Learning My Lesson
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Chapter 1
Being a sixteen-year old male, there was one thing that was prominent in my mind: sex. I had a girlfriend at the time, she was a freshman in my high school, Debbie, and I'd finally gotten her to take off her top and bra. She had really pretty breasts, nice and firm and pointy with hard, dark red nipples that we both loved my sucking.
She would also jack me off but didn't let me in below her waist. Of course, I tried but she was adamant. She told me she wasn't on the pill and all that but I tried an end-run telling her I'd get condoms but that didn't work either.
Then, one afternoon, after school, at my house up in my room, she had just given me a handjob when she asked, "Frank, would you give me a picture of this?" as she lifted up my dick.
"My dick? You want a picture of my dick?"
"Yeah, it would be cool. But I want it really, really hard. And close-up, too. Not fuzzy, really clear."
"Sure, I guess. Just for you, right?"
"Of course, silly, you don't think I'd stick it up on the bulletin board at school, do you?"
So, that evening, I got it good and hard and took a couple of pics which I emailed her. I just knew that it meant that I was soon to be getting her into bed. We were both virgins, neither one of us had had sex with anyone yet and I just knew this was going to be the key to getting her naked and us doing it at last.
But several weeks, even a month, went by with no mention of doing more and whenever I pressed on a bit, she refused to go any further.
Then, one afternoon, I went over to her house without calling first. Her mom answered the door, "Oh, Frank, Debbie's not here but come in, I really want to talk with you," and I followed her into the kitchen and we sat at the table.
"As Debbie's mother, I really need to talk with you about something I saw on her computer this morning. Did you send her a couple of pictures of yourself? Like from the waist down?"
Oh, shit, I thought, I'm done for now. I guessed the truth was the best way to go so I told her, "Um, yeah, I did."
"So, that's you? There's no face, of course, but I figured it would be you, she's not involved with anyone else. So, I want to give you something," and she got up and left the room to return a minute later to set down a box of condoms in front of me.
"Um, what are these for?" I asked.
"I want you to use them when you two have sex. Every time, too. I don't mind that you two are having sex, you both seem mature enough I suppose and it's bound to happen. I'm not ready to be a grandmother and I don't want Debbie getting pregnant. So, you'll use these every time? Each and every time you two have sex?"
"Well, um...".
"You've used a condom before, right, Frank?"
"No, ma'am, I haven't, but...".
"You haven't? Oh, Frank, please begin using them. You do know how to put it on and all, right?"
"Um, I kind of remember from middle school I think."
"I really don't want to take any chances like that, Frank, let's go upstairs," she said as she stood up, picked up the box and went up to the second floor and turned the other way in the hall from Debbie's room into her bedroom.
"Well, it's a good idea to show you just how it's done," and she knelt down in front of me pulling my belt open and unbuttoning my jeans. She was taking my pants off. My girlfriend's mom was taking my pants off to show me how to put on a condom. I stood there stiffly, no not my dick, I was too scared to have a hard-on, that was far from my mind right then.
She got my fly opened then gripped my jeans and my briefs together and just tugged them straight down to the floor. My face was so hot feeling and no doubt beet-red. I didn't dare look down, I just stared straight ahead as I felt her hand take my limp dick and lift it up.
Then, something happened that I absolutely had no idea was coming, I felt her lips suck in the head of my dick to begin sucking on it. It was something that Debbie had never done, she didn't like the idea at all and now her mother was the first to ever suck my dick. My heart raced and raced as she sucked, every pull helped pump more blood into my cock expanding it like never before.
I stood there panting as I finally got the courage to look down. She was sucking away, looking up at me, a faint smile on her face.
Then, she pulled away leaving my hard cock hanging wetly between us. She opened the box, took out a packet and tore it open, then holding the reservoir tip, leaned forward for a few more sucks, then put it on the head and rolled it down all the way.
"There, see, you need to be nice and hard, then hold the tip, that's what catches your semen, you want that empty when you enter Debbie. These are lubed, see, feel, that'll make it easier to enter her. So, are you two enjoying sex together. I think you must be her first boy to have sex with."
"Um, well, actually, we aren't having sex ... we haven't done it."
"You haven't? I surely expected, after seeing your picture that, well, I don't know why she doesn't, it appears to me that you have everything that's needed to make her quite happy. Sometimes, Frank, I really just don't understand my daughter. If I were her, well, it would be different."
Then she lifted her hand and wrapped her fingers around my dick stroking it back and forth, still kneeling there, looking up at me as she said, "It's really a shame that she's not enjoying such a nice cock as yours, Frank. She just doesn't know how wonderful it can be. But I do. Have you ever gone down on Debbie, eaten her out?"
Wow, that's pretty personal, I thought, but after all, I was standing there with her slowly masturbating me. And it felt better than when Debbie did it, too.
"Um, actually, I've ... um, she's told me she didn't want me to do that. I would but she didn't want it."
"Well, my daughter doesn't know what she's missing then," she said as she stood up, still holding my sheathed cock, still stroking it back and forth.
"Frank, I can't explain my daughter, but I'll tell you her mother admires this very much," she said as she squeezed it gently. "I'd certainly let you do oral sex on me, it's something that I fondly love and I'd love to be the first one you have sex with, right now, this afternoon, if you'd like."
I was, for the first time in my entire life, speechless. She looked at me and laughed, saying, "You look a bit stunned, Frank. I'm sorry, I know it's a huge deal for someone your age but when you've my age, well, sex is something much more normal, something you get much more relaxed about. I didn't mean to upset you if I did."
"No, no, I'm not upset, it's just that, well, this was hardly anything I was expecting. I mean, all this," as I nodded down to her hand playing with my now very-hard cock.
She laughed and leaned to me and kissed me as I felt her tongue press into my mouth.
Now, before I go any further, maybe I should tell you a little about my girlfriend's mother.
Debbie is a very cute girl and has a very nice figure. I've seen the top half of her and she could be in Playboy in a couple of years. And she gets it all from her mother. Her mom is as tall as I am which is about five-eight, blond hair usually in a ponytail, blue-gray eyes, nice smile and a very nice figure. She's curvy in all the right places, nicely proportioned, what all my friends would call a MILF.
I knew that the next step was her getting naked and my heart was pounding harder than it ever had before.
"If you're interested, Frank, we can go further but, if not, I'll understand and we can just get you dressed so you can go home, it's really quite alright."
"I'm, I'm pretty interested Mrs. Perry, if that's okay?" I managed to squeak out.
"I think if we're going to be intimate with each other Frank, we should use our first names, at least at times like this. Call me Susan."
She smiled and began to pull up my tee shirt and after she had it off, she helped me step out of my jeans and briefs which had still been around my ankles, then stood up and pulled off her top, reached around back and dropped her bra on the floor. She reached down for my hands and brought them up pressing them to her breasts.
"You're really beautiful, Mrs., um, Susan, really pretty. They're so nice," I told her as I kneaded them in my fingers.
"Have you seen Debbie's breasts? You can answer, I won't be at all angry."
"Uh, yes, we've gone that far, she lets me, um, suck them," I admitted.
"It's something most of us really love, would you like to try mine?" she asked as she lifted one slightly.
I sat down on the bed behind me and took in the nipple she'd led to my mouth. Her nipple was larger than Debbie's and really sexy to suck. Her fingers could reach my dick and she pulled the condom off softly telling me that she didn't need it for protection.
As I sucked, I was massaging her other breast as she rubbed her hand over the tip end of my dick, her other hand softly stroking my cheek.
"This is nice, Frank, I'm glad you decided to stay."
Chapter 2I smiled up at her but I really didn't want to quit sucking her boobs. I had just moved to the other one and was enjoying every second. I didn't know it then but I since learned that Susan was thirty-six and had the body of a woman in her twenties. She didn't sag at all, she was nice and round and firm with C-cups and small, hard, dark red nipples that were really popped out. They were delicious to suck.
"Mmm, well, we don't have all day, I suppose, though this is very nice. Let's get me naked and we can enjoy each other even more," she said as I let her nipple out of my mouth. She undid her belt and slid her shorts to the floor, then dragged her pink panties to the floor and kicked them away.
"Wow, you are really beautiful, all over," I gasped as I drank in the beautiful curvy woman standing naked in front of me.
"Let's get comfy," she said as she drew the covers down and got in bed, patting the spot next to her. I got next to her and she pulled me down as we kissed and our hands began exploring one another.
Then, her mouth came to my ear as I heard her whisper, "Are you ready to give oral sex to your first lover, Frank?"
Lover? Wow, she called me her lover. Well, I guess I was and now I wanted to start being like a lover as I moved down as she opened her legs welcoming me into further intimacy.
Her pussy was beautiful, plump, so nice, some wetness along her slit, perfectly smooth, she must shave it, I'd heard most girls my age did though they seemed to never want to show me and now, my girlfriend's mother, now my lover, she says, is stretched open showing me her's and I've never been more excited.
I'd seen it done on the internet, especially the guy flicking his furled tongue up and down so I tried what I'd seen. I've always thought that instead of teaching us sex-ed, they should just turn off all the filters in the computer lab at school and let us all watch porn.
I leaned forward and kissed it right in the center, then began licking wetly up and down. I also went all around her pussy up onto her inner thighs, then began doing the tongue-flicking thing.
"Mmm, Frank, are you sure you haven't done this before? No, don't answer, just keep going, it's lovely."
So, I did just that, licking and tonguing, as she lifted her legs up and put them on my back.
"Mmm, oh, right there, mmm, just like that, yes, oh, OH, OH, UUH, UUH, mmm, mmm, oh, Frank, mmm, come up here, I want you up here," she moaned as she pulled me up over her. I felt her hand snake down between us as it gripped my cock. She pushed herself down until my dick was right at her pussy, then lifted her legs high up and said softly, "Push it in, Frank, fuck me, I want you to fuck me," and I did just that.
My dick went inside her pretty easily, she was really wet and slippery inside and as soon as I began going back and forth, the feeling was simply stunning. This was so much better than jacking-off. I knelt there between her legs, thrusting in and out as my hands enjoyed her breasts.
"Mmm, so good, pinch my nipples, Frank, you can do it hard, I like it that way." Again, I did just what she wanted and she was writhing and squirming under me.
"Oh, so good, Frank, this is so good. Poor Debbie just doesn't know what she's missing, but I'm sure enjoying it, you have a very nice cock, Frank, and you're using it very well."
"I think I'm really getting close to cumming. Should I pull out?" I asked having all my sex-ed flash back through my mind.
She laughed and said, "Oh, just fuck me, Frank, my tubes are tied, no way I can get pregnant, just fuck away, cum whenever you want."
I knew that 'whenever I wanted' was coming up pretty quickly, after all, this was the most sex I'd ever had and while Susan was older, quite a bit older, like twenty years older, she was still a very attractive, very sexy woman, certainly sexier than her daughter.
She raised her legs up in the air and put her hands up under her hips, lifting herself up, to begin rotating around in a circle while I fucked her and that was so good, it was all I could take. My cum began shooting deep inside her as she cried, "Cum, Frank, cum in me, fill my pussy, mmm, good, mmm, so good."
The feeling was the best I've ever had; I now knew that sex with a woman, a woman who had the skill and experience Susan had, was the best thing a guy could have. I knew then that I wanted to have this woman much more than this one time.
"Get me off, Frank, mmm, fuck me, make me cum," she moaned as I plowed back and forth. It was even feeling like I might cum a second time.
"Mmm, close, oh, yeah, just like that, keep ... uh, UUH, UUH, UHN, mmm, mmm, oh, Frank, I love your cock. Mmm, just don't stop, okay, just keep fucking me, mmm, so good."
I didn't want to stop, it felt so good even after I'd shot my cum, I just wanted to keep going, it was even feeling like I had a second cum on the way.
Makenna
- 31.10.2021
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