I am not Sure How this Started

I couldn't believe I was doing this. This wasn't an accidental fling, a drunken hook up. I was actually arranging to meet this man in a hotel room. In the back there were some warm wet wash cloths. I gave myself a quick sponge bath as I got out of my work cloths. The man thought of everything, including the fact that I would need to freshen up a bit after working 8 hours. The French maid outfit was one of those red, Fredricks of Hollywood, outfits. Red thigh highs, garters and black shoes to boot. I had seen one in the catalogs, with a head piece, but there wasn't one here. I guess it would look to obvious when I went through the hotel lobby. There also weren't any panties. At 4:45 I fastened up the garters and put on the overcoat. The lipstick I put on was bright red - to match the outfit.

I was escorted out of the limo and walked into the lobby directly to the elevators. I knew where they were because my husband and I had stayed here to take a night away one time. We weren't on the penthouse floor, however. Even though the overcoat went down to my knees, I tried not to look at anyone in the lobby for fear that they could tell what I was wearing and know what I was there for. I was so thankful that when I got to the elevator there was nobody on it. It allowed me to fumble with the key access thing to get to the top floor of the finest hotel in the city.

I was already prepared for what I was going to do in the role play, having thought of nothing else during my last hours at work. So many times my husband had asked me to do things like that, but I felt silly and just wouldn't do it for him. For Mark, however, I wanted to give an academy award performance - never break character and give him the best fuck of his life.

I opened the door to the penthouse and it was more impressive than I expected - two floors, a bar area, living area and a master bedroom and bathroom on the second floor. I announced "Housekeeping!" in my most feminine voice and saw there was a feather duster near the door that I was obviously to use. There was no response to my call so I did a pretend dusting of the place while I searched around for him.

In addition to a bedroom upstairs there was a sitting room and when I entered, he was sitting in a silk robe, reading. His feet were up on an ottoman. "Excusez-moi, monsier. I didn't realize there was someone here. I can come back."

"Don't be silly," Mark responded. "You are not disturbing me. Do what you need to do while I sit here and read."

I then proceeded to dust the sitting room without talking to him. Making sure I bent over so he could see my ass and leaned over so he could see my size C cleavage. Though I was sure I was getting a stir out of him, he continued to read and only one time did I catch him glancing for a look.

I asked him if he would like me to turn down his bed for him and he agreed. When I returned I asked, "Is there anything else that you will need me for?"

I was hoping he would take the lead here, but he responded with, "no, that will be all."

Not wanting to break character, I inquired, "Are you certain. The hotel wants me to make sure that our best guests are taken care of in any way possible." With this I leaned over quite a bit to give him a clear look at my breasts which were ready to fall out of the outfit.

"Well," he responded. "I have been quite stressed out lately. I could really use with some relaxation."

At this prompting I said, "I will serve you how you like."

"In that case, how about you come over here and do what you do best," he said as he undid his robe and I could see his fully erect cock. He kicked aside the ottoman and I knew that I was to get on my knees in front of him. "For starters," he continued, "Let's see if you can do better than the skank I had Saturday night."

It didn't even bother me that he called me a skank. He could have called me whatever he wanted at that point. I was bound and determined to give him a better blowjob and to get that cock in my mouth. Down on his cock my head bobbed and I didn't even bother to give him eye contact. My eyes were watering with how deep I was taking him. After a few minutes he said, "I want you to go lie on my bed and get that pussy of yours ready because I am going to cum deep in that cunt of yours."

I quietly stood up, adjusted my outfit and laid down on the bed. As I spread my legs I started to rub the top of my pussy so as to stimulate my already erect clit. I slid my middle finger in and out of my snatch as I stared in his eyes, not the least bit embarrassed that I was masturbating in front of him. He let me go for quite a while like that and I swore I was going to cum - something that I was never able to do masturbating in front of my husband. Instead he laid his face between my legs and started to lick my clit at the same pace I was fingering it. Between his warm tongue and everything else, I went over the edge quickly. I wasn't ready to stop and I was literally begging him to come and fuck me. He came up between my legs and while he kissed me with his pussy juice mouth, he buried his cock in me with one big push. I had forgotten how good it felt and my pussy, still having spasms from my previous orgasm, I quickly started to build again. I begged him to fuck me deep and he lifted my legs over his shoulders and started to drive his cock so deep that I though he was going to bust me out. He lasted a lot longer than I thought he would, but I didn't mind because I loved having his muscular body against mine as kissed me on the lips. Before long, he was building and just the thought of having this man cum in my pussy took me over the edge again. I could feel the cum squirting inside of me and for the longest time I was wishing that I was not married so that I could fuck this man again that night.

As I lay on his chest and we had some pillow talk, I was startled by the things I was revealing to him. Without him prompting me in the least bit I had shared my sexual history, experiences and even told him things that I refused to do. He laid there quietly absorbing it all and stroking my hair. Before I knew it, the time was 6:30 and he told me that Ben would be waiting for me downstairs. While I really didn't even need to dress any more (the outfit was still on me), I did need to check my hair so that it didn't look like I was a hooker leaving the room - even though in some ways I felt like one. When I reached the elevator, the fact that my outfit had no panties became very apparent as I could feel his cum run out of me and down my leg.

When I reached the car, Ben let me in and I was pleased to find that the washcloths were warm and clean again. I cleaned up, and was even more surprised to find that the panties I wore the other night were laundered and I had clean underwear to change into. Ben dropped me off at my car and held the door for me as I got out. The drive home was exilerating and I couldn't help but look in the mirror and feel see that FFF (freshly fucked face) look.

As I reached my neighborhood I realized that it was very possible for my husband to tell what had happened by my look and smell. I could swear that the smell of Mark's cum was permeating through the air and my husband would be able to tell. I put a look on my face of utter exhaustion in hopes that he would think that I had a long day at the office (what with the meeting and all), and that I just needed a shower and to get to bed.

I walked in the door, not to find my husband watching TV or anything, but dinner had been made and he was helping the girls with their homework. He told me to go grab a shower and he would heat up a plate for me. As I got into the shower and rinsed off the sweat and fluids of my affair, I felt really guilty. My husband was such a good guy. Why was I doing this? Still, I was glad that my husband didn't try to get me to sleep with him that night.

It was several days before I heard from Mark again. I realized that following Friday that I knew very little about him. I only knew that he ran an investment firm and that he was wealthy. I didn't even know for certain that he wasn't married. While he told me his last name the night we met, I wasn't really certain what even that was. I felt so guilty that I was risking throwing my marriage away to sleep with him and yet here I was thinking about him non-stop and yearning for him to get in contact with me.

Once again a currier came, but this time it did not draw the attention of the ladies at work. They had already commented on how glowing I looked that week and just assumed that I was having great sex with my husband. In reality, outside of that blowjob, I had not had sex with my husband in over 3 weeks.

The package was even more of a shock. It was a catholic schoolgirl outfit with the white thigh highs. What was shocking was that it was clearly a size smaller than what I was currently. The note attached to it was very simple:

I will be out of town for 2 weeks. I will return on the 19th and you will be expected to report to the principal's office in this outfit - no excuses. If you want to stay out of trouble and graduate, you will need to follow instructions and be in full uniform. Ben will pick you up at 5 pm sharp.

PS - schoolgirls do not have hairy pussies.

Oh my god? What was he saying to me? Was he really telling me to shave my pussy? I hadn't done that in 16 years. I will admit that I did it for my husband when we were dating, but once I was married, it was just too much trouble to maintain. Likewise, I will admit that I felt wrong having the jungle down there when Mark was eating me out the other night, but to shave it cleanly? How could I shower at the gym and not have the other women notice - or my husband. Speaking of the gym, did Mark intentionally get the outfit one size too small? Was he meaning for me to lose weight when he told me to report in "this outfit." I know I have put on some weight since the girls were born, but this bothered me. I was seriously worried that despite my efforts, I was not sexually pleasing to him. I so much wanted to keep seeing him.

By the close of work that day, I made a plan to do all of that. I was going to look sexy for him. I was going to please him to the fullest. I knew that I could fit in that outfit if I dropped 10 - 12 lbs and I scheduled an appointment to be waxed a few days before he got back. It would involve a lot of extra time at the gym and less eating.

I let my husband know that I wanted to get back to the gym some more and asked if he could pick up some of the slack with the girls. He is a good dad, but I know he was being helpful because he was hoping to have sex that night.

I worked really hard at the gym that day - even did 20 miles on the bike. When I got home I was exhausted and while I intended to have sex with my husband, I just wasn't up to it. I went both days that weekend, hitting the gym Saturday afternoon and Sunday after church. By Sunday night I knew I couldn't put it off any longer and even though I was sore as hell, I knew I needed to have sex with my husband.

The sad part was, I actually felt like I was cheating on Mark while he was away. My husband was more than passionate, even trying to say the right things like "You look beautiful the way you are." While the affection and emotion were there, the passion was just not in it (for me) and for the first time in my marriage, I faked an orgasm. My husband wanted to cuddle with me afterwards, but I just wanted to get some sleep so I didn't think about eating.

I am glad my husband didn't really initiate sex those next two weeks because my body was tired and sore. By about the 9th day I was feeling better and the scale reinforced what I was doing. I was down 10 lbs and tried on the outfit in the bathroom at work. While I couldn't exactly step out of the stall and look at myself in the mirror, I could tell that the shirt and skirt fit around the waste. At this point I began to think about what I would be doing with Mark and actually considered masturbating right there. Instead, I masturbated that night before my husband came to bed.

The day of the waxing had arrived and I knew that this was going to cause other problems. How was I going to change without my husband noticing? His actual birthday was coming up in a week and in some way he was going to find out. I just hoped that I could hold off until then and tell him it was a birthday present.

If you have never been waxed down there, let me tell you - it hurts. I was amazed at how raw I felt and actually regretted not doing it a day or so earlier. Fortunately, all the redness went down by the time the 19th rolled around and none of the stubble had returned.

I went to the limo and once again, Ben pulled up right as I got out of the elevator. I changed in the car and even put my hair up like a schoolgirl. The only problem was, there was no overcoat in the car. When I asked Ben about this he said, "Not to worry, ma'am. We aren't going to a public place, we are going to his office." The fact that I was going to a new place and had no idea what to expect had me a little nervous. I honestly think this was Mark's plan in hopes that he would make me as nervous as a schoolgirl. Walking down the long lit-up hall with all of the offices that could open up at any time had me more than nervous. When I reached his office - the big one in the corner - I walked in, shut his door and asked, "You wanted to see me, sir."

Mark was in a suit, and working on some paperwork on his otherwise cleared off desk. Without looking up he responded with, "Yes, young lady, have a seat for a minute."

I sat down in my outfit of white thigh highs, plaid skirt and white shirt with cleavage. I felt rather sexy, but as I looked around the office, I was more than intimidated. Here and there were pictures of Mark with famous athletes, musicians and even two presidents.

He finished his paperwork and looked up at me for the first time. I could tell that he was pleased with how I looked. He spoke for the first time and his voice was like that of a school principal lecturing a student. He said, "We have ourselves a bit of a problem, young lady. It appears that you are failing 2 of your classes and are in danger of not graduating. I hate to inform you of this so soon after your 18th birthday, but unless you come up with something, you are not going to graduate."

I took the queue and said, "No sir, my parents will kill me if I don't graduate. Isn't there anything I can do for extra credit or something?"

With this, he came around the front of his desk, took a seat on his desk so that he was looking down on me (and also into my cleavage) and asked, "What do you think you can do in such a short period of time that I could justify telling your teachers that you did extra credit for me?"

"Well, sir," I responded as I took out a lollypop and started to lick it. "I am 18 now and I do have some talents that some of the boys enjoy."

"Are you seriously offering me a blow job in order to pass your class? Is that what you are saying?"

"No sir," I responded and upon seeing the look on his face changed it to, "Yes sir, I mean, I am a virgin and all."

"Well, if I am going to pass you in two classes, you are going to have to do more than a couple of blow jobs for me. You are going to have to submit to my needs for a couple of weeks." I took the queue and got up from the chair and said, "I will do whatever it takes to get my diploma and I started to kiss him on the mouth. Before long I was in his favorite position - on my knees and sucking his cock. This time, however, he was standing up and his pants were around his ankles.

Before long he kicked off his shoes and pants and had me lay down across his desk. His only words out of character were, "Let's see if you followed my instructions." I could tell he was please as he went down on me and ate me out for what felt like 20 minutes. He was so good at it - just seemed to know how to put the right amount of pressure on my clit and how quickly to move his tongue. After one very intense orgasm he got off of his own knees and pulled me closer to him on the desk. As he moved his penis closer to my pussy he said, "Being a Catholic School, the use of rubbers is forbidden, so we are going to have to take some other precautions so you don't get pregnant."

I took this to mean that I was going to be swallowing another load of cum, but I was so desperate to have him inside me that I said, "I will do whatever you want so that I can pass." He slid his cock inside of my extremely wet pussy, but because it had been so long since I had a dick in there (especially one of his size) that I groaned a little like a virgin.

He stayed in character and looked at me and said, "Not to worry, it will start feeling good, soon."

He was right about that and before long I was building into another loud orgasm as I wrapped my legs around him and came some more. I desperately wanted him to cum inside of me so I stayed in character and said, "you can cum in me if you want."

"Oh, I intend to do that" he said with a smile, and he pulled out of me and told me to lay down on the desk face down.

He lifted up my skirt and I am not sure when I realized what he had in mind, but I quietly reminded him that "I don't do that."

"Well, if you are going to graduate, you are going to have to please me. If you are going to please me, you will need to let me fuck your ass or get out of my office."

Was he seriously giving me an ultimatum? Was he going to throw me out if I didn't do this. I didn't want it to end. It couldn't end. But he knew I never did this with my husband. Sure, we had tried, but it hurt too much. I wasn't going to lose this man, however. So I looked at him with a crooked smile and I bent back over the desk, grabbing the other side to be prepared.

With this he said, "I knew you were a nasty girl," and I didn't know whether to take it that my character was or that I was. All I knew was that I was about to give this man something that I had never given to another man - and he knew it. He rubbed a little lubricant on my asshole and started to slide it in, getting the tip of his dick wet with my still lubricated cunt. In fact, I tried to tighten my cunt around his cock as he did this in hopes of getting him to finish there, but he was not about to miss out. With a little bit of a groan, I could feel the tip of his large penis break the seal of my sphincter. He let it sit there for a bit adjusting to the size. I was surprised because while it hurt, it didn't hurt near as bad as it had in the past. Before long he was giving me steady even strokes and went back into character. "Yes, I am going to cum in your ass. If you are going to graduate, you are going to be my little ass-fuck girl, do you understand? "

"Yes," I responded through slightly gritted teeth. "I'm your ass slut." I could tell that talking dirty like that was turning him on so I kept it up a bit with "Oh god, make me your ass slut. I've never done this for anyone else but now I am yours to use as you want. FUCK MY ASS! Make it yours. FUCK MY ASS!!"

Before too long his thrusts became much stronger, but I let him go because I knew he was about to cum, and cum he did. With one final thrust he buried his cock to the base of his dick and held it there while he came. As he held it there for a few seconds he said, "God I love a good virgin ass" and he withdrew his slightly flaccid penis with a tiny pop, and I could feel his cum run down my ass. I lay across his desk for a few more minutes hoping the pain would subside some, but it didn't. When I finally pulled on the panties, he looked at me and said, "On Monday we will be meeting at my house and we will continue to meet until I feel you have earned the credit to pass." While he didn't say so directly, I realized I was being dismissed like one of his students or one of his employees. I started to walk down the hall in the outfit and I realized that I was walking a little funny from the ride I had. I also realized that there were people talking on the phones in the various offices I passed on the way in. Were they here when I arrived? Could they have seen me? Did they HEAR ME?