Babysitter Loses Control

Next message. She was sitting on a couch next to Joe, looking upset. He had his hand on her knee. The caption read "Her bf yelled at her. Joe trying to console her."

Next message. "She was sad and almost left but we talked her into a game of flip cup." The video only showed the end of the game, with Amy finishing chugging a beer and then flipping the cup successfully on the first try. "Yes!" she squealed, and celebrated by running to Joe and jumping into his arms, straddling him. He spun her around and the video ended her perfect butt faced the camera. Joe's dick was visible between her legs, her pussy must be resting directly on the base of it.

Next message. "Deciding the wager on the next game." It was a video of Amy negotiating the rules. "It would be cheating if I cum. You guys can cum if you have to but I'm not helping you cum, that would also be cheating. I have to draw the line somewhere!" She was smiling and appeared to be enjoying the conversation.

I went to the next message. "She lost, and I let your husband have my reward for winning, Avery," the caption said. The video started with a zoomed in version of Amy laying on her back, it was zoomed it to where only her face and tits were visible in the frame. She put her forearms against the outside of her boobs and squeezed them together. Suddenly, a dick slid into the frame. The camera zoomed out a bit and Kyle must have walked behind Amy's head. Joe was sitting on her stomach, straddling her, and fucking her tits as she pushed them together.

"You guys.... oh my gosh you guys this is so wrong. It feels like I'm cheating." She looked like she was into it though, and she alternated between giggling and a look of concentration as she held her tits in place.

"You aren't helping him with your hands and he's doing all the work. It's not cheating," Kyle assured her from behind the camera. I couldn't believe this. Amy had never let me fuck her tits before. The video ended.

Next message was a still shot. I nearly stopped breathing. Amy was in the same position on the couch, and her entire chest was completely covered in cum. She was smiling but was flipping the camera off with her left hand, her engagement ring glinting. "She saved us all from blue balls," the caption read. I was nearly hyperventilating again.

The last message was a video of Joe leading her by the hand as they walked toward a hallway. "Hitting the showers at the end of a fun night," the caption said. They walked past the camera and the last thing I saw was Amy's beautiful butt disappearing around the corner.

I don't know how long I lay in bed before I passed out. This was the worst day my life.

Day 5- Tuesday

I woke up almost panicked. I had to talk to Amy. I was at the store when it opened to buy a new phone to replace my broken one. I got that done pretty quickly and was on my way to work. I dialed Amy's number, still straight to voicemail. Damn.

I made a decision and dialed another number. I hated that I had to resort to this but it was my only option. "Hello?"came a sleepy on the other end of the line.

"Anna, it's me, Ace," I said. "I need your help."

"Ace, what the hell... its early in the morning and I'm hung over. Besides why would I help you?" Anna grumbled.

I recounted in detail the events of the day before and told her I needed her help finding out what happened and where I stood with Amy. And to make sure she didn't stray further.

"Wait, so Amy's all pissed at you and getting jizzed on by random guys?" She laughed. "Ace you are so fucked."

"Look, I didn't ask for your assessment of the situation, Anna. Will you help me or not?"

"Yeah I'll go by there, but only to make sure she's ok and because I'm curious now."

I grudgingly thanked her and told her what condo they were in. She agreed to call me when she spoke to Amy.

Work was torture all morning as I waited to hear something. Finally around 11:15, Anna texted. "I convinced her to go to lunch with me. We're headed there now. She's pretty hung over and she hasn't said much."

An excruciating hour later, Anna called.

"Ok, I found out a bunch of stuff for you. You owe me bigtime," she said.

"Just tell me everything," I said.

"Relax, Ace, nothing happened. She just hung out naked for a bit with some hot guys with big cocks."

"Dammit, Anna," I said, exasperated. "Why would I care how big their cocks are?"

"Well I care about that part- it was my favorite part of the story. Actually you should probably care too if they're as big as she described. She said the one guy, Kyle is even bigger than Seth and she said Joe's pretty hung as well. Josh is apparently... well, more like you- a little smaller than average." She seemed to take pleasure in relaying that last part.

"She said that? I mean- whatever it doesn't matter. But she's lying about 'just hanging out' right? I mean I saw her covered in cum in that Snapchat. Does she know I've seen those?" I asked.

"Well, now she does because I told her. But get this- Kyle sent those to Joe's wife Avery also. Apparently he saw two Avery's in Joe's phone and just thought she had two numbers, or that one was an old number. Anyway, she didn't fuck anyone, apparently she told them she considered it cheating if she got off with them or if she got anyone off. She lost a bet though so they compromised and decided if she let Joe tit fuck her, it wasn't like she was touching him. Then the other 2 guys were horny so she just let them jerk off. She said she didn't know they were going to cum all over her when she said she didn't mind if they jerked off, but Joe already had painted her pretty good so she figured it didn't matter much."

"Fuck," was all I could think to say.

"Lighten up, Ace, you got off easy. You're lucky Amy thinks it's cheating to cum with another guy. As far as I'm concerned, it's not cheating unless you're fucking, especially if you aren't married," Anna said.

"Thanks for your opinion Anna," I said testily, "but I think I'm in a better position than you to define what cheating is in my own relationship."

"Whatever man. Anyway, she said you were a dick to her on the phone. Called her a whore and everything. Not cool, Ace." This girl was insufferable.

"Is she still mad?" I asked. "I mean, did she say anything about her and I going forward?"

Anna sighed. "Look, against my advice, Amy's wants to offer you a deal. You give her a pass for her behavior this trip and she'll forgive what you said to her. Fresh start tomorrow. It's a good deal- I told her to forget about you for the record.

I hesitated, but what choice did I have? I still loved my fiance, and at least this would put an end to this nightmare. "Ok," I said quietly, "I'll do it. I forgive her."

"Great, now say goodbye to Amy, she insisted on being on speakerphone to make sure she heard everything."

"Hey, babe," I heard Amy say.

"Amy- can we just talk-," I started, but Anna interrupted.

"Nope, she'll talk to you tomorrow," Anna said, and the line went dead.

I breathed a sigh of both exasperation and relief. As much as I still felt like I was getting the short end of the stick, I could at least stop worrying about further issues. And I did have Anna to thank for it, albeit reluctantly. Maybe she wasn't so bad. I texted her, thanking her for helping put this behind us and asking what they were up to this afternoon. I figured it was best to stay on her good side.

I turned my focus back to my work. Maybe I'd finally get something done.

My phone vibrated- Anna had texted back. "No problem, loser. We are headed back to Joe's condo, of course. I gotta see these big cocks for myself."

"Ha-ha," I texted. "Very funny. You guys don't spend too much money shopping. We've got a wedding to pay for."

15 minutes later, a picture came in. It was Amy and Anna in a hot tub. Wait an minute! It was Joe's hot tub! I recognized the railing on the balcony. In spite of myself, I had to admire how sexy they both looked. They were wearing their tiny yellow bikinis they'd bought at the store a couple days back.

"What the hell are you guys doing there???" I typed.

"Waiting on the guys to get home from golf. I bet they'll be all sweaty. Amy's so nervous she's chugging beers," said Anna.

"Nervous? Why would she be nervous?" I asked. My mind was reeling.

"Because you're the only guy she's ever fucked, so she's never been dicked properly. I told her it's going to be like losing her virginity all over again."

I couldn't believe this. "What?! Anna, we had a deal! No more naked and borderline cheating stuff on this trip. Please get her put of there."

"Nope, none of that was part of the deal. The deal was you give her a pass on this trip. I didn't say 'this trip so far'. No matter what she does today, she has your permission."

"No, Anna that was not my understanding," I texted as fast as I could.

"The thing is, I'm kind of the go-between here so it really doesn't matter what you believe the agreement was, only what I believe it was. And my interpretation is that Amy has a full hall pass tonight."

"Anna, this is bullshit. Please just let me talk to her."

"No way, Ace. Look, believe it or not, this comes from a good place. I'm her friend first and foremost and what I see in my friend is a girl who is on edge from planning a wedding and the events of this week, which was supposed to be relaxing until you made her feel bad about herself. She needs to party and she needs to cum, and she doesn't need you interfering. Allow her just get it out of her system. As far as she's concerned, you already have."

I just stopped responding. I couldn't believe I was going to have to endure another day of this. But my phone buzzed again.

It was Anna. "Who knows, Ace. Maye you'll get lucky and she'll chicken out. Do you want me to keep texting? I'll keep you updated if you want, but if you don't want to know I'll stop with the updates. I'll never tell you what happened tomorrow though, and I doubt Amy will either."

I buried my head in my hands and wanted to scream. I never should have trusted Anna. "Fine," I responded. "Keep me in the loop." Maybe Amy would just get tired or her conscience would kick in and tell her this was wrong, even though Anna had brainwashed her into thinking it was ok.

"Good choice, Ace. You are gonna get some spank bank material tonight" I almost had to admire how steadfastly slutty she was.

"Don't you have a boyfriend?" I asked. "What about Seth?"

"Eh, these guys are hotter."

I told my boss I was sick and drove home. I nervously waited for any updates, allowing myself to hope none would come. I resolved to not respond to the any texts I received from Anna tonight. She almost seemed to enjoy torturing me and take it as further provocation when I asked her to stop. I decided not to play into her hands. As much as I didn't want anything to happen, at least I'd probably get some more photos of Anna being slutty and quite likely in the nude. She was easy to look at and she was definitely an exhibitionist.

Finally after a couple hours an update came. "Flashing the guys on the balcony next to us". With the text was a picture of Amy and Anna, still clad in their yellow bikinis, but apparently flashing a couple guys who were about 15 feet away and looked to be in their 30's. The guys raised their drinks in approval. Anna was turned just enough sideways that I got a pretty good side boob view from behind. Their asses looked great in the miniscule yellow bikinis, Amy's just small and heart shaped, and Anna's more muscular.

I'd lost count of how many guys had seen my fiance's tits in the past few days.

30 minutes later another picture came. It was Amy sitting on a guy's lap, both of them naked. The guy's dick wasn't in her but was pressed up against the front of her. It was average size, I'd say it went a little over halfway to her belly button from the bottom of her pussy. I started to groan but then realized what I was looking at. This was my room in my apartment, and that was my dick. It was one if the few sexy pictures Amy's ever let me take of her.

Despite my pledge not to respond, I typed "Nice try, Anna. That's my dick."

"No shit idiot. We needed a starting point for comparison," cane her reply. With it was another picture. This was Amy in her yellow bikini, sitting in the same position on Josh's lap. The dick appeared to be the exact same size as mine.

Another picture followed shortly after. Same position but she sat in Kyle's lap. This one went well past her belly button. It seemed to be only an inch from touching the underside if her left breast. It looked like it would never fit inside her.

Finally, a third picture. Joe's dick obscured hid belly button with about an centimeter to spare. At least she still had her bikini on.

About 5 minutes later, another text came in. "Holy shit, there's drama. Look who just walked in." It was a brief video of a petite woman standing with her hands on her hips, looking at Joe as Amy scrambled to get off his lap. "Isn't the babysitter a little cliche even for you, Joe?" It was Avery. She turned and walked toward the door to one of the bedrooms, scoffing at Anna as she walked by. Anna turned the camera on herself, making a mock "cringe" face. Her top was still on but the cups were folded under her large boobs. I guess she hadn't bothered to put to it back on after flashing those guys. I felt my cock move a little.

This had to be good, right? Avery was about to shut this party down, right? I couldn't believe my luck.

My relief was short lived. 5 minutes later, another video came, a longer one. It was Avery emerging from the bedroom, in a red bikini. "What's everyone staring at?" She asked. "She walked to the fridge and opened a beer. She took a big sip as she walked toward the others. Setting her beer down on the counter, she remarked, "Hey, I thought this place was a naked only zone." Without hesitation she unsnapped a clasp between her bikini cups amd let her top fall. Her tits were not huge but they perky and were perfectly proportioned to her petite frame. She slid her bottoms down and kicked them off across the room. Kyle cheered and she told him to shut up. She walked straight to Amy and shucked her bottoms to the ground. Then she spun Amy around roughly by the shoulders and ripped the knot holding her top on loose, tossing the top aside. Amy reflexively covered her tits.

"Don't get shy now, Amy. Joe, take your trunks off. You're about to fuck the babysitter, we are going to have some fun tonight and then tomorrow we are going to repair this marriage," Avery said.

Amy finally found her voice. "Avery we don't have to-,"

"You do have to, Amy."

Amy argued no further. She got on her knees and was eye level with Joe's dick, which she started stroking. Soon after, she put her hands down by her side and wrapped her mouth around it. She bobbed her head back and forth for a couple minutes before Joe offered her his hand and helped her back to her feet. He lifted her off the ground and placed her on a padded barstool next to the counter. Amy was facing him with her legs spread wide as she braced the soles of her feet against his shoulders. Anna guided the camera closer as Joe slowly plunged himself into her wetness. I heard Any shudder violently as it went in. Her face was all nervous excitement as she used her feet on his shoulders to control his depth on the first few thrusts, letting him slightly deeper each time. The look on her face hid nothing- it was almost incredulous with disbelief at the pleasure she was feeling. Suddenly, the video ended.

About twenty minutes went by with no updates. I wasn't feeling anything more than a general surreal numbness. Then a new text came with another video, about 12 minutes long.

This one started with Anna showing herself in selfie mode, she'd folded her long slender body into a barstool as well. Her big tits were bouncing and I realized she was being fucked as well. She panned slightly to her right, and it was revealed that her barstool was side by side with Amy's, who was now being fucked hard and fast. She moaned and sighed as her tits jiggled with the rhythmic slapping. The camera panned back to Anna and then slowly down, to reveal a large dick going in and out of her pussy. Had to be Kyle.

After a couple more minutes she pointed the camera the other direction, between Kyle and Joe toward Avery, who was standing and watching the action. Josh was standing behind her with his right hand reaching around her side and fingering her, and his left groping her tits. She gasped in pleasure. Suddenly I heard grunting off camera and the view quickly swung back to Amy, whose mouth was wide open in ecstacy. The dick that I could see going in and out of her was suddenly removed and white cum sprayed all over her stomach and tits. She massaged her own tits cum covered and sighed.

"You didn't give her an orgasm, that's rude," Avery said. "Kyle get that dick over here, she continued as she walked toward Amy." Kyle pulled out of Anna and lay on the ground. Amy obediently climbed off the barstool and slowly lowered herself onto Kyle's dick, while Avery held it in place. "Fuck this little slut until she cums," Avery ordered. It was clear right away from the look in Amy's eyes that this wouldn't take long. She moaned loudly and started bouncing up and down on his cock. I couldn't believe it was physically possible that his whole length and girth was fitting inside. The pace picked up steadily. Soon, her tits bounced in circles and slapped together rhythmically as she squealed in delight. After about a minute, she came, collapsing as she screamed in ecstacy onto Kyle's chest. Her toes curled and she was visibly shaking. She put her mouth on his and kissed him passionately. Strangely this bothered me more than anything else I'd seen.

Avery rather forcefully lifted Amy by her arm off of Kyle and sat down in her place. As a saw his dick glide smoothly into her, I heard Joe start to object off camera to Avery fucking his friend. She just shushed him and kept going. Anna briefly pointed the camera to the couch where Amy was just sitting down next to Joe. She lifted his dick from his lap with a hopeful look on her face, but it remained flaccid and fell back onto his leg when she let go. "Reloading," Joe said with a sheepish smile.

Anna tossed the camera to Amy. "Make yourself useful," she said. Amy picked up the camera and recorded for another few minutes as Avery rode Kyle reverse cowgirl and Anna was taken doggystyle by Josh. Both girls came loudly and simultaneously. When Kyle started to show signs of finishing, Avery lifted herself off of Kyle and took him by the hand, then grabbed Josh's hand and led both guys to the couch where Amy sat. "Make sure and finish on the designated cum slut, just like last night."

Amy handed the phone to Anna as Joe fled the couch just in time. Both guys erupted directly onto her face, and for the second straight night, all three guys had cum onto my fiance.

"Ew," she said, cum dripping from her chin. She sighed. "Time for a shower I guess."

She stood up and walked toward the bathroom. "Hey Amy, blow Ace a kiss," Anna said.

"Good night babe, see you tomorrow," Amy said as she complied.

I spent the next several hours staring at the ceiling, feeling almost nothing. I couldn't bring myself to even begin to process what had just happened or how I would handle it tomorrow. It must have been well into the early morning hours when I finally drifted off.

I awoke mid-morning to a text from Amy. "Phone's working! Good morning babe!"

"Good to know," was all I could reply.

"Look there's one thing you should know, just so you aren't surprised when I get home."

I remember thinking that almost nothing could surprise me at this point. A picture arrived.