Lady Emily's Guardian

Lady Emily’s Diary

17 May, 18—

So many strange, terrifying, and wonderful things have happened here at Wainwright Hall these last few days! In my wildest dreams, I never believed that my dear Mr. Singer, my guardian and beloved friend, would also become my master. Since he gave me my first sexual encounter as a birthday gift, he has been leading me down a strange and dark path of pleasure and submission. As terrified as I was at the start (and I will admit, I am still quite afraid), I am excited for what our future together will bring.

Mr. Singer has arranged for us to go away to India for a month-long tour. A friend of his and Father’s from their South Africa days will host us in Calcutta, and we will use that as our home base as we explore the country hand-in-hand. He says that we will marry during our time there. I have so longed to be a wife, so that I may know the forbidden love between a man and a woman.

I must confess that I carry a heavy burden of guilt in my heart, that I am deflowered before my marriage. My betrothed comforts me; I had not been given a choice. “If your god wishes to judge you for it, you may explain to him that you were forced,” he teased me, and I suppose that it is technically the truth. Oh, I was so afraid when I woke tied to his bed, with him leering hungrily over me. Had he given me the choice, I would have run from there and locked myself in the bedchamber. But I enjoyed it…so much, more than I can attempt to put into words. I find lately that words escape me in describing my emotions in this new situation. I may say that I am terrified and excited, but I do not feel that those words adequately illustrate the feelings that weigh on me. I can scarcely sleep (not that my new master has allowed me to do much of that lately), and every time I think about it, I feel nauseous.

Mr. Singer is not a religious man, and has never made a point in hiding this fact. I had always attended church services in the village with Nanny every Sunday, but I had always viewed this as an opportunity to socialize with the other young ladies and steal flirtatious glances at my many suitors. I have stopped attending since Nanny’s departure months ago. I suppose that the teachings of the church have had some effect on me, as a part of me fears that I will burn in hellfire for indulging in these forbidden passions.

But it is not so much that which is bothering me. No; I cannot help but think of how my parents would feel about this situation. My father would most certainly be unhappy; I cannot think how he would approve of my fornicating with a man more than twice my age, his own friend and the man who raised me from the tender age of four. I was so young when I lost Father, but I remember him well. Or perhaps my hazy memories have been supplemented by my good friend, Mr. Singer. I do know that my father was a handsome man, and very intelligent. Mr. Singer has often remarked that I remind him of my father, and I have always taken pride in that fact.

My mother’s feelings on the situation would be more difficult to guess. She died birthing me. I have never felt guilt about this fact; it is unfortunate, but women die in childbirth quite often, and I had not done anything to cause her harm myself. Terrible circumstances, that is all. Anyway, I never knew her at all, and I don’t remember much that Father may have told me of her when I was so young. Mr. Singer did not know her very well at all, so he is no help in preserving her memory. I have, however, learned some things about my mother while exploring the house as a child. I will never forget the day that I found that curious, forbidden book among her things in a spare room, off the unoccupied east wing. I was twelve when I found that book, and I read it privately in my room, blushing at the lewd descriptions. I hid the book and referenced it often, when I was alone at night, touching myself under the covers…

I have a strong feeling that my mother would not necessarily disapprove of my activities. If she could enjoy a book so perverted (and it had been well-read, even before I laid my eager hands upon it), then she could certainly understand the desires that it stirred in me. But I did not know that my seemingly innocent little foray into nipple torture would lead to this.

But I have expressed my feelings of guilt, and even now, as I write this, I feel unburdened. I feel much more ready to enjoy the life that Mr. Singer is so graciously offering to me. And every day since the first has been more exciting. It has only been four days since we began our journey (I of course mean this metaphorically; our actual journey will not begin for a few days yet), but I feel as though we have lived this way for years, and we have always been meant to live this way.

The day after our first encounter, Mr. Singer was gentle with me. He wanted to spend the day getting ahead on his work, closing out some cases, in anticipation of our long excursion. I spent the day alone, catching up on my reading and reflecting on the events of the previous night. We did not meet again until we dined together in the evening. Then, he took me by the hand and led me up to our bedchamber, and gently made love to me for the next couple of hours. Oh, it was heavenly. He restrained me, as he had the previous night, which made it all the more exciting. I’d had fantasies about being tied up, as I have laid out here in this very diary. But the reality of being completely at another’s mercy is quite a different thing from the fantasies, and my body shook uncontrollably with fear and anticipation.

I of course have no basis for comparison, but my dear old friend is an expert lover. He has already brought me to the heights of pleasure countless times. I know that Mr. Singer has spent much time with other women over the years; every few weeks or so, he would stay out so late with one of his “lady friends” that he wouldn’t return to Wainwright Hall until the early hours of the morning. But he says that he is saving all of his love for me from now on, and that I am his one. I have never felt insignificant in my life; I have always been petted and adored by the people around me, Mr. Singer included. But to know that I am his only love, the object of his strange desires, makes me feel so special. I will give him everything that I have to offer.

I perform fallacio on him willingly. I remember giggling about this lewd act with two of my friends, Miss Tatiana Howard and Miss Victoria Simonson. One of them had read about it in a strange book, and we all laughed and swore that we would never lower ourselves to such a degrading act, never. But I remember thinking, at the time, that I could do that. I would, possibly, to my husband, if he so desired. The idea even made me feel a little hot, so much so that I had to excuse myself from the conversation and find the nearest lavatory. I was so pleased when Mr. Singer allowed me to do it. It was a bit frightening at first; I wondered how I would fit his large cock down my little throat.

But my dear patient friend, he helped me, putting a hand on the back of my head and guiding his cock to my waiting, wide-open mouth. He slowly forced himself deeper and deeper down my throat, and I worked to relax my throat muscles and not gag on him. Eventually, I began to bob my head, wrapping my lips tightly around his shaft and sucking him with enthusiasm. His moaning and the tightening of his hand in my hair assured me that I was doing it right.

The taste of his semen was a shock, but he instructed me to swallow, and I obeyed. On my knees before him, I looked up at him eagerly, and he lightly touched my face. I could see the adoration in his eyes. I know that he loves me. He told me that I was a good girl, his good little whore, before helping me to my feet and allowing me to dress for the day.

Our second day was relatively tame compared to yesterday’s adventures. I still blush, thinking of how my master degraded me in the horse stables. I did not know his plans when we sat down to breakfast. He declared that it would be a lovely day to take a long ride on the grounds, and I eagerly agreed. After changing into my riding gear (which I would soon find out was unnecessary), I met Mr. Singer down in the stables. I own four fine horses, and they all get frequent use. Though I am a young lady, I do not ride side-saddle daintily unless I am in town amongst many people. With friends, like my dear Mr. Singer, I may ride as I please.

But Mr. Singer had his own intentions in the stable that lovely morning. When I entered, the horses were still waiting in their stalls. He was examining the small collection of whips and riding crops on the far wall. We have them, but we do not use them much. I do not use them at all; my horses respond to gentle handling. The only fall I’ve ever taken from a horse was not from one of my own; as a matter of fact, it was one of the horses owned by my friend Miss Catherine Gainsley, near two years ago. Not a bad fall, but I swore never to ride any horse but my own ever again.

Mr. Singer turned when he heard me enter the stable. He smiled, and I immediately recognized the wicked glint in his eye. He had plans for me; my eyes fell on the riding crop in his hand. He beckoned to me. “Come here, Emily,” he said with a smirk.

I had no choice but to slowly walk to the other end of the stable, trembling in anticipation. I have found that I enjoy the physical punishments. I know that most children are punished this way for their childish crimes, but I have not experienced such treatment. I find that it excites me, perhaps even moreso than the sex itself. As I approached Mr. Singer, I eyed him fearfully. He playfully slapped the riding crop against his open palm.

“Lady Emily,” he said, “Take off your clothes. You may leave your boots on, but that is all.”

I nodded and did as my master instructed. I slowly removed my riding dress, and he took it from my hands, draping it carefully over the empty stall. I was not wearing a tight corset that day, just a form-fitting slip, which I handed over as well. This left me in my near-nakedness, except for my brown leather riding boots and my nipple clips. Mr. Singer eyed me with approval, and I blushed. It was certainly one thing to be naked in our bedchamber, but it was yet another to be naked in the stable, with the door wide open. If any of the servants happened along…

“I have a surprise for you, Emily,” Mr. Singer said, and I couldn’t help smiling. His surprises these last few days have been so wonderful and awful, and yesterday’s gift in the stable was certainly so. He reached into his pocket, pulling out a short strip of leather. It was fashioned like a small belt, and even had a small brass buckle. Mr. Singer beckoned to me, and I stood before him, holding still as he fastened this homemade collar around my neck, buckling it at my throat. “Not too tight, is it, my dear?”

“No, sir,” I said. I trembled as he ran his hands down my shoulders, staring into my eyes. My nipples hardened, and the pressure against my clips made me moan. I wanted Mr. Singer to grope my chest, and I even pushed my breasts towards him, inviting him. He smiled, but instead reached around the back of my head, untying the haphazard knot that I’d tied. He let my hair flow down my back. He likes my hair worn loose, and has ordered me not to wear it in tight curls at home any more.

Mr. Singer ran his strong hands through my hair, pulling me to him in a tight embrace. He cupped my chin in his hand and kissed me roughly, his tongue plunging into the depths of my mouth. Before our first night together, the only kiss I’d given to a man was a small, shy peck on the lips to my former suitor, Mr. Gainsley. We had been walking in his family’s orchard. He had been talking about something…I don’t remember what, but I remember that he liked to ramble on about boring topics. I think I kissed him just to shut him up. I stood on my toes and kissed him quickly. We had stared at each other in surprise, and as my cheeks flared up, I turned and ran all the way to Wainwright Hall. I would not receive Mr. Gainsley for another week, and when I finally did, we did not speak of the incident. I was afraid that he would find me too audacious to wed.

But Mr. Singer encourages audacity, and so I reached for his riding jacket, pulling it down his shoulders before he reached up and seized my wrists. He grinned in my face. “Eager for me, my Emily? Would you like to play a game?”

I nodded, and he instructed me to stand facing the door to the empty horse stall. I did this, and listened to him walk away from me. When he returned, he lashed my wrists to the bars of the stall door. He used a leather strip to restrain me, and it dug into my skin. I still have the ugly marks on my wrists. But that was nothing compared to what the riding crop did. Mr. Singer had dropped it while playing with me. I watched him over my shoulder as he picked it up and stood behind me. “Face forward,” he snapped, and I turned my head, staring into the empty horse stall through the bars.

Mr. Singer came behind me and whispered, “Open your mouth.” I did, and he shoved his handkerchief in, to muffle my cries that his punishment would certainly elicit. I gasped as Mr. Singer kissed and nibbled on my neck. He has already found the places on my body that are the most sensitive, and he gives them attention whenever he can. I shuddered as he stepped back from me. I felt the tip of the riding crop against my back as he teasingly traced it over my bare skin.

“Spread your legs, Emily,” Mr. Singer instructed, and I did so, without hesitation. “Emily,” he said, continuing to trace the riding crop against me, “Is your little ass feeling all right?”

Truthfully, it had been a little difficult to sit since Mr. Singer’s rough treatment of me on our first night together.  He had left my ass alone since then, but I knew that he wanted to have me again. I was determined to prove to him that I could handle him, so I nodded.

“Good,” he said, and the first blow of the riding crop was delivered to my ass. I didn’t scream that first time so much as let out a gasp into my gag. But as Mr. Singer continued to rain blows on my ass and back, my groaning turned to dull screams, especially as he quickened the pace. It is difficult to describe, because as badly as the beating hurt, I wanted it. I forced myself to hold still, but I was shaking uncontrollably when Mr. Singer finally tossed aside the riding crop.

He quickly came behind me, pushing me against the stall door. With one hand, he reached around and groped my breasts; with the other, he pulled down his trousers. He forced me to bow my head and bend forward, so that my back was in-line with my restrained wrists. Mr. Singer put his hands on my hips and began to rub his cock against my cunt. I realized then that I was very wet down there; he was using my pussy juices to lubricate his cock for my ass. I held my breath as he took his cock away from me. Then, he shoved himself into my asshole, full hilt. Though he’d taken me there before, I swore that I could hear the lining of my asshole tearing to accommodate him.

He fucked me quickly. His hands stayed at my hips. I longed for him to stroke and rub my clitoris, but he was waiting to please me. For now, it was about his pleasure. He has explained to me that it may be this way at times. That is what it means for me to be his sex slave; his needs always come first, before my own. I find that I like it this way. I enjoy pleasing this man who has given me so much over the years.

He thrust into me once more as he came, holding himself inside of me as he started to go limp. I groaned, gripping the bars to which I was restrained as he removed himself from me. He stood beside me for a moment, rubbing the cuts and bruises that his beating had left on my back and ass. “Ready to ride?” he asked.

I nodded, and Mr. Singer untied me and removed the gag from my mouth. He kissed me softly. “Go saddle up your horse.”

I reached for my clothing, but Mr. Singer seized my arm. He did not grip me too tightly; besides his rough treatment of me just a few moments ago, he is usually quite gentle. “Did I say that you could put on your clothes?”

“No, sir,” I said, and suddenly realized what he would have me do. I blushed at the idea, even after what he’d just done to me. “Oh, sir,” I said, “please…”

He spanked me once on my bare ass, and I yelped out in pain. “Saddle up now, or you will get another punishment.”

I had no choice. The idea both excited and terrified me. “Yes, sir,” I said helplessly as I went to retrieve my favorite horse, a gorgeous black stallion. As I’ve written before, I do not name my horses. I don’t find it necessary to do so; they respond to my touch and to the sound of my voice, not the words spoken. I opened the black stallion’s stall door and coaxed him to me.

As I prepared my horse’s saddle, I wondered how the saddle would feel on my bare, beaten ass. Not pleasant, I knew. But as I mounted my black stallion (after an approving nod from Mr. Singer), I found that if I leaned forward, putting the pressure on my pussy, then I felt better. Much better, in fact.

Mr. Singer had chosen the other stallion, the chestnut. He rode slowly up beside me. “Emily,” he said, “is this not a dream come true for you?”

And so it was. I had forgotten the dream that I’d had years ago, which I had recorded in this very diary. I dreamed that I was riding naked through the fields, past the villages, just riding on and on. No one was around; it was just me, in my nakedness, and the horse. Mr. Singer confessed to me that he has read this diary, and that he will probably do so again, with my permission or no. He is welcome to it; I will even insert a personal greeting just for him right here. Hello, sir. I hope you enjoy reading my recollections of our lovemaking.

Mr. Singer led the way as we rode from the stable. He had allowed me to place a blanket under my ass, to further ease the pressure there. It could also prove useful on the slim chance that we encountered anyone. I could not recall one time, in all of our years of riding on the grounds of Wainwright Hall, having ever come upon another person. At the very least, I’d be able to draw the blanket around my nakedness before riding quickly away. I prayed that it would not be necessary, as it would not do much to lessen my humiliation.

We rode slowly at first, as we usually do. We rode silently up the first steep hill, which leads out to a small valley and more hills for several acres. The hills beyond the pond slope gently, creating a pleasant ride. I found that this is especially so when each step of the horse set waves of pleasure through me. Mr. Singer noticed this, and he smiled at me.

“Enjoying your ride, Emily?” he asked.

I nodded. “Yes, sir,” I managed, and I bit back a moan.

Mr. Singer laughed and urged his horse faster. I followed suit and we quickened the pace to a full-out gallop. My breasts bounced freely, the clips pinching my nipples more than ever as the steady motion brought me to an intense climax. I screamed, resisting the urge to pull the reigns. The horse seemed to sense that it was time to slow down, and as he slowed to a gentler speed, I nearly collapsed on top of him.

Mr. Singer, several yards ahead, noticed that I had not kept pace with him. He turned around, and we stopped, meeting at the top of a larger hill overlooking much of the yard. Mr. Singer climbed quickly from his horse, a look of mixed amusement and concern on his face as he helped me (nearly pulled me) from my saddle. I weakly fell into his arms and he swept me up, he was so strong, and held me tight, kissing me.

I will have to continue my narrative at another time; even now, Mr. Singer calls me to his side. We have not played as much today, and I am eager to see what surprises he has in store for me now.

19 May, 18—

I’ve had hardly a spare moment these past couple of days. Between preparing for the trip to India and paying last visits to my friends in the area as a single woman (won’t they all be surprised when I return as a married woman?), as well as spending time (lots and lots of time) with my dear Mr. Singer, I’ve hardly had time to even think. But Wainwright Hall is quiet now. Mr. Singer has gone to visit with a client, and now that all of my trunks are packed for the trip, I think this would be a good time to sit quietly and reflect on the last few days.

When I left my previous entry, I was describing my pleasurable ride on the grounds. When Mr. Singer and I stopped, we left the horses to run as they pleased (knowing they would quickly come back when summoned), and Mr. Singer spread the blanket out on the grass. He motioned for me to lie down, and he did, he lying beside me as we touched hands and looked up at the clear blue sky. A light spring breeze was in the air, and I shivered slightly, my nipples hardening again. I felt chilly between my legs, and realized that I was very messy from my climax on the black stallion.

Mr. Singer noticed my trembling, and he removed his riding jacket, wrapping it gently around my shoulders. “Better?” he asked. I nodded, and he kissed my forehead softly. We sat together, and I rested my head on his chest and closed my eyes. I felt wonderful. Mr. Singer ran his fingers softly through my hair. We sat this way for quite some time, enjoying the comfort of each other’s bodies. As my guardian, Mr. Singer had not doled out much physical affection. This is not so unusual; indeed, it would have been seen as improper if he had given me the hugs and kisses of an affectionate father. But how I craved it as a young girl, ever since he’d held me in his arms and comforted me after Father’s death. It is different now. I will get all the love that I need from my dear old friend.

After a time, Mr. Singer whispered in my ear. “I want you, Emily. Lie down.” I slowly but eagerly obeyed. Mr. Singer got up on his knees and smiled down at me as he slowly removed his shirt. I returned his smile, anticipating the pleasure that he would deliver. He did not fully remove his trousers, and he kept his boots on as he straddled my hips. I wrapped my legs around his waist, and as he fucked me, the heels of my riding boots tapped against each other. I rose up on my elbows and raised my hips higher to allow Mr. Singer to fuck me as deep as he could. I wanted to feel him all the way up inside of me.

Mr. Singer grabbed me by the front of the leather collar and pulled my face to his, kissing me roughly as he pounded me. He breathlessly whispered in my ear. “You’re my whore, aren’t you, Lady Emily?”

I groaned. “Oh, yes, sir!” I cried.

“Say it, Emily!” he cried, tightening his grip on my collar. I stared into his eyes; he looked crazed and wild, and I feared and adored him.

“I am your whore, sir! Oh, sir!” He released my collar and grabbed me under my knees, forcing me to put my legs straight in the air. It was difficult to hold them up with the heavy boots on, but I spread wide and allowed him to slide between them, fucking me harder and harder, and closer and closer to another climax.

It was almost, though not quite, as intense as the climax on the horse. We came simultaneously; it was beautiful to feel him relax inside of me. He carefully helped me to lower my legs. I felt weak, and I trembled slightly and closed my eyes, laying back and relaxing as Mr. Singer pulled off my boots and gently rubbed my feet. His hands did not travel up any further than my ankles as he worked them, but even that touch made me sigh contentedly.

When Mr. Singer stopped rubbing my feet, I opened my eyes and gazed up at him. He was kneeling beside my feet, looking back at me with a smile. I always thought he was handsome, but at that moment, he was almost blindingly beautiful to me. It really is no wonder that my good friend Miss Tatiana Howard has been infatuated with him since we were young girls. Even now, the thought of her jealousy upon my return as Lady Emily Singer makes me smile. I am afraid that I am turning into a petty, wicked thing…and worse, I am enjoying it very much.

“Well, my lady,” Mr. Singer said, “are you ready to go home?”

I felt so exhausted. All I wanted to do was collapse onto my bed (or rather, our bed) and sleep the afternoon away. I nodded weakly, and he whistled for the horses while I pulled on my boots. I was still wearing Mr. Singer’s riding jacket, and he allowed me to keep it on as we traveled slowly back to the stables. I found that the ride back was much more uncomfortable than the ride out, since my pussy had gotten such a workout at that point.

Mr. Singer allowed me to dress while he put the stallions back into their stalls. I realized, as I finished pulling on my dress, that nobody had seen us. I’d ridden around the grounds naked, and nobody was the wiser. Mr. Singer and I had committed lewd acts, right there in the open, and only God was there to witness, if He cared to do so. The idea made me giggle uncontrollably, and I was in near hysterics by the time an amused Mr. Singer came to my side.

He wrapped his arms around me, and I calmed, my laughter dying down to a girlish giggle as he kissed me softly. “You had lots of fun today, Lady Emily, didn’t you?”

I nodded. “Oh, yes, sir,” I said, and I knew that the insane grin on my face told him everything that he needed to know.

“Good girl,” Mr. Singer said softly, and he kissed me on the forehead. “Would you like to take a quiet nap before lunch?”

I nodded. By now, I know the difference between a “nap” and a “quiet nap.” A quiet nap is just that, a quiet little afternoon snooze in each other’s arms. A “nap” is something entirely different, and much resembles the activities we’d just performed in the field. It’s hard for me to believe that our affair began less than a week ago; we’ve already gotten into the habit of “napping” after tea every afternoon, the time that I would normally reserve for receiving gentleman callers.

I told Mr. Gainsley of my betrothal this very afternoon. I would not say to whom, and he was terribly upset. It was quite an ordeal, actually; after explaining to him that I was going to India to make arrangements for my marriage, he nearly flew into a rage. Mr. Gainsley, usually so mild-mannered, stood from his seat and accused me of leaving him on a hook. “I was denied when I first proposed marriage to you, but I had hope that, when your guardian granted you freedom to marry, that you would choose me. I have waited for you, lady, and you care nothing for my feelings.”

I was very upset by then. I truly did not think that Mr. Gainsley would take the news so hard. I felt it only right to tell him, because he has courted me for so long. But since Mr. Singer first denied his request for marriage, his visits to me have been much fewer. I am surprised that he has not yet proposed marriage to Miss Beatrice Howard, whom he has been courting for some months. I told him as much, and he snapped back, “I care nothing for any other girl. I had to pass the time somehow while you…led me on.”

I had dissolved into tears, I am ashamed to say. Mr. Singer came to my rescue; he was preparing to leave for the village, and when he heard Mr. Gainsley’s shouting and my distress, he came into the parlor. In his calm way, but with anger in his eyes, he ordered Mr. Gainsley out. “You will not speak to the lady of this house in such a impudent manner. Especially after she has confided information to you, as a friend. Leave here now; do not return, or you will meet with the end of my revolver.”

Mr. Gainsley did not dare challenge my brave Mr. Singer, and with one last, contemptuous glance in my direction, he left Wainwright Hall. Undoubtedly, he will tell his sister all about the incident. Fortunately, the information will be delayed, as she is away visiting relatives in the south. I do not think he would risk hurting his pride by announcing it to anyone else. By the time the news gets around that I am betrothed to a mysterious man, we will be well on our way.

Mr. Singer kissed me softly before departing to town. “You’re not upset, are you, my dear?” He always cares for me so. I assured him that I was all right. I was shook up by the confrontation, but otherwise, my feelings were intact. And so, Mr. Singer departed.

I am planning a surprise for him this evening. Rarely do I spend time in the kitchen, as we’ve always had a cook on hand, but when I was young, my nanny taught me how to make the most sumptuous tipsy laird, a Scottish variety of trifle. My nanny is Scottish, and I think of her now, far off in the Highlands, tending to her ailing sister. I do not know how I will break the news to her that I am going to marry Mr. Singer. I will wait to write to her upon our return from India, but I do not know what she will make of the situation. The odds are against my ever seeing her sweet old face again, anyway, but still, I do not want her to remember me ill.

But I will not worry. I will be happy in my newfound love. I cannot believe that, in just a few short days, I will be on my way to India, and on my way to becoming Lady Singer. My heart races just thinking of it.

22 May, 18—

We depart for India on the morrow. Mr. Singer and I came by train to London this very afternoon, and are only staying the night at the home of an old friend. We will set sail very early. I have been on ships for several weeks at a time, our longest trip being to America some years ago, but I am nervous. I don’t believe that it is the possibility of seasickness that worries me, but rather what awaits us in this mysterious land.

Mr. Singer knows that I am anxious, and he attends to me with kind patience. Our sleeping arrangements are separate tonight; our host, of course, does not know the nature of our relationship. But Mr. Singer has assured me that he will creep to my bedside in the night, and will hold me gently and listen to all of my concerns. He constantly reassures me that what we are doing is right. I am ashamed that he knows that I still have my thoughts of doubt, try as I might to hide these from him. But he knows me so well. He knows what is in my heart.

At times I feel that I may burst with love for him. Oh, my Mr. Singer is such a goodly, handsome, wonderful man, and I fear that I am not worthy of his worshipful love. I try so very hard to please him. Last night, after he finished tying me down and having his way with me for a time, I couldn’t stop crying, and I had no answers to his questions of why. I still am not certain of the cause of my outburst; my emotions are out of control as of late. I am usually a very controlled person, so this frightens me more than anything else. But around others, such as our host here in London, I am myself, smiling and polite and occasionally witty. It comforts me to know that I may show my true feelings to Mr. Singer. Even if we don’t understand them, he does not judge me harshly. He is still my friend.

I am exhausted, so I will leave this tonight. When I write again, we will be on the ship and on our way to India. Perhaps by then, the excitement of our adventure will overtake my apprehensions.

My Mr. Singer is at the door! Out with the light, and into bed we go.

30 May, 18—

My head still spins with the events of last night, of the past week! My dear Mr. Singer is a wicked and wonderful man, and under his influence, I have done things that only a fortnight ago, would have made me dissolve into screams of horror. I do love him so, for he challenges me and gives me the wildest and most wonderful pleasure. I tremble now to think of it all.

I will come to the events of last night in a moment. Our first few days on board were not out of the ordinary, but were wonderful in themselves. We are onboard a small passenger vessel; there are perhaps 150 on board, not including the crew and the captain (oh, that wicked Captain! On that in a moment). Mr. Singer and I technically have separate quarters, but he does not fail to come to me in the night. His room is a decoy, really, as it would be most improper for an unmarried man and woman to share a room. During those first few days onboard, when we would sit amongst the other wealthy passengers at dinner, Mr. Singer would give me the most secretive, dirty little glances, enough to make me blush and giggle briefly behind my napkin.

We do not know anyone on board, but Mr. Singer has quickly become a favorite among the ladies, married and single alike. It has always been this way; Mr. Singer is so handsome and charming, yet he does not become inflated with the praise as a lesser man might. I remember feeling a little jealous before, when I would see him flirt mildly with a lady at one of our neighbor’s balls. But it does not bother me now to see him talking with other women; indeed, it is all the better, as I know that I am the only one who belongs to him.

Last night, we had the honor of dining at the Captain’s table. The Captain (whose name, for reasons that will soon be obvious, I do not wish to commit to paper) is a young man, perhaps even a bit younger than Mr. Singer himself. He is Portuguese, but his English is very good. I was seated right beside him, and I could not help but notice how handsome he was. He is tall, like my Mr. Singer, but has a more solid, wide build. He has a lovely dark complexion…oh, goodness! I blush to think of him.

He regaled our small party with stories of trips he’d made all over the world. All the while, he would specifically address me, giving me flirtacious glances, and at one point, he reached over and lightly brushed my hand. I am no stranger to the advances of men; if you ask my dear Mr. Singer, I am the most beautiful girl in the world. I am not so convinced of that, but I know I am pretty. I am not blind.

I cannot help myself; I do so enjoy the attention of men. I returned his attentions, but glanced frequently at Mr. Singer. He was attending to the lady beside him, and when our eyes met, he gave him a little wink and a nod. He approved of my accepting the attentions of the handsome Captain. And so I fully enjoyed what I had thought would be an innocent flirtation.

After dinner, the other ladies and the older gentleman in our party departed for their rooms. The Captain invited Mr. Singer and me back to his private chambers for a nightcap. I was surprised by the invitation; it is not customary for women to enjoy a drink after dinner with the men (though Mr. Singer and I had always done that, well before we were lovers). I looked at my master nervously, but he was nodding his head. “I’m game,” he said. “What say you, Lady Emily?”

“All right,” I said. I smiled at the Captain. “Thank you.”

He took us to his large chambers. His bedroom was separate from his sitting room, and that is where we sat, in high-backed chairs, enjoying coffee mixed with whiskey and cream, a drink that the Captain had been introduced to in Ireland.

“Lady Emily has done quite a bit of traveling herself,” Mr. Singer said. I gave him a look of surprise; it was almost as though he were trying to set me up with the Captain! He had a wicked glint in his eye, a look that, by now, I am very familiar with. What was he up to?

But the Captain began to question me with earnest, and I told him about the excursions that Mr. Singer and I had made to various points in the world. “I have never been to Asia before,” I admitted.

“This will be my third voyage to India,” the Captain said. “There is much profit to be made these days. This will be my last voyage as captain of this passenger vessel. I have been appointed to a trade ship.”

“Which do you prefer?” I asked. And the Captain and I talked on for nearly a half hour. I had almost forgotten that Mr. Singer was in the room, until he cut in. And his comment was most unexpected.

“Captain,” he said, “I do believe that you are attracted to Lady Emily.”

I nearly gasped. I glanced at the Captain, but he did not look at all fazed. He even laughed a little. “I can’t deny that,” he said. He gave me a familiar look, a look of longing. I had seen that look more than once, and on more than one man. “She is not only beautiful, but intelligent and fun.”

“She certainly is,” Mr. Singer agreed. “She is a lot of fun.”

I sat in shocked silence as Mr. Singer revealed our secret to the Captain. “Lady Emily is my whore, Captain. She does anything that I ask her to. Isn’t that right, my dear?”

I swallowed quickly. “Yes, sir,” I said quietly. Mr. Singer grinned.

“Captain,” he went on, “You are an attractive man yourself. I’m sure that you’ve had a few romps with some female passengers.”

“Well,” the Captain admitted, “Not as often as you might think. Many of the ladies on these voyages are stuck-up and pampered.”

“Lady Emily is pampered, to be sure, but she is anything but stuck-up,” Mr. Singer said proudly, and I could not help smiling at that, as mortified as I was. “Captain,” he said, “you have been very kind to us since we arrived on this ship. And I can tell that my Lady Emily, as devoted as she is to me, is quite taken with you as well. Isn’t that true, my lady?”

I had to confess; I had no choice. “Yes, sir,” I said, my voice faltering.

“Captain,” Mr. Singer said, “I would like to properly thank you by offering my whore to you for use. What would you like to do to this pretty young lady?”

I looked at the Captain as he eyed me. He looked both lustful and contemplative. “Would she…would she suck my cock?” he asked, addressing the question to my master, as was appropriate.

Mr. Singer nodded. “Certainly. Lady Emily, stand up and remove your clothes, please.”

I did so; the thought never even occurred to me to resist. I looked at the Captain as I removed my evening gown. When I was down to my corset, I turned around. “Will you give me a hand, please?” I asked. As the Captain awkwardly untied my corset, Mr. Singer gave me a smile of approval.

Completely naked (save for my nipple clips, which the Captain eyed with curiosity), I stood before the Captain. I wasn’t certain what he would have me do next. Did he want me to remove his clothes? Get right down to it?

He looked a bit uncertain himself, until Mr. Singer resolved the issue. “She can take a little rough handling, Captain, but do not be brutal to her.”

The Captain nodded and advanced towards me, an eager look in his eyes and a grin on his face. He seized my shoulders and forced me to my knees. He pulled down his trousers, only enough to reveal his huge, stiff cock. Oh, God! He was even bigger than my Mr. Singer. The Captain seized the back of my head, and I knew what to do. I quickly swallowed his engorged member, deep-throating him with only a little difficulty. He fucked my mouth quickly, but I’d had enough practice with Mr. Singer at that point that I knew how to breathe properly. As he fucked me, he moaned in ecstasy; it had been a long time since he’d had it like this. As apprehensive as I’d been about my task, I felt good, knowing that I was giving the Captain this pleasure.

The Captain did not hold out as long as Mr. Singer, and he gripped my hair harder and grunted as he came. I swallowed him with his member still lodged down my throat; this was a trick I’d perfected with Mr. Singer, and the Captain moaned one last time, stroking my hair as he removed himself from me. He looked down at me, looking surprised and grateful for what had just happened.

“Thank you, my lady,” he managed. He helped me to my feet.

“You’re welcome, Captain,” I said. He leaned in and kissed me roughly, grabbing my face in his hands. I did not stop him; I leaned in to his kiss. His tongue was a little too active for my taste, probing my mouth intrusively.

I felt a pair of hands on my waist; Mr. Singer had come up behind me. As the Captain kissed my mouth, Mr. Singer kissed the back of my neck, left exposed by my elegant hairdo. He briefly addressed the Captain as he gave my neck some attention with his teeth. “Captain, you may have her ass while I take her cunt. You game?”

The Captain responded by grabbing my hand and leading us into his bedchamber. His bed was quite large. He grabbed my other arm and threw me on the bed roughly.

Almost in an instant, he and Mr. Singer were on me. I did not know how to position myself to accommodate both gentlemen, but they resolved this for me by putting me on my side. Mr. Singer positioned himself to face me. “You’ll need lubricant, Captain,” he said. He addressed me next; “Spread wide, Lady Emily.”

The Captain seemed to be prepared for an impromptu sexual encounter, because he had a jar of lotion in his bedside drawer. He lubed up quickly, and positioned himself behind me. The men entered me simultaneously; I yelled out in pain before Mr. Singer put his mouth on mine, kissing me roughly.

The Captain’s huge cock tore up my ass; it is still in pain as I write this, laying on my stomach on my bed. I have not sat down all day; I don’t know how I will get through dinner tonight. To muffle my moans of pain and pleasure, Mr. Singer pushed my head against his shoulder, allowing me to scream against him. Oh, God, that Captain was very rough with me. He had seen the bruises on my back, and he knew what kind of treatment I was accustomed to. He came only moments before Mr. Singer and I; for a few moments, the three of us lay in our cum-soaked mess, sweating and panting. Mr. Singer reached for me, kissing me softly, and the Captain reached over and played with my nipples, fascinated with the metal clips.

Mr. Singer and I departed soon after. The Captain kissed me once more after I’d dressed. “We will have to do this again, very soon,” he said to me and Mr. Singer, as though we’d just enjoyed an evening of cigars and drinks, nothing more.

“That would be nice,” Mr. Singer said.

“Yes,” I agreed. “Goodnight, Captain.”

Because it was so late, and the only passengers still up and awake would be too drunk to notice us, we walked hand-in-hand back to my room. We said nothing, though, until we were in my room, with the door closed. Mr. Singer pushed me against the door and kissed me roughly. But as I thought he would reach for my dress to rip it off, he stopped and stepped back. “Did you enjoy yourself this evening, Emily?”

I must confess, I did not know what to say. I felt my face flush, as though I’d only suddenly realized what had happened. “Yes, sir,” I had to admit, but I was burning with humiliation.

Mr. Singer smiled. “You are an adventurous little whore, Emily. I like that. It turns me on to see you with another man.”

I had figured this much, but hearing him say so was still surprising. “Really, sir?”

He nodded. “You’re a very special girl, Emily. You enjoyed giving the Captain pleasure, didn’t you?” I nodded; goodness, it was as though he had read my mind! Mr. Singer smiled. “From now on, you may give pleasure to any man that you please…with my approval, and while I am present, of course. I will protect you from harm, and we’ll all get to enjoy ourselves.”

I nodded, not certain of what to say. My master would offer me to other men? The possibilities were nearly unimaginable; it frightened and thrilled me. “And,” Mr. Singer added, that wicked grin on his face, “Perhaps we might invite women to join as well.”

I giggled at the idea, and instantly, one woman came to mind. My very good friend, Miss Tatiana Howard. I’ve always thought she was so beautiful, and she was very attracted to Mr. Singer. It had also been rumored that she had had a brief affair with a young gentleman in London; though she had denied it publicly, she had confessed it to me in confidence. If any woman I knew would be willing to join us in our bedchamber, it would be my whorish friend.

The rest of our voyage will be very exciting. Though I don’t see any other men on board who would be much fun to play with, I know that my Mr. Singer and the Captain will keep me plenty busy. For now, though, I will enjoy my quiet time alone. I am quite exhausted from last night, and I want to be well-rested for the next time my master and I meet with our new friend.

1 July, 18 –

I have neglected my writing this past month, but I have been as busy as I previously predicted. My days and nights have been spent serving Mr. Singer and the Captain, ensuring that both men are fully satisfied at all times. They are never shy about returning the favor; however, Mr. Singer does not allow the Captain to have me in my pussy. “This little whore is to be my wife, and her cunt is my property,” he explained to our friend. Still, the Captain adores my ass. He has become fond of spanking me, while Mr. Singer watches. He has a heavier hand than my master, leaving me sore for days on end after a night together.

But now, my mind is preoccupied. We will be in Calcutta the day after tomorrow, and I am very excited to begin the next part of our journey! Mr. Singer has told me a little of his old friend, our host. Mr. Charles Morrison works for the British government. He and his young wife live on a large estate. As I previously noted, Mr. Morrison knew my father. But Mr. Singer recently revealed to me that he also knew my mother. In fact, “he knew her very well,” Mr. Singer said, with a wicked look in his eyes. I am eager to know exactly what he means.

This morning, Mr. Singer and I sat down with a large map of India. He pointed to all of the places where we would travel. He has been eager to travel to India himself, and I am so honored to be taking this trip with him. He is especially eager to view the Buddhist temples; though he is not a religious man, he has a fascination with religions of the world, particular the eastern ones. His excitement is contagious, and I cannot wait to see all of these exciting things with him.

Tomorrow night, there will be a feast at dinner. I know that the Captain will host Mr. Singer and me in his chambers when the party is over. I am surprised that the other people on the ship do not even seem to suspect our activities; indeed, the other women (most of them older, and, as the Captain observed, snobbish) are impressed that I am such a frequent guest at his table. I fabricated a tale, that he and my father had served in the naval forces together. It makes me laugh to think of it; I do not know these people, and whether or not I encounter them again is of no consequence.

I will probably never see the Captain again, either, but I do not leave our voyage with any regrets. We have had our fun with him, but I will always have my Mr. Singer. I will confess, I have fantasized about being with him and a lovely Indian woman. I believe that Indian women are some of the most beautiful in the entire world, and if I am able to strike a friendship with a woman there, I may be bold enough to invite her to our bedchamber. Mr. Singer would be so pleased.

I think about my life two short months ago. I was a virgin then; though I was not innocent, I could not imagine that I would ever do the things that I have done. I find that my shame is leaving me; I no longer blush so easily when I stand naked before a man. I can hear Mr. Singer’s dirty remarks to me, and can answer him in kind. I am finding that my Mr. Singer is right: I am a whore, and I love it.

I will rest tonight, to be fully prepared for a full night with the Captain and Mr. Singer tomorrow. The day after that, we will be in India…and my new life will really begin.