Rita was growing up, but her parents hadn’t really noticed. To them, she was still just bubbly little Rita, the gymnast, the social butterfly, the solid B student. But her body was changing. She was a late bloomer at age 18, but finally her development was beginning to show. It wasn’t just that the old princess pajamas she always wore around the house were getting threadbare. They were also getting short in the ankle and filling out in all the right places. Her mother Cheri didn’t notice. She was working 12 hour shifts as a nurse and trying to keep a roof over her head.
And her step dad Brian didn’t pay much attention either. He had never been much of a lady’s man, which is partly why she married him after an acrimonious divorce from Rita’s father. Cheri needed someone who would be a force of stability for their family, someone who was not given to fits of violent rage like her ex. Brian was sweet and kind, and Rita liked him. He wasn’t much in bed, but that wasn’t the most important thing for Cheri at this point in her life. She only wished he could find a decent job. With the little money he earned, it made more sense for him to stay at home and keep house than to work. He was handy and a decent cook and kept the place clean. That’s why her idea to convert the basement rec room into an AirBnB was so brilliant. It would take advantage of all of Brian’s talents and earn a steady income while allowing him to stay home with the kids.
There weren’t as many applicants as they expected. They settled on Nick, who had recently relocated to their town for a job as a computer security expert. His job allowed him to work from home part of the time, but he sometimes got called in at odd hours to attend to a security crisis. His contract was for a year, so it seemed like a good way for them to try things out before committing to a long term lodger. Nick was confident, friendly and charming. He knew magic tricks, which won the children over to him immediately. Brian felt uneasy around him from the beginning, but he wasn’t sure why. Maybe he envied Nick’s stocky physique, or his confidence and easy charm. The downstairs bathroom was right over Brian and Cheri’s bathroom, and the sound of Nick urinating was easy to hear if the house was quiet. He wasn’t sure if it was because the sound was muffled by the intervening floor, but Nick seemed to have a much stronger urine stream than his. It was a growl compared to Brian’s tinkle, and was over much more quickly. Brian wasn’t worried about Nick hearing him since he usually sat while he peed in order to keep from dribbling on the rim of the toilet, which he would then have to clean. After hearing Nick, he resolved to sit every time.
Some months passed and they adjusted easily to having a lodger. Nick was quiet and clean and friendly, but mostly kept to himself. It was Covid time and the kids were doing school from home on the computer. Cheri was working one of her long shifts. Brian was trying to fix the dishwasher, which wasn’t draining properly. Rita came in and asked if he would help her with her algebra homework. Brian said he was busy and suggested she see if Nick was around since he was a computer expert and so must be good at math.
So Rita knocked on the door to the basement and called down, “Nick, can you help me with my algebra homework?”
She heard a muffled “sure”, and so tried the door knob and it was open. The door could be locked from either side, but they weren't consistent about locking it. Rita wasn’t shy about going down there since it used to be her rec room.
Rita was a willowy blonde whose Latin sounding name didn’t really suit her, but she liked it better than Margarite or Marge. She was wearing a baggy pink t-shirt with a picture of a princess on the front, her old threadbare blue pajamas, and pink flip flops. The t-shirt only half covered her plump little bottom, which was nicely revealed by the thin clingy pajamas. She had a fine little rump on narrow boyish hips, impossibly plump compared to the rest of her body, which was otherwise thin and bony. If she had much in the way of breasts, the only thing that showed through the baggy t-shirt was an occasional sharp nipple stabbing Princess in the eye.
Nick was at his desk in front of his computer scrolling through lines of code. He was wearing a thick fleece jacket over his t-shirt, since it was always a little chilly in the basement, and gray sweatpants. He used an infrared space heater under his desk to help stay warm. Rita put her laptop on his desk and stood next to him.
“I don’t understand the quadratic equation,” she said.
“No problem, I can help you with that,” Nick replied. He did his best to be his usual cool and casual self, but he was actually feeling a little excited and uneasy with this young maiden standing next to him. He could smell her shampoo, and it was difficult for him to keep his eyes off her body. Her protuberant little bottom was a source of endless fascination, and once he received a glimpse of something soft and pink through the loose sleeve of her shirt, his eyes searched hungrily for more.
“I don’t understand what it’s supposed to do,” she complained.
Nick was a good and patient teacher, but the proximity of the young maiden was more than a little distracting. She sidled right up to him since they were both working on the same laptop, and also it was cold. After 10 or 15 minutes had passed and they were making some headway with her homework, Nick found that she was half sitting on his thigh.
Suddenly she exclaimed, “Oh, I get it!” and slid her full weight onto him so that the two cheeks of her buttocks were straddling his thigh, and her flip flopped feet were dangling above the floor. It felt much more comfortable for her to be warm on his lap in front of the heater, and it felt much, much more comfortable for him to have a young maiden squirming on his thigh. He felt his cock growing. They kept working. They were doing sample questions now, and every time they got one right, she danced a little jig on his thigh. Soon, Nick’s cock was full hard and straining against his sweatpants.
Rita had to hoist herself back up every so often as she slid down Nick’s thigh. When she put her hand down to do this it landed right on Nick’s cock, and he let loose an involuntary groan, not necessarily one of pain.
She pulled her hand back quickly and exclaimed “I’m sorry! I’m sorry!” genuinely worried that she had offended him or violated him.
Then after not more than a beat or two, when she realized he wasn’t offended, she said “What was that? I mean, is that part of you?
“Yes,” Nick said sullenly, ashamed and not sure whether he was in trouble.
Then Rita said plainly, “It’s much bigger than my daddy’s.”
Nick said quizically, “How do you know how big your daddy is?”
Rita shrugged and said, “I’ve seen it. I spied on him when he was masturbating in front of the computer, and also he put pictures of his cock on the computer for some kind of sissy website or something. It’s ok because he’s not my real daddy.”
It took Nick a few beats to digest all this. Then he said, “It’s not really that big. I bet I could fit it through that little hole.”
There was a small cigarette hole in Nick's sweatpants part way down his right thigh (Rita was sitting on his left). She was used to Nick making outrageous claims for his magic tricks, then proving them right with a trick. So she immediately took the bait, exclaiming, “You cannot!!”
While Rita watched in open-mouthed excitement, Nick then took hold of the fabric of his sweatpants near the hole and forced it over the head of his cock. A reddish pink button about the size of a small strawberry emerged with a pop and the stretched fabric held tight just under the corona. Rita gasped and said, “It looks just like a little mouse! It’s like Ratatouille!” (referring to the cartoon movie about a cook who receives instruction from a rat living under his hat).
“That's right,” Nick said, “I don’t actually know anything about programming computers. He tells me what to do.”
With that, he took a Sharpie marker from his desk, and drew mouse ears, eyes, nose, and whiskers on the head of his cock. The opening was the mouse’s mouth. Then he squeezed it between his thumb and forefinger so it looked like the “mouse” was talking. Using ventriloquism, he made him say in a thin voice, “Hi, I’m Mick. Nick doesn’t know anything. I’m the brains around here. I tell him what to do.”
Rita burst out laughing, and such hilarity ensued that she fell off his lap and rolled around on the plush sheepskin rug in a pile of hysterical giggles. This went on for several minutes.
By this time Nick had put “Mick” back inside, afraid that all the noise would attract attention from the people upstairs.
Once Rita regained control of herself, she came to rest facing away from him on her side with her bottom leg extended straight and her top leg flexed knee to chest. This gave Nick the perfect view of thin pajamas stretched over her perfect ass, and his erection raged so that he dared not get up from the chair and expose a scandalous “tent”. She convulsed a few last times with laughter. Then the mood suddenly changed. She got up sullenly and, without making eye contact, took her laptop and started to trudge reluctantly upstairs. Nick was worried now.
“Don’t tell anyone about my little mouse, okay?” he said sheepishly.
Rita turned around, looked him in the eye, and said “Don’t worry, I won’t tell.” Then she went upstairs, closed the door, and locked it behind her.
We have to talk about Nick’s little mouse, aka Mick. Nick in fact had a very large penis, but it was a special type of penis. The head of it, the glans, was relatively small. But the shaft that supported it was much thicker, so that it looked a bit like a comic book hero with a tiny head planted on broad shoulders. That is why he was able to pop the head of his cock through that tiny hole, while remaining confident that the fabric would not slip further down his shaft. To add to the freakish nature of his endowment, his shaft got thicker and thicker towards the base, inch after inch, so that at the point it connected to his body, it was very thick indeed. Among connoisseurs of cock, this type of cock is known as “the despoiler”, since the tip admits easily into the most constricted orifice, and then wedge-like shaft relentlessly pries it open. The possessor of such an evil instrument has the option to gently despoil his virgin consort with shallow thrusting using only the first portion of his cock. But the fires of lust are rarely satisfied with this kind of restraint.
Ch.2
Since the Mickey Mouse episode, things were different between Rita and Nick. She went down to see him with her father’s permission once or twice per week for help with her math homework, but she was more stand-offish around him. She kept at least a couple of feet distance between them at all times. At the same time, she seemed to feel the need to show off around him. One time she was showing off a yoga pose that she had learned when… Rip! Her favorite threadbare pink pajamas split right at the crotch.
“Oh no! I can’t go back up like this. Brian will have a fit!” said Rita.
Nick said, “don’t worry, we can sew them up right here.”
“No way I’m taking my pants off for you, Mister,” Rita shot back.
Nick, cool as a cucumber, said “you don’t have to. I can sew them up with you still wearing them”
Rita thought about this for a few seconds. Though she did not admit it to herself, she secretly craved Nick’s touch. The situation seemed to give her the opportunity to satisfy her longing while at the same time denying it. Nick meanwhile had no illusions about his motivations, and was merely trying to create an opportunity to get closer to her.
Rita finally made up her mind.
“Ok, but no funny business,” she said.
“No funny business,” assured Nick.
She bunched up the torn part of her pajama crotch behind her, and lay face down on Nick’s couch clenching her buttocks tightly. She was wearing tan colored satin panties - old lady panties. Her ass was fantastic. Nick mustered every bit of coolness and professionalism he could, sat down beside her, and started to sew.
“Stop squirming,” Nick said
“I can’t help it, you’re tickling me,” replied Rita.
“I’m not even touching you,” said Nick.
“I know, but it still tickles,” she said.
“Just keep in mind I’ve got a needle in my hand,” said Nick
He went back to work. She continued to squirm. Then she bucked her rear up suddenly and the needle went in her left thigh, just under the panty line.
“Ow!” she said.
“Shhh!” hissed Nick, “he’ll hear upstairs.”
“I don’t care, you hurt me!” said Rita.
There was a small bead of blood appearing on her white flawless skin.
“I better get some alcohol to clean it,” said Nick, and got up to get it in the bathroom.
He was now officially shaken, worried about where this was headed. He returned with a bottle of isopropyl alcohol and a cotton swab. He poured the alcohol onto the swab, unwisely holding the bottle right above her. Too much came out, saturating the cotton ball and spilling right into Rita’s crotch.
“Oh shit, that stings,” she said, feeling the alcohol on her needle stick.
But the alcohol also saturated the gusset of her panties, and after a few seconds, she began to feel an intense burning in her anus and pussy.
“Ow Ow OW OWW!” her voice started to rise.
Nick instinctively put his hand to her mouth to keep her from screaming. She bit down hard on the fleshy part of the hand opposite the thumb while she whipped her pajamas and panties off as quickly as possible.
“It’ll stop burning once it evaporates,” said Nick. “Please just don’t scream. It’ll be over in just a minute.”
The young maiden was breathing heavily and holding her breath at the top of every inhalation, scrunching up her face and biting hard on his hand. The only thing he could do is watch her perfect backside squirming and heaving up and down on his couch while she held her pussy in front and bit him hard. It was exquisite and well worth the pain of her biting his hand.
Soon her bucking and moaning began to slow and she eased off her teeth from his hand. Her bottom was so white and round and lovely that it seemed to glow in the dim room.
He covered her with a blanket that was on the backrest of the couch and said, “I’ll fix them now.”
She didn’t say anything. After a few minutes he had them sewn up and handed them back to her. She put them on under the blanket and got up in a hurry to leave.
This time, it was her turn to turn around on the stairs and ask, “don’t tell my mom and dad about this, ok?”
“Don’t worry, I won’t,” he reassured her.
She had left her panties behind. They smelled delicious.
—--------------------------------------
While all this was happening, Brian was upstairs on the computer in the spare room. Something was happening to him that he did not understand. He had been using internet porn now for many years.
It satisfied a strange curiosity in him. You see, Brian had a small penis. For almost all of human history, the little-cocked man would normally never get to see a big cock. He got to see his own of course, and he saw other men’s soft cocks in the locker room. He might hear rumors about how big another man’s cock was. But the little-cocked man would never actually see a large erect penis, and so would never know how he truly compared. The internet changed all that. Now the poorly-endowed man could see large erect cocks in action from the comfort of his home. After watching internet porn for many years, Brian believed that his cock was smaller than almost any male who was past puberty. This made him feel physically deferential and submissive around other men.
At first he justified these proclivities by his own meager endowment. “This is an experience I would never have except by watching it,” he told himself. “This is the closest I will ever get to having a big cock.” Nature had given him a bit less than 5 inches, not quite a micropenis, but definitely small by any standard. But to make matters worse, the shaft of his penis was very thin. The head of his cock was comparatively normal, but the shaft was not much thicker than a grown man’s thumb. This type of cock, among connoisseurs, is known somewhat disparagingly as the ‘lolly-pop.’ It was the exact opposite of Nick’s cock. By a strange coincidence, though he would not discover this for a while yet, the head of his cock was exactly the same size and shape as Nick’s. But while Nick’s relatively small cock head stood on top of a thick burrito, Brian’s cock looked like a mushroom on top of a stick of asparagus.
Brian noticed that his taste in pornography had changed over time. In the beginning he would look at softcore pictures of beautiful women, and over time progressed to harder and harder material. Soon he was watching men and women having sex on video. He preferred to watch well-endowed men having sex with petite women. It was fantasy fulfillment on two levels, because he always dreamed of being with a beautiful young woman, and he always dreamed of having a big cock. He searched for videos featuring men with bigger and bigger cocks. He would sometimes imagine one of these beastly men satisfying his wife in ways he never could. Sometimes he imagined them forcing open and ‘resizing’ his young daughter’s virgin pussy.
In time, the woman became less important and he only cared about seeing men with big cocks. Eventually he came to prefer to see cocks from a woman’s perspective, up close and from below. The progression in his attitude to other men’s cocks over time went from outrage, to envy, to admiration, to adoration, to submission. When he finally discovered sissy porn, he realized who he really was inside. He wasn’t a woman, but he also wasn’t really a man. He was a sissy.
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