My Mom's Best Friend
This all started the day my mom walked into the bathroom just as I was stepping out of the shower. Now before you start with, 'Oh, now he fucks his mom,' no, that's not it at all. So, let's just start over. I was stepping out of the shower, my cock hanging down, as my mom walked in with an armload of towels. She looked down and said, "Oh, my. Um, well, Jeremy, um, mmm, I want to ask you something after you get dressed," put the towels down and left as I dried off. Well, what she saw was my cock right after I had jacked-off in the shower so while it wasn't rock-hard, it was still engorged and almost full-sized. That, for me, is about seven and a half inches. I had measured it just a couple of weeks ago. Any way, as I got dressed, I'm wondering, of course, what my mother wanted to talk about after seeing my equipment. All manner of things were going through my mind but I just decided to go find her and see. "Hi, what did you want to talk about, Mom," I asked with a bit of a tingle in my cock knowing it was liable to be the topic of conversation.
"Well, I couldn't help but see, well, your manhood, shall we say. I was wondering if you remember my friend, Dorothy Dobson?" I did indeed, remember, Dottie Dobson, especially from the last pool party my parents threw for their friends. She came in a sexy little red bikini, easily the best looking woman at the party. "Yeah, sure. Red bikini, I'll never forget it." "Ah, my eighteen-year old son, never one to miss a pretty figure." "Well, she sure has that. She doesn't look her age, that's for sure." "She happens to be two years older than me, to tell the truth, but she is lovely. Um, the reason I mentioned Dottie Dobson is, well, I saw you with your...well, naked, and, let me ask you, do you find Dottie attractive?" "What a question. I've already said she's hot in that little red bikini. Oh, Mom, of all your friends, well, she is certainly the best looking. She's a fox." "Well, as you know, she and I are very good friends and, well, she told me that her husband, well, he's been cheating on her for some time now and she's just devastated."
"Oh, I'm sorry to hear that, Mom, she's really nice, doesn't deserve that, for sure." "You're right. I asked her if he was willing to drop the other woman and, I guess he's not. She doesn't want to divorce because of their two teenagers so she's just living with it. But, she's lonely and not getting the attention and satisfaction she should be getting from her husband." "Yeah, that's tough," I added. "Well, frankly, when I saw you a while ago, getting out of the shower, well, I rather thought that Dottie does deserve something like what I saw." I listened to what my mother was saying but it did take a second or two to fully comprehend what she was saying. "Me? Are you saying that, well, that Dottie Dobson deserves, well, something like what you saw, like what I've got?" "I am." I laughed. I just couldn't help it. "You're suggesting that I, um, entertain Dottie with my, well, what you saw?" "I'm sure what I saw would make her very happy, Jeremy." "Well, sure, I guess so, but, she's your friend." "You're not suggesting that I have an affair with her?" "No, no, I didn't mean that, it's that you're asking if I want to, um, be of service, so to speak, to your friend, have sex with her?"
"Yes, that's what I'm asking. I know it's a strange request from your own mother but, well, Dottie is in need of, well, some of what I saw and I thought perhaps you, being a healthy young man, well, might enjoy cheering her up." "God, Mom, you're incredible. I...I really don't know what to say? She is a real looker, that's easy." "Oh, I'm sure she'd be thrilled to hear you say that about her, I'm sure of that." "Well, I'm only eighteen, how do you know I could make someone like her happy?" "I saw you coming out of the shower, Jeremy, trust me, I know you can." "So, just how might this work. Oh, look I'm talking with my mother about how to have sex with one of her friends." "That's exactly what we're talking about, yes. Well, I suppose I could tell her that you find her attractive and, um, well, I suppose I can just pose it to her and see what she says. I'll try to describe what I saw, that should get her interest." "This is so weird, but, hey, she's a MILF for sure." "Well, I could tell her my idea, if she likes it, then have her over and you can take her back to your room." "Well, I don't even need to think about it, Mom, she's hot," I said as my mind churned at the thought of fucking my mother's best friend.
I have to say, it was the strangest, oddest thing in my life so far, my mother asking me if I'd be interested in fucking one of her friends. And, a friend that's really hot. I let my thick, seven-and-a-half inches answer for me and agreed. I'd seen Dottie in her bikini, now, maybe I get to see her out of her bikini. Nice. So, a couple of days went by when Mom told me that Dottie was all excited, she had described my equipment in detail to her, and that Saturday was possible for her visit, the afternoon, it seemed, if I was up for it. I rather naughtily told her I was very up for it and winked. Right after lunch on Saturday, our doorbell rang and Mom went and brought back her friend to the kitchen where I was still sitting. "Jeremy, here's Dottie, you surely remember her," she said. "Oh, the red bikini, what male could ever forget," I said as we kissed. It was a kiss rather unlike any I'd ever gotten from my mother's friends before, a look at what lay ahead, I think. "Oh, what a sweet thing to say. Yes, that bikini has gotten me a few compliments, none nicer than yours, Jeremy." "Well, I know Jeremy is eager to show you his room, Dot, um, you two enjoy yourselves, I think I've got some shopping to do," my mom told us and we went up the stairs to my room and closed the door. "Well, it's just you and me, Jeremy. This is quite wonderful of you and, I must say, I'm quite excited and just a bit nervous. I'm afraid I've never done anything quite like this before." "Oh, me either, it is kind of a nervous situation."
"Here, let me undress you, I think once we're out of our clothes, we'll feel more comfortable and relaxed," and she soon had me naked as she pulled my briefs to the floor and, kneeling there, took my cock in her hand. "Oh, yes, your mother was right, Jeremy, you have a wonderful cock; and so young and hard, oh, it is so hard," and she surrounded the tip end with her lips. As soon as she started sucking, all my nervousness fell away, she was wonderful. Her hand was up under my balls rubbing them back and forth as she sucked. Then she stood and asked me to undress her. Truthfully, it was the first time I'd ever undressed a girl or a woman; with others, it had always happened so quickly that we each had disrobed hastily to get to the main business of fucking. But, I was able to work my way through the various layers of clothing and, soon, we were in each other's arms, kissing and feeling, pressing our naked skin together, both eager for what was to come. We stopped kissing for a minute as I stood back to look at her. I have no idea if she's ever had plastic surgery but her body was terrific. Her nipples were small and erect, her pussy as bare as the girls I went to school with. I took her hand and led her to my bed, swept the covers back and she lay down. I sat on the bed, leaned over and crawled between her legs.
I rubbed the head of my cock up and down in the abundant wetness along her slit, then pressed forward as I watched her body take me in. I went in about two-thirds and began to cycle back and forth. She was much tighter than I had imagined. I'd heard that older women tend to have loose pussies, that they stretch as they get older and get fucked more. Well, not Dottie Dobson. "Mmm, oh, I wonder if I should tell your mother how good you feel, so hard, nice and big, so hard, mmm. But she was right about you, Jeremy, you've got a great cock." "Well, I can't believe how beautiful you are, Dot, and so tight, you're like the first girl I ever had." "I'm enjoying your nice cock, so generously offered, I'm indebted to your mother and, especially to you, my dear," she said softly as we fucked on my bed. My dick was feeling so good, I knew I was close to cumming, really close, then she started moving under me, twisting around, both of us fucking each other, now beyond the shyness and reserve that we had just minutes before, but now we were fucking, and enjoying it greatly. "Uh, oh, I'm...uh, UH, UH, UNH, UNH, mm, mmm, oh, feels so good, mmm," as I jammed down into her spurting my cum inside my mother's best friend, she tensed, then pushed up hard as her body quivered under me. Oh, OH, OH, Jeremy, oh, yes, mmm, UHN, UHN, UH, UH, mmm, oh, you were wonderful, kiss me, Jeremy, mmm, don't stop," and she pulled me down to her as I kept stroking my cock in and out of her, I was still hard, she was so sexy, it was wonderful. We fucked three times that first time together and that wasn't all. She gave me a fabulous blowjob just before she left, one that rattled my testicles. She really knew what she was doing.
I knew after she left and I came back out to watch television with my mother that she was dying to ask but just didn't want to, so I helped her out. "So, are you curious, Mom?" "Oh, Jeremy, I'm just dying to know, yes, tell me." "Well, how much detail do you want?" "As much as you'll share," she said with a naughty look on her face. "I can tell you that it's the best sex I've ever had." "And her body, well, I've seen her in that red bikini, but naked, oh, she's so hot." "She seemed to stay longer than I'd first thought." "Oh, Mom, we just did it over and over and then she gave me head before she left. She sucks like an angel. Or is that too much detail?" "Mmm, almost. So, is she coming back?" "Tomorrow, even a little earlier. We're both pretty happy with how things turned out.