Chandler Mendes
When I get home, I head into our room and lock the door. I go to PornHub and do I search I have never done before:
Top guy bottoms for first time
I lube up the toy, then start to slide it in…
It doesn’t fit at first, so I sort of wiggle it around a little.
First, it burns. But finally something seems to click, and it slides into me…
And then feel my whole body rock.
Okay, this feels…odd, but good. Very good.
I know that when I fuck River from a certain angle, he comes almost instantly, because he described I hit his prostate. So I try to find my own, and mimic the angle I use with him.
I kind of flip my finger and angle it upward, then do a little motion…
And bam.
My cock jerks. My heart pounds. My toes even curl.
I push in deeper, deeper, deeper…
And soon I am about cum all over myself.
~
I leave work and head to Whole Foods for my guy’s favorite kind of Pinot Grigio. Whatever’s gonna happen tonight, I want to be ready for it. But on the way there, a tall, pretty woman appears at my side out of nowhere.
“Hi,” she says, “I don’t know you, but please walk with me for a second. I’ll explain soon.”
I look from side to side. “Um…? I’m sorry, if you’re looking for a date, I’m actually bisexual, and have a boyfriend…”
She gives me a cutting look. “Good for you. I happen to have a girlfriend, myself. I don’t want a date with you, or any man, for that matter.”
“Then…”
She throws a nervous glance backwards. “Please don’t ask questions, just walk next to me while I talk and pretend that I know you. I am in danger.”
Danger – the word makes my hair on my arms stand up, so I start down the sidewalk with her.
She starts talking animatedly about nothing at all, laughing here and there, and I am so confused, I go along with it. Soon I realize we’re at Whole Foods, my intended destination.
“Hey – um, I was going in here,” I say. “Wanna come with me?”
She glances backward again. “Whatever gets me off the sidewalk is fine. After you, sir.”
We head into the store. She turns and watches the window. Suddenly I see three shady-looking guys walk past the door, look into the revolving door, then shrug and keep walking.
She visibly relaxes, her shoulders falling. “Holy fuck, thank you,” she says, turning to me. “Those guys made a comment and then started following me. Without you, they might’ve pounced a block ago. Thank you.”
“Um, I’m sorry…pounced?”
She sighs. “I’m trans. This happens sometimes. Some sketchy-looking guys will decide I’m a target, and start yelling shit and following me. I do this every time, I find a nice-looking person and pretend I know them – I’ve found it helps.”
I stutter. “I didn’t…I’m sorry, I didn’t even know you were…um…”
“You didn’t know I was trans?” she asks. “That’s because queer people usually aren’t looking for people and traits to single out. Other people are. They notice things that just aren’t on your radar.”
“Well I still feel bad…I should’ve just said yes.”
“You’re good. I’m Diamond, by the way.”
“Chandler,” I say as we shake. “So…are you good now?”
Just then, one of the guys walks by again.
“I think I just answered my own question,” I say. “Wanna shop with me for a minute?”
“You read my mind.”
I start down the vegetable section, and she follows me.
“I really am sorry that happened, by the way,” I tell Diamond. “This world is really fucked up.”
“I agree,” she says. “And it’s okay. What are you shopping for, anyway? Typical Valentine’s dinner with that boyfriend you mentioned?”
“Err…not really.”
Her eyebrows rise.
“God,” I sigh, “where would I even begin…”
“Ah! So you’re shopping for something big. Are you proposing?”
“No, nothing like that…ugh. I wouldn’t know how to explain…”
Diamond leans in. “Okay, now you have to tell me, because you’re just making me curious on purpose.”
I pick up a cucumber. “Okay, I’ll explain this way. I have only ever used this, during sex. I’ve never let him come near my, um…”
I spot a peach and pick it up.
“This,” I say. “But my boyfriend really wants to utilize it, and…well, I don’t know what to do.”
She laughs, then looks around and lowers her voice. “So you’re a top who is afraid to bottom for the first time, huh? You think getting fucked in the ass will make you less of a man. or whatever?”
I blush. “I mean, when you put it that way, it sounds pretty bad…but I guess, yeah, that’s the gist of it. And how did you know what my issue was, anyway?”
Diamond’s face gets softer. “Look. I’m a sex worker. You’d be shocked by how many straight-presenting men will hire and me and then proceed to make incredibly self-hating homophobic comments about queer people.”
“Actually, I’ve heard of that whole aspect. I’m not like that, I swear – I fully accept myself. I just don’t know if I’d…you know, like it. Enjoy it. That’s the thing.”
She crosses her arms. “Well, I’m guessing it’s obviously important to your guy that you try it, or else you wouldn’t be asking me?”
“Yep. He really misses topping, and asked me to compromise. But what if I don’t even like it?”
She pauses, then looks over at the shelf. “Cholula,” she says.
“What?”
“Cholula,” she repeats, picking up a bottle of orange-red hot sauce. “I’m a Tabasco girl, always was. I put it on almost everything. Then I dated this girl who swore on Cholula, and I was totally thrown.”
“So…you tried it, and liked it?”
“No. It was so gross, it made me retch. I went back to Tabasco and never looked back.”
“Oh, thanks…”
Diamond laughs. “My point is, I tried it. I didn’t know whether I’d like it or not, so I tried it out. So why can’t you do the same? What’s the big deal? What have you got to lose?”
“I mean…well, you kind of do have a point…”
She steps a little closer. “Hey. You said you identified as straight until recently, right?”
“Yeah, actually.”
She nods. “Take it from someone who had to learn the hard way: accepting yourself is never a straight line. It’s not overnight. I’d guess you’re still grappling with this whole thing a little more than you knew. And who knows? Being vulnerable to your boyfriend might help you confront some of that.”
I think about this.
“Thanks for the walk,” she says, grabbing some Tabasco. “Now if you’ll excuse me, I’ll be on my way.”