[M]aking my [NB] virgin best friend cum in his pants

[This is my first-ever post on here! I’ll start with some background, but feel free to skip to the ~~~ if you just want the hot stuff. Enjoy!]

I met Simon at an academic competition when I was 15 and he was 16. I had just come out, and he was the first person I ever introduced myself to using my new name and pronouns. He had grown up in a tiny conservative town and was homeschooled by his extremely traditional Catholic parents, so I was the first openly trans person he’d ever met. I would go on to be a lot more firsts for him.

I had an instant crush on Simon and often dreamt of becoming more than just his friend, but he was sheltered as all hell and I know in retrospect it wouldn’t have worked when we were younger. I did, however, spend a lot of our time together wondering what the worst thing that could really happen would be if I just grabbed him, kissed him, sucked his cock, and begged him to fuck me.

We stayed friends through high school and college, though. While he remained pretty much the same person well into his twenties – very hot, with a lean build and tanned skin and sandy hair and bright hazel eyes, wickedly intelligent, but awkward, repressed, and naive, too – I grew up an awful lot after turning 18. I got better glasses frames that suited my face, learned how to do my eyebrows, cut my hair short (but left just enough that someone could pull it if they wanted to, which people often did), started dressing in ways that concealed my gender but flattered my body, started acting a lot more confident as I got more comfortable in my own skin, and consequently started having a lot of sex. Like, a *lot* of sex. (I may detail some of those adventures in future posts, but for now I thought I’d start with Simon.)

Once Simon graduated from college and had a global pandemic’s worth of self-reflection, he realized he didn’t want to go on being awkward, repressed, and naive. So he turned to me, his most experienced friend and his longest friendship, to remedy that. He called it “exploring” when he asked me. “Exploring” to “help him figure out intimacy” and “discover what he enjoys.”

That made me smile. It was just like Simon to use twenty words when two would do. We have that in common. Despite the circumlocution, though, I know a request to take someone’s virginity when I hear it.

He drove up to meet me at the house I shared with several other people, and we sat down on my bed.

“I’ll be upfront,” I said. “I’m excited about this, but since you have no idea where your boundaries are yet, I’m nervous about crossing them. We can start really small if you want to. Like just kissing or whatever.”

Simon shook his head. “I understand why you’re nervous, but it’s okay. Remember that I’m asking you to do this. I’ll stop you if I don’t like something. And what about you? Are there lines I shouldn’t-”

I laughed. “Babe, I promise, I know exactly where my hard limits are and they are *well* beyond anything you and I will be doing tonight.”

~~~

Despite his inexperience, Simon was a good kisser, pressing his lips gently to mine and tangling his fingers in my hair. I cupped my hand around the back of his neck and pulled him closer, and I felt him gasp a little, lips parting, and took the opportunity to slip my tongue into his mouth. He eagerly did the same. As we kissed, I gently pushed him back until he was lying down on the bed and laid down with him, straddling one of his legs so my leg was between his thighs. I felt something hot pressing against my thigh and tried to shift my weight around before realizing it was Simon’s cock.

*Holy shit, already?*

Having never done so much as kiss someone else before, it didn’t take much to turn Simon on. I didn’t mention it, but I did press my thigh a little harder against his cock, acting like I was just readjusting my body position, and felt him gasp again into the kiss.

Eventually I broke away from Simon’s mouth and tugged at his hair to tilt his chin upward. I kissed his jawline, his neck, over his throat and all the way up to his ear, where I gently nipped his earlobe before pressing a kiss to the skin just behind his ear.

I felt his hips buck under me. His cock throbbed, and he let out a noise halfway between a laugh and a whimper.

“You okay?” I asked.

He nodded. “That… tickled.”

“Oh, shit, sorry.” I moved to back off – as a ticklish person myself, I know how annoying it is to be distracted during sex by an accidental tickle. But Simon shook his head.

“No, no, it felt really good. Do it again.”

I did it again, turning the gentle kiss into a much harder one, sucking just enough to leave a mark behind, and Simon gripped my waist tightly and moaned. I did it again, then kissed across his neck to the other side and kissed him behind his other ear, too. By the time I finished he was nearly panting.

“It, like, goes beyond tickling,” he said between breaths. “And comes out the other side somehow.”

I didn’t say it aloud, but I took a great amount of personal satisfaction in realizing that I was making brilliant, wordy Simon struggle to describe something. I also decided to make it my personal mission to make Simon struggle to form words other than my name.

I unbuttoned his shirt and began working my way down his chest, leaving the occasional hickey as I went, before he tugged at the hem of my shirt and asked to take it off me. Of course I wouldn’t say no to such a polite request, so I let him run his hands up my sides and over my chest as he pulled my shirt up over my head. Then I went back to work kissing every inch of his chest and taking note of what got the biggest rise out of him, pun intended.

When I nipped gently at his collarbone, he whimpered and his cock twitched. When I ran my fingers down his chest all the way to his stomach, he gasped. And when I flicked my tongue over his nipples, he moaned and began grinding his cock against my thigh. I pinched his other nipple between my fingers as I ran my tongue around the first one and the thrusts of his hips got harder and more insistent.

I smiled against his chest and said, “Does that feel good?”

“Mm-hm.” Simon took a deep breath in. “Keep going.”

“I’m gonna have to take your pants off for that.”

“Please.”

*Good, we’re down to one-word sentences. That’s progress.*

I unbuttoned and unzipped his khakis – yes, he wore khakis to his first-ever hookup – and pulled them far enough down his legs to begin kissing just above the waistband of his underwear and tracing circles on his thighs with my fingers. It took a lot of effort to avoid touching his cock, both because I wanted to and because Simon’s hard-on was massive. His cock strained against his underwear, visibly twitching as I touched his thighs, and there was already a bit of a wet spot of precum near the head of his cock.

Seeing how hard he was, I couldn’t help but slip my hand past my own waistband and touch myself. I’d been dreaming about this since I was a teenager and now Simon was right there in front of me, flushed and out of breath and rock-hard.

“Do you want me to…?” he asked, and I realized he was watching me touch myself. I smiled.

“That’s lesson number two,” I said. “For now, let’s just focus on you.”

I kissed my way back up from his thighs all the way up to his neck and behind his ear, finding the hickey I’d left before and sucking on that same spot again. This time, I straddled him completely so his erection was between my legs and started slowly rubbing against his cock. Simon moaned and rolled his hips against mine. In between kisses, I murmured in his ear how badly I wanted him to fuck me.

“Do you want to fuck me?” I asked.

Simon looked up at me, wide-eyed, and nodded.

*No words. Goal achieved.*

“Good,” I said. I stood up and faced away from him, slowly stepping out of my jeans and bending over to take my underwear off so he got a perfect view of my round ass and toned thighs. Behind me, I heard him whimper.

I turned back around, completely naked, and put a hand on his thigh. “We will have to take these off of you,” I said, and ran one finger across his thigh and up his throbbing cock.

The moment my finger made contact with Simon’s cock, he let out a loud gasp and a moan and his hips began to jerk. His cock pulsed under my hand and a new wet spot suddenly appeared on the front of his underwear. As his cock kept pulsing, sticky white cum began to leak through his underwear and drip down onto my hand. I realized what was happening and rubbed his cock through his underwear as he came. He moaned and rocked his hips, shooting more and more cum into his underwear and onto my hand until finally, after several more seconds, his cock finally stopped moving. I wiped my hand on what little of his underwear was still dry and laid down next to him.

“I…” He trailed off. “That felt really, really good.”

“Welcome to sex, babe,” I said. “Take some time to recover, because as soon as you’re ready for round two, you get to fuck me. And trust me, that feels even better.”

Source: reddit.com/r/gonewildstories/comments/u59pw1/making_my_nb_virgin_best_friend_cum_in_his_pants