Cindy's Bikini - More Sex w/ Teens

Note to reader: All characters are at least 18-years-old, even if not specifically stated in the story.

My best friend Ashley and I were about halfway through fulfilling the sexual fantasies of the high school age boys that held our sex tapes.

For the second round of sexual request, we kept the same order as the first. This meant we were due to see Don next. Don seemed to have a fetish with sex in places where he might get caught. This time he wanted to fuck us at his high school. The same high school I graduated from five years ago. Ashley and I agreed to this, but we got to choose where we did the deed. Don agreed provided we do it during the school day.

I convinced Ashley I knew the best spot to do this, not that I ever had sex at the school before. The music wing of the school had a series of small, soundproof rooms where students could go in and practice their instruments or singing. The doors locked and had no windows. It would be perfect. I expected Don to throw a fit that I had picked a location where getting caught was nearly impossible, but he agreed and we were set to meet him at the school the next day.

The first challenge was explaining why two college girls needed to enter the high school. Ashley and I entered the main office and explained that we were Don's older sisters and that we had some bad news to deliver. When the office attendant offered to call him to the office we insisted it would be best if we went to him ourselves. Calling him to the office would likely set him off. That somehow worked and we were set free in the school.

Don met us outside the music wing and we headed in together to find a free room. Heading down the hallway we ran into the band director, Mr. Ryan. I had taken a few band classes with him in high school. I was hoping he didn't recognize or remember me from 5 years ago.

"Cindy?" He said almost immediately upon seeing me.

"Hello Mr. Ryan, it has been a long time."

"It has been. Why are you and this other young lady here with a student?"

I hadn't planned on this. Claiming to be sisters of Don wouldn't fly here. I panicked and made some shit up.

"My partner and I are here to give private singing lessons to Don. He is very nervous about the upcoming choir tryouts. I know it's very unusual for private teachers to use these facilities, but Don insisted."

Mr. Ryan gave the three of us a look over.

"Choir tryouts were two weeks ago. I'm afraid you are too late."

"Don acquired special permission from the choir teacher to have a late tryout." I was grasping at straws.

"I have never heard of Mrs. Finch giving someone such permission," Mr Ryan said starting to become agitated.

"You will have to ask her why. If you are done, I need to get started with Don."

Don snickered at that last part. I pushed him into the nearby empty room and closed the door behind us. I went to lock the door but found no lock.

"What the fuck? This room doesn't have a lock, let's go to the next," I said.

"Don't bother," Don replied. "None of them have locks. People were using them for sex so they uninstalled them from the doors."

Ashley gave me a horrified look. "Why wouldn't you tell us this?"

"You chose the location. I figured you must have known. I thought maybe the idea that anyone could walk in at anytime while we had sex was exciting for you too."

I peaked out the hallway. "We need to go find a better location."

Don stomped his feet. "That wasn't the deal. We are having sex right here, right now." He started taking off his pants.

"Fine asshole," I said bracing the door closed. "Ashley, you go first. I'll make sure no one comes in."

Ashley started taking off her shirt. "I can't believe I'm having sex in a high school as a 23 year old woman."

"I can't believe you are either slut," Don said as he got his pants off.

Ashley and Don quickly got naked and got right into having sex, no foreplay needed. I kept my shoulder braced against the door, ready to keep anyone who tries to come in out. Don must have been holding off on masturbating for days as he came inside Ashley within only two minutes. Ashley got dressed and took my spot holding the door closed. I got naked and blew Don until he was hard again and ready to fuck.

"You better fucking be quick," I said as he entered me.

"Someone is anxious to get creampied," Don smiled

Not even 20 seconds into it and I heard the handle shake. Ashley managed to keep the door closed, but whoever was on the other side kept trying.

"We're using the room, please find another." Ashley yelled. This didn't deter the person outside.

"Get off of me Don. We are going to caught."

Don wasn't having it. "We aren't done until there are two cum filled sluts in this room."

"Then fucking do it already," Ashley yelled. My best friend was ordering an 18-year-old high-schooler to cum inside me.

"Give me a minute, I'm getting there." Don said as he humped me even harder.

We could hear the voice of Mr. Ryan on the other side. "You will open this door immediately! What are you doing in there?" The door moved open half an inch before Ashley got it closed again.

"I'll fuck you in the parking lot, okay?" I pleaded with Don.

"Staring at your tits is helping. Like 10 more seconds."

Ashley kept trying to calm Mr. Ryan down. "Please. We are in a delicate stage of Don's singing lesson. You mustn't interrupt!"

I finally felt the spraying of a warm liquid in my pussy. I had never been happier to have a high-schooler cum inside me.

I pushed him off and reached for my panties. It was at that exact moment that Mr. Ryan found enough strength to push Ashley away. I stood there fully naked, next to an equally naked, still very erect high school senior.

"My god Ms. Cindy. This is what your life has come to? You are whoring yourself out inside our great school to its students?"

I had no more excuses or quick-witted responses to get me out of this situation. I had been caught.

"Please don't tell anybody about this Mr. Ryan." I finally realized I should maybe get dressed. As I was doing so, I inadvertently gave my old band teacher a great view of my naked body.

With his eyes taking in the sights, he started lecturing me. "I had such hopes for you as I do all my former students. But I see now you rather spend your talents having sex with young boys for money."

Don was laughing at me until Mr Ryan cut him off. "Don, you will be assigned 2 weeks of detention. Ms Cindy. You and your fellow whore will leave now and not return. If I see you here again, I will call the police."

I finished getting dressed and quickly left with Ashley. I don't know what was worse. Mr. Ryan calling me a whore for young boys or it maybe being true. At least that was the last sexual favor I owed Don.

When I got home, I immediately changed clothes. My panties were covered in cum that had leaked out of me since I got dressed. In the past weeks since this all began so many of my clothes ended up soaked in the cum of the many people I have had sex with. Beyond just my panties, often my bra and shirt would also stain as many guys liked jizzing on my chest and face. Some days where half a dozen or more loads got shot into me, the mess would be so great that it would leak out into my pants. I've really come to hate ejaculate. To hide all of this from my parents, I've taken to doing my own laundry. Often though it seems my panties would become permanently stained, causing me to simply throw them out. After all of this is finally done I likely will have completely replaced all of my underwear.

The next night we were back with Richie. We arrived at his place, where he promised us his parents would not be home.

Richie met us outside and said, "Okay listen. My two cousins are inside. Remember the deal. You both pretend you are my side pieces okay? You are obsessed with me and want to have sex with me all the time. To prove it to my cousins, we are going to have sex in front of them. You will greatly enjoy it, lots of orgasms, blah blah."

"Your cousins are both 18 years old right?" He actually had their driver licenses and showed them to me. "To be clear, we are fucking you only. They will not touch us, only watch." Ashley said, wanting thing crystal clear.

"Of course." Richie responded.

We walked inside Richie's house through the front door. Inside, sitting on the couch were two guys. They were small and unintimidating looking. I highly suspected this was going to be their first time seeing a woman naked in person. One of them stood up as soon as I walked through the door.

"Wait, Richie wasn't kidding? You guys have had sex with him? At the same time?"

Richie replied, "Yep! And they are going to have sex with me in front of you right now!" Their jaws dropped to the floor.

Richie looked to Ashley for something to confirm his boast. Ashley looked at me and finally I came up with something to say. "Yes sir. We love sex with Richie so much that we are even willing to do it in front of you two strangers."

Judging by the look on Richie's cousin's faces they bought that terrible lie.

"Cindy baby. Give them a sneak peek at what they will be seeing. Lift up your shirt," Richie said winking at me. I gave him a dirty look but muttered 'fine'. I lifted my top and showed off my bra. Rickie took me by the hips and spun me around.

"Richie, how did you end up getting these girls to agree to bang you?"

Richie smiled, "I've had several college girlfriends whom I became sexual with. Apparently, I have a way with sex because those girls quickly started telling everyone in at the university how good I was at it."

He looked at us expecting us to agree. I responded in the very monotone voice, "Yep, I heard from his girlfriends he was good at sex."

Richie continued, "Cindy here approached me about trying sex with me. I wasn't keen at first with having sex with such an older woman so I said no. She then approached me later with Ashley here and asked if I would agree to sex with both of them. I finally agreed and here we are."

Again he looked at us and again I responded with a monotone voice, "Yep, had to talk him into sex."

"Okay, enough talk, let's get to it. Ladies, why don't you strip down to start us off."

The two boys looked like zombies staring at us. I have already shown my naked body to close to 10 different people of a vast variety of ages, all of whom have had sex with me in whatever way they wanted. What was two more? At least they would not be having sex with me. I started by taking my top off revealing my bra underneath. Both boys quickly gripped the sofa they were on with all the force they could muster. Ashley looked at my exposed bra and took a breath. She looked me in the eyes and nodded with a bashful look. She took off her shirt as well and the two sets of eyes began darting back and forth between our chests.

"Keeping it going girls, my dick doesn't want to wait all day," Richie said showing off for his family.

I un-buckled and un-zipped my jeans and pulled them down revealing my silk pink panties. Ashley did the same revealing a white thong. I felt embarrassed for her being in a thong but realized we would soon be naked in front of these guys anyway.

"You are both so hot. Are we really going to get to see your boobs," one of them asked.

"Well? Answer them Cindy," Richie said with a smile.

"Yes. And our asses and pussies. Plus you'll see Richie here plow us and blow his load in both of us. You will get to see all of it," I said not giving a shit anymore.

I then immediately took off my bra and pulled down my panties and stood stark naked in front of yet more high-schoolers.

"Told you. Like what you see?" I said.

Ashley stared at me and then followed my lead and slowly stripped. We have given these boys probably their first encounter with nude women.

"Okay! Let's keep this going. Cindy, come over and suck my dick. Ashley, make out with me."

Richie's dick was out and erect. We both headed over to him. The sooner we get this over the better. I got on my knees, grabbed his dick and began moving my lips up and down the shaft. Ashley stood right next to me.

Ashley quietly asked him, "How many times are we going to be with you tonight?"

Richie responded, "Till I can't cum anymore. I haven't masturbated in over a week. Buckle in girls." He then brought her face to his and put his tongue down her throat.

"Holy cow, these girls and sucking his dick! Sluts!" One of the cousins said.

Whatever. Not like you'll get any of this.

It didn't take long till Richie grabbed the back of my head and filled my mouth with his cum. Another day, another 18-year-old blowing his load in my mouth.

"Fan-fucking-tastic job Cindy. One of your best. And that's saying something considering how many of those you have given me."

Fuck you, fuck you, fuck you, I said over and over in my head.

"But now it's time for some real fucking. Ashley, lay on the floor. Cindy, how about you dance some for our guest?"

Again I figured arguing was going to be pointless and likely to backfire. I'm already naked and soon to be fucked. Who cares if I dance? Richie put on some stupid music and I swayed my hips back and forth.

"Another thing for you guys to notice is these girls aren't asking me to wear a condom. They want my dick raw and unprotected. They want to feel my seed in them."

With that, Richie mounted Ashley on the floor and started pumping her. While having sex with her, he also began giving me instruction on dancing. He had me bending over, laying on the ground spread legged, touching myself (essentially masturbating), among many other things. These two new strangers were getting eyefuls of the entirety of my body.

Not taking long, Richie came inside Ashley and had us change places and had her dance in the same manner I did with the same moves. Richie fucked me and came inside me, not noticing or caring how I reacted. We kept up this rotation for a while, one of us dancing naked, the other getting fucked. He fucked us in different positions each time. From behind, us on top, and everything else he could think of. Most awkwardly was when he did us from behind. He positioned us facing right at his cousins. Every time I looked up I had four eyes starting at my breast swaying while getting plowed by their cousin from behind. Dancing was also weird as the night went on. Each time we danced, more and more cum from the previous sex would drip down our legs. Richie was on point that night. He eventually came in each of us five times and by end it was flowing out of us while we danced. If my past self from a month ago could see this sight now she would die of shock. For my current self, it's a Tuesday.

Finally Richie declared himself spent. The boys were in shock from what they watched. I hate to think how seeing this tonight will sway their view of sex and women, but the damage was done.

Richie stood up from cumming inside me a last time and declared, "Okay, now which of you two wants to fuck them now?"

"What!" All four of us yelled at the same time.

"I'm kidding," Richie said laughing. With that I quickly got dressed. I could already tell I ruined another pair of panties. No matter, I was done with Richie forever.

After that session, we technically had a break, but in reality we didn't. Our next session was with Shawn who had a request I had been expecting, anal sex. After Shawn brought this up all of the boys quickly stated they wanted anal sex as well. I refused stating my ass couldn't take that. I talked Shawn into only allowing anal sex at one of his session's and no other to which he agreed since it was his idea first. Shawn had done his research though. He explained that if we went straight to anal sex it would prove way too painful for us and likely not very good for him. We needed to prepare our asses essentially. Several days before the session Shawn gave Ashley and I a series of butt plugs. We were to insert and keep these in our asses all day, and each day we would use a slightly larger one.

The butt plugs were very awkward. Walking around school, sitting in class with something shoved up my ass proved uncomfortable and humiliating even though no one but Ashley knew I had it in my ass. With every person I talked to all I could think about was the object currently shoved up my ass. But I knew if I didn't, anal sex would prove to be very painful.

After a week of increasingly larger plugs, the night came to pass. Shawn and the two of us met up and we didn't waste any time. Shawn had us perform some typical foreplay in which we got naked and gave him some head. He announced he was ready and chose Ashley to receive anal first. Ashley laid on the floor in a downward dog position and Shawn knelled behind her. He spent ten seconds or so positioning and working his penis into position until he finally got it at least partially positioned into her ass. Ashley reacted with a large squirm, continuing to do so with every thrust. To Shawn's credit he took it slow, but you could tell she was struggling having a dick in her ass.

It took about five minutes but finally Shawn finished inside her. Ashley had now given every type of virginity that existed to these guys. She laid on the floor and recovered while I took my turn. I took the same position and her with my ass sticking up in the air. I had also given up so many first to these guys (not as many as Ashley though) and I was about to give up yet another one, my anal virginity. I had never intended to lose it as it never appealed to me. I never understood why any woman would agree to it, yet here I was about to get pounded in the ass by 18-year-old high-schooler. Before I knew it, Shawn was behind me and I had a dick shoved up my ass.

The experience was intense for me. Yes it was painful, but there was something else too. I was being touched in an area I had never been touched before. It was an odd feeling. The pain never increased nor went away, but the odd tickle increased in magnitude. Suddenly Shawn shifted slightly and the sensation caused me to let out an audible moan. Shit! Shawn actually stopped for a brief moment before starting up again. I didn't dare make eye contact with Ashley.

I soon realized that the odd sensation was turning into pleasure. I was getting off on anal. In fact, I could feel an orgasm building fast. So fast in fact that before I could formulate any plan or think what to do, the waves of cumming hit me hard. It was a vocal orgasm and I found myself humping my ass on Shawn's dick. I quickly got back to my senses and realized there was no hiding what happen. Shawn kept humping but I could feel the smile on his face even if I couldn't see it. In my mind I begged that he cum already so I could quickly get dressed and leave, forgetting the events of tonight. Somehow this night was more embarrassing than having hardcore lesbian sex with my best friend.

But Shawn kept going, lasting a lot longer than he did with Ashley. I think he wanted to see if he could get anything else out of me. Unfortunately he could and did. In almost the same manner, a small sensation turned into large one which turned into an intense orgasm. Shawn finally came in my ass.

"Well what do you know, Ashley gets off on anal sex," Shawn said.

I didn't say a word and didn't look at either of them. I got dressed, not bothering to clean myself up, and left. What the hell is wrong with me?

I slept horrible that night. Firstly because my ass was quite sore, but mostly because of the embarrassment of what went down that night. I had climaxed multiple times and hard from a Shawn sticking his dick in my ass. The next night, while my parents were out, Ashley came over to have her last session with Tommy.

"Not a word about last night, I'm not in the mood," I said sharply to her when I opened the door to let her in.