I had spontaneous anal sex for the first time last night with my boyfriend, and it was the best sex I have EVER had. We've tried in the past with no success because he's on the larger side and I have trouble relaxing, so it usually ends in immense pain and frustration (on my part). Last night, though, was the complete opposite--no pain whatsoever and lots of orgasms
We've always used lube when attempting anal in the past. Last night, though, that was not the case. I was out of town for the weekend while my boyfriend stayed home, so the sex we had when I got back was a bit more intense (increased physical and emotional need for one another) than it typically is. Foreplay was lengthy, and I came about six times from oral before we progressed to missionary PIV penetration. I probably came twice during PIV, but I was so wet at that point that I began to lose sensation. I didn't say anything to my boyfriend about my lack of pleasure because a) I wasn't uncomfortable by any means, and b) I had already cum 7-8 times so I was happy and wanted him to be able to finish. After what I'm assuming to be a few minutes, though, he pulled out and began to massage the head of his penis against my anus as he sometimes does, which seems to be his way of asking for permission for anal. At first I said no, as usual, but I was so relaxed and content at this point, and anal sex is something that I've been wanting to successfully try for so long with my boyfriend, that I caved. I guided him through it to ensure that I didn't experience any pain or discomfort, told him when to apply more pressure to go deeper, and when to lay off when it began to feel overwhelming. Because I was so wet and relaxed at this point from having multiple orgasms, there was no pain at all and it wasn't long before I was asking for it harder and faster. The first time I came from anal was due to some light clitoral stimulation, but it honestly didn't take much because I was experiencing so much pleasure from penetration alone. My second, third, and fourth orgasms were simply from doing kegels as my boyfriend penetrated hard and fast, no clitoral stimulation involved. Those four orgasms that I experienced during anal were absolutely mind blowing, and WAY easier for me to achieve than with PIV. When we finished, my eyes began to water because I just felt so amazed and content.
I'm honestly shocked that it was so easy to cum from anal, because most of what I've read online has said that not many woman do. I think the recipe for our success last night was, of course, getting me extremely wet beforehand (the sounds coming from my vagina were not cute), and giving me so many orgasms that I was too relaxed to tense up and/or really care about what was about to happen. Unfortunately it wasn't an all-around success because my boyfriend was unable to finish due to cocaine use the previous night, and we both kind of get off on the idea of him cumming in my butt, so we called it quits once I began to feel some friction and didn't feel like my body could handle another orgasm. Despite that, though, my first time having anal sex was by far the best sex of my life. I CANNOT WAIT to try anal on LSD
