Jennie Goes to New York City

"Yes, yes, absolutely", Jennie replied. "And I'll call you Colleen," she added. "I feel as if we are already friends as another good friend of yours sent us down here, she continued.

"And who might that old friend be?" Colleen inquired.

"Old Mickos. He's the bartender at the Roosevelt Hotel up on Madison Ave. You do know him, don't you?" Jennie asked.

"Mickos", Colleen screamed, "I love Old Mickos," she added enthusiastically. "He has the sexiest Irish brogue, and I won't tell any tales out of school, but we are very good friends and have enjoyed many an evening together playing footwear games, if you know what I mean," she added with a smile that hardened my dick. "But enough about me and old Mickos; come over here and sit down, and let's talk about you two, and how I can help make your trip to New York City fabulous," she offered.

Colleen was fucking-amazingly hot. She was probably 40- years old or so, over 6' tall in her heels, and very slender. Her tits were small, but they were perfect tits for her size and shape. She had very fair skin, long reddish-auburn hair that she wore over the top of her head and down the other side. Long, beautiful fingers, perfect nails, thin legs, and a tight little ass, all added up to a beautiful woman. Best of all were her large, well decorated feet. She was dressed in a sheer black top, that was semi-transparent to allow a view of her black, lacey bra, a red, leather, pencil skirt down to mid-thigh or so, bare legs, and a beautiful pair of black, tall, strappy, leather heels. She was stunning!

"Tell me a little bit about yourselves," she asked, "like where are you from, what do you do, and what do you want from your new pair of shoes?" she added. I wasn't sure how much personal information I wanted to share, but I did have an odd sense that if we shared ourselves with this woman, we might just have an interesting evening.

"Well, we're from the Philly area," I offered slowly. Then I followed with "and we've been in love for over thirty years, and to this day can't get enough of each other," I added almost robotically. "And I won't speak for Jennie, but I want her to have a pair of shoes that will make her feel as beautiful as I think she looks," I added.

"Oh, so nice," Collen responded. What about you, Jennie", Colleen asked. "What do you want out of your new shoes and this weekend?" our hostess queried.

What do I want out of my new shoes, and this weekend? What a great question! What I wanted to say, was that I want to be the hottest woman Jamie has ever seen this weekend, and I want the entire weekend to be filled with mind-blowing sex, the likes of which neither of us have ever had. But not being that brazen, I didn't say that. What I did say was that "I wanted to be like Cinderella for the weekend. I want to be beautiful, and happy, and sexy till Sunday evening when Jamie and I had to part. Was that asking too much?" I asked Colleen.

"Absolutely not you beautiful girl," Colleen responded. "I know we can make this the weekend of your dreams," she added encouragingly. "Come with me, and let's have some fun browsing to find out what you like," she suggested, while grabbing my hand and dragging me towards the back of the store. "Jamie, you sit here and fantasize a bit while I tend to Jennie for you."

"In the front part of the store we have more conservative footwear," Colleen intimated, as she began her guided tour of the shop. "Conservative however, is a relative word," she added with sarcasm. "These shoes could be worn to work if you were a little daring, and you were thinking about fucking your boss on the desk," she said while laughing. "Hey, but who would do that?" she asked, while continuing to laugh. "Good, I've got you smiling now," she added while caressing my hand, and beginning to seduce me with her eyes.

As Colleen walked, she also touched while she talked, adding humor and explanation for much of what I saw. There was the conservative section, the platform and pump section, the stripper shoe section, boots, flats, sandals, and finally the section she called CFM, to which I naively asked, "what does CFM stand for?"

Colleen pulled me in close and whispered in my ear, "Come Fuck Me, honey, CFM stands for Come Fuck Me". And while she was whispering into my ear, she was also grinding her pelvis into my hip, revealing the fact that this beautiful, sensual lady either had a cucumber under her skirt, or a very hard cock. The scariest part of that reality was that I was incredibly turned on by it. I have never had a sexual relationship with a woman, nor do I have any experience with transsexual, or transgender persons. But at this very moment, I was horny as all-fuck, certain that Colleen was fucking-beautiful, had a hard cock, and she was coming on to me. And I thought to myself, "welcome to your fairy tale weekend Cinderella."

I watched as Colleen led Jennie by the hand around the store and I was getting very turned on by the obvious possibilities. Not only did Jennie look great wandering around this woman's shoe store, but it appeared that she was being subtly seduced by this fucking-drop-dead gorgeous saleswoman. Around the store they went, holding hands, stopping to hug, a whisper here, a grind, or a stroke of the leg there. They almost looked like lovers if I didn't know better. I watched as Jennie tried on, then walked around in a variety of the shoes Colleen suggested. She tried on platforms, and pumps, and peep toes, and boots, but then got a little more serious when she got to the section with the strappy sandals, which she knows I love. It seemed to me that every pair of sandals she tried on was better than the last, until she finally tried on a pair of black velvet sandals with jeweled embroidery on the strapping, and 5" heels. Oh, my fucking-God were those shoes hot! She was wearing a short black skirt, so the shoes coordinated well with her existing outfit, and they made her legs look like they were five-foot tall by themselves. Those shoes really did seem to make Jennie look like Cinderella, if Cinderella was a slut, without panties, or bra, and was leaking pussy juice down her leg. And fucking-Colleen, was near seducing her with her hands and eyes, as she assisted with the shoes. In my new fantasy, Jennie was the newly crowned princess with the beautiful shoes, and Colleen was her hand maiden tending to her every need. As I sat there and watched, I unwittingly started to stroke my growing cock through my pants thinking that I just might be the prince in between the two of them.

As we were trying on the different CFM shoes, Colleen was slowly but surely increasing the sexual heat in her sales technique. And it was really getting me turned on, although I was certainly confused as well. Colleen was a beautiful woman, but before tonight, I had no sexual interest in a woman, beautiful or not. Interestingly though, she most-definitely had a hard cock, which I do happen to like. A lot! And I caught myself finding Colleen's feminine beauty, combined with her hard dick, totally fucking-HOT. Oh, my fucking-God!

"I've got one final pair I want to show you Jennie," Colleen proffered. "These are a really special pair of shoes that I think will be perfect for your Cinderella weekend," she continued. "This is the latest design by Giuseppe Zanotti," she said while gently stroking my bare thighs. "He named them Coline Embroidered Velvet Sandals, and the list price is $1,595.00. But because tonight is such a special night, and you are such a special girl, they're on sale for 70% off," she added. "Let me help you try them on and tell me what you think," she continued, as she caressed my naked thighs seductively.

"Colleen, they are exactly what I was looking for," I screeched as she fitted the shoes onto my feet. As Collen was strapping on the shoes, it seemed that she was also intentionally pushing apart my legs, which just happened to have a bare pussy at the top; and a very wet bare pussy it was. And as she was fitting up the shoes, and pushing my legs apart, she was also caressing my feet, and legs, and just absolutely working me into a frenzy.

"Oh Jennie, you look so HOT in these shoes," she complimented. And then, surprisingly, she leaned in and kissed me. It was soft, and tender, and loving, and just delicious. Even more surprising was my response. I fucking-loved it, and her kissed her back!

"Colleen, I'm getting all worked up and I may not know how to handle myself if we keep this up," I warned her.

"That's OK Jenn," Colleen said to comfort me. "I'm very worked up myself and just enjoying your company. Why don't you walk over to Jamie and see what he thinks of your new shoes. I suspect he's worked up a little bit of a lather as well," she added with a coquettish smile.

"How do you like these shoes, Jamie?" Jennie asked with a distinctively seductive smile as she strutted up to me.

"I love them, and more importantly, I love you," I replied. "And tell me what's going on between you and Colleen? It looks awful hot between you two," I added.

"She is very hot," Jennie confessed. "And she fucking has me very hot" she also confessed. "But I think she, is a he, or something like that, and I am horny as fucking-hell, and confused about what I want, and who I want. All I know right now, is that I want these CFM shoes, and I want somebody to fuck me," she whispered to me not so softly. The combination of these shoes, Colleen's attention, and you Jaime, has me totally ready to explode. I need to cum, and I need to cum now, Jamie," she concluded.

Jennie was almost panting in her need for sex, and I was a little confused myself. Colleen was fucking-beautiful, and smoking hot, and normally I'd love a three way with Cinderella and the hand maiden. But the revelation that she had a dick, gave me pause. Theoretically, I don't have any problem with transsexuals, homosexuals, or whatever your sexuality might include. But on this night, I didn't know if I was ready to suck a cock, even if it was attached to a drop-dead gorgeous woman. "Come on, let's talk to Colleen and see where this yellow-brick road might lead," I suggested.

I took Jennie by the hand and we both sauntered back over to Colleen. Jennie, naïve Jennie, was most definitely the prey in the midst of two very horny predators. Dressed in her short skirt, sheer top, beautiful bouncing tits, and the Cinderella, black, velvet, 5", heels, made the possibilities seem endless. Although, truth be told, I think both of us had mixed emotions about the whole thing. When we left the hotel tonight, my only plan was to flash Jennie about town a little, buy her a new pair of shoes, get her sex gears engaged, then take her back to the room for a killer fuck session. Now though, it seems the two bumpkins from Philly, had a larger bite of the Big Apple available to them. The thought of a threesome with Colleen seemed entirely possible. And while I loved the thought of watching Jennie make love with this beautiful, transsexual woman, and I will also admit that fucking Colleen in the ass had tremendous appeal to me as well. However, I wasn't entirely sure where I fit into the equation. Was Colleen into us as a couple, or was Jennie her primary target? I didn't want to be odd man out to the beautiful chick, with her beautiful dick, even though the thought of Colleen really turned me on, dick and all. Even if she responded to me, and my cock, I didn't know if I was ready to cross over to the other side and suck her dick, or even more disconcerting, experience her dick in my ass. Decisions, decisions....

Anyway, as both Jennie and I walked up to Colleen, we stepped right into a group hug, upon which both ladies began sensually kissing. Both also simultaneously reached out and began stroking my hard dick through my pants. While the kissing continued, I started a little breast play, alternating between Jennie and Colleen. Both had smallish tits, but luckily, I happen to be a guy that prefers his tits on the smallish side. Without a bra, Jennie's exposed nipples were rock hard and fairly begging to be squeezed. Colleen's tits on the other hand, were shrouded by her bra, but they also appeared to have hard nipples, and were perfect to the touch. Colleen then, moved off Jennie's lips and onto mine, for a slow, sensuous kiss, while her hands snuck under Jennie's skirt to finger her wet pussy. Jennie was moaning, I was groaning, and Colleen was working the two of us like an orchestra maestro.

Just as I was about to jump right into the fantasy full bore, the bells attached to the front door began to chime, announcing the arrival of another customer. Each of us backed off quickly, putting our respective body parts where they belonged. Colleen excused herself, to quickly run towards the front of the store to greet the new customer. Jennie and I remained in the back to regroup a little prior to facing the rest of the world.

I asked Jennie what she wanted to do? She demurely responded, "it's up to you Jamie."

I grabbed her tight, kissed her hard, and told her I just wanted to go back to the hotel and fuck her, to which she replied, "Let's go," adding, "I'll put the shoes back in the box while you pay."

On the way out, we stopped to pay for the shoes, and say a special 'good night' to Colleen. (The fucking best $450.00 I ever spent) We each gave Colleen a salacious hug and kiss, a tremendous thank you for a great evening, and a promise to do it again sometime. And with that I grabbed Cinderella, and her box of new shoes, and we ran out into the New York City night seeking a cab and sexual release.

"Taxi, Taxi" I screamed as we ran up Avenue C towards 8th Street. At least I was running. Jennie, who was now back in her original, 4", strappy, leather heels, was hopping at best, trying to keep up. Thankfully, the cab stopped and waited for us, allowing us a little more leisurely pace to get to the corner.

"Thanks for waiting," I said to the cabbie as we got in.

"No problem, sir. "I am Happy to wait for you, and your beautiful lady friend,' he added.

Sometimes I think it's just me who finds Jennie so fucking-beautiful. Then, I'll get into a situation like this, and find people do the nicest, and sometimes most amazing things, just to spend a few moments with Jennie. Maybe it's just to get a better look at her, I don't know. From the moment I first saw Jennie, I was mesmerized by her unique beauty. It is so entertaining to observe others as they encounter her beauty for the first time and watch how they near hurt themselves trying to get a better look. She is that good looking.

"Where can I take you two this very fine evening?" the cabbie asked. He was a young Indian man, maybe 25 or so, years old.

"The Roosevelt Hotel please, Madison Ave., at 45th St.", I replied.

"Oh, that is a very fine Hotel sir. I will get you right there in a hurry," he added

With that, I replied with a "thank you," then leaned over to give Jennie a kiss. "We'll be at the hotel in no time I assured her."

"Good", she replied, "I am boiling over in anticipation."

"Just the way I like you," I countered. "Here, lean back against the door and put your feet up in my lap," I directed. "I'll give you a little foot massage as we ride."

At this point in the day, a foot massage sounded wonderful. I had been traveling all afternoon, getting to NYC, then making the trip down here to the East Village, so I had been on my feet for hours. And as much as I love the way heels make my legs look, a woman can only wear heels for so long, before she begins to tire.

As I was beginning to relax, Jamie leaned into me and I thought he was going to kiss me again, but instead, he whispered into my ear, "unbutton your coat and pull up your skirt."

I was a little uncomfortable with that request knowing I was not wearing any under garments, with my short, little skirt, and see-through top, leaving very little to hide behind. But, by nature, I am sexually submissive, and have always responded to Jamie's more dominant character. Tonight, was no exception. As directed, I unbuttoned my coat and spread it apart to expose my barely covered breasts, then hiked up the skirt enough so that my bare behind was now on the seat cushion, with the top of the skirt still somewhat covering my private area.

"Beautiful," Jim cooed. "Now, put your feet up on my lap for that foot massage."

He started rubbing each of my feet with the shoe on at first. Beginning with a gentle caress of the toes, then a soft massage of the instep, and more rubbing of the Achilles, and heel area. It felt absolutely- wonderful! Then he took off my right shoe, gently undoing the buckles and straps, letting the leather heel fall to the floor of the cab. He took the bare foot in both hands and began a thorough massage of the toes, the arch area, and the bottom of my foot, which again, felt unbelievable. After unbuckling the left shoe, he continued with the massage of that foot as my mind and body began climbing the hill towards the next explosion. Unconsciously, I reached down and began rubbing my bare pussy. Oh God that felt good!

Jamie again leaned in, but this time he actually did kiss me. A hard, wet, and passionate kiss that went direct to my loins like everything else that evening. Then he went to my ear again and whispered, "keep rubbing your pussy while I put on your new shoes." Wild horses could not have pulled my hand off my pussy at that point, so I just nodded and complied like a good girl.

Eventually, he reached over and opened the box of new shoes. After taking each shoe out of the box, he took a deep inhale, smelling the shoes, then brought each bare foot up to his mouth and began kissing, licking, and wet massaging each foot again before eventually putting it in its respective shoe and buckling it up. All the while I was rubbing myself and climbing higher and higher up that mountain

"Oh, Jamie I'm getting close, and I want to cum so bad," Jennie quietly pleaded. "Cum for me Jenn. Cum for me right here, and right now in this cab. Cum right now Jennie!" I ordered. As I said that, I looked up and saw our young Indian cabbie staring back at us in the rear-view mirror. I smirked at him, and he smirked right back at me, then I returned my attention to Jennie. She was becoming highly agitated, so I reached out and began fondling her beautiful titties right through her thin, transparent top. God, she has great tits! Her nipples are small, but pointy and hard, and they were begging to be played with. I was getting a little crazy and decided to see if I could take Jennie to that crazy place with me. "The cabbie is watching you Jenn, and he wants to see you cum," I told her; "Cum for the cabbie Jenn. Rub your pussy and cum for both me and the cabbie. Cum for us Jennie, right fuckin-now, CUM RIGHT THE FUCK, NOW, JENNIE". And with that she exploded! She was frigging her wet cunt, and I was squeezing her nipples hard, and she was grinding her high heeled feet into my hard cock, and the fucking-cabbie had his eyes popping out of his head and most likely his dick in his hand while Jennie was thrashing, and groaning, and having muscle convulsions in the back seat of his taxi. Welcome to Fucking-New York Cinderella!

I cannot believe how dirty this was getting. Here I was, "Sweet Jennie," in the back seat of a New York City taxi, masturbating like a wild woman, while the cab driver was enjoying the whole scene through the rear-view mirror. My mountain was about to pop like a volcano. As I was masturbating, Jamie was pinching my nipples, and pushing me along; telling me to cum, and cum now, and cum for him, and cum for the cab driver, and the next thing I knew I exploded, screaming "Jaaaammmmmiiiiieeeeee, Oh Fuck, Oh Fuck me, OH FUUUUUUUCCCCCKKKKKKKKK!!!