Like most couples in a long term relationship me and my partner have experimented with sex, and I'm sure like most couples when we talked about what we wanted sexually we soon got on the subject of anal sex. Anal sex was a subject that terrified me but my partner was obsessed with the idea of doing anal and even though we had attempted anal sex several times the pain was always horrific and I couldn’t find any enjoyment from it, well saying that the only time I had been able to ‘put up with the feeling’ was after a drink (really quite drunk actually) but I still wouldn’t say this was pleasurable, It was more of a ‘pleasure pain’ type of feeling and even with some parts of the experience feeling ok it wasn’t the experience to convert me. The strange thing is that I actually enjoy anal play and even though it was my partner that started off playing with my ass during sex I enjoyed it so much that i find myself sometimes asking him to play with my ass when I’m about to come to an orgasm because the feeling is so intense when he has a finger/thumb in my ass and I’m cumming. This was something he would mention when we would be talking about anal sex and he had a point I guess. If I found anal foreplay enjoyable and exciting I should really be able to find anal sex enjoyable, and this is probably why I kept attempting anal sex for him (couples will do silly things for the partner they love) So if anal sex was really something that he wanted (needed) in our relationship I decided to do my research, and found a lot of useful information about anal sex. Also a friend of mine had some good advice from her own personal experiences so this is why I’m posting here because I’m hoping that if anybody else is having a similar situation this story may help you the same way it has helped me? So.. With me already enjoying anal play I would start by trying some gentle massaging (either yourself or your partner) during sex, my partner would apply lubrication to my anus area and with his finger/thumb rub (gently) on my ass and my partner said he could tell when I was enjoying it because he would feel me relax. This is when he would start applying a little pressure on my ass with his finger/thumb and if I was relaxed enough his finger/thumb would quite easily slide in my ass, please note (especially men) this is not a time to start thrusting/penetrating the finger/thumb as this would hurt and it always made me more tense and if you’re not enjoying the foreplay you will never enjoy anything further I always enjoyed anal foreplay anyway so then we got to the next stages of foreplay which was toys. Some couples do also try analigus when experimenting with foreplay, and even though we did have one time during oral sex when he went a little lower than he was expecting this was something we wasn’t really that interested in getting involved with (it did actually feel amazing at the time, we carried on just that once, as he was already there so we put it down as new experience) Anyway… My partner has used a small bullet vibrator on me before (anally) but we decided to purchase a plug which was a lot easier to insert and felt better because with a bullet type vibrator it isn’t designed to sit in place and let you adapt to the feeling of having something inside your anus, it was the movement of a vibrator that made me feel uncomfortable and tense up which then caused pain. So with a small plug purchased during sex (after the stages of him massaging my ass with his finger/thumb) when i felt relaxed he would slowly apply pressure to my ass (using the plug) until the plug was inserted then we would just carry on sex as normal leaving the plug inserted and removing once we had finished so to speak. I would prefer the plug to be slowly removed as I was cumming because my mind was more focused on the pleasure I was feeling rather than having to have a plug removed from my butt (sorry to be so graphic) We continued using a plug during sex for a few months before trying to move on to actual anal penetration and I guess the only way to explain how my body was working is that I knew what to expect so i found it easier to relax myself and was use to the feeling of having something in my anus. I think the best bit of advice here is breathing, when he was inserting the plug breathing out helped because (sorry its gross) it relaxed my anus and helped open my ass, when I would inhale it was clench my buttocks and tighten up which then of course caused discomfort/pain. We were then ready to try anal penetration, in the past when we had discussed trying anal we would pretty much go straight into anal I would be nervous and he would just apply loads of lubrication and try inserting his penis in me. This time we was more prepared and we started with normal oral sex (he went down on me) so I was relaxed and felt turned on then when I was wet and horny we started normal vaginal intercourse and then introduced the plug as we had been doing for the last few months. When I was feeling like I was starting to get close to coming to an orgasm we changed to anal intercourse (because once I have come to an orgasm I feel too sensitive to carry on having sex) Me and my partner were already laid side by side (in the spooning position) and he slowly pulled out of my vagina then removed the plug from my anus, he then started to push the head of his penis against my ass and I reached back to hold him (hold his penis) so I felt more in control of the pace he was inserting, told him to add lubricant to his penis (it was easier to insert him when we lubricated him rather than cover my ass in lubrication) then once again breathing out as I kind of rocked/grinded against him so his penis wasn’t actually inserting into me but was putting pressure against my ass, I slowly pushed further back with each rock/grind until I felt the head go inside of me. This is where I had to stop and just lay stationary for a few seconds and breathe because this felt bigger than a plug I was use to inside me so I just needed those few seconds to adapt to the size and relax myself, added some more lubricant (on the shaft keeping the tip inside me) and then when I felt ready I started grinding my hips again not really taking any extra length inside of me just feeling the motion of the tip of his penis inside my anus gradually pushing back a little further so a little more of his penis would insert into my anus. We carried this slow grinding motion on applying lubrication when needed until he was starting to feel close to ejaculation, and as we only had less than half the length of his penis inside me i slowly pulled him out of my ass before he cum I then rolled from my side to my front and told him to masturbate over my ass because. I didn’t want the excitement of him ejaculating inside me to cause him to push deeper into me and ruin the experience by hurting me right at the end. He always liked me to spread my buttocks and masturbate over my ass in the past before i would try anal sex with him so after I pulled him out of my anus and rolled onto my front and spread my cheeks (sorry again to be so graphic) he was more than happy to cum over my ass. I then got a big kiss a cuddle and lots of thank yous. This was the first time I had been able to have anal sex and enjoy the feeling and my partner was so excited that we had successfully achieved anal sex I of course got the most attention I’ve ever had from him in our relationship lol.