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Thoughts On My First Experience At 27

15 minutes
My parents are strict. Our helper would bring me to and from school when I was a child until I reached college. After I graduated from school, I went to live with my aunt and her family in Manila and started working there. It was expected of me as a Filipino-Chinese to meet and marry another Filipino-Chinese. I went through several introductions, but none worked out. When I look back, I wonder if I was being too picky. I don't think I look bad, but I don't think I am beautiful either. During my early 20's to early 30's, I was slim at a height of 5 feet and 5 inches, with a weight ranging from 115 to 120 pounds. I have grown heavier now that I'm in my late 40's. I never really liked exercising since my back ached even with doing simple crunches.

When I was in my early 20's, I was always curious about the male genitalia, what it looked like and what it felt like to touch it. I have also always wondered what it felt like to kiss and be touched. I'm not really sure when it started, but when the internet became more readily available and I was doing some research, a pop-up ad came up. I wondered what it was. I clicked on it and came upon a porn site. Curious as I am, I started browsing through it. I saw pictures of both nude men and women. It was interesting to see the different sizes of women's breasts, both natural and surgically enhanced. It was even more so when I saw the different colors and sizes of men's penises. The sexual acts shown in the pictures also titillated me. I felt horny just looking at the images, while at the same time, I felt nervous and afraid of how it would actually feel to be having sex. I heard from some married colleagues about how much it hurt the first time, and even more so when they got pregnant and gave birth.

While I kept surfing through the porn sites, I started getting some ideas as to what I would like to see in real life. I was beginning to think that I might actually be bi-curious since I also have a penchant for the female body. Don't get me wrong, but it's all about preference and not about discrimination. I like looking at both nude men and women. With women, I like their breasts to be natural and not too small. I don't care about a person's body type. As long as I like how they are and feel an attraction, I'd want to be with them. For men, as long as there is no weird stuff, no pain, and no anal sex. I have seen some porn that involves anal sex, and I was quite grossed out as that is where poop comes out of. Years passed, but I never got to see any nudes.

When I reached the age of 27, I was introduced to yet another Filipino-Chinese guy. He was 8 years my senior. He was taller than I was, which I liked, and that was it. After our first meeting, the matchmaker asked if I was willing to see the guy again, and I assented. For the second meetup, he brought yellow roses. I felt happy because even though I didn't really care much for cut flowers, it was my first time receiving them. Days passed, and I would receive text messages and calls from him, and then we'd meet up during the weekends. For some reason, I have fallen for him, and he was my first love. On one of those occasions, he asked me out to watch a movie. After the movie, we ate dinner and went back to his car. This was when he suddenly started kissing me. I was really disappointed with my first kiss. It felt as though he was slobbering all over me. I didn't expect kissing to involve so much tongue with lots of saliva going all over my lips and around them. When he finally stopped, I had to wipe my face. We put on our seatbelts and he drove me home.

Another week has passed and we went to see another movie. I was wearing a blouse and jeans, as I usually do when we meet. We walked a couple of rows to the back of the theater and waited for the movie to start. While watching the movie, I felt his hand touching my knee. I didn't know what to make of it, but since his hand was slowly going up my thigh, I began to feel really nervous and tried to push his hand away. He looked around and started doing it again. I tried to push it away again, but his hand was so much stronger. His hand slowly went to the insides of my thighs as he tried to pry them wider in order to reach my groin. I was shocked by how he was acting. Never, in my wildest dreams, fantasies, or nightmares, have I ever thought this would happen to me. I kept pushing his hand away, but he just kept at it. Even though I was afraid of getting caught, I couldn't take it anymore and started getting turned on. I opened up and he started pressing into my clit from outside my jeans. He started rubbing up and down my pussy, and it felt so good that I held onto his hand and closed my eyes in ecstasy. I have never felt anything so good. He just kept at it until my jeans were soaked through. When he finally stopped, he leaned over me and whispered that he couldn't believe how wet I got with just his touch. I felt ashamed of what happened, but at the same time, it felt so good that I wanted it to happen again.

When I got home, I still couldn't believe what had happened. I also didn't expect to feel the way I did. It felt so good for my pussy to be touched, and I wanted more of it. My mind kept repeating the scene at the movie theater. I wanted the week to go by fast in anticipation of being touched. I want his hand on my pussy. But it wouldn't go the way I wanted it to. The week went by unbearably slowly as I went to and from work. We'd still send text messages or call each other, but we never spoke of what happened in case other people heard our conversation. I forgot to mention that he lived with his father and siblings, while I lived in a dorm.

Anyway, the work week finally came to an end, and we went out to see another movie. He selected our seats, waited for the movie to start, and started touching my thighs. He slowly caressed my inner thighs while I opened up, eagerly waiting for his hand to touch my cunt. He used his middle finger to press down against my clit a little slowly and lightly at first, making me squirm in my seat. As time gradually went by, he started pressing down harder while making his finger go up and down my entire pussy lips. It felt so good that I started to want more. He must have read my mind because he suddenly stopped, started to unbutton my jeans and zipped down my zipper. I bolted up in alarm and looked around. Seeing that nobody seemed to have noticed what we were doing, he slowly slid his hand into my pants, on top of my panties. My pants were already wet, but he touched my pussy through them. It felt so much better since there was just a thin layer of cotton fabric between his finger and my pussy. I began to hump his hand while his finger kept going up and down my twat. My panties became sopping wet with my cunt juice and I wondered how it would feel to actually fuck. My senses were overcome with lust, and my fear of the pain from losing my virginity was slowly being drowned out. Once we were done, he smiled, and we went back to watching the movie. Afterwards, we went to his car and he drove off.

As he was driving, I asked him where we were going because he took a different route going home. He told me that it was a surprise. I felt alarmed since the roads are unfamiliar and we seem to be going farther out. Then we came upon a building with an underground parking lot. He drove down, paid the attendant, who handed him a key and motioned for us to drive towards one of the doors, and he parked his car in front of it. I was puzzled and just followed him out of the car. He used the key to open the door and led me to it. When we entered, I saw a large white bed in the middle of the room. I started feeling horny again, but I was also feeling fear building from the pit of my stomach.

While I was debating as to what I was going to do, he began undressing, leaving his boxer briefs on and was looking at me. I decided to undress, leaving my bra and panties on. He sat down on the bed and motioned for me to join him. As I sat down beside him, he started moving backwards and led me to lie down with him. He slowly moved the straps of my bra away from my shoulders, put his arm on my back and unhooked it. He removed my bra, stared at my tits with a smile, and bent his head down to give my nipples a lick. Then, he kept on licking my nipples while sucking at them. I felt warmth overcoming me and wetness coming out of my slit. He immediately removed his boxer briefs and asked me to suck his cock. It was my first time seeing his dick, and it looked big, thick, and beautiful to me. I started licking and sucking the tip of his hard pecker. He moaned and asked me to remove my underwear. I removed it and he went between my legs and rubbed the tip of his tool up and down my snatch. My mind was in a trance. The tip of his cock was coated with my juices, and he pushed the penis head inside my dripping wet pussy. I was suddenly paralyzed with fear and immediately pulled back. He didn't put on any condoms, and I was afraid that I'd get pregnant. He looked disappointed and pointed out that the head was already in. I told him I wouldn't have it, so he settled for a blowjob. I kept on licking and sucking on his cock until he came in my mouth. In all fairness, I loved the taste of his cum. It tasted nice and sweet.

After a few more weeks of meetups and making out, he suddenly told me that he wanted to break up and was seeing someone else. Five months into the relationship, and he tells me he wants to break up. He divulged that he was seeing someone at the same time he was dating me and that she was loaded and had a job that paid really well. He said that he's sorry, but he wanted to marry a rich woman and that I should forget about him. I became quiet and couldn't believe what I had just heard. I started tearing up and was thinking to myself that it must be untrue. He drove me home and I continued to cry. The unfairness of it all was overwhelming. I took out all the medicine I had on-hand and drank it all up. I just ended up with an upset stomach and felt really bad all over. I puked and slept it off and was fine the next day. I was depressed for more than three months and would suddenly tear up over nothing. My friends tried to console me and took me out with them. My colleagues also tried to console me and told me that the guy didn't deserve my tears because he was a big jerk.

Despite all the consoling, I was still miserable and wondered if I was devirginized when the head of his penis entered my cunt. I couldn't get it out of my mind and eventually decided to look for a guy to have sex with. I know, I know. This might not be what people would normally do, but it's what I thought of at that time. It could have been a stupid choice, but nevertheless, it was over and done with. It's all in the past.

After searching all over the internet, I was able to hook up with a handsome German guy online. I can't, for the life of me, remember the name of the website. Anyway, after chatting with him, I came to like him because he knows what he wants and is quite honest about it. I told him of my situation and that I wasn't sure if I was still a virgin or not. He assured me that he would make sure that I didn't feel any discomfort. We agreed to meet up, scheduled a time and place, and he picked me up. I was quite anxious and he saw through me. He held my cold hand, smiled, and told me not to worry. I smiled back shyly, still feeling nervous. He had a really nice smile, and it did put me at ease, just a little bit. He drove to a motel where each room had its own parking lot for privacy. When we got into the room, we talked for a minute before going in to take a shower.

Subsequently, he took two towels and handed me one. We both wiped and wrapped ourselves in it and went straight to bed. We both lay there with him facing me. He started kissing me, and it felt really nice. It was totally different from my first kiss. At first, his kisses were soft and tender. He then went down a little and began licking and kissing my neck. Next, he sucked my earlobes while tugging them gently with his teeth. He kissed me again, more passionately than when we initially began kissing. It all felt really good and I was very wet. He kept kissing me and gradually went down to licking and sucking my tits. I was moaning and my mind kept saying, "Please fuck me." While licking and sucking on one breast, one of his hands was fondling the other, and vice versa. Both of my tits are occupied by either his tongue and mouth or his hand. It was driving me crazy. His mouth let go of my tits and he used both his hands to caress my breasts while rubbing my nipples between his fingers. He continued doing that while kissing my body deliberately from between my breasts, down to my stomach, going down between my legs. He pushed up my legs, opened them wide and started licking my inner thighs. He kept on licking while I squirmed. He kept a firm hold of me while licking from one to the other, and then he started licking my pussy. I was going wild and kept squirming while pulling at my hair. It was mind blowing. It was the first time that anyone had gone down on me. I was so wet and he just kept licking and tongue fucking my pussy. Afterwards, he inserted one finger while still licking my clit, then another. I couldn't take it anymore. I thought I was going to die. He got up, rubbed my pussy with his hard cock to coat it with my juices, and slowly inserted his cock head. He kissed me passionately as he slid his shaft into my already wet pussy. His prick was bigger than my ex's, and I was worried that it would hurt. It didn't. He made me feel so horny that my mind was literally screaming for him to enter me. We fucked for what felt like ages, then he pulled out, guided me sideways, and shagged me while massaging my tits. I turned my head and he kissed me. We kept banging until he knelt, placed two pillows on top of each other in front of me, and had me kneel with my stomach lying flat on the pillow with my bare bottom in front of him. He again inserted his hard member and screwed me. He asked me where I wanted his cum, and I told him that I wanted it in my mouth. His semen tasted different from my ex's.

We washed up and went to eat lunch. My stomach started cramping. I went to the bathroom and saw some blood on my underwear. It's when I realized that having my ex's penis head inside my pussy didn't mean that I was no longer a virgin. I felt regret for having lost my virginity, but at the same time, I felt glad that I did. Having had sex with the German guy was well worth it because he's very experienced and since he made me feel good from start to finish. I went back and he had even ordered hot tea for me. After lunch, we went somewhere else to chat while having coffee. Then he drove me back to where he picked me up. After that, we met up a couple more times before he went back to Germany for work.