Senior Year at Sommerville High Ch. 03

Unfortunately, she said, "I'm too sore to take another round of fucking from the both of you. But I'm willing to give head to the first one who goes down on me." Matt was on his knees in a flash and waddled his way to Sydney. He lifted her legs and placed them on her shoulders and dove into her crotch.

He must've been good because Sydney was biting her lips and looking at Matt like she would do anything for him. She slowly thrusted her hips and had a finger or two rub her clit.

Matt was relentless at eating her out. Sydney shrieked and said, "Oh, yes, stick your tongue in further." I couldn't tell exactly what he was doing, but he got her to cum not too long after. She bit her bottom lip hard to muffle her moan and had her eyes shut tight. Once, the orgasm had passed over her, she opened her eyes and took deep, heavy breaths.

She motioned for Matt to stand up so his cock was pointing directly at her face, and said, "Now time for me to suck your dick," and she swallowed his cock whole. I repositioned myself to get a better view, and she was already deep throating him. The sounds of her gagging on him made me want to jerk off. I tried holding off, but I failed and started to masturbate.

Sydney saw what I was doing, and took a break from giving Matt a blowjob to say, "If you can stop yourself from masturbating, I'll do it for you after I'm done with Matt."

I had never resisted anything harder in my life. I even thought about looking away, but I didn't want to miss out. Sydney looked like she could suck a dick just as good as she rides one. Running her tongue up and down, fondling and sucking the balls, sucking the head; she did it all.

She went back to bobbing her head on his penis when she stopped for a second, and asked me, "Can you hand me my panties?" I dug through the pile of clothes till I found it and gave it to her.

She sucked him off a couple more minutes before she pulled his cock out of her mouth. She wrapped his cock with her panties, and proceeded to jerk him off till he came. She said, "Sorry, but I don't swallow or let guys cum on me." Matt came hard, and she didn't let go till she was sure he was done.

She unwrapped and looked at the mess he made. She offered it to him, asking, "Want to keep it as a souvenir?" Matt took it from her, grabbed his jeans from the floor, and stuffed the panties into a pocket.

Sydney turned her attention toward me, and pulled me closer by my erection. She spit on the head of my penis, and rubbed it all over. Once, it was slick to her satisfaction, she jerked me off.

She was sensual and thorough, making sure both of us were enjoying it. I was already close to cumming just from watching her give Matt a blowjob, so 5 minutes into the handjob, my cock started to throb.

She asked Matt to grab her a couple of tissues, and she used that to catch my cum. She said, "You're going to have settle for this. I only have 1 pair of panties down here, and I know your load isn't big enough for my bra."

"I don't care. All I care about is you making me cum right now." Right on cue, she made me cum into the tissues. She put the tissues near the used condoms and said, "I think we're done for today. Hope everyone is happy as I am." Matt and I nodded, and got dressed while Sydney used the basement bathroom to get cleaned up.

Sydney popped out of the bathroom, and said, "You don't have to wait for me. I think I'm going to take a nap down here before heading up. No awkwardness, right?"

We shook our heads. Matt asked, "Uhm, Sydney? Was this a one time thing?"

She answered with a smile, and said, "We'll cross that bridge when it gets there. But, personally, I hope it's not."

I then remembered about the text in the morning, and asked, "You said something about an incentive. Was that the game or?"

"Oh, right. I forgot about. She then jogged across the room, still nude, which left me with a memory I would never forget. She reached into her bag, and pulled out a pair of panties.

I said, "I thought you said you only had 1 pair down here."

"I only did have 1 pair. These are Amanda's." She tossed them in my direction, and I caught it. "I haven't washed them, so I hope they still have their scent." I took a sniff, and I did pick up a smell though I wasn't sure what it was.

I decided sniffing panties weren't my thing and offered them to Matt who happily accepted his second pair of panties.

Matt and I grabbed our backpacks, said goodbye to Sydney, and headed upstairs to leave. We were almost at the front door, when we heard, "Hello boys, hope you guys had a great day today."

We turned around, and it was Sydney's mom. I replied, "Hi, Mrs.Augustyne. Oh, you know, just your typical school day."

"Really? Having sex with my daughter is a typical day?"

Both Matt and I turned white. She saw how uncomfortable we were, and said, "Relax, I'm not mad at you two. Sydney's old and smart enough to be making her own decisions and to know their consequences. I just hope you know the consequences too. Have you ever thought about how the rest of your friends might react if they found out?"

I was once again thinking with my penis instead of my brain. There was a chance it could tear the group apart. I had to think if the risk was worth the reward.

Mrs.Augustyne continued, "When I was your age, I was part of a group just like you guys are. And I let my urges take priority which led to a huge fight. It took years for us to get back to being on good terms again. I'd hate to see that happen with my daughter and her friends. I'm not telling you to stop, but I recommend putting it on hold, at least until you discuss with your other friends."

I took a minute to think about what she said and thanked her for the advice. Matt and I turned around to leave, but then I thought, how did she know we had sex with Sydney. I turned around, and asked, "How did you know we were having sex?"

"I saw your cars parked out front, so I came down to say hello. I was halfway down the stairs when I saw Jake...uhm, fucking my daughter. I assume she wasn't cruel to Matt by making him watch and not get a go."

She then unclenched her fist to reveal she had been holding something. She was holding Sydney's panties that were soaked in Matt's cum. "Before you leave, I think one of you dropped this on accident."

Matt turned bright red, Mrs.Augustyne smiled, and said, "I take it my daughter gifted this to you, Matt. I'll put this in a Ziploc bag for you." She did as she said, and handed the bag to Matt. She reminded us of her advice before we walked out the door.

Once outside, we looked at each other, unable to comprehend what had just happened. Matt asked, "That really happened, right?"

I nodded, and said, "Yes, it did."

"Are you also turned on by Mrs.Augustyne right now?"

"Yup."

We heard static behind us, and Mrs.Augustyne's voice came through a speaker, "I'm flattered. Now why don't you head home. It's already dark outside." We looked at each other again, and got in our cars to drive to our homes.

FRIDAY

Another school week was in the books, and everyone was flooding out of school to start their weekend plans. I, however, was waiting in front of the main entrance, looking for Madison. I asked Tyler to wait by the back entrance and text me if he saw her.

On Monday, Madison said we would discuss about us some time later. But she dodged me the entire week. Either she skipped school entirely or ditched Chemistry class. Yesterday, we had a test, but she took the entire period to finish a test everyone else finished in half the time.

I had waited for 15 minutes when I saw Tyler walking towards me. "No luck, dude. The janitor locked the back entrance. You see her?"

I shook my head, and said, "Didn't see her come through here either." I took out my phone to text her. I saw a long chain of my messages without a reply. I sent another text hoping for a reply and put my phone away.

Seeing I was dejected, Tyler asked me to tag along to a new Boba place with Soniya and him. I placed our order while they grabbed us a table. I found them at the table, and sat down with a tray of our drinks. I asked, "Soniya, don't you have any last minute prep to do before your cousin's wedding tomorrow?"

"I've got everything ready since last week. I hate running around at the last minute. I hope this guy has everything ready," as she nudged Tyler.

"I bought a new suit, and haven't taken it out of it's body bag or whatever that thing is called."

"The fact that Ray helped you pick out the suit is the only thing making me feel better."

"Hey! I got style."

"Babe, your outfit right now looks like something my dad would wear, and that is not a good thing."

"You don't have style," and he took a loud sip from his boba which drove Soniya mad. They bickered for a while before I butted in to break it up. "So, Soniya, tell me more about Indian weddings. I've never been to one."

Soniya got in one last hit on Tyler before she went on to explain in detail about their wedding traditions and events. She was 10 minutes into her explanation, when I got a text. It was from Ms.Santiago, and I immediately checked it.

Ms.Santiago: Hey Jake

Jake: Hey Ms.Santiago

Ms.Santiago: That was quick XD

Jake: Yeah, I was on my phone. Totally not waiting for your text

Jake: What's up

Ms.Santiago: I was wondering if you could spare some time and stop by my house tomorrow

Jake: I'll be there

Ms.Santiago: Great. Noon tomorrow? You can have lunch at my place

Jake: Lunch it is. See you tomorrow

I put my phone away, and saw Tyler and Soniya staring at me. Soniya asked, "Are you head over heels for a girl? Will we finally have another couple to go on double dates on?"

"No, nothing like that. It was my mom," I lied. "She asked me to get some stuff from the store on the way back."

"Ok, whatever you say." We spent another half hour at the Boba place before leaving. I went back home, while Tyler dropped Soniya off at her home.

I got home and went straight to my bedroom. I was thinking about tomorrow, and what Ms.Santiago could have planned. This would be the first time it would be just the two of us. My mind was going wild thinking of all the scenarios that could happen. I decided to text her.

Jake: Can't wait for tomorrow

Ms.Santaigo: XD

Ms.Santiago: I'm sure a high school senior has plans on Friday night to keep his mind busy

Jake: lol, I'm at home with nothing to do

Ms.Santiago: Interesting. So am I

Was that an invitation to go to her house now? I was trying decipher what she meant when she sent another text.

Ms.Santiago: Ugh, men. Can never pick up on the hint. You're welcome to come over now

Jake: omw :)

I changed into a nice button down and new jeans. I put on some cologne, and headed downstairs. Mom was busy making dinner, and I told her, "Sorry, Mom! Won't be here for dinner. Love you! I'll be back later." I was out the door before she could say anything.

I pulled into her driveway in record breaking time. I spent a minute in my car to collect myself. I got out, and rang her doorbell. She opened the door wearing a black robe that went down to her thighs. She had a white top with spaghetti straps that showed off a little bit of her stomach and her bra straps. She had on black shorts that came down just below her ass.

She let me in, and we sat on the sofa in her living room. She started talking first, "Since, you came on such short notice, I didn't have time to make anything. I hope pizza is fine."

"I'll eat anything."

"We have some time before the pizza arrives, so why don't we talk." I nodded. She continued, "I'll go first."

"First off, I want to make it clear, I have no romantic feelings towards you. Now, just because I'm not romantically interested in you doesn't mean I'm not sexually attracted to you. I think you look great, Jake. But, I hope you understand that I am putting a whole lot on the line." I nodded, remembering what Nurse Mapleton had told me at the mall.

"I know all about my friend's sex lives and mine seems so vanilla in comparison. And that is the reason that led to what happened in the store room." I wondered if Nurse Mapleton was among those friends.

"As long as you consent, Jake, I would like to continue fooling around, but I'd like to take it slow."

"Of course, I consent!"

She laughed, and said, "In that case, we have maybe half an hour before the pizza arrives. Can you think of anything to pass the time?"

I thought of a lot of things to pass the time, but she had said she wanted to take it slow. After some thinking, I said, "How about we get naked and see where it goes from there?"

"I like that." We both got up, I unbuttoned my shirt, and had stripped down to my boxers in seconds. She took her time, she slowly dropped the robe from her shoulders, and proceed to seductively pull off her top. She shimmied out of her shorts, and she stood before me in a matching black bra and panties set.

I asked, "Is this the bra you wore that day?"

"It could be, I have a few black bras. Do you want to go first or should I?"

"You."

"I figured." She reached around her back with one hand while the other held on to the front of her bra. She unclasped her bra and held it up with her hand. She said, 'I don't know why I'm so nervous. It's not like you haven't seen them before." She took a few seconds before she let the bra drop to the floor.

I was staring at Ms.Santiago's boobs for the second time ever. I wondered how I had gotten so lucky. She moved onto her panties next, she turned around, and bent down as she took off her panties. That wonderful bubble butt everyone in school had obsessed about was now right in front of me. I wanted to grab and smack it but I held back.

She turned back around, and said, "Your turn." I wasn't as graceful as she was, I took off my boxers, tripping on my jeans in the process. Nonetheless, I took it off and stood before her naked. My penis was pointing directly at her, just a few inches separating us.

She asked, "Now what do we do, Jake?"

"Uhm, well you gave me a blowjob last time."

"How about we build up to it this time?"

"How?"

"I do like it when men play with my breasts. But no one ever does it properly."

I sat on the sofa, and pulled her down next to me. I got her to lay back while I got on top of her. I teased her by licking each of her nipples. I then started to circle them with my fingertips. She started to twitch, which I took as a sign that she was enjoying it. I took one entire nipple in my mouth, and started to suck on it with force, flicking it with my tongue occasionally.

She started to moan, and said, "How does an 18 year old know how to suck a tit so well. I feel like you can make me orgasm just from this."

I took my mouth off, and let my hands go to work. I replied, "I've dreamt of this so many times, that I'm basically an expert now."

"Oh, yeah? What else have you dreamt of doing to me?"

"I've dreamt of bending you over your desk, and fucking you from behind."

"You naughty boy. Are your classmates watching?"

"Uhhh, if you want them to be watching."

"You said you're fucking me from behind, but where is your cock? In my pussy or ass?"

Hearing her say those words made my cock pulse. I even felt a little pre cum leak out. "I want to do both, but we'll start off in your ass."

"I've never had a man in my ass before. I've always wanted too but they've never proved they're worthy of it. Do you think you're worthy enough to fuck me in the ass, Jake?"

HOLY SHIT!! She was a total freak, and I was loving it. I was tempted to flip her around, and fuck her in the ass right then. Instead, I said, "I'll prove it to you."

"Oh, yeah? How?"

"I'll start by doing this." My index and middle finger slid into her wet pussy with ease. I used my thumb from my other hand to rub her clit in a clockwise motion.

She started to pant and say, "Yes, yes, that feels so good." We were in a good rhythm when the doorbell rang. We looked at each other alarmed but relaxed when we remembered it was most likely the pizza.

She asked me, "Can you go get it? I already paid for it online."

"Why don't you?"

"Cause it's easier for you to get dressed."

"You said you want have some fun. Use this as an opportunity. Get the pizza with just your robe on."

She looked at me till the bell rang again. She sighed, got up, put on her robe, took a deep breath, and walked over to the door. One more deep breath, and she opened the door.

"Hello ma'am, I have your extra large supreme..." He paused once he saw she was just in her robe. The robe showed a good amount of cleavage, and I could tell his gaze was lost in it.

Using one hand to keep her robe in place, she used the other to get the pizza. "Thank you. If you can wait, I'll get your tip."

"No, thank you, ma'am. I'm good."

"Oh, but I'll feel bad if I don't tip you. There's surely something I could do."

The delivery guy was trying to say something but he kept tripping over his own words.

I got an idea, so I put on my boxers and walked over to them. I took the pizza off her hands and suggested, "How about you flash him?" I directed my eyes to the delivery guy, and asked, "Would you like that?" He nodded his head furiously.

Ms.Santiago gave me the death stare. I mouthed at her, "Have some fun."

She turned her attention back to the delivery guy, and her expression changed from a death stare into a pleasant smile. She asked, "Would you like for me to flash you?" He once again nodded furiously. She looked at me, and I gave her an encouraging nod. She closed her eyes, grabbed her robe and exposed herself to the delivery guy.

His jaw dropped, and he started to drool. She closed back up, said thank you, and shut the door in his face.

She grabbed the pizza from me, and tossed it onto a nearby table. She then placed her hands on my shoulder, and started pushing me back. As she was doing that, she was saying, "You are in so much trouble. Making me expose myself to some stranger. What were you thinking?" The back of my legs hit the sofa, and I sat down on it.

I asked, "Did you like it?"

That made her think for a second. I repeated my question again, and this time she replied, "I think I did."

I stuck my hand under her robe to feel her pussy. "Your body seems to have enjoyed it."

"No fair, I was already wet."

"But not this wet. I think we may have found your kink."

She dropped to her knees, and took off her robe. She slid her hand along my inner thigh till she reached my penis and took hold of it. "Maybe, but we have more important matters to attend to right now." She gave me a few pumps before she took me into her mouth.

The first several minutes, she spent bobbing her head up and down on my cock, with at least half of it in her mouth at all times. She then deep throated me for as long as she could before she had to come up for air. Her hand was gliding on my cock effortlessly thanks to the mix of pre-cum and saliva. With her hand still jerking me off, she sucked one of my balls into her mouth. I could feel her tongue playing with it inside and it felt euphoric.

Unfortunately, for me, the feeling was so good, I started shooting cum. The first spurt of cum landed on her hair. She felt it and changed her head just in time for the next few to hit her on the face. My cock lost momentum after that, and the cum just oozed out after that over her hand.

After I finished, she said, "I prefer it when you cum in my mouth. The clean up is much easier."

"I like both." She smiled and walked over to the kitchen to clean herself off using paper towels.

I got the pizza, and brought it over to the dinner table. We took our seats and ate the pizza while we talked. We mostly talked about her sexual history and her unlucky streak of having sex with 'one pump chumps'.