Chloe & Me – ebook



Chloe & Me by S.M. Ackerman

After being caught entertaining his deviant fantasies by his step-sister, Chloe, at the top end of their parent’s garden, Chris finds himself in quite the quandary. Either risk humiliation beyond words by her leaking pictures and videos of him birching himself while wearing Chloe’s clothes or become her absolute submissive. What is a boy of nineteen to do with a choice like that? Weighing his options, he goes with the obvious choice, much to Chloe’s happiness. Their parents are shocked by the complete turnaround in one weekend when they notice the step-siblings, who have clearly hated each other, are now getting along quite nicely.

S.M. Ackerman presents a twisted tale of debauchery with Chloe & Me. Chris not only complies with becoming his mistress’s personal maid, but has to wear women’s clothing, collars and leashes. Deep down, however, he finds he is overjoyed at the prospect of serving her every whim.

Soon, Chloe informs Chris that not only will he serve her, but he will also be serving her girlfriend, Ann. Sweet, shy, little Ann is the one girl that Chris always imagined as having for his own. Now the situation has changed. When Ann isn’t being spanked or flogged by Chloe, she controls Chris’s every move when their mistress is away.

Will Chris be able to leave Chloe’s service once she tires of him? Can he finally convince Ann to be his and his alone?

Includes: bondage, flogging, birching, whipping, caning, gags, collars, leashes, feminization, lesbian scenes, oral sex and much more!

Additional information

Artist Credit

Cover Art elisanth –

Publish Date


Page Count


Word Count





This is my sordid tale, my darkest secrets, deeply concealed, yet so easily revealed to the one person who would know how best to benefit from them. I had been stealing my stepsister’s clothes, dressing in them for my personal sexual enjoyment, with little thought to the consequences of being caught.

By eighteen I was taking every opportunity to walk free and cross-dressed out in the open, though not through the city streets, and certainly not in any places that I might actually be seen! I walked alone around the large grounds of my parent’s home, always late at night, always hidden by the dark.

Aroused by wearing short skirts and stolen panties; often with a bursting erection filling them. My excursions were frequent but always whilst they, my family, were all out.

As I got older I began to feel guilt, I developed a need to be punished, not as myself of course, but as my alter ego, Chrissie. I took to administering a variety of implements to my bent, panty covered buttocks. At any opportunity, I thrashed myself soundly as punishment deserved for my shameful behaviour. I was nineteen and my stepsister had just turned eighteen, when the true horror and consequences of being discovered exploded into my self-satisfying life.

Chloe, my step-sister, returned early from her friend’s house, she had been supposed to be away for the whole of the weekend, as were our parents. When she returned home that fateful Saturday evening, I was not in the house; I was out in the grounds. Cross-dressed and bent over my favorite low hanging tree branch, thrashing my buttocks as hard as I could. Unwittingly I presented her with an entertaining display, along with ideas for the future.

Cane is not exactly the right description of the implement that thrashed my naked buttocks. Instead, I had selected four, thin, very pliable switch cuttings taken from our apple tree trimmings pile. Trimmings which Dad had gathered together on the far side of the garden, ready to be burnt sometime later. Being desperate, I had not even taken the time to bind them together. Instead, I relied on my tight grip to hold them bunched as I beat myself.

It is never easy to reach around and lash one’s own bottom. To a degree it is possible, though the strength behind each stroke, and the duration of the torment are of course under your own control, unfortunately. A level of self-control which detracts from the pleasurable feelings generated by being whipped. Much as I might desire total helplessness, it is clearly impossible to achieve when alone.

To replace real subjection, I used daring. By that I mean that I secured all but one arm with leather belts, strapping myself tightly to the bough. Thus making my escape from the branch a slow process to complete, leaving me with the fear of discovery ready to explode into my dark games. The switch twitched as I hesitated, nerving myself to deliver the next stroke. Thrashing through the air, driven by my own wrist, all four wood strips contacted my flesh, bending and whipping across and around my thighs; where individual tips cut thin lines deep into the tender receptive flesh of my outer thigh.

With each lash, my over charged cock forced my panties to tent upward and out, my flesh sought the cooling caress, and relief offered by the night air. The flexible material of my panties stolen from Chloe’s bedroom were gathered around my aroused protrusion, which somehow remained contained and covered by her flimsies. I lashed again and again as I generated a rhythm of strokes. Enjoying the pain each lash created, always trying to vary the points of impact on my flesh, because I knew that later, once I was back inside our house, and still alone. I would be admiring and touching those lovely swollen indicators of my torment.

Then, and only then, once I had suffered the self-infliction of punishment to which I had sentenced myself then, would I allow my bursting erection release from the panties I wore. Stroke after stroke lashed against my skin; what a picture I present I told myself to add to my torment. Secured by all but one arm, and that free arm whipping at my partially reveal buttocks. Swoosh; the twigs had cut through the air, impacted hard certainly, but never hard enough as far as I was concerned. To make up for the lightness of each stroke I administered numerous strokes. I had passed sentence on myself yesterday, deciding to administer at least one hundred lashes of the four-switch whip. It might sound excessive, but when I whip myself, I can be quite cowardly in a subconscious way. Stroke followed stroke, beating a tattoo against my arse, each lash driven by my inner guilt and sexual excitement.

“Hi there,” the voice had exploded in my ear. I knew that voice, I struggled to pull upright hoping to cover my behavior. Ridiculous really, there was no way a witness could misinterpret what they had seen, and besides my bottom and thighs were covered in welts, if any conformation was needed.

I knew that voice. I desperately wanted that voice to be a part of the fantasy I was indulging in, but it wasn’t! She grasped my free arm, wresting the whip from my clutching fingers by bending and pinching my thumb, she then forced it downward.

“Stay still you disgusting little worm!” She whispered into my ear.


There are no reviews yet.

Be the first to review “Chloe & Me – ebook”

Your email address will not be published. Required fields are marked *

You may also like…