Please, Mr. R. Ch. 01

Forward: I wrote this story (series of chapters) for my friend, Jay. Well, for me, too, but mostly as a present for Jay. At a time when I really needed a friend, Jay was there for me. Through my endless bantering, mindless emails and never ending drama that surrounded me for months, Jay was there everyday, offering me support, advice and a shoulder to cry on. Jay, my dear friend: I love you for the tenderness and attention you gave me, and, for the way you listened and opened my eyes to see things about myself, and the special person in my life now. I can never repay your thoughtfulness and generosity, but, I hope you'll read this story as my love sonnet to you and know that next to Daddy and Brent, I love you the most.

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His directions were easy to follow. I parked my car on the street, just as he directed, several houses down from his own. I was wearing exactly what he requested – a thin, button-up sun dress with no bra underneath. I was totally shocked when he suggested I unbutton my sun dress all the way down to my waist once I was safely in my car and on my way.

On top of that, he suggested I pull the top of the dress open several inches so my breasts were exposed as I drove to his house. In a way, I felt fortunate he didn't ask me to unbutton my dress all the way down, or, remove it completely. I'm almost sure I would have done it, though. Actually, I'd have done whatever he asked, but, I think he knew I was literally scared out of my wits to be exposed like that, and he didn't want to push me past my breaking point.

On the flip side, however, the excitement that had been building up inside me for the last three days cancelled out every ounce of fear, nervousness and anxiety I was feeling. The anticipation of what he'd arranged for me, what ever it was, and the anticipation of not knowing was killing me.

I'd tried in vain to busy myself in the previous days, hoping it would take my mind off what was going to happen to me today, and that seemed to work okay for a little while. But, I literally soaked a pair of panties yesterday rubbing myself as I sat at the computer chatting with him online, trying to get him to tell me what was going to happen once I arrived at his house.

"You don't need to worry about that, Sally." He typed. "I've got everything arranged. I promise you'll be safe and I'll be there to oversee everything. That's all you need to know."

I begged him to let me touch myself numerous times since Tuesday. The secrecy and expectation of what was going to happen was making me crazy and leaving me with an unsatisfied feeling between my legs. As a result, I daydreamed constantly, trying to figure out what he had planned – what he was doing, and what I was in for. And as each day passed, my excitement grew and my need to masturbate grew, too. I needed to cum, but he held firm regardless of how many times I pleaded with him. He simply said "No, Sally, no touching yourself down there."

Finally, growing tired of my incessant begging, yesterday he gave in. While we were chatting online, he told me I could touch myself and give myself one very much needed orgasm. But, I could only touch myself outside my panties, he said. He first made me promise I wouldn't cheat, though – no direct contact with my vagina, and no sneaking my fingers into my pussy in the shower, either. He assured me the reason for this would be clear when the time came.

But, there was a price to pay for being able to have my orgasm – even though I had to do it through my panties. "You have to bring them with you tomorrow." He said. "In a plastic bag, Sally. Take your panties off as soon as you cum, put them in the plastic bag and seal them up. Then, bring them with you when you come."

I can't believe how fast I agreed. Honestly, I didn't stop to think why he'd ask me to bring my panties. But, once I'd cum in them, and seen the way they were completely saturated with my vaginal secretions, I began to worry. And, as I was folding them up and putting them in a zip top sandwich bag, I realized he obviously had some plan - there was some reason, some significance to these panties. A feeling of disgrace swept over me as I looked at the wet panties in the baggie, knowing I was going to hand them to him and he'd have them – maybe even keep them.

I'm sure the man in the pick-up truck next to me at the stop light saw my tiny boobs between the open folds of my sundress. The top of the dress was gaping open as I waited for the light to turn green, and out of the corner of my eye I could see him looking right at me. I felt utterly embarrassed as his eyes stared at me, and I was almost tempted to close my dress and speed away so he couldn't see my pitiful excuse for boobs any longer, but I thought, "I'm supposed to let him look. That's what Jay wanted. That's why I was told not to wear a bra and to open my dress."

"It's all part of it," I mumbled, "its all part of what's happening to me today."

I was trying to convince myself that letting someone see my little boobs was part of my unfolding adventure, but, it was a hard pill to swallow. I'd always been ashamed of my breasts – or, lack of breasts, I should say. Then I remembered what Mr. R. said, "You can't really be an exhibitionist unless you're willing to let someone see your breasts, Sally. Don't be ashamed of them, they're beautiful."

I guess I'd describe them as 'Petite'. One of my boyfriends once called them 'Perky', but, to me, they're just small, and I honestly felt cheated by Mother Nature. All my friends had these full, womanly breasts and they weren't shy about showing some cleavage. Then there was me – good ol' flat Sally. Well, maybe I shouldn't say 'flat' because that's not completely true. I can almost fill an A-Cup when I do wear a bra, which is usually only when I go to work. Any other time, there's no reason to wear one.

One thing I do like about my boobs, though - my nipples are cute. When they get hard, they stick out proudly and even though I'm small on top, when my nipples get hard it's very obvious. Everyone can tell and everyone looks. And, that part I really like - when everyone looks.

So, arriving at his house, I parked my car carefully down the street, buttoned my dress up, turned my cell phone off and grabbed my overnight bag with the items he told me to bring. As I stepped out of the car and shut the door behind me, I wondered if he was watching me from his house. I was extra careful not to draw any attention to myself as I walked along the sidewalk, but with each step, I knew I was getting closer and closer to something that was going to test my courage, and something I hoped would be so exciting, so new and so satisfying, that it would forever change my dull existence.

I'd met Jay, or Mr. R., as I referred to him from time to time in our emails, several months earlier. He sent me a comment in response to one of the chapters of my story, "The Doctor Is In", and we instantly became email pals. He had this incredibly gentle, mature style about him, and I was drawn to him right away. It was inevitable that our emails eventually got personal and intimate. It was easy for me to feel comfortable with Jay because I've always been attracted to older, more experienced men, and as our emails got more and more intimate, I began to fantasize about him during my nightly finger dances down between my legs.

Before long, we were telling each other about our sexual desires and our most secret fantasies. Since I'm a professional, single woman, I enjoyed the anonymity of having a male email friend to confide in, correspond with and trade nasty thoughts with. We even exchanged very short stories we wrote about each other, all with explicit sexual overtones – his stories, putting the two of us in sexual situations which excited him, and mine putting us in situations I was fantasizing about nightly.

In one story, I had myself as a school girl who had a crush on her handsome teacher, Mr. Richardson – Mr. Jay Richardson. Of course in my story, my skirts were always too short and my school blouses were always too small. I never wore a bra and my legs just couldn't stay closed as I sat at my desk. Of course, day after day I treated Mr. Richardson to a direct view up my skirt and as each day passed, I found him looking more and more. Each successive day, my legs opened wider to encourage and facilitate his view.

The night I wrote that specific short story, I spent more time masturbating myself sitting at my keyboard than I spent writing, and by the time I was done, my panties were literally drenched and I was gasping for breath as I tried to type. Needless to say, I think Jay enjoyed the story when I sent it to him, but, I seriously doubt he enjoyed reading it as much as I enjoyed writing it and playing with myself.

In return, I found the short stories he wrote for me to be something I was forced to read time after time with my hand between my legs, stroking my lonely pussy. I'd usually carry parts of his story in my head during the day and add my own ideas to them as I lie in bed at night, masturbating furiously while my mind conjured up the visions of what he'd written. His writing had a special gift of being lewd, but not raunchy, and some of the sexual things I did in those stories touched me in a way I never thought possible

Along the way, Jay taught me it was okay to use the word 'Cunt' in my writing and in my emails. I'd never liked that word before – and I resisted it for a long time. The word seemed so demeaning to women, but, as our emails continued, I became comfortable using it to refer to my sex starved, wet, lubricated pussy. I actually grew to enjoy using the word openly, for example, telling him how I'd always fantasized about being exposed, and letting other people see my cunt clearly.

One night after dinner, I sat down to answer some of his emails with a glass of wine. The subject of the emails we were passing at that time was our most secret, deepest and darkest fantasies. One glass of wine turned into another, and then into a third for me, and before I knew it, I'd written three pages describing to Jay the things that excited me the most – all of them too shameful to ever be spoken aloud – but with Jay, I was going on and on about things I'd never even had the courage to share with my boyfriends, much less anyone else.

In that email, I went into detail on my submissive desires and my exhibitionistic fantasies. I spilled my guts telling him how I'd love to be exposed to strangers, friends and family; being made to stand in front of them naked, allowing them to touch me and look at me for the longest times..... posing me in positions that could only be described as 'hardcore'. I confessed to Jay how I'd lie in bed at night and see myself with my panties pulled down to my knees as I allowed myself to be seen and examined, maybe even photographed, or, how much I'd love to be forced to be stripped naked while someone watched.

I confided to Jay that I loved the taste of sperm and coveted the feel and texture of a man's cum in my mouth. I wrote a full page describing my fantasies of being blindfolded, stripped and used by a group of people for their sexual gratification; being made to perform oral sex on them and having my mouth filled with a profuse amount of sperm – so much so that I could drink it. I explained my desires to willingly open my legs to accept their cocks into my needy, wanton cunt, hoping they'd fill me so full, my pussy would overflow, leak out and run down my legs in the most disgraceful manner possible.

Admittedly, there was a part of my note I had to word very carefully – the part where I explained my school girl fantasies. As I wrote it, I was filled with both excitement and shame. I intentionally left out key pieces to my fantasy – hoping he might ask me to fill in the blanks. I'd already sent him a short story where he was my teacher and I was the student, but even that little teaser didn't go as far as what happened in my mind.

That note was, without a doubt, the nastiest thing I've ever written. As soon as I sent the email, I regretted it. I'd poured out my submissive, exhibitionistic and slutty heart to Jay. The things I wrote in that email were deeply personal and damning. But there was a part of me that felt good about sending it – like I was set free in some way for finally saying those things to someone. I worried about how Jay was going to take it, though.

I needn't have worried because Jay's response was calm and accepting of everything. He said he could definitely understand why someone might have submissive desires.

"Fantasies of being submissive, being blindfolded, stripped and exposed, intimately examined or even being sexually used," he explained, "doesn't mean you're a slut, Sally. It just means you'd get pleasure from someone you trust making decisions for you and putting you in a position to face exaggerated sexual conditions. I don't see any real harm in those kinds of fantasies."

Jay went on to say that giving up control and letting someone else decide your fate took a great deal of trust. He never once chastised me, criticized me or condemned me for my wicked thoughts. And, it was his gentleness and understanding which proved to me he was an honorable man who would keep my secrets safely to himself.

So, not too long after I sent that revealing email, we learned we actually lived in cities remarkably close to one another – only an hour apart. That revelation pushed my interest in Jay up a few notches, but due to his job and his position in the community, we agreed to continue our nasty friendship via chat and email, and, we both agreed it would be best if we never met in person.

Then, three weeks ago he happened to mention in an email that his wife was going out of town for several days and he'd be by himself while she was gone. As a joke, I intentionally teased him, telling him I was planning on doing some lingerie shopping, and since his wife would be gone, I asked if he wanted to help me pick out some new bras and panties.

Knowing full well we'd agreed to never meet, I taunted him, telling him I'd drag him from store to store for hours, pulling him into the changing rooms with me, and making him watch me undress as I tried on every bit of slinky, sexy and revealing lingerie I could find. I went on and on about how I'd tempt him and tease him – how I'd stand in front of him naked, turn around and bend all the way over exposing myself to him from behind and visually torture him for hours. I really laid it on thick knowing it would never happen.

When I read his reply email, he laid it on just as thick back to me, saying there was no way he'd be able to withstand that kind of torture, and how he'd have to pull his cock out and stroke it while he looked at me. He told me he wouldn't be able to control himself. He said he would beg me to let him hold my panties and he'd rub them all over his face and his cock. He told me he'd be so excited, he'd probably erupt and spray the dressing room with an unbelievable amount of cum, drenching me with streams of his hot, thick sperm. His response was so graphic, the visual I got from it made me think of him holding his gushing cock out with both hands – like a fireman holding a fire hose. I read it time after time dreaming about how much I'd love to see him cover me with his cum.

"You bad boy!" I replied back to him. "You know I'd have to make you clean me up with your tongue, don't you?"

"Oh! Really?" He said in his final reply of the night. "It's a good thing we agreed never to meet, Sally. That's something I just might enjoy."

Our emails continued on, almost daily. And, each day, we discovered more about each other. I confided to him more about my submissive desires and my yearning to role play a naughty school girl, and he told me how he'd love to go down on me from behind, licking, sucking and kissing me everywhere – and I do mean everywhere. With each email, we pushed each other more, teasing and tweaking the other to the point of premeditated orgasms.

Then, the morning his wife left for her trip, I received an email from Jay asking if I was really going shopping for new lingerie, or, if it was just a joke. I replied back telling him it was no joke – I was going to hit the big mall out towards his house. Not even ten minutes after I replied to his note, I received another email from him with just two lines.

"I know we said we'd never meet, Sally." Jay wrote. "But, if you think you'd like some company while you shop, I'll promise to be on my best behavior."

For the next hour, we went to the online chat and discussed the pros and cons of us meeting in person, and me taking him shopping for my lingerie. He even offered to pay for whatever I picked out. "Jay, do you know just a single bra can cost $30, or more?" I asked.

"Who cares!" Jay replied. "I'll bring five hundred with me. As long as I can watch you try everything on it sounds like a bargain to me."

The whole time we were discussing it, my panties were flooding and my fingers were diddling my clit and grazing up and down my pussy lips. When it became clear we were both leaning toward doing it, we laid down some ground rules. First, I made him promise not to try to touch me – he could only look. When he agreed to that, I also made him promise that he'd masturbate for me. Of course, he was just as excited as I was, and once we agreed to the rules – I told him where and when to meet me at the mall and asked what he'd be wearing.

So, to make a long story short, I met him there, at the big sign in the middle of the mall where they have the mall map. He suggested we go to the food court to get some coffee and get to know one another. After a few minutes, I was just as comfortable with Jay in person as I was through email and before too long, we were talking like old friends. His graying hair made him look so distinguished, and several younger guys – about my own age - did a double take when they saw us together. "Maybe those guys think he's my boyfriend. No wait!" I said to myself, giggling. "He could be my father!" Then, for a moment, I began to think how twisted it would be to pretend he was Daddy and I was taking him with me as I shopped for my lingerie, and, oh Gawd, letting him come into the dressing room with me.

Shaking that nasty, forbidden thought from my head, I turned my attention back to Jay and what he was saying. I felt so proud and special as I sat there with him. He was amazingly polite; he actually listened to me when I talked and the longer I sat there with him, the more excited I became thinking about this man being inside the changing rooms with me and watching me take my clothes off.

Once our coffee was gone, he leaned over close to me and whispered, "You still want to do this? The shopping and, uh.... you know, the rest?"

In the instant or two I took to think about it, I asked myself if I could really go through with something like this – if I could take him into a store and have him help me pick out my bras and panties. Could I allow him into the dressing rooms and bare myself in front of him? My heart was beating fast, and before I knew it, I was nodding my head up and down and blushing profusely. "Yes." I answered. "Definitely."

Seeing my answer, he stood up and offered his hand to me. "Well, we should get started, then." Jay said. "I'd hate for you to change your mind on me."

So, a few minutes later, we were walking arm in arm down the middle of the mall looking for our first store to visit. The story of our shopping trip still burns in my memory, but in the interest of time, I can tell you this – it didn't last hours and hours and we didn't go through every store in the mall as I'd initially envisioned.

The truth is, it took us a while to find a store that would let Jay come into the changing room with me. As stupid as it sounds, many stores won't allow a man in the dressing room with you. But, we finally found one that would. The sales girl looked at Jay, who was standing next to me, smiled a little grin and nodded her head.