Road to Becoming a Sissy Bitch Boy

The road to becoming a sissy bitch boy

I never fully understood why I just didn't seem to fit in. 22 years old, a recent high school graduate, decent looking. Just painfully thin. Most of the guys I knew at high school seemed to fall into some sort of group. Athlete, scholar or nerd. I was not masculine enough for sports, nor smart enough to hang with the book worms, or terribly good with computers. I just sort of "existed"

I always imagined myself as a normal, good-looking boy, but in reality, I was more feminine than male, and I knew it. I never developed the chest hair, or the muscles most boys have at my age. At 5'7 and 118 lbs., I was the kid the jocks picked on. Often called names like queer, twirp, sometimes worse. Gym class was a nightmare. When I was forced to shower, I often grew the stares of the other boys. While my appearance was frail, hairless and timid, my genitals developed out of proportion to the rest of me. More like that of a well-endowed man. A seven-inch cock really stands out on a boy so skinny. If the guys in the shower at school ever saw me fully erect, the name calling and teasing would have been far, far worse. I quickly noticed I was bigger in that department than every other guy in the shower. And most guys I've seen in porno clips. Although I never measured, I guessed my cock was ten or eleven inches hard.

I'd always been attracted to the girls at school, but just never had the nerve to talk to any of them. I seemed to notice things like their shoes, or the clothes they wore. I fantasized about what they were wearing under their fancy skirts and blouses. I soon discovered the world of internet porn, and that remained my only release for the hormones I felt maturing inside my body. Jerking off two or three times a day was not unusual for me. Usually to older women feminizing young men movies. This seemed to arouse me the most, but I strangely found myself fascinated with the men in the films. How large their cocks were, how obedient and subservient they were. The look of humiliation as they were dressed in panties, bras and stockings and forced to service their Mistress, and other slaves. I felt ashamed, but I usually shot my load a lot quicker if the guy in the film was strong, well hung, and wearing panties. Another thing I discovered from his porn addition was my fetish for panties. How they looked, and how they felt against my throbbing cock. I "borrowed" a few pairs from my mom's laundry basket and wore them for most of my private sissy jerk off sessions. I soon decided to wear panties all the time. They were easy enough to order on line, and my mom would never find out as long as I did my own laundry. Ejaculating into my pretty panties became the rule, not the exception.

Due to financial problems at home, I was not provided the opportunity to attend college like all the other kids at school. I remained living at home with my strict mother, stuck in the small town I grew up in.

My mother had arranged a summer job for him down at the Local garage, changing tires, cleaning up the shop, and various other duties the mechanics didn't want to do. I hated it. The work was too strenuous for someone my size, and I struggled lifting the tires. And just like school, the men there made fun of me, and laughed at me due to my lack of physical strength. I knew he'd better get out of there, or it would not end up good.

At the end of the summer, I applied for a position at a coffee house a few towns away. Busing tables, cleaning up and restocking the supplies were all things I could easily do. I was accepted, and looked forward to leaving the humiliating job at the garage. After two weeks, things were going well. I seemed to fit in, and made my first real friend. Xander, the assistant manager, was only two years older than me and we seemed to have a lot in common. I figured his real name was Alexander, but everyone called him Xander. Xander also had a small build like me maybe ten lbs. heavier. And he never talked the macho smack most guys did. In fact, we often laughed together when we noticed girls coming into the bistro wearing outrageous outfits, or shoes that didn't match their purses. Life seemed good now. I had a job I liked and a friend to hang out with, one that didn't seem to hung up on masculinity. Based on his body language, I suspected Xander was gay but I wasn't about to judge the only friend I had. On more than one occasion, I noticed a large bulge in Xander's tight jeans, and caught him checking out my ass. I didn't care, I was just happy to have friend I trusted. Having someone "check me out" was something I had never experienced, and it excited me in a way I had never felt before.

One night as our shift was about to end, Xander invited me join him at a local bar a few doors down for an after-work beer. Although not a huge drinker, I did love beer. The thought of socializing with my new friend outside of work seemed like a great idea. After locking up the store, we walked the short distance to the bar, and found an open booth. Xander ordered us two beers, and seemed to know most of the people working there. The bartender and the waiter both called him by name, and asked to be introduced to me. I was impressed with the friendliness of everyone. The bar was small, but had that home town feel that was appealing to me. A pool table, a small dance floor and lots of neon bar lights took up most of the room. I also noticed a few doors marked "staff only" which seemed odd, but I shrugged it off.

After finishing our beers, we agreed it was time to head home. We were both off from work the next day, and planned to spend the day together over at Xander's house. Xander lived with his mother and stepdad. He told me they would both be at work, so we had the house alone for most of the day. A day of hanging out, playing video games and having fun sounded good. Plus, Xander had a pool at his house, even better.

I woke up early, and made myself breakfast. Then packed a small bag. A towel, extra shirt a pair of panties and a bathing suit. I knew all I had to swim in was my spandex speedo. I figured it would just be just Xander and I, so what the hell. It was hard to hide a 7-inch bulge in pair of speedo shorts, but it was all I had, and planned on staying in the water most of the time.

When I arrived, Xander was out back by the pool. Music playing, beer in hand. I grabbed a beer and sat by the little bar they had set up. Xander was sitting on the edge of the pool rocking to the music. It was apparent he had a few beers before I got there. We sat around the pool, drinking beer and talking. Xander made it known after a few subtle hints, he was in fact gay. Or bisexual at the very least. By my reaction and body language, he could tell I didn't really care.

After a few beers in the hot sun, I felt a beer buzz beginning, so I went to the cabana to change into my skimpy speedo. When I returned, Xander stood up to get another beer, and I noticed the huge, almost erect outline of his cock in his swim suit. Amazed, I couldn't take my eyes off his crotch. l felt my cock instantly harden. Xander walked over and said "like what you see?" I couldn't speak, but I think the semi-hard cock in my speedo answered his question. Without saying another word, Xander slid his hand slowly into my suit, gently grabbing my cock and slowly massaged it. I didn't protest, and semi-hard went to rock hard in an instant. I just closed my eyes and let the events unfold. All my thoughts about why I was different were becoming clear. "Am I gay" I thought? At that moment I didn't care. Gay, BI or Straight, it didn't matter. This felt incredible, and it was the first time someone else had touched my cock. Xander guided me over to one of the beach chairs and sat me down. "Pull my cock out" Xander ordered. Mindlessly following the older boy's command, I pulled his suit down to his knees. Xander's hard cock sprung out of his tight suit and was at eye level. "Omg, his cock is just as big as mine" I thought. "Stroke it pool boy" purred Xander. Without hesitation I did as I was told. Starting slowly, I felt this huge hunk of meat throb in my hands. Gliding my hand up and down the shaft, over the tip, and back down to his balls. I watched Xander's eyes roll back, and heard a low moan coming from my new friend. I knew what was coming next, and knew there wasn't much I could do to stop it. Xander lowered his hips, and slid the tip of his hard cock into my mouth. I thought about protesting, but knew I wanted this. Xander started slowly at first, then picked up the rhythm. His hips thrusting slowly, his cock sliding in and out of my mouth. I felt like I had been transported into one of the porn movies I often jerked off to. I knew at that instant; I was a born cock sucker. I reached down, and pulled my cock out of the leg band of my speedo. I began jerking my own cock, trying to match the rhythm of my friend's cock thrusts. It felt so naughty, so humiliating, but I didn't care. After three minutes, I felt myself going over the edge. The muscles in my legs started shaking, my balls tightened, and with a grunt that sounded more like woman than a man, I shot my huge load of cum all over my leg and pool deck. Two large spasms, and three smaller ones. Xander had watched my orgasm and got more aggressive. Thrusting into my mouth over and over. Face fucking me like a faggot. Feeling his cock about to explode, he grabbed me by the hair, and sunk his cock deep into my mouth. Spurt after spurt of sticky cum shot out of his spasming cock, filling my mouth and running out the side and down both cheeks. I had no choice but to swallow it.

We both collapsed into beach chairs and tried to catch our breath. Before either of us could speak, the unthinkable happened.

The music playing went silent. Both our heads spun in the direction of the stereo. Standing there, with her arms folded across her chest was Xander's mom. Standing directly behind her was his stepfather. They both look pissed off beyond description.

With an "OH SHIT" we leaped to our feet, trying to pull up our swim suits, and wipe away cum at the same time.

The story continues, with Ian's Road to femdom.