Jennie Goes to New York City

Jennie Goes to New York City, by StrappySandals              

(Writer's note: Our favorite, old, high school lovers find themselves together in New York City for a long weekend filled with fun, frolic, and incredible sex. The Big Apple offers excitement like they have never imagined. Jamie's perspective is typed in standard text, Jennie's perspective is in italics. Enjoy!!

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As I sit in New York's Penn Station, the old Simon and Garfunkel tune, "Homeward Bound" started playing on my I-phone. "I'm sitting in a railway station, got a ticket for my destination...ooohhh....ooh....oh..." What a great song at suddenly a very appropriate moment. In reality, I didn't buy a ticket, and I wasn't technically going home. But I was meeting with Jennie, and something about being with her always felt like being home. We are two Philly kids (albeit 55- year-old kids) meeting in New York City, with this railway station becoming the gateway to our relationship. Jennie is soon going to emerge from one of these doors and we are going to spend three glorious days together in New York City. Both my dick, and my nervous system, are churning in anticipation.

To update those readers who have not had the opportunity to read our saga from the beginning, I'll offer a little background. Jennie and I had a wonderful loving relationship 35- years ago in high school. Long story short, I loved her immensely, but was a little bit of an asshole at that young age, and when Jennie got tired of waiting for me to mature, she took-up with a guy who had his priorities more in order. It broke my heart, but eventually I moved on as well. Both of us lived fine lives for 30-some years, until fortuitously reconnecting through a website called "HighSchool.com". We are both married, but once reconnected, our desire for each other has just overwhelmed any reservations we may have had about our existing relationships. Our love for each other has exploded into a passionate, fun, loving, sexual relationship, that is only harnessed by our fear of hurting our innocent family members.

All that being said, I am so looking forward to seeing her today. It's been over three months since we'd gotten together last, and the time apart only serves to increase the desire in me. Jennie is an absolutely, beautiful woman, even after all these years. She is tall, blonde, thin, with beautiful C-cup tits, to go along with the sweetest disposition ever; which only serves to camouflage her incredible sexuality and willingness to play sexual games with me. As I sit here waiting, I am dreaming about what she'll wear this weekend, and what adventures we might get into during this three-day romp through the city. I love her so much and cannot wait to see her exit that train.

The gentle rumbling of the train has me feeling so stimulated, it's becoming difficult to ignore the urge to touch myself. I've been dreaming of this day for so long and to finally be going to New York City to see Jamie seems like a dream come true. We were both born and raised in Philadelphia, and that is where we met, fell in love, and where most of our memories were made. But he's working in New York now, and I love the city, so we've been discussing this New York rendezvous for a long time. I am so excited that it has finally become a reality.

Although, as stimulated as I am, I am also nervous as hell riding up here on this train in my current state of dress. I know Jamie has a sex filled weekend planned, so I want my arrival to be a tempting little reminder to him that I like to play the games as well. As I sit here, I am wearing heels, a short, black, wrap-around skirt, and a semi-transparent white blouse, all covered by a black overcoat. No panties, no bra, no stockings. Nothing but me underneath. And nothing to stop my churning sex from dripping moisture down my leg. However, that bit of inconvenience will be well-worth it to see Jamie's expression when he realizes I've gone full commando.

"TRACK 14 - NEW JERSEY TRANSIT TRAIN NOW ARRIVING FROM PHILADELPHIA - TRACK 14."

As soon as I heard the announcement, I made a beeline for gate 14. I wanted mine to be the first face Jennie saw when she poked her head through the door. When she did finally show, she was a site to behold. Jennie has a way of being stunningly beautiful, but in a very casual way. Today, under her short blonde hair, she wore a beaming smile, black overcoat, and heels. Her bare legs looked great, and I could only imagine what she was wearing underneath. Generally, she dresses somewhat demurely, but her natural gifts are so special, she can make even the most mundane outfit look sexy.

As soon as I could get her out of the path of the departing herd, I gave her a great big bear hug and kiss. She felt great and her smell was intoxicating. I could have stayed wrapped up with her for hours, but the night was young, and our time was limited, so I finally released her and stood back to admire her beauty. The only comparison I can make is to the late Princess Diana, and that is a compliment to both ladies.

Navigating Penn Station in New York is a nightmare at almost any hour, but at five pm on a Friday, maybe even a little more so. As I was trying to fight my way through the horde to get to the exit door, it occurred to me how humorous this situation could be if I wasn't careful. Wearing near see through clothing, no underwear, and 4" heels, while racing a mass of lunatics to get through a single door was almost a sit-com worthy script in some HBO comedy. I can almost hear my mother warning me to wear clean underwear in case of an accident. Ha ha, guess what mom? No underwear, but thankfully, no accidents.

Once out of the gate, I was glad I had the heels on, as they gave me a good view over the crowd to find Jamie. My God, he is good looking! Even after all these years, his look still sends a serious tingle into my loins. Today was no different, except for the bare bottom. Anyway, after the initial hugs, and kisses, and general looks at each other to get past the wonder of simply being together again, I asked Jamie about his plans for the weekend. With that came the most devilish smirk I have ever seen, and his response was to take my arm and say, "follow me lady". I did, and I just knew it was going to be memorable.

"First, we are going to the hotel to drop the bags and refresh a little bit. Then a few drinks, something to eat, and then back to the room." "We are going to explore each other tonight; we can explore the city tomorrow," he added.

It was a cool, but beautiful, early fall evening in the city. A lot of people certainly, but they all seemed like props in two-person play. Nothing mattered but me and Jennie. As we walked to the hotel, we held hands, occasionally stopped to hug, and kiss, and generally act like a couple of teenagers. It was so good because it also allowed us a little time to get re-acquainted. Just touching her makes my dick tingle. Tonight, my dick was tingling like a church bell on Christmas Eve.

"This is so beautiful," I exclaimed as we entered the world-famous Roosevelt Hotel.

It's definitely old-school, but a true classic," Jamie said. It opened in 1924 and has been serving New York City ever since. It's also known as the "Grand Dame of Madison Ave." due to its early 20th century history, and decor, and has guested movie stars, politicians, world leaders, star athletes, and now Jamie and I. "Let's go up and drop off the luggage, get cleaned up a bit, then we'll come back down and have a drink, Ok," Jamie suggested?

"Good for me," I responded.

After checking in, we caught the elevator up to our room in the penthouse, which in this hotel was on the 18th floor. An exceptionally beautiful room it was. New York City hotel rooms are notoriously small, but this one was roomy, elegant, relatively modern, two huge beds, and a beautiful view of the city. "It's perfect," I commented.

"You are perfect," Jamie responded, sending another jolt into my uncovered pussy.

"I'm going to the bathroom to pee, and no peeking," I scolded Jamie. He has a little voyeuristic thing about my peeing, but I prefer privacy when doing my bathroom business.

"OK, no peeking," he promised, likely with fingers crossed.

"So, what's the plan?" I hollered out to him while doing my business.

"Well, first we're going down to the world-famous Madison Club bar for a drink, or two, to help set the mood for the evening. Then maybe a lite snack to sustain us through some shoe shopping. I'm thinking you need a new pair of elegant, heels for the weekend." he added. "Then, I'm planning a nice, but very dirty dinner date with the woman I love. I expect we'll return to this fine room about eleven, whereby you can try on your new heels, and I can unleash my desire to make crazy love to you." After a moment's thought, he added," and I'm waving a big, yellow caution flag to advise you that I have four silk ties in my bag and have every intention of using them this evening," followed again by his implacable smirk

"Oh my," I responded quietly, as my heart and pussy fluttered in harmony. Jamie is a very creative guy, and I love that about him; but tonight, may require a small leap of faith. We have kidded about a "Shades of Grey" evening together for a while now, but I should have known he doesn't do kidding around. The idea does have my submissive mind, heart, and loins all racing though, and I am totally up for anything tonight.

Excellent, I thought to myself, as we exited the room and strolled to the elevator. I had dropped the bondage teaser on her and got virtually nothing but silence. I'll take that as a nervous, but positive response. Oh, I do love this woman!

"You look great tonight, Jennie," I complimented her. "Especially those beautiful, unencumbered breasts of yours. A little daring for you though, isn't it?" I questioned.

"It is," she responded shyly, "but not as daring as my bare ass under this short skirt," she added to up the ante a bit.

Oh my God, I do love this woman, I thought to myself!

"Good evening, folks, and what will you be drinking", asked the distinctly Irish barkeep upon our arrival.

"Jennie?" I deferred gentlemanly.

"Well, seeing as I have such an exciting night ahead of me, I think I'll go right for the hard stuff and have a Stoli-O over ice, with an orange wedge if you have it," she asked.

"Oh, I can definitely do that," concurred our Irish barkeep. "And you sir?" he asked while still staring at Jennie.

"I'll have the same, plus a Bud Light to go with it," I added.

"OK then, coming right up and I'll be quick with it," he promised.

"It's so great to see you, and I am so happy to have you for these next 36- hours without interruption," I started. "We're going to have such a good time together," I added.

"So good, that you think you have to tie me up to keep me here," Jennie countered while laughing.

"Touche! I didn't think you heard me," I said, just as the bartender arrived with our drinks.

"OK, here you go then; two vodkas with orange wedge, and a Bud Light," he said while offering the drinks, then adding, "anything else for you Miss? A water, or club soda, or anything?"

"No, just the vodka and orange, thank you," Jennie replied.

"OK, have it your way," he said. But our barkeep wasn't quite finished just yet. "So, what is a good-looking couple such as yourselves doing in the big city this weekend?" our bartender questioned.

I would have rather taken the conversation back to tying Jennie up, but our barman seemed like a nice enough fellow to share a little banter, so I replied, "Going to the Knicks game tomorrow afternoon at the Garden."

"Oh, basketball fans, are you?" he asked.

Jennie clarified that immediately by allowing "he's a basketball fan, we're also going to the theatre tomorrow night to see 'Come from Away."

"Now that makes a little more sense to me", the barkeep said. "An excellent show, and truth be told, I didn't picture the little lady here being a big Julius Randle fan," he joked. "And what do you have programmed for this evening?" he continued getting a little deeper into our business.

"Well," I started. "A little dinner, maybe some music, then back to the room early. We had a long day," I added, hoping I didn't sound like too much of a pussy.

"And we're going shoe shopping," Jennie blurted out somewhat hastily, and somewhat with regret as soon as she said it.

"Shoe Shopping, are we?" Now that's a subject Old Mickos knows a little something about," he added suddenly, with a huge smile on his face. "Where might you be headin' for those shoes, if you don't mind me asking?"

Both Jennie and I shrugged our shoulders and looked at each other with blank stares knowing we had no idea where we were going. And, quite honestly, I wasn't exactly sure how much information I wanted to share with our new Irish friend. But finally, I confessed, "we're not really sure. We were just going to stroll around town with hopes of finding a good shoe store," I added.

"Well then, allow me to be of some assistance," Old Mickos offered. "I have a very good friend here in the city, and she is in the specialty shoe business; ladies-shoes to be precise. And to be even more precise, shoes for a woman, with beautiful legs, wonderful feet, and who obtains a certain pleasure in flaunting those assets," he continued along in his melodic, Irish brogue.

I found myself a little curious, but also a little wary, and a little intimidated by the whole thing. I didn't want to seem like a rube, or some jerk-off, or pervert, and I especially didn't want our little shopping trip to end with a New York Post headline tomorrow either. So, I stammered timidly, that we didn't need the address, and would just wonder around the streets of midtown.

"Suit yourself," old Mickos replied. "But I am going to give you the address all the same. I'm just knowing that your beautiful lady friend will love the experience. And when you get there, you tell Colleen that Old Mickos sent you. She'll treat you right, knowing I made the recommendation," he promised as he walked away.

"Where is it?" Jennie asked, after Old Mikos had delivered the address.

"It's in the East Village, on Avenue C, between 8th and 9th streets," I replied. "He said it's a little basement shop called Colleen's, and it's open from 7pm till midnight every night except Sunday. Why, do you want to go?" I asked her.

"Well, I'm not really sure, but I would like to visit a fun shoe store," Jennie said. "We don't have anything else to do, and maybe a little adventure will be fun," she added, looking extremely curious and sexual at that moment. "We have all night for the hotel room, let's try it," she added

"OK, let me hit the restroom and pay the tab, then we'll get on the road for this adventure," I said, feeling like Gilligan, about to embark on a three-hour cruise. And with that, I stopped by to say thank you, and good night to Old Mickos, hit the restroom to pee, and wash up, then made my way back to grab Jennie to begin our night of adventure.

"East Village; Avenue C, at 8 ^th St., Jamie directed the cab driver as we got in. In my mind I was a little uncertain as to whether this was a good idea or not, but under my dress there was absolutely no uncertainty. My juices were dripping down my leg. The thought of shopping for high heels with Jamie, coupled with the sexual possibilities of this mysterious shoe shop, had me melting down below.

As we drove away from the hotel, Jamie leaned over to kiss me. It was a good kiss. Soft, passionate, with a lot of moisture, and tongue; just the way I like it. His hands were wandering as well. Tickling my breasts, rubbing up my legs, and playing with my hair. "You know this is killing me, don't you," I said, as he pulled back for a half-second.

"I hope," he admitted. "I want you to be a bit excited when we get to the shop," he added.

"Excited?" I questioned. "I've got a running faucet right now," I whispered quietly. Then rhetorically asked him, "How about you, big fella?" as I stroked his groin area, and his obviously, hard cock. "Hard as rock, and just the way I like it" I noted while giggling. We continued the kissing and fondling until we heard the cab driver announce "We're here folks, that'll be $47.50.

As we exited the cab, I climbed out the driver side door, then ran around to assist with Jennie's door. Interestingly, the cab driver also hustled out to Jennie's door as well. Both of us stood mesmerized as we watched Jennie climb out with her skirt riding up to her waist, and her beautiful, bald pussy on full display. I looked at the cabbie and he looked at me, and we both concurred; Nice! Then I patted Jennie down a bit to help her skirt find its intended position, before walking away. What a beautiful woman she is! I do truly love her.

After the cab departed, we searched for signs, as we tried to find our bearings, and the mysterious little shoe shop. As we strolled up Avenue C, we began to realize that the block was full of quirky little shops designed for the buyers of specialty items. There was a hat shop, a dress shop, a lingerie store, a smoke shop, a bookstore, watchmaker, leather goods, men's fine clothes, and a few other old-time shops that one might picture having filled New York City way back in the early 1900's. What a unique block it was. Finally, after a short search, we found the little shoe shop right in the middle of the block, exactly as Old Mickos had described it. The sign was small and understated, simply offering "Colleen's Elegant footwear." I took Jennie's hand as we descended the steps into the basement shop, both excited about what we might find.

Truth be told, I do have a shoe/foot fetish; a secret I don't hide all that well. And I love Jennie's feet and her footwear. She knows my weakness and has been teasing me with jokes and shoe memes for a long time, but this is our first endeavor into directly mixing my shoe fetish with our sex life. I think I am going to like it.

"Oh My God," I blurted out after entering the shop. "Look at all of these beautiful shoes." I had never seen a shop so filled with elegant, but extremely sexy shoes in my life. This place was a treasure trove of woman's footwear, and I knew that Jamie and his little foot fetish must be mesmerized as well. As I looked around the store, I saw all the famous designer names such as Louboutin, Jimmy Choo, Michael Antonio, Vince Camuto, Kristin Cavallari, Badgely Mischka, Giuseppe Zanotti, and even Ivanka Trump, and many others. I've previously seen each of these designers in stores, and on-line, but never all together like this. Is this store, it seemed as if every shoe they ever made was sexy, and elegant, with tall heel, and beautiful strapping; all waiting to tease me and Jamie. "Oh My!"

"Hello, hello, hello, and welcome to my little shoe shop," came the greeting from the beautiful sales lady who popped out from behind the curtain. "My name is Colleen, and I do hope I can help you find something you like this evening," she offered. As she came out from behind the counter, I realized that Colleen was a beautiful woman. Very tall, likely six foot or so, a little over the top in her make-up and style, but a stunningly unique, and attractive woman.

"Hi, I'm Jamie, and this is the love of my life, Jennie", I said in response to her greeting. "We're looking for a special pair of shoes for Jennie to wear this weekend during our visit in town."

"Well, I am glad you found my little shop and I know that I can find something for Jennie to wear that will accent her natural beauty," she said, while staring intently at Jennie. "It is OK for me to call you Jennie, isn't it?" she asked apologetically.