Jerry, Jerry Quite Contrary

by Victor E

Copyright© 2017 by Victor E

Sex Story: For some time, Jerry Jackson has suspected that he was more than just a wimp, a sissy as they called him in grammar and then high school. But he didn't know if he was gay or straight or something in between. He's been picked on and humiliated a lot in high school and had a very humiliating experience at Boy Scout camp, but it wasn't until he went off to college that he found out for certain about his inner-self. He thought he was going to pledge for a fraternity. Instead it was a sorority.

Caution: This Sex Story contains strong sexual content, including mt/ft   Ma/mt   Consensual   Reluctant   Gay   CrossDressing   FemaleDom   Humiliation   Light Bond   Spanking   Group Sex   Masturbation   Oral Sex   Sex Toys   .

Jerry Jackson was a nerd. But the lad wasn’t always called that; in grade school the boys called him a ‘ Mama’s boy’, in the Boy Scouts he was called a sissy and in high school he was usually referred to as a wimp.

At age 17, Jerry graduated from Chicago’s Smyth’s High as the school’s brightest student in its 160 year history. He had achieved what no other Valedictorian had: straight A’s or 100% marks in every course entered from Kindergarten to his senior year. Jerry accomplished this by dint of a brilliant academic mind and by getting medical exemptions from all PE classes and sports participation which, had he been enrolled in these studies, he would have failed miserably.

Jerry was a near genius but the effete labels, stamped on him by bullies of both sexes, continued to scar his psyche even as he won the most prestigious awards in academia. What cut Jerry to the quick was not so much the public approbation and humiliation that goes along with all childish name-calling. It was that, in his heart of hearts, Jerry knew it was all true. In fact, he thought of himself not so much a sissy, as a pussy.

These days, through all-inclusive psychology, Jerry would likely be diagnosed as a ‘contrarian youth with opposing but complementary gender-identity issues’ ... aka, a mixed up kid who was a horny sissy.

Although he was a mature male teenage boy by his 17th birthday, Jerry had always thought his true gender was female. He was a guy physically and he had the balls and decent sized morning wood to prove it. But his feelings and certainly what he dreamed about were decidedly female.

And this wasn’t just because at age ten his mum had mentioned to him that after giving birth to his two older brothers, she had desperately wanted a girl. She told him his chosen name would have been Geraldine, but they had to settle for Jerry. That probably reinforced his girlish ways in his preteen years. But he had soft feelings a lot earlier. At age four he played ‘Doctor’ as a naked patient for the little girl next door. He played dress-up for her and three of her older girlfriends; they supplied panties and skirts for Jerry who slipped into the bathroom to change out of boring boy stuff and into glamorous girl garb. The girls had fun dressing him up as one of their own. Jerry even learned how to apply make-up. He just applied powder, rouge and lipstick, but with his long blonde curls he really did look like a little girl.

Years before Jerry hit middle-school, he had developed a rep as a Mama’s boy and was constantly picked on by bullies. He was used to being called sissy and having older boys try to pull his pants down in the schoolyard in front of giggling girls over a dozen times. Lucky for him, each time they tried he managed to escape with only a few inches of his underpants’ elastic hem showing.

He was even luckier that all those times he had been wearing his own boy underpants, not the panties he’d secretly bought at the Dollar Store and which he’d often slept in, stroked his cock in, and even shot his wad in after puberty.

Not that he was unaffected by these taunts and disparaging slurs to his developing manhood. He wanted to be seen as ‘ a real boy’, even though he secretly felt that he was, in his heart of hearts, really a girl. By age 14 he had had many dreams wherein he wore girl’s clothing, stripped naked before boys as well as girls, and even played with boy’s private parts.

When he awoke from the naughtiest of dream about boy balls and cocks, Jerry always found he’d creamed the underpants or panties he’d worn to bed. Once, after an especially naughty dream, his panties were soaked in his cum. He hadn’t been dreaming about naked girls. That was a turning point for the confused young lad. He felt the need to declare his manhood by day. But he dreamed of being a girl at night. He had to deal with this but just didn’t know how. Two years before graduation from high school, when he was fifteen, his family sent Jerry out of state for a few weeks, to the Las Vegas area, where Jerry joined the Boy Scouts in an attempt to pick up manly skills, like lighting a camp fire, trekking in the bush and canoeing. He wanted to prove to himself that, even if he was a sissy-wuss, he could at least appear to be a macho-male teenage boy. Maybe that would help him be a boy and not the girl he really wanted to be. He was conflicted but was trying to solve his problem.

Still, he just couldn’t leave his favorite panties behind and, secretly at night, he’d slip into them after lights out. He made sure he awoke early enough to change out of them and into his pajamas each morning before the other lads in his six-man tent woke up.

What Jerry didn’t realize was that (1) sometimes on hot nights he’d kick the bed covers down a bit and that (2) the Scout Master made tent checks at 1 a.m. to make sure everything was okay with his young charges. That’s how, on the fourth night, Brad, the tall and muscular 22 year-old Scout Master, came to notice Jerry’s pink, lace-hemmed panties as the lad lay on his tummy, thus showing off Jerry’s cute bubble butt. Brad made sure to drop in the next night too and was treated to the panty-clad lad lying on his back with the blanket dropped to mid-thigh which gave Brad a good look at Jerry’s swollen boner tenting those pink panties.

Brad made his move, quietly but firmly. He gently woke Jerry up and shushed the boy as he pointed his flashlight beam at the boy’s panties then back up to Brad’s own grinning face. Brad winked and tapped Jerry on the shoulder letting the boy know he had to follow the Master ( as it turned out, in more ways than one!) Brad made Jerry walk to the Scout Master’s tent in only those pink panties. There Brad spoke in a soft voice but with hard words.

“Jerry, you’ve been very foolish,” began Brad. “ If the lads in your tent ever saw what you’re wearing at night, you’d be teased and jeered at for the next twelve days of camp. You wouldn’t want them to find out, now would you?”

Jerry could tell by the sneering look on the Scout Master face that this was not sympathy being shown; it was blackmail. Jerry hung his head more in fear than shame and nodded his head.

Brad spoke slowly, “ Jerry, you’re a very bright young boy so you must know that for me to keep my mouth shut, you will have to keep yours open.” And with that, Brad placed his hands on the lad’s shoulders and pushed Jerry down to his knees. Then Brad, standing over him, slowly unzipped his pants and tugged his underpants down and out of the way as the Scout Master’s considerable manhood popped out glancing on Jerry left cheek. Only two words from Brad, “ Suck it!”

Jerry had resisted at first. But the lad loved the smell of his own cum when he masturbated at home. Also he had often licked up his own cum from fingers or palm of his hand. He was no stranger to the scent and taste and that always re-energized him to a second and even third erection. This night, kneeling before the Scout Master, was no exception. Brad noted Jerry’s facial expression and body language which told him Jerry was getting as much pleasure out of this as he was. Mischievous thoughts entered Brad’s head.

The rest of camp week was, for the most part, normal. Brad made a couple of late-night visits to help Jerry perfect his cock-sucking skills. He wanted the young lad to be good at it before the traditional final night games when boys will be boys and naughty boys are allowed to be very naughty as they try to prove their manhood.

The game, ‘Soggy Biscuit’, was pretty much standard humiliation and masturbation fare for boys Jerry’s age and younger. The usual rules of the game called for a bunch of boys standing in a circle masturbating over a bun or slice of bread. They would each cum on it and the last one to add his contribution to the now soggy, cum-soaked ‘biscuit’ had to slowly eat it.

But at Scout Camp there would be 24 lads, a whole troop of hormone crazed boys. So Scout Camp rules accommodated the larger than usual number in a few ways. First, two slices of Wonder Bread, not one, would be cum-soaked and eaten as a soggy semen sandwich. Secondly, as Scout tradition demanded, all members of the troop had to participate in Scout activities. So any boy who tried to cop out with some lame excuse would have to pay a forfeit but would still end up playing ‘soggy biscuit’. First year scout campers were not informed of any of this. They were just told they had to play a traditional Boy Scout game or else pay an embarrassing forfeit. Although only the scouts, and not the Master, participated in the game, it was Brad who set the rules. And this year he told the senior scout in charge about a new rule to be added, which made the forfeits much more interesting and amusing.

On the final camp night Brad took Jerry aside before lights-out to tell him to be wearing his panties that night and that he better refuse to play the game everyone was going to play. If he didn’t refuse, Brad would expose him for the little panty-wearing, cock-sucking sissy he really was. Jerry didn’t need to be to twice; he would refuse to play no matter what.

At midnight one boy in each six-person tent took charge, rousting everyone and leading them to an isolated spot where a campfire had already been lit. Next to it, on a tree stump that stood three feet off the ground was a paper plate on which there lay two slices of white Wonder Bread.

The object of the game, but not all the rules, was explained to the first-year campers most of whom were eager to show off their manly prowess. The returning scouts smirked as they knew all but the latest rules about forfeits. Carl, the sixteen-year-old scout in charge, explained it all like this:

“Every boy here has to prove his manhood. If he can’t or won’t, that means he’s a sissy. So I need a pledge from all of you that you’ll play ‘Soggy Biscuit’ by the rules and pledge that the last boy to cum has to eat the biscuit. Signify your pledge now by unzipping your pants, pulling out your manhood, and stroking it to attention before the game begins.”

Some first-timers hesitated but within a minute all the scouts except Jerry had their pants unzipped and hardening cocks on view. Jerry declared his refusal out loud in a whimpering voice. Carl went to Jerry and hissed in his ear, “ Play or pay, sissy scout!” Jerry refused again and boldly said, “You can’t make me.”

That’s when Carl drew everyone’s attention saying, “ I had hoped I wouldn’t have to explain the first forfeit. But I guess Jerry here is making me.” Laughter was heard from some of the older scouts and giggles from the younger ones.

“Okay,” continued Carl as the laughter died down, “ First penalty: any boy who refuses to play ‘Soggy Biscuit’ will be stripped down to his underpants which will be pulled down to his knees for a bare-bottom strapping with a belt. After which the spoil-sport scout will still be forced to masturbate over the biscuit and play our game. So I ask you again, Jerry Jackson, do you refuse to play?”

Jerry was in a real bind now. He had to keep refusing to play because Brad had so much over him. So he answered “ Yes, I still refuse to play.” And so Jerry was stripped, strapped and turned out to be the one who came in last. So he ended up eating the soggy biscuit. Had Jerry suffered the greatest humiliation of his entire 15 year-old life? Or had he enjoyed this humiliation as he pretended in his mind that he really was a girl, a real slut at that, who enjoyed eating the cum of a whole troop of Boy Scouts. Even he did not know for sure which was closer to the truth.

What he did know for sure was, as he dressed and packed for his journey home to Chicago, was that what happened in Vegas, stayed in Vegas, so his secret was safe and his reputation would not suffer.

Jerry Jackson had learned a lot at Boy Scout camp that year. But he was as confused as ever about his manhood. He found out how mean boys could be, how easily he could be blackmailed into doing all sorts of stuff. But, most of all, he learned how being made to do as he was told and being sexually humiliated somehow felt exciting and aroused him.

He tried to put his Las Vegas experience out of his head as he headed back home to Chicago. In high school, Jerry knew enough to keep his head down, avoid sports and get medical exemptions that would spare him from gym classes and keep him out of the boys’ locker room. He was afraid if he was caught with his pants down, so to speak, he’d revert to a submissive state of mind. Unfortunately, his avoiding being seen undressed just made other guys suspicious about Jerry’s sexual preference or at least that he was afraid to be naked among guys. In other words, either gay or a sissy.

So some guys did call him a sissy to his face and worse behind his back. A few girls joined in subtle teasing and not so subtle pranks at Jerry’s expense. Those included trying to pull his pants down in the school hallway. On their first attempt, Jerry managed to dodge them. He ran away but strangely found himself wishing that they’d caught him.

On the girls’ second attempt they failed again. But again Jerry felt he’d missed out on a great opportunity. He decided to arrange his own pants removing dilemma. The next day Jerry made sure he was wearing tight, speedo type underpants ( as close as one can get to panties and still be considered boy underwear) when he deliberately bumped into and even knocked over one of the bully girls who’d been chatting with a bunch of her friends.

Jerry stuttered a sincere apology as he helped the fallen girl up. He looked so shy, guilty, and embarrassed. His act was so convincing that the girls immediately pounced on this easy target. The seven of them surrounded him and pushed him against the bank of lockers. Jerry quickly said he was sorry, but a couple of the girls punched him in the gut and pulled him by the ear as they told him he didn’t know what sorry was but he was about to find out.

Jerry whimpered and looked frightened as he pleaded with them, “ Please, “ he sobbed with real tears falling down his cheeks, “ it was just an accident, don’t hurt me.”

When those girls only laughed and poked him in the balls doubling him over in pain. The girls figured they made their point and turned to leave. But before they could, Jerry cried out, “ Please, don’t pull down my pants, I am really sorry.” Jerry had decided to use reverse psychology a la Uncle Remus and Br’er Rabbit’s Briar Patch ploy.

“Please don’t embarrass me that way,” Jerry pleaded, “ I said I was sorry. Don’t pull down my pants.”

That’s all the girls needed to hear. Three of them grabbed their sissy captive as two others yanked his jeans right down to his feet. What they saw make them giggle and whistle appreciatively. Jerry speedo underpants were tenting and it was very impressive.

Flashing humiliation did not stop there, though. Jerry blushed for real, but his heart was beating a mile-a-minute in excitement, not shame. He reacted to his dilemma in a manner as confusing to the girls as his own feelings were to him. Jerry cupped his hands over his bulging crotch, but at the same time, whimpered, “ Please girls, don’t make me take off my underpants too.”

He could just as well have attached an RSVP to that pathetic plea. One girl grinned and stepped right up to Jerry, grabbed his pulsating package through his speedo and said, “ Okay, you don’t take your underpants off.” paused for a few seconds then added, “ until you cum into them.”

As she massaged and stroked his hard cock, she added, “and make sure you shoot a full load. We want your panties to be soaking wet!” It took about three minutes for her demand to be met, during which time her gang of girl-bullies kept Jerry hidden from view. They wanted to keep his torment all to themselves.

When Jerry had cum at last his masturbation Mistress smiled softly and said, “ Okay, you can take your panties off now ... and then shove them into your mouth.” To their amazement, Jerry did as he was told. But he had to slip off his shoes to get his pants off before removing his speedos. Jerry stood in the hallway stripped naked from the waist down, his mouth now stuffed with a cum-soaked pair of underpants. All this time, Jerry was crying as if he was scared at what he’d be made to do next. But for now, his tormentors were satisfied and the main bully-bitch told him to leave his speedo panties in his mouth for now, but to put his jeans back on before anyone else sees what a sissy he is.

They left him, moving away one at a time, so that Jerry had a minute to get dressed again. That’s when the opening bell rang and Jerry, underpants still in his mouth, had to rush to homeroom for the morning sign-in. There the teacher called out each student’s name and awaited a ‘here’ response and hand up before checking them off for the attendance roll. “Jerry Jackson” the teacher called. Jerry’s hand went up but all he could say was ‘ Mmsrrehtff’.

Some of the kids laughed at him. But one girl, the youngest of the seven who had just accosted Jerry in the hall, was sitting in the back of the class and shouted out, “ I think he’s chewing gum, teacher. That must be a really big wad he has in his mouth. Maybe he should spit it out.”

But the teacher ignored her and continued calling other names until the first dismissal bell rang. Now Jerry had a chance to slip into to boys’ washroom and remove the panty-gag. In a toilet stall he took the speedo out of his mouth and was about to stuff it into the back pocket of his jeans when he paused, held the cum-soaked panties to his nose, sniffed, smiled and then put the panties-speedos into his back pocket.

Jerry’s contrary gender feelings were to continue all through high school. He cleverly managed to get bullies, especially girls, to privately humiliate him, mostly by his being stripped, spanked, and forced to masturbate then eat his own cum. Always his torment took place in private areas of the school, like locker rooms, washrooms, janitor’s closet, empty classrooms etc. Or else he’d be confronted in secluded areas near the school, like the wooded park that stretched for a few blocks. These girls were tough bullies but they weren’t stupid. They knew they’d get into trouble if any of their antics went too far and were seen in public.

Jerry’s reluctant but coerced reaction each time made it look like he hated it. In fact, he often put up a feeble fight which he always clumsily lost on purpose. Of course, that just encouraged his bully attackers to push him further and further. Each time, in the end, Jerry let them do whatever they wanted.

The odd thing is, Jerry really did hate it, but it was a sort of hate-love addiction for him and as horrible as it felt during his abuse, it felt just as wonderful after and it left him wanting more. It was an act of submission to his contrarian dilemma. For him it was win-win. His rep as a wimp was reinforced, he’d get excitingly humiliated, and everyone assumed he was a regular guy who was such a scaredy-cat, he could be bullied into very embarrassing situations. Only a dozen or so bully-girls and a lot more bully guys actually put Jerry through the wringer. But it was rumored throughout school that Jerry was a wuss and easy to pick on.

By graduation day, Jerry Jackson had been maltreated and humiliated many times. He’d also had lots of nasty nicknames given to him by bully boys and babes. Most of the student body just called him ‘genius Jerry the jerk’ because they’d seen the straight-’A’ student being so shy and clumsy; also they’d heard about, but not witnessed, some of his humiliating adventures. Most of his school mates only mocked him behind his back.

But the most horrible nicknames Jerry had to endure were addressed right to his face by the bullies themselves: ‘Jerry Jack-off-son’ was one. ‘Jerry-Fairy’ was another. The worst came from the girls who first accosted him and continued for years to get him to strip in the girls’ washroom and told him to take on a metro-sexual look, that is, shave his pubes like a little sissy-slut girl. They called him all sorts of wimp, sissy, nerd type nicknames too but what really got Jerry was their sing-song reciting of this sadistic jingle:

‘Hairy-Jerry, he’s not scary! He shaves his balls like a fairy That’s because he is so wary Of the scissors which we carry. After school he dare not tarry, Lest we maul and de-ball Jerry.

For we’ll cut off his family jewels Should he ever break our rules. He must have no pubic hair And so we often strip him bare. We must make sure that there Is not a single hair down there.

If Jerry dares have hairy nuts, He’ll find that our scissor cuts Off that which makes him a boy. His manliness we will destroy. So much fun we would all enjoy If he became our eunuch toy.

It was only teasing, of course, and it was only sung when no one else was around except Jerry and his bully-bitches. But to make it seem real, one of the girls occasionally would have a large pair of sheers in her purse when they pulled Jerry into the girls’ washroom, made him strip naked for pubic hair inspection and would use the sheers’ blades to lift his balls back and forth to get a better view. Jerry soon got to enjoy his prissy pubic shaving routine almost as much as these mock-scary surprise inspections that happened unannounced two or three times a month.

On occasion Jerry would also be dragged into the boys’ gym locker room, forced to strip and then mocked for his lack of manly hair ( the girls had also insisted Jerry keep his armpits hair-free too ) The boys weren’t as cruel as the girls, but they did treat Jerry to bare ass towel whipping as they laughed and jeered at the poor lad.

That was Jerry’s high school sissy-humiliation experience. He managed to keep it secret from the teachers and school administrators who saw the boy as a quiet, shy but brilliant student. Jerry graduated magna cum laude. The bully girls once made Jerry ejaculate into a full Starbuck’s coffee mug and then drink it all down. So they sneeringly referred to the scaredy-cat scholar as graduating ‘ Mocha Cum Latte ‘.

Jerry was still divided in his mind, body and soul as to his gender-bender ID and inexplicable enjoyment and sexual arousal at being humiliated and forced into sissy circumstances. He wanted to leave all this behind as he prepared for his freshman year at Harvard. In another state, where no one knew him or his history of sissy-taunting, he might be able to come to some resolution of his split dread-desire dilemma.

Jerry knew he had to choose one way or the other: To be a man or to be unmanned; that was his question. “ Aye, there’s the rub...” he thought to himself as he stroked his hard cock beneath the panties he was wearing under his jeans. They were the pink panties one of the bully girls had given him as a mock graduation present. Little did that girl know how Jerry treasured them.

Boston in late September was busy and beautiful with the leaves just starting to turn and young men and women scurrying about preparing for a new term at Harvard University or the other colleges in the city. Jerry Jackson had settled in to a dorm and was getting to know his roommate, George, who was a bit of a slob but was affable. George was a few years older than Jerry and a good listener.

After a couple of weeks getting to know his roommate, Jerry found himself chatting openly about his difficulties in high school, portraying himself as the unfair target of bullies who were jealous of his superior intellect. He even told his sympathetic roommate about the humiliating taunts he had to suffer for years. George seemed to empathize and admitted to Jerry that he too had been picked on by tough kids all through grade school, but that bullying stopped in tenth grade when he joined a high school fraternity.

Jerry was curious. “ How did that help you, George?’ he asked.

“Well, I suppose it was partly a case of strength in numbers, “ explained Jerry’s roommate, “ but I think it was a change in my own self-esteem that turned things around. A fraternity is like a well-structured gang Manliness and growing up as men ought to are what fraternities are all about.”

“Really!” said Jerry who had always considered fraternities and sororities to be social groupings designed to bolster the insecure and feckless. That it gave strength to its members was news to him. “ Tell me more, George. Did your sense of self change when you became a frat-rat?”

“Not a ‘frat-rat’, Jerry.” scolded George, “a tested and true member of the society of men. Not macho, just a responsible self-assured man. It’s the same with sororities where girls who pass the initiations come of age and become women in their own right. I’m thinking of pledging next term for one of the fraternities, or ‘Greek Societies’ as the posh guys call them. High school groups are okay for self-esteem, but for future connections in law or the business world, there’s nothing like a fraternity key and fellowship for male support.”

“We didn’t have frat houses or sororities in the high school where I grew up, “ said Jerry “ Maybe I’ll think about joining one here, though. Can you recommend one that might take in a guy with a less than macho rep?”

George laughed and replied, ‘ You mean you were pussy-whipped all through high school and you want to man-up now?”

“Not so much pussy-whipped,” thought Jerry who was blushing deep red now, “ as sissy-wished. “ But what he said to his roommate was, “ Yeah, I kind of buckled under to bullies and jocks who made me feel like a wimp, even though I knew I’d be succeeding at college while they or their type would soon be working for me.”

“That’s probably true, Jerry,” conceded George,” but being your own man and not scoffed at or shunned by others is worth more than money or professional prestige. When you go to bed at night, it’s not Professor Jackson who dreams; it’s just Jerry. It could be scary-Jerry or fairy-Jerry. Which one you feel you are, is up to you.”

It wasn’t hard to convince Jerry that what was needed was for him to make up his mind and act on his decision. The contrary complementary conundrum he’d been in all these years had to end somehow, one way or another. Was he a lion or a pussy? The next day he brought the subject up again and asked George how to go about getting into a fraternity. George surprised him with his answer.

“I think, from the little you’ve told me about yourself, Jerry,” began George as they sat in their dorm room, “ is that you need to join a Greek group with a very demanding pledge initiation. One that that will turn you into the person you really want to be. And I happen to know of one such a group, Lambda Gamma Beta. If you like I can put in a word and see if you can try out this weekend for an initial pledge night to see if you’ll fit in for a full initiation.”

“Lambda Gamma Beta? What’s so special about them?” asked Jerry.

“LGB specializes in being supportive. They take the weak-willed, the wary, the wusses and put them through rigorous support-training to turn them into the person they were meant to be. A lot of psychology majors are in LGB and they know how to make an initiation an introduction to a fabulous future and a farewell to a pathetic past.”

Jerry couldn’t believe his good luck. Not only did this promise to be a fraternity to bolster his manly self-esteem but one, George assured him, whose members would understand and support him in his struggle with past humiliation. Help him to overcome it and become stronger and positive and, as he thought to himself but did not mention to George, to become an undivided man, no longer gender-confused but willing and able to commit to his real inner self, whatever that turned out to be.

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