Obsessed With Anal

Dear Readers,

This is a story that I immensely enjoyed writting. It has a bit of everything in it except quickies. I hope that you all enjoy it. Comments are appreciated!

~M

Chapter 1

I loved masturbating. My problem was that I loved it more than having sex and it was getting frustrating. I didn't want it to be that way but I couldn't seem to help it. I figured that it was just something wrong with me.

One of my problems was that I was always dissatisfied after sex. Two minutes after my guy left or went to sleep; I was masturbating to get myself off. It wasn't that I didn't cum during sex, but the orgasms that I had during masturbation were so much stronger that sometimes I did not even want sex.

This was making me stay horny. I liked sex but I was sure that if I could have great orgasms then I would love sex. I hated to admit it but my problems with sex were entirely my fault. I just could never express what I wanted and could never let go entirely. When I masturbated I could let my fantasies go crazy and didn't have to be shy about them.

I was always too shy to voice my opinions about sex with whoever I was with. I never initiated sex. I never told them about what I wanted to try. It was always up to them. Therefore, I was always bored during sex. I just didn't want to have to tell my guy what to do. I felt like they should want me enough to explore and figure me out.

I felt bad that I was always so horny. Some of my boyfriends got frustrated and felt that I needed to initiate sex. I just could not do it. Part of me felt like it was my guy's responsibility to take the reins, but another part of me secretly felt that I would just go completely wanton if I began to assert myself sexually. My fantasies were always on the kinkier side and truth be told, they scared me a little.

My fantasies tended to range from tender love-making to full out bondage. I'd never tried anal but it had been a persistent thought for a while. Besides the fact that I was shy about sex, I also wanted to save something for when I got married. I wasn't a virgin but there were a lot of things that i'd never done. I wanted to keep some mystery and experience everything with the person i'd spend the rest of my life with.

Unfortunately, I wanted more and more out of sex but was getting the same results. I began masturbating more and having sex less. I hated the fact that I was compiling my grocery list or wanting to watch tivo while having sex. While masturbating I was beginning to fantasize more and more about doing anal.

I noticed that the pornos that I watched were beginning to lean more towards doing anal. I had bought them without consciously knowing why. It was getting so that it was my only fantasy when I masturbated.

Pretty soon anal was all I thought about but I wasn't into my boyfriend enough to do it with him. Plus, I really did want to save that for whenever I got married. Now my problem was that I was horny no matter what I did. I would have sex and masturbate afterwards. I would masturbate but then feel empty.

I realized that I needed an outlet for my pent up desires and I needed it soon. I felt like I was turning into an absolute hornball. I guess I just loved the idea of achieving the ultimate orgasm and that is what made me stay so horny. However, the reality of my situation left me jaded and feeling like sex was overrated.

With that being said, I decided to dump my current boyfriend. Don't get me wrong, I knew that the sex was more of my problem than his, but he was a jerk on top of it. I was willing to try going without a man, but I was still so horny that I upped my masturbation to three times a day.

I knew that deep down I did not enjoy sex as much because I had a hard time just letting go and letting my body feel everything. In my fantasies I could be as loose and free as I wanted. In reality I was uptight, shy, and unsatisfied. I didn't even know where all of my buttons were so I knew that without me speaking up, whomever I was with would not hit them.

I figured that I was obssessing over anal because it would help me give up control in an area of my body that I really had to trust someone with. I thought that it would break through my shyness and my control. I wanted to have a complete sexual experience and I couldn't do that if I remained so uptight. I had wanted to wait until marriage but I needed a solution fast. I was spending more time taking showers after masturbating than enjoying the life I had.

I guess its past time that I introduced myself. I am Kristen; I'm 23, 125lbs, 5'2, with curvess in all the right places. I have all natural 34DD breasts. I am a thick girl, but I work out to keep it all toned. I have shoulder length brown hair with small facial features. My eyes have a slight Asian slant that I thank whoever my ancestors are everyday for them. Finally, my lips, perhaps my favorite feature, are the only thing on my face that is thick and lustrous. I am of African descent. I was pretty sure that I wasn't one hundred percent African-American, but that is neither here nor there.

I had decided to enlist the help of my best friend. He had been my rock through all of the bad relationships and I knew he would help me out. I knew that what I was about to ask him might put a strain on our friendship, but I was desperate and I knew that he would eventually forgive me. I called him up and asked him to come over. We were the odd couple. He was tall and lanky, blonde spiky hair with bright blue eyes. That is about where the oddities stopped. I could talk about anything with him and I had, everything except my growing obsession with doing anal. I needed to butter him up, so I made his favorite pie, chocolate crème.

He walked in and sat down. I placed the pie in front of him and gave him a fork. He dug right into the center and began working his way out. Wow this guy could eat. It never ceased to amaze me the amount of food he was able to put away. I walked over to the couch while he ate. I was flipping through channels when he swiveled around on the barstool and asked, "What do you want Kris?" Damn, half of the pie was gone. He had chocolate on his mouth and I smiled.

"Jake, what makes you think I want something?" He rolled his eyes at me and pointed to the quickly diminishing pie that he hadn't stopped eating yet. "You made my favorite, you only do that when you want something, so spit it out." I handed him a napkin and went back to the couch. I wasn't sure where to start.

"I need your advice on something and i'd like you to listen to the whole thing before you say anything." He just nodded and kept eating.

"I know why I end up dumping or being dumped by all of my boyfriends. It's as if I have this block or wall when I have sex. I am too afraid to speak up and tell what I want, partly because I feel that they still wouldn't get it right, and partly because I don't think that it would break down the wall anyway. I have a problem letting go. I want sex to be an experience that I can lose myself in. I find myself thinking of all the things I need to do while i'm having sex, and sometimes i'm putting together my grocery list or thinking about tivo during sex. I'm so frustrated, that's the real reason I don't have a boyfriend."

I risked a glance at him and he was starring at me with his fork poised in the air. Damn, I had shocked him already. I thought he would at least be stuffed off pie and lulled into a false sense of security before I started springing the big stuff at him.

I held my hand up to signal to him that there was more. He arched his eyebrow but thankfully said nothing.

"I've been thinking about this for some time, and I think that I have a solution. You know that I have had this fascination with anal sex, but you also know that I wanted to wait until marriage. I've decided to let go of that conviction because now its all I can think of. I think that letting myself be vulnerable enough to have anal sex will knock down the wall between sex and me. So what do you think?"

He had all but forgotten about the pie and that was not a good sign. "Kris", he sighed, "I don't think that your problem can be solved with anal sex. You're a romantic to the fifth power. I think if you really love someone then you won't have this problem and I know that if you don't wait to have anal sex then you'll regret it."

I felt like crying. "I know Jake, but that doesn't help me now! I'm so horny all the time and I don't know what to do about it because sex is no longer satisfying. I don't know what to do. It is getting to the point where all I think about is getting my ass split open over and over. I've never told anyone, but i'm scared that if I do let go then i'll be a slut. That i'll want it and need it all the time and that i'll do anything to get it. I don't know how to do anything half-way. Either I am unsatisfied because I hold back or i'll be a slut because of an overactive sex drive. You know how I feel about love and marriage; I just can't be a slut."

I didn't even know that i'd started to cry until Jake handed me some tissues and came to sit by me. He wrapped his arms around me and kissed my temple. It was a comfortable position that we had been in countless times before. I leaned into him and was vaguely aware that he seemed much larger than his lanky frame suggested.

"Ok so I understand now. Why don't you go out and meet a nice guy, make sure you trust him and then ask him to help you out. You're a sexy girl, i'm sure that you can get someone. And once you really trust them, you can reconcile within yourself that not waiting until marriage was something that you had to do for your wellbeing."

"J, you know I don't trust people easily. It would take forever for me to get that close to someone. Plus, with all the jerks out there, they would tell me they love me just to get at my ass. I just don't want to risk it."

"Kris you aren't giving yourself a lot of options. I know i'm more of a sounding board than any actual help, but you've painted yourself into a corner. You want sex, but sex is not satisfying. So, you want anal to try to shake things up, but you don't trust anyone to pop your anal cherry and you don't want to wait for love anymore. Have I missed anything?"

This was my chance, it was now or never. My heart was racing and if I were light, I swear that I would be blushing beet red. "Yeah Jake, you did miss something... I trust you." I starred at him head on and he moved to the other end of the couch. His mouth was partially open and the look would have been comical had I not been so nervous.

"This is what you wanted. You didn't want my advice, you want me to... to... you know! You can't really want me to do something like this. We have never gone there and for good reason. You don't love me, we don't like eachother like that i'm not even your type. Plus, i'm gay! I just can't."

I rolled my eyes and thought, not the gay thing again. "Please Jake, I know that we're best friends, and I have respected you a lot by not prying into the whole gay thing, but I just told you something really deep and important about me so I thought it would make you come clean about being gay. Fact is, I do not think you're gay. For whatever reason, you don't date, but I still don't think you're gay."

He was turning beet red by now. Oh man, I never wanted to embarrass him or argue. "Why would you say such a thing? I wouldn't admit to being gay if I wasn't, what kind of person does that?"

"I know, I just figured that it had to be something big in order for you to lie like that so I didn't push. However, you can't deny that you get an erection looking at women. How many times have you plumped watching something on television? And there have been numerous times that you were erect without there being a male in sight. How do you explain that?"

He hung his head and I knew that there were tears in his eyes. I hugged him and he just sat limply holding me back. "I just can't tell you, I hope you understand. No, i'm not gay, I don't know why you didn't call me on it before, but i'm glad you didn't. I don't know if I can help you with your problem. There are so many reasons for me to say no, reasons that you don't even know but i'll think about it." He got up, got the rest of his pie and walked out.

Well, that didn't go like I wanted it to but it wasn't a complete disaster. At least he remembered the pie.

Chapter 2

I had heartburn. I'd had it since Kris came to me with her proposition. She couldn't have stumped me more if she'd told me she wanted to try women. It had been a week and I still hadn't seen or talked to her. She knew I wasn't gay, man it was a relief but it also filled me with a sense of dread. Now that she knew for sure, she wouldn't have far to go to find out the truth. I just couldn't see going to her and saying, "Hey Kris, I told you I was gay so that you wouldn't know that I'm a twenty-three year old virgin who is in love with you."

She'd even seen me get erect. Man, I couldn't be more embarrased. At least she hadn't guessed that it was her who made me plump up. She hated to wear underwear when she was at home so everytime I was at her house I saw nipple or the roundness of her ass uninhibited by jeans or almost anything for that matter. Most of the time I could ignore it but when she was overly excited she tended to jump and skip. It was like softcore porn for me. I just sighed and took some tums.

When I first met Kris, we were on the same floor in the dorms. We became friends almost instantly seeing as both of us were English majors. It was fun to have someone to just talk to who didn't want me to go to some party and fuck anything that moved. I know college is supposed to be the craziest time for students, but we were the only sensible ones. We gorged on ice cream and every kind of movie imaginable. In our second year of college, I started to fall for her, but being her friend, I knew that I was nowhere near her type. I'd only seen her date dark skinned guys and no, I don't mean just inside her own race. So far, she'd dated a Cuban, a Hispanic, and an Indian amongst a host of black guys. All of which were large football types. I couldn't be more different.

It wasn't as if I was trying to be a monk or something, but in high school, i'd gone through a really awkward phase. I wasn't exactly a geek, but i've never been extremely big. Needless to say, I had an inherent shyness that didn't enable talking to girls a lot. When I met Kris, I think we clicked so well because she didn't pressure me to date or even get laid. She was just supportive of me in all my decisions. Then all other girls started to pale in comparison to her so I just stopped dating. When Kris called me on it, that high school shyness returned and I chickened out. I told her I was gay. That may not seem like the easy way out but trust me it was. I knew she'd leave me alone about it and she did.

When I saw that she'd made my favorite pie I knew she wanted something. I never told her that she really didn't have to butter me up because there was little I could refuse her, but on the other hand, who'd pass up free pie. When we were in college it used to be vending machine snacks but after we moved into our respective apartments, it became lip-smacking pastries. Normally when she made my favorite, whatever she wanted was big. This time it blew the roof off.

I knew what I wanted to do, but I wasn't sure that I had the courage. My plan would enable me to lose my virginity with the woman of my dreams while keeping my dignity by not letting her know that she was the woman of my dreams. It wasn't that I didn't want her to know... eventually, but I planned to take advantage of the opportunity. She opened the door to Pandora's Box, but in order for me to win the ultimate prize; I had to be really clever. I planned to make her fall in love with me without even realizing it. All I had to do was not chicken out.

Chapter 3

I knocked on her door fifteen minutes after telling her that i'd be coming over to talk. When she opened the door, I handed her the plastic box with three of her favorite sweets.

"Oh My God! Are those dark chocolate covered strawberries?!" She groaned and started mumbling about her thighs while digging into the tart treats. Seeing what her lips were doing to that chocolate had me damn near groaning myself.

Finally, I said, "Yeah, it's a peace offering, i'm sorry for running out that last time."

She started shaking her head and waving to signal that it wasn't a problem. "I knew you'd need some time to soak it all in, so I understood."

You have no idea, I thought. I rubbed my palms on the front of my jeans and braced myself for what I was about to say. "Kris, i've made a decision about what you asked me." She was on her way to the third and last strawberry when she stopped, tongue out strawberry raised. She looked at me and then replaced the treat into the carton and put it in the refrigerator. She came back from the kitchen, sat on the barstool and simply said, "Ok".

"I've decided to help you out as you put it, but there are some stipulations." I got up and started pacing. "There is something about me that you don't know. Something that is important if you still want to go through with this. It's what I couldn't tell you before and partially why I told you that I was gay." I moved over to the window and looked out into the nothingness that was night. With my head down, I told her as much of it as I dared. "I'm a virgin Kris. I've never even had oral."

When I turned around her eyes were like saucers and her mouth was wide open. I continued anyway. "You know all about how I was in high school. I never really had a girlfriend. When I got to college, I figured things would be better, but they weren't. Waiting in high school to get a girlfriend made me realize that I wanted my first time to be special. I dated once we got into the dorms, as you know, but they thought I was weird for not trying immediately to get into their pants so it never worked out. You and I are such good friends because you didn't ask too many questions. Since then it's pretty much been the same story. The older I get, the harder it is for women to understand that I need more than just a physical connection, plus it isn't the hottest thing to be a virgin at my age."

She got up and walked over to me. "I admit that it's a shock, but it explains so much and now I understand. You have nothing to be ashamed of. You waited until you were mature enough to respect and be able to cherish something that we all wish we had waited for. It makes you special not weird or a freak and any girl who can't see that is a fool."

She made her way over to the couch and placed her head in her hands. "That does put a different spin on my problem. Now I don't want you to help me. You should wait until you find someone special."

I couldn't help my reaction; I cupped her cheek and whispered, "You are special, very special to me." I pulled myself back and sighed. "Besides Kris, I trust you too. I never wanted to wait until marriage and who better to teach me than someone I can trust with this very dark secret." I was so playing her and she knew it, but she started it.

"So..." she gulped, "you're basically saying that we both need something that the other can provide, and since I asked you because I trust you, you finally decided to tell me the truth and ask me to do this for you. You realize that there is no way that I can refuse you now, that is, if I still want you to help me."

"Kris, it's a win-win situation because we trust each other. It couldn't have worked out more perfect if we'd planned it."

Chapter 4

Wow, what a revelation. I was trying not to stare too hard at Jake. It took guts to stick to your guns and not let people persuade you into doing things that you don't want to do. The fact that he trusted me with this and even enlisted my help spoke volumes about him. I thought I knew him. If I were honest with myself, I still knew him, but I certainly had a more clear picture of my best friend. I couldn't help but get a little hot when he said he trusted me enough to take his virginity. I mean who wouldn't?