I put this under relationship because it has to do with the relationship between me and my best friend.
I am a straight female and my best friend is a gay male, He had to have a circumcision done a little over a year ago due to some health complications (I don't exactly know what) We were just messing around one night and I asked if it was all healed up and he talked about how weird it was to have it look completely different than it used to, I asked if I could see his...Stuff, He thought for a minute and said ok and yanked it out, I looked at it and was a bit surprised, He is not a real big guy but his stuff was bigger than I thought it would be, I asked if it was more or less sensitive and he said it started out more sensitive but now he thinks it is less.
We talked for quite a while while he sat there with his pants around his ankles before I asked if I could touch it, He looked a bit apprehensive and then shrugged and said to go ahead, It wasn't hard or anything so I took it in my hand and was kneading and feeling it but then it started to get hard, I looked at him and he just shrugged so I asked why, He explained that he is definitely gay but if you play with it that it will get hard no matter what and sometimes you don't even have to touch it for it to just get hard for no reason, It was kind of half hard and probably twice as big as before so I told him he was really big compared to the ones I had seen and he told me he is almost 8 inches from his pelvis to the tip.
I spent a few minutes checking out his b**** which he explained was the biggest difference since there is less skin now and his b**** don't hang down like they used to before he had the surgery, By that time he was all the way hard and I just flat out asked if he would put it in me, He shrugged and said he didn't really want to but I have to say that I was way h**** by then. I told him it didn't have to be weird and I just wanted to try it, I asked if he had ever wondered what a v***** looked or felt like and he said he had but more the other way, I quickly took off my pants and got him to feel me, I had him slip a finger in and he was quite interested in what he could feel inside me, I think he may have found my G-spot once or twice but then couldn't find it again.
By that time i told him he either had to do it or I had to excuse myself to go shower which I have come to quite enjoy a long shower in recent times, He thought for a minute or two and agreed to try it, I bolted to my brothers room because i know he keeps a stock of "Stuff" in his closet hidden and came back with a condom and some lube, I tried to put the condom on him and it was not working at all, Apparently he is way bigger than my brother, I decided to go "Bareback" since I know for a fact he has not been with anyone and he agreed to it.
It took a LOT of work but we got it in and got started, I couldn't help it and didn't last long before having my first "big o" and had to stop for a break, Once I caught my breath we went again and again I finished ahead of him, I offered him a blowie and he agreed so I was in the middle of that when he started to go soft, I stopped and asked what i could do to help him and he asked if he could touch my butt, I said ok but to go slow and that I didn't think he would be able to "Put it in there", i got on my knees and piled up a bunch of pillows under my hips, He started just rubbing and playing back there and it felt REALLY good, I was playing with my nippers and really getting into it when he started licking it, That started out a bit awkward but he soon had it going real good and we were both very happy with how things were happening, He was jerking himself and licking me while I rubbed my button with one hand and my nips with the other and then he slipped a finger in my butt and that felt good so he went for two, Not so good but I let him and then he asked if he could put "It" in, I agreed to try but told him I didn't know if it would work.
Lots of lube, Lots of time and lots of pressure and I felt it slide in, I made him stop and just work it with the tip in, After a while that started not being the worst thing ever so I let him put a bit more and a bit more and he told me after he was about half way in when i told him no deeper, I was on the verge of a THIRD which I don't think is normal but I was right there when he told me he was about to finish, I didn't know what to say when he asked where to do it so i said inside which was a super weird feeling but he finished and I finished again right after which he said almost chopped off his p**** when I clenched but it just pushed him out.
He went and cleaned up and then I did and we laid in my bed talking for a long time just talking about everything we had experienced, I took my brothers lube back and hid it and everything was cool for about a week and then we were hanging out and I couldn't help it, I asked him if we could do it again, He told me he had been waiting for me to ask because he didn't want to. For three weeks now we have been doing it every time we can get alone and it is so weird that I am having a purely sexual relationship with my gay best friend but he totally knows how to get it done now, He is completely happy to finish me first and it pretty much goes exactly the same every time.
Starts out missionary until I get off, He licks me from behind and then has his way with my you know what and then he is totally happy to finish me on my back while fingering my butt for my second time which happens almost every time and he for some reason loves to play with my nips, He says he doesn't know why but they excite him (maybe because I have no b****) but he likes to play with them when we are just sitting around, He will put his arm around me and just slide his hand up my shirt and play with them for an hour or more.
I fully enjoy our relationship and I know one day it will end but for now we both get everything we need.