In Deep

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.

It had been the most frustrating week of his life, and he wouldn’t have thought about it if it wasn’t the only other thing that would keep his mind off how much the wind was freezing his balls. As soon as he thought of his balls he thought of the two week gap since he had last had sex. He thought of the opportunity he and Simone had had just a few days ago on Sunday morning. The heating and hot water had been off at the training ground, so he had gone straight to her house for a shower. When he arrived she had been just getting out of the bath, wearing only a smile, and he was enthusiastically pulling off his clothes when they were  interrupted by a text from Tony’s dad to say he would be home early. They had got this far without raising suspicion by being cautious. Fucking his dad’s girlfriend against the clock before a family dinner didn’t seem very cautious…

Instead he had sat, his balls as blue as the sky, while they ate and his brother, Mark (who was really only there for a lift to the bus station later), mooned over Simone’s daughter, Helen. Helen was often at Sunday afternoon dinner, but she was in her late twenties and had no interest in either of the brothers. Tony usually ignored her to save himself from her eye-rolls and sighs. Instead he talked to his dad while Mark embarrassed himself.

After an hour or so, Tony managed to relax and finally his dad took Mark to catch his bus. As Tony helped tidy away the plates he heard Helen complain about the heating being too high and Simone told her that she should just take her sweater off if she was that hot. He was sure he heard Helen say she would have, if it weren’t for Mark ogling her. When Tony took the plates into the kitchen he finally saw why. Side-by-side in the kitchen, Simone and Helen were carbon copies of each other, separated by 20 years. The same blue eyes, the same blonde hair, although Helen’s was in a neat bob rather than Simone’s wayward curls. They were the same height and their figures were almost identical. Tony had to quickly avert his eyes from Helen’s chest as she turned around and, as he knew he would, he got a sigh and an eye-roll. When he looked at Simone she was smirking at him. All he could make out was a sensible bra under her top, but he was now well aware what those sensible bras could contain.

And that was that, blue balls all over again. If there had been any chance that he could have gone upstairs and taken care of himself he would have, but it never presented itself. Simone looked at him in sympathy and Helen did her best to avoid him (as well as folding her arms across her chest a lot).

And that had been that. Once his dad came back, and before he outstayed his welcome, Tony went home. He had a blissful hour to himself before his mum got home and quickly jerked off so he didn’t go crazy. In amongst his mental images of large tits and blonde curls appeared Helen’s straight bob and flat stomach. He imagined himself flipping her over and finishing over her back while pulling her hair. He decided he wouldn’t be sharing this particular fantasy with anyone, even if he was asked.

Three days on, 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, was enough to take his mind off things until now. As the cold air stung his face and whipped round his testicles everything rushed back. Two weeks ago, Simone had told him she had a special treat planned for him and his mind was ablaze with ideas.

The problem was his ‘treat’ wasn’t the only thing he was imagining. While he was finding 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, at least not yet. All of this mental discomfort made him walk slowly, as his stomach turned, then quickly again, in the hope of keeping Simone satisfied.

His imagination teased and tormented him until he reached Simone’s front door and went inside. He took off his coat and shoes, then stood in the hall like Simone had two weeks ago. He let 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, the door obviously closed.

“Go in your room, darling!”

Ten minutes later he heard Simone come out. 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, and 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 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 you can be. The second is when you are hard as can be the woman needs as much control as you can give her. Do you know what I mean?”

“Yes,” 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 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 ass. 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, 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 in the feeling was different. It wasn’t like her pussy, with its flexing walls and the solid bone in one area. 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, 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.

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, tightening her ass 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 also made herself comfortable and moved her bottom gently. Tony’s balls ached and his cock felt both crushed and swollen at the same time. 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, 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. The shower started as a thorough clean of their loins and Simone’s ass, but being naked together was too much temptation. Tony worshipped Simone’s boobs, first with his mouth, then with his soaped-up hands. Once he was done it was Simone’s turn to run her hands all over him. She covered him with suds then rinsed him down and smothered him with kisses. She finally took him in her mouth, sucking his sensitive tip and making his knees go weak.

Tony held himself up as best he could as Simone eagerly sucked at his cock. He responded quickly as she indulged his tip with her tongue and rubbed his shaft with her hand. The water created friction which intensified the feelings and quickly his sore balls started tingling. Straining at first he came in her mouth and she swallowed his second load.

Simone stood up and kissed him on the lips.

“Sorry, darling,” she said, “I was greedy. I should have brought some to share.”

“I don’t mind,” he said, already reaching between her legs.

“Go slow,” she gasped, “I’m still…. ahh…”

Tony went as slowly as he could, manoeuvring her away from the shower jet so it didn’t wash away her juices. As his fingers worked their way around and into her she raised one of her boobs to suck. once it was in his mouth she held onto him with both hands.  She dug her nails into his skin as he hit her g-spot and cried out when her final orgasm washed over her.

Satisfied at last, they shut off the shower and towelled themselves dry. Simone picked up a tube of ointment, looked at it for a moment, then handed it to Tony.

“Your last job for the evening, darling,” she said as she bent over, showing him her asshole again. It was red and slightly swollen.

Without needing to ask Tony rubbed the ointment onto it then washed his hands. When he was done Simone wrapped a towel around her waist and he did the same.

“Come on, darling,” she said, “If we clean up tonight we can have a lie in.”

They stripped the bed in Simone’s room and talked. Tony even managed to have the conversation while Simone’s tits were on show.

“When do your parents get here?” he asked.

“Tomorrow evening,” she replied, “They like to travel late so when they arrive they can eat then go straight to bed. I don’t blame them, but it feels strange to not have a proper conversation with someone until they have been in your house for over twelve hours.”

“And… how long are they staying?” he asked, knowing Simone could hear the second, implied question.

“They will be here for a while,” she said, smirking at him, “Their flight home is two weeks on Tuesday. The next time will depend on a few things which we can discuss tomorrow.”

Tony could feel his disappointment at such a long time between sessions with Simone. He was also trying to work out whether her time of the month would cruelly impose itself on their next opportunity. If that was selfish of him, he didn’t realise.

Satisfied everything was either in the wash or ready to be in the wash they finally went to bed, which tonight was the sofa-bed in the upstairs office. Simone and Tony’s dad only ever used it when her parents visited. Before Simone could lie down her phone rang and she rushed to get it from where she had left it in the bathroom. Tony lay there, naked under the duvet, wondering who it could be at this time of night. Simone came in fifteen minutes later, naked herself and crawled into bed with him.

“I don’t suppose you know who that was?” Simone asked, cheekily.

Tony felt himself tense up.

“It was my Dad, wasn’t it,” he said.

“Yes,” she said, “He was checking we didn’t need anything for tomorrow. He’s been acting guilty ever since he took on those new shops. Maybe he thinks he isn’t being a good husband. It’s a shame he can’t know I’m being taken care of while he’s away.

Tony tried to say something but Simone just kissed him and laughed.

“Relax, darling,” she said, “We have been careful, and I assure you I do not sound guilty when I speak to anyone.”

“I know,” he said, trying to relax, “But it still makes me nervous.”

“OK, darling,” she said, “No more talk of anyone finding out. Just one more thing.”

Tony tried to look at Simone but she lay down close and put her arm and leg over him.

“Tony,” she said, nuzzling his 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. He thought of a younger Simone, longer blonde hair, blue eyes, big tits… and a saucy image of Helen sprang into his head. He shook it away and looked Simone in the eye.

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

“Good,” she whispered, “Then you can tell me all about it.”

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One response to “In Deep”

1. Alex Hewes says:

   April 10, 2021 at 8:37 pm

   Hi. Be kind and leave a comment! There is one more in the series for you… ‘In Luck’.

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