The Begin of Something Fun – Take 04 – Anal


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Part 4

Matt and Olivia’s relationship had progressed over the next few months. Olivia was living with her Mom and had her daughter 3-4 days a week. On the days her daughter was not with her, Olivia stayed at Matt’s. She liked the proximity to the bar so she walked to work and it got her away from her Mom who was sort of a drunk. Whenever Olivia was at Matt’s, and they were alone, they fucked…constantly!

It was a Friday and Matt had to go into the office for some onsite meetings. He hated going into the city ever since he was given the ability to work from home due to the pandemic. In his mind it was a total waste of time. Matt’s job responsibilities required him to work with buildings and people in other states across the country, so going into the office didn’t change his way of working. When he did go in, it stressed him out to no end.

Lucky for him, Olivia was getting close to completing her schooling in massage therapy. Since they started seeing each other, Matt had received no less than 20 massages so Olivia could “practice”. In all cases, his massage ended with them fucking or Matt getting jerked off!

Matt would tease Olivia saying, “Is this going to be how you end ALL your massages once you start working? Because, damn, you’ll make great tips!”

When Matt walked through the front door, exhausted and stressed, ready for a cocktail, he was greeted by Olivia standing in the living room completely naked. She had put plastic down on the floor and her massage table was set up.

“Surprise!” Olivia said, “I know how much you hate the office so we’re gonna practice a new type of massage…get naked.”

Olivia had practiced all types of massage techniques on Matt. Sports, deep tissue, shiatsu, reflexology, and any other type she was taught in class. Matt did not like any of the focal, deep tissue type massages, he was partial to the traditional Swedish massage that was basically getting rubbed all over with oil (and getting a happy ending).

Matt was undressing and asked, “New? I thought we’d done all of them?”

“Well, it’s one we talked about, but it won’t be one I ever practice…not unless we move to Japan!” Olivia said giggling.

She patted the table and Matt hopped up, laying on his back. His cock was hard already!

“Roll over, you perv,” Olivia said jokingly as she pinched Matt’s nipple, “We’ll get to that later.”

Matt did not put his face into the hole at the end go the table; he was staring at Olivia and taking in her gorgeous, tan, naked body. She just smiled and took a bottle of oil, taking off the cap, and dumped the whole thing onto herself! Olivia slowly rubbed the oil into her entire body, taking her time as she massaged her tits, pulled on her nipples, gliding her hands down her flat tummy, lingering at her pussy a few minutes, and finally making sure her legs and feet were covered as well.

“WOW!” Matt said as he was slowly grinding his dick into the table, “What kind of massage is this?”

“It’s called Nuru,” Olivia said as she started to pour oil all over Matt’s backside, “It’s Japanese. I’m gonna use my whole body to massage your whole body…sound good?”

“Sounds fucking great!” Matt answered.

Once Matt’s back was covered in oil from his neck to his toes, Olivia climbed on top of him. She laid flat and slowly started gliding her body along his. Matt could feel Olivia’s hard nipples as they slid across the top of his back and her pussy rubbing along his ass crack.

“Mmmmmm,” Matt moaned, “This feels fantastic! Can’t wait for you to do my front!”

“You are such a horndog, Matt,” Olivia said, “but I can’t either!”

She took her time. Sliding her body against his for a good 30 minutes. Matt could feel the stress leaving his body, and even though it was also making him horny and wanting to cum, it was also totally relaxing.

“Before you roll over,” Olivia whispered into Matt’s ear, “I need to try something. Just go with it baby.”

Matt wasn’t sure if he should be scared, but he was too relaxed to care at this point. Olivia was now again laying completely flat on Matt’s entire body, but she then put her knees on either side of his hips and pushed herself up onto all fours. She then pushed her hips forward so just her pussy was in contact with Matt’s ass. She started grinding…almost like she was fucking him from behind!

“Mmmmmmm,” Olivia purred, “Just the right amount of pressure on my clit…feels SO good!”

Olivia had now moved up just a bit so her clit was in direct contact with Matt’s tailbone, giving her the perfect amount of pressure as she continued thrusting her hips back and forth.

“Oh fuck,” Olivia grunted, “I’m gonna fucking cum super hard…fucking so good, baby!”

Matt just laid still, but he could feel his cock swell beneath him as the pressure from Olivia’s body was forcing him into the table. He was pretty sure he wasn’t gonna cum, but it did feel really good at this point knowing Olivia was so turned on!

“Oh, oh, oh, oh, fuuuuuuuuuuuuck!” Olivia screamed as her pussy let loose and her juices flooded onto Matt’s lower back and ass, “Cumming so fucking hard!”

Olivia went stiff for a brief moment as her orgasm overtook her body and then she collapsed on top of him.

“Holy fuck…I felt that one in my toes!” Olivia said sounding exhausted.

Matt laid still for a minute before he started to maneuver himself to roll over onto his back. The oil and pussy juice was the right amount of lubrication to make it very easy to do. Matt, now face-to-face with Olivia, started kissing her tenderly on the lips and neck.

“Wow,” Olivia breathed, “That was just as much for the massager as the massagee…”

They made out for a few minutes, grinding into one another as they laid on the table. Eventually Olivia slid down Matt’s body, dragging her tits along the way, stopping briefly so his hard cock slid between them, and then climbed off the table.

“Time for more oil,” she said grabbing another bottle and dumping it on Matt’s chest.

As Olivia applied oil to Matt’s front, she also rubbed more onto her body as well. Matt wondered ‘It’s a good thing she put down the plastic on the floor!’ as there was oil everywhere at this point. Matt’s cock was throbbing and he couldn’t wait for Olivia to climb back on and continue the massage.

“Soooo…” Olivia said as she straddled Matt on the table, sitting up and slowly grinding her pussy on his hard shaft, “You need to let me finish the massage before you finish…got it mister?”

Matt chuckled saying, “No guarantees on my end, but I promise to try!”

Olivia now laid flat, their bodies pressed together chest to chest…and cock to pussy. Again, she slowly slid her body along Matt’s, using mostly her tits to massage his body. As she slid down his chest to his stomach, Matt closed his eyes and concentrated on NOT cumming! It wasn’t easy when Olivia finally slid down so his cock was now resting firmly between her tits and she pushed them together, accentuating the pressure.

“Holy. Fuck.” Matt groaned, “I want to fucking cum on your tits.”

“Not yet, baby,” Olivia said as she slid back up his body, “You have to hold off a few more minutes for me.”

Olivia slid her body all the way up so she was now straddling Matt’s chest, kneeling up and massaging her tits. She then inched her way forward so her pussy was directly over Matt’s face. He tilted his head forward and ran his tongue up her slit, stopping to flick the tip across her now hard clit.

“FUCK YES!” Olivia moaned, “Fucking lick my pussy, baby…please…”

Matt hooked his arms over her thighs and dove in. Licking, sucking, and fucking Olivia’s pussy while she was grinding up and down on his face. She arched her back as she pulled on her nipples with both hands, moaning her approval as his tongue worked her slit. As Olivia started thrusting her hips a bit faster, Matt slid his hands back and gripped her ass cheeks in both hands, trying to control the pressure she was putting on his face. The oil made it difficult to keep a steady grip and Matt’s right hand slid further into her ass crack, coming into contact with her tight little butthole.

“Finger my ass!” Olivia commanded, “Finger me while you suck on my clit!”

Matt probed for about 2 seconds with his index finger and then felt it slide easily into Olivia’s ass!

“OH FUCK!” Olivia moaned as she thrust her pussy harder into Matt’s face, “SO PERFECT!”

Matt started working his finger in and out of her ass while continuing to suck and lick her clit. Olivia reached back with one hand and was now slowly stroking his hard cock while the other hand continued pulling and twisting her nipple. Matt knew he needed to make her cum soon as he wasn’t sure how much longer he was gonna last. Just as he wondered this, Olivia announced her oncoming orgasm.

“OH FUCK I’M CUMMING MATT!” she screamed as her hips bucked hard against his face and her pussy let loose.

Olivia fell forward, hunched over so her hands were now above Matt’s head, resting on the end of the table, as he continued sucking her clit hard into his mouth and slamming his finger in and out of her ass! She had let go of his cock which gave him a bit of relief, even though he was very near cumming himself. Now his worry was drowning in the sea of pussy juice flooding his face!

“Keep fucking my ass, baby,” Olivia grunted, “Fuck that feels SO good! I want to cum again!”

She was now bucking backwards more than forward, searching for another orgasm from Matt’s finger in her butt. He did not let up until she told him to stop. Olivia shuddered through another orgasm and then collapsed on top of Matt. Panting heavily with her face buried in his neck, Olivia was spent and somewhat exhausted.

“Fuck,” she said, short of breath, “That. Was…amazing…”

Matt was patient, waiting his turn, knowing he was gonna be cumming soon. He kissed her lightly on her neck and, pushing her up a bit by her shoulders, nibbled on her tits. Olivia eventually sat up straddling Matt, bracing herself with her hands on his chest. She looked so fucking sexy all sweaty and covered in oil. Her body glistening! Matt slowly started to move his hands up and down her arms, then slid across to fondle her breasts, gently tweaking her nipples, and then down her stomach to grasp her hips. Olivia was now slowly grinding her pussy against Matt’s shaft, her pussy lips gliding up and down without penetration. They both felt really, really relaxed!

“It’s not gonna take you long, is it,” Olivia said, not asking, “How do you want me?”

Matt answered by thrusting his hips and pushing Olivia down by her waist as his cock slid into her waiting pussy until he was balls deep!

“Uuuuuuugh!” they both groaned in unison.

Matt slowly started fucking Olivia as he held her tight against his body. Her arms were trapped and she wrestled a little to get one free. Reaching back she slid her own index finger into her now slippery asshole, fucking herself as Matt fucked her pussy nice and slow. They kissed while fucking. Tongues battling in each others mouth, little bites and nibbles on each others lips.

Olivia broke their kiss after a few minutes and nuzzling her face into Matt’s neck whispered, “I want you to cum in my ass…”

Before Matt could answer, Olivia slid her finger out and grasped his hard cock, moving it to her waiting little butthole. He slid inside her with absolutely no resistance!

“OH YEEEEEESSSSSS!” Olivia groaned loudly as she now sat up, pushing herself down further onto Matt’s cock inside her, “Your cock feels fucking fantastic in my butt! So unbelievable!”

Matt gripped her hips again and held on for dear life as Olivia was slamming down hard onto him, his balls being squished as he thrusted into her. He knew it wasn’t a matter of minutes, but of seconds before his load filled her!

“You need to cum for me, baby!” Olivia said through her gritted teeth, “Fucking cum in my ass Matt!”

Matt felt his cock puff out and his balls tighten immediately! He pushed up hard into Olivia, filling her with spurt after spurt after spurt of his hot load!

“FUUUUUUUUUUUCK!” Matt yelled, “Fucking cumming in your ass!”

They didn’t move. Both of their bodies tensed as Olivia felt Matt’s cock burst inside her, filling her with his warm cum. Likewise, Matt felt the release of Olivia’s orgasm as her pussy juice flooded all over his lower body and the table below! Again, Olivia finally collapsed on top of Matt and they laid motionless for a good 10 minutes. Neither of them moving, but breathing heavily, huffing and puffing from exhaustion, trying to catch their breath.

Finally, Matt broke the silence, “That…was fucking amazing! Nuru massage, eh? I love it!”

Olivia lifted her head and smiling at Matt said, “I know…that WAS fucking amazing!”

Dropping her head back down, Olivia started kissing Matt for a bit. They both felt his softening dick slide out from her butt and she was leaking cum everywhere. They had quite a mess to clean up once they were rested.

Now laying at his side, Olivia propped up her head and asked, “Have you ever fucked someone’s ass before?”

Matt shook his head no saying, “Almost…it was a disaster.”

Olivia had a enormous grin on her face, “Almost…so what did you think of definitely yes?!”

“It felt incredible!” Matt answered beaming, “And I’m hoping it happens again…”

“Fucking-a right it’s gonna happen again!” Olivia said as she sat up further, “I fucking love, love, love getting my ass fucked! I play with it all the time whenever I play with myself…I may even have a butt plug or two…”

Matt’s grin got even bigger! Did he finally discover the perfect woman?

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