This is the second excerpt from Travels with My Aunt. Here is Part 1.

Set in the hippie, Free Love era of 1969, Char is an 18 year old sissy who runs away from home with his hippie step-aunt to escape his stepfather's wrath. This part is right after Chloe discovers Char's sissy secret.

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“So, you’ve been doing this for two years, you fantasize about being a girl, really becoming one, but you’re attracted to women. What about guys?” Chloe asked. “Do they turn you on?”

“Not really. I’ve let my fantasies go there a few times but I always felt kind of icky…”

“After you came?”

I nodded, blushing. I could still barely believe I was sitting in my bedroom with this nearly nude hippie sexpot.

“How can you know for sure until you try doing it with a guy?”

Now I was really blushing. “I guess I’m scared to, Aunt Chloe.”

She thought for a long moment. “Char… do you trust me?”

“You—you seem nice. I guess so. Sure!”

“May I see you dressed up... as Charlene?”

My skin tingled, my breathing shuddered and my cock stirred. This was one of my main fantasies: to be dressed up by a sexy woman. These fantasies usually ended up in fucking, with her on top of me. Aunt or not, Chloe was as beautiful as any woman I’d seen, and she was near naked in those thin, wet T-shirt and panties. I was getting a new boner, so I thought of Chester’s threat to make it go down.

“Why… why do you want to see me... like that?”

She told me of her special friend Tanya back in Los Angeles: born a boy but miserable as one but now very happy living full time as a girl. Tanya was one of Chloe’s dearest friends, almost like a sister. Tanya had introduced her to many boy-girls like herself, who lived in little enclaves all across the country.

“LA, San Francisco, Houston, New Orleans especially.”

I felt like a caged bird who’d just learned there were many like him who flew freely all over the world. A deep yearning came over me. Suddenly I realized what I’d been doing was barely the tip of the iceberg. It was immediately followed by intense dejection. I had little money and had never been on my own before.

“How about here in New York?” I asked.

“I’m sure there is, but Tanya and I never hitched here together.”

“Hitched?”

“Hitchhiking, silly. It’s the best way to see America, especially if you don’t have a lot of money. You get to really see way more, meet a lot more people. It’s the best!”

“Wow, you’re kind of blowing my mind here.”

And your boobs showing through your top. And your crotch…

She gave me a smile, half playful and half sultry. “Yeah, I have that effect on people.” She rested her warm hand on my forearm. “So… are you going to let me see Charlene?”

Delicious electricity shot from her hand, up my arm and into my body, bringing a rush of excitement and anticipation. I looked into her loving green eyes and saw she really meant it. For whatever reason, she really wanted this. I looked around the room, suddenly uncertain and embarrassed. “Do I… should you… I mean…”

She smiled gently. “I get it. You’re nervous about stripping in front of me, who has a few clothes on. Let me even the scales.”

With that, she peeled off her T-shirt. Her breasts were perfectly round and large, her nipples almost as big as sewing thimbles. Her belly was mostly flat, with a pleasing swell and a deep navel. In that instant I wanted to be her as much as I wanted to make love to her. Chloe’s smile made her more beautiful than any centerfold.

“Oh, god,” I breathed.

“Okay! Your turn!” she chirped.

With trembling fingers I took off my boy clothes and dropped them in a heap. She made sweet cooing sounds at the sight of my satin panties and how my cock nestled in them… my hardening cock. She picked up my pants and shirt and tossed them out of view on the other side of the bed, saying she didn’t want the sight of them ruining this.

She knelt in front of me, eye level with my cock pushing madly against my panties and nearly poking its head out of the waistband. She smiled impishly, then flicked her finger hard against the underside of the head. I yelped in pain and my cock deflated to its flaccid state.

“They’ll be time for boners later on,” she said with a giggle. “Let’s see you model that new bra and panty set.”

After I’d tried on the new lingerie and modeled it, she frowned a little. “Your long hair really helps, but I think Charlene needs to be made up for this. So we can really see what a pretty girl you are.”

“I don’t think that’s a good idea. What if my folks come home?”

“They’re in Easthampton,” she assured. “They won’t be back until tonight… Charlene. We have plenty of time.”

“Are you sure?”

“I thought you trusted me,” she chastised mildly.

With excitement trembling my tummy, I watched Aunt Chloe set up all the makeup I bought. As I sat on my bed, she deftly painted my face while she commented that many hippie women were clueless when it came to makeup, but she’d worked as a stripper, off and on, for years. The thought of her stripping brought my boner back, quickly tenting my panties. It ached so good!

My step-aunt talked as much to herself as to me as she made me up. She said I was fortunate to have such a smooth, fair skin, that my complexion really needed little foundation. She said my eyes were pretty, my lashes naturally girly, and my eyebrows were perfect as is. My insides felt fluttery at the gentle touch of her painting my face.

She stood, laid a hand on my shoulder and led me to the mirror. “Look at yourself, Charlene. You’re such a beautiful girl.”

 I sighed out a rush of air at the sexy girl in the mirror. That was me! At that moment I wanted to be Charlene forever! “Th-thank you, Aunt Chloe! I… I don’t know what to say. I’m so happy right now!” My boner throbbed in my panties. I was dying to touch it.

Chloe fluffed my shoulder-length hair with her fingers. “I could do so much with this. But first—” She held up a finger. “I have the perfect dress for you to try on. I’ll be right back!”

She snatched up her T-shirt and left my room. I watched those large, round asscheeks as she sashayed out the door and closed it. I couldn’t wait for her to strip those panties off! Then I turned my attention back to the mirror. I toyed with my cock through my panties, fantasizing about licking Chloe’s pussy—like lesbians!

Mmmm—me eating my aunt’s pussy while she blows me!

I was so far gone in my erotic reverie I never heard the front door close—never heard Chester and Mom plodding up the stairs as they griped something about the car. So when I heard the doorknob rattle, I turned to face the door with a big smile, expecting Chloe bringing in one of her dresses.

I froze with shock at the sight of my stepfather standing there with surprise on his face, a look that became a dark scowl. Without closing the door he stomped off, growling I’d get the treatment I needed if I had so little control over myself.

I was so worried about going to a mental hospital, I started to go after him—dressed as I was. Chloe got to my door at the same time I did. She’d changed into a simple cotton shift. She clutched a dress that was meant for me. Her face was filled with worry.

“That was terrible,” she said. “I can tell how mad he is. Uh… When he said ‘treatment,’ do you think he means—”

“He’ll put me in a psych ward or something,” I wailed.

“He seems serious. I thought maybe you were exaggerating a little bit before.”

“He called me abnormal. Said I had a sickness.”

“Damn it, Chess. He’s more uptight than I remember him... You think he’d really do that?”

“I know he would! Shit! What am I… What am I gonna do?”

Aunt Chloe gave me a long look. “Well… do you think you’re sick? Do you want a bunch of shrinks trying to change you? Or do you want to be Charlene? Really be her?”

What was she talking about? I was in serious trouble!

“I don’t want to go to some hospital!”

“I know, but that’s not what I asked. Do you want to be Charlene? And… do you want my help to become her?”

Her words sunk in and I felt hope. Chloe had become like a hippie angel of mercy. “What do I have to do?”

“You and I are leaving tonight after Chester and your mom go to sleep. Now, no more questions, okay? You’ll need a duffel bag or a cheap suitcase and pack the following stuff…”

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