I Came, I Saw, I ConqueredbyChrono©
Let me tell you about a time about one year ago. This summer would be very interesting, as it would consist of my second trip to Europe. What was even better is that I was able to convince my parents to let my girlfriend to come (who is now my ex). Let's face it, I'm a jealous person, and I feared that in the month I would be gone, she would have found someone new. So, anyway... that month would mark a couple of milestones in our relationship. One of which would be the 10 month anniversary, and the other being the first time we played around with anal a little bit.
See, I always had a little fascination with the female ass. I mean, I always look at a pretty girl (who most of all happened to be my girlfriend especially)... she brushes her hair neatly, wears lovely perfume, paints herself with make-up... and yet, beneath all of that beauty, she still has an ass, which no matter what, is considered to be dirty. And to me, that dirtiness translates into naughtiness. Its like I shouldn't be intrigued with that area of a girl's body, but I am for the sheer fact that I shouldn't! So... anyway...
In the beginning of our relationship, my girl (her name was Sara), laid down a rule which would of course be broken during this trip, that she wouldn't do anything anally. I agreed to it, and thought nothing of it, since I never really found it too be that important. But, after many months of having regular sex, I found my fascination stir, and her ass appeared quite tantalizing. It was foreign ground... never invaded, never a point of interest. It would suddenly become my point of interest!
It all began in some bed and breakfast in north western Ireland. For some reason, my parents let Sara and I share a room together, alone, at each place we stayed. I was only 17 at the time... she was 18... yet, they trusted us. I simply told them I was a virgin (a lie) and I promised we wouldn't 'do anything'. Well, of course we did. We went to sleep together naked for god's sake. One night, at this B&B (the name and location I cannot remember off hand), she was lying naked, and I decided to give her a back massage. So, she laid on her stomach across the bed, and I kneeled between in slightly spread legs. I worked all of her muscles, from top to bottom... of course, her bottom was the intention all along, but I spent a good 15 minutes working everywhere else first. Then, I came to her butt...
So smooth, nice and perfect. God, it still excites me to this day thinking about her ass. I slowly rubbed each cheek individually. Each time I would press against her firm little cheeks, they would spread slightly, and I could see that mysterious, almost elusive little hole of hers come into view. I had seen it once before when we 69ed (which we ended up not liking, because it was uncomfortable)... and I can remember it being dark, and sweet, with light, almost invisible little wispy hairs around it. During the 69, I restrained myself from touching it (she did after all have my cock in her mouth, and I didn't want to risk surprising her in such a way that would make her bite down suddenly!!). But this time, I couldn't hold back!
After I finished massaging her, I took her cheeks and spread them -- this time, she could tell this wasn't an accident -- it was definitely pre-meditated! Almost immediately, she asked, "What are you doing?" And I told her I wanted to look at her butt up close. I put my face down closer and blew on it... she instinctively tensed her round muscles, and little goose bumps appeared. "Why are you looking at my butt, its nasty!!" she said, at least very close to what she said. By the way, it should be noted that any quotes I make in here probably aren't 100% exact, since this was a year ago. I'll be quoting the best I can!
Anyway... I reassured her that her ass was far from nasty, and that I was interested in looking at, since I never really did before. She seemed a little excited at this point, which I was happy for -- I didn't want her to think I was weird or anything. I could see her getting more wet, as my fingers circled the skin between her cheeks. "No one's ever paid attention to my ass before... this is interesting, and different..." she said, which of course, fueled me to continue. I took my pinky finger in to my mouth, and added a little spit to the tip of it, and proceeded to line it up with her untouched hole. I pushed against the opening a little, and it gave some resistance initially, but with just a little push, it popped through.... she was now shocked by this!
"Oh my god... Andy, what are you doing!?" she asked, in a nervous tone. "Just feeling around... exploring..." "But... its my ass..." she retorted...
Ha! What better reason is there I thought to myself! I moved my finger around a little, and I was extremely excited by this point. I had never felt that area of her body... it was so taboo. The inside of her was exceptionally warm, and the skin of tight, yet soft... smooth even. After a minute, I removed my finger, and licked it (don't ask me why, I was just so turned on at that moment, I needed to feel even more unclean). Next, I stuck my pointer finger in, and she seemed to be ok with this... I realized that her ass was more tight than I thought. After the resistance of getting my finger in, I wondered if getting my cock in there would even be possible. I decided to save that question for a later date. After I was done, she laid on her side, with her back to me, and I pressed my hard cock against her behind (I was naked by this point as well). I had no intention of entering her, I just poked around so to speak. After that, I decided to stop, because she just seemed a little tense about it. Great sex would ensue!
A few days later, while driving to Northern Ireland to see the Giant's Causeway (it has big stacks of naturally cubed blocks), her and I sat in the back seat, my parents were up front, my dad was driving. She laid her head down on my lap, and curled her legs up onto the seat. I suddenly got a weird idea. I placed my hand on her back and moved it slowly down her spine, until I hit the waist of her jeans. Stopping only for a few seconds, I pushed my hand in further, and I could feel her cheeks, warm against my hand, and the tightness of her panties against the top of my hand. I slid my finger down her crack until I found the little hole that I now found to be most intriguing. She looked up at me with inquisitive eyes that seemed to be saying, "What the hell are you doing!!??"
I must have been out of mind, my parents sitting mere feet from us in the front seats. Oh well, it made me even more excited nonetheless. I curled my finger and I began to massage her little rosebud. Occasionally, I slipped another finger even further down, and pushed into the opening of her pussy, while the other continued playing with her ass.
I pushed it a little more, and I got about a centimeter of my finger into her rear end. She seemed both thrilled and very nervous at the same time. I could feel her pussy growing very wet, as I did this. Finally she sat up, not able to take anymore, and I was forced to remove my hand. My parents were oblivious to the fact that I had my fingers in my girlfriend's ass and pussy... and I was so horny that I could have screamed. After that day, we would play around a little with anal, on and off. It was just sort of messing around... but it was fun!
On the last day of our stay, my parents decided it was alright for us to get smashed. We went to the pub (which was in Wales... we were there for our last few days) and I got to the point where it was tough walking straight. We got to the car and waited outside while my parents finished their drinks inside. We were alone, and in this drunken state, we didn't really care about decency. She unzipped my pants and I was more than happily surprised when she took me in her mouth. Before my parents got back, she had sucked me dry and I had managed to finger her. We got back to the B&B, and went to the room, horny still. She took off her clothes, I locked the door, got undressed, and the fun began. This time, I tried something new that I heard about called "shocking". This maneuver consisted of sticking two fingers in the girls pussy and the pinky into her ass, at the same time. I did this, and it lived up to its name. I fingered both of her holes rapidly, and this turned her on to the point where we just fucked like animals moments later.
However, even though I never stuck my cock in her ass during the trip, it opened the door for it later. After we got back, I kept bringing up the possibility of trying it once. She declined each time. I told her "...think of it as like giving me head, but with the other end of your mouth, and you actually feel something, plus you wouldn't have to swallow!" Finally, up in her bedroom (which is where I was a lot when I was at her house), we were talking dirty. And I pleaded with her to let me get her in the butt. She finally agreed, because she believed I wouldn't be able to get into it anyway. Excited and determined, I busted out the lube and began applying it to her little ass hole. I stuck a finger in it, and after awhile, another one. I had her loosened up at least a little bit.
Getting my cock in would be a different challenge altogether. First, I decided to try doggie style... it seemed the most obvious way. She got up on her hands and knees, and there I was behind this naughty girl... looking at her naked ass, her head down... I was in control of her body and she willingly handed it over. I lined my cock up to her lube drenched hole and pushed my very erect dick against her opening. In an almost humorous way, it slid up her crack, unable to get in. After a few attempts, I realized that the doggie style may not be the best way. I laid her on her stomach, and tried again... once again my cock ran up between her lovely cheeks time and time again.
Then we tried to do the position that we did a lot in our normal sexual activities in which she was on top, facing away from me... basically, she would get on her knees, and sit on my cock. This always thrilled me, because I could see my dick slide into her pussy between her butt and she raised and lowered herself on me.
Well, this didn't work well at all. I was about to resign, but I had one last plan. The spoon position! I asked her to lay on her side... this time I applied more lube, as it was quickly drying up. She drew her knees up towards her chest, and I laid next to her, behind her with my cock pressed at her cute bottom. Finally, her hole relaxed a little and it slid in...
"Oh my god... its going in... oh my god..." she panted. At first I didn't believe her... I thought I was going into her pussy and she was just saying that to make me believe I was in her ass. But I looked down, and low and behold, my head was in her forbidden hole. This took a long time to get all the way in, because I didn't want to hurt her. Her ass was very warm inside... it was the tightest hole on her body... the tightest hole I had ever been in. Her ass gripped my cock with true force. It felt like a hand, but wet and hot and naughty. This was it! I finally got my cock into her ass... a place she told me I could never go. After it went all the way in, I found myself pumping easily, in and out. It felt like a pussy, but more rigid and far more tight. She had never had a person there before -- one guy before me had his dick in her pussy, but I was the only one to ever get her there, and it felt like I was taking her virginity in some new way. She pushed against me and rubbed her clit, and I could feel her rear end crash into my lap again and again. Finally, I exploded in her bottom, coming inside of her secret, unfucked ass. I pulled out, and I could see the cum leaking out of her now loose, and gapingly open butt. I was shaking in my thrill.
However, she said she didn't really like it too much. I respected that opinion, and by the time our relationship ended, she let me have her ass four times... one of those times she actually came. I can honestly say that overall, pussy is better... but there's just something about fucking a pretty girl in her rear that turns me on more than pussy ever can! She knew it was wrong... I knew it was wrong. In the end, to me though... it was right!