Me, My Best Friend, and his Mom

Shoving my tongue into Matt's mouth I felt Ms. Karen reach around my waste. Focused on her but embraced with Matt I could feel my belt release. Her hands now doing their best to avoid contact with me gripping the button on my shorts to undo it. Matt moved his hands to my chest as his mother finally pulling my penis to the side away from my zipper just before lowering it. My shorts fell instantly and my erection bounced out to freedom. I stepped out of my shorts as instructed earlier.

As soon as my feet replanted Matt's hand was back. This time exploring more. With two fingers and his thumb explored the head of my dick discovering its circumcision and the size. He grabbed the shaft next and gripped it quickly in an attempt to measure it. Then finally to my testicles. He reached low in order to start at my inner thigh before gently cupping my balls.

As I stood there being explored, I couldn't help but open my eyes to search for Ms. Karen. Standing behind Matt was his mother. Staring back at me. Her son's tongue in my mouth his hand on my cock and she's there for it all.

Without losing eye contact she lowered his shorts. I could tell he was hard from his kiss so I didn't need to move immediately to his dick. Ms. Karen refused to wait on me however and grabbed my forearm. She moved it guiding my hand to Matt's dick.

I gave her what she wanted and began to caress him. With the back of my hand, I confirmed what I seen minutes ago, he was in fact clean shaven. His cock was also circumcised but a bit smaller than mine. It didn't matter to me but I remember getting excited about touching one so different than my own. I began soft strokes until he finally pulled away from our kiss to moan.

"Ok that's where we'll pause then boys." Ms. Karen seeing her opportunity to direct.

"Open your eyes and face me. Both of you." She commanded.

"Good. Did you guys enjoy that?" She said as she sat back on the TV stand.

"Yes Ms. Karen." I volunteered to admit it. I had liked it. I liked her seeing me with her son. I liked that she liked it.

"Yes mom." Matt also agreed.

"Look at you two. Scott you're much bigger than Matt." She said as she leaned back pushing her chest out.

"I guess that's ok. BUT! Scott, since Matt has a smaller dick than you, I think you should take bottom." She said smiling as she looked into my eyes.

Shocked, I looked at Matt.

"Mom, I'm ok with taking him, I really I am." Matt attempted to get me off the hook.

"Well, I guess you guys can take turns. It's important to have experience with both. First however, I want you to suck his cock, Scott. Get on your knees in front of him please." Demanded Ms. Karen.

"Ms. Karen, I'm not sure I'm ready" I pretended to argue while I began taking a knee in front of Matt.

"You'll be ok Scott. I will help you" she said as I got into position.

Face to face with a hairless, tan and pink, circumcised, fully erect, penis. It was just under 6" and starting to drip precum. I hesitated for a moment after seeing the drips but knew I had no choice. I adjusted my height to meet him and opened my mouth to receive.

"Stick out your tongue Scott" Ms. Karen instructed.

I did as I was told. She grabbed Matt's cock from around his back and tapped it on my tongue 5 or 6 times before shoving it in my mouth.

I began to suck him.

"Good boy Scott. How does that feel Matt?" Ms. Karen spoke as an audience member.

"Good mom" Matt said softly.

"Don't tell me Mathew, tell your friend" She insisted.

"Scott that feels amazing" Matt said looking down at me as he began to give me a reassuring pet on the head.

I didn't think I would like being this submissive but I had to admit, it was turning me on. Maybe because Ms. Karen was forcing this. Or maybe because I just liked it. I wasn't sure. I continued to suck. I flicked my tongue, grabbed his ass pulled him into my mouth further. I was really getting into this.

Suddenly Ms. Karen walked out of the room. Was she leaving us? Were we on our own?

Alone in the room sucking a cock felt immediately less exciting. I thought about stopping for a moment but just then Matt put his hands on the back of my head and forced himself deeper into my mouth almost at my throat.

He began to fuck my mouth. Moaning louder each thrust I hoped Ms. Karen would at least come back to check on us. I relaxed my jaw and clinched my cheeks and allowed him free range of my mouth.

I started to worry without her there to watch, he might just decide to cum in my mouth. I wasn't ready for that yet.

Just as all hope seemed lost Ms. Karen returned. Her shirt was untucked and she was now barefoot. She looked amazing. This was the first time I had viewed her as a woman and not just a second mother.

Comforted by her presence I could refocus on Matt's swollen cock.

I went back to sucking. Harder and deeper I was on a mission to impress her.

"Oh my gosh oh my gosh I'm, I'm, I'm Cumming" Matt cried out just mere seconds before exploding into my throat.

I began to swallow to avoid the taste as now there wasn't time to pull away safety. After several swallows with what must've been a half a cup, I decided he was finished and released him from my mouth.

"Good boy Scott, how did that feel Matt?" Ms. Karen asked

"Good. Amazing" Matt said as he caught his breath.

"Now, get on your knees Mathew." Ms. Karen commanded Matt as I began to stand.

"Scott, face Mathew." She demanded

I turned towards her son who was now eagerly awaiting my cock in his mouth.

"Mathew, I know this was your first time but, you should always wait for the person to say ok before cumming in their mouth. Now, I think we owe him a thank you." She suddenly sounded submissive.

She stepped back and sat down on the floor back against the couch next to both of us.

"Mathew, I want to see you suck his penis. Go slow though, I want to really embrace the site of you with another boy's dick in your mouth." Ms. Karen spoke as she got into her chosen viewing position.

Matt wasted no time. He grabbed my shaft and positioned his head between my legs. He raised my dick to point straight up and on his own, gave my cleanly shaven balls a few licks before laying his head on my hip and licking from the bottom of my shaft to the tip. I tilted my head back to show him that I was enjoying this and he immediately he began sucking my cock, his eyes closed. He was clearly enjoying himself. I looked down at him and seen he was getting hard again. Not sure why but that turned me on to see him getting excited for me. I forgot Ms. Karen was there for a moment and began rubbing Matt's head.

"Oh my gosh Matt, that feel amazing. I love this." I said temporarily losing my cool. I may have said too much. Love? But to be honest in that moment I was already hoping this would happen again. Even without Ms. Karen I knew right then that Matt and I would be having sex again.

"Mm, Mathew I love seeing you with a dick in your mouth. Do you enjoy it too?" Ms. Karen reminded us all she was still watching.

He shook his head in agreement.

"Good. My little boy all grown up. It turns mommy on so much. I love you so much and it sounds like Scott may too hehe" She giggled as she stood up.

"Do you mind if I undress boys?" Ms. Karen asked softly as she began to tuck her thumbs into her waist band.

"I'd love that!" I couldn't hide my excitement anymore.

"Good." She said as she began to undress.

First her shorts. She lowered them exposing her bright hot pink thong. It was a great color on her. I stared at her as my cock went in and out of Matt's mouth.

She picked up her shorts and put her hand in the pockets. She pulled out a small tube of lubricant. She hunched over and set her shorts down while uncapping the tube. She squeezed a good amount onto her finger tips and reached under Matt.

"Matt, don't be afraid. You're going to get fucked, and it's going to happen in front of mommy for your first time." she said as she reached behind him messaging the lube onto his hole.

His eyes opened for second and he looked up at me. We caught eyes and both of us knew we'd be on different ends of this but we'd both enjoy ourselves.

Ms. Karen stood back up and looked at me.

"Be gentle with my baby, but I want you to give it to him good." Ms. Karen ordered as she all at once took off her shirt revealing her perfectly perky breasts.

"Sorry they are not as perky as your little girlfriends were earlier." She added.

But they were better. Amber and Sara had great boobs, almost perfect but nothing you couldn't see easily online. But Ms. Karen's were the type you would have to seek to find. Breasts that usually were not on display but should be. Up until this I had not seen as much as her cleavage let alone her full breasts.

Her nipples were hard and the areolas were bigger than I'd expected. But for her age they were amazing. She wasted no time taking off her panties after that.

Now completely naked she laid on the loveseat and with her legs spread she began touching herself.

"Now Scott, I need you to sit next to me. I'd like to be close enough to touch you. Mathew, you're going to straddle Scott and work his cock into your ass until your comfortable enough with his size then I want you to bounce up and down on his lap" Ms. Karen again ordered as she began to position herself.

I wasted no time. I planted myself down with a great view of Ms. Karen. Mathew pretended to be shy at first slowly walked over to us.

Leaning back, I closed my legs a little to make it easier for him to hover over top of me.

He hovered over me then reached back behind him to grab my cock and guide it between his cheeks.

Ms. Karen grabbed the lubricant and squirted it all over my private area and then, with 1 single stroke of my cock she completely coated it and Matt began he decent.

"Good, now relax and breath baby you're almost there" She coached him.

He sat with the tip only now breaking the plane. "Keep going baby, it's almost there, shhhhh I know, I know, it will loosen us so. just relax"

He was tight. I mean, what was I expecting? But wow, i wasn't even sure how long I would last as he finally sat all the way down and rested.

"Hold there baby, get used to it." Ms. Karen instructed.

"I want your first time to be special. I made sure you could see each other while this happens. Now, I want you to lean in and kiss while you bounce on his cock Mathew"

He immediately leaned into me and before I could even agree his tongue was entering my mouth. As his hips began to rock upwards. He was riding my dick. I took some liberties here and reached over to touch Ms. Karen. She allowed me and I grabbed her breasts with my right hand. I explored her while making out with her son who was on top of me riding my cock. This was amazing!

I wanted to touch all of her. I slid my hands from her breast to her tummy then finally to her vagina. She had a bush but it was maintained. I had never seen bush before in real life. I liked it. It reminded me that she was a mature woman and I, with my barely hairy pubic area, was still developing. It turned me on knowing there was years of experience between us and that she didn't care. In fact, she was the one pursuing this entire night. I began to insert my fingers. She grabbed my hand end exhaled as she pulled it into her.

I couldn't believe it. Mother and Son. I was fucking Matt while fingering his mother. Matt wasn't even paying attention to the fact that I was two fingers deep inside Ms. Karen since I was 7 inches deep inside of him. Matt's cock was so hard now, it was barely hitting my stomach as he bounced.

Ms. Karen must have seen this because just then she reached over to stroke it for him.

As soon as he felt his mother's warm hand on his hard cock, he broke our kiss. His eyes still closed, face filled with pleasure, and his dick harder now then even before when I had him in my mouth, he leaned back. Grabbing my thighs for support while his erection aimed straight at me, Ms. Karen began stroking it. It didn't take long for this to overwhelm him and again without warning, he came. This time shooting his sperm onto my chest, neck and face. I couldn't believe how hard he had came.

The thought of him Cumming from my cock in his ass was too much. I couldn't even think to wipe off my chin and lips before I felt the pressure of my own sperm building. I began to lick my lip instinctively tasting his cum as he continued to bounce on my lap, playing along for me now so I could finish.

"I'm going to cum" I moaned.

"Do it Scott, cum inside of him. Fill him up. Fill up my son." Ms. Karen instructed as she grabbed my hand from between her legs and squeezed it forcing it deeper.

I didn't waste any time. I came. I came harder than I ever had before. So much cum that I felt dehydrated immediately after. I thrusted upwards while ejaculating due to the intensity and Matt rocked forward on top of me into a hugging position. My cock was deep inside of him while his chest now pressed against mine, split the cum he had given me. His cheek found mine and I reached around his back to complete the hug. Ms. Karen still watching, was now heavily breathing and moaning. She was about to explode. I momentarily had forgotten about her as Matt had brought me to orgasm.

I refocused attention to her just before Matt slid his face back in front of mine and went in for a kiss. This kiss was slightly different and somehow more meaningful then the previous kisses. Softer, more passionate somehow. At least it felt that way in the moment.

Right then, I felt a warm liquid that I had not felt before wash onto my hand. Ms. Karen was squirting. I didn't even know at the time women could do that, but I liked it. She moaned loudly and closed her legs almost spasming as she turned towards me. Matt and I broke our kiss, feeling her looking at us. She leaned over to us and without asking permission, began to kiss us. First Matt and then me, her tongue was subtle at first but apparent during the second pass. Matt offered to lean in and it quickly became a 3 way kiss.

He rolled off of me and laid to my left with his mom still on my right. She began to shake and gasp for air. Me in the middle completely drained but in complete euphoria. I used my left hand and placed it on Matt's thigh. Rubbing it as I made my way back to his cock. Then with my right hand, I glided it across Ms. Karens stomach up to her breasts. I gently caressed them while they met in the middle at my crotch, Ms. Karen first to my cock but Matt not far behind her exploring my balls.

We all just laid there exploring, while looking straight up at the acoustic ceiling above, wrapping our minds around what had just happened and still catching our breath.

We were all in complete silence until finally someone spoke.

Ms. Karen decided to break the silence "Boys, tonight, well it wasn't, I mean... It's not gay because I was here. And it's ok to like it and like each other in that way if you do. I really liked watching. I want to help you guys so, just tell me next time you want to do stuff together. Or if you guys want, I'll let you both practice with me. I have a special toy too so we could all kind of be boys next time."