Tropical Escort Pt. 1: Monday

So, this is a series of stories that are 100% true. I went through a separation from my ex a few years ago. This is when I really gave into my desires to dress and be with men. And as a gift to myself, I decided to go on vacation! To San Juan Puerto Rico at that. Needless to say, my shopping trips leading up to the vacation were rather fun and expensive, but who cares! This is a once in a lifetime chance, and I wasn’t going to let it pass me by. Besides the obvious thrill of being able to dress when I want, go out when I want…. I also wanted a man for my vacation. At least one. So, a few weeks before going, I placed an ad on Craigslist to see if there were any businessmen there for a week. The subject line read “Your e****t for the week”. Well, I got a ton of the usual “hey baby, come on down and suck my dick” or “let me pee on you” types with hairy beer guts and small cocks. After a few days I almost gave up checking. But luckily for me I gave it one more chance. An email popped into my inbox from a man named James. He was from Sarasota Florida and was staying at the luxurious La Concha hotel in San Juan on the same dates I was. Right down the street from the apartment I had rented. I emailed him back with a few pics and he emailed me back with some of his. Besides appearing to be pulled together and “normal”, he was HANDSOME! Let me make it clear how hot this man was. 46 years old, firm body, well built, tan, smooth, dark hair, hazel eyes, and after a few email exchanges, I asked to see his cock. He said no and informed me, he wasn’t into quick hookups or endless banter. He wanted a girl like me for the week to be by his side, look pretty for him, dress the way he wanted me to, and please him the way he wanted me to. WOW! What a dream come true! He told me to bring casual clothes, a very fancy dress, and business-friendly clothes so I can meet him at the conference. He said he loved my retro-esque style, and left the lingerie and looks to me.

So, there ya have it. I had two weeks to go before I left, and was filled with anticipation. I packed two suitcases full dresses, makeup, accessories, suits, heels skirts, jeans, and even a pant suit. As instructed by James, I was to bring only mens clothes for the flight in and out.



DAY 1

I didn’t sl**p the night before. I was so excited. I had packed the night before and was ready for my early am flight. James emailed and told me he would send instructions for meeting him once I got in. My flight left at 5am, and I got in around 11:30 and got the keys to my apt and moved right in. I checked my email and James instructed me to put on business appropriate clothing, and meet him at the Hilton where the conference was. He was taking a late lunch, so I had plenty of time. I had shaved smooth that morning before leaving and only did some touchups. I put on some concealer and foundation, and my trademark eyeliner look. I decided to make a good impression and laid my white Ann Taylor skirt suit out on the bed. It fit me like a glove, and any woman in her right mind would know that unless you wanted toy look like trash, a thong would be needed with that skirt. I pulled out a peach shell and decided on a light green lace bra and thong. I pulled my lingerie on. Stumbling as I pulled the thong up and adjusted it in my ass. I was shaking! Not only was I going out in public which I had only done a handful of times before, but I was going out in broad daylight to a tech conference! Would people know? What would happen if they did? Who cares right?! I can pull it off pretty good and did my best. I clasped the bra in place and with my special little adhesive bra underneath to give me some nice cleavage. I then pulled the silkie shell over my head and reached for the white pencil skirt, which was high-waist/at-the-knee length, and pulled it on over my smooth legs and up to my waist and tucked the shell in. Next I pulled on my open toe tan slingback heels from Anne Klein. They were quite conservative and thought they would contrast the tightness of the skirt. I looked in the mirror, and fixed my shoulder length bob, sprayed myself with a little Estee Lauder perfume, pulled on the matching suit jacket and grabbed my purse. What a thrill it was to leave my apartment and step outside. I pulled on my sunglasses and went across the street to the Marriott and grabbed a cab. The cabbie was very sweet and opened the door and closed it for me. Off to the Hilton and my adventure began!

The cab pulled up in front and I paid and got out. I walked into the lobby and texted James. “I am here in the lobby”. Instantly, he asked me to meet him in the lounge. He was there in a booth. Well, I walked in and pulled my sunglasses up thru my hair and saw him across the room. I nearly melted. Tall, strong, handsome. A dream! We walked to each other and kissed each other on the cheek and I left a little of my peach colored lipstick there. He ordered me a drink and we exchanged conversations about our lives. Nothing sexual at all….. other than there was an incredibly handsome man that desires me across the table from me. I reached my hands across the table and he grabbed them and held them. I melted again! He said, “Claire, you are gorgeous, and we will have a great week together, but I am in control here. You wear what I tell you that turns me on, and with that said, I want you to meet me this evening for a cocktail at the Atlantic. Wear a casual dress.” I gulped and coughed out “OK!”. At this point, I knew I was his toy for the week. He needed to return to the conference. Instead of taking a cab, I decided to walk. I felt so confident after our meeting. I could feel mens eyes glaring at me as I walked down the street. With each step, my hips swayed more, and I began to strut. It felt amazing!

So, I got home and took a shower. I was meeting James at 5 at the Atlantic beachside and wanted to get ready. I poured myself a cocktail and went to it! I got my white linen halter dress from Banana Republic out and ironed it smooth. I realized I didn’t bring a slip with me, and that a white linen dress under city lights would be quite see-through. I decided to let the rum take away all my anxiety on that. I fixed my makeup and pulled my hair back and started getting dressed. I decided to wear a tan colored wonder bra ensemble underneath (no black thongs making me look like slut Right ladies!). Once again, I fixed the g-string in place, and clasped the lace strapless bra. I pulled on the dress and tired it behind my neck. I decided on some VERY sexy lace up sandal/heels (in one of my pics here on xhamster), and finished it with a turquoise block necklace and large hoop earrings. I grabbed my cocktail and stepped out on the deck to take in the view. The breeze blew through my dress and I felt beautiful.

I decided to go a little early and check the bar out. I pulled up to the bar and dropped my purse next to me and ordered a drink. The bar was beginning to fill up and just as I was thinking I was going to get stood up, I felt someone walk up behind behind me, grab my hips and pull me close. Ahhh…. it was James. He kissed me on the neck and cheek in a sweet way, but the message was made clear. The sexual energy he put out made me just want to start making out right then and there. Besides, I must say, this man was hot ladies! He was in a new tan suit and light blue button down shirt. An adonis! We giggled like school k**s at each other’s jokes and James was very affectionate towards me. He would hold my hand, rub his hand on my legs, and after a few drinks, even let his hands glance against my butt which sent shivers down my spine. Well, as expected, the subject turned to sex. He asked me how many men I had been with and I told only 3. He asked me what I like to do to please men, and told him that I love being their toy. We pulled closer together and continued the chat and finished our drinks. “One more?” he asked. “No way! I gotta walk in these heels handsome!” Well, he asked if I would like some company at my apt, and I gleefully obliged! We left and walked the 3 blocks back to my place and I unlocked there door and we stepped inside. By the time the door was closed, he pressed me against the wall from behind and began kissing my neck and nibbling my earlobes. His hands ran up and down my body, caressing my ass, hips and legs. I was breathing heavy and heard him whisper in my ear that he loves a woman that wears a thong band that he saw mine under my dress when he walked in and hew had been semi-hard since. And he was hard alright! I could feel his cock growing in his pants as he ground it against my ass. I spun around and began kissing him deeply as I stroked him through his pants. I pulled his jacket off and began unbuttoning his shirt. I got about 3 buttons down, and he said no. He had plans. He pushed me down to my knees in front of him and unzipped his pants and out popped a gorgeous cock! Not huge. Not small. Just smooth and gorgeous and hard. He held my head between his hands and guided his cock slowly into my mouth. One inch at a time he slid it in and I gladly accepted it. He slowly fucked my mouth until he was rigid. He pulled me up and said he wanted to fuck me, but asked if I might be into a more public place as he glanced behind me at my porch. I was on the 17th floor, facing across a main street and ocean. The Marriott was right there. I was a bit concerned, but then again, the sun had gone down, and if we had the lights off, no one could really see…. at least thats what I told myself. Well, I grabbed his hand and walked him to the porch. He was again behind me, kissing my neck and whispering dirty words in my ear about how slow and deep he was going to fuck me. His hands went up my dress, pulling it up so only he could see. He grabbed the straps of my g-string and pulled them down to my ankles. I then sensed he was fumbling for something in his pockets…… ahhhhh warming lube. He gently rubbed his fingers around my hole with the lube. I moaned as I bent lower and lower over the railing…… looking down at people walking by. One finger. Two. I wanted him badly. He grabbed me by the hips and slid his cock between my ass cheeks slowly….. as he continued, his cock would come closer and closer to going in. Each time I tried to adjust until finally, the head of his cock pressed hard against me, and felt him push….. In it went! His gorgeous cock was now getting pleasure from being wrapped in my tight asshole. He slid in slowly, out slowly. Taking it very slow. He fucked me like I had imagined a handsome middle-aged gentleman would. In a way that would please us both. I was breathing heavily and tried to keep my talking to a minimum as his hands grasped my hips and his cock pumped in and out of my ass. There I was on the 17th floor balcony with a white linen dress hiked up, heels on, panties around my ankles and a gorgeous man’s cock in my ass. He never fucked me hard. Just deep and slow until I felt him begin to swell inside me. He then pulled out and jerked his cock with one hand, and pressed me against the rail weigh the other. I had never felt a mans cum on my ass, but knew I was about to. One warm spot then another and another. He groaned as he exploded. He had aimed right at my ass and I could feel his warm seed on my hole and dripping down my legs. I turned around and cleaned his cock with my mouth and tasted his cum for the first time that week. It was delicious and sticky. He pulled me to my feet and kissed me deeply before he began stroking me until I came in buckets. Some was on his hand and he gave me his fingers to lick clean. We were both exhausted from a busy day and before parting for the evening, told me that I was to meet him at his hotel at 8:30am, and ask for room number 418 at La Concha. I would be attending the morning seminar with him, and he told me to wear another suit which I was thrilled I had. He exchanged a few more cum-soaked kisses before he zipped up and left for the night.

The week had started off right, and I couldn’t wait for the morning!

Part 2 coming soon……

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Posted by elpaulito
9 months ago    Views: 2,450
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9 months ago
Wonderful capture of your personal experience. Thank you for sharing. I look forward to hearing about part 2. Hugs, Jenna
9 months ago
luvly story hun, part 2 plz
9 months ago
Great story! I hope to read a lot more about your vacation.
9 months ago
Love it!, Can't wait to hear about the rest of the week.
9 months ago
nice tale!
9 months ago
excellent......can't wait to read more!
9 months ago
Nice and hot
tomjohnso...
retired
9 months ago
Awesome story