Frist time for everything, BDSM & Crossdressing

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PrinceOfAllSaiyans
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Joined: 04 Oct 2015, 07:29

Frist time for everything, BDSM & Crossdressing

Post by PrinceOfAllSaiyans »

Foreword

I have loved visiting this forum for years now, I thought I would share with you the story of how I got into this community. I apologize for the length, I thought the story would only be a few paragraphs but as I typed it grew into an essay. Most of what you are about to read is true although I have taken some creative license and exaggerated a few details. I hope you enjoy!

Childhood

I grew up in a neighborhood called Warroad in Minnesota. As a child I was very antisocial and mostly kept to myself. I loved to explore and Warroad had much mystery to offer, the community bordered Woods Lake and was surrounded by ample wilderness and swamp land. However there were all the amenities of the suburbs; well groomed parks, a tavern that was kid friendly with an arcade, a convenience store, a marina and plenty of fishing. Some of Warroad's mysteries included islands that could be seen far off in the lake on clear days, ruins of 19th century houses hidden deep in the woods (they were rumored to be haunted), the plainly visible but unreachable “Banana Dike” that was just across a tributary. As a young child I loved nothing more than to hop on my bike and explore these places all day, seldom returning home except of course for supper.

Warroad was a magical place to me, I didn't mind that the other kids wouldn't play with me and would often harass me. I just wanted to go farther, deeper and uncover the secrets of that place. I would often venture to the extreme edge of the marina and look through binoculars at the Banana Dike, wishing I had a boat so I could explore it. I was happy to be alone as I trudged deep into the wilderness with basic building materials and set up crude structures which I called “forts”. I also enjoyed visiting the tavern where I would order a large pizza, secure my high score on whatever games they had available and load up on candy for my next excursion into the wilderness.

Cody

At the tender age of 8 or 9 I met a kindred spirit named Cody. He was a young boy like me, perhaps a year older and had dark, straight hair and brown eyes. I first met him while I was walking deep into the woods to survey a more suitable area to construct a fort. I came to a large pile of stone that was once the foundation of an ancient domicile, I was very familiar with this site but was surprised to see someone else examining it with all the same curiosity as myself. As I paused, he hopped down from the pile of rocks and asked me “what do you suppose it was?”, I smiled and said “perhaps an ancient Mayan Temple”. The mysterious boy smiled back and we began speculating about the people who must have inhabited the area. Cody was also antisocial and enjoyed exploring the same mysterious areas of our community as I did.

As time wore on my friendship with Cody deepened, he was the only other kid I could share my interests and beliefs with. Cody and I would often set out on our bikes and explore farther than I had dared alone. With him at my side I ventured farther into territory I was previously too scared to explore. Cody showed me that there were no ghosts or monsters swirling about the swamp or the wilderness and that two best friends can unlock all the mysteries of the world.

The Big “S”

Cody strongly preferred to visit my house, rarely was I over at his. Through my adult eyes I now understand that his parents were often intoxicated and abusive, as a child I was naïve. Cody always wanted to venture into the woods, as if to be safe from the adults. When we were together and alone he began to show me an extra special way that best friends play together, he called it 'sex'. For Cody and myself sex was always a game, we would follow each other into the woods to a place where we were certain no one could observe us and we would have to decide who went first. Usually we would 'rock, paper, scissors' or just flip a coin to determine the loser. The rules of the game were that the winner would get to suck the penis of the loser. As an adult this seems backward, but as children we honestly didn't know any better.

On any given session, if I had won the coin toss, I would collect my reward. First I would kneel in front of him and unbutton his pants, I would then pull his pants down quickly but not his underwear. I liked to stare at his underwear and admire the various comic book heroes it was adorned with while I dreamed about what was just underneath. Then I would dig my fingers into the elastic and slowly slide his underwear down, revealing his small but hard boy penis. I would then close my eyes, lick my lips and lean forward to take his boyhood into my mouth and suck on his penis for as long as I liked. Eventually he would get impatient and demand for his turn, at which point I would let go and stand up. Since he was the loser he didn't have the right to undress me so I would throw my pants and underwear down and allow him to suck my penis for a short while.

Cody explained that our game was only for the best of friends and that I was forbidden from mentioning any detail of it to the adults, as they could not possibly understand and would most likely separate us. We came up with a code phrase: the Big S. On any lazy summer day Cody might arrive at my house and we would play together in my bedroom or the back yard for a few hours. Eventually one of us would look at the other and say: “it's time for the Big S”. Then we would go out into the woods and play our game to decide who got to go first.

Eventually Cody introduced another element to the Big S that I didn't quite understand but he insisted upon. After we would take turns sucking each other's penises the loser would have to bend over and grab their butt cheeks. The winner then would grind their erect penis against the loser. Cody seemed to enjoy this much more than me, I didn't understand why someone would want to do that and wasn't interested in sucking his penis afterward. Whenever he would win our game I endured the feeling of his juvenile cock against my ass and patiently waited for him to get tired. When I won I would substitute the grinding for other things I liked. Instead of poking him with my hard penis I would lick his nipples or kiss him on the mouth, Cody never liked that but I did and it was my right if I was winner.

Robert

After a few years Cody disappeared from my life, I'm not too sure where he went but I suspect his family moved to another city in Minnesota. Time went by and I was alone again, I grew into a teenager but lost none of my childhood wonder. I still explored deep into the woods and built many forts, I had also reached the Banana Dike and walked some of its length. I was still a loner, having no friends and only my exploration and video games to entertain me.

Over the course of one summer I met another boy, I cannot recall his name or even what he looked like but I like to call him Robert. Robert was a much older than me but still a minor, I believe he was from another state and only visiting Minnesota for the summer. I cannot even recall how we met, however I am quite sure he was also a loner who was harassed by the popular crowd in Warroad.

Robert, like Cody, was also interested in sex, he and I even used the same code: 'the Big S' but the main difference was Robert only wanted to do it in the house and his appetite was much more mature. Much of my adult fetishes stem from memories of my short time with Robert. I remember he was a nudest, whenever he was over and I had the house to myself he insisted on both of us being naked. I also remember Robert had a very thin and pale body and how astonished I was by how huge his penis was compared to my own and the fact that he had hair down there! It was difficult to get the place to myself and Robert seldom wanted me over where he was staying, so I always had to invent excuses to stay home alone. Often I had to sacrifice valuable trips into the city where I might buy some remarkable new toy or game so I could call Robert and let him know I was home alone for a few hours.

When he received the call Robert would promise to be right over and remind me that he had been waiting all day for me to clear the house. Upon arrival Robert would enter the front door and hastily lock it behind him, he would ask “how long 'till your folks are back?” and I would smile and say “not for a few hours” he would then throw off his cloths and become completely naked. I was never allowed to take off my own cloths, instead Robert would undress me slowly. And completely naked the two of us would head to my bedroom to play together.

A new level

Robert and I had a system for the Big S, we would lock all doors (which I was told to do anyway) and put the family room TV on mute. Then we would start a game on my Sega Genesis (usually Mortal Kombat) and play until there was a clear loser, Robert always chose Scorpion and I always chose Sub Zero. I intentionally lost to him because I loved what he would do to me and didn't understand what he wanted me to do to him. We would then put the Sega on pause and have sex with each other, due to the gravel driveway in front of my house and the locked doors we would have plenty of warning to unmute the TV, throw our cloths back on and jump in front of the Sega and resume beating the hell out of each other's characters.

Some kids play 'cops and robbers', we played 'prisoner and prison guard'. Robert would invent new and novel ways to imprison me and I would be forced to comply with whatever rules he made up, most of which involved sucking his penis. Robert never truly understood that I enjoy sucking his cock, even though it makes me gag, and that I always lost or misbehaved so that I could see his beautiful hard cock in front of me, so that I could part my lips and take it inside. Robert become more demanding as time went on, he often wanted me to do and say specific things while his huge cock was thrusting in and out of my young pink mouth. He wanted me to massage his butt or fondle his balls or look up at him and smile while I pinched my nipples and caught my breath long enough beg for more. He always thought it was punishment or degrading, but he never understood how much I enjoyed it!

In the closet, literally

One day Robert introduced a new requirement for prisoners like me, in addition to being completely naked I was required to wear a dog collar. The spiked dog collar was literally from a family pet but it felt great against my skin and somehow made sucking his cock even better. I remember one of our games where I lost (as usual) he made me wear the dog collar and sit in my closet. He then produced a nylon rope and tied my ankles to my thighs, then he tied my writs together and pulled them tight over my head to the wardrobe bar in my closet. As he was doing this I stared at his giant cock and wondered when it would get close enough for me to suck it, but he kept too far away. Then, once he was done tying me up he stepped back, his giant hard cock pointing right at me, and slammed the closet door shut, leaving me in darkness. I sat there in the darkness, my teenage body aching for Robert, but was not able to move or escape. After some time I heard footsteps approaching my bedroom, I had nodded off and didn't fully realize what was going on, I thought it might even be my big sister! And she might throw my closet door open and discover what I was doing!!

Instead, as the door flung open and my eyes adjusted to the light, all I saw was a huge beautiful cock right in front of my face. I closed my eyes, opened my mouth and leaned as far forward as the cruel robes would allow, shortly thereafter I felt the penis slide over my bottom lip and tickle the top of my mouth. As I was sucking Robert's penis a strange calm fell over me, I no longer felt the pain of the ropes pulling against my flesh. I only felt euphoria and was perfectly happy in this place, but without warning he stepped back, ripping his cock from my aching lips. I opened my eyes just long enough to see the door slam closed.

For the rest of that day Robert left me tied up in the closet, wearing nothing but a dog collar and nylon rope. At random intervals he would fling the door open and shove his hard cock in my face before I even had an opportunity to think. All I understood was when I saw that cock, to suck as hard and fast as I could before he pulled back. I was in Heaven!

69 and my first taste of BDSM

I lost bad, I really lost bad! Robert kept using one combo against my Sub Zero and I wasn't able to score a single hit, flawless victory!! I knew this would mean an extra special punishment!!! Robert grabbed the rope and tied it to my dog collar (which I wear even when he isn't around) and led me outside the house and to the back yard. Robert threw my naked body against a pear tree in the back yard and held up some hand cuffs, I didn't know where he got them from but they were the real thing. I obediently held out my wrists as he slapped the hand cuffs on, then he tied the rope to the hand cuffs and threw it over a branch above my head. He pulled tight on the rope, stretching my young naked body against the harsh bark of the tree. Robert then walked around me with the rope, crossing my bare chest and belly with it. As he walked I stared at his huge hard cock flopping from side to side with each step and I wondered: how am I possibly going to reach it while I am tied upright!? Once Robert had made the final pass behind me with the rope I realized I was completely helpless, but this was different, I was in plain view of the public! Robert stood in front of me, completely naked and with a full erection and smiled his classic smile. He said “just hang there a while and think about how much you would rather be on your knees”. With that Robert disappeared inside the house and left me hanging naked against a tree.

As I hung there I noticed the cars that were coming down the road perpendicular to my house, I wondered how much of me could they see if they were paying attention. I also saw the bike trail next to my back yard, I knew it went from main street to the Fire Department, I wondered how long until someone comes up that trail. I began to panic and struggle against the ropes that held my nude body to the tree. It was no use! I couldn't escape!! I began to whisper for Robert and when he didn't answer I yelled his name. The back door of my house flew open as Robert angrily walked out, still naked, and without word he approached me and unlocked the hand cuffs. He loosened the ropes and grabbed my collar, pushing me down on my knees and led me back in the house. Robert threw me into the dining room against our large, Amish built, dining table and locked my wrists around one of the table's legs. He then said that I would have to receive a higher level of punishment for chickening out so early.

As I remained naked and hand cuffed to the dining room table, wearing only my dog caller I heard him walk into my bedroom. He came out shortly after holding only his hard penis which was larger than I had ever seen and a belt from my closet. I began to ask him what the belt was for but before I could finish he began to whip me with it. I held my head up and focused on nothing more than his huge cock as it wagged from side to side as he whipped me with the belt. The pain was incredible but I was mesmerized by his cock pointing right at me and his stomach mussels as he lined up each stroke of the belt.

Unfortunately it was too much pain for me and I began to cry. Robert stopped whipping me and dropped the belt, he began to apologize profusely and said he would make it up to me. He unlocked the hand cuffs and led me into my bedroom. He instructed me to get into my bed and lie on my back, despite the pain I obeyed. Robert then straddled my head, his cock pointing straight down at my face and as I reached up to take his penis in my mouth he leaned down and took my penis in his mouth. The feeling was so amazing I actually enjoyed having my cock sucked for the first time in my life! The aching of my ass went away as I felt his wet tongue wrap around and tickle my cock, I closed my eyes as I felt him slide deeper down my throat than I had had ever let him. As his balls came to rest on my face there was a true calming and zen that washed over my body, I could do this all day!

From then on the 69 became a common practice. I would allow him to hurt me more and more just so I could enjoy his cock in my mouth and mine in his.

My first time

Most prominently I remember one day with Robert. I had called him and told him that my family was out of the house, within 10 minutes he was at the front door and we were both naked. I put my dog collar on and we began our usual game. On that day Robert was especially aroused. Usually I had to lick, suck or touch him to get his penis to swell but on this day as soon as he pulled his underwear off I remember his huge cock flopping up and down and threatening me with its presence. Instead of deciding a loser we went straight to the bathroom and assumed I was the prisoner (as usual). Robert sat down on the edge of the bath tub with his monster cock pointing straight up at me and told me to get down on my knees and suck it. I obeyed and got down, closed my eyes, licked my lips and felt the tip of his penis slide into my mouth. As I did so I felt his hands on the back of my head, something he had never done before. Robert began pushing me farther and farther down on him to the point where I began to gag as the position wasn't comfortable for me. Robert said in a commanding voice “you can go down further than that, you took it all before.” I pulled my head off of his cock and looked up at him through teary eyes and explained “it's too much for me right now”.

Robert flashed me the most warm smile I had ever seen and said “alright, we will try something new this time”. He then told me to spit on his cock, I gave him a puzzled look but his eyes told me that I had better obey. I bent back down and began slobbering all over his penis until it was drenched in my saliva. I looked back up at him for instructions and he told me to stand up, turn around and bend over. As I bent over I remembered all the times in the woods with Cody and wondered if he was going to do the grinding thing like him, I wondered how I was going to explain to him that I didn't like it. I then felt his warm hands caress my butt cheeks and cradle them as he willed me to sit down on him. I was confused but I obeyed, I began to step back and place more of my body weight into his hands. As I settled back I felt the slimy head of his penis poking right on my opening and wondered how could I possibly sit in his lap, his rock hard penis is in the way.

Then it happened.

His hands pulled my butt cheeks painfully apart and I felt him slip inside me, I was so shocked by the feeling that I fell backward right onto Robert as his giant cock went deeper into me! My breath was gone, I tried to come to my senses and looked up at the mirror, all I saw was my naked body resting on Robert's who was sitting on the edge of the bath tub. I looked down and saw my cock was larger than it had ever been, it was so hard it hurt. My best friend was inside me!

Being Fucked!

Nothing could have prepared me for what happened next. I was in such complete shock that all I could do was look at my gaping mouth in the mirror when he wrapped his arms around me and began to thrust. For a few seconds (it seemed much longer) Robert was bouncing me up and down on his lap, his giant cock thrusting deeper and deeper inside me and there was nothing I could do but take it. Robert placed his arms on the edge of the bath tub and with one powerful thrust threw me off of him. I was now standing upright and in such a daze that I braced myself against the sink and once again stared at myself in the mirror. I saw Robert stand up and walk over to me, his gargantuan cock waging as he walked. I fixated on it and reminisced about how much I love watching him walk with an erection. He walked right up behind me and slammed his cock back into me, once again the surprise was too much and my mind went blank. Robert began thrusting harder than ever, he pulled me back and thrust so hard that I thought I felt my feet leave the ground. I lost balance and slumped forward against the sink, he didn't stop or let up one little bit, he kept thrusting harder and harder.

I watched myself in the mirror as my steel hard penis flopped up and down with each powerful thrust from Robert. He started breathing heavily as he thrust faster and deeper. I felt like this was true bliss. I believed there was literally nothing better I could do with my life than to be right here, right now, riding this cock. I felt like I didn't need to play video games or watch movies or read books, this is my place! All I need is hard cock inside me, nothing else matters!! Then without warning he paused and leaned in as if to whisper something into my ear. My whole body ached as he stopped, I couldn't even hear what he was saying I could only focus on the warmth of his penis inside me. I only wanted him to resume thrusting, I wanted it to hurt!

Then our moment together was interrupted as I heard the crunching sound of a car pulling into the gravel driveway. Robert jumped back, pulling completely out of me. I turned around and looked into his eyes with all the pleading of a lost puppy but he ran out of the bathroom and towards my bedroom. I solemnly followed him as he unmuted the TV, we both threw our cloths back on, unpaused the Sega and launched right into Mortal Kombat. Moments later my big sister poked her head into my room and announced that she had acquired some pizza for us as well as a few movie rentals. Robert and I had to remain in my room for a little while because we both still had raging erections. We ate pizza and watched a few movies, all the while I was looking at his crotch and dreaming about when I could next feel his huge cock inside me. He left for home late at night and I went to bed touching myself, thinking only of different ways I could get him hard.

Robert's bag of tricks

It was a long time before I was alone with Robert again. After the one incident he started to visit more often but I wasn't able to clear the house. I begged and pleaded with him to go out to the woods and engage in the Big S like I had previously with Cody. Robert could not be convinced to have sex in the woods. Instead we would spend time in my room playing video games and watching movies. Very often he would place his hand on my thigh and caress my boyhood but I was forbidden from touching him, I believe he liked to make me hard and let me suffer.

On one night my mother had to drive up to Roseu for some emergency while my dad was working. I feigned illness so I wouldn't have to go on that boring car ride. The very second I heard the car pull out of the drive way I grabbed the phone and called Robert. When I heard his voice on the line my penis instantly became so hard I just had to unzip my jeans, Robert heard it and scolded me. He told me to do whatever it takes to get my penis back in my pants until he arrived. I hung up and walked over to the fridge, extracted an ice cube and began rubbing it on my cock. It worked, my penis was now small and flaccid, I lied down on a couch in the living room and placed the ice cube in my mouth as I thought of Robert.

I heard the front door open and close, followed by the turning of both locks. I remained motionless on the couch with my eyes closed and listened to all the telltale signs of Roberts presence. I heard shoes thud against the ground, the unzipping of pants and the rustle of clothing followed by soft footsteps approaching me. I opened my eyes and was amazed at what I saw, Robert was standing very close to me, his huge cock pointing down at my face. I saw that the hair was gone, he had shaved! Somehow it made his penis look even larger. Robert was also holding a small backpack that seemed stuffed full to the brim with new mysteries. He ordered me to stand in the middle of the living room as he went about the house closing the curtains and checking the back door. He playfully jumped onto the couch and reclined while he brought the backpack over and unzipped it. He told me to slowly pull my shirt off and to just unbutton the top of my pants. I obeyed as Robert reached into the backpack and pulled out a pink dog collar with silver studs. He walked over to me and placed the collar around my neck as he explained that it was a gift for me to be a little more lady like. He then pulled his set of hand cuffs from the bag and handcuffed my hands behind my back. Robert then knelt down in front of me and used his teeth to unzip my pants and pull then down, as he did my penis began to stress the elastic in my underwear. I stepped out of my pants and kicked them to the side as I wondered what else was in the backpack of his and how long would he make me wait for the magical feeling of his cock deep inside me. Robert then grabbed the edge of my underpants in his teeth and pulled them down, revealing my fully swollen boy cock and smooth hairlessness. He then opened his mouth and took me in, effortlessly bringing his lips down the full length of my shaft. As he sucked my penis I watched and wished I could suck cock like him, I began mentally preparing my self for the sensation of the head of his penis pushing past my lips. I thought about how I might spend more time tickling it with my tongue and how I could align my jaw and throat to go all the way down like he wanted without choking.

After a few moments Robert stood up and walked back over to the bag, he pulled out an improvised device that seemed to be leather shoe strings that he had cut to length and taped together at one end to a wooden handle. He turned and gave me a mischievous smile as he held the whip in one hand and slowly massaged his giant cock in the other. Robert said “you know, ladies don't have these” as his fingers glided over his penis, which seemed to be glistening some how. Then without warning he whipped the tip of my penis, there was an explosion of pain which caused me to cry out. Robert paused and said “don't be a baby, I've already tried it on my self” and resumed whipping my penis until it went soft and red. When he stopped I stood trembling and embarrassed by the sheer contrast between my penis and his, mine was tiny and pathetic while his was glorious. He stepped forward and began rubbing my chest, paying close attention to my nipples. Robert then commented that my boobs were too small to call myself a lady and he would have to try and fix that. He leaned in and began sucking on my nipples with a lot of force, occasionally biting and pulling on them as if to draw them out. As he did this I felt his cock push into my abdomen and the head of it rubbing up and down my mid section. I wished badly that I could touch it but my hands were still cuffed behind my back. With shock I realized the head of his penis was actually moist. As it moved and rubbed around my body it left a thin trail of some sticky and colorless liquid!

Robert again bit down hard on one of my nipples prompting me to say “ouch.” He let go and stood back to look at me for a while. He turned around and began rummaging through the bag while saying “I don't think you get it, you are my girl and I can do whatever I want.” He pulled out two spring loaded binder clips and walked back toward me, bending down to grab my underwear from the floor. He tied a knot in the middle of my underwear and placed it in my mouth saying “this will keep you from crying so much,” he then placed the clamps on my already tender nipples. As I felt the burning sensation grow in my chest he then began to walk around me and whip different parts of my body. Each new sting of the whip took my mind off of the nipple clamps and made me fear where and when he would strike next or how hard he might whip me this time. My whole body began to burn, especially my butt cheeks. I bit down on the knot in my mouth to stop from crying and only focused on his erection as he walked. I noticed that even his balls seemed bigger, they were huge compared to mine and he had more and more of the liquid dripping out of the tip of his penis!

He stopped whipping me and sat back down on the couch, his giant cock was pointing straight up at the ceiling now. I wondered if maybe I could jump on him and finally be able to ride that glorious cock, I realized it would be difficult with the hand cuffs but I was certain the feeling of him thrusting into me would take away the pain I was in. Robert then ordered me to walk around the house a few times so he could get a good look at his “girl”.

Like a Lady

Robert smiled as his eyes observed every exposed inch of my flesh, he continued touching himself as his other hand went into the backpack for more of what I suspected would be torture devices. Robert said “you look like an alright chick, you can spit that out now” I didn't realize I still had my underwear in my mouth and gladly dropped it on the couch beside him. Robert then pointed to my penis, which was still flaccid and very small, and said “we need to do something about that though.” He then pulled out wads of clothing from the backpack and untangled a bra. He stood up and gently removed my nipple clamps, the pain become momentarily worse as the blood rushed back into my poor abused nipples. He then unlocked the hand cuffs and let me slip my arms through the bra straps, he stepped behind me and hooked it as tight as he could get it. Robert than produced two water balloons from his bag and said “this will have to do for now until you figure out how to grow some boobs like a good girl,” he carefully placed the balloons into the bra cups with the knots facing outward to create the illusion of nipples.

Robert then slid a tight fitting black blouse over my torso, taking care to align to the bra straps. He then pulled out a roll of duct tape and tore off a 5” strip, he instructed me to tuck my penis into my scrotum as much as I could. As I obeyed he warned me that if I got hard again we would have to start all over, he then smoothed the duct tape over my groin. Robert had reduced my teenager boyhood to nothing more than a small bump! He returned to the bag and as I was wondering where he got this stuff from he pulled out some black panties and pink skirt. I slid the panties up over my streaked red ass thinking that 'these will just get in the way' and put on the skirt. Robert then produced a roll of hot pink lip stick and told me to put in on because it would match my dog collar. I had never understood why some children like to play dress up but realized I was having a lot of fun.

We walked over to the bathroom so I could see myself in the mirror. I was absolutely stupefied by my reflection! The illusion was powerful; my pink lips, pink collar, full boobs and short skirt just barely covering my ass revealed nothing but my panties. The only thing that might have been missing was a wig. I twirled around to get a look at myself from every possible angle. Robert smiled broadly as he watched me, occasionally feeling my fake boobs and flicking my skirt up to make sure there wasn't any nasty erection to spoil the smooth panties. Rob then spun me around and kissed me gently on the lips, it felt as though a jolt of energy had shot through my whole body. I had kissed Cody before when I was much younger but I didn't recall it feeling so good. I started to melt as I felt his right arm wrap around me and his left hand slide down and begin caressing my butt. As he held me my boobs pressed against him and his now indestructible cock pressed against me. His penis felt so strong that I wondered if I could balance an encyclopedia set on it.

Going Deeper

Robert let me go and I stood staring at his lips and trembling slightly as he slid his hands over my boobs and up to my shoulders. We stared into each other's eyes for a short while and I felt compelled to lean in for another kiss but before I could he pushed me down onto my knees. I fell and saw his cock right in front of me, I felt ecstatic that I would finally get to suck it. I saw that the the clear liquid that had been dribbling out the end of it was now running down the length of his shaft all the way to his balls. I wondered what it would taste like so I decided to sample a small amount. I leaned in with my tongue and gently flicked the base of his cock with it, as I felt the warm sticky liquid coat my tongue I was surprised that it was almost completely tasteless, just a hint of sweet. I ran my tongue under the length of his penis to clean as much of the marvelous liquid as I could, ensuring none might go to waste. I once again felt a sense of euphoria and belonging as my lips wrapped around the head of his penis, my whole body tingled as he slid deeper into me.

Unfortunately I found it was still too much for me to take in this position and began to gag once his cock started push on the back of my throat. I backed off a little and instead focused on massaging the tip with my tongue, Robert started to breath heavily and groan like he did when he had penetrated me a few weeks earlier. I became aware that every time I closed my lips behind the head of his penis and sucked I drew more of the fantastic liquid out and onto my tongue. I wondered how much there was, but felt I absolutely had to swallow it all! I felt Robert's hand on the back of my head once again and suddenly he slammed his enormous cock all the way down my throat. My body began convulsing and I pushed against his pelvis with my hands but he held me down on him. As I struggled with his powerful shaft filling up my airway he said in a whisper: “It's alright, just relax. I know you like to watch yourself so just look in the mirror.” I glanced up and to the right and saw a spectacular sight, my body stopped convulsing as I observed my reflection in the mirror. There I was: pink lips wrapped around a powerful cock, my ample breasts hanging down as I held my lover's hips in my hands, my throat stretched against the ping dog collar. Robert's hand fell away from my head as I pulled him closer, I wanted him deeper inside me. I truly belonged like this.

Playing House

As my body grew calmer Robert began to groan with more urgency. He pulled my hands off of his bare ass and stepped back, ripping his cock out of me, as well as a little of my heart. With my throat clear I suddenly remembered that I need oxygen and we both stood in the bathroom breathing heavily. Robert caught his breath well before me and said: “that was close! But I think you need to work for it if you want more.” With that he turned and walked back toward the living room, I stood up and followed while enjoying in my mind the still fresh image of me all the way down on him. Robert sat back down on the couch and picked up the whip, he then gestured for me to come closer and told me to lie on my belly across his legs. He instructed me to place my butt as high in the air as I could as he grabbed hold of my collar with his left hand. He then pulled on it hard enough to choke me slightly as he flipped my skirt up and over with his right hand. I felt him pull my panties down and say: “awww look at that, your ass is the wrong color. That's OK, I know how to fix it!” Robert then began flogging me across each cheek, I quickly learned that the more I yelped the tighter he would pull the collar. As I remained quiet and accepted my punishment he would relax his grip and allow me to breath.

When Robert saw that I was no longer flinching with each stroke of the whip he stopped and told me to stand up. He then told me to go to the kitchen and get him a soda, I instinctively pulled my panties up and turned to walk to the fridge. As I walked away I felt the sharp bite of the whip snapping against my back, I jumped and walked a little faster. I poured some Pepsi into a plastic cup and walked back to him holding it, as I did I caught my reflection on something and admired how pretty I looked carrying a soda to my Robert, I felt my crotch to make sure it was flat and thought I should really be wearing high heals for him. I handed him the cup and he casually drank about half as I stood before him, craving his penis. I noticed that despite my efforts earlier there was still a little precum coming out of the end. Robert saw my gaze and smiled as he held the cup just under his penis, with his thumb and index finger he grasped his cock at the base and pulled upward toward the tip. A small drop oozed out and flashed with light as it fell into the cup. Robert said “don't worry, I've got a REAL surprise for you if you are a good girl!” He handed me the cup and I drank it immediately. Unfortunately the taste of his juices was overpowered by the sugary drink.

For the next few minutes Robert sent me around the house to do basic chores; I had to make my bed, my sister's bed, clean up my toys and wipe down the bathroom. I always sought out and enjoyed the reflection of my feminine form as I did so. As I was wiping the sink and my beloved mirror I watched as my boobs swung around with each energetic pass of the paper cloth. I smiled to myself as I thought what my parents will think when they come home to a clean house and I wondered if there was anything I wouldn't do for cock. In between each task Robert would deliver a fresh whipping to me based on his satisfaction with my attentiveness. Occasionally he would make me crawl from one room to the other as he followed, constantly massaging his cock to remind me what I was doing this for. When I finished my last chore Robert told me to stand up. He then eyed my body with a mischievous grin and said: “I think you have been a good girl today, good enough to fuck.”

As the words hit me I went weak, I almost felt like I might faint from the tingling sensation that ran down my back towards my toes. This is the moment, what every essence of my being cried out for! I felt my womanhood ache with anticipation that his titanic, powerful cock was finally going to slip into me, that his mighty thrusting would raise me to ecstasy. And no one to interrupt it, I had all day to enjoy him! He grabbed my hand and led me to my bedroom.

At last!

Robert walked me over to the side of my bed and he lied down on the middle of the mattress, his nude, hairless body splayed before me as I noticed his tremendous cock aiming for the sky like a rocket on a launchpad. He looked at me with his mischievous smile as he gently rubbed his penis, which appeared to be more ready for me than ever, and he said “drop 'em.” I turned away from him and slowly slid my panties down to the floor, as I felt the soft fabric slide off of my butt I felt an exhilarating sense of freedom. Finally there was nothing in between me and him. I turned back around for more instructions and he reached out with his arms and gestured for me to lie down next to him, I realized he wanted me to stay dressed up for our fun. As I lied down he grabbed me and pulled on top of him in the classic 'cowgirl position', I then instinctively leaned down for a kiss. We made out passionately while he massaged my butt with both of his hands, I kept trying to lean back so I could feel the head of his cock probing my womanhood but his cruel hands kept me off of him. After a few moments Robert pulled away from my lips and scooted his body up. He then reached into his backpack and pulled out the most tantalizing object it had yet produced, a condom! I knew what condoms were but had never actually seen one. I stared, mesmerized as he pulled the condom from it's foil and rolled it over his giant penis. He then tore the top off of a small package of lube and rubbed it all over his cock as he stared into my eyes, he said “this will make it easier than last time.”

Robert tossed the backpack over the side of the bed and reached up to grab my shoulders and pulled me down to him. We began kissing again as I felt him scoot his body across the mattress to get into position, finally I felt his cock against my bare opening. As we kissed he moved his hips, rubbing his cock up an down the crack of my ass. With each pass I prayed for it to find it's way in, I felt that every fiber of my being was anticipating him, my soul was begging for penetration. I arched my back and with one final pass I felt the tip finally hit the right spot. I froze and held my breath, I listened as Robert gave out a soft sigh as he slid into me. We both remained motionless for a few seconds, looking into each others eyes and I wondered who was going to start it. I slowly leaned further back, willing every glorious inch of his tremendous manhood deeper inside me. I felt pain as his penis pushed harder against my opening, but I continued to direct more pressure down on his lap. Robert said in a soft whisper, “you've got to relax and wait for it.” Then his cock suddenly pushed its way into me as my body opened up to receive him!

The feeling knocked the breath out of me as I settled down on top of him. Once again my mind went blank and I could only think of the warmth of his cock inside me, where it belonged. I felt like the entire world no longer mattered, all I need or want out of life is a nice big penis to ride on. Robert's hands grasped my hips firmly and the silence of the room was broken as he let out a powerful grunt. He thrusted up into me with incredible force, almost throwing me off of him. I felt his titanic cock slip out partially as I was launched into the air only to slam back down on it. Robert began bouncing me up and down energetically while grunting and tightening his grasp on my hips. The pain I felt melted away into ecstasy as my body opened up even more to allow him in. I began panting with each stroke as he thrusted ever harder and faster, his hands held me down to ensure there was no chance I could escape my rightful place on top of him. As my young body reciprocated in response to each powerful thrust from my beloved Robert I noticed my boobs flopping excitedly with each wave of energy. I leaned back and put my arms behind me and couldn't stop my self from moaning from pure, raw pleasure. The posture exaggerated my ample breasts and I could tell from the renewed power and frequency of Robert thrusting his cock even harder that he liked what he saw. I looked down and saw my pretty pink skirt resting on his abdomen and admired the tightening of his stomach muscles with each new thrust. As I saw beads of sweat begin to fall from my head onto him I realized with alarm that the duct tape had come loose! My pathetic boy penis could no longer be contained and was now harder than I had ever felt it. With each new thrust I watched as my penis flopped up and down beneath my skirt. Robert breathlessly whispered; “that's alright, that's alright” in between each groan and sat up slightly. He lifted up my skirt and grabbed the tape, gently pulling it off of my scrotum and tossing it in a corner.

The big finish

Robert pushed me off of him and got on his knees. I panicked as I realized his cock had slipped out, I desperately wondered what I could do to get him to resume. I thought he was offended by my penis, I wondered if I could tie it down with string or something. Robert positioned me on my hands and knees and maneuvered behind me, my fears were put to rest as I felt him flip my skirt up run his hands up my back as he got closer. With no effort he slipped his cock back into me, all the way down to the base. My head reeled with pleasure as he started fucking me from behind, I braced my self for each stroke and moaned in response to each, ever louder grunt from Robert. In this position Robert had much more control over me, I was loving it. Robert began teasing me by thrusting hard fast and occasionally switching to slower strokes where he would pull his penis almost completely out of me. Each time he would pull back I would try to lean into him for fear of his penis accidentally slipping out. I wanted this to go on forever, I didn't know if I could withstand the shock of not being fucked.

After teasing me with shallow thrusting for a few minutes Robert slammed into me with all the force his slender body could muster and grabbed my dog collar, pulling me upright. Robert held my dog collar as he fucked me even deeper, he began to let out very loud grunts and moans. Suddenly he stopped and threw me back down into the doggie position. Robert slumped down onto my back and came close to my ear, as I listened to him panting I was reminded of the time in the bathroom when I thought he was going to whisper something to me. Robert caught his breath and whispered; “are you ready for it”? I said yes, not knowing what I was ready for but being absolutely sure I wanted anything he was about to give me. He then leaned up and pulled completely out of me, as my panicked mind tried to grasp his motivations he spun me around to face him. I watched has he peeled the condom off and presented his giant red penis inches from my face. For a moment I was hypnotized by the splendor of it, I admired the protruding veins and glistening shaft, I watched as it seemed to pulse with each heart beet.

As I had done hundreds of times before I closed my eyes, parted my lips and took him inside my mouth. This seemed to be a good position as I found I could slide my lips all the way down to the base without gagging. Robert began breathing very heavily and groaning with intense urgency as I gracefully sucked his cock with all the force I could. He grabbed my head and held it in place as he yelled out; “oh fuck!” I felt an explosion of warm, salty goo shoot into my mouth and fill my cheeks. With shock I wondered what was happening and what should I do. Robert continued to hold my head as he let out more groans and hisses. I felt shoot after shoot of wonderful cum squirt into my mouth, I couldn't move away so I swallowed it all in one large gulp. Even after swallowing I realized there was still more cum squirting out of his penis, I continued hungrily swallowing it. I felt an indescribable warmth spread throughout my body as my best friend deposited more and more of his seed down my throat.

After those few exalted seconds Robert relaxed his muscles and resumed catching his breath. I felt his penis start to go soft in my mouth and began sucking it furiously. I brought my lips all the way down to the base and glided my tongue up the shaft, pulling every last drop of marvelous cum out until there was nothing left. I realized this was the surprise he had promised, the new part of sex. I didn't care how many times he whipped me or what he wanted me to wear, I only felt that every spectacular drop of glorious cum he can produce must go inside me. I fantasized about what Heaven must be like, I wished that everything I eat or drink contained cum, I wished that every where I turned my head there would be a huge cock ready to explode. I wanted him to fill me up! Robert stood up and walked out of the bedroom towards the living room, I heard him collapse onto the floor and ran after him. As he lied there, his slender naked body sprawled out, his chest heaving, his cock resting on his belly he looked up at me. He flashed me a very warm smile and said; “what are your plans for tomorrow?”
noble
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Posts: 49
Joined: 27 Jun 2015, 18:49

Re: Frist time for everything, BDSM & Crossdressing

Post by noble »

This made me think of Michael G, who has been out of my mind for 50 years.
He was a neighbor and we used to play "tie up" games in my back yard.
(I have often wondered what my mother thought about that when she saw us.)
Neither of us seemed to prefer which role we took.
And them, when I was about 16, they moved to Saint Louis.
I've often wondered if he kept up with the bondage or self-bondage, as I did.
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