In high school, a group of us hung out at our friend Tommy’s house just about every other weekend. We would hang out and play video games, watch movies, and the coolest thing for a bunch of teenage boys was that Tommy’s mom would allow us to drink beer, as long as we were not going anywhere, and staying the night. Tommy’s mom was a single mom. She had gotten pregnant with Tommy when she was still in high school. She had worked hard to go to college and get a good job, while also taking care of Tommy the whole time, with the help of her parents. Of course, the other thing that we all liked about going to Tommy’s, was that his mom was most definitely a MILF. She was one of the hottest moms any of us knew.
One weekend, things got extremely crazy. It was a Friday night, and 4 of us were at Tommy’s house. There was myself(Grant), Danny, Will, Mike, and of course, Tommy. We had all went to his house straight after school. Also that evening, Tommy’s mom went on a date, and wasn’t sure when she would be back. Tommy had convinced her to let us try a bottle of rum that night, as we had been watching the Pirates of the Caribbean movies. She agreed, and left us the bottle and a case of Coke.
As the night went on, we were extremely drunk. At one point, Tommy, Mike, and Will were all passed out; Tommy and Will on the two couches, and Mike had somehow made it into Tommy’s room to the bed. Danny and I were playing Black Ops, and decided we were hungry. We went up to the kitchen to get something to eat, and found Tommy’s mom in the living room, with a bottle and glass of whiskey. Apparently her date had not gone as well as she had hoped.
We said hi, and had asked about her date. Then she asked us to come sit and talk a bit with her. As I stated at the beginning, we all thought that Tommy’s mom was an absolute MILF, and we were extremely drunk by that point, so we were happy to sit down with her. As we were talking, she told us to stop calling her miss Smith, and just call her Tammi. For some reason, I guess in our drunk minds, that brought her more to a human level and less to a ‘mom’ level, helping things progress the way they did.
As we were talking, she offered for us to try the whiskey. She said something about it being a ‘manly’ drink, and of course we both sucked that up, and tried to act cool as we tried it. As drunk as I was, I don’t remember the whole conversation, but I do know it turned sexual quite fast. She started asking us about experiences with girls, interjecting with some of the thoughts she had at our age, and even a few of the things she had done. Then the flirting and complimenting started. At one point, Tammi mentioned how hot it was, and if we were okay with her taking off her sweater. We of course said yes, and she pulled it off, revealing just a bra underneath. Under normal circumstances it would have been hard for us to not look, but being extremely drunk stupid teens, we just kind of sat there and stared at her tits. She giggled and asked if we had not ever seen a pair of tits. Danny responded, saying ‘yes, but none like yours!’ She frowned a bit and asked if that was an insult or a compliment. Danny quickly stated that it was definitely a compliment. He said that he had never seen tits that big or nice before. She giggled a bit, and downed what was left in her whiskey glass.
She handed me the glass, and asked if I could go get some more ice. I went into the kitchen, got some ice for all of us, then went back into the living room. I couldn’t believe what I was seeing. There was Tammi, very passionately kissing Danny. They continued until I sat down on the couch next to them. Tammi broke away, and was smiling giddily. She looked at me, then asked Danny to pour us all another glass. As he was doing so, she leaned over and started kissing me like she had just kissed Danny.
After a few moments, she broke away and we had some more whiskey. She started asking us more questions about things we had experienced, finally ending with questions about whether we had ever shared a girl. Neither of us knew what to do at this point. She downed the rest of yet another glass of whiskey, then told us how it had been a very long time since she was kissed and touched by a man. She next asked if we would like to touch her tits, and of course, we both nodded our heads. She took off her bra, and we both started playing with one of her tits each. She was definitely enjoying it, and soon she pulled her skirt up and slipped her hand into her panties, playing with herself as we played with her tits.
The next thing I knew, she was standing up and pulling her panties off. She leaned over Danny and started undoing his pants. Once she had them off, and his cock was standing straight up, she straddled him and slid herself down onto his cock. I couldn’t believe what I was watching. As she bounced up an down on his cock, she looked at me and told me not to worry as I would get my turn soon.
After a few minutes, she leaned over and whispered in my ear, asking if I had ever fucked a girl in the ass, and if I wanted to try. Of course I said yes, I want to try it. She told me to get up and do it to her right now. I quickly pulled off my pants and got behind her. I quickly started to push into her, but she told me to go slower. I did, and once I was in, she started moving back and forth on Danny and my cocks. It wasn’t long before Danny cried out, and started filling her pussy with cum. After he was done, and slipped out, Tammi told me to put my cock in her pussy now, so of course I did. It wasn’t long after that when I added my cum to her pussy as well.
By this time we were all pretty spent, so she left to her bedroom, and we went back down to the basement. Now, as I said before, Mike had gotten into Tommy’s bed, and Tommy and Will were asleep on the couches. It had just sort of happened that pretty much every time we were over for the night, Tommy would always go to his room, I would always sleep on one of the couches, while Will slept on the other, and Danny and Mike would normally sleep in the extra bedroom. So, we were not all in our normal spots that night. I just ended up on the floor this time, as I was so exhausted.
A couple hours later, I woke up to the sounds of slurping. I looked over and saw someone was bent over the side of the couch, with their head bobbing up and down. It was dark, and I couldn’t see who it was, but unless there was something one or two of our friends hadn’t told us, it could only be one person; Tammi. I watched as she sucked a few moments more, then I watched as she straddled the person on the couch. I could see the outline of her nude body as she began to slowly move up and down on the cock below her. Then it hit me. That was the couch I always slept on. But I wasn’t the one on the couch that night. It was Tommy!
I was caught in a dilemma. Do I continue to watch, knowing she is fucking her son, and not say anything, hoping that neither of them realizes what is happening? Or do I stop it now, with her knowing she fucked her son, but at least him not knowing? I was getting turned on watching, so I of course didn’t do anything to stop it. Tommy must have thought he was in a fantastic dream. I could hear him starting to moan, and even say a few things, though I couldn’t make out what he was saying. I did hear something about cumming soon, and then Tammi told him she wanted his cum. That was when something started to click in Tommy’s mind. Tammi was bouncing up and down harder as she started to cum. Starting to recognize the voice, Tommy started to say ‘mom’. Of course, being drunk and horny, Tammi wasn’t exactly in her right mind by this point. She started saying, ‘yes, call me mommy! Cum in mommy’s pussy baby!’
Obviously Tommy was too close to do anything by that point. And just about the time he started cumming in her, Mike walked in and flipped on the light, asking what was going on. That’s when both Tommy and Tammi realized what was going on, though it was too late by this point, as he had just filled her with his cum. She jumped off him, trying to cover herself up. ‘Mom, what the hell!’ Danny cried. ‘I thought you were someone else! You never sleep on the couch!’ That’s when it hit Tommy, ‘you mean you thought I was Grant? Have you been fucking my friends!’ ‘No, of course not,’ she said. ‘At least not before earlier tonight.’
None of us went over to Tommy’s for a couple of months. I’m not sure what all happened between him and his mom. I do know, that when we finally did start going back, Tammi staid at home any nights we were all there, and over time, had all of us multiple times.