Me, My Best Friend, and his Mom

Growing up I had a ton of friends but only one best friend. We were close. Eventually we got maybe a little too close.

My best friend Matt was just a few months younger than me, and lived not far from my house. So, I pretty much lived at his house most weekends and summers. His dad Mr. Paul was a bit of a drinker. He was loud and kind of cartoonish in a way, but we all liked him. His mother Karen was the opposite. Quiet and intelligent, classy to say the least. She wore thick glasses with retro frames, (before they were popular) she wore her hair down mostly. Her hair was long hair with slight curls, her bangs pinned back but never really wore makeup. She was short, probably around 5'1". Yup, she he was your average mom alright, around 115lbs eatly to mid 50s.

She worked and was a home maker so she couldn't keep up with her hair dye and the once dirty blonde would occasionally have streaks of grey. She had smile wrinkles around her mouth and that small fold between her eyes when she removed her glasses and had to squint. She was in pretty decent shape considering i never knew her to work out. Her breasts appeared perky for their size at about a C cup and her tummy was flat with a small waste. Her butt was average but tight, as it still had a shape and did not just run into her back or thighs. She was the authority in Matt's house too. She was the top earner since Mr Paul worked Construction so he was constantly being laid off for long periods. Ms. Karen however worked long hours at her job and had been in her position for over 20 years. She wasn't mean but when she did speak you naturally would listen.

Matt and I would take turns spending the night at the others house. My mother did not particularly like my friend Matt so eventually it was easier to just stay at his house instead of pleading our case for a night at mine. We would stay outside late while at his house though so I preferred it anyways. His parents were always less likely to set a curfew for us so we'd ride our bikes or hang on friends' porches until their moms kicked us out. We'd play capture the flag or box free as long as we had others to join. As we got older, we'd sneak to neighborhood girls houses pretending we had a clue, and would attempt to lure them out to hang with us. Summers we'd found sneaking into pools was a good way to cool off and a victimless crime if you didn't make too much noise.

Kind of where our story begins. One early June summer night it was hotter than the rest. We had been in a heat wave with no relief even at night. It was a Friday night and I was geared up to stay the weekend at Matt's house. I skipped even going home after school that day, even at 18 and in my senior year I typically still checked in before heading out. But today it was just too hot to travel again after I would have gotten home. I figured I could have my mom bring me some clothes later or just borrow some of his as we were basically brothers and around the same sizes. We were both 18 finally, similar builds, about 180lbs, 5'8-5'9 I was slightly taller than him but not by much. He had dark brown hair and a natural tan, I was dirty blonde and had to work on my tan to achieve it.

It was about 7pm and we were sitting on his porch, basically melting.

"Matt, man. It's too hot to be out here" I complained.

"Scott... Dude! I know! But my parents asked us to stay outside a while tonight. I think my mom's mad at my dad or something. I'm not sure but when she gets like this she needs a few hours to cool off or she's just a pain in the ass" He said with very little actual concern for their situation. There wasn't really any reason to have concern though. His parents were great together and had been married too long to break-up.

"Well we got to find something to do or somewhere to go" I continued to whine.

"Want to walk to the mall?" He suggested.

"Nah, too hot. We'd be soaked by the time we walked all the way down there. What about Ambers?" I asked. Amber was the girl who lived behind Matt. Right across the ally in fact. She was a year younger than us and has been in LOVE with Matt since her family moved in when she was just in kindergarten. He however, did not feel the same towards her, so naturally I gave him a hard time about it.

I never really understood why though. She had developed early and was definitely cute. We were horny guys and she was a willing participant so it never made sense that he'd never made a move just to do it. I on the other hand constantly tried, but was rejected because of her hapless devotion to Matt.

Whatever it was he was going to need to get over it with her tonight. It was 105 degrees and she usually invited us right into her house with her glorious AC running overtime.

"Absolutely, not." He had rejected my suggestion immediately.

"Matt, let's just go hang out with her. We can figure out the next move from the comfort of her living room, where we won't be sweating so bad. Besides she loves you and it's Friday night ha-ha" I joked as I pushed his shoulder.

"Fine." Matt said clearly not happy to have to give in.

We walked around the block to the front of her house. To our surprise when we arrived, we found Amber sitting with her friend Sara outside on her porch.

"What's up?" I said eagerly, forgetting we were only there for the AC.

"Nothing. What are you guys up to?" Amber asked.

"Hey, Sara." I said while tapping her leg to make sure she noticed me "Not much Amber, just bored and it's hot as hell out here."

"Yea, I know! Our AC broke too!" Amber sadly said as she looked at her feet.

"Hey Scott, what are you up to?" Sara jumped in with a flirty tone.

Sara had never been flirty with me. In fact, not sure we ever really spoke. She was pretty though and I immediately started thinking about the potential. Sara had enormous breasts. I mean so big you could forget she was even able to speak. She was only 5 ft tall but all boobs D cups or even bigger I'd thought.

"We were coming to see you two" I attempted to flirt back. "We were going to see if you two wanted to come pool hop with us?"

Matt fired a look my way of complete disgust.

He did not want them tagging along but he was going to play cool. I hoped.

"Who's pool?" Amber asked.

"No idea. It's too hot to go hunting for a pool and it's still too early for people to be asleep" Matt tried ending this discussion before it began.

"No way! We can go to Miss Beverly's pool" I quickly responded.

Miss Beverly was a, 70-year-old women who lived on the corner house and had a pool she never used. She was cool with us using it all we had to do was ask so i knew whether she was awake or not right now we were swimming.

"Miss Bev! I forgot she had a pool!" Amber said excited.

"Yep!" I said smirking at Matt. "Let's go!" I said turning to walk away.

"Wait, we need suits." Sara stopped the group.

"We can swim in our clothes or underwear." Amber said silencing her friend.

Matt was quiet. He knew if we were all in our underwear in a pool, he'd have a hard time fighting Amber off.

We giggled and joked as we walked across the alley towards Miss Beverly's.

"Should we knock?" Sara asked.

"It doesn't look like she's even home." Amber said.

Miss Beverly was old but not dead. She was attractive for 70 and that wasn't just the teenager in me speaking. In fact she had a younger boyfriend in his 40s and spent a lot of time with him. They were likely out tonight which meant her pool was ours!

"Fuck it, let's just go swimming!" I announced.

I tore off my shirt and started to climb the stairs to the pool deck.

Everyone followed but you could tell there was nervousness and excitement in each of us. We stopped at the top and paused briefly.

"Who first?" I asked.

No one volunteered. We all smiled and looked around for someone to take control.

Finally, of all people Matt said something "I'll go!"

He took his shirt off and tossed it over the railing. With all of us watching he undid his button, lowered his zipper and dropped his shorts. Stepping out of them he asked "Underwear, right?"

"Hell yea! I joined in dropping my shorts and kicking them off the deck eager to imply I'd no longer be needing them. I jumped into the pool and went under the water. I resurfaced quickly though as i didn't want to miss a moment.

Matt took the lesser approach and climbed down the ladder holding his elbows up over the water's surface and shivering.

The water was cool, but not cold. Plus, it was 105 degrees out.

"Come on in Sara" I leaned with my back against the side.

Nervously smiling, Sara began to unbuckle her belt. "Ok, but don't watch me"

"No chance" I said laughing "You too Amber"

They undid their belts and lowered their short while facing us. It was an amazing sight. These two moments away from being in the pool with us basically naked. I could feel my hard on spring up and had to make sure it didn't pop out of the fly of my boxers.

"Don't watch us!" Sara demanded as she smiled and held back her laughter knowing we were not going to be looking away.

Slowly the two of them began to lift their shirts. Here we go! The whole world went silent. I couldn't hear a thing. The higher their hands lifted their t-shirts the louder the silence became.

It was right around the time I realized Sara wasn't wearing a bra that Ms. Karen entered the yard.

"Stop!" Ms. Karen said sternly. "Stop it right now young ladies."

The two girls wasted no time. They yanked their shirts back down and grabbed their shorts. They ran out of the yard passed Ms. Karen in their underwear, carrying their shorts and flip flops.

"What are you two thinking? That you're just going to sneak into Miss Beverly's pool and take advantage of those two?" Ms. Karen spoke loudly.

Ms. Karen wasn't mad though. She sounded more inquisitive than mad.

"Not at all mom, we were just swimming." Matt responded.

"Yea Ms. Karen, we didn't have suits and I forgot to bring a change of clothes for the weekend." I added thinking she'd buy it.

"Well, what about your boxers? Didn't think of that did you? Now stop lying. I know you guys were up to no good. Miss Bev seen the alert on her ring cam and called me to come over and open her cellar so you guys had access to her basement bathroom. I didn't know there'd be a party going on." Ms. Karen said surprisingly calmly.

"Sorry, yea guess we didn't think mom." Matt apologized.

"You're fine Matt, you have clean dry clothes at home. Scott on the other hand will not have and dry clothes tonight." She continued to badger me.

"It's fine I'll just take off the wet boxers and put my shorts back on. They'll dry I'll hang em on the fence. It's still early and plenty hot out." I exclaimed.

"Or, we could just put them in the dryer." Ms. Karen replied.

"Haha, I guess that's an option too." I laughed.

"Come on, we'll use Miss Beverly's dryer. Your father is sleeping Matt so we're not going to run ours right now." Ms. Karen said walking towards the cellar door while pulling Miss Beverly's spare key from her pocket.

"Grab your clothes guys I'll open the door for you."

We grabbed our stuff from the deck then I walked to the fence to grab the shorts I so carelessly kicked away. Trying to catch up to the group entering the basement I jogged.

"Ok, just go into the bathroom and take off your wet boxers Scott. Matt, you might as well go over there and do the same. No reason to not just dry them both" Ms. Karen sighed.

I went into the bathroom and took off my wet boxers. I could hear Matt doing the same outside the door. I pulled my shorts up and zipped them back, then buckled my belt and picked up the wet boxers. Assuming we'd both be finished I threw the door open.

Matt hadn't quite worked as quickly as me however, to his embarrassment he was still bottomless. I got an eye full before I turned back towards the bathroom and pretended to readjust my shirt.

"Come on out Scott." Ms. Karen now entering the back of the basement with her arms extended to receive my wet laundry.

"Matt!" She said shocked. "Why are you not dressed?" she dialed it back trying not to embarrass him further.

I walked out towards the TV room and plopped onto the couch trying to mentally change the channel. I wanted to remember Sara's boob but that short flash was being drowned out now by my bottomless buddy.

"Go out to the couch I'll start the laundry. Go!" I could hear Ms. Karen from the laundry room commanding Matt.

Matt came in and sat across from me. I knew he was embarrassed and may be a little pissed because all this was caused by my idea.

"Dude, is there a baseball game on tonight?" I asked to lighten the mood while I looked for the remote.

Ms. Beverly's basement was old school. Plaid brown couche and love seat sitting L shaped, tan shag carpet, an old tube style TV and wood paneled walls light colored but still from the 70s.

"We're not hanging out here guys. Don't get too comfortable. As soon as the dryer stops, we're leaving." Ms. Karen said as she entered and sat between Matt and I.

"So those were some pretty girls Matt, I'm sorry if I made that weird. I just was doing what any parent would do. Scott I'm sorry too." Ms. Karen had never apologized before and I wasn't even sure she was wrong.

"It's ok mom"

"Yea it's cool Ms. Karen" I followed up with Matt.

"No, I shouldn't have come so aggressively. I had to stop that as your mother Matt and Scott, your part time mother. But I could have waited at least a little longer. After all, boys are boys."

Shocked I boldly blurted "Yea, it'd have been nice to have gotten to see a little more."

I froze. I was speaking to my best friend's mom. This was not another likeminded guy. Maybe I went too far.

"Scott there will be plenty of time to be a deviant" she said now smiling "You're still young, you have the rest of your life to chase these girls around." Ms. Karen said seemingly mentoring us.

"Enjoy these last years as friends. You guys will probably be too cool for sleep overs and pool hopping sooner or later. I mean when I was your age, I was already working driving and having boyfriends. I wish I would have waited."

"Hard to imagine you before Dad, mom." Matt chimed in.

"Haha well I married your father when i left college. I didn't meet him until my senior year. Obviously, you would have known I'd have had other boyfriends. Don't let it fool you, I used to be hot!" Ms. Karen explained playfully.

"I can see it" I added.

"Thanks Scott. Means a lot when you young bucks take notice of us old hags." Laughing now.

"In fact, I even had a girlfriend before your father." Ms. Karen shocked the room with her statement. I could feel my cock rising to attention for this story as i postured up and sat on the end of the couch.

"Really?" Matt asked clearly as curious as I was but in a different way.

"Yep." she sat back and crossed her legs. Ms. Karen was wearing white shorts which were fairly short but not too revealing other than them being almost see-through. She had a green silk tank top that revealed her bras texture and white flip flops which she had just thrown on to walk to interrupt our pool party.

"I thought in high school it would be important and maybe fun to explore." She brushed off the question with ease.

"Did you date her long? I mean like, how serious?" I asked maybe exposing my intent.

"Yes. we had sex Scott. I know you're waiting to ask." She politely replied to my hidden question while glancing at Matt.

"It was easier for me to be with a woman my first time. It didn't make me gay or bisexual although I don't mind the label of a bisexual." She continued "It just helped me be comfortable."

I was shocked. This was an adult conversation. Or maybe it was just like the birds and bees? Either way I needed more. I was as hard as a rock now and I couldn't turn back.

"So, are you boys virgins?" She asked looking back and forth between us. "It's ok to say yes. You're not too old to be virgins even though your friends might give you a hard time about it."

"I am" I said ashamed.

"Me too." Matt added which allowed me to look back towards the group.

"No big deal. That's actually good guys." Ms. Karen smiling now at the thought of her only son being still so innocent.

"Well, are you guys waiting to make it special or just a little scared like I was?" She asked.

"Honestly Mom, just a little scared I guess." Matt admitted.

"Yea me too I guess."

She smiled and stood up. She walked across the room and sat in front of the TV on the edge of the stand to ensure she had our complete focus. "Well, you guys are close enough, why not just do what I did?"

"Wait, what!?!" I blurted.

What was she saying? Was she asking us to have sex with each other? Confused I was at a loss of words so I stayed quiet and looked at Matt.

To my surprise he was looking at me already. He looked as if he was already agreeing as long as he knew I was going to agree.

"I mean... Wait, what?" I asked again, now slightly smiling, beginning to warm up to the idea.

"Yea. Why don't you two just mess around. Take it as far as feels right. No pressure because you're friends. No awkwardness either because you two are both learning." Ms. Karen explained.

"If you need it, I can guide you two." She continued.

Her last sentence gave me chills. It sent a warm sensation through my body. I couldn't believe it. She was going to watch us and honestly, I wanted to perform for her.

"Umm... ok Ms. Karen" I said holding back my excitement.

"Yea... uhm ok Mom" Matt also responded.

"Ok then. It's settled." She shifted. "I'll just start giving directions then, I guess. Ok, I want to see both of you stand up and walk towards each other."

We didn't waste time. I stood up immediately and faced Matt forgetting how hard I already was. Clearly, he had too. We each took a step trying not to giggle but making constant eye contact to assure one another we were not chickening out.

"Wow. Look at that." Ms. Karen said as she stood up and walked towards us. "You guys are so hard for each other."

She stood next to us as we faced one another.

"Now, I'll give instructions to get you guys going. But if you don't want to do something or if you DO want to do it just tell me." She warned us before she began.

"Now... First, I want you both to close your eyes, then slowly lean towards each other and slowly and softly begin to kiss for me."

We looked at one another for a second and then gave in. Closing our eyes, we pushed our faces forward blindly until our mouths met.

"Good boys" she said as she stood and watched her son's first gay kiss.

It wasn't much different than a women's kiss. I wasn't sure about Matt at that point but I had kissed girls. I've just been stranded at 2nd base for 3 summers.

"Now stop. I want you to take your shirts off before you two begin again."

We did just that. We took our shirts off and threw them on the couch. With the same slow start, we went right back to kissing again. Eyes closed, clumsy and mostly pecks but long meaningful pecks.

"Good job guys, good boys." Ms. Karen said seductively.

"Now, I want you two to start touching each other. Your choice where. I want to just watch you two explore." She added.

Immediately I felt his hand on my cock as if he had been waiting for the opportunity. He clumsily smashed the head of it with his palm at first causing my to briefly open my eyes but we never broke our kissing. He recovered well by turning his hand and cupping it, forcing my dick upward instead which gave the same thrills of burying a morning wood into the mattress.

I took the less direct approach and placed both hands on his love handles.

"Wow Matt, so eager" Ms. Karen said stating the obvious.

"Ok, now keep kissing. Start using your tongues. I'm going to come behind you guys and lower both of your shorts for you. When you feel your shorts at your feet you may step out of them." She instructed.