Ladyboys Moving to Thailand and my first Ladyboy
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My First Sex, Boy On Boy free porn video
My mother and father had recently divorced and we moved to a new town for my mothers new job. This was a great thing, my mother had been working as a waitress in coffee shops and we had been poor, really poor. This new job was a new beginning for her and our little family, all four of us. I have two older siblings, a brother whom I constant fought with and is 5 years my senior and a sister who liked to dress me up and was 6 years older. She was mischievous, she once painted my nails and I didn’t notice and went to school like that. Surprisingly no one else noticed either, or at least if they did they didn’t say anything.
We moved into our new house and in the suburbs, the American wet dream. On one side was an older retired couple and on the other side was a family similar to ours, except they had two boys only named William and Jeff. William was the older and about 15 or 16 at the time. He was very good looking, naturally athletic and actually resembled a mini bodybuilder. Jeff, he was about 13 and not easy on the eyes. He resembled more of a toad that got run over in the middle of the road with his bulging eyes and round head.
I was about 13 going on 14 when we first moved in. We were friendly enough but not the sort to go over to the neighbors and introduce ourselves. We settled in and quickly had the older couple next door pulling their hair. My older brother had a habit of listening to his Rock music at full volume and working on motorcycles all day. This drove them bonkers. When he wasn’t doing that he was fighting with me. I was no match for him, but I could run faster! One day, for no reason other than PMS he started a fight with me. I quickly left the house for a run. He took chase and I ran across the neighbors yard and there was William. He stopped me and asked what was up at which time my brother arrived told William that he was going to “Kick his ass”. William told him, “No, he is half your size. You need to go home and calm down.” A little background, William had a reputation of being a ultra nice guy in High School, but with a temper you didn’t want aimed in your direction. He once was bullied and slammed the bully’s head into the side of a school bus causing a dent and an unconscious student. He was as strong as a bull.
I went into Williams house and we got some drinks then went to his bedroom. There we found that we both liked history and reading. Soon we were discussing topics and basically geeking out together. We became fast friends. Later that night I went back home and my brother had locked himself in his room for the night. I grabbed something to eat, went to my room to listen to music and read. At this time in my life I was pretty much asexual. I had compared penis with another kid once when I was much younger, I had kissed a girl and held hands but that was it. I was no Casanova by a long shot. I had very soft features, never very “masculine” and I did have a bubble butt which my sisters friends liked to point out. They used to grab my ass and ask her, “you sure you don’t have any black in you?”
Days and weeks went by and I would occasionally hang out with William. We would do crazy kid stuff and always manage to evade trouble. I was really comfortable at his house. After our outings we would go hang out in his living room and watch TV or go look at books that interested him while in his bedroom. One day after we made it back to his home he sat on one end of the couch and I lie my head on the other. I slipped off my shoes and we were watching TV. I was in a fetal position and he was just there watching the television when I stretched my legs and as a joke began to nudge him further compressing him into the arm of the sofa. “Hey! I can’t go over any farther!” he laughed. I remember I kept pressing him with my feet and laughing. My right foot slipped. It grazed his crotch. My sock slipped over this bulge in his jeans. I remember I did not move my foot, I left it there for a second then without thinking I rubbed the arch of my foot along the length of his bulge. Slowly up and down a few times. I really was not thinking, but now that I think back on it things could have gone horribly wrong. He then put his hand on my foot and began rubbing it against his increasing bulge. I wasn’t even looking at him, I was acting like I was watching TV. Was I shy? I remember my heart was racing and it was like I was getting tunnel vision. He then reached up my leg and began to slide his hand up my loose shorts. I remember the shorts were black gym shorts from school, they were comfortable. As his hand went further up my shorts leg he pulled aside my white briefs and began to fondle my little cock. I remember my breathing changed to a heavier, deeper pattern as I shifted more onto my back to give him easier access. He then asked, “Do you like that?” I remember I just looked at him and shrugged, I guess I did like it, I really didn’t know. “Do you want to stop?” he asked. “No” I said in a whisper as my foot continued to massage his bulge and he continued to fondle my penis. Then he told me, “I have a really big dick.” “Yeah, right. It is probably tiny.” I giggled. “No really, do you want to see it?” he asked. “Sure, I guess so.” I replied feigning no interest. ”Ok” he said as he unbuttoned and unzipped his jeans.
He reached into his white briefs and pulled it out. It was big, long and thick. He grabbed me by the wrist and helped me sit up. “Touch it.” He said. I reached over his lap and placed my right hand around the shaft of his hard cock. I had never really seen another boys penis before, at least never this close. The skin was so smooth and supple, the color of the shaft was slightly darker than his skin tone. It seemed to be the most perfect penis in the world. It was easily 4 times bigger than my own. If my penis were that large I would masturbate all the time I thought. I continued to stroke his cock enjoying the warm feel in my hand, a hand that could not cover the circumference due to its girth. I was still completely calm at this time, he was completely aroused. “Do you want to suck it?” he asked. “I dunno” came my reply. “just try to suck the tip” “ok” I said as I lowered myself off the couch to get kneel on the carpet between his legs and he as he shimmied his pants and underwear down to his knees. My heart was racing!
I had never sucked a dick before. I had no idea what to do or expect. With my hand still on the base of his cock I lowered my head and my lips parted. The head of his penis was filling my mouth. I began to suck his head in and out of my mouth. He pushed my head down gently and was able to take about another 2 inches in. He was big and my mouth was small. I was thoroughly enjoying the experience. I loved the taste, his smell and the way his cock was filling my mouth. I got a little “cocky” and tried to go deeper, I wanted his whole cock in my mouth. I gagged and pulled my mouth away as I began to cough and sputter. “keep sucking it.” He coaxed me while pushing my mouth back down around his cock. My lips wrapped tight around his head and shaft as my mouth continued to milk him. Small passionate moans escaped him as he began to gently thrust his pelvis forcing his cock into my eager mouth. Then he spoke in a strained voice “I’m cumming, I going to cum!... Ahhhhh!” as he released his warm, thick load of sperm into my mouth, shooting some to the back of my throat making me cough and sputter again. Much of his cum mixed with my saliva dripped down the length of his cock. I immediately got up and made my way to the kitchen sink to spit it out. “I’m really sorry. I told you I was going to cum.” He apologized. I washed my mouth with water and told him that it was “ok.” He then told me that his parents were going to be home soon, I told him I needed to get home too and left.
That night the scenario kept repeating through my mind of what had happened. I knew that boys my age had homosexual experiences and I knew that it was normal. Was it normal to enjoy it so much?
I waited two days before I went over to visit. I was still confused about all that had transpired, and slightly embarrassed. Boys were NOT supposed to suck off other boys. This was a bad and shameful thing. Right? I went over and his brother Jeff was there on the couch watching TV so William and I went to his bedroom to goof off. Everything was back to normal. The blowjob was never mentioned. I was relieved; I was really concerned about losing him as a friend. He excused himself from the room and I told him I was going to check out his music collection. The stereo was on a low stand so I was kneeling on the carpet flipping through the tapes and CD’s. CD was the latest thing back then and very cool. I was putting on some Led Zeppelin as he came back in the room. He casually stood next to me when I noticed his cock was out. I was shocked but knew what he wanted. He looked down at me and told me that the door was locked. I reached up and grasped his cock by the shaft and spread my lips for his large mushroom head. It was like a natural thing for me to suck his dick. My head bobbed up and down as my lips and tongue began to milk his cock. I loved the taste of cock in my mouth, the smell was intoxicating. It was my drug of choice. When he did cum, I let him cum in my mouth again only this time I blocked my throat with my tongue and spit out the off white, creamy liquid onto his briefs crumpled up next to me.
This went on for weeks. I would come over to his house, we would go to his bedroom and I would suck his dick. I loved it! When we first started I was shy, but a few weeks in I was hungry for his cock. It consumed my thoughts daily. I would think about the smell of his cock and how good it felt in my mouth I sucked him off. It took a concentrated effort not to run to his house after school. We did other stuff too, not just sex. We would go hang out with other friends and skateboard or play basketball, normal kid stuff. We always got that blowjob time in though.
One day we were in his living room and he was kneeling on the carpet working on something for school and I snuck up behind him and tried to put chokehold on him, just wrestling around. He slipped me off and I was on my back at his knees. I remember looking up at him still laughing as he lifted up the leg of his loose gym shorts. He was not wearing underwear that day and the length of his cock was ready for me. I rolled over onto my side and took his cock into my mouth. I put my hand on his ass and was pushing him to feed me more of his big cock. I loved it, my mind was clear as I sucked his dick. I worked his shaft into my mouth but could never get more than half of it in. He was too long and too thick for my little mouth. I would later figure out that he just really had a huge dick. At one point we had measured it in his bedroom and it was about 9 inches and other times almost 10. Of course I didn’t know any better, I just thought I had a really tiny dick and that all other boys were his length and girth. I continued sucking him off and he began to tell me how good it felt and this just encouraged me to suck harder. I got a taste of his pre-cum and I had no problem swallowing it. In fact I liked the taste of his pre-cum. As usual he gave me a warning, “I’m cumming! I’m cumming!! Ahhh!” he would groan and shoot his thick ribbons of cum into my eager mouth. I would let him cum in my mouth, but I would never swallow, even though I had fantasized about it daily.. and nightly. I would always go home and masturbate to the thought of sucking his cock. It was a huge turn on, no pun intended.
I spit his cum out on a blank sheet of notebook paper. Then with a sneak attack I jumped at him and he fell to the carpet on his back. I had him pinned to the floor. Of course he was much stronger than I and could have easily threw me off, but his hands were too busy feeling my body. It sent electric currents racing through my body. His hands on me was driving me insane. His hands rested on my round ass and with natural instinct I began rubbing my ass against his crotch. I remember slowly grinding my boy pussy on his bulge, feeling him grow under me while looking him in his eyes. It felt wonderful, I was loving it. I remember biting my bottom lip and letting out a slight moan as I continued to grind my virgin hole onto his cock. He reached up to my chest and began to play with my breasts. I have always had small titties my whole life, a small handful. “You want me to fuck you?” he asked. “if you want to, ok.” I replied. “Let’s go to my room” he said. I got up and walked to his room. My head was in a cloud, I felt dizzy as if I might faint as I entered the room. “Take of your clothes and get on the bed, I’ll be right back” he told me.
I removed my clothes and lie on his bed. I was embarrassed of my little penis. Compared to his mine was nothing. So I rolled over onto my stomach to hide it from him. Like I said before I was a virgin, I had never been fucked before and had no idea what to expect. Looking back, he had done this before or had read all about it. He came back into the room with a bottle of Baby Oil. He stripped his clothes and stood before me completely naked. He had a perfect body.
He sat down next to me on the bed and rolled my torso over by the shoulder, I was still hiding my penis from him as he leaned down and began to suckle my nipples. I was thinking, “WOW” the electricity coursed through my body as his tongue flicked my nipples and his mouth suckled my breasts. My hand was on the back his head, I was thoroughly enjoying every second as his hand moved to my ass. He began by rubbing my smooth round bubble ass, then squeezing and spreading the cheeks. His middle finger then found its way to my virgin, pink hole. He was not entering, just massaging it. My head rolled back, my mouth slightly ajar as my breathing became more rapid and shallow. Was this what sex was like? If so, I was LOVING it. I wanted his cock in me. “You still want me to fuck you?” he asked. “yes, I want you to fuck me.” I replied. I was on the verge of begging him to fuck me! “It’s going to hurt. I have a big dick.” He warned me. “I want you to fuck me.” I whined.
I was again flat on my stomach, my head on the pillow. He squeezed the warm Baby Oil onto my very tight, virgin hole and with that same middle finger began to fuck me slowly. I grew accustomed to his finger when he added a second. “Ahhh!” I wailed slightly. I could feel his fingers stretching me open. My sphincter muscles complained with sharp pains and a spasm as if to remove the intruder. I slightly grimaced,”Ow, ow, ow!” and he stopped and let my hole grow accustomed to the stretching. Then slowly he began to move his two fingers in and out of my tight virgin ass. It felt amazing, I wanted more as he removed his fingers and began to lubricate his stiff cock.
He spread my legs and poured some more Baby Oil onto my pink hole. “You ready?” he asked. “Yes” I replied simply as he lowered himself onto me. He placed the tip of his massive cock center of my ass pussy and began to gently thrust. The pain was incredible, and not in a good way. It hurt. Sharp shocks of fire shot through my body as I at first gasped then grimaced clinching my teeth only to open my mouth and say, “Fuck that hurts, it hurts! Stop! Stop!” and instinctually tried to crawl away to escape. “I told you it was going to hurt” he said. “I know, I know. Just give me a few seconds.” “My head wasn’t even in” he replied. I lie there thinking, ‘Fuck, if he wasn’t even in, what’s it going to be like when he is in!?’ He tried again with the same results. It was just too much pain. My virgin hole was throbbing with pain and he was growing frustrated.
“Let’s try a different position” he suggested as he rolled me over onto my back got off the bed and pulled me to the edge. He was now standing and my feet were resting on his chest. I wanted him to penetrate me, I wanted him inside me. “Let’s try again” he said as he added more lubrication to his massive cock. “Just be gentle, ok?” I pleaded. “I will, I don’t want to hurt you.” He replied. He began to gently push his cock head against my hole applying more pressure, then more. The burning was back, I looked away and bit down on the pain whimpers escaping me. “Oh fuck! Are you in?” I asked. “Yes I got the head in.”
“Ok, Ok, hold on a second. Let me try to relax.” I begged. He stood still for a few moments with his cock in me letting my boypussy get used to the stretch. The pain began to subside a bit and he tried applying pressure to enter me farther. “Oh fuck, oh fuck it hurts!” I whined. “Want me to stop?” he asked. “No, I want you to fuck me” I responded. He then began to pullout and somehow that eased the pain, then he penetrated deeper again. The pressure was intense, the pain mind boggling. In deeper then he pulled out, then in again… only to relieve me by pulling out. Soon I noticed the rhythm. He was fucking me slowly and gently. I was looking up into his face, he was concentrating deeply on fucking me. It was now feeling good. I could feel his cock pushing up against my stomach or something.
“Does that feel better now?” he asked. “Yeah, you can fuck me faster now.” I replied. He did, he began fucking me at a faster pace, every so often he would release a grunt. I lowered my legs from his chest and tried to wrap them around his torso. I barely noticed that I was pulling him closer to me increasing his rhythm. I was still watching his face when I closed my eyes and begged him to fuck me faster. “Fuck me! I want you to fuck me faster!” I murmured. He increased his pace, he was fucking my once virgin ass much harder now. He still couldn’t get all that cock into me. It was too big and my hole was too small. Even though I wanted it, I couldn’t take it. He began to fuck me in a more frantic pace making my head lift from the pillow and whimper out, “Fuck me, fuck me!! Please fuck me!!” He complied and continued to abuse my now plundered hole.
“Ah! Ah! Ah!” he grunted loudly as he emptied his cum into me. “AH!” again as he thrust once more. His chest was sweaty, he was beautiful and he had just taken my virginity.
We lived next door for about 2 years. In those two years William and I were over sexed. It was a routine, I would come over and, depending if anyone was home, he would fuck me. I always sucked his dick almost daily. We did experiment. Once had sex in an empty house. I gave him a blowjob by a lake. Used different positions, Cowgirl, reverse Cowgirl, doggie(my favorite), flat on my stomach. We just always had fun with it. Until I finally had to move with my family out of state. We did keep in touch. He eventually got married and had kids. I did visit him after several years. He still looked great. I sucked his cock in his kitchen while the wife and kids were away. After he let me know that we couldn’t do that again because he was married with kids. We lost contact after that. -->
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