Penance 15

I'm Amy. I thought that I had made a really bad mistake; only later did I find out the truth. I ostensibly got caught cheating on my wealthy husband and got booted out of the marriage with little to my name in view of a prenup. Only humiliation followed until...

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I guess that I had a relatively typical middle class childhood, although I wasn't much into girly things. I was a pretty good athlete and must have had a decent body given all of the guys that hit on me. However, I was always a good girl and gave my virginity to my first love, and first husband, John. John and I got married too young, just out of High School. I continued being a good girl and never cheated. One thing about marrying too young – especially against family advice – is that we didn't realize the work necessary to both hold down a low skill job and keep a marriage interesting. We lasted only three years and divorced by mutual consent, with virtually no assets to distribute.

I wanted to go back to school to get some sort of associates' degree but I really couldn't stand living with my parents as a failure, and after a two month transition period where I was forced to live with them I was looking for a way out. I was working a low level retail sales job after my divorce while living at home when I met Charlene Peters. She was sophisticated and level-headed and I liked her right away. After we knew each other about two months her roommate moved and Charlene offered me the chance to take her place; I quickly accepted.

Charlene sold beauty products, primarily to stores but also to some individuals. She experimented with some products on me and told me that when I had decent makeup on that I looked "hot." She may have been right because when I went to work after Charlene had done my makeup I got lots of male attention, so much so that my crusty female supervisor told me not to ever again wear anything more than simple lipstick to work.

Charlene not only experimented on me but she taught me lots about makeup and other beauty products, and I was like a sponge absorbing it. In addition to learning everything that Charlene could teach me I actually enrolled in a cosmetology course dealing with makeup artistry at the local community college. I didn't really have the time or money to get a cosmetology associates degree, but the one course that I took really helped. Charlene told me that I should apply for a job in the cosmetics section of one of her customers – a job that would pay me twice what I had been making and also have me dealing with a better healed clientele. After a thorough interview where I was asked all sorts of detailed questions about cosmetics I was hired on the spot and started working in the cosmetics section of a high-end store the next day, which store I will refer to as Nordstrom, even though it wasn't.

My love life was decent just before and after I started working at Nordstrom. I got hit on even more during that time than I did during High School and had my share of good sexual experiences, though I didn't find someone that I wanted a long standing relationship with. Then I was swept off my feet by Chauncey Crichton.

Why Chauncey Crichton was in Nordstrom with his daughter-in-law Megan I have no idea; but he was. Chauncey was 43 at that time while I was 25. He obviously came from money in view of the way that he dressed and talked. While he didn't have the body of an athlete he was handsome, and at first I couldn't believe that someone like him would take an interest in me. However, the entire time that I was helping Megan, putting different high-end cosmetics on her face so she could get an idea of how she would look, he was chatting me up. After he paid for a happy Megan's cosmetics he walked away with her but came back a minute later and asked me to dinner that Friday night. I accepted.

I admit to being star struck by Chauncey's life style. Had I been more sophisticated growing up I probably would have realized how shallow he was. However, with stars in my eyes I accepted his proposal of marriage after six months of dating even though he wasn't all that great in bed, and seemed much more interested in his pleasure than mine. Of course I had to sign a prenup, but I guess my lack of sophistication and my enchantment with Chauncey's life style led me to not read it as carefully as I should have.

Having lived simply much of my life I quickly adapted to living a life of privilege. Since I was pretty good looking and had a nice C+ cup pair of tits Chauncey seemed to take great delight in showing me off to his male friends, sometimes much to my embarrassment. I did have trouble, however, making friends with the females in the social circles Chauncey travelled in. Mostly my life was good – certainly the material things – although I never warmed up to Chauncey's haughty son Mitchell – who was my age. I did have a decent relationship, however, with Mitchell's wife Megan, who I had met at the same time that I met Chauncey at the Nordstrom cosmetics counter.

My life with Chauncey effectively ended when after about 18 months of trying I found that I couldn't have children because of what my OB/GYN said were "structural problems in your reproductive system." I never understood exactly what that meant, but accepted her diagnosis. I didn't find out until then how interested Chauncey supposedly was in having at least two more kids aside from his adult son Mitchell, and I never did find out why other children were so important to him.

I was distressed with Chauncey becoming cool toward me when we arranged to go on a vacation to the Bahamas. I thought that it would be a way for us to reconnect; I didn't find out until much later that it was a way for Chauncey to dump me without any economic consequences.

While Chauncey was busy playing golf he set me up with a tour group, led by Julian, a guy about my age originally from Boston. Julian was a hunk and to be honest I was quite flattered that he paid much more attention to me than he did to the other fifteen or so tourists in our group, even though five or six of them were comely college girls. After the tour he extended an invitation to lunch about a half hour after the tour ended; he passed out slips of paper supposedly with the address; mine said the hotel that I was staying in. I called Chauncey on his cell phone to find out when he would be done with golf and he told me that he was going to play another 18 holes so to go ahead with lunch.

I was surprised when I got to lunch that I was the only one there. Julian acted surprised too, but merely asked the hostess in the hotel restaurant to give us a table for two instead of the table for ten he had ostensibly reserved.

Julian was very solicitous of my happiness and when our waitress was too slow for his tastes got us refills of our rum drinks by going up to the bar himself. Julian was being so nice that it took me a while to realize that I was getting a little dizzy. Julian asked me if something was wrong, quickly paid the bill, and then offered to help me up to my room. As Julian was undressing me in my room I tried to stop him, but not only was my body not reacting properly, but my words were slurred. I realized then that he had drugged me, but it was too late. The only good thing that happened in the next hour was that for the first time in a long time I was properly fucked. Julian sure knew how to use his talented tongue and girthy cock and even though I did little to actually participate because my body was sluggish I do remember having at least half a dozen orgasms and receiving at least two discharges of cum into my vagina.

I either passed out or went to sleep only to wake up to a seemingly angry Chauncey shaking me and calling me a slut – among other names.

I regained cognizance surprisingly quickly, and realized that I was lying naked on top of our hotel room bed with cum oozing out of my pussy. One of Chauncey's friends, with a big shit-eating grin on his face, was standing behind Chauncey as he yelled at me. I covered up and when Chauncey's tirade had subsided I told him that I had been drugged and fucked against my will. He scoffed at that but getting some real backbone for one of the few times in our marriage I demanded that he take me to a hospital for a blood test. After making a phone call Chauncey relented, I got dressed – with his asshole friend refusing to leave while I did so – and the three of us – I didn't know why we needed the friend – took a cab to a local hospital.

I was surprised at how solicitous the hospital administrator and doctor who drew my blood were toward Chauncey; and how they treated me like a piece of meat. We sat in the administrator's office, saying little, until an orderly came in with the test results about an hour after my blood was drawn. The administrator looked over the test and said "No drugs, although there is some alcohol."

I snapped the test paper from his hand, looking to see if there was some obvious mistake. The test indicated that the blood tested was "A negative," which is my blood type, and "Amy Crichton" was on the top of the sheet, but I couldn't believe the negative results for a dozen different drugs, including GHB. I did notice Chauncey and the administrator exchange furtive knowing smiles, which I didn't realize the significance of until much later.

Chauncey informed me on the cab ride back to the hotel that he was divorcing me and to take an early flight home and be out of the house by the time that he got back. I waited until I got back to our hotel room before crying – I didn't want Chauncey or his asshole friend to see me. I was a wreck on the flight back.

To make a long story short, Chauncey did divorce me enforcing the morality clause in the prenup (which I unfortunately found out only then was one-way; just for me, not for him). Within three months we were divorced and I had little to my name after two and one-half years of marriage.

I probably could have made it economically working full-time at the Nordstrom cosmetics counter if I still had the same tastes that I did before I married Chauncey, but I no longer had those tastes. Within six months I was out of money and had received an eviction notice at my apartment. It was then that I ran into Beatrice, one of the females who was in the group of "friends" in Chauncey's social circle. Beatrice was a good-looking woman married to a toad of an old man, obviously for his money. She and I weren't particularly friendly while I was married to Chauncey but she hadn't been haughty toward me either, which put her in the top half of the people that I met while married to Chauncey.

Seeing her now, after my divorce, I was surprised that Beatrice was remarkably friendly. She treated me to lunch at a restaurant that I could no longer afford and after I had two drinks in me she asked me about my circumstances.

"I'm working part time at the Nordstrom cosmetics counter hoping to get my full time job back, but I'm really having trouble making ends meet because my tastes have changed after being married to Chauncey," I lamented.

"I'd like to let you in on a little secret," Beatrice said in a giggling whisper. "Promise not to tell anyone and I'll relate it to you."

I was intrigued, so as I sipped my third drink I replied "I promise."

"Some of us society women who have husbands that can't possibly satisfy us, as well as some of our single friends, have a little side business. It is fun and provides us with a good deal of spending money that we don't have to account to our husbands for. Want to hear more?" Beatrice responded.

"Of course," was my retort as I chugged the last of my third drink.

"We have a little escort service. Those of us who are married deal mostly with out-of-town businessmen staying at upscale hotels. However, the single members of our group do local events as well, and make lots of money," she smiled.

Of course even after three drinks I knew what she was talking about, but asked anyway: "By escort service do you mean call girls?"

Beatrice smiled brightly. "Some of us only escort; others fuck and suck." After a long delay while we stared at each other, her with a shit-eating grin on her face she asked "Interested?"

"Maybe," I replied.

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After further discussions over the next few days – with my impending eviction approaching rapidly – with both Beatrice and Susan – a woman I had never met but who was in charge of the business end of the "escort service" – I came to the conclusion that this was a lifeline that I had to accept, especially since at the same time Nordstrom was cutting my hours, not increasing them. Susan loaned me $2500 to stave off eviction and starvation, and booked me for that weekend "only" as an escort.

The organization that Susan ran was called "Events, Inc." and had two classes of contractors, "sweet" and "bold." The "bold" ones were sure things for sex, and payment for them was up front. The "sweet" ones the client had no expectation of sex with but the "sweet" women were consenting adults and what they did at the end of the evening was their business – as long as they gave "Event, Inc." a cut the next day. I was in the "sweet" group.

The next six weeks I worked as an escort, being arm candy for mostly older gentlemen who needed a "date" for some event or the other. I rarely ran into people from Chauncey's circle but when I did I was surprised that they were cordial, and sometimes even friendly. I had already paid Susan back and was making more money than when I worked full time at Nordstrom without working on my back, but still not enough to support the lifestyle that I wanted. Then I met Richard Hawkins.

Richard was not a typical date. He was young (a year younger than I was), big, bold, and handsome, and obviously had been born into money although he seemed to be making his own too as a Princeton graduate. He was from out of town, attending a big charity ball in our large city. He treated me extremely well at the ball, and was an accomplished dancer, and declined on my behalf when others asked me to dance – for which I gave him a big smile.

When the event was almost over we left; as we rode in a limo Richard kissed me and said "I don't want the night to end. I know that you're not on the 'bold' side of Event, Inc., but I really need to fuck you. If you stay the night I'd like for you to get yourself something nice." That was his way of paying for sex without really paying for it. He took ten $100 bills out of his wallet and pushed them into my hand.

I didn't really have a decision to make. I probably would have paid to fuck Richard, and if it was a real first date likely would have given-it-up just for the asking. I shoved the $1,000 in cash into my clutch and planted a scorching hot kiss on his lips.

Richard got his money's worth that night in his hotel room; I was a bad girl and didn't make him use condoms. I also got the most genuine orgasms in a nine hour period that I ever got in my life too. There was nothing I wouldn't do for that stud especially after he insisted on giving me two orgasms by sucking on my clit and fingering my pussy before I saw to his needs. By the next morning I was so wasted, and still so anxious to please, that even though his cock was too girthy to comfortably fit in my asshole I gave it to him anyway. He was diligent in lubricating me and his cock before penetration and was slow in burying his hog. I can't say that it was one-tenth as enjoyable as when he fucked or sucked my pussy, or fucked my C+ tits, but it didn't really hurt much and it made him happy so I enjoyed it too.

When I staggered out of his hotel room at 9:15 the next morning he pressed another $200 into my hand "for cab fare" and asked if he could call on me the next time he was in town. "I'd be really upset if you didn't" I snickered as I gave him one last kiss – not a real scorcher since my lips were sore from sucking his cock and testicles and from feverishly kissing him.

After that I moved to the "bold" side of the ledger at Event, Inc., although I was more picky than most of the other women. Since I was the new girl on the "bold" side and since I was picky I was just barely at the earnings level that I needed to support my desired lifestyle. Then a great opportunity came up, if I really was "bold" enough to accept it.

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Susan met with me about an upcoming bachelor party. They wanted a stripper to pop out of a fake cake – so cliché – with the expectation that the groom-to-be would get properly serviced. Susan showed me a photo of the groom; he looked to be just 21 years old – which Susan confirmed – good-looking and even if not slim far from fat. "This pays $2000 for two hours," she said, "although I need to warn you that sometimes the attendees also want to lay some pipe. It is totally up to you if you do so, but you'll get $200 for every blowjob and $400 for every fuck, with 15% of each rebated to Event, Inc. I'll have one of my guys there acting as a waiter to be sure that you're compensated and that things don't get out of hand. Plus, they specifically asked for you after seeing your photo in our composite. Are you up for it?"

I was – up for it.

That Saturday night at a remote location – which I was driven to by Susan's "guy," Walter, who is 6 feet 4 inches tall, weighs 270 pounds, and carried a .357 magnum hidden by his waiter's uniform – I made sure that I was properly dressed and made up and then got into the stupid fake cake. Walter wheeled me into the main room which filled with cheers and whistles as I was rolled in. Once the music started I popped out of the cake and started going into my routine; I had been taking "strip aerobics" classes ever since I started at Event, Inc., and though this was my first actual performance before this type of audience, I was confident.

The room setup was a little intimidating, though. I was on a stage with lights in my eyes, but with the room dark so that I could see little meaning that I didn't have any idea about how many guys were there. The only person I could see clearly was the groom-to-be, sitting on a chair right in front of the stage with a big shit-eating grin on his face; his name was Ben.

I must have done a good job – or these guys had never seen big natural tits and a shaved crotch before – because during my entire thirty minute performance I got cheers, taunts, and applause. The noise level ramped up several decibels, however, when once I was naked I leapt off the stage toward Ben and laid a lick-lock on him. He had the biggest grin I had ever seen when I undid his belt, slowly pulled off his pants and then his boxers, and lowered my wet pussy toward his throbbing cock.

Ben's cock was average size with a perfect aspect ratio and stuck out from a pair of big testicles. I teasingly put the condom on his cock and then licked my lips. He was buried after a minute or so of lowering and twisting on my part, and once he was buried in my pussy he grabbed hold of my tits and started bouncing up as I was moving up and down. The poor bastard came much too fast, but I did my job and pretended to orgasm too.

As I moved off the groom-to-be he had an enormous shit-eating grin on his face and kept groaning "holy shit, holy shit, holy shit!"

I was now hot – and unsatisfied in view of his quick ejaculation and also because I needed a real good fuck to get off with a condom – and hoped to have at least one other taker for my pussy, so I provocatively danced around some more, still naked with a slight sheen of sweat on my tits and thighs. I needn't have worried.

Another young guy came up to me, handed Walter some cash, and as he hugged and fondled me asked me to get on my hands and knees on a foam pad on the stage that had a few towels next to it, which I did after rolling a condom onto his cock. This young stud did me doggy, and though I orgasmed it wasn't the most intense one ever probably just because of the condom, but I played it up, much to his joy. He had no sooner extracted his cock when I felt my pussy being wiped off with one of the towels and another condom-sheathed dick slithered into my pussy.