Step Father Makeover

by Cheryl Anderson

 

It Just Makes Sense

My step daughter Kari and I had never gotten along, really. She hadn't approved of her mom's divorce, and she certainly didn't approve of living with her mother and me. She was sullen, hostile – then again, aren't all girls?

Still, I should have been suspicious when she started burning me CDs of some of my favorite music – Irish folk songs mainly – that at one point she had described as about as far from cool as you can get. At this point she was a psychology major at a local university, doing her master's thesis on the effects of hypnosis on cognitive/behavioral therapy. I had no idea at the time what that meant, and I really didn't care as long as she graduated quickly and got out of our house ASAP.

One night she made dinner and gave me a CD just before bed. Normally I don't go to sleep until after Letterman, but for some reason after dinner I just couldn't keep my eyes open, and slid under the covers early. With the headphones on, I began listening to some romantic ballads, and promptly fell asleep. I was surprised that I woke up with the headphones on, and still playing. I must have hit the "continuous" button by mistake.

Anyway, before she left for breakfast, Kari pulled a circular compact out of her purse, and handed it to me, explaining that they were special vitamins for men my age that she's picked up from a pharmacist friend of hers. Prescription only, so very good. I felt this immediate flush of gratitude. I literally blushed and couldn't thank her enough – which was odd, in retrospect, because usually our conversations were civil, at best. Anyway, I popped a little blue pill, put the compact in my pocket and promised Kari I would take two more pills. One at lunch and one at dinner. It just makes sense to take them three times a day, she said. And I repeated, "Yes, it just makes sense." In fact, when noon came around, her voice saying: "It just makes sense" immediately echoed in my head, I turned away from my computer, walked to the water fountain, and took a pill. The same thing happened at 5 p.m., on the dot. My legs seemed to move by themselves, and I couldn't wait to take that pill.

There were 30 pills in each compact, and after ten days were up, Kari presented me with a new pill case. About the fifth time this happened, she also gave me a small leather satchel with a shoulder strap to carry them in. And she also suggested I keep my wallet and keys in there. After all, it just makes sense to keep all my things together, she pointed out. Yes, I thought, that makes perfect sense to me. She also said it would be best I not let her mother see me with my new satchel, because she might mistake it for a purse. "Doesn't that makes sense?" she asked, sweetly. I had to agree to made perfect sense.

It was around this time that I noticed my nipples had gotten quite puffy and sore, and I couldn't lift as much weight at the gym as I could before I started my pills, which seemed odd. You'd think they'd have the opposite effect. Then again, I wasn't that big to begin with: Only 5'7" and 160 pounds. Still, it seemed curious enough that I asked Kari about it. She was becoming my real confidant lately, and I found myself telling her everything. It just made sense that we would become friends, after all. She explained that girls loved guys with sensitive nipples, so I should look at it as a benefit. When I questioned that, she became very stern, and said to me: "Are you questioning me?" I immediately went pale, and said: "I would never question you, Kari. You always know what's best." That really surprised me, but before I could question her further, she had reached over (not up, we're about the same size) and pinched both my nipples. Hard. And she wouldn't let go. The pain was intense, but somehow very very pleasurable. I felt my knees grow weak and my eyes have shut. "Ohhhhhhhh," I said. It almost sounded like a moan a girl would make. "See," Kari said, her steady blue eyes looking into my brown ones. "Sensitive nipples are want women like, and what men should like, therefore." I had to agree, that just made sense.

I wasn't so sure, frankly, about how women would feel about big rears on men. Because, while I was losing weight, I definitely wasn't losing weight back there. So while my waist was getting thinner because of my vitamins, the fat seemed to be migrating to my hips, rear and thighs. I tired to ignore it, but when my wife commented on it, I decided I'd check with Kari. She said she was glad I'd come to her, which made me feel good. But when she asked me to drop my pants so she could have a better look, I hesitated.

That was a mistake. She immediately looked angry, and again I felt that sick sensation. So, I did as she ordered. She said part of the problem was the boxers I wore were so baggy, they made my rear look bigger. Which made sense. She suggested I wear tighter underwear, and gave me a couple pairs of hers. But she warned me not to let her mother see me wearing them. She also said panties would look silly on a man unless he was hairless, so I should "get smooth" from the waist down. Wow. I'm sure her mother would notice that, but Kari said I'd just have to stop "being intimate" with her until Kari could think of a reason to explain it. I was so grateful, I almost found myself crying. Well, I actually did cry a little. Kari was so sweet, though, she put her arm around me and comforted me. She said it was okay to cry. I dissolved in tears at that, and said I couldn't understand why I was such a basket case.

She explained that as I got more in touch with my feminine side, it would be natural I would act more like a woman, or like a girl. And women love sensitive men. "But won't they see me as a sissy?" I asked her. "Charlie," she said, "you obviously are looking more like a woman now, and crying like a girl. Don't be ashamed of who you are." Which made sense, of course.

But then she said: "Be proud of being a sissy. Metrosexuals are the in thing, you know, and women think they are sooooooo hot! I'm sure my mom will love you even more, the more feminine you become. And I will help you."

Wow. I was amazed at how our relationship had improved. She gave me a card where I could have laser hair removal, and immediately began coaching me on my walk – nothing too dramatic, but a bit of a feminine sway to my hips. When I did well, she rewarded me with a little slap on my rear, and praise of, "Good sissy!" She also said that subconsciously she knew I would fight becoming a sissy, so she had programmed the CDs she had given me to make me lose my inhibitions, and to be made easily suggestible. It was part of her master's thesis. She also said the vitamins were really female hormones. I freaked.

"You conniving little bitch," I screamed. Stamping my foot in anger. "You're the reason I've lost 30 pounds, have little boobs and a bubble butt?"

"Yes," she answered, "and why you find it so hard having an erection, and why you're less and less attracted to women."

I tried to take a step toward her, but my feet seemed glued to the floor.

"Oh, and why you can't raise a hand against me. I am your secret Mistress, aren't I sissy?" She purred.

"Yes, you are my secret Mistress," I responded automatically. The phrase "secret Mistress" made all the life drain out of me. I knew in my heart she wouldn't do anything to me except what was in my own best interest, of course. It only made sense the way she explained it. Women like sissies, I am becoming a sissy.

"You'll feel better after a good cry," Kari said, and with that, she lay me over her lap and smacked my bubble butt until I cried like a baby. I did feel better afterwards, thanked her for the panties, and left her room, relieved.

So, my sissy lessons continued for the next several months, though it was obvious my wife was finding me less attractive, not more. We never had sex, and she couldn't understand why I insisted on having no hair below the waist, and no chest hair. Things finally came to a head in our bedroom one night, when she said that everyone was beginning to notice my "strange" behavior. And she and Kari were embarrassed by it. "Kari even says you're turning into a faggot," she said. "I am not a faggot!" I screamed. "I am a sissy. It's who I am. And if you don't like it, you don't love me for who I am." I burst into tears, of course, and she just left the room. And the house. I didn't hear from her again for two days, when I was ordered out of the house and received divorce papers.

At my new apartment, Kari tried to console me, but I was pretty upset. She told me to look on the bright side: "Mom will come around, she just is seeing you in transition right now. I'll help her understand, really I will." She also said this would be a great opportunity to increase my sissy training. That night we went to the mall and bought some cute stretch pants, some blouses for work, had my ears pierced and had my hair – which was past my shoulders now – styled into a "professional" feminine cut. It didn't look professional to me, and required I learn how to use a curling iron. But Kari said all the secretaries at her college wore their hair that way.

Needless to say, my coworkers weren't really wild about my new look. But, as Kari explained, I was an accountant and therefore surrounded by uptight fellow accountants. When the next wave of downsizing happened a couple months later, I wasn't surprised when I was let go. The good news was I got a huge severance check, which was sorely needed because my wife had gotten our house and all our savings. I'd been living paycheck to paycheck.

Now came decision time. Since people obviously weren't accepting me as a sissy, I needed to either become a real man again, or become so feminine I would be accepted as a woman. I posed this problem to Kari, and she said she'd been thinking the same thing. Given that I now had b cup breasts, and a curvy rear, it would be easier to become a girl, she said. Besides, my "equipment" wasn't working anyway, was it? I said it had been a while since I tried, so Kari made a decision that made total sense: Try to cum, and if I could in a reasonable amount of time, I'd become a guy. If I couldn't, I'd start living as a girl. This was a very big moment, and I was nervous, so it wasn't surprising that I couldn't cum. I dropped my tailored slacks to my ankles, pulled down my panties, and tried as hard as I could. It didn't help that Kari stood there making fun of me, and that she made me cry saying what a pathetic sissy I had become. But, she was right, after all.

It took all of my severance package to become a girl. I had facial feminization surgery, breast augmentation, and a couple other things. Kari was great through the whole thing, coming to the plastic surgeon with me, and discussing what needed to be done. She and the surgeon became quite close, in fact, so close that when I was under the anesthetic, she had him make some modifications to what we had agreed upon. Instead of a leaving my already pouty lips alone, she had them puffed up. My nose was made smaller, and pert, instead of classic. My breasts became a double d cup, instead of a C, two ribs were removed and I had liposuction to get me down to a 24 inch waist, and my cock and balls were removed, and I was given a vagina. This last modification was very painful, but Kari watched me dilate it regularly with a dildo, and encouraged me to go with bigger and bigger ones until I was fully functioning and orgasmic. She also programmed me with mental "triggers" so if my big nipples where pinched hard enough, or I was spanked, I would have orgasm after orgasm, and be helpless to stop them. This would help when I started dating men, she said, because men don't like to perform a lot of foreplay.

MEN? I guess I had always assumed I would be a lesbian, but Kari pointed out that I was pretty helpless, and needed a big strong man to take care of me. I let that pass, because she also said she had gotten me an interview for a new job, and I was desperate to make money at that point.

The job interview, I was shocked to hear, was with her biological father, Ken. Ken needed a bookkeeper/secretary at his construction company. I begged Kari not to make me go, but she pointed out that there was no way Ken would realize I was the man who had stolen his wife away from him. To make sure, Kari had me legally change my name from Charles to Charlene, and my last name from Kurtz to Goodbodie.

To my surprise, Ken hired me on the spot. I think what I wore helped convince him that I would be a good employee. I had a very low cut blouse with no bra, and an ultra short skirt and high heels. Kari explained that Ken had a lot of real mean – rough types – who would be more likely to do business with him if Ken had a hot looking secretary in front of his office. That made total sense, given the way men looked at me now. Part of it was my big boobs, but Kari also showed me how to wiggle, lean forward, toss my hair, etc. in ways that would get men interested in me.

That was fine, but she also programmed me into thinking how bad it was to be a tease. That if I were to get men all worked up, the least I could do was satisfy their needs. Luckily, it turned out I was excellent at giving blow jobs, and after just a few lessons with Kari and her strapon, I could deep throat like a hooker, she said. It was humiliating, and I never got used to the taste, but at least I could keep my job, and I seemed to want to please Ken almost as much as I wanted to please Kari. Weird.

I guess then what happened next came as no big surprise. I was still a virgin, but one day Ken asked me into his office to do some filing, and while I was bent over I felt my skirt lifted off my ass, and my panties pulled down. I looked behind me and saw Ken guiding his huge cock toward my bare rear, and started to scream. He immediately starting spanking my ass, and the orgasms started. The next thing I new, I was begging Ken to fuck me and moaning like a cheap whore. He pulled my top over my head and put his hands on my boobs, which where bouncing all over my chest. That made me cum even harder, and when I arched my back my long, carefully curled hair, now colored honey blonde, spilled all the way down to my mid back. Just as I felt his hot cum shoot inside my vagina, he said: "Hey Charlie, How does it feel to be fucked by your wife's ex-husband? You pathetic little sissy." I burst into tears and had to leave the office early that day. Though the next day I was back, and at Kari's insistence, apologized for missing work.

For the longest time, I thought that I was just Ken's little whore, especially because he seemed to be dating some mystery woman seriously. Then one night when I was giving Kari a pedicure, she gave me some incredible news: I was getting married! Ken had apparently decided to make an honest woman of me. Wow. I cried, but they were tears of joy. Kari had told me so much about what a wonderful man he was, that despite my treatment by him at the office, I realized I had fallen in love with all 6 foot 4 of him.

Preparations for the wedding became a whirlwind, luckily for me, Kari handled most of the details. The day of my wedding, I was waiting with her in a little room in the church, looking very sexy in my strapless, mermaid style wedding gown, when the first of the days surprises walked in. It was my father. He and I had never really gotten along, but I'd seen a lot of during the years I was married to Kari's mom – her father had died when she was very young, and my father kind of became a second father to her.

"Hello, Charlene," he said (Thank god he didn't realize who I was, but what was he doing there?) I understand your father couldn't be here to give you away, so Kari asked that I do the honors, as long as I was here."

"Ummm, grandpa, I think Charlene has something she needs to tell you," Kari said, and then whispered I needed to tell my dad who I was, and left the room. I sat him down, but before I could begin my story, I noticed he was staring at my chest. I could hardly blame him, of course, my gorgeous tits were on full display, and my creamy globes could give a heart attack to any man, even one in his sixties. I instinctively gave them a little bounce as I sat down across from him, bent over a little to give him a full view, and took his hands in mine. I admired my long, french tipped nails, and noticed how big and strong his hands were, by comparison.

"Let me tell you a story, sir," I began. "I actually knew your son, and he's been going through a very difficult time lately …" I started telling him about "Charlie" and his marriage, meanwhile bouncing my boobs, flipping my hair, leaning close to him, and subtly licking my lips. All this came so automatically to me, from Kari's training, I couldn't stop it, even if it was my own father I was getting arroused. When I'd gotten to the point of how Charlie was becoming a sissy, I casually reachedover to unzip the fly of his tux, and got down on my knees in front of him. I had to talk, of course, and didn't want to mess up my makeup, so I started giving him a good hand job. Then I took my breasts out of my chest, and placed his hands on them as I explained that I was his son, but that I'd become a sissy and then a woman, because I could never have been a real man like him. He looked horrified, I have to admit, but he didn't get up. I started to moan from his pinching of my nipples, and actually came a few times. And just as I was finishing my story, I felt he was about to cum. Not wanting to stain my gorgeous wedding gown, I quickly leaned over and took my father's cock in my mouth, and sucked it dry. When I got up, I noticed Kari was standing there with a video cam, and she quickly explained to her grandpa that he'd better go through with the ceremony, or else.

He started to say something hurtful to Kari, and I slapped him. Hard. And told him to NEVER address my Mistress that way. He left, and Kari helped fix my makeup and told me that I was the best sissy ever (I looked down at my boobs and saw them flushing red) and that this was the happiest day of my life.

Well, sort of. When I left the room for the long walk down the isle, another bride emerged from another room and stood on the other side of my father. I couldn't tell who she was, because of the veil, but when I looked up to the altar, I noticed that it was going to be a double wedding. Ken was on one side (the wrong side, I thought. I was heading up the right side of the isle, but he was on the left), and his foreman Brock (a man I had to show I wasn't a tease dozens of times) was on my side. When we reached the preacher, I suddenly understood that I would be marrying Brock, and Ken would be marrying …

Yes. My ex wife. She looked lovely in her gown – and I realized that while she looked beautiful and classy, I looked like a tramp with my big boobs spilling out over my tight dress, and my hair curled and down while hers was elegant and in an updo.

Kari just smiled and smiled from her position as our maid of honor. I didn't see her until after the honeymoon and I had settled into Brock's small house, taking care of his three kids. His wife had left him just several months earlier. Luckily, Kari gave me some special hormones and a breast pump, so I was soon lactating, and could breast feed Brock's six month old son – my stepson. I didn't like the rough sex, but that's all Brock seemed to know how to do. Many nights, after putting the kids to bed, I cried myself to sleep.

Kari came over for breakfast one morning, casually lifted my huge left boob out of my nursing bra, and squirted milk into the coffee I had just served her.

"I look at it this way," she said. "I may have lost a step dad, but I gained a milkmaid." Which was true, after all.

  

  

  

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