A Story of Four Winters

I developed a reputation as a 'good time girl.' The word out on me was that if a boy spent enough money on me, he was assured of a good time, usually even a very good time. Consequently I was taken to the best restaurants, to the theater, and I was showered with small gifts. I had, shall we say, a rather rich and varied sexual life.

My only constraint was that all men had to wear condoms. To make sure, I bought my own condoms, $100 worth at a time. That way if a man claimed to have forgotten his condoms, and I still wanted to do it with him, I could give him one of mine. Also the ones I bought were lubricated and they were both expensive and the best for my taste.

One amusing story was when a boy at my school took me all the way to Boston for the Harvard-Yale game. We were students at Yale, and our team had a good chance to beat our perennial rival Harvard this year.

I wore a nice blouse, a wool skirt, and warm stockings, along with a warm car coat with a fur collar, and a cute fur hat. I looked pretty but not especially sexy. But it was a football game, and it was cold. Snow was forecast.

We drank a lot and my date was pretty drunk by the time the game started. He had been drinking rum and coke throughout the first half. By half time he was telling everyone around him how he was going to have sex with me after the game, giving explicit details of how he would do me and what I liked in bed. He even described my body to the boys around us.

It was as if I were not even there. I was blushing and trying to hide as men leered at me, imagining they were going to do to me what my date was describing. A small irony was that we had only had sex one time before this date.

I excused myself to get some more Coca Cola, and then disappeared. That's easy to do in a huge football stadium. I went over the Harvard section, and asked a nice looking guy if the seat next to him were taken. He saw my Yale hat and looked at me.

"Yes, I'm from Yale. I hope that's okay?" I said, slurring my words just a bit.

"Are you drunk?" he asked.

"You betcha!" I said.

"Do you put out?" he asked, and I could not believe how crass and rude he was.

"I'm not that drunk, asshole. What kind of question is that? Anyway I'll answer: If I end up liking you, and if you put me up for the night, then yes, I'll put out. But ONLY -- emphasis on the only -- if I end up liking you," I replied.

Then I gave him a sloppy, drunk kiss to seal the deal. I opened my car coat, and unbuttoned my blouse and opened it, showing him my lacy bra. Then I closed my car coat, giggling. I gave him another kiss. "Deal?" I asked.

His name was Henry Richard III. I knew guys with names like that at Yale. Usually I did not like them. He called himself Hank.

"Ma casa es su casa," he said, and I smiled and kissed him a third time. He tried to molest me a little in the second half, getting his hands under my car coat. I took off my bra to let have some fun, and he exploited it for all it was worth.

I texted my date telling him the date was over. He behaved like such an ass I did not want to see him anymore. After I sent the text, I turned off my phone.

Then he proposed a deal: "If Harvard wins, you'll do whatever I ask. If Yale wins, you can stay with me and I won't try to molest you, unless you want to be molested. Want to play?"

"You're on, McDuff!" I said. "I'm sorry there will be no sex for you tonight: Yale is sure to win." Yale was up by 14 points just then.

Harvard then scored two touchdowns and a field goal, and won the game in the final seconds. I was not too worried; the boy seemed reasonable. He took me back to his room, we took off our clothes, and he went down on me. I liked him already.

After his talented tongue made me cum, he mounted me and lovingly fucked me in missionary position, filling the condom I gave him up to the max it could handle. Then he took me to a surprisingly nice Thai restaurant for dinner.

At the end of the dinner he invoked the clause that I had to do what he told me to do. "Fair is fair," I said. "I lost the bet. And it turns out I like you, too -- an added benefit."

He told me to go to the ladies' room and to remove all of my clothes. Put them in my duffle bag, and come out naked underneath my car coat. My car coat was rather short and would barely extend down far enough to cover my ass. I was not even sure it would. I told him that. "Nevertheless, that's what I want," he said.

This was pretty weird. The idea of walking back to his room naked under the car coat kind of turned me on so I made a show of reluctantly complying, but I was kind of into it. In fact anyone could see the bottom of my two ass cheeks as we walked home. It was hard not to conclude I was bottomless under the car coat.

To prove I was naked under the car coat he had me quickly flash him, opening the coat briefly once we were outside the restaurant. I was careless and flashed perhaps a half dozen people as well as Hank. Hank loved it.

As we walked home from time to time he slipped his hand underneath the coat to fondle my bare ass. I knew he was raising the coat a bit when he did that, showing off my nudity to his friends walking with us. I just let it go. Let him have his cheap fun.

Of course we had another romp once we were back in his room. His technique was not great, but he had a lot of enthusiasm, and I had the impression I was his first girl in some time. The man was horny.

His shower was down the hall. It was a shared showed. I wanted to shower after all of the sex we had just had. He wanted me to walk to the shower naked, in order to take a shower. "Is there a sign or something to let people know a woman is in the shower?" I asked.

"Yes," he said. "But don't use it."

I argued a bit and begged for a little mercy, but I lost. I went to the shower, walking stark naked down the hall but carrying my soap and my towel as instructed. The shower however was in use, so I quickly walked back.

"I want you to join whoever is in the shower, Alessandra," Hank said.

"That's ridiculous, Hank. It will be taken as an invitation to molest me. Don't you think you're taking this bet a little too far? I did after all parade naked through your hallway just now, both to the shower and back." I did not add that nobody saw me doing it, thank goodness.

"This will be the last thing I ask. Then the bet is over, and I'll take you out for a drink, to go dancing, to a late movie, for ice cream, whatever you want, okay?" he said. He was trying to be nice I guess.

"But what if it leads to sex?" I said. "Do you really want me to have sex with another man on your floor?"

"Do you want to?" Hank asked.

"No," I said. "You are more than enough for me. Plus I like you, which is the best part. I hope you like me, too?"

"Alessandra, you appeared magically out of nowhere. You are the stuff dreams are made of and I am hopelessly infatuated with you. Infatuation in my case is usually the precursor to love. So yes, I like you. But it would really turn me on to watch you shower with another man. I'll join you."

We walked down the hallway again. I was nude, totally exposed, and Josh had on exercise shorts. A man named George was in the shower, and I asked him if I might join him. George looked at my naked body and was so surprised be could not speak. He was struck dumb.

George feebly managed to nod, and then he gestured for me to enter the shower. I left the curtain open so Hank could watch. I quickly washed myself and then shampooed my hair. George studiously did not touch me, not knowing what to make of the situation.

I leaned over to him, my hair full of shampoo and my eyes closed, and I whispered to him, "You can touch me if you want to. Wherever you want. Use soap and wash my back, okay?"

I turned and presented my back to him, and he eagerly soaped up my back. I was enjoying the warm water after having been chilled by my walk home after dinner, when I was naked underneath my car coat.

George got bolder and reached around me to wash my boobs. I think my boobs were never cleaner than they were by the time he got through soaping them up and re-soaping them up several times. It felt nice.

I turned to face him, still with shampoo in my hair, and I filled my hand with shampoo and massaged his erect cock. Apparently men really, really like a hand job when shampoo is involved. He got very turned on, and then stuck a shampoo filled finger into my cunt, then two, then three, and pumped away.

My knees got weak and I gave up my hand job and sank to the floor. George put me on all fours and then quickly entered me from behind. I broke my condoms omni tempore rule, to say it in Latin. His very soapy cock entered my equally soapy cunt and he gave me one hell of a shower fuck. He shot his load deep inside me in a matter of minutes.

George was embarrassed. He felt he had taken advantage of me, and he quickly left the shower, grabbed his towel and wrapped it around his rapidly shrinking and still soapy cock, and rushed back to his room.

Hank entered the shower and said, "I really need to go to Yale more often."

"I'm not typical of Yale women," I said.

"I don't want Yale women, Alessandra. I want you," Hank said. Our romance continued for three months. He always wanted me to do other men with him watching, and I always refused except for that one time in his shower. Finally I had had it, and I broke it off.

I recounted this anecdote to illustrate the kind of life I was leading in college. It seemed always to be filled with drama. Lots of drama. Too much drama, actually.

Finally, I need to mention that of course I did not forget my brother Andrew, but for my sexual favors I extorted favors from him, too, but of a different sort. I made Andrew promise to solve my problems with Susie and her father.

The next Thanksgiving break Andrew and one of his friends, Keh-Shin from college, went home. They stayed with my parents, and went on a double date with Susie and Billie Jane. After they had fucked their brains out at Susie's house (her father was away, at his girlfriend's home), Andrew drugged their drinks, and the two girls passed out.

Andrew's friend was a computer science major and he was able to get into their not so well protected system and to remove all digital files that were pictures, or might be pictures. Videos too, of course. He did the same for Susie's phone, having seen her punch in the four-digit password one time that evening.

He also deleted the pictures from their Dropbox backup, and from all of the USB keys, and anywhere else they might be stored and backed up. He then inserted a virus into all of their computers.

Meanwhile Andrew searched the house for prints of me in compromising positions, such as underneath Andrews's cock, or my gangbang. He finally found a secret compartment where they all were, but to be thorough he searched absolutely everywhere.

This took time, and the two girls were in danger of waking up before they finished at 5am. They were both naked, so Andrew and Keh-Shin tied them each up naked and spread eagle. They also gagged them.

When the two girls work up, the boys took turns doing each of them, bound and gagged like that. When they removed the gags, Susie smiled at them and was rewarded with a kiss. Billie Jane was furious, but a kiss, untying her, and another fuck, this one in the ass, calmed her down. They never knew they were drugged, they thought all was due to their massive alcohol consumption.

Indeed, the two girls assumed they had agreed to bondage and then passed out. They thanked the men for their consideration to wait until they awoke to have sex with them. This showed an assumption of a certain lack of self-respect. What kind of man would fuck an unconscious girl?

Andrew took several pictures of Susie bound spread eagle. He took a video of Keh-Shin fucking her like that, and then he took a picture of her, still bound and spread eagle, but now with Keh-Shin's cum oozing out of her cunt.

I loved the pictures. I had an 8 x 10 glossy made of the one where Susie was bound and naked, spread eagle, and waiting to be fucked. I bought a nice frame, and I displayed it prominently on my desk. Every man who came to my room noticed it. I told each of the men I was going to invite Susie to visit me.

When Susie finally did come to visit me, I organized a gangbang for her that was truly over the top. The poor girl did not know what hit her. She could not protest, because I had her father's own videos of the two of them fucking, and of her being gangbanged by the poker men in her living room, including a particularly wild fuck with her father, and then being showered with thirty $100 bills after the gangbang.

I showed her these, pointing out they were backed up off site, and then she had no choice but to comply. I did have some mercy, however. Too many men wanted to do her, having seen the glossy 8 x 10 photo on my desk, and a few others Andrew had printed out for me.

So I arranged for a few of my girlfriends, and of course myself, to help out a bit. We each fucked one of the men. I chose for us girls the ones who fucked the best (all of the men had previous carnal knowledge of yours truly, the flaming slut). The other seven I gave to the naked, bound, and gagged but willing victim, Susie.

My revenge was sweet. It became worse however, or maybe better depending on how you look at it, when Susie thanked me. First, she had actually enjoyed the bondage gangbang! I had foreseen that.

Second, she explained that because of Andrew and Keh-Shin's invasion of her father's home the night they ravished Billie Jane and her, she found the courage to say no to her father. That chapter of her life was over. She was deliriously happy about that. I realized that sex with her father probably went back a long, long time, the poor girl.

I was happy now, too, and freed from all the blackmail. My deflowering video of my time with Adam, and the fuck with Mark the same night still circulated. But it was hopeless to try to change that. There were just too many copies in circulation.

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

I was older and wiser now, and I had enough sexual experience to last a lifetime. Graduation from college was looming, and the issue of what do after college was occupying much of my time. I began to interview for jobs.

I quickly discovered I could get almost any job I wanted if the HR person interviewing me was a man. Somehow I conveyed my availability, it had become almost automatic. The men would follow up by calling me the next day and, for example, asking to discuss the possibilities with their firm at my hotel bar.

The discussions would sometimes continue in my room, with both of us naked, and with me lying on the bed, my legs apart, and the man on top of me. I would get the offer and usually turn it down, since I wanted better pay and better conditions. But both the men and I enjoyed this process of recruitment.

I finally landed a high paying job on Wall Street, having fucked the head of recruitment three different times, since I kept being called back for repeat 'interviews.' By the time I got the job the recruiter had solved every mystery my body might ever have presented to him. He could probably recite my moans with the right order and with the right pitch, in his sleep.

I then discovered I had to service my boss at work, too. We were working 80 hour weeks, and when everyone else had gone home, and the nighttime janitor had finished his rounds, he would take me bent over his desk. Every time it was exactly the same way.

One time I decided to rock his world and I removed my clothes and lay naked on my desk, even before the janitor had made his rounds. I spread my legs and edged close to the edge of the desk. It was near Christmas, and I said, "Hey boss. Come get your Christmas present!"

He did, and we fucked with great enthusiasm. At one point I noticed the janitor was watching us, and I winked. Then I mouthed the words, "you're next." The janitor was named Clarence, and he had a big black cock. It was my first.

My boss got to watch me being ravished by this gorgeous black man, and he got hard just watching me do it with him. There is something about interracial sex that many people find sexy. I don't. I just have always liked the janitor.

We have enjoyed some philosophical discussions in the past, discussing literature for example, in ways that my colleagues on Wall Street are not incapable of doing. Sex is better when you like and respect your partner.

Everyone was happy. Especially me. Soon after Christmas I met the love of my life: Joseph. My brother Andrew gave me away at our marriage. I had fucked, at one time or another, most of the male guests at our wedding. This included my boss, Clarence the janitor, the recruiter, my brother of course, and Adam and Mark, my very first two lovers who sent me down the slippery slope to the land of the flaming sluts.

My maid of honor was of course Billie Jane, who pleasured Andrew during the after-party, and my head bridesmaid was Susie. The rest of the guests were college friends, work friends, church friends, and some of my neighbors in New York.

Yes, I had fucked my neighbors, especially the male ones. Recently I have branched out and I have also had delightful, even wonderful, sex with some of my female neighbors.

Everyone there enjoyed my wedding dress, which was white and largely transparent. Under the dress I wore bright red lacy bikini underwear, bought for me by Jeremy, the man I fucked in the dressing room at Bergdorf's.

My poor groom Joseph was innocent of all my prior behavior, and he just looked at me with love mixed with lust. He did know I was a bit of an exhibitionist, and he was okay with that. He also knew I was not a virgin: far from it. He was okay with that, too.

I decided once married I would not betray my true love Joseph's trust. But my boss insisted, and I wanted to keep my job. He also insisted I do Clarence from time to time. Those were my only indiscretions. Well, except for my brother Andrew of course, and I could not deny the neighbors. But that was all.

Except of course there was this one time when Adam was in town and he looked me up. How can you not have a soft spot for the man to whom you gave your virginity? So we did it, too, one dark winter night (near Christmas, actually) in an isolated corner of Central Park.

There were a couple of other occasional exceptions, but for the most part I was loyal to Joseph, especially when you consider who and what I am. There was one period when I was completely loyal to Joseph, no exceptions, and that was when we decided to have our first baby.

I wanted no drama about who the father was! Once I gave birth however, my boss wanted to make up for lost time, and so did my neighbors, and so did my brother Andrew. Well, you get the picture. My life was complicated, but quite enjoyable.

In addition to Joseph being the most wonderful man imaginable, as well as being wonderfully non suspicious and naïve, our baby girl Billie Jo is a gift from the gods, straight to us. She is my hope for the future of the world, all six pounds of her.

Billie Jo was a newborn. But her grandmother was my mother, and I was her mother. I could not help wondering if she would grow up to be a slut too, and keep the family tradition alive? I could not decide if I wanted her to become a slut, or I did not want it. I let it go. After all, it was not up to me, was it?

**********

Note to the reader: This is my second entry to the Winter Holiday Contest for 2016. My first is Jane & Julie Go Home for Christmas. I hope you like them, and please vote!