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A Vacation Of Firsts

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We find Eric St Clare naked and under the sheets of king size hotel bed, oblivious to the rain and thunder outside. His arms are wrapped around a stunning dark haired beauty clad only in nylons and garter belt. They are sharing gentle kisses on each other's necks and lips as Eric allows his hands to run across her naked breasts as well as her nylon covered legs.

A soft moan escapes the brunette's red parted lips as Eric slowly draws his fingertips up the back of her leg and he marvels at the feeling of the warm flesh underneath her black nylon stockings. Between the tactile sensations and the sounds of her moaning, Eric is hard again in no time.

His erection soon is evident to his bed partner who stops kissing him.

"Is that for me?" she asks in a breathy whisper as her hand gently encircles his hard cock.

Eric only smiles and a moan of pleasure escapes his lips as she commences to jack his cock and kiss and lick his hard man nipples at the same time.

This was Eric's first trip to Hawaii to escape the harsh Winter of the midwest and he planned to stay the whole season. Money was not an issue as Eric was wealthy, very wealthy and had retired at fifty. Normally he spent his winters in Vegas where he became known to a number of casinos and hotels, as well as a regular to a select few of the full-service escorts.

He wasn't bad looking for his age thanks to an aggressive weight lifting and diet program that he had adopted shortly after he retired, that and his decision to banish the salt and pepper hair and go full grey. However, it was evident to many of the girls that he encountered that he was well past thirty and while they considered a handsome and entertaining host they showed no romantic interest toward him. This problem seemed to be a constant plague to him and tonight was no different.

Having no luck with the ladies he encountered that evening at the local clubs, he decided to head back to his hotel. During the cab ride, he came to the conclusion that maybe he had made a mistake in coming here. He decided that tomorrow he would head to Vegas and the sweet charms of his favourite escorts. 

It was as he crossed the spacious lobby that he saw the attractive brunette sitting by herself at the empty bar. She was so stunning that he had to see her up close, so he approached the bar and took a seat a few stools down from her and ordered a Bloody Mary.

Up close he discovered that her black dress with silver threads running through it was very short and very tight and the thin material clung to every curve. Her long slender legs were covered in black pantyhose and stiletto heels adorned her tiny feet. She was the personification of everything he desired in a female.

She looked in his direction and gave him a faint smile when he sat down. She then took another drag off her cigarette and returned to staring at her glass and that was all the encouragement he needed to speak to her.

"Rough night?" Eric asked.

"You could say that. I was stood up," she responded without looking up.

"Well, from what I see, all I can say is it was his loss," Eric commented.

The brunette lifted her head and looked at him and gave him another a brief smile.

"And what brings you back to this quiet place at such an early hour?" she asked.

"Well, I am staying here for one and most of the ladies that I encountered this evening believe that I am too old for them," he answered honestly.

"Well, to paraphrase what you said, from what I see it is their loss," she replied as she slid off her stool and moved over next to Eric's

"Tonya," she said extending her small hand.

"Eric," he replied as he took it and was able to study her face.

Tonya was quite attractive in a tomboy sort of way. Her long dark hair framed a pretty, tanned face and that alone was an attraction for him as brunettes had always been his favourite. Another round of drinks was ordered and they commenced to talk. She was born and raised on the big island and hoped to visit the mainland someday. This hotel was her favourite dinking spot as it attracted a much nicer clientele than her regular haunts. 

Eric told her stories about his travels around the world and the exotic places he visited, but it was his stories about Las Vegas that she enjoyed the most. The rainstorm came out of nowhere and sent all those lounging at the poolside bar inside. Eric saw the crowd begin to trickle in and he quickly grabbed a booth designed for two and asked Tonya to join him.

Moving from the bar to the booth allowed Eric to take in the sight of her slender legs and tight butt as she walked ahead of him. They continued to talk, laugh and drank oblivious to the crowd at the bar and the increase in the noise level.

"So, I take it that you like my legs? Don't deny it, as I've seen you staring at them the moment you sat down," she said out of the blue. 

"I won't deny it, you have great looking legs. Great looking legs encased in black pantyhose have always been a turn on for me," Eric admitted.

Tonya gave him another smile and crossed her legs again which caused her hemline to inch upwards. She then told Eric to take a good look again. He moved his eyes down and there, peeking out from under her minidress he saw the hint of lace tops of nylon stockings along with the ends of the ribbons that secured them to an unseen garter belt and a bolt of desire shot through his body.

Tonya slid closer to him and allowed him to place his arm around her slender shoulders.

"Pantyhose are all right, but when I'm going out its always nylons," she confided in a soft voice.

Eric had no reply as he continued to enjoy the view. Girls in exotic lingerie were a favourite of his and the escorts in Vegas knew this and always wore them when he was in town. Between the sight of her legs and the feeling of her firm body pressed against his, he began to get hard. He stared into her liquid brown eyes and the cherry red lipstick as she spoke while her perfume filled his nostrils

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When she suggested they move to quieter surroundings, she felt Eric withdraw.

"Look, I'm not a working girl if that's what you're thinking and I have never made such a suggestion before, but it's getting too loud in here to talk. Plus I don't kiss in public," she stated.

Knowing he would be given the opportunity to kiss those cherry red lips was all Eric needed to hear. The tab was paid and arm in arm, he escorted the stunning dark-haired beauty to his luxury penthouse suite. She took a seat on the couch while Eric fixed them drinks.

He was now offered even a better view of her crossed legs as he approached her with drinks in hand. They continued to talk more and allowed him to run his hand over one of her nylon covered knees. She only froze when he leaned in and tried to kiss her.

"I probably should have revealed this to you when we were downstairs, but I was afraid of what your reaction would be. It's the reason I was stood up," she said quietly with downcast eyes.

"Reveal what?" Eric questioned.

There was a moment of hesitation on Tonya's part before she took hold of his hand and placed over her crotch. Through the thin material of her dress, Eric felt a small hard cock pressing against the silky fabric. Now Eric was too jaded to react in a negative fashion. He had visited many exotic clubs in his travels and seen others like Tonya so he was not too shocked. What shocked him was his attraction to her despite his discovery.

"Yes, I'm a T-girl," she admitted. "I was stood up when my blind date discovered my secret and exclaimed out loud that I was a dude in a dress before he bolted. That will be my last attempt to date online."

Eric allowed his hand to leave her crotch area and gently slide over her left breast, it was firm and full and he could feel her nipples pressed against the material. 

"Yes, the girls are real and all mine," Tonya purred as she placed her face mere millimetres from his.

Eric could see no hint of a male in her face and his desire to kiss her grew even stronger.

"If you want me to leave now that you know my secret, I will," Tonya continued in a soft voice."But I'm hoping you'll ask me to stay as I find you very attractive."

"Please stay," Eric managed to say in a stranged voice as his mind wrestled with all this new information about her.

Now in his travels, he had been with girls from all walks and ages, but this was a first for him. This female looked and dressed as he wanted all his females to dress. He finally gave in to his desire and very slowly moved his lips toward Tonya's. The first soft touch sent a shiver of lust through his body and wound up in his groin.

He looked at her pretty face before slowly attaching his lips to hers again. This time, he parted his lips as she did and their tongues touched. Their kisses grew longer as Eric's hand ran the length of her crossed leg. This was another first for him. He knew that she wasn't born female and still had some of her male parts, but he didn't care.

Tonya unravelled herself from Eric's embrace after awhile and stood up and then turned to face him. She reached behind her back and unzipped her black minidress and slowly tugged it down as Eric stared with unblinking eyes. The material cleared her full breasts first and revealed a black silk bra trimmed with delicate black lace.

As the dress travelled down her body, a hard and flat abdomen with a glittering piercing in her navel were visible. Tonya wiggled her hips so that her dress cleared them and now Eric had a chance to see her black silk garter belt that held up her black nylon stockings and her tiny black panties that covered the last evidence of her birth gender.

Now Eric had been to more strip clubs than he cared to remember. From the cheap dives to the top-of-the-line establishments and he was had never gotten this excited watching a female remove her clothing before. Tonya returned to her place next to him and they resumed kissing. It was gentle at first but soon escalated into a tongue sucking frenzy as the minutes ticked by.

Tonya stopped him only long enough to remover her bra and Eric's mouth and lips soon were kissing and licking her satiny smooth breasts. Tonya emitted soft moans at the attention he was rendering to her erect nipples. She stopped him once again and began to remove his polo shirt and kissed and licked every exposed piece of flesh as the shirt was pulled up over his head.

Tonya's lips soon attached themselves to his chest where they kissed and licked his hard nipples. Between her soft lips, the feeling of her silky hair against his warm flesh and her perfume enveloping him he became fully erect. Tonya saw the bulge in his dress slacks and ran her finger over the top of it.

"Oh my," was all she said as she removed her lips from his chest.

Tonya stood up and pulled Eric to his feet, She then knelt down in front of him and removed his loafers before she commenced to undo his belt and pull his zipper down. She then slowly pulled his pants down to his ankles thus revealing muscular legs and boxer briefs. What really pleased and surprised her was that he was not one of those hairy men she had encountered in the past.

They embraced again and the kissing became even better for Eric as her full breasts were pressed against his chest and he was now able to run his hand over her firm silk covered bottom. It was when he reached for the waistband of her panties that she ended the kiss and froze.

"Are you sure you want to do this now that you know the truth?" she asked.

"I'm sure," he responded.

"Then let me," she responded as she began to slide her silky undergarment down her slender legs.

 

To be continued.

Published 
Written by ThePhantom
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