Jamie Clout

Miss Johnson asks Jamie a personal question about why he wants to wear feminine things. Jamie does his best to explain.

Jamie has been eating his lunch daily in front of Miss Johnson's lingerie store. She takes the initiative to invite Jamie into her establishment.

I found some gorgeous lingerie advertised in a window and just did a little shopping.

Haven't written in a while. Mother and Auntie took away my computer and electronic gadgets to experience life as a Quaker Gal.

I think it's Adema's fault for leaving her shoes in the apartment hallway. They become too great a temptation and James steals a pair.

Oh, how I wish I could have had better conversations about cross-dressing with my Mother. So I continue that dream here, with Mother encouraging me to cover a little on top. I have nothing to support but Mother insists I cover my nipples for modesty sake.

Jamie helps Megan try on a skirt in the dressing room of Madge's Boutique. She asks for a few pictures of him wearing her panties.

I've often wondered what a Mother/Daughter conversation would be like and this is what I would have dreamed it would have been with my Mother.

Finding a strange panty in my laundry basket was only the beginning. I love an understanding Mother!

Mother caught me surfing the Victoria's Secret web site and playing with myself. She decided to teach me lesson and make sure I had plenty of opportunity to see the undies I admire so much.

Karen and her new lover, Jack, decide this little sissy bitch should be a real bitch, as well as their personal maid and cock sucker.

It's finally over - A successful Southern Ball. We didn't win any contests, but Tammy and I were accepted at the ball, and even in the swimming pool. Thank you to all those commenting and giving me ideas for this short story.

Mother walks in on Tammy and me while I'm under her dress. Kind of an awkward moment. She should have knocked. We try out eating while wearing hoop skirts. You can't imagine how difficult it is wearing a ball gown.

Serendipity - the faculty of making fortunate discoveries by accident. The middle school girls are wearing old fashioned prairie dresses. The school board is talking about adding ballroom dancing to the high school curriculum. You see, one little idea can blossom into a wonderful world. Womanhood is wonderful!

Two weeks till the big event. Thought you might like to see Tammy's ballgown. Tammy and I have become a lot closer. We went to see my counselor and talk about the big event.

The farm story continues. Tammy spent the night comforting Jamie in her time of sorrow (not!) and Jamie explains her idea on how these girls can attend the ball and both take lead and follower roles while ballroom dancing. Waiting to determine where the ball will take place. The Governor's mansion might not be big enough.

The breakup with Jack - It was bound to happen. So Jamie needs a date to the ball. Mother suggested Tammy! What do you think?

Karen makes James sit with the Bridesmaids at the reception. He dances and leaves with Bill. Seems like this was all planned but Jamie didn't know anything.

The ball drama continues, with Tammy visiting the farm, and an unexpected sleepover. It's kind of different being the expert on transgender issues in a community.

A little update as to the ball situation. A note to say that Brittany is doing well and her mother is seeking therapy. Jamie is angry with Jack so you'll have to read why and Mother has a Mother/Daughter talk about the birds and the bees. How fun is that?

Hey, there is a new girl in town, I mean, someone like me. Miss Davis brought her son in for a bra fitting. This is the story of how I met Tammy, and I hope she'll be a close transgendered friend some day.

It's been agreed by the Governor and his wife, and just about every community in Iowa to hold a Southern Ball fundraising event. So Jamie now has a new objective to pass through. She did fine with the prom. How is she going to do on a state-wide event?

Well, it's the holiday season, and Jack has bought me some 'not so thoughtful' gifts. My brothers are asking me what they should get their girlfriends. I thought I'd drop a note about the holidays to help those clueless male individuals what a girl has to go through, especially this first year as a girl.

After the successful high school prom, our quilting bee has decided to 'up the ante' and come up with a more successful event. Needless to say, a much bigger event comes to fruition. A state-wide ball might be just the trick to make the quilting fund successful.

Karen has decided how she's going to let James know she knows about his wearing her clothes and she's going to do it publicly. Poor James doesn't know what he's in for.

An update to the Farm Story - What on earth happened to Jack and Jamie? How are the brothers making out with their prom dates? Just a note to respond to the questions. I guess the story did end abruptly, didn't it?

Brittany spends the night with Jamie. Church on Sunday is very successful in introducing the new Brittany to boys in the community. Jamie and Mother have a serious conversation. A good week!

Trying to teach a real girl about bathroom routine can be a bit awkward, but I'll do my best. This isn't gross or anything. Just stuff girls need to know about.

Brittany has asked for Jamie's help in getting rid of her 'frumy' look. Turns out this is a bigger project than Jamie expected, but worth the effort.

Mother and Brittany have asked Jamie to make Brittany more popular at school, and they decide a new wardrobe will probably do the trick. Jamie has also been asked to wear a corset and increase his breast size as he's now assistant manager at the boutique.

Someone left her panties in the dressing room for Jamie. Let's see how this story develops.

James has to work at Auntie Madge's boutique after school each day. He's getting good at it, and Madge invites him to accept the assistant managers' position.

Well, the prom is finally here. There's the day's before preparations, and Mother and the women prepare for a big pre-prom dinner. Then PROM NIGHT! And of course, afterwards.

Jack saw one of the football jocks smack me on the behind. I need to set down with him and lay the ground rules for a what a girl expects in a relationship.

Some have asked for me to provide a little more information about the girls in my clique. We hang out at school of course, and I thought I'd describe what it was like to visit them and see them in their prom dresses before the big event. I think you'll agree, they are all awesome friends and I'm glad my brothers are all dating this bunch of wonderful young women.

A quick picture of the dresses each of the girls will wear. Two weeks left and our clique is helping with the decorations. Maybe we can get Gus to wear a black tuxedo.

We girls went girdle shopping, then tried dancing practice with the boys so we'd be ready for the prom. It didn't work out as planned. Kind of funny if you think about it. But all things work out in the end. So you find out who's taking whom to the prom. Yeah! One month.

Well, this chapter is all messed up, as I've added the sleepover with the dress shopping, an adorable swimsuit I just had to have, and little about the dinner with the brothers. My mind's all over the place with this prom thingy coming up in one month. And now Audettes' acting a little lesbian. I'm okay with it.

Getting closer to the prom. Got to start doing some serious shopping. The girls are coming over for a dinner and sleepover. Trying to find dates for the prom. I'm responding to some of the many questions asked as well. Thanks to the reviewers. Good Questions!

Well, the story continues, per reader request. I'm introducing the girls, Audette, Claudia, Amy, and Connie. Four brothers, all possibly going to be attending the prom. Even Father is becoming involved with the continuation of life on the farm.

Well, I've made Jack commit to taking me to the prom. Enough of this nice girl bull-shit! But Miss Johnson wants to be involved with the prom girl excitement, and Jack's her only son, no daughters. Jamie gets a sex toy! And Tammy doesn't get to play anymore. (She's a bitch anyways)

Well, Jack invited me to dinner at his house. That's weird. He hasn't been talking to me for the last week since he's been dating Tammy. Now he wants me to sit down to dinner with his mother, Carol. Life as a young woman is lot tougher than I thought it'd be!

Karen observes James staring at a pregnant woman so decides that he should get to experience being pregnant. They do a little lingerie shopping at a maternity store for a dozen new undies. And something for Karen and Alice.

A farm story continuation - Jack went out with a real girl and put prom plans in jeopardy. What does a cross dresser do when 'her' guy starts going out with a 'real' girl?

A transgender counselling session, recorded and written with permission of the counselor. Somewhat of an autobiography and responses to questions about what it's like growing up in a transgender, yet hidden, world.

Unless by popular demand, I think this is the last of the Jamie / Jack stories. It ends on a sad note - Thank you all for the kind reviews. This has been an assignment from my counselor. She really does expect journal entries (In a pink journal). There are plenty of Jamie stories to read, as you might have noticed. I'm surprised that some of my favorites have no reviews. My counselor thinks I'm making progress :)

That third date is supposed to involve sex. I don't know why this is the rule, but I was going to follow it. Mother and Mrs. Johnson set me up on a third date with Jack. An over-nighter, it turns out. And the first indication that a counselor might get involved.

Jamie wants to develop a better relationship with Father and decides a fishing trip might be the best way to resolve any differences. Thanks for the comments!

In response to readers questions about Jamie's life on the farm, I've described the living conditions. And I've gone on another date with Jack! Yes there is sex, and it turned out to be a wonderful first sexual experience.

For those requesting this story continue, I've gone ahead and finished it. No hormones or treatment, just a closer relationship to Mother and a date with a boy!

A variation on the 'Karen catches James wearing panties at work' with Karen taking James to the JC Penney semi-annual bra sale. James has a few interviews on the way and they meet up with Alice.

Karen and Alice have decided that James isn't big enough for big girl panties, so they decide to take over, redecorate his spare room, and let him live the way he wants to.

A continuation, per request. Thank you, reviewers for your observations. Jamie and Mother go for a swim on an August weekend. Jamie and the girls try on some swimsuits, and then a movie and a sleepover. Just regular old girl stuff!

Too many sons. The youngest is just going to have to stay at home and help Mother with the 'women's work.' Another Jamie fantasy with a not so unwilling young man, and Mothers' approval, James starts working around the house while his older brothers get to do the farm work.

Another Caught with Consequences short story. James doesn't tuck his shirt in properly and Karen can see he's wearing Hanes Her Way panty briefs. She takes the initiative and brings him out to lunch. A run in her pantyhose and he has to buy her some new ones.

The final installment - definitely autobiographical. A lot of explanation. Encouragement to read any of the other stories I've published. And please feel free to review any of them.

By request, I'll continue this story - James and Mother start working out a Mother / Daughter lifestyle, with a bra fitting on Thursday afternoon. How cool is that!

James accidentally put one of his bras in the laundry room. Mother took the initiative to confront him and resolve this mystery once and for all.

After a night of sexual passion, Karen leaves Jamie's house wearing his intimates. But she invites him to her house to continue their sexual fun.

Karen notices the lacy waistband on James' panties. A conversation ensues leading James to invite Karen over for dinner and an opportunity to look into 'Jamie's' panty drawer.

The new 'Glamour' magazine arrived and Mother has found some lingerie that she wants Jamie to get.

Imagine what it would be like if Mother and Aunt Madge got together to humiliate James and Timmy. They enjoy the dress up games so I guess it won't happen but I can dream of what one day would be like.

Another story of James getting trapped into wearing women's clothing. An office story.

James compliments Hedda on her clothing and perfume. He keeps staring at Hedda. For punishment, Hedda takes him shopping with her so he can purchase her a gift.

A young woman makes a fashion blunder by not wearing a slip. Mother tells James to inform her and help her out a little. This turns into a shopping for dresses day for James and Tammy.

Tammy had a run in her hose, and Mother didn't have a pair to lend. It's about time to borrow something from James' room. A little bit of incest but still nice and sentimental, I think.

A continuation of that awkward moment when Mother confronted me with my feminine tendencies. She's been visiting with a gender identity counselor and this is how things develop.

Typical Mother finds girly clothes in son's room story. I just like to imagine the acceptance of a caring mother.

James has to stay at Auntie Gail's for the weekend. Tammy and her friends show up for an afternoon swim. Luckily, Tammy brought Jamie's suit as well.

James spends his summer days at Tammy's house. It's getting hot and he forgot to bring his swimsuit. Tammy has one he can borrow.

Mother and James enjoy a board game in the evenings, but Mother says she'd play better if she weren't so distracted by James' old, ragged pajamas. Time to get a new pair.

Mother went looking through James' dresser and found a hidden bra and panty set. This is the conversation they had afterwards.

A continuation to the psychologist visit with Jeanette. Does James have to tell Tammy he's really a boy? I wonder what happens during the meeting with Mother and Miss Johnson?

Why Mother and James moved from Texas, starting new in Oshkosh. New friends and a gender counselor as well.

The final installment of A Party Dress for the Holidays. Jamie and Mother go to a beauty parlor for a haircut and manicure. An evening at the ballet is Jamie's Christmas present.

Mother and Jamie spend a day at the mall, training Jamie for his evening out at the ballet.

Mother and Tammy sit with Jamie and explain the situation as they see it.

Dinner and a gift exchange at Tammy's house, then a visit with a sleep over at Jamie's house. It's a joyous holiday week for everyone.

It's Wednesday before the holiday and Tammy invites James over for dinner and a gift exchange. Mother had James' room redesigned as a really big Christmas gift.

Shopping done, Mother asks Jamie about some new furniture, and don't you just love Duchess Kate's summer dress?

The continuation of Jamie's shopping experience with Mother, dressed as a boy (this time).

James agrees to tag along with Mother as they go shopping for that little black dress and some lingerie for a holiday outfit for Jamie.

Mother asks James' advice on a dress for the holidays. It turns out she is suggesting the dress for James.

With too many panties in the laundry this week, Mother decides that James should have his own underwear.

This is a fictional recording of a James / Jamie session with a therapist. Please review!

James get made fun of on the school bus because he's staring at Tammy's tights. It's all a misunderstanding but Mother makes a bigger issue than it really is.

Jamie's 2nd night sleeping over at Tammy's house. It turns out that Mother and Miss Johnson had planned this little get together all along. Jamie and Tammy become closer friends and attend service in pretty dresses. How cool is that!

Thank you to those responding - here is a 2nd chapter. James gets to spend the night at Tammy's house for a real girl's sleep over. He gets to experience a dance class with Tammy, Leah, and Cindy. My stories are my stories and they are as long as I write them. Complaining about length won't make them any longer though I appreciate your interests in reading more about James and his desires to have a feminine relationship with his mother.

Tammy and James have been best friends for years. Mother needs to leave town for a few days for work and asks Tammy's Mother if James can spend the weekend there. "It's not going to be like a sleepover or anything," Tammy explains.

Mother finds a pair of holiday panties in the dryer. She confronts James with the discovery and he tells of how he got those undies.

Karen and Margaret have an innocent (maybe not so innocent) little chat about James' fetish for women's lingerie.

James and Tammy are close friends, and James buys her some mascara as a gift. Things get out of hand when James visits Tammy's home to do some homework.

Mother finds an extremely feminine purple nylon brief under James' mattress. She explains to Miss Johnson all that transpired since discovering James' little secret.

For some reason, Tammy agrees to go home with James, but finds his lingerie chest full of his intimates. I think he was more surprised than she about the panties in his drawers.

James gets invited to go on a date with Tammy, but he has to wear those panties she gave him.

James can't keep his eyes off Tammy's legs. She gives him a better treat than just looking during lunch.

A brief overview of why a guy might want to dress up like a girl. My story.

Karen tells me to compliment Miss Robin's skirt and ask for the pattern. Karen helps me to get the petticoats and pantaloons.

James gets caught and reported that he'd flipped Tammy's dress during school. Mother selects an unusual form of punishment, with Tammy and her mother involved.

Jamie and Mother return from their shopping trip and start emptying the bags.

Father has left the home to Mother's satisfaction. She hates men and decides to remove every bit of evidence that a man(or boy)ever lived there.

A little more personal information about my relationship with Lisa. Thank you to those asking about her!

James graduates college and visits Mother's house. Things change quickly when Mother informs him that an old middle school friend is interested in asking him out on a date.

Mother volunteers to help with the High School Halloween Dance and suggests that she and James go shopping for a costume. The Minnie Mouse costume catches her eye.

This is a little bit of history about James' growing up - at least how he'd have wanted it to happen.

Another inner conversation about gender identity issues. I'm conversing with someone, (I don't know who) who questions my fashion selections.

Jackie wakes up Jamie on a wonderful Sunday morning. Miss Robins like to watch. Miss Robins likes to get involved.

Jackie wakes Jamie up on a wonderful Sunday morning and Miss Robins gets in on the action - Very short!

Miss Davis gets an unexpected opening at the beauty parlor and Jamie gets volunteered by Mother to babysit. The girls have a ballet class at Miss Johnson's School for Girls and Jamie gets to assist.

This is a day (I wish!) in the life of Jamie and Miss Robins.

What goes on in my mind when I'm totally bored and think about getting caught!

After Miss Robins hears Jamie ask Jackie where he gets his pretty lingerie, she decides to take them both to Tammie's Intimates.

Mother helps Jamie prepare for a date with Jackie. It seems Mother has a date with Miss Robins as well.

The first day of Miss Johnson's School for Girls with Jamie and Jackie a little unprepared for the day's lessons.

After Mother screams across the house asking about her bra, Jack tells James that doing laundry is 'maids' work. Mother and Miss Robins decide to let James and Jack experience real maid work first hand. They need a little extra training at Miss Johnson's School for Girls.

Mother and Miss Robins catch Jackie and Jamie satisfying each other. They'll be attending Miss Johnson's School for Girls for Maid Training.

Miss Robins and Jack come by to visit and prepare for Jack and James' introduction into 'Maid's' work.

Mother screams across the house asking if I'd seen her pink 'Olga' bra. I have to explain to Jack why she is asking me. Jack thinks I'm being treated like a 'maid'. Mother is going to make me feel like one.

Jamie is caught watching his sister at her ballet class. I first published this in 2007 but have fixed it up a bit since then. Please review, I appreciate your comments.

James suggests that Mother might damage her lingerie by washing it in the washing machine. He becomes the laundry person for the home. When Tammie is by to work on homework, James has to explain why he's washing one of his mother's bras. A conversation about bra comfort ensues and James now has to 'walk a mile' in a bra.

Karen has decided to give James what he's always desired. Alice and Susan just come over to rub it in.

Jamie prepares for the big date with William. She tells him 'why' he dresses this way, and they enjoy an evening out to dinner and the movies.

Jamie gets to attend a real girl's birthday party w/sleepover. He shows off his new bloomers which seem to be the hit of the party. Mother picks him up for a beauty parlor session on Saturday for his date with William.

James and his friend Robert are spending some time together on a Saturday when they go down to make lunch. James unfortunately describes what his opinion of a maid is, and Mother hears him. She decides to show him what a maid really is.

Jamie accepts Mother's hatred toward men, but for some reason sets Jamie up for a date with William. William knows Jamie's a special girl, but just needs the practice. Susan invites Jamie over for a birthday party (girls only!)

James picks up a report that he'd dropped and Tammie sees his undies. James thinks his life is about to end but Tammie has other ideas.

Am I the only one bothered by wearing a nylon brief and a cotton bra? What do the 'experts' say on transvestite chat lines?

Jamie makes the mistake of not coordinating her bra with her panties and Mother has a bit of a Obsessive-Compulsive breakdown. Luckily Tammie comes by to visit.

Tammie secretly filmed James prepare for a quickly with Jack, his best friend.

The final chapters of the story of James, asked by Michelle to be a bridesmaid for her wedding to David. Mother helped out and Jamie gets to enjoy this major event in any girl's life.

The big days are finally arriving. Jamie gets some bad news but things work out for the best.

Michelle shows up for the wedding week, hooks up with Jamie. Jamie wears the bridesmaid dress for the first time in front of Mother and Michelle. Jamie and Michelle have a little intimate time in Jamie's girly room. Thank you all for your suggestions and reviews!

Jamie prepares for his bridesmaid debut. He'll need a corset and has to lose a few pounds (don't we all?)The bridal shower comes first.

James fell in love with Michelle five years before, and now she's marrying David. But Michelle needs a bridesmaid to be escorted by Richard, David's brother. Michelle talks to James' Mother for some interesting reasons, and of course, Mother agrees.

Mother takes Jamie shopping for some dance clothes, and they go to Aunty Gaile's for a swim

Mother noticed James surfing the internet for women's intimates. She suggests placing an order, then does it for him. A ballet instructor also suggests some girl time for Jamie.

James accidentally left a pair of panties in the dryer. Mother want to have a conversation about his choice of undies.