Dating Diana

Published on Sep 19, 2020

Transgender

Dating Diana Part 2  

Dating Diana Part 2    

by Bill Beaumonte (oral_guy_2000@yahoo.com)  


This work of fiction contains explicit material intended for adults over 18. If you are under 18 or are offended by non-traditional sex, do not continue.  


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Author’s note: _I found trans women to be really hot and badly wanted to date one. But when I got the nerve to do so it changed my life! I hope you enjoy this work of fiction.

_

" That sounds good," Diana agreed, "But a lot of guys who date girls like me just want to get off and bale out on us."

"I would never do that!" I protested.

"We'll see," Diana responded, "But most of the guys I've known had a change of heart as soon as they cum – I hope you're different."

"I'm not sure I understand," I said.

"Jeff, you know I'm not like other girls?" Diana asked.

"Yes, of course," I agreed, "I think you are better."

"That's good enough for now," she said, "I won't put you on the spot by asking you why." I breathed a sigh of relief, since I wasn't sure I had a suitable answer.

"I'll tell you what seems to be on the mind of many guys," she continued, "They either want us because they think we are 'easy', or because they just want a girl with a dick."

I was startled by her directness, which felt like it was hitting too close to home for my comfort. I wasn’t looking for a girl that was “easy”, but a girl with a dick was incredibly hot to me! I just nodded and said nothing.

"But when they cum everything changes," Diana added, "They are suddenly ashamed and just want to leave – how do you suppose that makes a girl feel?"

"Pretty bad," I replied, "But I'd never do that!"

"I hope not," she replied, "I hope you are different, but can't be sure just yet."

"So do you want to test me somehow?" I asked.

"I'm not sure I want to test you," she answered, "But I do want to know what kind of guy you are."

"Okay," I said, "I know you are different than other girls, and I do want to be with you, and want it to be good for you as well. I don't know what else I can say."

"No need to explain," she said, "Let's just see how it goes." While remaining seated she reached under her dress and slipped her panties down to her ankles, then over her feet.

Diana handed me her panties and asked, "Do you know what this means?"

Stunned, I found my words and replied, "I looks like a pretty solid green light." Diana scooted her chair closer to me and spread her knees. I cautiously slipped my hand up her dress.

It delighted in the wonderful soft skin of her inner thighs. I was in familiar territory here, and confidently proceeded. Now I encountered what made Diana special. This was entirely new, and I was really nervous as I took her into my hand. I gently squeezed her and felt her harden in my hand. Diana leaned over and kissed me passionately as I fondled her, saying, "I think you're on the right track, but are you willing to finish what you've started?" I nodded affirmatively, but not entirely realizing what I was agreeing to.

As I nodded Diana said, "Come with me."

As she stood up, I could see her visibly "tenting" her dress. Diana held her purse in front of her to cover and took me by the hand. She led me to the bar, where another pretty girl was working. "We'll be in the office Marci," Diana said to her.

"Have a great time!" replied Marci, smiling knowingly.

Diana led be down a hallway past the restrooms and into an office. Entering, she closed and locked the door behind us. "Ready for this?" she asked.

"I think so," I said nervously.

Diana kissed me as I reached under her dress and resumed squeezing her. Her kisses became more passionate as she hardened, and then she said, "Now show me how much you want me," she said.

She lifted her dress and said, "I'm all yours," she said. I'd fantasized about this many times and dropped to my knees. She was just inches from my face when I got cold feet.

Sensing my hesitation, Diana said, "You can do this – show me how much you care."

I was really torn – I really wanted to do it but wasn't gay – how could I? "I'm sorry," I said, "I just can't."

Diana stepped back and was visibly upset as she dropped her dress. "I don't think you know what you really want," she said, "But it doesn't seem to be me!"

I didn't know what to say and felt so embarrassed. We returned to the bar area and Diana sent me away, saying, "I really hoped you were different!"

I left, completely humiliated. I returned home and thought it over. I wanted to suck her but didn't want to be gay. I didn't want to be a cocksucker, but did want to suck Diana. I really messed up tonight – I had exactly what I'd hoped for but froze.

To be continued . . .

Feel free to contact me with your comments or requests.

–Bill Beaumonte (oral_guy_2000@yahoo.com)

Next: Chapter 3


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