Lucky Over 40 Ch. 04: The Waitress

"No, I want to touch it," she replied, a little shyly, then continued teasingly, "and maybe do something else with it, Ok?"

"Hey, like Jill told us both, I'm all yours to do what you'd like to do, so you don't really need to ask," I reminded her. "And believe me, I'd really like it if you touched my cock, and maybe do something else with it, even though I don't know what that would be."

As I spoke, she took hold if my nearly throbbing cock. She bent down, looking closer, and said, "I wanna taste it. I want it in my mouth. I'm gonna suck on it some, and play around some, like I never really got to do when my boyfriends had me blow them. And I may want to try some stuff Jill told me about." She sat on a chair and pulled me over with my cock right in front of her.

"I have to remember to thank Jill for being such a fount of information," I said somewhat sarcastically. "But all that sounds good to me," and she started to cup my balls with her other hand. "Do you want me to take off the pouch, or to lie down, or...," but her mouth was on my cock before I finished. Her hand came off my cock and held my ass, with the other rubbing my balls and starting to slide between my legs, which I parted some more for her. That hand went to my butt crack, the other one pulled one cheek aside, and a finger searched for my anus.

I tried to part my legs more, to better expose my ass to her. Her mouth was good at pleasuring my cock head and her tongue explored all around from its "eye" to around the ridge. I began to moan a little, and lightly stoke her hair. "That feels really good. You're very good at this," I told her. "I hope you're doing what YOU want to, and enjoying it."

"Um hum," she moaned back in agreement. After too short a time, from my perspective, she withdrew her mouth, then her hands, and stood up again. "That was nice, and thanks for not pushing my head down farther, like my boyfriends would. I wanted to see what that felt like to do my own thing, and it was nice. Ok, I've been getting wet since before you got here, and I think I'm soaked now, so I wanna do something about that. I want you to do something for it. Jill says you're good at it. Would you eat me? I'd like it if you would eat me and make me come, please."

Sweetie, it would be my absolute pleasure to do that to, and for you," I said earnestly, I really want to see what treasurers those shorts were hiding, and I never met a nice wet pussy I didn't want to eat. "Do you want to lie down, or sit in the chair, or what? Don't just stand, I don't think you'll be comfortable enough, or did Jill already tell you that, too?"

"Sorta," she replied. "She told me she had to sit or she woulda collapsed when you did it that way once. I think that coulda been the first time you licked her butt. Will you do that for me? It's one of the things on my list, ya know?"

"Yeah, I know, and I don't think there's anything Jill didn't tell you about us," I said with a half laugh. As I fully removed the thong pouch thing and took off my socks, I said, "I really would love to do that for you. How about you sit in the chair again. I think that should work well. But first I need to get you out of those shorts. Honestly, I've been wanting to do that since you walked up the stairs in front of me. Your ass is very nice. And when you told me you were wet, my mouth started to water." As I said all that, I knelt in front of her, and started to pull down her shorts.

I saw she had no underwear on and her short, curly, dark pubic hair came into view, trimmed so that most of her labia was nicely visible. My cock started to twitch at the sight and scent. She saw my involuntary reaction, gave a little sound of surprise, smiled, and asked if she caused it. "Yes, sweetie, you did, you're hot, and your bush is beautiful. Sit down near the front of the chair, and we'll put your feet up on the edge of the seat. Now open your lovely legs so I can pleasure you, and myself in the process." I helped her get in a comfortable but accessible position. I knelt on the floor, in close, and she watched me smelling and adoring the beauty between her legs. My cock was sticking straight up and starting to throb, she was probably watching that, too.

I leaned in with my hands on the bottoms of her thighs, near her ass, so my thumbs could part her pussy, or move to spread her ass. I started to kiss the inside of her thighs and opened her pussy lips with my thumbs. She moaned as I licked up her slit, pushing my tongue between her lips, then tickling her vaginal opening while my hands rubbed and groped her ass. Soon I was trying to push my tongue as deep into her as I could, wishing again that it was longer. Her juices tasted delightful and seemed to be flowing. I kissed and licked all around, savoring all of her.

After a couple minutes, she was trying to push herself onto my face, but her feet slipped off the chair. I help her put them back without interrupting the work my mouth was dong on her pussy, but it disrupted my attention to her ass. My hands returned to her back side, this time by spreading it with my fingers in her crack, using one to rub circles on and around her hole. My mouth moved up her pussy until I found her clit with my tongue, she quivered and her feet came off the chair again. This time I lifted them over my shoulders. She had slipped off her sneakers, but was still wearing socks, which felt nice wiggling around on my bare back.

My mouth was still at her clit, and I sucked it between my lips. I accidently brushed my teeth against it apparently causing her to shudder and moan loudly, but in a pleasant way. I swirled my tongue around it, in apology for my teeth and she dug her heals into my back in an attempt to pull herself tighter to my face. Meanwhile, my finger was back at teasing her asshole. "Oh yea, I like that, I really like that," she said, in a breathy kind of voice. I didn't know what exactly she was referring to, but I kept up everything I was doing, just a little more intently.

She pulled off her top, and I think she began to rub her breasts, but I couldn't see clearly while my face was still buried in her snatch. The idea of it, though, spurred me on and I left her clit, moving my mouth down, while parting her ass more with my hands. My tongue, and really my whole mouth, was thoroughly lapping at everything as I went down her vulva, across her perineum, and towards her anus, which was my final target. I took my time getting there.

She didn't seem to mind my change in attention at all, saying, "Oh this is really, really good, but I wanna continue it up on the bed, `cause I also want your cock in my mouth some more. Um, oh fuck, Oh, OH" she exclaimed as my tongue started to near her butthole. "Ok, we'll... Oh Yeah, we'll stay here... Yeah, do that more, oh wow..." I had started to tease and poke her asshole with my tongue, while my fingers explored her pussy. "Oh, yeah, baby, yeah, lick me there. And push your fingers deeper, yeah, Yeah, fuck yeah," she encouraged, as I found her g-spot and started to rub. "Fuck! Fuck me with your fingers, and your tongue, push it in, FUCK, YEAH."

After another couple minutes she exclaimed, "I'm getting close, make me come baby. Make me come. Oh! You're making me ka ug ug UG UM UM!" She moaned loudly and tensed up her legs, her feet were trembling against my back, her hands held my head so tightly into her ass that I had to pull my fingers from her cunt, which might have been a good move right now anyway.

When she relaxed, I gave her ass a couple final licks and a kiss. I licked up across her pussy and gave her another kiss near her clit. She shook a little, and released her grip of my head. I started to lean back and her legs came off my shoulders. I stood, taking her hands and pulling her up, into my arms, kissing her fully with open mouth. She was nearly limp, but held onto me around my neck and put her tongue in my mouth. After a moment, I picked her up with my hands under her nice round ass, she wrapped her legs around my waist, and I carried her to the bed, my cock occasionally rubbing against her as we moved.

We climbed into bed and cuddled. I asked her if she could check that off her list, and she said, "I'm moving it to the list of things you're gonna do to me again. That was really something. I don't know if I've ever come like that. No one ever took their time or paid attention to me like that, or, I don't know what, but it was great. Thank you!" She kissed me again, deeply, playing with our tongues. Her hands were roaming all over, playing with my chest, my back, my ass, my cock, and my balls.

Eventually she broke the kiss and took hold of my cock again, saying "I think this guy needs something now. What should I do with him? I wanted him in my mouth again, but my pussy's feeling empty and needs filling with more than your fingers. Since this is supposed to be about what I want, I think I'll put him to work. Fuck me, please!" She seemed much more relaxed and less shy now, and so was I, in part because I was horny as hell.

"I'm yours to do with as you want, and am happy to oblige," I said. "Do you have a preference as to position? Would you like me to do most of the work, or to you want to ride me so you have control of it all? What's going to get you off best, or what do you need, or want, more experience with?"

"Hmm, I never had to, or even got to, make that decision before," she mused. "Let's start out with you doing the work, that's what you're here for isn't it? Climb in there between my legs and shove that bad boy in my pussy. I should be plenty wet enough." And she bent her knees, opening her legs and stretched out her arms toward me, welcoming me in. I wasted no time getting into position and my cock did slide right in as I embraced her. She wrapped her legs around my waist again and said, "Oh, yes, that's good. I felt him tickling my twat when you were carrying me, and it was nice, but he feels much nicer inside. Push him up farther, baby, push him right in and fuck me."

I was very happy to do as she instructed, and slid forward, gently burying myself in her center as I snuggled on top of her. I wanted to kiss her again, but didn't know if she would want it; this wasn't about me, or even "us," it was supposed to be what she wanted. So I just watched her and said, "You feel really good, and you certainly are nice and wet. It feels wonderful sliding in and out of you. You're quite the hottie, with a really hot, wet, wonderful pussy."

"I bet you say that all the women you get loaned out to," she teased. "Jill was right that your cock feels really good in there, and it'll probably feel really good in my mouth later." Right now, though, just kiss me, and fuck me until you fill me with cum. Then I have something else that's on my list."

"What didn't Jill tell you about me or my cock?" I wondered out loud. "Anyway, I really do need to thank her for loaning me out to you, and for arranging so this could happen. It's been fantastic so far."

"She didn't tell me how much better your cock would be than any of my boyfriends," she said, and I didn't know if she was teasing or what. Then she reminded me of her last instructions, "But it's really time to just shut up and kiss me, and keep fucking me with that really nice cock. Push it in `till your balls hit my ass. Uuummm." And she pulled her head to mine and kissed me so well that I swear my cock grew some more.

I picked up the pace of my sliding into her. She grabbed my ass, pulling me into her more, and also pulling my cheeks apart. The cool air hitting inside my crack was arousing, and I moaned a bit, which made her grope my ass more. Eventually her finger found my pucker and started to tease it. That got me wiggling and squirming some on top of her, which also made my cock wiggle inside her, and got her moaning back at me. She broke the kiss and said, "So, you do like your ass played with, don't you, bad boy?" She kept fingering, I moaned and started kissing her jaw, then kissing and sucking her neck, working up to her ear, pushing my tongue into it. All the while she moaned, I fucked, and she fingered.

After a while her finger cam out of my ass and she said, "It was fun to feel you react to my finger, and I'm gonna do more of that with you. But, it's time to get serious about working that cock some more. It's time for me to do the driving so roll over lover, and let me get on top." She started to roll, so I did my best to follow. Doing that with a guy's cock still inside can be kind of dangerous, and lead to a very unpleasant injury if you don't move together correctly. I guess I was worried because I pulled out before we had moved too far.

"That's not good, he isn't done yet," she chided. Get on your back so I can put him back where he belongs," and she quickly straddled me as I turned on my back. She took hold of me and slid down on my eager dick. Then she rocked and bounced and wiggled, a little slow and first, but soon quite a bit faster than I'd been going. "Yeah, that's good, he's working me nicely this way," she giggled. "Such a very nice cock. Rub my nipples, Rob, since you're supposed to be giving me what I need right now."

"Sure, I'd love to," I replied cheerfully. "I didn't get much of a chance to have a good look at these beautiful breasts until now. They were out of view with my face buried between your legs, or with them pressed between us, rubbing against my chest. I got a hint of them with your shirt on, and was looking forward to getting to say hello. They feel as nice as they look, and I love these erect nipples," I said after briefly fondling her tits and now rolling the nipples between my fingers. "I bet they taste great too! I want to lick and suck them, and tease these hard nubs with my tongue."

She leaned forward, took one breast in her hand and brought it to my mouth. "If you insist, I guess I can let you," she teased. "You can bite them, too, carefully. They're very sense-a-TIVE, OH! Yeah, like that, and suck on it too," she said as I gently pinched the other nipple with my fingers. After I had sucked on each of her tits for a while, she said, "I'll have to get you to give these ladies lots of attention later on. Right now I need to concentrate more on riding this cock, but keep using your hands on my tits," and she sat back up. My mouth was no longer able to play with her nipples, but I had another idea.

As I continued to fondle a breast with one hand, my other hand slid behind, into her ass crack, and began to tease her hole once more. As soon as I did, she squirmed on my cock and said, "Oh, you dirty boy. That was sneaky. But since you're there, can you push it inside this time? Get some pussy juice on it and slide it in? Yes! Oh that's nice! Can I get one in you, maybe, just about, but not very deep," she said, reaching behind herself and fingering my ass. "Does it feel good, though? You feel good in me, but not quite as good as your tongue did, oh I liked that! You'll need to do that some more, later."

She was tickling my asshole, and squirming on my cock and I was getting pretty close to going off. "Yes, it all feels really good, and it's really hot, and you're really hot, and I want to do it all again. You've lost your shyness and this side of you is really turning me on," I told her.

A few minutes later I said, "I think I'm gonna come pretty soon if you keep doing all that." By now I had to give up on playing with her breast and had both hands at her ass. She was leaning back more and trying to push deeper into my ass, and squirming more on my cock. It was all getting me closer and closer.

"So you like my naughty, dirty girl side, do you? Good, `cause I want you to come. Come in me hard, fill me with your spunk. Do you like my finger in your ass, like I do? Do you like me riding your nice hard cock? You feel good inside me. I want your cum inside me baby. I want your cream inside me and then we'll have some more fun. Do it baby, come for me, fill me up. Fuckin' fill me with your cum." She bounced and wiggled on me more, working at pushing her finger deeper into me. Though the position wasn't good for deep anal penetration, she was tickling my inner sphincter and it felt great.

Finally, I felt the orgasm build beyond the point of no return and called out to her, "Yes Dee, I'm coming, I'm COMING, URGH, AHHH, Oh Yes, FUCK ME!! UUmmmm, Yeah, oh lover, yes, that was good." I had felt myself shoot at least a few times inside her, and now was feeling spent, though my cock was still hard enough to stay inside her.

She realized I had shot my load, and decided to try another item on her list. She pulled her finger from my ass, leaned forward and slid off my cock, then crawled forward and brought her legs by my head, holding her pussy above my face, visually teasing me with it as she spoke. "That felt great, but I didn't cum again. I think you need to fix that. I think you need to finish me off and clean me up at the same time. You need to lick my pussy and suck my clit and whatever it takes. You can do that for me, can't you, baby? Do you want to do that for me? Tell me you want it, baby." She was getting into being charge, and there was not a hint of shyness any more.

"Yes, I do. I want to make you cum. I want to use my mouth to make you cum, right on my face. You're so hot and you taste so good. Let me eat you, sweetie," I pleaded. I knew she was getting into this, and that she really needed a guy to want to make her happy, to get her off the way she wanted, no matter what that was. And I didn't really mind. I wanted to make her come again, I wanted to give her what she wanted, I wanted to taste her pussy again, I wanted to lick her ass again, to get her to squirm with pleasure again.

It wasn't a control thing, or about dominance or submission or humiliation, none of that. It was about giving this hot, young thing a good time, like she did for me, and, about the arousal that her arousal brought out in me. Did I want to eat my cum from her, not particularly, but I didn't really mind it either, it was just another sexual fluid, part of the territory so to speak, and it would be mixed with her juices that I really liked. And well, there was that pineapple juice thing that I had yet to see a result from personally.

While I was thinking about all that, she lowered her snatch to my mouth and rubbed it around. I put my tongue in her, or on her, whatever she was presenting to me. My hands groped her butt and when a thumb touched her anus she scolded, "Don't put that in there, leave that for your tongue. You can finger me later." And she slid forward, presenting her ass, and pulling her cheeks apart to give access to her hole. "Lick me baby. See how far you can get that tongue in me now," she gently commanded. And I did my best to comply.

Sex juices were smeared all around her butt, hers, mine, ours, and I did like the taste of it all mixed together. I pushed as hard as I could with my tongue, and moved it in and out, tongue fucking her ass. "Yeah, baby, do me, do me in the ass, do my ass with your tongue. Fuck yeah." She was also rubbing herself with her hand, sticking some fingers in her pussy as she rode my tongue. Cum was starting to come out with her fingers and was dripping on my face, my eyes were now closed and I felt it on them.

"Oh that feels good. Oh fuck, yeah. Lick my ass! If you do a good job I may get you to fuck me in the ass with that beautiful cock of yours sometime. Would you like that, baby? Do you want to fuck my ass? Your cock might feel really good in my ass. It felt really good in my pussy. Oh yeah, and it's going to feel really good in my mouth. I want that cock in my mouth," and she swung a leg over me, turning herself around, leaning forward and taking hold of my cock.

She positioned her pussy over my mouth again and said, "I'm so horny, and I want to come, lick me and suck my clit and make me come. Make me come while I suck your beautiful cock. Suck your cum from my cunt and I'll suck some from your cock." Then she leaned all the way down and slowly slid my cock between her lips and deep into her mouth. She slid back and started bobbing her head while she sucked on me. She moved her pussy on my mouth and I ate her, until she moved so her clit was on my lips.