Just Sex Mates (boyxboy)

Chapter 13: Jenna.

In all the time I'd known Jenna, we had never had a real heart to heart discussion about her transgender journey. Yeah, it had been mentioned and it had come up in conversations, but we had never really got into the nitty gritty details of it. Why should we have, anyway? I just accepted her as who she appeared to be. A girl. A beautiful one at that, both in looks and personality. I had never felt the need to ask questions about her gender or sexuality just as she hadn't questioned mine. But now, as a friend, I felt that she needed someone to unburden to. A friend that would not judge or preach. The thing was I knew very little about transgendering so I couldn't give any advice, but I could listen and give her my uneducated opinion, couldn't I?

I placed a hand gently on her shoulder. "I just thought, with you being all tearful like, that something was worrying you and I hoped that you would think me a good enough listener to unburden yourself to. That's all. Do you want to talk about it?"

Jenna nodded. She then played with her phone, obviously searching for something. Then she raised her eyes. The look she gave me was sad, yet inviting. I sensed that I was going to be included in on something very personal, something very private, as she handed me her phone.. "I want it gone..... It's just once it's done, it's done. It's not going to be easy saying goodbye to Joseph forever."

On the screen was a picture of a very handsome, young teenage boy. I assumed he was this Joseph who had since morphed into Jenna. I drew in a deep breath. "Wow Jenna! If I had known you at school I would have definitely hit on you."

"Thanks, but with both of us wanting to ride cock you would have been well disappointed, wouldn't you?"

I handed the phone back. "True..., but you were as handsome as a boy as you are as beautiful as a girl. Whichever gender, you sure look a cracker."

"It's fine looking good on the outside, but I needed to feel good on the inside too," she answered as she flicked through her photos before showing me another of her as she was transitioning.

She looked drawn and dark eyed. It was clear from the photo that it was a difficult time for her. "Saying a permanent goodbye to someone you know outside as well as inside, can't be easy. Let's go get another drink...." I suggested. "Then you and I can talk until the cows come home. They say that a trouble shared is a trouble halved, don't they?"

Jenna followed me into the lounge area and slumped on the sofa.

"Hows' about we chat about this with Jack?" I ventured after producing a bottle of Jack Daniels from a cupboard and waving it at her. "I've been saving it for an important occasion and nothing is more important than this."

After filling two tumblers with ice I handed it to her and generously filled it.

She necked it.

"Easy Jenna. It's good stuff, is that. Jack likes to take his time in getting to know you," I chided, as I filled her glass again.

She smiled weakly at me and took a small sip. "I just didn't feel right as Joseph. I've never felt right. I've always thought I was in the wrong body. Even from a young age, whenever I went out, I wanted to wear a skirt and a frilly top, just like my older sister, Julie. I desperately wanted my parents to address me as 'her', just like they did Julie. They wouldn't. They never ever let me dress how I needed to be dressed and I always felt self conscious and that everyone was looking at me."

I sat down beside her and we both twisted in the small space so that we were facing each other. "You said to me ages ago that you started to transition when you were 15...., but how old were you when you first dressed as you wanted?"

"I was 8. I was round a school friend's house, Amy was her name, and she dressed me up in her party clothes. I remember it vividly. It was a pink taffeta dress with a big bow on the back. It was wonderful. It was frilly.... and so girly. It was the most fantastic feeling ever. She then put her mother's makeup on me..., you know..., just lipstick and eyeshadow.... Oh yes, and mascara ...., and a bit of rouge on my cheeks." Jenna chuckled, obviously recalling something amusing that had happened. "She got well told off for that. Not so much for dressing me up in her party dress but for touching her mum's things. I got bollocked at home by Papa and was never allowed to go round Amy's house again and her parents banned her from being friends with me at school. Amy told her friends what happened and it spread around the school. That was the start of me being rebellious and from then on I started to wear girls clothes and makeup."