Chasing Paradise Ch 21 25

No character in this story was under 18 when they had sex.

I will leave it to the reader to decide what is true and what is fiction. I have been around long enough to know that each person decides what is true or not based on their own experiences, and NOT based on what is actually true.

Chapter 21 -- Kathy

Her name was Kathryn, but she went by Kathy. I have always been partial to petite Filipinas. There is something special about these little women that pulls me toward them. I love the way they look, the way they smell, the way they taste, and the way they treat a man. Even then, Kathy was a very special Filipina. I met her in Angeles City, but not under the same circumstances that I had met so many others. I was transiting back to the US from Southeast Asia when I arrived at Clark for my normal layover.

I first met Kathy at the checkout counter in a local grocery store. OK, there isn't much special about that except that unlike many other Filipinas I had met, Kathy already had a real job (as a cashier). That meant that she already had some stability in her life. Most Filipinas I met around Angeles City had absolutely no stability in their lives. Filipinas coming to Angeles City seemed to mostly have no assets and were living on the edge of chaos.

There weren't many people in the grocery store at the time, so I got to chat with Kathy for quite a while. In fact, I went through her checkout stand several times as other customers passed through. It got to the point where she asked me if I needed some help remembering what I had come into the store for in the first place.

I smiled and told her that I knew what I was looking for, and that I had found it, but I just wasn't sure how to get the object of my desires out of the store. That confused her, so I just told her that she was the object of my desires. I asked if she had a boyfriend or a husband before I did anything stupid. She told me, "No. I have never had a boyfriend."

I think by now she was intrigued by this young American man who was paying so much attention to her, and when I asked her if she would go to dinner with me, she replied, "Let me think about it." A few minutes later (and another trip through her counter), she said, "Yes. I will go to dinner with you, but no funny business."

I asked what time she got off, and where she wanted me to pick her up. She told me that she was off at six, and asked if I would pick her up at the store and take her home so she could change before we went to dinner. She said that it would also give her mother a chance to meet me. I agreed to her terms, and I was back at the grocery store at six that evening. We took a trike to her house, and she introduced me to her mother. I talked with her mother while Kathy went to her room to get changed.

I guess I passed her mother's criteria for a prospective husband because when Kathy returned from her room, her mother smiled and told Kathy, "You have found a good man. Treat him right." Like the mother and daughter that I had met at church, I got the impression that Kathy's mother wanted Kathy to get married and give her grandbabies, but she wasn't nearly as pushy (at least not in front of me).

We caught a trike and went to my favorite Italian restaurant for dinner. I ordered a sweet wine with dinner, and Kathy liked the choice. I kept her glass topped off all through dinner and the conversation. Unlike many girls I had met, Kathy had grown up and graduated from high school in Angeles City. She had no formal education other than that.

Kathy's position at the grocery store was proof positive that connections were more important than knowledge or education in the Philippines because she had gotten a job as a cashier at the grocery store right out of high school. Although that wouldn't be unusual in most countries, jobs are notoriously hard to get in the Philippines, and successful applicants are often vastly overqualified for the position they seek. I have met many girls with accounting degrees working as cashiers in stores and restaurants.

She got her job because a friend of her mother owned the store. Kathy was, however, much more interesting than that little bit of information. Kathy was very smart and had learned her job as cashier very quickly. Connections had gotten her the job, but her brains let her stay on beyond her initial six-month contract (normal in the Philippines).

Kathy confirmed my suspicions about her mother's desires. She told me that her mom thought that Kathy needed to find a good husband and start having babies with him as soon as possible. Kathy said that she wasn't opposed to the idea, though, and she said that when she found the right man, she would freely give herself to him.

I took a chance and asked, "Do you think that I might be the right man?"

She looked at me and then replied, "Maybe. You are smart, you are confident, you are a gentleman, and my mother likes you. Those are some of the biggest hurdles in my list."

I ordered gelato for our dessert, something that I seldom did. Kathy loved it. When we were done with dinner, I asked Kathy if there was something she wanted to do next. She replied, "I should ask you to take me to my home, but I would rather stay with you and talk awhile. Who knows where that might lead?"

We decided to take a walk in the evening air (which isn't all that clean in the Philippines), and our walk just happened to take us by my hotel. I asked Kathy if she would like to come up and see my room. I fully expected her to say 'No', but she said, "Yes, I would love to see your room." This was not usual for a conservative Filipina, and there were many Filipinas whose stories never graced the pages of this story because they said, 'No.'

So, we went up to my room to continue our conversation. I asked her what her dreams were, and Kathy said her dreams were fairly simple. She basically wanted what her mother wanted for her. She wanted a good, stable husband and several well-behaved children. Most importantly, she wanted to be the best wife and mother that she could possibly be.

When we were sitting on my bed, I asked how she would know when she met the right man to become your husband, and she surprised me when she said, "What makes you think I haven't already found him?"

I was puzzled and said, "But you said you didn't have a boyfriend."

"That was true," Kathy replied. "But that may have changed tonight."

"Oh," I said, catching her meaning for the first time.

It seemed like the perfect time to take a chance, so I asked, "May I kiss you?"

She lowered her head and softly said, "Yes."

I lifted her chin and leaned in to kiss her softly. My lips touched hers and I pressed against her in an embrace. Kathy backed away at first, but then leaned into the kiss. I didn't get too ambitious with that first kiss. It was sweet and soft, with no expectations, and she was smiling when the kiss ended.

"That was nice," she said. "It was better than how I imagined my first kiss."

I leaned in again, and used my tongue a bit in our second kiss. Kathy was unsure how to react as my tongue searched for her mouth, but she finally opened her mouth a bit and my tongue entered between her teeth and sought out her tongue.

I sucked in her lower lip, and then let my tongue dance with her tongue inside her mouth. Kathy's reaction was to suck on my tongue, which was encouraging. I kissed her again and again. Each kiss went a little further until our tongues were dancing between our mouths, and our hands were wandering.

My hands came up Kathy's sides until they were resting on her breasts. She made no move to push them away, so I began massaging her breasts as we kissed. When Kathy started moaning into my mouth, I knew that this might go much further than I had originally anticipated.

I broke the kiss long enough to look into Kathy's eyes, and took the ultimate gamble. I asked her, "Do you want this to go further?"

She nodded, blushed, and then whispered, "Yes."

It was all the encouragement I needed. My hands found the zipper in the back of her dress, and slowly pulled it down. Kathy shuddered a little as my fingers touched her flesh, but made no effort to stop me as I undressed her. I pulled her dress straps off of her shoulders and kissed down her neck at the same time. She shivered a little, partially from the cool air hitting her skin, and partially from pure excitement.

I pulled her to her feet and let her dress fall down and off her body as I continued to kiss her. Kathy stepped out of the dress puddled up at her feet. Now, she was in her bra and panties. I asked her to take my shirt off, and she started undoing the buttons. Once they were all undone, Kathy pushed the shirt from my shoulders, letting it fall to the floor behind me.

As my shirt puddled on the floor, I asked her to take off my pants. This would be the point where she would either back down or fully commit. Kathy committed. Her hands went first to my belt, then to my snap and finally to my zipper. I stepped out of them as my pants fell to my feet.

It was now my turn again, and I leaned down to kiss across her upper chest. Kathy pushed her chest against me, so I reached around to unhook her bra. I was still fully expecting this to end, and that her hands would come up to protect her breasts, but they didn't. Her hands stayed down at her sides, and my lips found her nipples instead. "Oh my God," she cried out. "This feels so good."

Kathy's nipples rose up and became fully erect to meet my lips. As I sucked her nipples into my mouth, they seemed to grow more. Kathy didn't have large nipples to start with. In fact, they were quite small. But they grew significantly larger as I sucked each of them into my mouth. I had been worried because they had started out so small, but I needn't have. They were perfect for suckling once they had attained their full size after stimulation.

Kathy had maybe A-cups or small B-cups, but there was plenty to play with and stimulate. Her nipples were very sensitive, and she enjoyed having the rest of her breasts played with and sucked as well. Suckling her nipples made her cry out in pleasure, and I made sure that happened over and over again.

Before long, Kathy was literally begging me to, "Put it in me now." I knew what she wanted, but I also knew that she wasn't ready for my cock yet. I continued suckling her nipples, and then I let my hands drag her panties down her legs. Kathy was once again flat on her back, and she was pushing my boxers down my legs at the same time her panties were coming down and off her feet.

Once we were both naked, I shifted my attention to her pussy. Her vulva was tight, pink and compact, but her labia opened like a flower at my first touch. Everything was already wet, with Kathy's natural lubrication oozing out of her vaginal entrance and all surfaces glistening. I kissed my way down to her clitoris and sucked it into my mouth.

I think Kathy was going to protest, but her protest died as soon as she felt my lips draw her little button into my mouth. To say that she loved the feeling of my sucking her clitoris would be a massive understatement. My fingers found her vaginal entrance, and along with it, they found her hymen. Kathy's hymen was just inside of her vaginal entrance; not right on the surface, but not deeply buried in her vagina either. It was pink and fat, with a tiny hole in the center.

I tested her hymen with my finger several times, but any pressure on the hole in her hymen caused her pain. I finally decided that I would just have to break it with my cock and not worry about the pain it might cause her. This was one of those cases where there was nothing a man could do to prevent the initial pain of defloration. Every woman is built differently, and a man has to adapt to the situation he finds. There was never, "One method fits all."

All I could do was to get her as ready as I could before I penetrated her vagina with my cock, and with a lot of oral and manual attention to her clitoris and labia, Kathy was orgasming multiple times before I moved quickly, lined my cock up with her entrance and thrust my cock through her hymen and deep into her vagina with all of my strength. Her hymen ripped, and Kathy screamed, but it couldn't be helped. I kissed her to muffle her cries as I shoved my cock into her, but still, there were a lot of tears running down her cheeks as I pushed the remainder of my cock into her now bloody vagina.

I apologized for the pain I had caused her, but then I told her that there was nothing I could do to completely avoid that with her. It was just because of the way her hymen was built that caused her pain, and that I had prepared her as best I could. However, whereas she had been begging me to 'put it in' just moments before, Kathy was now pleading for me to 'take it out' as soon as possible. I think a lot of women are scarred for life when their partner heeds their request to remove his cock after a painful entry, but before the woman can get any pleasure from it. If they don't experience any pleasure the first time they have sex, women will likely always be afraid of sex.

I knew that the worst was already over for her, and that we should continue until Kathy felt pleasure again, but it was still hard listening to her cry and sob. It tore me up inside, but I held my cock deep inside of her pussy until the pain in her vagina had mostly subsided. Then, I started slowly withdrawing and thrusting back in, just a little each way at first, and then lengthening the strokes until my cock was almost slipping out of her before pressing deeply into her again.

Once I had freedom of movement, I started speeding up the tempo. By then, Kathy was no longer crying or begging me to stop, and she was pushing back against me as I thrust into her pussy. Each thrust drove my cockhead deeper into her vagina until every stroke was pressing firmly against her cervix. Her enthusiasm and her pleasure increased the deeper my cock went into her.

Just when I thought there was no hope that Kathy would ever come on my cock before I climaxed, her body started to shudder and her vaginal muscles started to squeeze my cock rhythmically. I was on edge anyway, and her orgasm (as small as it was) pushed me over the edge. I pressed my cock as firmly against her cervix as I could and pumped spurt after spurt of my sperm deep into her womb.

Kathy bled quite a bit when her hymen was torn. It was lucky that I had a towel on the bed under her, but even then, there was still some blood on the sheets. I knew that it needed to be cleaned, but my first priority was to take care of Kathy herself. She was still breathing rapidly, and her skin was flushed. That indicated that she was still excited by what had happened.

I asked her if she could forgive me for hurting her so bad. She replied, "I already have. If you had stopped when I asked you to, my memories of sex would have been horrible. As it is, I was still traumatized, but the pleasure at the end gave me hope that it can be better when we do this again."

"It can and should be a lot better in the future," I said, "But I think we need to give your body a rest for a day or so before we try again. I really didn't want to hurt you like that."

She smiled up at me, "Even now, you are thinking of my well-being before thinking about your own needs. I know for sure now that you were a good choice for the first, and hopefully only, man to make love to me."

I asked Kathy if she would like to get a shower with me. I could get her cleaned up and feeling better. She agreed, and I helped her into the shower. I took the towel into the bathroom and put in the sink with some warm water to soak.

Once in the shower, I adjusted the water temperature to warm and started soaping her body. She protested that she could wash herself, but I insisted that this was something that I wanted to do for her. She was quite sensitive around her pussy, and I had to be very gentle when washing her there. The bleeding from her broken hymen had stopped, but there was quite a bit of blood on her skin.

I carefully cleaned her, and then soaped up the rest of her body for good measure. After I rinsed all of the soap off of her, I asked if she would like to wash me. She smiled and picked up the soap. Kathy gave me a thorough scrubbing, and by the time she was done, I was not only clean but hard as a rock. She looked at my cock and said, "That will never do. Let me take care of this."

"How do you propose to do that?" I asked.

"Like this," she replied, and she started sucking the tip of my cock. "I don't know if I am doing it right, but my girlfriend told me that guys like this."

"You are definitely doing it right," I told her. Kathy continued to suck on my cockhead, using her small hands to stroke the shaft as she sucked. The shower kept everything lubricated, so her actions never caused any bad friction for my cock. The longer the blow job went, the better it got.

I told her that I was getting close to an orgasm, but she just kept sucking, so I pumped my sperm into her mouth. At first, Kathy was startled, but then she started swallowing as I pumped more sperm into her mouth. I never asked her to do that, but she just thought it would be the most pleasurable way for me. When the flow stopped, she sucked and licked me clean, and then soaped me up one more time for good measure. This girl might be a keeper unless things turned south.

I toweled her dry and kissed her deeply. Then, I asked what she wanted to do now. "Let's go back to bed," was her answer. That caught me off guard, as I expected that I would have to take her home. I asked Kathy if her mother would worry about her, but she said that she told her mother that she would be staying with me before we left the house. Now, I was really surprised, and I have to admit, I was quite shocked.

It was now obvious that Kathy had planned the whole thing to lose her virginity to me. I'm sure that she had no idea that it would hurt so much when she planned it out, but she understood that there might be pain. It was plain now that Kathy wanted to marry me and figured that, if we fucked enough, I would get her pregnant, and I would be obligated to marry her.

We snuggled up together in the bed, and I was nestled in behind Kathy's back holding her against me. That was how we fell asleep. A few hours later, I woke up to a hard cock. I hadn't planned to do anything else that night, but Kathy had other ideas. Even though it obviously hurt her, she backed up against my cock until it slipped inside of her vagina. Kathy was obviously pretty sore at her vaginal entrance, and she grimaced and moaned in discomfort as she took my cock inside of her vagina, but she persisted until my cock was pressing against her cervix.

I started thrusting and withdrawing as she rocked her hips to meet each of my deep thrusts. It wasn't long before we had a good rhythm going. I rolled Kathy up onto her knees, and without letting my cock slip from her pussy, I started fucking her doggie-style.

"Oh," she cried. "That feels so good. Fill me up with your sperm and make a baby in me. Please."

I was up on my knees behind her slamming into her pussy with my full force. I was no longer worried about causing her pain because Kathy had just accepted the pain as part of the deal, and she would do whatever was necessary to get pregnant by me. My cock was repeatedly pressing against her cervix every time I thrust into her, and it wasn't long before I was shooting long ropes of sperm through that cervix and deep into her womb.

Kathy didn't orgasm that time, and I'm sure the pain from her sore vaginal entrance was part of that, but she still seemed to enjoy it immensely. Who knows how much of that was real. She was pushing back at me hard as I unloaded my sperm into her womb, and then she stayed tight against me, holding my cock deep inside her pussy as long as possible. There was no doubt that Kathy was hoping to get pregnant that night.