Annas Diary Ch 03

-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 adventure. I have collected them here in small groups because individually some of them are kind of short.

This one blew me away. I wish I had have the experience in college that she had.

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 20 2013

Last night sure was a new experience, at least for me. Jemila invited me and Brad to go hang out at another one of her boy-toys apartment. This one's name was Stan. Thinking it was going to be a night of drinking filled with conversations about nothing important we said yes. Jamila drove Brad and I to the apartment. It was far enough outside town that it'd be an especially long walk back to the dorms. I'm wondering now if she took that into consideration beforehand. Within ten minutes of arriving I knew we were in for more than we had figured. There was an uneasy energy in the air and I felt like an animal must feel when the trap springs and it knows it's been duped.

I've met Stan before but his roommate Quinn had to be introduced. Both of them were skinny and tall, I'm starting to think Jamila has a type. Stan had brown hair and blue eyes and Quinn was blue eyed also but had a very carrot colored mop on top of his head.

A mixed drink of vodka and 7 up was put in our hands mere moments after we arrived. As we were seated around the table there was a knock at the door. Jemila got up and answered. Turning around I was pleasantly surprised to see Yolanda would be joining us for the evening, she's one of Jamila's good friends. I've met her a few times now and find her pleasant to be around. I'm not into girls but I can surely appreciate the beauty of one and Yolanda is a knockout. Tall and thin but still curvy in all the right places. Her hair hung down to the middle of her back in tight small braids. Deep purple in color it looked amazing against her milk chocolate skin tone. The eyes that gaze back at you are a soft brown that sparkle majestically, inviting you to get lost in them. Taking the chair next to Jamila she looked around the table and presented each of us with her warm smile.

Quinn playfully said, "hello there gorgeous." There was definitely some history between them that I had not known about.

"Hello to you," she responded but then quickly added, "handsome fella."

"So," piped up Stan, "the rules to strip thirty-one are."

"What thirty-one," I blurted out.

With the sliest smile I have ever seen Jemila present she said, "oh, did I forget to tell you. Oops."

Brad and I looked at each other knowing what the other was thinking. Finally he spoke up and said, "I'm game if you are," so the decision was made and we decided to play. I was a little mad at Jamila for setting me up but that quickly changed when I thought about potentially seeing Stan and Quinn in the buff.

The rules were simple enough. You get three cards, on your turn you pick up from the deck or the discard pile, you discard the one you don't need. The objective is to get thirty-one, or as close as you can, in the same suit. When you think you have a good hand you knock and everyone else gets one more chance. The closest to thirty-one wins, the furthest away loses. If someone gets thirty-one they don't have to knock, they just lay their cards down and everyone else loses. If you lose you lose a piece of clothing. For that game Stan said that because there were so many of us that shoes and socks each counted as one.

First round went to Stan while Jamila lost. I was happy she lost, she deserved it for ambushing me and Brad. The rule was you had to stand up and take your piece of clothing off. That wasn't a big deal when it was shoes or socks but pants or undies, that seemed to make the game even more risqué. The second round went to Brad, yay, and Quinn lost. My drink seemed to disappear faster than I realized and I became more comfortable with the idea of being nude in front of all of them. That's not to say I wanted to lose, I was just less nervous.

It went round and round with everyone losing pretty evenly, except for Stan. Into the seventh round he still hadn't lost. The best part of that was right after he opened his mouth and bragged about it he lost two in a row. Once Quinn lost his shirt the evening seemed to become much more exciting. His chest was toned and hard, he had a tattoo of an American Eagle on his left pec. With its wings spread wide and its talons extended it looked like it was about to strike.

Jamila was the first girl to lose her shirt, again I couldn't help but feel she deserved it. She stood up and methodically unbuttoned her blouse. Each button revealed a little more of her pastel orange bra underneath. It seemed to glow against her dark skin. The lacey garment struggled to contain her substantial chest. I noticed Brad relentlessly staring at her. I imagined he was comparing her size to mine. I wasn't jealous. The only real difference between hers and mine is the skin tone.

The next round I had the lowest hand so I had to remove my socks. I was very aware that if I lost again I would be showing some real skin. Because I wasn't warned about the plans I hadn't made preparations. I had on my sheer black bra that I knew got Brad riled up. It didn't even cross my mind when I put it on that someone other than Brad was going to see it. Of course I lost the next hand also. I was so nervous. Yeah, Jamila and Quinn both had their shirts off already but I knew much more of myself was going to be on display. I was very aware that every pair of eyes were focused on me, on my chest to be precise. On the ride over I teased Brad by grazing my hand over his crotch and whispering in his ear what I had on under my clothes, so he knew what kind of show I was about to put on. I looked over at him and he was grinning like a cat who just swallowed the canary. After taking a big drink from my glass I stood up, quickly and matter-of-factly removed my shirt and then quickly sat down.

"Wait a minute, " Stan said, "aren't you supposed to give us a twirl?"

I stood, twirled and then sat back down, all within two seconds. Everyone laughed and moved on but the two boys sitting across from me could not stop staring at my chest. I felt so uncomfortable but it also excited me. The slight tingle between my thighs told me I was enjoying myself more than not.

The first thirty-one was accomplished by Quinn. Everyone else had to lose a piece of clothing. The other two boys lost their shirts as well as Yolanda. Stan's toned chest had no tattoos on it but both his nipples were pierced. That was the first time I had ever seen that in person. Yolanda had on a cute little purple bra that matched her hair perfectly, apparently she got the courtesy of being informed about last night's activities. The bra covered up her small breasts completely with ease but it was still erotic.

Jamila and I had to remove our pants. We waited until the other three were done before we started. Simultaneously we stood and dropped our pants to the floor. Jamila was wearing a miniscule black thong that barely covered her. The fact was, if someone looked close enough, and apparently I did, they could see her bush creeping out the sides and top. She did a slow spin and even bent slightly over to display her nearly bare ass. I was beginning to understand just how much of a flirt my roommate is.

Again, I was not informed of the night's activities. I had worn panties that matched my bra in every way, right down to the sheerness. I know my slit was visible. The panties covered some of my ass but the transparent fabric left little to the imagination. I did my spin and sat down.

The next loss fell to Brad and he had to remove his pants. Standing up he undid his button and fly and slid them off. His red boxer-briefs hugged his erection tightly. It was pushing against the stretchy fabric seemingly begging to be set free. The other two ladies couldn't take their eyes off of my man's bulge and it made me even more aroused.

Jamila lost the next hand which meant she was the first girl to show titties. Mine were pretty visible but technically covered. Having seen them many times I watched the boys' reactions. Stan's expression told me that wasn't the first time he saw them. Quinn and Brad though, they were like kids on Christmas morning. The gleam in both of their eyes was cute. Their smiles grew as the bright orange fabric slid down her arms. Her nearly black nipples were pert and so alluring. When she did her spin Jemila's large breasts bounced and swayed, captivating everyone else in the room.

After the next hand it was time Quinn to show off what color underwear he was wearing. His shorts slid down to the floor revealing a pair of white bikini style undies. They were tight and it was very obvious he had a boner. Unfortunately it was also obvious his sausage was more like a hotdog and not even a bun-length hotdog. It was a relief to know Brad wasn't the smallest.

Yolanda seemed pretty happy sitting at the head of the table. She and Stan were tied for the most clothes remaining. That all changed when she lost the next hand and had to remove her skirt. It was long, tight and made of black leather. Yolanda turned around and slowly unzipped. Each centimeter displayed more of her smooth milk chocolate skin. When the waistband of her panties came into view it was revealed to be the same color purple as her bra and the highlights in her hair. As the skirt slinked down her thighs that small alluring backside of hers caught all of our attention. Her skin was perfectly smooth and her ass was so tight that I felt a hint of jealousy. In my whole life I never had an ass like that. Before I could implant her perfection to memory she did a quick spin and sat down ending the show.

Yolanda's luck did not change. She lost again immediately. With exaggerated disappointment she stood and unfastened her bra. Turning around to face away from the group Yolanda tossed her bra over her shoulder. Like a dirty version of throwing the bokey it remarkably landed in Quinn's lap. We all laughed as Quinn mocked putting the bra on but when Yolanda turned back around our attention emeditly went back to her.

Her hands covered her small breasts entirely. She teased us by spreading and closing her fingers all the while skilfully continually covering her nipples. When she finally exposed herself totally we all cheered. Her breasts were beautiful. Superbly round they were as smooth as chocolate milk and the same color too. Her dark brown nipples pointed away from each other, I think it's called east west style boobs. They extended outwards, doubling the length of her breasts. I've never seen nipples that long before. My own thoughts kinda shocked me, all I could think about was what it would be like to suck on them. The only flaw, if you could call it that and I wouldn't, was that the left one was a little smaller than the right one. It made no difference to me, or anyone else in the room I'm guessing, those little tities of hers were flawless.

The game abruptly neared the end with the next round. Brad slammed down his cards in triumphant glory. He had thirty-one. The smile on his face was full of bravado I had not seen before. That one hand ended the game for Quinn, Yolanda and Jamila. My roommate took her panties off first. Again Brad and Quinn unapologetically stared at her. She didn't seem to mind a bit. During her spin Jamila bent slightly and gave herself a good smack on the ass. Brad instinctively began rubbing his cock through his underwear while Quinn pulled his out and began stroking. His penis looked smaller beneath his underwear than it did on full display. It was still smaller than Brad's but bigger than I had anticipated. The most noticeable thing about it was Quinn's orangish-red pubes. I had never seen that before and I must admit I didn't really like the way it looked. That certainly didn't stop me from staring though. When he did his spin Quinn made sure to flop his hard-on numerous times before sitting.

Stan stood and unceremoniously dropped his pants and spun around. Luckily I was looking because it happened fast. All I remember was noticing he had boxers emblazoned with the college's colors and logo.

It was my turn. As calmly as I could I removed my bra allowing my boobs to drop. With both nervousness and excitement I watched them ogle me. I knew Quinn and Stan were committing every inch, every bump, every soft blue vein that was visible beneath my skin to memory. I slowly did my spin. Allowing the room full of people, three of which were strangers two hours ago, to leer at all I had to offer. The total exposure exhilarated me much more than I care to admit, even now. Just before I came full circle I began to bounce. The reaction was exactly what I expected. All the boys began to hoot and holler, even Brad. I sat down and looked to the head of the table.

Everyone could see Yolanda was not happy. She stood up with a jerk. "I wasn't supposed to lose," she snipped. I couldn't tell if she was being serious or not until she let a smile escape. "I never lose."

"Well tonight you did," responded Stan, "now let's see what you got hiding beneath those cute purple panties."

Yolanda smiled in a playful manner. She turned around and slid her panties to the floor. Her butt was small and tight. When she faced us again her nakedness was truly on complete display. The boys were practically drooling and I can't say I blamed them. A small inverted triangle shaped patch of perfectly manicured fur was surrounded by skin as smooth as it could possibly be. Her pubic hair was as purple and as bright as the highlights on her head. It was the prettiest vag I've ever seen.

Yolanda sat down and our attention reluctantly went back to the game. There were only three of us left. Me, Brad and Stan. We only went around twice before Brad knocked and after laying the cards down I was the loser. Brad gave me a look as if to apologize. Stan and Quinn on the other hand were both ecstatic. All the girls were about to be naked.

I decided to not be upset about losing. If I had to put myself on display, and I did, I was going to put on a show. I'm sure the third glass of Rum and Coke had something to do with that. Standing up I slid a hand into my panties. The sheer fabric gave them an almost unobstructed view of my fingers gliding over the soft bare skin of my pussy. All around me eyes bulged. The boy's reaction exhilarated me much more than I would have previously thought. I think I like being watched. Like really like it. I got so into it I slipped a finger between my lips and rubbed my clit. I closed my eyes and threw my head back slightly. A little moan escaped before I could stop it. That's when I lost my nerve. Opening my eyes I saw everyone staring at me and it felt so awkward I simply pushed my panties to the floor and sat down. I didn't even do the spin. Nobody complained though. I guess they figured they got enough of a show.

Brad leaned in, kissed me passionately while one of his hands squeezed my breast. Whispering into my ear he said, "that was fucking hot," and then gave my hardened nipple a light pinch. It was intoxicating. My hand made its way under the table and back between my thighs. Gliding a finger just past the surface of my slit I felt the warm sticky sap exuding from with-in me. God I was so horny. I would have let him fuck me right there on the table in front of everyone if he asked me to. Of course he didn't though. Insted Stan interrupted us by clearing his throat. He smiled at him and proceeded to shuffle the cards. "One last hand," Brad said with conviction.

"Last hand," Stan repeated. "You know, we both already won. We both got to see what we wanted. We could just stop."

I could see Brad contemplating the idea. Before I could speak up Jamila beat me to it. "To hell you can," she said with authority, "we can all get dressed right now and never play this again."

"I was only kidding," Stan said, trying to backtrack.

"You better be." The smirk on Jamila's face told everyone she wasn't upset. "Deal the cards Brad, us girls want at least one more show." Looking directly at Brad she continued, "personally I hope it's you. I want to see what puts that smile on Anna's face."

Brad's cheeks turned red. I would have scolded Jamila but I was thinking nearly the same thing about Stan. "Take him down honey, I want to see what puts that smile on her face." Jamila and I both giggled while Brad dealt the cards.

After a couple turns Brad still didn't have two of the same suit. All he could hope for was that Stan was having the same problem. When he picked up a fourth high card and had every suit I let slip a "jeez" which made Stan immediately knock.

Brad gave me a look of disappointment and then said, "thanks alot." If I hadn't been sitting there completely naked I probably would have felt much worse. Brad discarded and immediately picked up another card, an Ace to go with his Jack of spades. Too late though. He laid down his eleven.

Stan laid down twenty-six. "Yeah, thanks Anna," he said in triumph.

Brad stood and removed his underwear. His cock was at full erection. "Enjoying yourself I see," I said playfully and then squeezed his stiffness. He instinctively shuttered in pleasure but pulled away from me and gave me a stirn look. I could tell he wasn't mad but I think he was punishing me for helping him loose.

Quinn broke the moment, "now what?"

"Now Stan removes his undies and we all move to the living room to drink and bullshit," responded Jamila.

"What if I don't want to," Stan said with a playful grin.

Jamila just glared at him. Yolanda on the other hand spoke up, "well, we could all get dressed. Is that what you want?"

Stan didn't say anything. He just pushed his boxers to the floor. He was definitely bigger then Quinn but he probably wasn't bigger then Brad. I would have liked them to stand next to each other and compare but I was too shy to ask.

We all moved into the living room. Yolanda and Quinn shared the recliner. With her strewn across his lap I was disappointed his penis got covered up by her legs. Immediately after they got situated Quinn's hand began delicately caressing Yolanda's breast. His fingers slid around her pert nipple in tiny circles. My whole body warmed up. Every few seconds he would pinch her and she would moan uncontrollably.

The rest of us sat on the couch. Boy girl, boy girl of course. I was wedged in between Brad and Stan, my hips touching Brad's hip and Stan's butt. Jamila and Stan faced each other and kissed passionately and loudly. I didn't know how to react so I just downed my fourth Rum and Coke and turned slightly to kiss Brad. My ass pressed against Stan's and my hornyness increased. "Are we going to do this?" I whispered. I didn't know what "this" entailed but I wanted to get a read on Brad.