Anna's Diary Ch. 02

-Anna's Experiences at College-

I started dating Anna about six months ago and she moved in with me last month. Last weekend she took her kids to visit their grandfather on the other side of the state so I once again had the house to myself. While rearranging our bedroom closet I found a box full of old diaries and decided to read them. I was completely shocked. Of course we've talked about our past but not even in her most inebriated state did she mention most of the exploits I read.

Anna is a short girl of five foot one inches. I've seen photos of her when she was young and although Anna was never a thin girl she held a lot of her excess weight in the best place possible, her ample chest. She's always had very long hair and while in her late teens and early twenties it hung down clear past her ass it's now only a little past the middle of her back. Her hair is dirty blonde and although I've never seen her with a bush I have no doubt that her hair color is natural.

Anna went to Western for only two semesters but apparently during that short time she had quite an adventurous time. I have collected them here in small groups because individually some of them are kind of short.

The only form of editing I've done is choosing which entries to submit and which to not. These are all her stories in her own words.

September 17 2013

Met a guy in my Applied Mathematics today. I've noticed him ogling me a few times but today he took the leap and sat next to me. It was so cute, he was so nervous I thought he wasn't going to be able to talk to me. When the class ended he must have gathered up all his willpower and introduced himself as Brad while looking everywhere except for into my eyes. He's not a tall guy, definitely taller than me but as far as men go he seems a little short. He was wearing basic blue jeans and a red Polo style short sleeve shirt. I can't say too much about the features of his face because Brad has a well maintained but thick beard.

His dark brown eyes darting everywhere made me giggle inside. But after a few awkward back and forths he started to gain a little more confidence

I guess he figured I wasn't going to shoot him down right away. We walked and talked about normal stuff like where we were from and what we were studying until we got to a point where we had to part ways to get to our next class. Before we did he asked me if I wanted to go out, I said sure and then we exchanged phone numbers.

September 18 2013

A couple of hours ago I met Brad at a coffee house. We sipped our coffee and bs'ed about almost everything. He's from Ludington and this is his second year here. He's majoring in political science. I can't believe this, people actually study to go into politics. I just thought any idiot can get elected and then you work your way up but no, you can actually take classes to learn how to be a politician. I don't know if he's practicing or not but he is a good listener and he really seems to care about the subjects we discuss. The only thing we didn't talk about was politics. When I brought it up he kind of sidestepped the conversation and quickly moved on to something else. "Brad's gonna make a good politician," I thought.

Overall he seems like a nice guy and by the end of the date I decided I would give him another so we're going to meet this Friday for dinner.

September 21 2013

Last night was my date with Brad. He took me to an Italian restaurant in downtown Lansing. I got lasagna and he got chicken marsala. The food was excellent, it tasted really authentic and homemade. He was kind enough to let me taste his because I've never had chicken masala before. I'm definitely going to have it next time though. We talked some more about everything and nothing at the same time. You know, favorite colors, favorite cars, favorite animals, those types of things. We just dove a little deeper into each other's likes and dislikes then we did on our first date. After getting to know him even more I still like him so again we planned on another date.

Now I have to decide, because this will be the third date, on whether I want to sleep with him or not. I mean, I probably will, this is college and that's what you do right, experiment and try to expand your boundaries. To me that includes sexual experiences but that doesn't mean I won't be nervous about it or wonder if It's the right thing to do. I've only been with one other guy and he was a tourist so we only had sex seven times before he had to leave. I'm sure if he initiates it I will probably have sex with him. My biggest question is where. Should it be in his dorm room or mine?

September 23 2013

Well, Brad definitely didn't try to coax me into having sex with him. We had a passionate make-out session that I thought was going to lead somewhere but Brad stopped it abruptly. He didn't even try to get under my shirt. I can see wanting to take it slow but it couldn't get much slower. I think I'm going to have to push this along.

October 4 2013

It's about time. I mean, it's not like I was looking to have sex on the first date or anything but it's been like ten. I think Brad was a virgin, at least I kinda hope he was, because everything he did seemed like he learned it from a movie or the internet. He knew all the mechanics but he didn't have any rhythm to his movement. Even though the lights were on it felt like he was fumbling in the dark.

Jemila went out with her basketball friend and before she walked out the door she whispered, "don't expect me back tonight."

Knowing the place was mine completely I invited Brad over with every intention of getting laid, even if I had to set up road flares directing him to my vagina.

Brad's not much of a drinker but I made sure I had two glasses of wine ready when he arrived. After about half a glass Brad started to get a little looser with his touching. I wore a skirt to give him easier access but his hand didn't seem to want to go much above my knees. Once we began passionately kissing each other I took it upon myself to place my hand in his lap. I wasn't even being subtle about it, I rubbed him through his jeans. Feeling him grow beneath my touch was exhilarating but he didn't reciprocate. "This guy," I thought, "is either incredibly shy or incredibly dense."

After about ten minutes of making out and him still not getting the hint I excused myself to the restroom to freshen up. When I came back out I was wearing a sheer nightgown with matching panties. Brad couldn't take his eyes off my chest. His gaze followed my tatas as they jiggled and bounced with every step I took towards him. When I reached the bed he finally placed a hand on my breast, though it was very gentle. I in turn grabbed the back of his head and buried my tongue aggressively deep into his mouth. I was tired of his slow, meek approach. I took complete control of the situation, either he was going to get scared and run away or he was going to give in to the power of a woman who knew what she wanted.

When he responded with a tight squeeze of my boob I knew Brad finally relented to my seduction. I guided him to lie on his back and then climbed atop of him. As I started grinding I quickly realized that his jeans were going to hurt my delicate little kitty so again I took it upon myself to rectify the situation. As he kicked his shoes off I unbuttoned his pants and yanked them to the floor. He wore loose fitting checkered boxers but I could clearly see he was aroused. Climbing back on him I felt the full extent of Brad's manhood for the first time. It was bigger then I would have guessed, thicker too. Spending the past few weeks fantasizing about that very situation I longed to feel Brad's hardness fill my tight hole. I thought about it while I touched myself, I said his name under my breath as I brought myself to completion and on more than one occasion I dreamt about him and woke up wet and horny.

In that moment I ached to feel him, my body was nearly quivering in anticipation. Throwing myself at him like I did gave him no doubt of what my intentions were and he didn't disappoint this time. Maybe I ought to be ashamed of the way I behaved but the fact is I felt sexy and empowered.

Brad began sliding his erection up and down the length of my engorged lips. With each thrust his dick pressed against my clit shooting pulses of arousal throughout my body. Neither of us could take the teasing anymore. As I stood to yank my panties off Brad pushed down his boxers. There it was, on full display. I wanted to see what my tiny fingers would look like wrapped around his girth, I wanted to find out how much I could fit into my mouth but as charged up as we were I was afraid he'd explode prematurely. I was determined to bury him inside me. All in one motion I straddled him, grabbed his throbbing cock and guided it into my eagerly awaiting pussy. It felt so good as it went inside me. It stretched my walls more than anything had ever done before and I loved it. He filled me so completely that I had hints of pain like I did when I lost my virginity.

With every slow thrust Brad penetrated deeper and deeper until it couldn't go any further. Gaining speed and intensity he soon pounded that large member inside of me. It hurt so good I could hardly contain myself. I wanted to scream out in pleasure but restrained myself so as not to let the whole dorm know what was going on in my room. The intensity grew wilder as I met his thrust with my hips. My titties swayed violently in all directions as our bodies smacked together. More than a few times I felt one of my boobs hit Brad in the face but he only reacted with a smile.

Ten minutes in it was perfectly clear that Brad was not going to cum too quickly as I had feared. Paul wasn't a two pump chump or anything but if he lasted five minutes it was like a marathon for him so I was now in new territory. Brad rolled us over and once on top he began to pound my pussy relentlessly. If that was his first time, like I still think it was, he was a quick learner. His rhythm got better but he tried to do too much at once. He fell out of me more than a few times while attempting to also suck on my nipples. One time he nearly entered my back door unexpectedly. When his cock pressed against my asshole my brain screened right before my mouth did. I had to stop him and tell him to concentrate on one thing at a time for now.

After twenty minutes of intense fucking in multiple positions I was getting tired and my little kitty had become sore. I already had two orgasms but he wasn't showing any signs of even reaching one. Repositioning us I went down on him while I stroked his shaft and played with his balls but to no avail. I felt bad, and still do, but what was I supposed to do? Luckily he didn't seem to mind and we just climbed into bed together and Brad stayed the whole night. Amongst many highlights of last night, falling asleep in his big strong arms was up there as one of my favorites. I had never literally slept with a man before and unsurprisingly I enjoyed it immensely.

Sometime in the early morning I felt his hardness pressing against my butt and immediately got horny for another round. I arched my back and raised my leg, giving him an easy pathway to slide his manhood inside me once again. Slowly and methodically he made love to me. It felt so wonderful but after a few minutes I was ready for a different position. Guiding him to his feet I bent over the side of my bed and Brad took me from behind. Of course he started off slowly but soon he was gripping my hips tightly and crashing his pelvis against my ass intensely. Before I knew what was happening Brad had pulled out and was ejaculating all over my back. He shot his spunk all the way up to my shoulders getting plenty of it in my hair which led to another new experience for me. I got to shower with him.

Showering with Brad was awesome. We ran our soapy hands over each other's naked bodies not missing a bit of flesh. It wasn't as sexual it as I figured it would be but still very nice. After we were finished we wrapped ourselves in towels and sat down together in my desk chair. I sat in his lap while we shared a small bag of chips and a pop. It was only six in the morning. I honestly expected him to get dressed and head back to his dorm but was pleasantly surprised when he laid down in my bed and as cute as can be he patted the mattress gesturing me to join him.

Once again we fell asleep in each other's arms and it wasn't until I heard my roommate's voice that I woke up again. "And what do we have here," Jemila said playfully.

Barely awake I said, "oh, good morning Jemila." For a split moment I forgot that there was a naked man pressed against me.

"Good morning indeed, though I would probably guess you had more of a good night, huh?"

"Shh," I said, "you'll wake him. "What are you doing home so early anyway?"

"Early, it's nearly ten thirty."

"Oh," I said, starting to wake up completely, "well go take a walk or something and I'll get him up and..."

"And dressed?" Her smile was pure evil. "Nah, I think I'll sit here and enjoy you two trying to put your clothes on without exposing yourselves."

"That's not funny, just give me ten minutes and then come back," I thought for a moment and then added, "please."

Adding just a little attitude Jemila responded with a snippy but fun-loving' "fine, I guess I'll be taking a walk." Even before I could say thank you she added, "but I'm getting details."

"OK, just go before he wakes up." The purposeful slam of the door woke Brad up. That was too bad because I was thinking of a much more enjoyable way to do it. I've been told by a couple of guy friends that the best way to be woken up was by a blow-job and I wanted to do that for Brad. I wanted to make every bit of our passionate night together memorable but Jemila altered that plan slightly. Instead we kissed and before long he was maneuvering me onto my back so he could climb on top of me.

"Jemila's going to be back any minute," I said.

"So."

"So you want her to walk in on us," I said firmly.

Brad surprised me by seemingly thinking it over for a split second. He's definitely gained some confidence from last night. I guess it's true what people say, sometimes you just need to get laid. "No I guess not," he said before rolling off of me.

I got up and quickly started to get dressed while Brad followed close behind. By the time Jemila opened the door again we were both sitting on the edge of the bed, fully clothed, holding hands and lightly kissing each other. She smiled a wicked little smile at me and made her way directly to the bathroom. When she emerged I asked her if she wanted to join Brad and I for breakfast. She agreed and all three of us spent the afternoon together.