“So dude, I don’t want to sound weird or anything, but I think you should hook me up with Mrs. Skye or Janet again. I’ve been going through a bit of a dry spell,” Jon said to me on our walk home from school. I knew it would only be a matter of time until this came up, but since then, there had been a bit of a complication. Not only was I fucking Janet and Mrs. Skye, but I’d also started fucking Jon’s mom, and she wouldn’t be happy if she found out that I had arranged something with the other two without including her.
“Yeah man, maybe soon, but I don’t want people to start thinking something is up,” I responded, trying to dodge the topic.
“Don’t fuck me over man. How can you take the two hottest fucking MILFs around and not even give me a shot?”
“Fine!” I almost shouted at him. I just wanted to end the conversation. “Tomorrow night I’m going to Mrs. Skye’s house with Janet. If you just shut the fuck up, I’ll let them know you’re coming too.”
“Thank you, thank you, thank you!” I nodded at him, upset that I had to share again, but happy that he was finally going to shut up.
Now I just had to hope that his mom didn’t find out. The last time I had fucked her, she suggested something a bit bigger. I didn’t want to risk not fucking her by leaving her out just to get her son laid. When I got home that night, I texted Janet, letting her know that I was bringing somebody. She was more than happy about it, letting me know that she was looking forward to it and that there would be a surprise for me and my friend. That made me instantly hard, but I didn’t jerk off, hoping to build up some tension for the following night.
The next day after school, I met up with John and we walked around the block to Mrs. Skye’s house. John wasn’t even trying to be subtle about how excited he was. He was wearing basketball shorts and you could tell that he was already getting hard walking down the street. Luckily no one was around long enough to figure out what was going on. As we approached the house, Mrs. Skye came up to the door and hurried us inside. She obviously didn’t want to make a big scene either. When we walked inside, Janet was sitting on the couch with a glass of wine in one hand and her other hand down her unbuttoned jeans. The TV had a porn DVD playing where a small blonde girl was getting gangbanged by 5 or 6 black guys. Janet turned her attention to us as we walked into the room. “Oh about fucking time! Mikey, who is your friend?” She said to us. “Janet, this is Jon, but you’ve already met him. Actually, you’ve fucked him,” I said to her. “Oh, well, I guess I didn’t recognize him. Sorry honey, I’ll make it up to you. Come on over here,” she motioned to him. He immediately complied, taking a seat next to her on the couch and pulling down his pants.
“I didn’t even need to tell you to take your dick out for me. That’s what I like to see in a young man,” she said as she took Jon’s penis in her hand while still playing with herself. I immediately turned toward Mrs. Skye. She was closing up the curtains on the windows and not facing me when I approached her from behind. I, also wearing basketball shorts, eased my schlong out and lifted her skirt. Not yet completely hard, I slapped up against her tight, round ass cheek. She didn’t turn to face me but rather started teasing me by moving her hips and grinding against my crotch. I reached down and lifted her shirt off over her head before unhooking her bra to unleash her huge tits. By now, she had also reached down and grabbed ahold of me. She slowly started stroking, up and down, getting me harder and harder.
“Dude, did I say thank you?” I heard Jon say. I looked over at him and saw him laying back on the couch, his cock all but hidden, its entire length devoured by Janet. “Hey Janet, you promised me a surprise,” I said while playing with Mrs. Skye’s titties. “They’re on their way. You definitely won’t be disappointed,” she responded. The way she said “they,” made me rock hard in anticipation. I turned Mrs. Skye around and started to kiss her while she stroked me off. I reached up under her skirt and started to rub her pussy through her thin thong. I could feel her getting wet. I grabbed her hand and led her to the couch. Jon sat up and I sat down next to him. Janet and Mrs. Skye got down on their knees in front of us. They switched positions and Janet started blowing me while Mrs. Skye went for Jon. Janet gave me the sloppiest, wildest blowjob that I had ever gotten right then. Unfortunately for me though, she was still completely clothed. I couldn’t believe that Jon hadn’t at least tried to get her naked. In a quick motion, I got down on the floor with Janet and nearly tackled her to the ground. I ripped open her button down shirt and buried my face in her chest. She managed to pull her pants down and, in the heat of the moment, I jammed my cock right into her pussy. She let out a scream and then started biting my neck. I thrusted in and out of her wet cunt, faster and faster, while Jon got his dick swallowed by Mrs. Skye. Within a few seconds, I heard a knock at the door and jumped. “There’s your surprise honey,” Janet said as she got up, kicked her shorts and panties off from around her ankles and walked over to the front door. Mrs. Skye didn’t miss a beat and continued to blow Jon, who didn’t even seem to realize where he was. When Janet opened the door, I couldn’t help but crack a huge smile. In through the door walked my English teacher, Mrs. Robinson. She seemed a little timid, but any sense of hesitation must have went away because when we made eye contact and she saw me sitting on the floor, my legs extended, slowly jerking off, she returned my smile. “Hi Mikey. I hear you and I have a mutual friend in Janet.” “Looks like it,” I responded. “This really is a nice surprise!” “Well that’s not all,” Janet cut me off. Following Mrs. Robinson was Emily. My jaw dropped. This was not good. “Hi there…” she started saying before she saw Jon getting his cock sucked on the couch. We were fucked. “Jon, is that you?” She asked, breaking what seemed like an eternity of silence. “Oh fuck,” was the only thing that he could muster. He didn’t even try to grab his shorts. He just sat there, his cock still hard, looking up at his mom, who had come to have a wild orgy with me. “Do you two know each other,” Janet asked. “That’s my son,” Emily responded. “You know, we couldn’t keep doing this forever,” I said, trying to end the situation before it got uglier. “What do you mean? I’ve done crazier things than this,” Janet said. The fact that she was suggesting we continue both baffled me and turned me on. “What do you say, Emily? Is that ok with you?” Janet asked.
“Jon, if you can keep your mouth shut, I can too,” Emily said. Jon, not knowing what to say, just nodded affirmatively. Mrs. Skye smiled and went back to blowing him. I didn’t know what to think, but I knew what I wanted from Mrs. Robinson. She was wearing tight jeans that made her ass look really sexy and a shirt that was clinging to her body. Unlike the other women that were in various states of undress around the room, Mrs. Robinson had rather small tits, which was a nice change of pace. Her long, flowing dark hair rested on her shoulders as she unbuttoned her light blue shirt. Janet had made her way back to the couch with Mrs. Skye, and they were both busy playing with Jon.
“Well Mrs. Robinson, I guess you came here for a reason,” I winked at my teacher, jerking off a bit faster now. Emily looked like she didn’t quite know what to do. I figured Jon knew something was going to happen, but I looked at him for approval just in case. By now, he was being ridden by Mrs. Skye and Janet was sitting on his face, so I took that as my go ahead. I got up, grabbed Emily’s hand, and led her to a chair on the far side of the room. I beckoned Mrs. Robinson to follow us. I had Emily sit down on the chair and knelt down in front of her, sliding her legs apart and slightly hiking up her skirt. Mrs. Robinson knelt down with me, and we took turns eating out Jon’s mom.
“I’ve never done anything like this with a student before Mikey, but this is pretty fucking hot,” Mrs. Robinson said to me after lifting her face from Emily’s pussy. “But, you can’t tell anyone.”
“Mrs. Robinson, why would I tell anyone about this? Plus, you’re not the one who should be worried. Jon is over there jerking off while watching me lick his mom’s cunt,” I responded. It was true. Janet was still kind of sucking his cock, but she was really concerned with Mrs. Skye who was now eating her out. Jon’s gaze was focused on us, and I suspected he was actually looking at Emily, because Mrs. Robinson was still wearing a bra and pants. He sure wasn’t looking at me.
“Well, in that case, would you let me suck your cock?”
“Please do,” I answered. I laid back and Mrs. Robinson unhooked her bra before leaning over and starting to blow me. I ran my fingers through her hair as her tight ass in even tighter jeans waved in the air. Left to her own devices, Emily started fingering herself while watching Mrs. Robinson suck my dick. I turned my gaze and saw Jon walking across the room toward us. Janet and Mrs. Skye had progressed further into each other, so I guess he had gotten a bit bored. I thought he was going to play with Mrs. Robinson, but to my surprised, he approached Emily. He rubbed his dick a few times before easing it toward his mom’s open legs.
“Mmm, Jon, are you sure you’re ok with this,” Emily half asked, half moaned.
“Oh, absolutely,” Jon said as he slid his cock inside. Believe it or not, this made me even harder. I had Mrs. Robinson stop sucking me off so I could slide her jeans down. To my pleasure, she wasn’t wearing any panties and was already quite wet, so I mimicked Jon and slid myself inside Mrs. Robinson. He back was against the floor and she looked into my eyes as I slowly started to fuck her. I pumped in and out of her pussy with increasing speed in missionary position on the floor. I reached up to the chair and started rubbing Emily’s thigh as her son, my best friend, pounded her cunt.
“Look over there Janet, looks like those girls are having some fun without us,” Mrs. Skye said to Janet. I had nearly forgotten they were over there. Janet immediately got up, walked over, and knelt down over Mrs. Robinson’s head, sitting on her face. I leaned back so that Janet would have some room, and she leaned forward to stick her tongue down my throat. I couldn’t resist her big, beautiful tits, so without breaking rhythm with Mrs. Robinson, I grabbed ahold of Janet’s chest.
“Holy fuck Mom!” Jon had momentarily stopped fucking Emily and was now playing with her big tits, the same tits that I had been playing with just a few weeks prior. Mrs. Skye wrapped her lips around Jon’s length while he sucked on Emily’s hard nipples.
“Hey Emily, these guys give a really nice DP. You should try it,” Janet suggested. Emily looked at me and then at Jon.
“You guys do that,” Emily questioned us.
“Just once, but I’d be willing to try it again,” Jon said to his mom. Emily stood up and pushed her son down on the chair. She got up on top of him, facing out, and eased her ass down onto him. I took that as my queue and entered her pussy. While we started fucking both of Emily’s holes at once, Mrs. Robinson started sucking my balls from behind. Nothing had ever felt better.
Janet and Mrs. Skye were back to eating each other out, which made me feel a bit sorry for them. I pulled out of Emily’s pussy, grabbed Mrs. Robinson’s hand, and motioned to Janet and Mrs. Skye.
“Why don’t we leave mother and son alone for a bit. Let’s take a trip to the bedroom.” The Janet and Mrs. Skye led me to the bedroom and I led Mrs. Robinson by hand. When we got in bed, I laid Mrs. Robinson down on her stomach and slowly approached her asshole.
“Wow Mikey, you know what you want,” she said, not slowing me down. “Of course Mrs. Robinson. And right now, I want to fuck you in the ass,” I responded, trying hard to sound uncharacteristically cocky. As I fucked my teacher in the ass, I could hear what was going on in the other room. “Fuck my ass Jon! Fuck me right in the tight ass!” I was about ready to cum, but I hadn’t yet fucked Mrs. Skye or Janet. I had to pick between the two, because the next place I put my cock, I was going to explode. In a split second, I decided on Janet. I pounced on her while she was in the middle of grinding and making out with Mrs. Skye. I went right for her wet cunt and slid in. I fucked her harder than I had ever fucked while passionately kissing her. After a few seconds, I shot rope after rope of hot cum. It was the best orgasm I had ever experienced. When I pulled out, Mrs. Skye sucked my cock clean before Emily walked in the room.
“Mikey, that was fucking amazing,” she said to me.
“Well, I’m glad you liked it,” I answered. “Where’s Jon.”
“He’s showering off. I’d love to do that again,” she said. “I’m sure we all would.”
“Oh fuck yeah, that was great. Thanks ladies,” I heard Mrs. Robinson answer. The fact that my smoking hot English teacher just let me fuck her in the ass and loved every second of it made me ready to go again. And again.
Source: reddit.com/r/sexystories/comments/2fz00c/yet_another_milf_partywith_a_twist_str9_mmffff
Keep them coming man