lay on my stomach in contrast, off it came. Mark found me after a while, and I was topless on my stomach. "True to your word, Alison," he said.

His voice startled me, and I explained my strategy, rolling over topless to face him, and of course to tease him with a prolonged look at my boobs. He said, "That's because you're at the hotel beach. Tomorrow if you want I can show you a beach that is much more open and relaxed." I told him I would think about it. I did not say this, but first I wanted to see how this evening would go. I put my top on as we talked. I did it,\ slowly so as to maximize his viewing time of my boobs. I wanted him to long to touch them.

The evening went well. I did not fret about what to wear, because I had only two outfits. My bra was all sweaty and smelled, so I washed it in the sink, but it was still wet when it was time to get dressed for the evening. So I went without a bra. Rules are different in beach towns, and I was sure it would be okay.

Mark was right on time, and he took me to a nice seafood restaurant, where the local fish had just jumped out of the water and onto our plates. I drank a fair amount, and was feeling little pain, when Mark commented on my lack of a bra.

"I was wondering if you would notice," I said.

"Oh, I noticed a long time ago. I just wanted to get enough wine into you to relax you, so I would not offend you if I brought it up," he said.

"Why did you bring it up in any event?" I asked.

"Because, sweet Alison, I want to see your luscious boobs again," Mark said. "I figure maybe if you're drunk enough you might flash them for my viewing pleasure."

"Sorry, Charlie," I said. "I'm not that drunk! And I doubt I could ever get that drunk, anyway. No way I'll flash in a crowded restaurant."

"How about in an empty parking lot, then, after dessert?" he said.

I did not reply. I just smiled and took another sip of wine. It was time to order dessert.

That's when it happened. I saw one of my old boyfriends, Adam, from a few years ago. He was there at the same restaurant with a bimbo blonde. The bimbo blonde was poured into her outfit and looked as cheap as an Omaha whore.

I hated Adam. I had posed for some nude pictures for his personal use and pleasure, and some of them were quite explicit, just for him. I had been only 22 at the time, young and naïve. One had a dildo sticking out of my cunt, and others were even worse. When we broke up, he posted scans of all those photos on the Internet, at an ex-girlfriend revenge site.

I was embarrassed and shamed for a long time. Lots of men who I knew saw the pictures. I did wonder how they found them; do they regularly peruse such sites? Men are so strange.

When the men looked at me after the pictures were out, it was obvious to me that they were mentally undressing me, imagining they were fucking me. They probably imagined their cock was the dildo. And then there was the picture with two cocks in me: one in my mouth and the other in the more customary place. It was horrible.

This was really not my month! I wanted out of the restaurant right away, so I said to Mark, "Let's go now. I can't wait to flash you."

Mark got us out of there in lightning speed, and I kept my word, raising my blouse in the parking lot and showing him my boobs. He reached for my boobs, keeping my blouse up above them, and fondled them openly right there in the parking lot. I pulled away from him, pulling down my blouse, and I was angry with him for taking advantage of my attempt to tease him a little. But also the exhibitionism of showing my boobs in public turned me on.

Then I realized that people in the restaurant could see into the parking lot, since the walls of the restaurant were largely windows, and there were lights keeping the parking lot from being too dark. I wondered if any, or more likely how many, people had seen me exposing my boobs in the parking lot.

I wondered even more if Adam had seen me. I looked at the restaurant and saw Adam looking out, right at me. Our eyes met. Shit. Double shit. Well, he did not know where I was staying; there are lots of beachfront hotels in Aruba. Given how my luck was going, he saw me flashing.

I noticed that the bimbo spoke to him, and he turned to look at her, and then I ducked away, entering Mark's car for the drive back to the hotel. And no, I did not invite Mark up to my room for a drink. This was our first date. It was obvious Mark was disappointed; I'm sure that he had delusional ideas about bedding me that very night. That much was clear to me. Well sometimes delusions are just that: delusions.

The next day I went to the beach and there was a French woman who came to the spot next to mine, and she quickly took off her top, exposing her beautiful breasts to the sun. This was all I needed, and my top came off, too. I suddenly became popular.

When I went to lunch at one of the many seaside lunch places, I of course put my top back on, but several men who had been ogling me on the beach tried to strike up conversations with me. Amused, I welcomed their flirtatious attempts.

I kind of liked one of them, the one named Jeremiah. He proposed that the two of us rent a pedalo, which is a type of paddleboat. I thought it would be fun, and after lunch we did exactly that. We went far from shore, so that if anyone were looking at us, he would need binoculars to see us in any detail.

Liberated from prying eyes, I removed my top, and this excited Jeremiah. He thought I was asking for sex, not just trying to get a little sun on my boobs. So he surprised me by leaning over and kissing me. It felt nice, so I kissed back.

We kissed for a while and he fondled my boobs, and it all felt nice. Then his hand went into my bikini bottom, and he began to move his fingers around my cunt. It was decision time. Nobody could see us, and I got turned on with him doing that out in the open. So I let him, and soon my bottom was off too. I was naked on the pedalo.

I leaned over him, pulled his trunks down, and took his cock into my mouth. My previous partner, the one I kicked out when he cheated on me, had really wanted me to deep throat him. It took me months of trying before I finally learned how to do it. I sucked him off several times a day, every day, trying to learn how to deep throat. He did not mind, and when I succeeded, finally, he was thrilled.

He was so proud of me; he wanted to show me off. I said no. But he kept the pressure on relentlessly. One day we had another couple, Steve and Susan, over for dinner. Our friends were complementing me on the great meal I had cooked, and I was enjoying their praise. Then my boyfriend bragged that being a great cook was only one of my many accomplishments. Recently I had mastered deep throat blowjobs, too.

I sunk in my chair trying to hide my face and disappear under the table. To my surprise, Susan said, "I've never really believed it to be possible. I would love to see you do it! Do you think you could do it to Steve? I warn you, he has a long cock."

I was stunned by this, for so many reasons. Then Steve said, "Susan just volunteered me, but if you're willing, Alison, I would be forever grateful."

I did not know what to do. I said, "Excuse me everyone, I'd best clear the table now." Then I took everyone's dishes to the kitchen and slowly rinsed them off and placed them in the dishwasher. Everyone followed me into the small kitchen, making it crowded and rather intimate.

The three of them ganged up on me and would not let it drop. Steve volunteered to eat me in exchange for a deep throat. I was still stunned. Then Mary said, "I could let your boyfriend fuck me if you like. I know he's wanted to do me for a long time."

Anyway, this turned into a group sex session. Susan undressed me in front of the men, Steve ate me to an orgasm, and I sucked off Steve, deep throating him, of course. Steve shot his load into my throat.

My boyfriend had been fingering Susan as Steve and I went at it, and when we finished he took her from behind while Steve and I watched. As we watched, Steve began to kiss me, and he fondled my boobs. I ended up fucking Steve too, and letting my boyfriend take me after Steve. It was a wild night, and what everyone took away from it was that I could really and truly deep throat a man.

Jeremiah benefited of course from my determined previous efforts, the consequences of which I just described. I kissed his cock, swirled my tongue around its head, sucked gently on his balls, and licked his shaft. Then I took the head in my mouth while I pumped his shaft with my hand. He was groaning loudly.

I gradually took more and more of his cock into my mouth, pumping it in and out, effectively letting him fuck my mouth. Then when I was ready, I took the entire thing in my mouth, right down to his balls. That was when he started to invoke the deity in exultations of his pleasure. That is, he said, "Oh my God, oh my God Alison. Jesus, you are amazing!" It sounds better when I said he invoked the deity in exultations of his pleasure, doesn't it?

I deep throated him right there in the pedalo. His cock was a little shorter and not as thick as the one of my previous boyfriend, and much shorter than Steve's had been, so I had confidence I could deep throat him. He was groaning up a storm as I gave him the best blowjob of his life with the sun burning down on us. I was certainly the only girl who had ever deep throated him. I may be the only one who does it to him for his entire life.

I knew it was the best blowjob of his life because he told me, repeatedly, after he had shot his load into my throat. It was warm, sticky, salty, and had a slight sweet taste to it. Actually, it was not that different from drinking the liquid that comes with oysters, except spunk is more viscous. A pedalo far from land seemed a good place to swallow his spunk.

So here I was, having met Jeremiah only hours ago, and I was naked with him on a pedalo, having just given him the blowjob of his life. He was now gently fingering me. I began to get freaked out. I know it had been a bad month: my father died, my boyfriend turned out to be a creep, my luggage is someplace in the near east, but did that mean I suddenly had to become the world's easiest slut? It sure looked like it just then.

I let Jeremiah finger me until it became clear to me I was not going to cum being fingered naked in a pedalo at a crowded beach. I guess I am still a little uptight. I gently removed his hand, and put my bikini bottoms back on. It turned out to be just in time, as a friend of his had swum out to our pedalo and was cheerfully hanging onto the side, gawking at me. I did not know how long he had been watching us.

His friend, named Zeke, spoke with Jeremiah, and Jeremiah jumped into the water while Zeke climbed aboard the pedalo. I did not know what to make of this. I just stared at Zeke, and also at Jeremiah now in the water, dumbfounded. I suspected Zeke wanted me to do him, too. Good luck with that, I thought to myself.

Zeke introduced himself. I said, "Pleased to meet you, Zeke. I'm a bit surprised, too. I thought we were alone out here."

"You were of course," Zeke said, "but I like to swim and I saw you two out here from afar, so it gave me a destination. I did not realize it, but it also gives me the chance to meet a truly beautiful woman."

Flattery usually works on me, but I was nevertheless fairly freaked out. I decided to confront the elephant in the room, and said, "How long have you been out here, Zeke? Did you see us fooling around?" Bare in mind I was still topless.

"Yes I did, pretty woman. That blowjob you gave Jeremiah was completely amazing. I've never known nor seen a woman give such a total deep throat before. Hats off, I say," replied Zeke.

"Hear, hear!" cheered Jeremiah from the water. I was blushing up a storm, I'm sure.

Strangely, while I had thought we were alone and we were fooling around with discretion, the fact that another man had watched, and now thought I was some kind of sexual marvel (and also pretty), got me fully aroused. This had never happened to me before. It was a turn on to have been watched, which nevertheless shamed and scared me. But the sexual arousal was undeniable.

I put my top on and announced it was time to pedal back to shore. Zeke tried to convince me to give him a blowjob, too, but he stopped trying when he realized if he did not, I would evict him from the pedalo. We compromised, and he seemed happy when I agreed to let him spend a few minutes feeling me up.

Zeke removed my bottoms, rendering me naked again. In no time at all he was playing with my boobs while fingering me with his other hand. Next he surprised me completely by eating me out. It was an awkward thing to do in a pedalo, to be sure, but that was his problem. While Zeke went down on me, Jeremiah was there in the water cheering him on. This was the most erotic moment of my life up to that point.

I began to moan to encourage Zeke. It felt so wonderful I was desperate for him not to stop. I needed to cum, and I was so close! But inexplicably he stopped, and he left me breathing unevenly, confused and unfulfilled, naked with a soaking wet cunt, under the hot sun in a pedalo far out in the water.

Even though I was sexually frustrated, I got over it quickly and put on my bikini again, and asked Jeremiah to help me pedal back to shore. "Give me a blow job in my room at the hotel, and sure we can go back right now," came the reply.

I said, "Fuck you, Jeremiah. You're a boor. Zeke, could you help me pedal back to shore?"

"Me? When I didn't even get a hint of a blowjob? I don't think so," he replied, and he began to swim back to shore.

I'm a good swimmer, and I'm healthy and strong, so I thought I too could swim back. Jeremiah had rented the pedalo, not I, so I guess it was his problem to bring it back. I jumped off it and swam back to shore. I could hear Jeremiah calling after me, but ignored him. I could still taste his cum in my mouth, a constant reminder of what I had just done. Maybe the swim could undo my slutty behavior of which I was so ashamed right now. Who am I kidding?

I skipped going back to the beach, unable to deal with Jeremiah and Zeke and whomever else they had told about my antics, and went straight to my room. I drank a lot of water to get rid of the semen taste. The water was good, but it did not get rid of the taste. So I drank a Coke from the minibar, and then I took a shower.