Sissy College Ch. 01

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All characters 18 and above. This series will eventually be filled with all the raunch you desire, but I like a little foreplay first. So sit down, slip down your panties, and enjoy!

I love your comments!

Chapter 1: Mathematics

Welcome to Chester College: An exclusive all-boys Sixth Form College catering to talented young men from across the country aged 18 and up. Students apply from the farthest corners of the country for a chance to be part of Chester’s unique learning environment. Indeed the college principal, Mr Blackwood, actively seeks out the best and the brightest students, offering full scholarships to those who are deemed worthy of the Chester badge. Athletes are especially sought after as Mr Blackwood believes that a strong athlete makes for a strong future leader. Most of the athletes at Chester, with a few exceptions, turn out to be black. It seems as though whether it’s football, basketball, or track and field, young black males have the numbers on their fair-skinned counterparts.

The key to Chester’s success lies in its specialised training streams. So while the jocks are out on the courts, sweating it out and jousting for dominance, the boys of a more “delicate” disposition are offered a completely different kind of education. You see, the students at Chester fall into one of two groups: the men and the bois.

The bois comprise almost exclusively of slender white sissies, sent to Chester by their parents to blossom into intelligent, feminine human beings. In general, the sissies are kept separate from the rest of the boys. Sure, you can hear them giggling and squealing in the hallways whenever a particular hunky jock walks past, but for the most part, they have different classes to the men. Unlike the rest of the school, the sissies are required to wear a uniform to prevent the little vixens from becoming too competitive. It consists of a pair of pink booty shorts and a skimpy white halter top that never reaches below the navel. The sissies are required to keep their bodies shaved at all times and their lips moist with lip gloss. Sexual relationships between students are not encouraged by the Chester board, but it is not uncommon to see a sissy draped around the arm of a black athlete in the hallways, or see a sissy locked in a lover’s embrace moaning into the mouth of her man while having her pert ass felt up by a confident hand.

Many attribute Chester’s success to the special relationship forged between these two groups of students, and Mr Blackwood wouldn’t have it any other way.

But enough about Chester. This is the story about a boy called Lenni.


Lenni Ümraniye Fetiş Escort was a slim white boy that had the opportunity to attend Chester College. He managed to get in because of his excellent Maths and Science ability. He lived with his single mother in a modest apartment. Lenni loved his mother and was determined to work hard and get a good job so that they could both lead better lives. He took classes with the other men at Chester, excelling in the classroom and winning many academic accolades. Due to his slight build, Lenni never really excelled in sports like the rest of his hyper-masculine peers. No matter what he tried, his frame would not develop muscle, his face would not grow hair and he could never quite lose the soft, boyish features of his face.

The fact that all his classmates were all growing bigger, stronger and faster made Lenni feel very insecure about his body. It had also made him very curious about the bodies of “real men”: men with big muscles, hairy chests and big cocks.

Call it insecurity or call it curiosity, Lenni’s was drawn to the bodies of these men. Whenever he watched porn, Lenni began focussing more and more on the men in the videos and less and less on the gorgeous women being fucked. He always felt a tinge of inadequacy when he compared his penis to the cocks filling his computer screen. Of course he didn’t expect to be hung like a porn star, but at only 3 inches erect, Lenni couldn’t help but feel he had been short-changed in the manhood department.

Lenni especially enjoyed interracial porn. He loved watching pretty young white girls being made to suck and fuck Big Black Cocks. He loved the way they squealed when they were first penetrated; the way their eyes rolled to the back of their heads as they were fucked and the way they smiled when their faces got coated with sticky black cum.

But Lenni didn’t really watch it for the girls being fucked. He watched it for the black men doing the fucking. One of Lenni’s favourite parts of any porn video was the shot where the girl was seeing the black cock for the first time. Lenni couldn’t help but open his mouth in awe whenever he saw a black dick spring out of a pair of boxers. Even completely flaccid, those black fuck poles were bigger than his tiny white penis. Black cocks commanded attention – they were regal, masculine and even beautiful, Lenni thought.

His fascination with black men quickly evolved to a point that most of the porn on his computer involved black men. He had a special folder filled with pictures of only black cocks: fat, virile black cocks. Whenever Lenni got the chance, he would open his special Ümraniye Gecelik Escort folder and jack off his tiny pecker to a slideshow of all the dicks he had collected over time, moaning and squirming involuntary and achieving the most satisfying orgasms of his life.


Mr Judd was Lenni’s black Maths teacher. Handsome, smart and funny, Mr Judd was a favourite among students at Chester College. Mr. Judd had always liked Lenni because of his strong numerical ability and the fact that Lenni always paid attention in class.

In today’s Maths class, however, Lenni’s mind was not on what Mr Judd was talking about. Lenni’s attention was instead focussed on the bulge in Mr Judd’s pants.

“He probably has big dick,” Lenni thought to himself as Mr Judd explained how to solve differential equations on the board.

“It’s probably long and fat with those sexy veins running down the side of it,” continued Lenni.

“I bet he has big heavy balls filled with enough cum to have a shower in.”

Lenni had involuntary started sucking on the pen he was meant to be taking notes with and his tiny penis began to stir.

“He probably has to wear tight boxers to prevent his big cock from flopping around between his thighs while he walks. They must smell really sweaty when he takes them off at the end of the day. I wonder if he masturbates with that monster.”

The thought of Mr Judd jerking off his cock sent an involuntary squeak out of Lenni’s throat. Mr Judd stopped the class.

“Is everything alright Lenni?” The sound of Mr Judd’s deep voice stirred Lenni out of his cockdream.

Startled, Lenni responded, “Yes, Mr Judd. Just feeling a bit sick. That’s all. Do you mind if I take a bathroom break?” Lenni needed to get out of there before he had another fantasy about Mr Judd’s cock.

“Sure Lenni, but don’t take too long.”

Lenni got up and made for the door. Most men would be weary of getting up if they had a hard-on but Lenni had discovered long ago that his boner was so small, it hardly showed at all through his pants.


In the bathroom, Lenni splashed some water on his face. He needed to cool off and get the thought of cock off his mind before he went back to class. He looked up and saw his face in the mirror.

A smooth pale face, with long brown hair and full pouty lips. He even had a cute dusting of freckles on his face. Some of his mother’s friends had called him pretty in the past.

“Am I ever going to be a real man?” Lenni thought to himself.

His train of thought was interrupted by a shuffling sound coming from one of the bathroom stalls. Ümraniye Genç Escort Lenni immediately froze and listened closer. It sounded like there were two people in there!

Curious, Lenni inched his way closer to the stall. He began to make out two voices: one deep and masculine and the other high pitched and feminine. Lenni put the pieces together: there was a sissy in there with a man! The man spoke first:

“So, gurl, you think you can send me pictures of your sweet white pussy, all dressed up in girly shit and expect me not to want to fuck that ass?”

“Oops. Did those pictures of my pussy make your big black cock all hard and angry baby?” giggled the sissy, obviously being a tease.

“Damn straight, bitch! I knew I had to have this ass today.”

Lenni heard something being unzipped and then a stifled squeal from the stall.

“Oh Gawd! Your cock is so fucking big! I need it in my pussy baby. I need your nigger dick sliding in and out of me.”

The man laughed, deeply and confidently. “Na gurl, after teasing me all week with that ass of yours, the only way you’re going to get any of this meat is if you beg for it.”

“C’mon baby, don’t make me beg for it. I’m so hot for you. My clitty has been dripping all day thinking about this,” came the deploring voice.

“Let me hear how much you want this donkey dick.”

“Please baby! Please fuck me. Fuck my sissy pussy with that black monster cock. Make me your sissy bitch. Fuck my gay ass – you know I need it!” The desperation was dripping from her voice.

“Haha. Much better. Come sit down on daddy’s lap.”

Lenni was rock hard listening to the sordid events taking place and had started rubbing his penis through his pants. Lenni heard a long moan coming from the stall.

“Yesssssss! Fill me up. Fill me up with black meat!”

The voices died down and gave way to stifled moans and grunts coupled with the distinctive sound of flesh smacking against flesh. Lenni couldn’t help but feel jealous that this sissy had got to see what a real cock looked like. He also couldn’t get himself to leave the bathroom.

After a few more minutes of rhythmic humping, the man finally spoke:

“I’m going to cum.”

The sissy squealed in obvious delight.

“Yes baby! Cream my cunt! Fill me with that nigger seed. Gawd, I want to have your babies,” panted the delirious sissy.

The humping picked up pace. The slaps of flesh got harder and faster. The man started groaning louder and more often. The sissy was panting heavily. Lenni could even make out the sounds of passionate kissing.

“Here it comes!” The man erupted.

“OH GAWD! Fuck meeeeeeeeeeee!!!” squealed the sissy.

Lenni was panting furiously too. Realising that they would be coming out of the stall soon, Lenni decided to quickly head back to class before he was caught eavesdropping. Lenni raced back to class, with his mind still full of images of Big Black Cocks.

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