Back over the winter break from school, I was staying with my girlfriend, Jean, at her house and she was off doing something that day, so after I'd taken a shower, I went back to her room and laid down, feeling rather horny which seems to be a constant state, according to Jean, so I took cock in hand for some entertainment.
Not having my laptop with me or any Playboys or such, I just closed my eyes trying to imagine all sorts of hot women as I stroked up and down.
It was really feeling good when I heard, "Ryan, I was wondering ... oh, sorry," Jean's mother said as I looked up and saw her framed in the doorway. It had been so sudden that I didn't have time to cover myself, I just figured she would quickly depart.
But no, she stood there, beginning again, "Um, I was wondering if you and Jean will be here for supper tonight, that's all."
"Um, yeah, I think so," I managed to choke out as I laid there gripping my cock, having no idea what to do. She seemed totally nonchalant about it but I was sure uncomfortable, though there was also a feeling of sexual exhilaration having her stand there watching me.
"Well, I was thinking of either roast chicken with roast potatoes or, maybe, manicotti. Do you have a preference?" she asked just like we were sitting in her living room having a nice discussion.
"I ... I like both, either one is fine," I managed as I felt my cock deflating in my hand.
"Look, Ryan, don't mind me, it's nice to see a healthy young man, go ahead and don't lose the feeling, go ahead, I'm fine with it."
I figured, what the hell, and began stroking again.
Now, my girlfriend's mother was over forty, in her lower forties, I think, and quite nice-looking, more or less an older version of Jean.
"Well, if I do the chicken, we can have green beans as well. Do you like them?" she asked as I stroked myself.
"I, yeah, they're fine."
"I'll fix a salad if you'd rather have the manicotti, I know Jean loves them both," she said as I slid my hand up and down.
"I've also been trying some spicier things lately, might fit with what you're doing, Ryan," she laughed. "Do you like curries, Indian food and such?"
"Yeah, it's good, so is Mexican and Thai. I like hot stuff."
"You're looking kind of hot stuff yourself, Ryan. Are you close? I'll stay if you are. If you don't mind."
"I ... I guess not, um, fairly close, I guess," I squeaked out as my hand kept moving.
"I have a brother, so I know how guys are, don't worry. I think I'll do the manicotti and salad. We can have a nice red wine with it. Jean tells me you drink beer sometimes, do you like wine, too?"
Now, there was a real oddness to this as you can imagine but it was also really turning me on to have a woman, a pretty and sexy woman, watch me masturbate as we talked about food and wine.
"Yeah, wine's good. Like a Cabernet or something?" I asked.
"I've got Cab, several bottles, and some Merlot and some Pinot Noir. Do you have a preference?"
I was almost about to cum and was trying to decide whether to tell her or just let it happen.
"I don't know that much about wines but I know I'm just about there," I groaned as arcs of cum went spurting up as I slid my hand up and down gripping tightly.
"Oh, my, you are certainly healthy, Ryan. That's quite a display. I guess I'll leave you to clean up," she said as she picked up the box of tissues from the dresser and handed it to me. "We can talk about the wine later," she added, smiled and left the room.
I laid there astonished. The whole thing was surreal. Jean's mom, Teresa, just came in as I was jacking-off and stood there and had a conversation until I cummed. I was still hard as a rock and so turned-on by the whole thing that my cock got an encore.
I fell asleep after my second cum and awoke when Jean stood there in the door laughing.
"Oh, look at you, I can just guess what you were doing before you fell asleep. Well, get dressed, I'm gonna help Mom stuff the manicotti," she said and went downstairs.
Since it was hard again, well, look, I'm twenty years old, it gets that way, I gave it another thrashing and then got dressed and went down to see how supper was progressing.
As I neared the kitchen, the aromas were wonderful, I just followed my nose.
"Well, here he is, Mom and I were just talking about you. You must have put on quite a show for her, she's right impressed with my choice of a male partner."
"Oh, that, yeah, um, yeah, she kind of walked in and, well, I stopped but she kept asking me things and said for me to go ahead, so, well, I did."
"I guess you did. She tells me that you certainly seem virile and that she's pleased that you are comfortable enough here to just continue what you were doing. I knew you would make an impression on my mother but, well, it wasn't exactly what I was expecting."
"Now, Jean, be nice to him, I enjoyed every minute. It's not something I get to see every day, you know," her mother said, then added, laughing, "or even every five years, unfortunately."
"Oh, I'll bet Ryan would give you another showing, wouldn't you, hon?"
"I think maybe that was enough for your mother," I told my girlfriend.
"Hmm, I think I'll be the judge of that, Ryan. Actually, I went and had to have a little private time myself. It was quite erotic, if you want to know the truth."
I laughed, telling her, "I'm glad I was able to help."
"Well, it's not often I have anything so exciting to think of in moments like that."
"Maybe we should have him do it again, for the both of us. What about it, Mom? You up for seeing him do it again?" Jean asked her mother.
"Well, dear, it seems that Ryan should have some say in that, don't you think? Ryan?"
Now what was I going to say to that? Then, I thought of the perfect answer, "I'll do whatever you two want me to do."
I have to tell you that masturbating in front of my girlfriend's mother, while scary at first, it became a huge turn-on. I loved her watching me, especially when I started cumming. I never thought I might be an exhibitionist but now I was seeing that I was sure looking that way.
"Mom?" her daughter said.
"Do you need anything, Ryan, hand lotion, I've got canola oil right here, something else?" Teresa asked. It was looking like I was going to masturbate once again for my girlfriend's mom.
"I can't wait to see this, sorry I missed you two this afternoon but this is going to be great," Jean said as her mom handed me the bottle of canola oil and I pulled down my pants and briefs, sat down and poured a small pool of the oil in my palm and used the fingers of my other hand to spread it up and down my shaft.
Then I looked up at them, grinning, as I began to stroke up and down while they watched. I'd never masturbated for anyone, for anyone to watch, until today but I was really liking it. I'd never even done it for my girlfriend, until now.
I usually have hand lotion nearby to use and the oil was somewhat slipperier and felt really good. Having an audience, especially Jean's mother, was greatly adding to the feelings I was having and it wasn't long before I was getting really close.
Then, I knew there would be just a few strokes more.
Spurts of cum went flying out the end as Jean and Teresa both began laughing and hooting.
"Look at it all," Teresa said.
"Yeah, and what you don't know, Mom, is he can keep going, oh, it's nice."
Jean tore off a paper towel and I used it to clean up the floor and my hands, then pulled on my briefs and pants.
"Well, that was quite a show once again, Ryan. Um, I think I'll take a few minutes upstairs if you two don't mind delaying our supper a bit. Just give me a bit, okay?" her mom said and left the kitchen.
"You know, Mom's by herself, she doesn't have a man in her life. Would you, um, would you think it awful if I suggested that you go up and, well, help her with whatever she's doing upstairs?"
That was a request I never saw coming. I stood there, my mind swirling, as I asked her, "Um, help her masturbate or something else?"
"Whatever she wants."
"You really mean it, go up and do whatever she wants?"
"I'll just pour myself a glass of wine, go have some fun with my mom, make her happy, Ryan," and she leaned forward and gave me a kiss. "Oh, our supper is in the oven on warm, take your time."
So, I trotted upstairs and went down to the end of the hall, knocked, then said, "Um, Jean sent me up to see if I could help you with anything. Are you decent?"
"Yes, now I am, come in, Ryan," she said and I turned the knob and went in. Teresa was on her bed, the sheet pulled up over her but it seemed that she was naked underneath. She looked good, her breasts rose under the sheet, looking like they were nice and firm.
"Jean sent me up to see if I could help. She said in any way you wanted, so I think that gives you a lot of leeway," I said grinning.
"She sent you up? For whatever I wanted with you? Am I getting this right? My daughter is lending me her boyfriend? For whatever?"
"Yeah, she said to take our time, dinner is in the oven keeping warm."
"Well, Ryan, perhaps I should ask if you'd rather back out of this. I am twice Jean's age, after all."
"I think you're quite pretty, Teresa. I not only don't want to back out, I can tell you this, I'm really turned on at the idea of us being together."
"Even sex, fucking?"
"Especially sex, yes," I told her.
"And Jean knows this and sent you up here to be with me?"
"She said you don't have a man in your life and that I should come up and we should have some fun together. She really did."
She slid the sheet away showing me her naked body as I began pulling off my polo shirt and undoing my pants. As I was pulling down my briefs, she was opening her legs for me and I crawled up between her thighs, bent down, kissed her pussy giving it a few licks, then held myself right up to her as we pushed ourselves together.
"Oh, I'd forgotten," she groaned as her eyes closed and a look of pure happiness took her over as I began moving in and out of her. "Yes, oh, wonderful, mmm."
I didn't have any experience with older women and didn't know what to expect. She was tight, however, just as nice as Jean, really, and she was an eager participant under me, moving this way and that, clenching herself as I went back and forth, generally adding her own spice to our lovemaking.
"Mmm, I'll certainly have to thank Jean for this, and, of course, you, too, Ryan. This is rather naughty but, well, quite lovely. I hadn't realized how I had missed a man inside me like this. I hope this is good for you as well."
"Oh, it's quite wonderful. You are a sexy woman, just like your daughter, I see where she gets it from," I said, looking down at my cock sliding in and out of her as she moved under me.
I had always thought that Jean's mother was quite attractive ever since I met her but I never ever for a single minute thought I'd be having sex with her, especially at the suggestion of my girlfriend. But here I was, stroking back and forth in her mother with her full permission and even encouragement. Wow.
"I'm beginning to not even care about supper, Ryan. Not even it if dries out and burns. This is quite wonderful."
"Well, we may have other times as well," I told her.
"If we do, I think that would be quite wonderful."
"I think I might be a busy guy, at least I'm hoping so. You're really amazing in bed. There should be guys all over you, Teresa, I can't understand why there aren't."
"You're the only one in a long time and, well, it is kind of a mercy-fuck, I suppose."
"Oh, you're wrong, so wrong. Believe me, I find you very exciting, you can feel what you do to me, right?" I asked as I pushed hard down into her.
"I supposed you're right, that's pretty hard to disguise and it's pretty hard," she laughed.
"Mmm, it is pretty hard and it's you, Teresa, who's making it that way. It's looking like maybe I have two girlfriends," I joked and she agreed.