Senior Year at Sommerville High Ch. 05

Linda was a tall, slim, brunette beauty. Her wavy hair went past her shoulders and had light blue eyes. She had enough in her chest and ass area to not be called flat, but had the least curvaceous body among the females in the room. She looked to be in her late 30s, early 40s.

The four of them were in various states of undress. Samuel was in his briefs, Jorge and Adam in undershirts and briefs, and Linda was in a long t-shirt with possibly panties underneath.

Hannah then said, "I've known Linda and Jorge for a while. I met Samuel and Adam today. Adam piloted our flight to Boston."

We all got to know each other. They ordered room service and while we waited, we took shots of the tequila they had snuck in.

We got to know each other to the point where it didn't feel like a one night stand.

Jorge is from Arizona, bachelor and had been a pilot for nearly half a decade.

Samuel is married and has a kid. His wife is aware of his lifestyle and to my surprise, is ok with it.

Adam is divorced because his wife wasn't ok with his lifestyle. He said it was the best decision of his life.

Linda is also married and has an open relationship with her husband. He had even joined a couple of times.

The room service arrived, and it was all finger food.

I had the munchies after a couple of tequila shots, and was chowing down. Out of the corner of my eye, I saw Samuel and Linda kissing. I stared at them as Samuel snuck his hand under her t-shirt and started to play with her pussy.

Hannah caught me staring and said, "I would hurry up and finish eating. It looks like we're about to begin."

My sister whispered to Hannah, "There's 4 guys and only 3 girls. What is one guy supposed to do?"

Hannah smiled, and replied, "Linda and I have experience handling 2 guys before, so don't worry about that. Also, no pressure for you to do the same."

Hannah was right about it starting soon. Jorge and Adam got naked and both of them walked towards Dani.

Hannah said, "Hold on there, boys. One of you is gonna have to share Linda or me."

Adam looked at Jorge and said, "Seniority has to come in play here."

"Fine, but only cause this is my first time meeting you."

They shook hands and Adam made his way to Dani. Jorge looked over at Linda and Samuel, who were now naked.

He looked back at Hannah and me, saying, "Don't want to interrupt them."

"Fine by me," Hannah replied happily. "Dani and Adam, mind taking the rollaway bed or sofa bed. We're gonna need the queen bed."

They moved to the sofa bed which was out of sight. I was happy because I didn't want to see my sister get fucked or her see me have sex. But, a small part of me was a disappointed because I wanted to see her naked body.

Jorge was naked, and Hannah was half way to joining him when she asked, "Are you going to watch or join?"

"Join," as I started stripping and joined them in the nude.

Hannah and Jorge had already started kissing. I sat on the side of the bed stroking my dick as I watched them.

Hannah stopped kissing him to get on her knees and forearms, and faced me. We started kissing and a few seconds in, I felt her moan into my mouth. I looked and saw Jorge had started to eat her out.

I was still stroking when she said, "I'll take over from here."

She dove down on my penis and started giving me a blowjob. She didn't do much except for just bobbing up and down on it, but it still felt amazing due to her lips and tongue.

I was already on edge from the whole situation, that I was ready to cum after 5 minutes. A few more seconds and I would've came in her mouth but she unexpectedly stopped and pulled my penis out of her mouth.

She turned around, and rhetorically asked Jorge, "Didn't your dad teach you to always finish what you start?"

He had gotten up and was positioning himself behind her. He replied, "Don't worry. I'm gonna finish, and so are you." He slid into her and began to fuck her.

She went back to sucking me off and I came 3 minutes later. She swallowed it all without struggle, and not a drop spilled.

She stopped Jorge and said, "We need to get into a position where we can all have fun. Jorge, you're on the bed, I'll get on top of you."

Jorge did as told and Hannah got on top of him, with his cock finding a place in her vagina. She looked at me, and asked, "You ever fuck a girl in the ass before?"

I shook my head.

"Ever want to fuck a girl in the ass before?"

I nodded.

"Tonight is your lucky night. Get the lube and make yourself comfortable back there."

My mouth went dry. I slowly walked over to the pharmacy bag and got the lube. I got on the bed behind her.

She instructed me to lube up her entrance and my cock. I did as told and then placed my cock at her asshole. I took a moment to etch it in my memory before I pushed in. She didn't even seem to be fazed by it.

Jorge started drilling into her and I took that as my cue to start also. One or two thrust was all it took for me to get into my flow. We both started fucking her hard, and she was loving it. Her ass rippled with each thrust and it made me want to go harder.

I started to get tunnel vision. I didn't care that another dude had his dick in her vagina. I didn't care two people were having sex on the bed next to me. I didn't even care my sister was probably getting fucked in the next room. All I wanted was to fuck her ass to my content. I was so absorbed in it that I didn't even realize I came.

I was broken out of my trance when they called for a switch. I was confused and asked, "What do you mean by switch? Switch holes or?"

"Switch partners," Linda replied from the other bed.

Jorge pulled out of Hannah and quickly made his way to the room where Dani was.

Linda looked at me, asking, "What do you say? Want to give this old lady a try?"

I looked at Hannah for some reason wanting her approval.

She replied, "You can fuck whoever you want. That's the beauty of an orgy."

I walked over to Linda and she asked, "Ever been with an older lady before?"

"Uhm, I've never had sex with one but I've been to third base."

She laughed saying, "Third base? You are young if you're still using those terms. Let me show you what two decades of experience looks like."

I was caught off guard when she threw me on to the bed and mounted me. She started by nibbling my ears, then kissing my neck and slowly making her way down my body.

When she reached my cock, it was rock hard. She held it in her hand and once again caught me off guard when I felt her tongue near my ass. In one continuous lick, she went from my ass to the tip of me penis.

I still had some residual lube on my penis but she still spit on it a few times to make it even wetter. She started licking the tip of my penis and that made me twitch from pleasure. The head of my penis soon entered her mouth and I felt her tongue circling it and her pressing it against the inside of her cheeks.

After teasing me for a few minutes like that, she started to take my cock inch-by-inch till she had half of it in her mouth. I felt her suck hard, creating a tight suction like grip on my dick. Her tongue was doing all kinds of tricks that I can't even explain.

Linda gave me a blowjob while maintaining that grip. As she was doing that, I felt her fingers play with my balls. She occasionally would slip a finger near my ass but it was just a tease as she never put a finger in there. Despite ejaculating twice in the past half an hour, I came in her mouth. Like Hannah, she had no trouble swallowing the entire load, although it was much smaller than the one Hannah swallowed.

I was spent but she was ready for sex. She worked on my penis to get it erect again, saying, "There's no way a young stud like you can't get his cock up again."

"I've came three times in less than an hour."

"Let's see if we can make that four."

"If you can get him up again."

"Just close your eyes and let me handle it," she said in a motherly tone.

I closed my eyes and relaxed. I felt her hands on my penis. It felt relaxing, almost as if I was getting a massage. Having three orgasms in such a short time had drained me. My eyes were getting heavy, and despite my best efforts, I fell asleep.

I didn't know how long I was out for. I woke up on the rollaway bed and saw Hannah on a bed with Samuel and Adam, and Linda with Jorge. I guess the activities were done for the night since they were just chilling in the nude.

Jorge saw me wake up and said, "Morning, buddy. You fell asleep and I had put you on the rollaway to make some space."

"Oh, sorry about that. I think I'm going to freshen up." I checked my phone to make sure that it wasn't actually morning. It had just turned 10:30.

I walked in to the bathroom and saw Dani washing her face, nude. I saw her ass which was nicely shaped. I also saw her boobs through the reflection and they were big like her bra suggested, and had no sag.

I was going to walk out hoping she hadn't seen me, but she said, "Usually, girls are the ones to fall asleep after sex. Hannah and Linda must've done some job you."

"I'll come back after you're finished."

"Stay. It'll only be awkward if we make it awkward."

I walked to the other sink and splashed my face with cold water.

Dani took a seat on the vanity top, and asked, "How was your first orgy?"

"It was good. Wished I could've stayed up for all of it. How was it for you?"

I had a hard time not looking at her boobs. My eyes would naturally gravitate towards them before I had to pull them away.

"I can see you looking at my boobs. If I'm comfortably sitting naked in front of you, there's no reason why you shouldn't be comfortable looking at me."

"Oh, ok. It's just that it's a little weird."

"Yeah, it is for me too but I'm doing my best to act like it's not. As for the orgy, I never thought I would have sex with three guys in one night."

"Yeah, same here Except with girls, not guys. Don't we have to get back?"

"I think everyone will be asleep at home by now, so we don't need to rush."

Hannah walked in to the bathroom, closing the door behind her. With a big smile on her face, she said, "I hope I didn't miss any brother-sister action."

Dani replied, "Definitely didn't miss anything."

"Hmm, let me know if you do anything. I love brother-sister porn, real life would be even better."

"Uh, sure."

Hannah was eyeing Dani's boobs just like me. She however had the courage to ask her to play with it, which Dani agreed to.

Hannah took them in her hands, playing with them like a kid plays with toys. At the end, she said, "I wish my tits were great like yours."

"Your ass is way better than mine. We can call it even. Don't you think so, Jake?"

"Of course."

Hannah replied, "His cock certainly agrees. How did you guys enjoy your first orgy?"

"He's upset that he fell asleep halfway through," Dani replied.

"Oh, I'm sure Linda's down to have sex. Finish what you guys started."

"Really?" I asked eagerly.

"She should be. She's a nymphomaniac. I've heard some of her sex stories and they get pretty crazy. Doesn't hurt to ask her right?"

"Yeah, but I feel weird asking her. Especially in front of other guys. What if she says no? I'll never live that down."

She sighed, took my hand and dragged me out of the bathroom.

In front of the other guys, she asked, "Linda, do you want to fuck Jake?"

At that moment, I felt like a little boy whose mom was fighting the bullies for him. I didn't lift my head up, making intense eye contact with the hotel carpet.

"Of course I would." She got up from in between Adam and Jorge and walked over to me.

"Let's head to the sofa bed. More privacy."

Hannah looked at me, and said, "You're welcome," before heading back to the bathroom.

Linda laid down on the sofa bed which was a mess from all the sex that had taken place on it.

She spread her legs inviting me between them. "I think we've both had enough foreplay that we can go straight to the sex."

I put on a condom and accepted her invitation. I put my body weight on top of her and started pumping into her hard.

The nap had done me good as I felt fully recharged. I was going at full speed but wasn't sure how much of a load I could produce. Having sex with Linda also helped. She was very vocal and great at dirty talk. It made me want to go even harder than I could.

My penis was still burnt out from the blowjobs and sex from before, meaning I could enjoy for a while. It took me 15 minutes before I came. In that time, I watched Linda cum twice.

The first time, she let out a loud groan, letting everyone in the room know that she was having an orgasm.

The second time was even better. She clawed my back, dug her heels into the bed and her hips thrusted upward. I felt her clench my cock hard inside her vagina.

After we had finished our session, she said, "I would love to throw you on the bed and fuck you wild, but I don't think either of our bodies can handle any more pleasure."

We laid on bed and started talking to each other.

She asked, "Was I better than the other older lady you had sex with?"

"I didn't have sex with her."

"Oh, yeah. That's right, only reached 'third base'. Is sex in the books?"

"I don't know but I certainly hope so."

"I would give you pointers but you seem to know what you're doing. Only tip is make sure you take a nap ahead of time."

I blushed and apologized by saying, "Sorry about that. It had nothing to do with you. I never had came that much before in such a short time."

"I understand. The first orgy I had, I left early because I was so tired of having sex."

"How many have you been a part of? Hannah made it seem like it was a regular thing among air hostesses and pilots."

She laughed before replying, "It does happen but not every single time. I have lost count though."

I got the sudden urge to pee, and made my way to the bathroom. As I entered, I was greeted by the sight of Hannah kneeling and eating my sister out.

My sister saw me walk in but she was too busy enjoying Hannah's tongue to say anything.

I said, "I guess I'll come back later."

Hannah turned around, and said, "I don't mind the audience. Do you?" as she asked my sister.

"I don't care if my dad or mom were watching, just make me cum."

Hannah went right back to doing what she was before.

I walked over to the toilet and relieved myself. Instead of heading back out, I stayed in the bathroom to watch.

Dani was really enjoying it, as she held Hannah by her hair to make sure she didn't stop. Her panting was replaced by, "Yes, yes, yes, almost there, AAGHHH!!!!"

She came, and she came hard. She squirted like they did in porn videos. It cleared Hannah and almost made it's way to me.

She slumped back against the mirror and said, "I can't believe I just did that."

"Neither can I," I replied.

From her knees, Hannah said, "That makes three of us."

Witnessing that made me semi-erect.

After Dani and Hannah cleaned up, we left the bathroom to join the others.

We noticed that it was almost midnight so Dani and I decided to leave. We got dressed, said our goodbyes and headed downstairs when our Uber arrived.

The car ride was silent. We reached our grandparent's house and let ourselves in with the spare they had given us.

A note had been left on the refrigerator, saying, "Dani can take the guest bedroom. Jake you can sleep on the sofa but it does get very cold there. If you two don't mind, I'd recommend Jake sleeping on the floor on an air mattress in the guest bedroom. Love, Gramma."

I said, "I don't think sleeping in the same room would be all that weird. Do you?"

She chuckled, then replied, "Of course not. This would be normal compared to where we just came from."

I took the sheets and air mattress and we both headed to the guest bedroom. I worked on making my sleeping arrangement while she went to shower.

When she came back, she joked, "I brought my bra back. Do you want it so you can cum on them again?"

I laughed dryly, saying, "Very funny. Plus, I don't think I can cum anymore. Hannah and Linda drained me good."

I was feeling sleepy so I took a quick shower and was under the sheets all within 10 minutes.

I was about to drift off to sleep when Dani woke me up. "Jake, did you sleep yet?"

"I was about to."

"I know I already asked this but did you really enjoy tonight?"

"Of course. What guy wouldn't enjoy having sex with 2 hot women in one night. You?"

"Loved it."

"Who was the best?"

"I would say Hannah but if you meant guys, Samuel."

"She was that good huh. Did I miss anything?"

"Nope, she went down on me. Nothing else happened."

"This is going to sound weird but I don't remember Samuel's dick. Was it really that big? Like the stereotype?"

"It was definitely big. I can't speak for all black guys but he fits the stereotype. Uh, you're pretty big too."

"Uhm, ok. I wasn't wondering that, but thanks."

"Oh. I thought you were feeling insecure about your size."

"No, I'm not. I've done my fair share of googling and know I'm comfortably above average."

"Comfortably?"

"Five and a half is average, I clear it by 2 inches."

"Congrats. I guess?"

We both laughed and I asked, "Speaking of sizes. Your boobs are pretty big."

"I know, I got it from Mom."

"How.."

"It fluctuates a lot but most of my bras are 36C."

"Hmm. Uhm, I think we've crossed a lot of brother-sister boundaries we weren't supposed to."

"Without a doubt. But I think as long as we don't cross anymore, we should be fine. Right?"

"Yeah."

She yawned and we said good night before sleeping.