So, the other day, my buddy straight up told me that she has a nice ass. I was a bit taken aback since he never had a girlfriend before and me and his older brother have been trying to motivate him to talk to girls, up his game, etc. We helped him text, go on dates, and it mostly worked out, but it never moved on to an actual relationship. Just bad luck I guess. By accident, he sent us a dick pic in our group chat with me and his brother. It stood there for solid 5 minutes before anyone noticed. Later he realized that he shared it together with multiple photos and deleted it.
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But boy was I shocked when I saw the picture. It showed his penis, next to a book
from his granddads library. Judging by the size of the book, which I have in
fact read and borrowed from them, he must've been around 23-24 (9+ inches) cm
long. And it had a decent amount of girth to it too. And when I saw him years ago he was like a peanut.
So as it was an odd thing for my day, I told this tale to my girlfriend after a
long day of studying. After telling her his supposed size, she told me:
"Oh baby, at least you're not SMALL small.", and joked about his
large size. Her size preference is large girth, and over average length. I figured
that out by the shapes of her dildos. She knows about my cuckold fantasy, just
hasn't been able to act on it due to her own anxiety, body dysmorphia etc.
For context, I am around average at 16 cm (6.3 inches). She likes my size, but she
would prefer having sex more often and if I could last longer. For even more
context, his older brother is 18 cm (7 inches) long. That's what shocked me,
that big difference of more than two inches between the two brothers.
To further illustrate the situation, let me tell you a bit more about our friendship dynamic. Me and the two brothers have been best buddies since elementary school. We grew up in the same neighborhood and went through all of school together. The younger one has always been a bit shy around girls, while his older brother was more outgoing and had no trouble getting dates or girlfriends. I remember when we were teenagers, the younger brother would often ask me for advice on how to talk to girls he liked. We spent hours talking about it. He really wanted to impress the ladies but struggled with confidence. I tried my best to help him, telling him to just be himself and not worry too much about what others think.
Even though his older brother was more successful with women, he never rubbed it in the younger one's face or made fun of him for still being a virgin. He understood that everyone develops at their own pace. The brothers have always been very close and supportive of each other, despite the age gap.
So when I found out about my girlfriend's interest in the younger brother, it was a bit surprising because she usually prefers more mature guys. But I guess his impressive size got her attention. And knowing how much he admired women and wanted to gain experience with them, I could understand why he would be attracted to her too.
A few days later, yesterday, I found out that they started following each other
on instagram and that they are sending each other memes. He is talking very
often about my girlfriend, even in our groupchat. The talk is innocent, but is very often about her (for example "Is she going to be there", "She really dressed nice" etc.. When I talked to him in
person, he commented some potential girls that he could date, but told me that they
definitely don't come close to my girlfriend's thick bottoms. I thanked him, but he continued to talk about how good she looks.
The real dilemma for me is deciding whether to let nature take its course or intervene somehow. On one hand, it could be a great learning experience for the younger brother to have his first sexual encounter with an experienced woman like my girlfriend. And I know she's been curious about trying something new and exciting in bed.
But on the other hand, if word got out that I was "pimping out" my girlfriend to the younger brother, it could cause issues with all of us. The older brother might feel betrayed since we've always had each others backs. And who knows how the younger one would handle the pressure of being thrust into this situation.
I also have to consider my girlfriend's feelings. She's expressed interest but I don't want her to feel obligated or pressured into anything she's not 100% comfortable with. Her anxiety and body image issues are important to me. The last thing I want is for this to trigger a relapse of her dysmorphia or self-esteem issues.
So I've been wrestling with these thoughts, trying to weigh the pros and cons from all angles. I trust my girlfriend and our communication. I value my friendship with the brothers. And I want what's best for everyone involved. But it's a complicated situation with a lot of moving parts and potential consequences.
So, is it a good idea to let the situation unwindle? He could get his first
experience and I could finally live out my fantasy. Also he is still in puberty
and I heard that his libido is extremely high as he has urges to orgasm
multiple times daily. That could be a good experience for my girlfriend.
Or should I separate them, make a stop for this situation? I don't know how his
older brother would react if I asked him beforehand. We are very good friends.
I wrote the events a bit longer and detailed, considering some might like it. I
think it also explains the situation a lot better. This is a repost after being deleted for no paragraphs and being too short.
TLDR:
Hung younger guy and my girlfriend are interested in each other. It would be
his first experience and my fantasy come true. He is still in puberty with an
extremely high libido, and I think it might be a superb experience. His older brother might react negatively if I ask him
beforehand, but we are good friends.