Month: March 2014

Assfucking 101

I was an 18 years old college freshman and living in a coed dorm. I was also quite a shy kid and didn’t know very many people in the dorm but I did make friends with the RA. She was a 21 year old Puerto Rican senior pre-med major. Since I was also pre-med, she sort of took me under her wing when I came to the school.

One evening I was preparing to take a shower, so I slipped on my robe and was walking down the hall to the showers. The RA was standing in the hallway, she complimented me on my robe, which was a black, silk robe that barely came down to my knees. It was a high school graduation gift and since I never used a robe at home, I had no other robe to use, so I used it despite the many jokes from the other guys in the dorm that called me Hugh Hefner whenever I wore it.

Well I thanked her for the compliment and she said “before you take your shower I wanted to give you that book you were asking me about, however, I am about to go out so come and get it now.”

I said “Ok” and followed her, actually I was walking behind her staring at her soft ample behind. She normally dressed down with sweats and t-shirt but tonight she had on a tight black dress with her hair and make-up done to perfection.

As I walked in her room, I noticed that it wasn’t in its usually state of student disarray but neatsome may even have considered it clean.

I said to her jokingly, “expecting someone over?”

She said “yes.”

“Ok, let me get the book and go before they get here, I said.

She said, “it’s over there on the desk.”

So I went to retrieve it. As I did, she closed the door. This was strange because anytime myself or any of the guys in the dorm was in her room, the door was to remain open, university rules.

So I got the book and was about to leave when she said, “do you like me?”

“Sure,” I said naively, “I like you a lot, you have been a great mentor.”

“No,” she said, “I mean if you had the chance, would you want to sleep with me?”

Now I was completely stunned, here is this gorgeous woman and she want to know if I wanted to have sex would her, was she crazy, of course I did, shit, I had sex with every day in my fantasies.

So I said, “Uhh…yeah…uhh, I think so.”

I was scared as hell not knowing what to say or do next. She told me to go sit on her bed and told me to lean back.

“Don’t be nervous” she said, “I like you alot and I think we can be real close.”

She then began to kiss me. She kissed me more than I kissed her because I was still shocked. She saw how nervous I was and asked if I was a virgin.

I said “no,” which was technically true, I did have sex one time with my old girlfriend but she chickened out midway through so I never came. But I did penetrate, so I wasn’t a virgin. I don’t think she believed me.

She said “I going to treat you real nice, we can take it nice and slow.”

Best Friends Girl

I have known Rick since we were seven years old. We are completely different people but we have stayed best friends. Rick is smart and ambitious. He is handsome and good with the ladies. I have always envied his charm. He seems to attract women without even trying. I am more of a quiet person. I enjoy being alone with a book or a movie. I have accepted the fact that I will never be cool or part of the “in crowd.” Still, Rick and I have always been tight. There is a bond between us that I don’t understand but I know exists.

Over the years, Rick’s taste in women has been awful. With the wide variety that he had to pick from, I never understood why he chose the ones he did. He always picked the air heads and the bimbos. Fake boobs, too much make-up, and really big hair. That was Rick’s type. I don’t know, maybe with his ambition he just wanted something that looked good and wasn’t a threat to him.

A few years ago, Rick called and said that he had met someone new and wanted the three of us to go out for dinner. We agreed to meet at our favorite Italian restaurant at 8:00 that night. While I was waiting for them to arrive (Rick is always late) I tried to imagine what this new girlfriend would be like. I thought she would be like the rest – tall, blonde, big boobs, long legs, and no personality. I couldn’t have been more wrong.

Rick walked in with a petite, dark-haired, dark-eyed, Asian woman. He introduced her simply as Amy. I was dumbstruck. Amy was beautiful. She couldn’t have been any taller than 5’3”. She had shoulder length black hair with a few brown highlights. Her eyes were big and brown. She had a tiny little body with full, natural breasts. I could not believe how beautiful she was. She didn’t wear any make-up. Her skin was smooth and flawless. I must have starring but I couldn’t take my eyes off her.

As we ate, I was repeatedly shocked by what I learned about her. She was a second grade school teacher. She lived at home with her mother. She read and wrote poetry in her spare time. She even went to church every Sunday with her mother. She seemed shy and innocent. This was the kind of girl that you just instinctively try to protect. Amy was not Rick’s type of girl. This was my type of girl.

It’s difficult to say when I first realized that I was in love with Amy. I just looked up one day and knew. Of course, it was wrong. Rick was my best friend and he loved her. It went against everything I thought was right. There was no possible way for Amy and me to be together but it was all I could think about. I thought about her laugh. I thought about her smile. And yes, I thought about her soft lips and her perfect body. I couldn’t get her out of my mind.

Slowly, Amy and I had grown close. One of our favorite pastimes was for the three of us to go to the local sports bar. Amy and I would talk about books or current events while Rick would catch the highlight reel on the TV. I loved those talks with Amy. She was so smart and funny. I would sit across the table and wonder why someone who was so perfect for me could be so unattainable.

It hurt Amy to think of me being alone. She tried to set me up a few times with her friends but I always turned her down. “I’m still hurting,” I would say. Amy thought I was talking about my last disastrous relationship but really I was referring to her. I felt like I could never love anyone else. For me, there was only Amy.

My birthday is in the middle of June. I hate to work on my birthday so I always take a weeks vacation. Of course, Rick and all my other friends had to work so we agreed to have my birthday party on Saturday.

On Thursday, I slept in. I had no plans and no obligations. I took a long hot shower and looked forward to a quiet day alone. I sat on the sofa and turned on the TV. I really just wanted something to distract me from my thoughts of Amy. Lately I had begun to fantasize about her almost constantly. I wanted her so much that it hurt.

Webcam Fun

Matt was a pretty cool guy. I had chatted with him online for over a year now, and due to the distance between us we hadn’t met each other yet. He was a computer tech based out of Silicon Valley, and I was an Administrative Assistant living in Florida. However, that was all about to change.

Matt had it all. He was smart, good looking, funny, and a good friend. Our chats had started out completely innocent. Mostly stuff like ‘how was your day’, and, ‘ what do you like to do for fun’. As months passed by, though, our chats became more serious. We had discussed everything from what we want in life to how many kids we’d want to have. Also, around this time, our chats got a little more risqué. We began exchanging fantasies and having cybersex.

We had done everything that people do when they first chat. Exchanging pics back and forth. As in our chats, the intial pics were purely innocent. Pics of us with our friends, at the beach, of us with our families. Normal stuff. However, just like with our chats, our pics became less and less innocent. From me in my lingerie, and him in his boxer briefs…to nothing at all. We eventually got to the point where we would specify how we wanted each other to be positioned in the pics we were taking.

About a month into our chatting, we had both decided to purchase a webcam. Unlike the chatting and the pics, this didn’t start off innocent. We knew exactly why we’d each purchased the cams, and what we wanted to do. I told him for my first inital act, I’d like to perform a striptease for him. I told him the song I was planning on stripping to, and how we could, through online microphones, be able to hear each other while performed.