She started getting nervous on the drive to the hotel. She caught herself biting her lip and checking her nails to make sure her manicure still looked perfect. It should, she had just gotten a full mani-pedi last night. She forced herself to breath deep and relax. It wasn't like this was the first time she had ever met a man for a first date, but the little butterflies in her stomach had her feeling like she was the freshman cheerleader who had just been asked to the Senior Prom. The questions kept surfacing: What if he stood her up? What if he was not like his description? What if he smelled? Or had bad teeth? Or onion breath? She forced herself to pay attention to the road and the drive to the hotel.
It was a nice hotel, one of those with "Inn" in the name. Not top of the line but not a cheap little one-star job either. She was early, very early, if she really wanted to admit it but she wanted everything to go as smoothly as possible for this first time. So she was getting to the hotel a couple hours early. It would give her time to relax a little and get everything set-up just the way she wanted it.
She almost couldn't believe it was happening or that she was finally going through with it. Thinking back it was hard to believe that she had only put the ad on that website a week ago and she was already on her way to meet a man at a hotel. Last year she wouldn't have dreamed of doing anything this daring but what is the point of living life if you don't do something interesting with it. She had recently graduated from college and was working an entry-level position with a company but really wasn't enjoying it as much as she thought she would. The work was mundane and didn't challenge her at all. She wanted to like it, but it was the same tasks every day and she was already finding herself working on autopilot half the time. She knew she didn't want to keep doing it and thought she wanted to maybe go back to school and work on a Master's degree, but with the economy the way it was she was just happy to have something that paid the bills and still let her explore her options.
Besides having a dull job and settling into the responsibilities of the nine-to-five grind and paying bills, her dating life (and more importantly her sex life) was nowhere near what she would have liked. So, she decided to do something about it. At this point she really wasn't looking to get tied down into a long-term relationship; she was just enjoying life and having a good time exploring what the world had to offer. It wasn't like she was drop-dead gorgeous but she wasn't anywhere near ugly either. Sure she could have worked a little harder and really gotten some muscle built up, but she liked having some curves and the way most peoples' eyes followed her when she walked past, it seemed they did too.
Meeting guys in the bars had stopped being enjoyable even before college ended and she always seemed to meet the same type of guys. They had different hair, bodies, and faces but underneath it all they seemed to be cut from the same cloth. She would flirt, dance to bad techno music, have a few drinks and then end up having some okay, but less-than-stellar, sex with a half-drunk guy whose belief in his skills was vastly out of sync with reality. And none of them seemed to get the hint that she didn't want a relationship with them. She had lost count of the number of times she had had to tell them to stop calling. Sure there were a few that were worth dating and she had enjoyed her time with them, but she just wasn't ready to settle down until she was sure she was ready.
Of course she had heard all the horror stories about what she was doing. It was part of what had made her hesitate to go through with it right away. She had started thinking about it and doing her research months ago. She had read the reviews and looked at all the different websites out there before narrowing it down to the one. It seemed the safest and had the most thorough verification and safety practices for the members. She looked at other profiles that were out there and spent time tweaking hers so it was descriptive and hopefully alluring without giving any real information or giving a false impression. It helped that the website had a standardized template to enter a lot of the basic descriptive information, too. She had done her homework on the Internet reading several articles and websites on how to be successful and safe. There was so much out there and so much to learn! Finally she picked a few pictures that she felt accented her physical traits the best and still kept her face hidden, it wasn't like she would want anyone at work to stumble on her profile and recognize her.
After first loading it to the site and making it live she nervously checked in several times a day seeing if there were any messages—even though the site would forward notification of any activity on her page and would send along any e-mails (she had decided not to put her phone number on the actual page just to keep a little more safe). It wasn't very long before she got her first messages. They varied all across the spectrum. Some were quite graphic, some assumed a level of familiarity that obviously didn't exist yet, some made her a little nervous, some were short little one lines that didn't say anything, but a few were interesting and polite and got her attention enough to respond. After a few exchanges with some of the guys, she had decided to take the plunge with George Reeves.
She had checked up on him to be as safe as possible. She knew he had passed the safety checks from the website and she looked to made sure he wasn't on any of the do not see lists she knew to check out and he had even given her the names of a couple of other ladies from the site he had met in person so she could contact them. She could have gone further and asked for more real and verifiable information like his real full name and where he worked, but she knew that many of the guys out there weren't comfortable giving out there information until they knew you. Obviously they would be just as worried about meeting a stalker as she was. And really, who would think that Penelope Layne was her real name; parents weren't that cruel were they? He was definitely outside of her normal range of guys—mid-fifties, slightly balding and a touch of a belly according to his own description after she had inquired. She gave him points for his honesty and also for not immediately going into a description of his genitalia as so many of the guys had done. His messages were well written and he seemed well-educated and articulate which were definitely qualities that were different from her college hookups.
They had arranged the meeting for Friday evening and to be safe she gave him her Google Voice number and told him to call a little before the scheduled time of the meeting. That way if something went awry, all he would know about her was a number that she could easily get rid of and was tied to a Gmail account that she had set up using Penny's info. She had heard that a lot of people used throw-away phones and things like that, but it seemed a bit costly when you could easily get a number for free and even make calls from your computer.
She finally arrived at the hotel after a short drive since she had chosen one on the other side of town for the meeting, again caution won out over convenience. The check in went smoothly and simply since she was paying cash for the room instead of using her credit card. She had a room with a lovely view of the parking lot on the side of the hotel so she could come and go using the side entrance instead of the lobby if she wished. She got her key and went up to check out the room. As expected it was nothing fancy but definitely comfortable. In the corner was a small table with two chairs, a couch along the wall, a nice flat screen on the wall (not that she expected to watch a lot of TV), and a king-size bed with a very nice down comforter. She turned into the bathroom and checked out the shower. It appeared to be recently updated and had a nice large shower and, after turning it on to confirm, very nice water pressure.
Before leaving the bathroom she put her hair care and make-up products on the sink and headed out to the main room. She unpacked her small bag as she wandered around. She put a couple of bottles of water on the dresser, put a few toys in the bedside drawer in case things went either really well or really not well along with some condoms, and then laid out her chosen outfit on the bed. He hadn't requested anything special so she had chosen a nice floral print sun dress, a matched set of white bra and thong panties and, since George had mentioned he liked them, a pair of sheer stockings and a garter belt to match. She had a nice but simple pair of white heels that would go well set next to the bed to slip on to complete the outfit. She placed a few scented candles around the room to get rid of the smell of cleaning products and also to set the mood a little.
Seeing she had a little over an hour before he was supposed to arrive she decided to spend her time getting ready. She stripped off her driving clothes, hid them away in a dresser drawer with her bag, made sure her phone was on and her Google account was set to forward calls to it, and headed for a quick shower to clean up and settle her nerves. She set the water to a nice hot level and climbed in. She had to admit for all the nervousness she was also very aroused and excited by the upcoming meeting. It was so far outside of anything she had ever done and though there were risks involved they too added to the excitement.
She slowly and luxuriously allowed the heat from the shower to soak into her while she washed her hair and soaped up her body, admittedly spending more time than was necessary making sure her naughty bits were thoroughly cleaned. She had made sure to shave her legs and pussy the night before but took out her waterproof electric shaver to touch it up and make sure it was perfectly bare and smooth with just a nice patch of hair on her mons. The buzzing of the razor so close to her sex only heightened her awareness of how much she was looking forward to the meeting.
Climbing out of the shower she dried off using one of the plush towels provided by the hotel and wrapped her hair with it. She next got out her body lotion and massaged some into every inch of skin making it silky smooth and soft. She couldn't help running her fingers across her body reveling in the feel as they glided across. She got out her hair dryer and used it to clear the steam from the mirror and then used it to dry and style her hair leaving it mostly loose and not overly done up. She put on a light amount of make-up leaving her skin looking natural rather than overly done up and just as she was finishing her phone rang. Glancing at the face she saw it was about half an hour before her date with George and the call was coming from her Google account.
She smiled before answering, "Hello, this is Penny."
"Well hello, Penny, it is nice to hear your voice. This is George," she was greeted by a nice baritone voice that was only slightly different than what she had imagined his voice to be like. "I'm headed your way and wondered what my final destination would be."
"That would certainly help both of us I imagine," she chuckled. She gave him the name of the hotel, "Do you know how to find it?"
"I know where it is and should be there in 25-30 minutes. I will give you another call when I get close."
"Thanks, I will be waiting," she smiled as she hung up.
"Seems he has done this a few times before," she thought.
Until now she wasn't sure how she would react to someone who had done this a lot and found it more reassuring and actually helped to settle her nerves a little bit. If it had been someone completely new to it like she was they wouldn't have known any better how it was supposed to go, but she had been unsure how she would react to someone who knew what they were doing.
Her make-up and hair done, she decided to enjoy just lounging around naked for a few minutes before getting into her outfit. She hopped on her notebook for a few minutes checking some e-mails and browsing. When she had about ten minutes left she put away the computer and got dressed. She started by sliding her stockings on one at a time and smoothing them up her legs. She put on the garter, made sure the straps were straight, and clipped them to the tops of the stockings. Next she pulled on her panties over the garter and worked into her bra. She dropped the dress lightly over her head and smoothed it down while she slipped into her shoes. She checked herself in the mirror for a moment and was very pleased by what she saw. The light fabric of the dress hugged her curves and the white of her lingerie was just visible through the thin fabric giving a titillating glimpse of what was hidden under the dress.
In short order her phone rang again. Recognizing George's number she greeted him again teasingly, "Hello, sir, are you getting close?"
"I am about a half mile away and getting more excited by the minute."
"Well then, we'll have to do something about that. I am in room 257. It might be easier for you to take the back entrance."
"That is quite thoughtful of you, I will be coming soon."
"Not too soon I hope," she needled. "See you in a little bit."
She smiled as she hung up the phone and moved to the window to see if she could spot him as he came in. While she did that she put in a call to her friend Dawn telling her to call her in two and a half hours if she hadn't called before then. She then set the phone to silent except for the special ringtone for Dawn's number. She believed in safety first, but there was no need to have undue interruptions either. As she finished she saw a rather ordinary looking middle aged man approaching the door of the hotel. He matched the description she had from George and decided it was probably him so she put her phone on the nightstand and moved towards the door. She was rewarded with a slight knock shortly after.
"Just a second, I'll be right there," she called.
She stopped to check herself out in the mirror, replaced a stray hair or two, and smiled at herself before moving to the door. As she got there she looked through the peephole and as she expected saw the man from moments ago. He was waiting patiently in the empty hallway. As she opened the door his face broke into a large, friendly smile as he saw her for the first time.
"Well, Penny, I must say it is my very great pleasure to meet you in person."
She smiled demurely as she motioned him into the room and closed and latched the door behind him. "The pleasure is definitely mine," she replied as she turned to him and gave him a nice long hug in greeting.
"Don't you look stunning," he replied causing her to blush slightly. "I saw your pictures on the website, of course, but you are much more beautiful in person. Do you mind if I make myself a little more comfortable?"
She shook her head in a slight no as she motioned towards the table and chairs. He took what looked like a card out of his pocket and set it on the bureau under the television then set a bottle of wine on the table and took off his jacket.
"I came right after work. Would you mind preparing a couple glasses while I go freshen up?"
"No, go right ahead, I'll get it open so it can breathe," she replied seeing that he had also set out a portable wine steward.
She turned to follow him and he thanked her with a brief peck on the cheek as he passed her the glasses. As she worked the cork out of the bottle she heard the shower kick on. She decided to make herself a little more comfortable to greet him when he came out and took off her dress hanging it up in the cabinet. She began to slip off her shoes, but caught a glimpse of herself in the mirror as she began to bend over and realized they really pulled the look together.
She heard the shower turn off as she straightened up. She went over to the table, grabbed the glasses and moved over to wait on the sofa with her legs stretched out along its length and her body casually draped on the arm. He emerged from the bathroom a short time later in his pants with his shirt hanging open loosely in front, but in his bare feet and running a towel through his closely trimmed hair to finish drying it. He had fibbed a little in his description. If he called that a little overweight, she would hate to see what he called skinny...the man didn't have washboard abs but you could tell he worked to stay in shape.
"Wow," he stammered as he looked up and saw her laying there. "It may be cliché, but I could swear an angel fell from heaven."
"Just come on over here and help me with these heavy glasses," she blushed.
He smiled and dropped the towel as he approached, then lifted her legs and slid underneath them letting them come to rest across his thighs as he reached and took one of the glasses from her.
"Here's to meeting new friends and pleasant times," he toasted.
They lightly clinked glasses and shared some light chit chat as they got to know each other a little and sipped their wine. When he had finished his glass, she set hers aside as well even though most of it was still there. She wanted to make sure she kept all her senses intact during the meet. The entire time they were talking, she felt herself getting more and more aroused as the anticipation of what they both knew was going to happen continued to build. With a quick glance towards his trousers she could see he was getting excited too. Since he was being so gentlemanly she decided to make the first move.
She sat up, took his glass and set it on the table then leaned into him and kissed him deeply. Their lips pressed against each other as she traced his lips with her tongue and ran her hand along his chest. She casually teased a nipple while their tongues tenuously touched and their kissing grew more intense.
She broke the kiss and smiled at him as she continued to excite his now erect nipple. She kissed her way down his neck and chest opening his shirt to fully expose his sparsely furred chest. She ran her fingers through the soft, thin hair and continued teasing one nipple with her hand while simultaneously wrapping her lips around the other and giving a playful bite. He let out a sharp "Oh!" in exclamation but didn't make any moves to stop her or even really squirm. Deciding to fully take control she moved in front of him on her knees and kissed his way down his abdomen. She let off from plying his nipples to run her hands along his sides and massaged his thighs as her lips approached from the opposite direction.
Feeling the fabric of his trousers under her lips she quickly unfastened the catch and opened them exposing a tuft of neatly trimmed hair. He had either left his underwear in the bathroom or had gone without all day.
"Let's just get this out of the way then, shall we?" she asked him while peering up at him with her half lidded, sultry eyes.
He quickly lifted his hips and helped her slide them down and off his legs. She lifted his feet and slid the pant legs off first one, then the other, and tossed them over the back of one of the chairs. Returning her attention to him, she glanced back to see his fully erect cock surrounded by a neatly trimmed patch of hair. She didn't know what she had expected but it was perfectly ordinary. It was of average length and girth, but she did like how it was swaying back and forth and would twitch occasionally in response to some mental stimulus she could only imagine.
She leaned forward and tenderly kissed the tip and then all the way down the shaft. She wrapped one hand around the base and began stroking as she continued kissing and nibbling the shaft and back around the cockhead. She then used her tongue to stroke across the mushroom head giving it a full lick as she would a rapidly melting ice cream cone. She continued lapping the shaft, the head and around the tip before wrapping her lips around the head and slowly sliding her suckling mouth down to her hand at the base of the shaft, running her tongue firmly along the underside of the shaft as she descended.