Learning Not To Ask Questions

By Melancholy033.

James and Lilly were college sweethearts. Lilly had several boyfriends before James, but for James, she was his first. They both attended a small university in the Northeast.

James and Lilly loved each other very much, but both were fairly naïve early on in their relationship. James’ first indication that maybe he and Lilly were not completely compatible occurred on their second date.

James and Lilly had just seen a movie together and were heavily petting each other throughout the film. After leaving the movie, Lilly suggested they spend some time in the backseat of James’ SUV.

James was worried about getting caught, but Lilly insisted she had done this kind of thing plenty of times before, and it would be fun. James relented, excited to start a real sexual relationship for the first time in his life.

Lilly had begun unbuckling James’ belt in the backseat when James nervously asked her, “Are you sure you are comfortable doing this?”

Lilly giggled, “Just keep an eye out for the theater security, and quit worrying about me.”

James felt Lilly pull down his jeans and then his boxers. He was more excited than ever when he felt one of her small hands grab his cock and start vigorously pumping it as her other hand began to massage his balls.

James was always proud of his manhood, being average, maybe slightly above, according to the internet. So, he was not at all expecting what Lilly was about to say.

Lilly, after getting him hard, innocently asked, “Does it get any bigger?”

James had no idea what to say and insisted it was the odd angle he was positioned in, in the back seat of the SUV.

Lilly immediately regretted her awkward question, and after James squirmed around, she insisted his cock looked much bigger from the new angle.

James, although a little embarrassed by Lilly’s question about his size, stood no chance against Lilly’s impressive oral skills. After a couple of minutes, Lilly’s hot sucking sounds, wet mouth, and skilled tongue were able to coax a large load of cum out of James.

James, a young man in college, was more than happy to go for round two back at his dorm, but Lilly insisted she needed to get back to her dorm by herself.

Lilly’s question, “Does it get any bigger?” still rang in the back of James’ mind when he got back to his dorm. He did not want to come off as insecure, so he did not bring it up with Lilly in their late-night texts later that evening.


The next night, they were not able to see each other, but James was still bothered by the question. He knew he had no experience with the opposite sex and was not sure what was appropriate to ask, but he still sent the text, ‘What did you mean last night when you said ‘does it get any bigger?

Lilly took a while to text back, ‘I didn’t mean anything by it. I was just wondering if you were fully erect or not.’

James responded, ‘Got it, but I just wanted to confirm with you. Were you expecting something different?

Lilly texted back, ‘No way, I loved your size. Honestly, I don’t know what I was thinking when I asked that.’

James’ insecurities were not satisfied. He had to press on for validation, ‘Am I the biggest you’ve had?’

Lilly, knowing that honesty was the best policy, replied, ‘James, I love the size of your cock. It is perfect for me. I would prefer not to talk about anyone else’s size.’

James would not take no for an answer and repeated, ‘Am I the biggest or not?

Lilly replied candidly, ‘I don’t want to hurt your feelings, but I just had unrealistic expectations for your size because the last guy I hooked up with was just a little bigger than you. I hope this doesn’t mean we can’t continue to see each other.’

James tried to play it off coolly, ‘Oh, no, that’s okay. I was just curious and wanted to make sure we were still compatible. Thanks so much for being honest with me. That’s what is really important.’

Lilly replied, ‘OMG good, I was worried that would hurt your feelings. Of course, we are still compatible. The last guy I was with was a dick. I mean, he had a really big dick, maybe a little more than 1.5x yours, but that didn’t matter because I hated his personality. I swear we only went on like one date, and I was done with him.’

James now regretted bringing this up and learned a valuable lesson not to ask questions he did not want to learn the answers to. He would only need to be taught this lesson one more time in his relationship with Lilly.


In the fall of their senior year, Lilly and James got engaged. It was a hectic time for both of them as they prepared to transition from college to working life. Unfortunately, both were still young and dumb.

In between the holidays, the two of them got into a fight. Although they spent many nights together, they both still had their apartments. They agreed to separate temporarily and give themselves some time to think about their relationship.

Lilly and James met up for coffee. Neither of them saw each other for a couple of days. James let Lilly know he was going out of town for the night with some friends but would be back early in the morning. Lilly was nervous but always felt a need, to be honest. She let James know that one of her classmates had asked her out to coffee that night, and she asked James for permission to meet him.

Their relationship was already strained, and James was unsure how to respond. He wanted to seem confident, but he said he did not mind if Lilly went and got coffee with her classmate.

At around 9 pm that night, James got a text from Lilly telling him, “I am going to be busy the rest of the night. Won’t be able to call or text. Don’t wait up. Will fill you in tomorrow.”

Alarm bells went off in James’ head, but his texts and calls to Lilly for follow-up information went unanswered.


The next morning, James went to Lilly’s apartment. She did not answer the buzzer, but her roommate Lisa did. James asked Lisa if she had seen Lilly. Lisa immediately squirmed at being asked this awkward question.

Lisa liked James and hated to be the one to tell him, “Lilly went out last night. They had dinner and stuff here, then left at around one am. Honestly, I thought she had gone over to your place.”

James sat on Lilly and Lisa’s living room couch, dumbfounded.

About half an hour later, Lilly came in through the door, carrying her duffle bag. Her hair was a mess; she was wearing an oversized gray men’s university t-shirt, and the skimpiest pair of blue cotton shorts James had ever seen her in. It was pretty clear to James that Lilly had done more than just coffee or a dinner. Lilly immediately knew she had messed up. She started crying, grabbed James’ hand, and led him into the bedroom for some privacy away from her roommate, Lisa.

Lilly, still sobbing, explained to James, “I had just wanted to go for coffee with my classmate, Tom. Then Tom insisted he was hungry, so I offered to cook him dinner at my place, as Lisa was not supposed to be home.”

Through her sobs, she continued, “Tom then offered me a massage in the living room, on the couch. I accepted the offer, but it was just supposed to be a massage.”

She continued, “I was worried Lisa would come home early and judge me for getting a massage, so I had Tom give me a massage in my room. You know how much I love massages.”

James replied, “Lilly, what the fuck happened last night?”

This is the last time James would ever make the mistake of asking his future wife very dumb questions.

Lilly answered him, “One thing led to another. Tom was making me feel so good with his massage that he stripped me down, supposedly to not get lotion all over my clothes. Tom was really working on my ass when I felt his cock. He had somehow taken off his pants while massaging me, and I could feel the thick head of his cock lining up to penetrate me. I was scared and did not know what to do…”

James, unsure how to feel other than upset, replied, “Did he rape you?”

Lilly responded, “Yes, I mean, no… I had to get him off of me. I would never cheat on you. I knew the only way to get him to leave was to give him a blowjob. I know it’s bad, but it was better than letting him fuck me. So I flipped around and started to suck on his cock… Babe, are you hard?”

James was hard, and he did not know why. Was it because his beautiful girl was sitting in front of him in a skimpy pair of shorts, her puffy pussy lips protruding through the fabric, or was he hard because of her story of the events of last night?

James did not respond. He just pulled the blanket over his crotch to hide his erection.

Lilly continued her story, “James, I don’t want to hurt you. I think you’ve heard enough.”

James angrily rebutted, “Just tell me. Get it over with, please.”

Lilly picked up where she left off. “James, you know, before we met, I was really into guys with large cocks. Well, Tom, he had an amazing cock and an amazing body. Not only that but as I was sucking him off, he started to play with my nipples and my pussy…”

James, still hiding his manhood, responded, “Lilly, I don’t need to hear every detail. What did you end up doing?”

Lilly answered, “Well, James, he made me feel a lot more beautiful than you have lately. His message made me feel wanted. Sucking his cock felt like a favor. Honestly, he flipped me around before I could get him off with my mouth. He flipped me around, doggy style, and he fucked me. He fucked your girlfriend, your fiancé, your ex, whatever I am to you, he fucked it. He took his big cock, and he fucked me. Tom fucked me like you never could. I knew he was deeper in me than you could ever be, and I loved it. I loved thinking about that as he fucked me… I loved it because you have been treating me like trash lately. ”

James said, “I am not the bad guy here.”

Lilly, realizing she had gotten too emotional, apologized, “I know, I am so sorry, Babe. I was thinking with my emotions and my pussy, not my brain. When he had me bent over, I had to bite the sheets due to his size. I asked him to put on a condom. I really did, but with the sheets in my mouth, I don’t think he heard me.”

James again, “Lilly, I can’t believe you.”

Lilly responded squeamishly, “Babe, I swear I didn’t want Tom to be the first guy to fuck me raw, but he wouldn’t take no for an answer… Babe, the only way I can get through this without you freaking out on me is if you trust me.”

James grunted. “You’ve broken my trust, and there is nothing you can do to repair it. You’re a real slut”

Lilly, an expert manipulator of men, reached her hand under the blanket and started to gently rub James’ hard cock.

Lilly demanded, “Take out your cock now, I miss it so much, it’s the only one I care about.”

James gave in. Lilly truly had him wrapped around her finger, or perhaps more accurately, had her hand wrapped around his cock,.

Now Lilly was stroking James’ cock, James feeling very conflicting emotions.

Lilly continued her story, “Tom was fucking me from behind, you know I never orgasm, but he had me so close. That’s when he did it. He stuck his finger in my ass, and I came. I came for the first time in my life, with his finger in my ass and his oversized cock pumping in and out of my tight pussy, reaching places that you have never reached.”

Lilly stopped stroking James’ cock, knowing that if he came now, he would leave and never come back.

Lilly assured James, “Baby, first off, I regret cheating on you. I am so sorry. Second, I promise I will make this up to you. Any girl, one night stand, you have my permission. Thirdly, baby, please keep in mind that you have not made me feel loved lately. I did this out of desperation. I really needed to feel love from someone, and he gave that to me.”

James replied, “Are you crazy? Relationships don’t work like that. You can’t just cheat on me and then give me permission for my one-night stand!”

Lilly hushed him, “Quiet. Do you really want Lisa to hear all of this? Besides, we were on a break, so technically, it is not cheating.”

James replied, “I can’t believe you. You are heartless.”

Lilly started slowly stroking James’ cock again to calm him down and continued her story, “Baby, I need you to let me get it all out. Unfortunately, my orgasm triggered Tom’s, but he was a perfect gentleman and pulled out in time. I was sure to catch it all in my mouth to make sure he did not get me pregnant.”

James replied, “Is that supposed to make me feel better? You never give me oral anymore, and you certainly never let me enter raw. I can’t believe you did all this for him!”

Lilly shushed him again, “Keep it down. I don’t want Lisa to know the details. I was so ashamed of cheating on you, even though we were on a break. I didn’t feel comfortable kicking Tom out, though, because now Lisa was in the kitchen, and I was terrified she would find out.”

James replied, “Oh my God, you got fucked by a stranger when Lisa was home, this is so embarrassing, you should be ashamed.”

Lilly continued, “Unfortunately, Tom was ready for round two pretty quickly, but I refused him. He then started to spank me loudly, and I did not want Lisa to find out, so I headed back to his place with him.”

James grabbed Lilly’s hand, stopping her from stroking him anymore, disgusted by her.

James retorted, “That’s enough, thanks for being honest. I hate you. I am leaving.”

Lilly, unable to stroke him into compliance, was only left with her tears as a defense.

Lilly started to sob and begged James, “Please reclaim me. We don’t need to get back together. I need to be yours again, just for one day. Please, I am begging you.”

For James, this was a decision he needed to gain experience making. The love of his life had just betrayed his trust, but at the same time, she was just a human. As she sobbed in front of him, he pitied her. He knew humans make mistakes. He knew that whatever decision he made, he would regret it. Take back a cheating partner? Throw four years of love down the drain?

All because he had to keep asking her these dumb questions he did not even need the answers to.

He relented. He made up his mind. He was going to salvage this relationship. He was thinking with his cock this morning, just as Lilly had been thinking with her pussy last night.

He pushed her back on the bed. She lay there on her back, her cheeks still wet with tears, in another man’s t-shirt, in a skimpy pair of skin-tight cotton shorts she would never bother wearing for him. He pulled her shorts down.

He was in shock.

He pulled down her shorts to reveal no panties, just big gobs of cum still clinging to her inflamed pussy lips. Cum on her thighs, cum in the crotch of her shorts, cum now leaking onto her bed. Now, he realized why she had been stroking him throughout their talk. He would never have done this if he was thinking with anything other than his cock.

For the first time in his life, he fucked his girlfriend, fiancé, future wife, or whatever you want to call her. He fucked her raw. He stuck his cock in her used, gooey, stretched, inflamed pussy. It was not how he imagined his first time raw would be. It was not how he imagined a loose pussy would feel.

Her stretched pussy didn’t feel ‘loose.’ It felt velvety. It felt softer than ever before. It felt broken in. It felt amazing. James fucked her as hard and as deep as he could, doing his best to reclaim her. If he was being honest, it was the best sex of his life. James might have been pushing Tom’s cum back into her, but now he would be adding his own too, and lots of it. He came harder in her used pussy than he had ever cum in his life. He was exhausted, lying on top of his lover, but deep down, he knew he just had the best sex of his life.

It was the best sex, not just because it was his first time without a condom, but it was his first time giving her unconditional love. She fucked up, she would pay for it, but for now, he was making her his again. He nodded off, his cum deep inside of her velvety soft, slutty, used pussy.

He enjoyed the moment of reclaiming her, part of him loving her more than ever, much of him hating her more than ever.

He had yet to make up his mind if he was taking her back for just one day or forever.

He did know one thing for certain: do not ask questions you do not want the answer to.


The End.


*This story has been edited to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story has been previously published on other free sites and is now public domain, which is why we can publish it here.

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