Sharing a Room

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May 29, 2021 // By:analsex // No Comment

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Note: The characters depicted in this story are not real people and any similarity to real peoples’ names is coincidental.


It was springtime in Portland, Oregon. Our senior college class was leaving high college for a two week vacation, of sorts, in Florida. The professors kept telling us that we were the luckiest senior class in the history of the entire college, because our college had received an award or grant of some kind from a wealthy philanthropist who wanted to do something for youth across the country.

Anyway, all that I knew was that it meant the entire senior class got to spend two weeks in Florida – staying in a hotel, sightseeing, and attending seminars hosted by important people who I didn’t know.

I was very much looking forward to the entire experience. It would be kind of like how our business trips had been back in twelfth grade – only longer, and much cooler. It was a chance to escape regular classes and do something different. Everyone had been talking about it for weeks.

So the day finally arrived when we were to leave Portland and fly by plane to Florida. We were going to stay in a hotel in Orlando, but we were told there wasn’t going to be much time to spend in Disney World, since there were seminars and other activities planned out for us.

I drove to college on the Monday of our departure with my baggage and belongings. I boarded a charter bus along with many of my fellow college seniors – the A-G bus. Unfortunately, the college had arranged us alphabetically in buses, so many of my friends weren’t in the same bus as I was.

I sat next to Jordan Brooks, who was practically the only friend I had who was on the same bus. We didn’t talk much though, as he was listening to music on his Walkman. I decided to do the same, because there wasn’t going to be much to do until we actually got to Florida. Pretty much the only thing we talked about was lamenting the fact that we couldn’t bring cellphones along on the trip. The college had set down strict guidelines for what we could and couldn’t bring.

It didn’t take long to reach Portland International Airport and go through security. Only about a fourth of the college faculty had come with us, and they were split between the different buses – about four professors to a single group. There were five buses.

After we left the buses, we were split into groups of about ten or so – ten students to a professor. Fortunately, Jordan was still in this second group, so I had somebody to talk to as we went through security and stopped to get snacks and pizza at the airport’s many kiosks.

We boarded our plane for Orlando and took off shortly thereafter. It was a nice day, so there weren’t any delays, which was nice. Even in the spring, Portland can be a bit cold, and everyone was talking about the warmer weather we were heading for.

It was much later in the day when we reached Orlando, because of the time shift, and we stuck in our groups of ten students and headed for the hotel. We first boarded vans to get to the hotel and then were dropped off only a couple blocks away.

“Do we get to pick our own rooms?” I asked Ms. Anderson, who was our assigned professor. Ms. Anderson was widely considered to be one of the hottest professors in college, and as much as I admired her looks, I really wasn’t interested in the faculty that much.

“No, your roommates have already been picked out for you,” she said.

“What’s up with that?” Jordan complained. He was walking next to me, dragging his luggage along.

“The rooms were picked out by a computer,” Ms. Anderson answered, with a smile. “Gives you a chance to maybe meet someone you haven’t met before.”

Great. Well, I wasn’t really interested in meeting new people. It was ridiculous that they wouldn’t let us pick our own rooms. Still, there was nothing we could do about it.

Our group headed into the hotel lobby and received directions from one of the hotel staff members. We went into a large adjoining ballroom and set our luggage and belongings down in one of the corners. Then we waited while Ms. Anderson went to get our hotel room keys.

She came back about twenty minutes later and handed them out. “You can all go up to your rooms,” she said. “That’s what the dean said.”

So I said goodbye to Jordan and headed for the elevators. My room was on the tenth floor of the hotel. I took the elevator up to Floor 10 and got out. The elevator lobby was cleanly lit and the carpet looked expensive.

In an alcove, there was an ice machine and a Coca-Cola dispenser. Opposite from the alcove was a larger nook with a couple of small tables and view outside the window. There was a stack of USA Today newspapers on one of the tables.

I walked down the hall at stopped at Room 1012. I pulled out my card key and unlocked the door to the room. Opening the door, I found myself in a fairly nice hotel room. There was a king sized bed against the main wall, which I dumped my belongings onto.

There was a closet right by bahis firmaları the door, and oppose the closet was a nice bathroom with a mini-jacuzzi. It appeared to have room for at least two people.

There was a large desk at the wall perpendicular to the wall the bed was against, and an office chair. A coffeemaker sat on the desk, as did a welcome pamphlet for the hotel and a telephone. In the corner, there was a lounge chair with an ottoman, facing a cabinet against the opposite wall, which, as I soon discovered, had a television inside of it.

I began unpacking. After about ten minutes, I heard a noise at the door. I got up from what I was doing and went to open it when it suddenly opened by itself.

I was expecting some guy whom I didn’t know or like to walk in…but instead, Katherine Phillips walked in, tugging her luggage. Katherine was what I considered to be one of the hottest girls in the entire college. She wasn’t a cheerleader, but she could have easily been one. She was a medium sized, sweet brunette who was generally nice to everybody she came across.

She looked up, and suddenly stopped, dropping the handle of her suitcase. Her jaw dropped as she saw me, and I’m sure mine did simultaneously.

“What the hell are you doing in here?” she asked accusingly.

“Um…this is my room. At least, this is the room they gave me the key for,” I replied.

“There must be some mistake,” she replied flatly. “Guys and girls don’t sleep together in the same room!”

“Your guess is as good as mine,” I returned. “Maybe we should go find a professor and get it cleared up.”

Katherine was agreeable to doing this, so we went out in the hall to find the nearest professor. We found one, Professor Johnson, very quickly, because there were a huge crowd of kids around him. We approached the crowd and listened in to what Johnson was saying.

“Look, I don’t have anything to do with this. That’s the way the rooms were set up. The people who are putting this on for you thought that you were mature enough to handle it. They wanted to give you a new experience – pull you out of your comfort zone. You don’t have to sleep in the same beds. For those of you with rooms that don’t have separate twin beds, the hotel has put rollaways in the closets.”

It quickly became apparent that everybody else was rooming with somebody of the opposite gender. There was no mistake. It was completely intentional. The moment Johnson stopped talking, some of the kids started shouting again, but it was no use.

“Will you guys stop complaining?” Mr. Johnson asked, irritably. “Can’t you appreciate what a tremendous opportunity you’ve been given? This isn’t going to be a problem unless you make it one. So please go back to your rooms and unpack. Get to you know your roommate. You’ll be spending the next two weeks with him or her.”

Mr. Johnson swept down the hall to his own room, leaving the crowd of students behind. Some had apparently been just following along and didn’t seem to mind the fact that they were rooming with somebody of the opposite gender.

A few grumbled, but returned to their rooms, as did Katherine and I. She said nothing as we walked back down the hall and into Room 1012.

I let her in first and shut the door afterwards. Katherine sighed and said, “So where is the rollaway?”

“Do you want the king bed instead?” I asked.

“No, you were here first, and besides, I want to be next to the window,” she replied. I hadn’t spent much time looking out the window, but when I pulled the curtain all the way back, I discovered the view was actually very nice.

I got the rollaway out of the closet and set it up for her. She went into the bathroom and began unpacking her cosmetics, blow-dryer, and whatever else she’d brought.

It was certainly going to be an interesting experience, I thought.

That evening, before we headed down to the general session, our floor met with Mr. Johnson and Miss Miller, who were the professors assigned to our floor. I gathered that the people who put all the guys and girls into the same rooms with each other had done so merely to shock us – get us out of our “comfort zone” they said – and that since we were a private college and it was written somehow into the travel agreements all our parents had signed – it was legal.

I had been uncomfortable with the idea at first, but now I thought it might be kind of fun. I’m not sure if Katherine thought the same way. She complained off and on at first, but then stopped, and didn’t seem to be angry at me or unhappy with the way things were going.

After dinner and the general session, we headed back to our rooms for the night. I made a point of not spying on Katherine or unduly bothering her. Maybe she took comfort in the fact that the bathroom was spacious, and it had a lock, so at least she could shower and undress privately.

A few days went by, and the senior class seemed to be having a lot of fun. When we weren’t attending seminars or going on day trips, we were kaçak iddaa swimming in the hotel pool, enjoying the use of the fitness machines, sightseeing, shopping, and eating out at different restaurants.

It was perhaps the fourth day, or the fifth day, into the vacation when we took a day trip out to Cocoa Beach and Cape Canaveral. Katherine and I had different schedules, and we always let the other know what they were, so we could rendezvous to get together for meals and so forth, since we were supposed to be in groups to do that.

Anyway, the tour we were on was shorter than what had been planned for, so we came back to the hotel a couple hours early. I was actually pleased, because I hadn’t had much free time for the past couple days, and I thought I might watch some TV or something.

I got up to Room 1012, and opened the door to the room. I walked into the room….and froze.

Katherine was lying on the king bed. She was naked, and she was masturbating, rubbing her clit and moaning in pleasure. I’d always wondered how big her tits were, and now I could finally see them. They weren’t huge, but they weren’t tiny either – just the right size, probably 34Cs, I thought. Her pussy was gleaming because she’d obviously been masturbating, but apparently, she hadn’t climaxed yet.

I immediately dropped my backpack on the floor, speechless. At the same moment, Katherine suddenly realized I was there, and she screamed, though not that loudly. She grabbed the bath towel laying on the bed next to her and spread it out over her body.

“I’m sorry,” I said. “The tour ended early…so I came back to the room. I didn’t realize…” I trailed off, not knowing what else to say. For about twenty seconds neither of us spoke.

Then Katherine finally said, “It’s not your fault. I shouldn’t have been doing it. But it’s been a long time and I just had to get some relief. I hope I didn’t offend you or anything.”

“Not at all,” I reassured her. Then, somewhat jokingly, I said, “What kind of guy is offended at the sight of a naked woman?”

“I didn’t know you were interested in girls,” she said.

“Trust me…every guy is interested in girls, unless maybe he’s gay, and I’m certainly not gay,” I said.

“Well,” she said with a sigh, “as long as you’re here, you might as well give me your opinion.” She threw the towel off and fell back onto the bed so I could survey her. “What do you think?”

“You’re absolutely gorgeous,” I said. And I meant it. She had round, firm, perky tits, an angelic face, what looked to be a tight and inviting pussy, a shapely ass, and long, slender, legs. A body that practically every guy must dream of fucking.

She smiled. “How do I know you’re not just saying that?”

“Because it’s true!” I practically shouted. “I’m serious. You have a beautiful body – more than anybody could ask for.”

“Well, I’m glad to hear that,” she said.

“So where were you when I came in? Did you reach your climax?” I asked.

“No, I was almost there, and then you came in,” she replied.

“Well, don’t let me stop you,” I said, firmly. “I don’t mind if you want to finish.”

“But I’ve never masturbated in front of anybody else before,” she said. “Besides…I don’t want you to think…”

I cut her off. “Nonsense. It’s a perfectly normal thing to do. I masturbate all the time, and you might be surprised to know that pretty much every other guy out there does, too.”

“Really?” she asked.

“Absolutely,” I said. Suddenly, a thought occurred to me – why shouldn’t I join her? It might make her more comfortable, and make her feel better, if I was naked too. It seemed like the gentlemanly thing to do.

“In fact,” I said, “How about if I join you? I haven’t jerked off since I left home.”

Her eyes flickered with doubt for a second, but then she smiled, and said, “Really? You’d do that?”

“Why not? As long as you’re turning me on, I might as well get off too.” By now, of course, my cock was fully erect and straining against my pants, begging to be free.

“Okay. I’ve never actually seen a guy naked before,” she said. “This will be fun.”

I started undressing. “Not even in pictures?” I asked.

“Well, yeah, I’ve seen pictures, but this is the real thing,” she said.

I unbuttoned my shirt and flung that off. I suppose I have a fairly good physique for a guy – I run cross country, and that helps keep me in shape.

She watched me unzip my pants and take those off, and I also removed my socks. Finally, I pulled off my boxers, and my cock sprang free.

Her eyes widened as it came into view. She gulped. “It’s huge!” she said, in almost wonderment.

“Well, it’s not that big, but it isn’t small either. Certainly not when it’s erect,” I said with a smile. “Now, show me how you masturbate.”

“Well,” she said, “I don’t have any dildos or toys – I just use my hands, and sometimes the shower jet. I rub my clit with one hand and massage my boobs with the other. What do you do?”

“What most guys do,” I kaçak bahis answered. “I stroke my cock. Like this.” I made a fist around the base of my erect cock and moved it up and down, then stopped. “Ready?” I asked.

“Sure, I guess,” she replied. She cupped her left breast with one of her hands and began squeezing it. With the other, she began rubbing her clit. She closed her eyes and began to fall into a rhythm.

I watched her for about twenty seconds and then I began, too. I watched her as I furiously stroked my cock. I’d build up to where I felt I was going to cum, then slow down, and then speed up again. It took her a few minutes for her to get back to where she had been, and soon she was oblivious to me, moaning and writhing as she pleasured herself.

I decided to wait and hold my own orgasm until just after she came.

Soon, I heard her moaning, “Oh fuck yeah…I’m cumming….oh yeah…”

I glanced down at her pussy, which was now gleaming and very wet from all of her juices. I kept stroking my cock and watching her. Her fingers were slick and sticky from her orgasm. After twenty seconds or so she sat up and stared at my cock.

“Want to watch me cum?” I said, panting.

“Hell yes,” she said. So I began to stroke faster. And faster. And faster. I could feel it coming on.

“Shit,” I groaned. White, hot cum erupted from my cock, burst after burst, onto my chest, on the bed, and on the carpet. It was the most I’d ever cum in my entire life, and it lasted for half a minute.

“That was so hot,” Katherine said, excitedly. Her breasts bounced as she jumped off her side of the bed and she came around to where I was. She sat down right next to me and turned to look into my eyes.

“Ron, I want to say thank you,” she said. “You caught me, and you’ve been a true gentleman about it – you made me feel comfortable.”

“No problem, Katherine,” I said. “I really enjoyed that. That was the best orgasm I’ve ever had.”

“Really?” she said. “Me too!”

We both just sat there for a few minutes, thinking, until finally Katherine said, “You know – since you’ve seen me naked, there’s really no point in getting dressed until we need to leave. Do you mind?”

“Not at all,” I said. “When I have the house to myself I sometimes go naked as well. I think I’ll do the same thing.”

“I never really have the house to myself,” Katherine replied, smiling. “I’m always doing it in the bathroom or something.”

“Well, whenever you have the urge – feel free to masturbate,” I said. “I don’t mind at all.”

We watched TV for the next hour and then got ready for the evening. We were having a big formal dinner out at a fancy restaurant, and so I played the role of the gentleman, escorting Katherine down to the lobby and then to the restaurant. For the first time during the whole vacation, I felt like she was paying attention to me. We conversed over dinner and laughed during the ride there and back.

After what had happened that afternoon, I was horny, and I couldn’t wait to jerk off once we got back to the hotel. Katherine had dressed sexily for dinner, with a low cut blouse and a short, revealing skirt. On the way back to the hotel room she told me she wasn’t even wearing panties. This turned me on even more, and I couldn’t stop fantasizing about her.

When we got back into the hotel room, I threw off my clothes and laid back on the king bed. Katherine went into the bathroom to get ready for bed, and so I decided to wait for her. I picked up a magazine off the nightstand, that I’d brought, and began reading. But I wasn’t really focused on reading. I shut my eyes, still holding the magazine, and began fantasizing about Katherine.

I lost track of time, and was still daydreaming several minutes later, when I suddenly felt a hand on my cock. And then…a tongue licking the head of my penis. I dropped the magazine, just as Katherine lowered her mouth onto the top half of my cock, and began sucking me off. She was completely naked, and on all fours as she sucked.

“Katherine…what are you doing?” I asked, completely amazed, but also delighted.

She took her mouth of my cock and replied, “Giving you a blowjob. Don’t you want one?”

“Hell yeah, it’s just that I didn’t expect you to do that, all of a sudden.”

She smiled, and again took my cock in her mouth, rolling her tongue around it and moving up and down the length of my shaft, taking careful pains not to let her teeth scrape it. I shuddered with pleasure. My cock was in heaven. I’d never felt this good before. Ever.

“You sure you haven’t done this before?” I asked.

She took her mouth off my cock again and replied, “No…this is the first time I’ve given a guy head. I’m only going off what I’ve seen and read.”

“Well, you’re damn good at it. Keep going,” I said.

She smiled, and again took my cock in her mouth, trying to take in more of it. She began to slide her mouth along my shaft faster and faster, lubricating it with lots of saliva. She cupped my balls with her hand, and I groaned with pleasure.

After a couple more minutes I could feel myself getting ready to cum. “Katherine, I’m going to cum,” I warned her. “You can take my cock out of your mouth if you want.”

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