Hall Pass Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Tom told Mary that he found it hard to believe that she continued to have sex with Alex even though it was painful. Mary said the pain was worth it. When Tom asked how it was worth it, Mary told him that when a woman has sex with a man who has a big cock, she is getting the best sex she can get.

Tom shook his head and told Mary that she had been severely misinformed.

Tom asked Mary to be honest and tell him if sex with Alex was more fun, or if jamming on the drums, racing go-karts, or playing pinball was more fun. Mary told Tom that drums and go-karts and pinball weren't as painful.

Tom asked Mary where she learned all the shit she believed.

Mary was caught off guard. She wasn't sure how to answer. Tom said, "Somehow you've learned that pain is pleasure and everything else is less. And that's bullshit. You're a young woman who should have fun in her life not pain that you believe is pleasurable."

Mary responded, "Alex has a big cock. That means that he can get any woman he wants. Alex wanting me means something. It means I'm special. It means that I am getting what few other women are getting." Tom nodded, "Uh-huh."

Tom told Mary that he wasn't saying that they would have sex, but if they did it would not be painful. He explained that if they hooked up that it wouldn't just be a hookup. There would massage and kissing and oral sex and a lot of foreplay, more kissing, and then slow, romantic lovemaking. Mary smiled, "Kind of like in romance novels." Tom nodded.

. . .

When Alex and Kathy left their office, Alex asked Kathy if she liked anal. She told him that they would both have to see if that's even a possibility.

Alex asked Kathy whose house they were going to go to. Kathy said that she wasn't sure. Alex told Kathy that they could just find someplace and get it on. Kathy asked Alex if he thought it might be better if they got a hotel room. Alex laughed and said, "It doesn't matter where we fuck, as long as we fuck."

Because Kathy seemed dismayed, Alex asked her if she still wanted his dick in her. She said that she did. Alex told Kathy, "It's not getting any earlier. So, if we're going to fuck, let's do it."

Kathy told Alex that the office parking lot probably wasn't the best place for them to fuck. Alex told Kathy to decide how important getting fucked by him was. Kathy caved and told Alex that maybe they could go to the other side of the office complex. Alex agreed.

Alex drove himself and Kathy to the far end of the office complex. On the way, Kathy asked Alex if he had any lube. He said no and asked why. Kathy told Alex that with his size, lube would make it easier for him to enter her and far less painful for her. Alex scoffed, "Mary never needs lube." then he added, "Maybe she wants my cock more than you do." Kathy quickly rebutted, "Oh no. I want it more than she does. Trust me."

Kathy knew she'd just made a huge mistake. She did want Alex's cock in her, badly, but she'd hoped that he would have had lube. Kathy knew that unless she was exceptionally wet, Alex fucking her was more than likely going to be more painful than pleasurable.

Kathy went through her purse, hoping that she had her lip balm with her. If she rubbed her lip balm on her labia, at least it could help some. She had never done that before, but she felt it could work to cut down on the friction.

It was obvious to Kathy that Alex was not a romantic and he just wanted to get his dick wet. She had hoped for more, but she wasn't going to complain.

When Alex and Kathy parked under a tree at the far end of their office complex, Alex told Kathy to take off her top. He wanted to see her tits. Kathy unbuttoned her blouse and then undid her bra. As soon as her bra was undone, Kathy's breasts dropped. She wore a D cup, and gravity was a bitch. Alex commented, saying, "Now those are some big titties."

Kathy was relieved that Alex wasn't put off by her breasts and the fact that they hung down instead of stood straight up like they did when she was much younger. Alex reached around and unzipped Kathy's skirt. He told her that he wanted to see all of her.

Kathy struggled to get her skirt and panties off. When she was naked, Alex told her to suck him. And she did the best she could. Kathy could get little of Alex's cock in her mouth. He was a lot bigger than Tom was. Kathy felt like a fool because she couldn't deepthroat Alex the way she could Tom. And she hoped that Alex didn't see this as a failure n her part.

Kathy asked Alex if he liked to eat pussy. She hoped he say yes because Tom always did, he was damn good at it, and he always got her wet by doing so. Alex said, "Pussy's made for fucking, baby."

Things weren't going the way that Kathy had hoped, but at least she knew that Alex was going to fuck her and she was going to get to experience a big cock like the ones she had fantasized about.

. . .

Tom told Mary that he didn't want to offend her, but he felt that Alex was a jerk and an asshole. Mary didn't argue. She told Tom that Alex wasn't her dream guy, but he did have the big cock that she always wanted. Tom told Mary that a painful big dick isn't worth fucking.

Mary tried to argue by asking Tom if he'd ever been fucked by a guy with a huge cock. Tom laughed and said that he'd never been with any other guy, big-dicked or not. Mary said, "You can't knock it if you haven't tried it." Tom responded, "The same can be said about smaller cock men."

Mary asked Tom if she could see his cock. Tom looked around, "Right now?" Mary smiled and nodded. Tom unzipped his pants, then told Mary that he wasn't wanting or expecting her to go down on him. Mary asked if that was his choice or hers. Tom said, "I'll be honest, I'm not going to try to stop you if you decide to."

When Tom revealed his cock, Mary was very interested. The only cock she'd ever seen was Alex's. And Tom's cock looked entirely different from Alex's. Mary bent down to get a closer look at Tom's cock. Tom was sure that Mary was going to go down on him, and in one way he wanted her to, and in another way, he didn't.

Mary fondled Tom's cock and stretched it. It was like a new toy for her. Tom couldn't help it, his cock got hard. Luckily, Mary didn't seem offended. Although Tom's cock was fully erect, he still didn't want Mary to go down on him. He didn't want to be the reason that Mary went against her morals.

Mary told Tom that it was cool how his cock grew in her hands. Tom told Mary that her hands were very soft. Mary laughed and said that he wasn't.

Mary looked up at Tom then went down on his cock. Tom knew that he shouldn't let Mary go down on him, but he had also told her that he wouldn't stop her if she did.

Mary liked that she could get Tom's entire cock in her mouth. That was a new experience for her. Mary was never able to get more than some of Alex's cock head in her mouth. and every time she sucked Alex, her jaw got tired and sore.

Tom decided that he and Mary needed privacy. So, he started the car, put it in drive, and got on the freeway again. This time he drove to Look Out Point.

Mary sucked Tom the entire drive from Guitar Center to Look Out Point. This was a new experience for Tom. When Tom parked at Look Out Point, he thanked Mary for sucking him the entire way there but also reminded her that he hadn't intended to have sex with her. Mary asked, "Who said anything about sex? All I did was suck your cock."

Mary had never been to Look Out Point. This was the first time she'd seen the whole city from that point of view. And she was impressed. Mary told Tom that she'd had a great time with him, and she thanked him for everything, including letting her suck his cock. Tom thanked Mary again for sucking his cock and told her that she was an amazing woman.

Mary got out of the car and leaned against the hood. It was warm out and the breeze felt good. Tom got out of the car and stood next to Mary, put his arm around her, and kissed her temple. Mary then asked Tom if he liked to kiss, and he said yes. Mary turned toward Tom, put her arms around his neck, and pulled him closer to her. Kathy wasn't into deep kissing. She said that it was gross. Tom loved to deep kiss, and he found out that Mary liked deep kissing, too.

Without thinking about it, Tom pulled Mary closer to him and he began to gently squeeze Mary's ass with both of his hands. Both Mary and Tom were breathing heavily now. Then Tom put his hands to his side and told Mary that she was incredible and that Alex was a very lucky man to have her.

Mary was confused and asked Tom what she did wrong. Tom smiled and told Mary that she had done everything right. It wasn't her, it was him.

. . .

Alex had Kathy lie on the hood of his car. she was naked, her legs were wide open and Alex was fingering her. Alex was nowhere near as gentle as Tom had always been, but Kathy knew that sex with Alex was going to be different than the sex she had with Tom.

Alex was very aggressive, and his fingers were long and rough. Tom usually used one or two fingers when he fingered Kathy, but Alex was using four fingers.

Alex's fingering wasn't exactly painful, but Kathy couldn't say that all four fingers felt comfortable in her. Kathy knew that she had to let Alex do what he wanted to do if she wanted the best he had to give. So, she let him take the lead and do what he wanted to do.

Alex used his right hand to finger Kathy and his left to tightly squeeze her breasts. As Alex fingered Kathy, he told her that she was a slut and she was going to love his cock. Kathy agreed.

Although Alex was fully engaged in getting Kathy aroused, he wasn't aroused himself. His cock was partially hard, but not hard enough to penetrate Kathy. Alex stopped fingering Kathy and told her to suck him. Kathy got off the hood of the car and knelt before Alex. His cock looked amazing. It was thick as hell. Kathy did her best to get Alex hard so that she could experience the best he had to give her. And that took some time.

Kathy was down on Alex for a long time, and her legs began to ache. Kathy got down on her knees and continued sucking Alex. Kathy had never spent that much time sucking Tom, but she knew that she had to with Alex. Alex fingering Kathy had made her raw, but she knew that if she told Alex that she was sore that two things could happen, either he wouldn't care or he'd not fuck her. She preferred that he didn't care because she was obsessed with his cock.

The harder Alex's cock got, the more of it he wanted to get in Kathy's mouth. He put both of his hands on the back of Kathy's head and jammed his cock into her mouth. Kathy couldn't help but gag, and that turned Alex on. Kathy liked that Alex was being so dominant and aggressive. He was just like the guys in her fantasies.

When Alex's cock was almost fully erect, he had Kathy stand up and lean over the hood of his car. He had her spread her legs and then he put the head of his cock to her already sore pussy. Kathy asked Alex to use his spit as lube because it would be easier for him to enter her if he did. Alex told Kathy, "You're not the first whore that I've fucked. I know what I'm doing."

Alex spit on his cock and then rubbed the head of his cock around and up and down Kathy's vaginal entrance. Within seconds, Alex shoved his cock into her. Kathy screamed and her legs gave out. Kathy had never felt such immense pain in her life. It felt like her vagina was on fire. Alex pushed Kathy's shoulders down and pounded his cock into her saying, "Your pussy belongs to me now, bitch."

Tom had never been one to talk dirty, and it turned Kathy on that Alex did. It worked to Kathy's advantage because Alex's dirty talk helped her to get wet. When Kathy's vagina began to lubricate and Alex was more easily able to slide in and out of her, Alex said, "See? I knew you loved my cock." Kathy told Alex that she didn't just love his cock, she needed it."

Kathy wasn't about to tell Alex that his cock was too big for her, or that his cock hurt more than felt good. She wanted his cock in her, and to have him in her, she wasn't going to complain or tell him to slow down or to not go so deep.

Kathy knew that it was only a matter of time before Alex came inside of her, and then she could recoup and rest awhile. Then Alex told Kathy that she better be ready for a good, long fucking because he took some Cialis.

. . .

Mary told Tom that he was a sweet man. And she liked that he was being so careful around her. Mary told Tom that it was obvious that he loved Kathy. Tom agreed that he did. Mary rubbed Tom's cock and told him that she really liked him.

Tom was between a rock and a hard place. He loved Kathy and didn't want to cheat on her, but he also knew that Kathy was expecting him to have sex with Mary, and he wanted to. Tom wanted to stay true to his wedding vows, but Mary was so beautiful and so amazing. Tom knew he had Kathy's permission to have sex with Mary, but deep inside it still felt wrong to him.

Mary looked around, seeing as they were alone, she took off her T-shirt and bra. Tom was used to seeing Kathy's size D breasts, and seeing Mary's B cup breasts was new to him and they turned him on. Tom had always liked smaller breasted women. Mary's breasts were soft and supple. And her nipples were erect, just like his cock was.

Mary took both of Tom's hands in hers and put them to her breasts. Tom let out a heavy sigh and smiled, "This is amazing." Then he asked Mary, "What happened to me being more a father figure than a lover?"

Mary smiled, "Some girls have daddy issues."

Tom leaned down and took one of Mary's nipples between his lips and lightly sucked on it. Mary leaned her head back and moaned. Tom told Mary that she had the most beautiful breasts he'd ever seen.

Before sucking Mary's other nipple, Tom kissed Mary again. Alex had never paid much attention to Mary's breasts, and when he did, he usually squeezed them hard and often bruised her. Mary had never felt the soft touch of a man's tongue on her breasts or nipples, and she loved how it felt.

As Tom sucked and licked Mary's breasts, he pulled down her shorts and panties. Tom got Mary to lie back on the hood of his car and spread her legs. Tom looked at Mary's pussy. The area around Mary's vagina was plump and puffy. And she had large labia. Tom told Mary that he loved her pussy, and that it was as beautiful as the rest of her was.

Tom leaned forward and began flicking his tongue on and around the tip of Mary's clitoris. Mary started breathing heavily. Alex had never cared much for giving oral. He was more into receiving. Tom, on the other hand, was much more giving.

Tom used both hands to pull apart Mary's vaginal entrance. Then he licked and sucked Mary's labia and darted his tongue in and out of her vaginal entrance. Mary was already wet, and Tom liked that he excited her the way that he had.

Tom always enjoyed going down on Kathy, but Mary's pussy didn't have the smell that Kathy's pussy did, and he felt that he could stay down on Mary for hours if she'd let him.

While eating Mary out, Tom gently twisted Mary's nipples between his fingers. Mary had never felt the way that Tom was making her feel, and she never thought that someone as old as Tom would be as good as he was. Tom spent close to an hour eating Mary's pussy, and in that time, Mary experienced her first-ever orgasm.

. . .

Alex had been slamming his cock in and out of Kathy for close to an hour. She couldn't feel her legs and her pussy was sore and raw.

Alex told Kathy, "I gotta say, you've got one tight pussy."

Kathy had tears rolling down her cheeks. She'd gotten the cock she wanted, but the sex wasn't what she'd expected it to be. Kathy had expected Alex to take his time and maybe do some foreplay, but, instead, he used her.

Alex told Kathy, "I haven't cum yet." Then he asked Kathy if she had.

Kathy was out of breath, but she managed to tell Alex that a lot had happened.

Alex commented to Kathy that he liked fucking her, and he'd be willing to do it again. Then he reminded Kathy that he still hadn't cum.

Kathy told Alex that she couldn't feel her legs. Alex told Kathy that a lot of women tell him that.

Kathy had Alex help her sit on the ground. She was naked, her pussy was sore and raw, and now she was sitting naked in the parking lot of her office complex. Alex saw this as an opportunity to get his cock sucked again. So, he put his cock to Kathy's mouth and had her suck it.

Kathy hoped that she would be able to get Alex off by sucking him. She knew that if she didn't get him off by sucking him that he would want to fuck her again, and she wasn't sure she could handle Alex fucking her again the way he had. Kathy already felt like she'd just given birth to triplets.

. . .

After Mary ad experienced her second orgasm, Tom gently slid Mary off of the hood of the car and kissed her again. Mary and Tom deep kissed, and Mary told Tom that she had never felt anything that good before. Tom told Mary that when she's with a real man, that's what happens.

Tom looked at Mary's tight, young body in the moonlight. He couldn't believe that he had actually eaten Mary out and made her cum.

Mary told Tom that she had so much energy. She felt so alive. And this was the first time in a very long time that she felt happy.

Tom told Mary that she had made him happy, too.

Tom told Mary that she deserved better than Alex.

Mary told Tom that Alex wasn't that bad. She said, "Alex may be aggressive, and an asshole at times, but I think he loves me."

Tom told Mary that she deserved to be with a man that would treat her like he did.

Mary retorted, "Are you saying I deserve to be with you?"

Tom smirked and said that he was a married man.

Mary responded by saying, "Yeah, you're married to a woman that probably has my husband's cock so far up her that she can taste it."

Tom tried to picture in his head what might be happening with Kathy and Alex, but Mary's body was what he was interested in. Tom told Mary that Kathy may have Alex's cock in her, but she was still his wife and Alex was still her husband.

Mary asked Tom why he was fighting his natural urges so much. She told Tom that it was natural for a man and a woman to want to be together.

Tom asked Mary if her parents were monogamous.

Mary told Tom that her parents were Christians and they would never cheat on each other. Tom then asked Mary how she could be so flippant about sex, then.

Mary explained to Tom that she and he hadn't had sex. They'd just played around. She said that if they'd had intercourse, then they'd be having sex.

Tom told Mary that in his mind he and she had already had sex.

Mary giggled, "Until your cock slides past my labia, we haven't had sex." Then Mary added, "And to be honest, I can't wait until we do."

Tom looked at Mary's slender naked body and thought to himself that if he did have sex with Mary that he'd regret it. Then he thought to himself that if he didn't have sex with Mary that he'd regret not doing it.

Tom decided that having sex with Mary wasn't the worst thing he could do, and he told Mary that he wanted to make love to her. Mary said, "It's about time."

. . .

Alex looked down at Kathy and said, "Enough sucking. It's time for some more pussy fucking."

Alex had to help Kathy to her feet. Kathy told Alex that she wasn't sure she could handle much more. Alex told Kathy that she could. Then he turned her around and leaned her against the hood of the car again.

When Alex entered Kathy this time, he felt even bigger than he had the first time. And he didn't use any spit this time. He just rammed his cock into her and started pounding.

Kathy began to regret hooking up with Alex. Yes, Alex had a huge cock like the ones that she'd fantasized about, and if Alex had been someone else, it might have been pleasurable. What Kathy learned from the experience was that big cocks aren't always attached to the best men.