My Evil Stepsister Returns
Chapter One – An Unexpected Visit
I knew that there was something wrong the minute I opened the door and walked into my house. The first clue was that I could smell fresh baked cookies and my wife does not bake. In fact if it was not for the pizza joint around the corner, the fried chicken place down the block and the Chinese takeout we would probably starve to death. Of course I do cook just to shake up the menu from time to time. So at this point you are probably wondering why I would have married a woman that can’t cook. After all an old adage does say that the way to a man’s heart is through his stomach. But, in my case the way to my heart starts a little bit lower than that. So, if you could have just one look at my wife you would know.
If you look up Goddess in the dictionary you will find Pamela’s picture in the description. She is not overly tall, about 5 feet 6 inches in her stocking feet. But when she is dressed to thrill with either her fuck me pumps or her high-heeled boots she is much taller and very intimidating. She keeps herself in excellent shape so even without the aid of heels her legs look long, shapely and gorgeous. If you shift to the top of this perfect woman you will find honey blonde hair that hangs below the shoulders framing a perfect face. Drop a little lower and her c cup breasts are something to be amazed at. Oh, I know, many men prefer breasts that are larger, but I never got into that idea. I think if a man spends too much time thinking of huge women’s breasts he probably has an infantile complex.
There was laughter coming from the living room and one of the raucous voices was plainly that of my wife, but the others I was not so sure about. A couple of them sounded vaguely familiar but the memory was too far in the past for me to put my finger on it.
Something told me that I needed to find out what was going on before I let it be known that I was in the house. So as quietly as possible I slipped up to the doorway to the living room and peeked around the corner. No one noticed I was there as their’ attention was riveted to the big-screen television on the far wall. Their backs were towards me so I did not recognize anyone in the room with the exception of my wife. I did however recognize who was the center of attention.
On the television screen was a video of what appeared to be a young woman wearing a frilly dress that hung down to just above her knees. She was holding hands with a young man as they walked through a flower garden. I gasped loud enough so that I gave myself away.
“Well, look at this,” a voice from my past declared. “Here is our favorite girl now. Come on in and have a seat, your stepsister, wife and I have been baking cookies and reminiscing about old times. I am sure you will enjoy watching some of these old movies that I took of you dressing up and living as the girl you always wanted to be.”
I was flabbergasted. All I could do was stare at the hideous pictures playing on the screen, remembering how my stepmother and stepsister would deliberately dress me up in female clothing and humiliate me in front of my friends.
Finally I got my breath back enough to confront the wicked woman sitting in my living room. “How in hell did you find me? I thought I had rid my life from you and your evil and twisted ways.”
“Don’t you dare talk to your stepmother in that tone of voice!” My wife interjected.
I stood with my mouth open looking first at my wife and then back to my stepmother who was sitting, her booted legs crossed with her right foot swinging slowly back and forth. I wanted to run, to get away before I knew that she and my stepsister would again entrap me. But I could not run, in fact I could not take my eyes off of that booted foot. It was almost as if I was hypnotized much as a cobra is hypnotized by the flute of the snake charmer. The room was completely silent except for the slight swish of nylon being brushed against boot leather.
“Pamela,” my stepmother began. “Do you see how he stares at my boots? In just a minute his tongue will sneak out of his mouth and lick his lips. Do you mind if I ask you a personal question?”
“Of course not,” my wife answered. “Ask away.”
“Well, I was just wondering, does Jason lick your boots for you?”
“My lord, no!” Pamela declared. “Why in hell would he want to lick my boots?”
“Look at him dear. He can hardly keep himself from falling to his knees and crawling over here. Look at his face. See how flushed it is. And look at the front of his pants. His little clit is so hard that it is causing the front of his pants to tent. Of course since he has always been a little short in the manhood department it is a little difficult to see clearly. Maybe you should have him take off his pants for a better view.”
“Are you suggesting that he wants to lick the boots of his own mother?”
Nobody bothered to correct the fact that she was not my real stepmother and the woman with her was not my real stepsister.
“I am sad to have to say it, but yes he does. I have to accept the blame. You see when I found out he was licking my boots behind my back I figured it was better to have him do it in the open rather than sneaking around and then lying about it. I really don’t think there is anything worse than a liar, do you? I bet that if you think about it, you will remember some times when you found your shoes or boots in a place where you did not remember putting them.”
“Are you suggesting that Jason has been licking my shoes and boots without my knowledge?”
“I am absolutely sure of it. Once a bootlicker always a bootlicker as the saying goes. You can never break him of the habit. You might as well either divorce him or live with it. And if you decide to do the latter then make him do the job right. Once he has cleaned them he should be made to polish them as well, don’t you think?”
“I cannot believe this. First I find out that he is a closet cross-dresser and now you tell me he is a bootlicker as well.”
“Don’t take my word for it dear. Sandra here will tell you the same thing. Tell her Sandy about your sister’s perversities.”
“Mom is telling you the God’s honest truth. For a long time after I found him stealing into my room and putting on my clothes we tried to break him of the habit. And then when we found out about his fetish for our shoes and boots we tried to reason with him. Mom grounded him and even took him over her knee and used her hairbrush on his bottom but nothing worked. So we finally decided if he wanted to be a bootlicking girl then we would help him achieve his desires. And truthfully it was kind of nice always having clean polished footwear. But I think you should ask him yourself.”
“Jason, for Christ’s sakes speak up. Is what they are saying true?”
I wanted to deny it. I wanted to say that ever thing they had said was a damned lie, but I could not make my tongue form the right words. The problem was, part of what they were saying was true. At least the part about my fetish for shoes and boots was true. The part about me wanting to wear my stepsister’s clothing was a damned lie, but that did not alter the fact that I had worn he clothes many times. And I still could not take my eyes off that swinging foot. And to make matters worse my stepmother’s precognition about my tongue wetting my lips came true. I could not stop myself; I had to wet my lips.
I could hear heels tapping out a quick tempo and coming across the room towards me but even then I could not take my eyes off that pendulum of a foot. But then my wife was in front of me blocking my view. She reached out and grabbed me roughly by my hair and then delivered a resounding slap across the side of my face.
“I asked you a question, damn it. Now answer me. Is what your mother and sister telling me the truth?”
I shook my head more to clear it than to deny her question. I swallowed hard to try and get my heart out of my throat. Trying hard not to get myself into deeper trouble than I already was, I began to speak.
“Some of what she says is true.” I hesitate to say more.
“Some of it you say? So tell me which part is not true?”
I appreciated that she had worded her question in that form as it at least gave me an opportunity to answer without going into a great amount of detail about my footwear fetish. “The part where they said I insisted on dressing in Sandy’s clothes is not true.”
“Really? Bring a straight backed chair from the kitchen and set it so you will have a good view of the television but not your mother’s boots.”
I did as she instructed but I took more time than needed to bring the chair back. I wanted to be able to prepare myself for what I was sure would be a video of me performing wearing Sandy’s hand me down clothing. I brought the chair back into the room and tried to get just the right angle where I could watch the show without being able to see my stepmother’s boots. Finally I had it positioned in the right place and sat down on the hard seat.
No words were spoken as the video began to play from a preset position. On the screen was my younger self, smiling like I was the happiest little girl in the world and dressed like one. My lips were painted bright red as were my fingernails as well. My hair was curled in such a way that it framed my face and my eyelashes were long and black.
The video played for a few minutes and then stopped. “So where in that picture is the boy who hated being dressed in his sister’s clothes?” My wife demanded.
“I didn’t say I hated dressing up as a girl. I said that I did not insist on doing so. That was Sandy’s and mother’s idea. Mom said I made a better-looking girl than a boy and so I might as well dress like one. After a while I just gave up and did what she wanted. I am sure that she did not show you all the times when I railed against being dressed up and paraded in front of all my friends.”
“So,” mom began to speak. “I guess then that since you have left my house you have never worn women’s clothing again?”
I had not anticipated that question and my faced flushed with embarrassment. I wanted to lie but I knew that somehow I would not be able to do it with a straight face. So I just kept silent as one might in a courtroom taking the fifth against self-incrimination.
“I think your silence speaks volumes.” Pamela stated. “Is that why some of my panties are stretched out? Have you been trying on my lingerie when you are alone in the house?”
Again I hesitated to answer knowing that the truth would be worse than my silence. I could see Pamela starting to stand up and I turned directly towards her. She crossed the room with such speed that I had barely gotten my head all the way in her direction when I felt the flat of her hand strike me hard against my left cheek. It was hard enough to snap my head in the direction away from the blow and then she backhanded me across my right cheek.
“I have had just about all your efforts to avoid my questions that I am going to take. I asked you if you have tried on my lingerie. I expect an immediate answer.”
“Yes, ma-am.” I blurted out. “I am sorry. It won’t happen again.”
“I think we all know that is a bald-faced lie.” My stepmother said. Then she turned her words toward my wife. “Pamela wouldn’t you like to see how Jason would look all dressed up like the woman he desires to be?”
“I might as well.” Pamela replied. “Everyone else has seen him in all his feminine splendor. What did you have in mind?”
“Well, it just so happens that I have a complete outfit in the bag that I left on the kitchen table. Sandy why don’t you take your stepsister upstairs and help her get ready for her coming out party?”
“I am not doing this! There is no way in hell that I am going to allow you to dress me up like some tart in front of my wife.”
I watched my stepmother reach down and put her hand into the large leather purse she had beside her. She brought out a large wooden hairbrush and began tapping it lightly against her boot-covered leg. I forced my eyes to look away from her and toward my wife to see what her reaction to all this would be. To my amazement she had a huge grin on her face.
I knew I was in deep shit. My stepmother fully intended to use that brush on my bottom and she would not do it with my pants on. Now the true horror came to my mind for I was at that moment wearing a pair of my wife’s older panties that I had stolen from her sometime in the past. Once my pants came down then my cross-dressing would be fully out in the open.
“Okay, I will go with Sandy.” I announced.
“Too, late little girl. You know once I have the brush in my hand someone is going to get a paddling and that someone is you. So make it easy or hard on yourself. Either come willingly and drop your pants and shorts or Sandy and I will force you over my lap. Either way you are going to get a red bottom but if we have to force you it will be not only red but also black and blue. Which will it be?”
I looked over at my wife and she was smiling from ear to ear. Please Pam you aren’t going to let them do this to me are you?”
“Let them? Of course I am going to let them. In fact I am going to cheer them on. You deserve everything that your mother dishes out to you for lying. Now I suggest you walk over there, drop your pants and climb over mom’s lap. And do try to at least act like a man when she uses that brush. Try to see how long you can go without begging and pleading.”
I really had no choice. Unless I was prepared to physically fight my stepsister and stepmother, I was going to end up over her lap. And all though I might want to hit either or both of them, I would never raise a hand to a woman. So I stood and slowly made my way across the floor to where mom sat. Hesitantly I undid my belt and the top button on my trousers and lowered them down to my knees. I was wearing a long white shirt, which covered my backside although I knew that would not be allowed for long.
“Take off the shirt, girl. I don’t want anything to get between my brush and your ass.”
Slowly but surely I unbuttoned my shirt and allowed it to slip off my shoulders. Carefully I folded the garment and set in on the table beside my stepmother. I could hear the giggling coming from across the room and I knew that Sandy and my wife had discovered my deepest secret, the fact that I was wearing a pair of women’s underpants.
“Well, mom, I guess you called it right. The little bastard has been stealing my undergarments and wearing them when he thought he could get away with it. I hope you are going to give him a few extra swats with the brush for being such a bald faced liar.”
“Why don’t I just keep paddling his bottom until you tell me he has had enough? My arm needs a good workout anyway.
“Mmm, I like that idea. Jason pull down the panties and crawl onto your mother’s lap.”
Having no other choice I did as she commanded. Reaching down I not only lowered the panties but pulled them and my trousers completely off. As I folded them I held them in front of my now erect cock to try and hide it as best I could. But at some point I had to put them down on top of the folded shirt and I quickly lowered my hands in front of my now straining cock hoping that no one would notice. But my stepmother was having none of that.
“Drop your hands down to your sides, girl and turn around and face Pamela. I want her to see how your little clit is straining straight up so she will know how much you are looking forward to having your bottom turned as bright red as your flushed face.”
As I turned I heard my wife suck in her breath slightly. Her hand came up to her mouth to stifle a laugh or a sigh, I could not tell which. But the sparkly in her eyes told me she was really enjoying the spectacle in front of her.
“Dear God, he loves the idea of being punished. I would never have believed it until just now. I hope you are going to make him suffer enough so that his tiny excuse for a cock will not be hard for long.”
My stepmother turned me roughly around and forced me down across her lap. She had made sure that her skirt was covering her nylon clad legs so that my cock would have no opportunity to sneak down between them and rub against her thighs. Once she had me firmly locked into place she raised the brush and brought it down across both my ass cheeks as hard as she could. Mom did not believe in warming up her victim. I couldn’t help it; I released a cry of pain although I did not beg at that point. Again the brush came down this time just a bit higher than the last stroke and fresh nerves screamed, as the heavy brush compressed them. This time I managed to hold back my cries of pain although I did expel a large whoosh of air from my lungs. I could not see Sandy’s or my wife’s faces but I could hear them urging mom on. I could imagine my wife smiling with glee with each blow from the brush.
Again and again that brush fell against my ass cheeks until there was no more fresh skin to hit. And then she switched her aim so that the brush crisscrossed the already screaming muscles of my ass. By that time I was bawling like the little girl my stepmother accused me of being. Finally it was over and this time when I stood up I did not have a hardon. My cock hung down totally flaccid and to my chagrin pulled almost back into my body cavity.
Sandy came across the room and handed me a tissue. “Here sis, daub your eyes and wipe your cheeks and then let’s go upstairs and get you properly dressed.”
“Don’t forget to rid his body of all the hair below his shoulders. I brought an extra-large bottle of Nair just for this purpose. I can see he has not been taking his hormones so removing his body hair will take a little longer this time. I will see if I can get Pamela to start him back on estrogen so that unsightly hair will not grow back as quickly. And perhaps in time he will develop a little more girlish shape as well. How does that sound Pam?”
“I am not sure, why don’t we talk about it while Sandy helps her get dressed.”
I noticed how my wife had now changed the gender to feminine when she was referring to me and deep inside I was thoroughly conflicted. On one hand I hated the thought that my wife might go along with my stepmother’s suggestions of forced feminization but on the other hand the idea of being able to wear women’s clothing without having to hide the fact thrilled me.