First Times (Suck!)

Alright, Jim Kirk has always had one simple rule when it comes to sex. He fucks people, but he does not get fucked. Ever.

Maybe it's due to "trust issues". Maybe he just prefers to be in control. But the second fingers come near his asshole, he has always offered a distraction or turned the tables somehow. He's had gorgeous girls offer to peg his ass and built hunks offer to do even more. It doesn't matter because if they won't play his game and follow his rules, he can always find someone else who will. He is Jim Goddamn Kirk and he oozes sex appeal,right?

But when he decides he wants Spock, really wants him for as long as he can have him, Jim quickly determines that his partner has never had sex of any kind in his life, maybe not even of the self variety considering how reserved Vulcans are about anything physical.

It took a week to get him to kiss with tongue and another month to talk him into letting Jim give him a blow job (which blows Jim's mind 'cause since when do you have to convince a guy to let you suck his cock, really?) Six months into the relationship Jim realizes it will be a lot easier for Spock to be the penetrator rather than the penetratee (is that even a word?) so he decides that he will be the one to lose his ass virginity first. Once Spock sees how fun it is, it will be easy to convince him to reciprocate, right?

Except, all those people who said anal sex was so hot and fun, were obviously either lying or doing something different, because at the moment there is at least half of Spock's
dick up his ass and it goddamn hurts!

Jim bit his lip as hard as he could, and wondered how to relax muscles when they were automatically tightening up due to pain. His fingers grasping the edge of the desk, and his breath was coming out in little pained hisses. He held back the whine as long as he could before it finally exploded in a string of explicatives.

"Fuck, fuck, shit, damn, fuuucckk!!!"

Instantly, Spock withdrew and the part of Jim's mind that wasn't practically sobbing with relief at the sudden cessation of discomfort dimly realized that he may have just scared
his lover off sex permanently and he better repair the damage quickly somehow.

Thinking logically (contrary to Spock's opinion, he did sometimes manage it), Jim realized that maybe having sex for the first time bent over his desk, with little more prep than smearing a bit of lube on Spock's cock maybe wasn't the best way to lose one's ass virginity. It had sounded good at the time though.

Jim looked up, and saw Spock's face looking flushed green and embarrassed, but at least he wasn't distancing himself physically. They both stood awkwardly eyeing each other a moment before Spock said "Jim, I don't desire to cause you pain. I believe our activities would be better served on the bed."

Okay, so Spock wasn't the shaken up mess that Jim was at that moment, and he was willing to continue what they had started, which was even more surprising. Truthfully, Jim was trying to decide if they should simply call off the experiment and spend the rest of the night in the comfort zone of blowing each other, but he was game if Spock was.

He was much more experienced in every kind of sex, so it was a bit of a shock when Spock guided him to the bed and sure hands turned him on his side, facing away from his partner.

He lay tense, wondering when he had lost control of the situation when Spock commented, "I did research human sexual practices and their most effective implementations in the likely event that you would wish
to engage in such activities."

"Hmm... So you've been watching porn?"

"No Jim. It would be unwise to use sex being performed by paid actors as a guide for realistic sexual activities. There are excellent technical guides on the subject."

Oh, okay. Jim mused that maybe he shouldn't have been using what he had picked up from viewing pornos as instructions for this experience then, since obviously the actors in them were a lot more used to having things shoved up their asses than he was.

"So what do the technical manuals say we should do now then?" he asked, perfectly willing to let the person who had actually studied this be in charge for awhile.

He could practically feel Spock's eyebrow smirking at him in response.

"You will relax and you will inform me if you feel pain."

"Alright." Jim said as he took a deep breath and let himself relax into what was practically a fetal position. What he defined as "pain" and what Spock meant weren't necessarily the same thing after all.

He stayed still, even when a slick finger began to work it's way in, pushing and pulling tender tissues out of the way. It wasn't really painful, it just felt uncomfortable. Just as he began to get used to the feeling and push back into it, another finger was added, and he found himself wishing he had done this a little in the past so it wouldn't feel so damn weird right then.

It seemed ages but finally the muscles there did seem to loosen up. He didn't let himself dwell on the fact that Spock's cock was substantially larger than a few fingers until it began pushing into him again.

It was the burn that he couldn't get used to. Jim had figured the point of the lube was to keep muscles from stretching and burning, but it didn't really seem to work. Within seconds he was gasping out short, panting breaths.

There was just this slow, constant pressure that never seemed to let up, and Jim heard a low, whining sound that he dimly realized was coming from his own mouth.

Spock's breath against his neck seemed labored, and the arm that had Jim's upper leg pushed up was shaking. The pressure kept going and at some point Jim became aware or the fact that all of Spock's dick seemed to be inside him now, and he vaguely hoped they might just stop with that. He didn't dare look back and see where they were joined, but he could feel Spock throbbing inside him, life a heartbeat. He was stretched wide, with muscles that felt pulled and a deep ache inside. If they stayed like this, he could deal with it.

Then Spock pulled out a bit and gave a short thrust back in. Jim felt his ass clamp down and let out a sharp cry before he could help himself.

"Jim, Do you desire that I stop?"

He had never heard Spock's voice sound so strained, and dammit he hadn't come this far just to back out now.

"Don't stop! Just hurry up! Dammit!" Getting this over quickly seemed like the best solution now.

Then his whole world narrowed to the back and forth pull of Spock moving in and out of him, and he simply hung onto the pillow under his head so he wouldn't claw at Spock's arm that was underneath him.

He tried to remember to breath and tried not to let out the hoarse cries that kept threatening to escape.

There was this point where something felt almost good, where he could kind of see where if the angle was different or he was less tense this might actually feel really, really good. For now all he could feel were little jolts of pain from the dick slamming into him too deep and wish it was over already so they could not do this again for awhile.

Except there was the part of him that wanted payback, and wanted to pound into Spock's ass in return, cause it sure had to feel better on his end.

Then Spock's hands were turning his more on his stomach, and a strong hand was wrapped around his flagging erection. The feeling wasn't so bad when he had that to distract him, to push him towards his own orgasm as he felt Spock stiffen and pour into him. He lay there a minute, thinking "He did not just come before me, when it was just getting more decent!"

Spock pulled slowly out, and Jim didn't think about the irony of it hurting more then than it had when Spock entered him.

"Oww! Fuck Spock, don't move so quickly!"

But he wasn't complaining when Spock turned him on his side towards him though, moving down to lick and suck on him until Jim finally came, shaking and convulsing down Spock's throat.


Afterwards they lay next to each other on the bed, only their shoulders and hips touching. Jim could feel muscles he hadn't know he had, stretched and sore. He ached deep inside and it felt like he could still feel Spock's dick inside him, and he wondered when that extremely strange feeling would fade.

"Do you think you be inclined to engage in such an activity again?" Spock said quietly, but Jim thought he detected a note of insecurity in his voice. Well hell, the Vulcan had been a virgin in every way prior to this, so Jim didn't really blame him. How he had dated Uhura for an entire year without managing more than some kissing and groping was beyond Jim's understanding.

His first instinct was to say "Hell, no!" Then he thought about the first time he was with a girl who was a virgin and she bled a bit and he held her after while she cried, or the first time he gave a blow job and nearly choked to death before leaning over and vomiting (granted he'd been very drunk at the time). It actually could have been a lot worse, probably. Easily in fact.

With an exasperated sigh, Jim turned to look Spock in the eyes.

"I think first times suck when it comes to sex and they improve with practice. and I think you need to let me borrow some of those manuals before we try this again."

"I believe I can arrange that, Jim." was the reply, and damn if his lover wasn't doing the Vulcan equivalent of smirking.

"Don't think it's happening again anytime soon though. God, I'm sore."

He decided if it still hurt the next morning, he would go visit sickbay to relieve the pain. It would be hilarious to see the look on Bones' face when he spelled out graphically what he and Spock had been doing to incur the injuries.

Jim rolled off the wet spot, draped his arm around Spock's chest and slept.

Until two hours later when Jim woke himself running to the bathroom, cursing Spock all the while. There were seriously things he needed to figure out before he could master this type of sex.