Senior Year at Sommerville High Ch. 06

I pulled into the parking lot of a motel and it looked sketchy. I took out my phone and took a picture of a big neon sign that said, 'Welcome to Up & Away Motel'.

I sent the photo to Ms.Santiago and texted her.

Jake: Is this the right place?

Ms.Santiago: Yup. Take the stairs on the left and come to room 231.

I followed her instructions and found myself in front of a room 231. After a deep breath, I knocked on the door. The door creaked open before opening all the way. I walked in and was treated to the sight of Ms.Santiago wearing a silk robe with black lingerie set underneath.

"Oh, boy. The wait was definitely worth it," I said.

"Really? We haven't even done anything yet."

"I know, but if you're wearing this, I know it'll be a good night."

She slowly walked over to me and pushed me onto the bed. She took off her robe and then straddled me. I felt my cock filling up with blood, and then Ms.Santiago leaned down to kiss me.

"Wasting no time, huh?"

"I already wasted one day. And the quicker we start, the less time for my brain to think of reasons not to do this." Her lips met mine again leading to an intense stretch of making out.

We had been making out for a long time when I grabbed her shoulders, ready to flip her over and get on top.

She stopped me by saying, "Uh huh, not tonight. I need to remind you that I'm the teacher here."

I let go of her shoulders as she unclasped her bra. She smothered me with her rack and I was enjoying every second of it.

Other than the normal sucking on her nipples and playing with her boobs, I adopted Tyler's technique and ran my finger under her boob.

Her response was great as she said, "Oo, I like that. Where did you learn that trick from?"

"Just experimenting."

After being in boob heaven for 5 or 6 minutes, Ms.Santiago started undressing me and kissing my body as she did.

Once my jeans were off, she grabbed my penis through the opening of my boxers and took it out.

"Long time no see, big guy. I hope I can make up for all the days we missed, tonight," as she gently began to stroke it.

She used her spit as makeshift lube and it felt even better than lube. Ms.Santiago was taking her time using full-length, slow strokes. Occasionally, she would tease me by licking the tip or taking the head of my penis in her mouth to stimulate my nerves.

I was on edge and felt my cock throbbing in her hands. All of a sudden, she stopped giving me a handjob and said, "Looks like we can move on to the next part."

"What's the next part?"

Instead of answering with words, she got off the bed, turned around, and took off her panties seductively. I saw her asshole and it led to flashbacks of fucking Hannah's ass. I hoped that Ms.Santiago would let me do the same but I knew it was unlikely considering we hadn't even had vaginal sex yet.

She got back on the bed, this time standing, and walked over me until she was standing over my face. She turned around, squatted, and leaned forward so we were in the '69' position.

"I know you're good with your tongue, but for extra incentive, I'll suck your cock depending on how well you eat me out."

I didn't wait to hear anything else. I dove in and pleasured her. After a few seconds, I felt the warmth of her mouth on my penis.

Out of curiosity, I decided to test if what she said was true. I slowed down and stopped focusing on her clit.

With a loud pop, my penis came out of her mouth, she turned around and said, "Don't test me. Now get your tongue back in there and use a finger or two."

"Yes, ma'am."

As instructed, I slid two fingers into her while I used my tongue to stimulate her clitoris. I felt her sucking on my cock and it get better the longer we went.

My fingers and tongue had brought her to the edge of an orgasm, and I could hear her moaning as she gave me a blowjob. My penis was begging to ejaculate but I held on with all my might wanting to make her cum first.

Once I felt her body begin to buckle, and the moans turned into groans, I let it out. By holding it in for a bit, when I finally came, it shot out like a cannon into her mouth.

She turned around, and her chin was glazed from cum and spit. "Someone was clearly pent up," she said as she wiped her face with her hands.

She took a quick bathroom trip before getting back on top of me. My penis was sandwiched between my toro and her vagina, and she was gently grinding on it.

As she was teasing me, she said the words I had been waiting hear for a long time. She said, "Let's have sex."

We had never had sex before, and I had been patiently waiting for that day. So, when she said those words, my body jolted with excitement.

Ms.Santiago propped herself up so she could sit back down on my cock. I could feel how tight she was as my penis disappeared into her vagina. Once she had bottomed out, she placed both hands on my chest and began rocking on me.

It had been over 5 minutes, and Ms.Santiago was still rocking on me at a snail's pace. If this was any other women, I would've flipped her over and started fucking her hard. But since this was Ms.Santiago, I was happy. I was enjoying the sight as my teacher fucked me.

She leaned down to nibble on my ears and neck, picking up her pace as she did. My ear and necks were new erogenous areas I had recently discovered. The feelings from her nibbling and her squeezing her pussy on my cock as she rode me was overwhelming. In a desperate need to grab something, my hands found their way to her ass, and each tightly gripped one of her cheeks.

She whispered in my ear, "You like my big, fat ass? Do you like how it feels in your hands? Is this what you imagined it felt like, or even better?" She gently bit my earlobe and I was having sensory overload.

Even though I had let out a big load 10 minutes before, I was ready to cum again. In a guttural voice, I said, "I'm cumminnggggg!!"

I felt my cock shoot spurt after spurt of semen deep into her womb. Her big, brown eyes made contact with mine, and she gave me a calming smile. We began kissing and this wasn't like the other times. This had more emotions behind it.

Well after I had finished cumming in her, we were still kissing. She was the first to pull away. She redid her hair, and I enjoyed watching her boobs move as she did.

I assumed we would go back to kissing, but she pivoted on me, and now her back was facing me. She turned her head around and said, "I know how you and every person in school with a dick loves my ass. I hope you like this show."

She started bouncing on my cock, sending ripples through her ass each time she came back down on my body. This felt even better than when she grinding on me. I grabbed hold of her hips to have some control over the pace but she wouldn't cede control.

She was slamming down hard as she went up at least half of penis each time. The pleasure was easily triumphing over the pain leading me to moan.

My phone went off, and when I checked, it was my mom calling. I cut the call not wanting anything to disrupt this.

This happened a few more times before Ms.Santiago asked, "Who the fuck is calling you?"

"It's my mom. I'm going to put it on silent."

"No. I want you to talk to her while I fuck you."

"What?" I asked stunned at what she had said.

"I said, I want you to pick up your mom's call and talk to her while I fuck you."

The next time my mom called, I answered the phone. "Hey, Mom," I said giving it my all not grunt from pleasure.

"JAKE! Why did you cut my call?"

"Sorry, Mom. I was busy with something. Why did you call?"

"I'm worried about you. Where are you? You didn't say you would be late today."

"Something, came up last minute...." I had to stop and let out a grunt as I felt the beginning of my next orgasm.

"Jake? Are you okay?"

"Yeah, I'm okay."

I saw Ms.Santiago's face in the reflection and she was loving every second of this. When she saw me looking at her through the mirror, her hand went to my balls and started playing with them.

I had shut my mouth tight, not wanting to let out a sound, but despite my efforts, I squealed.

"Are you sure you're ok, Jake?" my mom asked, this time more concerned.

"Yeah, Mom. I'm fine. I'm kind of busy now. I'll call you when I'm on the way home."

"Ok, fine. Love you. Don't be late."

"Love you too, Mom." I cut the call and let out a loud groan.

"Did you like it when I fucked while you talked to your mommy?"

"Yes, I fucking loved it."

She picked up her pace and I came for the third time that day. That didn't stop her as she kept going harder and harder. She went up too high, and my penis fell out of her vagina. Both of us scrambled to put it back, desperate not to lose the feeling

She tightly gripped onto my shins and powered through her third climax of the night. She moaned even louder than I did, and when the feeling had washed over her body, she bent down on her forearms.

I saw her back rising up and down as she caught her breath. A few minutes of heavy breathing later, she unmounted me and crawled up next to me to cuddle in my arms.

"Was it worth the wait?" she asked.

"I would have happily waited another month if I knew this was going to happen."

"Are you saying you're ok waiting another month for our next meetup?"

"No, never. Now that I experienced this, I'm hooked."

She chuckled and started to trace my nipple with her finger. It caused a tingling sensation over my body that felt nice. Using my hand that was over her shoulder, I began to fondle her breast.

There was a long period of silence that was becoming uncomfortable for me. I grabbed the TV remote and asked her, "Mind if I turn on the TV?"

"Go ahead."

After some channel surfing, we found an old rom-com to fill the silence. We both dozed off during the movie and was woken up by my phone vibrating on the night stand.

It was my mom again and I picked up and told her I was on my way back home.

I got dressed as Ms.Santiago went to the bathroom to wash her face.

Once she had got dressed, she said, "You head to your car first and text me when you get in. I'll leave after waiting a safe period of time."

"Don't you think you're being too paranoid at times? I understand there's a big risk involved but you did say you wanted this to have fun. How much fun are you really having if you're worrying all the time?"

She smiled, walked towards me to plant a big kiss on my lips. While caressing my cheek, she said, "Jake, I appreciate you wanting me enjoy to the full extent but one tiny slip up and both of our worlds come crashing down. I still am having the time of my life whenever I'm with you. That's enough for me. So, do as I say, ok?"

I nodded and left the room to head home. I got in my car and texted her like she asked and drove home.

It was 8:30 when I pulled into my driveway. I walked in and saw my parents sitting at the kitchen table waiting for me. My mom had a stoic expression while my dad was angry and I had no idea why.

My mom said, "Jake, we need to talk."

"Ok, what about?"

"Take a seat first."

I sat opposite them and waited to find out what this was about.

"We know you're 18 and legally and adult but as long as you live in this house, under our roof, we expect you to keep us updated on your whereabouts."

"Uhm, okay? I'll text next time."

My mom lectured me for a solid hour but she was pretty much saying the same thing in different ways. Once she was done, we got up, hugged, and said good night.

My mom headed upstairs first leaving my dad and I downstairs and I apologized to him.

My dad said, "Jake, that is not what your mother wanted to say. She knows you only got a few more months left at home before you're off to college. She wants to spend as much time with you as possible. Same thing happened when Dani was a senior in high school. I'm not telling you to completely give up your social life but spend a few days at home and get back earlier. Have a talk with your mother."

"Will do, Dad. Good night."

"Good night," and he walked over to the living room.

"You're not going to sleep?"

"Your mother made me miss Monday Night Football yesterday waiting for you. I couldn't watch the game today either because she made me wait for you again. Now, I can finally watch the highlights in peace."

"Oh, ok."

I went to my bedroom and ran into Dani in the hallway. She followed me into my bedroom and closed the door behind her.

Not knowing what was going on, I asked, "What are you doing?"

"Who was it?"

"Huh?"

'Who did you fuck?"

"What? No one."

"Don't lie to me. Your hair is rustled, I can smell women's perfume mixed with sweat, and you have a stupid grin on your face, exactly like in Boston. Now tell me who it was?"

"Why do you want to know? Is someone getting jealous?"

"Jealous of what?"

"Your little brother having a fantastic sex life while you're not."

"I don't care about that. Listen, I'll make sure you telling me is worth it."

"How?"

"I'll let you cum in my bra whenever masturbate."

"Been there, done that."

"Bra and panties?"

"We're getting somewhere."

She sighed and said, "I'll send you nudes. Final offer."

"I've already seen you nude in person. How about whenever I want to jerk off, you pose naked for me?"

"I already said final offer."

"It looks like I'm the one in control here. Are you gonna take my offer or not?"

She thought about it and countered, "Once a week."

I stuck out my hand and said, "Deal."

We shook on it to make it official, and she asked, "Who was it?"

"Promise you won't tell anyone?" after she nodded, I said, "Ms.Santiago."

"Are you fucking stupid?!"

"Geez, quiet down. You'll wake up mom."

She lowered her voice and asked, "Are you fucking stupid? You know how dangerous that is."

"We know and we're ok with it. And it's not like we're being reckless, Ms.Santiago and I are playing it safe."

"Fine but if shit hits the fan, don't come to me begging for help."

"It won't and I won't."

"Since we did make that deal, want to strip down for me?"

"Please, you're two seconds from falling asleep. And if the sex was good as it looks like it was, no way you're getting it up or cumming."

She was right. I was spent and I would enjoy it more if I didn't have sex an hour before.

Dani went back to her room while I went to shower.

As I was showering, I wondered why Dani agreed to the deal. It was clearly more favorable for me unless there was some angle that I wasn't seeing. I focused more on thinking of why Dani agreed to the deal than showering that I had to spend another 15 minutes to actually clean myself.

After showering, I went to bed and gave up trying to come up with a reason. Dani was right as I was drained from the sex and slept off.

SATURDAY

I woke up at 10 and instinctively went for my phone. Sydney had created a group with Zoe, her and me.

Sydney: Morning! I hope you guys don't have any plans today. Julian said he's free today.

Zoe: Julian?

Sydney: The guy I met in Cancun.

Zoe: Ok, his name is Julian. Nice to know.

Sydney: Does 2pm work sound good?

Zoe: Anytime is good as long every cent we spend comes out of your pocket

Sydney: Of course. Where is Jake? Is he not up yet?

Zoe: Probably sleeping in. He should be down, not like he has anything important to do

Jake: I happen to be a very busy man with important stuff to do. But yes, 2pm works for me.

Zoe: o_o

Sydney: Great!! I'll come by your houses at 1:30. Love you guys <3

I rolled out of bed and opened my door to head to the bathroom when I was startled by my dad standing there.

"You scared me there, Dad."

"Sorry, about that. I was going to knock on your door."

"What's up?"

"Remember the talk I had with you about spending time with your mother."

I bit my teeth and sucked in hard, "Yeah but I made plans with Sydney and Zoe today."

"That's fine. Like I said, I don't want you to give up anything. Do you have time to take your mother to breakfast or brunch? It would mean a lot to her."

"Of course. Let me brush my teeth and get ready real quick."

He handed me his credit card, saying, "Take this and thank you." He headed downstairs while I made a beeline to the bathroom.

I got ready in a hurry and went downstairs to meet Mom in the kitchen.

She asked, "Where are you going?"

"Brunch with you."

"Huh?"

"Let's get brunch. We haven't hung out just the two of us in a while."

"You don't have plans with your friends?"

"I do but they can wait."

"Are you sure?"

"Mom! Hurry up and get ready."

"Ok, ok. I'm going," as she excitedly ran up the stairs.

I wasn't sure if I would have enough time to go to brunch, come back and get ready by 2 so I texted in the group.

Jake: Does it have to be 2?

Sydney: Why? What happened?

Jake: Taking my mom for brunch. Can we do 3?

Sydney: Awww, how sweet. Yes, we can do 3.

Jake: Thanks a lot, Sydney.

My mom came down wearing a casual outfit.

"Looking good, Mom."

"Oh, stop it. This is something I just threw together quickly."

We grabbed our coats from the closet and got in my dad's car which he insisted we take.

I took her to one of the fancier places in town which also happened to be a place she always wanted to go to.

A waiter seated us and gave us time to decide our order.

We both got the Full English Breakfast with a Bloody Mary for her and orange juice for me.

"Is my son dating anyone?"

"Wow, Mom. Straight to the chase. And no, your son is not dating anyone."

"That's a shame. Any girl would be lucky to have you as her boyfriend."

I chuckled and said, "You're not the first person to say that."

"Who else told you that?"

"Too many people that I can't remember them all," I joked.

"Is it because you're going off to college next year?"

"Not really. I just don't think I'm ready to put everything aside to date someone."

"In a way, I'm happy. I barely get enough time with you as it is. If you get a girlfriend, that time would be even less."

"Hey, I'm here now, aren't I?"

She smiled a bit but I could tell she was sad. "Oh, honey, I don't want you to go off to college."

"Mom, that's still way down the road."

"No, it's not. It's nine months away and those nine months will go by in a flash."

"If time goes by in a flash, that means you're enjoying it. That's a good thing."

"Ugh, I know. Promise to visit every vacation?"

"Of course, I will. And you're looking way ahead into the future. Focus on now. Let's not bring down the mood."

She agreed to end the sad talk and the rest of brunch was great. On the drive back home, I started feeling the same sadness she was when I thought about going to college.

I parked the car in the garage and before heading inside, she hugged and said, "Thank you, Jake. This was nice."

"It was, Mom. We'll do it again and more regularly."

"I would like that."

It was a quarter to 2 meaning I had roughly 45 minutes to get ready. I went to get a cup of water in the kitchen and Dani was there.

"How did brunch with Mom go?"

"It was good. What were you up to?"

"Nothing much. Worked a lot late nights this week so caught up on some sleep."

"Wish I could sleep for a few hours but I have to the state university with Sydney and Zoe."

"Why?"

"Sydney met a guy from there and doesn't want to drive alone."

"Can't she afford a chauffeur?"

"Yeah but I think she wants us to meet him as well."

I was about to head upstairs when she said, "Have you forgotten about the deal?"

"No." I looked around to make sure it was only us two, and said, "I actually haven't jerked off since we made the deal. I want to make sure it's worth it."

"Have you had sex?"

"Nope. I haven't came since Tuesday."

"When are you going to call it in? It's already the last day of the week."