Anna's Diary Ch. 05

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 was quite adventurous. I have collected the best stories 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.

October 31 2013

Well tonight's the night. Jamila, Brad and I are spending Halloween at a frat party. Over the last month Jamila and I have been going to dollar stores, resale shops and the Halloween store to put together the perfect costumes. The frat is having a theme, "Totally 80's," so my roommate, and apparently mentor, decided she and I would go as slutty eighties girls. Think Madonna in her early years of stardom. She suggested that we be twinsies, except her costume is hot pink with black accessories while mine is black with hot pink accessories. Of course she wanted us to show a lot of skin. I argued a little but she pointed out we'd be wearing big glasses and heavy makeup so no one that didn't already know us would know it was us. I guess that logic worked enough because I relented and agreed.

We found the accessories, lace fingerless gloves, lace hair bow, rubber bracelets and those glasses that are just plastic lines instead of lenses online for cheap. The tutus were found at the Halloween store, luckily for us they had exactly what Jamila was thinking of. The bustier was a little more difficult to find, we looked everywhere. She was insistent that they be lacy but transparent and finding one in hot pink was not easy. We ended up getting them both from a lingerie store online. They were a little more than we wanted to pay but Jemila assured me it would be worn more than once. Trying it on last week I was surprised at how much of me was visible and how little my roommate cared. She reassured me that with the top it'd be fine.

Just outside of town there's a topless bar with an adult store attached to it. That's where we bought the rest of our outfits. She couldn't find a hot pink garter belt so she had to settle for a black one. They did have the right fishnet stockings and lacy G-string panties though. The fishnet shirt was shorter than we expected but we have the lace corset so we both agreed it would work.

Brad just texted me that he's on his way up. He got off easy, his costume makes him look like Bruce Springsteen. Blue jeans, a white shirt and a red hat sticking out of his back pocket. Lucky fuck. The jeans are tight enough to show off his bulge though and the shirt accents his muscles so there's at least that.

October 31 2013 (part 2)

Ok, waiting for Jamila to finish her hair. I am nervous as hell. Even with the fishnet shirt our tities are very visible. Hers more than mine but still. She doesn't seem to care at all. In fact she surprised me by not even thinking twice about changing in front of Brad. I mean, we had our strip card game a month ago but it still shocked me how nonchalantly she dropped her towel after her shower. I could see it made Brad uncomfortable also. His eyes darted everywhere else in the room except directly at Jamila.

"What, it's not like you haven't seen all of this before," she teased him. Standing there casually drying herself she added, "come on Brad, you know I love it when people see me naked. Incidentally, so does your girlfriend."

"No I don't," I tried to protest.

"Yes you do," Brad said with a smile, "and I guess I like seeing others look at you."

Soon Jamila and I were both nude before putting on our costumes. I'm sure Brad was in his own little heaven watching us get ready. In fact, I know he was. We both noticed him shifting in his seat as he readjusted that thing growing just beneath his jeans. I asked him to grab me something just so I could see him stand up. The view of his rod embossed on his jeans was more erotic than if he had pulled it out and showed us. The desire for him to take me instantly consumed my every thought. For a split moment I pondered giving in and letting my roommate watch us go at it. Then the memory of her suggesting to Dwayne that I join them entered my mind and I had to quickly talk myself out of beating her to the punch and offer up my boyfriend first.

Once my costume was on I looked in the mirror and it was obvious that the fishnet shirt did little to hide how much of my boobs were showing through the bustier. I wanted to protest but Jamila was so excited at how we looked.

Taking a big drink of my wine I turned to Brad and asked, "how do I look?"

His eyes kept running up and down my body. The smile on his face told me everything but I needed a verbal confirmation. "Well, I guess I'll put it like this, if Jamila wasn't here I'd be all over you."

"And what about me," Jamila said over my shoulder, "would you be all over me if Anna wasn't here?"

Putting my arm around my roommate's waist I baited him some more, "yeah sweetie, if I wasn't here would you be able to control yourself?"

Brad said nothing. He just stood there getting redder and redder. I don't think he realized he was doing it but his hand was adjusting and readjusting the growing appendage trapped inside his pants. Already being a little buzzed from two glasses of wine I found it fun to tease him more. "What if I was here and wanted to watch you two?" The words that left my lips shocked everyone in the room, even myself. The alcohol was lowering my inhibitions again.

Brad's eyes opened as wide as they could while his jaw dropped slightly in amazement. On the other side of the response spectrum Jamila joined in the torture. Cupping one of my breasts and squeezing slightly she looked directly into his eyes and said, "I'm game if you are."

Watching Brad squirm combined with Jamila touching me was turning me on. I found myself imagining him and my roommate together and it made me even hotter. Again the words came out before I thought them through, "I'm game if you are," I said looking directly at my boyfriend.

He didn't say a thing, Brad just slowly undid his pants. His cock sprang out fully erect and ready for action. This was the moment. Either I ended it right then or I was going to watch my man be taken by my roommate. Jamila and Brad both looked at me for confirmation. Again the words surprised me. "Just a blow-job," I said softly.

Brad began stroking himself in anticipation while Jamila kissed me on the cheek and said, "that a girl." It was like she accomplished something, like she'd been educating me, guiding me to that point and was proud of her pupil.

I sat in a chair and took another big sip of wine as I watched my roommate and mentor descend to her knees and take my boyfriend's member into her mouth. Brad stared at me, watching my reaction. Watching for any negative feelings, any regrets. There were none. My eyes darted back and forth from his face to the action, trying not to miss a second of either.

Before I realized that it was happening I had parted my knees and was slowly, methodically caressing myself over the skimpy panties I had on. They were sopping wet. With one finger I pushed the fabric aside while another one slid effortlessly into me. I could read it in his face that Brad was getting close but before he could erupt Jamila pulled away.

"Ok," she said, "we got to finish getting ready," and went into the bathroom grinning at me the whole time.

To my surprise Brad darted over to me, lifted my legs up and quickly entered my pussy. The rush of feeling his manhood stretch my hole was overwhelming and with-in thirty seconds I was gushing with orgasmic bliss. He lasted about two seconds more before he pulled out and spurted his cum into his palm. He was concerned about getting it all over my costume, what a gentleman. I thanked him by bringing his hand to my waiting tongue and lapped up every last bit.

Ok Jamila's done, time to go.

November 1 2013

Well, we just got home and Jamila is now in the shower, I'm next. I really screwed up. I just got off the phone with Brad and he told me we were through. Unfortunately I have no one to blame but myself. I would love to put some of the blame on alcohol but I chose to continue drinking and no one forced me or drugged me.

After what happened in the room before we left all three of us were charged up. I was so horny I didn't care a bit about how revealing my costume was, every time I thought about it I felt myself getting more excited. From the back seat Brad reached both arms around me and fondled my breast. With little conviction I playfully swatted his hands away but was secretly loving the attention. Jamila half-hazardly told him to cut it out, that she was trying to drive. Brad took that as an invitation to slide over to her side and do the same to her. Jamila squealed and jerked the car into the oncoming lane. Luckily there were no cars in it at the time. We all laughed it off as if it was no big deal.

Brad was in a mood like I had never seen before. I'm sure it had a little to do with how many pre-beers he consumed and a lot to do with the blow-job he got from my roommate. Contorting himself around the headrest he shoved his tongue down my throat while those strong hands massaged my breast.

I was about to jump in the back seat and take him right there when Jemila spoke up, "we're here."

The party was packed. It was difficult to move through the crowded "dancing area" to get to the bar. With one hand I held on to Jamila while Brad held my other as we zig-zagged our way through the sea of people. Along the way I brushed against stranger after stranger, mostly with my breasts. I didn't purposefully do it but I didn't mind either. More times than I can remember people also grabbed my butt and at least twice someone brushed their hand up my front. Normally I would be outraged by someone being so disrespectful but I was so sexually stimulated that everything around me seemed to be turning me on more.

Many of the party goers had fun with the eighties theme and most of the women went with the lingerie as clothes part of the eighties like Jamila and I had. There were barely covered breasts everywhere. More than a few boys wore only a fishnet shirt with skin tight tiny spandex shorts that left nothing to the imagination. I noticed two or three were so excited that their stiff peckers stuck halfway out above their waistbands.

We three danced, drank and flirted with each other. I incuradged Brad to squeeze Jamila's butt and at one point he took it upon himself to lean down and suck on her nipple. I couldn't believe how much that excited me.

Going to get us all another drink Jamila came back with a boy in tow. She introduced him, I didn't catch his name but after another couple songs we all followed him back to his room where we drank our drinks and smoked a joint. With all our drinks empty Brad volunteered to go get us some more. When I turned back from watching Brad push his way through the crowded hallway I observed Jamila in full blown make out mode with her friend. It took about ten seconds for her to go from making out to going down on him. I watched in amazement, as did many people standing in the hall as she unzipped his pants, pulled it out and took it into her mouth.

In my drunk and stoned state of mind I just stared at them. His member was a beautiful dark chocolate shade of brown with a little bit of milk chocolate color wrapped around the base of the head. I'm not sure but I think I was unconsciously rubbing my breast and celevating. When my roommate noticed me she released him and asked me if I wanted a turn. I didn't know what to say but that didn't matter because my lust took over and before I could stop myself I had her friend's cock in my mouth. It wasn't huge like the guy she was with last week but it was a little bigger than Brad's.

As I knelt down my ass went up in the air for all to see. I honestly didn't even think about how exposed I was. Some in the crowd began cheering and my arousal skyrocketed. Jamila and I took turns devouring his thick member. She's almost as skilled as I am and we were both able to deep-throat his entire length. The hairs at the base of his long shaft were much coarser than I had ever touched but his skin was smooth and soft.

A hand grabbed my ass and squeezed it with a light touch. I was too busy with Jamila's friend to look and see who it was and honestly I figured it was Brad. His hands roamed around my nearly bare ass, occasionally grazing his fingers across my painty covered pussy lips. The ruckus around us became more prevalent as the crowd edged their way into the room. When the first finger entered me I nearly had an orgasm. He pumped me a few times before adding a second one. I looked behind me to smile at Brad but it wasn't him. Knelt behind me was a complete stranger. A light brown skinned man with flowing long black hair. In my mind I screamed and pulled away but my body wasn't moving. When he pushed his cock inside me I lost all concern about what Brad would say. With all those eyes on me I felt like the whole world was rotating just for me, like the concept of pleasure was created for that moment, like I was the center of the universe.

Jamila straddled her man and began to bounce up and down on his erection. My face was five inches away from her vag. I played with his balls but didn't touch her. I thought about it but wasn't prepared to go that far. I absolutely loved watching her get fucked while I was feeling the same thing though.

It didn't take long for Jamila's guy to cum. He pulled his cock out and the first shot hit my nose. I quickly took it into my mouth where he finished erupting. I was acutely aware that I was tasting another girl's juices for the first time. I couldn't even describe it because I mostly tasted his cum. The whole experience made my body tense as another orgasm ripped through me. Just as I was calming down I felt the stranger pull out and spray hos cum all over my ass.

The whole room erupted in vigorous applause and whistling. With the moment past we all became aware of the amount of people that just watched us fuck. While in the moment it was a huge turn-on it was very awkward after. The two guys scooted everyone out and closed the door. Jamila's friend lit up another joint and we began to make small-talk. The stranger that fucked me excused himself after the joint was smoked. I never did get his name.

After about ten minutes it hit me that I hadn't seen Brad in awhile. I left Jamila with her friend and went off to look. I roamed all over the house but couldn't find him. I called him but it went to voice-mail. When I made it back to the room I found Jamila still with her guy. We decided that Brad must have walked in on us and didn't like what he saw so he's somewhere sulking.

Jamila was too messed up to drive home so we crashed in the guy's room. The three of us shared his bed until Jamila and him began fucking again. I was worried about Brad and not in the mood anymore so I moved to the floor. At some point in the night I woke to the noise of my stranger fucking some other girl in his bed. By then my head was pounding so I positioned myself away from them and went back to sleep.

When I woke up there was a text from Brad. It read, "I'm sorry I left but when I saw you and that guy I realized you were much too adventurous for me. I tried and had some fun but I can't share you with other guys. It's just not in my nature. I don't want you to restrain yourself for me either so I think it's best if we just end it before someone really gets really hurt. Goodbye."

This sucks but he's probably right. I'm a little ashamed about last night but I enjoyed myself also. I don't know what's gonna happen next but I don't want to be tied down with someone who isn't up for anything.