Thanks for the advice everybody. Anal just doesn't appeal to me right now and I think trying to do it for the first time with a larger guy would probably be counter productive anyway. I might try the speculum thing as although the pelvic exams I've had haven't been fun they have left me curious as to what my cervix looks like especially as I have an ectropion cervix which I may be having treated in the near future so it may serve a double purpose! Fortunately the guy is very understanding and a great kisser but I do generally get further along through g-spot rather than clitoral stimlation so hopefully we can work something out so that being penetrated by him ceases to be uncomfortable.
Hi Ginger. This has Allways in the past been an issue for me. All though I have now been married for 25 yrs it's no longer an issue for us other than anal, this has to be dictated by my wife. She has to be really relaxed and turned on. We do it doggy and I have to stand still whilst she holds her cheeks open and backs on to me.
I digress slightly. I actually got turned down twice in my teens due to size and the two women being inexperienced. From a man's point of few this is actually quite upsetting. Blokes are all macho and brag about size ect, but actually it can be very counter productive. Having been a rugby player the whole dick size thing was alleviated to stupid levels. I found myself sleeping with a lot of older more experienced women.
So first of all whilst you are trying to deal with his size just be a little mindful to his feelings too. Rejection due to size is very weird for a bloke.
However it seems that he is understanding. So why I am giving all this background it's struck a chord with me what you are describing about trying to stretch your self. The things you are describing are exactly what my Wife and I did when we first got together. All the apprehension you are describing are exactly what she had and the answer was the same. She was average in size but had only had two previous lovers. We found that spending a lot of time on foreplay and it did turn into a real turn on for us both but very much so for me gently stretching her. We still do this in a way some times, I think there is nothing more erotic than a woman's pussy. So I would ask him to help you with this he may find it a great turn on, it was a great relationship starter and drew us closer together.
To start with we would as you described do a lot of kissing and cuddling and fingering. We then moved onto me lying between her legs and using first of all the first 2 fingers on both hand to stretch her open gently all the time looking at her and communicating that she was comfortable. When we had done this a few times we were both but especially me were really enjoying it, very horny and such a turn on. We built up to a couple of fingers on both hands and within a couple of months we didn't need to to it really again.
We bought a speculum but my wife didn't like it to clanky and medical and cold. Shame because the view was beautiful. Might be worth a try for you but I would from our experience try a plastic one. There is a lovely new intimate spreader on L H. I will post a link in my next post here. (My tablet will loose all this thread if I try to do it now.) But it Won't help with your concerns.
The other think to consider is you must try and relax your hole body any tension will transmit to your vulva. Try the whole nice evening approach, food, bath and massage. Include in the massage the stretching before intercourse. Also remember having sex doesn't have to mean intercourse over the years I think we are about 50/50 on intercourse / oral and manual. So if your just to tight and can't relax leave it , do something else. Something we stall do quite a lot is I will make my wife orgasm before intercourse this can help too.
Finally you go on top and make him lie still so you can control the speed and depth. What man wouldn't love a bit of domination of this form. " I want you, I am going to have you but at my pace and my control. You are such a big boy, now lie still whilst I use you". Good luck and enjoy.