My name is Jackie, and in the My Son’s Best Friend Part 2 story I told you about my experience with Zack – my son Ricky’s best friend – and how Ricky discovered our adventure and joined us in a wonderful afternoon when I took the virginity from both of them.
After that, I occasionally had sex with Zack or Ricky, but I avoided the three of us together. I recognize 3-sums as a reality and the first I had was actually with them, but I didn’t want them do be too used or addicted to that situation instead of a good and pleasant man – woman relationship.
It was hard for me as it was for them, but I started saying no: they wanted to fuck me all the time, and I thought it would not be appropriate. I had my urges as much as they had and – as I said –in some special circumstances we slept together, but I encouraged them to date girls their own ages and to start their own sex lives.
I also mentioned to you that Ricky was failing in Chemistry, and his supplementary support classes actually led to my first affair with Zack and that’s how everything began. He was not getting better even with these classes, and I decided to challenge him: I told him to choose a prize if he passed, and he said he would think about it.
I was thinking about a new videogame or even a trip, but over dinner he asked me if I wouldn’t be mad with his choice. I was surprised and not sure then, but I said I would not. “Mom, when I watch porn I am always crazy about DP. Have you ever done it?” In my defense, I have watched porn and enjoyed it, but I’m not an expert, so I had to ask what DP stands for. “Double penetration” he answered, flushing, and I must have flushed too. I’ve seen it on flicks and it made me feel hot and wet, but I never really thought about actually doing it. Anyway, my ex-husband was too conservative even to consider a 3-sum, not to mention a double penetration. “No – I replied slowly and carefully – I have never done it” and, to my surprise, I felt my pussy getting wet. “Well, what I want is a DP, of course with Zack.” I was speechless. “So?” he insisted. “Let’s not talk about that over dinner, right?” I dodged, and we changed subjects.
We were both very quiet. After dinner, he helped me with the dishes as always, we watched some TV and went to bed. I couldn’t sleep, I kept thinking about that question. And I was too horny to sleep. I stood up, undressed my ugly but comfortable PJs, put on a sexy negligee, and went to Ricky’s bedroom. He was still asleep when we spooned in his bed, my back to him, but he was fully awake when I felt his hard cock pressing against my ass. We were both very horny, and soon my negligee was open at the front and up to my waist, his hands grabbing my boobs and his cock penetrating my needy pussy from behind.
He pumped furiously, we both moaned louder than usual, and very soon we came in an urgent, fast, strong orgasm together. No preliminaries, no nothing, simply a much needed, urgent fuck. We stayed there, his semi-hard cock still inside me, when he asked again: “You were hot, Ma, have you thought about that?” The rascal had gone to the point. “You really aroused me, Ricky, I won’t deny it, but I don’t know.” “Have you ever had anal?” “Yes.” “Do you like it?” “If it’s done right, yes.” I couldn’t believe I was opening myself so easily to my son’s very personal questions, but what the heck? His cock was still inside me! “So, Mommy, I don’t understand: you like it in the ass, you certainly like it in the pussy, so you will like it twice as much in the ass and in the pussy at the same time. Why don’t you know yet?” and he sounded as if he was smiling cheerfully. I laughed, grabbed his hands on my boobs and pressed my ass against his pelvis. “OK, smartass, I will do it, but you still have to pass your tests, and it must get a C at least.” “Leave this to me” he said. To my surprise, he was getting hard inside me again, and then we made passionate, this time calm and comforting love.
There were still three weeks for the tests, and Ricky really studied hard: no more videogames, no more TV, he simply focused on the books and exercises after arriving from school and after dinner until bed time. He worked so hard that I started preparing my spirit – and my ass – to my committed reward. Yet, it was a big surprise when he came home with a big smile and waving a B+ Chemistry test. He had earned it!
Well, now I had to prepare myself: I am not ashamed to admit that I had to watch a few porn flicks to get some ideas about DP positions and obviously had to buy K-Y. I also wanted to surprise the boys, so I went to a salon and fully waxed my pubic hair. It was funny to feel bald down there after all these years. I was also excited, I can’t deny it.
Finally, in a Saturday, Ricky invited Zack to spend the day with us for a small celebration. We made sure he didn’t know about our little arrangement, so it would be funnier.
We have a small swimming pool and sauna area in the backyard, and as it was a nice sunny day I was already there when Zack arrived. The boys swam a little and I sun tanned in a tiny bikini that caught their attention, as it was a secluded area not seen by the neighbors. My small top did not hide a lot of my boobs, so when they sat in deck chairs to sun dry I saw some interesting volumes forming in their swim trunks. I decided to tease them more, and innocently asked if they wouldn’t mind if I tanned topless, as I’d rather avoid the sun marks. They opened a big smile and said “No” in unison. I slowly removed my top, releasing my melons and laid face down in my lounger. I could feel their eyes piercing me.
After a while, I continued with my plan: I sat down and started spreading sunscreen generously, starting down in my feet and up to my calves, thighs, belly, arms, and finally spending a long time in my breasts. “They don’t see a lot of sun” I justified, and they giggled. The volumes were bigger. I laid face up and stayed there, practically naked, except from a thong that barely covered my pussy.
Ten minutes more or so, I turned over, saying “Wow, it’s too hot! Can you help me with some sunscreen on my back?” They both darted to help me, and I kept the game: “Ricky, please, do my back and Zack can do my legs, OK? I am burning already” And so they did. Ricky spread generously at the side of my breasts too, of course, and Zack carefully handled my legs, between my thighs and shyly asked if it was OK to do my ass, “Of course, darling, my buttocks don’t see a lot of sun too” and he spread sunscreen into all my ass and even under my small thong, close to my butt crack.
I was wet, and they were hard, I could see it. “Boys, by the way – I continued – these trunks are too big, you will look funny white down there and tanned all the rest. Why don’t you undress into your speedos?” Ricky said it was a good idea and stood up to undress, but Zack said he was not wearing anything else under his shorts. “Don’t worry, dear, you can feel at home, both of you can make yourselves comfortable, just use a lot of sunscreen. I will do the same.” Ricky, already in his speedos showing the big contour of his erection, immediately released it, while I stood up and let my thong fall to the floor. They gazed at my bald pussy and its dark lips, while Zack slowly undressed his shorts, releasing his long hard cock like an iron rod. I held both cocks gently, feeling all their length, and suggested: “You are too white down here, and it hasn’t been long since I waxed too. We should better go inside for a while, or we will get burned.” I walked sensually, shaking my ass, to my bedroom and they followed me with their armed dicks.
Once we got there, they started kissing me in the mouth, playing and sucking my boobs and grabbing my ass. I went to bed and then they took turns in the top and bottom parts, kissing and licking my pussy, and handling and sucking my melons. Considering the way they devoured my pussy, they were aroused and were enjoying the new hairless look. I tried to grab and caress any cock close to my hand, marveled by their hardness and the effect I had on them. I didn’t want them to come in my hand or mouth, so I decided to move on more quickly.
“Zack, dear, we have a surprise for you. Ricky wants to do a double penetration today to get a reward for his grades, what do you think?.” When I said that, I still had Zack’s cock in my hand and I felt a spasm, I thought he was going to cum right there, but somehow he managed to hold it. “Ricky – I continued – Zack will fuck my ass, OK?” “No way, Mom – he objected – it was my idea, I am crazy about your ass, and it’s my reward anyway.” I froze. “But you are thicker than him!” “I will take care, Mom, pleeeeaase!” I was lost, and told Ricky to get the K-Y at the bedside table.
Before Ricky did anything, I told him to lick my asshole. He opened my buttocks and started licking me furiously, first just the butt crack, and then I told him to probe his tongue inside my asshole and to keep fingering my pussy to relax me even more. Zack was still sucking and playing with my boobs, looking at what Ricky was doing. I told Ricky to smear some K-Y into my asshole and to insert slowly one finger in it. He did, and it was not bad. I was too hot. Then two fingers, and my pussy and asshole were seriously ready for cocks.
I told Zack to sit at the edge of the bed and to lean back. So he did, and I sat on top of him and started the pussy penetration. Soon he was all deep inside me. I leaned over him, releasing about half of his cock. I relaxed as much as I could, and asked Ricky to smear K-Y in his cock, aim it at my asshole, and to start pushing very, very slowly. When he started sticking it in, I was amazed to find out that I was already more relaxed and excited with Zack’s dick in my pussy then ever, and it seemed that Ricky’s penetration was easier: soon the big head was in, and all the rest was easier.
When I felt he was all in, I moved to bring Zack’s cock deep into my pussy again, and started moving. Actually, I couldn’t move much in the middle of that human sandwich, but it was a signal for them to start doing so. Ricky was standing up and had all the freedom, so he held my hips and started pumping. His strokes pushed my body against Zack’s and into his cock, who in his turn did his best to raise his pelvis, pressing it against my pussy when I came down pushed by Ricky. He said: “Mommy, it’s so tight, so hot, much better than I had imagined!”
I was in heaven. I felt replenished in a way I had never felt or thought possible, and I could feel both cocks frictioning each other through a slim membrane separating my vagina and rectum. It seemed I was going to explode.
Actually, the scene was so steaming hot that it seemed all of us were going to explode, and in a few minutes we did: Zack came first, holding my hips and pulling me hard against him, his spitting cock deep inside me. I started moaning and coming too, and I also felt Ricky increasing the power of his pushes, deeper and deeper, slapping stronger against my ass, and yelling that he was coming. I shook all my body and had one of the most intense and longest orgasms ever! I couldn’t feel anything else but those cocks inside me, my whole body was limited to my pussy and asshole.
Ricky collapsed over me, but fortunately I was fit enough and Zack even more to support us all. Finally, we turned over in bed and stayed there for a while. It had been intense: my nips were tender, my pussy was swollen and my asshole was sore. But pleasure had been intense! I was sure Zack would demand his turn in my ass, but certainly not today!

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