[Warning: Smut ahead (bet some of you didn't read the notice, but I forgive you).]
***DYLAN'S POV***
"Why are you shying away? It's nothing you haven't seen before," Cupid was currently shirtless as we sat in front of each other.
"But it's different now, I mean we both know where this is going and I'm nervous," I looked away.
"Don't worry," he got closer to me, "I'll be gentle," he jokingly whispered in my ear knowing full well it makes me blush.
"Wow, you even have jokes in the bedroom, hilarious," I sarcastically spoke crossing my arms.
"Of course I do, now," he grabbed my chin and made me look at him, "do you want me to help you take your clothes off or can you do it alone?"
My face was extremely red, "I—I can do it alone!" I escaped his grasp and rushed to remove my clothing but ended up being too nervous to succeed.
"Look at you, you're so eager you can barely even focus," He spoke up placing his hands over mine that were attempting to remove my shirt.
"I—I'm not eager! I j—"
"Save it," he shut me up by kissing me.
It's normal to be scared right?
Of course it is you virgin, don't worry, I won't be rough.
Wh—Who let you read my mind?!
I figured you'd be thinking seeing as you don't like to be this honest when you speak out loud.
I pulled away and pouted.
"Come on Dylan, don't pout, I still love you dear," he hugged me pushing us down on the bed.
"I know," I relaxed a bit feeling better.
I felt him smile on my skin and suddenly started biting and sucking on my neck.
"H—Hey! What are you doing?!" I tried to move away but he pinned me down.
"Just let me leave one I won't make anymore, please?" He said in a low voice.
I sighed giving in, "Fine, but only one."
With that, he continued until he was satisfied with the mark he made.
"Are you ready?" He asked when he was done.
"O—of course I'm not, you may be, but I'm not, I—" he suddenly kissed me.
"Don't worry, I'll make it good," he said before continuing to kiss me.
His hands made their way under my shirt, which surprised me and made me tense.
Relax Dylan.
I looked at Cupid who looked back at me before closing his eyes and deepening the kiss. I relaxed a bit more and kissed him back allowing his tongue access into my mouth as he slowly removed my shirt.
He pulled away from the kiss to fully remove the shirt and began trailing down kisses on my neck all the way to my collarbone until I spoke up. "I—I thought we had a deal that y—"
Before I could finish he stopped and groped my chest.
"Wh—Wh—What are you doing?!" I blushed.
"Just having some fun with you're reactions," he innocently smiled as his fingers brushed my nipples.
A weird surge of pleasure ran through my body as I suppressed the urge to moan.
"Sensitive are we?" He looked at me knowing I was embarrassed by it, but his sadistic self decided to rub his fingers over them again but in a slower motion.
"A—Alright! That's e—enough! There's nothing there for you to touch!" I became flustered and tried to move his hands away but he just pinned me down.
Well, at least his hands are busy holding me down.
"Oh, there's a lot to touch and who said I needed to use my hands?" He smirked as his face made its way near my chest.
"W—Wai—" before I could finish he sucked on one of my nipples catching me off guard so I couldn't hold back the moan that escaped my lips.
"I can't wait to hear more of you," he said switching off to the other one.
At this point my mind was fuzzy and I was mumbling nonsense as my pants grew tight.
Ughhhh this is embarrassing...
He stopped once he noticed, "Already hard from something as small as having your nipples touched?"
"Y—You're one to talk, all you've been doing is kissing and touching me and you're also h—" he rolled his hips causing friction between both our problems down there making me shut up.
"What were you saying? I couldn't hear you," he smirked. "You should see the face you're making Dylan, it's making it hard to go easy on you."
"Sh—shut up," I covered my face with one of my arms.
He removed it immediately, "I want to see you."
"It's too embarrassing," I covered my face again.
He once again pinned my arms so that I wouldn't move them. "We should buy some cuffs or ropes to restrain you since you aren't listening to me," he gave me a mildly pissed-off look.
"And let you do whatever you please? Hell no," I spat back knowing it would piss him off even more.
"You're really getting on my nerves Dylan," he leaned forward and connected our lips instantly shoving his tongue into my mouth as he moved his hips forward again making my breath hitch.
He kept teasing me enjoying the noises coming from my mouth and the impatient look on my face until he finally decided that he wanted to go further.
He reached down and managed to remove both our pants after a couple of minutes not struggling at all.
"You got lube?" He asked after breaking our make-out session.
"Lube?" I asked as I was trying to catch my breath.
"Oh, I forgot you're completely dense when it comes to these things, lucky for you I am Eros," he snapped his fingers and a small pink bottle that looked like lotion along with a condom appeared in his hands.
***CUPID'S POV***
"What's that bottle for?" Dylan curiously asked.
"It's lube, uh, well, I don't know if anyone has ever told you, but wh—wait, do you even know what we're about to do?" I asked him hoping he was at least a little bit educated on this topic.
"No...I was hoping you knew, of course I don't know! I'm a virgin," his face turned red while he spoke.
"I know what I'm doing, I was just hoping you knew so that you won't be surprised when I start, but I guess there's a first for everything," I shrugged reaching to remove his underwear.
"W—wait!" He stopped me. "I don't want to be the only one completely exposed," he looked scared.
"I'll take mine off after you're ready."
"But—"
"Don't be scared, it'll be fine," I kissed him so that he could be distracted.
If he's this worried about taking off his underwear, I can only imagine how he would feel about having fingers up his ass.
I managed to remove his underwear while he was focusing more on the kissing.
I pulled away, "See it's not that bad."
He immediately covered himself with a pillow.
I sighed as I opened the lube bottle and put some on my hands. "Dylan I'm going to need you to move the pillow aside."
"For what? You haven't taken off your underwear yet so I'm not going to be naked yet," he was being stubborn.
"You're already naked and I need to stretch you out before we do anything," I explained easily removing the pillow.
"Stretch out? Stretch what out?!" He looked worried.
"Dylan, how the hell do you think I'm gonna fuck you?"
How is he so dense about this?!
"Wait, you're going to...in there?! That is not possible! N—No way," he scrambled to sit up.
"Don't worry, if it wasn't possible, then I wouldn't be doing it, it's not that bad," I got closer to him.
"Cupid I swear to god, if it hurts, I will ban you from this apartment complex," he seemed to have agreed.
"Trust me," I pushed him back down on the bed kissing him so that he was busy while I slid one finger in.
He instantly parted, "No, nope, that feels weird and degrading take it out."
"I promise it will feel different just give me some time," I tried to reason with him.
He looked away probably out of embarrassment.
"Do you want me to distract you?"
"How is that even possi—"
Before he could finish that sentence I used my free hand to stroke his hard-on which instantly shut him up.
I kept doing that while stretching him out and in all honesty, he was being really loud to the point that I began to worry about the neighbors possibly yelling at us to shut up so I made out with him in order to shut him up.
I stopped stroking him so that he wouldn't cum so early which seemed to dissatisfy him. He got used to the stretching, but I wasn't sure if he was ready yet.
"Fuck, God damn it Eros just fuck me already!" He moaned.
Seriously, like he's really, really loud in bed. I'm totally not complaining though.
"Who do you think you're ordering around?" I teased wanting him to suffer a bit more as I took my fingers out.
"Ugh...whatever..." he mumbled as he started moving his hands down.
I grabbed his hands getting pissed off, "Who said you could touch yourself?"
"Just...hurry up," his face looked so desperate that I couldn't take it anymore.
I took off my underwear and saw his eyes widen. "What?"
"That is not going to fit, no, that's going to hurt," he anxiously gripped the bedsheet.
"It should be fine, I stretched you out and if it hurts a lot, we'll stop," I reassured opening the condom and putting it on.
"F—fine..."
I towered over him, "Now since you asked so erotically earlier, I'll fuck you." I smashed my lips onto his while grabbing his hips and entering.
He gasped in between the kiss and I didn't blame him because I almost did too, but he looked uncomfortable.
"Relax, I won't move until you're ready," I don't know what face I was making, but I really hope I didn't look stupid.
He nodded pulling me back into the kiss trying to calm down. We deepened the kiss touching and feeling each other up not being able to keep our hands off each other.
After some time Dylan parted, "M—Move."
I listened to him and he still looked like he was in pain, but I knew he would get used to it after a while, I, on the other hand, had to suppress the urge to make any noise. I kissed all around his face and neck while groping his chest trying to distract him from the pain.
After some time of moving rhythmically, he let out a loud moan, which immediately made me cover his mouth because that one was sure to be heard next door, upstairs, and downstairs.
I looked down at him, his face was flushed, eyes a bit watery, and though the description doesn't sound like it, he looked like he was enjoying the whole thing.
I kept moving and he seemed to start feeling more pleasure than pain and his erotic face was really making me want to make a mess out of him, but I said I would be gentle so I held back.
"Do...you know what kind of face...you're making?" I said between breaths.
He just looked at me completely out of it, he probably didn't hear me at all.
God, I wanna fuck the shit out of him, he's probably gonna be pissed about all of this tomorrow.
I gave him a quick kiss before moving down to leave more marks on his neck. Once I started sucking and biting on a spot he started moaning louder wrapping his arms around me. I pulled away.
"Dylan, try being a bit quieter I want to be the only one who gets to hear you make such noises," I said before leaning in to roughly make out with him.
After a while, things seemed to start reaching their climax and before we knew it, it was over.
***
After the whole thing, I helped Dylan shower—know lucky me—helped him put some clothes on, and made him wait until I fixed the bed changing the sheets and pillows making it less of a mess—I'm such a good boyfriend. Once that was done I carried the now-sleeping Dylan to the bed, took a shower myself, and finally got some shut-eye.