Cindy's Bikini - Best Friends

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

Ashley arrived at Cindy's house about half an hour late but she was already in her swimsuit and ready to sun with her best friend. She was excited about this day. First it was going to be the first day she spent by the pool thus far this summer. A good chance to get tan and not worry about anything else. Secondly, she gets to spend it with Cindy. A few weeks earlier Cindy had bought a bikini at the encouragement of Ashley. At the time it had surprised her as it was a bit more revealing than she figured Cindy would be comfortable with but having heard her say she thought it would be cute on her, she had bought it. Now was her chance to see her in it. Cindy was not a lesbian, in the sense she didn't seek female sexual companionship. She had dated a few guys and enjoyed kissing them (but had yet to go beyond kissing them). But something about Cindy peaked her interests. It wasn't just physical. She was emotionally her rock. She genuinely cared for her well being. But yes, she did find Cindy gorgeous and wanted to see her in that bikini.

Cindy had mentioned something about her jerk of a brother and his friends also being at the pool, but it was easy enough to ignore them. Not sure if she was by the pool yet, Ashley went to the front door. Bobby answered the door and a big smile appeared on his face. Creep is probably looking forward to watching me in my bikini all day.

"Is Cindy out by the pool yet? I'll go around to the back if she is."

Bobby responded still with his dumb grin "No, she's upstairs. I'll take you too her."

"Ummm, okay," I said confused.

Why did I need to be escorted inside? I've been over many times before, I know my way around. But nonetheless I walked behind him up the stairs and to her room. At the top of the stairs we turned right and down the short hall. Before we got to the door, Bobby stopped and turned, gesturing his hand towards Cindy's room. I stopped and gave him a weird look and continued on.

Outside of the room there was a strong odor. Not bad, but not something I had smelled before. I heard odd noises coming inside. I looked back at Bobby who urged me to go on in. Once I got in the room I stopped dead in my tracks, not knowing how to react to the scene.

Cindy was on her bed completely naked. Two guys surrounded her, also fully naked. The one behind her was obviously fucking her while she had the other boy's dick in her mouth. A third boy, Don, was standing naked and erect holding a video camera. Was Cindy in trouble? I didn't see anything that told me she was being held against her will. Was this who Cindy really was? Did she let guys gang bang her and film it? Had she been hiding this side of her from me? Furthermore, she seemed to be enjoying the sex. I could hear her muffled moaning, as she seemed to be enthusiastic sucking the dick in her mouth.

I turned towards Bobby, wandering what his role was in all this. He paid his sister no attention, instead he appeared to be intently staring at my ass. I had no idea what I had walked into, but it didn't seem to be incestuous at least.

Cindy suddenly became aware of my presence. She pulled back her head to get the dick out of her mounth and yelled "Ashley I..." but was interrupted by a load of cum from Richie splatting over her face. She attempted again saying, "Ashely I..." but she was again interrupted this time by Shawn rather loudly cumming in her pussy with an accompanying drip of cum leaking from behind her.

"Fuck! Stop cumming for one minute, Jesus," Cindy exclaimed.

She moved away from Shawn and stood up. A large amount of cum gushed out of her as she stood up. Her chest, face and crotch all had cum on them. My eyes darted between her face and her naked flesh. In all our years of friendship I hadn't seen her naked to any degree. Now her body was on full display for me, but in very precarious circumstances.

"Ashley, I can explain. This isn't what it looks like. I got myself into a situation here and I was forced to do these thing. I had no choice!"

"Are you in trouble? Should I get help?"

"No! Don't get anyone else involved! Please just trust me. It will be over soon."

"Cindy, you are having sex with three high-schoolers! God, how many times even? What about Mike..." I trailed off staring at her cum covered tits.

"I know, I know! I didn't want this! If I didn't do this I would have been exposed to the whole school, Mike would break up with me, and my parents would never let me leave the house again. It's hard to explain, but please trust me that I had to."

"Okay, I know you wouldn't have done this without reason. You're not a slut. Is there anything I can do to help," I pleaded.

"Maybe you just leave. I don't want..." I interrupted her, "I'm not leaving you here like this."

Shawn chimed in, giving me a look I didn't like.

"None of that is true is it Cindy? At the pool she started teasing us, daring us to show her our dicks. When we didn't, she took off her bikini and had us take pictures of her. Do you want to see them?"

"That's bullshit you all know that," Cindy said angrily.

"However we got here, you've seen the truth. Cindy let us fuck her for the past hour or two, all of which she let us film. Now that she has been caught, she is trying to back track. That isn't fair to us," Shawn said swinging his still hard dick around while speaking.

"The tapes are ours by right, now she wants them back. I don't see why we should have to do that, unless you have an idea Ashley?"

I didn't respond, instead I just stared at Cindy who gave me a pathetic desperate look.

"What, so I let you guys fuck me and you give us the tapes? Yeah that seems like a shit deal for me," I said in a rather unconvincing manner.

Don spoke up, "Cindy is a cum covered mess. Her pussy is still leaking all of our seed. Maybe you just clean her up, but not with a towel if you understand."

The room was silent until Richie spoke up, "He means lick her body and pussy with your tongue."

My heart started racing. I've admitted to myself that I have a crush on Cindy and have created scenarios in my head in which I get to explore those sexual feelings. But they were never going to happen. Now I'm faced with an opportunity to have sex with Cindy and afterwards I can blame it on these three, maintaining our friendship. The smell of cum in the room was having an impact on me as well. I wanted to find out what taste like, and licking it off her body made it even more appealing. Was I really considering having lesbian sex in front of these four losers?

I realized I needed to put on a show of resistance first.

"I'm not a lesbian and nether is Cindy. We're best friends, almost like sisters. What you are asking for isn't possible," I said hoping that covered what I was prepared to do next.

"Then prove that you will do anything to help your sister best friend," Shawn said. That gave me the all clear for what I was about to do next.

After an uncomfortable silence, I approached the naked, cum covered Cindy, keeping eye contact with her.

"I didn't want this to happen this way" I whispered to her as I began kissing her cheek. "But I'll do what I can to help you get out of this."

The boys watched in silence as I kissed and licked the cum off her cheek. Having never been in a situation with it before, this was my first time tasting cum. Salty and warm, combined with the sweetness of Cindy's skin. I'm licking cum off my naked best friend. Cum which came from 3 boys currently naked in the room becoming erect watching the act.

"Better start getting that chest of hers cleaned up. It's going to be a big job as you can see," one of the boys remarked.

I leaned over and took her naked tits into my hands and started licking them. God they were gorgeous. All the while Cindy stood there not knowing how to react. After a while they instructed us to move the bed which we did and I continued to move lower and lower down her body as instructed. Eventually I got to the point where I licking around her inner thighs, inches away from tasting her pussy.

"Cindy, I'll bet Ashley is becoming very self conscious being the only one in the room who isn't naked. Help her out."

At that my head raised up and Cindy sat up looking at me. Was I really going to get naked in front of these boys? Cindy gave me a look which I interpreted as meaning, "I don't know what to do or what would happen if I say no. What should I do?" "It's okay" I mouthed to her without saying a sound.

With that Cindy reached behind my back and undid my bikini top, exposing my b-cup breast. I sat up and she pulled down my bottoms, leaving my ass bare for everyone to see. Not knowing what else to do and not wanting to sit there naked in front of the boys and Cindy, I went back down to kissing and licking her inner thighs. Suddenly somebody else got on the bed with us, right behind me. In what seemed like an instance, someone entered me from behind in a single push. All this happen before I could explain I was a virgin, having never had anyone or anything inside me. My hymen had long been taken care of my years of sports and other activities. But it was still a startling experience for me both physically and emotionally. Before I could react they gave a few humps and suddenly I felt a warmness enter me, its source obvious. They had cum inside me and I was without any protection, pills or otherwise. In a matter of seconds I loss my virginity and may have been impregnated.

"Damn it Bobby! They were just starting to get into it. You couldn't have waited?" Richie said in protest.

"Fuck you guys. You just spent that last two hours having sex, what, like five times each? I couldn't wait any longer!" Bobby replied.

Cindy's little annoying brother Bobby. He will forever be the first man to have sex with me and may well prove to be the father of my child. I laid there stunned while the boys argued.

"Well we might as well get back to it, I want a turn with Ashley," Don announced. A turn? Was I going to have sex with everyone here?

I found myself on my hands and knees with Don right behind me, getting ready to penetrate me. I finally snapped out of the shock of getting creampied and sat down, avoiding becoming Don's latest lover.

"I didn't agree to having sex with you guys, let's stop things here," I said looking back behind me at the 8 inch cock that was almost inside me.

Don was quick to protest, "But you just fucked Bobby and let him cum inside you."

I stumbled my words in reply, "I... but... why aren't you guys wearing condoms?"

That was all I could think to bring up. I regretted it immediately as it made it sound like I was good with sex as long as they wore protection.

"Jesus, we went over this with Cindy, we don't have any and you girls are on birth control anyway," Don said, obviously becoming quite impatient to have sex with me.

I couldn't say that wasn't true in my case. That would be too embarrassing to admit while Bobby's seed sat in my womb. I looked to Cindy for help, but apparently during my short argument with Don, Richie had gotten on top of her and was pumping his cock in and out of her pussy. She stayed silent to my gaze, giving a look of embarrassment and sorry. Also was she starting to get off on his dick? I felt confused but then shock when I looked up and noticed Shawn with the video camera. Fuck, I had forgotten all about that. How much of me had they filmed? Was my deflowering and possibly impregnation captured? Did they manage to film me exploring Cindy's body? I could not have a video get released that would make me look like a lesbian. My parents would kill me. I saw no other path forward.

I picked my ass back up without saying a word and welcomed the second lover of my life and of the day to enter me. Unlike Bobby, Don didn't give me a couple of pumps before seeding me. He was much calmer in his motions. The feeling of a dick in me was still weird, but with Don it wasn't unpleasant. I tried to get myself to be less tense. Richie had finished with Cindy and she was laying there on the bed motionless but breathing hard and looking flustered. How many times did they cum inside her? Bobby had mentioned something about 5 times each. How many was I going to get filled today?

My thoughts were interrupted by appearance of Shawn's dick in my face. I hadn't even considered I would have to be giving blow jobs as well. I almost protested, but when you are letting four guys blow their loads in your unprotected pussy, a blow job seems like an odd boundary to set.

Shawn directed his dick around my lips. I had never done this before and was clueless on what I was suppose to do. I positioned my tongue underneath his dick and waited. Shawn began moving his hips back and forth gliding his dick across my lips. Despite how jarring it was to have my first dick in my mouth, the sliding cock on my tongue was erotic. Shawn spoke up, "God damn Ashley you give fantastic head. Even better than Cindy. How many guys have you blown?" I couldn't answer obviously but I was oddly proud that my virgin mouth apparently was a natural at sucking dick?

My 'gift' paid off for Shawn and the twitching of his dick lead to my first ever mouth full of hot cum. He pulled his dick out and for a minute I kept his spum in my mouth. Not knowing what to do with it, I finally swallowed it. Another feeling of warm liquid occurred in my pussy as Don released fresh cum in me. Thus doubling the number of people who might have got me pregnant to two.

From there, the boys started running on a train on us. Sometimes we had sex with only one of them at a time. Sometimes we would also simultaneously give head while getting our pussies seeded. Regardless, there was rarely a moment we didn't have one of them inside at least on of our orifices and they always came in us, never outside. For obvious reasons, I spent more time with Bobby than any other boy. I started thinking about how many other girls in school had have as many sexual partners as me, which was now four. Besides Cindy obviously, had any of our female classmates ever had sex with two different guys in the same day, let alone four? We could be the biggest sluts in school now. I've gone from prude to biggest slut in an hour.

I also became more aware of the video camera and how extensively it was being used. When one the boys not currently having sex with us they picked it up and brought it close to me. The angles they were getting were so embarrassing. Every inch of my nude body was likely captured by that god damn camera. The small refractory period of the guys was surprising. Soon I found myself with cum almost pouring out of me when I moved. It was hard to see how I wouldn't become pregnant from today.

At one point, I was laying on the bed while Richie was taking me in a missionary position. I started finding myself staring at Cindy who was having sex with Don in a cowgirl position where she was on top. Her breast where glistening with sweat and cum and bouncing in a rhythm. I soon realized I had gotten myself quite sexually excited. My breathing increased and I was actually humping in sync with Richie. Soon I realized what was happening and after first trying to fight it, I looked back at Cindy's body and accepted it. Ten seconds later I let out an audible moan and came. The sounds of my orgasm instantly led Richie to finish inside me while the rest of the room was staring at me. Cindy gave me a confused, slightly disgusted look. How could I have let one of these jerks having sex with me get me to climax.

All I could do was look away from her and say "I'm sorry! I don't know!"

"It's okay Ashley, it's a very weird day," she responded and I remembered her moaning loudly when I first encountered her today.

Bobby quickly took Richie's place and I was having sex for the likely the 12 or 13th time today (and my whole life). I laid there with my eyes closed, still embarrassed by what happen. Oh well, I doubt that moment will be all I remember regretfully about today. After all this time having had so many private thoughts and desires about Cindy, when it finally happens its associated with so many other weird events today involving sex with high-school boys. I began to think back earlier in the hour seeing her naked for the first time. Getting to feel and kiss those breast and later coming so close to her private areas. Even having her remove my swimsuit was an amazing experience. Was she also excited by seeing my body?

I found myself again staring at her bouncing breast a few feet from me as she had sex with Shawn now. Again my head separated itself figuratively from my body as I reflected on these past events and the images in front of me. When I became self aware again, I immediately became panicked as my body began to betray me and was on the cusp of another orgasm. A few second later I let out another moan, somehow louder than the last as I had my second orgasm of the day.

"Are you cum again?" Cindy yelled at me with an accusing voice while she was getting fucked by a guy she hates.

"It's not from having sex I swear. It's from watching you...." I quickly shut myself up and saw Cindy look away.

"From watching what? Cindy? Do you have a thing for Cindy huh?" Shawn said while humping Cindy from underneath her.

"It's okay. I to find her jiggling breast to be a turn on. We have that in common." Suddenly Cindy bent over and started kissing him open mouthed just to shut him up.

The boys then started getting more adventurous in their positions. They situated Cindy and I on all fours facing each other. Shawn and Bobby then took us from behind while they instructed us to kiss, which we did. The first time we ever kissed, but I didn't quite imagine it with her brother's dick cumming inside me at the same time. As a break for our vaginas, they instructed us to give them 'boob jobs' in which their cocks were rubbed up and down in between our breast. Cindy was the most popular for this position, but I did my share too. This had the added effect of covering our breast even more in cum. After this they realized they could have one girl (me) pleasure all four of them at once. Arranging me they had me hold two cocks in each hand, one in my mouth, and another had intercourse with me. It was exhausting but all four managed to cum in this position. They made Cindy do a similar act, albeit with just three of them thus allowing her to use two hands on a single penis. As a final insult, they handed me the camera and had me film Cindy as she was getting double teamed by Don and Richie.

Finally they were reaching their limit. Richie, Shawn, and Don were spent while Bobby gave me a few more 'deposits' before finally being completely done. The boys departed downstairs with the camera in hand while Cindy and I laid motionless on her bed. My best friend, her brother, and 3 high-school seniors five years younger than me had all witnessed me lose my virginity (vaginal and oral), explore my lesbian side, orgasm twice, and likely get impregnated. All to ensure the video proof of all of this happening wouldn't be released. A video I just realized we let walk right out the door....

*Writers note: Shorter story this time I know. This story is far from finished though. A lot more to come.