This is a story about two mature people (49 yo woman, 55 yo man) who meet up for a romantic getaway.
Chapter 1 - The Drive
I looked at myself in the mirror. 49 years old. Brown hair with grey streaks. Ugh. I was starting to feel my age.
I know I was my own worst critic. I'm 5'5" and 145 pounds. I'm not as svelte as I'd like, but I like to think at least I look like I'm turning 40 rather than on the verge of a half century. I could see the years catching up to me, though. The crow's feet around my eyes, or laugh lines as some people called them. Other people say I looked cheerful, but I think that's just a polite way of saying I looked chubby. Still, God blessed me with this face and this body, so I may as well make lemonades out of lemons.
I rolled black stockings up my legs, and then I put on a red sleeveless silk dress with a plunging neckline. The neckline came down so low, I couldn't wear a bra, but I know that he is turned on by braless women. I'm a bit nervous as I stare at myself in the mirror, but my B cup titties are still fairly firm with only a little sag. I'm not used to going out braless, but I'm intending to do a lot of things I'm not used to doing over the next few days.
The hem of the dress came down a few inches above my knees. It was a little more leg than I was used to showing, but it was nothing outrageous. I put a jacket on over the dress, mostly to avoid questions from my prying parents, whom I could hear lurking downstairs.
I applied make-up to my face. It was a lot more than I usually wear, but this was a special occasion, and I wanted to look my best. I didn't plaster it on like some women tend to do, but just enough to cover up the wrinkles and make my eyes and lips stand out just a bit. A little foundation, some eyeliner and a touch of rouge lipstick. I put up my hair and teased it a little.
I took another look in the mirror. I didn't look like a model, but I looked far better than most days. Oh well, I sighed. It was about as close to lemonade as I'd be able to squeeze out of the lemon that is my life. I just hoped he wouldn't be disappointed when we finally meet. I strapped on my high heels, and the extra three inches somehow worked wonders for my confidence.
My bags were packed, although I was traveling light. If things went right, I'd hardly even need clothing at all.
"Well, don't you look nice?" my mom commented as I came down the stairs. "If I didn't know better, I'd think you were going out on a date rather than a business conference."
I blushed and hoped my mom didn't notice. Her instincts were right, as usual, but I didn't want to tell her that.
"I can't thank you and dad enough for watching the kids for me while I'm out of town," I said, quickly changing the subject.
"They're teens now," my mom said as she waved her hand. "They hardly even need watching. I think they'll be taking care of us more than we're taking care of them, but we'll see."
I kissed my parents on the cheek and then threw my bag in the car, and I was off on an adventure.
I was nervous as I set the GPS. It was the first time I had done anything like this. It'd been over ten years since I was divorced, and I devoted myself to raising the kids ever since.
It'd been over ten years since I've been with a man, and I was nervous as hell if I'd know what to do anymore. The few times since then that men even came on to, it's like I didn't even know how to flirt anymore, and I worried that I'd be awkward and clumsy with him.
I met Taylor a few months ago on a dating app. At first, I didn't even want to return his messages since he lived so far away, but he had an honesty and quick wit that I found endearing.
We quickly began a regular correspondence. Then emails turned to texts and late-night phone calls, and now we were meeting up for a romantic getaway.
I called it a romantic getaway, but it could just as easily be referred to as a sex hook-up. After ten years, I was so sex starved that my rabbit vibrator and no longer did the trick. Now after so many late-night steamy phone sex sessions, regular sexting, and shared fantasies with Taylor over the past few months, I was almost shaking in excitement to feel a man inside me again.
As I left Erie, Pennsylvania, I drove to the Poconos where Taylor made a reservation at one of the resorts. He was driving in from upstate New York where he lives. Although we had an obvious attraction to one another, life circumstances kept us apart.
We both had our lives that we couldn't uproot, and I just didn't want to commit to a serious long-distance relationship if it wasn't going to lead to anything permanent. That said, I was more than open to a purely physical relationship.
It was refreshing to have someone actually interested in me, which was more than I could say for my kids and even my parents. I know they mean well, but it often feels like everyone is always asking things OF me, and rarely doing things FOR me. I suppose maybe that's just where I am in life, although it's burdensome. My kids can be a handful, and my aging parents seem to need more care and attention with each passing year.
As a divorced middle-aged woman, I come with tons of baggage, but who doesn't by the time they get to my age. It was just that I had enough baggage myself to scare away most suiters, and the few suitors that seemed okay with my life situation had a "creepy" factor that made them a hard nope. Any way you cut it, there's reasons most people my age are single and can't maintain a marriage... myself included.
So, Taylor's interest in me was a welcome relief. I knew his interest in me may be driven by purely physical reasons, and he was only trying to get into my panties, but I didn't mind it so much.
As I drove along the highway, I couldn't help but wonder if Taylor would still be enamored when he met me in real life. Since we had never met face to face, I couldn't help worrying he'd fantasized me as a goddess on a pedestal with impossible expectations for my flawed self.
Me, on the other hand, I had my bar set so low at this point, that as long as he had a pulse, he'd clear the hurdle. Still, the pictures Taylor's sent me depicted a ruggedly handsome 55-year-old man that still had a full head of hair. He was fit since he regularly jogged and exercised (which is more than I could say for myself), and he seemed to do well enough financially to pay for the resort, which was a nice touch.
Part of me wondered if I should have insisted on paying for half the resort cost. Even if we didn't hit it off, I'd feel guilty that I owed him something since he paid for our getaway. There was no mystery on his expectations for the rendezvous. He wanted me to accompany him on a nice dinner and then spend the night with him. I'm not sure why I was so worried, though, since I wanted all the same things, yet I couldn't help still feeling apprehensive.
Nevertheless, my soul was flush in excitement as I sped around the curves and winded along the highways through the Allegheny mountains. I told my family I had a work conference out of town, which I usually did have a few times a year, so it was a plausible excuse. It was a Wednesday, and we were meeting up for Wednesday and Thursday nights. Just a quick two-night getaway before returning back to reality on Friday.
I took off the light jacket while I drove, and the small hairs on my arm stood up as the cool air conditioning shot out of the vents. I looked down at the plunging neckline on the dress and shook my head in disbelief. I hadn't worn anything this daring in public before. Not even back in my 20's when I had the figure to pull off something like this.
My pussy was moist and tingling in excitement. I wore a thong, and my juices were soaking through my panties. I smelled the scent of my arousal. My braless nipples were practically poking through the thin fabric of the silk dress. I really wanted to make a memorable first impression for Taylor, and I hoped he'd appreciate all the effort I put out for him. I felt giddy, and butterflies fluttered in nervous excitement. I hadn't felt this way since I was a teenager. It was strange how life comes full circle.
30 years later, and there I was, still lying to my parents and heading out to a secret rendezvous with a lover. I remembered being 18 years old, and doing the same thing, only now I was lying to my kids in addition to my parents. I could only imagine the grief they would give me if only they knew what I was up to, although for different reasons. My parents because they would be horrified that I was a "whore" for going on a trip to have sex with a man I'd never even met. And my kids because I may as well have been an asexual nun in their eyes.
But this excursion was a welcome relief. A chance for me to be someone else. Not the devoted daughter looking after her aging parents or the tiger mom always providing for her kids. These next few days were all about me, and I couldn't wait to indulge the private side of me, the side that my family would be mortified by. The side that longed to be wined and dined. To be romanced and danced. To light a flame on the candle that hadn't been lit in years and years.
It'd been long enough, and I was ready for some action in my life.
*****
Chapter 2 - Dinner
I walked through the front door of the restaurant. I made good time on the drive and ended up waiting in the parking lot outside for a half hour before our dinner reservation time. Those 30 minutes felt like the longest half hour of my life. I'm a nervous Nelly by habit, and my anxiety tends to overtake me, and I sat there, my mind just running through every possible scenario. I contemplated the possibility of love at first sight to me being stood up and everything in between.
Finally, it was 7 pm, and I gathered myself together. I checked one last time in the sun visor mirror and decided I looked about as good as I ever would at this point in my life, and then I got out of the car and nervously made my way to the restaurant lobby, searching every face in the crowd for the man I'd only seen in pictures up until that moment.
"Belinda?" a voice I'd only heard on the phone called out from behind me.
"Taylor?" I said as I turned around in tense anticipation.
He was standing there, an overjoyed expression on his face, as he took in my appearance, and I blushed, embarrassed to be the center of attention. I'm so used to being invisible, a wallflower, that his deep gaze felt like a spotlight. My goal in life was to blend in, but tonight, I was dressed to have the exact opposite effect.
"You look stunning," he said with a warm smile as he stepped up and gave me a friendly embrace.
I felt a huge sense of relief, and my heart leaped as I saw the genuine look of attraction on his face. Taylor himself was even more handsome than in his pictures. His full head of light blonde hair was neatly combed, and he was dressed smartly in dark dress pants, a blue dress shirt, and a dinner jacket.
It was somewhat strange meeting someone for the first time you felt like you already knew so well. My breasts pressed against his chest, and I took in the scent of his cologne as he inhaled the perfume in my hair. I wanted to kiss him, but I think both of us were awkwardly navigating the waters, both of us excited but not wanting to move too fast for the other.
"We do have reservations. How about we take our table?" he proposed after we finally broke the embrace.
"That sounds lovely, I'm starving" I replied, still amazed to be in the moment.
The maître d showed us to our table, and Taylor graciously pulled out my chair.
"Why, thank you," I blushed, clearly unused to being pampered.
A waiter immediately appeared at our table, and Taylor ordered a bottle of chardonnay. We were seated in a quiet corner of the restaurant, half hidden away from the rest of the patrons. The resort was clearly a weekend getaway, and the restaurant was less than half full on a weeknight as opposed to the overflowing crowds I assumed they hosted on Friday and Saturday nights.
"You look amazing," Taylor remarked.
