Cuckold dreaming!

[hwc]

"It felt so good knowing that Amanda's date was going well! But, at the same time, I was jealous. I knew that I might feel that way, so I'd prepared myself for it by expecting to feel jealous. I know it sounds weird. Like why would I want my girl to go out with another guy if I was expecting to be jealous about it?"

You should definitely tell her about your jealousy! It will remind her that you care about her, despite wanting her to enjoy a boyfriend/girlfriend relationship
with someone else.
You could even tell her that you enjoy the jealousy, so if she can think of little ways to make you feel even more jealous, you would enjoy that and it could be amusing for her.

[desertsub]

You should definitely tell her about your jealousy! It will remind her that you care about her, despite wanting her to enjoy a boyfriend/girlfriend with someone else.
You could even tell her that you enjoy the jealousy, so if she can think of little ways to make you feel even more jealous, you would enjoy that and it could be amusing for her.

I agree! I am not a jealous type and it used to bother my wife, she would start thinking that I didn't really love her because I didn't get jealous in nay way when she fucked another guy. We had a talk about it and I told her that for the most part I wasn't jealous but under certain circumstances I would feel some jealousy. Since then, whenever I do feel some jealousy I always tell her and it makes her happy that I am having those feelings. Jealousy, when controlled, can be a big turn on to a woman!

[ChrisCuck]

I'm definitely keeping the jealousy to myself for now. I'm lucky to have even made it this far. I don't want to blow it before Amanda has even had sex with another guy. Jealousy games like you guys are suggesting, where Amanda tries to make me jealous on purpose, seems like a more advanced form of cuckolding that I don't think Amanda or I are ready for. We may never be ready for something like that. Or maybe we will be one day. But, definitely not now.

For now I'm just hoping that she and Matt finally have sex. Their second date is happening later today. But, Amanda and I probably had like 20 dates before we'd gone all the way. That was back in high school and she had zero experience before me, so it's obviously different than the current situation. But, still. Amanda is obsessed with her image. She's not going to do anything that ruins her reputation. So, I'm guessing Matt's night will end with blue balls.

[Anders86]

When do Amanda and Matt has their next date?

[wingman]

Did they go out on date #2?

[ChrisCuck]

Did they go out on date #2?

Yeah. This past Saturday. I was right about Amanda leaving Matt with blue balls.

I was supposed to see Amanda today. There was a nice window of opportunity when my roommate Steve wasn't going to be around. I wanted to talk to Amanda in person about her second date. I wanted to make love to her. But, she blew me off.

She messaged me earlier.

"Hey. Hate to cancel, but Matt's roommate is going to be working on a project in the library. So Matt will have the dorm room all to himself. He invited me over to watch a movie. I don't think I'll have enough time to squeeze you in before I head over to his dorm."

"It's cool. But, you know he's probably hoping to do more than just watch a movie?"

"Yeah. I know. That's why I'm cancelling with you. I think I'm ready."

"For real?"

"I can't be accused of being a slut if I hold out until the third date, right? Lol!"

"Right!!!"

"So you're not mad I'm blowing you off?"

"No. Not mad. Just please let me know how it went as soon as your date is done. K?"

"Will do! <3"

Amanda is over there right now! It's all I can think about! I can't believe how bad I want this. I hope Matt's big dick is inside of my girlfriend at this very moment!

[Anders86]

Chris, all I can say is wow. What a great update, and arousing.
I am crossing my fingers for you and I too are hoping that Matt is balls deep in her.

[yielding william]

After holding off this long, she is going to get fucked so good! I hope his dick is all the way in her hot pussy. She will love it.

I understand your excitement. You must be jerking on your little dick just thinking about it all. I love the way this is working out.

[lonelyhubby]

Really hot stuff! Are you and her equally turned on by the danger of her possibly falling in love with Matt over time?

[ChrisCuck]

Amanda messaged me yesterday after she got back to her dorm room.

"It's official. I can now say I've been with more than one guy!"

"That's great! Did you enjoy it? Was it good?"

"It was okay."

"Uh oh. Just okay?"

"I'm just messing with you! Lol! It was great!!!"

"Oh good! That's a relief!"

"I think I like big dicks. Or at least I really like Matt's."

"I was hoping you would! So is he much bigger than me?"

"Much! And he's good at using it too! I'm a lucky girl!"

"Think you'll have sex with him again?"

"Lol! Of course!!!"

"Did you let him cum inside of you?"

"No. You're still the only guy who's cum inside me. Matt wore a condom. It was the right thing to do. Maybe one day though. Have to see how things go with him. But, so far, so good!"

"This is great! I'm so horny right now!"

"You should go pat off your little dickey then! Lol!"

"That's a great idea! Can I see you soon though?"

"Of course! Thursday?"

"Yeah! Thursday."

"Ok. Ttyl. I gotta go shower."

"Night!"

Chris, all I can say is wow. What a great update, and arousing.
I am crossing my fingers for you and I too are hoping that Matt is balls deep in her.

Yeah. Matt was definitely balls deep in Amanda yesterday!

After holding off this long, she is going to get fucked so good! I hope his dick is all the way in her hot pussy. She will love it.

I understand your excitement. You must be jerking on your little dick just thinking about it all. I love the way this is working out.

Things are definitely working out great!

Really hot stuff! Are you and her equally turned on by the danger of her possibly falling in love with Matt over time?

It's only been 3 dates. So I'm not really thinking about them falling in love. But, it could happen. Or maybe it's already happening? Some people fall in love at first sight, after all. Amanda and I already discussed the possibility that she could fall in love with someone else and break up with me. It's not something we talked about as being a turn on though. More just being realistic and deciding it's worth the risk.

[yielding william]

I'm glad she is getting dicked so well. I think if he can satisfy her needs with his bigger cock she will appreciate you more for letting her have a real man when she needs him. You can be happy just stroking your little dickie.

[wingman]

How’s things?

[wingman]

How did it go last night?
Had she been with Matt after Sat evening (ie have they had date #4?)
Did she get to tell you, better yet...tease you, about the sex with Matt?

[ChrisCuck]

I saw Amanda Thursday, as planned. We had my apartment all to ourselves.

I didn't want to just jump right into talking about sex. So I was asking how she was doing, how her classes were, and stuff like that. I told her how good it was to see her and we started kissing. When we took a breather, I asked her about Matt.

"So, I'm sort of dying to hear about you and Matt!"

"Yeah, I figured. You pervert! So what do you want to know?"

"Everything!"

"Okay. We went to his dorm and were sitting on his bed. He was going to put on a movie. But, I couldn't wait anymore. I started kissing him really aggressively and clothes started coming off. I felt his hands all over me and it just felt right. When I took a good look at his dick, all I could think about was sucking it. So that's what I did. I was sucking him for quite a bit and I really liked it! He told me how good I was and that he'd cum soon if I kept going, but that he really wanted to be inside of me."

Before I continue. I need to explain something to all of you. In all the time Amanda and I have been together, she's never given me a real blowjob. I'm not saying she's never had my penis in her mouth. She'll lick it, maybe suck on it for a few seconds. But, she's never sucked on it for any extended period of time. She's never been into that. So hearing about her blowing Matt made me both very jealous and very horny. But, mostly horny! Insanely horny!

"I stopped sucking him," Amanda continued. "And then he was licking me all over. His tongue felt good on my tits and then down my belly and then he was licking my pussy. His mouth waa doing some amazing things down there! I was ready to have him inside of me. I'd brought a couple condoms that I'd picked up for free from the condom bowl on campus. But, before I had a chance to ask him to put one on, he got up and grabbed a condom that he already had in his room. Part of me was glad he was ready to play safe, but part of me wondered how many other girls have been up to his dorm room that he needs to have condoms at the ready. I was determined to show him I was better than any other girl he's had. As soon as he had his dick inside of me, it was like passion and thrusting and all animal like, but also sensual at the same time. You'd think it would have been over quick, but Matt would slow it down to keep from cuming too soon and then we'd switch things up. We did missionary. We did doggy style. I even did cowgirl for a little bit. I had multiple orgasms! Matt eventually let himself have one too. And then we laid in bed and kissed and cuddled and talked."

"What did you talk about?"

"All sorts of stuff. Just getting to know each other better, I guess. I did learn that I'm the only girl he's had up to his dorm room. He got the condoms from the condom bowl, just like me."

"You weren't his first time, were you?"

"No. Just his first at college. He's had girlfriends before me."

It was a weird way to phrase it, I thought. As though Amanda was now Matt's girlfriend. But, I knew that wasn't what she meant. Or at least I assumed that wasn't what she meant. Three dates was too soon for anything like that.

"When are you seeing him again?"

"Tomorrow night."

"Cool. So, how much bigger is his dick than mine anyways?"

"Much bigger!" Amanda said. She said it so proudly and confidently.

"How about a number?"

"Way thicker. Lengthwise, I'd say at least 2, no more like 2 1/2, but not a full 3, inches longer."

"Seven and a half inches! That's great!"

"Wait. Why 7 1/2? Are you saying you're 5 inches?"

"Well, yeah."

"I don't think you're 5 inches."

I laughed. "Are you saying you think I'm bigger than 5 inches?"

It was Amanda's turn to laugh. "Um, no. Definitely smaller. Do you have a ruler? We can settle this right now."

This was so humiliating! My girlfriend thought my penis was even smaller than 5 inches! I grabbed a ruler from my desk.

"Take off your clothes!" Amanda commanded.

I took off my clothes and lay down. I was completely hard. Amanda pulled out her phone and quickly looked up the legit way to measure a hard penis from the base and showed me. She put the ruler against me.

"I'm reading 4 inches!" Amanda announced smugly. "Maybe a little more, but definitely below 4 1/4. So I'm just going to call it 4! Do you disagree?'

A little movement of the ruler and I could have had 5. But, that would have been cheating. Maybe I had cheated when I'd previously measured myself to convince myself that my penis wasn't actually as small as it really was. But, here was proof of the reality of the situation right in front of me. I had a tiny 4 inch penis. It was an indisputable fact. My humiliation increased, but I was even more turned on because of it.

"Wow. I really do have a tiny dick, don't I?"

"You sure do! I'd still fuck you though!"

And she did. And the sex was great! The best I'd ever had.

Amanda had her fourth date with Matt last night, but they couldn't get some privacy this time. So no sex. They're having another date tonight though. And Matt has already arranged with his roommate to have the room to himself!

[Anders86]

Wow as usual a great update and hopefully Amanda will get another great pounding by Matt today. Looking forward for your next update.
Btw would be hot if you were able to post a pic of Amanda.

[hwc]

Wow! Fantastic update! cannot wait to hear how things progress, and do not worry about long posts - the longer the better, honestly! You are so good at presenting the details, in an unfolding story that flows naturally, that it's a pleasure to read.

[Wannabee]

Loving this adventure. So hoping Amanda really opens up to multiple guys.

[wingman]

Wow is that 5 dates in NN a week and a half?

[Bent_n_Twisted]

A publicly available free condom bowl? On a college campus?

I went to college, a long time ago. Some of those folks, were of a mind that might find it amusing to stick pins through randomly selected condoms that were left out like that. Are kids more mature and responsible these days?

Stupid question, I know.

[bufaker]

wow

[ChrisCuck]

A publicly available free condom bowl? On a college campus?

I went to college, a long time ago. Some of those folks, were of a mind that might find it amusing to stick pins through randomly selected condoms that were left out like that. Are kids more mature and responsible these days?

Stupid question, I know.

It's really messed up that anyone would think to do something like that. I don't know if us young people are more mature these days or if you just had bad luck and ended up going to college with a bunch of assholes. Or maybe there's assholes like that at my college and I don't know about it? But, I feel like the condom bowl is safe either way. There's no one specifically standing guard over it, but it's in a safe enough location.

[ChrisCuck]

So, it looks like Amanda is hooked on Matt and has no time for me at the moment.

Well, that's not completely true. We've hung out on campus. I've even hung out with her and Matt together. Seeing my girlfriend hold hands with Matt and be affectionate right in front of me is a crazy rush! I'm jealous of Matt, but I love seeing them together like that at the same time!

I watched and heard Amanda tell Matt, right in front of me, "I'd realized for a while that Chris and I were transitioning into being just friends. It was just a matter of us making it official. We haven't even been broken up that long, but it feels like him and I being a couple is such ancient history. And it's a totally mutual thing. I know Chris agrees one hundred percent!"

And then, out of my own mouth, "One thousand percent! Amanda and I are like brother and sister. I love her like my own flesh and blood. It's like a weight being lifted that we can just come clean and say we're best friends, close like family, and leave it at that. No more trying to force our friendship to be something more."

Amanda had messaged me afterward to let me know that I made a good impression on Matt.

"You did great! Matt is 100% sold on you and I being just friends!"

Unfortunately, Amanda hasn't been able to come to my apartment since the last time she was over. We've agreed not to even bother trying to get some alone time for now.

Amanda had messaged me. "There's too much I need to get done for school before Thanksgiving break. And I'm trying to make lots of time for Matt too, because he and I won't see each other again until the beginning of February once Thanksgiving break comes around. No more in person classes for the rest of the semester. Matt and I will both be back home, far away from each other. But, it'll be easy for you and I to see each other during that time. You'll have me to yourself for over two months!"

"It's cool," I messaged back. "I've got school stuff too. And work. It was hard enough finding good windows of time when you could come over here without worrying that Steve could walk in on us. All this extra school work just makes it harder. I also don't want you to have to trade any time with Matt just so you can come over to see me. You're right. The two of you aren't going to see each other for over two months once Thanksgiving break comes. So I can wait."

"Thank you! I'll make it worth your while!"

"I know you will. In the meantime, enjoy Matt's big dick!"

"I will! Lol!"

"Try not to miss my 4 incher too much. Lol!"

"Ha ha! I'll try to make due with Matt's 6 1/2. Have I mentioned it's much thicker than yours too?"

"Yes, you have. But, I don't mind being reminded."

"Okay. Good! Because it really is way thicker! It fits really well inside me. It's a really good kind of snug. Your little dickey just doesn't compare!"

"So, is it fair to say that you like having sex with Matt more than you like having sex with me?"

There was a long pause.

"The truth?"

"Of course."

"The answer is yes."

"I'm cool with that. I know we'd worried about what if something like that happened. But, now that it has, I don't mind. Neither one of us had hoped that sex with another guy would be less enjoyable for you. So, why would it be a problem for it to be more enjoyable? It's not a problem."

"I think we were worried because what if I decided I wanted to only be with the other guy instead of being with you. But, without any pressure to make a choice, it doesn't matter how much I enjoy being with Matt. I can enjoy being with Matt and enjoy having you as my secret boyfriend. Matt and I aren't an official couple. Plus he and I will be separated for over two months soon. So I'm free to enjoy him as much as I want with no consequences to my relationship with you. So you're right. It's not a problem that I like having sex with Matt more than I like having sex with you. I still like having sex with you. I'm still in love with you. I'll miss Matt's big dick when he's away, but I'm looking forward to it just being you and me for a while."

"I love you so much!"

"I love you too! Thank you for being so amazing and for encouraging me to do this! You're great!"

[hwc]

A really good update! Thanks. Their budding relationship really looks like it is taking off, what a shame it's going to be shutdown for a couple of months, just when it's getting hotter!

[AlmostDoneIt]

Exciting story so far! Here's a question though: have you guys considered Amanda hooking up with Steve? It would be exciting, and especially convenient for you as you may get to hear Steve & his girlfriend (Amanda) have sex as their roommate. What's Steve like, is he a hot guy?

[Bent_n_Twisted]

It's really messed up that anyone would think to do something like that. I don't know if us young people are more mature these days or if you just had bad luck and ended up going to college with a bunch of assholes. Or maybe there's assholes like that at my college and I don't know about it? But, I feel like the condom bowl is safe either way. There's no one specifically standing guard over it, but it's in a safe enough location.

LOL, immature assholes are everywhere, some of them aren't even in college anymore.