Winning Over Whytt

It had been over a month since I'd had any kind of sexual interaction - since I'd lost my anal virginity to Tyler - bisexual Tyler, not throat GOAT Tyler. I was still working six days a week, which left me with little time - or energy - for sexy shenanigans. Zane was working a lot and although he had reached out to me to say that he missed me, I wasn't sure what was even happening between us. By the time I got done with my work week, I was so burned out with human interactions that all I wanted was to be left alone with my cats.

I had started going on Grindr a lot more, mainly to see what was available in my area. Aside from John - the same John who had had syphilis twice in his twenties - nobody on Grindr was really interested in me, which honestly wasn't anything new. By then I was more than used to not being anyone's type; I didn't take it personally anymore, but it still sucked that I was allegedly in my prime and was unable to find any decent guys to spend time with. It didn't help that in my area cute guys emigrated more than they immigrated

Late one night, I was bored, doomscrolling on Grindr when I came across the profile for a twenty-year-old from Bay City. I figured he wouldn't want to talk to me since I was fifteen years older than him, but surprisingly, he responded. I learned that he was a stoner and found me attractive, which shocked me. It's not that I think that I'm hideous or anything, but I'm never quite sure how to process the idea of someone finding me attractive. He wasn't bad looking, though he had his septum pierced - a huge turn-off of me - and was a bit more heavyset than I'd normally go for, but considering I was heavier than I wanted to be and didn't want to be denied because of it, I figured I'd get to know him and see if there was a spark there. Over my years of playing the field I had learned that bigger guys were the best cuddlers, which was a major plus for me. We exchanged nudes, which definitely made me want him more: he had a very nice, long dick. I gave him my Snapchat username and was pleased when he added me. His name was Whytt - pronounced like Wyatt.

Over the next few weeks, we snapped each other throughout the day; he quickly became one of my top friends. After about two weeks, I was comfortable enough with him to share that I was feeling especially horny and wanted to suck dick; I knew it couldn't happen, but I wanted to put it out there. He responded acting shocked, but later that night, I was in bed playing the remaster of the original Tomb Raider when he sent me a snap of his rock-hard cock. My mouth instantly watered, and I paused the game, telling him that I would love to suck it, if only he were there. He replied instantly, saying that he could be with me in about twenty minutes if I wanted him to be.

I hadn't actually thought that he would be willing to drive to me, but once the scenario was presented to me, I wasn't opposed. I'd already brushed my teeth and showered; all I'd have to do is show up and perform, which I loved doing. He said that he wanted to blow me, too, but I knew that since we were doing it in his car, I'd probably be too nervous to be able to enjoy it. He assured me that he was clean - showered and disease free - but warned me that it took him awhile to cum from head. My game was pissing me off anyway, so I figured, why not go have some fun?

I was sitting in my car at our designated meeting spot when I saw Whytt pull in from the opposite direction and park facing me. It was almost three in the morning and it was dark, but I was excited. The summer heat had started to wane, so I'd thrown on a heavy sweater and a light jacket in case I got cold. I walked up to his car and got in the passenger seat. He looked exactly like he had in his pics, which was a relief; I had never been catfished, but I was always worried that it would happen and I'd be too shy and uncomfortable to remove myself from the situation.

We sat in silence for a few seconds before asked, "So, do you want to just start or...?"

"I don't know," I confessed, looking down at my shoes. "I'm actually really awkward about this stuff. Like I like doing it, but I'm shy and I'm not good at getting it started."

"Maybe I like awkward," he replied and I could hear the smile in his voice.

"I don't like to just do it," I reiterated, looking him in the eyes. "It's less awkward if I'm comfortable with the guy."

"I can do it either way." He shrugged. "I sucked a lot of dicks in school; I was kind of a hoe."

"Oh?"

"Yeah. I sucked dick in the bathroom."

I balked. "That's crazy! I wish I'd been like that in school. I wasn't even out then." I could see his boner through his sweatpants. "You're already hard."

"Well, yeah." He said it as if I should be used to guys getting erections from being around me.

"I haven't even touched it yet..."

"You can if you want..."

I was still feeling uncomfortable, but I reached over and started rubbing his hard cock through his sweatpants. It was big and juicy, and I knew that I was going to love having it in my mouth; it wasn't too thick and wouldn't hurt my jaw.

"Are you okay with me grabbing the back of your head?" he asked, pulling my attention away from the distraction in his pants.

"For what?"

"So I can grab you and kiss you."

"I've never had someone grab me and kiss me," I confessed, feeling embarrassed. "I talk a good game online, but I'm very shy and awkward in person."

"Maybe I like awkward," he said again, smirking.

"I don't know why you would..."

"Because you're cute."

"You're just saying that because you're horny and I offered to suck your dick."

"It doesn't just have to be that. We could go on a date, maybe."

I stared at him in shock for a few seconds. Even though it was very dark and the only illumination was from his dash, I could see that he was looking at me with interest, not getting frustrated with my shyness.

"You want to go on a date with me?" I asked, trying to not laugh at the absurdity of it.

"Maybe. Why not?"

"I'm almost thirty-six, and you're, what, twenty? Doesn't that bother you?"

"No, not if we vibe."

I'd be lying if I said that I wasn't mostly into younger guys, but I also didn't want to be inappropriate; I knew that he was a legal adult, but an almost sixteen-year age gap wasn't something to dismiss off-hand, either.

"Do you have daddy issues?" I asked, joking, trying to stall while I thought of something suaver to say.

"Actually, yeah," he replied. "I just found out who my dad is a few years ago. I hate him. He tried to kill me."

"What?"

"He tried to kill me with drugs."

I was speechless. I had signed up for a late-night dick sucking expedition, but now I was getting a plot that was even juicier than the cock. Could Whytt be more than just a random hookup story for me to tell my friends? I reached my hand into his pants, underneath his boxers, and started to stroke his bare cock.

"Yeah. He's your age too..."

I felt as though a loose connection had been remedied. "Oh, so you just want me because you have major daddy issues and we're the same age..."

"No!" He laughed. "I think you're cute."

"Well thanks..."

"So...can I grab the back of your head?"

"Do you want to?"

He rolled his eyes and then grabbed the back of my head, pulling me over to him. As our lips met, I found myself relaxing, quieting the voices in my head that told me that I wasn't good enough, that I was a freak, and just enjoying the feeling of his lips pressed against mine, of his tongue teasing the entry to my mouth.

When he broke away, I saw that his eyes were hazy. "Want me to suck you first?" he asked, his lips swollen.

"I'm not hard," I told him, "I probably won't get hard. I like doing car stuff, but it also makes me really nervous."

"Not me, but I get it." He grinned. "Want to start on me then?"

"Maybe..."

Whytt dropped his seat back, yanked his sweats down, and without hesitating, I leaned over and took him in my mouth; as I suspected, he fit perfectly and tasted good.

As I bobbed my head up and down, I swirled my tongue around the head of his penis and along the underside before licking down the length of his shaft. He started moaning, gasping, "Oh, fuck!"

After a few minutes, I came up for air - it was getting hot in his car. "You really are good at that!" he gasped, panting. "You're a good kisser and you're great at sucking dick."

"Yeah?" Even though I knew that my oral skills were hard to beat, I still liked hearing it.

"Best head I've ever gotten."

"You're only twenty, but I'll take the compliment," I said, laughing, before I went back to sucking him off.

As soon as I found my rhythm again he asked, "How do you feel about me pushing your head down?"

Once again, I lifted my head. "Are you willing to risk me throwing up on you?"

"No."

A few minutes later his panting grew quicker and more intense. "I'm gonna cum!" he said, barely more than a whisper.

"Mmmhmm," I said, vibrating his dick, which was in my throat. He tensed up and I kept sucking, milking every last drop out.

"I came," he said, as if I couldn't tell.

"I know, I just wanted to get every last drop."

He shot me a lazy grin, gazing at me through heavy-lidded eyes. "That was the best head I've ever gotten."

"I'm gonna need that in writing," I quipped, smiling.

"Want me to leave you a review on Yelp?"

"Yes, and also Grindr. Tell all the guys who say I'm too old and fat and ugly that at least I give great head."

"No one says that."

"They do, trust me."

"Well, I don't think you are."

I thought it was sweet that Whytt was being kind to me, but I also knew that he was in a post-orgasm haze of dopamine.

"How did it taste?"

"It went right down my throat; I didn't really taste it."

We chatted for about another half hour. I was boiling alive in his car but wasn't quite ready to go back home to my empty apartment. As he talked, I dabbed my precum on his knees, making him laugh. It felt good to talk to someone who didn't know me from my work, someone that I could be my authentic self with, not the cunty bitch I had to be to deal with my customers day in and day out. When he left, I figured that was the last that I would see of him.

Whytt and I have stayed in touch via Snapchat. The day after our hookup he dyed his curls black and red; looking at his curly hair makes me want to get a perm again, even though the last time I got one the bangs didn't take too well and just like of limply hung there like loose ramen noodles.

I broached the subject with Whytt about his date proposal. I don't expect him to do it, but I also don't want to start something up with anyone else if he's serious; he asked me if I was really okay with him being twenty and then asked when we're going on a date and where. As of right now, our date is set for next Monday at six o'clock. I'm not really nervous or excited; I've learned not to get my hopes up too much because I almost always end up getting disappointed. Whytt seems like a nice enough guy, but there is an almost sixteen-year age difference between us; I'm not sure how that will come into play. There's also the issue of Zane, who's been talking to me again; I don't want to hurt him or have him think that I've been using him, but we also haven't progressed past friends with benefits in the nine months that we've known each other, so maybe he won't even care. Should I even care?

I am curious to see how the date will go; it's always weird for me to backtrack with a guy after getting sexual with him. Whytt says he wants more than sex and that a relationship should be more than just sex, but it's hard for me to believe that a guy would want me for anything more than that. Hopefully I'll be more comfortable with Whytt than I've been on most of my previous dates, since I've already met him and we're going to a place of my choosing; I'm not sure what the future will bring, but it would be nice to have a boyfriend on my birthday - last year I was going on dates with Max, but that quickly fell apart. I can't expect Zane to do anything when I was too busy to do anything for his birthday back in July; maybe this could be the fresh start that I need, something in my life besides work and my cats.

Maybe none of us truly knows what we're doing or what will happen next; maybe it isn't for us to know. Maybe all we can do is breathe deeply, take a leap of faith and hope that we'll land safely on the other side.