As I climbed up on Ricks bed I noticed he reached in a drawer of the bedside table and took something from it ( it was lube). He had me stand on my knees and handed me a couple of pillows and instructed me to press them against my stomach and bend over, letting me head and shoulders lay on the bed with my ass sticking up in the air. As I did so I started to feel a little scared but also excited. He had me reach back and spread my ass cheeks wide open with my hands. I felt something touch my asshole and jumped a little and I think let out a little gasp or squeal, at 17 years old I had never had anyone touch me there before. I realized it was his tongue and I wanted to ask him no, it seemed nasty to me, to but fuck it felt so good as he licked around my tight butt hole. Then I felt like it was pushing against it and I realized he was pushing his tongue in my ass. Now that felt fucking great. He licked and tongued my ass hole for several minutes and then stopped. I heard him doing something back there but could not see what it was and then I felt his finger rubbing my little hole and then it slipped inside my poop chute a little ways. It did not hurt but felt a little uncomfortable as he worked it gently in and out, slipping a little deeper as he went until I think all of it was inside me. He moved it around some and then pulled it out and then I felt something a little bigger going in and this was two fingers. This was a little more uncomfortable but still did not really hurt too bad, but I was starting to wonder just how bad it would hurt. I knew before I asked him to do this that it would really hurt  but after my best friend had gotten knocked up at 16 and told me how bad it was having a baby come out and taking care of it and me not being on the pill I chose this. I wanted Rick so bad and was so fucking horny all the time I had to try, but I knew I would never talk him into fucking me again, I had to almost black mail him into doing this so no matter what there was no backing out, no matter how bad it hurt. His fingers pulled from my Butt hole and I knew this was it, I braced myself as he told me to try and relax.
I felt something big touch my hole and I almost backed out but I held my cheeks open for him and waited for what came next. I felt pressure against my tight hole and knew it was that enormous mushroom head of Ricks big dick. I had not seen it until this night and was amazed at how big it was. The couple of guys I had dated and actually felt and jacked off their cocks had been nothing compared to his giant meat. They were like the size of hot dogs and here he was a big around as a coke can almost and almost twice as long. I felt the pressure getting harder and harder and suddenly I felt the pain. FUCK ME it felt like a telephone pole was being shoved up my ass hole, I mean a telephone pole on fire that is. It hurt like fucking hell, a kind of ripping, burning pain like I was being split wide open. It was that damn hellacious head of his dick opening me up and slipping in my shitter. Oh how it hurt, the tears were flowing and I screamed a little and he froze and asked if I was okay. I just nodded I could not speak, hell I could not even breath. Oh why did I do this I was thinking, but i knew why, I loved him and wanted him to be my first, maybe I should have asked him to fuck my pussy and use a rubber, but I did not want that to be how i had sex the first time. I felt the pressure continue and felt the pain going deeper and deeper and I swear I felt that fucking head pop through my as as it finally went all the way in. It still hurt like hell and he started to push and pull his big cock in my ass, it was so tight I had to steady myself so it wouldn't pull me and push me with it. I could tell it was going a little deeper as he fucked me and it seemed like it went on for hours but it only lasted a few minutes. He pulled out real slow and easy but damn when it came out I had to yelp in pain. He had me lay on my side and he lay there holding me. I was hurting so bad but nothing like when he was inside me.
After several minutes he helped me up and took me out to the hot tub and had me soak in it. My fucking ass hole burned but the hot water eventually soothed it.  I sat in there and smoked a cigarette as he sat there with me. I asked him did he cum and he said no Baby it takes me a while and I knew it would hurt you too much, I only put a few inches in you also because I knew you could not take it all. I felt a little disappointed, I wanted it to be so special for him but then he told me I know it took a lot for you to do what you did and it means a lot to me, I know you really care about me and i will always remember this. I was so happy I almost forgot about the pain. I dressed and went home, trying not to walk funny, but no one saw me come in anyway. I felt different, no not because my ass hole had been stretched from here to next week, I felt like I had grown up some, I showered and went to bed. I gave my fingers a good workout that night thinking about Rick and his giant dick.
Rick called me the next day and asked how I was doing, it still hurt some and I told him. I asked him could we try it again after it quits hurting, he got quit a minute and then said probably, we'd see. It was three days before it had stopped hurting completely and I called him and asked if i could come over that night, he said we'll see about the fucking but he would take me out to dinner. I was so fucking happy, we were going on a date. I didn't know what to wear but remembered he had said something about liking Women to dress slutty for him so I finally decided on a short skirt and a low cut top that showed my big ol tits off, I knew he loved big tits. I did my makeup and put on a little extra hoping it would look good and slutty. I was to go to his house and we were to go from there since it would be obvious if he came to pick me up looking like I did. He came to the door and the look he gave me told me I did good. I was hoping he would fuck me
right there but we went out to eat. He took me to The Cheesecake factory, I had never been and damn it was good. It is one of our favorite restaurants now and you would not believe what we like to  do there, that will be another story.
After dinner he took me his house and gave me a little gift bag. I kissed him and looked inside. I wasn't sure what they were then but he had given me a set of butt plugs, there were three of them a little one and medium one and a larger one and a bottle of Astro-Glide lube. He explained that i could use them to stretch my ass hole and make it easier. I kissed him again and we went to the bedroom and were both naked in a heart beat. I got on the bed as before and he licked my ass hole again, I no longer thought it was gross but loved it. He lubed up the small plug and eased it in  twisting it as he did he told me to practice every day leaving it in a couple of minutes the first day or so and then longer and longer. It hurt just a little and soon he pulled it out and lubed up the medium one and eased it in as he had the other. This one hurt pretty bad but he left it in for a few minutes and then to my surprise I felt his big schlong pushing against my ass hole and finally slipping in again it felt like it was ripping my ass hole out. He fucked me a little longer this time and told me later he had put about a third of his cock in this time. The rest of the evening was pretty much the repeat of the previous time. But he told me if I wanted to keep on fucking him he would like that and I was completely happy. We waited two more days and repeated, I worked on my ass with the plugs and after a week was taking the bigger one. After about 5 times it got to where it started feeling good toward the end of him fucking my ass and he was giving me all but a few inches. By the 8th time he finally came up my ass and I was really happy. By about 12 times it only hurt bad when he was putting it in and sinking it deep inside my tight butt.  The 15th time I had my first anal orgasm, fuck my first ever orgasm of any kind really. Now 10 years later no pain and it's fucking awesome. He fucks my ass hole almost every time we have sex, sometimes 5 times a night. Oh after a month of fucking my ass he took me to the doctor and got me on the pill. Six weeks after he first fucked my ass I gave him my pussy oh and it hurt like hell too lol, why did I pick a man who is hung like a horse to give my pussy and ass hole too first the first time. I would never have dreamed 10 years ago that something that hurt so fucking bad would end up to be the most pleasurable thing of all? Now when I feel the tip of that enormous round mushroom head of his dick touch my tight (yes it is still as tight as ever) sphincter I almost cum with anticipation. Then as it enters, stretching me so fucking big I feel pure ecstasy and as that thick shaft penetrates deeper and deeper stretching and  filling me up so completely it just can't get any better than that. He is the only man who has ever and will ever fuck me in my ass, and he broke up with me and told me I had to try other men before he would take me back so I did, I fucked 5 others and after I begged him and told him I only wanted him then he took me back. I know now why he did it so I wouldn't wonder years later what I had missed and now I do not want any other men. Now women, that's a different story. Oh I finally got up the nerve to suck his dick about 3 months after he first fucked my ass, I had trouble because of the size but had gotten pointers from my whore Aunt Sandy and managed to do fairly good. Now I can give a fucking great BJ and I always swallow every drop.