Elijah #5
“Then let’s...” he began, leaning up again.
I waited as he moved behind me, and fought the urge to see what he was doing.
I figured it was another toy, but also figured it was better I didn’t see it.
Anal obviously had to feel good for guys; otherwise, why go back repeatedly?
Didn’t change the fact that having something dick sized pushed into your ass would be painful, and I wasn’t looking forward to that part.
Something bigger pushed against me, and when it inched in, it was with.
..okay, not quite pain, but it was close.
I took a deep breath as Milo was careful, easing it in, and the uncomfortable pressure inside me returned.
That was until I felt his mouth on the inside of my thighs, kissing and licking his way up to where his other hand was seating the toy inside me.
That one was also longer, so it reached some part of me that hadn’t been touched before.
I lay there, torn between the delicious tingles of his mouth on my body and the awkward feeling of the toy inside me.
“Raise your hips,” he said from between my legs, and I did, pushing back onto the toy and tensing before getting into position.
It wasn’t until I felt his free hand between my legs, grabbing my softened dick, that I realized what his intention with the position change had been.
He worked the toy as he stroked me, my dick stubbornly staying half hard at best, but it drew more attention to the pleasure from the act.
It was still softer than I expected, but it was better than discomfort and a faint feeling of almost pleasure.
The next toy was the one I worried about the most, even though I knew it was the final step before we got to what I’d suggested.
I felt the blunt tip push against me and braced for something worse than the previous two.
When he pushed it into me, it was easier than expected.
In fact, it wasn’t all that different than the second toy.
It was thicker, but the second toy had apparently stretched me enough that the discomfort was about the same, and just as pain-free.
“Oh,” I grunted as the toy slid inside, filling me completely as Milo never stopped stroking me. “That’s...huh.”
“I’ll take that as a good thing,” Milo said with a chuckle.
“Y-yeah,” I managed as the toy moved, slow at first but then with growing ease. The discomfort faded, and in its place was something warm and electric, growing inside me as I felt myself stiffen in Milo’s hand. “Oh shit, okay.”
The longer he moved that toy, the more I realized why Milo was okay with bottoming.
The combination of toy and hand worked together to make me squirm and breathe heavier.
Pleasure rippled through me, and I found myself gripping the bed cover, not out of pain or worry, but because all I could do was lie there and ride out wave after wave of pleasure.
It was like the pressure of the initial entry, but with the promise of ecstasy and none of the discomfort.
“God, if this is what a dick feels like,” I moaned, not caring that it sounded a little pitiful. It was the same tone Milo used when I was deep inside him, and that was one of the hottest noises he could make. “I’m ready.”
“I’d like to think my dick will feel better.” He laughed. “Got a position preference or just like this?”
“You’re the one topping,” I said, ready to get the party started.
“Okay, on your back, legs in the air,” he said without hesitation, and I did as he said with an equal lack of hesitation.
I could see just how much he had been affected.
His dick was hard enough that I wouldn’t be surprised if he complained it was ready to burst, leaking furiously at the tip and bobbing in front of him as he knelt before me.
There was an intensity in his eyes, held in check by what I suspected was care for me, wanting to fuck the hell out of me but not wanting to hurt me.
His movements were stiff and jerky as he pulled the other bottle of lube out to coat his dick before reaching down to pull the toy from me.
“Oh,” I grunted at the sudden feeling of emptiness. “That’s...weird.”
“Feeling a little empty?”
“Yeah.”
“It’s worse when it’s someone’s dick, especially if it’s someone you’re into.”
“Great, so I’ll be pining for your dick after this.”
“Let’s hope,” he said with a grin, shoving a pillow under my ass and holding my leg and the base of his dick.
Angling down, I felt the head push against me, and despite having no experience, I knew he was thicker than the last toy.
Not that that was going to stop me, I knew what a good-sized toy in his hands felt like, and I was more than willing to deal with discomfort if it meant having him inside me.
He breached me more easily than the toy, and we both groaned when the first couple of inches pushed inside.
Whatever discomfort I’d been expecting was dismissed immediately as I felt him slowly thrusting into me.
It was worlds different than the toy; it was harder, thicker, hotter, and better .
My breath stuttered and shook as he took his time over the last few inches.
Milo hovered above me, his eyes burrowing into mine as he held himself steady, buried completely. He leaned forward, lips brushing mine. “God, you’re beautiful.”
“You feel amazing already,” I told him, catching his mouth with mine and groaning when I felt his cock move as he shifted to get a better position.
Then he began to move, and at first it was like the toy, but it quickly became so much more.
One of his hands held my hip, and another held my leg as he rolled his hips, shallow at first, but steadily his strokes became deeper and longer.
I had gone soft temporarily, but watching him, feeling him, brought me back to full stiffness in no time.
He was so hard and taking his time, but I could feel the tension in him, begging to be released.
“Fuck me,” I told him. “I won’t break.”
He didn’t need any more encouragement, and his hips began to move.
Milo shifted his grip as he leaned forward, one hand staying on my hip, my leg on his shoulder, while his other hand rested beside my chest on the bed.
I had to angle my hips up more, and his next thrust was harder.
Stars sparked in my vision as the place inside me that he’d prodded at before was now set alight.
Gasping, I reached out, not caring what part of him I grabbed as his hips picked up their pace, sending explosion after explosion of pleasure through me.
I didn’t care that my moans were growing in intensity, that they sounded needy and desperate, because I was desperate, desperate for more, to keep feeling him inside me, to feel him when he came, buried and lost to his own pleasure.
“Look at me,” he said in a strained voice, and I opened eyes I didn’t know I’d closed.
He was above me, eyes burning with lust and pleasure as he buried himself in me again and again.
Our bodies rocked together as I held on, feeling like every nerve ending had come to life in ways they never had before.
I ached for release, but I didn’t want it to end.
“I, uh…” he began, slowing down. “Might have oversold how long I could last, I’m sorry.”
“God, fuck no, don’t be,” I gasped, pulling him closer with my leg. “Do it. Just like you said, come in me, make me yours.”
A new light flashed in his eyes, and I groaned when he buried himself with a snap of his hips.
He was close, and I wanted to be right there with him, though I knew it wouldn’t take long.
I reached down, wrapping my hand around my straining cock as I felt him thrusting with renewed vigor.
He didn’t have to hold back for fear of going too hard or coming sooner than he thought he should, and that was obvious.
Not that I was going to complain. My body was one burst of pleasure after another, and even the feel of his thrusts beginning to stutter and lose rhythm sent a new jolt of pleasure through me, filled to the brim with anticipation as I waited for the inevitable.
With a grunt, a gasp, and a final thrust, he shoved himself deep.
I felt something jerk inside me, and I groaned harshly, pushing onto his dick as my own orgasm took me.
Milo cried out, and I knew from experience how it felt to have someone come while I was getting off.
Your already sensitive cock suddenly had a renewed grip wrapped around it, and you were left feeling like the other person was trying to drain you of every last drop.
His hips jittered as I coated my stomach, my free leg wrapping around his waist and holding him tight, making sure he stayed inside me while we both rode out the full length and breadth of our orgasms.
When we were done, he proved himself right when he gently pulled out.
He was far gentler about it than I had been the first time I’d pulled out of him, but I’d learned, and I didn’t have to deal with the weird feeling he’d described when someone did that.
But there was that aching sense of emptiness left, and a yearning to have his dick back, not necessarily in the sexual sense but just.. .existing.
“Fuck,” he muttered as he reached into the box where the toys had been and pulled out wipes to clean us up.
We’d forgotten to put a towel down again, though, so there was lube all over the place, and we were going to have to clean his bed cover before it could be used again, but that was alright.
There were two beds in the apartment after all, and ever since that night in the hotel, we hadn’t slept without each other, sex or no sex. “Guess it’s your bed tonight.”