Children of the Boss

Chapter 46: Dean

May 20th

Ever since being dumped, I started hanging out with Angela more. Ever since school let out a couple weeks ago, I started being lazy. I didn't work and I didn't even work out that much. Instead, I got on social media more. I was on Snapchat a lot in general and had a lot of people on there watch my story. I also had tons of followers on Instagram and always had people commenting something thirsty on my posts. I had a Twitter, but I actually didn't use it that much, but I started to get on it more.

I searched my name on Twitter and looked at some of the thirst-tweets about me, but then I came across a certain post. 

It was a photo of me shirtless and in running shorts and shoes on the street. There was also another photo of a guy I didn't know who was overweight and eating cheetos. The caption said "Dean Jeff-Lane looked like this when he was sixteen but also the guys I know my age look like this."

The photo was from when I was sixteen. I was already really in shape at that point, but that was me at my least healthiest though. It's when I had my breakdown and over-exerted myself so much I had to go to the hospital. It's when I was drinking nothing but protein shakes and working out non-stop. I was one step away from taking steroids at that point, and refused to eat a normal diet.

I decided to quote retweet it. I said, "Fuck off with your fatphobia. This photo was taken of me when I was suffering from an eating disorder. It's literally me at my unhealthiest. But people only care about people's health when they're fat right?"

My notifications went wild. A lot of people favorited it and retweeted it. The comments were less, but most were asking if I was okay now. I replied to my own tweet and said, "I am much healthier now by the way. I enjoy exercise but sometimes use it like a drug when my mental health is shit. I'm getting better though." 

The girl replied with some bullshit apology but I just ignored it. Eventually I turned off notifications.

"You're trending on Twitter," Angela told me later as we got lunch.

"Riveting," I said flatly.

She snorted. "Some people are talking shit."

"Like what?"

"This guy said, 'Dean Jeff-Lane is like his dads, just as gay. Go suck some dick.'"

"Now I remember why I'm not on Twitter anymore," I said, but pulled up Twitter anyway. 

I found the tweet she was talking about and spent five minutes figuring out what to say. I quote retweeted it with, "I'm not gay, the only dick I suck belongs to a girl."

Angela laughed for a whole minute. "I can't believe you actually said that. Everyone is gonna think you're gay now," she said, quickly typing away on her phone.

"I clearly said I'm not though. I would never suck a guy's dick, I don't like masculine appearing people."

"Sadly there are a lot of people who won't understand what you mean."

"Which is dumb," I said. "My parents did a good job of teaching me that gender is dumb and genitalia doesn't mean anything. Like you're a girl with a dick, big whoop."

After my last tweet, people started calling me a voice for the people, and I was "white boy of the month." It was kind of cool though, because some trans activists I liked connected with me on Twitter. However, it soon blew out of proportion, because suddenly people were saying I was such an advocate. So I sent a few series of tweets that said:

"I'm an advocate for the LGBTQ community but I'm not somebody to really put on a pedestal. I respect women but also literally only ever think about having sex with women. My fwb is a trans girl who has nice boobs and a fat ass. I've never sucked her dick because she isn't into that and neither am I, I just tweeted it because I don't care if you think I'm gay. At least I'm not transmisic. My fwb is a beautiful, intelligent woman and I don't care what's between her legs, she loves going down on me and letting me give it to her from behind. Honestly fuck any guy who fetishizes trans women, and fuck the guys that act like they've never imagined being with a trans woman. Women are awesome, and I'm sorry I'm a pig who literally only thinks about boobs, but that's why I don't want any of y'all to treat me like I'm special. My dm's are open, please sent me tit pics as long as you are of age. Thank you."

"You are so..." Angela shook her head.

"What?" I asked.

"You're honest, that's for sure. What are your dads going to think about this?"

I shrugged. "They can't really expect much from me can they?"

My series of tweets ended up making people like me more (besides the transmisic ones). Peolple said they loved that I said to not give me a platform, and that they were more than willing to send tit pics to a woke king. One trans activist, a Vietnamese-American woman named Lisa Nguyen messaged me, asking if we wanted to get dinner. She was hot. I said yes.

So the following week, I went to a small, closed off restaurant by Central Park and met up with her. She was even more beautiful in person. She was the kind of trans woman where people would assume she's not trans, but it didn't matter. She was stunningly gorgeous. 

She was twenty-three but very involved in New York City's trans community, and was also a model. She was in the process of publishing a book, was touring universities to give talks, and was going to be in the new Savage Fenty lingerie line. 

After, we went to her apartment around the corner. 

We started making out on her bed with satin sheets. She was wearing just a black, bodycon dress, and I really mean just that. It hugged her curves, her super soft skin. Her boobs were hugging the fabric, and it didn't take me long to slide it off her shoulder so her dress was around her waist. I really did love boobs, and I took hers in my mouth. It didn't matter if they were fake or not, they did not feel fake. They felt like any other amazing pair of boobs.

She pushed me back onto the bed and stood up. Slowly, she slid her dress down her body, and she was naked except for her black heels. I have to admit, I was not expecting her to be post-operational, but she was. No male genitalia in sight. Then, I was not expecting her new genitalia to resemble female genitalia so much. I didn't know anything about sex reassignment surgery, but apparently I did not have the right idea. 

Lisa stood in front of me and pulled my shirt off. I kicked off my shoes and removed my belt. I kissed her chest as she slid my pants and underwear off. She put a condom on me, lubed me up, and then sat on me. Again, I was not expecting her to feel like any other vagina, but she did. She was warm and wet, and she rode me so well. 

After I came, I rolled her onto her back and kissed down her body. I ate her out the way I ate out all the others girls I had been with, and she moved her body against me in pleasure. She came, and we made out some more. I stayed the night at her place, and in the morning we got coffee. My mind was blown. 

At the end of the day, I told myself that if Colette hadn't dumped me, I would never have been able to experience Angela and Lisa, and I wouldn't have gained them as new friends either.