Anna's Adventures

Chapter 5 "WTF now Anal Sex?"

Over the next month sex became boring. Even after Prom when Paul and I planned a gang bang. Paul, Steve, Pete and Carlos fucked me. I especially enjoyed Carlos and peaked every time he fucked me. But still was a little annoyed that I never quite reached the heights I had previously.

Maybe it was the newness of the situation with Paul and Carlos the first time that I felt was the best. Or maybe it was the 10 guys. Or, maybe close to that, was the older men. But I knew I wanted that totally satisfied feeling again.

Paul and I broke up soon after Prom as I kept wanting sex with more men and he wanted more of a relationship. I never did tell him about the teacher night or Cody. I felt telling him would hurt him even though he was the one who started me down this path.

Mr. Hanson and I talked after class leading up to the final exam.

I said, "So this final... I'll give you Monday night after graduation for an A on the exam. One night, it doesn't matter how I do on the exam. I get a A!"

He didn't rebuttal just excepted what I laid out. I suppose he knew I would be leaving soon and this was his last chance to fuck an 18 year old student for a while.

I didn't study for the test but tried on the test anyway. I knew probably half of the answers and felt I made a good educated guess on a lot more. I would have guessed that without studying I would have gotten a C. Hey at least I'm not a dumb slut I figured.

The same crew was waiting for me that Monday. I was actually hoping for something or someone new. The only change was they skipped the poker game completely. I just brought them drinks and we chatted about school, life, and other things for the first hour before the fun started.

But really it was a repeat of the last time without as many peaks. Don't get me wrong, the sex was great. I was just hoping for something spontaneous or new.

My parents wanted me to get a job for the summer. I asked Carlos about the pizza place.(After Paul I called Carlos for regular booty calls probably 2 to 3 times per week, and with Cody another 2 to 3.)

He got me a job delivering and he "moved up" to taking orders and prepping boxes.

It was a low end job but something I could do to earn a little money. My second night on the job I had sex with the manager, #20 on my body count. This was not only good sex, as it was new and spontaneous, but it led to quite a bit of leniency for me. He showed favoritism toward me and he was obvious about it, Carlos got pissed and actually wouldn't have sex with me for a week. Then he got over it and we ramped it up to 5 nights a week. I also continued the sex with my manager once or twice a week too. Some nights both. Manager got me first then Carlos got round 2. One night I had Cody become round 3. Yeah. I was a slut for sex and I was loving it.

I was getting used to Carlos and Cody. Each had their own special qualities. Carlos with his size and aggressiveness could get me to cum anytime and anywhere. Cody with his experience and variety of positions and his dirty talk. With each man I would be dripping before their cocks even touched my pussy. The manager, after the first time when it was good, now I would just fake it. It worked though. He got to fuck me and I got an easy job out of it.

One night when I was working a larger order came in from a richer part of town. Me and another delivery guy were waiting for our next one. It was his turn but I talked with the manager as I wanted this one. I had dollar signs in my eyes. The other delivery guy was a little upset. But I couldn't deal with that. I had my reasons and well I "did some extra credit" with the manager to earn my rewards.

I put the 3 pizzas in my warmer bags and off I went. When I arrived I could see a party was going on. I knocked on the door and it swung open. A chick about 20 years old was standing in the door with just a towel on. I glanced inside as I assumed she was dared or something and there were 4 guys watching her. She looked at me and sighed.

She yelled to the guys, "Pizza GIRL is here!"

She looked relieved but when one of the guys came to the door he looked upset. I suppose they were hoping for the guy. I knew the situation probably better than anyone my age and I didn't want to disappoint.

So I said to the woman, "Mmmm coming to the door in a towel!"

She looked at me and stared!

I looked to the guy. And said, "Here I thought this night was going to be a bore!"

He seemed to get what I was throwing down and motioned for the woman to do what she was supposed to do.

She seemed to plead with the man but in the end she faced me and as I handed her the 3 pizzas her towel fell down. She looked quite embarrassed probably from the guys but also that I was a woman.

I said, "Oh dear, your towel fell. Let me help you. Those guys might see too much!"

I walked inside and took the pizzas back from her and shielded her body from the men.

I put the pizzas down and now with her totally naked in front of me I said, "Mmmm, you are something to admire! You're hot!"

Truth is she was hot. Larger boobs than me and a fuller ass. Still skinny. With her basically larger body I figured her to be about 125 pounds while I was around 113-115.

Her face got even more red if that was possible and she muttered, "Thanks."

I reached down and grabbed her towel to hand it to her. But I peaked at the guys watching us. I decided to see where this would lead. I continued to hold the towel in my hands.

I said to the guys, "I suppose my gender caused a problem with your plan this evening! But just so you know, I think she is damn sexy!"

The guys seemed to be in a relative state of shock as I really didn't know what to do either. I looked back at the woman and said, "Dare? Lose a bet?"

She said, "Dare!"

I said, "Been there! Now let's have some fun."

I looked at the guys and tossed the towel toward them.

I said, "So... whose idea was it anyway?"

They all looked at one guy.

I looked toward the guy and said, "I get it she's really sexy. And... mmmm probably a little adventurous! But..."

The one guy who they were staring at said, "But what?"

I said, "How come it's always the girl getting dared to show off for pizza and not the man?"

He said, "Um... just the way it is I guess."

I said, "Now... I dare you sir... let's try this again but with you in a towel, and answer the door for me!"

He said, "Fuck no!"

The naked woman next to me said, "Yeah Frank! I dare you!"

He said, "Um... no.... I can't."

The guys were starting to come around to my idea were egging him on to do it.

I said, "Why not! You like women teasing delivery men. How about a man teasing a delivery chick! Sounds fair to me."

He tried to get out of it but finally resigned himself to doing it.

I went back outside with the pizzas and waited. I was so excited. I texted my manager that I wouldn't be back even though I still had an hour left. He was concerned but I told him everything was fine. I just wouldn't be back in that evening.

Then after a minute or so I rang the bell. The guy opened the door in a towel. He was quite good looking. Tanned, toned. Maybe a hint at a six pack. Actually quite tall dark and handsome. I took a breath.

I said, "Um... sir I have your pizzas. It'll be $42!"

I held them out and when he released his towel it fell to the ground. I quickly moved the pizzas to the side so I could get a good look at what he was carrying. It was a half erect nice sized cock. I figured when fully erect it could be close to Carlos.

I said slowly, "Mmmmm. Happy Birthday to me!"

I then handed him the pizzas and he sheepishly took them and covered his cock with them and placed them on the nearby table.

I held out my hand for the money and as he approached me again I took a long look.

I said, "Now that's better!"

I took a step toward him and let the door close behind me.

I said to the woman who now had her shirt and shorts on, "What do you think of Frank now?"

She said, "Yeah. It's about time he got naked instead of me!"

I said, "mmmm with a body like that he should flaunt it!"

He was red in the face and I decided to take this a step further as my pussy was raining fluid.

I reached out and put my hand on his hip. He stepped back as he was surprised.

I said, "Oh, did I shock you! What would you have done if the delivery guy would have touched her?... cheer?"

He looked at me and stepped closer. So I could return my hand to his hip. Then I reached around and took a grip of his firm ass.

I said, "Nice! What do you guys think? Pretty good shape don't you think?"

They really didn't really speak. They seemed quite shocked at this turn of events.

I looked at the woman. I said, "mmmm, sexy man! Have you ever?"

She said, "What?"

I said, "Um. Played with his...?"

I pointed at his cock that was now becoming 3/4 erect.

She said, "No, we're just friends!"

I said, "So you wouldn't mind if..."

I reached and touched his cock. He backed off as instinct took over but I reached further and took a hold of it.

I said, "Mmmmm it's really nice. And... mmmmmm... it looks yummy!"

I looked at Frank and gave him a slutty smile. Then I got in front of him and took a more firm grip.

I looked back at the guys and girl. I said, "I think I have to give this a try!"

I turned back to Frank who was now shaking and I knelt down in front of him and I licked his head. Then taking the head inside my mouth and swirling my tongue around it. I could taste precum already dripping.

I moaned, pulled him out and said, "Mmmm tasty."

I looked at the woman and said, "Want to give it a taste? It's yummy!"

She looked at me and nervously shook her head no. I didn't really know how to get this group into a big old fuck session but I knew if I wanted it I would need this woman to be more comfortable and either partake or leave. I had never been into women but for the sake of getting my pussy pounded I needed to get this chick in the mood. I stood up and walked over to her.

I said, "I know you want to give it a try. It's really a nice cock."

She shook her head no again.

Then I thought. She came to the door in a towel. Maybe some more exposure.

I said, "So... you came to the door in a towel. And it dropped. Maybe we can give these boys a nice show!"

I took her by the hand and we stood in front of the young men. Then I lifted her shirt up and off. She didn't resist. She had nice tits. Probably c cups and looked quite firm in her bra. Then I reached out and started massaging her tits. Telling her and the guys how nice they were. She began to moan as I played with them. Then I unclasped her bra and they popped out. Man they were nice. I couldn't resist and had to touch and suck on them. They were so nice and firm and her nipples begged to be sucked. I licked one and soon was sucking her nipple. I could tell she was enjoying this as her heart rate jumped and she made some moaning sounds.

I stopped and said, "Frank. Come here. Give this a try. She has the most amazing tits!"

She didn't seem to mind what I said so I backed away and let Frank suck her nipple. Then I motioned for another guys to suck on the other one. Then I stood next to her and quickly took my shirt and bra off and had the other two guys come forward and suck mine. Damn it felt good. I looked and saw the tops of 4 guys heads all sucking the 4 tits in front of them. I reached over to feel her tummy and get her in the mood to go further but I already felt an arm down there. So I backed off. I instead reached down and began to open one of the guys pants in front of me. Once it was unbuttoned I reached for the other guy. And did the same. Soon I pushed them off my tits and got on my knees in front of them and began to suck on one then the other. I then reached for the pants of the only man with pants still on and opened his pants too. After I gave a nice suck session to each man making sure they were good and hard I turned to the woman. Then I undid her shorts too. I slid them down and then for the first time touched another woman's pussy. I started on top and soon had found her clit. As I touched it I moved my mouth closer and actually pushed my lips against it and then started licking her clit. I felt her shake as I must have hit the right spot. After a few seconds I put my finger on her clit and had Frank put his mouth on her clit and I watched as he began to get her going. I then unbuttoned my pants and let them fall, then, as the 3 guys gazed on, I took off my thong as well. I wanted the guys to be as comfortable as possible but I didn't want to be facing away either so I leaned back against the arm of the couch and spread my legs a little. Then I motioned for one of the men to come forward. I took his cock and after a few short strokes I pulled him forward until his cock was touching my soaking wet pussy lips. Then I released his cock and he slowly slid his cock into my pussy. I was so wet that it slid right in all the way to the top. I moaned loudly as Frank and the women must have heard as they both looked. I looked at them and smiled and as the man fucked me faster and faster I got louder and louder too. I also heard the woman getting louder as Frank continued to give her pleasure. Then I heard her begin her orgasm. She shook and tensed up. Her arms would move then stop as she seemed to spasm. I wondered if I looked that way when I climaxed. Really quite undignified but I guess in that moment... Who really cares? Watching her cum was making my waves of pleasure stronger and soon I was getting louder and saying some naughty things.

I don't know if it was the whole not being prepared for the situation that had me cumming this early or what cuz, this guy wasn't that big and he wasn't that great at fucking either. But I sure seemed to be enjoying it. And the guy was too. As I told him to fuck me harder he started going as fast as he could. It was like a jackhammer pounding my pussy. So fast and hard. The speed and aggressiveness pushed me over the edge and I began to peak. It started strong and I was yelling and swearing. Then I felt the man tense up and begin to shoot his load inside my pussy and my peak hit another high. It felt so good to have a strange man who I never met and I didn't even know his name fuck me silly and cum inside of me. As he finished, I motioned for another man. He took his place and hard and fast slammed his cock inside. He began to fuck me as my orgasm slowed but really never fully went away. The woman came over to me and leaned down and asked, "You fuck random guys, um... without a condom?"

I said, "mmmm fuck yeah. Birth control!"

She seemed quite interested and asked, "So you enjoy fucking random guys?"

I said, "yes. It's a high for sure. I love sex. And new or strange new guys well... This is a sort of a first for me and it's awesome! Have you had sex before?"

I didn't want to tell her how much of a slut I was. So I resisted saying any more.

The guy fucking me continued to pound away as I chatted with this woman. However I felt my pleasure ramping up again. This man was bigger and he was taking the time as he fucked to make sure his pelvic area was hitting my clit and then he did this move that really seemed to stimulate my clit as he fucked me. I didn't think I would peak twice with the first two men but it seemed to be a fore gone conclusion.

My moaning began to get louder and the woman barely said she had sex before and I began to cum again. Again I felt another man I've never met dump his seed in my womb. The riskiness and sluttiness was having its effect on my peaking that's for sure. I began to come down and yet another man stuck his cock in my pussy. I looked to the woman who now was sucking Franks cock. I guess turnabout is fair play. The man busy fucking me didn't take long and soon I felt his seed spraying my insides. Frank was still being sucked off my this woman but I wanted him to fuck me. But I didn't want to take Frank away from her. Heck maybe she was getting into this so I looked back at the first man. I got on my knees in front of him and started sucking him hard again. Then when he was almost to full staff I leaned over the arm of the couch this time face down and had him go for round 2. Since I didn't really know the men other than numbers 1, 2, 3 and Frank I didn't even really look back at the guy pounding away. I just closed my eyes and enjoyed the feeling of being used like a slut. They called me the "Pizza Slut" and I didn't mind as I peaked 3 times more as each guy and even Frank fucked me. After the second session I stood up and thanked the men for the orgasmic feelings I felt and I put my clothes on and left.

In my car I sat on the towel which I had kept in there for this very reason. I thought. Numbers 21-24. Fun. Really exciting. And so fun with complete strangers. Now I was a "Pizza Slut!"

I would have thought that opportunity would have come up again but it didn't and I was ready to head to college. The last week before school I got a text from Paul(I haven't spoken to him since school ended in the spring).

He said, "How are you?"

I said, "Great! You?"

He said, "Good, so..."

I said, "What?"

He said, "the reason I'm asking is because I know you well... and you'll like it... so don't be upset by my request. Just let it sink in first."

I said, "Just lay it on me..."

He said, "I'm having an end of summer party. I would like you to be the entertainment like at Steve's party."

I didn't respond. I hadn't talked with my ex in almost 3 months and now he asks me to be a slutty stripper for his party. That's the reason we broke up. I didn't want just one man. And I couldn't bring myself to reciprocate his "I love you's." Now he wants me to fuck multiple men in front of him! Gosh men are confusing.

I said, "Details?"

He said, "Around 8 guys. Steve, Ben, Pete, and me. Then some guys you haven't been with. At least as far as I know!"

I shot a response back, "What is that supposed to mean?"

As he was typing his response I knew I was in... 8 guys. And some of them new! This is what I've been craving...

He said, "I know you! You might have found a guy I don't know.... In a store somewhere and took him in the bathroom and fucked!"

I began typing, "Fuck you asshole! I'm not a slu....." I was going to write it but... I was a slut.... He knew me. He knows I want to do this show for him. But he's rubbing my sluttiness in my face. He's kinda pissing me off. I decided to let it go. And I deleted what I started to write.

I texted, "Very funny, when is this party?"

He texted, "Tomorrow at Steve's house. 6 o' clock."

At least I was familiar with his house and stripping and fucking there. A wave of excitement came over me when I thought about my greatest accomplishment to date. 10 guys. Many who were virgins.

I said, "Fine. I'll be there."

After hit send I thought. Damn. I should be charging for these events. I could probably take in over $500. Maybe even a $1000. Yet I'm doing them for free. I guess I'm just a slut not a whore. But I was thinking about it more. I mean, I whored myself out for an A. And basically to my manager to get some benefits. Or was I just using my assets to my advantage. I decided that unless I was taking cash for sex then I was just a slut and not a whore.

I was still in thought about my whore vs slut dilemma and my phone beeped.

Paul texted, "Good. Wear that red dress! No bra or panties!"

I shot back, "I'll wear what I want!"

Paul came back with, "Fine, but you know you want to wear it for us! Just do it!"

Fuck he was right. I loved the way I looked in that thing. It was so sexy and slutty. Everything about that dress showed exactly who I was. It bugged me that Paul knew me so well.

The next day I was busy packing for my college move out of my parents house, but had to stop to get ready for my evening. I decided to wear the red dress without anything under it. After all... I was a slut.