I’ll bet you remember your first time. I sure do. It was a total surprise and, at the outset, kind of scary. Yeah, scary.
I was staying over at my best friend Gordon’s house, I even had my own room since I stayed over there pretty often. Gordie and I had known each other since second grade and we’re now sixteen and in high school.
Since I first knew Gordon, his parents had gotten divorced, it seems his father was a teacher in a small junior college and was screwing around with some of the girls he taught. So, Gordie lived with his mom who was about thirty-five, I would guess.
While his mom was quite attractive, I never particularly looked at her that way, she was simply my best friend’s mom and that was that. Now, that doesn’t mean that I never thought about girls and women and sex. I was sixteen. But a very inexperienced sixteen. Not even a feel of a girl’s breast.
The particular night in question, it was during the summer and after playing some computer games and watching TV, Gordon and I went off to bed. As I said, I had my own room at Gordie’s and was soon drifting off to sleep. It had begun to rain softly, one of those summer rains that start slowly, then can pick up rather quickly.
I heard footsteps in the hallway, then my door opened and Mrs. Foster came in and went over to pull down the window as it had begun to rain rather harder.
She walked over to my bed and bent over to pull the sheet down to the foot of the bed. It was a warm night and I just figured that she was making it more comfortable for me.
I lay there on my back, wearing my usual boxers to bed, as she put her hand gently over my mouth and whispered, ‘Shhhh, Greg, it’s okay, just Gordie’s Mom.’
I couldn’t really see much but I sure felt it when she pulled my boxers down, then off my feet. Her hand took hold of my dick which was suddenly being called to action and began rubbing me up and down.
I didn’t dare move, I just was frozen. I mean, it felt good, oh, really good, but it all happened so quickly and unexpectedly that I just didn’t know what to do. She leaned over and whispered, ‘It’s okay, Greg, don’t worry. Do you want me to make you cum, make you feel good?’
My heart was pounding and my breathing heavy as I whispered, ‘Yes.’ and she bent over and, in the darkness, I felt her wet lips slide over my dick as she began to suck me.
I just didn’t know what to do, so I just lay there doing the only thing I knew to do, just lay there and let her suck me off. Her hand reached under and cupped my balls right as I began spurting my cum into her mouth. I have never, ever felt so good in my life. Gordie’s Mom raised up and gave me a soft kiss on the mouth, her tongue probing me, as her hand slowly rubbed my oh, so happy dick.
Here I am, in bed at my best friend’s house, his mother has just given me a blowjob and is now kissing me very sexily as she plays with my dick.
‘Did that feel good, Greg?’ she asked softly.
‘Oh, it felt wonderful. I’ve never felt anything that good ever.’
‘Would you like something even better?’
‘I don’t know, I’ve never done anything like this.’
‘That’s all right, I’ll show you everything. Let me get more comfortable, okay?’ and she stood up and, in the dim light, I could see her raise her nightgown over her head and drop it on the floor.
I felt the bed move as she got in with me and laid down along side me. She took my right hand and placed it on her breast. I thought my heart would stop. It was so soft and nice and I rubbed my thumb across her nipple.
She raised up and led her nipple right to my mouth which eagerly took it in to suck. Her soft hand wrapped around my dick and began moving up and down on me, oh, this was heaven, I was nervous, but it was heaven, nonetheless.
‘Don’t worry, Greg, everything’s all right. We can just enjoy each other, okay?’ she whispered as she pulled me up over between her outspread legs. She reached between us and gripped my dick and led it right up to the middle of her legs.
‘Go, ahead, Greg, push it in, I want you to make love to me,’ and I pressed toward her as I felt my dick enter her. She was warm and slippery and soft inside as she pulled me by my hips back and forth in and out of her.
‘Is it good, Greg? Does it feel good to you?’
Truthfully, with the combination of pumping in and out of Gordie’s mom and the nervous state I was in, I was rather short of breath, ‘Uh, uh, yeah, it’s, uh, uh, really, uh, just wonder…uh…ful,’ I managed to whisper.
‘Mmm, it feels good to me, Greg, really good. I’ve missed having a man in my life like this. I was hoping you would want me, that you would want to fuck me, Greg.’
‘I just can’t believe this is happening, I mean, I just never expected something like this could ever happen.’
‘Are you glad it happened, Greg?’
‘Oh, yes, I could have never done it, you know, started something like this, I just wouldn’t have had the, well, you know, the balls.’
‘Well, Greg, I don’t have any balls, being a woman and all, but, I’ve watched you grow into a very desirable young man and I knew tonight that I just wanted you, I wanted you inside me. You’ve never done this before, am I right?’
‘No, this is the first time I’ve, um, you know.’
‘You can say ‘fuck,’ Greg. You’ve never fucked a woman before, or a girl?’
‘No, but it’s wonderful. I never knew how wonderful it would be.’
‘So, you like fucking me?’
‘Go ahead, Greg, go ahead and tell me, like a man would, like a lover.’
‘Oh, yes, I love fucking you,’ I murmured and she pulled me to her, kissing me as she wrapped her legs around my back and pulled me deep into her.
It was all I needed, my cum began spurting deep into my best friend’s Mom as she tongued my mouth.
I lay there over her, still fucking into her, she was rubbing my butt with her hands, my dick still pretty hard when she said, ‘Gordie is going to visit his Dad this weekend, Greg. You can tell your parents that you’re coming over to spend the weekend here and we can be together in my bed all weekend. Would you like to do that? We could fuck all weekend and I’d just love to suck your nice dick some more.’
‘All weekend? Like from Friday night to Sunday afternoon? The whole time?’
‘Yes, Greg. There’s so many things I can show you about sex. Things I’ll do to you, things I’ll have you do to me, things we can do together. All weekend long.’
‘And, Gordie will be away, I’d worry about him finding out, it kind of even scares me right now.’
‘I know, we’ll have to stop in a minute, just to be on the safe side but this weekend, we can just be naked with each other all weekend long and sleep together in my bed. Just like lovers.’
I did probably exactly what you would do.
So, on Friday, about six, I strapped my overnight bag on my bike and pedaled over to Gordon’s house.
As I walked up the steps, the door swung open and Gordie’s mom stood there in a halter top and shorts. She was pretty, what the guys at school would call a ‘MILF.’
As soon as she closed the door and I was inside, she swept her arms around me and kissed me as her hand went down between us and began rubbing on the bulge in my pants.
‘Let’s go upstairs and take your bag up. Then, we can change.’
‘Change?’ I asked as we entered her bedroom. Within a few seconds, her clothes were on the chair and now I had my first clear view of my lover for the weekend.
She stood about three inches taller than me, blond hair to her shoulders, her skin was creamy and pale white, her breasts, oh, her breasts, they were large with large, brown nipples, soft-looking, just beautiful, her waist was slim and her hips fuller and between her legs, her pussy was bare, no hair. And her legs were pretty, my dick was hard as a rock.
‘I shaved for you, Greg. Like my pussy?’ as she raised her right leg and put her foot on the bed. It was the first pussy I’d ever seen and it was pretty, perfect halves that I was to become very familiar with over the weekend ahead.
‘Oh, it’s really pretty, I mean, you’re pretty everywhere but your, um, pussy is beautiful.’
‘Come here, so you can kiss it, Greg. It’ll be the first one you’ve ever kissed, right?’
‘Yes, I’ve never done that before.’
‘Well, first, let’s get you out of your clothes, Here,’ as she began stripping me of everything I was wearing. As she pulled my briefs down, she took hold of me and started sucking the end of my dick for a minute.
As she raised back up, she said, ‘That should keep you interested for a while,’ and she got up on her bed, spread her legs wide and motioned me to get between her legs.
‘I’ve been dreaming about you licking my pussy ever since the other night, Greg. Make me happy.’
I got down and began licking up and down her slit and she reached down and spread her pussy lips open and whispered, ‘Lick me inside, Greg, up inside my pussy.’
I got my tongue as far up into her as I could. She was moaning and moving around which made me think that I’m doing something right. Then, she began groaning more and more.
‘Oh, Greg, you’re making me feel so wonderful. Oh, yes, right there, lick me round and round, oh, yes, it…UUHN, UUHN, oh, oh, mmm, oh, yes,’ and she pulled me up and began kissing me over and over.
Then, we just lay there in each other’s arms. It still felt strange to me to be with a naked woman, especially my best friend’s mom. But, it wasn’t as scary as the first night. I was slowly getting more and more comfortable in this new role in my life.
After a while, she said, ‘I think I’ll take you on a little tour of the female body, maybe go over some things that I’ll bet didn’t cover in sex-ed at school, okay?’
I quickly agreed and, as the sunlight was fading, she turned on the bedside lamp and had me sit in front of her between her legs as she showed me all around and inside. Her clit was the most interesting part and she showed me exactly how to please a woman there without hurting her. She also gave me some lessons on oral sex and lots of tips on fucking.
She described a number of sex positions and said that we would be trying many of them this weekend. I had an erection to end all erections.
‘Now, Greg, you gave me a lovely orgasm with your tongue and I want to give one to you with my mouth,’ and she got between my legs and bent over me, took my dick and began licking circles around the head.
I laid back just engulfed in such wonderful feelings, then she slid her mouth down taking me fully inside and sucking up and down. There was no way I was going to hold off with her doing this to me. And, as I knew would happen, it seemed that my whole body froze as I raised my hips and began cumming into her mouth. She sucked right on, just like nothing had happened, as I relaxed and just seemed to melt.
‘Oh, wow, that was the best, really the best,’ I panted.
She got up off my cock and moved down next to me, her hand rubbing me on my chest and said softly, ‘I loved sucking you, Greg, and when you started cumming, I just knew that it was because of me, what I was doing to you. You really had a good orgasm, didn’t you?’
‘I think that was the best one I’ve ever had. I just feel dizzy after,’ and I pulled her toward me and kissed her over and over.
We played with each other in bed, I was, by now, much more relaxed and comfortable with Gordie’s mom, I just touched her wherever I wanted and knew that she wouldn’t mind. In fact, she seemed to really want me to be sexual with her. So, I was trying to look at her more as a lover than as the mother of one of my friends. But, having known her so long as my friend’s mom, that wasn’t so easy.
‘I have some porn DVDs, if you want to watch them? Do you like that sort of thing?’
‘Um, I’ve seen some stuff on the internet, they’re pretty hot, yeah, I guess.’
‘Here’s a robe to slip on, I’ll put mine on too and we can go watch some.’
In the den, she got it set up and soon we were watching a couple undressing each other, kissing everywhere they took their clothes off of. Our robes were open and she was slowly stroking my dick as I rubbed my hand up and down her pussy.
‘See how he flicks his tongue on her clit? See, right there?’
‘This is giving me some ideas. Is that something you think you might like?’ I asked.
‘Oh, even watching it is making me hot. I love oral sex and anything you do to me like that will make me very happy, Greg, very happy.’
‘Let’s see if I can get some more ideas, then,’ and we watched as the woman in the video got up over him and started sucking him off. She looked like she knew what she was doing but she really didn’t look any better at it that what I just had a while earlier.
‘Watching this reminds me of having your cock in my mouth, Greg. And how sexy it felt when your cum started spurting as I sucked you. That was good, huh?’ she asked as she rubbed the precum around the head of my cock with her thumb.
‘It might have felt sexy to you when I cummed in your mouth but it was heavenly when it happened to me. And, you’re prettier than the woman in this video.’
‘That’s very sweet, Greg. I’ll have to think of someway to make you happy for being so nice to me.’
‘But, you’re the one being so nice to me. I mean, you can have any man you would want.’
‘Oh, Greg, don’t you see, I want you. I’ve watched you when you would come over to see Gordie. You’re a very handsome young man and you’re very nice in bed. I just knew you would be.’
‘But, I’m just sixteen and you must be used to men older than me. I’ve never done hardly anything with sex.’
‘Oh, Greg, you’re such a charming young man. Remember, you gave me a very nice orgasm the other night and a lovely one tonight. I suspect there will be many more this weekend. I just love the fact that sex is all new to you, it makes me want you even more. So relax and be happy we’re together like this.’
Well, I guess I couldn’t argue with that, it made sense, I guess, and I was sure better off than most guys my age, that’s for sure.
The couple in the video were now on top of each other, he was turned facing away and they were both sucking each other.
‘That’s sixty-nine, right?’ I asked and she told me it was. ‘Can we do that?’
‘Right now, Greg?’
‘I’m sure ready after watching this and after you rubbing me there,’ I said as I nodded toward my dick.
‘Do you want to do it here on the floor or up on my bed?’
We decided to go back upstairs and I followed her up the stairs admiring her nice butt which had her pussy peeking out from underneath. It just made me want her even more.
The video showed the woman on top and so I just automatically laid down on the bed as she got up over me and lowered herself down until her pussy just touched my mouth. As I was putting my tongue forward, a warm, wet sensation slid down over my dick, oh, it was wonderful, so, so, good.
I began licking up and down her slit as she sucked me. Oh, did I love this. This was sex, sex, for sure. I heard her moan a few times and reached up to pull apart the lips of her pussy and got my tongue up inside her and licked all around in a circle.
It was obvious that she really liked what I was now doing, she was moaning loudly and twisting her hips around as I tongued up into her. Then, I moved my mouth to her clit which my tongue could feel and I began sucking it as I put two fingers up inside her.
Her head pulled up off my dick as I heard her orgasm, ‘Oh, Greg, oh, OH, OH, UHH, OH, oh, that feels so good, do it more, oh, more, please, mmm, more, yes, yes,’ and she went back down and sucked me on.
I did exactly what she wanted, I licked and sucked and probed her until she had a second orgasm. Then she sucked the cum right up out of me, I almost fainted when I cummed, it was so hard and strong. I have never had a cum quite like that one, it was enormous. Sex was so good and Gordie’s mom was fantastic at making me cum.
She turned around and held me in her arms, kissing me, tonguing my mouth, pulling me tight to her.
‘Oh, Greg, you are such a wonderful lover. You’ve made me feel so wonderful. Did I make you feel good?’
‘I never knew anything could feel all that good. It was just the best.’
‘There’s lots more ahead for us this weekend, Greg, lots more. Right now, let’s just snuggle together and enjoy each other’s bodies.’
I sure was, I was running my hands all over her, her’s was the first naked female body I’d ever been with and I wasn’t about to lose a chance like this. We laid like this, kissing some, feeling even more, rubbing against each other, it was great.
‘You seem pretty hard, Greg, think you’d like to make love to me?’
‘Oh, yes, I just hope I do it right.’
‘There’s no right or wrong, Greg. You’ll be fine. You did it really well the other night.’
She pulled me over on top of her as she spread her legs wide. I thought my dick would burst I was so eager to be back inside her again. I got up on my knees and pressed my cock right inside where is was all nice and wet and warm.
‘Oh, yes, it’s just as nice as the other night. Mmm, it feels so good. It’s wonderful doing this with you.’
‘Yes, Greg, and we have all weekend.’
All weekend, sex all weekend long. Wow. A sixteen-year old guy’s dream come true. This was heaven as far as I was concerned. Her pussy inside felt so good as I went in and out, just so much better than jacking-off.
I was glad she had sucked me at first because I wanted to get her to have an orgasm and knew I had to last a while to do that.
‘Mmm, yes, Greg, you’re doing fine. You are a wonderful lover,’ and she pulled my head down and kissed me hard with her tongue swirling in and out of my mouth. What a wonderful situation to be in. A whole weekend of sex.
‘Just push in hard, Greg, then stay right there and let me do it.’
I pushed my hips forward, pressing as far into her as I could and she began circling her hips around making my cock feel wonderful.
‘Oh, wow, that feels really good. I like this, the way you’re doing it.’
‘There’s a lot more, Greg. This is making me feel really good, too. We’ll be trying lots of things this weekend, this is just one of them.’
‘You’ve sure got me close. It feels great, really great.’
‘Oh, honey, you’re making me feel good, just like I was sixteen again. That was my age when I first had sex. Rodney Hicks was his name. He was beautiful when I got him naked. Just like you, Greg, just like you. I sucked him and he was mine forever. He just wanted it all the time. Well, until I let him in my pussy. Oh, then, that’s all he wanted, well, no, he still liked me sucking him. What a boy. But now, I have a new boy and I love to suck him and fuck him even more.’
‘It sure makes me happy, this is wonderful. Especially, doing this, going around like this.’
‘Oh, it’s got me right there, oh, push in me, Greg, push hard,’ and she tensed and went up and down on me real fast.
‘UUNH, UUNH, OH, OH, Greg, oh, you make me feel so good, Greg…just wonderful. Give me your cum, honey, oh, fill me full, do it,’ and it was as if my whole body seized as I arched forward, thrusting deep into her as my cum flowed inside her once again. Oh, it felt so good.
I drooped over her as she held my head and kissed me, still moving under me, still making me feel good. Then we lay there, me over her, tight in each other’s arms, my dick still hard inside her as she whispered, ‘I’m so glad I came in your room the other night. I was just so wanting you, wanting you like this, in my bed, your cock in me like it is right now. Oh, I feel it inside me right now, it’s wonderful, Greg, just wonderful.’
I did roll off her after a bit and we snuggled and kissed and felt each other for quite a while. Being sixteen, I was soon hard again and she whispered, ‘I’d love to suck your nice, hard cock, Greg. Would you like that?’
Without answering, I swept the sheet back as she got up over my flagpole cock and began rubbing me all around my abdomen and pubic area as she took me in her mouth.
I reached up to rub her butt and found her wet pussy peeking out between her thighs. I started rubbing it up and down as she spread her stance so I slid a finger up into her as she sucked on me.
‘Mmm, mmm,’ she moaned as I rubbed my finger in and out. Her sucking was so good. I was breathing hard, knowing I was getting closer and closer to cumming, then, my cock exploded in her mouth.
‘UUH, UUH, OH, oh, mmm. Wow, you do that so good, it feels so good,’ and she turned around and held me as we kissed again and again. Oh, she does make me happy, so happy.
‘It’s getting late, Greg, we need to get us some sleep, we can’t just be having sex and more sex, now can we?’ she asked with a smile.
‘Oh, why not?’ I asked with a grin.
‘There’ll be more sex, Greg, lots more. It’s something that I’ve just never gotten enough of. Remember, if there’s anything you ever want, all you have to do is ask me, I’ll do it for you. Okay?’
‘What if I asked you to suck me again? Right now?’
I know, I know. But I’m sixteen.
She didn’t answer except to get back up over me and begin licking around the tip of my dick.
‘Oh, that feels so good. I know you just did it but it still feels good. I’ll do it to you after if you want,’ and she sucked me on and on until my semen burst into her mouth once again and I slumped back, happy and contented.
She turned around and held me in her arms as she kissed me all over my face and neck and chest. Then, as we snuggled together, she said, ‘Do you still want to do oral sex on me, Greg?’
‘Oh, yes, if you want it.’
‘I’d love for you to make me happy that way,’ and she pulled the sheet aside and spread herself as I moved up to in between her legs and began licking her. She had her legs open very wide as I tongued up into her.
‘Mmm, Greg, you make me feel so good, I really feel wonderful when you do this to me, really wonderful.’
Her pussy was really wet, I kept licking it off and there would just be more each time. It was making her feel awful good, though, the way she was moaning and writhing around. I decided to lick up onto her clit and suck it some, it was sticking out a little, and as I did, I put a finger up into her as well.
‘Oh, Greg, Greg, that feels wonderful. Oh, you make me feel so good, I just knew you would be a wonderful lover. Suck right there, oh, yes, right there, UUNH, UUNH, UHH, uh, uh, oh, Greg, oh, Greg. Come up here, Greg, so I can kiss you and hold you. I’m so happy, you’ve made me so, so happy.’
We drifted off to sleep in each other’s arms, warm and naked and blissful. I was exhausted and, I think, emotionally drained from my new role as lover to a grown, adult woman. But I was loving it.
The rest of the weekend? Well, there’s no other way to describe it except as the most sex-filled weekend of my life. I was sixteen with a raging libido but it was completely satisfied every minute of every hour of that weekend. She kept my testicles drained like no other woman since.
Did I fall in love with Gordie’s mom? I was sixteen, sure, I did. At least whatever love is to a sixteen-year old boy. We continued our affair until I became engaged to Julia when I was twenty-two, that was fourteen years ago. My wife says I am the perfect lover: considerate, skilled, assured, thoughtful and tender. She’s met Gordon’s mom and has thanked her for showing me the way to being a generous lover.
Thanks, Mrs. Foster. From us both.