My Best Friend's Mom

The Usual Disclaimer: This is a work of fantasy. All characters featured in sexual situations are over 18. The characters in these stories are fictional. Any resemblance to actual persons living, dead or undead is purely coincidental. Do not try this at home.

This story started out as two paragraphs in The Outsider, but it didn't really fit within that story. I liked the characters and the chemistry between them, so I kept writing it as a separate story. Thanks as always to my friends who reviewed this story for me. In particular, I need to thank Pat, who pointed out a glaring hole in the plot.

* * * * *

I was best friends with Kevin since about the third grade. I always thought his mother was pretty, but I never would have imagined anything would happen between us. She was incredibly strict and prudish, and if you had told me I would fall in love with her I would have said you were crazy. I never saw her wearing anything that would give away the marvelous curves of her body. It wasn't until I was eighteen and started having sex that everything changed.

I was a virgin until well after my eighteenth birthday. Oh, it wasn't like I had never dated or kissed a girl, but I hadn't gotten much further than that. In retrospect, I guess I had been operating under the assumption that women just weren't interested in sex the way guys were. The obvious clues that women were interested in me went unnoticed, because I simply wasn't looking for them.

Before I go any further, I should explain that I had to repeat the seventh grade. I got really sick a few times that year and missed a lot of school. I was pretty big for my age, and I was a basketball player all through junior high and high school. I started on our varsity squad my freshman year. Most of my friends from childhood were still my friends in high school. They were just a year or more ahead of me in school.

That was why, when I was eighteen and finally got laid for the first time, I was only a junior in high school. The girl I was with was nineteen. Tamara had gone to our school, but she had graduated the year before. I ran into her where she worked, and we had a nice chat. I missed the obvious signals, like when she laughed a little too hard at my jokes, kept saying, "You're so funny," breathily, and her subtle glances at my body. She invited me over to her apartment after she got off work, and I went along just to continue our conversation. I still had no clue she was interested in me.

I was completely gobsmacked when she started kissing me on her couch. When I got over my surprise, I eagerly returned her kiss. When she got up and dragged me back to her bedroom, I couldn't believe it was happening. My eyes were wide when she stripped right in front of me. It was the first time I had seen a woman's breasts, and Tamara's were mouth-watering.

I would love to say, "It was magical and perfect," but it was far from that. It wasn't Tamara's fault at all; I just didn't know what I was doing. Still, it was my first time and Tamara was lovely. I was a klutz and it was fortunate I didn't injure her.

When she lay back on the bed and slipped off her panties, I could not take my eyes off her pussy. I leaned in closer and then I started to lick her. I was doing it wrong and I was sort of jabbing her with my index finger. She looked down at my face and it was obvious from her expression she wasn't enjoying it.

"Steve...What are you doing?" she asked.

I felt like an idiot. "I'm sorry, Tamara," I stammered. "It's my first time doing this. I thought you'd like it."

Her expression changed in an instant. "Oh!" she said softly, and her eyes went wide. "Wait. You've never licked anyone before, or never had sex before?"

I blushed. "Any of it," I replied.

A lot of what happened is clear to me in retrospect, like the way Tamara took over and tenderly made love to me. She gently told me what to do as she rolled over on top of me in her bed and guided my hard cock into her. I thought she was being bossy and selfish when she directed me how and where to touch her, and when to speed up and slow down when she spread her legs for me. It wasn't until much later that I figured out she was trying to be helpful and make me a better lover.

I sought her out early in the summer to thank her and apologize. By then she was engaged, but she had such a loving expression on her face that I had to wonder how it could have been if I had stayed with her.

Once I started to figure out that women might actually be interested in me, though, I started seeing the signs more and more often. Less than a week after that first time with Tamara, I had my second time with a girl in my high school that I had long fantasized about. Gabby was a lab aide for my chemistry class. She had always seemed so much more sophisticated and clever than other kids our age. When Gabby carefully guided me through how I needed to use my tongue and lips to please her pussy, I followed her instructions carefully. She told me I was "a natural" after I got her off several times that way, and it made me proud.

Gabby lived up to her name. After that one time with her, I was approached by several girls who were keen to have their pussies licked. I fucked all of them as well, and started learning how to get women off repeatedly before my own orgasm. Usually I got a second or third time with each of those high school seniors, but all of those were just hook-ups without much emotional attachment. Some of those girls had on-again, off-again boyfriends they went back to. Some of them had cheated on their boyfriends with me.

I dated two girls after that initial barrage of quick, meaningless sex. Valerie and I were together for almost a month. We got busted having sex at her house, and her parents were furious. My parents were upset, but they tried to be reasonable when they sat me down after they got that angry phone call from Valerie's parents. They explained that I had to be more responsible, and that led into a longer and more embarrassing discussion about safe sex. Valerie's parents were adamant that she could not see me again, and that was the end of us as a couple.

A few weeks later, I started dating Kylie. We only lasted two weeks before she dumped me and got back with her previous boyfriend. Later on she would confide that it was a mistake, but she had loved that guy for a long time. When I was with Valerie and Kylie, we had sex almost every day. I probably learned more about pleasing a woman from those two girls than all the rest combined. I also learned how to read a woman's body language and gauge her arousal, which would prove useful when I met other women who were interested.

After Kylie, I had several more brief hook-ups before I dated Leslie. We were much more serious as a couple and continued dating until well into the summer. By then she had graduated, and she would be going away to college. It made sense that we should break up when she left, but it still hurt when it happened. What made it worse for me was that my family acted like it was a good thing that Leslie and I broke up.

This is another thing that I can look back at and know that I completely misread what was happening at the time. I was heartbroken after Leslie left, and my family tried to console me and let me know I would be alright. I was just overly sensitive and thought they were bad-mouthing Leslie.

I thought my mother said something snide about Leslie, and I blew up. Again, in retrospect I know my mother simply misspoke. She didn't mean to imply that Leslie wasn't good enough for me, but that was how I took it. When I snapped at her, Dad immediately stepped in to try to calm me down. I thought he was taking Mom's side, and I yelled at him too. My dad has a bit of a temper, so that didn't go over well.

It escalated into a screaming match there in our living room, and my dad and I nearly came to blows. Even my older sister seemed to be against me, and that just made me lose it. I stormed out of the house, thinking that my family was a bunch of condescending assholes. Instead of going for a long walk and thinking clearly about everything, I just got more and more upset. Then my phone started ringing and I angrily turned off the ringer. I didn't want to talk to them at all.

I spotted my dad's car before he saw me. I ducked into the bushes beside the nearest house and watched him drive by. From the way he was looking around and driving slowly, it was obvious he was looking for me. He still looked pissed, and I shook my head. I did not want to deal with them.

An hour or so later, I pulled my phone out of my pocket to check the time. I was stunned to see dozens of missed calls and text messages—not just from my family but from several of my friends. Goddammit! I thought, Now they've dragged all my friends into this!

It was that text from my best friend Kevin that changed everything. He was on vacation in Hawaii with his family—one last big family adventure before he went off to college. Their house was sitting empty while they were away, and I knew they kept a spare key under the welcome mat on their back porch.

Long story short, I stayed at Kevin's house for five days and used that time to chill out and think clearly. I called Kevin to let him know I was there and spent much of my time cleaning their house. Eventually I returned home and had a calm, healing talk with my parents and my sister that put the whole incident behind us. My parents actually treated me like an adult after that, and even allowed me to have girls over to stay the night in my room. Over the next three days, it felt like I couldn't go anywhere without running into a woman who was interested in having sex.

* * *

I ran into Crystal in the mall. She had been one of my babysitters almost ten years earlier. I had barely seen her since, because her family had moved away from our neighborhood. Crystal had been one of the first women I could recall having a crush on, even though I was far too young to know what that meant or express myself clearly. Even after ten years, I saw her slightly curly auburn hair and the side of her cheek and knew instantly it was her. She looked amazing, and I noticed right away she wasn't wearing a ring on either hand.

"Crystal!" I called out. I walked up to her with a huge smile on my face. When she turned and looked at me, she looked me over and turned her head slightly. I did my best not to stare at her voluptuous body. Then her eyes went wide when she realized who I was.

"Steve?" she asked in disbelief. "Wow," she gushed, putting her hand lightly on my chest. "Look at you! All grown up." She shook her head and the way she looked me over and licked her lips, coupled with the look in her eyes when she looked back into mine, let me know she was ripe for the taking.

We talked for a good twenty minutes, and that only reinforced what I had already figured out. Crystal wanted me. We went back to my house under the pretense that my parents would love to see her after all these years. Of course my parents weren't home. We started making out in the living room and then went upstairs to my bedroom. When we tugged off each other's clothes, I could not believe how incredible her big tits were. I felt a little guilty about staring, but when I looked up at her face she was staring at my body just as hungrily.

Crystal could not believe how much I made her come once I got her panties off and dove in to savor her sweet pussy. Even though she was almost eight years older than me, I was already almost as experienced a lover after the whirlwind of sex my life had become.

Crystal was really vocal when I filled her with my hard dick. She was embarrassed later, when we went downstairs and discovered my parents were both home from work. My parents were incredibly smooth about the whole thing, putting her at ease and inviting her to stay for dinner. After we had eaten, we sat around and talked for another couple of hours. I actually learned more about Crystal and her life from that conversation than I had ever known. I just remembered her as that really cute, busty babysitter from when I was eight.

After my parents went to bed, Crystal looked at me wide-eyed again. "Did they really just tell us to have a good night?" she asked incredulously.

I nodded.

"So, we could go back upstairs and...?"

I nodded again.

Crystal kept her voice down, but she was every bit as turned on when we picked up where we had left off before dinner. We had sex for over an hour, and then we used the upstairs bathroom to share a shower. I scrubbed her back and paid particular attention to her shapely ass. She looked over her shoulder and gave me a sexy moan.

"Ohhh. Are you going to fuck me in the ass?" she asked.

I looked up at her and blinked. "Um...I've never done that."

"Oh, really?" Her eyes lit up.

It excited her something fierce to be my first. She shooed me out of the bathroom after we were dry, and pushed me onto my back in my bed when she joined me in my room. I watched in disbelief as she impaled her tight puckered asshole on my dick and pumped her hips up and down. It felt incredible, of course. With her taking charge like that, I didn't worry about hurting her. She had lubricated her tight backdoor thoroughly before we started—one of the few things I knew was really important about having anal sex.

The next morning, before she left, she whispered that she had "rushed it" and was now paying the price with a sore butthole. That made me cringe, but she laughed and said it was totally worth it. She kissed me and joined me briefly in the shower before she hurried to get dressed and leave for work. I had no idea if I would see her again, but I hoped I would.

* * *

Freshly showered and freshly fucked, I was in a great mood when I jogged down the stairs. I'd heard the doorbell, of course. I grinned when I saw Kevin standing in the dining room talking to my dad. He looked awesome with that deep tan; it really suited his complexion. I strode over and gave him a hand clasp and half-hug, clapping him on the back.

"Welcome back, Kevin," I said warmly. "Thanks again for letting me stay at your place. It really helped me get my head together. I owe you big time."

He looked uncomfortable when he stepped back and looked at me. "About that..." he said, shaking his head. "Dude, you did too good a job of cleaning up while you were there."

My dad coughed out a laugh when he heard that, but muttered, "Sorry," when he realized Kevin was serious.

Kevin's face was grim as he continued shaking his head. "Mrs. Maxwell spilled the beans that you were actually staying there the whole week, and she said she saw you cleaning the house every day. She also said you only had one person over the whole time, right before you left." He blew out an exasperated breath. "My parents think I blackmailed you into coming over to clean up our house, man."

Mrs. Maxwell was their nosy next-door neighbor. I should have known she would be a problem.

I started to say, "That's crazy," but I knew Kevin's parents pretty well. They always suspected that their kids were up to some nefarious scheme. The resulting close scrutiny had made it really hard for Kevin to date and damn near impossible for him to get laid, so I nodded in understanding. "Kevin, we should go to your house right now. I'll explain everything to your folks." I clapped him on the back again. "I was serious when I said I owed you big time. Now let me prove it."

* * *

Once we were in his car and on the road, I asked, "So, how was Hawaii?"

"Oh, man, it was amazing," he gushed. "Everything was so unbelievably beautiful." He glanced over at me briefly and gave me a lopsided grin. "The women were...just smoking hot. I hooked up with this female diver, man. She was a little older and had her own place. I got to sneak over two or three times a day. It was fantastic."

"Congratulations!" I said. I knew he hadn't gotten laid much with his mom always watching him like a hawk. That vacation had to have been more sex than he had gotten before in his life. Like, all of his life combined.

"Thanks," he replied. The grin didn't quite leave his face. "So, what are you going to tell my parents? You know they're pissed at me for lying to them. They really do think I made you clean our place. They just never actually used the word blackmail."

"I was thinking I would tell them I broke in without asking," I said breezily. At his sharp glance, I chuckled, "Not in so many words, of course. I'll tell them..."

* * *

"...So after I screamed at my parents and ran away, I really didn't have anywhere to go. I knew they would find me if I went to one of my friends' houses. I spent an hour or so walking around and it started to get dark. I sat on a bench at the park and thought about leaving. I had some money, so I could have just caught a bus out of town and never come back."

Kevin's mom gasped at that. Her expression told me how horrified she would have been as a mother if her son had simply left and never returned. Kevin's dad was leaning forward in his seat, hanging on every word. Kevin blinked as my story unfolded. He seemed surprised to hear this part of the story.

This part of the story was all bullshit, of course. I had embellished to make sure my best friend's parents did not blame him for my actions. I never made it all the way to the park, and I had made my way into Kevin's house long before it got dark that night.

"Then I got a concerned text from Kevin," I continued. "I wasn't answering my phone or any of those text messages. After all, what was I going to say? But I realized you guys were still in Hawaii and I knew you kept a spare key under the welcome mat on the back porch. I figured I would sneak in and sleep here so I didn't get stabbed while I was asleep on some park bench.

"As soon as I let myself in, I called Kevin to let him know I was here. He said I could sleep in his room, but he said I couldn't have anyone over or make a mess. I was just grateful I wasn't out on the streets. I certainly didn't want to get my best friend in trouble. I am sorry I didn't ask you for permission, but if I had...you really would have had to call my parents. I just wasn't ready to face them. I really needed time to think—to get my head clear—before I could figure out what to say.

"It was actually kind of therapeutic to wash laundry and vacuum while I was thinking. After that, I just kept going. It felt like I was accomplishing something and made me feel a little better. Also, I think I was able to focus a little more clearly on my life and my situation while my hands were busy cleaning something."

"Kind of like Zen meditation," Kevin's father muttered, nodding.

"I guess so," I said dubiously. "I've never done any meditating. The afternoon after I got here, I went to the grocery store and bought some food. I didn't want you to come home to an empty fridge." I grinned. "The last thing I wanted to do was get Kevin in trouble. I thought it was really cool and understanding of him, letting me use his room while I got my head straight. I hadn't considered staying more than a day or two, but when I came back from the store, Mrs. Maxwell saw me. I told her I was house-sitting for you guys while you were in Hawaii. Then it wound up being the truth. I stayed longer than I had planned to, but I took good care of the house and never made a mess."

I let out a prolonged sigh and leaned forward, giving them the most grateful smile I could muster. This part of the story wasn't bullshit.

"I am so thankful I had the opportunity to stay here. When I calmed down and looked at everything rationally, I realized how badly I had overreacted. I apologized to my mom when she came to get me, and we had such a healing talk as a family after we got home. There is no way that would have happened if I had not had the opportunity to stay here and get my head on straight. I know you're mad at Kevin, but if you were planning on punishing him..." I shook my head, "I'll take whatever punishment you think is fair. He was just trying to help me out."