Senior Year at Sommerville High Ch. 07

"Thank you, guys! I love it," hugging them.

Next was my turn, and I had gifted her a decorative piece. I also attached a small note to it.

'It'll look great at your new place.

P.S. Please let me crash at your place when I visit the city :)'

She gave me a sly smile and hid the note from our parents as she handed them the decor to look at.

Mom asked, confused, "Where is she supposed to put this? In her room? This is more of a living room piece."

"I'm sure I'll find a place for it, Mom," Dani replied.

I grabbed the last box from under the tree, and Mom asked, "Dani, didn't you get your brother anything?"

"I did. I just forgot to wrap it. I'll give it to him when we go upstairs."

I opened the gift from Mom and Dad. It was the PS5. "You got this! I've been looking for this since it was released!"

Dad sarcastically said, "You're an 18-year-old boy happy about a game console."

My mom slapped him on the arm and said, "I hope you like it. But studies are still priority number 1, mister."

"Yeah, yeah, I know, Mom. Thanks, guys."

It was pushing 3 in the morning, and relatives would start coming in at 10. We cleaned up the wrapping paper and went upstairs.

I was in the middle of changing when someone knocked on my door. I peeked and saw it was Dani. I told her, "Hold on, I'm changing."

She raised her eyebrows and said, "Are you serious?"

"Oh, right. Come in."

She handed me a piece of paper with an email and password written on it.

"What's this?"

"You're Christmas gift."

"A Gmail account?"

"Open your laptop, log in, and check the drive."

I did as she said and saw a folder called 'Jake's Christmas Gift' on the drive. I looked at her and asked, "What's in this?"

"You'll see. In case you don't want it. I have a backup gift, too."

I opened the folder, and inside were images. The thumbnails had a woman wearing lingerie, but it wasn't Dani. I clicked one of the images, and a full-size image of Mom wearing sexy black lingerie filled my screen.

"What is this?" I exclaimed.

"Shush! You'll wake up Mom and Dad."

"Where did you get this? Why do you have this? And why did you give me this?"

"Mom is attractive, and you know it. You were already masturbating to one woman in the house, so I thought, why not the other one."

"How did you get this?"

"I went lingerie shopping with Mom. That's her gift to Dad. I convinced her to let me take pictures to go through them all. I uploaded them to a drive and gave them to you. If you don't want it, I'll delete the account and give you a check for 100 bucks."

Instead of answering, I was going through all the photos. There were more than 50 photos of her trying different sets of lingerie.

"I take it to you like this gift," Dani said.

"Uh, yeah. I'll keep this. Thanks."

After Dani left my room, I waited 5 minutes before whipping out my cock, and starting to masturbate to the pictures.

I came in under 2 minutes, which I hadn't done in a while. In my eagerness to jerk off to pictures of my mom, I forgot to check if I had tissues.

I made the awkward walk to the toilet, careful not to leave any more cum stains.

After cleaning up, I was walking back to my room when I heard a whisper, "Busted!"

I jumped and saw that it was Dani.

"I didn't think you'd use my gift that quickly. Or that you would cum that fast. And I'm slightly offended you don't cum that quickly when I get naked for you."

"I was already on edge. Now go back to your room before they hear us."

Back in my room, I went through all the pictures again and even contemplated masturbating again but decided against it.

I put the laptop away and dozed off to sleep.

CHRISTMAS

When I jerk off before going to sleep, I wake up late the next day. This day was no different. Dani barged into my room and shook me awake.

"I'm up! I'm up!"

"How many times did Mom make you cum last night?"

"One. And why did you wake me up?"

"Because it's 9:15, and you're supposed to pick up Grandpa and Grandma from the airport."

"Can't you do it?"

"No."

"Why?"

"Because I don't want to."

"Hurry up! Their flight lands at 9:20."

I quickly got ready and went downstairs. I grabbed a protein bar and a water bottle to eat on the go.

As I put on my shoes, my Mom said, "There you are. I've been waiting for you."

"You have?"

"Yes. I'm coming with you to pick up your grandparents."

"Uh, you don't have to. I can go by myself."

"I need to stop at the store and grab something for lunch."

"Tell me what you need, and I'll get it."

She looked at me and said, "What's up with you? I'm coming with you, and that's final."

I saw Dani smirking at the breakfast table and had no doubt she purposefully made me go.

We got in the car and went to the grocery store first. After she bought what she needed, we got in the car and set off for the airport.

"I forgot to ask. What did Dani get you as a gift?"

"Uhm, nothing."

"Nothing? I asked her this morning, and she told me to ask you."

"It's a photo album."

"Oh, that's nice. Can I see it?"

"No! Well, I mean, you can't. It's on the cloud. It's a hassle to get it."

"That's sad. Why are you kids making everything digital nowadays? What's wrong with an old-fashioned photo album? That way, everyone can see it."

"Uh, yeah."

Once we got on the highway, the driving became tough. I thought of the lingerie photos, wondering what she was wearing underneath her clothes now.

I noticed how large her breasts were and even imagined what it would be like to play with them.

My cock started straining against my jeans, and I had to think of other thoughts to calm down. It wasn't easy because her boobs jiggled as we drove on the highway.

We reached the airport and spotted my grandparents waiting for us. I walked awkwardly to hide my boner as I loaded their luggage into the trunk.

Fortunately, my mom sat behind me on the drive back, meaning she and her boobs were out of sight.

When we got home, I rushed to my room to jerk off. I opened the folder and picked a random photo of my mom.

I was about to cum when I remembered I didn't have tissues in my room. Not able to stop myself, I came into my hand. I opened my bedroom with one hand to see if the coast was clear and ran to the bathroom.

After washing up, I rejoined everyone downstairs.

Dani asked me, "Did you go upstairs to enjoy the gift?"

"Yeah. That car ride was torture."

"Let me guess. Her boobs were a big distraction."

"Yes, a BIG distraction."

"There are more photos. I selected the best ones and put them in there."

"Can I get them?" I asked eagerly.

"It's gonna cost ya."

"How?"

"Hmm, I need to think about it."

The rest of the family started arriving, and everyone got preoccupied with Christmas. It was great as I got to see relatives I only saw a few times a year. This went without saying, but the gifts were also great. Overall, I got a decent haul on Christmas.

After dinner, the men and older boys went downstairs to watch basketball. The kids played, and the women and older girls talked in the living room.

People started leaving near midnight. Only my grandparents stayed at our house, as everyone else got a hotel room.

Alone for the first time since noon, I was tempted to open the folder and masturbate to my mom again. However, I didn't want to overdo it.

Instead, I did something I hadn't done in a while, watch porn. I was browsing videos when Matt texted me.

Matt: You up?

Jake: Yup. What's going on? How was Christmas?

Matt: It was fun. Nothing special. Yours?

Jake: Same. Are you ready for the ski trip?

Matt: That's what I wanted to talk about. Did you have gear?

Jake: Nope. I need to buy some this week.

Matt: Perfect. I need to get new gear, too. Want to go together?

Jake: Sure. It'll help since you know what to get.

Matt: When do you want to go?

Jake: My grandparents leave tomorrow. Does the day after tomorrow work for you?

Matt: Works for me.

Jake: Alright, I'll see you then.

Matt: Okay.

After texting Matt, I didn't feel like masturbating, so I went to bed.

DECEMBER 27TH

The Christmas rush was over, and I had the first time to relax in what felt like forever. Matt and I agreed to meet up in the afternoon.

During breakfast, my mom said, "One of my college friends is in the city. She'll be coming sometime today."

"That's cool. This is the first time we're going to meet one of your old friends, Mom," said Dani.

"Hmm, that is true. She's the best person to meet. We did everything together in college."

"What's her name?"

"Linda."

"What time will Linda be coming? I'm going with Matt to buy ski gear," I said.

"Oh, she didn't tell me exactly when. Probably in the evening, and join us for dinner."

"Just make it quick, or come home when I text you."

"Will do."

It was one of the coldest days of the year, making it perfect to nap under warm sheets. I wrapped myself into a burrito and fell asleep. I woke up when Matt called me, saying he was waiting outside.

I changed quickly and ran downstairs. I saw my mom and asked, "Did Linda come yet?"

"Not yet, honey. Where are you going?"

"I told you. To get ski gear with Matt. He's outside."

"But you didn't have lunch."

"It's ok. I'll get go through a drive-thru."

"Ok. Don't forget. Come home when I text you. I want you to meet Linda."

"Yeah, yeah."

I hadn't noticed it before, but Mom wore a low-cut top showing cleavage. This was different from what she usually wore. She dressed conservatively, hiding her curves and body. I hadn't even noticed how big her breasts and ass were until Dani gave me the photos.

The blood started rushing to my penis and made me debate whether I should masturbate before leaving. But Matt called me again, and I ran outside to get in his car.

"Hey, how's it going?" I asked as I got into the car.

"Good. My uncle took me to this amazing house he may buy."

"To live in or to rent out?"

"Rent but maybe flip. It's a winter cabin, so it'll be busy in the winter but not so much in the other seasons."

"Can we stop at a drive-thru? I didn't have lunch."

"Sure. McDonald's, Burger King, and Taco Bell are on the way. Which one do you want?"

"McDonald's. On the topic of your uncle and his properties. Why do you get a summer job? Doesn't your uncle pay to help him with his properties?"

"He does. But my Dad and my uncle didn't have the best relationship at the time of my Dad's death. My Mom and I were surprised when he came and looked after us. I like to think he's a nice guy, and his bad blood with my Dad hasn't carried over to us, but my Mom is skeptical. She doesn't want us to be reliant on him."

"Makes sense."

We reached the drive-thru, where I got a meal for myself and nuggets for Matt.

The store was a short drive away, so we finished eating in the parking lot.

Neither of us was picky with looks as long as it got the job done. I went with slightly cheaper stuff, knowing the chance of me using it again was unlikely. Matt splurged a little, using his Christmas money early.

During checkout, I asked, "Why didn't Ray and Tyler come with us?"

"Ray's parents bought him ski gear as a Christmas gift. And you know Tyler, he got some second-hand stuff from the thrift store."

"That is on par for him. What about the girls?"

"Sydney already has. Zoe and Soniya went the day after we booked everything."

On the walk to the car, Matt asked, "Do you think we'll ever have sex with Sydney again?"

"I gotta come clean. I already did."

"What?!"

"It's a long story, and it wasn't planned. She was going through some stuff, and I happened to be there. I'm sure that if you were there instead of me, she would've had sex with you."

"When was this?"

"Last month."

"Last month! And neither of you thought of telling me. I thought we were a trio and did that stuff together."

"Chill, Matt. Maybe we can talk to Sydney, and she'll even it out."

"She's not a prostitute!"

"That's not what I meant. Dude, listen, I'm sorry. Again, it wasn't planned. It happened out of the blue."

"Did you even think of me when you were fucking her?"

"Uhm, I don't think of guys when having sex with a girl."

"Stop making jokes. You know what I meant."

"Ok. No, I didn't think of you. Like I said already, it just happened."

"Whatever. Get in the car, and let's go."

The car ride back was dead silent. I turned on the radio to break it up, but he turned it off.

We pulled up in front of my house, and before getting out, I asked, "We good?"

He grunted and left as soon as I closed the door.

I got in my house and went straight to my room. I took out my phone to FaceTime Sydney.

She answered the phone from her tub. She was nude, and I saw her breasts covered in soap suds.

"Woah. I'll call back later," I said.

"Are you serious? We've fucked, and you're acting shy about seeing me naked."

"This feels different."

"Live with it. What's up? You usually text."

"I told Matt that we had sex last month."

"Okay, and so what?"

"I think he feels left out. When I told him, he got mad at me. He thought we excluded him."

"Why? We never made a promise that we'll only have sex when all 3 of us are together. If he feels bad, let him. We're in the clear."

"But still..."

"Jake, it's alright. We did nothing wrong. He's just butthurt that I fucked you instead of him. If it were him instead of you that night, he wouldn't have passed up the chance to have sex with me and think about your feelings."

"You may be right, but I feel bad."

"You can't please everybody all the time. One thing my dad taught me is that you can't take into account feelings. Now, changing topics, are you ready for the trip?"

"Uh, yeah. I bought my gear today."

"Good. Do you think you can get some alcohol? My brother got us two bottles, but I don't know if that'll be enough."

"We're only there for two nights. That should be more than enough. I'll ask my sister to get us a couple of cases of White Claw if you think we'll need more."

"We will. If you don't mind, I want to enjoy my bath. Bye!"

"Bye."

I stayed in my room until I heard my Mom calling for Dani and me. I got out of my room just as Dani got out of hers.

"You think Linda came?" I asked.

"Must have."

We went downstairs and saw our parents talking to someone, who we assumed to be Linda. Her back was facing us, meaning we couldn't see her face.

My mom saw us and said, "Linda, I'd like you to meet my kids. Dani, my oldest, and Jake, my youngest."

At that moment, Linda turned around, and my jaw dropped. My mom's friend Linda was the same Linda I had sex with last month in Boston. The same Linda that was part of the orgy Dani and I went to.

I was broken out of my trance when Dani mumbled, "Act cool."

Linda walked towards us but did not indicate if she remembered us.

"Hi, I'm Linda. Your mom and I were best friends in college. It's a shame it took me this long to meet you guys."

After introducing ourselves to her, everyone headed to the living room.

Linda said, "I was in Boston during Thanksgiving. I didn't know you were there until your mother told me. We could have met a month earlier."

I was worried that Linda would rat us out about what happened in Boston. Dani subtly calmed me down and reminded me to act cool.

In the middle of the conversation, my mom got up. She said, "I didn't think you would get here so soon, Linda. I haven't even started dinner yet."

"No worries. The hunger hasn't kicked in yet."

"How about while I prepare dinner, the kids take you out and show you around town? There isn't much to see, but it does have its charm."

"I would very much appreciate that."

The three of us got into Dani's car, with Dani and me sitting in the front and Linda in the back.

We hadn't even pulled out of the driveway when Linda said, "Brother and sister, huh? I never would have guessed."

I immediately broke down and began begging her, "Please, please, don't tell our parents. They'd kick both of us out of the house. It would be so embarrassing. It wasn't even our idea. Hannah made us come to it. We weren't even interested..."

"Relax there, Jake. Who said anything about me telling your parents?" Linda said.

"Yeah, shut the fuck up, Jake," said Dani, not happy with me.

Linda started talking again, "I find it quite hot. I've been to my fair share of orgies, and never have I seen a brother and sister there. It's cool. You're both adults capable of making your own decisions. No reason for me to get involved."

"So you won't tell our parents?" I asked.

Dani smacked me on the arm and said, "She already said she wouldn't. Stop bothering her."

"Oh, it's not a bother. So, Dani, where are you taking me?"

"I was thinking of going to Stella's. It's a famous diner with great shakes."

"Sounds great."

We pulled into Stella's, and surprisingly, it wasn't busy.

We sat in a booth and ordered shakes and some fries.

I asked Linda, "Why are you in Sommerville? It's not exactly a Christmas destination."

"I flew into the city, and your Mom texted me. When I told her where I was, she insisted I visit, so here I am."

"You and my mom went to college together, right?" asked Dani.

"Yes, we did. Has Stella told you any college stories?"

"Not many. She's told me some stories, and it sounded like she was a nerd."

That made Linda burst out in laughter. "Your mom was not a nerd. She did get good grades, but she was a party girl."

"What do you mean?" I asked curiously.

"Let's just say that you two aren't that different from your mother."

The waiter arrived with our food, and after the waiter left, Dani asked, "Care to tell us some stories?"

"The stories I remember are not something I should be telling her kids."

"I think you can agree that we're an exception."

"That is also true."

"So, how was Mom like in college? I asked eagerly.

"I'll start from the beginning if that's okay with you two."

"Yeah, go ahead."

"First year, your mom and I were in rooms across from each other. We developed a bond, and in the second year, we moved into an apartment. This is where it got interesting."

Linda took a long sip of her shake before continuing her story.

"I'd consider myself a slut from the day I stepped on campus. Your mother, however, was more conservative."

Dani interrupted to ask, "Was Mom a virgin in college?"

"No. She told me she lost her virginity in high school, and I know she slept with at least two guys our first year. But she was far behind me when it came to sex. That changed when we moved in together."

"Was our mom a slut in college?"

Linda smiled and said, "I'll tell you about your mom's sexual escapades and let you decide. First, your mother and I became good friends because she didn't judge me like others. I was shamed for my sex drive, but she encouraged me to be myself and ignore the hate."

"There is no way that happened," said Dani. "When I went off to college, she gave me a lecture and made me promise that I wouldn't sleep around."

That made Linda laugh, and she said, "Your mother is a hypocrite because she slept around in college...A LOT."

I was eager to know more about my mom's past sex life. I was desperate to find out if she was as slutty as Linda made her out to be. I hurried Linda to continue her story.

"Can you get to the part about my mom having sex?"

"I would think kids wouldn't be this interested to hear about their mom having sex."

"You can probably tell we're not like other kids."

"Oh, yes, I can. I won't be able to tell you all of your mom's sex stories because that would require a lot more time. I will tell you some of the more adventurous ones. I'm sure you both will appreciate that, especially you, Jake."