I am not sure if i will ever be ready for gay anal sex , i always make excuses to get out of it but its because i think my arse is just to tight , i can only get one finger in , nothing more , is their anything i can do , to open my arse to a least have the size of a penis come in. Anyone esle have had this problem , please share as i am young and don't want my life ruin.
Heya Island Club Guy; greetings from a fellow South African
I need to warn you that I have the tendency to go all encyclopedia on peeps, so brace yourself
:biggrin1:
I can appreciate where you are coming from because of my entering the realm of m2m sexual intimacy just over a year ago, but most especially because of one of ex's. A lot of your fears and concerns resonate with me because they echo his own.
At the time of his meeting, much as I was still a relative n00b to things, I had topped and bottomed while he had never been with a man before. He told me point blank that he refused to ever bottom whilst being in a relationship with me because of his fear of the pain etc. Since I'm versatile, it didn't bother me so I reassured him that it wasn't an issue. About four months into our relationship, much to my surprise he told me that he wanted to bottom for me; that his desire to give all of himself to me outweighed his fear. I told him to hold that thought because there was no rush; that he needed to make sure that it was something that he wanted to do. (I can tell you from my own experience that sometimes the emotional aspect of things is overlooked. To decide to bottom for someone for the first time is a giant emotional leap and often times includes the need for trust because of the emotional vulnerability that is experienced...so for me, much as he thought that he was ready for it, I needed for him to make sure that he was emotionally prepared for it as well)
About a month later, he confirmed that it was still something that he wanted to do and that he felt that he was ready for it. It coincided with plans for us to go away for 8 days, so I told him that we had more than enough time to give it a try but that there were no demands or expectations from me, so if he wanted to back out at any given point it would be perfectly okay.
On the first night of our "sexploration" he lay on his back and masturbated and I eventually lubed up my index finger and penetrated him. Much as it was the beginning of preparing him for penetration, my main focus was on pleasuring him with my finger. He has an athletic build but a small frame, so your description of your tightness sums him up very well; I had to slowly and gently work my finger into him. Once it was inside of him, he clearly derived much pleasure from it because of his reaction. It was my intention to leave it at one finger, but he relaxed due to the pleasure so I could feel him loosening up on my finger which prompted me to lube another finger and give it a try. To my surprise, it entered him much easier than the first. He continued to derive pleasure and I once again felt him loosen up which led to me inserting a third finger. Bear in mind that at that point, an hour must have passed. I made him aware that three of my fingers were inside of him and he was shocked; he thought that it was still only one finger that was pleasuring him.
I didn't take things further than that because it wasn't only a case of him giving me his body but he was also entrusting me with his trust and fears as well. If he was willing to give me a gift as great as that, then I was unwilling to tarnish his first time with regret and a negative experience.
On the following evening, things started out in pretty much the same way. He was much more relaxed so it was easier to insert my first finger. I once again made him aware of the fact that there were three of my fingers inside of him. I was willing to once again leave it at that, but he asked me to take things further and to make love to him. I was wary but complied. I told him that we'd take things very slowly (bear in mind that much as I am not long, I am thick so I was very concerned about hurting him in any way) and if at any given point he experienced pain or wanted to back out, he needed to tell me immediately. I told him that he needed to talk me through it: Was there pain? Did he want me to pause? He needed to keep me aware of what he was experiencing at all times because much as I was topping him, we needed to work together as a team. I made him aware that in the event of pain, I wouldn't withdraw from him immediately because he'd most probably clamp down on me which would cause him more pain...so I'd stop, wait for him to relax and he could then tell me whether he wanted me to continue or if he'd rather have me stop and withdraw.
Long story short. We made love that evening and on every occasion of our sexual intimacy thereafter. He told me that when I made love to him for the first time, there were times when it hurt a bit but he never experienced any pain.
I'm sharing this information with you so that you can draw whatever information you'd like from that experience whilst it also explains why I'm going to offer you the following advice:
For me, I believe that an experienced versatile person is best; he's topped and bottomed so he doesn't only have experience with topping, but since he's bottomed he's able to do so whilst putting himself in your shoes.
I believe that you stand a better chance of having a good experience of bottoming if you are sexually intimate with someone with whom you share a connection....it doesn't imply marriage, but someone who's able to identify that you're a human being and who cares about your well being. It's going to require time and patience and chances of you being given that from someone who doesn't know your first name are slim.
There's also the element of being relaxed and a lot of it hinges on trust...which adds to the previous point that I've mentioned.
When it comes to selecting the person (if you're looking for something more along the casual side of things) my advice would be, "don't be afraid to be picky". Granted, it may take some time before you are able to experience bottoming, but it will be well worth it. Take the time to get to know the person, to have a good idea of what kind of person he is and what his approach will be. If the guy is in a rush to hookup for a shag it will be an indication of how much time and patience he'll be willing to afford you during the actual experience. During this time, you'll also have the opportunity to build up a rapport with him and it will enable you to be more trusting of you.
Don't be afraid to make him aware of your fears and concerns. Give him enough information to enable him to not only know where you are coming from but for him to be able to put himself in your shoes. Also be very clear about boundaries. A good way of broaching that topic would be for you start by asking him about his boundaries and what it is that he'd be looking for; the fact that you are treating him with respect whilst displaying interest in his own feelings and needs will encourage him to offer you the same kind of treatment.
Lastly, I'll chime in with everybody else: LUBE! LUBE! LUBE! lol
Don't overlook the fact that you don't have to do anything until you feel that you are emotionally ready for it.
All of the very best!
