Halflings are, to put it quite simply, exactly what it says on the tin. They are almost exactly like humans at half-scale, which includes their internal anatomy. This means that they are extremely tight by comparison to any other race. If you are particularly well endowed, be aware that you are likely going to stretch your partner out very thoroughly and leave her extremely sore immediately following and for much of the next day. If you are less well endowed, sleeping with a halfling woman may be beneficial to both of you, as you will likely still be comfortable for her while she will still be tight and enthusiastic for you. Additionally, halflings are obviously very light as well. If you like to manhandle your lover, this can be a bonus, and I recommend trying it with a halfling if you haven't.
-Alex's Racial Sex Guide, 3rd Edition entry on Halflings
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We had rescued Sampson from a bandit camp and he was very excited to get back to adventuring. We almost had to hold him back from going off on his own again, but he seemed happy enough with the idea of joining our party once we offered it. He may have been a warrior, but there was strength in numbers...and size for that matter.
As a halfling, Sampson didn't cut a particularly imposing figure. He was barely three feet tall, (3'2" he proudly informed us) and although he had very well defined muscles, he didn't wear much to cover or protect them. The handful of weapons he had strapped to his body looked more like toys than implements of war. Still, we'd seen him in action at the camp and he was a surprisingly powerful fighter, not to mention nimble to the point of being nearly impossible to hit.
And he was a very attractive man, too. If he'd been human, it would have been difficult for human women not to swoon over him, although I'm sure halfling women did in spades. Maybe it was my particular mission that let me see it, or maybe it's just that he really was that handsome, but I caught myself staring at his magnificent form embarrassingly often.
He had messy red-brown hair, most of it pulled back in a ponytail that ended just between his shoulder blades. His handful of pale scars were all the more visible against his sun kissed tan. His handsome face was dominated by piercing sky blue eyes that saw right through you with a glance. His chiseled jawline that looked sturdy enough to break a hammer against.
There were certainly less attractive men for me to seduce, and I won't pretend I wasn't looking forward to sleeping with him. But for the sake of taking good notes, I did want to wait until I could be alone with him to do so, and our party was starting to get a little crowded. It was about a week before we made it back to civilization and had rooms at an inn. I made sure to have a room all to myself for that exact purpose, although I'm sure the owner thought I just wanted some modesty or privacy.
But finally, I had a place to seduce the gorgeous specimen of a halfling. I privately invited him to my room that night. After Gaius proved denser than steel armor, I had planned to make this a more direct approach. I closed and locked the door behind Sampson as he walked into my room. I was not expecting to be disturbed, but I wasn't taking any chances either. I had spoiled the rest of the party with copious amounts of sex, and I didn't want to chance them feeling entitled to it now of all times.
"So, let's get started then!" Sampson declared with a broad smile.
"You know why I asked you to come to my room?" I said, feeling slightly embarrassed now at having gone through the trouble.
"Of course!" he replied. "When a woman invites you to her private chambers, there's only one thing she could want you for. You learn these things when you're a dashing hero like myself." He was joking, but I had no doubt it was true in his case. "I must give you fair warning though: you may have my body this or any other night, but my heart is untamable and my soul belongs only to Enetha, the mistress of war."
I giggled childishly at the declaration. I'm sure the line was necessary for most women he slept with, and I'm sure they ignored it all the same. I wondered how many broken halfling hearts he'd left in his wake, but pushed the thought aside knowing I wouldn't be one of them. I had no need for his love. I was in it for the science. Well, and because he was so damned handsome, but I kept that part to myself.
"I'l just try to manage my expectations then," I said, stepping toward him. "Is there any particular place you'd like to start?"
"Well, I don't mean to seem greedy or overeager, but since you invited me to bed, would it not be most appropriate for us to begin with you servicing me?"
"That makes perfect sense to me," I said. "Hop up on the bed and I'll get to work." He kicked off his boots and dragged his pants down before hopping up onto the bed. I sank to my knees before him, ready to perform for him as I had countless times by now for the others.
His penis was already hard, and looking at it in scale to the rest of his body, it was a pretty good size. I imagine it was quite impressive by halfling standards, but I was a human, so it was actually almost disappointing. It was about four and a half inches long and not much bigger around than my thumb. I know it was probably the best I could hope for with his physiology, in fact I considered myself lucky that it wasn't any smaller. But given that the dicks I had been servicing lately were all above average for a human, I somehow doubted this was going to stretch and fill me the way I was now used to.
But like I said, it was probably very large by halfling standards, and I was lucky it wasn't smaller. I certainly wasn't going to turn it down, especially not at this point. So I leaned down and took the head of it into my mouth, running my tongue over it as I applied suction. I didn't bother trying to get my hand around it to stroke too, there wasn't a lot of room to start. I just took it a bit further into my mouth and reached my hands down to unto my own clothes' laces.
I worked my way out of my pants while testing how deep I could take his cock. I was slightly disappointed to find the answer was not quite all the way. Sure, I could theoretically deepthroat it, but it would barely enter my throat and I don't think either of us would get much out of that. So I stopped my advance with his pubic hair just starting to tickle my nose. I pulled back and bobbed up and down to give a little motion to it.