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An Unusual Request

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College

The Usual Disclaimer: This is a work of fantasy. All characters featured in sexual situations are over 18. The characters in these stories are fictional. Any resemblance to actual persons living, dead or undead is purely coincidental. Do not try this at home.

*****

My parents divorced when I was very young. I know that my father was in the Air Force, and that I was born in Oklahoma, but I don’t remember any of that. The earliest memories that I do have were well after my mother remarried, when we lived in central California. I always referred to my stepfather as “Dad” and everyone was fine with that. I did meet my father twice. He visited very briefly when I was twelve and again when I graduated from high school.

Mom died of ovarian cancer when I was in my early twenties. It was horrible. Dad was left to raise my two younger brothers on his own, but he remarried after just a few months. That was tough for me to swallow, and it created a rift between us. After that wedding, we drifted apart and I stopped being a part of their lives. I certainly hadn’t been a part of my biological father’s life. I was on my own and became comfortable with that.

None of this would really matter except that I have an older sister. When our parents divorced, Tonya went with our father to Georgia. I had no recollection of her whatsoever, and she had not accompanied my father on either of his visits to California. Tonya was six years older than me. I had five pictures of her, spread out over fifteen years. The last one was from her college graduation almost a decade ago.

We had never talked, so it came as a complete surprise when she called me. At the time, I was working on my master’s at UCLA. I had brewed a fresh pot of coffee and was on my way back to my desk with a steaming mug when my phone rang. I looked at the screen and saw an unknown number from Georgia. It didn’t seem like one of those telemarketer numbers, so I answered it.

“Hello?” I said.

“Scottie?” a woman’s voice asked. That took me back a bit. I hadn’t gone by ‘Scottie’ since junior high.

“This is Scott,” I countered, “Who is this?”

“It’s Tonya, your sister,” she replied.

“Wow, this is an unexpected surprise,” I said. Of course, I immediately thought that our father must have passed away. It was the only thing that made sense, and I braced myself for that news. “To what do I owe the pleasure?” I asked.

“I’m in L.A.” she said. “Dad told me that you live here now, and he said I should look you up while I’m here.”

“Oh,” I said. Since I had been preparing my response to the bad news that wasn’t coming, I was not sure what to say. I thought for a moment. “Are you at the airport?” I asked.

“No,” she replied, “I’m at a hotel in Anaheim. It took a couple of days to get your phone number.”

“Okay,” I said. “What brings you to L.A., Tonya?”

“I was visiting with a friend from high school,” she said. “But that…well, it just got too weird for me. I called Dad to let him know I was heading back to Georgia, but he said I should look you up and visit with you before I leave.”

She had a rental car with GPS, so I gave her my apartment address. It was not terribly far away, and it was late evening so the traffic wasn’t horrible. I had time to shower and change clothes before she arrived. “You never get a second chance to make a first impression,” my mother’s voice said in my head during that shower. I had to smile softly. The woman had been gone five years, but she was still with me.

I put on khaki shorts and a light blue polo shirt. It was what I almost always wore unless I was working on something that required me to dress up or dress down. Civil engineering projects might mean that I would be inspecting a sewer system or addressing a board of directors. By now I was equally comfortable in either environment.

Tonya called when she got close, and I headed downstairs to meet her and show her where to park. It was a little awkward when she got out of the car; she started to give me a hug and I held out my hand. Then we switched—she held out her hand as I opened my arms. We both laughed at that, and settled for an uncomfortable hug.

Tonya looked me over after that brief hug, and I did the same. She was shorter than Mom, with darker hair. Her blouse revealed generous, creamy cleavage. Her blue-green eyes matched my own. I realized that she was not wearing a wedding ring, which made me a little curious. Years before I had heard she got married. She smiled up at me after that brief inspection, and I turned and walked next to her as we headed for the elevator.

We were still a little awkward around each other. Even though she was my sister, we were essentially complete strangers. Tonya seemed nice enough. She was clearly only uncomfortable because the situation was as unique as it was. I could relate. When we got to my apartment I asked if she wanted a drink.

“Nothing too strong,” she said with a lovely grin. “I am driving.”

“Meh,” I responded with amsterdam shemale a shrug. “If you get too wasted you can always crash out here.”

That broke the ice for both of us. She looked through my selection of liquor and settled on a rum and coke. I made one for myself and we sat and sipped our drinks while we chatted.

“I hope you don’t mind,” I said, “I heard you were married, but you’re not wearing a ring. So…?”

“Yeah, that didn’t work out,” she replied. “We figured it out right away, and we got divorced less than two years after we got married. I’ve dated off and on since, but nothing long term. How about you? Should I expect to meet your significant other?”

I shook my head, briefly considering and discarding the idea of making a bad joke. “I haven’t been seeing anyone for the past few months. The last two women I was seeing were…very casual relationships.”

Tonya nodded as she took another sip of her drink. “Is everyone like that out here?” she asked.

“What? Casual?” I asked. She nodded, and I had to think about it. “Not really,” I said. “I think everyone’s just really…permissive, if that makes sense. They go to great lengths to not be seen as judgmental, as if that was the worst thing you could possibly be. It doesn’t stop people from having intense relationships.”

“I see,” she said thoughtfully.

It reminded me that she had said something on the phone about visiting a friend here. I didn’t know if I should bring it up. Instead, I opted for a safer topic.

“I presume you’re still living in Georgia, then,” I said. When she nodded, I asked, “What are you doing these days?”

“I work in a fertility clinic,” she said.

“Are you a nurse or a doctor?” I really didn’t know.

“No,” she chuckled, “I’m a paralegal. I make sure all the paperwork is in order and cover our butts so we don’t get sued. I have a certain amount of oversight to make sure everyone follows procedures, and that nobody’s privacy is compromised. That sort of thing.”

I tried to picture that, but couldn’t. “Do you like it?” I asked.

“Nope,” she replied, taking a big sip. “That’s part of why I came out to California. A guy I knew from high school thought he had a more ‘interesting’ job for me out here.” She shook her head at that thought.

I was completely in the dark. I didn’t have the first clue what she was talking about, didn’t know enough about her or her friends from high school to even conjecture. I also didn’t want to press her if she didn’t want to talk about it. I sipped my drink and swirled it in my hand while I waited to see if she would volunteer anything else.

She looked at me speculatively for a bit. Finally, she did speak up softly.

“Scottie—sorry, Scott—you would give me your honest opinion if I asked, right?”

I thought about that for a couple seconds. “Sure,” I replied.

“Should I be insulted that this guy offered me a job as a fluffer?” she blushed a bit just asking the question.

I was familiar with the term, but hadn’t ever met anyone involved in the adult film industry. I opened my mouth to answer, but then closed it and made a ‘hmm’ as I thought about it. Tonya was looking at me closely, so I made myself form a response.

“My immediate response would be ‘yes, you should be insulted.’ However, I realized as soon as I was going to say that that I really don’t know. I mean, I don’t know what is actually involved. It is one of those terms that probably gets misused. It sounds like a really demeaning job, but I…” I trailed off and blew out a breath, taking another swig of my drink. I gathered my thoughts and looked at Tonya. “Is the job that you would suck guys’ dicks to get them hard before they go on camera?”

Her blush deepened. “Yeah, that and showing them my tits to get them hard. Not just before they go on camera, either. If they go soft during a scene, they would expect me to get in there and get them hard again.”

I shook my head. “Why on earth would he think you would want to do that?”

Her voice was just above a whisper. “Because…back when he knew me in high school, I loved it.”

“Oh,” I said. Even though I had been sipping that drink, my mouth was suddenly very dry. I shook my head and tried to stop picturing Tonya sucking a dick. “I thought they didn’t do that anymore,” I finally managed to croak out. “I thought all those guys used Viagra now. Maybe this guy was just messing with you.”

“It wasn’t a joke,” she said, shaking her head. “He had a contract and everything. It would have paid me three times what I was making.” She drained the rest of her drink. After she swallowed it, she asked, “Mind if I have another?”

“Yeah, no problem,” I replied, getting up to walk over to the counter with her. I couldn’t help myself. I began checking her out from her feet up her shapely thighs, and she caught me ogling her gorgeous ass. It was my turn to be embarrassed. I blushed when she chuckled.

“Are you picturing me naked?” she asked.

“No! rotterdam shemale I…” I immediately started. Then I rolled my eyes. “Well, now I am. But I wasn’t before you said that.”

She laughed at that, and her body shook in a way that made my eyes roam over her breasts even though I was trying hard not to. I covered my eyes with my hand, and she just laughed harder. I waited for her to stop laughing, and then I peeked out between my fingers with my left eye.

“Are you done?” I asked. Of course, that just made her start giggling again. She turned away from me to mix her drink, but she shook her hips slightly. I couldn’t help but notice. She was enjoying this, I realized.

I stepped around her to mix my own drink, and my mind was reviewing what little I knew about the adult film industry. It was all from HBO specials that I had seen years ago. I had always assumed those documentaries were accurate, but I didn’t really know. I could not recall any episodes that dealt with fluffers. All of it was directors, actors and actresses and aspiring actresses. It did make me think of a question.

“Were you insulted that he offered you a job as a fluffer, instead of as a porn star?” I asked.

“Not really,” she replied. “I had told him, when I found out what he did, that I couldn’t appear on camera. I mean, I’m thirty years old, and I might still pursue a career as a lawyer. Most women in the industry are retiring by the time they’re my age.”

“Really?” I asked. “I thought there was an awful lot of ‘MILF’ porn out there.”

“Thanks a lot,” she said dryly.

“No! I wasn’t saying you look…” I trailed off when I realized she was grinning. I grinned back, shaking my head. I realized that the awkwardness had changed subtly. We had started off being awkward because we were siblings who didn’t know each other at all. Now it was this subject matter that made everything awkward. We took our drinks back to the couch.

“Did you talk with your dad about any of this?” I asked. I winced. “I mean Dad. I know I could never have had this conversation with Mom.”

She looked at me thoughtfully. “I didn’t, but now that you mention it I think Dad knows what this guy does for a living.” Her eyes had a faraway look as she slowly took another sip of her drink. After a bit, she looked at me again. “I turned down the offer, of course. I felt like I should be insulted, but he was just so…casual about it. He said I should think it over and get back to him. I wasn’t even going to think it over. But I’ve had two more days here and I have to admit I’ve thought about it a lot.”

I raised my eyebrows, but had no idea what to say. I sipped my drink instead. Tonya was licking her lips a lot as she talked, and I doubted that she realized she was doing it. Every time she did, I could almost picture her licking the swollen head of a fat porn star dick. It was disconcerting, and I realized that I was shaking my head an awful lot trying not to picture that.

“So, what are you thinking?” she asked.

“I’m trying not to picture you doing that,” I replied, shaking my head once again. “This is really weird, Tonya, you have to admit. I know next to nothing about the adult film industry, outside of a few HBO specials. I am certainly not qualified to offer you any sort of career advice. Anyway, I thought you weren’t going to consider this seriously.”

“Oh, I wasn’t,” she said wistfully. “It just seemed so outrageous. But…I just didn’t think I could do it. It’s just been so long.”

“What?” I asked. I felt like I had missed something there.

She looked right into my eyes. “I used to love giving blowjobs. Back in high school and college, I could not tell you how many guys I went down on. That was a long time ago, though. I have only given…twelve or thirteen blowjobs in the past two years.”

I grunted at that. I hadn’t had that many blowjobs in the past…hell, ever. Tonya looked at me.

“What?” she asked.

I shook my head. “That’s more blowjobs than I ever got,” I replied.

“Are you serious?” she asked. I nodded and she grinned as she shook her head. “It’s a shame I’m your sister,” she went on. “I have been thinking about sucking dick almost the entire past two days, and it’s gotten to me.”

My cock stirred in my shorts when she said that. It did not go unnoticed. Tonya looked from my lap up to my face. Then she turned and looked at her glass. It was a little over half full. She set it on the coffee table.

I felt like I could follow that thought process. We had not had enough to drink that we were drunk, or even buzzed. The glass and a half that I had consumed had been relaxing me, but I felt myself tense slightly as I tried to figure out what she would say next.

“Scott, do you watch a lot of porn?” she asked.

That hadn’t been what I expected. “Actually, I don’t,” I replied honestly. “Maybe once or twice a week I will watch some. Usually, I’m just too busy.” I stood up and offered her my hand. “Let me show blog shemale you my office, and what I was working on when you called.”

My apartment has two bedrooms, but one of them serves as my home office. I have a long workstation set up along one wall, with a really large flat screen monitor attached to a fairly powerful desktop computer. There is a docking port for my laptop, which keeps the two of them synced. It makes it easy for me to carry my current projects around, while giving me impressive computing power. I wiggled the mouse to clear the screen saver, so she could see the project notes, blueprints, and a 3-D rendering on screen.

“This is the kind of thing that takes up most of my time,” I explained. “This is one of five projects that I am currently working on. I’m also taking two classes, and I am the TA for another. I stay pretty far ahead of schedule, which is why I’m not freaking out about not working on this right now. But this is what I do, and it takes up so much time that I haven’t dated in months. About once or twice a week, I need to…you know.”

“Oh,” she said. She licked her lips and her eyes dropped to the bulge in the front of my shorts. “When is the last time you…you know?”

This time I managed not to blush. “Five days ago,” I replied.

“Five days’ worth,” she breathed. I could tell she hadn’t meant to say that out loud. In fact, I don’t think she realized that she had.

“Why did you want to know if I watched a lot of porn?” I asked.

“Well, I was thinking about the guys who are in those pornos,” she said. “They see gorgeous, naked porn stars all the time, and they get to have sex with them. I just didn’t think I could be any good as a fluffer; I can’t compete with those women.”

Her eyes were downcast when she said it. I looked her over, and couldn’t help myself.

“You look amazing to me,” I said.

“Thanks,” she whispered. Her eyes were once again on my crotch. Just knowing she was looking there made me harder. She licked her lips again and looked up to my face. “I was thinking, if you watched a lot of porn, that I could see if I could compete with that,” she said.

“I…don’t understand,” I said. She thought about what she had said, and shook her head in annoyance.

“Yeah,” she said slowly. “I guess it’s just too weird to ask.”

“You’re in the land of weird,” I laughed, “Try me.”

She looked intently into my eyes and then shrugged. “Okay,” she said. “I was thinking that if you looked at some porn—at the hottest porn star you could think of—and then you jacked off, I could see if I could get you hard after that.”

I had pushed her to admit that, so I stopped myself before asking if she was serious. Clearly, she was embarrassed that she had said it out loud, but she did appear to be serious.

“That’s…an unusual request,” I said.

Tonya reached up with her right hand, and her fingers toyed with the edge of her blouse where it revealed the inner curve of her right breast. I was aroused. I had no doubt that I could find some porn and jack off. At that point, I was intensely curious to see what she would do to get me hard afterward.

“Okay,” I blurted out, surprised to hear myself say it.

“Seriously?” she asked.

It was my turn to shrug. “This whole conversation has been weird, but it has got me turned on,” I admitted. “I would probably be looking at porn and jacking off as soon as you left anyway.”

I saved my work on the computer, making sure it was backed up to the laptop before I closed that screen and the associated documents and files. I slid into my comfortable office chair and brought up my favorite search engine for porn. I turned in my seat to face Tonya, and gave her a wry smile.

“I guess we’re really doing this?” I asked. She nodded and bit her lip.

Now, I had expected that either she would change her mind, or she would let me know she was serious before leaving me alone to jack off to porn. I did not expect her to stand there and watch me do it. Quite honestly, I did not know if I could do that with her watching me. So I sat there and she stood there, while I tried to think just how to put it into words. Instead, I chickened out of saying anything. I swiveled my chair back to face the screen, and began to search for a hot porn star.

I clicked on the first link that caught my eye and switched to full screen view. A busty porn star filled that large screen as she demonstrated her cocksucking skills. I rubbed my hard dick through my shorts. Behind me, Tonya cleared her throat.

“Are you really planning to jack off in your shorts?” she asked. I turned and looked at her. “Go ahead and whip it out,” she said. Her tone was light, but the look in her eye told me that she really wanted to see my dick.

It wasn’t as if I had never let a woman watch while I stroked my dick before. This was different in a lot of ways. I realized that it wasn’t so much that she was my sister as it was that she was a complete stranger. I wished that I had the excuse of being drunk. From experience, though, I knew that if I got drunk Tonya would have no chance. If I managed to get it up long enough to jack off, my dick would be dead to the world afterwards no matter how amazing the stimulation.

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