Olivia

You never forget your first time, and in my case the first time was the best time. I was 19 years old and just out of Navy boot camp and radio school, and my first assignment was in San Miguel, Philippines. I had been there about a month when a bunch of guys in my unit decided to spend a few days in Baguio, a resort community in the mountains of Luzon.

Her name was Olivia. She was a working girl, and a bartender in town hooked me up with her. She walked into the bar with an air of confidence, probably about 30 to 35 years-old, taller than average for a filipina, maybe 5'6”, shoulder length platinum blond hair, a nice bust line, blood red manicured nails, and a beautiful heart shaped ass that made her jeans look like they were painted on. She was not a super beauty but attractive, with the look of a survivor and the attitude of a street fighter.

She wasted no time in sizing me up, checking my military ID card, commenting on my young age, then following with a hard interrogation; where are you from? Are you married? Do you have a girlfriend in the States? Do you have a girlfriend in the PI? My answers to all her questions were “No,” and she was skeptical with regard to my denying the girlfriend stuff.

Olivia stared at me for a moment, and I had seen that look before, put on me on more than one occasion by my mother, grandmother, and various teachers when I tried to BS my way out of trouble.

Satisfied for the time being, Olivia said, “Let me see your wallet.”

Without hesitating, I handed it over. She pulled out the money, counted it, then asked, “So what are you looking for?”

Being shy by nature, and pretty much intimidated, she caught me off guard.

“Well, if it’s okay, I’d like to spend the night with you.”

Olivia smiled, no, it was more of an impish grin while she drummed my wad of bills up and down on the table, “Oh wonderful...we could watch some television, and I could maybe read you a bedtime story?”

In a way, that took the edge off, and I put it to her plain, “No, I hadn’t planned on TV and a bedtime story. I want to make love to you...you’re gorgeous, I….”

Olivia stopped me, counted out $40, and handed it to me, “Yeah, yeah, okay, this is your pocket money, I’m keeping the rest...let’s go.”

I watched Olivia pass a few bills to the bartender and put on sunglasses as I followed her out. She held out her hand as we walked down the street, “Here, take my hand.”

I grasped her soft hand, and as we walked she told me a bit about herself.

“You know John, I’m married. I work as a school teacher, and I have a son and daughter in grade school. My husband is disabled, and I do this to get extra money, so my kids can go to college after they graduate. They don’t know I do this. The bartender back there is my cousin, and he is careful with who he sets me up with. I’m just telling you this….you know, just so you know your first time is not with a street walker or stripper. I’m a good person”

“What makes you think this is my first time?”

She giggled, “Oh, so it's not your first time? You’re an experienced lover...been with lots of girls?”

I just gave up on that one, smiled and admitted, “Yes, it’s my first time.”

Olivia flashed that impish smile again and squeezed my hand, “We’re gonna have fun tonight; you have the best teacher.”

We left the main street that ran through town and entered the lobby of a small hotel. Olivia greeted the guys at the front desk who seemed to know her, paid for the room, and one handed her a couple of towels, washcloths, and bars of hotel soap. The room we got was small, and the furnishings, a double bed, overstuffed sofa, and writing table with two chairs, appeared to be pretty old. There was a ceiling fan that rattled briefly when she turned it on, and when I looked out the window, I got a nice view of an alley, some trash bins, and several stray cats.

Olivia excused herself and went into the bathroom. I heard the toilet flush twice, then the sound of water running. After about 15 minutes, she came out, barefoot and wrapped in a white towel. She was holding a blond wig and sunglasses in her hand, and ran her fingers through her long, black hair, “Like it?

She was smiling, and I laughed, “I like it better, beautiful eyes, and I love the hair...was wondering about the Filipina Marilyn Monroe.”

“Like I told you, I’m a school teacher, and Baguio is not a very big city...I can’t be seen...you know, doing this...gotta have a disguise.”

That said, Olivia took me by the hand, “I thought we could get to know each other better by taking a bath together, come, come…”

I followed her like a puppy and saw the tub, an old and partially rusted white clawfoot number, and the bathroom was steaming up.

Olivia smiled and started to untuck her towel, “Get undressed John.”

I had already kicked off my shoes and had my shirt and pants off in seconds, pausing briefly to watch as Olivia shed her towel. She was magnificent, no hint of shyness what-so-ever, like nudity came very naturally to her, and she was used to men seeing her naked.

She had an olive complexion with tan lines around her hips and breasts showing that when she went to the beach, she wore a bikini. Her breasts were perfectly symmetrical and lovely, maybe a little more than a handful, with very dark brown nipples and large areolas.

I moved closer and fondled her left breast...must’ve been clumsy on my part because
Olivia turned away and leaned over to turn off the water. Then she stood there with one hand on her hip and the other cupping her vulva, “Are you getting in with those undies, or will you be taking them off?”

I stood there for a moment, aware I was becoming erect, then pulled down my Fruit of the Looms. I started to cover myself, but Olivia stopped me, “Nice, can I?”

Without waiting for a response she took my penis in her hand and squeezed gently which startled me. No one had ever touched me like that, not even the doctor who administered our sports physicals.

Olivia told me to relax and kept stroking my cock. She took my hand and placed it back on her left breast, “Here, you can touch me too, but let me show you how.”

She positioned my hand so that her nipple was between my middle and ring finger, and showed me how she liked her tits played with...soft squeezes with slight finger pressure on her nipple, maybe four or five times, then roll the nipple between my thumb and forefinger and repeat.

“You see, that’s how you do it...my titties aren't silly putty...be gentle.”

Olivia turned her attention back to my penis and grasped it...like it belonged to her, “You gotta nice dick...cute, pink fat boy and big, but not too big...perfect size for me.
Then she took my scrotum in her hand, “I like these too, fun to play with, and if a guy gets out of hand, well...get in the water.”

I slipped into the tub, and Olivia sat on the edge behind me and started to shampoo my hair. Then she rested her feet on my thighs and used the soap on my chest, arms, and shoulders. It wasn’t long before her little feet found my cock and began to tease it with her toes. I heard her mumble, “Mmmm, Musculado,” under her breath, then she asked, “Do you lift weights or play sports? You gotta nice body.”

“Yeah, I did all kinds of sports in high school...and I lift weights on the base when I can.”

She laughed, “Can’t believe the girls back home never took you to bed...well, their loss. Get up on your knees.”

I did as told and leaned forward, grasping the tub as Olivia used the bar of soap on my ass and genitals and scrubbed my feet with the washcloth. That got a response from me as I am extremely ticklish, and she giggled, “Hah, good to know your weaknesses.”

Satisfied with my cleanliness, Olivia told me to turn around…”Now you wash me.”

She turned and knelt, cocking her hips to present her ass and pussy. Her vagina was covered with a thick growth of pubic hair that ringed her asshole. In contrast with her olive skin, her genitals and anus were almost black. A thin pink line was visible between her thick labia. Her ass was tattooed on the left side with the outline of a heart with a question mark inside

I was still staring at her when she said, “My pussy isn’t going to wash itself...soap me.”

I lathered up her ass then soaped up her genitals. Olivia moaned and wiggled her ass as I massaged and lathered up her pubic hair and vagina. It was so soft. I ran my finger up and down the crack of her ass as I leaned forward, reaching around her hips, and began to wash her breasts and belly. Like before, she began to respond, rotating her hips and stroking my cock with the crack of her ass.

“Finger fuck me...now, do it now.”

I backed off as Olivia took my hand and guided my finger inside her. She was warm and tight, but wet with desire, and my finger slid all the way in.

“Mmmmm, feels so good...fuck me slow, in and out, yeah, that’s it, two fingers now.”

I was fucking her with my middle and index finger when she began to wink her anus at me. I rinsed the soap off, and licked it which brought an immediate response.

“Oh you like that? Such a dirty boy...soap your finger and put it in my ass.”

I coated Olivia’s anus with soap, then my finger and pressed on her, slowly increasing the pressure until the tip of my finger entered her.

Olivia grunted, “Uggggh, okay, slow now...put it all the way in.”

She groaned some more as I pushed all the way inside, feeling her sphincter muscles squeezing me, “Okay, in and out now, go slow.”

I finger fucked her ass for a minute or two, then put my thumb in her pussy, and held her like that while she pushed back on me. This went on for a bit, and then, “Let’s get in bed.”

We dried each other quickly, then she pushed me down on the bedspread and mounted me. Reaching behind her, she guided me inside her and began to grind. Her pussy was hot, and I could feel her pelvic muscles gripping my cock. I didn't last long...it was over in less than 5 minutes.

After I finished ejaculating inside her, there she was looking down on me with that impish grin again, “So, ‘Speedy Gonzalez,’ your first time...how did you like it?”

I was still inside her, and she was still slowly grinding on me, and I was still holding her feet, “That was the best...can we do it again?”

Olivia laughed, “Of course, but that will cost you another $40.”

She got up off me and went to where my trousers were draped over a chair, took out my wallet, and helped herself to the rest of my money.

“Would you excuse me for a moment?”

Olivia went to the bathroom, and spent about ten minutes inside. I heard water running, the toilet flushing, and she reemerged with a wet washcloth. She cleaned my genitals, and then we cuddled. I must’ve dozed off, and when I awoke it was dark outside, and I was looking up at her pussy...she had straddled my face.

"Okay, time to take you to Fucking School, lick me, lick my pussy." At that point in my life, I had never given head to a girl, so she taught me how to do it, caressing her clit with my tongue, while she grinded her ass into my face. She tasted so sweet and was so wet. I must've been doing something right because she was moaning and riding me hard. At one point, my jaw cracked when she pushed her pubis down hard.

Then Olivia turned about, and we started doing 69. It was dark in the room, but we left the light on in the bathroom, and that, combined with the lights from the street shining in, illuminated her asshole...I had my nose right in there, trying to capture her scent. I was sucking hard on her clitoris and labia, and suddenly she squirted in my mouth...I had thought I made her come...that's how inexperienced I was.

She jumped off me and ran to the bathroom, and I could hear her peeing. When she finished, she got back on top of me and admonished me, "You made me pee...you don't suck so hard,,,just lick it like I tell you. Then she cowgirled me. She was okay with brushing her titties on my face and me massaging them, seemed to like me sucking her rock hard nipples, but I could tell from the shudders and squeals she was ticklish.

Olivia was on top of me, back arched, with a far away look in her eyes as she played with her tits and rocked back and forth on my cock. Whenever she sensed I was about to come, she'd clamp onto my nipples, pinching and twisting, and order me, "Not yet...don't come."

We kept this up for about 20 minutes when she started to hyperventilate, then she cut loose with a violent orgasm...I thought she was going to break my dick off in her. We dozed off again, and I woke up with my cock back in her mouth, staring up at that thick bush of pubic hair covering her genitals and ringing her asshole. We were back to 69, and this time we used just our mouths until we made each other come. Then we slept for a couple hours.

It was starting to get light out when Olivia started playing again. This time it was all kissing and petting. I tried again to suck her nipples, and she pushed me away, but I wanted them bad. I put my arm around her and used my body weight to pin her to the mattress, then held her free hand down and she was powerless protect those delicious brown nipples. She screeched, squealed, and struggled in protest while i sucked, nibbled, and softly bit her...what i still remember was that sound the soles of her feet made as she rubbed them together while she struggled and begged, “Please stop, just fuck me.” I accommodated her, and we fucked again and went back to sleep.

After sun up, I woke her in the shower. When she came out, she was wearing a nice business suit she had brought in with her, and told me she was on her way to school...to her second grade class...told me she was running late.

We exchanged addresses as I was leaving that day, and we began a pen pal relationship, with her being married, my letters went to her cousin’s address. We spent two more weekends together when I was notified I had been accepted for Navy Salvage Diver training. I had to leave suddenly, and didn’t get to say goodbye, but we continued to write while I was in training. I told her there was a good chance I would be assigned to the salvage unit that was based in Subic Bay. Then, right around the time I graduated, her letters stopped.