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It All Started With A Craigslist Hook-Up

Ringfinger

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This late at night, I don't feel like going into too much detail, but here is my situation.

I am 18 years-old, and am exclusively attracted to older and heavier men. My ideal age and weight range is 40-45 and 220-250lbs. Not incredibly old, not incredibly big; but definitely out of the ordinary. The youngest guy I have been with was 35 and the oldest, 55. May have been with older if they weren't being completely honest, which I could see in a few cases. Call me shallow, but I can not be with someone who doesn't at least somewhat fits these categories. Guys skinny, average or muscular, and guys 18-40, generally, really do not do it for me at all. The guy who was 35 looked in his 40's. I don't know what it is, and I wish it were different considering how many people would like to see me with someone my own age, including my mother who I made aware of my attraction, and how many difficulties can arise with such a large age difference. But it's not, and there has to be some sort of physical attraction for me to want to pursue a person.

Now, because of this type of attraction, and because I have for most of my life accepted my sexuality, I have not done anything sexually or romantically with anyone, not even a kiss, until I was 17. Because I have been fine with my sexuality, I felt no need to pursue a girl to try and 'change' myself or cover up who I was. And because of my type of attraction, I have not fooled around with anyone before I was 18 as the guys in their 40 and 50's who would fool around with someone under 18 seemed creepy to me. One exception is the guy I lost my virginity to who was 35, who I slept with months before my 18th birthday. Although it seemed odd he didn't want to wait a few months until I was 18, I was blinded by the lust I had built up for the past 17 years. I was nervous as hell, but that wasn't enough to stop me. So we rented a room in a cheap motel.

That held me over until my 18th birthday, June 1st of this year, and at that moment, I went all out. Of my 15 hook-ups, I'd say about 12 of them were in the months of June and July. I know, I was a slut. But with so many other kids my age having their first experiences of any sort at 13-15 years-old and even more so past that point, and with me watching from the sidelines while I knew I had to wait years before I got to experience any of this, I could not get enough the moment I turned 18. Ages 15-18 were incredibly hard for me to resist anything sexually, as if I even had a choice. But I knew it'd be worth it once I finally did turn 18, and that it was.

In August, I made the decision to move out of my mother's house into my college dorms. I had the idea that with the freedom I was soon obtaining, the next few months would be filled with even more hot monkey sex, as Lex would put it. However, once this freedom was obtained, I felt that I had absolutely no rush at all to start putting myself out there, and maybe look for something a bit more relationship-oriented. At my mom's house, I had to plan the hook-ups very carefully as she didn't know at that time I was 'sexually active,' and she probably wouldn't like the idea of me going out and having sex with guys 20-30 years older than me, most being older than herself and a few being older than my father. In that environment, whenever an opportunity spawned that I could take advantage of, I felt I had to do so immediately. I suppose these opportunities spawned quite often.. however in my dorms, I felt I had no rush to hook-up with anyone as I could at any given time (especially considering how quick many older, out-of-shape guys would go after a guy my age and build). Thus, the frequency of hook-ups slowed.

Sort of.. about a week after moving into my dorms, I put a picture-less ad (as I always do, a bit discrete here), up on craigslist and, as usual, got about 40-50 responses (Hey, my age range!). Not trying to brag here, especially considering I posted an ad on fucking craigslist, but you can imagine how many responses "Younger Looking for Older" would get. Not a single one sparked my interest, and most of them had face pictures, which is necessary for me. You see, even with such a defined attraction, I am quite specific with the people who fit said defined attraction in who I actually find attractive. Kudos if you got that. Anyway, a response maybe four hours after the ad was posted caught my eye. Wasn't enough to have me go to the guy's house as there was only a picture of his chest, but his chest was indeed enticing. His stats were of my interest as well, and his email read as follows:

August 16th, 7:16 PM
Evening...


41 5'10", 230,shaved/bald, gotee, 5"c

Into lots of body contact, kissing, touching, sucking...whatever feels good between two adults. Love having my nips sucked....woof!

I'm drama/disease free and expect the same.



I can host in caphill.



Interested?


I responded:

Great body, got a face pic? I'll find one of myself.


And him:

Hey Andrew...sorry no face pic....super discrete guy here....I'm not a troll :-)...good skin...nice teeth :-)...very big on personal hygiene :-)
How about a pic of you


At this point with any guy, I will tell them that I need a face picture to continue. That is exactly what I told this guy, and somehow, through his next email, he was able to convince me to meet him at a coffee shop and if there was no mutual attraction, he would not be offended and expected me not to be offended either. What made me feel even more comfortable is the fact that it was at a Dazbog I am at almost everyday of the week, so a very familiar location for me. Wish I had the email to show, but somehow it and the follow few got deleted. But a few more emails are exchanged, I get his phone number, shower, get ready, and drive to the coffee shop.

I just now had to sift through the texts between him and I to find out the time we first met. Between then and now, we have had a lot. But it was around 10:00 PM. I waited for about 15 minutes before he showed up, and at first didn't see him when he told me he was there. As the coffee shop was closed at the time, I was on one side outside of the shop and he was on the other. I walk around to where he is standing, assume the 40 year-old, chubby, bald guy standing by himself is the guy, and we make our first mildy awkward, craigslist-esque greetings. We talk for about ten minutes, find we are fairly comfortable around each other, at least comfortable enough for two people who just met, and he asks me if I'd like to go back to his place. The thought of this night alone almost four months ago gives me the chills.

Now, I found him to be surprisingly attractive, and I really wasn't planning on going to this guy's house as I had a great deal of doubt in how hot he'd be. As I previously mentioned, I am a bit picky in my tastes; even with guys who fit my type. This guy wasn't absolutely stunning, but he was definitely in the top five (although I really hate to rate guys like that, forgive me). I told him I'd love to, and we walk to his house, which is actually less than a block away from this coffee shop I had come to so often, but I had never once seen him in my life. We enter his house, which isn't the largest but is very nice in terms of hygiene and decoration, and what happened from then on is honestly a blur. I've been to his house so many times at this point that I really can't distinguish certain nights.

Except for one. Fast forward almost three months later to a point where a well-established friends with benefits scenario is in order. It is now starting to get to the point where I am at his house every other night and going out for dinner occurs frequently. Earlier on, within one of the first few hook-ups, he told me that he was not interested in a relationship at the moment and was making an attempt at focusing on himself at this point in his life. That was quite alright with me as he was someone to simply have fun with. A bit later, he lets me know that regardless of whether or not he wants a relationship, he wouldn't want one from someone as young as myself. He says he wants something that is 50-50, and doesn't feel as if he can achieve that with an 18 year-old, although he very much so enjoys my company regardless of whether or not we even have sex. This makes me feel a bit sick, because at this point I have grown somewhat attached to the guy, and knowing that a relationship could never occur down the line was quite disheartening to me. I tell him that I had to use the bathroom; I just needed to breathe.

A few weeks and numerous hook-ups later, I text him saying this:

November 7th, 11:24 PM
Hey.. I think I'm starting to fall for you.. not sure what that means we should do..


It's one of those texts you send out late at night and mildly regret in the morning. For some reason I feel much more productive at night, and with this comes the desire to get things accomplished including letting people know certain things with the anticipation of a productive reaction. The next morning, he responds and asks if I'd like to talk about it later that day and I agree. I go to his house around 5:00 PM and we have our usual flirty, light-hearted discussions. Then he asks if I needed to discuss anything regarding the text I sent the night before and acknowledges a time I told him that I thought I liked him too much. It's established that at a certain point, I will get hurt. If I break it off now, it will be much less painful than down the road. He tells me that the last thing he wants to see is for me to get hurt, so I need to do whatever I must for me to prevent that, even if that means never coming back to his house. It takes me a while to process everything and finally come up with a decision, but I eventually make one. I tell him that however senseless it may sound, I am willing to risk whatever heartbreak may come in the future to spend even just a little bit more time with him. He tells me that he respects my decision and that it is okay if I continue to come over if I am willing to deal with the consequences that may ensue. I tell him that it's probably a bad idea, but that I am.

At a certain point during this night, something very strange hit me. Something I had yet to experience at his house and something I haven't experienced since. In case you haven't figured it out yet, this is the one night that is crystal clear to me that I was referring to earlier. But this feeling that hit me just stayed for several hours, and all of a sudden, I hated being around the guy. Every time he spoke to me, I'd almost entirely shut out everything he was saying and was emotionless and vague in my responses. He annoyed me, and the fact that he was hurting me made me feel disgusted in him and I really didn't even feel like going near him. We eventually went to his room and he continued to talk about something, and after a while I told him I was going downstairs to get something to drink. Again, I just had to breathe.

I came back upstairs, was in his room with him for about five more minutes, and then he asked what I was thinking; I assume he noticed something was off about me. I didn't respond for about ten seconds, then told him that I had to leave. He immediately understood why and said that that was okay with him. He proceeded to tell me that we could still be friends and maybe get coffee every once in a while. Looking back on that moment is a very depressing memory for me. Well, that moment was very depressing for me, and it all felt incredibly surreal. He gave me a very long hug, walked me downstairs, and told me good luck in what I was trying to find.

I felt numb the entire drive home. Felt like I wanted to cry, but simply couldn't. I got to my dorms, went in my room, and started listening to One Man Guy by Rufus Wainwright, a song that for several reasons reminded me of this guy. I almost immediately started crying. I literally don't remember the last time I cried before this. My grandma who lived with my family and felt like another mother to me passed away when I was 12 of breast cancer. During that experience, I felt shock, numbness similar to this situation, and then just general depression. But I never cried. Since then, I have had several family members pass away, including a grandfather who killed himself, parents who have gotten divorced, a straight guy who I fell madly in love with for over a year, and a father who was fired for several different jobs because of a cocaine addiction, each causing my family to move halfway across the country. In none of the situations had I even come close to crying. Before this current experience, I, again, literally can't remember the last time. I'm just not a very emotional person. But this was too much for me. I felt stuck and extremely depressed all of a sudden. Even more so because I really needed someone to talk to, but the only person I wanted to talk to about it was him. It felt as if talking to anyone else about it wouldn't achieve anything at all for me emotionally, and I really needed to be in a different state of mind than what I was in. I told him exactly that through text, and he said that he could lend an ear whenever I wanted.

Now what occurs next may very well have been a huge mistake on my part. For all I know, at this point, I might of already been over him. But after he told me that he could lend me an ear, I asked if he could lend one that night. No sex or anything, just someone to be with. Plus, he was going out of town for a week the following day, so that would give me time away from him to think things over. He said that was okay with him.

So I went back.

The walk to my car at my dorms was one of the happiest of my life. I literally went from extreme depression to a state of euphoria within a minute because I knew that, for that night at least, everything was going to be alright. I would be falling asleep that night in his arms, and that is something I thought I'd never have back just moments ago. I honestly wasn't expecting him to have me back even if I asked, but he a big believer in letting people make their own choices and mistakes, so I guess I should have expected it. However, like I said, I wasn't expecting it, and now that I had everything back, I felt incredible. I went to his house, expressed my embarrassment for what had just happened, and we started talking again as if the entire ordeal never even occurred.

Since that night of November 8th, I have repeated the routine and am at his house again every other night. After I returned, things went right back to normal and have been that way since. I have accepted that he may very well find a potential partner in the near or distant future, at which point we would have to break off what we are doing. This would result in me mostly likely getting hurt. However, if I get to spend another half a year with him in the process, it will be well worth it. This is the first guy out of quite a few that I have had big crushes on that I am actually able to be with; at least sexually. I am having a blast being with him and 4/5 nights, we don't even have sex; usually just have dinner, watch a movie or TV, and go to bed. I could see myself simply doing this with him for a very long time.

Now, we are still not in a full-blown relationship, but I do believe it is much more than just a friends with benefits type of situation. First of all, I foresee the two of us remaining very good friends even after this whole thing ends. I can't say that about a single one of my other hook-ups, a few I've known for several years longer than I've known him. Second of all, I would feel guilty if I fooled around with someone else and I believe he would as well. The two of us maybe a month ago or so each ended up hooking up with another person coincidentally on the same night. We talked about it with each other and the situation was quite unnerving for us both. Since then, I haven't hooked up with anybody else nor as he, in which I entirely trust his word. So, this is a relationship where a very strong friendship has been established, an exciting and romantic sex life is still ongoing, and is basically monogamous. The only part that doesn't quite feel like a relationship is the fact that I haven't met any of his friends or family and he hasn't met any of mine. Most of my friends and family know about him, but I doubt I could say that about him with the exception of a few friends I know he's told. This alone makes me wonder if he doesn't want a relationship with me because of the age difference or because of what other people may think about the age difference. In my friend's and family's eyes, I look like a victim and it looks as if he's abusing me; several which of my friends and family members have even told me this. In his friend's and family's eyes, he looks possibly like a bit of a creeper and may lose a bit of respect from them. That's what sucks about this age difference. Not necessarily that two people 20-30 years apart can't connect well. This has already been disproved with my relationship with this guy. But that other people don't take the relationship seriously and assume that either the younger one is being abused or that it is a 'sugar daddy' sort of thing (fucking hate the whole sugar daddy thing by the way, really makes a bad name for people like me). This is especially true if the younger guy is still in his teens. I'm sure if I had a normal attraction, I would judge these sort of relationships as well; it's hard not to.

Now, what I'm asking for isn't necessarily advice, just people who can read and understand my situation. I suppose if I had to propose a few questions, they would be:

1. Should I leave him? And why do you believe so?

2. Do you believe I am being abused?

3. Do you believe that at any point he was lying to me about something?

4. What do you believe his real motives are for not wanting a relationship?

Answers to these questions would be interesting to read, but I am happy with where I am at right now and highly doubt I will leave him anytime soon as it seems quite beneficial to the both of us.

Guess I wrote a bit more than I planned..

EDIT: Don't really feel like proof reading this post at the moment.. it's almost 6 AM and I haven't slept yet. I apologize for any grammatical errors.
 
Well, mind and hearth are really very complicated things. Although you say you are not emotional person, that may be the reason, why you were so emotional about breaking with him. Sometimes feeling just need to be released and what other reason would one need then his first love.

As for the questions:
1. You shouldnt leave him immediately, but you should be prepared that it can happen one day. By preparation I mean finding other close friends you could talk to about these things and maybe one of them may become something more one day.
2. How did you get to that? If you were abused, only by your hearth, not from him, so don't think like that. But maybe you though he abuse you by keeping you near him with no future, which would be the reason of that losing control before.
3. No. And be careful about getting too suspicious. That would kill the relationship.
4. We can't know. My guess would be he's afraid about looking like a victim - you making him your sugar daddy.
But I really hope it would be bad experience with other guys, changing his partner quite often, because you could change his mind in that.

Good luck, Ringfinder
 
I tend to like younger guys so here is my opinion for what it is worth.

1. Should I leave him? And why do you believe so?

I can't tell you, it is really up to you to decide. I would tread very carefully though. Are you staying with him because you feel he will eventually have a change of heart and want a relationship with you? I just went through the same thing with a 22 year old, except I was the one who wanted a relationship, and when it ended it definitely put a strain on our friendship. So if his friendship is truly what you want be careful. You have all ready got mad at him and left him, imagine what will happen a few months down the road.

2. Do you believe I am being abused?

No I do not think you are being abused. It seems like a very mutual relationship.

3. Do you believe that at any point he was lying to me about something?

From what you have wrote, he seems to be very honest and telling you up front that he is not looking for a relationship.

4. What do you believe his real motives are for not wanting a relationship?

He has told you his motives do you not believe him? And now my perspective. Younger/older relationships will almost always be frowned upon, even within the gay community. How ever that is society's problem and not yours. I know one of the things going through my mind with my friend is what are people going to think that I am dating someone half my age? I truly believe they can work and I even know a few couples in this situation some who have gone on to get married. But maybe that is something that he is thinking about.


I think you have a lot of thinking to do, what do you really want out of this relationship? I know in my case with my friend he was telling me the whole time that he just wanted to be friends, but I refused to hear that, and read things into his actions and saw signals that really were not there. :wave:
 
This is the best post I have read on this website. I wanted to read it all and see what happened.

As for your questions:

1. Should I leave him? And why do you believe so?

One of Dan Savage's great lines about older/younger relationships is the campsite rule: "leave him in better shape than you found him". As long as this man is treating you well and honestly, it should be a good experience for you.

You don't need to leave him unless things change in a negative way or, after time passes, things don't change at all. There may come a day when the status quo is no longer satisfying for you. You seem like you have a pretty good point of view about the whole thing and you will probably know when it is time to move on. Until then, enjoy yourself and him.


2. Do you believe I am being abused?

I didn't see a single red flag in the entire post. Sounds like a great deal for you so far.


3. Do you believe that at any point he was lying to me about something?

I don't think so. Do you think he was lying about something?

4. What do you believe his real motives are for not wanting a relationship?

First of all, no matter what either of you say, you are in a relationship with each other right now. 4/5 nights a week at his house, dinners, movies, and most importantly, not seeing other people. That IS a relationship. And a fairly committed one at that. Just because it isn't a "declared" relationship to friends doesn't make it "just a hook-up". So I would venture a guess that he doesn't want to be seen having a relationship with someone young enough to be his youngest son. Because those kind of relationships aren't supposed to work out. And yet, they do sometimes.

So enjoy what you have while you have it. Realize that it may end someday. Maybe when he meets someone closer to his age. Maybe when you meet someone closer to your age (preferences change over time).

Or maybe you two are one of the exceptions. Don't over think it too much and be happy.


BTW, I'm just an amateur at psychology, but if you are wondering why you have an attraction to much older men, take a look at the relationships you had with your father and grandfather.

Good luck with it all.


Michael
 
So, to summarize....
  • You have been experimenting sexually- mostly with guys that are much older than you which is your preference.
  • You are met a guy for a casual hookup.
  • You ended up making a fuckbuddy out of the guy.
  • The guy treats you well but doesn't see a future in the relationship and he's been honest with you about this.
  • You're getting emotionally involved and you've told him this.


1. Should I leave him? And why do you believe so?
If you're happy, why would you?

2. Do you believe I am being abused?
You're both consenting adults. You chose to go there 4-5 nights a week. If anyone is being used/abused then both of you are doing it to each other. But that's a choice you both are making.

3. Do you believe that at any point he was lying to me about something?
We wouldn't have any way of knowing. People in relationships don't disclose everything about themselves, so it's safe to assume that is the case here.

4. What do you believe his real motives are for not wanting a relationship?
Since you included the word "real", you're implying that you don't know or you don't believe what he has told you.
Why don't you put that question to him?
 
Now, what I'm asking for isn't necessarily advice, just people who can read and understand my situation. I suppose if I had to propose a few questions, they would be:

1. Should I leave him? And why do you believe so?

2. Do you believe I am being abused?

3. Do you believe that at any point he was lying to me about something?

4. What do you believe his real motives are for not wanting a relationship?

Answers to these questions would be interesting to read, but I am happy with where I am at right now and highly doubt I will leave him anytime soon as it seems quite beneficial to the both of us.

Guess I wrote a bit more than I planned..

EDIT: Don't really feel like proof reading this post at the moment.. it's almost 6 AM and I haven't slept yet. I apologize for any grammatical errors.

You are a very intelligent guy, and despite the length of your post, I enjoyed reading what you had to share. Thank you for being a refreshing voice asking for advice here (and paying attention to the rules of grammar).

As for your questions, here are my responses:
1. There is no reason for you to leave him. You are happy and content with the way things are, and you are accepting of the outcome in the future. From what I've read, he sounds like a trusting individual.
2. You are not being abused.
3. I believe so far he has been honest with you.
4. Here is my complex answer:
I am curious to know what kind of past he has had being gay. Many of us grow up and experience burns and heartbreaks in relationships. Some of these age difference relationships can be challenging because the older man's intentions were not right or the younger one was too young to be ready to settle down with someone for the rest of their life. I believe his hesitation has two parts. First, his past experience concludes you will eventually want to move on from the relationship. He's too old to risk investing more years into a young guy only to have his heart broken again. Second, his family and friends would not accept you as your family and friends do not accept him. A life-long relationship would face many challenges where both families and groups of friends will constantly belittle your relationship and never accept your love. He recognizes that, which is why he sees himself growing old with a man his age. His love for another man would be accepted that way.

You are very intelligent, open-minded, and full of promise; however, the world is not the same. Society is full of ignorant and cruel people. He's lived his whole life around those attitudes. In his time, gays were even less accepted. You can live your life the way you want to, but sometimes the relationship you want is not possible with the person you're with or the society you live in.

I'm not saying your friends, family, or society is right. They're wrong. I think what the two of you have is special. However, you can't change them, AND you have to live with them. Your family will alway resent him. Your friends will always find the motives to the relationship suspicious. His will too. You can't change it, but neither can you get rid of your friends or family. They are part of your life, so you must accept the limitations of your relationship with this man. Enjoy it for how ever long it lasts.(*8*)
 
since he is asking for advice ill throw in my 2 cents and not just tell you something you want to hear

1. Should I leave him? And why do you believe so?
maybe. how long have you known him?
and how well do you know him?
does he seem genuine? your man sounds like a sketch

2. Do you believe I am being abused?
emotionally yes. but if you want to make yourself believe you are ok than be it. could be denial

3. Do you believe that at any point he was lying to me about something?
not to sure. but there is no way he is 100% truthful with you
4. What do you believe his real motives are for not wanting a relationship?
if he wanted you as a partner it would have been established a long time ago. i just believe its a one sided relationship
 
1. Should I leave him? And why do you believe so?

Ask yourself this do the costs of staying outweigh the benefits?
If the answer is yes; stay. Otherwise; leave.

2. Do you believe I am being abused?

Not at all.
In situations like yours it's usually the young man who searches out the older guy, and everything you've posted suggests that this is the case.

3. Do you believe that at any point he was lying to me about something?

Everyone lies. (But there's nothing you told that suggests he might be lying about something big).

4. What do you believe his real motives are for not wanting a relationship?

Some older gay men (such as myself) often don't have the patience to endure the many emotional/ attitudinal changes young men go through between the ages 18 - 30.

For instance, your apetites can be expected change dramatically over the next ten years.
There's a fair chance you'll leave this person behind soon, and he might already see it coming and doesn't want the drama should you leave.

It's also just possible he doesn't want to be tied down at this point. Why don't you just ask him?
 
Since we've listened to the story only from your side, keep in mind that we're only replying according to that. If there are things you forgot to say etc, we may be totally wrong. Anyway here's what I think.

1- That depends on how you'll react in the future. If a year later he decides to finish it and be with someone of his age, will you say "at least he made me happy for a year" or will you say "I should've left him and found a boyfriend who wants a long term relationship with me".

2- Unless he's making you do stuff that you don't want to, I don't think so.

3- From what you've wrote, he seems like an honest person but we can never be 100% sure just by reading about him over the internet.

4- Two reasons come to my mind. First one is he may be scared of the society and the second reason is that the age difference is too much. For example there may be times when he wants to feel like his partner is dominating or his partner is protecting him etc but it may be harder to feel that way with someone who is much younger. Also he may think that only people around his age can understand some of his issues. These are only my guesses though. I may be completely off.
 
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