Thank you to all who enjoyed my first story. As promised, I am continuing on with my entries.
Myself and David continued on with our relationship into high school. We didn't make it known among our peers in fear of being ridiculed, so it was secretive from peers and still parents. After school, we'd be mostly at his place, engaging in oral sex or humping on each other till we came. This continued throughout the first year of high school. We'd get adventurous in our time, doing stuff in public places such as sucking each other off in public washrooms or going down to the local beach at night for a skinny dip and some fun. However going into summer, things started to calm down and when David got a part time job over the summer, we began to see little by little, less of each other. It was almost like I was losing some part of me. Never the less, when we got the time, we made the most of it. I remember one night, meeting up with David after work. He was closing up shop at a grocery store and I was hungering for him for a good two weeks. Being the last one to leave, he was the last one there. I remember attacking him with kisses after the last person left. I didn't care if anybody came back. I ripped open his t-shirt that he wore, and attacked at his pants. Getting them down, I literally tore open his underwear, before attacking his cock. I sucked his cock like a crazed nymphomaniac. It wouldn't be long before he exploded all on my face.
Yet, our time with each began to diminish. I too also began work at the beginning of the next school year. Soon we stopped seeing each other after school. We would still talk to each other in school, yet it didn't seem like the times before. David avoided the topic of us. It turns out as I learned amongst peers that at the of the last school year, David went to a party. There he met up with a female, whom he engaged in sex with, and was seeing on the side besides another female that he was dating. It crushed me. Seems David was playing both sides of the fence, literally. One with two females, and one with two sexes. I thought to myself that the relationship I built with David was for real and serious. However, it turned out just to be a sexual relationship where David got his thrills from. After learning this I stopped talking and seeing David. When asked what was wrong by David, I simply answered that I was busy with other things. He took the hint, and unfortunately it was the end of us talking to each other for a good while.
I began to focus on my schoolwork. It was lacking a bit since my afterschool visits with David. My marks improved, and made honour role a second year at my school. As a reward, my mom had given me an opportunity to take a trip to any destination I chose. She was saving up money for a vacation, and decided for me to use it for the hard work I put for school. She also said it was a sweet 16 gift as I just turned that age. I decided I wanted to visit Cuba. I read up on the brochures of it, and was interested to go. It was there that I would I lose my virginity.
As the plane taxied onto the runway, this became the first experience on my own away from my parents. I was to be shacking up with a group there that catered to foreign students for one week. It was hot and sticky and I could feel the heat in the air. On the bus ride to my quarters, I looked out, gazing on the country and it's people. I would be staying 15 minutes outside of Havana. I kept up on my Spanish well to speak it there, since I took Spanish courses at school. The first couple of days there, I toured the sites and walked around Havana, visiting the little stores and shops. Being at the student quarters, we were due back by 12:00am the latest. We got breakfast and dinner served to us optionally. I found it surprising that we were allowed to tour alone. If we got in trouble, we were given a number to call the quarters in case of emergency or if we were lost. There I met a group of students, both male and female. Some were not only from the US but from Canada, the UK, and France. We shared stories of school experiences and our experiences in the country so far. For some reason as well, I started to shave my pubic areas. My pubic hair began to sprout, so I trimmed my cock area, keeping a nice lightly shavened area, keeping my cock and balls clean. I also made sure that I shaved my ass hairs as well. I don't know why I began to do this. It could have been the fact that I saw one of the students in the shower there, Juan, who barely had any area hair around his pubic area. It was on my third day there that I met Carlos.
I was roaming once again the streets of Havana with a group of the students in the marketplace district. I strayed away from the group, and was in a cigar store, admiring the fine tobacco artistry. There I was approached by an older male. What at first began as small chit chat, became a conversation. I learned his name was Carlos. He was an older man, 48 years of age. He was a balding man who had a receding hairline of curly afro like brown hair. He had brown eyes with a bushy moustache. He was slim in figure and about 5'11 in height. He had a dark tan on him. The shirt that he wore was open and he had little curly chest hairs that were exposed. He was dressed very nicely, and a thick gold chain around his neck. I thought he was a drug dealer at first but he was an entrepreneur in Cuba, at what business I never found out. He offered me a coffee. I was nervous at first but accepted. We sat down and chatted. We exchanged conversation, both in Spanish and English. He spoke English very well, and said he had to learn it as he travelled a lot. He was very eloquent in the way he spoke and I admired that. He asked if I wanted to tour around the city a bit more with him. I agreed.
We took his car and we travelled for the day through Havana. He showed me some shops and even bought me a few trinkets here and there. Here I was in Cuba, touring with a stranger from a foreign country, but yet I felt very comfortable and safe around him. He then asked me if I wanted to have dinner at his place. At first, I was weirded out by this. I was wondering if he was attracted to me. Was he gay? I accepted, seeing that I didn't want to spend money on dinner as I had planned a group night out with some of the students. He took me to his house which was absolutely beautiful. It was on a hill that overlooked the sea. There was an outdoor patio with a dining table setup on it for outdoor dining. Near the garage there were two other nice cars, confirming my fact that this guy was loaded. When I entered his house, it was like walking into a mansion. Art and decorations were abound with beautiful furniture. He even had a lavish entertainment unit. I got to get comfortable in his house before he whipped up dinner for the both of us. We sat and ate dinner. He offered wine even though he knew my age. I declined the first time, but curiosity got to me and I had a glass on the second offer. After dinner we both stood out on the patio with a glass of wine, enjoying the night sky and the sound of the ocean. I remember him putting his hand on my shoulder. I felt the same tingle that ran up my spine when I was with David for the first time. It was then that Carlos came clean with me and said that he was attracted to me. He told me that I was the most beautiful male he had seen on the island and wanted to kiss me and that even if I wasn't gay, he wanted me to know that. I blushed from his compliments. I didn't know what to say, but I knew what I wanted to do. I put my wine glass down and went approached Carlos. I gave him a hug. It was then when I looked at him face to face, that I leant in to kiss him. Our lips met and it was the softest most romantic kiss I ever had with a man to date. His moustache tickled my upper lip. Our kiss became deeper. I remember myself getting instantly hard. I pressed myself against as it got deeper. My hard cock pressed up against the bulge the grew in Carlos' pants. He pulled away, saying he couldn't do this as I was young to be his son. However I insisted and pulled him back to kiss him once more. I told him that I didn't care and that I wouldn't tell anybody. He wrapped his arms around me kissed me deeply. He took my hand and led me inside.
Leading me through his house, my heart was beating like crazy. It wasn't like the times I had fun with David. I had never experienced anything with anybody older than my age, and this being especially with an older man twice my age. Carlos lead me to the bathroom. What an extravagent bathroom it was. Not only did it have it's usual sink and toilet, but it had a large bathtub that looked like a hottub, a door that led to a built in sauna, and a section for the shower which had no walls. It almost reminded me like a public shower. Carlos began to undress me slowly, taking off my t-shirt, my khaki shorts, and finally my underwear which exposed my erection. Carlos began to take his clothes off. When he got this underwear, I got see the head of his cock being exposed from his underwear. When he removed them, I saw probably the biggest cock I had ever seen so far. My estimation must have been 8 to 8.5". He was very hairy all over his body, with a big tuft of pubic hair behind his enormous cock. Pretty impressive for a 48 year old. He led me into the shower, and got the water running. He held me. I could feel his huge cock press against my ass. He soaped me down, running his hands all over my body. I got excited when he ran his hands on my cock and my ass. I likewise did the same to him, soaping him down and running my hands on his ass and huge cock. We kissed intimately again. He held me, tilting my head back to kiss him. It was amazing. We stepped out of the shower, drying each other off with the towels available. Carlos once again took my hand and led me to the sauna. There he took a bottle of oil that I assumed was used for the sauna. He started to oil me down, rubbing it all over my body. This time he rubbed alot around my ass, particularly my asshole, and I could feel him slightly fingering me. The sensation was amazing. I again did onto Carlos, oiling his body down. His hairs glistened from the oil. I concentrated on his cock, stroking it a few times. Once I was done he once again took my hand and led me out of the sauna and out of the bathroom. We were naked walking through his house, but it seemed he didn't care. He led me to the bedroom. There was a bed with a canopy and a white see through material over it. Quite a few candles lit the room. It was almost like he had this prepared for me. He led me to the bed and laid me down. He began to kiss me again. I felt the tip of his cock touching mine, and again a sensation ran through my body. He began to kiss my neck. I moaned to let him know he was doing good. The oil on our bodies made to so smooth when he glided down to kiss my nipples. I was in exstacy. He then got to my cock. However he wasn't like David who sucked me off. He instead kissed like he was kissing my lips. His moustache hairs tickled me even more but yet it felt good. I moaned in pleasure. I sat up and kissed Carlos again. I began to kiss his nipples. His chest hairs tickled my tongue. I then got in the kneeling position. Carlos knew what I was going to do and sat down, laid out. I got to his enormous cock. I began to copy what Carlos did. I kissed his cock like he did to moan. I heard a slight moan from him. Finally I opened my mouth and closed it over his cock. I began to suck him. He moaned loudly and I felt his hand on the back of head, running through my hair. I could only take him in halfway. I couldn't deepthroat like I used to do sometimes with David. Each time I bobbed down, he moaned. The tiny hairs on his cock tickled the top of my mouth. With each bob, his moans got louder. After a bit, he pulled me away and turned me onto my hands and knees. I knew that he wanted to fuck me in my ass, but this would be a first time, and I was nervous about how it would feel. He spread my cheeks apart and I felt his tongue on my ass. It sent a sensation through my body. I felt his moustache hairs tickle the area around my hole. He got off the bed and opened a drawer, taking out a bottle of lubricant. He squeezed some into his hands and began to rub it all over his cock. He squeezed a bit more and came back onto the bed. He began to rub it all over my hole and around it. I soon felt his finger tickling my hole, before it literally slid in. I gasped and gripped the sheets. He began to finger my hole and I loved it. It seemed he kept hitting the right area, for it got my cock really hard and it sent a wave through my body. After getting my hole nicely lubed and relaxed, I felt the tip of his cock press against my hole. He was going to enter me. Slowly he slid it inside, stretching me open. After a slight shove, it slid right into my hole. I moaned. He began to slowly pump my ass with his cock. My breath became deeper. He was hitting that spot on me a lot more now and it got me going. I began to rock back to how he was pumping me. He along with myself moaned in pleasure. It was an amazing feeling. He leaned forward, putting two fingers in my mouth, and I sucked on them as he kept pumping me. He started to pick up the pace and I began to moan louder. My cock was erect as it ever was and I could feel that tingling sensation around my cock. It wasn't long before I felt myself cumming, spraying my jizz on the sheets below me. I gripped the sheets tightly, moaning loudly letting Carlos know that I came. It seemed to turn him on more as he started to pump me faster, this time gripping my ass so much to his cock, that he got every inch into me. I soon felt myself after a bit getting hard again. I never got hard so quickly after cumming, but it seemed that anal sex got me going like no other. Sweat beaded off our bodies. Carlos' moans became louder and his breathing deeper. Managing to balance myself, I grabbed my cock and began to stroke it fast to make myself cum faster. I moaned louder, trying to get Carlos to release. It wasn't long before I felt his cock inside me begin to jerk. He moaned loudly, cursing in Spanish and saying he was cumming. I felt each shot in me. He shot at least 5 to 6 times. It was on the last shot that I came too, spraying once my jizz onto the sheets below. He slid out of me and we collapsed in a heap of sweat. It didn't even occur to me that I was lying in the dampness of my cum. I could feel Carlos' jizz oozing and sliding out of my hole down my back thigh. I was so taken in by my first anal experience that I wanted to go again. Carlos kissed me again and held me for a good while.
We'd later go out at it again. This time Carlos made me lie on my back, with my legs cocked in the air. Though it was somewhat uncomfy, he once again got me going. Every inch drove deep into my ass and I got the pleasure of jerking myself off while he did this. I came twice again: once during sex, and finally when Carlos blew his load into me again. My cum covered my stomach and chest. Carlos smeared and rubbed it on me. We called it a night as I began to get sore and lost track of time. Before we left, I kissed Carlos passionately and thanked him for an amazing night. Carlos would drop me off at the complex around 1:00am in the morning. I kissed him again in the car before leaving. This would not be the last time I saw him in Cuba. We'd have two more experiences again that I'll share with you all in my next entry.