Lucky Over 40 Ch. 10: Date with JJ

Finally, I fell into a rhythm of I pushing the Feeldoe in as my cock moved out, and vice versa. JJ slowly gyrated her butt around a bit, and moaned a little with each stroke. I began to add a little twisting motion to the Feeldoe as I slid it in and she seemed to like that. It felt a little strange against my cock, but in a good way. Then I remembered there was a vibrator in it.

I turned on the vibe and JJ held still for a second. I guess she realized what had happened and she pushed back into me harder. She wiggled her ass a little, saying "Ok, that's interesting, not strong, but it adds a little extra something. I felt it a lot more when I was wearing it and doing the fucking, I guess `cause the vibe is buried in the base." As I pushed it deeper in her she said "Oh, there it is, against my ass cheeks. Oh, and on my asshole when you burry it in me. Umm, that tingles!"

"Yeah, I remember that," I confirmed. "Right now, every time my cock head rubs past the lower part of this thing the vibrator really gets me, too. Uhhmmm"

After another minute or so I asked her, "Is this good, baby?" I was trying to make her come first. She had wanted my dick to screw her ass after the Feeldoe and I was hoping I could keep myself from coming in her pussy first, but I was worried it might not be easy to hold off.

"Oh yeah, stud. Reeealll goood," she moaned. She moved a hand between her legs and rubbed herself, moaning more. I minute later she dropped her head back down onto the bed and pushed her butt back into me harder. "Fuck, fuck, FUCK," she called out and then froze up, her legs trembling just a bit.

After a few seconds her whole body slumped forward, off my cock. She reached back taking hold of my hand to pull the Feeldoe out as well. "Yeah, that was good," she sighed, and slowly moved back up on her knees. "Ok, Rob, time to see how your nice cock compares. Lube it up and slip it in my backdoor."

I wasted no time grabbing the bottle and adding some more lube to the pussy juices already coating my cock. I pressed my cock against her open asshole and slid it in with very little resistance. "Oh yes, your head is definitely bigger, and it feels really good," she cooed. "Now fill me up with that thing."

I obliged, pushing my hard cock part way into her ass. "Ugghh, that's good, baby." She was slick, but tight and hot, and it looked so fucking sexy!

Her hand went back between her legs and rubbed across her pussy as I entered her. She pushed herself back, then pulled forward a bit and pushed back again until I was all the way in. Now she could fondle my scrotum with the hand between her legs. We both moaned as I moved in and out of her ass while she rubbed whatever she found between her legs.

"Yeah stud, that's feels good," she moaned. "Now fuck me good with that thing." It seemed she wanted me to fuck her pretty hard, so I pulled most of the way out and rammed back in fully. She moaned deeply, "Oohhh, yesss."

Her hand met me and began rubbing my balls. I pulled back and plowed in again. I started to pound her with full, hard thrusts, grunting with each one. She kept rubbing herself, in sync with my pumping, and began to moan louder, "Aaaahh. Yeah, fuck my ass."

I reached up and grabbed her tits, squeezing the nipples between the second knuckles of the first two fingers of each hand. My mouth gave her shoulders tiny bites. After a few minutes she was squirming and moaning constantly, as her hand moved franticly between her legs.

"Oh fuck, fuck. Fuck my ass. Yeah, pull my nipples. Oh Fuck, I'm gonna come. I need you to come, Rob. Come in my ass. Or on my ass, or... Or... OH! Fuck." She threw her head back as she cried out, "FUCK. Uurrgghhh." She grabbed my balls for a few seconds as she arched her back and froze. Then she exhaled with a grunt, "Uugmmm," throwing herself forward off my cock.

I wasn't done yet, and if she wanted me to come, and to be rough, well... I pumped my cock with one hand and pushed her over on her back with the other. I moved beside her on my knees, stroking my cock. She opened her eyes and watched me jerking off, a smile coming across her face.

"Oh, I like seeing you do that. Yeah. Gonna come for me? Where you gonna come for me? Shoot your spunk on my big boobs, Rob." She had a good plan and was pushing her big tits together, egging me on. It looked hot. I was very close and definitely wanted to cum someplace purposeful.

Suddenly I felt my cum about to explode, I leaned forward with one arm on the bed past her head and moved my dick just as it began to shoot, aiming it at her pretty face. She was looking at her tits and the first line of cum splashed right on her nose, covering it and her lips. She laughed, and closed her eyes and turned her head as the second shot coated both eyelids. She opened her eyes and lips, moving her face to catch the final shots in her waiting mouth, some landing on her cheek.

When it was done, I sat back on my heels and groaned with satisfaction. She chuckled and licked her lips, making a show of sticking her tongue out, saying, "Mmmm, that was tasty. Good for you, Rob! Better than on my tits. And you can still lick it off. Come on, lick your hot cum off my face, stud."

"That was my plan, baby," I said as I straddled her and bent down, licking her eyes and her cheek. I pinned her hands with mine as I leaned in and covered her nose with my mouth, licking and sucking the jizz from it. She giggled and squirmed beneath me until I moved my mouth to hers and kissed her deeply, pushing some cream in with my tongue.

I released her hands and moved mine under her shoulders, lifting and cradling her. She put her arms around my neck. When I broke the kiss she said, "Oh, that was bad. Fun, but bad. I know just what you deserve for it. I think it's my turn to fuck your ass now. How about that? You liked the Feeldoe the other day. Are you ready to feel it back there again?" she asked with a sexy grin.

"Well, maybe bad boys should get fucked by naughty girls. I guess that sounds fair," I teased back at her. Normally, I might have been ready for a short rest, but she had me going, even though my cock hadn't yet finished its reset. I was still horny and the ass play with her got me thinking that maybe I'd like some of the same. I was sure my prostate would enjoy her attention.

"I have to clean it off first, and need to clean you up too, before I can put either of those things any place else. Plus, I really need to pee," she said as she hopped off the bed. "Come on, stud."

Now that she mentioned it, I realized that I needed to pee, too, since my cock had relaxed. I followed right behind her. I hadn't seen her bathroom yet, and was surprised by the somewhat spacious walk-in shower with a bench. "That's a really nice looking shower."

"Yup, my former boss, and benefactor, had it installed when his health started to decline and his mobility began to go. He tore out the tub and a small linen closet to make room. Come on in and try it out with me."

"I thought you had to pee. I know I do."

"Yup, so get in here. Anything I want tonight, right?" she said with that sly smile she shares with Jill.

I knew where this was going and though I still found it a little weird, it also got my cock stirring. I walked into the shower and she gently took hold of my penis as she backed herself over to the bench and sat down. "Jill told me about you two peeing in the shower and I had to admit it was something I always wondered about but never tried. So indulge me, big boy." She held my dick gently, pointing it at her chest.

"If you insist, I'll do my best," I told her. "Understand it isn't that easy to pee when a beautiful woman is holding your dick, and especially if it tries to stand up and cheer, so to speak." I tied to relax and let it flow, finding I had to close my eyes to not to think about it.

After a few seconds it started, but in spurts, then finally I seemed to relax enough to let it go, and opened my eyes. JJ was covering her beautiful breasts with my pee and smiling, then she lifted my prick enough to hit her neck. Then she surprised me by closing her eyes and taking it right in the face, but she was still smiling, her lips closed tight. Watching her, and feeling her holding my cock, was getting me hard. She let go as my stream dwindled, and watched my cock stiffen while it sprayed on her. "I guess you like this," she said in a soft teasing voice that was quite alluring.

My bladder was almost empty, and the growing erection interfered as it twitched. The stream soon became a trickle. She guided it again so that what was left ran over her crotch as she sat on the bench. By the time it was done I was fairly hard, and she gave me a couple strokes before standing up. "My turn to go, and your turn to have a seat, big boy."

She steered me by my dick until I was seated on the bench, then straddled my legs as she stood before me, her breasts nearly in my face. I was a bit nervous about being peed on, even though I liked it when Jill had done it, but my cock couldn't seem to decide if it wanted to swell more or shrink.

JJ put her hands on my shoulders, bent her knees to squat a little and started to pee. The warm liquid trickled over my semi erect dick and down across my balls, then the stream got stronger, hitting me in the lower abdomen and running down over my crotch. She let go of my shoulders and used her hands to spread and lift up on her labia as she leaned back, directing her stream higher. She hit my mid chest but no higher. She then put her hands back on my shoulders and sat on my legs, with my cock pressed between us. Her warm urine continued to gush all over my cock, which now responded by stiffening much more. She squirmed a little and said, "I think you like this, too." She was right.

JJ wrapped her arms around my neck and kissed me as she finished peeing on my lap. Fuck, it was pretty sexy; much more than I would have guessed. I thought about her squirting when I had eaten her, and I wondered what it would be like if she squirted on my cock while being fucked. I imagined it'd be somewhat similar, except that definitely wasn't urine. The thought aroused me more.

"Mmm, that was kinda fun, wasn't it," she stated, more than asked. "Little Robbie really seemed to like it, and I'd love to sit on him right now, but he needs washing up first, considering he was pounding my ass a few minutes ago." She got up and turned on the water, then took me by the hand and led me under the spray from large, round shower head that was almost a foot across. It was like standing in a very warm summer rain. She pulled me in for a deep kiss as we embraced under the cascade.

During the kiss, JJ, stroked my cock with a soapy hand until it was fully lathered, not to mention fully erect. After the kiss she grabbed the Feeldoe she had brought from the bedroom and got another hand full of liquid soap. "I thought I'd wash this up in here, too, and then give you that ass reaming you deserve. You up for a shower fuck, from the receiving side?" she said with that sly, but incredibly sexy, smile.

"Sure, if that's what you want, baby," I replied as I hugged her from behind and kissed her neck. She moaned softly and tilted her head to the side to give me better access. I moved a hand up to caress her breast and my cock pressed into her butt crack. I could see her rubbing soap on the Feeldoe like she was giving it a sensual handjob. My other hand slipped down and covered her pussy, rubbing a finger along her slit and between her lips as warm water continued to rain down on us.

After a minute or so of my caressing her, kissing her neck, and nibbling her ear, she turned in my arms and reached behind me to slowly shut off the water. "That was nice," she said, softly, as she gave me a gentle kiss. "Now it's time to peg that cute ass of yours, stud."

She stepped away from me and took a bottle off the shelf in the back of the shower. "I keep some lube in here for when I spend a little extra 'me time' in the shower," she said with a wink, and poured some on her fingers. "Turn around and bend over with your hands on the wall, big boy. Let me get that lovely ass ready."

I did what she said and felt her pull one butt cheek aside as slippery fingers rubbed around my anus. One finger soon slipped inside me and tickled my rectum. I moaned softly and pushed my butt back towards her involuntarily. The finger slid out and was quickly replaced by two, slowly pushing in and out. They twisted around and bent inside me, rubbing against the walls, and across my prostate. "Ohh, umm, yeah," I sighed, slowly squirming my ass against her fingers. My cock was fully engorged.

"I'm glad you like that, honey," she purred in my ear. "Just a moment while I get this in my pussy and then I'll fill you with the long end. Bend over a little more." The fingers slowly slid from my ass and down across my perineum to gently stoke my scrotum before being taken away. My cock twitched with arousal.

After what seemed like forever, but was actually less than half a minute, JJ pulled my butt cheek aside again and I felt her press the head of the Feeldoe against my eager asshole. The cool lube on its firm silicone skin made me clench a little until she slowly pushed it into me. The head is rather pointy, hardly any thicker than the shaft, with a pretty narrow ridge below. It slid in with minor resistance after the preparation by JJ's fingers. "Ungghh," I exhaled once it was in.

JJ paused, adding more lube I assumed, then pushed in farther. She pulled back slightly and pushed in deeper still. "Do you like this big boy? Does it feel good sliding into your hot ass? Almost there," she said as she paused briefly and then advanced again twice more. I could feel more pressure against my butt. She put her hands on my hips and said, "There now, balls deep, if I had balls. Are you ready to get your man pussy properly fucked, stud?"

Man pussy? "Um, yeah, feels pretty good so far. But be a little gentle with me, please JJ. I'm still new at this." That sounded so girly. Shit...

"I'll try not to get too carried away," she said with a soft sexy whisper near my ear as she pulled back and slowly pushed into me again. I moaned my appreciation. "Yeah, this is nice. It rubs me just the right way. Is it rubbing you the right way, stud?" she asked in a cheeky kind of way.

"Yeah, pretty good. Uunghh. I mean, it feels good, but not a lot of prostate stimulation right now, I don't think. I assume, ungh, you might want a sort of user review, for your product research. Uhuh," I said in a relaxed tone, but with a little groan when she pushed into me.

"Yeah, I do, but I want to be sure you enjoy it, too. How about if I add this," she said just before I felt a little tingle of vibration start. "Oh, that's good for me, does it add much for you, honey?" she asked.

"Um, yeah I can feel it some," I said. We again discussed what the vibe added, as she continued to thrust in and out of my ass at a moderate tempo. It felt good, and the vibe did help, but maybe the critique didn't do too much for my arousal. Still, it was important feedback for her about a product she wants to carry in the store, and what better time to comment than during use.

"Ok, thanks, that was helpful. Now let's just enjoy ourselves," she said. She moved one hand off my hip to my now semi-erect cock and my balls. "I know you won't always be hard when your ass is getting all the attention, but did I distract you too much? Can I make it up to you, honey?" she purred at me. She started to move her pelvis around as she fucked me, the Feeldoe sort of stirring inside me as it moved in and out. That increased the stimulation on my prostate. Her hand held my cock and squeezed it, then began to slowly stroke it.

"Uhmm, yeah, that's nice," I half moaned. "Anything you like baby. The way you're moving that thing in me feels real good."

"Glad to hear it, it feels good for me, too. I wish I could be sucking that nice cock to get it really hard, but stroking it is fun, too. You like me stroking your cock while I fuck your cute ass, honey?" Her voice was soft and sexy, almost teasing. Shit, she was hot.

"Yeah, I do. My cock loves anything you do with it, baby."

"Do you like me fucking your ass, stud? Tell me if you like this."

"Yeah, JJ baby, I like feeling you fuck my ass. Peg me baby. Make me cum, baby." I figured she wanted me to ask to be pegged. I was hoping she wasn't getting into a really femdom thing right now. But then again, maybe that could be kinda fun. I was really horny...

"Mmmm, good, `cause I like fucking your ass right now, and stroking your cock. I wanna see you cum for me, stud," she said with a sexy, lusty voice. "Shoot your load for me. I just wish it could be in my face or my mouth, while I fuck you" she said with a sort of sigh. "It's fun to fuck you like this, but I can't get the rest of me where it can more of the action. It's a little frustrating."

I was bent over almost 90 degrees at the waist, my hands on the shower wall, as she pounded my ass doggy style, and jerked me off from behind. The position was fun and sexy, but it didn't let either of us put our face near anything really interesting, if you know what I mean.

"Yeah, I got ya. I'd like to be kissing you, or nibbling your nipples. Umm, I'd love to be eating your hot, juicy pussy right now." Thinking about those things, especially her pussy, and when she squirted on me, was winding me up even more, as was her thrusting. And maybe it aroused her, too, since she started fucking my ass harder and sped up stroking my dick and pumping my ass.

"I'd love your mouth on my cunt right now. Ughh," she grunted as shoved hard into my ass. "But I also like what this Feeldoe is doing. Ughh. And right now I want to see you, ughh, shooting cum out of that cock. Ughh. So come on, come for me. Ughh. Shoot you cum for me, honey. Ughh."

She was getting me so very close, and in under a minute I felt the wave of an orgasm starting to build. "I'm almost there, baby. Gonna come for you, baby." She slammed into my ass and wiggled the Feeldoe as she did.

"Ooohhh, fuck me, baby. Gonna come. Uunngghh. Fuuuck." I shot a stream of semen longer than I expected. I was looking down at my cock and JJ was pulling up on it as she stroked me, so it hit my upper chest and chin. It might have hit my face if I if my head were bent down any lower.

She laughed and moved her other hand off my hip, in front of my cock to catch to next shot. She quickly pushed my face back up with her cum filled hand, wiping it across my nose and mouth before reaching back down to try catching some more.

She held the Feeldoe pushed tight into my ass, my prostate pulsing on it and the vibrator tickling my anus. She kept stroking my cock and I shot again into her hand. She wiped it on my mouth and told me to lick her hand while she squeezed hard on the base of my cock.

As I licked cum from her hand she slid the Feeldoe slowly out of my ass, making me twitch from the sensations on my over stimulated prostate and sensitive asshole. She took her hand away from my face and pulled me around with the hand still tightly gipping my cock.

Quickly yanking me to her, she sat back on the bench and put her lips around the head of my cock. When she loosened her grip and stroked me again I shot one more load into her mouth. She moaned "Mmm," and smiled around my cock as she sucked the last of my spunk out of it. My dick started to soften.

Releasing my cock, she stood and wrapped her arms around my neck, pulling me in for a kiss. I felt spent, and my knees were weak. I wrapped my arms around JJ and pulled her in for support as we kissed. Of course, she still had cum in her mouth which she swirled into mine with her tongue. Her hand rubbed the back of my head and my hands gripped her by the ass.