The Roommates Ch. 02

He knew that it was unusual, or at least unexpected. He hadn't made any decisions before this moment, but he wanted to try. "Yes. I know it's going to hurt and it won't be easy, but I do want to do it," he told her.

"Well, I'm normally much more of a bottom, but I like to play top once in a while. Plus, I promise to be gentle."

A couple of minutes later, Daphne was pushing two heavily-lubed fingers up inside his slowly relaxing bum.

"That's it just relax. You need to practice relaxing, and it won't be easy, but once you do, you'll really start to enjoy it," she said and smiled at him.

He was laid out on his back, with his knees pulled up, exposing himself to her. Amazingly, his cock had become half-hard itself, without any attention being paid to it at all.

He'd watched Daphne's little cock maintain a rigid erection the entire time. She'd pulled off her top, but still wore her pink, cotton thong, bulging dramatically with its barely contained payload.

Daphne pulled her fingers out, and produced a condom, and with a practiced movement, slipped her hard-on out the side of her panties and rolled the condom on, before slathering lube along it.

She looked him in the eye again with a big smile, "Are you ready?"

He gave a nod, trying to be confident, but failing.

"You're going to love it. Just remember, try to relax."

He couldn't control it, the fear just had him clenching the moment her spongy head contacted his bum.

She was patient though, gentle, and murmured encouragement, support and tried to sooth his fears.

When she slipped in it felt like a tree trunk, even though he knew she was smaller than he was. Again though, she was patient, soothing and gentle, and waited for him to nod his readiness for her to continue.

It was a strange feeling, very pleasant, but not at all like any kind of sex he'd ever had before. But it was new, and obviously his own cock was not involved right now. This was mostly for Daphne, and a bit of experimentation on his part.

It took a while, but eventually Daphne had worked her little rod all the way inside him. Then she started to stroke. Very slowly she pulled back, probably about halfway, before slowly pushing back inside again.

"Oh," Brad gasped at the changing sensations.

"You okay?" she asked him.

"Yes, it's just... oh god, it feels big."

She graced him with a grin, "Such a compliment."

He smiled weakly at her.

"More?" she asked.

"Yes, but slow."

"Of course baby," she told him.

Brad wasn't counting strokes, but he had noticed they were going faster and faster. He knew they'd reached a good pace for Daphne when she started to praise him.

"Oh yes Brad, such a tight arse, such a nice, tight arse."

By now Brad had his hands on her jiggling jugs, the distraction had helped him relax his arse a bit more. Sometimes she'd spend a few strokes while she was lowered down, rubbing her big breasts against his chest.

His legs flailed as he tried to keep them up out of Daphne's way, and occasionally she helped him by pushing back with her hands.

"Oh god Brad, your arse is so nice, it feels so tight wrapped around my clitty. Mmmmm, so nice."

"Oh, Daphne... fuck, you're so big. Feels like you're splitting me in two."

"That's right baby, take my big clit inside, make me feel so good... so good... oh god... OH! OH! OH YES! OH GOD YES! OH FUCK! OH GOD! I'M CUMMING! OH YES!" she screamed.

She was now pounding into Brad, and there was no doubt that it was hurting, but he was willing to take it, to put aside that pain for Daphne to fully enjoy her pleasure.

The feeling of her shooting her spunk inside a condom, inside his arse was undeniably strange.

They'd worked up quite a sweat, or at least, Brad noticed he had. He was sure Daphne's fitness regime included much worse than this.

"FUUUUUUUUUUUUUUUUUUUUUUCK!" she exclaimed, obviously having reached her peak.

Her strokes slowed, and finally stopped. Brad's arse tingled from the sensations having finally stopped. He still felt full, but really, all the pain was gone.

She gave him a soft kiss on the lips, a supremely sweet gesture. She then whispered to him, "Don't look," and started to withdraw. He followed her instructions.

Once she was off the bed she quickly turned away and Brad could tell she was removing the condom, and he heard it hit the trash.

"Okay, come on, we need a shower," she smiled at him and beckoned him to follow.

* * *

They shared a shower, and both enjoyed rubbing up against the other's body, and they even soaped one another. His cock again got half hard, but neither acknowledged it, content with their sexual activities for the morning.

After the shower, Daphne got dressed in her room in relatively casual clothes and headed for the door.

"See you later Brad?" her tone making it a question.

"Oh, yeah, definitely. Dinner?"

She smiled, "Sure, later then."

Brad smiled and checked his phone to find a text from Jeff, asking him to go for a drink again. He replied with a nearby cafe, and said he'd be there shortly. He really wanted to see Jeff and tell him what happened, maybe try to work out how he felt about it all. He was really thankful for the chat he'd had with Jeff yesterday, and was hoping for some more advice.

Brad had fucked his transgender roommate, Daphne, up the arse, twice now, and thoroughly enjoyed it. Then he'd asked her to take him up the butt, and while it had hurt, he was pretty sure he'd liked it. At that point in time, he was forgetting all about Sara.