An Uncomfortable Situation

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A brother and sister at college make their way.
7.5k words
4.76
399.9k
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Part 1 of the 6 part series

Updated 10/24/2022
Created 11/01/2008
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It's nothing new that college students will go to great extremes to pay for college tuition. My sister Allison and I are no exception.

It was challenging enough on our folks financially that we were twins. Growing up, it was always twice the expense for almost everything. An older brother and a younger sister just added to the stretch put on the dollar at our house.

Alison, my twin sister and I, were born about five minutes apart. She's never let me forget that she's the oldest. It's all fun and games until I call her an old lady, and then, depending on her mood, she gets real pissy.

We both did pretty well in school and managed to swing partial scholarships to college when we graduated. Suddenly, we were almost four hours from family, alone, but together.

Our freshman year was tough. We stayed in the dorms, and although we made a lot of new friends, it was tough, especially when big weekends would come around and we were working odd jobs of one sort or another to pay bills.

Did I mention Ali's a hottie? She doesn't like to hear me say it; she thinks I'm mocking her. But it's true. She's beautiful, in a natural sort of way. And when she decides to get herself all made up, like when she's going on a date? Wow. More than once I've really wished it was me taking her out. The only problem was the money thing.

Because we weren't money privileged, a lot of the people we would have liked to call friends looked down their noses at us. Ali endured a long string of guys who seemed to want just one thing. I only went out on three dates the entire year; it seemed I didn't have enough to lure the material girls.

As our freshman year came to close, we both managed to land jobs for the summer. The only problem was housing. We couldn't afford the dorm for the summer, and we couldn't find roommates. Finally, in a last ditch effort, a t out parents' urging, we rented an apartment together. We each had our own room, but other than that, it was definitely no frills. Most people hadn't made the connection between us, and we overheard at least one person remark that the two of us had started dating and were moving in together.

Home sickness had been a scourge that entire first year away from the nest. The first week we were alone in the apartment was brutal. Almost all of the people we knew were gone for the summer, or at least until the summer session started.

It finally became too much one night. I thought I heard something coming from the apartment next door. After all, the walls were pretty thin.

I got out of bed and made my way out into the hall. The noise grew louder as I came closer to Ali's room. She lay in her bed, facing the wall, hugging her pillow to her body and sobbing.

"Ali? Ali, what's wrong?"

She sniffed hard, wiping at tears she didn't want seen.

"Nothing," she said. "I'm fine."

I walked into her room.

"I can hear you crying, Sis. What is it?"

Alison rolled over to look at me.

"It doesn't bother you at all, does it?" she asked. "Being this far from home and everybody?"

"I'm not that far from everybody," I said. "I've got you."

It was the wrong thing to say; it was the right thing to say. The tears started again, but Ali reached for me, her hand grabbing mine. I began to think I was never going to get my hand back; I thought she was going to keep it.

We talked for almost an hour, me sitting on the edge of her bed wearing nothing but boxers, her laying there, bed sheet pulled up to her waist wearing only a thin night gown. She kissed my hand.

"I love you, Tommy," she said.

"I love you, too," I said. "Even if you are a whiny old woman."

Her mood was light and playful. She swung her pillow at me.

I went back to bed.

I'd just gotten comfortable, sleep coming swiftly when I felt her beside my bed.

"Move over," she said as I looked up at her.

Easier said than done; twin beds aren't noted for their bounty of space.

Ali slid in the bed beside me. She grabbed the covers and pulled them so that she had enough to cover her. I felt her lay down behind me, tangling her feet with mine, her naked legs brushing mine. Her nightgown wasn't just thin, it was short, too. Her arm slid under mine, looping around my body as her head nestled next to mine.

I felt her lips on my shoulder.

"Goodnight, little brother," she said.

The two of us in bed together wasn't a new concept. In fact, it was a fight we'd waged against our parents for years. From the time either of us was able to crawl out of our toddler bed into the other's toddler bed, we'd been forever crawling in to sleep with each other, the warmth and comfort of our twin sibling. It was a hard habit to break, and one that continued off and on well into adolescence. And then it became awkward for a host of reasons.

But tonight, it just felt right. We were alone. We were together. It never registered that I felt her breasts pressing against me, only a thin layer of cloth separating us.

Ali lucked out right before the summer session, landing a veritable cash cow of a job. A couple of local artists were constantly in search of models for their artwork. If they found a subject they liked, it was not unheard of for the student to find a full year 's employment as the focus of the artist's pencil. Ali answered one of the ads before the spring semester ended, and after two meetings, she was promised work for at least the summer session, the fall semester, and maybe longer if she wanted it.

My sister was suddenly like a new woman. The modeling would have been her third job, but she cut back so that it was only her second. She began carrying herself differently, and I was really happy for her.

Two weeks after she started posing, I came home and found her jumpy and irritable.

It took me most of the night, but I finally got her to tell me what was bothering her.

"She wants me to pose naked," Ali said. "With my clothes off."

"I think they call it 'nude,'" I said.

"'Naked, 'nude,'" she said. "She wants me to pose without any clothes on!"

"What's the big deal?" I asked. "Models pose nude for artists all the time."

Ali stared at me in stunned silence.

"How can you be so insensitive?" she asked.

"I'm not being insensitive," I said. "When you answered the ad, she told you there would be some nude modeling."

"I know," she said, folding her arms across her chest and sitting back hard.

"I just didn't think about it," she said, "and next week, she wants me to start out partially undressed, then she wants me to strip down to my underwear, and depending on how time runs, she wants me to take off my bra and panties."

I took a sip of my soda.

"Well," I said, "there aren't any guys there watching."

"No," she said, "but part of me thinks I'd prefer being naked in front of a man instead of a woman."

"That's just silly," I said.

"Really?" she asked. "So you wouldn't have a problem being naked in front of a man as opposed to in front of a woman?"

"That's different," I said.

"Different because it's me and not you," she said.

"Look, Sis," I said. "Think of it as though you're going to the doctor."

"The doctor at least gives you that ridiculous gown to put on," she said.

She at least had a few days to warm up to the idea. The only problem with the time she had to warm up to the idea is that it was time she had to warm up to the idea.

I came home from my job three nights later hot and sweaty from work. I did a double take as I shut the front door. Ali sat on the couch wearing nothing but panties and a tank top.

"What?" she asked, noting that I'd stopped to stare.

"Nothing," I said. "But when did you start sitting around in your underwear?"

"I'm getting used to being undressed," she said.

She stood up off the couch and walked toward the kitchen. Her nipples were hard buds of flesh clearly outlined against the fabric of the tank top.

"I'm going to go take a shower," I said.

"Okay."

I turned to go to my room, but not before I watched Ali pull open the freezer, clenching her butt cheeks together as she stood on her tiptoes to peer into the back of the freezer.

I crawled into the shower ignoring two really strong urges; the first was to take a cold shower, due to the fact that, second, my cock was hard, excited by my sister's scantily clad state.

It had been a long day, and when I came out of the shower, I donned my boxers and went straight to my room, my cock still annoyingly erect inside my boxers. I crawled into bed and pulled my pillow into my lap as I flipped open one of my school books to do some reading.

A few minutes later, I caught Ali walking down the hall toward my room, still scantily clad.

"Did you read this section yet?" she asked, flopping down on my bed.

My hand scrambled to grab the pillow as she pushed at it in an effort to make room for her to sit down.

No luck. The pillow slid out of the way, revealing the tent in my boxers.

"Oh! Wow! I, uh..."

Her close proximity wasn't helping any; my cock swelled, making the tent bigger as she brushed against me.

We made eye contact. Both of us blushed.

"Sis, I'm sorry," I said.

"Don't apologize," she said. "I think it's sweet."

Alison leaned forward and kissed me on the cheek.

"I like it that I'm pretty enough to make you hard," she said.

She sat back, a sudden troubled expression on her face.

"That is... why you're hard," she said, "isn't it?"

"Y-yeah," I said.

I know you're not supposed to have the hots for your sister, but we were closer than we'd ever been and it was undeniable she was gorgeous. The fact the she was my best friend and beautiful were conspiring with her lack of clothing and proximity to arouse me. It wasn't cold in the apartment, so I guessed, or hoped, her nipples were an indicator she was aroused, too.

Alison looked down at my crotch again, licked her lips and stood up.

"I'm gonna... it's been a long day," she said. "I'm gonna go to bed."

She bent over and kissed me on the cheek again.

She paused bent over for a moment too long. On purpose? I caught a good glimpse of her breasts swaying from her chest.

I watched as she turned and walked out of my bedroom.

"G'night, Sis," I said.

I tried to get back to my reading, but to no avail.

To make matters worse, Alison left the light on in the living room when she went to bed.

I asked her if she needed me to get it, and she said she'd appreciate it.

I crawled out of bed and took a deep breath. My cock was still obviously hard as I walked out of my bedroom. I glanced into Ali's room as I walked past. She was at the edge of her bed, one knee on the bed, one foot on the floor, naked save for the night gown she was pulling down over her body, her breasts just covered.

I turned out the light and headed back to bed. I glanced in at Ali as I passed her room again. Her night gown covered her body and she sat on the edge of her bed. She smiled at me as I paused in her doorway.

I crawled back into bed, my erection throbbing.

The next week, Ali came home from her first day of modeling nude walking on a cloud.

"It was great," she said, sliding into my lap and hugging me.

"I thought you were really upset about it," I said.

Ali sighed and laid her hear back against the chair.

"That was before I knew how exhilarating it could be," she said. "When we stopped, she showed me some of her sketches, and... wow..."

My sister took a deep breath and sighed again.

"Did you say sketches?" I asked.

"Yeah," Ali said, nodding. "Lisa does sketches, lots of sketches with pencils and charcoal. Some of the sketches she uses as a reference for her paintings."

"I'd like to see some," I said.

Ali's jaw dropped.

"You want to see me naked?!"

"I didn't say I want to see the sketches of you!" I said.

"So you don't want to see me naked?" Ali asked.

I couldn't win.

Ali laughed, satisfied that she had frustrated me.

"You're silly," she said, kissing me as she hopped off my lap.

I watched her skip down the hall to her room, peeling her t-shirt overhead before she entered her room. A moment later, Ali walked out of her bedroom and headed for the bathroom wearing only her bra and panties. She turned on the bath and closed the door behind her.

As the first summer session drew to a close, I stayed up really late studying for my exams. One of the classes I was taking was on the verge of eating my lunch, and I was determined to pass it.

Alison had been in bed for more than an hour when I felt her walk up behind me. Her arms wrapped around my neck as she bent over and hugged me.

"How much later are you gonna be up?" she asked.

"Not much longer," I said. "How come you're not studying?"

"Hmmm." Ali laughed softly as she slid into the chair beside me. Tonight she was wearing pajamas.

"I was able to study while I was posing," she said.

I looked at her.

"You're kidding," I said.

"Nope. I was butt naked lying prone resting on my elbows. Perfect for studying."

"It's not fair," I said.

I sat back, rubbing at my eyes.

"You interested in making some easy money?" she asked.

"What did you have in mind?" I asked.

"Lisa wants to do some couples sketches," she said. "You know, simple stuff. Me lying down with my head in your lap; the two of us holding hands; nothing elaborate."

"You already told her I'd do it?" I asked.

"No," she said. "But if you don't do it with me, she's going to bring in someone else and I'll be holding hands with a complete stranger for hours."

"You wouldn't be strangers after all that time," I said.

"Funny," she said. "Think about it. Let me know tomorrow."

She kissed me on the cheek and went back to bed.

It wasn't that much to think about, really. One of my part time jobs was so slow right now I might as well not be working there, and the extra money could come in handy. I decided to call it a night, killed the lights and went to bed.

The next morning, I told Ali I'd pose with her.

I found out that afternoon that Alison had put off asking me to pose with her for nearly a week. Lisa actually needed us to pose for her starting that evening. I rushed through the shower and got dressed as Ali fidgeted and fretted.

I hadn't met Lisa before, and I immediately realized my choice to pose with my sister was the right one. Lisa was warm, personable and very easy to feel at ease around. She and Ali had a little fun at my expense as they had me sit in a couple of positions while Lisa drew quick profile sketches of me.

Then, it was time for the two of us to pose together. It started out simple, warm; some would say sweet. Ali and I stood there, holding hands. It seemed like forever. Then, we stood embracing. All to soon, it was time to call it a night.

Because the summer session was over, Lisa had arranged to make the most of the next few days and she told us she'd see us the following morning.

Walking from the parking lot to our apartment, Ali grabbed my hand, her fingers linking in with mine.

We realized we had long days ahead of us, and so we quickly called it a night. I had just turned out the light in my room when I saw her silhouette walk in.

"I want to sleep with you," she said.

She sat on the edge of the bed, rolling her feet up onto my bed. Neither of us even gave it a thought that I wore only my boxers and she was clad only in a thin gown. She pulled my arm around her, bringing my hand up to her chest.

There was something about the warmth and the innocent intimacy of being that close to my sister for that length of time that made it easy to go to sleep that night. And then I felt her pull my hand to her breast.

We got up the next morning and got ready to go.

Once we were at Lisa's studio, we picked up almost right where we left off. Lisa had me sit down, and as Ali had predicted, Lisa had her lay down with her head in my lap. One minor pose alteration and we were done with the morning. A series of increasingly comfortable, intimate poses rounded out the day.

As we were breaking for the day, Lisa stopped us before we got to the door.

"I'm sure Ali told you she's done some nude posing," she said.

I nodded, looking at Ali, who blushed.

"Great," she said. "What I want to do, starting tomorrow, is some more relaxed, revealing poses."

Ali and I exchanged glances, trying to hide the alarm in our eyes.

"We'll start with you taking your shirt off and her blouse unbuttoned," Lisa said, "the two of you hugging. We can progress to the two of you in your underwear or swimsuits, and eventually, I want to do a series of sketches of the two of you nude together."

"Nude?" I asked.

"Together?" Ali asked.

"Yes," Lisa said, looking at me, then at Ali. "It's not the sort of thing I usually have couples do. But the two of you have a lot of chemistry, and I'd like to take advantage of it. There'll be extra money in it."

"How much extra money?" I asked.

Lisa told us, and Ali and I both raised our eyebrows.

"We'll think about it," I said, "and let you know in the morning."

Ali grabbed my hand before we made it to the stairs.

"What are we gonna do?" she asked.

"What are we gonna do?" I repeated her question. "She thinks we're a couple. You told her we were a couple?"

"No," Ali replied, shaking her head vigorously. "She told me she wanted me to do some posing for some couples sketches, and said if I had someone in mind, it would cut out the awkwardness of doing it with someone I didn't know. I never told her we were a couple."

It was a dilemma.

"What do you want to do?" I asked.

"It's a lot of money," she said. "We can't afford not to do it."

"Rent wouldn't be an issue for a while," I said.

"No," she said. "It wouldn't be that bad, would it?"

Dinner was pretty quiet that night, not much conversation. Ali and I picked out the clothes we were going to wear the next day, and then we got ready for bed. Like the night before, Ali crawled into bed with me. This time, she pulled my hand to her breast almost immediately as she snuggled against me beneath the covers.

We got to Lisa's studio the next morning and could sense an immediate difference in the atmosphere. The lighting wasn't different, but the music was. It was softer, more relaxed.

Lisa, herself, was dressed a little different, too. Her normal t-shirt and denim shorts were gone in favor of a button down blouse and baggy khaki shorts. The blouse was unbuttoned low enough to reveal that her well proportioned cleavage was supported by a swimsuit top.

"What are we going to do?" she asked.

"We're gonna do it," Ali said.

"You're sure?" Lisa asked.

"Yeah." I nodded.

"Okay," she said, clapping her hands together. "This will be slow paced. Let me know if you get uncomfortable. I'm wearing a bikini, too. Since you two will be wearing less and less as the day goes on, I've got the heat up a little, and if it starts to get warm, I'll just ditch the shirt."

Alison looked at me for reassurance. I squeezed her hand.

"Let's start," she said, "like I said yesterday."

I started pulling off my shirt as Ali's fingers began unfastening her buttons while Lisa explained to us that it would be just like we were standing there on the beach with getting undressed to go swimming. It sounded good in theory.

Lisa had a disarming way of interacting with us to get us positioned exactly how she wanted, and when she helped me position my hand under the edge of Ali's blouse, my fingers on the skin just above her waist, it was almost natural.

I could feel the tension in Ali's body as we stood there. Ali closed her eyes as I looked down between us, taking in the view of her breasts, covered only by the thin bikini top she was wearing.

"Relax, Sis," I said, whispering.

"What was that?" Lisa asked.

"I was just telling Ali to relax," I said.