So, I am a gay bottom and my best friend for 10 years is a female from a prior job. I am not going to use any names, ages, or give a lot of background or I will go on and on. Anyways, we are tight and talk about everything, we bar hop, spend the night at each other's place when we are drinking. She feels safe with me and I feel safe with her. We talk a lot and are open with each other. A Saturday night this summer, I was at her place to watch some stupid shit but I wanted to hang out with her and we sacrifice for one another doing what the other wants. So, the stupid movie is over, we are having a Campari and soda and on our laptops. She said to me, "You know what I like to watch?" and she shows me gay porn. She has mentioned this before but has never pulled a video up in front of me. I was just like... "Why do you like dudes boinking each other, I don't get it?" I still don't get it yet she said she likes it because in the videos she watches, the guys are hot and sexy, plus it seems genuine. They are really enjoying it versus all the fake chicks moaning. She gravitates towards the little fem bottoms and hung power tops. Other girls have told me they like gay porn. This video was hot with some young fit cock. We have talked about me being a bottom and experiences I have had... which isn't a lot... one. All the time, she jokes about my butt being hot, knows my package is less than stellar, and I talk about my insecurities... lack of size, boy balls, small loads, and not being explosive. I am just a little sub bottom. She has wanted to see my ass before... just f'ing around. I would shake it in my jeans or shorts and just laugh at her. Tell her she needs cock. This time, maybe it was the video and just the relaxed mood we were in, she really wanted to see it. She was like serious. I was getting a bit prissy, but I was like, ok, I decided to pull my jeans down over my little Calvin briefs asking... "Will you be happy?" She said I had a really nice ass. She was asking me questions about whether I play with myself... which she already knew. She was staring at my bum and said she was imagining me taking cock as in the vids. She told me to take my jeans off and she wanted to see me. So, I did. I turned to show her my front but she told me she wanted to see my bum. I was not hard. It was like modeling and kind of fun. It is nice to be seen as desirable. She said 'Take them off, please". Telling me it's not a big deal. "Just show me, I don't want to have sex, I just want to see your ass". I told her I need another drink which she made but then I had to comply. So, I pulled my white briefs down but pulled my shirt down and she got pissed. Hah. I took my shirt off and said "See". She told me to turn to each side, and said I had a sprinter's ass. Next, she had me lie down on her bed on my stomach. We were hanging out in her room. I was acting like I didn't like it but did. I am gay but its hot for a chick to think I am sexy... or at least my bum. She asked me again about playing with myself and how I do it. I said I usually pin my feet behind my head and play. Flat out, she said, "Do it, I want to cum". I looked at her with a Geez look, and she said "B, come on, I want to do what we have talked about". At this point, it was clear she was becoming dominant which isn't difficult with me. She told me she needed to cum and wanted to watch me play with myself. I told her I didn't have anything which was dumb because she had toys. She got me this thing she had for guys with a part that vibrates inside and another part outside under your balls. I just wanted her little vibrator and she got that for me and some lube. I was turned on because she was super horny. I am on the bed with my feet on the bed and my knees up, touching and using the vibrator. She is kicking back in her chair. Next thing, she is touching herself on the outside of her sweats. She took them off as she got hornier. She reached down into her little panties and was fingering herself. I've seen her in her panties before but not while she was playing with her pussy, lol. What turned me on is the fact I turned her on. She told me to give her the vibrator which she slipped under her panties. I had never been with a woman but she was acting the way I thought she would... shifting around and moaning a bit. She made me put my feet behind my head and go deep with the male vibrating toy while I stroked my dick which is around 5.0"-5.5" in length and 4.25"-4.50" in girth. She was in total control, it put me at ease. Her glances turned me on. I was told to cum at the same time she did. We were talking to each other about how close we were and she wanted me to start cumming first because hers would last longer. In other words, she wanted me to get her off. I told her when I could feel it stirring but she wasn't there yet. So, I stopped and squeezed the base of the shaft. Her legs were spread wide over the armrests. I was on edge and didn't need a lot of warning. Her breathing picked up. I could see her tense up and she said, "I am gonna cum, cum now, cum B!". I could feel the cum build at the base of my cock, I told her "I feel it" , and it was intense. When I ejaculated, there was one spurt that traveled maybe 2 inches... I caught air (LOL), it was heavy for me, and some drops followed. It was a very powerful orgasm. With me, it is more about the orgasm, the intensity of the contractions, and less about the feeling of release. The way the toy vibrated under my balls felt really good when my little hole contracted rhythmically around the toy. I was moaning, asking her to cum. She was on the verge and looking at me as I had my legs out from behind my head. They were spread wide and vertical. It feels better that way when I orgasm. She couldn't see any cum due to how I cum. It isn't a heavy load of thick white cum that shoots out in ropes. I came the way I do and she accepted me as I am. I was very vulnerable with my legs up, fully naked with just footie socks, a toy in my hole, my little cumshot and dick , yet I felt SO safe with her. She knew I was cumming because of all my "Oh oh" moans. It must have been the trigger because she orgasmed hard. She would have ripped my slender dick off if I had been inside her, lol. Initially, she was lifting her hips up and down and the power was evident. Her body became more rigid next with her mouth open, gasping. It lasted a long time. I mean, I am spent in 4-6 seconds but she was going for much longer. The tension was intense yet she sounded more and more satisfied as it went on and let out a big breath at the end. That actually made me smile... I mean, I love her and want her to feel good. The tension dissipated. I did my job well, hah. She "only" had the one massive orgasm and I was empty after one load. We were fine afterwards, not awkward. I spent the night, wore her pajamas as usual, and I snuggled her as she came down from her orgasm. She said it was one of her biggest ever, and hearing my soft moans turned her on. I know she cares about me and often tells me I deserve to receive pleasure. Being cared about that way is super comforting. She asked if it was good for me and told her I felt each contraction deep in my body. Sharing our orgasms was amazing. The intimacy and vulnerability of cumming with her was super stimulating. I felt... I don't know, everything about me was exposed... my body, my imperfections, the submissiveness, little whimpers, my orgasm face, yet I felt totally safe and protected without performance anxiety. Holding her afterwards was the most calming moment in my entire life. I had allowed myself to actually let go and not hide anything. We were good and she fell asleep in my arms. It was just a one time deal so far. I think she was pent up, curious, and I am a pleasure giver, so yea.