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Sexual Escapades

"The very beginning of my sexual escapades"

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I've had a high libido ever since I can remember. I dated my very first boyfriend, who I lost my virginity to, for about three years up to the middle of college. We moved in together halfway through freshman year and we were intimate almost daily. This excluded busy periods like exam season, but on most nights, we would have sex before going to bed. Sometimes it was a short fuck, other times it was long and passionate. To me, sex was just part of my daily routine, a moment I shared with my boyfriend each night. It was purely by coincidence our libidos matched.

At the time, I felt deeply embarrassed about my high libido. Often feeling insecure and couldn't help but think that something was wrong with me. I remember bringing it up one time with my family doctor and she quickly dismissed it, saying it just had to do with age and hormones. "Keep yourself busy and exercise, burn off your energy," the doctor would tell me. I often had dirty thoughts throughout the day and found myself craving sex, intimacy, and orgasms. As I entered my 20s, my sex drive really came in waves, I would occasionally have days where sex wasn't on my mind, but also days where I was uncontrollably turned on.

Growing up in a small Filipino-American community, I didn't really date much growing up and never really explored my sexuality. I was often told by friends and neighbors that I was beautiful. “Pretty enough to be a model if you wanted to,” they would tell me. Standing at 5'6", I towered over most of my Filipino friends, both boys and girls! My height made me self-conscious despite the steady stream of compliments I received growing up on my honey colored skin and long black hair, features I only noticed because people pointed them out so often. The very first time I realized that guys found me desirable was when I overheard Jose, a troublemaker from my school, joking around with his friends and saying, "...yeah Kristine... that tall girl, she's sexy, would love to spread her wide open." I remember feeling offended and turned on at the same time.

Anyways, towards the end of my junior year of college, my boyfriend broke up with me. It was my first serious breakup and I took it hard, becoming depressed. At the time, I truly believed we were eventually going to get married after graduation and start a family! That summer, I stayed with my family back home, and my parents suggested a trip to the Philippines, hoping a change of scenery might help me move on. It would also be my first time returning to my home country as an adult.

As a 20-year-old in Manila, I was often bored or irritated by the pollution, heat, and general chaos of the city. To save on hotel costs, my family stayed with relatives, squeezing into a tiny apartment that seemed too small for so many people. Despite my parents' disapproval, I would frequently venture out into the city, preferring to spend time alone than with family. I would often spend a few hours each day wandering alone at malls or parks.

I first met Rob at a popular neighborhood bar. I had only gone there that day because it was the closest bar nearby and the humidity was unbearable, and I needed a drink to cool down. The bar seemed to cater to foreigners and I recall hearing all kinds of different European languages. Rob approached me first. He later told me he was initially impressed by my well-spoken American English but then became more interested in my beauty.

Rob was an American from the East Coast, in his late-40s, and spent most of the year living in the Philippines. He came off as a really cool guy. He was mature, stylish, and tall, with long greyish blond hair, a chiseled face, and had these interesting bird tattoos running down his arms. We talked at the bar for a while, though I can't remember exactly how long. He was easy and fun to converse with, full of fascinating stories. Eventually, Rob invited me over to his condo, which was only a few blocks away, and I found myself spontaneously saying yes.

Arriving at Rob's condo, we sat on the sofa and continued our conversation over drinks. It must have been early afternoon by then, because I could hear the rush-hour traffic growing louder on the streets outside. Rob started by talking about his painful divorce in America, his ex-wife and kids, and his experiences in the Philippines. Then he shifted the focus to me, asking about college, my studies, and my plans after graduation. His questions soon became more personal and intimate, asking about my dating life, past relationships, and my breakup.

Rob scooted closer on the sofa and took my hand. Sensing no resistance, he pulled me closer to him and gave me a kiss on the lips. Truth be told, I was very hesitant at this point so I kind of froze. I only met Rob a few hours ago and he was more than twice my age. I've never done a "one night stand" before and didn't know what to expect. But since I haven't had sex since my breakup, I was an easy target. I recall becoming instantly wet as Rob began kissing the sides of my neck. It's been a while since I was last touched by a man.

"Here, stand up and undress... undress in front of me," Rob instructed.

I recalled feeling a combination of insecurity and boldness, just really complex and conflicting feelings all coming at once. I stood up and slipped off my shorts and tank top, then took off my panties and bra. Standing in front of Rob naked, I was initially trying to cover my breasts with my hands while standing crossed legged. Rob smirked. I later learned that he wanted me to undress slowly, not strip off all my clothe in a second. He could tell I was probably super nervous.

"Relax, relax, relax... you're incredibly sexy and perfect... own it, believe it," Rob said. For some reason, his words really stuck with me.

Sitting on the sofa with a drink in his hand, Rob closely examined my body. He guided my hands away, having me rest my arms against my sides. He commented on my height, how tall and lean I was, my small brown nipples, and my smooth, soft skin. Having me stand closer to him, he briefly ran his hands across my body, squeezing my butt and breasts. His motions were gentle but his hands felt firm and rough against my bare skin. At one point, he moved one of his hands in between my thighs, touching my pussy. It caught me by surprised and with how sensitive I was, it made my legs buckle.

Setting his drink on the counter, Rob got up, undressed, grabbed my hand and pulled me into the bedroom. I remember my bare feet sliding on the tiled floor, nearly losing my balance a couple of times. He was almost forceful, filling me with a mix of danger and excitement. I got onto the bed and laid flat on my back, expecting Rob to move on top of me. I usually preferred having sex in the missionary position, at least with my ex-boyfriend. My pussy was soaking wet by then and I knew I would orgasm with just a few gentle strokes. Instead, Rob grabbed my ankles with each of his hands and slowly pulled my legs up and apart. He was moving his arms around, so my legs were hovering in the air uncontrollably.

"Stop that," I murmured, remembering how I had complained. I felt insecure because Rob was staring directly in between my legs, at my pussy and butthole. I haven't shaved since arriving in the Philippines, and we didn't shower beforehand, so I felt dirty and gross.

"You're breathtakingly beautiful, you know that?" Rob replied. I can't remember his other compliments exactly, but Rob really had a way with words. He knew exactly what to say and when to say it. That's when I began to open up myself completely for Rob.

"Please, can you just hurry? It's getting late, and my parents are going to be looking for me," I said. By then, I really just wanted Rob's dick inside me, fuck me hard, finish, clean up, and go home.

"Just relax, Kristine," Rob whispered. Rob wanted to take his time with me. He moved one of his hands between my legs, massaging my labia and then rubbing my clit.

"Ohhh!" I recall instantly moaning with pleasure. My face was burning hot, and my skin was so sensitive. "Just put it in...," I complained.

Rob continued to tease me, massaging my breasts and nipples, kissing my inner thighs, and finally licking my pussy.

"Aaahh!" I yelled softly. The moment his tongue made contact with my pussy, I felt like I was about to orgasm right there and then. I curled my toes and resisted the urge.

Rob finally put on a condom and entered me. The sensation of a dick never felt so good. It had been a few months since the last time I had sex with my ex. I don't remember much other than Rob going slow but deep at first, then moving to quicker thrusts. Rob's dick was bigger than my ex's so it felt a little painful at first.

My orgasm came suddenly and caught me unprepared. I think it was when Rob touched my clit while he was thrusting me, but I don't know. I don't even remember when Rob finished. I just remember grabbing onto Rob's forearms with each hand, arching my back, and letting out a loud, uncontrollable, moan as the orgasm began to unwind out from between my legs. Every muscle in my body goes rigid as if I'm being electrocuted. My legs briefly jolted, and my toes clinched in the air. It's a long, pleasurable one as the climax flows through my body. I remember feeling lightheaded and dizzy, with beads of sweat running down my forehead. As my orgasm subsided, I went limp, and I began to cry. A wave of conflicting emotions had suddenly washed over me. Maybe it was from the orgasm, maybe it was from the drinks I had earlier, maybe it was pent-up emotions after my breakup; I don't know. I felt embarrassed and stupid. Rob held me in his arms as I sobbed, he knew he had me.

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I stayed in bed with Rob for an hour or so before finally getting back to my family. My parents were upset that I stayed out for so long, but I brushed them off with a lie, saying I made new friends at a nearby mall and hung out with them longer than expected. I knew my parents would explode if they found out I just slept with a 40-something-year-old man I randomly met at a bar.

For the rest of my summer vacation in the Philippines, I would meet up with Rob almost daily, spending anywhere between five and six hours with him each day before venturing back home in the evening. Rob lived maybe half an hour away from me, but I was still paranoid at the time of being seen in public with Rob by a family member.

Rob and I didn't have sex every time we saw each other, but when we did have sex, it was amazing sex. He showed me different poses, how to move my body, and how to pleasure him. Rob encouraged me to embrace my high libido and explore my sexuality. While with him, I felt like I could be myself and not have to hide my urges. At Rob's condo, I would often be fully naked, before and after sex.

Spending time with Rob, he taught me a lot about attraction, especially what turns a man on and what doesn't. He was forthcoming on how I dressed and encouraged me to ditch baggy clothing and boring underwear and instead wear things like dresses, skirts, and designer lingerie. "Life is too short to be boring," he once told me. I remember feeling so anxious the first time I walked around in a Manila mall wearing this short, tight skirt Rob bought me.

As my summer vacation in the Philippines came to an end, I began to feel like I was falling in love with Rob. The day before my family was set to fly back, I confided in Rob that I wanted to drop out of college and stay in the Philippines with him. To my surprise, Rob rejected the idea and wanted me to leave and finish college. I was heartbroken at the time, and my sadness soon turned to uncontrollable anger. I lashed out at Rob and told him I never wanted to see him again. I ignored all his subsequent messages and deleted his contact. On my flight the next day, I regretted my decision but it was too late. I was not able to get back in contact with Rob ever again. But the summer I spent with him was unforgettable.

Published 
Written by KristineKay
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