tagTranssexuals & CrossdressersStepsister's Surprise

Stepsister's Surprise


I was twenty when my father re-married. My mother walked out on us when I was six and Dad was always right there for me. Fourteen years raising me all by himself, sacrificing his own personal needs and desires and now that I was grown it was his turn. I believed that and I was happy when he found Jane. ‘His Jane,’ I would say making a spoof on Tarzan.

Jane was a little younger than Dad and pretty, a redhead with big, sparkling green eyes. She had a real nice figure and best of all; Dad adored her. I didn’t meet Jane’s daughter, Ellen until the wedding. Ellen was a charming girl with wonderful manners. Ellen was as pretty as her mother but with brown hair and blue eyes. I didn’t ask her age at the wedding but I guessed her to be around thirteen judging by her flat chest and no hips figure.

We were now stepbrother and sister and we got along well all through the reception. Intellectually, Ellen seemed far beyond her apparent years. I left looking forward to our next meeting. That came sooner than I expected. Dad and Jane went on an impromptu honeymoon and I just assumed that Ellen must have gone with them. They had moved into the home I’d grown up in where Dad still lived and I had only recently acquired my own apartment so a lot of my things were still at the house.

It was Saturday and I wanted to get a few more things from my old room. It was early and the house was empty, or so I thought. The door was locked and I used my key to get in. My steps on the stairs were silent and as I reached the top I heard something. I stopped, listening. The sound was coming from my room. It was a moaning sound as if someone were in pain or experiencing intense pleasure. What the hell! Had someone broken in and somehow hurt themselves in my bedroom? I slowly approached the door and gently pushed it open ready for anything except what I saw there.

Ellen was standing, facing my dresser with a picture of me in her hand. She had on one of those cute little tee shirts that expose a girl’s tummy and belly button. They drive me wild. The cute denim shorts she wore were down around her knees and she was obviously pushing her pink panties down to facilitate playing with herself. She hadn’t seen me and I started to quietly close the door to leave the child to her pleasure in privacy. I glanced into the mirror on my dresser before I closed the door completely and what I saw stopped me in my tracks.

Ellen’s small girlish fingers were busily playing with her very erect six-inch cock!

“What the hell. . .” I began.

Ellen froze then quickly pulled up her panties and her shorts fastening them before turning to face me. “Jason,” she said as she looked into my eyes.

I caught myself before I went too far. “It’s alright, Ellen,” I said, “you’re a child and there is nothing unusual about what you were doing. If I’d known you were still here I would have knocked, I’m sorry.” I paused. “Hey, wait, why would Dad and Jane leave a thirteen year old home alone?”

Ellen’s mouth dropped open. “Thirteen. I’m eighteen, Jason. Why did you think. . . Oh yes, I suppose so. As a girl I do look very young. Now I am beginning to understand. You did see, didn’t you?”

I looked down and the erection in her shorts was still very obvious. “Yes, I saw.”

“Jason, I’m sorry. I honestly didn’t meant to deceive you there simply wasn’t enough time at the reception to cover everything. The short of it is that Mom wanted a little girl and I was born. She made me into a sissy boy, or her version of her very own little girl. When my father found out he couldn’t take it and left us. I was eight then.” She stopped and watched me for a reaction but I was too stunned to respond. “Your father knows and he is very cool with it. He even said that I am very pretty. He wanted to know if I planned on getting an operation to make me completely into a girl.” She smiled at me. “I’m not going to though. I just enjoy too much being a sissy boy. I will understand if you are disgusted but I truly hope that we can become friends if not actual brother and sister.” She stopped talking then.

I had been intimately involved with two girls in my life at that time. I was not involved with anyone at the moment. Until this instant I would have sworn to you that I was straight with out a doubt. You can imagine my own surprise and horror as I felt my own cock rise in my pants looking at this eighteen year old boy dressed and looking every bit like a schoolgirl with a hard cock in her shorts. I was walking toward her. I couldn’t stop myself.

Ellen looked down at me. “Jason that’s big!”

My cock is eight inches and very thick when hard.

“I’m a virgin, Jason. You can well imagine that I find my secret difficult to discuss. My boy name is Elam and all through school I dressed as a boy during the day and a girl in the evening and on weekends. I’ve never had an interest in girls. . .”

She stopped talking as I kissed her. I put my arms around her slim waist and kissed her pushing my tongue deep into her warm mouth loving the taste of it. I touched her tummy and loved the heat that came from her. She eagerly returned my kiss and she sighed deeply into my mouth as my fingers slipped down over her crotch and stroked her throbbing cock through her denim shorts and the silk panties.

Our kiss broke for just a second. “Oh Jason take all of me,” she gasped.

I dropped to my knees and undid her shorts pulling them down frantically with her pink silk panties loving the way her cock sprang out into my face. I opened my mouth, licked the pre-cum from the tip of her shaft and then engulfed her all the way to her sissy balls. Instantly I felt her swell and heard her groan. As my fingers closed on her balls she exploded into my mouth with the sweetest sissy cum ever. I loved it, swallowing every drop.

I kept sexual lubricant in my end stand for when I’d had sex with my girlfriend here in my bedroom. They had both insisted I use rubbers and lubricant made sex so much better with a rubber. Now I pushed Ellen back on the bed and pulled her shorts and panties off and then took off her shirt to expose her flat little titties. As I sucked her hard nipples I took the lube from my drawer and pushed my pants down. Kissing, sucking, hugging, and wrestling with my clothes and we were soon naked.

I spread my cock with the lube. I was going wild; I had to have her. I pushed her legs up and spread them. Her cock was fully erect again and I pushed lube deep into her ass hole and made her very slippery. I kissed her deeply as I pushed the head of my cock into her.

“Unghhhhhh! You’re so big, Jason. Anghhh!” Ohhhhhhhh yes, no, not too fast, I never did it before.”

I bent and gently kissed her cute little nose. “Ellen, I won’t hurt you, honey,” I whispered.

“I dreamed of this after the reception, Jason,” she replied.

As we spoke I felt her anus relax and I pushed hard feeling my cock sink all the way into her steaming depths.

“Anghhhhhhhhhhhhhhhhhh,” Ellen moaned.

“Did I hurt you?”

“No, please don’t stop, Jason, oh it feels so good. Oh Jason, you’re fucking me, just like a girl, Jason thank you!”

It was so hot in her, so tight and her ass muscles were so strong. As my balls sucked up tight and I felt the fire of my cum shoot through my cock I grabbed Ellen’s cock and she exploded filling my hand with her sweet spunk as I came with a force I had never realized possible deep inside her tummy.

We just laid there holding each other after that.

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