All Nifty Rules apply. If you're not an adult you should not be reading this. This is PURELY FICTION and should be treated as such. Kindly donate generously to Nifty.
This incident took place many years ago, when I was but 15. I was convinced I was born in the wrong body in the wrong part of the world. I was born to a family of 5 girls, the last boy, but would I ever be the man my parents wanted, well not exactly. Unlike my sisters I was blessed with feminine beauty. My eyes were naturally round and interesting, my lips pouty, my cheekbones high and my body well was no different than an hourglass shape. For a medium build boy I had big nipples and a bit of flesh, giving me the teenage blossoming girl boobs, much to the disappointment of my 17 year old sister who was as flat as an ironing board. My butt was round and protruding making it difficult to get the right pants. I was smooth all over as most Asians were and was blessed with a tiny cock that well never grew more than an inch longer than what I was born with. I was not fat, my tummy was a bit pouchy and I had fuller thighs than most Asians.
We lived in a town close to the big city and very close to the beach. The sea was nothing but a source of fish for my people and as a result it was not enjoyed as it should be. I on the other hand LOVED the beach and would spend hours on it when I could. I didn't have too many friends as I was ridiculed for my figure, the more masculine jock type boys pinched my bottom. The older college kids often ambushed me in dark alleyways and felt me up and would insist on having me hold their cocks, when I refused and fought back I would be beaten and thrown to the ground. The beach was my escape. The ocean endless and the warm sky. I had sun kissed skin as a result.
Clothing was an issue for me, I liked fashionable clothes but I could never find good clothes. So I would often wear women's pants. Swim suits were a nightmare, a culture that was heavily influenced by southern Europe, we had all sorts of speedos but hardly any shorts. I bought the shorts I could find and they were short! Most men wore speedos no matter what their size, but because of my butt I always felt uncomfortable and because of my tiny tits I always wore a tank top.
Hygiene was also important to me. The many times the jocks and other college guys or sometimes the random drunk near me disgusted me with their sweaty armpits etc. As a result I made sure my pubic hair was always shaved, it wasn't difficult in a home full of girls to find razors and lately wax to do so.
One hot summer Saturday when the whole family was going away to visit some cousins, who were celebrating a birthday. I managed to get an excuse to stay home. My dad was always grateful not to have me around lately because even uncles would comment on my booty or my tits or my femininity. I waited for my family to leave and I got dressed for the beach and walked the 4 blocks to the beach. When I arrived it was pretty full of locals and then I realized there must be a party on the beach that day. I was disappointed. But I realized a 30 minute ride up north would get me closer to the beach villa area and there I was assured of privacy. So I counted my money and saw that I had enough for drinks, for the bus ride back and forth and I headed up north. I arrived closer to noon and I was rewarded with a quiet tranquil beach. There were a few people around mostly tourists though.
I started walking and as I got closer I saw a man sitting partially under an umbrella. For some reason I couldn't keep my eyes off of him. He was big, very tall probably 6'4 to my 5'4 frame, he was muscular yet beefy. He did not have abs but his stomach was strong. He was in his early fifties by the look of the greying temples and the bits of grey in his chest hair. He kept his hair very short, he was balding in front but the sides were grey. His neck was big, and the muscles were big. I had seen many a muscle man before, but there was something about this man. He didn't look like he was a gym kind of guy but he was certainly well built. He had big feet and huge thighs. He was wearing black running shorts. He caught my eye looking at him, and for a moment we locked eyes. He too looked at me longer than usual. I looked away first and then looked again and saw him looking at me.
I walked past and found a spot, and got comfortable. A few minutes later the man got up and walked down to the water's edge did some stretches and started running, he passed by me and looked at me. Now I was in my swim shorts, no tank top (as the beach was deserted) on my tummy reading a book and facing the ocean. We locked eyes again and he ran past. I followed him with my eyes and couldn't help notice the muscles of his legs as he ran, the muscles on his arms and the back and the glisten of sweat all over him. I felt my cock twitch, was I horny? I didn't think I was gay! I was confused. Then I imagined him with a woman and how his strong hard muscles versus a woman's soft body would look and how he would be an insatiable lover as one saw in the porn movies my dad tried to hide. I adjusted myself as I was hard now. I tried to focus on my book and after a bit forgot about the man. It must have been about an hour later when I heard someone running from the left of me, I looked up and he was back, drenched in sweat and was coming towards me and seemed to be slowing down. And surely he stopped a few feet to my right and bent over to catch his breath. When he was caught he stretched his body and looked around, I tried not to look at him but I was conscious of his glare on me, every time I looked up I saw him looking at me. After a few minutes he walked up to his stuff, dried himself with a towel had some water and took his shoes off exposing his big feet. I found myself turn to my right to watch him, he wasn't really looking at me now. He took his running shorts off, I could hear them flap in the breeze as he flapped them hard to shake the sand off. I could tell they were wet with sweat. He put it down to dry and stood up and stretched again. This time he was wearing dark blue speedos. And I couldn't stop but stare with my mouth wide open. The front of his speedo was bulging, it wasn't an overly tight or tiny speedo it was decent sized, one of those that made allowances for a big man with a big package, but even then he was bulging. If I had to give a visual, I would say that it was likely two bananas and two peaches in his speedos kind of bulge. Our eyes met again and this time he smirked and smiled and then adjusted his speedo. Embarrassed I looked away. He sat down and I continued to read. The Harlequin novel got interesting and got to the part where the damsel was in distress, the hero rescues her they fall in love and have passionate and violent sex. After what was an hour since the man had returned from his run, I looked up and saw him sitting in his chair. He caught me looking again, this time he sat on the edge of the chair, and I thought he'd crush it with his might. The bulge even more protruding between his legs, I wondered if he could ever cross his legs with that in between. He got up, and I quickly looked away. I heard him walk close to me and my heart was beating out of my chest. I was on my back so I turned quickly to my front and tried to concentrate on my book. But he came near me and sat down very close and said. "Hey there, do you speak any English?"
I looked at him, my mouth was dry I didn't know how but I managed to croak "Hi.... Uhm yes."
He smiled and said "Name's Jake, and yours?" And he put his hand out to me.
He was American, had a deep voice, smelled lovely.
I muttered my name and shook his hand, my hand was limp and weak in his strong grip. When he let go of my hand I realized just how big he was.
"I couldn't help but notice you starring." He said
I didn't know what to say. I tried to mutter something but all I could do was deny it by shaking my head.
"Don't worry, I know I am a big guy" He said with a smile. "In fact I couldn't stop starring at you. Never seen a boy like you, so hairless, so smooth." With that he ran his hands from the top of my shoulders to the small of my back sending 100,000 volts of electricity through me. "so smooth" he said again. Then licking his lips he said "I'm here for work and have the weekend before I go home back to my wife and kids. What do you do? How old are you?"
This time I managed to mutter my age and told him I was in school. He smiled.
He said "look I am not a man of many words, and I like to be straight. I have never cheated on my wife and I am not a homosexual, except for the one time in high school, but boy something about you makes my Johnson stand up to attention." He said that and he parted his legs to give me full view to his crotch, which was pitching a massive tent in his shorts, almost lifting them up from his waist in the front. He traced his finger from the back of my knee up to the bottom of my shorts and then pushed up the shorts with that finger and rested his hand cupping my ass.
I was so confused, shocked and scared I didn't know what to do.
"Have you ever done it with a guy?" He asked seriously, looking me straight in the eyes in a way that made me shiver. I shook my head. "Do you want to try?" He asked again looking straight at me.
I said "I don't know."
Looking straight at me, he said "I don't want to waste time. If you're interested, come back to my villa." He pointed to a house behind us. "Let's see what happens. We'll have some drinks, if you like what I want then great, if not I can drive you home." I am no rapist I promise. He had sincere look on his face. He got up and gave me his hand to help me up. I found myself giving him my hand and getting up.
He helped me collect my things, and he picked up his shorts and sneakers and lead the way to the villa. When we got the gate, he punched in a code, let me enter and then closed the gate loudly behind us. The garden was lush there was a small pool and showers near it and double glass doors leading to the house. It was a bungalow type. He lead me near the showers and instructed me to put my things down on a table near the door. Then he called me over to the showers. He turned them on, he stripped down exposing his naked manhood to me. I couldn't help but stare again, he was well endowed. Beyond my imagination ever. His penis was at least 8-9 inches big by now, with a circumcised head, which was unusual in Asian cultures. I gawked! He smiled, and said, "I know I am bigger than most men here, right." With that he laughed heartily and got in the shower and started to wash himself, I stood there watching him in awe. The water splashed off of him and he scrubbed soap in every crevice and washed himself. Then looking at me he beckoned with his fingers and instructed, "strip now and come on in." I found myself reluctantly taking my clothes off and stepping forward to the shower.
Even though I was aroused my tiny penis had shrivelled in fear and anticipation of what was to come. I walked hesitantly to the shower, now beginning to comprehend what was happening. My mind was racing and all the religious and social teachings came flooding into my mind, the impacts of what I was going to do and the health implications nearly froze me, but the water cascading off of Jakes' body was mesmerizing. His voice broke the trance, "come over before the blasted water tanks run out."
I walked over to the shower near him. He was watching me, taking in every bit of me. I stood in the water, it was welcome it was cool on the hot day. I bent my head to allow the water to wash over me, my eyes caught Jake's dick, it was bigger if that was possible, it was now sticking out and up engorged with blood, a few veins popping out. I looked down at my own cock, or lack thereof. In embarrassment I turned away to my left and let the water wash me. I heard him approach me, from behind. I felt his hand on my shoulder, he said "Let me soap you." His voice boomed over the water. I felt his strong and big hand on my shoulder curving around my shoulder blade, I instinctively reached up touch his fingers, two of my slim fingers could fit into one of his. The cold gold wedding band felt like ice on my skin. Reminding me of the sin I was to commit. His other hand picked up the soap, it was foreign it smelled good. He lathered it up and started to apply it onto my neck, both his hands and fingers massaging my throat, neck and below my skull. I had never been touched like this, he was slow but purposeful. He massaged my shoulders and arms, then his hands went down to my hands and fingers and he lathered them up, he moved closer and I felt his dick stab me in the back, I jumped forward, he pulled me back by my arms and firmly stood me closer to him. He continued to lather my hands, I could easily fit both my hands in the palm of his hand. He had hair on his knuckles I noticed, something I hadn't seen on any man.
He lathered my stomach and then moved up to my chest, he swooped his hands up and he cupped my tiny tits in the palms of his hands and he squeezed them. They hurt and they jumped. He did it again and again and circled them with his hand. He pulled me closer which got me under the shower head again and the soap started washing off me. He adjusted us and now he began to wash my back and the small of my back and ever so slowly but firmly he made his way to my buttocks. He knelt down and now he was almost at my buttocks. He soaped the two mounds, massaging them, then he separated them and put some soap in the crack and massaged them again. His hands moved down to my thighs and my legs. They trailed back up, and I heard him say "Damn you're smooth." Then he soaped my ass again and this time I felt a finger go into my crack I felt the intrusion the foreign object inside me, I winced and clenched. He grunted in frustration and with his left hand opened my cheeks and his right hand explored what my ass cheeks tried to hide and protect. I felt his finger at the opening of my hole, gently massaging soap on the outside. The water began to sputter indicating pressure was getting low. He stood up and let me rinse the soap off. He turned the water off and we stood wet and naked, he turned me around to face him, I was hard now but barely 3 inches in length. I caught him looking down and he smirked. I believe he instinctively reached for his own cock, wanting to perhaps measure in comparison his to mine. I saw his big fingers try and circle the base of his cock, even they barely made it around.
He reached up and came closer. I saw him lower his head, I thought perhaps he would try and grasp my cock, but I saw one hand go around me to embrace me and the other to hold up my right tit, he squeezed it and said. "Can you feel it when I touch you here?" He asked curiously. I nodded, his mouth opened and with his tongue out, he brought his face to my chest and next thing I knew is his mouth was on my nipple. He sucked on it, with a vacuum like force pulling it, as though it would produce milk. After the initial assault he loosened the grip with his mouth and gently sucked it. Then sucked the other, I found his hands were now pulling on my ass cheeks, massaging them, and pulling them apart and squeezing them back together. He started to gently lick and tease my nipple and it was pure ecstasy. I had never been touched, had never imagined such pleasures existed, I was overwhelmed by the smell of soap and him, the feel of his tongue so wet, so gentle so rough so pleasing. Big strong arms around me, feeling safe and loved like my heroines in the novels I read, and his hands squeezing my buttocks, the envy of many women. I didn't notice his finger at the entrance of my hole until it penetrated me. The swirling tongue on my left nipple was captivating. When he penetrated me I was alarmed and excited at once. He said from between my nipples looking up to me "damn that ass is tighter than a virgin's twat." He spit on the ground and resumed what he was doing, now on my right nipple. He put it in his mouth, suckled it like a baby would, then let it go and lick it with his tongue. I couldn't contain the ecstasy and the next time he released my nipple I just burst, I came and ejaculated. A squirt left my tiny penis and shot onto Jake's thigh. I moaned so loudly I surprised myself. Embarrassed I began to apologize and he just laughed and looked down at the drop on his thigh, he let me clean it off, and turn the water on to help me wash my hands and his thigh. I enjoyed stroking his hairy thigh.
Just then a bunch of gardeners, locals like myself appeared from around the villa. In fear and haste I panicked and was rushing to my clothes. But Jake pulled me by my arm and said "What's the problem sweetie?" Confused I looked at him and with panic said "Look they are coming they will see us. You know its illegal to do what we are doing." I surprised myself with my knowledge of the law.
He laughed, and said "I don't care, I don't give a damn what they see or if they see. I will fuck who I want."
The three men came up and stared at the naked bodies, as soon as they made eye contact with Jake they lowered their gaze and made themselves busy with the work at hand.
Jake led the way to the house. There were three doors, two on the sides that looked like screen doors, as we got closer, I noticed one of the screen doors was leading into a bedroom with a big bed, the other into a sitting area. Jake led me into the middle door which led into the middle of the house and where the room separated the living area to the bedroom area. I was fascinated with the room. We the locals had never had such luxury housing before. He saw my amazement and he decided to show me around. He saved the bedroom for last. When we entered he let me enter first as a change. I entered and stepped onto the plush blue carpet. The cold Air conditioned room made me chilly. The room was dominated by a big high bed with lots of pillows, bright and clean white sheets, and covers. The bed was high enough to reach the bottom of my chest and the top of my abdomen.
Jake closed the door behind us. While he didn't slam it, it was loud enough and made me panic. He proceeded to lock it as well, which also made me feel scared. He walked to the bed and lay on top of it and called me to him, when I got near the bed he pulled me up and got me on his side. He then put his left arm under my neck and with his right hand stroked my body, and my arms and said "you're really smooth and sexy, those cock sucking lips are naturally pink and that ass, hmmm I am going to have a hard time stopping myself from Cumming. Has anyone fucked you?" He asked. I said no. "Well damn it you're a fine virgin sissyboy." I managed to ask him, "do you have sex with guys all the time?"
"Heck no!" He replied. Then he added, "I am very faithful to my wife, I am just very backed up and find the Asian people very tantalizing. I even brought a hooker here last night but I was stinky and foul, I kicked her out right away."
I processed what he said and then said "But I don't know what to do."
He laughed and said "Don't worry, I will tell you. You just need to be very very good. Never say no." He paused and looked me in the eyes with a serious face, and repeated "never".
I have a video I will show you shortly of what we will do.
With that he got off and went to the TV and put a DVD in, and returned to bed. He put his arm around me and continued to stroke my body with his fingers. He leaned in and kissed my lips gently at first and then forcefully as the movie started up. He got off and said "Good your breath doesn't stink."
The movie showed a young blonde girl and her husband sitting in bed watching TV. The movie quickly proceeded to the wife undressing the husband and herself and stroking him, sucking him and then straddling him. As I began to stroke him Jake took my hand to his cock and made me wrap my fingers around it to stroke him. I began to masturbate him. He was very hard and firm in my hands, and too big for me to really get a good grip on. When the girl on the TV started sucking her husband, Jake got up, turned around to face me and got on his knees and came up to me. Put his hands on my shoulder and pushed me down in the bed a bit until his cock was pointing to my face. He put one hand behind my head and held his cock with his left hand and brought it to my lips. I kissed it instinctively and he pushed it in and moaned. My mouth was full in no time and he instructed me on what to do and what not to. I had a lot of difficulty breathing but he didn't seem to mind and he kept pulling me head closer to his torso and his pushing he penis deeper. I couldn't take it and gagged and it only made him do it more. He continued this for what seemed a long time and finally let go. Got in bed near me and said "damn your lips are lovely but your mouth is too small, we'll have to work on it later." Not understanding him I didn't say anything, he instructed me to open the drawer and take out the tube. I saw the drawer had lots of condoms and a bottle. He said "give me the bottle". I did and he squeezed some clear liquid onto his penis and told me to wet his cock with it and stroke him. I did and he seemed to enjoy it.
"On your stomach baby-girl," he said.
Jake pilled up several of the pillows into a mound and instructed me to put it under my stomach, which left my ass up in the air while my head and knees were on the bed.
"Beautiful baby-girl ... you have such a pretty tight round ass. Do you like my calling you my baby-girl? You're not a boy are you? You're a sissy, a girl. And I'm your daddy, ain't I?"
His big hands grasped my cheeks, squeezing them hard and a moan escaped me, I buried my head into the sheets beneath me. Jake settled himself on his knees between my legs, making it impossible for me to close them even if I wanted to, and his hot mouth landed on the crinkled bud of my asshole and his tongue flicking out to lick it. The sensitive bundle of nerves around that virginal orifice flared with pleasure. I moaned as he started to probe my asshole with his tongue, it felt so strange and foreign but so good too. It sent tingles up my spine.
His big frame leaned over me and I froze, feeling the length of his cock sliding up my asscrack. Was he going to fuck me here now? My brain screamed a warning even as my asshole throbbed with needy excitement.
But he was just reaching for the bedside table. Sliding open the drawer he picked up a tube of lube as I watched in amazement. A quiver of anxiety ran through me; there was no stopping Jake now, not until he had his fat cock crammed up my tiny asshole.
The lube squirted and then I could feel something thick and hard prodding at my tiny hole. I almost panicked when I realized that Jake wasn't going to loosen me up with his fingers, I hadn't been expecting to have to take his cock immediately! But he wanted me to be tight, and he figured that he'd given my virgin asshole enough of a workout today that I should be ready.
"Jake wait! Pleaaaaaaaaaase... Oh god!" My voice dragged out as Jake pushed inwards, the head of his cock popping past the tight ring of my sphincter. It felt HUGE. I could barely breathe as I grasped, my fingers scrabbling at the sheets, trying to find purchase... trying to do something. I screamed "please wear a condom, please." He ignored me.
My bottom automatically clenched, trying to force him back out, but the way my legs were spread hindered my attempt and I couldn't close them because Jakes legs were in the way.
"Oh baby-girl... you're so tight... just relax it'll get better..." My hot little asshole was squeezing his cock like there was no tomorrow. "Bear down on my cock baby-girl, it'll help."
I did what Jake said and moaned as he slid deeper rather than pulling out of me! I thought that since I was squeezing that it would push him out, but instead he just managed to slide more of his cock into my burning tunnel. His dick was so much thicker than his fingers, I could feel the channel straining to hold him, my ring clenching down as my body tried to force itself back into the size it had been a few minutes again.
"It hurts... Jake please take it out!"
"Shhh..." It was sheer torture but he stopped his forward progress, holding himself immobile in the tight vice of my virgin asshole. I mewled as Jake rubbed his hands over my cheeks, biting back a little sob. My anus burned with the straining effort of being stretched so wide, I could feel a kind of deep throbbing cramp in my gut that even Jake's soothing hands couldn't rub away.
The log in my backdoor shifted and I groaned as I felt Jake pull out a little; it was so strange, igniting another kind of ache as he receded, and then he gently pushed back in and I shuddered. The amount of cock that was sliding back and forth in my now deflowered asshole was only a few inches but it felt like a battering ram, breaking through inferior defences.
"Good bitch... fuck you've got such a tight little asshole... that's it... squeeze my cock with your virgin ass ..."
I moaned. After all, I wasn't actually trying to squeeze his cock in a pleasurable way, I just couldn't stop my body from clenching down and trying to force the uncomfortable object out! The lube kept his length slick, my gripping muscles couldn't get a firm enough hold to stop him from sliding deeper, but instead my protesting anus just massaged the portion of his cock that he'd worked into me.
Groaning, Jake thrust in deeper, spearing me with a little more than half his cock and I cried out, trying to fall forward and get away from the fiery log that was forcing its way up my asshole, but the pillows piled beneath me and Jake's hands on my hips held me in place. My fingers dug into the mattress as I gasped for air, feeling as though my lungs were being tightened in a vice, the erotic pain blossoming inside my lower body.
Leaning forward, Jake's cock slid even farther inside of me. Bucking in response, I yelped as I accidentally forced my asshole further back onto his cock and he groaned, reaching around with his fingers and placing them over my tits. When he found them, he squeezed, I bucked again and the rest of his cock slid easily me.
Whimpering, I rested my head on the mattress, hmy hole spasming around the base of Jake's cock. I knew that he was finally all the way inside of me because I could feel the rough, wiry hairs of his groin rubbing against my splayed cheeks.
anus burned despite the slickness of the lube as his cock rubbed roughly by...
About halfway out he stopped and began to plunge back in, making both of us groan for different reasons. When I tried to jerk forward, to get away, I ended up hurting my head on the headboard. The sharp pain of my anal defloration was slowly subsiding into a more generalized, duller ache as my body began to become accustomed to the new dimensions.
I lay quiescent and submissive as Jake began to thrust in and out of my asshole a little harder, feeling the burn but no longer fighting it. Closing my eyes I tried to focus on something else on how my heroines enjoyed their men, feeling the eroticism of the slick cock moving in and out of my body even if it was the wrong hole was somewhat pleasing. My nipples rubbed against the mattress beneath me with every thrust of Jake's cock and that felt good too.
When I started to moan a little with mixed pleasure and pain, my body instinctively moving up to meet Jake's cock as my tingling need to cum increased. The anal fucking I was receiving still hurt, but it was starting to hurt in a good way.
"Oh fuck... that's it baby girl... give up that ass to me..."
Now I was moving with him, humping my hips. The strangest sensation was building up in my core as Jake started fucking my ass with abandon, taking it as roughly as he could and I squealed and squirmed beneath him. It hurt so good and I could feel his cock rubbing over some place deep inside me that was building a tension I'd never felt before. My asshole still burned.
Pain and pleasure clashed together inside of me as he ravaged my virgin ass, his strong hands holding me in place. The friction of his pistoning cock flared as he savagely fucked my ass, mewling cries forced out of me with every thrust.
Dimly I was aware that that the cock in my ass was becoming thicker, the thrusts harder and rougher. I sobbed with the overwhelming sensations and
Jake's hands were now on my hips, holding me in place as he ravaged my asshole.
His cock pumped and burrowed into my dark cavity as I finally went limp beneath him, unable to move. Only the inner muscles of my rectum were still moving, massaging his lengthening cock as the cum boiled up in his balls. I could feel him moving, pummeling me from behind, and my little whimpers were finally drowned out by his shout of triumph as he surged forward particularly hard, burying himself in my ass and hot cum jetted into the dark space.
The pulsing of his cock made me moan, I could actually feel each spurt forcing its way past my tight sphincter and into my body. The liquid bathed my insides, filling me up even more with Jake's cock blocking the way for its escape. I moaned, my asshole clamping down and milking every last drop of cum from him.
His heavy weight collapsed on top of me, covering my tiny frame with his own extra large body. Hands ran underneath to cup my breasts as he tenderly kissed my shoulder, both of us panting as our breath returned and they came down from the sensual high. I turned my head to meet Jake's lip for a kiss; it was a very soft and gentle one, belying the savage fucking he'd just pounded my virgin asshole with.
Not virgin any longer, I thought. Now Jake had taken my cherry.
This was repeated savagely a few more times until it started getting dark and I begged Jake to let me go. He finally acquiesced and let me go home.
Feedback is always welcome at funnstuffdude6@gmail.com