Chapter 9

I had difficulties getting dressed because my recalcitrant cock kept ‘rising to the occasion’. In the end, I had to retrieve an ice pack from the freezer and hold it against my balls until my dick had wilted enough to be taped away. To meet Grant, I chose my olive-green A-line midi dress and my backless, halter-neck top.

I did my makeup to look as feminine as I possibly could at this early stage of my transition and added some light jewellery to intensify my feminine appearance. I chose sheer black stay-up stockings and black slave-collar high-heels to complete my look.

I’m sure I chattered like a bird the whole way to the Pig ‘N’ Whistle pub and restaurant, but I really don’t remember the journey because I was so nervous. Aunt Liz parked a little away from the restaurant, but I couldn’t make myself leave the car. I sat beside my aunt, shaking and too scared to move.

“You need to do this to move on, little one,” Aunt Liz said encouragingly. “You need to reconcile your fear with your desire for this man.”

I knew she was right, so I took a deep breath and stepped out of the car. My knees shook, and I looked beseechingly at my aunt, but I squared my shoulders and glided into the bar/restaurant. I spotted Grant as soon as I stepped up to the ‘Please Wait to be Seated’ sign. Grant was much leaner and more handsome than I remembered him being.

When we were at school together, Grant was taller than most, but he was a pudgy kid. My mother had speculated that Grant became a bully almost reflexively. He was bigger than most and clumsy to boot. Therefore, he hurt the other kids even when he didn’t mean to. My mum conjectured that becoming a bully was better for him than being known as big and clumsy. If he was a bully, he was intentionally hurting kids and not just because he couldn’t help it.

Grant was looking expectantly at the entrance but hadn’t realised who I was. The greeter guided me to his table, and Grant stood up disbelievingly. “Jaysus!” He exclaimed. “Dylan? Wow, dude, have you changed!”

Strangely, I winced at ‘dude’. I did correct him by saying, “I prefer Jillian now.” Then, I thought, ‘Wow! How did that happen so quickly?’ I’d been given a new name only a couple of hours earlier, and weirdly, I’d immediately adopted it despite being a male and my new name being feminine.

Grant offered his hands, and I placed mine in his. His thumbs wonderingly touched my long, dark-red painted, false nails. Then he raised them to his lips and kissed the backs of my hands. A shiver of unwanted desire raced up my spine, and my cock lurched in my panties despite being taped away.

Still not a good idea!

Grant helped me into my seat and then sat opposite me. I’d instinctively rested my hands on the table, and Grant took them in his again. His thumbs stroked my nails again before he kissed their backs again. I watched Grant’s eyes, mesmerised. I knew that if I didn’t pull my hands away, I would be lost, and Grant would soon be my first male lover. But I couldn’t pull my hands away. My cock lurched again, and unfortunately, Grant thought I was grimacing because he was holding and kissing my hands. He released them as they’d scalded him, and he blushed embarrassedly.

“Sorry,” Grant mumbled as he nervously picked up the wine list.

I put my hand on him in what I imagined was a seductive manner and tried to use a sultry voice. “No, Grant, I wasn’t bothered by you touching me. It’s a pain thing.” I hesitated before lamely finishing, “The way I’m dressed means when certain things happen, I hurt.”

“Like what?” He asked, taking my hands in his again.

I blushed before answering, “Well, if this goes well, then you might get to find out.”

Grant looked at me quizzically before his eyebrow arched, and he said, “Oh?” Then realisation hit, and he blushed as red as I was and said, “Oh! Umm. Well, I guess that’s good for me and bad for you, huh?” Changing the subject, he asked, “What would you like to drink?”

“My mother and I couldn’t afford to drink alcohol,” I replied shyly. “My aunt is teaching me how to choose the best wine to go with my meal, but I’m still woefully ignorant. Do you think you could choose for us?”

“I was sorry to hear about your mum,” Grant said sympathetically. “I wanted to come and say hello and offer to help, but I was pretty sure you wouldn’t want to see or talk to me.”

“You’re right,” I replied. “I would probably have freaked out if you’d turned up at my house.”

Before Grant could answer, a waitress came to our table and asked if we were ready to order. He muttered something about being a beer drinker and having no idea what to order. Then inspiration hit, and he asked the waitress, “What would you recommend for two inexperienced wine drinkers to have with their meals?”

The woman looked at me dubiously before saying, “After I’ve seen some ID, I’d recommend a basic Chardonnay for chicken dishes or, if you’re eating steak or lamb, then a simple Cabernet Sauvignon would be best. They’re both lovely, drinkable wines that don’t require an experienced palette.”

“We’ll have a glass of each,” Grant said confidently.

“Yeah, I’ll need to see some ID first,” the waitress demanded.