This short story is about Jess and the big changes she faces.
Jess was a 17 year old senior who was surrounded by females. His dad had died several years ago and he had no brothers, only two sisters. Michelle who was in 7th grade and was almost 13, and Amber who was 19 and pregnant. Her husband had been killed in an auto accident a couple of months ago, even before either of them knew she was pregnant. And now she was living back at home and was 3 months along. Jess’s mom was an OB/GYN so they had quite a comfortable lifestyle
“Oh man, my nipples are so sore and itchy I don’t think I can stand it,” Michelle was saying at the breakfast table. “They feel like they are on fire sometimes.” “Honey, don’t worry. That’s very normal when your breast buds first begin to form. In a few months the soreness will go away and they will just continue to grow,” Her mom told her. “Yeah, and then they only get sore when you have your periods….or when you get pregnant….or when your boyfriend plays with them too much,” Amber stated while laughing at the same time. At that moment Jess came up behind Michelle and put his fingers on her chest and started squeezing her nipples through her thin training bra. “There, that’ll give you something to complain about you little wimp. You won’t get any sympathy from me with your stupid moaning and groaning,” he said .
“Stop that this instant young man. She isn’t making this up and you better keep your hands to yourself,” mom said. “If you girls want to know what real pain is, you have to have balls and sample what it feels like to be hit in them. Now THAT’S pain. I can squeeze my nipples and it doesn’t do a thing to me,” Jess said. “God, I wish you could be pregnant and feel the things I do. There’s no way a guy can really understand what all a girl goes through. So just keep your big mouth shut and your hands off our bodies or you might get hit in your balls by one of us wimps,” Amber yelled. Jess stomped out of the room to finish getting ready for school. He knew he couldn’t win what with being surrounded by all those females
After he and Michelle got on the school bus and it loaded with all the other kids on the route, Jess started teasing Michelle about her poor, sore titties. And he was saying things loud enough so all the others on the bus could hear him. Some giggled and others were embarrassed by his behavior. Michelle got very angry but said nothing. She was used to this but knew something had to be done. “If you don’t stop that I’m going to start telling everyone about YOUR little problem. Do you want me to do that, sweetheart?” his girlfriend Amy whispered in his ear. “Would you like all your friends to know how “quick at the trigger” you are when we mess around? Maybe I should stand up and tell them how I barely get it out of your pants before you start squirting in my hands. Is that what you want them to know?” Well that stopped him from saying anything else, at least this time. He hated when Amy brought that up. After all, he couldn’t help it. And she really didn’t seem to mind most of the time. But he sure didn’t want anyone else finding out about it .
That evening before Michelle went to bed she had a long talk with her mom about what had happened on the bus. And all the other times Jess had embarrassed her in front of her friends. Amber walked in as they were talking and she told mom things that Jess had teased her about, too. Like what a cow she was going to be when her titties started producing milk and she would have to feed her baby with them. And they both kept on and on with things he had done to them. Dr. West (mom) knew something had to be done to stop that behavior, but she had tried everything in the way of punishing Jess and nothing seemed to work. “Mom, if only he knew what it was like being a girl and had to put up with not only the physical things but the teasing by boys as well I’ll bet he would be nicer to us,” Michelle said as she started crying. That message stayed in Dr. West’s mind as she went to her office the next day.
She had a few minutes before her first patient so she started reading through some of her medical journals and did a lot of research for the remainder of the day as she had time. She found out some very interesting things that she thought she could put to good use with her son. She decided that although her plan might not be totally ethical to her profession, she would go forward with it for the good of her family and friends. She smiled inwardly as she thought about what an education Jess would be getting over the next few months. She also decided to not tell anyone, including her daughters, what she was up to until it became necessary. Her plan was to most certainly tame her unruly son’s behavior once and for all. And he most likely would get first-hand knowledge as to what Michelle was going through. And maybe even become much more sympathetic to Amber. “The nerve of him calling her a cow…we’ll see how well he can moo,” she thought to herself
Things went along pretty much the same for the next couple of months although Amy was doing a fairly good job of keeping Jess in check. But he still did tease the girls whenever he could. He faithfully was taking the medicine his mom had unexpectedly brought home one night a few weeks ago since she told him his last physical had showed a mineral imbalance that needed to be corrected. He had to keep his body in shape for the upcoming baseball season and he hoped the pills would help. It sure seemed like a lot of pills, though. He had to take 2 of the big purple ones both morning and night and a pink one in the morning. He thought they must be doing something good for him since his premature ejaculation problem seemed to be getting better. Amy had noticed too and thought his body was just straightening itself out .
One thing Dr. West had talked to Amy about, although she didn’t tell her everything, was she felt Jess needed to get some of the same treatment a girl gets from a guy in order for him to start appreciating some of the feelings. She knew Amy and Jess were sexually active because she had prescribed Amy’s birth control pills. She told Amy she might want to play kind of rough with Jess’s nipples, like lots of sucking and squeezing, to get even with his mean comments. Amy thought it strange but felt it served him right and she did get very turned-on when she did it, too
One night when Jess and Amy were fooling around in the living room she had his shirt pulled up and was nuzzling his chest and started licking around his left nipple. He had noticed lately how sensitive he felt there but her licking felt very good. She then wrapped her lips around it and started sucking but he suddenly pushed her away. “Ow, that is hurting me when you do that. Could you take it a little easier? My nipples are so tender for some reason,” he said. At that moment Michelle was in the hallway and heard his comment but didn’t say anything. All she thought at that moment was how glad she was that her nipples weren’t as sore now as they had been.
But the next morning as soon as she saw him she remembered his words. And she ran up to him and put her fingers around his nipples and squeezed as hard as she could. “Oh God, what are you doing…..you’re hurting me you little bitch.” And he just sat there for a moment to recover after she let go of him. “Na na na na na naaaaaaaaa….Jess has sore nipples,” Michelle said as she just laughed and stuck out her tongue at him. Mom didn’t say anything and Amber just sat there enjoying every minute. Jess also didn’t say another word because he knew the teasing he would get if he did. He couldn’t understand why his chest hurt so much last night and now again this morning. He figured it would go away soon. But boy was he wrong about that !
About a month later he was getting dressed for school and pulled a sweater over his head but as it rested on his chest it seemed to itch him something awful. He had noticed lately that his nipples seemed to react to almost everything he wore against them. He quickly changed into a cotton shirt and that helped some, but all day long he was constantly having to reach up and scratch his nipples. The itching was driving him crazy. But there was no way he was going to tell anyone about it. He had even gotten to where Amy’s attention to his nipples were all that really seemed to ease the pain. Her gentle sucking and wet tongue seemed to sooth them a lot. But as soon as she finished and he pulled his shirt on again, they were irritated. Amy noticed this and said “Look sweetie, you’re going to have to do something about that tenderness. It almost seems as though you need something to cushion your nipples from your rough shirts. I have an idea but I know you aren’t going to like it. I think you need like a bra or something.” “A bra, are you crazy? I’m no limp-wristed wimpy queer who goes around wearing a bra,” he shouted at her. She said “suit yourself, I’m just trying to help,” and got out of the car and stomped into her house. He sat there for a moment thinking of what she said. But no way was he going to wear a bra, was he? He also noticed that he seemed to be getting bigger in the area of his hips. He found that out one day when he was pulling his jeans on and had a little trouble getting them past his upper thighs. It also seemed funny that they were not as tight in the waist but were very tight in the seat. But the things that concerned him the most were his irritated and now bloated nipples. He wondered if Amy’s constant attention to them were responsible. They were a deep red colour and were protruding from his chest about an inch. They had always been totally flat before. During the next few weeks it had gotten to where he could hardly stand any of his shirts rubbing his chest. He kept thinking about what Amy had said, although she hadn’t mentioned it anymore .
One day when she was over at his house he told her what he was experiencing and asked if she thought a bra was really the only answer to his problem. “Well, sweetheart, you could always just put up with the pain. Other than that a bra is all I can think of. Besides, I wouldn’t think any less of you. In fact I think it would be way cool to have a boyfriend who knows how it feels to wear a bra. Haven’t you ever wondered about that? Does it turn you on just a little bit thinking about doing something like that? I mean, how many guys would do something like that for their girlfriend?” As she said that she was stroking his crotch and she could feel him start to respond, so she went further.
“You aren’t very big in the tittie department, at least not yet, so you really wouldn’t need much of a bra. Probably just a teeny little training bra….kind of like Michelle wears.” And with that she started working his now hardening penis even more. She thought about all the teasing he had done to Michelle about her sore titties and wearing a training bra and felt this was definitely justice being served. She couldn’t understand why this was happening to him, but she thought he was the perfect guy for it to happen to. And she loved him, in spite of it. Maybe even more because of it
“I’ve got an idea….let’s go up to Michelle’s room and see if she will lend you one of her bras…you know, to just try out.” He started to object but her rubbing him had kind of put him in a trance. So she led him upstairs where Michelle was in her room doing her homework. Amy told her that Jess had something to ask her. He couldn’t get up the nerve to do it, so Amy said “Jess seems to be having a little problem we hope you can help out with.” She wanted to know what kind of prolem. So Amy lifted his t-shirt so she could see his bloated nipples. Michelle gasped and had to hold back a giggle as she stared at a chest that looked very similar to hers. In fact if anything, his nipples were a darker color and even a shade larger than hers
“Wow, Jess, where did those come from?” she asked. He told her he didn’t know what was going on and then to the surprise of both girls he said, “I’m real sorry I was so mean to you, Michelle. I truly didn’t have any idea what was happening to you, but now I guess I do. Please forgive me. And, although this is probably the most embarrassing thing I’ve ever asked, do you suppose you could loan me one of your bras? Amy thought it might help with the soreness.” Later they would find out he just apologized to make it easier and to get away from her room quicker. It still hadn’t all sunk into his brain about what a pig he had been .
Michelle went over to her dresser and pulled open a drawer that was filled with panties and bras. “Do you just want a bra, or do you want a pair of my panties, too?” she teased. Amy thought it was a cute thing to say, and for a moment tried to picture Jess in panties, too, but quickly rummaged around for as plain a bra as she could find. The one she selected was white, very thin and had flat AAA cups. But there was a cute small flower sewn between the cups. She thought it would be good for Michelle to witness Jess being put into a bra for the first time so she had him remove his shirt and he slipped his arms through the straps and when in place she fastened the tiny single hook in the back. It was almost a perfect fit. Michelle thought it was neat that she and her brother were the same bra size……and that he was wearing a bra she had worn many times. She even started to get a little wet between her legs as she watched him start to pull his t-shirt on again. She knew she would have to do something about that when they left the room. Her little clitty started to tense up as she thought about that.
Jess did have to admit that Amy had been right about the bra. His shirts didn’t irritate him at all anymore and he soon got used to the feel of the bra. In fact it kind of turned him on a little knowing he was doing such a secretive thing. And Amy constantly reinforced his feelings as she told him how much she liked him in a bra as she unhooked it and pulled it off so she could attach her sucking lips to his turgid nipples.
Of course all the family knew that Jess was wearing Michelle’s bras all the time and once in awhile they would tease him just to get even a little. But once when Amber said something to him about it he snapped back, “Well at least I’m not a fat cow with big udders like you.” Mom was there when he said that and went to comfort Amber when she left the room crying. She told her that Jess would soon find out how she felt. Amber didn’t understand what that meant but thought nothing further about it. But mom knew she would have to follow-through with the next phase of his education .
One day Jess and Amy were at her house and up in her room messing around. She was happy that Jess no longer had the problm of shooting his wad too soon. In fact it seemed like he was getting to where his orgasms were taking longer and longer. But that just made it better for her. His semen also seemed to be thinner and less copious. She wondered if that had anything to do with his titties and hips filling out. “Jess, have you noticed your jockey shorts are so tight on you lately and that your jeans seem to be ready to split between your butt cheeks? Let’s try something out just for fun.” She went to her dresser and got a pair of her every day, but frilly anyway, panties and told him to put them on. He protested but she saw his penis start to get hard at the mere mention of the word panties. So she started stroking him and said “Oh come on, they will probably fit you much better than your old icky shorts and I’m sure will feel nice up against your big round butt. You know your rear end is looking a lot like mine, so do this for me.” She started sliding her panties up his legs and his penis came to full attention as she did so. But the panties were nicely filled out by his cute butt and full hips. Just an unsightly bulge in the front. She started stroking him through the nylon, telling him how cute he looked in her panties and Michelle’s bra and what a pretty little girl he was becoming. She even went so far as to say he should be called Jessica now that he was wearing pretty lingerie.
As soon as she said that he orgasmed and filled the front of the panties with his watery semen. “Oh, naughty, naughty Jessica. Now we have to get another pair of my panties because of the mess you made.” The next thing Amy did was to get a pair of her jeans for Jess to try on to see if they might fit him better than his did. Again he resisted but soon she had him pulling them up his legs and he noticed how much easier they went over his hips. And to his and her amazement, they fit him like a glove…..almost better than they did her. Well, one thing led to another and Amy found herself playing dress-up with him just like she used to do with some of her girlfriends. Almost all of her clothes fit him and she and he both were very excited and turned-on as she dressed him in her pantyhose, slips, teddies, camisoles, dresses, and even her shoes all were a perfect fit. She wondered if some day he might be able to wear her B cup bras.
About 6 months had gone by and Dr. West knew she couldn’t keep Jess at the very high dosage of female hormones he had been taking and besides he was at the right point for the next part of her plan. Although his breasts were fairly small, she was sure he had developed all the necessary mammary tissue including milk glands and ducts. She knew his poor body had been bombarded by many times more potent hormones than even teenaged girls have in their bodies. In fact the dosage had been so high that Dr. West knew an abrupt cessation of the hormones would trick his body into thinking he had given birth and, in turn, begin manufacturing high levels of prolactin on it’s own. And with all the sucking and squeezing that Amy was doing to his titties, she knew that would provide the proper stimulation to quickly cause him to begin lactating. She felt her panties begin to get wet just from the thought .
Jess’s breasts had grown to about an A cup. They had dug out some of Amber’s old A-cup bras from the attic when he got too big for Michelle’s training bras and Michelle wasn’t keeping up with him in the growth department. His mom told him he didn’t need to take the pills anymore. He was glad because he didn’t think they had done any good. He didn’t even make the baseball team this year because he just didn’t have the endurance or stamina for it. Plus there were other obvious reasons he didn’t want to have to use the guys locker room .
Jess was so conditioned to female clothes by Amy encouraging him and stimulating him when they were together that he now spent a lot of time, in private, dressing himself up. He seemed drawn to Michelle’s clothes, maybe because it was her bra that was the first item he ever wore. He would sneak into her room and gather some of her panties, slips, pantyhose, socks, dresses and shoes. Then he would put them on all the time getting a tremendous hard-on from the sensation of her sleek clothes on his body. He always masturbated while wearing them thinking about how her young, feminine body had worn them. His orgasms were very intense at those times and since stopping the hormone pills his ejaculations were always a huge amount of semen that he had to be very careful to not get on her things. I’m sure he would have loved to have known that Michelle, ever since that day he put on her bra in her room, was frequently masturbating also thinking about him wearing her things. They would soon find out about each other’s activities and share many exciting adventures together .
About two weeks after stopping the pills, Jess noticed every morning that there seemed to be some stains on his nightgown (actually Michelle’s nightgown that he had started wearing to sleep in) and he also noticed that his breasts seemed to have gotten a little more swollen, and that there were dark blue veins circling his nipples around the swollen tissue. One morning he went into the bathroom and looked in the mirror and saw what he thought was a drop of liquid on his right nipple. So he squeezed it and a few more drops came out. It happened with the left nipple also. This scared him and he kind of made a gasp that Amber heard as she was passing by, so she came in to see what was wrong. She was amazed when she saw the milk dripping off of Jess’s nipples. But she also gave a quick smile, knowing how he must have felt at that moment.
“Don’t worry, Jessica. The same thing is happening to mine.” And with that she pulled up her maternity top, undid her bra and let her huge breasts fall out. As she squeezed her nipples, Jess saw milk flow out of her almost exactly the same way it was flowing out of him. “Guess you can help this old cow breastfeed little Brittany as soon as she is born in a few days. Won’t that be fun?” He just whimpered and wondered what else was in store for him………but that’s another story