Theater kids go to senior week! [MFF]

A recurring theme in all of these stories is that they involve friends I knew from my high school theatre days. This particular story involves two girls who were best friends all through high school, Jessica and Rachel.

Jessica and Rachel were inseparable in high school. They were always in the plays though neither of them ever played the lead. They mostly just hung out as extras on stage and sang in the choir. They were also the kind of best friends who would constantly talk shit about each other when the other wasn’t around to the point you wondered why they were friends at all.

They were both objectively very attractive but while Rachel was clearly very pretty, Jessica was one of those girls who is so hot it’s frustrating to know she exists. Jessica was easily a 10 but she was also one of those girls that was really awkward in middle school and early high school that she had no idea how hot she had become. Jessica had brown hair that hung to around the middle of her neck. She wasn’t pale but she wasn’t particularly tan either. She had a perfect, hourglass figure. Without working out she somehow had a tight little stomach and also had D-cup boobs. She also had these big, round, brown eyes that could knock you on your ass whenever she flashed a smile.

Rachel had long curly red hair and pale, freckled skin. She had ruby red lips and a bit of the crazy eyes. She was slightly curvier than Jessica, with large boobs and a little more pudge around the belly. I think Rachel developed sooner than Jessica and had become accustomed to getting all the attention and I think it bothered her when Jessica came into her own and started to outshine her.

I made friends with both of them after they started hanging out at parties at my house senior year. My parents were never around so my house became the home base for underage drinking parties in my area.

Rachel and Jessica both liked attention. They both used to dress really slutty whenever they would come to parties together and I think they always felt like they were in competition with one another. They both liked to have fun but Jessica would never get too crazy. If we were playing beer pong, Jessica and Rachel would make out in order to distract the guys they were playing against. Jessica would often joke about flashing her boobs to get what she wanted but she would never go through with it. I used to stand at the beer pong table getting ready to throw and I would watch as she would grab the bottom of her shirt and raise it above her bellybutton to just under her bra, teasing that she might just flash me to throw me off my game. In my entire life, I’ve never fantasized more about seeing a girl naked than Jessica.

Rachel was a bit more notorious. I had heard stories about her. She had flashed her boobs at the cast party for the spring play that year but I wasn’t in the room to see it. My friend John also swore that one night after a party he walked her to his car and she gave him a handjob, but that story has never been confirmed.

This story took place at senior week.
A handful of my guy friends all pooled our money together to get a hotel during senior week. Rachel and Jessica and three other friends of theirs did the same. It turned out that our hotels were right near each other along the boardwalk. The first night we were there, my friends and I walked down to the girls hotel room to pregame before going out on the boardwalk that night. What followed was typical young underage drinking shenanigans. We went to an under 21 club. We wandered the boardwalk and the beach. Met other drunk graduates and sang along with street performers.

As we intermingled with different groups on the street, different people started going in different directions. I ended up with Jess, Rachel, CJ, Steph, Eric, and Melanie. After Eric almost got into it with a cop we decided it would be best to head back to the room.

On the way back to the room, CJ was asking me about Rachel. He clearly had a crush on her and was trying to stake out his territory. Eric was a bit of a loudmouth who was always just kind of around. I didn’t dislike him… I just didn’t like him all that much either. Steph and Melanie were in theater with us too. Melanie had moved to our school this year and made friends with Steph who in turn was friends with all of us.

We get back to the room and we start playing that card game “Asshole” (I think some people call it “President”). I don’t really remember the rules because it’s been so long but I remember that, in the way we played, the president (whoever won the round) would get to make a rule that everyone else had to abide by for the rest of the game. It was usually like, “Drink anytime someone says the word ‘the’” or something foolish like that.

As the game progressed everyone started to get really hammered. Eric kept saying that as soon as he was president he was going to “see some titties”. Alas, Eric was not the one to make a rule that involved nudity. Steph won the next hand.

“My first decree is that the next guy who says the words ‘shit’ or ‘fuck’ shall have to whip out their dick”, Steph said with authority.

“What the fuck?! I don’t want to see another guy’s dick!” Eric shouted, stupidly.

“And now you gotta show YOUR dick, dumbass!” Rachel pointed out.

“Why?” Eric asked.

“You just said the ‘F’ word, those are the rules,” Steph replied.

Eric froze for a moment trying to think of a way out of it but couldn’t. I won’t try to be all macho and pretend like I didn’t look. I looked as he unzipped his fly and whipped out his cock. Now I’m not small but Eric definitely had me beat. He was sporting a chubby and his dick was veiny and thick.

“You guys are in so much trouble once I win a hand,” Eric said, defiantly.

The girls were all staring at his cock and giggling and I began to feel myself getting aroused. Eric tucked his cock back in his pants and we went back to the game.

I won the next hand and decided to be bold.

“Fine. If we have to whip it out if we say the ‘F’ word or the ‘S’ word, then so do you. Any girl who says the ‘F’ word or the ‘S’ word has to flash her boobs for 10 seconds,” I decreed.

“Psh Whatever,” Rachel scoffed.

We kept playing and to my dismay, none of the girls said either of those words. Four or five rounds later, Melanie went to toss a card into the center of the table and accidentally threw it too hard and let out a reflexive “FUCK!”

“Uh oh! You said the ‘F’ word, now you have to flash!” Eric said, excitedly.

Melanie rolled her eyes back in acceptance, lifted her shirt and bra up to expose her B-cup boobs. They were pink and perky and I felt my erection strain against my jeans. I was really taking care not to say those words because I was insecure about my size compared to Eric and now I was sporting a full on erection which would be doubly embarrassing.

A few rounds later CJ broke a rule, I don’t remember what the rule was, only that we all had to drink. Jessica was sitting next to me. She took a swig from her beer bottle and when she went to pull it away a little bit of beer spilled on her chin.

“Shit,” She said quietly as she cupped her hand under her chin.

Everyone was laughing and carrying on that no one else heard her say it.

I leaned into her and whispered, “Be careful, you just said the ‘S’ word.”

She looked at me mortified but I assured her I was the only one who heard it and I was going to give her a pass.

Jessica whispered back, “Thank you.”

The game continued and I was kicking myself for not holding Jessica to the rules. For all I knew that could have been the only chance I would ever get to see her gorgeous tits.

During the next round, Rachel broke a rule that Melanie had made which required her to tell an embarrassing story. Rachel told the story of a time she was giving her ex-boyfriend head in her parents house when her parents came home early, unexpectedly.

“I hear the car door slam and I’m like ‘oh fuck, my parents are home’,” Rachel recounted.

Poor CJ had passed out drunk earlier in the night and was going to miss seeing Rachel’s big tits.

Eric, without missing a beat goes, “Uh oh, you said the magic word! Let see some boobies!”

“What?! No way! I was telling a story! That’s not fair!” Rachel complained.

“Those are the rules, slut!” Jessica, chimed in playfully.

I thought it was funny that Jessica would be such a stickler for the rules since I had given her a pass earlier, but she was three sheets to the wind at this point.

“Fine,” Rachel said, defeated.

Rachel stood up and started unbuttoning this tight corset-like vest she was wearing. Once it was open, Rachel lifted the shirt she had on underneath up to her bra. Then she wedged her fingers under her bra wire and stretched it up and over her big tits. I could have cum in my pants right there. She had big, round, pink nipples and her tits were covered in freckles.

Rachel cupped under her tits and pushed them together and said, “Happy?”

Rachel pulled her bra back over her boobs and we went back to the game.

I was really angry at myself for not enforcing the rules on Jessica when I had the chance. It was starting to get late and everyone was getting tired. Jessica leaned down to her purse on the floor so she could check her phone and see what time it was. When she came back up she bumped the table and her beer tipped over. It wasn’t very full and didn’t make much of a mess but Jessica absentmindedly shouted, “SHIT,” loud enough for everyone to hear.

“Who’s the slut now, bitch?!” Rachel teased, gleefully, “Let’s see those boobies, woo!”

Jessica started to pout. She wasn’t really upset she was just feigning, hoping sympathy might get her out of it.

“Boobies! Boobies!” Rachel and Steph started to chant in unison (Melanie had fallen asleep by this point).

“No way I’m showing Eric my tits,” Jessica said, firmly.
“Wait! What’d I do? That’s not fair!” Eric protested.

Finally I decided to speak up.

“Look it’s only fair, everyone else who broke a rule faced the consequences,” I said, “However since I made the rule I will let you choose, either you flash us all here or you can flash just me in the bathroom.”

Without hesitating, Jessica said, “Ok fine, let’s go to the bathroom.”

My heart started to race. I never thought this would actually happen. I stood and followed Jessica as she got up and walked past me. Eric kept griping and I felt bad about leaving a man behind but I was not about to pass this up.

I followed Jessica into the darkness of the bathroom. I closed the door behind myself and felt like my heart was going to explode out of my chest. Once I heard the click of the lock, I found the light switch by the door and turned on the lights. We both winced and squinted our eyes at the sudden brightness. The hotel bathroom was huge and had a jacuzzi tub. I went and sat on the edge of the tub and turned to face Jessica. Jessica stood with her hand shading her eyes for a minute.

“Those were the rules, I let you off once,” I reiterated.

“I know, I know,” Jessica repeated, “I’m just nervous. I think my boobs look funny. Promise you won’t laugh,”

“Are you kidding me? Your boobs are perfect. I can tell that much even with your shirt on!” I reassured her.

Jessica lowered her hands to her side.

“Ok, ok, are you ready?” she asked.

I felt my heart flutter. I had been in denial up until that point but this was really going to happen.

“I’m ready whenever you are,” I replied.

Jessica lifted her shirt up over her bra and held it there for a moment. Her cleavage pouted out perfectly from the tight black bra she was wearing.

“Ok, here you go…” Jessica said as she lifted her bra. Her incredible tits dropped out and I was staring as if they were the only two things that still existed in the world. To this day I’ve never seen a more perfect pair of tits. Not even in porn. They were full D-cups on a tight little body. Her nipples were smaller than Rachel’s and they were totally erect because of how nervous she was.
“Holy shit, Jess. What could you possibly think is wrong with your boobs?” I asked, “They are literally perfect.”

“I don’t know, I just think they look funny,” Jessica replied as we both just stared at her bare chest.

“Well you are crazy. You have the best boobs I’ve ever seen,” I insisted.

“Oh shut up. You’re just saying that,” She scoffed.

“It’s true. Look, full disclosure, I’m, like, really hard right now, and it’s because of you,” I revealed.

“Nuh uh! Really?!” Jessica asked, skeptically.

“Seriously! I’ll prove it to you if you want,” I don’t know where I got the guts to say that.

Jessica looked down at the stiff bulge at the front of my jeans.

“Is that your dick?” Jessica asked.

“Yeah… Do you want to see?” I offered.

Jessica considered it for a moment and said, “…Yeah.”

I leaned back on the edge of the tub, unzipped my jeans, and pulled out my hard cock.

“Holy shit. You weren’t kidding!” Jess said in surprise.

“Do you want to touch it?” I offered.

Jess just stared intently at it and said, “Just for a second.”

Jess, with her tits still out, reached down and wrapped her hand around the shaft of my rock hard cock. I’m average sized but in her tiny hand, my dick felt HUGE. Then Jessica started to stroke it. I sat back in that uncomfortable position and let her play with my dick a little longer but then I felt myself getting ready to cum. She realized what was happening and stopped.

“Ok, playtime’s over,” she said, abruptly.

Everything in me wanted to beg and plead with her to keep going but I didn’t. Jessica lowered her bra back over her tits and I put my dick back in my pants. I then got up and followed her out of the bathroom.

When we went back into the next room, Rachel pointed out, “Hey! That was way longer than 10 seconds. What were you two doing in there?”

“Oh shut up, Rachel,” Jessica deflected.

We went back to drinking and eventually Eric open a bottle of rum and we started doing shots. We sat around telling stories for a while. Jessica eventually decided to go to sleep and went and passed out in one of the two queen sized beds where Melanie had been sleeping.

CJ was passed out in the armchair in the corner and Steph had fallen asleep on a cot. Eventually Eric made a pallet on the floor and Rachel and I got into the other queen bed. At this point it was about 3:30 am and the only ones left awake were Rachel, Eric, and I. Eric had been acting salty all night after missing out on Jessica’s boobs.

Eric and Rachel had a flirty but contentious rapport and they were giving each other shit as we laid awake talking. We were all really drunk and we started doing that thing where you finally all agree to be quiet and go to sleep only for one of you to start giggling which then triggers all of you to giggle. Eric was giving Rachel shit for giving a sophomore a handjob at the theater cast party. He called her a slut, but not in a mean way. They just had that kind of rapport. Rachel gave as good as she got.

“I am not a slut!” Rachel said in defense.

“Oh please,” Eric said, “If we told you to give us both head right now you would!”

“Nuh uh! I would NOT just give you both head!” Rachel insisted.

“Fine. So we’d have to flip a coin!” Eric said, sarcastically.

I thought it was just a joke, but out of the darkness I hear Rachel’s voice say, “Ok I’d probably do it if you flipped a coin.”

She said it so matter of factly and started to giggle. My dick immediately went fully erect. I think she just meant it as a joke but as soon as she said it I could hear the blankets on the floor rustling. I saw Eric get up and go to his jeans that were draped on the dresser.

“What are you doing?” Rachel asked, pretending like she didn’t know.

“You said you would give one of us head if we flipped a coin. I know I’ve got a quarter in here somewhere!” Eric replied, excitedly.

I sat up and turned the bedside light on. Eric walked up to the bed and said, “Heads or tails?”

I looked at Rachel who just looked back at me with her eyebrows raised.

“Tails!” I replied. I always pick tails because I feel like everyone always picks heads.

Eric flipped the quarter up into the air and it landed back down on the bed. It was tails…

“God damnit!” Eric said in a whispered shout. He put his jeans back on the dresser and slumped back into his bed of blankets on the floor.

I turned and looked back at Rachel.

Rachel rolled her eyes and said, “Ugh, Fine! But be quick!”

She pulled the blanket down to where my boxer briefs were uncovered. I was pitching an obvious tent with my erection. Rachel wrapped her hand around the shaft of my penis while it was still inside my underwear. She started to stroke me over my underwear. I was really nervous because anyone in the room could see this happening. They were all asleep but I didn’t think for a second that there wasn’t a chance someone could wake up.

Rachel reached down with her other hand and pulled my cock out through the hole in my shorts. She kept stroking me and I was so turned on I didn’t care if someone woke up and saw, there was no way I was going to stop this from happening.

Rachel shifted down to where she was face to face with my rock hard cock. She looked up at me as she started licking right underneath the head of my dick. I looked back at her and our eyes met. Then she took my hard cock all the way into her mouth and down her throat until her nose touched my stomach. I watched as her curly head of red hair bobbed up and down as she slurped loudly on my dick.

“Oh my god!” Eric responded to that sound from the floor below.

“Shut it!” Rachel replied before she went back to sucking me aggressively.

In hindsight, there is no way that some of the other people in the room didn’t wake up. Rachel was voraciously bobbing her wet mouth up and down on my cock, sucking and slurping all the while. But if someone did wake up, they never said anything.

I reached my hand down into Rachel’s shirt. She had taken off her bra when she went to bed and I took a handful of her braless tit. Rachel moaned when I squeezed and I could feel the vibration of her moan on my dick. I was getting close.

“Rachel, I’m going to cum,” I whispered, desperately.

“Mm kay,” Rachel replied in a muffled mumble.

I watched her head bob up and down faster now. I focused on the sounds her mouth was making as my dick hit her in the back of the throat. I honestly don’t think she would have gone through with this if it weren’t for her feeling of competition with Jessica. Either way I was starting to cum.

I felt a warm swell rush through my body. All of my muscles clenched as I grabbed Rachel by the hair on the back of her head. I felt my dick throbbing in her mouth as I started shooting hot cum into her throat. She held her mouth down on my cock as far as it would go as my dick made its final few cum spasms.

Rachel took my wet cock out of her mouth and wiped the corners of her lips.

“Holy shit,” I said, exhausted.

“Aren’t you glad you picked tails?” Rachel asked with a smile.

“Oh my god, yes,” I confirmed.

Rachel crawled over me and turn out the bedside light. I was completely spent and fell asleep not long after that. For the rest of the week we pretended like nothing happened, as did everyone else who might have woken up.

Source: reddit.com/r/gonewildstories/comments/57f0pz/theater_kids_go_to_senior_week_mff