Found Bigger Condoms in Girlfriend's Room, Help

[HenryB12]

Update:

Hey everyone, I thought life would get less busy, but I was wrong. Mia and I have been doing really good. We haven't been using condoms as much while having sex which feels great. We alternated from using them and not, as I was still apprehensive and was nervous about getting her pregnant. The fear has gone down and so going raw has been super enjoyable. We've also been talking more about Justin. I have gotten her to be more comfortable comparing us. One thing I got the balls to ask that was super hot was while she was stroking my dick was for her to show me how big Justin was compared to me. She wrapped her hand around my dick while adjusted the size to what Justin's would've been. I didn't last much longer after that lol. All in all, our relationship has been good and was strengthened during her sharing past details.

I think I'm ready to move to the next step and bring up cuckolding. However, as I've brought up in other posts, I'm really nervous to bring up cuckolding. If you guys could tell me what went well when you brought it up to your women, that would be great. I've been overthinking this conversation for months so having some go to lines that you guys think would work would be awesome. Also, should I bring it up from a threesome angle or just go to cuckolding? That's one thing I've been thinking a lot about. Also, I need some cuckolding resources to show her to ease her into this. Obviously I can't show Mia this website as she would recognize these posts as being about us as well as some of the posts on here are a bit out there. Just come websites, articles, or anything that would be good to show someone new. I don't want Mia to be overwhelmed with information or scared off by the extreme parts of the kink. Thanks for being patient with my situation and for the advice so far.

[Dream Weaver]

My 2 cents. I was successful, it just took a very long time, and then she stopped it again, never to return.

I'm not saying this is definitively the best advice.

1. I'm hesitant to advise you to be so "open" with the word and concept "cuckolding". In the "real world" this type of bold honesty seems to fit best with a couple that ALREADY is into swinging.

Because you two are so young and inexperienced (wrt open relationships) I think there is a 90% chance it will freak her out and make it tougher.I don't think you can "introduce" her to it via websites or articles on the subject. The concept is radioactive.

2. We had the "cheating" conversation before we got married. I think most couples with any sense have this talk. It's the one where you tell the other person what you would do if they cheated on you. This is where I gave her the "hallpass", told her I wouldn't hold it against her, but I want to know. (Note - this is not a guarantee that she will actually tell you . It's more useful to set the tone.)

3. The "threesome" conversation seems like a nice step if you think she'll go for it, but I kind of think she has to have already showed some interest.

4. Be supportive if she shows interest in other men. Like if she gets a crush on somebody at work or something. Many girls won't admit this sort of thing, but some will. My wife was this type of person, honest about it. Let her know it turns you on!

5. I did the following. I told her something like "I have to be honest, based on on some of our pillow talk we've had, I've thought about it, and if you ever find yourself in a situation where you are attracted to somebody and want to sew your wild oats or try somebody out, I'll support you 100% but you have to, must must must, tell me, because that's the only way I'll enjoy it."

6. Once you have definitively brought it up, there's no need to keep bringing it up if she gives you a hard no. That's not to say she won't do it, but the #1 complaint you'll see from women is "he won't shut up about it". It turns them off. It's your fantasy, not her fantasy, and you can't make it her fantasy if it's not already. Maybe she's ready to slut out and you'll get lucky. But if not, be cool, not a pain in the ass, and be satisfied with the long game.

[user322]

Hi,
I think you can approach the subject very simply.
During moments of excitement, you suggest the idea to her. Or you can talk to her about it during a discussion dedicated to this topic.

Just be sincere and don't pressure her.

Just tell her sincerely that you fantasize about what turns you on, and then listen to her to see if she likes it or not.
If she doesn't like it, you have to respect her choice.
If she likes it, you can arrange sex with another man.

If you want to have a threesome, you can suggest it to her; if you want to be a cuckold, suggest it directly. You'll adapt if she asks you for a threesome.

In any case, DON'T PRESSURE HER.

It has to be fun, and pressure kills fun. And then be honest and communicate, especially if there are any doubts; it's essential for a healthy relationship.
Good luck!

[mattyg_2671]

If you want to open the discussion with her in a non-threatening way, you could try the “I had a weird dream last night and I don’t know why but it really turned me on “ approach. Or find an online story that fits what you want and tell her you find it hot and ask her to read it and let you know what she thinks.

User above is 100% correct, pressure is a killer! I made this mistake in the early days many times, it’s so tempting to push too hard.

[wittol]

My suggestion:

[You]: "I had a dream last night. It was, Justin and you, you two were fucking, and you were loving it."
[Mia]: "Wow. What happened? Anything else?"
[You]: "No, I just woke up with a huge hard on."

If Mia asks more questions or wants to discuss, answer her. If she doesn't ask for more info, just leave it, the seed is planted.

[Wantsomefunto]

I agree with the last post,
Tell her you had a dream she was being fucked and you woke up very hard with lots of precum and had to finish yourself off. Just say you don’t know why bot the thought of Mia having better sex with another guy is really turning you on now

[Cuckcuckgoose1]

I agree with the i had a dream scenario and I'm not talking about MLK...

[hwlurker88]

I think most are in agreement that the dream idea is the best baby step. Then maybe 2 weeks later you have a similar dream but maybe it has a few more details in it.
When she was giving you the hand job compariing Justin's size to yours, what was her reaction to the conversation/comparison? Did she comment/react to you having a quick orgasm from it? Did you share why it made you orgasm so quickly? I think it was a good opportunity to maybe have said something like "it was so hot to see your hand adjust to his size and I couldn't help but imagine you stroking and sucking and fucking his huge cock. When I imagined watching you doing those things with a cock bigger than mine, I just got so turned on I couldn't help but orgasm!"

[avid fan]

Dream or wet dream definitely the way to go....you could even play it as embarrassed..."I know this is odd, but in my dream you were being fucked by this big cock, I was watching and you were telling me how much you were enjoying it, teasing me about how good he made you feel... and seeing you so turned on turned me on...."

[Funpa99469]

I think all of the ideas are really good suggestions. The dream or fantasy one is the easiest to bring up and during sex makes it even easier, but make sure you follow it up with a conversation about it outside of the bedroom to let her know your sincere interest. Open communication is the best and it sounds like you two have really developed a great level of communication already.

[HenryB12]

Update:

This morning, I woke up before Mia did and wanted to use the dream idea (thanks for the suggestion everyone). I got myself basically 100% hard by stroking my dick and thinking of her and Justin. Then, I rolled over and started grabbing her boobs while rubbing up against her. She woke up after like 5 seconds of me doing that. She started tapping me to wake me up as I was pretending to be asleep. Kinda childish but I thought this was the best way to introduce the dream. I “woke up” and acted like I didn’t know what was happening. Mia asked what I was doing. I said “ I don’t know, you just woke me up.” “You were humping me, what were you dreaming about? You’ve never done that before,” she laughed. Before I could answer, she said “it better not have been about another girl.” I told her it wasn’t and she just stared at me, waiting for me to tell her what my dream was. I told her that I didn’t remember all of it. I was at my highschool, walking through the school parking lot and I found her car. As I walked up to the car, I noticed it rocking back and forth. I see her riding Justin in the back seats. Then somehow we are back at my house and I am fucking her in doggy while she is sucking Justin. “Then you woke me up,” I told Mia. “I don’t know why that turned me on so much," I stated. She laughed and said the dream doesn’t make sense as Justin didn’t go to my high school. I said it was a dream and sometimes my dreams are all over the place. Mia asked if I remembered anything else and I said not really. "Well, it really made you horny. You were sleep-humping me", Mia exclaimed. She asked some other random questions, trying to get an understanding of this new dream world as well as poking holes in my dream and how it doesn’t make sense. Then, she grabs my dick and strokes it twice before getting up and informing me she is gonna take a shower, leaving me with a boner. No sex this morning but we had some normal sex last night.

I don’t know how it went. I thought it was good, but I was mostly focusing on answering her questions and improvising the “dream”. She seemed very intrigued and thought a lot about her questions. I didn’t put any pressure on her and don’t think I have over these past months.

[3532734dreamer]

Heya Henry!

I think you did good!

The seed has been planted. Mia didn't seem completely turned off by the idea of you dreaming of her having sex with Justin. And she was turned on by your arousal/reaction to the dream.

You still have to go slowly. She might come with more questions. But eventually you'll want to get around to "dreaming" about her having sex with Justin in the present/near-future... Not in the past, but while being in a relationship with you, and have sex with Justin. And it turning you on thinking about her. Or something like that..

Well done! And continued good luck!

[hwlurker88]

Good start. And dreams almost hardly make any sense so don't worry about it not sounding "plausible" to her. I think the next dream should probably take about 10-14 days before it happens again. But in the meantime, when the opportunity is right, you can take fun jabs at her about riding Justin's big cock in the car. For example, if she talks about going to get groceries, you could say something like "sure you are, you just want to end up in the grocery parking lot riding Justin's big cock in the back seat like in my dream". Then she might be roll her eyes at you. That's when you follow up with, "if you do, please record it for me ".

[Wantsomefunto]

Now that you told her you had the dream, tell her that you just can’t get what happened in the dream out of your mind. And tell her you get hard when you think about it. Tell her you think she maybe should try to reach out to Justin to see what he has been up to?

[Funpa99469]

That’s a great start! What’s the summer situation going to look like for you and Mia? Maybe knows the time to drop the hint about where Justin will be??

[scarfolamew]

You've made amazing progress Henry. Justin, her sexual history with him, and your aroused reaction to it, is a topic that you can just casually bring up!

Your diligence and discipline in not forcing things and letting it all develop naturally is an inspiration. Maybe it will lead to something more intense and actionable, maybe not, either way you two are creating an openness with each other that is the envy of many couples whether they're interested in these kinks or not!

[HenryB12]

I think most are in agreement that the dream idea is the best baby step. Then maybe 2 weeks later you have a similar dream but maybe it has a few more details in it.
When she was giving you the hand job compariing Justin's size to yours, what was her reaction to the conversation/comparison? Did she comment/react to you having a quick orgasm from it? Did you share why it made you orgasm so quickly? I think it was a good opportunity to maybe have said something like "it was so hot to see your hand adjust to his size and I couldn't help but imagine you stroking and sucking and fucking his huge cock. When I imagined watching you doing those things with a cock bigger than mine, I just got so turned on I couldn't help but orgasm!"

She was fine with it. I think us talking about her sexual past these past months has made her more comfortable doing different things. She was pretty focused while estimating the measurement. She was massaging my balls while showing me the length and thickness she remembered about Justin. No comment about cumming quick or anything. I did cum a lot, so Mia commented on that. I didn't share why it made me cum so quickly, but it's pretty obvious that it turns me on lol. I don't know if I have the balls to say that line yet.

Heya Henry!

I think you did good!

The seed has been planted. Mia didn't seem completely turned off by the idea of you dreaming of her having sex with Justin. And she was turned on by your arousal/reaction to the dream.

You still have to go slowly. She might come with more questions. But eventually you'll want to get around to "dreaming" about her having sex with Justin in the present/near-future... Not in the past, but while being in a relationship with you, and have sex with Justin. And it turning you on thinking about her. Or something like that..

Well done! And continued good luck!

I think she was a little turned on by my reaction to my "dream" but more so found it amusing that I was sleep-humping her. But yes, not against and no negative comments about the dream. She was curious about what happened in it.

I will.

Thanks for the good luck.

Good start. And dreams almost hardly make any sense so don't worry about it not sounding "plausible" to her. I think the next dream should probably take about 10-14 days before it happens again. But in the meantime, when the opportunity is right, you can take fun jabs at her about riding Justin's big cock in the car. For example, if she talks about going to get groceries, you could say something like "sure you are, you just want to end up in the grocery parking lot riding Justin's big cock in the back seat like in my dream". Then she might be roll her eyes at you. That's when you follow up with, "if you do, please record it for me ".

Yeah, I was actually proud of my performance/improv. It's easier when it doesn't have to make perfect sense though. I'm down to make those teasing jabs at each other as we do that already, just not with cuckolding stuff. Mia still doesn't know that I'd like for her to sleep with someone else. I've been taking it slow as you guys know.

[hwlurker88]

Well Henry, I'm a huge fan of your progress and path you want to take. You are doing great! And just to be clear, I hope my posts never come across as me sounding like my ideas are the things you should be doing. My posts are only meant to provide ideas about how to potentially seize certain moments. We are on similar paths and I'm just providing ideas that are working for me, but understanding that they may not work for you. Can't wait for your next update!!

[Wantsomefunto]

Hope to hear an update Henry!

[HenryB12]

That’s a great start! What’s the summer situation going to look like for you and Mia? Maybe knows the time to drop the hint about where Justin will be??

I've got an internship I'm doing this summer. Living at my parents over the summer. Mia has a job and is taking a class while living at her place she's at right now during the summer.

You've made amazing progress Henry. Justin, her sexual history with him, and your aroused reaction to it, is a topic that you can just casually bring up!

Your diligence and discipline in not forcing things and letting it all develop naturally is an inspiration. Maybe it will lead to something more intense and actionable, maybe not, either way you two are creating an openness with each other that is the envy of many couples whether they're interested in these kinks or not!

Thanks, I appreciate the support.

It's been difficult at points to be patient but I believe it is paying off. I agree with your last point. Even if this doesn't go anywhere, we still got more open in communicating, especially regarding sex, but in other aspects of our relationship as well.

Well Henry, I'm a huge fan of your progress and path you want to take. You are doing great! And just to be clear, I hope my posts never come across as me sounding like my ideas are the things you should be doing. My posts are only meant to provide ideas about how to potentially seize certain moments. We are on similar paths and I'm just providing ideas that are working for me, but understanding that they may not work for you. Can't wait for your next update!!

Thanks. And I have no problem with your posts. I like reading them to hear out other people's ideas. I get that they are just ideas. I just wanted to clarify where Mia and I were at as far as things that I would say. Again, I have no problem with your responses.

Hope to hear an update Henry!

Here's the update:

Mia and I have been celebrating our 1 year anniversary together. Just had a relaxing 3-day weekend, went out for a nice dinner, exchanged gifts, saw the new Mission Impossible. And had quite a bit of sex. Nothing really related to cuckolding or the dream until this morning. Will get into that in a second. But yeah, 1st anniversary of hopefully many for us.

This morning, while Mia and I were eating breakfast at her place, I brought up that I had a similar dream to the one where I started "sleep-humping". Side note, what a weird phrase I use for it lol. Anyways, she started laughing and said that she was "safe last night and didn't get attacked by me." This quickly caused her to tell me about her actual dream that she had last night. The conversation ended with her saying "We both got really weird dreams," jogging to her bathroom to shower. Not much of an update. I wanted to show her a good time this weekend for our 1year. Didn't want to push and make her uncomfortable during a time we should be celebrating. Sorry if it's not much. I appreciate all the support and ideas.

[Wantsomefunto]

It is all good! Slow progress, maybe coax her to tell you all the details from her dream.

[elina]

It is all good! Slow progress, maybe coax her to tell you all the details from her dream.

[Wantsomefunto]

Hope you had some more good conversations with her today Henry

[HenryB12]

It is all good! Slow progress, maybe coax her to tell you all the details from her dream.

It is all good! Slow progress, maybe coax her to tell you all the details from her dream.

Sorry, I wasn't clear in my update. Mia's dream wasn't about anything sexual. It was just a random, wild dream. So nothing to coax out.

[Wantsomefunto]

Probably time you tell her how much your “dream” excited you and ask if she would ever consider send a message to the hung guy