All characters (that have sex) in this story are at least 18.
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To me, my stepmom (we'll call her Debbie) is fairly average - nothing I thought any of my friends would call a MILF - probably really cute when she was younger. (A 7 out of ten maybe?) She was, however, very nice, doing all the things a kid like me could ask for from a mom. And she liked it whenever I had friends over after school.
All through school, I was never very popular and only had one or two friends that only visited occasionally. In my senior year, however, as we all started turning 18, I began to have more and more guys befriend me and join what became a regular study and gaming group at my house. We would all do our homework and studying together, then most of us would all go jump on the game systems, taking turns gaming. Those that were waiting their turns usually ended up discussing video games and movies or playing cards around the dining table.
It all started about half-way into the school year, when I commented to my stepmom, that both of my friends had turned 18 this last weekend and wasn't that a cool coincidence. She got this odd look in her eye and asked, "Aren't you turning 18 next week?" I knew she knew when my birthday was.
Once we'd finished our homework, the three of us decided to take turns on a one-on-one fighting game, leaving Mike out for now. Debbie asked Mike if he could help her reach something for her, and we didn't see him until just before his turn on the game. He seemed to be a bit unfocussed, but he snapped out of it pretty quick as he and I battled.
I didn't notice Jeff's absence until it was time to switch again. He came out of the back hallway, a bit unfocussed, like Mike. "Are you okay? What were you doing?"
"I was just helping your mom put something away. I'm fine. Is it my turn again?" And nothing more was said.
Thinking back on it, this seemed to happen every time my friends came over, which now was every day, not just a few times a week. Soon, some of my other friends started coming over, too. This is how the group grew, as I'd described above. Debbie was very interested in how old each of my friends were and seemed to need a lot of help with various projects in the back of the house and garage. Every time she needed help, she would ask a different guy to help her (never me, though, as she explained I was the host and should always tend to my guests), so that just about everyone had helped her with some small task by the time they left. She even made it a rule that only guys that had turned 18 could help her - for "insurance purposes," as she put it.
A few months in, my dad went on a business trip, and Debbie commented at dinner, that I was the man of the house until he got back. We laughed and she asked me if I wanted some wine. Like any kid, I'd tried alcohol on the sly - one time I snuck a beer out to the back yard, and couple of times my friends and I had snuck a bit of whiskey. But this would be my first time with wine, so I said yes and she poured me a glass. I liked it a lot more than the other stuff I'd tried.
We talked and drank wine through dinner, then took more wine out to the living room and sat on the couch, me pretending to be an adult and enjoying myself to no end. I vaguely noticed that each time she got up to do something, she'd sit a bit closer, but didn't give it much thought. I was feeling mellow and enjoying talking to her like this, as she and I had never really talked much before. I started to understand why my dad had been attracted to her. She was very easy to talk to. Sooner than I'd realized, she and I had cuddled up close to each other. I commented that this was nice, admitting I was very awkward with girls. Before I realized what I'd just told her and gotten embarrassed, cuddling close was her favorite thing.
Then her face flushed and she stared at my lips, as she brought her face close to mine, her hot breath smelling of wine. Why I didn't protest, can be blamed on my drunkenness, I suppose. But we started kissing and couldn't stop. At one point, she threw one of her legs over mine, straddling me. We made out like this for a while and just went with the flow from there. I found out she was very experienced and very patient, as we took what we began on the couch, to finish on her bed.
The next morning, over breakfast, Debbie told me that she never expected that to happen and that we should do our best to forget the event. She didn't let me blame myself, putting all blame on herself. She swore she'd never done anything like that before, never cheated ever, and that she deeply loved my dad. I was embarrassed and swore this would be our secret. But I had to admit to myself that I really wanted to do it again - this time sober!
So, we agreed to sweep it under the rug and go back to normal. My dad got back from his trip the next day, and neither of us said a thing. As the next week passed, I struggled not to think about it, but failed. I couldn't help wishing we could do it again. In fact, one day, just after my friends had all left, I cornered my stepmom in the kitchen and tried to put the moved on her. She rebuffed me, shocked that I would try anything like that. She reminded me that she was married to my dad and that we had agreed that one time was a mistake. She wasn't a cheater and hated herself for getting drunk and allowing what happened to take place. I sheepishly backed down. I could see she was right and I was very ashamed of myself. It took a while, but I put it behind me. I went back to concentrating on school and enjoying my after-school gatherings, and Debbie went back to being a really great step-mom, who needed help with various afternoon projects.
During one such gathering, I noticed Debbie didn't need to ask anyone to help her any longer. In fact, they kept asking if she needed help and practically fighting over the opportunity to assist, always coming back very relaxed. My curiosity piqued and I went down the back hallway, to see what she was working on that demanded such eager participation. As I neared at the closed door to her office, I heard an odd sound and bent my ear to the door. I could make out a repeating "thup-thup" sound, followed by a breathy gasp, and Debbie's muffled voice. I carefully opened the door, so as to make no sound and peeked in through a narrow crack. I could see Mike standing with his eyes closed, in the middle of the room, leaning back against Debbie's office chair. I panned down to see a dirty-blonde head moving back and forth around the level of his waist. confused, I continued to watch. Just then, Mike grabbed the head of blonde hair, net forward, and jerked as if he was being electrocuted. Then he sagged and let go of the hair. That was when I saw the mass of blonde hair was my stepmom. Mike's dick was sliding out of her mouth with a popping sound, and she was smiling up at him. The last thing I saw as I carefully closed the door, was Debbie wiping her lips and Mike pulling up his pants. I quickly raced out to the group and blended in, just in time to see Mike emerge from the hall.
As he sat down, he coolly told Jeff that Debbie needed his help and reached for a handful of chips from the bowl. Jeff smiled, got up, and disappeared. I noticed that when Jeff got back, Dave approached him. Said, "I'm going next." they fist-bumped and Dave went down the hallway.
So, Debbie's been sucking off all of my friends?!! How long had this been going on? Weren't blowjobs the same as cheating? How come she'd never blown him? He'd sure like a turn, too! And why couldn't she let him fuck her again, if she was blowing everybody anyway?