Her Slow Descent into Degradation
written by:
Little tommy D.

Her Slow Descent into Degradation

I had written a short story that was published on an e-book Web Site. I received a number of favorable reviews that led to the story being rated as a four and one-half Star read. Needless to say I was more than pleased with the comments and the ratings. After the story had been on the online site about a month, I received an e-mail at my personal e-mail address with just the title of my story as the subject. I normally hesitate to open strange e-mails, but that one indicated that someone was inquiring about my short story, so with a little trepidation I clicked it open and learned that it was from someone named Lara who had read my story and had taken the time to go into my Author profile and get my home e-mail address. I don't know if that was the primary purpose, but it was the end result. Lara praised my writing style, my choice of words, and the thrilling ending of the story. It really was an effusive appraisal.

Since she had gone to the trouble to write, I took the time to write her back and thank her for all the kind words and for her rating of my story. I was not really surprised when she wrote back so I didn't hesitate to open her message the second time when I saw her e-mail address once again, but was somewhat shocked when she asked if I wanted to chat. I thought about it for a day or so, wrote her back and said okay, we can chat. I really wasn't familiar with Chat lines so she guided me to AOL and had me set up an account on their Chat program. Once it was operational, she had me send her an e-mail detailing my Chat name. In about an hour I noticed on the Chat icon that I had a message. I clicked the icon and was taken to a greeting from her that said, 'Hi, I'm online and ready to chat." Being new at the game, that's when I realized that we were on a 'real time' chat basis. I quickly typed in that I was there and ready for her to say something.

It was purely innocent chit-chat. I discovered that she was a mere twenty-one, some sixty years my junior, had been married for one year, grew up in an authoritarian religious-cult household, had attended 'Girl-only' schools, including the two years of college she had completed. Her husband of one-year was the only man she had ever dated or that had ever touched her. She told me she had a part-time job at an office for fifteen hours per week. Over the ensuing weeks, I also learned that she wanted to be able to shed the prohibitions she still lived because her husband was a dedicated member of the religious cult she grew up under. She yearned to wear high heels; she told me she cried herself to sleep because she wasn't allowed to wear mini-skirts or short-sleeve blouses. I finally was told where she lived---some fifteen hundred miles to the east of my hometown.

In later chats, she confessed that she was miserable in her marriage and that she wanted more from life than what she was allowed to pursue. She broke down and sent me a full length picture of herself. I was pleasantly surprised to see that she was a tall, slim, pretty-faced woman, but nothing else other than her hands showed. I understood her dismay when I saw that her skirt touched the toe-top of her plain black flat shoes. Her blouse came to the end of her wrist and her hair was covered in a plain black hood-like scarf. I then knew exactly why she must have been unhappy. I knew she couldn't be Amish because she had a home computer which meant electricity and she drove a mini-van. I didn't push her on which cult she was a member of because she had purposefully kept from saying anything about it. I only replied in the chat that she was a beautiful woman with a lot to be proud about.

She answered back that she had nothing to be proud of but a lot to abhor in her life. She thanked me for my praise of her beauty and said, "I think I would look great in a mini-skirt and high heels. You haven't seen them but in my opinion my legs are extremely attractive, my bust is to be admired and my butt is valued by my husband, but he only feels it with his hand, never kisses it or ever kisses much of anything else." I thought, 'Whoa, she's really beginning to open up with me."

I got my answer to that in her next chat line when I saw that it was a plea for me to be her guiding hand. She said that my age, my experiences, my business background indicated to her that she may be able to use me as her sounding board because she had no one else in the world to talk with or to bare her soul to in any way. I said that she was welcome to ask me anything about everything that was on her mind. She then asked if it was okay if she sent me more pictures. I said yes, please do. The next day she told me that her cousin had lent her a camera and that after her husband left for work, she would send me a few 'selfies.'

The next day, she wrote that she had taken a few 'selfies' after learning how to use the self timer on the camera and would send pictures to my e-mail address. In an hour or so I checked my e-mail and sure enough I had an e-mail with attachments from Lara. I opened them and found several shots of her legs. She was right; they were shapely, firm, unblemished and could be classed as whistle bait. One was of her head; face blurred out, but showed a nice, full head of coal black hair that hung shoulder length. The last one was of her full length from the back, in a black slip that emphasized a 'to die for ass' with a hint underneath because the flash penetrated the nylon of the slip and showed a thong strap in her crack. Nice! I would have more than been happy to have kissed it more than once and in many places. Her husband has to be a first class dumb fuck.

The next time I signed on I saw that the icon beckoned me so I opened the chat line and she was asking if I liked the pictures. I poured praise on her and I wasn't kidding or shitting her. She was dynamite under all that religious folderol. She asked if I would want to have more pictures of her and what's not to like about receiving 'selfies' from young beautiful women so you know my answer. Over the next few weeks her chats were depressing as she told me of family dinners that were boring with the diet restrictions they followed plus she said that after the dinners were over, everyone sat around and read verses from their religious manual that the church produced for study. She hated when those dinners were planned.

One morning when I opened the chat line, she was excited about an old friend of her Dad who was in the financial services business who had stopped her in the grocery store. He asked her to have coffee with him because he wanted to speak with her about an opening he had in his office. She was at first reluctant because if she had been seen with him, her husband and family would have raised Holy Hell with her being with a man without her husband present. But she agreed. He told her his assistant had quit because her husband had been transferred to Nashville. He told her if she wanted to try the job to get the feel of it, she could start next Monday at nine. In was a one employee office serving only him. She asked her husband about it and after thinking it over he said that they could use the extra money and for her to give it a try.

She was elated over being able to get out of the house to a real job. She was so elated that she sent me three more 'selfies' of her each more revealing. One was her sitting in the floor with the same black slip, face blurred, with her knees up and showing her bottom on the floor with black panties covering her pussy and just a hint of the string running up her ass. I sat up quickly when I saw the second one because my attention was swiftly drawn to her fully exposed left tit hanging out of the slip. No bra. The tit was bare, nipple hard and stiff. I could hardly wait for the third one, but it was a rear view shot of her legs as she tip=toed and tightened her calves. Nice but very common. I wrote my note on the Chat line telling her how thrilled I was in seeing the photos she had sent.

Two days later I received a chat note that said her boss had told her she couldn't work in the office the way she was dressed. He put her in his car, took her to the Macy's in a nearby shopping center, parked her in the Misses department and told the clerk to outfit her in two mini-skirts, matching blouses and the accessories to go with them. When they settled on a sky blue skirt, a black pin stripe skirt and blouses to complement the skirts and accessories to emphasize the outfits he took her to the shoe department and told the clerk to fit her with two pair of high heels that would show her legs to the best advantage. Back at the office, he told her to go change into one of the outfits and get to her desk. She was told to change each day when she came to work so that she become a showpiece for the customers, ninety five percent men, who came in to do business.

I wrote back and told her to beware. I warned her that he might be setting her up to be the attraction of the customers and of him. She pooh-poohed the warning and said that he only wanted her to look nice, nothing else. Later that evening, she sent me an e-message and a photo with her feet and legs in a pair of the high heels that she had sneaked home. I must admit that the heels made her look so appealing it was a disaster in the making.

She wrote me from her desk at work. She said that he asked her to come to his desk to take a note to a customer. She had her notepad and she stood beside him while he dictated the note. She told me that while he spoke, his knuckles on his left hand touched her calf, giving her a shock. She said she changed her stance but the knuckles again found the back of her calf. She told me she felt energized, had a warm feeling come over her because no other man had ever touched any part of her body before his hand touched her. I warned her that it wasn't accidental and to be very wary of what his next moves would be.

Two days go by and I'm wondering how her work is going so I leave her a Chat message. At home that evening she replied that the knuckles had turned to the fingers and the palm. And that at one point had moved up to the bottom of her mini-skirt. She said it excited her so that when he stopped feeling her lower thigh that she had to go to the restroom and clean herself she was so wet in her panties. I sent back a warning, a stern watch out, Lara. He's going for more. I wasn't satisfied with her response when she told me that she knew it was wrong especially for a married woman, but she also said that it was the most thrilling thing she had ever experienced. She was, in my opinion, over enthusiastic about the feelings she experienced when his hand touched her. I told her that he was thirty-two years her senior, had a lot more experience than she and that he knew exactly what he was seeking. I also told her to contact the previous employee. She may have left for the same reasons I was warning her about. It did no good.

Lara wrote me from home on a Saturday evening late, almost midnight. She began her note by telling me that she had been contemplating what had happened before she told me about it. What had happened Friday afternoon was truly shocking to me. He had called her to his desk and asked her to read a report that had come in from one of the companies he represented. While she was busy reading the report, his hand went up her right leg, into her panties and his fingers went inside her pussy. She froze when she felt them inside her. He fingered her pussy until she leaned her head down on his desk and he proceeded to bring her to an orgasm using his two fingers. She was in the throes on his desktop when he backed up, pulled her skirt up, dropped his pants and shorts, jerked her panties down and forced his prick inside her. She said she yelled loudly because she said he had a dick twice the size of her husband and her pussy had to stretch widely to accept his dick and it hurt painfully at the first insertion. She told me he fucked her hard as she grunted from the pain. She couldn't move as he held her to the desk while pushing his dick relentlessly in her until he raised his head and shouted, "Lara. I'm going to cum inside you. Hold still."

Her Chat continued as she said he backed up after he filled her with cum, used his handkerchief to wipe his dick and her pussy. He pulled his pants up and sat down as if nothing had happened. She said she hurried to the restroom and checked herself for any tears or blood but found none. She said she was awfully sore but no damage was done. She went back to her desk to continue working, but the cum dripped all afternoon and her panties were glued to her pussy. She hurried home so that she could hide the panties and douche herself before her husband got home and became suspicious.

The next day, a Thursday, she wrote that he told her that they would work from his home on Friday. When she arrived at his house, he brought her into the den and undressed her. He told her they had some work to do but that she would work in the nude. At eleven-forty-five, he came to where she was working and told her to come with him. He took her to the bedroom; he stripped, stood by the edge of the bed and told her to kneel in front of him to suck his dick. She protested by telling him that she had never done that before and his response--was---"Then it's damn time you learned how to handle a real dick." She knelt and took it in her hand and she said it was huge, but that she had no idea how big it actually would become until she began to hold his balls as he told her, "When you get it in your mouth, use your tongue as if you're licking an ice cream cone. But keep your hand moving up and down while doing that." She wrote that as degrading as that was, she had electric shocks going through her as she closed her mouth on the massive head of his dick. She told me that she followed his instructions and within about three minutes his cum filled her mouth; he reached down and clamped her teeth together and told her to swallow. She did and said it wasn't that bad. But once he had cum, he pulled her up, turned her around, threw her in the center of the bed and fucked for a least twenty minutes, she confessed that she didn't cum but that he shot his second load inside her once more but the force of his huge dick left her in pain once he had quit fucking her..

They showered together after their fuck and she felt much better about what had happened. She said that sucking his dick, a new experience, was so erotic especially while jacking his massive dick at the same time she squeezed his balls. I wrote back and said, "I told you to be wary. Now tell me what your true feelings are and how you now feel about your husband."

She responded by saying that she never felt more alive or wanted than she did at the moment. She said that his attention to her was giving her the excitement that she had been missing. She was even unhappy with her husband because he was denying her all the eroticism that she was getting from Simon, her boss, at work. I answered by saying, "Don't you think it would have been better to have found someone nearer your own age to have an affair with instead of someone that much older than you?"

She wrote back and said, "NO! My boss's experience, his ability to do what's necessary, his delay in Cumming, and his dick size is what the magic is. Someone my age would cum to quickly, like my husband does, and wouldn't be able to direct me to do the things Simon has me doing. I feel blessed that an older man is fucking me the way he does. Incidentally, he asked me to shave my pussy and I'm going to do that as soon as I figure an answer to tell my husband."

I wrote back and said, "I won't argue with you. If you want to fuck with old men I agree, I'm an old man remember. Just make certain that your pill is still working because you don't want to get pregnant from him. He would dump you in a flash."

"Don't worry. I take the pill religiously (a pun). Incidentally, since you reminded that you're an old man, why don't you send me a 'selfie' of you holding your dick. It's probably hard right now from your reading this conversation.

"Damn, Lara, you know how to hit the nail right on its hard head. I actually have my dick in hand as I type this to you. So, you want a picture of my hard on, huh? Okay, I can do that for you. Check your e-mail in about thirty minutes and you'll see what an almost eighty year-old can still produce. But I want a critique of your opinion of how it looks."

I took my iPhone, took a picture of my pride and joy, attached it to an e-mail and sent it to her while we were still in midst of the Chat. I told her it was on the way. In just a few seconds she wrote back and said, "Oh, my God! I wish you lived closer. I would love to suck your dick and have it fuck me. You are some stud for your age. The old women down there must love you."

"I wish. I haven't had any pussy in four years. And speaking of pussy, have you shaved yours yet?"

"Yes, I found an article about hygiene being better with a shaved pussy. I told my husband, showed him the article, but he still hasn't made a move to eat it. Pisses me off no end. Would you eat it?"

"Lara, I haven't seen it yet, but you can be damn certain I would eat it and founder on it. I would eat your asshole and both of your tits. But I have a question--"Can it still be a pussy if it doesn't have any hair now? Without hair it's jailbait looking. To be a woman it has to be covered with its fur piece to make it attractive. Or at least that's the way I feel. But I'd still eat yours, hair or not."

"Thanks. I have to go. Husband wandering around."

The next Monday she wrote me and said that there was a luncheon planned with a big, out of town client and she had been invited. She said she would write later this evening and tell me how it went. At nine, I used my iPad, called up the chat line and saw that she had left a message. I signed on, waited some ten minutes and she responded. She told me she had a terrible headache and had been asleep hoping it would abate. She said that they went to the hotel for lunch with the client and she drank Vodka Collins's during lunch and that not being used to drinking which happened rarely, she had become drunk. Her boss left her at the table with the client. The client took her to his room, undressed her and fucked her for almost two hours. She said he must have fucked her three times, at least once in the ass, and that her asshole was so sore she could hardly sit.

I was through warning her or trying to guide her. She was in a descent that was spiraling out of control.

Her next note to me that her boss had given her a twenty-five hundred bonus and raised her pay by fifty dollars a month. She was overly elated by that offer. I told her what she was becoming---a whore for his business.

Her answer wasn't what I expected. She was honest in telling me that she was okay with what was happening because it broke the awful isolation of her past life. She told me she was totally overcome by the exhilaration she felt when fucking and it didn't matter who was fucking her or for what reason. She was enthralled by a dick, any dick, any size of dick. She once again reminded me that she so wanted me to be closer so that she could sample my own dick both in her mouth and inside of her.

Jesus Christ, her words made my dick hard again and I had to put aside my iPad and jack off in my recliner until I shot my load of cum into a hand towel. At my age that was degrading but damned if I didn't get a thrill when I cum and filled the towel. What I wouldn't give for some pussy, any pussy would do, but I'm beyond looking and hunting for the stink of a damp cunt. I know it's out there but I'm too damn tired to make the chase. Maybe I should plan a vacation in her town and have her prove her words. But I digress.

In the next week, she wasn't around much. On Friday I received a notation that she was online. I hurriedly clicked on the Chat line and she was ready to Chat. I asked her what was up and she responded that she had been fucking two other clients with great results. She also told me that during her period, her boss had insisted that she suck him off each morning as he sat in his desk chair. She told me that she had eaten more cum that she had ever seen in her life. I wrote her back and told her that it was high in protein and that she wouldn't have any backlash from it. She said that was good because she had given two other clients blow jobs in the office after they signed new purchase agreements. Her boss had given her a five thousand bonus this time with a one hundred dollar a month raise.

I asked her the situation with her husband and she said that he had questioned her about why her pussy had become so loose that he no longer felt as if she was tight around his penis. She didn't know how to answer him. She told me that he became pissed, packed his bag and told her he was moving back in with his brother until she could justify her actions. She wrote me she didn't give a shit what he did or how he felt. She said she now made enough to support the house and that the car was paid for and that he could fuck off.

In desperation I wrote her a sincere e-message about her actions and about what she had become. Not much more than a slut and a whore.

I was stunned when she wrote back and told me that it was none of my damned concern and that she appreciated my advice and friendship but that I should keep my nose out of her pussy doings and that she had never been as happy as she was at the moment. She said that her boss called her a slut when she was blowing him. She detailed how she loved to be fucked by different men with different sized dicks and the funny changes from man to man of how their balls looked as they hung down from their dicks.

She confessed that she had bought a digital camera, took photos of the men with hard ons and had an album filled with the pictures that she studied when she was home alone. She said that she masturbated while viewing the pictures and that she kept the one of my dick in mind until she could cum. I blew that off as her blowing smoke up my ass. She even told me that I was one of those pictures but that I was on a different page entitled her --'Want List.' She said it was the only picture on the page and pleaded with me to visit her so that she could fulfill her desire to fuck me.

The Chats waned. The last one I received from her was joyful and made me feel good. She had divorced her husband, had been ostracized by both his and her families but had no regrets. She indicated that her album now had over a hundred pictures of hard dicks and she said that it didn't contain the first seven she fucked including her boss. She said that she was delaying the picture of his because she was still fucking him. She told me that she appreciated that I told her that cum was filled with protein because she had swallowed at least two gallons in the last six months. I asked where it all came from and she was honest when she said that every male customer that comes to the office got nothing less than an blowjob but that many got to fuck her doggy style in the supply room as she leaned over the table..

She wrote---"I know how degrading my life has become in the eyes of society. But society never lived under the conditions I was raised. I found my talent and I proudly ply it regardless of what society would think. I am at last at peace with myself." She signed off, "Lara on a lark and as happy as she could ever be. I'll now say so long until I see you at my door with your fantastic dick in your hand."

I got the map out and figured how long it would take me to drive there while I held my dick in my hand, but I am just an old man dreaming of what once was his life.

(NOTE: This is a true story with only slight modifications to emphasize my role that wasn't quiet as exciting as I made it--unfortunately for me!)