Nikki Goes to Crete Pt. 02

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Our lead loses their virginity twice as a man then a woman.
4.9k words
4.68
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12

Part 2 of the 3 part series

Updated 06/23/2023
Created 06/17/2023
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AnnaV
AnnaV
82 Followers

Chapter Four

The next morning Nikki woke up as the temperature started to raise. It took her a few seconds to work out where she was.

Then it all came back to her.

She was in Crete, in the Sitia Beach Hotel's best suite. She'd met Michelle and admitted to her she was known as Nikki when she put on a dress. She'd met Michelle's barman husband, the gorgeous Michael who also knew she had a female side known as Nikki. He had seemed quite taken by Tony too!

Nikki knew she could pass in public, but decided to restrict Nikki to the suite. Tony would explore the rest of the resort for the majority of the holiday.

Having made the decision, Nikki got out of bed and headed for the shower. As she walked past the balcony, she noticed that the remnants of last night's meal had all been removed. Someone must have come to her room whilst she slept. If they'd walked past her bed, they'd have seen her sleeping in her nightie. She could only hope that it was either Michelle or Michael and that someone else hadn't found out her secret.

And so Nikki went in to the shower and Tony exited it.

Tony caught the lift down to reception, hoping that Michelle wouldn't be there.

"Well, hello Tony. How are you this morning?"

"Good morning Michelle. I'm fine thank you. Just fine."

"Breakfast is through there."

"Thank you Michelle."

"See you later. Oh and tell Nikki I love her nightie. Very cute!"

"I'll let her know."

Tony blushed and rushed out of reception towards the restaurant.

"Hello Sir. May I take your room number?"

"Room 61."

"Will your wife be joining us Sir?"

"Sorry? My wife?"

"Yes Sir. Our records show Miss Nicole is in room 61."

Tony took out his key and showed it to the waitress.

"Yes, it's room 61. See?"

"Sorry Sir. We must have made a mistake. My apology. Here. Please let me show you to your table."

The waitress weaved through the restaurant and led Tony to a table for two.

"Just a moment. I'll remove the remove the second sitting."

"Don't worry Miss. It'll be fine. Everything is fine."

"Can I get you a drink whilst you decide what you'd like?"

"Orange juice will be fine. And I'll have a small omelette and two slices off toast please."

"Of course."

As she walked away Tony couldn't resist watching her. She was a beautiful dark haired girl, probably in her early twenties. Her black pencil skirt was a snug fit on her tight bum. In her one inch heels, she had a sexy wiggle in her walk. Tony watched her walk all the way to the kitchen. He quite liked the raven haired, deep voiced waitress.

Breakfast turned up and Tony ate it whilst watching the other hotel guests. He kept an eye on the waitress who served him. Every time she walked by his table she gave him a big smile which he returned.

On his way out Tony waited until the waitress was back at the entrance to the restaurant so he would have the chance to say goodbye.

"Thank you. That was lovely."

"My pleasure. Have a lovely day, Miss Nicole.", she giggled. "See you tomorrow."

And she gave another big smile.

On his way back to his room, Tony was pleased to see that Michelle wasn't at the desk. He checked with the receptionist that he was entitled to a session at the spa. As he was, he booked it for later that day.

He went back to his room, brushed his teeth and packed a few things in his man bag, ready for a morning to explore the local town. His luck was still with him. The receptionist was on her own when he got to the foyer. He waved to her as he headed out of the door and hit the mid-morning heat. She waved back, smiling pleasantly.

Tony wandered along the sea front and took off his flip-flops as he walked along the beach. He loved the feel of soft sand as it swelled up between his toes. He walked the length of the beach and came back along the road looking in to the shops as he went. As he was planning on spending more of his time as Nikki back at the hotel, he decided to use some of his limited spending money on a few extras. He found a little boutique where he purchased two new bikinis. One was a simple black number the other was bright white with a little fringing. Both were slightly padded to make the most of any breast material they were designed to support. He also found a pair of coral hot pants which he loved. Finally, Tony selected a couple of cotton skirts, one just above the knee, the other would barely cover his bum cheeks, a selection of tops and a sexy little black dress that he could sit in when eating his dinner in his room.

"Thank you Sir. That's quite a collection of clothes."

"Eh? Oh yes. My wife's case was lost on the flight over. She'll need a few things until the airline find it and it catches up with us."

"That's terrible. Might I suggest your wife might need some underwear to go with these?"

"Oh... As luck would have it, her underwear was in my bag. You know what women are like? One bag is never enough for them!"

"Of course Sir." the assistant smiled and started to add up the prices.

"Can you add these too?"

Tony had found a pair of oversized sunglasses which would be the finishing touch to any outfit.

"Yes Sir."

Tony paid and headed back to the hotel to try out his purchases. He liked everything he had bought, but the favourite was the black bikini. The sides of the knickers were tied in a bow on the sides and the bra was two triangles to cover the majority of his tit flesh. He couldn't wait to have a golden tan and be able to show off this beauty.

It was time for his appointment at the spa. He hung up his new purchases and headed downstairs for his treatments. Tony had never been to a spa so didn't know what to expect. He was offered a whole range of treatments, most of which he didn't understand.

"I'll start with a massage please."

"Okay Sir. Here's your gown. Please get changed in the room over there and leave your clothes in the locker."

Not being sure what was expected, Tony removed all of his clothes, placed them in the locker and put the dressing gown on, making sure it was tied firmly at the waist.

"Thank you sir. Please follow me to the treatment room."

Michelle certainly knew how to pick her staff. The spa receptionist was ass cute as a button. She was about five foot nothing but had curves in all the right places. Her white blouse was struggling to contain her bountiful breasts and despite wearing flat shoes, her white skirt was wiggling away nicely as he followed her.

"Please take off your gown and lay down on the table. Your masseur will be with you shortly."

"Thank you."

Tony removed his gown and hung it over the back of the chair. Feeling a little exposed he then jumped on the table and laid face down awaiting his massage.

After a couple of minutes of nervous waiting, Tony heard the door opening and someone entering the room.

"Oh my! You're bold aren't you."

Tony stiffened up and looked over his shoulder. He had been expecting his masseur to be a woman, but that was definitely a man.

"Most of my clients wait to get to know me before offering me their ass!"

"Oh I'm sorry the lady at reception said to remove my clothes."

"Don't worry. I've been welcomed by worse sight than this sexy little thing."

The masseuse pinched Tony's ass cheek and wobbled it about a few times.

"We'll get on just fine. Just you relax and leave all the hard work to me."

And that's exactly what Tony did.

The massage started on his left ankle, working along the calf with strong, firm hands. Then above the knee and up the back of his thighs. Tony tensed as those hands were approaching his buttocks.

Would he stop?

Would he massage his ass?

Or something even more intimate?

And then he started on his right ankle, following the same process. This time as he approached the very top of his thighs, Tony held his breath. The masseur was now caressing both of Tony's butt cheeks. Tony could feel himself becoming aroused. If this man didn't stop soon, he would be making a mess on the table. His breath was now becoming a pant. The masseuse must have sensed what was happening as he moved on to Tony's torso.

He began with the shoulders releasing all of the knots that had been building up in Tony. His oiled hands were working wonders. Tony felt very restful and was close to sleeping. The masseuse hands moved down Tony's back, releasing knots as they went. Finally he had reached Tony's waist. Again he began to massage those firm buttocks.

Gently with one hand he was nudging Tony's thighs apart. In his near sleeping state, Tony was very compliant and let a gap appear between his thighs. He was barely aware that the masseuse had stepped away from the table for a moment. The massaging returned. With his oiled hands he was paying special attention to Tony's buttocks.

Tony then felt his butt hole opening up. The masseuse's finger kept rubbing the entrance to it. Then, almost my accident, an oiled finger penetrated his hole. Instinctively, Tony tensed up.

"Relax. You're in safe hands."

And Tony relaxed. He felt that finger slide inside him. It kept on going in and out of him, opening him up slightly. It was then followed by a second which he accommodated easily. He was beginning to enjoy this part of the massage.

But then it suddenly stopped and he was left with an open ass hole.

But not for long.

The finger was back. Probing his arse again. But it felt bigger now. Perhaps he was using one of his thumbs?

No.

Thumbs aren't that fat.

Or that long!

Tony looked over his shoulder to see the masseuse midway through mounting him.

"Just Relax Sir. I only do this for special clients. Michelle said I was to treat you as a very special client. Don't worry. I'll be gentle."

Tony just put his face back towards the table and prepared himself to be invaded by this Greek man.

He was true to his word and was very gentle. What he hadn't declared was just how big he was. When dressed as Nikki, Tony had often used dildos in his ass. He had a lovely 8 inch toy with realistic veins which he loved to use. But the man now fucking him was stretching him more than any dildo he had ever used.

He started off slowly, letting Tony get used to his size and gradually sped up. He was holding on to Tony's waist as he increased the tempo. Despite his initial reluctance, Tony was now meeting each down thrust with his own thrust upwards. Tony could feel two huge testicles banging against his own scrotum.

Tony began to prepare himself for the cum that was about to be deposited in his bowels.

"Oh yeah. Get ready gurl. You ready to feel my cum in you?"

"Yes please. Fuck me. Make me your bitch. Shoot your cum up my girly ass. Screw me like a dirty whore and fill my pussy with your spunk. Fill my belly with your jism. I want to feel your cock pulsing in my tight virgin channel."

Tony couldn't believe he was being fucked for the first time and he was talking dirty like a common street walker.

Tony was now on all fours as the stranger with his cock buried in Tony's arse had his huge, manly hands tight around his waist. Every slap of his thighs he penetrated deeper in Tony. Each thrust his erection was exanding, his veins pulsing.

And Tony knew what was coming next.

"Shit! I need it now. Please cum inside me. I can't take it any more. I'm begging you to cum in my pussy and make me feel like a sexy woman. Make me your sissy boy. Make me your cheap slut. Make me your future wife. Make me pregnant. Make me feel whole. Just shoot your cream in me again and again and again. White wash my hole."

And so he did. He filled that ass up with spurt after spurt of cum. When he finished cumming he withdrew his cock and wiped it across Tony's butt cheeks. As a good masseuse, he massaged his thick white cream in to Tony's cheeks. Without touching himself, Tony had made a similar mess on the massage table.

"There. How does that feel? They say that semen is a good moisturiser. If you ever need any more, you just come and find me. I think we might need some moisturiser on your face and tits!"

Tony just laid there feeling more than a little guilty. He had just been fucked for the first time. Not only had he been fucked, he had be a more than willing participant. He had acted like a cheap porn star, making out with a horny hunk. He hoped that if he bumped in to the masseuse around the restaurant, he wouldn't blush with embarassment.

More worryingly, he had enjoyed being fucked by a stranger. But when in Greece...

Chapter Five

After giving himself a few minutes to recover his composure, Tony stood up and went to retrieve the dressing gown. As he walked towards it he started to feel the cum dribbling down his inner thigh. He felt like a well fucked whore as he walked across the room. He tried to close his sphincter, but it kept on dribbling. He pulled the gown on and tied it tightly around his waist, heading back to the spa receptionist.

"How was that Sir? He is very thorough isn't he?"

"I can honestly say that it was like nothing I've ever done before!"

"Would you like to try and of our other treatments Sir? We have meditation which is very popular?"

After just being fucked, Tony had thought it would be best to head back to his room and have a good, long wank.

"That sounds lovely." he heard himself saying.

"Come with me Sir."

As they walked along the corridor the receptionist looked down and saw the obvious signs of cum flowing down Tony's legs.

"I remember the first time he fucked me. He's very big isn't he? I can assure you, you do get used to his size and next time you'll enjoy him even more. I now like to ride him so I can control when he comes. Was he your first?"

"Yes. Yes he was."

"Well, you be careful. He does like a good bit of ass and your bum is very fuckable. I know that I'd fuck you if I still could."

Tony looked down at the short woman with the huge breasts in shock. He couldn't believe that he was talking to this woman about being fucked in the arse by another man like they were two life-long girlfriends talking about what wine to have for dinner. And what did she mine by "... if I still could..."?

"Of course, his brother Michael is even bigger!", she dropped in casually, "And, despite what they say, bigger is certainly better!"

She winked at him and Tony just blushed.

What? He had just been fucked by the barman's brother. And the barman had a bigger cock than the one that had just taken his anal virginity!

"Here we are Sir. Sit yourself down, watch the screen and listen to the music."

Tony sat down in a daze, not fully comprehending what was going on. The spa receptionist had started the music and switched the lights off. The images on the screen were a little weird. With the relaxing music, soon Tony was a semi-hypnotic state.

"How was that Sir?"

"Is that it only a couple of minutes?"

"Sir, you've been in here an hour. It is very relaxing isn't it?"

"I guess so."

"Can we do anything else for you today?"

"I think I need to go back to my room. I need to sort a few things out."

Tony stood up and noticed that he'd left a pool of spunk behind on the seat. The receptionist looked at it.

"He does cum quite a lot doesn't he? But you will get used to him. And his fucking."

Tony nodded, shyly. She wiped her finger through it and brought it to her lips.

"Mmm I love how good he tastes. Don't you think so?"

She scooped up another couple of fingers full of the cum and held them up to Tony. Without thinking, he opened his mouth and found himself sucking her fingers clean. His first taste of another man's cum. He wasn't sure if he liked it but it tasted like something he couldn't quite put a name to.

"We reserve his spunk for special guests. We think they deserve a taste of his unique sauce."

Last night's steak sauce. He'd eaten a steak doused in spunk. He should have felt disgusted but it brought a small grin to the corner of the lips. Last night he'd gone to bed with a hunk's spunk in his belly. And tonight he was going to bed with more than a slither. A man had fucked his arse and pumped him full of his sperm.

What had started as a little grin was now a beaming smile of contentment.

"Lovely ro meet you, Sir. Don't forget your clothes in the locker. Feel free to wear the gown back to your room. I hope to see more of you whilst you're here"

"Most kind."

As Tony walked through reception he noticed that Michael was busy in the bar. He was busy serving another guest, but he waved as Tony walked by. Michelle was behind the counter and she beckoned him over.

"Did you enjoy your treatments Nik... er... Tony? I understand that you met Michael's brother, Georgio. Did you receive a good service?"

"Yes. He's very good at what he does isn't he?"

"When he has the right client, he performs very well. I see that you enjoyed him more than most."

Did she know that Georgio had fucked his ass and pumped him full of cum?

"You're welcome to call on his services again if you like."

"Thank you. For now, I'm going to my room. Would it be okay if you send up some fresh fruit? I think I need something to freshen me up."

"Of course. As soon as one of us is free, we'll send it up. You have fun now Nikki."

"Tony. It's Tony."

"Yes, of course it is. I'm so sorry."

Chapter Six

Walking through reception, Tony felt very self-conscious, He felt sure everyone was looking at him but put it down to the dressing gown he was wearing. Just to be sure, he held the gown tight around him, making sure no one saw that he was naked beneath the gown.

When he got back to his suite, Tony couldn't wait to become Nikki again. He removed the dressing gown and selected a sexy, lacy white matching bra and knickers. He had bought this for a friend's wedding he had been to earlier in the year. As one of the ushers, he had to wear a smart grey suit and a white shirt, but he couldn't resist wearing sexy underwear beneath the wedding gear. He just wished that he dared to show his underwear to one of the bridesmaids or better still to one of the fellow ushers.

Over the top of the underwear he pulled up the short, short skirt he had bought earlier in the day and matched it with a patterned top. After applying red lipstick and pulling on the blonde wig, Nikki settled down on the freshly made bed.

Whilst waiting for the fruit to arrive, Nikki switched the TV on. She wasn't expecting to find much on. Daytime TV is never good and Nikki didn't expect it to be any better in Greece. As she flicked through the channels most of it was international news channels and Greek soap operas. But then she found a channel which was two people fucking.

Nikki didn't expect that.

The girl had long blonde hair and had her back to the camera as she was bouncing up and down on the man's cock. She was reaching back and holding her ass open as she raised and lowered herself and what was obviously a very large cock.

Nikki soon had her cock out and was stroking it. Having just lost her virginity, she knew what the girl was going through. Judging by her moaning, she was obviously enjoying her ride. Nikki's cock was now poking out the top of her knickers with her skirt flipped on to her stomach.

She was wishing that she'd had the chance to do to Georgio what this girl was doing to her lover.

"She's good isn't she?"

Nikki looked up to see Michael standing in front of her with a bowl of fruit in his hand. She couldn't believe he had come in to her room without knocking. And for him to find her all dressed up was embarrassing. To find her dressed up and wanking whilst watching a girl riding a cock... she wanted the earth to open up and swallow her?

"Have you ever done that?"

"No. I've never met a woman who would let me fuck her arse."

AnnaV
AnnaV
82 Followers
12