This story starts back in my high school days. I grew up in a very conservative family. My parents always bought me clothes that hid my natural beauty. I always wore loose-fitting clothes, and although I had a nice body, no one ever knew it by the way I dressed. I was a loner because of that. I hardly had any female friends, and the boys shied away from me because I didn't wear short skirts and tight jeans and didn't show off any cleavage as my classmates did.

There was a boy whose family knew mine, and we spent a lot of time together because our families socialized frequently; his name was Randy. He, like me, was a bit of an outcast. It was our senior year when he asked me out on a date. I have to admit I thought he was a nerd, but I thought that was all I could attract, so I said yes.

Our dating was not like my classmates'. He usually came over to my house or I to his, and we sat either watching TV with our parents or playing board games. We were together all of our senior years until he went off to college. I was told I wouldn't be able to go to college because my parents couldn't afford it. Now that I've just graduated and gotten married, I'm expected to find a job in my field. Like I did my whole life, I didn't question my parents' decision and went to work at a grocery store near my house.

Randy would come home for school breaks, and I would continue to see him. Other than that, I went to work and then stayed home. My parents wouldn't let me visit Randy at school, so that was my routine for four years while he was there.

After Randy graduated, he was offered a job about four hours away from me. He told me he didn't want to be away from me and asked my dad for my hand in marriage. My dad granted it, and a few weeks later, Randy proposed to me. I accepted, and as I look back on it, I realize I only accepted because I saw it as a way to escape my hometown and my parents. It wasn't because I loved Randy, but I felt it was my only option.

We got married and moved to where his job was. We found a lovely little apartment and lived there for a few years until we could buy a house. Randy's job paid well, so we were able to live comfortably. I was now able to buy my clothes and would try to buy some fashionable ones that would show more of my body, as I had always wished I could look like the girls from home. Although this still met with some resistance from Randy. He would tell me no wife of his would be showing her body like a slut. Because of my upbringing, I never questioned because I felt I needed to do as my husband said, as my mom did.

I lost my virginity on my wedding night to Randy, and he lost his to me, so we were never sexually aware of anything. Our love life consisted mainly of one night a week, him crawling on top of me in the missionary position, and making love to me. He would shove it in me and pump a few times before he came in me. I never knew it then, but I never had a real orgasm while I was married to him. Even with our lack of a strong sex life, Randy did manage to get me pregnant. 

After giving birth to our baby boy, my life centered around him. Randy was home less and less. Our so-called sex life was now non-existent. Being alone so much, I would spend my time when the baby was sleeping on the internet. That is when I found porn. I heard of porn and knew it was out there, but I never watched a video. I found myself looking at it more and more, and I never knew all the things people did sexually. I also paid attention to the fashion trends and how other women were dressing. I was intrigued for sure.

I found out about a year later why Randy was not home often. He served me with divorce papers on my birthday. He has been having an affair with a woman from his office for quite some time, and he wanted to be with her. To say the least, I was devastated.

I put my trust in my lawyer since I had no clue what I was doing or what to expect. My lawyer fought, and I took possession of the house, along with all its contents and half of our savings.

I was in shock and didn't know what to do. The only thing I knew was that I was not going home to my parents' hometown. I was determined to make it to my own house. I sat down and went over my savings and expenses. There was no question that I had to find a job quickly, as I only had enough money to pay the mortgage for a few months.

I decided to buy some fashionable clothes to wear to interviews. I have to admit, this was the first time I saw myself in this light, and I liked what I saw. I felt sexy, and for the first time, I realized I had a smoking body.

I was 5'7" tall and had blonde hair, was 128 lbs., my legs were long, and with the new clothes I bought, I realized I had a nice ass. My feeling about my new look was only strengthened when I wore these clothes in public. I could see and feel the men looking at me and glaring at me. For the first time, I felt sexy.

I started searching for jobs, but I quickly realized I didn't have any experience except for working in a grocery store. I came across a few ads for secretaries, or as they called them, assistants. I was called for a few interviews, but they all went with the same results. "Sorry, we are looking for someone with more experience."

I was desperate and would cry myself to sleep at night, not knowing what to do. I received a call from a large advertising firm to which I'd applied, asking if I'd like to come in for an interview. I jumped at the opportunity. I decided to go all out. I picked out an outfit I bought two weeks ago. It was a black leather skirt paired with a white shirt, with the top three buttons left undone, black stockings, and black heels. I loved the way I looked in this outfit, and I felt confident. I stood there looking at myself in the mirror and thought to myself, I never knew I had boobs like this.

I gave the baby to a friend to babysit, and off I went to the interview. The man who interviewed me was lovely, and I could see him staring at my boobs and legs. I was not above myself to uncross my legs a few times to keep his attention. After all, I needed this job; I wouldn't know what to do if I didn't. I felt confident that I had done well, and I expected him to offer me the job after the interview. To my dismay, I was wrong again; I was told they wanted someone with more experience.

I felt my whole world end. I held back the tears until I got back to my car, but couldn't hold back anymore. I lost it. I sat there and cried, and to be honest, I thought about starting my car and just driving it over the edge of the parking garage. It was the thought of my son that stopped me from doing that. I got myself together and left to go home. A few miles away, I thought that instead of going home, I needed a drink and to get myself together before I picked my son up. I stopped at a hotel that had a nice bar. I knew of it because we occasionally went there for dinner. It was very upscale and amicable.

I sat at the bar and ordered a Captain Morgan and Coke. I sat quietly at the end of the bar and kept to myself. A short time later, a woman who had been sitting at the bar came and sat next to me. Asking me if I was okay, I assured her I was, but I told her it had been a bad day. When she asked me what made it a bad day, I unleashed on her. I would never share my problems with a stranger, but I just had to tell someone. She listened to me and consoled me. When I told her how I was going to lose the house, she assured me that it wouldn't happen. I looked at her, confused, and asked how she could know that.

She told me that she could be the answer to my problems and mentioned that she might have a job for me if I was interested. I looked at her with a blank stare, and she went on to tell me it was a bit unusual for a job and wasn't for everyone, but those who enjoyed it made a great deal of money.

She piqued my interest, and I asked her what kind of job it might be. She told me that before I give you the specifics, I want you to promise not to react and to listen to her, keeping an open mind. I agreed. She went on to tell me that she is a madam and has some women who work for her, and she feels I might benefit from this job.

I sat there numb, not knowing what to think. My first thought was that I could never. Then she asked if I would consider meeting her for lunch the next day. I found myself agreeing to my surprise. She smiled and asked me if I knew where Basilico's was. I told her I did. I knew where it was, but I never went there because it is an expensive restaurant. She asked me to meet her there at one o'clock.

"We never did formally meet she said, Hi, I'm Mary Ann."

"Hi, I'm Donna," I replied as I presented my hand to shake hers.

"Pleasure to meet you, Donna. I'll see you tomorrow at one, then." With that, she paid my tab with hers and walked out. I sat there admiring her beauty as she left.

My mind was wandering the rest of the night, rerunning my conversation with Mary Ann. After my son was put to bed, I did my nightly ritual. I got my laptop out and started to watch porn videos, pleasuring myself. I watched and took note of the acts that the women were doing—things I have never done, but ones that have interested me since I discovered them.

I kept thinking about how Mary Ann said her girls make thousands a week; some can make that in a night if they wanted to. I thought about how my problems would be solved with that kind of money. It was a long night, and I didn't get much sleep as I wrestled with this dilemma.

The next morning, after giving my son breakfast, I selected an outfit suitable for the restaurant. I dropped my son off at daycare before I headed to my meeting with Mary Ann. She was already seated, and when I was escorted to her table, I found two other women already seated with her. As she saw me approaching, she stood up, hugged me, and kissed me on the cheek.

She introduced me to the woman she was with. There were two who worked for her. She went on to tell me that she felt it might help some to have them share their perspectives and answer any questions I might have.

We ordered our lunch and spent the next two hours discussing Mary Ann's proposal and the job's responsibilities. I was straightforward in telling her how inexperienced I was and told her about my conservative upbringing. That didn't seem to bother her as she told me we could work through that, and she would be with me every step of the way until I felt comfortable. It did strike me that all during lunch, we were constantly interrupted by men who, when they walked by, would stop to say hello to Mary Ann and the two women. Mary Ann would always introduce me, and these men were doctors, lawyers, a judge, and a few politicians.

I must admit that I had a wonderful time with Mary Ann and the two women. When I had no further questions to ask or they had no more advice to offer, we decided to leave. Mary Ann told me that she understands she presented a lot of information to her and asked if I would honestly consider all we said, and either way, call her with my decision. She then discreetly handed me an envelope. It was filled with $5,000. I asked what this was for, and she told me it was to help ease some of your debt or to have fun and do something I wanted to do. I tried to give it back to her, telling her I couldn't repay her. She told me it was not a loan, it was a gift, and she didn't expect it to be paid back.

On the drive home, I have to admit I didn't feel disgusted by the offer; in fact, I thought the way they presented it would be more elegant than dirty. When I got home, I went upstairs to change before picking up my son. Before leaving, I opened the mail, and there it was. A letter from the bank telling me that if I did not pay the outstanding balance on my house, they would start foreclosure proceedings. I just melted and started crying. I felt all alone with no one to turn to for help.

I just needed someone to talk to who was aware of my situation. I opened my purse, picked up Mary Ann's business card, and dialed her phone. She knew something had happened right away, and after giving her some quick details, she asked for my address and told me she would be right over.

I settled myself and went to pick up my son, returning about five minutes before Mary Ann arrived. She brought the two girls from lunch. She told me we are all there to support her. They ordered dinner for us, opened some wine they had brought, and helped get my son to bed. I must admit that they were all wonderful with my son. One of the girls, a business major, came up with a plan that would satisfy the bank for now and allow me to prevent the foreclosure proceedings. I felt much more relaxed by the end of the night.

Once they left, I crawled into bed and for the first time, I didn't feel alone. Their support meant so much to me; I didn't want to lose it. That got me thinking about Mary Ann's offer.

Two days passed, and I called Mary Ann back, still unsure of what I would do. We chatted for ten or fifteen minutes, and I blurted out. "Mary Ann, I want to accept your offer."

As soon as O told Mary Ann that I would accept, I felt a sense of relief. Mary Ann and the rest of the girls were so helpful and supportive; I felt like we were all one big family. They took me shopping to buy a whole new wardrobe. One that would be my work clothes, as they called them. They helped me with some beautiful yet revealing dresses, the right shoes to pair with them, and were extremely helpful in teaching me the correct way to apply my makeup, as well as ways to accent my lips and eyes.

For a few weeks, Mary Ann would have me meet her "safe clientele." I was nervous when I went to the hotel to meet them. I wanted a review, but Mary Ann would only say that I did fine, and they were very pleased with me. That review came a few weeks later, when Mary Ann sat me down and told me she had been a little deceitful with me, but it was all to help me.

I looked confused, and I asked her what she meant. She went on to explain that the guys she had been with over the past few weeks were acquaintances she had previously dated, whom she used to bring out on dates to help make them feel more relaxed when they went out on their own. It also gave her peace of mind knowing that I would be able to present myself and not worry about potential issues. She then told me that all the men gave you rave reviews and felt any customer would be delighted to have me. Now, with all that being said, I have a client for tomorrow afternoon, and if you feel comfortable enough, I think you would do very well with him.

She went on to tell me he is a regular client whose wife doesn't give him any sex, so he comes to us to satisfy his urges. He is a kind man and very respectful towards the girl. It would be just like you met the guy at a club and went home with him. But I want you to be comfortable going with him.

I sat quietly for a few moments before I told Mary Ann that I would do it. She then told me to be at the Hilton on Jefferson Parkway at 1:00 PM. Go right up to room 503.

At home that night, I couldn't stop thinking about it all. I ran through various ways I would dress, style my hair, and apply my makeup. If I were honest with myself, I would have to admit I was a bit excited about the whole thing. I felt ready. The trials that Mary Ann had me go through made me feel comfortable doing things I hadn't done before. As I mentioned, my ex-husband Randy was very conservative, so we just had a conservative sex life. He crawls on top of me in the missionary position as he shoves his dick in me and pumps a few times until he comes in me. I never did oral sex. I tried to get Randy to let me do it to him, but he would never let me. That is, until I was with one of Mary Ann's friends, and I liked it. I liked the feel of his cock in my mouth, the way he moaned, and the feel of his body as he came.

I woke up in the morning and took my son to day care. I returned home and began getting ready for work. I wore a tight, low-cut black and red dress. It was very short and with a plunging neckline that barely contained my tits. I wore red heels and completed the look with bright red lipstick, paying close attention to my mascara so that my blue eyes stood out. As the other girls pointed out to me, those are two good things to do because it is hot for them to see both when you are doing oral on them.

I arrive at the hotel on time. I made my way through the lobby. As I did, I could see the two guys at the desk watching me and whispering. I knew they knew why I was there, and I didn't care. If I were honest, I would have to say it turned me on that they knew I was going up to a room to have sex that the man is paying for. I made sure I strutted right by them, wiggling my ass as I moved to the elevator.

As the elevator opened on the fifth floor, I stood there for a minute looking into the mirror, making sure I looked right. Once I was satisfied with everything, I made my way down the hallway to room 503 and knocked on the door.

The door opened, and there stood a balding man, about five feet ten inches tall and slightly overweight. I smiled at him and said, "Hi, I'm Mandy" (An alias name since Mary Ann wants all her girls to go by a different name than their own.)

He looked me up and down and smiled as he introduced himself as Stanley. He invited me in and told me that Mary Ann didn't do you justice when she described you. I mailed as I thanked him for the compliment. He asked if I wanted a drink, but I declined and thanked him.  

I asked him if I could go into the bathroom to freshen up. He agreed and headed into the bathroom, where I changed into a white corset, a white garter belt, and stockings, along with my heels.

When I came out of the bathroom, I saw his eyes widen; it was apparent he liked what he was seeing. I took a deep breath and thought about what the girls had taught me. I approached him very slowly, making sure I was swaying my hips as I walked, as the models do on the runways.

I placed my hands on his chest when I reached him and seductively whispered, "I hope you like what you see?"

"How could I not?" he replied.

His hands cupped my ass as he pulled me tight to him. He held me tight to him for some time as we talked about whatever he wanted to. I have to admit my heart went out for him as he told me how his wife has no sexual desire and he still aches for a sexual partner.

My hands then went to his belt and undid it as well as his pants, then pushed them down over his hips. As I did that, I asked him what his preference would be tonight. My hand took hold of his cock, and I caressed it as I awaited his reply. I could feel it twitch and grow harder in my hand. It wasn't anything out of the ordinary. I mean, it was of normal size and girth; in fact, it reminded me of my Ex's cock.

He nervously answered me in a soft tone and told me he wanted to watch me strip for him. I pushed him back onto the bed and put some music on from my phone. I slowly swayed to the music, grinding and rubbing myself as I slowly disrobed. He was mesmerized watching me. The last article I took off was my garter belt, but I kept my heels and stockings on. I crawled next to him on the bed, my tongue slowly licked up his neck to his ear as I whispered, "What else would you desire?"

In a shaking voice, he told me he would love oral. I thought to myself that a man who is buying a hooker is so polite about it. I remember the other girls telling me how helpful it is to talk dirty to them because it gets them going faster and they end quicker.

My hand reached down and took hold of his cock as I slowly stroked him. I told him I am glad he wants oral since I loved sucking a man's cock so much. I loved the feel of it between my lips, hearing him moan and groan, and feeling his cock twitch in my mouth. I could see that the girls were right; he was affecting him, for sure. I opened the condom and slid it onto his cock, (Mary Ann was adamant that all her girls made sure their Johns wore condoms). 

I leaned down and slowly licked my tongue from his balls to the tip of his cock. He let out a loud moan, which got even louder when I wrapped my lips around his tip and took him into my mouth. I worked my lips up and down on his cock, hearing him tell me how good it felt and how much he wished he could get that more regularly. I would, in turn, tell him how much I loved his cock in my mouth and how I would suck his dick every day if he were my husband. The girls taught me well, and I talked as naughtily as I could.

I have to admit I was working his cock thinking that was what he wanted tonight, so I was a little shocked when he told me to stop, and asked me to straddle him and ride him.

We all know the customer gets what he wants, so I straddled his hips. My hand reached down and took hold of his cock as I lowered myself onto it. I let out a loud moan as it slid deeper into my pussy. Telling him how good his cock felt in me and how I wanted him. Letting him know how I wanted to fuck him and drain his cock.

I have to admit, talking dirty does not come naturally to me, so I modeled my dirty talk from what the girls would share with me and from the porn I have become a student of. I don't know how I was doing, but he was responding to it.

As I bounced up and down on his cock, he started to thrust his hips up into me and reached up to cup my tits and grope them. I have to admit I was getting turned on, and as I felt his cock pound deeper, my moans filled the room. I begged him for his cock as I rode him harder. His hands pinched my nipples as I bounced on his cock.

I could feel my body start to shake, and my moans became louder. I put my hands on his chest to steady myself as I went up and down on him. I let out a scream as I pushed down on his cock, grinding harder into it, my body tensed, and my pussy clamped around his cock. I continued to shake more as I exploded on his cock. I rode my orgasm until my body went limp and I collapsed on the bed. It took me a little while to realize he didn't cum.

I felt like I didn't do my job, and I started to apologize. He was quick to comfort me and told me it wasn't me. He went on to say to me how he had some health issues a few years back and since he was put on the medication, he is now on it takes him a long time to cum, but he assured me he will cum eventually.

Well, now I saw it as my challenge to make him cum.

As I started to regain my composure after my orgasm, he repositioned me onto my back, pushing my knees back to my chest as he moved between my legs. I watched as he guided his cock to my pussy lips. He just looked down at me with a gleam in his eyes. Feeling his cock rest at my opening, I softly whispered, "Yes, oh yes, fuck me again."

I watched as a smile came over his face and he slowly pushed his cock into me. Opening my lips as my cunt swallowed his cock. I watched as he went deeper until his cock was buried deep in me.

His tone changed as he told me to take his cock. Telling me how he was going to fuck me hard and deep. His hips ramming harder into me. I could hear the sounds of our bodies banging together fill the room. His moans and groans became louder. I felt my body reacting to his cock pounding hard and deep into me.

I could watch his facial expressions, and I could tell he was getting closer. I started to beg for more and tell him how good his cock felt in me. Although I was using the dirty talk to excite him, I have to admit it was turning me on more.

I watched as his cock slid in and out of me, and how my cunt lips were tight around his shaft. Oh fuck, I was getting close again. I started to thrust my hips up into him to feel him even deeper. Suddenly, he let out a scream as he thrust into me, grinding his cock harder as he stayed deep in me. I felt his cock throb deep in me as he came hard. The excitement of his orgasm drove me over the edge as I held him tight to me, and I reached my second orgasm.

He collapsed on top of me as we both lay there gasping for air. I could feel his cock twitch in me as the last droplet of his cum filled the condom.

We lay there holding each other for a while before I got up and freshened up before I left.

Later that day, I got a call from Mary Ann asking how I did. I told her I felt I had done okay and that everything went well, as far as she knew. She laughed, "Okay, baby, I just got a call from him and he raved about you. Telling me how sexy you were and how he hasn't been that turned on in a long time, if ever."

I have to admit I was pretty pleased to hear that I got a good review. That was the first trick I ever did and one I have always remembered. He has become a regular customer, and we have spent several years together.

I know people would not understand what I am doing and would look down on me for doing it. Still, it has brought me out of my financial hole, and my son and I are enjoying a comfortable life, so I see it as I am doing what I need to do for my family, and fuck anyone who doesn't like it.