"Hollywood's Hottest Cougars 5" with Amy Poehler
Hollywood’s Hottest Cougars 5
Celebrity: Amy Poehler
Warnings: M/F, cons, oral, blowjob, cunnilingus, fingering, tit-fuck
Amy Poehler was dressed to the nines for our date.
She had a black dress on that wasn’t very short, but just short enough to catch the eye. Her chest was covered up, but the dress was form fitting enough to show she had a formidable pair bundled up. Above, her blond hair and blue eyes were done up just right, in that mix of being adorable and being fucking gorgeous that she mastered all too well.
I tried to honor that balance by not being too pervy in checking her out, but letting her see she was getting to me. I was kind of used to it by now, since this was date number three between us. And I was used to trying to hold myself back, given the sensitive state of her personal life.
It had been four months ago that she and fellow comedy star Will Arnett stunned their cult audiences by announcing their separation. It was clearly not the most ideal subject to talk about with her, but it was touchy enough for her friends at the Parks and Recreation set to prop her up.
I believe it was Aubrey Plaza and Rashida Jones who were most encouraging of her to actually date me when they saw us talk. It was certainly them who threatened me with playful/deadly serious warnings when it came to Amy. I already knew not to screw up with her, but there’s nothing like being threatened by famous friends to really drive it home.
There was a reason they were so protective and caring around her, though. Anyone who watched her on TV and knew anything else about her could figure it out. After watching her faithfully on TV and movies for over a decade before actually meeting her, I had a good idea.
I was a rather ordinary 28-year-old, non-famous person. Now someone as brilliant, funny, beautiful and full of life as Amy Poehler was trying to move on from her long-time marriage with me. I was well aware of how responsible I had to be.
On the surface, an outsider wouldn’t be able to tell Amy was going through that much. She was cracking jokes during her stories from the set, smiling brightly and seeming to be the light of the two-person party. It wasn’t anything unexpected from her, really.
When she brought up how this was our third date, and what that meant, I certainly got much less suspicious. Yet on the drive back to my place, the nerves did start to set in.
It was obvious that if we were doing….what third dates usually bring about, it would be her first time since her separation. Combined with the usual nerves before having sex for the first time with someone new, and the additional nerves of doing it with a beautiful celebrity and long time crush….well, it was both an ideal and unbearable combo.
I tried to get it together, since these nerves could turn into something….more embarrassing during the act. I was in a zone trying to get myself stable, all throughout the second half of the ride home. I was so focused, I didn’t realize I was still in a trance a minute after I’d parked my car.
Amy should have asked me what was wrong and gotten my attention by then. But when I snapped out of it, then saw she was perfectly still as well, I had everything put in a proper context.
All my nerves were nothing compared to hers right now. My trivial concerns seemed much smaller, compared to what she was about to do. What it was clear she was trying to rev herself up to do all night, but it didn’t stop her from getting cold feet anyway.
Even with four months to get herself ready for this, she was still getting out of a decade-long marriage and relationship. I assumed this was new territory for her in more ways than one. As much as I realized her friends were pushing her to do this, and she was pushing herself to do this as a way to move on, putting it in practice was another matter.
The worst part was how small Amy looked right now. She played characters with the biggest, most joyous personalities on TV, and seemed to live out loud the same way off screen. But seeing her apologize, try not to cry and explain herself by trying to lightly comment how “divorce sucks” was….just not right. Not from her.
So I got her out of the car and into my home, all the while assuring her we didn’t have to go upstairs – or do anything else she wasn’t ready for. She did say that she wanted to, although I had to ask honestly if it was for the right reasons.
If she only wanted to use me for rebound sex because she was forcing herself to, or her friends were pushing her, or for any other reason that had nothing to do with liking me as a person….some such reasons would be easier to accept than others.
When I brought up some of those theories, some of Amy’s old fire came back. It made me relieved, but also nervous, since she took offense with the premise that she would just pick any old random guy from the street for something like this. At least it told me she really did like me, even if I didn’t frame it the best way.
It was just a case of her being nervous to take the leap – the latest in a string of hard ones that confirmed she had to move on. Any other woman in her position would feel the same, as she reminded me.
Considering how I had Amy on a pedestal most of the time, it was a reality check. At that moment, she was just a regular, 41-year-old soon to be divorced mother of two, trying to come to terms with moving forward – and accepting that another man, 13 years younger of her, could want her and that it was okay to want him too.
Even though it was startling and sad to see someone like her so nervous and insecure, I still wanted her. When I let her hug me, I still had to hide the clear, hard signs of how much I wanted her, like usual. But I wanted her to be ready to want me too.
After a while, she was ready to try something. A test run, she called it.
She stood up halfway on her toes, making me relieved I wasn’t too tall for once. But I felt 10 feet tall – not just in one part of my body – when she began her first kiss with me.
It was slow and somewhat tentative, as I kind of expected. But when she broke off and tried again, it was almost filled more with promise, with an undercurrent of passion coming across as well. She then put her hand on my cheek and drifted it towards my neck, pressing her lips deeper and letting them move around a bit.
When she came off, I exhaled deeply and opened my eyes. Amy looked back and let me see the nerves, hope, bright light – and underlying arousal – in her deep blue eyes. Her lips also threatened to curl up into a little smile as well, which was almost as arousing.
Even with all her doubts, and her uncharacteristic hesitation to take a big leap, she did it and clearly liked it. And I hadn’t even kissed her back yet. That would have to be fixed.
Instead of exploding out of the gate, however, I was as careful as she’d been as I leaned down to kiss her. I was probably revved up enough deep down to go wilder, yet this didn’t feel like the time for it. When Amy kissed back at the same deep but gentle pace, I knew it didn’t.
Before I forgot, I broke off and led her to the nearest couch. Once she started snuggling against me, I brought her lips back to mine. The rest of our bodies stayed together against each other on the couch, even as our mouths and heads started moving around.
We experimented with many slow and fast clothed mouthed kisses, and then many slow and fast ones with our mouths open. She put her hands on my chest and almost grabbed my shirt during the more passionate tongue kisses, while I nearly did the same thing with her hair.
Otherwise, my hands stayed steady while in her hair, on her face and while they went down her body. When they got to the zipper on the back of her dress, I toyed around with it without trying to take it down. Still, she could tell it was on my mind.
When it became too hard to ignore, she insisted I should go first, however. Figuring that was fair, I slid back and gave myself room to take my shirt off. Once I was bare chested, Amy seemed amused that I was “letting it all hang out.”
Since our bodies had been pressed against each other for a while, I could guess she had a bra on underneath that dress, But when she stood and started getting herself out of it, my guesses on what that bra looked like were way off.
It was a tastefully revealing number, of an even deeper black than her dress. So was the matching, fancy, lacy underwear she also revealed in the meantime. They framed her nicely curved hips perfectly, almost as much as her bra framed the full open and hidden round curves of her chest.
As she said before and said again, she really wanted this to be the night, despite her late jitters. Otherwise, she came more than prepared.
Despite being over 40 and having two kids, and not being known primarily for her looks, I already knew how Amy had gotten more and more beautiful with age. This….was the ultimate validation for being right.
To do something other than gape at Amy, I started getting my pants off. Compared to her underwear, my plainer white ensemble looked a bit lacking. But when she pointed that out herself in a joking matter, I didn’t feel offended. Seeing her start to enjoy herself was enough, even if I had been offended.
Deciding I needed to see her enjoy herself even more, I had her lie on the couch on her back. Instead of going on top of her, I kneeled down in front of the couch, putting my hands on her bare stomach. After seeing she was fine and wanted more, I let my left hand drift to her panties while my right slid to her bra.
My left fingers brushed the center of her panties for a while, then made their way to the edge without pulling it down. My right fingers did the same to her left bra cup, then her right as well. Finally, I let two of my left fingers dip into her panties, before starting to brush them along her lower lips.
I let more of my right hand get involved in cupping more of Amy’s breasts, while my left hand started getting more involved on her pussy. I still didn’t remove any of her garments, however, trying to move her panties aside enough to start fingering her without removing them. I also let her bra stay on as I moved up to touch and stroke her cleavage.
Amy closed her eyes and exhaled, leaning back and seeing both relaxed and overwhelmed at the same time. It continued as I inserted more of my index finger into her and let my right fingers slide between her breasts. But after fondling and fingering her enough, I had to give her more.
At last, I slid her panties down barely enough to expose her wettening center, so that my mouth could start covering it. Although I’d heard Amy curse up a storm before, hearing her do it in this context for the first time made me feel overwhelmed now. Tasting her for the first time also played a part too.
I stayed focused enough to come up with a plan, tonguing her below while my fingers went back to work on her breasts. They played with the front of her cups and her bare cleavage, but I let her bra stay where it was. It was a little difficult fondling her tits and licking her out while kneeling down near a couch, yet I did the best I could.
My next move was to lift my head, go up to start kissing and licking her breasts, then use my left fingers to work on her pussy. There wasn’t as much I could do with my mouth up there, at least with the bra still on, yet my fingers filled the gap down there.
Finally, I let Amy sit up and helped her start unhooking her bra. When it was loose enough, I let my left hand go back to fucking her as she started shaking her bra off. Yet when it was gone and her bare chest was fully exposed, I gave my hand a rest.
However, when I was done studying Amy’s round, firm looking boobs, I put both my hands to work.
Leaving her pussy alone, I had Amy stay seated straight up, while kneeling between her open legs. My hands pushed her tits up and I put my face right between them, letting my mouth go to work. Half of it was to devour her breasts, and half of it was to make her wish I’d do that somewhere lower again.
But as Amy moaned, cursed and started getting particularly tingly down there, I stayed where I was. I kept lathering up and sucking each nipple one at a time, then going back and forth between suckling underneath her breasts. I pushed her tits against my face and slid them over my mouth, but it and my hands didn’t go any lower.
Amy breathed heavier and started thrusting her hips up, yet I did nothing about it. I kissed her chest quickly all over, then deeper and wetter, making her being to whimper. She made softer and huskier sounds while her legs began to wrap around me, weakening my resolve.
But I wanted to give it one more minute. I wanted to get her to such an extent, it wouldn’t take many licks to make her cum when I went back down. Given how it might have been quite a long time since she last came – thanks to a man, anyway – she must have been plenty pent up already.
Yet when she hissed and outright told me she really, really needed to cum, I really got the idea.
With no more warning or buildup, I deeply suckled and kissed both her breasts, then unwrapped her legs and dove my head back between them. After attacking her pussy with the same oral intensity I used on her tits, she gasped and dropped f-bombs all over the place until she pushed her hips right up.
In short order, she released what may have been months of pent up juices against my mouth. As hungry as she was to let them out, I was just as eager to swallow them down.
When I got them all, or as much as I could, I came up for some fresh air. Amy slumped back down on her back, as all the fresh air she had wasn’t quite enough yet. I just stayed on my knees on the floor, until I figured we both needed a bigger and more comfortable place to lie down.
After Amy agreed, I helped her onto her feet, leaving our various clothes behind as we headed to the steps. I led her to the bedroom and she promptly flopped onto the bed, although she did it head first at first. Whether she was doing a gag or legitimately too floored from her orgasm to fall right, I didn’t know and didn’t ask.
She did roll over onto her back before long, leading me to just sit down beside her. I watched her lie next to me, naked, before seeing more clearly that I was the only one with any garments on. I reached for my underwear and took the front of it down just as Amy took notice.
I saw Amy look up and down my shaft, but I rolled on top of her before she could reach for it. If I was afraid of going off from her touch, then my plans to get inside her should have really been red flagged.
Yet to give myself extra time to get ready, I reached down between her legs and gently made sure she was revving up again. In any case, this was another personal milestone that Amy might need time to be ready for anyway.
I looked at her and saw she still clearly had some nerves, but I could see more confidence and eagerness in her face and eyes this time. I still spent another several seconds fingering her and getting her ready again, however. If she was that set on this big step, I had to thoroughly reward her trust.
Leaning on my right elbow besides Amy’s head, I took my left hand out of her and tried to pump my cock. Hoping her juices on my fingers had coated it enough, I put my arm up and lined myself. At the same time, I saw Amy move her arms down and felt her pushing the back of my underwear down next.
Leslie Knope was a butt girl – so perhaps I was seeing where the inspiration for that running gag came from. Or rather feeling it, as Amy held my ass and gave me the clear signal to push forward.
After the tip got in, I waited for both of us to adjust. After I got the next few inches in, I slowly pulled out and made us both a little frustrated. After getting myself back in and slipping a little deeper, I could tell Amy was getting adjusted to having a new cock inside her.
Adjusting myself, I leaned on my elbows and let my hips start thrusting in earnest, all as Amy helped them along. I looked down at Amy beginning to enjoy herself, then just listened to her enjoyment as my lips dropped to her neck. I started giving it the same thorough treatment as her breasts, until I felt her pushing her hips back against me.
For a while, we were in sync bumping our groins together. After a while longer, it wasn’t quite enough, as weird as that concept should have been. But I wanted more room, and I figured Amy would benefit from it too.
I got up and sat on my knees, getting Amy to sit up and put herself down on my lap. When she reinserted herself onto me, I now had the room to let my left hand rub her pussy, while my right arm went around her. It pulled her against me as I rubbed her, gave her a one-armed hug and watched her begin to ride me.
Amy rested in my arm, letting her hips move up and down while the rest of her body relaxed. I gave her a few more deep rubs, then took my hand off her pussy and put it around her. While nothing but my cock was working her pussy, she seemed fine in both my arms as our hips came together.
It was easier to grasp the concept of Amy Poehler riding me while naked in my arms – on paper, anyway. Reflecting on it while trying to stay focused enough to keep thrusting my hips took up the next few minutes.
When she pulled back to look at me, my focus was taken away by her flushed face and bouncing breasts – so I stopped reflecting and went back to just enjoying.
I enjoyed it enough to bend down and suckle her breasts again, while holding on tighter to her bouncing ass and hip. Amy’s enjoyment got more vocal, slipping in more curses in between louder moans. They got louder still when my right hand left her ass to rub her pussy, all as I suckled down on her right breast.
Amy sounded somewhat surprised when she started talking about cumming again. I got an ego boost from that, until I remembered I should be close to cumming by now. Getting her off a second time while trying to hold off my overdue first time may have been a tall challenge.
I still had to try, though. And try I did by putting both hands on her pussy after Amy wrapped her arms around my shoulder. She held on and tightened around me, trying to look down with me as my fingers rubbed whatever they could get a grip on.
It was enough to listen to her groan for a few moments, but I had to look up before long. By then, she seemed to be trying not to throw her head back. Yet after I gave her a little pinch, she let out a big breath of air and had the biggest of smiles on her face for a moment.
Although her cries and curses already told me she was turned on, among other clues, seeing her smile like that – her natural big smile, even during all this – was the most encouraging thing of all. I could also see it reflected in her shining blue eyes, before she closed them after tightening herself harder around me.
That was the final trigger I needed.
Assured that Amy could hold on, I gathered myself and prepared to pound her harder and faster than ever. I only slowed down enough to let my hands go back to work, rubbing her deeper until I held her hips and slammed myself in and out of her.
Amy could only breathe heavily, unable to say anything or groan too long. But that changed soon enough when she shook and tightened around me. With a few more big thrusts, she groaned long and loud as she came long and hard on me.
Trying to hold on myself, I put my hand on the back of Amy’s head when she dropped it on my shoulder. I was as stiff as I could be, so that I could stay stiff in the area that counted just a little longer. But after she finished, Amy started wiggling and picking herself off me all too well.
My breath froze as Amy put herself back down on my lap, with my wet, throbbing cock out in the air. She looked down and saw just how wet and hard she made it, looking impressed as well as freshly fucked. Through all this, she hadn’t actually touched it with her hands yet, I realized – at the same time she did.
Unlike me, however, she took immediate action as a result.
And when she grasped my tip and shaft with her small, eager hand, my actions were inevitable and immediate as well.
It took just a few pumps for me to start shooting off into the air. Inevitably, it hit a few targets – on me and her. But by the end, much of it got on her upper body.
After all this, I shouldn’t have worried that it would make her upset. Yet after all that had gone well tonight, it was natural to think something bad would happen at the end to balance it out – and I wasn’t in the best position to be logical either.
To be absolutely safe, I quickly offered to go clean Amy up, as soon as I was free and coherent enough to do so. Without thinking, I put my underwear back on – which I never took completely off, mind you – and raced to get the nearest paper towels.
I was calmer by the time I found them and could think clearly again, and was assured by how Amy didn’t looked grossed out or impatient, despite my cum resting on her body. I made sure to wipe every drop clean, and to get the damp towels into the nearest trash can.
Now there was nothing to distract us from facing the actual aftermath of this thing.
My only idea to start off was to just lay back down in bed, staring up at the ceiling and feeling too shy to face Amy right away. If she was feeling regret, or feeling like this was too much too soon for her after all, I wanted to put off seeing it as long as I could.
But finally, I felt Amy’s face against my neck and couldn’t put it off any more. When I turned my head and saw Amy merely looking at me, I feared the worst.
Yet with every passing second after that, her smile grew. With every passing second in that span, my fear of the bottom dropping out diminished. The next several seconds helped me stop thinking altogether as she drew me in for more deep, sweet kisses.
Slowly, Amy’s lips and tongue went faster and more passionately over mine. Although we both just came and she was over a decade older than me, her libido seemed to have a much more instant recovery. She rolled on top of me as further proof, before dropping her lips to my neck – and her crotch right against mine.
As she kissed me lower, I thought I heard her say something about “all things being equal.” Or some other joke about equality, and her being a big believer of it. I wasn’t in the best state to translate any sexual meaning beyond that.
All I knew was that Amy was starting to kiss and thoroughly devour my body, like I had with hers. The equality line, whatever it was exactly, began to make more sense as she went further down – and I started to feel myself twitching again.
It then occurred to me that she had two orgasms to my one. If she believed in all things being equal….and if she was that eager to do for me what I did for her….
There was no doubt about it when Amy wrapped her hand around my half-hard shaft. Nevertheless, she poured it on by rubbing my tip and pressing my shaft against my lower stomach, while kissing me a few inches higher. She palmed my shaft and even went down to my balls as her lips got lower and closer to me.
When she put my staff straight up again, she hovered her face over my tip. After I looked straight ahead at her, she locked eyes with me and stayed locked as she kissed my head. When she slipped her lips over it, however, I nearly broke eye contact.
I did break it when Amy started sucking on me, though. Once I laid back and watched her, she had her eyes closed as her head went further down. I wasn’t completely hard yet, but I was getting there as fast as possible.
After that mission was accomplished, Amy began to slow down. In fact, it was almost too slow for comfort, as she torturously moved her lips up and down my shaft. She popped off and then did the same with her tongue, before twirling it over my head.
She let herself suck my tip again, then loudly came off and promptly crawled back up my body. Leaving my cock along – at least with her hands and mouth – she brought them back to my face as she resumed kissing me. My erection rested below her groin, which stayed still while her lips moved around mine.
Amy subdued me with her kisses for a while, breaking away just as I started to join back in. Nevertheless, she crawled herself down my body again, before her head hovered over my harder shaft once more.
This time, she took me by the hand and arched herself up enough to place my shaft over her chest. She rubbed me against her left breast, then her right, then slid my head underneath both her boobs. After teasing me with their soft weight, she put her even softer mouth back over me.
She let her head bobble down harder and faster, making my cock wet and throbbing. She gave me a deep suck after she got most of me in her mouth, then loudly came off again and sat up. At that point, my cock was wet enough to lubricate me when she put it between her tits.
Sadly and frustratingly, she pumped her breasts on me for only a few moments. When that was done, she crawled up yet again, this time stopping when she put her mouth on my neck. She kissed and suckled it as she began grinding herself against my aching cock
At that point, I began babbling, muttering words like “beautiful” “gorgeous” and “sexy” when I wasn’t cursing. I used them even more frequently when Amy came off my neck, looking right at me as she kissed down my chest one more time. I practically started thrusting my hips up, getting impatient for her third round down below.
Of course, if I got too impatient, that third round wouldn’t last very long. Regardless, Amy’s lips and eyes, and the memories of what she did and would do again with her mouth, made it more irrelevant. The rest faded away when she took me with her hands and stroked everything she didn’t start sucking again.
I had awoken a sleeping giant, obviously. However long it had been since she did something like this, she was done waiting. She set out to be done waiting from the start tonight, and any nerves she had to work through were taken care of. Apparently, she was very grateful to me for helping with that.
Maybe she wasn’t grateful enough to let me cum soon, though. Or maybe she was being more grateful than I deserved by prolonging it. With the way she was going, I was leaning towards the latter – mostly.
Yet I was leaning more towards insanity when she pressed me against my groin and went down to my balls. She suckled my left one as deep as possible while licking it, then did the same to my right, and then left them alone.
Amy just brought my cock back up, let me squirm from the sudden sensation she left behind, and hovered her mouth over my head again. I looked at her, saw the sweet and sultry smile growing on her face, oh so close to my cock, and saw the same emotions reflected in her deep blue eyes.
At any moment, I would either cum or start babbling again. Either way, something would explode out against my will soon.
My babbling won out when Amy sunk her mouth back over my cock way too slowly – or just right, depending. Yet as her lips slowly went down, her tongue went over me in rapid fire motion, all while she started humming. She took me out before long, only to blow a breath of air over the areas she licked.
Before I could thrust my hips up, Amy suckled me again and began bobbling up and down herself. She went faster and faster before coming off, leading to her blowing air on me again and then kissing me. After kissing my head, she wrapped both her hands on my shaft.
Already on edge, I didn’t know what would set me off for good, if all this hadn’t done it.
And then my date, one of the funniest people alive, one of the most physically attractive women I had ever known and one of my idols, put her mouth over my cock and told me, “I need you to cum in my mouth right now.”
All it took was one more suckle on my head for me to do as she said.
Willing myself to watch, I saw Amy close her eyes and keep her mouth on my cock, and felt her gulp down everything I shot off. My hips shot up and froze in place, slowly coming down as I felt more drained. I saw Amy visibly swallow most of my cum down before my hips and head fell, though.
I let out a breath, hoping Amy could breathe normally again too. Before that awkward silence came back, Amy crawled back up one more time, laid down next to me, and almost cockily said, “Now we’re equal.”
It was a little hard for me to believe it. As much as I tried, my mouth probably couldn’t match up to that.
But if she believed it enough to justify doing stuff like that again, and if it validated that other stuff….more power to her.
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