Date: Fri, 18 Dec 2020 22:22:35 +0000 From: S Hardman Subject: The Step Sissy teen transgender category **None of this happened. All the adventures of the characters were between completely consenting individuals. It's not real. If sex acts like this offend you or you are not 18 don't read. **Consider a donation to Nifty.org THE STEP SISSY Alexander came to live with me at my home in his early teens. We were strangers at first but feelings evolved in our relationship over the years. I never thought my sissy stepson would end up becoming my wife. I know it's strange to give away the ending of the story at the beginning but life comes at you fast and weird things happen. Don't they say that it's about the journey? What a journey we've had! Here is our story. In about my twelfth attempt at swearing off sissy traps I met Alexander's mother, Vanessa. She was gorgeous and always very exacting with her looks and wardrobe. Alexander was gifted good genes and was very attractive, too. He was actually gorgeous in a feminine sort of way. I noticed immediately that he was a sissy. I had to laugh because the minute I thought I'd gotten over femboys one moved into my house. I ended up marrying his mother and we had a great life. I adopted Alex at her request and we grew close. He had creamy white skin, long legs and kept his hair in a boy cut but in a sissy way if that makes sense. It was so hot! He was average height with feminine round hips and a perfect peach for a butt. His mother caught him dressing in girl clothes more than once and she was worried. It wasn't that she didn't support his lifestyle. She was just concerned about how he'd be treated by his peers and the rest of the world for that matter. I told her he'd be fine. I couldn't help to notice what a hot little mynx he made though. He flaunted that ass in front of me, bending over slowly or dancing all the time. After all I had a penchant for sissy slits and that femboy was delicious. We had a few incredible years of bliss. Our home was very peaceful. Vanessa and I had a wonderful sex life. Sometimes a vision of Alex would be in my head as I was fucking his mother. Alexander was discovering who he was. I'd seen him dressed several times many times, too. He definitely didn't try to hide it from me. He was actually pretty brazen around me. I never scolded him or said anything to his mother until she made the discovery on her own. He stopped hiding it altogether eventually. He wore light make up and was actually very popular at school. His best friend was a boy name Pierce who was obviously a sissy, too. He had a great support system between his friends and family. He would wear perfume and jewelry, too. His room was a girlish paradise. I was trying to be good but he was an incorrigible tease. I tried to pretend it was accidental when would brush me on the leg with his hosed toes under the table. We never acknowledged it to each other. It was difficult to stand up from the table when you dick is rock hard because your sissy stepson has aroused you. I was really lying to myself that there wasn't an attraction by both of us. I told myself he was blowing the quarterback or something at school. That was far from the truth. He didn't like boys his age. Older men is sissy kryptonite. Sissies are a mature man's kryptonite. All in all everything was wonderful but it couldn't last. One day tragedy visited our happy home. Vanessa was diagnosed with breast cancer and we lost her within months. I was distraught and Alex was inconsolable. He was very close to her and I knew I had to be there for him or he wouldn't make it. Add to it that he had just started to identify as non-binary and his world was full of complications. We were really devastated for a while and I really felt it was my responsibility to take care of Alexander. I needed him to know I was here for him and always would be. He had so many feelings he didn't understand completely. He was dressing as a female all the time now and asked me to call him Lexi and he changed his pronouns to she/her. So I started referring to her that way. She was so depressed and I did everything I could to cheer her up. I was in no mood to find another lover either. We pretty much holed up in our home when she wasn't at school. I usually worked in my home office. She only occasionally visited Pierce who was now Priscilla. Prissy, as she liked to called, spent lots of time trying to cheer her up at our house, too. It was actually good to hear their laughter and positivity. Sissies are born with self-esteem problems so they are a great support system for each other. When we were alone it was a different story. I wasn't sure what to say but I did my best and pretty much let her do anything she wanted. Probably not the best solution but it worked itself out. After all she was not only a truly knock-out looking femboy but very very smart as well. I know you sissy lovers are thirsty for when dicks are going to get sucked. Don't worry, we'll get to that!! I was definitely pounding my weasel because my view everyday was two hot sissy traps in skimpy outfits. Part of how she tested the boundaries was dressing pretty in shorter and shorter dresses and skirts. I asked to her tone it down but around the house I couldn't help but notice. She said, "Daddy it's how all teen girls dress." So I just sorta shrugged and enjoyed the view. Prissy dressed very similarly and also took every opportunity she could to sit on my lap. It was a little shocking at first but I settled into it a little too quickly. I couldn't help but laugh at the irony that I'd sworn off sissies and then end up living in the same house as one of the hottest ones I'd ever seen and her equally hot and obviously horny friend. When I say Lexi had blossomed I can't even begin to tell you how confusing it was for me. I shouldn't be attracted to my sissy step daughter. Since the school had a dress code, she and Prissy wore the tartan school girl uniform she had convinced the principal to let her wear. She wore a white button up and tan pantyhose with sky high heels. She didn't want to wear panties and it left very little to the imagination. After 3 notes home I made her put them on. I checked every day! She immediately shed them and the uniform for tiny skirts and skimpy t-shirts when she got home every day. She was still so sad at times. She had been having lots of nightmares and was very depressed at night being alone so she started coming into my room and sleeping next to me. She wore little see-through nightgowns and her hosed ass was usually snuggled up to my hip. She would usually start her night in her own bed but invariably ended up draped over me in mine. One night her hosed leg ended up laying across me, well more specifically across my cock. I woke up with my normal morning wood. I was especially horny that morning and I had become accustomed to taking care of myself. I quietly pulled down the front of my underwear and began working it up and down across the smooth fabric. It didn't take long until I tensed up and spurted ropes of cum across my stomach but some definitely ended up her sleek sissy leg. I immediately regretted what I'd done and slipped out to try and clean up. I was red with shame and as she stirred I was sure she'd see it and it would dry and crust on her pantyhose. She'd yell how gross it was and then call the cops. I'd be dragged off to jail to live forever. I was so wrong. She just climbed out of bed and came into the bathroom. She hugged me around from the back. "Good morning daddy! It looks like you really needed that. I'm glad I could help. Yum!" I looked up and I am pretty sure she had some my cum on her lips. She softly kissed my neck and then left. I was very stunned and confused and also really really turned on. As I was to find out later, she wasn't confused and also very turned on, too. Her confidence grew and I was pretty proud of her. Nothing else happened like that for a while. She acted in a few school musicals. She was a talented dancer and singer. She was very busy. She had landed a job at a local fashion boutique called House Fallus. That led to a significant rise in the amount of hot sexy outfits she owned. It was run by an old school buddy of mine, Miles Fallus. He loved to provide the girls with clothes to wear to help market the store. She was super happy and had a good support system because a two other sissies worked there as well. Boy was that a story, huh?! Those sissies and Miles really spilled a lot of semen on and in each other. Miles and his femboy friends loved to throw pool parties at his mansion and Lexi took me and Prissy to a few of them. There was always a bunch of nudity and frivolity involved. The cis girls that worked there even got a little crazy. I probably shouldn't have let my sissy teen stepdaughter go to these raunchy soirees but I was not a normal dad. Besides I shamefully ogled the hot girls and gurls, too. Yes, I was really lusting after Lexi in her tiny bikini. I was pretty ashamed! One particular Saturday when I skipped one of the parties to get some work done around the house the doorbell rang. I opened it to Prissy in a tiny skirt and huge smile. I started to tell her that Lexi wasn't home when she pushed in. She placed her hands on my chest and moved me to the couch. She said, "I know you big stud. Why do you think I'm here? I needed you alone so I can see your cock!" I sat back stammering as she dropped down and unzipped my pants. She extracted my dick and sank her pretty pink lips over it. We didn't even kiss. That came later. I was just about to protest but it felt too good. She was very talented and thorough ball guzzler. Femboys are masters of oral pleasure. I was moaning and she was making sexy gagging noises because she had my dick in her mouth. It was so fucking hot. I lasted a good 4 minutes before my sex starved organ started convulsing in her sweet sissy mouth. I filled it up with my man goo and it started running off her lips. She sat back and opened up to show me and then swallowed it down with a look of total satisfaction. "I've been trying to do that with you for two years. You never react when I sit on your lap. Lexi is always making fun of me when I throw myself at you. I know you have the hots for your little femboy stepdaughter but I've wanted you, too. I haven't said anything to her but I think she knows you want her. I don't believe I'll ever win out over her but I had to try." I wasn't sure what to say so I just said, "Thank you. I had no idea how much I needed that." Obviously I blew off the most embarrassing part about me hungering after my teen tranny stepdaughter. With that we began seeing each other on the sly. The sissy grapevine is very active and so word had gotten around about by past exploits with other femmes. She knew I couldn't resist a little sissy with a tiny peepee in their pantyhose. She wanted me naked all the time. She sent nudes to me several times a day. I would meet her in my car or have her over when Lexi was at work. Prissy came from a wealthy family so she didn't have to work. She was really good with dirty talk and with her mouth. She would beg me to blow it on her face or in her hair. She would get out of my car with cum still on her face. It was like a badge of honor for her. She was a total slut. I would get a real rise out of reaching under her skirt and massaging her little schlong while it was pinned under her sheer tights. I'd rub it until it made a real mess. She would show up to my front door and drop her coat on the front stoop and be there in nothing but sexy hose and heels and a smile. I was having so much fun with her but I never took her virginity. I didn't want to because I was waiting for someone else, my own former sissy stepson! She accepted what she could get. Alex's warm body still kept me company almost every night. I'd miss it if it wasn't there. One morning I awoke and felt her body next to me but her hand was in a place it had never been before. It was resting on my hardened cock over my boxers. I laid there silently enjoying it for a while and moved it up and down a little. She stirred and I stopped. She didn't stop though. She moved her hand past the waistband onto my manhood. I went to pull her hand away and she said, "Come on Daddy! You know we both want this. Besides I've been admiring it for so long. It's huge! I want to see it. I need to see it! I know you want to see mine." She was pleading and the way she said `Daddy' was different than she'd said it before. It had sensuality in the tone. With that she planted a kiss on me that was years in the making. It was better than I'd imagined and I'd imagined it a lot. Our tongues started wrestling and her lips were like velvet. My cock was harder than it had ever been and that is not an exaggeration. She pulled it out and worked it with a purpose while we kissed. I didn't last long and exploded all over both of us. She looked very satisfied. She popped up and went to the shower. If it had been someone else I would've joined them. I had immediate regret but I had to admit that is sure felt glorious. I couldn't help but to admire her oral talents. I swore it off forever immediately though. Never again! Yeah, right!! I was visibly uncomfortable for the next few days and she could tell I didn't really want to talk about it. She still came into my room at night. She was just too accustomed to it to change and I could never send her away. It was so reassuring to us both. My effort to not repeat what I felt was a mistake was not helped when I drifted to sleep and this gorgeous sissy appeared in my dream. I first saw her perfectly made up but oh so innocent looking face. She was looking back at me with those big doe eyes and cute haircut but the scene pulled out and closer in the foreground her boi pussy was winking at me. It was a thing of perfection. It was smoothly shaved and I could tell it was as tight as could be with her little shaved sac and dangling girl cock. God it was beautiful! She smiled at me and I heard, "Daddy? Daddy? Daddy?" It was so close but so far away. It echoed and as I was about to sink my tongue into it I realized I was being shaken awake. "Daddy, are you ok? You were moaning my name in your sleep." I looked up at my beautiful step sissy and I realized I was now powerless to her charms. I cleared my head and said I was fine and apologized. She asked if I was dreaming of her and I told her no. She knew I was lying. I could tell by the way she grinned with her stunning mouth. She looked pretty great for someone who'd just woken up or maybe it was that I'd just had a sex dream about her, my adopted sissy son. I was once again ashamed but not as much this time for some reason. Suddenly I said, "I know you want to see that new Brad Pitt movie coming out this weekend. Maybe we could go Saturday night." She practically leapt onto me and screamed, "YES, daddy, yes! It's a date!" She kissed me and ran out of the room. Once again confusion set in and she had said the word date. I was in deep trouble!! She wasn't as present the rest of the week. She was busy at work and even worked a shift early on Saturday at the boutique. She asked me to pick her up at her friend Andi's new apartment. It really was like I was picking her up for a date. When she appeared at the door I heard myself actually audibly gasp. Her make-up was meticulously done. She was in a short red dress with tan hose and open toed red heels. I could see the outline of her little clit pushing against the fabric. She'd obviously raided the expensive section of the boutique. Miles loved the girls to model his clothing around town. It really drove business. It certainly did something to me. Her short hair was styled and shining. She smelled like heaven. I was in for it for sure. Her friend Andi, who was absolutely gorgeous in her own right, waved a little feminine wave with a knowing smirk and said, "Have fun y'all." We drove to the theater and she snuggled up close on my arm. She laughed and said, "You should do the popcorn trick. I will go down on you in a theater! I can't wait to see your daddy dick again!" I turned beat red but it was pretty funny. There was lots of hand holding and footsy during the movie. Her hand was always pretty close to my cock. Afterwards we had dinner at a fancy restaurant. She got lots of lascivious looks from horny dads and looks of disgusting jealousy from the girls. I was so lucky! I then suggested we pick up her car from Andi's apartment but she said she just wanted to go home with her handsome date. She couldn't wait any longer so I took her to our home. She went in, freshened up, kicked off her shoes and settled on the couch. I actually let her have some wine and we relaxed. She took our glasses and set them aside after a few sips and moved in close. Our lips met for a wet kiss. It was one of the best moments of my life but I wasn't ready to admit that to myself. I really was a fool thinking I wasn't going to do exactly as she wanted. The petting started to get heavy then she moved her feet onto my lap. My dick hardened and the intensity rose. She lifted one up to my lips and I started licking and sucking her little sexy big toe. I worked down the leg planting little kisses as I went. I let it go and reached around and unzipped her dress and pulled down the top half off her delicate shoulders. I unsnapped her bra. She only had it on for looks anyway. She made a real show by flinging it to me sexily with a girlish giggle. I loved it. There was no turning back now. I grazed her nipple for the first time with my fingers then my lips and tongue. "Oh My God Daddy! That feels so good. Please don't stop!" That drove me on and I explored her girlish chest and neck. I nibbled her ear and blew in it and she started moaning. I worked my way of her girlish jawline to her lips. We melted into a creamy kiss. I whispered, "I want to make you the happiest sissy that ever lived!" She stood up and dropped the dress to her ankles and what was in front of me was the hottest `woman' I'd ever seen. She ripped off my shirt and pants and extracted my rock hard member and she swallowed it with purpose. She slobbered and sucked and then looked up at me. She said, "I've been dreaming of this moment forever. I can't believe it's here. I am going to savor it." That slowed her down as she explored every inch with her tongue and then she went to work on my ball sac. I was ready to explode. She kept edging me with her hand then she pulled me up and we raced to the bedroom. She got on her hands and knees and I stopped and said I didn't think we should do that yet. You would've thought I'd just killed her puppy. She was so disappointed. She turned and pulled me into bed. "Are you kidding me? We are destined to do this. My boi pussy is starving for your man cock! My bussy is so hungry for you. You need to take me now! I'm ready Daddy! Besides I know you want to. You've lusted after me since the first day you saw me. I'm your little playground now. I do whatever you tell me to" How could I say no after that little speech? After all it was the complete truth. I gently pushed her off and back to her hands and knees and ripped a hole in the hose. I admired her pussy and then my tongue dove into that smooth delicious hole. It was exactly like in my dream. It was so tight. I ate it with passion while I wrapped my arm around her and rubbed her little stiff cocklet. She quickly exploded in the hose and started moaning for more. After thoroughly lubing up her backside I put my cock at the entrance. I slowly started to push. It resisted a minute or so and then allowed access. I started to pick up the pace and it was like I was on a bucking bronco. She couldn't control her body because she was in heat. I then laid my full weight on her body and she settled in for the ride. I edged again and again and then I had her sit on my cock reverse cowboy and ride it a while. I eventually laid her back and rested her legs on my shoulders. I wanted to look into her eyes as I finished. I ramped up the strokes. "Oh fuck, Daddy. Oh fuck! God that feels so good! Ride your baby sissy! Drop your load in me!" With that encouragement I gave one last stroke and cum gushed deep into her boi pussy! I shoved it in to the hilt as I emptied my balls into her. I then collapsed next to her with pure lust. She put her body across me and did something super dirty. As the cream leaked out she reached back and put some on her finger and then put it in her mouth. "Damn Daddy! Your cummy is so yummy! Mmmmm!" I was shocked at what a whore I had living with me for all these years. I also absolutely loved it!! We didn't get her car until 2 nights later. We spent the next 48 hours in and out of bed, mostly in. I made that sweet honey hole all mine time after time. I explored every inch of that feminine little body I'd desired for so long. We explored all the things she could do with her little sissy mouth. I took the next week off from my job and she did the same. We had years of sexual tension to address. And we addressed it in every position possible and in all of her holes! Well I guess you could say I got over my hang ups pretty quickly. She was no longer my step daughter. She was quickly my girlfriend. 2 months later she pivoted into being my fiancé. I asked her to marry me and take the place her mother once held. We waited until Miles and his little femboy Sasha tied the knot. Then a few months later we celebrated in Miles' huge mansion backyard. Femboy weddings bring out the naughtiness in everyone. Prissy was Maid of Honor and Andi and Sasha were bridesmaids. Prissy met her future husband that night, the CEO of a sex toy company. He's a millionaire and she did a million dollar job at slobbering all over his schlong. Andi took care of two of my friends each oblivious to the other. She is a total slut. As I laid my new lady boy in our marital bed I told her she was the most beautiful woman I'd ever laid my eyes on. It wasn't a lie. This former boy was a gorgeous woman now. She said, "Daddy please make me your wife tonight and put a baby in my belly. I want you to fill me up with your seed!" I knew that wasn't possible but I sure tried. She is a natural partner to me. She told me she'd been wife in training for me the entire time in her mind. She had studied what it would take to make me happy since the first day she came into my life. She figured it was ridiculous for either of us to look for anyone else outside our home since we knew exactly how to take care of the other's needs. We were totally in love. We were soul mates. She admitted knowing that Prissy had sucked my cock and encouraged it because all she wanted was for me to be happy. She knew I needed the relief. I had been really depressed and a build-up of man seed is not healthy. I let her start hormones and I gave her all her injections, with the needle and with my hot beef. I would never allow her to cut off that beautiful little boi clit though. That little girly stick belongs to me. Eventually we adopted 2 children and a dog. We cum together most nights. Lexi is a like a 1950's housewife. She is up with the chickens, takes care of the kids. One minute she's cooking dinner then the next minute her pantyhose are around her ankles and she's sliding her pussy down my dong while her little prick is flopping in the breeze. She does all this while looking like a teen tranny supermodel! I usually get at least one text a day with a dirty pic of her all alone or naked with one her trashy tranny friends. The text might read something like this. "Damn Daddy! I'm so horny. When I get home I need you to hold my legs up and park your porker in my tight little hole while I pound my girl dick!" I always do it! I never say no to my little femboy freak. We are so in love. My little Step Sissy wife is pure pussy perfection!