A Story of Four Winters

Men had asked me out, and I dated in college, and I liked the men and often slept with them too. At the third winter vacation my boyfriend did not come home with me; he had to go to his parents' home for complicated family reasons.

Andrew now had graduated, and he was working in California, and he decided to stay there and have fun with his girlfriend, so I came home alone and enjoyed seeing my parents and even more so my local friends, even if fewer and fewer of them were returning to our isolated small town at Christmas time.

Susie came by, the woman who had changed me from a normal high school senior into a flaming slut with widely available videos of me having sex, even losing my virginity. Time heals wounds, and we were now friends, albeit uneasy friends.

Susie came by to ask a favor. Her father and a small group of his friends, five men in total, have a weekly poker game. When Susie is home from college she plays cocktail waitress, and since it's Christmas time, she wears her Santa's Helper outfit. The men enjoy ogling her body while she brings them beer or sometimes whiskey.

"You do this with your father there?" I asked. I was a wee bit incredulous.

"Especially while he is there, Alessandra. With him there, there is no touching, you know what I mean?"

"Few women know better than I what you mean," I said.

Susie wanted me to do it the very next night, wearing my Santa's Helper outfit, which is much too sexy, and unfortunately which I still had. Susie said she 'had a conflict.'

I said no, that was not something I wanted to do. I also felt I owed Susie no favors; absolutely none at all. Scratch me a little and I would hate her in fact. The betrayal of secretly recording Adam and I giving each other our virginity, and showing it live to 38 classmates, is after all not a forgivable event.

When I said no Susie began the blackmail. She showed me 8 x 10 glossy photos of Andrew's cock ravishing me. She told me she also had videos of my passionate fuck with Adam almost exactly one year earlier. She asked me again if I could be the hostess of her father's poker game.

I felt faint and had to sit down. My head was in my hands. Susie kept pushing me for an answer while my mind was doing cartwheels, and my stomach was nauseated.

"Susie, I am not your father's daughter. He might not protect me like he does you. Also my breasts have grown a little and the outfit is surely now too small on top. Do you remember the extent of the décolletage of my outfit? I'll look obscene and as if I'm asking for it," I said, in a halting voice that was almost a whisper. "Will the men behave?"

"They always have before," Susie replied, omitting that her father had been there in the room, and that she did not wear nearly so suggestive an outfit as she was asking, no demanding, that I wear. "Anyway Alessandra, if you deny me this small favor for only one evening, I'll go public with the photos and videos of you and Andrew. It's your choice."

Obviously, I had no choice. The next night I nervously tried on my outfit. As I feared, my boobs were spilling out of my décolletage to the point where even half of my nipples were on display. This would not do.

I had no more fabric, but I cut some off of my panties, now making my panties skimpier and revealing about half of my ass crack, and I made a little strap, with a button at each end, made two button holes about two inches above my belly button, which was how far down the décolletage went. That buttoned strap pulled the sides together, and while now my boobs pushed out at the fabric almost everywhere, at least my nipples and most of my areolas were hidden from view.

The cost was that now I looked truly cheap, with my boobs trying desperately to escape the constraint of the too tight outfit. In addition, my red velvet panties which had originally been modest, were now anything but that. They barely covered the top of my slit, and from the back you could see at least half of the crack of my ass.

I was now wearing a 'come fuck me' Santa's Helper outfit. I made a quick run to the local stores to see if they had a Santa's Helper outfit for sale that would work better, but I struck out and then ran out of time.

I rang the bell at Susie's house ten minutes late, dressed in my provocative outfit, but covered in a long coat. Susie answered the door and ushered me in. I knew her father from when we were kids and I had sleepovers at her place, but she introduced me to her father's friends. They all seemed like nice men.

Susie then explained she had to run, and offered to take my coat to hang up in the closet. I kind of clung to the coat, but Susie insisted, and when I took it off the effect was dramatic. The jaws of the men dropped and their eyes got wide. Susie smiled a malevolent smile, and wished the men luck in their poker game. She rushed out the door.

Susie's father thanked me for filling in for her. He told me he loved my outfit. I'll bet he does, I thought. Then he asked me to get them all drinks. I asked their wishes, and as I turned to go to the kitchen Susie's father gave my ass a friendly little tap. I ignored it, pretending I had not noticed. This fooled nobody.

I brought out the drinks, and as I gave the first man his drink he put his hand on my bare thigh. I moved away to the next man to give him his drink, and his hand rubbed my ass. The third man asked for a good luck kiss, and I smiled as I shook my head no. The fourth man tried to slip his hand under my outfit to fondle my right boob, but I pulled away quickly, almost spilling his drink.

I asked to speak to Susie's dad. We walked to a quiet spot. "Susie told me there would be no touching and the like, Mr. Simonson," I said. "I would like that to stop."

"Susie told you that? I can't imagine why! Susie works for tips, and the more the men touch her, the bigger the tips they leave. Sometimes it goes beyond just touching. Susie makes between $1,000 and $3,000 a night, depending on what she allows. My friends enjoy her a lot, and she seems to like it, too. She assured me you would be even more wild. Last week she showed a video of you and a boy in her room, apparently from two years ago. You looked great then, but from what I can tell from our outfit tonight, you look even better now. My friends are impressed with you. They're pumped for tonight," he said, with a tone of innocence in his voice. "They put the tips inside your outfit, by the way."

"I think I should go, Mr. Simonson," I said. "Susie lied to me, apparently."

"Yes, she does that. She's quite a deceitful young woman, my daughter. Like father, like daughter, I guess. Well, we'll be sorry to see you go. Susie told me she has some pictures that would destroy you. It would be a shame if they got out," he said. The threat was obvious. I felt trapped.

"Why don't you stay for a while. If you get uncomfortable, and want to leave at the risk of Susie revealing those pictures, then of course you are free to do so at any time," Mr. Simonson said, with an air of finality in his voice.

I stayed. It was not too bad; I could handle the ass pats and the thigh strokes. The men insisted I drink too, and when a man asked for a whiskey he would ask me to have one with him. I could tell their plan was to get me drunk, but I was so freaked out that I drank the booze happily, wanting to make the torture of this evening more bearable.

I had been receiving tips, always placed in my panties. When one of the men would tip me $5 he would put it in my panties, pushing them down on me. After one round of drinks, the four of them tipped me and my panties were pushed so far down my entire ass was exposed. One of the $5 bills dropped out, and when I bent over to pick it up I flashed them a great view of my entire naked ass, I'm sure.

I kept taking out the money when I would retreat to the kitchen. I placed the money on the counter in the kitchen. Then I would pull my panties back up. So far I had $125. The next time out the men began to tip me with $20 bills. With those tips the fourth man to tip pushed off my panties down to my ankles. I was too drunk to bend over; if I had I was worried I would fall over. So I stepped out of my panties, and just relied on my skimpy skirt to preserve my modesty.

The next time out I had no panties. They had disappeared from the floor while I was fixing more drinks in the kitchen, so now the men tipped me by slipping the money through my décolletage, feeling up my boobs as they did so.

The men also now enjoyed rubbing my naked ass, and their hands were getting dangerously close to my cunt with the liberties they were taking. In spite of myself, I was getting wet by being on display to the five men.

The fourth man offered me $100 to unbutton and to remove the strap holding my top together in order to cover my nipples. I was kind of aroused at this point, having been without panties for a while and never admitting it but actually having enjoyed all of the men feeling me up.

I unbuttoned and removed the strap. The two sides of my top immediately fell apart to the extent where both of my boobs poked out, nipple and areolas and all. The men gave a rousing cheer and applauded. I bowed deeply as an actress might at a curtain call. This further liberated my boobs.

At this point none of my charms were covered, and when Susie's father called me over and slowly removed my outfit, I did not stop him. I was now naked in front of the five men. The man who had asked me to remove the strap called me over. He took out a $100 bill, rolled it into a small tube, and he placed it inside my soaking wet cunt. He smiled when he felt how warm, wet, and inviting it was.

I quickly retreated to the kitchen to hide and to add the $100 to my pile of money, which was now $450. I began to wonder how Susie could make between $1000 and $3000 a night? Did they tip her more because she was Mr. Simonson's daughter? Or did she provide 'other services?'

After a while, I summoned my courage and returned, stark naked, to take the men's drink orders. They were all by now just as drunk as I was. Of course I am not an idiot, I saw where this was going, but also I knew how to say no, and had been doing it a lot recently, albeit to boys my own age, not to men the age of my father.

Mr. Simonson gave me back my Santa's Helper hat, and I put it on, so I was now naked except for the hat, which somehow made me sexier, I suspect. As I stood next to him, the man across the table from him asked me to clear his drink glasses, and I bent over the table to reach them.

Somebody held me down bent over the table, and I felt a hard cock poking at my entrance. This was it, I thought. This is what they wanted all along. You knew this, too, I told myself. Now what are you going to do? I asked myself.

I said, "Excuse me, Sir, but that is not on the menu tonight," I said, and I jerked myself up to a standing position. I quickly turned around to retreat to the kitchen. The man who had tried to enter me followed me into the kitchen. "Please excuse me, my dear. We were treating you as if you were Susie, you see. I should have explained that had you agreed, the tip would be $1,000."

I could not resist. "How much does Susie get?" I asked.

"The very same, my dear," the man said.

"I'm worth more, don't you think? I should think a lot more. You get Susie all the time, I suppose, but this is your one and only chance with this sexpot. And I'm good, too, you know." I could not believe I was bargaining with this man on the price of my virtue. I'm a whore tonight, I thought. Well, so apparently is that bitch Susie. And what kind of father pimps out his daughter? My mind was reeling.

"That is a good point, my dear. Let me discuss it, please. I'll be back in a minute," he said.

I sat down in the kitchen with a glass of Perrier. It was lime flavored, my favorite. I stuck a finger in me and it was as I suspected: I was soaking wet. Just as incest turned me on, so too did the idea of whoring. But I had limits: I did not want a gangbang.

The man came back. "Here is our offer: $1,000 for one of us, $3,000 for two of us, $6,000 for three of us, and $10,000 if you do all five of us." My mind reeled. All I retained was the $10,000 figure. Holy shit. $1,000 for only one man, something unthinkable at the beginning of the evening, seemed so small compared to $10,000.

"Could you repeat that, please? I went into shock and did not process it," I said to him. Here I was, stark naked and being ogled by five old men around my father's age, and negotiating my price as a whore. Being in shock seemed appropriate.

The man repeated the offer. "Double it," I said.

"Double it?" the man asked, true surprise in his voice.

"Yes. My price is $2,000, $6,000, $12,000, and $20,000. Cash on the table," I said.

The man excused himself and came back later. "We'll take your offer of two for $6,000. That's all the cash we have tonight."

I had manipulated myself into a situation where I was going to fuck two old men I did not know for $6,000. For reasons I cannot explain, and still do not understand, just then the prospect of whoring myself for a large amount of money was exciting for me, instead of shocking and abhorrent. After having committed incest with my brother repeatedly, how bad after all was this?

When I re-entered the room I had tied a dish towel around my waist, to give the men something to remove. They were just ending their squabble to see which two men would get to do me. They did what these kinds of men did: they drew cards.

Mr. Simonson and Mr. McCabe were the winners. I idly wondered how many times Mr. Simonson had fucked Susie, his own daughter? Many, I decided. I knew her mother had passed away when she was 10. Cancer was the cause, I was told. I began to feel sorry for Susie instead of hating her.

Mr. Simonson went first. He bent me over the poker table and took me from behind. His cock was enormous, but unlike some other girls, that does not do it for me. To paraphrase the words of the singer Maria Muldaur, "It ain't the meat it's the motion" that makes this mama want to rock. And Mr. Simonson's motion was routine.

Still it was a pleasant fuck, and I enjoyed it, especially as I thought about the $6,000 and the fact that I was whoring to get it.

He shot his load on my back, and then man number two led me to the couch. I didn't worry about soiling the couch when I lay on it with cum on my back. I did not give a damn. I hoped Susie would have to clean it up.

There was no foreplay of course, and he just stuck it in and I had another enjoyable but banal fuck. I was still highly aroused, but not even close to an orgasm, alas. When he finished he squirted on my stomach, so I was still not that sloppy.

The third man approached me with his cock hard and ready. I said, "No freebies, friend," and I pulled my legs tightly together and sat up on the couch.

"Three of us want to do you, Alessandra. Will you take a check?" he said.

"Let's see. That would be a check for $14,000, right? You can handle that?" I said, being sure nobody would pay that sort of money to take turns three, four, and five with me, or anyone else for that matter.

"We can handle $7,000," he said. "Have mercy. We've never seen such a gorgeous woman here before."

"Shut up, Frank," Mr. Simonson said. You are insulting my daughter." That may be, I thought, but I was loving it.

"Deal," I said, "Let's move to a bedroom." I led them directly to Susie's bedroom, the scene of my first sexual disaster. The remaining three men ravished me. I tried to give them their money's worth, too, and I sucked them hard so that they could fuck me twice. One man fucked me in the ass. They wanted to try double penetration but I said no, that was not on the menu at any price. Then at my most snarky I said, "Save that one for Susie."

"She does do it well, you're right," Frank said, and I did not see that coming and was shocked.

So I ended up giving the men a gangbang after all. But I got $13,000 out of the deal. Unknown to me, Mr. Simonson had recorded not only everything in Susie's room, but he had recorded the entire evening, and the seduction of me and the bribing of me, and my evolution into being a whore. Now that cursed family had even more leverage over me for the future.

That family was evil. I took a bath in their house to clean up. Probably that too was recorded. As I left, with a swollen cunt, wearing my miniscule Santa's Helper outfit, and before I put on my coat, all five men gave me lingering kisses goodbye, slipping their hands into my panties and into my snatch, and also slipping them under my outfit to fondle my boobs and tweak my nipples. I finally escaped with almost $7,000 in cash, and a check for another $7,000.

If you believe Susie's father, and for me he has no credibility, she makes between $1,000 and $3,000 whoring herself out to these men, and I made $14,000. That would have to be my revenge, because Susie and her horrible father held all the other cards.

I planned to lay all this at my brother Andrew's feet. He would find a way to get me out of this mess. Her would fuck me first of course, but then he would figure a way out. He is a clever and resourceful man.

********Winter Four**********

I was really glad to leave my home town and get back to college. After that experience I had perspective. Now when a college boy asked me out and pressured me to end the evening with a roll in the hay, so to speak, I rolled around happily. I'd fuck his brains out and then suck him hard and repeat. I would try hard to be the best fuck he had ever had, or ever would have.

In return, I became amazingly popular. I never went a weekend without several dating offers. Boys began to call me two weeks ahead to jump the queue. Reserving an evening with me was like trying to get tickets to Hamilton on Broadway in New York, but of course it was much cheaper. I let the boys buy me meals, or treat me to the movies, or both, but otherwise I provided my services lovingly and for free.

I saved half of my $14,000 in a bank account, and the other half went for new clothes and shoes. I encouraged boys to give me jewelry and perfume, by showing them what other boys had given me who wanted a second or third date. So I did not need to spend money on those things.

I got more wild, too. I needed new underwear, so I took a boy named Jeremy on the train for the long hour trip to New York City. We went to Macy's, Saks Fifth Avenue, and Bergdorf's in search of new lingerie for me.

He came into the dressing room with me when I tried on the lingerie. Bergdorf's is the stuffiest of the three stores, so I let him fuck me in their dressing room because it seemed to me to be the most perverse place to do it. This was after having teased him mercilessly in the dressing rooms of the other two stores.

Nice lingerie is expensive. It feels wonderful against the skin, and men find it sexy, especially if it is lacy and you can see some forbidden details at least partially though the bra and panties sets. That of course is the kind of lingerie I bought.

We then spent the night in a nice hotel. Our room had a tiny balcony, and I took him out on it and fucked him on the balcony. In theory people could see us, and some people in neighboring tall buildings probably did in fact see us do it. That thought almost made poor Jeremy lose his erection, but it turned me on and so I sucked his cock back to life. That allowed him to resume ou balcony fuck.

I moaned and gasped and said encouraging words such as, "Oh Yes, oh yes, oh my God, Jeremy, just like that!" I said them loud, not just for the benefit of Jeremy, but also for the benefit of any voyeurs who might be watching, or hear me and then begin to watch. Like a good actress, I knew how to drum up an audience.