Their First WeekendbyDeweyWoo©
Bill had followed her instructions to the letter. It was Friday, and he had checked into the hotel, getting a room with the best view possible. The clerk had a questioning look when he asked for the highest floor possible, and Bill found it necessary to explain it was for the view.
Once he got to the room, he got a large bucket of ice and put the wine in to chill. Then he unpacked, and put on the purple polo shirt she had requested. With everything set, except his nerves, he went down to the bar.
Sally had not given much of a description of herself. She said she was average height, slightly overweight, brown hair. There were at least a half dozen women in the bar fitting that description. Bill knew the purple shirt was meant so that she could check him out without him knowing who she was. He hated that, but if this woman was half as fantastic as she sounded in her emails, then it was definitely worth the discomfort.
Bill walked over to the bar, and took a seat, being sure to leave an empty one on both sides. He ordered a Bloody Mary, and when it came he finished it in to large gulps and ordered another one. Then he started scanning the room, looking at the women there. Of course, he ruled out the blonds immediately, as two of the brunettes were with other men, and 3 were with groups. The only one sitting alone was too hidden in a shadow to see details, but she certainly fit the few details he had. Still, he knew that approaching her could be disastrous. If it was her, he broke one of her rules. If it wasn't her, he would be very embarrassed. So, he sat there nursing his drink, and let his mind wander to the multitude of emails that they had shared.
He knew she had a great sense of humor. He also knew that, like him, she was way outside of her comfort zone in arranging this rendezvous. Yet, there seemed to be an attraction, much like the attraction in "You've Got Mail," though when he mentioned it, she said she preferred the Jimmy Stewart version. She was almost a decade younger than he was, but that didn't seem to bother her. In fact, she said she liked it when Bill jokingly said he was robbing the cradle.
Bill was startled when he felt the touch on his hand. He was so lost in thought that he didn't notice that the brunette from the shadows had sat down next to him.
"Buy me a drink, sailor?" she asked once she had his attention.
That wasn't the code-phrase she had said she would use.
"Sorry, but I am waiting for someone," Bill replied.
"Me, too. But I thought maybe we could wait together,"
Bill thought for a moment, but then said, "I would love to, but I'm not sure I should. My date is quite jealous," he lied.
"You don't know what you are missing," she said as she went back to her table in the shadows.
Bill called the bartender over and asked for a ginger ale and sent a drink to the brunette. He felt bad that he had to brush her off like that, especially because he didn't get too many women interested in him.
With that, Bill resumed his mental review of the emails he had shared with Sally for the last 6 months. He was attracted to her wit, sarcasm and obvious intelligence. He found it interesting that she had called herself a naturist, but when he asked if that was the same as being a nudist, she didn't respond.
And she said that she hated condoms, but when she had to use them, she preferred the Orange ones. Bill wasn't sure what that meant. Maybe it was some type of code; maybe a brand; or of course the obvious would be a color. He couldn't find anything on the internet about it being a slang term, though that search did turn up orange flavored condoms along with the orange colored ones. Still, that was such a puzzlement. He wasn't sure if tonight would be anything more than drinks and conversation, but just in case he did find some orange colored condoms on the internet, and bought a box. That, too, was in the hotel room several floors above him.
The brunette he had sent the drink to touched him on the shoulder. "Just wanted to thank you for the drink," she said.
"Looks like we have both been stood up."
Bill looked at his watch. "Mine still have 15 minutes. She said if she wasn't here by 8:00, she wasn't coming."
"Well, I'm leaving. Thanks again," the brunette replied as she slipped a business card under Bill's arm. Then she walked out of the bar.
Bill looked at the card. There was a name, but no company on the card. The name caught his eye, however. Sally Thorndike. He didn't know his Sally's last name, but he was thinking this was too much of a coincidence. The cell phone number was circled. He turned the card over, and read, "If your friend doesn't show, I will be in the restaurant. Feel free to join me. S." Not quite knowing what to do, he waited.
"Anyone here named Bill Sally," the bartender called out?
Bill wondered if that could be for him. Sally didn't know his last name, either.
"That's probably for me," Bill called, and the bartender set a phone down in front of him.
"So, what did you take from that brunette?"
"I didn't take anything. She gave me her card," Bill said as he scanned the bar to see if anyone was on a cell phone.
"What did it say?"
"It has a name, address and phone number on it," Bill replied, thinking it best to not mention the note on the back.
"You know who this is?"
"Yes, I recognize your voice from our phone calls. Where are you?"
"You don't need to know that yet. I will tell you that I like what I see, but I'm still a little nervous. I've only done this twice before, and both time it turned out to be men so fat they couldn't see their dicks much less use them."
"Blunt as usual," Bill replied. He knew that Sally's bluntness increased with her nervousness, confirming what she had said.
Sally knew that Bill was getting a little agitated. "Tell you what, go up to your room, and I will be there in 30 minutes, okay?"
Sally had hung up before he realized he didn't give her his room number. He waited a couple of minutes to see if she called back, then headed to his room, assuming that she somehow knew the number.
Still feeling guilty about giving the brunette the brush-off, Bill stepped into the restaurant to see if he could see her. She was sitting along the windows, and was having a drink and small talk with a gray-haired gent. Bill turned and left the restaurant, but was stopped just outside the door. The brunette.
"So, you were stood up after all."
"Not exactly, just a change of plans. I just wanted to apologize for being rude earlier. Not my usual style. But I see you weren't stood up after all."
"No, he was just very, very late. Still, I can't say much. He is my boss after all," Sally replied. "Did you keep my card?"
"Yes, I did," Bill said as he patted his pocket to be sure he had picked it up.
"Well, if you ever want to have drinks, give me a call. You're cute." And with that the brunette turned and walked back to the table.
Bill walked to the elevator, and pushed the button for his floor. Just as the doors were closing, someone called out, "Hold." Bill quickly pushed the door open button. A young man got on, followed by a 30-something redhead. Bill inquire as to the floors, and pushed the button for the floor the young man requested. The redhead didn't say anything. This confirmed that they weren't together. The young man got off 2 floors before Bill's, and Bill inquired of the redhead if she needed another floor. She just shook her head no.
When the doors opened on Bill's floor, he held the door open for the redhead, and then got off himself. She stopped to look out the window at the night sky, and Bill went to his room. As he opened his door, he noticed the redhead coming his way, but she stopped a couple of doors from his and fumbled with her keycard. Bill went in and shut the door. And he sat down to wait.
The clock said it had only been 10 minutes since he got back to the room, but it seemed much longer. Then, there was a knock on the door, which though expected startled him none-the-less. He looked out the peep hole, but it was covered from the other side.
"Sally?" he shouted through the door.
"Yes, Bill. Please let me in."
Bill opened the door, and standing in front of him was the brunette he expected. He already knew her age, but would have passed for younger. She was indeed curvy, but where most women who call themselves that are actually fat, Sally was actually curvy. She had hips, and a waist, and from what he could tell through her dress, she didn't have any real bags of fat hanging off her. Bill was pleased.
Bill stepped out of the way and let Sally in. As she passed, he picked up a hint of an elegant perfume, and something he was more likely to call musk. Her face looked somewhat familiar, though he couldn't place it. What Bill marveled at most was what she wore. It wasn't a dress, and wasn't a bathrobe. It was sort of a kimono-like outfit. The left side overlapped the right, and tied just under the bust, and again at the waist. The tie under the bust accentuated her breasts, much to Bill's satisfaction.
Sally started the conversation. "I know it was mean of me to get a peek at you before you got a peek of me, so if you don't like what you see, just tell me and I will go."
"After all those emails and chats, do you really think I am that shallow?"
"No, but fair is fair. Shall I leave?" Sally asked.
"No. Please. Sit down." Bill motioned toward one of the chairs in the room, but Sally stopped and sat on the edge of the king size bed.
Bill offered her some wine, and took a seat in the chair by the desk. They chatted for a few minutes, about nothing in particular. Even though they had shared so much through emails, online chats and the occasional phone call, they were still both nervous about meeting for the first time.
Bill got up to refill the glasses. Sally stood up and walked over to him. "Bill, we're good friends, right?"
"Yes, of course. How could you even ask that?"
"Well," Sally replied, "I was wondering because it is customary for good friends to kiss when they meet, isn't it?"
Bill answered by putting down the two glasses, took Sally's face in his hands and gave her a short kiss on her lips. Then he backed away, grabbed the glasses, giving one to Sally, and sat back down.
"That wasn't very much of a kiss," Sally complained.
"Sorry. Wasn't sure exactly how you meant that, so I took the safe route."
Sally was silent for a minute. Bill always took the safe route, so she wasn't surprised. But she wondered what "Mr. Safe" was doing here. Rather than sit down on the bed, she leaned over in front of Bill, placed he hand on the back of his neck, and slowly pulled his lips to hers. This was a longer, and frankly more passionate kiss. Bill couldn't believe how good it felt, how sensuous it felt, yet how soft it felt. He parted his lips slightly when he felt her tongue wanting access. The few women Bill had known well enough to French kiss usually had no finesse. They just shoved their tongue into his mouth and left it there. Sally knew the proper way, and teased his lips, grazed his front teeth, and sought just the tip of his tongue.
After several seconds of heaven, Sally pulled away, but kept bending over. Bill couldn't resist taking a peak at her cleavage through the top of her dress, but was sure to not stare too long.
"That was much, much better," Sally said as she sat back down on the bed. They chatted until their glasses were once again empty.
Bill got up from his chair and, feeling bold from the wine, took Sally's glass and set it aside. He sat down on the bed, placed his right hand on the back of her neck, his left hand circled her waist, and he kissed her. It was a long, somewhat sloppy, passionate kiss. They both collapsed back on the bed, and kept kissing. Hands moved up and down each other's backs, but went no further. It was about 20 minutes later when they finally came up for air.
"Wow," Sally thought. She wasn't sure if it was the kiss, or the feeling of Bill's manhood pressing against her side, but she noticed that her panties were quite wet, and very uncomfortable. She decided to take the next move.
"Bill," she said, "I have been lying to you about one thing all this time. It was just my way of protecting myself if you turned out to be a creep."
Bill looked at her with a puzzled expression on his face. She reached up and pulled her brown wig off, revealing a net holding her bright red hair.
"It was you on the elevator," Bill exclaimed.
"Yes, it was. Sorry I did that to you."
There was a moment of silence, then Sally spoke again. "You already know that I am a naturist, right?"
"You mentioned that, but you never explained it."
"A naturist is someone that is more comfortable without clothes than they are with clothes."
"A nudist," Bill responded.
"Well, we don't like that term. Too many negative stereotypes of orgies. And we don't play anywhere near the amount of volleyball the stereotype says we do.
"Anyway, here's the deal. While you have me quite aroused, I am not quite ready to do much more with you than we have. Yet, I am comfortable enough with you that I would like to get out of this dress. Would you mind?"
Bill immediately said that he didn't mind.
"And you won't think this is an invitation to sex, right?"
Again Bill nodded.
"Will you join me?" Sally asked.
Bill wasn't sure he was comfortable enough with the idea, but said he would try, as long as he could get dressed again if he got too uncomfortable. With that, Sally pulled on the strings holding her dress closed, pulled it looks and let it fall from her shoulders.
Bill was amazed by several things all at once. He was amazed by how comfortable she seemed to be naked. He was amazed at exactly how proportionate her body was. He was amazed at how little her breasts sagged.
"Before you ask, they are real. I just have good genes that help them fight gravity," Sally said.
Bill apologized for staring, and stood up. As he unbuttoned his polo, she asked if she wanted a show.
"No, this isn't meant to be sexy. This is meant to be natural. Just disrobe."
"In for a penny, in for a pound," Sally replied.
"But you still have your panties on."
Sally stood up, tossed her dress onto one of the chairs, then downed her panties and tossed them, too. Bill stopped his strip and looked again. She was shaved.
As he resumed disrobing, he remarked, "When you first told me you were a naturist, I thought you were going to be one of those women that didn't shave, didn't bathe, and didn't use deodorant. Glad to see I was wrong about that, too."
"Some are indeed like that, but most of us are very normal everyday people who are comfortable in our skin and uncomfortable in clothes."
"Do you know a lot of nudists, er, I mean naturists?"
"Well, yes I do. You can't just go out into any woods and wander around naked. You would get arrested. So I belong to a club that arranges trips to various naturist parks."
Bill was so interested in what Sally was telling him that he didn't realize he was completely naked until he was. He unconsciously pulled on his semi-erect penis and reached under his balls to free them from being stuck to his legs. Sally giggled, and Bill turned red.
"See, isn't it more comfortable that way?"
"Well, it's different," he said.
Sally patted the bed next to where she was sitting. Bill sat down.
"Now," she said, "how about kissing me again as you did last time?
"It might be harder for me to stop my hands from exploring," he replied.
"For me, too," Sally said. "So if I go too far, tell me. If you go too far, I will tell you. Okay?"
With that Bill took her in his arms and kissed her again. Soon they were once again entangled in each other's arms. Sally now both felt and saw Bill's erection. She was not disappointed. Her hands still caressed his back, but were slowly moving closer. Her right hand finally made it to his butt, and she pulled him closer, pressing his erection into her side. "God," she thought, "I want that thing inside of me. But, pace yourself girl." She relaxed her pull just a little, and Bill naturally moved away somewhat. However, his erection still touched her side. Sally was loving this.
After that, Bill decided that gave him some latitude, and his hands started to move, too. First, he briefly caressed her right butt cheek, but what he really wanted was to feel those boobs of hers, so his hand worked its way up and around the corner until his hand was just below her breast.
"Oh, don't stop there," Sally's mind screamed. When he seemed to be hesitating, she grabbed his hand and placed it on her right breast. Bill needed no further encouragement, and cupped her breast in his hand. They were soft and yielding, yet also somewhat firm. He sought her nipple, and found that it was already sticking out. It was larger than he expected it to be, but he enjoyed playing with it. From the sounds Sally was making, she was, too.
After a while, Bill fell away from her and lay on his back. Sally snuggled closely, and continued to rub his chest, playing with the hair and occasionally his nipple. Bill wanted to explore her breasts with his lips, but wasn't sure where she was drawing the line. They were silent for several minutes.
Finally, Sally broke the silence. "You happy you came?"
Bill couldn't resist. "I haven't come yet."
Sally laughed. "No, I meant here to the hotel to meet me."
"Yes, I am Are you?"
Sally didn't answer, but pulled herself up and kissed his cheek.
"As to the other, are you going to be okay if we stop here for today? You're not going to turn blue or anything, are you?"
Now it was Bill's turn to laugh. "Oh, I don't know. Maybe I will have to go see if that girl in the bar is still around."
Sally slapped his chest playfully.
Bill was feeling very worked up from their activities, but was also getting a little groggy from the hour and the wine.
"I think I'm about to fall asleep," he said.
"Then should I leave?" Sally inquired.
"Not if you don't want to. We can just turn out the lights and fall asleep like this."
"I would like that very, very much," Sally said as she got up and turned out the lights before returning to his arms. They were both asleep in just a few minutes.
But neither of them slept well. Sally found her hand creeping toward her crotch, but stopped because she didn't want Bill to think she was weird. Bill finally got up to relieve his bladder, hoping that would take some of the tension out of his loins. As he was in the bathroom, Sally reached for her love button, hoping to relieve her frustration before he came back. Unfortunately, Bill wasn't gone long enough.
Finally, Sally said quietly, "You awake?"
Bill wasn't sure he wanted to answer that. "A little," was his chosen reply.
Sally thought for a moment, then pulled the sheets back uncovering Bill. She crawled between his legs, and took his cock in her hand and started stroking it.
"You sure you want to do that?" Bill asked.
"Shut up and enjoy it."
Sally continued to stoke Bill's quickly hardened cock, changing hands, directions and twists, and it was obvious Bill was enjoying it. While she desperately wanted to taste his manhood, she was determined that this night not go too far, so she resisted. But she also knew that some form of lubricant would increase Bill's pleasure. Still, she couldn't think of anything she could use.
"Mind if I turn on the light to watch?" Bill asked.
"No, go for it," Sally said.
Bill turned on the light, then place a second pillow under his head to better view Sally. While he was enjoying what she was doing, he was enjoying what he was watching almost as much. As Sally stroked, her breasts had a movement of their own, sometimes swaying when her arms pushed one, and sometimes bobbing up and down with the movement of her hands. Sitting on her knees, Bill could see that she indeed had "A little in the middle," but she carried it well. Her position also caused her hips to spread, but Bill hardly noticed that at all. Indeed, Bill liked what he saw very much.