The Training of a Ladyboy

I met a wonderful couple at a resort recently, Chantal and Dave. We hit it off splendidly and were soon spending our evenings together at the poolside bar. By disclosing the nature of my own infidelities (which was fairly obvious through my hitting on their hunkish friends!) I earned Chantal's trust and she disclosed to me the nature of their own very interesting and secretive relationship. I asked for her permission to recite their story to my readers and she agreed so long as I changed their names. Otherwise, my retelling of their story and how they were to become lovers is exactly as she related it to me.

*****

My best friend is Dave. Dave is a super guy. We have been best buddies since our school days. Dave always took me under his wing and included me in events and parties when no one else really wanted me there. Dave is the best friend a guy could hope for. Dave has always been very popular. Tall, strong, good-looking, charismatic, both guys and girls are naturally drawn to him and quickly befriend him. I am his short scrawny side-kick. Not that short, 5 foot 6, but thin to the point of skinny, being only about 130 pounds. Naturally blonde my hair is very fine and the virtual lack of hair over my body was always a bit of am embarrassment to me. I have no hair on my chest or stomach and that hair that is on my arms and legs is so fine that is doesn't appear to be there at all. I shave my face just to try and feel like a man, but I really don't have to. To be honest, I have had to admit to myself that my physical features are really quite feminine. My voice is high pitched and soft, I have no real muscle mass to speak of, the skin is soft and pale, and I am rather timid by nature. In fact all through school I was commonly the butt of peoples jokes at parties, people calling me Dave's little bitch. Dave just smiled and rubbed me on the head, telling me not to mind them.

After high-school we moved off to the city together in search of work and shared an apartment to make ends meet. I work in a department store while Dave works at a hardware store. On weekends we head out on the town, myself ever grateful to be included. Dave chases girls, while I pretend to, knowing I have no chance of succeeding. While he is frequently successful and brings home very pretty girls, the truth is, I have never actually slept with a girl. I would like to, I like women, but the opportunity has never presented itself to me. And it is doubtful that it ever will. Even if I was ever that lucky I know that she would never return. I am, lets say, disappointing in the manner that a woman seeks in a man. My balls remained undescended all my life, so my scrotum is tiny and shrivelled. While my dick is barely 3 inches long when rock hard and barely noticeable at all when not. I had accepted that my life would be spent as a bachelor, and therefore was very happy to have a guy like Dave as my best friend.

After one night out on the town Dave and I came home alone (no surprise for me). Wolfing down pizza Dave said "Fuck am I ever horny tonight. God, I really needed some bitch to suck me off."

I replied "Ya man, I know what you mean, same here." As IF I even knew what a blowjob felt like.

We sat down and turned on the tube and watched the sports channel. Sitting beside Dave I was quite drunk and tired and began to doze off. My head fell onto Dave's broad shoulders from time to time and he kept pushing me away. After a while he couldn't be bothered anymore and just let me sleep leaning against him. I was awakened by a jiggling sensation and opening my eyes saw that Dave had pulled his pecker from his pants and was stroking himself. Must truly be horny, I thought. I knew he would be embarrassed if he knew I was awake so I just pretended to still be asleep. As I lay there trying to focus on falling back to sleep I couldn't help but notice how much bigger his dick was than mine. Christ, this guys got all the breaks in life. Looks, strength, height, personality. And a big dick.

I admit I kind of got hypnotised but the motion up and down on that big shaft and after a while noticed I wasn't sleepy anymore. My eyes were transfixed on Dave's cock. I felt weird and perverted for watching. But it was just a perfect big thick long dick. He was so lucky to have it. No wonder the girls loved him so much! As I lay against his shoulder admiring Dave's massive stiffy I was surprised when he raised his free arm and began to caress my hair.

"Long blonde silky hair, just like a girl from behind." I heard him mumble under his breath. I lay there in stunned silence. But I rather enjoyed the sensation of a hand running through my hair, so I relaxed and let Dave freely play with locks and continued watching him stroke that big thick cock. I noticed that the pace of his stroking increased and the stiffness of his dick further hardened once he started running his hand through my hair. I heard him say to himself "Fuck ya, I really need some pretty bitch to suck me off tonight. Some pretty skinny blonde slut bitch. " Not sure where he was going with the talking to himself I then felt his powerful hand clench around my hair and laying back into the couch to spread himself out he leverage my head off his shoulder and down along the length of this chest and down his stomach. Oh my God, that dick was now only inches from my face! I could smell the strong fragrance of his sweaty cock in my nostrils. I wanted to recoil, but I knew that then he would know that I had been awake all along and had watched him silently stroke himself. Unwilling to appear to be a weirdo in his eyes, I remained silent and motionless, convincing him that I remained deep in sleep.

Stroking my hair further Dave slid his hand down over my back and pulling up my shirt exposed my flesh. Then he ran his hand up and down my bare skin. I heard Dave say "Ya, pretty little blonde bitch, tall, lean, skinny, just the way I like them." And before I could think any further about what was going on Dave had pushed my lips against the head of his cock. I left my lips closed, scared into paralysis, maintaining my cover of sleep. Pinning my head in position by my hair he released his cock from his hand and pried my jaw open. He then simply pushed my head down over his cock. Oh my God I thought, I have half a Dave's cock in my mouth! Using the hair in his hand to force my head up and down he slowly began to fuck my face.

At first I was horrified. I wasn't gay, I didn't want to suck off my best friend. But I could do nothing at this point and unable to resist I let Dave do as he pleased with me, thinking oh well, it will just be over soon and then we will never speak of it again. Stroking the flesh of my bare back and even sliding his hand down over my small butt Dave continued to rock my head up and down over his dick. Too drunk to think clearly I found that the rocking motion of my head began to put me at ease and I soon found myself relaxed in Dave's arms. I began to think about the cock that was in my mouth. Smooth, hard, not bad really, didn't taste bad like I had imagined it would. The tension left my body and I realized that I didn't really mind my friends cock in my mouth. I was not gay or a cock sucker, but it was ok if I pleased him this one night, he had done so much for me over the years, I at least owed him this.

Sliding his hand under my jeans he began to explore the curves of my ass. As he continued speaking to himself I found his deep voice to be very soothing and made me feel ever more comfortable in his arms, and not minding at all now the thick hard penis in my mouth. The whole experience just became rather sensual and pleasant, relaxing and calming. Dave would pull my face off his cock from time to time and I came to almost welcome him pressing my head back down over him. His words filled my mind with thoughts and ideas. "God, a nice soft hairless ass as well, a very nice tiny little girls tush. Ya, I remember now, long skinny hairless legs as well. A skinny blonde slut. Ya, yes, you will do just fine. Good little cock sucker for when there are no other bitches around. Just need to tighten those lips, learn how to really suck a dick."

I realized that what he said was true. To this point he was just forcing a big dick in and out of my open mouth. But I was doing nothing in return with my lips or mouth. Again, yes, I owed him this much for one night, so I would do it right. Slowly, so as not to be appearing to be responding to his words, as I did not want to alert Dave to the fact that I was awake, slowly, ever so slowly, I began to close my mouth and tighten my lips. If I was going to suck off my friend Dave this once and only once to show my appreciation for all that he had done for me over the years, I might as well do it right. Soon I was sucking cock like a pro. My lips clamped around his cock as Dave pumped away at my face. "Fuck bitch you suck like a paid whore!" He exclaimed and then I felt his cock pulsating on my lips. Soon the wet warm fluid gushed in repeated bursts into my mouth. I knew that I could offer no resistance and so accepted my fate willingly, letting the hot jism slide down my throat, swallowing occasionally to avoid choking. I was pleasantly surprised. Cum didn't actually taste bad. Not bad all!

Pulling back down my shirt Dave lifted my head and placing a pillow under it simply walked away. I laid there, mouth tasting of semen, licking my lips and gulping down the last of it. I was proud of my performance. It was not so bad, sucking on Dave's cock, and if that is what it took to show my appreciation, then so be it. I felt that I had been a great friend to Dave.

The next morning I entered the kitchen and sat down to breakfast with Dave. I said nothing and neither did he. I smiled at him a lot, and he smiled back at me. Dave was truly my best friend now. More than a best friend. The bestest of friends! It was Sunday and I suggested we go to the local amusement park for the day. Dave was up for it so I went to get ready. As I was combing my hair I recalled the hair styles of the blonde girls that Dave always went goo-goo over, and so using a curling iron and some pins I styled my hair in the same way. I struggled with what to wear. It was going to be a hot day, so shorts made the best sense. The pair I tried on were way too tight, I must have gained a few points. They were tight around my butt and on my groin. But shoving my small dick down into the pants they wrapped around my body in a snug fit. Looking in the mirror I thought I looked a bit effeminate and also like I had camel toe showing, but I thought, what the heck, no one had ever noticed or cared what I look like. Putting on a tight T-shirt I met Dave at his car.

As we drove to the park I noticed Dave frequently glancing over at my legs. At first I thought he was thinking how silly I looked. Yes I had skinny hairless legs and I looked like a girl in shorts, but what choice did I have on such a warm day. Then I recalled his words, " Skinny legs like a girl." Maybe he was just checking me out to see how true to his words my legs were.

At the park we went on all the rides, my favorite the roller coaster. I sat close to Dave and screamed probably like a little girl as we crested each hill. I felt foolish but Dave would always look at me and smile. On one particularly long descent I screamed and sub-consciously seized onto Dave's hand. He thoughtfully held my hand all the way down. His large palm surrounding my dainty little fingers made me feel secure and safe, like being protected by a big strong man.

And we crested the same slope again I screamed and Dave took my hand in his one hand to comfort me, but his other hand came to rest on my inner thigh. Without thinking, over-whelmed by the fear and exhilaration of the descent I naturally spread my legs wider apart, and at the same time Dave's fingers bit deeply into my flesh. For some reason the pressure of his grip made me actually feel warm inside, but just for a moment, and then the ride was over. Looking down I could still see the red lines evident on my flesh where his hand had been.

Driving home Dave was rather chatty and to my surprise more than once he ran his fingers through my hair, telling me how he liked the new style I had it in. Also while laughing he would slap his hand down upon my knee as he had frequently done before in a friendly gesture. But he now sometimes slid his hand up the length of my upper leg, taking his time, and lingering on my flesh near my groin.

Nothing more was said of that day, or the night before, and we proceeded with our jobs through the next week as we always had. When Friday night rolled around Dave was eager to hit the bars and I was again always grateful for the opportunity to tag along and proud to hang out with such a cool good-looking guy. That night he didn't seem to try very hard to pick up girls I noticed, and he freely offered to buy my drinks for me. When we got home I was quite intoxicated and Dave suggested we sit and watch TV. As it was still a very hot and muggy August evening he suggested I also change into something I wouldn't sweat in, like the shorts I had worn earlier in the week.

Changing as Dave had suggested I do, not wanting to disappoint my best friend, I returned to find him stretch out on the couch also in a pair of shorts, but without a shirt. His large hairy muscular chest and stomach made me feel like such a puny girly man. He suggested I remove my shirt as it was too hot for one tonight. Suggested, or really commanded. I obediently followed his orders. Sitting beside him Dave continually glanced at my legs and hairless chest and soft stomach. I noticed the bulge evident in his shorts. But I was very tired and Dave suggested I relax and catch a few zees. Pulling my head down onto his shoulder I was soon cradled in his arm. He began to stroke my hair and the soothing action of his motions began to put me to sleep.

Feeling his shoulder begin to move I opened my eyes to see that once again he had pulled his pecker from his pants and was stroking at it. I admired the glistening fluid at the tip of the big bulbous purple head of his cock. I had promised myself that I would only suck him off that one time but now I found myself salivating at the thought of having that purple head back in my mouth to suck upon like an ice-cream cone. I did not resist as he slid my head down over his furry chest, almost welcoming the motion.

This time he did not have to pry my jaw open but rather found my mouth already stretched wide ready and eager to receive his cock. My lips instinctively wrapped tight around his thick shaft as his cock slid comfortably into its new welcoming cavity. Though he used his hand to guide my head up and down over his massive rigid member he barely needed to. The truth is, for some reason, I took to sucking on his cock like a fish takes to water. I willingly sucked Dave's cock tonight. Dave was my best friend. And I owed him for all that he had done for me over the years. So if tonight, and any other night, Dave was lonely and needed a blowjob, then I would be a good friend and let him use me to satisfy him. But I would always pretend to be asleep. And we would never speak of this. Otherwise I feared the magic of our friendship might be shattered.

I did not worry about this tonight. I would focus on sucking his cock, focus on perfecting my motions. When he pulled my head from off his cock I focused on licking the head, running my lips up and down the shaft. Dave was my best friend and if he wanted me to suck his cock then this was really the least I could do for him. He thrust my head back over his cock and then rested my head on his belly. Without thinking I reached out with my hand and wrapped my fingers around the thick penis. It felt good in my hand. I gave it a squeeze. Felt very good indeed. Dave let out a moan. I kissed softly at the big purple head licking the pre-cum from its tip. I didn't appreciate it at the time, but I admired this cock, such a perfect specimen the likes of which I would never have otherwise known existed considering my own enfeebled state. I was proud to suck Dave's cock, honored even. Without knowing it I began to worship this cock, love this cock, willing to serve this cock in any manner it demanded.

Pushing my head back over his cock I lay on Dave's stomach and softly sucked at the gift he had thoughtfully offered me. I enjoyed the sensation as his hands began to explore my body. His hand ran down my back, then around to my chest. I felt as he pinched my nipple between his fingers and made it grow excited and hard in response. He rubbed his hand over my flat soft hairless belly. Then he slid it down over my bum and onto my legs. I parted my legs instinctively and enjoyed the feeling of his strong rough hands rubbing over my soft flesh.

"What a pretty little girl you become at nights." Dave said to himself, as he continued to caress and fondle my inner thighs. "Such slender legs and tiny little titties, but hard nipples that like to be pinched. And a real slut. A slut that loves a big dick in her mouth. A natural cock-sucker. My pretty little sexy cock-sucker."

With these words of encouragement and appreciation, really only the first I had ever received in my life, my eagerness to please my friend grew exponentially and I increased the pace of my cock-sucking, teasing and torturing that big meaty cock between my lips. "Oh Christ bitch, yes, use that pretty little slut mouth of yours to suck me off again. Suck on my cock. Your cock. The cock that owns your sexy little slut body."

I sucked like a mad-man and soon that familiar feeling of his cock pulsing on my tongue and lips let me know that I was soon to receive my prize. I eagerly awaited the lovely gushing I experienced the week before and was not to be disappointed. I willingly gulped down my best friend's semen. He deserved this of me, he had earned it over his years of support and commitment to a person as weak and pathetic as me. I didn't deserve his friendship, but was honored for it, and wanted to repay him in any manner I could.

When Dave had finished cumming in my mouth tonight he was gentler with me afterward. Scooping me in his arms he carried me to my bed and placed me on my covers. Spreading my legs apart he once again explored the soft skin on my weakling legs. Raising my head slightly off the pillow he placed the head of his softening dick to my lips. Without opening my eyes I parted my lips and extending my tongue, licking up the cum dripping from the tip of his cock. Leaning over and putting a large palm on my belly he kissed me on the forhead and told me " I never noticed before, but you are actually quite pretty, like a girl. Yes, you are a girl, my girl. My little slut cock-sucking girl. The boys were right all those years. You are my little bitch. My pretty little cock-sucking bitch. Tomorrow, yes tomorrow, I think I will use you as my full little bitch. Night pretty bitch." He finished and leaned forward to kiss me on the cheek. I could not resist smiling from ear to ear at his words. Dave would be my best friend forever, I thought. And this was all that I wanted. Perhaps all that I had ever wanted.

The next day I got up early, as I wanted to do something special for Dave. I felt too pale, too boring, and I wanted to impress him and make him happy. So I slipped to a women's store and bought some basic make-up. You know, some foundation, a touch of rouge, just some light eye shadow, and maybe, yes, a very subtle pink lipstick. And a few more tubes of assorted colors. Men these days wore make-up, I had read it. Metro they called it. Yes, I was metro. And I thought it might make Dave happy to see some color in my cheeks.

I found him sitting watching TV and suggested we go to the park. I would make a picnic, and we could relax under a big tree. After making the lunch I told him I just needed to fix myself up. I came out of my bedroom later to find him impatiently waiting, wondering what had taken me so long. But he quickly calmed down when he saw me. I had put my hair back up in the style he liked. I wore a pair of tiny short shorts and some sandals I had just bought with high heels. I wore no top at all. I dolled my face up a bit, just subtly I thought. Put some color into my otherwise boring pale complexion.