Vacation in NYC

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CD meets his online lover in NYC.
1.3k words
4.69
7.3k
8

Part 1 of the 2 part series

Updated 06/10/2023
Created 11/25/2020
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Patticd
Patticd
10 Followers

This is my first story. I hope that you all like it!!

The 4 hour drive from Boston to NYC was full of excitement. I stopped along the way in CT and got a pedicure and then off I went. The lady looked at me strange when I asked for the hot pink polish, but that's why I stopped at a random place where I knew nobody. The ride was fast. No traffic at all. I drove most of the way in heels, which made the ride even more fun.

After checking in at the Marriott Marquis, I went upstairs and started to unpack. I was so excited. The next 4 days were going to be spent entirely as Patti. This had never happened before. Usually it was an hour here and a couple hours there.

I took a long bath and shaved every hair off my body. I had my outfit picked out long before I even arrived in The Big Apple. I started by pulling up my white lace thong. Next I put on a lace matching bra. Then I slowly rolled up my white thigh hi stockings, careful not to get a tear. Then the long, white, lace, sheer gown with slits up both legs. I put on my 5 inch clear platform, ultra sexy stripper shoes!! After admiring myself in the mirror for a few minutes, I went to the makeup table I had earlier setup. I put on my giant, gold hoop earrings and my fake nose ring. Slipped on my rings, anklet and bracelets. I put on my shoulder length, wavy blond wig. Finally, I did my makeup and applied my fingernails (french manicure, of course!!).

By this point, I was so horny. I stood in the window, glaring down into Times Square wondering if anyone was looking up at me. I bent over in front of the window, slid my thong string off to the side, and inserted a small butt plug. I loved the feeling of having the plug inside me. It adds to the feminine feeling that I get when transforming into Patti. I rubbed my pussy for a few moments, while still looking into Times Sqaure.

I poured myself a drink and slowly strutted to the couch and sat down. I crossed my legs and started to rub them up and down. I love the feeling of nylon clad legs. Soooo sexy. I was relaxing and taking in the moment when I heard a knock at the door. I put down my drink and stood up. I checked myself in the mirror and walked over to the door.

"Who is it?"

"Tony"

I pulled open the door and there he was. 6'2" of pure, hunky manliness. He threw his bags into the room and I jumped into his arms and we started to passionately kiss. Tongues were moving so fast and so deep that I felt his tonsils. We closed the door behind us and slowly made our way to the bed, kissing the whole time. "You look gorgeous", he said. I put my finger over his mouth and started to undress him. I was wasting no time. I ripped off all of his clothes. I took a second to take him in, laying on the bed, naked, and rock hard. I got back on the bed and started to stroke his shaft with my nails, something I knew he liked. He shivered and I cupped his balls. Slowly massaging them. I went in for another kiss while rubbing my very hard girlie cock against his. I had waited 3 long years for this moment. Tony and I had been talking and playing online for that long. We both had to make it so the time was right to meet, and that time was here.

I went down and started to lick his shaft, very slow. I licked his head and rubbed his balls. Slowly I scratched his balls with my nails. Knowing that he was so turned on, had me even more turned on. I was rock hard and oozing precum everywhere. I sucked on his sexy cock for a few minutes. By that point, I was going to cum. Tony saw me and said, "Cum in my mouth, baby."

Quickly, I moved towards his mouth. When I got to about 4 inches away, I blew my load. Most of it got in his mouth, a little on his chin. He sucked me dry and then pulled me close to him. I went in for the kiss, only to find that my cum was still in his mouth. He spread my cum all over my mouth with his tongue. I obliged and kissed him passionately. I knew that it was time for me to get back to business.

I started to rub his cock as I slowly turned around on the bed. My bum was near his face, my mouth was on his cock. I kept sucking and licking and he started to kiss my bum. Wow!! That felt amazing. I started to go a little faster and saw that he was starting to tense up. I knew what was coming. In and out I went. Faster and faster, until I felt Tony shoot his load into the back of my throat. I slowed down, but kept licking until all the cum was gone. I licked his cock clean, like a melting ice cream cone. I was not like him. No sharing here. I swallowed it all, and I must say, that it was quite yummy.

I moved up close to Tony and he wrapped his arm around me. We layed there for a little bit and then started to chat. Chatting led to kissing. Passionate kisses with plenty of tongue and nibbling. I put my hand on his cock and he was hard again. I still felt amazing and knew that I wanted him to fuck me.

"I see you are ready to go again", I said.

"I have told you that I am always ready!!"

I reached into the nightstand and grabbed the lube. "You up for some fun?"

"Are you sure you are ready for this? You said you would wait and see how it goes."

"I'm ready. Just be gentle." I got up on my knees and asked him to take out the plug. He slowly pulled it out and put it back in. I was rock hard again. Tony pulled out the plug and started to apply lube to my pussy. I let out a huge moan when he inserted a finger into me. I grabbed the lube and slathered it all over his dick. I threw a pillow under my belly and I leaned forward onto it. He started to rub the tip of his dick around the opening of my hole. OMG!! He slowly inserted himself into me. Once he was inside I felt amazing. I will admit that it hurt a little but the pleasure I was feeling was much greater. He fucked me slow for quite a while. In and out he went and without notice, my cum shot across the bed. I was breathing heavy, enjoying every minute. Tony was going at his own pace. He was still going slow, with an occasional heavy thrust all the way in. I could tell that he was getting closer to cumming.

"I want to cum inside you."

"What if I get pregnant?" As we both laughed, he shot his load deep inside me. I moved back into him a few times and he kept his dick inside me until it went soft.

I layed back on the bed, not caring that cum was dripping everywhere. I could barely move. Tony went to the bathroom and was walking back to the bed. He jumped down next to me.

"Wow. I can't believe we took 3 years to do this."

"I agree. It was well worth the wait. Keep me close all night."

I had no interest in cleaning myself off. I rolled over and quickly fell asleep, while in Tony's arms. Before I closed my eyes, I thought to myself, the first day was amazing. What will the next 3 be like? We shall see...

Patticd
Patticd
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Riki1942Riki1942almost 2 years ago

Wow, love your story and I can so empathize with most of the things you wrote! I'm gay, a crossdresser and a bottom.

While I don't dress 24/7, I do so much of the time and always while with my boyfriend.

He doesn't suck my cock or give me snowballs, (I'm the girl) but I have given them to him after sucking him off.

That feeling of rubbing your pantyhosed legs together is such and erotic feeling and the feeling of nylons and pantyhose on your smooth and hairless body is indescribable!

Knowing that your man is super turned, horny and loving what you are doing to him is a huge, HUGE factor in making it great sex!

Like in your story, I just love to cum before he does. When I cum while he is still fully hard and inside me, my ring starts to convulse, clamping down over and over on his hard meat and, at the same time, the knowledge he will soon be pumping his cum inside me is like no other feeling in the world. It's like having two orgasms at once; a regular one and and one in my "vagina" at the same time!

Naturally, we gurls love the physical feeling of something in our pussies, but there is more to the craving to be plugged than that alone. It's a constant reminder of who we are and what our bodies are made for. Also, there is something that seems to cause me to mince my steps more in heels and gives me a more sexy strut when I'm plugged. They also keep our pussies in shape and ready at a moments notice to take our man's cock when he is too anxious to get it in us to fool around with getting us properly opened up.

If I know we are going to be together, I always slip a butt plug to pre-stretch myself. However, after he cums and slips out, I often slip my plug back in to help hold his load inside me. I would rather none of it leaks out because it really turns me on to know that his sperm is swimming around in my insides.

Riki

CrossdressingChatCrossdressingChatover 3 years ago
Very yummy story

Thanks for for work. It got me very hot.

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