Author: Robertdoc
Celebrities: Jenna Fischer, non-sexual appearance from Alison Brie
Warnings: M/F, Cons, Oral, Anal, Analingus, Handjob

July 2012

I was back in New York and at 30 Rockefeller Center much earlier than usual this year. To add to how different this was, I wasn’t here to temp for “SNL” or “30 Rock” especially since they hadn’t resumed filming yet. In addition, I was actually a plus one guest at a party held above Studio 8H and in the actual offices of NBC. Being Alison Brie’s plus one also added a final kick to it as well.

I envisioned none of this three months ago when I was caught having sex with Lea Michele on the “Glee” set and made tabloid infamy. But thanks to some encouragement from the actresses in my past; and some in-person encouragement from Alison; I weathered the storm in the end. Alison plugged my work and my clothed talents every day on Twitter, while I used my account and my writing skills to counter the tabloids and blogs. Eventually they backed off; either because I beat them back or because they had other scandals to cover soon enough.

I did get a few words in to defend Lea and “Glee” from the criticism they were getting. The scandal did still stick longer to them than it did to me, yet I commented on every online article or editorial I could to stick up for them. Soon enough, it was safe for Lea to call me and assure me that she would be okay and would get through it. I still offered whatever help I could, whether online, over the phone or in person. I chose to be encouraged that she didn’t need to call that much after that, although my lines were always open to her.

Lea still had a lot ahead of her no matter what, while I had a more uphill battle. Determined to make sure that this scandal wouldn’t define me for the rest of my career, I hunkered down on every book idea or script idea I could think of. With no temp jobs on the way, I had more time to work on them and submit them everywhere I could. And fortunately, Alison had a few connections she could use to get them to the right people.

This brought me back to New York in July, as I would try to further sell my services to NBC at this party with Alison’s help. The network’s bosses and its various stars would all be there, so I had a few avenues to plug myself in. NBC was in dire enough strengths that they could possibly need me for something, whether to submit pilot scripts or give them rights to adapt my future books or to join a writing staff. Given that they finally brought “Community” back for Season 4; which helped Alison get invited to this and make me a plus one to begin with; maybe the network’s decisions were getting better.

Regardless, I couldn’t pass up another chance to go to 30 Rock, although my trip wasn’t all expenses paid by the temp agency this time. But I paid my own way with only a little bit of help from Alison. She still had enough for a sparkling gray dress to wear, while I used my spare bucks on a nice light black suit.

Since I was a plus one, this couldn’t technically be called a date. Technically we weren’t dating, although Alison made an effort to hang out with me in between “Community” work and promotions. Once the season ended and the show was officially spared, we did have a bit more time together; which included a couple more sex sessions. While we weren’t an item, at the least we were certainly friends; as she was actually more like my manager too in some aspects. So as a manager and friend, she got me this trip back to New York and assured me that the NBC bosses and stars wouldn’t just focus on my scandal.

I did get the occasional question and comment about it from the other guests, but I usually steered the topic back to the rest of my resume. I offered that with my experience at NBC and in this building, I could be a full time asset in some capacity for some show. I gave them business cards, told them where to find my online work, and made sure to plug my work and devotion to NBC shows in particular.

After all, this was the network that, for all its faults and bad decisions, aired many of my favorite comedies. And on a more personal level, it did play a part in about half of my trysts with actresses….including the one who took me here and the one who began it all for me.

With that train of thought, I thought I was seeing things in the ballroom when I glanced at Alison; the actress who brought me here; and saw her talking with Jenna Fischer; the one who began it all. But after rubbing my eyes three times, I realized it wasn’t an illusion. At about that time, they finally noticed me and waved me over to join them.

As I walked over, it hit me that this was the first time I’d seen Jenna in over four years. She was one of the actress who called me three months ago before Alison came over, so we were caught up in a way, at least. But seeing her in person was in another ballpark, particularly since she had on a purple dress for the occasion. Although I hadn’t seen her in person for so long and she had given birth to a baby boy 10 months ago, she still looked as beautiful to me as she did back then.

That was another reason for me to feel a bit uneasy when I got to her; not to mention the fact that Alison was right there as well. But Jenna broke the ice by asking “Do you need a laptop to type me a hello?” in a tongue-in-cheek manner when I didn’t speak up.

“No, no of course not. Hello…” I said with a growing smile as Jenna went over to hug me. I tried not to hug her back too tight or savor the feel of her, especially with Alison there. Yet the fact was that Alison was there and she already knew that Jenna was my first actress; which made me more curious why they were together. “I, um, see you’ve met my plus-one, Alison Brie.”

“And told her I’m happy we’re both still on Thursday nights,” Jenna filled in. “Don’t worry, I’m happy you got through your crappy spring too.”

“Yeah, I finally did. I still get bugged about it once in a while, but it won’t define my career for long. At least if my shameless promoting goes well tonight,” I added.

“From what Alison’s told me, you’ve already met half these people. I’ll bet the shameless stuff wins over the other half, too,” Jenna predicted. But the main thing I took out of that was that Alison talked to her about my NBC experience; so I wonder what else she mentioned.

“Hey, not everyone has a crappy spring to get past,” Alison pointed out. “I know Jenna’s been pretty lucky since you last saw her.” It took me a second to remember what she was hinting at, but I soon got it. “Oh right, the husband and baby! I already said congrats on the phone, but that deserves a few in person,” I realized as I instinctively hugged her again. “Did they, um, make the trip with you?”

“No, I let Lee have some daddy time back in L.A.,” Jenna explained. I noted that the corners of my lips almost went up into a smile before I caught myself.

“That’s really great, Jenna. It’s something how far you’ve both come from just four years ago,” Alison reflected. “I filled her in about you the best I could, but I probably can’t tell it as well as you can. So you can try proving me wrong while I go catch up with my friends, K?” Before I could think of anything to say, Alison nodded with a chipper smile and went off to find her “Community” co-stars. This left me all alone with Jenna, in a rather suspicious turn of events.

“So you actually found an actress girlfriend out of all this?” Jenna inquired.

“No….I can’t say that exactly,” I said when I snapped out of it. “We are friends, and that means a lot to me too. We haven’t talked about if we’re anything more yet. But as long as she’s around me, I’m happy to be whatever we are now.”

“And if she wanted to be more?” Jenna went on.

“Oh, that’d be no problem too. I mean, come on!” I exclaimed, pointing at Alison as she caught up to the “Community” gang across the room. Jenna nodded in understanding, stating “I guess I shouldn’t be offended. I was your first crush, I knew there were others, even before a few months ago.”

“Well, I think you already had an idea years ago,” I added, as I now pointed her attention to Tina Fey, who I once again made sure to run into earlier in the party. “I never did thank you in person for bragging about me to her. If you didn’t get me that job….maybe you would been the only notch on my actress belt after all.”

“I just gave you Tina, you handled those nine others without me just fine,” Jenna said, remembering to lower her voice in case people were listening. No bloggers or tabloids could crash this party, yet NBC big wigs and stars could be just as nosy and damaging.

“Nine? That’s quite specific…..so Alison told you a lot before I came over. Sounds like you don’t need me to fill in the blanks at all,” I mentioned quietly.

“Well, she could only go into detail about you and her. Tina filled me in on you and her, and I read all about you and Lea. It’s just Christina, Kaley, Kristen, Sofia, Mila, Anne and Emma that I have less on,” Jenna recounted.

“I couldn’t do that here….people might here, or they might see the….effect telling those stories has on me,” I tried to allude to gracefully. “It’s hard enough keeping it down around you and Alison already,” I went on before I could stop myself.

“So even after all those other hotties, you still have that….problem around me? Even though you have more on your resume now?” Jenna alluded.

“I’d have that problem around any one of them. And no matter who the others are and what I did with them, you were my first. Even if I got to do more with some of them, you set the bar no matter what. I can never repay you for that….even though you’re the one who said you owed me one over the phone.”

“Well, I meant that too,” Jenna said after a while. “I probably would have moved on and found Lee if I never met you. But you helped settle me down before I was ready to do that. Just like Alison settled you down and helped you through that mess a while back. You would have found a way through on your own, but it would have been harder without her. And a bit less fun.”

She had me on those points; especially the last one. “Well, she is fun, and I’m glad you still think I am,” I thanked.

“I do. That’s why I was interested when Alison told me where you were staying. And that she wasn’t staying in the same room.” I had offered to get a double room for us, yet Alison insisted we take separate rooms and save money. Now her insistence was starting to look more suspicious and puzzling, as I thought over why Jenna would bring this up. “Wait, did she tell you why she brought that up?”

“No, but I had some ideas.” I had a few things to say about that, but Jenna kept going before I went on. “You don’t have to say anything now. I can come over there after the party and we can talk…..and only talk if you want to. Until then, you can go back to being shameless for NBC.”

Jenna smiled and headed away without doing anything suspicious like kiss my cheek, squeeze my hands or hug me again. That was at least one less worry as I tried to make sense of it all. But I did still have to plug myself to NBC brass, so that kept me distracted for the rest of the party; to a point. At least I didn’t think about the situation and what Jenna may have been offering without getting a notable boner.

When there were no more executives, show runners or stars to target, and when I couldn’t put it off anymore, I finally went back to Alison. “I heard good things about you tonight. You must have made a good impression….probably went all out to do it too. You should probably get some rest in your hotel room to cool off.”

Now I had to get some clarity, although I didn’t know how to phrase it; so I went with stammering. “Are you trying to….I mean, me and Jenna….why? And what about you and me and…..”

“There’s no you and me yet, not officially. I’ll be happy if there is eventually, but we don’t have to worry about that now. You have a career to establish, and I have to help make sure fans didn’t save my show and make thousands of fake goatees for nothing. So I can’t be mad or judge you for….getting closure on some things before we do anything. Now, I’m going go out on the town with the guys, and we can talk about how our nights went tomorrow. K?” Alison kissed my cheek and headed off before I could say anything.

That answered both everything and nothing, yet there was nothing I could do about it but leave along with most of the party guests. I didn’t see Jenna, so she was either heading to my hotel or was already there. After saying goodbye to everyone else I’d talked to, I took a cab and headed back to the hotel. Jenna wasn’t at the lobby, and she wasn’t at my door when I got there, so I figured I’d have to wait around for her.

I stayed in my suit so I could keep looking my best for her when she got there; and I just had to wait 10 minutes before I could impress her. I heard a knock on my door and jumped out of bed to open it, seeing Jenna there in her same clothes as well. I greeted her and offered her a chair while I sat on the edge of my bed.

“For the record, Alison acted alone in….whatever she said to you about me. She’s doing more to tempt you to cheat on your husband than I am,” I explained.

“Did she tempt married women like Tina and Christina before they cheated with you too?” Curse her for using my own lack of moral authority against me. “You didn’t make them leave their husbands or ruin their marriage. I think I can take those odds this one time….for closure.”

“There’s that word again. Why do you and Alison seem to think I need it? I’m just fine with our last time, especially since it spawned….all this!” I insisted.

“It wasn’t a blessing a few months ago. But now that that’s over and you’re on your way now, Alison thought you deserved a blast from the past. Well, she explained it better when she called me last night.” Now that shot up to the top of things that needed clarity. “How could she have called you?”

“It wasn’t hard for her. She looked up my cell number from NBC, made sure I would be at the party, and then told me you were coming. Then she filled me in on how well you’re doing and all the things and people you’ve done. It got me anxious to see you….like I told you on the phone, I wished I could have come up and helped you back then. But she beat me to it, so I’m glad you were in good hands. At least hands that were willing to loan you out.”

“And you’re….sure you want to take that loan? Just to revisit an itch from four years ago and help me come full circle?” I triple checked.

“She was right, you do like to take every way out before you give in. You weren’t that hesitant with me last time….I hope you weren’t more insecure after me. But I did hear you weren’t restrained at all after that,” Jenna hinted.

“Well….I told Alison enough for her to get that idea,” I admitted.

“Like I said, she painted quite a picture. I still want to hear your take on it. Come on, at least give me that….let me know what kind of sexy monster I created,” Jenna tried not to plead. Given that way of phrasing it, I figured I owed her that much.

“Okay…..I assume Tina already told you about our masturbation on Election Night.” Jenna nodded at that, so I concluded I could move on to the events only Alison briefed her about. “After that was Christina….the seeds were planted when I heard her masturbating and she caught me. Me promising not to tell anyone helped things….proceed from there.”

“God, of all the people to be your second celebrity redhead,” Jenna pointed out.

“Yeah….I had a lot to devour that time. The only other actress with a figure like that is Sofia, and that started because she caught me masturbating that time!” Jenna laughed as I started to chuckle from the irony again. “Those incidents started differently, but their endowments were the same….along with how much I worshipped them.”

“I can imagine, and I have. You were pretty thorough with me, think how you must have been afterwards…..and with those women at that,” Jenna trailed out.

“I was thorough with actresses who weren’t voluptuous, you know. Like Kaley….that was the first time I’d been that intimate with someone after you. We experimented with positions, she actually gave me my first tit fuck, and she reversed cowgirled me into an explosion or two,” I mentioned as I started to stop censoring myself.

“Mmm, so blondes are more fun in bed after all? Like Kristen too?” Jenna asked as I began to notice her legs crossing.

“Kristen and I made our fun in back of the ‘Glee’ auditorium. If those bloggers saw what we did there too….mmm, she’d have shattered their ears and they’d have better thing to do than post dirty pictures,” I reflected as my pants got more uncomfortable. “But it’s not just redheads and blondes…brunettes are smoking hot too. I ran through three of those in a row with Anne, Mila and Alison. Anne was my first full fledged movie star, and what a star she is. Then Mila….that was by complete accident, but what a sensual and exotic accident. And Alison…..fucking sexy and gorgeous Alison….” I reflected before I finally noticed the tightness in my pants. That helped me notice how Jenna saw it too; as well as how her hips were shifting around in her chair.

“So I noticed….” she finished for me as she inched her chair closer to me and my bed. “I already read all about Lea…..but before that you had Emma Stone, am I right?”

“Uh huh…..she rounded out the sexy redhead trilogy,” I confirmed, more clearly noticing that Jenna was putting a hand near my pants; and starting not to care about it. “I even had phone sex with her before Alison came over my house. I forget if I even told her that.”

“But you remember everything else?” Jenna softly asked as she unzipped my pants and used her other hand to help unbuckle them. “Yeah….if I heard that voice more clearly through the phone, saying all those things, I never would have lasted as long.” Now it seemed Jenna wanted to test how long I could last from sexy words; by pulling my cock out and beginning to stroke as she gently asked “Did you last long with Lea before you got caught?”

“Uh huh….took a lot of effort, but I did. And…..ugh, now you know the whole story.”

“That’s a hot story….and you’re sure I was one of the hotter chapters?” It didn’t sound like she asked because she doubted her hotness; as if I could with her hand on my cock and a much clearer view down her dress.

“God yes…..those other chapters wouldn’t exist without you….your hotness and beauty made it all possible. I did wish I could have kept in touch more and thanked you more afterwards….but I didn’t wanna give too much away or look like too much of a pig….” I confessed as Jenna started rubbing my dick head.

“You just gave everything away and you’re not a pig to me. I don’t want to hook up with a pig….let alone fuck him twice.” And she apparently didn’t kiss them in the meantime either, as she was now doing to me.

Now that I was fully into Jenna and closure, my lips and tongue responded in a hurry. As she jacked me off, the heat of her hand and the sweetness of her mouth provided a double whammy on me. I wanted a triple whammy, so I placed a hand down her cheek and to the shoulder of her free arm, where I lowered her dress strap. I then helped her arm slip out of it, and although I couldn’t see her now bare breast since my eyes were closed, I was able to feel it.

We moaned into each other’s mouths as we kissed, while she stroked me, I palmed her tit and I started to wonder if she was trying to finger herself too. If she was, she was nowhere near as close as me, as Jenna’s faster strokes and faster tongue finally pushed me overboard. Before I could plan out where my cum would land, I felt it go off; then opened my eyes at last when I felt some of it land up on my chin.

Since my erection was sticking right up, it was shooting into the air and landed on me and my clothes. Luckily for Jenna, she backed away before it landed on her dress; which was fortunate since she would have to leave in that dress later. For now, she stood back and watch as my cum stained my suit and pants, although it avoided getting on my face again.

I didn’t fully take in the mess I’d left until I could breathe again, and even then I couldn’t bring myself to worry about how I ruined my nice clothes. I needed to take them off soon anyway, and they could stay in my suitcase until I washed them back home. So with that, I got up and took them off like I should have done earlier.

Jenna’s dress was somewhat down already, although I hadn’t actually looked at the results. I heard her lower the rest of her dress down while my back was turned, and I decided not to appraise her until we were both naked. Once I had my clothes off and threw them to the floor, I turned my head to the left and saw Jenna’s dress and a pair of purple panties landing on that pile. With that, I steeled myself before turning to see her standing in front of me and fully naked.

As it had been four years since I last saw Jenna naked, and she had a baby just under a year ago, her body did look a bit different than before. However, she still had the same supple breasts and gorgeously rounded ass; perhaps a bit more so after having a baby. To top it all off, she still had the same long legs and well defined curves as well. And of course, there was still that lovely face that still looked both shy and eager as I gazed at her naked form.

“Still so fucking beautiful,” I let out at the end of my inspection. To further show it, I went over and kissed her again, pressing our naked bodies together. While the last make out session helped get me off, this one unleashed more passion that built up after four years of being apart. Jenna snuggled herself into me, her ample breasts pushed right against my chest, as my hands slid down to her soft backside and I noticed that her pussy was brushing up on my resting cock.

I couldn’t help but think about how a baby came out of that opening 10 months ago. But with that thought, I then had no doubt on how I should start this off. Who knew if she was a bit more self conscious and more uneasy about her pussy after a baby came out of it; yet on the off chance she was, I would try to turn that around.

“Stay right where you are,” I requested after breaking our kisses, as I didn’t want her to sit down just yet. Instead I went down to my knees in front of her and grasped her hips as I lined my face up to her pussy. I didn’t really get to eat her out until the end the first time, and I wanted a bit more face time here to make up for it. Plus I would get a better chance to keep feeling the rest of her while she was standing up.

Once I was in place, I stuck out my tongue all the way and put it over as much of her pussy as I could. I dragged it up slowly over her for my initial taste, then was encouraged enough by her subsequent long moan to put the tip inside her. It slid up and down her a bit more rapidly before I went to work simply eating her out. I went back and forth licking her outside and inside as my hands went to work going up and down her hips and thighs.

Soon I landed my hands on her ass while my tongue and face went deeper onto her pussy. Jenna kept moaning long and loud, perhaps still being a bit more sensitive down there. It didn’t seem to bother her as she placed a hand on the back of my head to drive me in even further. Before long, it felt like my head was in the middle of a sandwich between her hand and her pussy.

Yet I had other delicacies to feel as my hands left her ass and trailed up her waist before grasping both of her tits this time. I bounced them up and down to go along with my tongue going up and down her pussy at the same time. When I got a hold of her nipples, I suckled and even nibbled a bit on her pussy lips, to stimulate how I would have done the same to her tits.

“Oh, I missed this,” Jenna admitted as she grinded her pussy against my face. “And to think you’re even more experienced than before….God, it shows….” I was glad she noticed as my tongue worked fast to show its experience. I just hoped it was too much of a veteran to tire out as it kept dancing in, out and around her.

“Fuck, I feel even better that I was your first! Is there any first you can try now?” Jenna called out. “Something you can do with me that you didn’t do to the others?” With that I finally pulled my head back and breathed regular air again.

“You want to be my first in something else this time?” Jenna just nodded, a bit flustered that my mouth wasn’t still covered up by her. “I’ve pretty much done everything I could with the others. I tit-fucked them, sixty-nined them, used doggy style and reverse cowgirl, did them against the wall…..the only thing I can’t recall is…..”

With that my hand went down to her ass again as it came to me. There was one technique and one body part I hadn’t played around with yet; one even more intimate and secret than a woman’s pussy. I almost hesitated to bring it up with Jenna, yet with that squeeze, she figured it out. “You want my ass, don’t you?” she guessed.

“Well….you don’t have to give it up just because no one else did,” I offered. “You’re already my first in more important ways, you don’t have to increase your lead. Besides, I’m not finished with your other hole yet.”

“You could play with them both at the same time. That should finish me down there and get me warmer up there…..probably mean I’ll last longer the next time too.” That could well be a fair compromise…..and I didn’t put as much effort into giving her a way out like usual. “Then let’s test that out….bend over and lie on the bed.”

I stayed on my knees as Jenna walked over to the front of the bed and laid down on her stomach. Her ass was sticking up with her legs hanging down the bed, spread far enough so that I could still see her pussy. Since I still needed to work on that, I knelt down in front of her legs and ass and resumed eating her out, this time from behind her.

I worked faster to help get her closer and to help get her juices flowing; since they would be needed for later. But I conceded that I’d have to let my fingers finish the job, so I pulled my face back and started to let them work. In the meantime, I put my focus onto Jenna’s ass and used my free hand to brush over it. When I got my feel, I leaned down and started kissing and licking her full right cheek, with my left hand on her left cheek and my right still fingering her pussy.

I soon put my left hand on her pussy and worked to get my forefinger lubricated enough with her juices. When I felt it was wet enough, I had it trail up her pussy and keep going until it entered the bottom of her ass crack. It then trailed further up, making the inside of her ass wetter with her juices; although I wanted to save enough for the center.

For the first time, my finger was placed on top of a celebrity’s asshole. I worked to get Jenna ready by fingering her deeper with my right hand and kissing back across her right ass cheek. Finally my left forefinger used its remaining lube to make it easier to inch inside her ass. It had to go very slow, although Jenna’s groaning suggested she didn’t mind; or that she wanted it in faster.

I stuck with the slow mode as the tip of my finger went slowly in and then slowly pulled almost all the way out. It repeated the pattern several more times, as her tightness down there began to get clearer. Soon I decided it was warmed up enough for the next step, as I pulled all of my fingers out and ate her pussy out again for a while. This was to get her juices on my tongue before I licked up her pussy and glided it up into her ass.

Fingers from both my hands were playing with her pussy, as my tongue circled her asshole and further lubed up the outside. Since Jenna was now moaning louder and pushing her ass right into my face, I now safely assumed she wanted me to get on with it. So I took the plunge and plunged the tip of my tongue into her ass, burying my face inside as well. With my tongue working her ass and my fingers working her pussy all at once, I figured it was a matter of time before Jenna blew up; hopefully just from her pussy.

“Yes….oh God, keep fucking my pussy and my ass,” Jenna demanded. The way her pussy was going, I wouldn’t have long to finger fuck it before it went off. So I circled my fingers inside of there while my tongue circled inside her ass, then it pulled out to lick up and down her crack. It kept going down until I moved my fingers away and stuck my tongue back in her pussy; hopefully having it go from up her ass to up her pussy would be the final blow.

My theory turned out to be quite correct, as Jenna further pushed herself onto me right when her pussy went off. Her cum soon drowned out the taste of her ass on my tongue, as I licked up and swallowed her for the second time ever. On the other side, Jenna’s mouth was free to cry out and draw out her ecstasy as mine finally stopped moving. We both took a while to rest our lips and tongues as we stayed in place, my face still up against her backside.

“Oh fuck….you are some first timer. But I already knew that,” Jenna finally got out. “Do you want to sit down now?”

“I don’t mind staying like this for a while longer,” I quipped.

“When you’re done and ready to sit, let me know…..so I can move and suck your cock before it goes into my ass.” That helped give me the kick start I needed to move around again. After getting up on my feet, Jenna rolled over and got on hers as I sat down right where she bent over. This time, she went on her knees in front of me and quickly got to work sucking my cock.

Like me, she didn’t get to oral work last time until the very end, so I did wish this could go on faster. Especially as she trailed her tongue all over my shaft, which was necessary to lube me up anyway. She soon went to bobbing up and down my cock and using the moisture from her lips to get me wetter. I tried not to throw my head back so I could keep looking at her go, but it was a losing battle on at least one instance.

Since I came not too long ago and working on her ass and pussy couldn’t have gotten me that close to going again, I could let her keep going a little longer. I was ready to follow through on that before she took her mouth off of me with a pop. “I think you’re lubed up enough….at least enough for you to last longer in me.” That evil little minx.

Since she wanted to get under way and probably didn’t want her saliva to dry on my cock, Jenna hurried and bent over in front of my room desk; which fortunately happened to be in front of a mirror. Now I could see the reflection of the front of her body while I fucked the very back of her; like I did with Christina, except I didn’t work her ass. But it would be different with my very first redhead as I stood up behind her to let her take my anal celebrity virginity.

First I worked some fingers on her pussy and collected up whatever wetness I could, then placed the wetness over her asshole to further prepare it for what was coming. I put some spare juices over the head of my cock just in case, then figured I needed to go in before my dick got dry again. With that, I gripped the table with my hands placed right next to hers, as my head made its initial push into Jenna Fischer’s ass.

I just kept the tip of my head in for a few moments and then tried to put more of it in. Jenna whimpered a bit, so I tried to soothe her by kissing her shoulder and going up to her neck. I wanted to kiss her on the lips, but then I realized why that couldn’t happen. “Dammit, I should have brushed my teeth before now. Then I could have kissed you and you wouldn’t have had to taste so much of yourself.”

“Too late now…..I’ll just have to risk it,” Jenna concluded before she turned her head to kiss me. I didn’t know how to feel that she might be tasting her cum and her ass on my tongue; yet her tongue didn’t recoil as it touched mine. Eventually it relaxed me and it even relaxed my cock as the head slipped completely in.

I started to very slowly thrust it into her ass as we kept kissing slowly. Kissing like that while my cock was starting to invade her ass was a contrast that I found pretty arousing. I added to the sensation by once again getting a hand on her tits, as I worked on them while I was working inside her mouth and ass. By the time we broke our kisses, my shaft was halfway inside her and beginning to more easily move in and out.

“Okay then….now fuck my ass, baby,” Jenna all but whispered. I never wanted to refuse the request of a lady; despite this very un lady like position. But I made the best of it as both my hands cupped her tits while I steadily increased my thrusts into her ass, despite not going all the way in yet.

I had to flash back to summer 2006, a year and a half before I met Jenna. Back then, she was in a nude photo for Jane Magazine in which she stood sideways, with a sheet covering her front while the side of her back and ass was exposed. Seeing how full and round and deliciously curvy that part of her ass was helped me through a few summer nights; and now here I was thrusting inside that same ass. So at the least, I was coming full circle in a way that predated March 2008.

But I didn’t want to come full circle yet, as I still had work to do. However, it would get a little harder to hold off now that my cock was almost all the way inside. Jenna did the rest by pushing her ass up again, covering the final inch of my shaft and putting my balls right near her pussy below. After all that happened, there was no way she would be able to cum before I did, so the least I could do was warm her up for now.

My left hand left her breast and slid down her stomach until it reached Jenna’s pussy. Once again, I would work both her holes at once as my finger teased its way inside. But I also still had a spare hand for her tits, with her right still grasping them and bouncing them up and down. With my cock in her ass, my finger in her pussy, my free hand going over her tits and my eyes trailing over the reflection of her face and body in the mirror, it was a major whammy for both of us.

I capped the multitasking off by leaning forward and placing my chin on her head, planning to then kiss the back of it and bury myself in Jenna’s red hair like I did with Emma. Jenna wasn’t able to multitask as much, as she could just grasp the table and press her ass back against my groin while she groaned; although less was more on these occasions.

I had gotten good at lasting inside an actress’s pussy, to an extent. But since this was my first anal experience with one and since this was Jenna, I knew I’d probably go sooner than usual. And that sooner felt like it wasn’t far off. “Mmm, God, oh…..gotta pick a place to shoot off soon…..”

“Keep it right there! Keep going and keep right there!” That order did make sense, since Jenna was probably extra careful about getting cum in her pussy so soon after her pregnancy. Plus there was no chance in Hell I was letting her suck me off after this event; not unless she asked. She didn’t, so that left me only one option.

I pulled my head from her hair and focused back on her ass to help drive me to the finish. My hands left Jenna’s tits to get a grasp on both her cheeks, moving them around to help push me closer. In between, my gaze also went to the mirror, where I could see Jenna’s flushed face, gaping mouth and her tits bouncing. I moved my head to my right so she might see my flushed, nearly orgamsic face in the reflection as well.

From that angle, we looked at each other without actually looking at each other, giving silent encouragement to reach our climax; or at least mine. Then it didn’t become silent as we both groaned while she clenched her ass tighter around me, even as I was already clenching it with my hands. I heard Jenna mutter “Come on” in between her groans, and soon enough, I became so driven to the edge that my yells drowned out hers in my mind.

With the noise filling my ears and my eyes almost seeing stars; which was preferable to a tabloid flashbulb; I finally managed to fill her ass to the brim. I hugged her backside against my groin as I nearly collapsed against her back, which made it fortunate that she stayed upright as well. “I think…the bed looks pretty good again,” I mustered, as I carefully slipped out of Jenna, backed up and let myself fall back onto the bed. After a few seconds, I heard Jenna do the same next to me.

“Now I guess you’ll have to fuck 10 more celebrity asses after mine,” Jenna spoke out.

“I think a formula like that only works once,” I pointed out, playfully tapping her on the top of her right leg. I then turned to my side to see the rest of her, looking up and down and stopping at her pussy. At that point, I remembered I was ahead of her in orgasms by 2-1. I figured what I just pulled off had to gotten her close, so it shouldn’t take that much to make us even.

I reached my left hand over to start working on her other opening again. For added stimulation, I finally decided that my hands had enough fun playing with Jenna’s tits, as I put my mouth back on them again. After a few moments suckling her right breast, I positioned myself on top of her to get easier access to both her boobs, as my fingers kept doing their job.

After the intensity of the last several minutes, I reasoned I needed a slower approach to relax the both of us. So my fingers circled around her pussy, rubbed her outer lips and occasionally went inside her without rapidly going in and out. In the meantime, my oral tactics on Jenna’s breasts also felt like they were paying off.

Since Jenna was vocal enough earlier, her moans were a little softer this time, but she still looked and felt plenty aroused. In case she was close, I decided to stimulate everything else that I could before it was too late. In addition to kissing her tits, I went up to her upper chest, neck and throat in the next minute or two. Finally I reached her lips, given how we established that this didn’t bother her.

While we were making out slow and steady, Jenna’s muffled groans were increasing in frequency as my fingers picked up the pace. Our tongues worked a little faster, as I tried to lick her tongue and the inside of her mouth like I would with her pussy. But when Jenna started to try and clench her jaw, I realized I should probably pull back before she bit my lip or tongue involuntarily. And it was the right call, as I felt her spasm into my hand several seconds later.

Once again, Jenna slowly came down after an orgasmic peak, only this time it was her own. With her ass worked out and her pussy now worn out for a second time, it was clear she was exhausted by now. Therefore, I brought my hand over and tried to lick it clean, then leaned back on the bed a little tired myself. With that exhaustive workout and the fact that our little sexual reunion was over, there was little we could say as we each decided to get a nap.

When I woke up, I found that it was almost 4 a.m. and Jenna was no longer next to me. Instead, she was standing up in front of the mirror again, only now she had her dress back on and was fixing herself up. “Oh! This saves me a few seconds waking you!” Jenna explained as she saw me get up from the mirror. She sounded no different than she did before she had anal sex with me, so at least she appeared rested.

“So you have to get going,” I concluded. “Thank you for wanting to wake me for that, then.” I genuinely didn’t want that to be taken the wrong way, since I did want to be up to have a proper goodbye. But I hoped it wasn’t too easy for her to see that differently.

“Are you going to be okay?” she asked. The first response that came to my mind was “Me? After what we did, I have more of a reason to ask you that.” That was the most delicate method I had to ask about the condition of her ass.

“I can walk and I’ll be able to sit, don’t worry. You left an impact on me, but not quite like that,” Jenna reassured.

“Good. Then I guess this is….” I trailed off before I said the “g” word.

“Let’s not say that yet. We’re old friends who caught up on old times….maybe we won’t do it like that again, but we can’t say we won’t see each other again. Once NBC or some other network or studio hires you, I’m sure we will.” That was as much of an optimistic way to look at it as any, I supposed, so I just nodded and walked with her to my door. In case she was wrong, however, there was no point holding any words back.

“Maybe we would have….gotten to where we are now without knowing each other,” I started. “I know you’d have done that even if I didn’t. But being with you meant as much to me than it did with the others, if not more so….it did even before tonight and it would have even if you weren’t my first. I just thought you should know.”

“I already had an idea, but thank you. And I hope you know how much you helped me and got me on my path too. Now four years later, I have special people to get back to and so do you. Whatever part you had in that….thank you for it. And I accept your thanks for getting you on your way too.”

Jenna put an exclamation point on those final words by leaning in for a final kiss. I didn’t act fast enough to return the first one, but I got into it for the second. Yet by the time I realized it might be our last one, she broke off and reached for the door. In somewhat of a panic, I put my hand on her face and went in for one more kiss, fully ready to savor it as a last one. After we went back at it for several seconds, I stopped myself and broke off before I went for a few more final intimate acts with her. On that note, Jenna just laughed warmly, opened the door and kept her eyes on me until she left my view.

That image filled me for the next several minutes as I went back to bed; not caring that I was still naked. But before I drifted off, Jenna’s comment about going back to special people finally registered; as did who she was probably referring to on my part.

I woke up again about four hours later and eventually made an effort to get dressed again. Once I did that, cleaned myself off and thoroughly brushed my teeth, I went down to the hotel lobby to get a newspaper and a few snacks. When I got there, I saw none other than Alison sitting nearby, right before she noticed me and waved me over. I braced myself and went over to sit next to her.

“I had a pretty good night with the guys. How about yours?” Alison asked as if it was a normal question.

“It went just as you hoped….or at least expected.” Alison smiled and nodded, yet I thought I should clear up some things in case it wasn’t all genuine.

“You should know that although I loved this….little favor, you don’t need to go overboard with favors like that again. If….what you set up made you uncomfortable or jealous in any way, I’m sorry. But I won’t ever need anything like that again. After that, now it’s all out of my system….whether or not that was one of your goals. I’m not a temp anymore, I’ll hopefully start some kind of career on my own two feet soon, and I’ve been with every celebrity crush I can name. Basically, I’m out of the sex with actresses game now….at least sex with multiple actresses. I just thought you should know that.”

“I….appreciate you sharing that with me,” Alison started to respond. “Of course, we can’t say what’ll happen in the future. Hell, we didn’t see stuff like this happening a few years ago, how could we? But whatever stuff comes out of nowhere later, I do want us to be there for each other however we can. I guess I don’t need to be that….thorough in the future…..but I can be there in smaller ways too.”

“I never doubted that for a moment,” I stated honestly, as Alison let out her bright smile. Looking back one last time, it did make sense that this all started with Jenna, and ended here with another NBC comedy scene stealer that played a funny, bright, adorable, gorgeous and secretly sexy character; while also being all of that and more off screen as well. Of course, Alison’s beauty was more openly flaunted on and off screen than Jenna’s, but I could ignore that nitpick. In any case, the premise of how the beginning influenced the end still stuck.

“Well, um….I originally came here to get the paper, read a bit and then pack up before checkout. But I can fit in a little walk and sight-seeing with you before we get going. If you’re not too tired,” I offered.

“If you’re not that tired for some reason, I guess I shouldn’t be too,” Alison answered. “But I should go back to my room and get fixed up first. Maybe get in a little packing so that doesn’t bug me later.”

“Yeah, I’m too anal to let that go too,” I stated, trying desperately to ignore my choice of words. But it helped when I proposed “Come on, I’ll escort you to your room and then meet you back here,” to Alison. She nodded and then got up with me, as I resisted the urge to do another “Milady/Milord” reprise bit with her; albeit barely.

We headed to the elevator and just had to wait a few seconds before the doors opened. I signaled for her to go in ahead of me, then I got in and pushed the button for Alison’s floor.

I then stood there with my hands behind my back as the doors closed; as if the last four-and-a-half years of sex, celebrity wish fulfillment, secrets, infamy, getting a foot in the door and winding up with Alison Brie standing next to me hadn’t just gotten their exclamation point.

THE END