Madison Fucks Her First Trans Woman

Megan saved me. Caught between two worlds, I felt out of place, out of body, and out of my mind. I'd always felt like I didn't belong in my body - a boy by birth. It wasn't until my mid-teens that I had the courage to say something - do something about it. Despite my dad's rejection, my transition to womanhood was pretty smooth. I took hormones and I changed - I became slenderer and sleeker. My waist pulled in, my hair turned fair and light, and my voice register went higher. Then there were my breasts. They grew and grew until even I was impressed.

My cock, however, did not shrink. It was still as big as ever. It became a problem that I tried to hide. I learned to tuck and blend in as a woman. It worked really well. Being tall for a girl worked in my favor. People - guys and girls - started noticing me... being attracted to me.

If it hadn't been for Megan, though, it would have stopped there. I would have remained a virgin - and not a part of either world.

The night I met her at Simone's party was the best night of my life. Tall herself, curly brown hair, full lips, nice boobs and legs. But most importantly it was her kind face and her kind eyes. She was full of compassion for me and pulled me out of my shell. We ended up having the most wonderful sexual experiences together, and I will always be grateful for her gentleness and openness.

I guess that's why I agreed to go to yet another party. Megan said it would be good to meet others like me. I wasn't so sure. Life was difficult enough being trans. I wasn't sure I wanted to borrow the trouble of others and add them to my own.

But since meeting Megan, life had been better - a lot better. I felt comfortable in my own skin and even ventured to have a threesome with Megan and Simone. That was wonderful. I learned to love the way my girl-cock felt as it entered a woman's pussy. With them, I could express the whole of me - the parts that were girl, and the parts that were boy.

So, in the end, I agreed to go.

"How do you know all these people?" I yelled over the music.

Megan was only inches from me but apparently couldn't hear me. She greeted person after person - giving them hugs or pecks on the cheek and lips.

We made our way through the crowd at a bar I'd never been to. Eventually we went into a side room where the volume decreased markedly. I breathed a sigh of relief.

I was wearing a red dress - silky smooth and flattering to my large figure. My make-up was top notch, and my blonde hair fell halfway down my back - sleek and silky. I'd spent time tucking my dick so for anyone present, I was wholly and totally a woman.

"Megan," I said, pulling on her shoulder to stop her forward progress. "How do you know all these people?"

Megan stopped and turned to face me. "You can't blame me for having a lot of friends, Madison. These are great people. You'll see. Lighten up!"

I shrugged my shoulders and followed her as she went into another room. This one was much quieter and featured its own bar and seating areas.

"Megan!" a voice cried out from the other end of the bar. "Over here!"

As Megan led the way, the voice became a person. And what a woman! As tall as me at 5'8", slender, with dark hair halfway down her back. Her boobs were a bit smaller than mine, but stood out like two globes, full and round. She was wearing a silky dress that clung in all the right places. What struck me the most, though, was her face. It was so open and filled with joy.

"Kiley!" Megan called as we approached.

Kiley and Megan hugged and kissed. I was a little surprised that they shared a brief kiss on the lips - it was more than just a kiss of greeting.

"Kiley, this is my friend Madison," Megan said, turning to me and pulling me closer.

"It's so nice to meet you, Madison," Kiley said, reaching out for a hug. "Megan's told me so much about you and I was excited to get to meet you in person!"

Kiley smelled like something sweet - I wasn't sure if it was her perfume or shampoo, but it added to the lightness of her personality.

"Nice to meet you too," I said, breaking from the hug.

"I've got a table over here," Kiley said, motioning across the room. "Let's grab some drinks and chat!"

We each got a glass of wine and got settled in a booth off to the side. I couldn't help but be attracted to Kiley. I'd been with women before (Simone and Megan) and really loved being a lesbian with a little something extra. She was funny and light-hearted, always joking and laughing. She was so at ease with herself. How I would love to be that confident!

"So... what do you do?" I asked.

"Oh, it's pretty boring," Kiley responded with a smile. "I'm a software engineer so basically I spend my days enslaved to a computer."

"Wow," I said. "Impressive!"

Kiley laughed. "Not really. It gets old after a while. But I do enjoy the money. And I've met some super interesting boys and girls."

The more I talked with Kiley, the more I liked her, and felt attracted to her. She had such an easy way about her. She'd reach across the table and touch my hand with her delicate fingers to make a point. I could see why Megan was so into her.

We talked for a couple of hours. Eventually, Kiley said she had to go - an early day coming up.

We stood and hugged. Kiley's hug lasted a bit longer than usual. I felt our breasts press together and smelled that wonderful sweetness in her hair again. She even kissed me on the cheek.

"We've got to get together again soon, okay, Madison?"

"I'd love it," I said - and meant it. I was getting infatuated with this beauty.

"Kiley's so great," I said as Megan and I left the bar a few minutes later.

"I know, right?" Megan said, taking my arm.

I live only a few blocks from the bar, so we headed to my place. I was curious about something but held my tongue until I was home.

"I thought you said we were going to meet other trans-women?" I asked, setting my purse down on a table near the front door.

"Mm hmm," Megan answered, going into the living room.

"But Kiley... she's so pretty and feminine. And very sexy. It almost seemed maybe like the two of you have been together?"

Megan looked at me funny, and cocked her head to the side, sending her curly hair across her face. "Well, yes, I have been with Kiley."

"You have?" I asked, my eyes widening. "What was she like?"

"Even more beautiful without her clothes on. We made each other cum so hard, I get aroused just thinking about it."

"So, you loved licking her pussy?"

"Her... pussy? Madison, I think you're confused here. Kiley is a person like you. She's a trans-woman."

My mouth dropped open. "But... she is so much a woman!"

"Oh yes," Megan responded. "She has a wonderful woman's body. But like you, she's also got a girl-cock. It's... um... not as big as yours but feels so wonderful inside me."

"Oh wow. I just wouldn't have guessed it. She's like me? I hope someday I can have her confidence."

I also thought, she did such a perfect job tucking that I didn't see any hint of a girl-snake between her legs. But it got me to thinking about what it might look or even feel like.

"She really likes you," Megan said as I sat next to her on the couch. "I can tell. I think she wants you."

"Me?" I said with surprise. "You think she wants me?"

"Oh, I know it. In fact," Megan said, looking at her phone, she texted that she's really into you and wants to know you better - much better!"

I had to admit that thinking this perfect woman would want someone like me was both surprising and arousing. I felt my cock begin to stiffen between my legs.

"Are you all right?" Megan asked. "You seem uncomfortable."

"Is it terrible that thinking about Kiley is getting me turned on?"

"Oh, no," Megan answered. "I was hoping that would be the case. Want me to help deal with your uncomfortableness?"

"Please!" I said, standing.

Megan kissed my crotch and at the same time, reached up under my dress and pulled down on my panties. As they came down my legs, my cock burst forward, tenting out my dress.

"Oh... someone's excited!" Megan said, taking my panties all the way off.

I pulled up my dress and my cock sprang out. Megan grasped it and squeezed along its length.

"Oh!" I gasped.

"I've been hungry for this all night!" She said, looking up into my eyes.

She kissed the tip and flicked out her tongue, touching the small hole at the very end. She then kissed down the length of my shaft, going back up to the tip with her tongue.

"Fuck, that feels good!" I said.

"Mm," Megan purred, her mouth on my girl-dick. "It tastes good too!"

She opened her mouth, and I watched my cock disappear into a warm tunnel of wetness. She put about half of me in, sucked in, and pulled back off. Warm feelings of arousal coursed through my body.

"Take off that dress, Madison," Megan said, coming off and holding my dick in her hand.

I used both hands to pull the dress over my head. Now all I had on was a lacy red bra that plunged and showed off plenty of cleavage.

"Mm," I love that bra," Megan said.

She reached up with her other hand and stroked across a breast, sending more good feelings into my body. I loved that after my hormone therapy, my nipples became super sensitive. Right then, they began standing up erect and hard.

Megan stood, still holding my dick in her hand. We kissed, trading tongues and mashing our lips together. She kneaded my cock, and I could feel it getting harder. I pulled in on her ass cheeks and ground my body against her, my cock pushing into her stomach and riding up.

I reached up and undid the zipper of her dress, pulling it off her shoulders. Megan stepped back and let the dress fall to the floor. She was wearing a matching pink bra and thong, which barely covered her mound.

We kissed again and I felt her reach behind my back to undo the clasp of my bra. As it came loose, I let it fall from my arms, my big boobs free at last. Megan tweaked my nipples, sending goosebumps all over my body. She bent over and took a nipple in her mouth, sucking in on it, making me gasp with pleasure.

With one of my hands I caressed her crotch, now wet with juice.

"Mm," Megan moaned, her mouth full of nipple and breast.

I went under the hem of her thong and let my fingers get coated with the clear liquid between her pussy lips.

"Ah!" Megan groaned as my finger ran down her slit.

She undid her bra and shimmied out of her thong. We came together and ground our bodies on each other, coating my dick with her juice.

"I love our slick pubes," she said.

"I know - we got that done together, remember?"

"I know - and then we made love all night to celebrate!"

Megan took my hand and led me to my bedroom. We got up on my bed and made out, our hands fondling our breasts, my she-dick, and her pussy. I was very hard and itching to be inside her.

As if she knew my wish, Megan turned on her back and pulled me on top. She positioned me at her opening.

"Fuck me, Madison!" she said.

I looked down and pushed, the head of my cock slowly penetrating her pussy lips. I backed out and she coated me with even more juice. I pushed back in deeper... out... then in more... out... then in all the way, my pubes rubbing up against her clit.

"Oh... fuck yeah!" she moaned. "Your dick feels so wonderful inside me. So, fucking wonderful!"

I got up on my arms and watched my boobs sway back and forth as I fucked her pussy. Megan took my nipples in her fingers and even got up on her elbows and put both of them in her mouth at once. I nearly came right then.

"Harder," Megan said. "Fuck me harder. I want to cum on your cock!"

I pushed in harder and faster, the feelings of arousal building all over me - in my nipples, and up and down my dick. I was getting ready to explode.

Suddenly, Megan's back arched, and her legs convulsed. She laid her head back and closed her eyes, letting out a glutaral sound as she came.

"Ah!"

That was all it took. An intense feeling started in the base of my cock and traveled to the tip. I knew in a moment that a fountain of cum would erupt from me and fill her pussy. I pushed in deeper and felt myself spurt the first load. It felt incredible.

"Oh! You're cumming in me. Oh, fuck! Oh, fuck! AHHHH!" Megan cried out.

I kept jerking and pushing and cumming, spurting a huge amount of jizz inside her. With every push I felt renewed pleasure that I didn't want to end.

Finally, I was done. I laid on top of Megan and we made out, her legs still jerking and her breath coming in ragged bursts.

I rolled on my back, satisfied, peaceful. Megan got on her side, and I watched as she played with my still erect nipples. My breasts stood up, firm and round. Megan took a nipple in her mouth, sucked on it, then spit it out. It felt great. Down further, I could see my now limp she-dick, with dribbles of cum oozing out of the tip.

I started thinking about Kiley, and what it might be like to be with her. I saw my cock start to lengthen and thicken as it traveled across my stomach.

"What're you thinking about?" Megan asked, looking up into my eyes.

"I'm feeling what you're doing to my nipple," I replied. "But I was thinking about Kiley. You know I've only been with you and Simone. I've never been with another trans woman. But you have, right? With Kiley?"

Megan nodded, reaching down to play with my dick. "I think you'll love playing and sucking on her cock, Madison. And you already know what it's like to have someone fuck you in the ass. Remember our threesome with Simone?"

I did remember. I fucked Simone's pussy while Megan pushed a strap-on into my ass. What a feeling.

"But I've never had another cock in my mouth."

"You will LOVE it, Madison. Besides. I'll be there the whole time. Kiley wants both of us."

"If you're there, then I'm up for it."

"I'll say!" Megan said, gripping my now hard cock.

We invited Kiley over the next evening. She readily agreed. I was excited and nervous at the possibility of making love to her.

I decided to dress up a bit. I chose a silky blue dress. I did my makeup and hair, then tucked myself in. Megan wore knit pants that clung to her mound and showed her pussy lips. Her tight top pressed in on her breasts, causing her nipples to show through. I hoped it would be sexy enough to impress Kiley.

Megan arrived at my place early and we did the final touches - candles, a nice meal, a bottle of wine - not knowing at all how the evening would go.

The doorbell rang and I answered the door. Kiley stood there looking even more stunning than the night before. Her green dress clung closely to her chest and showed off her figure. But what shocked me was that she was not tucked at all. She wore a thong that let the outline of her girl-cock show clearly in the front of her dress.

The effect was amazing. She was the best of both - girl and boy - and proud of it. I'd never been so impressed with anyone in my life.

"Are you going to let me in?" Kiley asked, smiling.

"Oh... so sorry!" I said, embarrassed.

"I guess you like my outfit?" Kiley said, moving in to give me a hug.

"Oh, yes!" I said, hugging her and feeling her chest against mine. "You look so beautiful!"

"And sexy, girl!" Megan said, coming up and taking a hug and kiss from Kiley. "You're rockin' that outfit for sure," she said, looking Kiley up and down.

"Glad you approve!" Kiley said, setting down her purse. "I'm ready for some wine!"

Megan and I exchanged a look.

"Have you ever seen her dress this way?" I whispered as Kiley went into the kitchen.

"No, but I love it, don't you?"

"Uh huh," I whispered back.

When we got into the kitchen, Kiley had already found the bottle of wine we'd chilled in the refrigerator.

"Hope you don't mind," she said, opening the bottle and beginning to pour into the glasses we'd set out.

"Not at all," I said, trying not to stare at her shape.

"Cheers!" she said, holding up her glass.

"Cheers!" we answered, clinking glasses.

We all took a deep drink and let the cool wine flow smoothly down our throats.

"Kiley," I said, setting my glass down on the counter, "can I just say you are the most beautiful woman I've ever seen."

"Flattery will get you everywhere!" Kiley said with a big smile. "I love dressing this way when among friends - it has a sort of impact."

"I'll say," Megan said, eyeing her crotch.

"So, I guess you approve, Madison?" Kiley asked. "Do I look appealing to you?"

"Absolutely luscious," I answered.

What happened next surprised me a bit. As I looked at Kiley, her nipples, her legs, her crotch - her girl-cock started growing - pushing out and lengthening in her thong. The dress clung so tightly that the effect was mesmerizing.

"You're..." I started to say.

"Getting aroused by you? Oh, yes," Kiley said.

"You're just so free," I said. "I'm loving it!"

"Then let's be free with each other," Kiley said.

"Oh!" I said, enjoying her forwardness.

Kiley set her glass down and stepped around the counter towards me, her cock pushing straight out of her dress. She took my head in her hands, leaned in, and kissed me on the lips.

"Mm," Kiley moaned.

I felt weak. Her nipples pushed in on one of my breasts, and her dick rode up on my stomach as she came in close.

I opened my mouth and felt Kiley's tongue enter, swirling her wet tongue around mine.

"Oh, wow!" I said as we broke off.

"Hope that was okay," Kiley said.

"More than okay," I said.

"I want in on this too," Megan said.

Kiley kissed her and I saw their tongues trade mouths. Megan put her hands behind Kiley's ass cheeks and pulled her in as she leaned against the counter.

When they broke off, the two faced me with arms open, beckoning me in. I joined for a three-way kiss. I felt Kiley's hard snake press against me again and my cock started getting hard, wanting to pull free from between my ass cheeks.

"Maybe we should take this to your bedroom, Madison?" Megan said.

We walked the few feet to the bedroom. Kiley turned her back to Megan. "Care to unzip me?" she said.

Megan unzipped her dress from behind. She let it fall from her shoulders to the floor. Beneath she wore the most beautiful black bra - plunging, lacy, pushing up on her boobs. Her panties barely contained her large wand.

"Want to touch?" Kiley asked me. "Why don't you start with my breasts."

I put out my hands and cupped Kiley's breasts, squeezing them and feeling their fullness.

"Mm," Kiley said softly, watching my fingers.

It was getting harder to contain my erection.

Megan reached around Kiley's waist, and I saw her hand cup her cock, pulling her fingers down its length. A small bit of wetness appeared at the tip.

"Oh!" Kiley gasped, grunting and pushing forward with her pelvis.

"Do you want to see it?" Kiley asked, looking into my eyes.

I nodded. This was a big step. I'd never seen another woman's wand before. My own was aching for release.

Megan pulled down Kiley's panties and her cock popped out, hard, big, throbbing and... beautiful. She grasped it and pulled down its length. I noticed more moisture appear at the tip.

"It's beautiful," I said, staring at her crotch.

"I'm so glad you like it," Kiley said. "Do you want to touch it?"

"Can I?" I said, looking up.

"You can do all sorts of things to it," Kiley said. "Whatever you feel comfortable with."

Megan offered Kiley's dick to me. As my fingers touched it, I realized what it must feel like for a girl to touch me. Her cock was warm to the touch. I squeezed slightly and felt the soft skin give way to hardness underneath.

"Oh, yeah," Kiley moaned. "Stroke me."

I gripped and pushed my hand down her length, causing her head to go back and take in a big breath. "Oh, fuck!" Kiley said.

I repeated the motion, coming back up, gripping and pushing down.