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Thread: "Hollywood's Hot Cougars Finale" with Christina Hendricks

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    fanfiction "Hollywood's Hot Cougars Finale" with Christina Hendricks

    Hollywood's Hot Cougars Finale
    Author: Robertdoc
    Celebrity: Christina Hendricks
    Warnings: M/F, cons, oral, blowjob, cunnilingus, big tits, titfuck, doggy style, virgin, fingering, masturbation

    This is the grand finale of my series, although I ended it with a little cheating. All my other stars have been 40 or over, yet I flash forwarded to this final star’s 40’th birthday next year so she could get in this series – and to include a birthday theme since this is getting posted on my real birthday.



    May 3, 2015

    I was celebrating my 21’st birthday tonight in a very private way in my apartment. Technically, it wasn’t even my birthday party. It was really for someone else’s birthday that happened to be on the very same day.

    The first time I found out about this was back on my 20’th birthday, which broke the ice with the other birthday person in question. A person who was 39 years old a year ago, was famous, a woman, and one of the most iconic figures on television – in more ways than one.

    I already knew Christina Hendricks before then, since I’d gotten to do some intern work on the ‘Mad Men’ set as they filmed their final season. But we didn’t actually start talking to each other until we found out we shared the same birthday. Although she got the actual birthday party on set – which took on extra significance in the show’s last days – she made sure to include me too.

    It was my first real interactions with most of these stars, and with Christina as well. Somehow, the interactions kept coming with her over those last weeks. When it was time to close the set for good – and for me to be assigned to another one – Christina made sure we even kept in touch after that.

    Then came the phone calls and e-mail exchanges. Then came the actual meetings. Then came actually watching some of the final episodes when they aired on AMC. Then came me actually seeing the final one in a cast party she threw.

    Then came how I noticed husband Geoffrey Arend wasn’t around in these parties. I assumed since he had his own show and career, his schedule kept him away. She explained that it was part of it, and that the other part was more by choice.

    Then came the stuff she said about her marriage – stuff that was probably more appropriate to say to a shrink or a girlfriend. Then came her lament about the end of an era, both professionally and personally, right as she was about to turn 40. Then came the deflective jokes about her turning 40 and me turning 21 on the same day.

    Followed by a really off color joke about how I’d be legal to fuck on that big day.

    I chose to believe emotions, personal problems and perhaps a little alcohol made her say that. I certainly didn’t expect her to bring it up the next time we talked, except to apologize for it. Yet she didn’t apologize.

    And before long, I didn’t want her to.

    She was entering the next big phase of her life and career, whether she’d enter it alone or not. I was still trying to figure out where to go next in my life, and whether I could really do something other than part-time work in the industry.

    We were both headed towards massive challenges in milestone years. So maybe starting it off on a…..physical note would bode well. She told me not to pretend I hadn’t thought about it, even when I was next to her and she was….leaning and standing a certain way.

    By now, I knew I couldn’t lie to her.

    Eventually, we worked out a little game plan. Christina would go out on May 3 with friends for a 40’th birthday party, and I’d be one of them. She’d incorporate a little 21’st birthday celebration for me, and after that, I’d say I’d have to be on my way. I’d return to my apartment, which would be vacated on that night, and she’d eventually show up as well.

    By then, I’d have a little dessert and side dinner made for us, so that we could have a more intimate birthday meal. Then it would get intimate in other ways. However, we both agreed we should actually set the mood first.

    It did make a big difference, really. Although there was more than enough room to admire Christina when I got to her party, I couldn’t really do it intimately and knowingly in front of others. No….I wanted to save much of my admiration for her in that black dress and obviously ample cleavage for when we were alone. As hard as it and other things were.

    I kept our shared looks and stolen glances to a minimum at that party, just wanting to have regular, light hearted fun before the more steamy fun arrived. We both limited our alcohol, we both didn’t eat too much, and we made sure to talk with other people more than each other.

    There was no need to give each other presents there, since the real gift giving was coming later. But it would be suspicious if we didn’t exchange something clean in public. This was keeping in mind how I couldn’t afford to be as extravagant as her other friends – and the wrong gift could send the wrong message in a context only we were familiar with.

    I was good at picking out funny cards, so that was an easy part of the gift. Fortunately, it wasn’t hard to find ones tailored to a 40’th birthday. That helped ease how comparatively less fancy my gift was to the others, I assumed/hoped.

    To her credit, Christina had her own talent in picking a funny card – although there were likely no shortage of them for a 21’st birthday too. Yet the card was bigger than the actual present – a much smaller card. A card with a phone number.

    A personal one for Matthew Weiner, according to Christina.

    Although they weren’t working together anymore, Christina still had enough pull to plug me to him. So whenever I was ready, I could call him and arrange a meeting with him, and he would try to find me some kind of work for him – perhaps on his next project or for day-to-day stuff. We would work it out when we met, according to her.

    She insisted she should have given this to me a while ago, and that she wasn’t just waiting until now because of what today was. I was the only one who fully understood what she really meant.

    I was overwhelmed enough that I probably should have taken my leave, if only so I didn’t kiss her. At the least, it could have been the perfect excuse to go and get ready for her visit. But I just hugged her and made it as warm and genuine as possible – which almost balanced out the side effects from having her tits pressed right into my chest.

    Somehow, I kept my glances and feelings on lockdown for the next 10 minutes, when I announced I had to go. I had the excuse that I should go home early and prepare to call Matthew, which was handy. So I said goodbye to everyone and exchanged normal looking birthday wishes with Christina, saying I’d see her soon.

    I only exhaled and let the rest of my emotions out when I was safe in my car. Between the feelings of gratitude, regular excitement and horny excitement, it was quite a batch to sort through. It took me the whole drive back home, and nearly the entire time preparing our meal, before I was somewhat settled.

    And on cue, the red headed devil reappeared at my door about five minutes later.

    Now that we were alone and the moment was at hand, the awkwardness really settled in – especially after our last encounter. At that point, I was truly convinced that eating first was the right call, since it bought us both more time.

    It took until we were halfway through for that time to run out.

    “I meant it, you know,” Christina started. “I didn’t give you his number just for the sake of a birthday present. Or because of….” she circled her hand around, supposedly to symbolize what was coming.

    “I know,” I assured.

    “I just wanted to get this right. Make sure everything will be okay. Even if….” she didn’t really have to finish that particular sentence. “I know you’re good enough to be okay. No matter what happens later on. I really should be too. But getting you on your way, feeling like I did something right, having something solid to hold onto….”

    “This is all about starting this year off right, right? This milestone year for both of us?” I reminded. “Even if….nothing else happens, I think you did that already. At least for me. I don’t know if what I can do can do the same for you….not that I won’t try like hell!”

    “I know you will. I trust you. You at least I can trust,” Christina shared. “No matter how old I am, what I do from here on in, who I’m with….at this moment, I made an impact on someone good and young and hot who worships me….for soul and body….”

    Maybe that line was a little over the top. But we both knew there was some truth in it. “Well….if it wasn’t true, I wouldn’t have set this dessert up first, would I?” I pointed out. “I’d just have you right here and now instead of drawing it out….no matter how much I want you here and now….”

    “But you know you’ll have me in the end. That’s why you can afford to take your time,” Christina figured out. “To savor it….make it more thorough and sensual instead of just straight out fucking….even if that comes later….” she hopefully promised. “That’s how a first time should be. As a man and as someone starting a new decade….”

    “So which way are we going with now?” I had to ask. Honestly, at this point I could go either way – but was leaning towards the quicker version. As Christina slid her chair and herself over next to me, I suspected she felt the same.

    “What do you think?” she replied, in about the sexiest way I could think of. It certainly distracted me from her hands – until one of them landed on my lap.

    “What…” was all I had before Christina went for my zipper. “You do it like that and I won’t….” was all I had before she found my cock inside my pants.

    “I know. But let’s get that first one out of the way now. Then the next ones will be longer. Trust me, I have the experience,” Christina said without any irony in her voices, if not her words.

    Christina stood up and actually rolled up her dress, showing what was underneath – absolutely nothing. Nothing when it came to underwear, anyway.

    She obviously didn’t come here with a bra, and now knowing she was completely naked underneath that dress….now knowing what her red headed, pink, wet pussy looked like underneath….well, my cock didn’t need to be touched to be on the brink now.

    Christina kept her dress up and sat herself down in front of me, on the front edge of the table, with her bare, long legs open and her pussy right in view. Yet when she bent down, all I could see in front of me were her legendary, barely covered tits. As if her pussy wasn’t enough.

    “Like I said, we should get more than a few things out of the way now,” Christina repeated. “Come here….”

    I leaned my head forward, yet Christina closed the gap by pushing it right into her chest. My face was utterly smothered in her cleavage, and I immediately knew I never wanted to leave.

    However, Christina wasn’t satisfied with just killing me this way. It became clear when she reached down to take my rather erect cock, now in a position to pump it while I was breathing in her tits. I couldn’t believe I didn’t cum all over her right then.

    But while I still had….maybe a few seconds, I would take advantage.



    I finally moved my head around, nuzzling the giant exposed tops and sides of Christina’s breasts while she jacked me off. The combination was dizzying, and it only got worse when I actually started kissing her ample flesh, sliding my tongue over her mounds and dipping it between them.

    Just when I felt almost ready to go, Christina stopped pumping me. She then took both hands and pushed her tits up further onto my head, practically tit fucking me with her cleavage. Taking the hint, I pressed myself deeper against me, using my lips and tongue even faster.

    “Hold them….but don’t take them out yet,” Christina warned. She then removed her hands and gave mine permission to come up, cupping the cup of her dress. Although a zipper was right between them and I could very easily lower it, I followed orders not to.

    My hands tried to stay steady while holding such abundant surfaces, which got harder when Christina took hold of my cock again. She stayed bent down over my face while I played with her tits and she stroked my shaft, although this couldn’t endure much longer on both our parts.

    Of course, I would be the one to give out first.

    “Tell me when you’re gonna cum,” Christina breathed out. “At least try….” she finished, hardly helping when she brought her other hand down to brush my balls.

    “Now, now, now!” I hurried up to give her fair warning, regardless of how I sounded.

    She paid no mind as she sat back up and took her chest off my face. “Aim for my leg,” she said quickly and with a much hotter tone than mine.

    With no time at all to question her, I shot off and tried to keep the damage right on her left leg. Not all of my spurts directly hit it, but with her dress hiked up, I at least didn’t stain it and cause incriminating evidence.

    The evidence on Christina’s leg, however, was easier to clean. Which she did by taking her shapely, cum stained leg in her hands, sliding them up and down to rub my cum right onto her skin. It was mind boggling, to say the least – and reminded me it wasn’t just her tits and ass that deserved pin-up status.

    The act was almost enough to make me hard again then and there. Since I’d gotten my first orgasm caused by another woman out of the way, and since I was 21 now, recovery time was on my side. Nevertheless, it wasn’t just me who needed my first birthday orgasm.

    “I want you to do to my pussy what you did to my tits,” Christina confirmed, taking me by the back of the head again. I stayed seated in my chair and bent my head down this time, placing it between her open, bare legs. Christina stayed seated on top of my table and prepared for me to eat her out.

    She had to know I wouldn’t be technically proficient at this – not right away. I could only slide my tongue against her, moan against her from her taste, rub my face on her and hope it helped. If she had waited for this as eagerly as I had, then maybe I wouldn’t need to do that much.

    Regardless, I tried to put some extra effort in, using the techniques I’d dreamt up in my imagination -- and some in porn videos. I also decided to put my hands on her upper legs, rubbing them and leaning on them to add extra sensation for her.

    But thinking of her legs, and what else I’d done to them, gave me an even better idea moments later.

    I took my head out of her pussy and moved back, staring at the leg I just came on. Christina already rubbed my cum into it, so I wouldn’t be tasting myself – but it might be hot for her even if I did. It felt like I was just tasting Christina as I kissed down her lower leg, though.

    As I did, I let my hand go back to her pussy and start fingering it. I let my index finger fuck her fast and hard, while my mouth kissed and slid up and down her leg. I added a second finger, hoping both of them weren’t too clumsy at this – and hoping other tools of mine could avoid that trap later.

    Christina groaned and pushed back against my fingers, while my free hand went on the back of her leg to stroke and rub it, just like with my lips. “Oh, that’s good….you did your research,” Christina credited. I hoped sliding both my fingers all the way in and wiggling them around proved it too, and it sure sounded like she agreed.

    “Fuck….fuck, fuck me. It’s been too long….” Christina gasped. “Wait, wait….I know what I wanna do. Back off….”

    I decided to finger fuck her for a few extra seconds before doing that. Yet I ultimately did back myself up, giving Christina room to stand up again. Her dress dropped over her pussy and upper legs again, but she quickly rolled it back up – only to turn around and then lay her upper body on the table.

    Leaving her bare ass right in my face.

    “Eat me out and fuck me from there….let me rub this all over your face too,” Christina asked. It was hardly a question one could say no too. Not with….a sight like that.

    Compared to her tits, Christina’s ass had few fewer moments in the sun, most notably way back in Season One of Mad Men. Now she was bent over and fully exposed to boot, fully showing that unbearably round, thick, curvy ass and presenting it for my disposal.

    Of course, I knew she just wanted me to finger and eat her pussy from that angle. Not other holes. That was something for….well after losing my regular virginity, if that. But the rest of that large, luscious flesh seemed to be fair game.

    As such, my hands went right to her cheeks and rubbed all over that ample surface, even more than with her tits earlier. Meanwhile, my face pressed right up against her ass, dipping my tongue back into her pussy and licking it the best way I knew how. I even suckled whatever I could, hoping that was a bonus.

    Christina pushed her ass back on me, so my hands cupped and jiggled it right back. Before long, I moved my face back and let my left fingers fuck her, while my right hand enjoyed moving her cheeks around. I saw them ripple as I tapped and played with them, saving that for future reference.

    I soon put my face back in and sucked her lips and clit as hard as I could, while pushing her ass up and apart as much as I could. Christina groaned and cursed, wiggling herself and forcing more of me into and against her.

    “Fuck….are you hard yet?” she moaned. Once I thought about it, it sure felt that way. Looking down confirmed it too.

    “Then fuck me. Fuck me right here. Pound your cock and balls against my ass and give me more of that hot young cum. Right inside me this time….” Christina panted.

    Well, that was what we were here for, after all.

    Possessed by something….purely primal, I supposed, I stood up, lined my cock up behind her and immediately slammed it right into her. She was wet enough and I was ready enough, so I didn’t have to ease my way in.

    I briefly figured that even though I got hard again in a hurry, it would still be a while before I came again. Therefore, I could afford to start fucking her fast and hard, losing control as I saw her ass bounce against my hips and heard Christina moan gutterally.

    I hoped her loud reactions and curses weren’t just acting to egg me on. I supposed since she was such a good actress, I wouldn’t know either way. I also wondered if she’d be this way if anyone else was finally fucking her like this again tonight, or if it was just me. Or at least partly me.

    Either way, I would make my case to her.

    The best way to describe it is that I stepped outside of myself. Someone inside of me who I’d never met before was the one fucking Christina hard now. He was the one celebrating his birth right now, by pounding Christina’s baby maker. By rubbing and stroking her lips as they tightened on his cock, by rubbing and jiggling her ass, and by following her orders to fuck her harder.

    “Fuck me, fuck me, I’m gonna cum…..oh, take that fucking cum! Take it and I’ll take yours, shit, fuck!” Christina called out, squeezing the cock inside of her and supposedly cumming all over it.

    That cock still wasn’t ready to blow, but it still wasn’t ready to slow down. It fucked her all through her orgasm, as if it could force another one before its own. It fucked her mercilessly and without thought in an attempt to try, though.

    Yet it was no use. Her orgasm, her dripping pussy, her big, bountiful, beautiful bouncing butt and her passionate cries were too much for that cock.

    So it did the only thing it could do – explode and completely cover her insides with long, hot strands of cum. The kind that never came out of it before, even in its previous orgasm.

    When it started to pass, I felt myself coming back to consciousness. I registered Christina’s pants and moans first, followed by the incredible wetness around my cock. I took it out and saw how drenched it was, as it finally started to soften.

    Christina stayed bent over with her bare, tired ass in the air, catching her breath and her own senses. I stumbled back onto my chair, slumped and barely sitting up as my cock stayed in the open. Some time passed before Christina moved and stood on her feet, her dress falling down over herself once more.

    “My God….” she said when she got a look at me. I hoped it wasn’t the kind of “Oh God,” one might say when they couldn’t believe they let themselves fuck someone, now that they were of sound mind again. Or at least that’s what I might have hoped if I wasn’t still mostly jelly.

    “Come on, let’s both get comfortable. In a different way this time,” Christina said. She helped me on my feet and led me to my couch, where we both sat/laid down. She was practically cuddled next to me, laying her head on my shoulder and her body against my side.

    Even after all that, we were both technically still completely dressed, save for my cock still hanging out. But Christina looked exactly the same as she did before I gave her my virginity, and so did I for the most part. There was something symbolic about that which I’d recognize once I thought straight again, I was sure of it.

    It was kind of surprising we didn’t go to sleep, but our eyes stayed opened as the rest of our bodies started to wake up. Finally, I felt alert enough to move around a little, if not enough to let Christina come off me. Before long, I even audibly exhaled and sounded like I’d be ready to say words again.

    “You okay?” Christina spoke first, easing me into it.

    “It’d be weird if I wasn’t, huh?” I rasped out. “If you’re not, it wouldn’t be, though….” I assured her.

    “No, it’d be weird if I wasn’t too. And I’m not. I mean….I’m more than okay,” Christina promised. I nodded my pleasure at that.

    “You don’t have to stay,” I said after a minute of comfortable silence. Perhaps too comfortable, considering some things. “You probably have to go soon, anyway.”

    “Not really. I covered all my tracks,” Christina shared. “It’s why I came here, it’s why I let you cum inside me, and it’s why I’m not going anywhere yet. We got the first time part out of the way….now there’s the rest of it. When we’re both ready, I mean.”

    “Are you sure?” I had to be sure before I really let myself start to go again. “If you needed this from anyone….I mean if it doesn’t matter who….it doesn’t have to be with just me.”

    “I know. I considered a few others. But I wanted you. And I didn’t settle for you,” Christina ruled that out. “I wanted something new, something hot and something great, with someone new, hot and great. I knew that was you even before you pounded me.”

    “Really?” I asked again, looking to see if there was any acting in it. Again, if there wasn’t, maybe I wouldn’t know either way. I had to try, though.

    “I want to have my way with you in every way. Not just the way we just did,” Christina said. “And I want to show you how to have me in every way. I want to be a very thorough teacher on that end….” To my credit, I didn’t make some gross pun about ends.

    We sat up as Christina put her hands on my shoulders, her body and cleavage starting to lightly brush against me. “I broke you in, and I want to reap all the rewards of breaking you. All the slow, deep, fast and hard rewards. Right now….I think we can only do the slow ones, though. And that’s good. Because I want to take my time now….”

    I watched her eyes study me, her full lips curl up, her chest heave and her hourglass figure look even more well defined in my eyes. “I want to take my time with you too….” I admitted. “If you’re sticking around….I want to take my time with every inch of you….I want you to teach me how….”

    “Only if you let me go first,” she said more quietly. ‘There’s so much I want to do….so much I want to let you do. But there’s one big thing we haven’t done yet.”

    As she brought her lips closer to mine, it did hit me that we’d skipped the kissing part. The moment her lips touched mine, however, I could have kicked myself for waiting this long. Then I brushed that aside and savored what was happening now.

    Christina glided her lush lips over mine, settling her body against me as I put my arms around it. As her seductive curves fit into my embrace, her seductive lips dipped between mine as her tongue made its way by. Keeping up as best I could, I let my tongue meet hers and rub against it, giving enough room for it to fully enter my mouth.

    Since we had been so wiped out early, we couldn’t really get revved up again this quickly. Even young people who’ve just lost their virginity have their stamina limits. But it was all for the better in this particular set up.

    I’d supposedly gotten my pent up, raging lust out of the way. Now I could just savor kissing her – and there was a lot to savor. In addition to her soft lips and her warm, wet mouth, not to mention feeling her chest pressed into mine, there was getting to touch that lush red hair, feel her moan gently on my mouth, and feel her embrace me and fit my body into hers.

    She did it well enough to lie me onto my back, putting herself on top of me. I hardly minded, having more room to caress the curvy shapes of her body, feel them pin me down and let her pin my mouth down. Her hands went on my shirt and went into my v-neck, seemingly trying to feel my bare skin without having to get up and take my shirt off.

    Christina just kept lying on me and kissing me, nonetheless, her tongue having its way inside my mouth. But I recovered to lay my hand on the back of her head, let my tongue slide into her mouth and navigate it right back.

    As much as we were rubbing against each other, I wasn’t hard yet, even with my bare cock pressed into her. Again, it wasn’t a problem, however. I realized I could be overwhelmed and in bliss just by kissing her and feeling her up, even if that was all we were going to do. Yet she did heavily hint that it wouldn’t be.

    She confirmed it by breaking off and saying, “Get to your bed. I’ll meet you there.” She then finally came off me and got off the couch, standing and waiting for me to lead the way.

    With no choice and no reason to ask for one, I got up and made my way to the bedroom. I turned on the light and stood next to the left side of the bed, waiting for Christina.

    I half expected her to already be undressed, in order to surprise me. Instead, she was still in that pesky black dress when she came back into view. Yet she leaned against the door, cocking her ample hip, then started walking closer.

    It wasn’t so much walking, however. It was the definition of strutting.

    She was putting on that famous little Joan strut for me, only more overly and obviously swinging those hips of hers back and forth. She was like a human version of Jessica Rabbit, only with a less tiny waist, as I could swear I heard sultry drum beats behind her.

    I couldn’t confirm that, since it was just my imagination. What I didn’t have to imagine was Christina finishing her seductive waltz about 15 feet away from me. On impulse, I threw my shirt off so she wouldn’t have to go through it herself.

    It also seemed to have the side effect of trigging her to grasp her zipper. So there was that too.

    Christina lowered the zipper on top of her dress, which instantly made the rest of her breasts spring out. I barely had time to take them in before she lowered her dress straps, then slid the rest of the dress down to my floor. And since I knew there was nothing underneath, I knew she’d be fully naked now.

    It still didn’t prepare me nearly enough for it.

    She only let me stare at her naked, hourglass body for a moment before strutting over again. With that walk happening with no clothes on, I didn’t know what to watch. This helped her bring me over to the bed and lower me down.

    I laid there as Christina saw my cock still hanging out, coming back to life anew. She started undoing my pants and lowering them, avoiding my erection nonetheless. Once I was just hanging out in my underwear, she made me lose them too.

    We were now both naked – and if I wasn’t mistaken, she was staring at me with a hungry look that almost resembled how I must look right now. I kept in shape, which I was especially thankful for now. But to make her look that hungry? That was….an ego boost, to be sure.

    Christina rested herself on top of me for the second time, only with nothing between us. She kissed my lips all too briefly, before guiding her lips and mouth down my neck, nearly unbearably slow. She made sure I could feel every inch of her lips on my skin, and feel the desire in her deep kisses and nibbles.

    After finishing on my neck and collar bone, she rose up and virtually straddled me, giving me one hell of a view. Yet she seemed to think she had one as well, judging by how she looked down at my chest. “I knew I’d enjoy this,” I heard her mutter.

    She started by leaning back down to kiss my upper chest all over, her own crushed against me. The slower she went with her kisses, rubs and licks, the more she looked at me as she did it, the more I felt her bare breasts across my lower chest and the more I saw her ass raised up, the more I felt that out of body experience again. I did really want to stay in my own this time, though.

    Christina dipped her lips and tongue down to my bellybutton, then made sure to kiss every inch of each of my abs. Her tits were now pretty close to brushing my cock, as if it wasn’t tingling again already.

    Yet when she reached up to hold my shoulders, she steamily slid her mouth back up my body, leaving a trail of kisses, nibbles and licks. It reached my neck, my chin and then finally my lips as she had her way with my mouth. I tried to keep up and have my own way with hers, yet I doubted it was matching up.

    “What now?” she asked against my lips. “You want to have these lips wrapped around your thick cock?”

    “I….I assumed you wanted it already,” I got out.

    “I guess you want it between my tits too, huh?” she guessed.

    “Well….if you really want it in your mouth, you should do that first. Once it’s in your tits, it might not last very long,” I felt honest enough to warn her.

    “You’d really go off a third time, just like that? I’m still stuck on one,” she helpfully reminded me. Well, I hoped it was to be helpful.

    “Shit, I….” I didn’t get to finish.

    “No need. I just have to get your cock working again….but not that much. Then you’ll have to make us even. And then you can cum again. We’ll work out if it’s in my mouth or in my tits later,” she figured.

    First and foremost, she went back down my body, dragging her hands down my chest along the way. She kept them on my stomach as she came face to face with my cock, in their first truly intimate confrontation.

    She introduced herself by batting her tongue against my head, sliding over it until she licked down and wrapped her lips over me. After sucking deeply, she went down another few inches, then came off and put her lips on my side, gliding them up and down. Once she took my cock with her right hand, she took my balls with her left and went down to kiss and play with them.

    Pushing my sack up with her tongue, she licked underneath it and then licked all the way from sack to tip, before fully sucking me off. Christina bobbed her head steadily, pleasing me while still soothing me as well.

    Her blowjob turned slower and more sensual, humming and gently stroking me while her tongue went all over my shaft. She came off and I placed my hand in her hair, resisting the urge to push it down. I was content to watch her suck my head, watch her look up at me and see how pleased she was to taste me

    She gave an especially deep hum while she licked my slit, getting out a little bit of pre-cum. Her eyes closed as she sucked harder, but went down deeper even slower. When she went all the way down, she sucked me as hard as a vacuum, before coming off just as quick.

    After deep throating and sucking a few more times, she placed my shaft against her cheek and rubbed it on her face, her fingers dancing on my shaft and balls. Just as I got used to feeling my head against her head, she surprised me by placing her tits over me then and there.

    With almost no preparation, I was at a loss as Christina tit fucked me and licked my head whenever it came out of her chest. When she took her breasts off, she sucked me hard and made sure her tongue got me extra wet, before putting her tits right back over me. It was a wet, quick fucking that I finally added to by thrusting my hips up

    Just as I got the hang of that, she took her tits off again. I thrust up again involuntarily, only to have her mouth drop over me again. She quickly bobbed hard on it, as if signaling me to fuck her mouth myself. When I was absolutely sure of it, I did just that.

    My hands stayed in her red hair, but they didn’t push down as I did all the work from pushing my hips up. Finally, she came off and put both hands on my cock, covering the top half with her mouth. She stroked me and practically made out with my tip, making me strain to hold back in more than one way.

    Just as it became too much, she came off me and said, “There we go….that takes care of that.”

    “It does?” I rasped out.

    “I got my taste. Now come get yours again. But you can’t stop until you make me cum. Then we can just take care of each other,” Christina promised.

    With those instructions, Christina laid on her back, presenting her voluptuous figure to me. Her instructions were likely to just eat her out and work her pussy – but seeing her like this made me want to bend those rules a little.

    I put my left hand on her pussy, rubbing it before putting my head down to get another taste. As my fingers dipped in and out of her along with my tongue, my right hand went up to the top of her breast. It teased her nipple while I fucked and licked her pussy below.

    I really did enough research, and enough late night fantasies, to imagine using these kind of tricks despite my inexperience. I hoped my creativity was making up for my execution, despite her soft coos.

    After licking my wet fingers, I shoved them back in and fucked her faster, kissing and sucking the side of her pussy and squeezing her nipple along the way. Finally, I took my fingers out and placed them on her left breast, then laid on my stomach and started full on eating her out, while squeezing as much tit flesh as possible with both hands.

    As my hands worked her chest over, my tongue circled, dipped into and teased her pussy, until my lips just sucked her. Christina’s moans got louder and I did feel her pussy getting wetter, so I felt free to get away with a few more ideas.

    Lifting my head up, I went up to put it on her chest, while keeping my left hand on her pussy. I tried to finger fuck her while having my way with her breasts, now that they were completely naked for me. Christina helped by pressing them on my face as well.

    I went to suckle her left tit while pumping her faster, timing my suckling with my thrusts. I also pinched her right nipple as a bonus, which got an extra groan from Christina. “You….you know your stuff,” she praised. “Not bad for….”

    Well, I wasn’t one now, really. In fact, I almost wanted to shove my cock in there now and prove it a second time. But I owed her another orgasm first.

    Ruling my cock out, I needed one more creative solution. The best I had was to come down and lay my head between her legs, then eat away while my hands touched her waist. After finally fondling her bare tits, I wanted to feel up every other curve she had.

    My hands massaged and rubbed Christina’s sides, from her waist, hips, ass and the top of her legs. I traced every inch of her curvy shape, all while noisily sucking and tonguing her. I tried to worship her as much as she did with me, even if I was only kissing her in one place.

    Christina helped by arching her hips up and humping my face, which fueled my mouth and hands even more. My hands landed back on her breasts and pushed them up, and when I looked up, Christina was closing the gap to tongue her own left nipple. I rubbed the other side of it to help along, then did the same with her right when she tongued it.

    I suckled her lower lips and dug my tongue into her, regardless of how precise it was. Desperate to do more, I asked, “Sit on me….sit on me, please….I can make you cum, I swear….”

    I got onto my back in time for Christina to sit up and straddle my chest. When she raised her pussy up over my head and set it down, I could tell she was careful not to put too much weight into it.

    I was less careful sucking her clit, running my hands all over her shapely figure, locking them onto her ass and bouncing it around, then doing the same to her tits. With more room to do it now, I let them really savor rubbing and jiggling every inch of her. Coupled with my vigorous mouth work, I hoped it would be enough soon.

    Several moments of my hands jiggling and borderline slapping her ass later, it was enough.

    Christina finally let herself lie on her back moments later, catching her breath because of what I did to her. By now, I shouldn’t have been so stunned at things like that. I would never stop feeling lucky and grateful no matter what, though.

    At that latest truth, I knew I wanted to truly worship her like she did for me. Even if I didn’t entirely know how.

    My cock had gone unattended long enough to last long one more time. I chose to ignore that and put my head between Christina’s legs, kissing her pussy and ensuring it was clean – for now. My hands went onto her legs and savored stroking them, as I started kissing up to her stomach.

    Christina relaxed and rested her head, while my head and hands went higher. I doubted I could kiss every inch of her stomach and lower chest like she did with me, yet I gave it my best shot. My hands massaged her perfect curves and every perfect shape they could cover, until they landed on the sides of her perfect breasts.

    My head rested between them and stayed in place, as I gently rubbed Christina’s breasts against each side of me. I felt Christina’s hands go onto my back as I bounced and rubbed her breasts on my face, feeling myself resting comfortably into her arms.

    It wasn’t feasible to just stay in this position forever, as sad as that was. Eventually, I lifted my head out of her tits to see her face, which almost looked….peaceful. Perhaps not just because of the orgasm.

    Compared to how she was when we first talked about this stuff, when we first set this up and when she first reflected on being 40, this was a hell of a relief. I helped give her that, if only for tonight. Leaving aside everything else about how this was set up….this really was perfect.

    This was the perfect way to become a man. Maybe the perfect way to enter a new decade of life. Certainly the perfect way to fuck one of the most desired women on television.

    However, I went up just a little higher merely to kiss her. It was worth it as she held me deeper and used her plush lips to part mine. I let myself rest my body on her breasts and her curvaceous shape and fell deeper into bliss.

    “Come here and fuck me,” Christina said when our lips parted, making me even more blissful. Especially when I actually entered her.

    It didn’t take long for Christina to slide her hands down my back and onto my ass. They grasped pretty securely onto each cheek, pushing them forward and pushing me deeper inside her. I left her do half the work and did my part slowly, but deeply.

    “This is nice,” Christina cooed. “It doesn’t always have to be dirty. But it doesn’t always have to be nice too….fuck, don’t you forget that. Or that,” she said when I angled my next thrust just right, or so it seemed.

    “I won’t forget anything,” I promised, going a little faster now.

    “Good….I think we still gotta go over a few things….tomorrow. Just to be sure,” Christina gasped, holding onto my ass tighter. “I got as much time as you need….”

    “Maybe you need it too,” I caught on.

    “Yeah, that too….” Christina confirmed, bucking herself against me. “I need to show you everything….I need you to remind me of a few things….and I need….” She trailed off as my left hand went between her legs.

    “Tell me. Teach me,” I tried not to beg.

    “I need you to fuck me hard. Then fuck my tits hard and cum on my face. Or in my mouth. I just wanna taste some hot young cum again….” Christina urged.

    “I’ll fuck you and cum wherever you want,” I assured. “I’ll give you all the cum you want….”

    “Then get up here now….” Christina gasped, and I gave her a few more hard thrusts before following orders.

    “Grab my titties and fuck me,” she ordered next as I straddled her chest. I placed my cock in her tits and pressed them over it, immediately getting to work and immediately hoping this would last more than 30 seconds.

    I did get distracted by how Christina put her left hand on my ass, patting and squeezing it again. She also put her right arm around me, and I turned my head to see her reach for her pussy, trying to fuck herself while I fucked her tits.

    “I might need a toy for that next time. We’ll talk about that later,” she got out, finally brushing herself and starting to finger her pussy. I just stayed upright and thrusted forward as much as I could, squeezing her tits and watching my head barely come out of them.

    This lasted longer than 30 seconds, to my relief. Sometime after that, Christina said, “Fuck me….cum on me and them cum inside me….fill me up….I wanna feel it in my throat….I still want that so bad….”

    Never deny a birthday girl anything. It was a handy rule in all scenarios, especially this one. But I drew it out by asking, “You really want to feel some cum?”

    “Yes, fucking yes,” Christina repeated.

    If we did this straight away, I would have given out a while ago and not had any chance to think. As it was, thinking was as difficult as trying not to come. But I did think enough to say, “Let’s start with yours.”

    I really had done a lot of research and thinking over this – more than the average virgin. Of course, the average virgin didn’t really have this kind of time to plan, with this kind of opportunity or partner. So I really drew up a lot of things I wanted, if she was willing – and I could almost safely assume she would be.

    She didn’t seem to be when I took myself off her chest and tits, and I almost wasn’t either. She changed her tune when I quickly replaced her finger in her pussy with three of mine, and I changed mine before long too. Especially when she exploded all over them in short order.

    I waited until my fingers were completely soaked before taking them out. With my index finger, I put it to her face and trailed it down her cheek, then onto her lips. Her face wasn’t soaked with my cum yet, but I let it feel her own for a bit, before licking It off her.

    When I got to her even juicier than usual lips, I kissed and sucked them clean as she softly moaned into it. I then put my wet hand on her right breast, wiping the rest of the juices on it, so I could kiss and lick them off that already glorious surface too.

    Once I took care of that, I put my fingers back into her to collect her last bit of wetness, then sat up and rubbed it into my cock. I used it to jack me back onto the brink, staring down at Christina’s flushed face, mouth and tits.

    She wanted me to cum on her face first, so I aimed it at her cheek – the cheek I briefly painted with her own cum. But Christina moved just as I lined it up.

    “Oh God, fuck it! I need to drink it all!” she groaned, before taking me completely into her mouth.

    Even after her sensual blowjob and my vigorous tit fucking, her desperate deep throating was the best trick of all. Or maybe I became biased when I shot every last bit of cum I had left for the night right down her throat, which she eagerly drank as she promised.

    Once she came off, I promptly collapsed onto my back. I heard her say, “Sorry….kind of your own fault. But we’ll get it on my face and tits tomorrow….”

    Mentally, I held her to that as I finally closed my eyes for the last time on my 21’st birthday.

    XXXXXXXXXXXXXXXXXXXXXXX

    That night was my entry into manhood, in more ways than one. It was also Christina’s first night of a new decade of life.

    But when I woke up that morning, immediately found myself pressed against Christina, and fucked her while lying behind her without opening my eyes, I knew the party wasn’t really finished yet.

    Christina kept her word and stayed for much of that day. She kept her word and let me cum on every surface I didn’t cum on the previous night. She kept her word and showed me the kind of moves I couldn’t dream up myself or research online.

    Even reading about them wouldn’t have been the same as actually fucking her while brushing an active vibrator from her purse against her asshole. Or sixty-nining until my face was literally bathing in her juices. Or us taking turns eating each other out from behind. Or posing while the other masturbated themselves back to life from it.

    It was like I had two birthdays in one year, although the year still had 363 days left. They would all have a hell of a bar to go over, though. Even the one where I actually got a paying job from Matthew Weiner sometime later.

    But there are no days like the one where you lose your virginity – and hopefully, that meant or will mean a good thing to all of you. Even if you don’t have or won’t someday get first time stories like this one.

    We can’t all lose it to one of the sultriest, bustiest, curviest women in TV history, though. Young men can’t all get that kind of hot cougar or soon-to-be hot cougar to educate us. They can imagine it enough to hopefully put it into use at the right time, though, no matter with whom.

    If that helps any of you, consider it my own birthday gift. If you don’t really need it, good for you.

    Sometimes, what you think you need can defy all expectations and hopes, however. I’d like to think tha happened to two people on their milestone days on May 3-4, 2015.

    Yet I suppose she wouldn’t have asked me to vibrate her asshole if it didn’t happen for her too. There’s that to go on.

    THE END

  2. #2
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    Great way to end the series! And I love the fact it's written ahead of time in order for you to "cheat" to include her.
    Also a good selection of celebrities used throughout that normally wouldn't have a story dedicated to them.
    Every chapter will be well worth a revisit in the future.


    :thanks: :notworthy:
    My "Claim Your Girl" Selection For May 2017:



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  4. #3
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    Thanks all around, for past, present and future reading.

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