Shemale Sister Molly

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Brother discovers his desire for his Transgender sister.
1.8k words
4.37
208k
214

Part 1 of the 2 part series

Updated 06/08/2023
Created 09/07/2017
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Ergon
Ergon
74 Followers

Graduation Day

Molly, my little sister had just graduated. It was after the ceremony as everyone was saying their goodbyes I gave her a hug. I hadn't so much as touched her in over a year. Her "transition" to female had freaked me out. I know it was wrong of me, but my brother seemed dead to me. I had a sister, she seemed so different from who she used to be.

I think on top of everything I was a little jealous. She finally started being happy, and my life still sucked. She was beautiful, most of the boys in her class found her attractive but wouldn't date her, but she did manage to date older men who didn't seem to mind the large cock in her pants.

I felt a light tingle as her breasts pressed against my chest. "congratulations Molly,"

She smiled, "Thank you," she said. Then as I began to let up on the hug she stepped in and placed a kiss on my cheek and held on to it a few seconds longer. "Thanks,"

I could already feel myself reacting to the embrace. I hadn't expected this, she was very feminine. I always considered myself perfectly straight, but after looking into trans porn online I found a had a thing for chicks with dicks. That thought of what I knew was in her pants made me go erect.

This was when she looked down, I had reached and tried to adjust as quick as I could but she noticed and ... looked right at me and smiled. She graciously stood right in front of me as more of her friends came to speak. I was pretty sure all of her friends were female, but I'm not entirely certain I can tell the difference these days.

A gorgeous blond with blue eyes and extra small breasts walked around Molly to me. "Hey Chris, how's it hanging?" Molly started laughing, clearly trying not to but failing. There were some confused looks and laughs following her.

"I'm doing fine Lisa how are you?," Lisa was my crush since I was a sophomore and her a freshman. I never had the courage to ask her out, and she never seemed to like me anyway.

"I'm doing better knowing my best friend and her brother are finally getting along again,"

"Hey, we've always gotten along."

Lisa gave me a 'you know what I mean' kind of look. I did, I had kept my distance from my new sister. I wasn't really in the mood for an intervention either, so I took a cheap shot and reaching for a hug said "I should congratulate you to for graduation." She pushed me away with one hand, then stuck it out for a handshake. I took it.

"Nice try perv," she said.

Molly turned around and berated Lisa with a look

"Sorry," Lisa said.

They hugged "Be nice to my brother," Molly said.

I barely heard. Damn, Molly hugging Lisa triggered something in me. The two girls were fantastic, and I couldn't help but picture the two of them having sex. Petite Lisa under Molly, then I wondered if it had actually happened. Again Molly caught me starring. She looked up and down Lisa suggestively, and Lisa, just blushed.

That night after my parents fell asleep me and Molly stayed up talking. We watched a couple of movies and I pulled out some beer for us to drink. We hadn't talked like this, even before she transitioned. We talked about being out of high school, our friends, and just life. I brought up Lisa, and asked "So you hit that?" I asked.

She looked at me with disgust on her face. I immediately felt ashamed, but she started laughing.

"Once," was all she said. I pressed for more details, but all she would say was Lisa wasn't sure she wanted it again. The blush made it clear she did, but I understood. Hell I wanted Molly's body, but it did seem so wrong.

"When we hugged earlier, you were turned on? By me?," She asked. I felt paralyzed by the question. The she confessed to me something secret, "I'm a sex addict. I live for pleasure, I mean I try not to sleep around too much, but one of the reasons I wanted to be female, I wanted to be desired. I wanted to feel desired. It turns me on."

I was in fact, very horny. My now fully erect penis was clearly showing through my pants. She hadn't notice yet she was looking away. I grabbed her hand and moved it to my crotch. Her eyes went wide.

"This is my body's answer. Right now I'm too horny to think straight," I said. "You're so goddamn sexy." I leaned over slowly and kissed her red lips. That's when the hand on my cock gave it a squeeze and I knew there was no backing out. She was my sister, she had a penis, and I felt nothing but lust.

Molly unzipped my pants and pulled my dick out. She started stroking it slowly and I kept kissing her on the couch.

"Lets go to my room in the basement, I really don't want to get caught doing this," Molly said pushing me back. I forced myself back down for one more kiss and she played with my balls a little. In the end we got up and moved to the basement, her holding my hand.

Once we got through her door, grabbed her other arm, and pulled her back into me. Pressed against her back my penis felt at home. I moved the hair to one side and began to kiss her exposed neck. Licking and sucking gently. Molly moved slowly pressing her ass around my erection.

I wasn't sure what she wanted at this point except that she wanted to be desired. So I gave her that, telling her how beautiful and sexy she was. Caressing her body slowly and gently, both of us enjoying every minute of it.

One hand found a breast as the other reached down, when I finally had the nerve, to her dick. It was only a little erect. I was a little shocked but I knew hormone therapy can affect that area. I stroked, and kissed her. Her penis throbbed in my hand and grew a little harder. Only half hard now it was as long as mine.

I was curious. I had never sucked a cock before, but it was attached to a beautiful woman. I knew she deserved pleasure, she wanted it, and would give me it in return. Her ass against my cock still, I knew she wanted me, but clearly she was letting me lead.

I picked her up and carried her to the bed. I gave her a small toss onto it and we both laughed a little. A small wrestling match ensued and it ended quickly with me holding her down arms crossing her chest. I pulled her shirt up exposing her bare breasts. They too were dark tan and perfect. They weren't overly large, and definitely not the small perky ones Lisa had.

I began to kiss them but didn't stay long; I moved down. When I got to her shorts with the penis sticking out, I pulled them off. I put my lips to the tip, I knew what to do it wasn't hard. It was just weird. All I had to do was look up at Molly, my sister, looking back with anticipation and excitement in her eyes. Her cock throbbed once, and I put it in. It grew larger in my mouth.

Now fully erect it was large, I couldn't fit much of it in, but Molly didn't seem to care. It pulsed as I moved up and down on it as far as was comfortable. Then she asked for more. She put her hands on my head and waited a few seconds. I left them there. She pushed I gagged. I felt it go down my throat, I thought I was going to puke, but she let go just in time.

Breathing heavy I said "Damn, your too fucking big." She laughed, I began again, this time I forced it down less and shorter. Between long licks and playing with the tip I tried to get it down that far again. After that first one the gagging didn't seem so bad and she seemed to enjoy it.

"Stop or I'm going to cum," Molly said. "Oh my god you are good at..." she stopped thinking she might insult me.

I was really enjoying myself. Her moans, her mostly naked body, and my hand stroking my cock I was doing fine. I didn't feel insulted.

I climbed back on top of her and kissed her again. "I'll get better with practice," I said. She kissed back.

Then I continued to climb her body, until my penis was in her face. She took my cock in her mouth. It felt amazing. I was so horny I almost couldn't take it. I gently pulled away and she got it. She smiled and asked "Fuck am I too much for you,"?

"You calm down yet," I asked. I turned around and she was stroking herself.

"Sorry I want to enjoy this more, but I really just want to fucking cum," She told me.

I turned around and waved my penis in her face again. She was a good girl and took it in her mouth again. This time I gently forced myself down into her. Unlike me she could deepthroat, and it felt good. She started stroking herself faster and I knew it was about time. I started humping her face and the noises she was making were sending me over the edge.

I pulled her cock to my face and as soon as it was in my mouth she went back to stroking. She came first. It wasn't much, and I didn't swallow it. I barely noticed the bitter salty taste because I was in the middle of the best orgasm of my life. I was in her throat, I could feel her try to scream. Then I felt her moaning and swallowing and it was amazing. I pulled out and after she took a couple of breathless gasps of air she grabbed my ass and shoved me back down.

I left her in my mouth. I couldn't match her skill, but I did grab her penis and forced myself down until i gagged and kept doing it for almost a minute. It was easier because she had already started to go soft.

"God," she said panting, "that was amazing." This time she leaned in to kiss me and mentioned we were a sticky disgusting mess.

"That ended too soon, want to take a shower and go again?" I asked suggestively. I received a very seductive smile.

Ergon
Ergon
74 Followers
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AnonymousAnonymous9 months ago
So hot

My sister transitioned 2 years ago, and ever since then I have been lusting after her. She's so fucking hot. I never had any desire for sucking cock, but since my sister moved home, all I can think of is sucking her off, and being fucked by her. I even bought some butt plugs and started using them when I masturbate thinking about her.

I'm obsessed. When she was my brother we were never close, but now that she is my sister, we get along like never before. She's so much more affectionate and loving. She's like a different person to what she was when she was unhappy trapped in the wrong body. I think I'm falling in love with her, and I think she senses it. I'm terrified to talk to her about it in case I lose her. What do I do?

AnonymousAnonymousalmost 3 years ago

I wish Molly have small dick thick thigh bubble ass wide hip and Chris should rape her in anal like sex starved wild beast, I wish molly resist little incest guilt face expression leg shudder orgasm and near faint ahhhhhhhhh!!!!

AnonymousAnonymousover 3 years ago

great story I'd love to have a shemale sister like her.

RodimusMikeRodimusMikealmost 4 years ago
Chris,Molly,and Lisa.

Honestly Chris and Molly seem like perfect siblings,but when it comes to Lisa I think she is just a condescending evil bitch,and Molly should dump her ass as a friend and just be with Chris.It seems like since Molly went thru HRT that Chris likes her more as a sister instead of as a brother.

So I wish both Chris and Molly take this further and start fucking each others asses the way they are meant to,man do I love trans stories more than sibling incest ones,but to combine the two is like a dream come true.

horny2doithorny2doitover 4 years ago

Your story is just right ! Both brother and sister go along together and he is not judging her but is helping her get to the next comfort level and embracing her.

He gives as good as she does and isn't judging but rather accepting and showing her its safe and mutually enjoyable. Now he wants to take his new sister to new heights and accept her as she is now. Of course, if he gets her so aroused and gets her off in the process that is a great acceptance of her new self. Cannot wait for more.

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