vacation-girlfriend
FIRST TIME SEX STORIES

Vacation Girlfriend

Vacation Girlfriend

by theinytourist
19 min read
4.04 (10900 views)
adultfiction

Based on a true story.

My previous job was based in the States but I traveled often to Southeast Asia for business. Since visiting the SE Asian countries and often lusting over some of its beautiful women, I had the idea of hiring a "vacation girlfriend" for a few days while staying in the Philippines. However, my work was demanding and the travel schedule rarely worked out for me to take time off while on the road. I also have a family so my free time was rather limited back home.

The stars aligned one particular month near quarter end, and I was able to hastily schedule a four-day stay in the Philippines after the conclusion of my business trip to Singapore, before being flown back to the States. My plan was to arrive in Manila, spend a day there, then spend the rest of my time at a beach resort in El Nido. My short stay in Manila reflected my concerns of accidently running into business acquaintances, and did not want to have to explain myself while accompanied by a woman who was not my wife.

Before arriving in the Philippines, I wanted to save time and arrange to have a "vacation girlfriend" picked out and waiting for me. I called my buddy Max, who had lived in the Philippines for many years, to have him put me in touch with a trusted local agency that offered the vacation girlfriend experience to expats. I consider myself to be picky with women and was really looking for the best I could find. Despite being almost 57 years old, balding, and slightly overweight, I was looking for an attractive Filipina if I was going to pay for her time. My wife was out of shape and no longer physically attractive to me, and I felt like I needed a change, I wanted to spend my valuable time with a beautiful woman.

"Look, I'm not interested in meeting the stereotypical short, flat faced, chubby Filipinas I see roaming the streets every time I come here, I'd rather save my money if that's all I can find," I told Max over the phone. "You know me Max, I might be in my 50s but I act a lot younger!"

Max was understanding of my needs and offered some valuable advice. He suggested I contact the agency a week prior to my arrival in Manila, and hire a woman from the list of profiles provided. Max mentioned to avoid girls in their 20s and focus on women in the early 30s age range. He promised I would not only find more attractive women in the 30s plus age bracket but also women that were more attentive and provided better overall service. Finally, Max recommended I manage my expectations since this was my first time partaking in such a service.

As part of this search, I even created an alias for myself, Tom, a common American name that is easy to pronounce but forgettable. Taking Max's advice, I contacted the agency while I was still in Singapore wrapping up work. Later in the afternoon, the agency responded with several profiles of women. The women's age ranged from late 20s all the way to 50s. I initially wanted a younger women, but heeding to Max's advice, I chose "Kristel", a 33 year old tall, lean Manila native. The pictures on her profile were stunning. She posed either fully nude or wearing lingerie, leaving little to the imagination. She had long black hair, honey colored skin, and a natural athletic body. Listed as standing 5'6β€³ tall, her breasts and ass were fully natural and plump. If this was truly how "Kristel" looked in person, I knew I was in for a real treat. I had a few message exchanges with the agency to confirm Kristel's scheduling, rate, and availability.

A final confirmation was then sent by the agency a few days later and I was good to go. The agency had me add Kristel on a messaging platform so I could communicate with her directly. Kristel was to pick me up at the airport once I arrived in Manila and she would accompany me during my entire four-day stay in the Philippines.

Day 1

My flight from Singapore was terribly delayed. I was scheduled to arrive around 4PM local time but ended up landing in Ninoy Aquino airport just after 8PM. By the time I exited customs, it was close to 10PM. I messaged Kristel to tell her that I was standing in the lobby of the "Arrival" zone. I was worried it would be hard for her to find me given how chaotic and crowded the airport was, but only a few minutes later, I heard a voice behind me.

"Hello, Kumusta, Tom? You are Tom?", I turned around and saw Kristel standing behind me with a smile.

It was my first time seeing Kristel in person and I was pleased she was even more beautiful than her photos. She was wearing a blue sleeveless sundress and black flats. Her cheekbones were high and she had a sharp nose and a small mouth. The silver heart-shaped earrings she wore complimented her long, flowing black hair. She had beautiful almond shaped eyes with pupils that radiated energy. Her pictures were real, she looked exactly as advertised.

Kristel spoke good American English but had a slight accent similar to many Filipinos. We didn't have any issues communicating. She felt welcoming and approachable. She took the suitcase from my hand and we walked towards the row of taxis parked outside the gates. Even though it was already late, there was still a lot of traffic on the roads and it took us almost 40 minutes to get to the hotel in Makati from the airport.

We checked in at reception and went straight up to the room so we could drop off our luggage. Kristel also had a small suitcase which contained her personal belongings. We then took the escalator up to the rooftop bar for drinks. We needed a proper introduction! I remember the rooftop bar being poorly lit and sparsely populated. I bought two overpriced cocktails from the bar and brought them over to our table.

"So Kristel, you're going to show me a good time here?" I teased with a smirk as I handed Kristel her drink. It was my attempt at flirting. Siting across from Kristel, all I could think about was fucking her for my money's worth these next couple of days. I will get what I paid for!

"Yes I will show you, Philippines can be beautiful, and Manila is an exciting city, you will see tomorrow," Kristel responded smiling. Her voice was soft and feminine. She was a pleasant woman to be around.

"Are you going to take care of me?" I joking asked, trying to add some spice into the conversation.

"Of course!" Kristel replied. "We will have a lot of fun together, in these couple days." She then changed the conversation topic and began talking more about the city, the parks and historical sites we are scheduled to visit tomorrow. It was boring for me to listen to so I decided to be more blunt.

"You're a very sexy woman Kristel," I said as I reached out and grabbed one of her hands. Kristel's hands were extremely soft and delicate. I played with her long thin fingers before moving up to her palm. She responded by laughing. Maybe she was nervous. In the Philippines, public displays of affection were socially frowned upon, but since the bar was near empty, I felt like I could take some chances.

Finishing our drinks, we decided to return to the hotel room. It was probably past 1AM by the time we got back. I was exhausted and wanted to sleep. However, I wanted Kristel to give me a blowjob since we haven't done anything sexual so far and the day was almost over. In the room, I fully undressed before turning around to Kristel.

"Can you suck?" I asked Kristel while pointing to my erect cock. I couldn't think of more elegant words to say. I haven't showered since coming from Singapore, so I knew my balls were sweaty and my crotch probably smelled. But I didn't want to wait until showering first.

Kristel softly laughed before having me sit down on the sofa. She then kneeled down and gently spread my legs so she could reach my balls and cock. She massaged my saggy, warm balls with her delicate hands, which gave me instant gratification. It was a combination of almost a ticklish sensation mixed with pleasure. The scrotum massage lasted maybe 30 seconds before she moved on to my shaft. She was giving me long, slow strokes. Her hands were soft, dry, and gentle.

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"Is that okay, do you feel good?" Kristel looked up briefly and asked.

"Yeah, keep going," I responded. I laid back further so I could rest against the sofa cushions. Letting out a loud exhale, I knew I was now in paradise.

Feeling heat and wetness, I knew Kristel had switched to using her mouth. Similarly, she started with licking and sucking on my balls before moving onto the shaft. I closed my eyes and felt her tongue explore and worship the tip of my cock. Putting my hand on Kristel head, I tried to control her pace and made sure she was taking in all of my cock into her mouth. I reached orgasm rather quickly and unexpectedly. As I was ejaculating, Kristel used her hand to continue stroking my shaft, making the pleasure last longer. I had ejaculated over my legs with some of my cum landing in Kristel's mouth and on her hands.

"Ugh that felt amazing, hope my cock didn't smell too bad," I said to Kristel as I got up from the sofa.

"You smell good, you smell like a man!" Kristel replied. I let out a loud laugh.

"Okay, I should clean up and shower first," I said. I was exhausted and dead tired by then. I took a shower and brushed my teeth before signaling to Kristel that it was her turn. I turned on the TV and watched the news as I waited for Kristel to use the bathroom. I was fighting to stay awake by then.

When Kristel came out of the bathroom, she was fully naked. She then spent a few minutes applying lotion to her body. I realized at that moment it had been decades since I'd seen another woman in person, that was not my wife, fully in the nude. Kristel's body was so soft, delicate, and sensual, which gave my drained balls a slight tingle. As she joined me in bed, I pulled her closer to me. I could feel the smoothness and tightness of Kristel as our bodies embraced. Kristel had literally no hair on her body. She smelled of flowers and the texture of her skin was lush and slightly cool to the touch, probably from taking a cold shower earlier.

"How do you want me to sleep? Facing you?" Kristel asked.

I didn't respond, I just wanted to kiss her. As we locked lips, I pushed my tongue into her mouth. Kristel kissed back and our tongues met. It felt like ages since I've properly made out with a woman. My hands flew through her body, squeezing her breast and grabbing her ass cheeks. Don't recall any other details before falling asleep.

Day 2

I awoke at around 6AM, likely because of jet lag. The frequent traveling across different time zones have ruined my sleep schedule. I often found myself tired throughout the day but unable to sleep at night.

The sun was rising and sunlight was pouring into our room. Kristel was still sound asleep. She had her back turned towards me and was sleeping on her side. I gently pulled off the comforter that was covering our nude bodies. Kristel's legs were crossed, revealing her pussy and her anus. Her anus was brown, tight, and very cute. I began to gently fondle her pussy lips with my fingers, causing her to awake.

"Good morning Tom," Kristel said in a sleepy voice, "you are up so early, would you like me to order breakfast?"

"No, no baby, just relax," I responded. My cock was hard from touching Kristel. My plan was to fuck Kristel as many times as I am able to since we were going to be only together for a few days. I didn't have the same stamina as I had a few decades ago, but I was sure twice-a-day sex, once in the morning and once at night, was still possible for me!

Placing my hand on Kristel's thighs, I gently rolled Kristel over so that she was lying on her back. Then, I began massaging and rubbing Kristel's pussy with my hand. She got wet quickly. She even spread her legs wider for me for better access. Feeling that I had warmed her up enough, I moved my face closer to her mount to deliver oral. Her thighs and pussy radiated warmth, and I felt a wave of heat as I moved my face into her sex. When my tongue touched her wet pussy, I began licking up and down, then kissing and sucking her pussy lips.

"Aaa...Tom...mmm," Kristel moaned softly. Her eyes were closed but she had her hands resting on my head, stroking what was left of my hair.

It had been a long time since I enjoyed eating pussy. My cock was rock hard and pre-cum was leaking from the tip onto the bedsheets. I could feel the pressure building and knew I was ready to penetrate Kristel for the first time. Putting on a condom I retrieved from my luggage, I moved myself between Kristel's spread legs and pushed my cock into her unresisting pussy. She was very tight. I started with a slow but deep thrust before pulling back. I only managed to get in two or three full thrusts before so much pleasure built up in my cock that I involuntarily ejaculated. I couldn't hold it any longer.

My cock was halfway in Kristel's pussy as I let out a loud, involuntary grunt as I came. I fully embraced the wave of pleasure pass through my body before I fell forward into Kristel. I laid on top of her as I rested, embracing her in a hugging position. Kristel's body fit perfectly in my arms. I needed a moment to catch my breath.

"That was good? You like?" Kristel asked.

"Yeah... just need a moment," I responded. I felt some embarrassment because I thought I could last longer. Kristel probably thought of me as a desperate old man who has never experienced a beautiful woman and can't control himself. It was true. My sex life back at home was nonexistent and I candidly lost attraction for my wife years ago. A beautiful, young woman like Kristel pushed my libido up to a level I haven't felt before in years.

I must have fallen asleep while resting in Kristel's arms. When I awoke and checked the time, it was already 11AM.

"Sorry, we're probably going to be late for our tour since we are still in bed, my fault... must have fallen back asleep again," I said.

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"Just relax and relax and relax Tom...don't worry, you're here to relax and we can do what you like," Kristel replied as she rubbed my back.

The cum filled condom slipped off my flaccid cock as I got out of bed. We both tried to clean up and get dressed quickly, but by the time we walked out of the hotel lobby, it was close to noon. In short, we did miss our scheduled tour of the historical sites but ended up taking a taxi to Rizal Park and walking along the waterfront. The mid-afternoon heat was absolutely suffocating, I remember being drenched in sweat and having to take shelter frequently in the air conditioned buildings we passed. We had a late lunch in a nearby mall, which gave me time to cool down. Kristel was less bothered by the heat but I could see she was sweating too.

"We should head back to the hotel, I'm feeling tried," I said. The original plan was to visit Fort Santiago in the afternoon, which was not far from where we were, but I felt like I couldn't handle anymore walking and navigating the crowded streets. I initially had a long list of planned activates and to-dos but I realized only then I was too ambitious!

The hotel room we were staying in had a small private pool connected to the balcony, so my new plan was to have a few drinks and hang out there. The pool was tiny, the size of a jacuzzi at most, but at least offered a cool sanctuary in the blazing heat.

We took a taxi back to the hotel and I called room service to bring up beers and cocktails. Kristel and I then changed into our swimsuits. Kristel wore this pinkish-colored two-piece swimsuit where the top looked like a short crop top and the bottom was a G-string. It was extremely sexy and I've never seen it in America before. She also loved the swimsuit because she said could just wrap a towel around her waist and be out in public without being too revealing.

Once the drinks arrived, it was time to fully lay back. Kristel initially wanted to read her book by the pool but I had other plans for her.

"Kristel, come here," I said while taking a sip of ice cold beer. "I want you to play and massage my cock and balls like you did last night." I pulled down my swim trunks and sat down on lounger.

She was obedient. Putting her book down, she walked over and kneeled down in front of me. I made myself comfortable and leaned backwards. Taking another sip of beer, I felt Kristel's long fingers gently squeeze my sack. This is what heaven probably felt like I thought to myself. Kristel was very attentive, she was not only massaging my sack this time but also rubbing and squeezing my inner thighs and other groin bits. The pleasure made my cock instantly stiff up.

"Does it feel good baby?" Kristel asked.

"Yeah...don't stop and keep going," I instructed. "Don't stop, I want a longer massage...use your mouth...you love sucking cock."

Kristel brushed her hair behind her ear and began to kiss and lick my cock. The wet sensation of her mouth felt godly. Even with Kristel sucking and stroking my erect cock, I felt like I couldn't orgasm again. I noticed my cock would get soft and then get hard again. Maybe two orgasms a day was really pushing my old body to the limits. After a few more minutes of trying, I had Kristel stop since my cock became soft. I felt the same embarrassment as I did in the morning.

"Take off your swimsuit, I want you naked, it's just us here," I said. "Come join me in the pool." The tiny pool was barely enough to fit the both of us. I held Kristel close to me as we took in the afternoon heat together.

We went out for dinner and took a stroll around Makati afterwards. Since our flight to El Nido was in the morning, I wanted to hit the sack early to manage the Manila traffic and chaotic airport. Kristel and I cuddled and made out in bed, but I was drained and had no energy for anything more beyond that.

Day 3

The morning was just as crazy as I predicted. We got up at 4AM, checked out of the hotel with our luggage, and took a taxi to the airport. We barely made it in time for the flight to El Nido. The flight was only 90 minutes and densely backed with tourists. Arriving at El Nido airport, we took a taxi to our all-inclusive resort. Nothing really eventful happened other than another Western tourist, likely Aussie, comment on how "gorgeous" Kristel was while we stood in a line.

It was close to noon by the time we checked into the resort and had lunch. I had booked a villa that included a private pool and gardens facing the beach. Wasting no time, we changed to our swimsuits, put on sunscreen, and headed out to spend a few hours under the sun by the ocean. The weather was perfect, the sun was bright, and the oceans calm.

Kristel changed to a new tiny bikini that was multi-colored with black lacings. The top was two small triangles barely covering her breasts. The bottom was essentially a G-string. She really knew how to perk a man's attention!

"Do you like it?" Kristel asked me after she caught me examining her bikini.

"Very sexy and looks comfortable, no more tan lines!" I joked flashing a thumbs up.

As we relaxed on the deck chairs, I realized after having spent almost two days with Kristel, I didn't know much about her as a person. So I started a conversation and asked more about her background.

Kristel shared that she spent the majority of her life in the greater Manila metro area. It was where all the opportunities are she added. In the past, she's done amateur modeling in her early 20s, played semi-professional volleyball at one point, but never had the chance to go to college because of money constraints. Kristel said she works a full time job as well, which was her primary source of income. She seemed hesitant to share information about her family.

"You are a beautiful woman, many men want you, what got you doing this? Just to earn some extra cash?" I pressed further.

Kristel laughed. "Salamat! I'm average woman Tom! I like pleasuring men, it makes me happy."

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