My Stepmom Made Me a College Sissy

This story contains topics of feminization, non-consent, forced-bi, incest, and watersports. If any of these things bother you, please do not continue. All people in the story are of legal age, 18+. This is a fantasized version of a real occurrence that happened between my stepmother and me when I was a college freshman at 19.

My parents divorced when I was young and my father moved to another state and remarried shortly after. My stepmother was 20 years younger than my father and my new stepbrother only 1 year older than me at 20yrs old. She was a gorgeous Korean-American woman with long black hair, small perky breasts that were always on display in tight or low tops and an amazing ass. I would visit my father twice a year; for a few days over the holidays and then for a week or two during the summer while starting college. He was a workaholic and did consulting so was always traveling. There was even a trip over the holidays where he picked me up and then flew out that night and that was all I saw of him. He was the strong silent alpha male type and it felt like he preferred my athletic stepbrother over me like I was his stepson and his stepson was his real son.

I had an absolute crush on my stepmom. She always wore sexy and stylish outfits, benefiting from my father's wealth. Almost like clockwork, every night after dinner she would announce she was going to get comfortable and go upstairs and return in gorgeous silk and satin gowns and robes. I couldn't count the amount of times I had to hide my erections. My stepbrother noticed once and punched me hard in the balls and called me a pervert. I think she noticed too. Both of them weren't very nice to me and she would often kick me out of the house telling me to go get exercise or go for a hike in the woods and stay out for a few hours to give her some peace. I realized later what she was really doing was getting me out of the house to entertain her lover. When I was left home alone, I would go through her hamper and find her lingerie and rub myself in them. She even had a few pure silk pairs of panties that felt amazing to rub myself in so I stole a pair to secretly masturbate with as well as a pink nylon and lace teddy. I quickly went from jerking off with them and quickly cleaning them to wearing them - they made me feel so good. I continued doing this whenever I could when I visited and even stole a cream pair of silk and lace panties that I took back to my college dorm.

My mother passed away my freshman year of college which destroyed me. Over the summer vacation I couldn't find a way to stay on campus so I had to go and stay with my father and stepmother. The only thing that brought me any pleasure was playing with, smelling, and wearing my stepmom's lingerie and eventually clothes. My stepbrother had joined the army so he was out of the house which gave me more alone time to play. I thought I was really stealthy until my 19th birthday. My father was 2 weeks into a 5 month travel engagement. He sometimes would come home on weekends, but usually not. This left just my stepmom and me to celebrate my birthday and I figured she would ignore it all together. She left leaving me a note she was going shopping and wouldn't be home till dinner, thus leaving me home alone.

Stripping down to just the cream silk panties, I went into her room and there next to her closet in a bag was a new set of lingerie, tags still attached: black satin and lace panties with matching bra and garterbelt and a matching satin chemise and robe. I couldn't help myself by try them all on. They felt so amazing and I even looked at myself in the mirror with my longish brown hair, thin frame. I could almost pass. Being so excited I took them off and laid them out on the bed. Knowing she would be out for a long time, I drew a bath in her huge jacuzzi and filled it with floral bubble bath. Luxuriating in the bath and my hormones racing, I grabbed her razor and shaved off what little body hair I had. Getting out, I dried off and used her moisturizer then went to put on the lingerie. I put on the garterbelt and the black back seamed stockings, rolling them and pulling them up my newly shaved legs. The thin nylons felt amazing but were a little tricky given the moisturizer. I fastened the garterbelt to them and then slid up the black satin panties with lace trim on the back and tingled as it slid over my hardening cock.

Next I put the bra on backwards and fastened it then slid it around until my nipples were covered in the smooth satin and stood out aching. I played with them a little and let out a moan, getting lost in the sensation. Finally, I slid the black satin and white lace trimmed chemise over my head to complete the outfit along with the short robe. All that satin against my now smooth skin had me in heaven and I wanted more. So I went ahead and sat down at her vanity and looked through her makeup and perfume. Not being great at it, but also not being my first time I was able to add some eyeshadow and eyeliner along with some blush and a dark red lipstick. I was checking myself out in the vanity mirror when I saw her standing there with a huge smile on her face. I was so entranced in femininity that I hadn't noticed her coming home early. I sat there completely frozen, made up and wearing her brand new black lingerie. She took a step into the room with arms full of bags. Setting them down, she stood up, hands on her hip, "Well well, someone apparently likes their birthday present."

I was in complete shock, "What?" I closed the robe tightly around me as if that would hide what I was wearing.

"Oh Jamie, did you think I wouldn't notice my panties periodically missing or a little stretched out? Stand up and let me take a look."

I hated when she called me Jamie. I started going by Jim instead of James just so she wouldn't call me that. Even my father hated it when she did it. She would tell him that she was just being cute and that I was a cute boy to which he would respond, "BOYS AREN'T SUPPOSED TO BE CUTE." It felt like more of a dagger from him like he wasn't defending me being called that but that he also considered me to be, "cute" and that I wasn't manly enough. Standing in front of my stepmother with a raging erection in satin lingerie maybe proved both their points correct.

I covered my erection with my hands timidly and felt it beginning to subside given the humiliation. "Cute enough," she said, "but you need to practice your makeup. You look like a cheap whore. Now spin around for me and show me the rest." My erection was returning as I turned around a few times quickly. "Slowly, let me take it all in," she stated calmly. I began to turn around slowly and she stopped me facing away from her. Walking up and grabbing my ass through the satin panties, "a little saggy back here but I know some exercises to tighten up this little tush." Her hand remained there rubbing against the satin.

She sat down on the edge of her bed hiking up the skirt of her dress and patting the space next to her for me to sit. I sat down and kept my legs together hoping to hide my excitement seeing enough up her dress to see the shiny red gusset of her panties. She grabbed my hand and put it on her knee and slid it up her thigh until she was pressing my hand against the warm, and slightly damp, crotch of her panties. My erection was bulging against my panties dying to be free as she used her hand to guide my hand in little circles over the satin material over her pussy and clitoris. I rubbed my fingers a little and felt her panties getting more moist as her hand let go of mine and moved over to between my legs, cupping my little balls through my panties. It was the first time anyone else had ever touched me there and it made me shiver and release a little more precum into the panties. I was fixated staring at her raised dress and my hand rubbing circles over the red panties.

I hadn't noticed my breath was staggered and little moans were coming from me as she slowly teased my little penis with her fingers over the satiny material. She pushed me back onto the bed and stood next to it pulling off her dress to reveal a white nylon slip over a red satin bra matching the red satin panties. She slid the panties off and crawled up onto the bed kneeling next to me as I was sprawled out. All I could look at was her lightly hairy bush and pussy peaking underneath the slip. I had seen pictures in hustler, but had never seen a woman's pussy before. She squated over my right arm and reached down to grab my right hand and bring it to her wet hot pussy. I slid a finger inside her feeling the slick warm wetness suck my finger in. At the same time she took her red panties and positioned the inside of the red gusset where they were wettest and pushed them over my nose letting me inhale her scent and leaving them over my nose and eyes.

My raging cock was still encased in the black satin panties under the black and white satin slip and was throbbing and leaking. I had two fingers inside her and she was wiggling back and forth on my hand as she lifted my satin slip and began to lightly brush her nails up the length of my shaft in the satiny panties. This drove me wild. I was lost in the lust of my fingers inside her and her hand teasing my cock through the silky material. My eyes were now closed and my head was back in ecstasy. I had never felt anything so amazing that I forgot this was my stepmom until she finally spoke, "you are such a good girl. I will make you into the perfect daughter if you let me. Will you let Mommy make you her girl?" The lust was overwhelming. I would have agreed to anything. "Yes Mommy," was all I replied. She squeezed my little cock in the panties forcing another big drop of wetness to form on the tip which she wiped up with her fingers and used to coat my lips. "Yes Mommy what?" She asked. "Yes Mommy, I will be your perfect daughter." I was basically moaning as I spoke the words so desperate to cum.

She continued to tease my cock through the fabric and then slid her finger down the satin from the tip of my bulging cockhead down to its base, sliding down between my balls and pressing underneath them against my taint which made my hips thrust up and another big dollop of precum to form on the tip of my cock in the panties. She had the one hand pressing under my balls while the other one was directing my hand inside her, basically moving my wrist to create a rhythm with which she was now fucking my now 3 fingers inside her. Her hand moved down from under my balls and slid the thin satin fabric into the crack of my ass, her finger rubbing up and down to my anus. "Does my daughter know she has a pussy like Mommy?" she asked as she continued to rub through the material against my asshole. The sensations were so intense that I was unconsciously thrusting my hips upwards as if trying to force her fingers inside me. "Oh, you do know it is your little pussy. I want to hear you tell Mommy you have a pussy. What do you have little Jamie?"

There it was, the name Jamie again. It snapped me out of the trance and into the reality of what was going on. My stepmother was seducing me! This was my stepmother. My father's wife was slipping a finger around the edging of the panty and pressing it into my ass. And with that glorious feeling I lost sense of who we were again, relegated to being her lover, her daughter, her toy.

And then she came! My fingers were coated in her wetness as she contracted and tightened around them and she begged me to stop rubbing my thumb on her clit, just holding my hand still inside her as her whole body trembled. She pulled my hand away as she slumped over onto the bed still moaning a little. I sucked her juices off my fingers like I would starve without them. I was so close to my own orgasm when she pulled away and my little cock strained against the satin like it was trying to reach out to her hand to finish. But she rolled off the bed and walked silently to the bathroom leaving me panting and holding on the edge. I could hear her pissing in the toilet and even that was a turn on. She walked back into the room in a long silk crimson gown. I was sitting up on the edge of the bed. She was holding her red panties as she returned and then shoved them into my mouth. They were soaking wet and the taste was instantly obvious. She had soaked her panties in her piss.

"You have been a very good girl and Mommy is going to reward you and let you make your little mess if you can agree to my terms. Is that understood?" She pushed me onto my back on the bed with her panties still in my mouth making any response impossible.

What terms could she possibly mean? I didn't really care. I just needed to cum so I nodded yes.

She sat down next to me and pushed me down onto my back. "Good girl. Rule #1. I am going to lock away all your stupid ugly boy clothes. You will dress like my daughter all the time you stay here: panties, bras, dresses, skirts and blouses only. Is that understood?" I nodded yes.

She ran her fingers around my breasts and then circled my nipples, "Rule #2. You will maintain a smooth and hygienic body. You will eat what I tell you to eat and nothing more. No more fatty snacks. You will follow my exercise routine. You will work to get the best girlish figure you can. Mommy doesn't want an ugly daughter." She pinched a tiny bit of fat around my belly (of which there basically was none). Her fingers over the satin on my nipples was almost torture. My hips were gyrating and thrusting against air and tingly sensations flooded my body from my nipples. It almost felt so good that it hurt. I again nodded in the affirmative.

"Rule #3," and she stopped and squeezed my cock making a good sized dollup of precum form on the satin panties. Scooping it up with her finger, she presented it to my lips, "Any messes you make, you will lick or eat up regardless of where it is. I've found your messy cummies on the toilet seat, in my panties, on my swimwear. No more! You either do it in a cup and drink it, in your own panties and lick them clean, or not at all. I will make you lick my toilet bowl clean if you cannot control yourself. If it becomes a problem, we may need to remove those pesky balls of yours. They are unsightly and gross anyway. UNDERSTOOD?"

Fear filled my eyes. She wouldn't actually castrate me, would she? I also couldn't think about eating my own cum either. Dressing up was fun, but I was not gay. Could I disagree to all these and go back to my normal life and just stop dressing up? I must have been thinking it over for a while because next thing I knew, she had my balls tightly in her hand, "UNDERSTOOD?" I cried a little in pain and nodded yes.

"Good girl! There will be more, but lets start with these 3 and lets start now." She began to rub my cock more steadily, using the satin slip over the satin panties to really drive me wild. I was not going to last long. And then she just stopped leaving my cock throbbing and aching.

"What are you going to do with your messy cummies? Tell Mommy!" She pulled my cock out of my panties with the skirt of the slip lifted up so my cock was now bobbing wildly in the air. She then removed the panties from my mouth and draped them on my cock. "If I let you make your mess, are you going to suck these panties clean for Mommy?"

She was holding my cock in the panties and using the palm of her other hand to rub circles around the head with the satin. It was so intense I knew it was only seconds now. "Yes Mommy! I will suck out my messy cummies. Please let me cum Mommy!" An evil smile spread across her face.

"Beg! Beg Mommy to let you make cummies." She was slowing down to draw it out again leaving my cock waving in my saliva soaked panties as she again focused on my nipples.

"Please Mommy!"

"Please Mommy what?" She retorted

"Please Mommy help me make cummies in my panties so I may suck them clean!" This felt wrong, but I couldn't control myself and needed to cum so bad.

She pinched my nipples, "What else would my little daughter do for Mommy? And tell me in your most feminine voice."

I tried to raise my voice, "Anything Mommy! I will do anything Mommy if you let me cum. I will eat it all and then wear them for the rest of the day."

"Would you eat Mommy's pussy?"

Oh my god, would I. She didn't need any of this to ask me for that. I've wanted to eat her pussy and fuck her from the day my father introduced me. I responded immediately, "Yes Mommy I would eat your pussy whenever you wanted."

"Even when mommy has her aunt flow in town?" She took a finger and rubbed it along her pussy and then wiped her juices off on my upper lip.

"YES MOMMY! Anything Mommy. Please let me make my cummies. I'll eat you whenever and wherever. I'll eat you during your period. I'll eat you as you pee. I'll eat you whenever you desire. Please let me cum Mommy!"

"Will you eat my lovers' cum out of me daughter? Will you lick and slurp up their creampies?" She was furiously rubbing her clit. It was obvious this was turning her on. "Will you eat your dad's cum from my pussy? Would you like that baby girl, to taste your own father on your mommy?"

"YES MOMMY! ANYTHING!!!!" Then it sunk in what she said. "NO MOMMY! Please NO."

She stopped touching me altogether and laid down opposite from me with her legs open towards me, her fingers inside her pussy. "Yes my little girl. Next time your father is back, I am going wear my sexiest lingerie and tease him. You know your dad has a really nice big cock? Unlike your little thing, he is a REAL MAN. I am going to get him all hot and bothered so he builds up a nice big load (he usually has big ones when back from work trips - it's how I know he isn't cheating). Maybe I'll put you in my walk in closet all dressed up and tied up, gagged with my wet panties anticipating what is going to happen. Her walk in closet had her toilet attached to it. She didn't like to share her toilet so my father has his own and she has her own. You can watch through the slits in the door and I'll make sure to give you a show, sucking your father's cock where you can see it bulging and straining. Then I will lay down on the bed, my ass raised on pillows to give him better and deeper access and you can watch as your father fucks me silly till he drops that enormous load inside me. And then I will excuse myself to clean up as he falls asleep and come into the closet and push my freshly fucked cunt into your face and holding your head as you lap up your own father's cum from inside me. That is what you want isn't it, my daughter?"

I shook my head vigorously NO but my cock was harder than ever. Using her feet, she began to stroke my cock through the panties with her feet as she rubbing her clit and fingering herself.

"Maybe by the time your father comes home, we will have progressed far enough that you will have little budding breasts and your hair will be long enough to style. I will take you out in the morning to have your nails done, your hair done, and your makeup properly done so nobody can tell you were anything other than a beautiful little sexpot. I'll dress you up nice and sexy in white virginal satin lingerie and turn the lights low in the bedroom and after getting your father all hot and bothered...." her feet were working and I was panting and breathing hard on the edge of a massive orgasm as was she.

"I'll get him all hot and bothered and then give him his surprise. I'll bring you out crawling. You know your dad likes his pets to be submissive? And before you or he know it, he will be holding your head as he thrusts his manly cock into your mouth. I'll be kissing him and then whispering to you asking if you enjoy your father's hard cock, watching your little red hot lips wrapping around his massive shaft and swallowing his cock. He will start out gentle, but your father is impatient as you know and he will grab your head and start forcing his cock deeper." She stopped a second as an orgasm wracked her body. She sat up and brought her sticky fingers to my mouth for me to suck off.