In Experience - In Deep (5)

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Tony stomped his way through the cold night air. He had somewhere to be, he really wanted to get there, but he couldn’t summon up a run. He just put one foot in front of the other as quickly as he could, eating the journey up in a thousand bites.

As she had predicted, there had been no chance for Tony to sleep with Simone, his ‘sort-of-step-mom’, for a week and he had been blocked at every other opportunity for relief. There was a late visit by his uncle and aunt, a night chatting with his dad, then this morning his dad had decided not to rush to work and instead waited until Tony’s lift arrived. Fortunately for Tony, a day with his best friend, including one of the biggest home cooked meals he had ever seen, had been enough to take his mind off things until now. As the cold air stung his face and whipped round his testicles everything rushed back. 

The last time they had been together Simone had told him she had a special treat planned for him and his mind was ablaze with ideas. The problem was his ‘treat’ was not the only thing he was imagining. While he was trying and failing to find time to jerk off, Simone had his dad to satisfy her. If she decided sneaking around was too much trouble she could call it off and still get fucked. He didn’t have any alternative, not yet. His imagination teased and tormented him until he reached Simone’s house and went inside. He took off his coat and shoes, then stood in the hall letting the warmth of the house seep into his hands and feet and loins before shouting for Simone. As soon as he did she responded from the bathroom. By the sound of her voice the door was closed.

“Go in your room, darling!”

Five minutes later he heard Simone come out of the bathroom. She peeked around his bedroom door and grinned.

“Strip off lover,” she said, “Then come to my room in two minutes. Knock first!”

With that she was gone. Tony heard her bedroom door close. Confused and horny he did as he was told, and exactly two minutes later he was standing naked on the landing. He knocked twice on Simone’s door.

“Come in, Darling!” she called.

Tony entered to find Simone lying on her front under a sheet. She was propped up on one elbow smiling at him as she looked him up and down. Tony’s cock twitched as he saw that under the sheet she was as naked as he was. Her backside was sticking up, as if she had something propping her up under her belly. The only thing she was wearing was a hairband with tinsel and a red bow on it.

“Merry Christmas,” Simone said, a cheeky purr in her voice, “I hope you like the little surprise I’ve got for you.”

Tony stood open-mouthed and she laughed, “Maybe it’s not so little. Come here, it looks like I need to wake someone up.”

Tony kneeled on the edge of the bed and Simone took his cock in her hand, then into her hot mouth. It didn’t take long before he was rigid with desire.

“You’ve learned a lot over the last month, darling,” she said, licking and sucking his cock, “And you have earned something special, especially after being so restrained on Sunday.”

Simone looked up at him as she squirted some lube on his erection. It was cold after the warmth of her mouth but it felt good as she rubbed it all over. He noticed there were towels on the bed and the duvet was nowhere to be seen.

“My special treat for you darling,” Simon said, rubbing him back and forth, “Has two lessons. The first is that sometimes you will need to be as hard as hard can be. The second is when you are that hard the woman needs as much control as you can give her. Do you know what I mean?”
“Yeah,” he said, “I mean, I think so.”

“Good,” she said, playing with the tip of his cock,  “But right now I bet you are thinking with this, so we had better move on to the practical.”

Simone gave his slick cock a quick kiss then, with a single movement, she swept the sheet away, revealing her naked body. Her bare round ass was raised up by a towel-covered cushion.

Tony reached over and ran his hand over her butt cheek. He slid it down the back of her leg then up the inside of her thigh. He went straight for her sex, running his finger around her already wet opening. When he explored a bit more his thumb hit something sold between her cheeks.
“Go down there and have a proper look, darling,” Simone purred.

Tony got off the bed and walked around to kneel between Simone’s calves. Straight away he saw a purple jewel, about the size of a quarter, sitting where her asshole should be.
“Have you found it?” Simone asked.

“Yes,” Tony said, rubbing the gem with his thumb and causing Simone to gasp, “Is that what I think it is?”

“What do you think it is, darling?”

“It’s a butt-plug,” Tony said, and Simone nodded, “What-?”

Tony didn’t want to ask what she wanted him to do. If she wanted to be fucked with that in place, he would do that, but he wanted to be where that thing was right now.

“A little warm up would be nice, darling,” she said, “Press your thumb on the jewel and move it around a bit while your fingers are busy.

Tony did as he was told, giving the butt plug some attention while he reached between her legs to rub her clit. After a while be eased two fingers into her pussy.

Simone moved slowly and deliberately against him. After a while she took a deep breath and opened her eyes. She reached back to hand him the bottle of lube. When he took it from her she put one hand on each ass cheek and pulled them apart.

“Take that out, darling,” she said, “Nice and gently.”

Tony took his fingers out of her and smeared pussy juices around her ass as he took hold of the butt plug. He pulled slowly, making sure he had a good grip. Simone moaned and gasped as the thicker part of the plug stretched her asshole. A moment later it slid out with a quiet pop. It was an odd looking thing, like a bullet on a stick about half the length of his cock but a bit thicker at its widest point.

Simone let go of her ass for a moment to direct where the plug should go. Once Tony had disposed of it she pulled again, showing him her slightly open asshole.

“Plenty of lube on there, please,” she said, “And a bit more on you.”

Tony squeezed the thick lube directly onto her puckered ring and pushed it in a little with his finger. Satisfied, he put a blob on the tip of his dick.

“You’ve fucked my pussy,” Simone said, looking back at him as best she could, “My mouth and my tits. Time to complete the set.”

Tony moved forward and put the tip of his dick on her asshole.

“Just gently, yes?” he asked.

“Yes, ah,” she said, still holding her cheeks apart, “Push… Ah!”

Tony eased his way in. At first she opened a little for him as his tip pressed against her rear entrance, but it took a few gentle pushes before her greased sphincter gave way. With each press Simone gave a little squeak of pain, with moans of pleasure in between. Her fingers dug into the flesh of her ass and when the tip of Tony’s cock finally entered her it did so suddenly and she cried out, releasing her cheeks to close around his shaft. Tony stopped, enjoying the feeling of being inside her tight flexing entrance, but worried this was as far as he would get before Simone changed her mind.

“It’s OK, it’s OK,” Simone gasped after a moment, “Go slow. Give me an inch at a time.”

“Oh, I will,” Tony said, “You’re really tight. Are you sure you’re OK?”

“Yes,” she said, “Yes I’m good. Merry fucking Christmas darling!”

“Merry fucking Christmas,” he replied, easing himself in an inch and back out again.

Tony continued, inch by inch, keeping his thrusts short. Simone’s moans came more frequently with only the occasional gasp of pain as he went deeper. Tony held her cheeks apart as he got about two-thirds of his length inside her.

“Stop,” Simone said. Tony froze, but it didn’t sound like Simone was in trouble. “Start going back and forth,” she continued, “Not deeper, just longer.”

Tony obliged, pulling out a few inches and pushing back in until he had a rhythm going. The lube was doing its job and he had a moment to think about how his cock felt in her ass. At first he main feeling had been her tight ring squeezing him as he pushed inside. Once inside the feeling was different. It wasn’t like her pussy, with its flexing walls and feel of solid bone at the front. Instead it felt like a soft tube stretching around him as he moved back and forth. Simone flexed her sphincter in time with his movements and pushed up towards him, changing the angle and pushing on the top of his cock. With her ass a bit higher she reached underneath herself and he felt her fingertips brush the base of his cock.

“How far is it in?” Simone asked, “How much is left?”

Tony looked down, not trusting his senses.

“Two inches or so,” he said.

“Shit,” Simone gasped, “OK, give me all of it. More lube, then give me the whole thing then fuck my ass until you cum.”

Tony found the lube and squirted it over Simone's anus and the last few inches of his cock. Satisfied it was enough, he pushed himself further in using little trusts until one final push mashed his pubes into the crack of her ass. He felt the warmth of her pussy and the delicate touch of her fingertips on his scrotum. Simone, pushed back against him.

“Argh,” she moaned, “Fuck, that’s so deep. Do it, Tony, fuck me. Fuck my ass. Fuck me hard until you cum. And make sure you cum deep, really deep inside me.”

“Are you sure?” Tony managed, “You want me to cum in your ass?”

“Yes,” she moaned, “Fuck yes.”

Tony didn’t ask again. He gripped her cheeks and started thrusting into her big, tight, delicate ass. Within a few strokes he had abandoned the gentle approach and was pumping away, slapping against her ass cheeks making them wobble back and forth. His only thought was not to go too far and to pop out of her, just in case he couldn’t go back in without hurting her. It was a struggle. More than anything he wanted to squeeze his tip in and out of her back entrance. 

Tony finally felt the familiar churning in his balls and pushed deeper into Simone with every thrust. At the same time he felt Simone wriggle and twitch as she played with herself. Her moans were smothered by the pillow and he couldn’t tell if she was there yet, or had been several times as he fucked her ass.

When he came he felt it twice. First, the familiar rush of orgasm, then the build up and release caused by the cum being forced past the part of his cock where Simone’s asshole held him tightly. Every pump made Tony grunt with effort and every grunt seemed to make Simone grunt harder. Spent, Tony rested forwards, putting his hands on the bed. His weight pressed down on Simone's pelvis and kept his exhausted dick inside her.

"Shit, that was intense," he said at last, "Best Christmas gift ever."

"I knew you’d like it," Simone replied, still muffled by the pillow, "I'm going to have to give you that again."

She moved her arms from under her belly to under her head. She licked her fingers then reached up to offer them to Tony. He strained to get a taste of her juices, then started to shift his weight.

"Hey," Simone said, flexing her asshole around his cock, "Stay where you are, darling."

"I thought you'd get sore," Tony replied, "I-"

"You'll do as I say," Simone purred, "It's the entrance that gets sore, especially when a big boy like you pushed in. Stay inside while you soften a bit. My big ass should be comfortable enough."
Tony laughed and moved his arms to get comfortable. Simone adjusted herself and moved her bottom gently. Tony's balls ached and his cock felt both crushed and swollen at the same time. He noticed that at some point her festive headband had fallen off. As they rocked together they talked about how it felt and even about their day and what they needed to do tomorrow to get the house ready for Simone's parents' arrival on Friday.

"Does it make you feel naughty, darling?" Simone asked, resting forward and moving one hand back to her pussy, "Fucking me in the ass in the bed my parents will be sleeping in?"

"As if I could feel any naughtier," Tony laughed, struggling with the word, "We've been pretty fucking naughty for a while now."

“Yes we have,” she said, “I was hoping you could stay inside and fuck me again, but maybe next time. The lube has worked but I don’t think there’s anything to sooth being stretched this much.”

Tony waited a moment. It felt like his hard-on had paused softening and was starting to get excited again. He withdrew slowly, but he was also squeezed out by Simone’s ass. His swollen glans resisted for a moment before allowing him to complete his exit as gently as he could. Simone just gave a satisfied moan then what sounded like a sigh of relief once he was finally out of her. He took a moment to look at her distended hole before Simone moved. 

“Straight to the shower I think, darling,” she said, “Help me up.”

Simone held a towel between her legs as Tony helped her up and they both walked awkwardly to the bathroom. As she adjusted the shower Tony held her from behind and played with her tits, looking at them over her shoulder.

“Tony,” she said, tilting her head back so he could kiss her neck, “You aren’t just going to spend the next few weeks waiting to fuck me again, are you? I mean, you should be putting all of this into practice. Promise me you’ll get out and find a girl.”

For a moment he tried to imagine who that would be. All he could think of was curves, blonde hair and big tits.

“I promise,” he said, without much confidence, “I will.”

“Good,” she whispered, shrugging him off and getting into the shower, “Then you can tell me all about it.”


Find out if Tony can keep his promise - “In Luck” is next.