Jen bucked against his face more aggressively, screaming loudly now as she rose higher and higher towards orgasm. Her pussy was gushing, soaking Matt with its wetness and drenching his face as though he’d just gotten out of the shower.
His confidence growing due to Jen’s excitement, Matt decided to kick things up a notch. He grabbed ahold of Jen’s ass cheeks and slid his thumb along the crack of her ass until he found her asshole. Using her copious pussy juices as lubrication, Matt rubbed the tip of thumb around the outer edge of Jen’s asshole a couple times to get her warmed up. Then slipped his thumb into her anus.
Jen let out a sharp, yelping gasp and her body froze up for a couple seconds before exhaling in a rush as an orgasm immediately passed through her. Her pussy released another wave of juices, drenching his face even further.
Jen’s legs shimmied for another few seconds, then she released her leglock on Matt’s head. Yanking on his hair, she lifted him up towards her face. She scooted forward and aggressively shoved her tongue down into his mouth while simultaneously grabbing ahold of his cock and jerking him off.
“You like sticking your thumb in my ass, do you?” she said, breaking off their kiss with a yank on his hair.
Matt nodded.
“Is there anything else you want to stick in there?”
He nodded again.
Jen laughed. “Yeah, I’m sure there is. You want to stick your cock in my little asshole, don’t you?”
He nodded yet again.
“Well, I’ll make you a deal,” Jen said. “If you do a good enough job licking my asshole, then maybe, just maybe, I’ll even let you stick your cock inside it.”
“Are you serious?”
Jen nodded.
“I didn’t know you were into that sort of thing.”
“That’s because you never asked,” she said.
“So you mean all this time, all I had to do was make an attempt and you would have let it happen?“
“Well, not just any time,” Jen said. “But certainly there was a couple times, where if you would have made a move towards it, I wouldn’t have fought you on it.”
Matt mentally smacked himself in the forehead with his palm.
“And here you thought the only girls willing to do that were the ones you watched on your movies,” Jen said.
“Little did I know I had one sharing a bed with me.”
Jen shrugged. “Well, now you know,” she said. “But you’d better do a great job with your tongue down there or we’ll have to wait until a different night to take things to the next level.”
“Oh, don’t worry about that,” Matt said. “I’ll lick like I’ve never licked before.”
“We’ll just see about that,” Jen said. “We’ll just see.”
To show Jen how serious he was, Matt dropped his head down and immediately started licking her asshole, his tongue moving up and down and around the edges.
“Holy shit that feels so fucking good,” Jen said, staring down at him. Her eyes were wide and her mouth was turned up in a huge smile. Matt didn’t think he’d ever seen her so excited. So he kept pushing the envelope.
Making his tongue rigid, he jammed it into Jen’s asshole as far as he could and started to tongue fuck her. Jen’s screams turned even more animated and her breathing rate increased.
“Oh my fucking god!” she said. “Tongue-fuck my dirty shithole, baby. Just like that. Yes, YES, YES!”
Getting off himself on Jen’s excitement, Matt spread her asscheeks with his hands, allowing him deeper access to her insides. Tilting his eyes up, he could see Jen fingering her snatch with one hand and squeezing and pinching one of her nipples with the other.
Matt continued working Jen’s asshole as aggressively as he could, jamming his tongue further and further inside it as she continued playing with herself, which opened her anus wider, allowing him deeper inside.
Just as Jen was about to cum again, she transferred the hand that was squeezing her nipple to Matt’s hair and held his head in place, his tongued jammed deep into her asshole while she rubbed her clit forcefully.
“Fuck, FUCK, FUCK!” Jen screamed. “I’m gonna fucking cum again!”
Half a minute later she did exactly that, her pussy squirting juices everywhere again and her body shaking and shivering for nearly ten seconds before falling still this time.
Using his hair, Jen pulled Matt’s head up towards her own. She pressed her forehead against his and said, “Okay. I think you earned the right to fuck my ass.”
Smiling, Matt slipped his tongue into her mouth and they made out for a little bit while Jen ran her hand down to his cock and started playing with it.
Matt was excited. Probably too excited, really. He’d dreamt about fucking Jen in the ass ever since he’d met her but figured it would never come to pass. And he was so wound up after all the foreplay that he doubted he’d last long. But those were the breaks. It was better to have fucked Jen’s ass for a couple minutes than not at all. Or something like that.
So he broke off the kiss and slid back down her body until he was standing on the floor. He was tempted to put Jen on her hands and knees so he could fuck her doggy-style, but considering how much he liked that position, he was sure it would just serve lessen the (already limited) amount of time he’d be able to fuck her before cumming, so he kept her on her back.
Matt grabbed Jen’s ankles and pulled her legs up, lifting her ass off the cushions of the couch and bringing her asshole closer to his cock. Jen hooked her arms under her knees to hold her legs in place and looked at him with a filthy little grin.
“Are you ready for this?” Matt asked her.
“I am,” Jen said. “The real question is, are you?”
“Hell yes,” he replied.
“Then do it,” she said. “Stick that hard cock of yours into my pretty little asshole.”
Matt couldn’t turn down a request like that, so he did as Jen had asked, grabbing ahold of his cock and sticking the tip of it against her asshole, then taking a deep breath and pushing his hips forward.
The tip of his cock slipped into Jen’s asshole. It was a tight fit but not uncomfortable. Just weird. Unlike her pussy, Jen’s asshole provided consistent pressure to every centimeter of his cock at one. Plus it was tight as shit.
But it felt incredible. So good, in fact, that Matt was afraid he was going to cum just from breaking the seal. After entering Jen, he stayed completely still, taking a couple of deep breaths while trying not to move at all.
Jen could tell the difference too. She was taking short, shallow breaths and her eyes were closed in concentration. A strange combination of pleasure and pain played over her features.
Matt knew how she felt. While the pleasure was undeniable, there was a certain level of discomfort there too. Too bad he didn’t have any lube; that would certainly help. Well, next time he’d know. For now, he would just have to make the best out of it.
Jen helped things a bit, spitting onto her hand and rubbing her saliva over his cock. That helped some, allowing him to move a little bit without too much effort. And when Jen started rubbing her clit it helped even more.
The more she played with herself, the more she relaxed, and the more her anus loosened up. After half a minute or so, Matt was able to move at a slow but consistent pace, his cock going deeper and deeper into Jen’s asshole with every pump.
“Your asshole is so fucking tight,” Matt said, staring down at her with an intense gaze.
Jen just nodded her head and continued playing with her pussy.
“It feels good though,” Matt said. “Doesn’t it?”
Jen nodded again.
And it did to Matt too, despite the tightness. There was just something about fucking Jen in the ass that was so nasty, so perverted, so flat-out wrong that it turned him on like crazy just thinking about it. And even though he was barely moving against her at all, it took everything he had to keep from cumming.
Matt leaned forward and stuck his tongue into Jen’s mouth, hoping to take his mind off how close he was to orgasm, but it didn’t work. If anything, her lips on his felt so good that it brought him even closer to cumming. Which wasn’t a surprise; kissing while fucking almost always had that effect on him.