I really don’t have a lot of friends in school, anymore. My plan is to go to the local community college for my first year or two to knock out a bunch of the general courses, since I am not at all sure what I really want to do in the long run, and hopefully decide on a course by then. Most of my old friends from school all plan to go to ‘real’ college and we have unfortunately all sort of drifted apart as new cliques have formed. Long story short, no one really says a word about my pierced ears, although I do get a few grins from some of my older buds and I do notice some of the girls looking at me more, but not in a mean way...

I find that sitting in the hard chairs with my sore butt is a big issue throughout the day. My backwards little guy is also really uncomfortable in his present position, but I find that I become more and more used to it as the day progresses—or maybe he is just getting so numb, I don’t notice the discomfort. Even so, by the end of the day, between my butt and my trapped little guy, I am really ready to get home and find some relief.

Speaking of relief, using the bathroom is also a real pain with my guy the way he is; I have to go into a stall to get him untucked…and then fixed back. I find it is actually easier to just sit and pee.

Finally, I make it through the day, all pain aside, and happily ride the bus home, enjoying the cushier seats. To my surprise, Mom is just coming home too—about an earlier than normal. She smiles at me and says, “Hi, Hon! Help me carry these bags in.”

I open the trunk of her car and see several grocery bags and a large pink bag with a ‘VS’ on it. Even I know that it is a Victoria’s Secret bag and am more than a little surprised that Mom shops there. I shrug my shoulders and grab the groceries, leaving the VS bag behind in the trunk, figuring she will just take it straight to her room.

I take the groceries into the kitchen and Mom follows me in with the VS bag. I set the groceries on the counter and she completely surprises me when she hands me the bag and says, “Here, put these away in your room and then hurry back down and help me with supper. Vicki will be here soon and I want it to be a nice affair. We are making your Grandmother’s lasagna…”

Stunned, I take the very pink bag to my room and look inside it. There are a couple dozen lacy panties of varying feminine colors, like bright pinks and oranges, or pale blues and greens. They all cut like the ones I currently have on. Mom had told me earlier it is a ‘bikini cut’; like I really wanted to know.

There are also the same number of silky undershirt-looking things, except they have string shoulder straps instead of sleeves and some lace around the neck; these are in white, beige, and black.

Finally, there is a black woman’s sleepwear set?!?!

I shake my head hard—I feel like I am in Wonderland, or something. In a zombie-like trance, I put the panties in the drawer that had previously held my undies. Since I don’t have an undershirt drawer, I just put the shirt-thingies in with the panties. I have no idea what to do with the night thingies, so I just throw them on my bed…

I pinch myself to see if I am dreaming and hiss when I feel the pain. I shake my head again and start thinking about changing to give my little guy some freedom. Right then Mom yells up for me to ‘hurry up’ and so I just go back downstairs as I am—the little guy is sort of really numb by now, anyway.

When I enter the kitchen, I look at Mom and ask, “What are all of those things? I mean, OK, I can maybe see some plain panties to ‘get in the mood’, but those are not ‘plain’. I have no idea what those shirt thingies are. And what in the world am I supposed to do with that night thingy?”

Mom hands me an apron and says, “Those are very nice panties and I paid quite a bit for them. Please take care of them! As for the camisoles, they are exactly that…undershirts. You should wear them under your shirts to get that feminine feeling of nice lingerie under your clothes—there is nothing more feminine than enjoying nice lingerie; it is something us girls really live for. As for the baby doll, well, it is to sleep in, of course. Now quit procrastinating and put that apron on. Your girlfriend is going to be here in less than two hours!”

I blush and take the frilly apron. I put it on over my head and struggle a bit, but finally get it tied behind my back. This is the first time that I have ever actually helped cook in the kitchen. Mom has me make the salad, giving me instructions and tips along the way. I also help assemble our family’s traditional lasagna recipe and garlic bread. Soon enough, the lasagna is in the oven, the salad is in the refrigerator, and the bread is ready to be toasted—and we have a little less than an hour to go.

Mom then has me set the table; this, I know how to do. I look at the clock; forty minutes...

Mom has me do several other preparatory things and keeps me busy, so the time passes quickly. Before I know it, the doorbell rings and I answer the door; of course, I forget to take the apron off. Vicki sees me and gives a little scream, “Gerri! You are so cute! She hugs me and kisses me and says, “And it smells so good! Lasagna? My fave!”

She follows me in and my mom gives her a hug. She says, “Hi, Claudia. Thank you so much for inviting me. It is a rare occasion that I get a truly home-cooked meal! We had a cook at home, but it is simply not the same. Oh, I brought my favorite wine—I hope you like red?”

Mom smiles and says, “Welcome, Vicki. It is an old family recipe; I hear you like lasagna, which is great. Gerry helped…and also made the salad and garlic toast… And, yes, I adore red!”

The meal passes quickly with lots of talk about Vicki and her plans for the future. Of course, Mom embarrasses me with certain stories of my past; she does however let me have a little wine as a consolation, though… I am starting to get more used to the taste, but still make the appropriate face when I taste it, and don’t give anything away.

One thing I find out during the conversation is my mom actually knows Vicki’s mom; somehow through Mom’s business. While they are not ‘friends’ in that manner, they are good business acquaintances. It surprises me even more when Vicki does not seem surprised by this, but I don’t say anything…at the moment.

I quickly help Mom clean up. Since it is still rather early for a Friday night, only about eight-thirty, Vicki makes a suggestion, “Why don’t we go to the mall? Maybe we can find some nice clothes for Gerri to try out. I am dying to use my fashion skills again on someone other than me. Of course, I am happy to give my opinion on things for you, too, Claudia—if you want, that is.”

My hopes that Mom will be too tired and not go along with this idea are dashed, when she says, “Vicki, that is a wonderful idea! I have been meaning to let Gerry pick out some new fall and winter clothes; the old ones are, well, so old… And as far as I am concerned, if Gerry gets an updated look in the process, so much the better! And, all of us going together would be so much fun and I would love your expert opinion. Let me just grab my purse!”

Fifteen minutes later, we are at the mall. Vicki gets a gleam in her eye and asks, “Should we start at Victoria’s Secret?”

I choke a bit and Mom giggles, then says, “I was just there a bit ago—I got Gerry some of the cutest panties and camisoles—and a darling baby doll nighty. I am curious to see what feminine things you would pick out, though. You can never have too much lingerie, right?”

Vicki giggles as I profusely blush and says, “Oooo, I wish I could take a peek…” And we enter the ‘forbidden zone’ of women’s intimates…

To say that my Mom embarrasses me to no end is an understatement—and she does it on purpose; I can tell. She is having too much fun with my insecurities as Vicki picks up several bras and asks my opinion.

She holds up one particularly lacy ‘push-up’ bra and asks me my opinion. Seeing my red face, she says, “OK, maybe it is a bit too soon for bras… I know you are still easing into this… I LOVE that you are doing it, though.” She whispers in my ear, so that Mom can’t hear, “You are really turning me on, right now!”

I nearly choke, but just respond, “Yeah…ummm…I don’t think I need any bras… Err…I don’t have anything that would…benefit…from them…”

Mom gives me a strange look and Vicki giggles. She then pulls us over to another section of the store. There is no stopping her here, though, and we eventually walk out of the store with two garter belts and accompanying hosiery ‘for that intimate feel’, as well as a couple more ‘nighties’.

Mom just giggles as she hands me the large, very pink VS bag to carry.

From there, we go into the same high-end women’s clothing store that Vicki had been coming out of when I met her. I give ‘the bench’ out front a forlorn look, wishing I could just go sit on it while the two women go into the store. Seeing Mom’s raised eyebrow, I put on a ‘happy’ face and follow them in.

I really want to draw the line at trying on some women’s pants, but I know that would let Vicki know that this is not really what I had intended when wearing Mom’s suit. Mom just gives me a smug look in anticipation of how I will react. I finally take the pants that Vicki picks out for me to try on. They are a size ‘12’, like Mom’s old suit, and feel sort of…luxurious. They are a simple black and sort of dressy, for a woman that is, but not overly. I guess you could say, they would be the equivalent of me wearing really nice khakis. I nearly faint when I see the price tag…$235.98!

I see this is as my opportunity and say, “Vicki! There is no way I can afford these!” I expect Mom to back me up.

Vicki says, “Nonsense! I talked to Mom and she has agreed to a small budget as part of her birthday gift to you. She couldn’t let my Dad outdo her!” She grins and winks.

I groan and Mom simply says, “Vicki, tell your mother thank you. I will set up a lunch meeting with her—of course, I can expense that, so we will have a nice one! It has been way too long, anyway. And we have lots to talk about.”

I am looking back and forth between them and finally give up. I shrug in defeat and head towards the dressing rooms.

My final hope is that they will stop me, an obvious guy, from going into this forbidden woman’s realm. I am surprised that the associate at the dressing room door does not put up a fuss, at all; she only asks if I need assistance. It seems she, and just about everybody else in the store, know Vicki very well and they are all just about helping—especially after Vicki ‘explains’ why I am here.

I blush again and go in. I don’t know what I was expecting…naked women, or something, I guess. It really is no different than the guys’ rooms…

I try on the expensive pair of women’s pants and I have to say they feel really nice; I even do say that as I come out for Mom and Vicki to see them on me. They both approve of the look and I wind up with three pair; the black ones, one navy blue pair (basically the same as the black ones), and one charcoal grey, really soft woolen pair. Then they pick out several tops for me.

Mom says, “These cashmere sweaters are adorable! They would great over your new camis.”

Vicki chimes in and says, “Yes! I agree…this will be an awesome new look for you! They will let you feel very feminine, but not look overly so—the same as the pants. I think we have you on your way down the right path!”

I think, ”Yeah, down the path to the rabbit hole…”

Mom says, “You will be the envy of the school!”

I nearly choke on that one and say, “Umm… You really think I should wear this to school? Isn’t that a bit overdressed? I mean…”

Mom giggles and says, “Well not every day maybe; you are right. That is maybe too much change at once… We can get you some new jeans, too.”

Of course, the jeans I get are women’s… Thankfully, not with bejeweled pockets; but the pockets are ‘decked’ out with embroidery. Overall, I guess they don’t really look too girly; a lot of guy’s jeans are like that now, too. At least, I tell myself that. I can’t deny that they feel so much better than my old jeans, though…

Of course, Vicki insists on paying. She just puts the total on her store charge, not blinking at the fact that it is over a thousand dollars. Mom seems a bit shaken, but thanks her again and I thank her, too. My thanks wind up ending with a kiss. Mom just winks at me at that.

My hopes that our shopping spree is over are dashed when Mom says, “OK, Gerri. You need new shoes, too.” She doesn’t specifically mention the accident with the wine, she just says, “Your old ones are a total loss. It is great that you can wear mine, but I think you should have your own.”

Vicki grins and almost bounces as she says, “Shoe shopping? Yes! My fave!”

I meekly follow them into a large shoe store with high-end shoes. I start to walk towards the men’s section when Mom pulls me with them to the women’s. I turn a little red and she says, “Come on, Hon. We will find you something appropriate, don’t worry. I think you need something ‘nice’ and something for ‘every day’. Of course, once you fully get into the feminine mindset, you will find that you never can have too many shoes! Right, Vicki?”

Vicki grins and says, “Absolutely! Oooooo! Look at these! They are DARLING! I HAVE to see if they have my size! Do you want some, too?”

She is grabbing some pink monstrosities with a heel that would put any self-respecting pencil to shame. I blush, not knowing if she is asking me—or Mom…

Thankfully, Mom says, “Those ARE adorable and would look really great on you, Vicki! I think I will pass, though. Pink is not really my color.”

Vicki is looking through the shelf for her size and says, “Nonsense, Claudia! I think you would great in pink. You just have to use it as an accessory color for your complexion; not as the primary one. Little pops of color… Ahh, here we are! They have my size! Gerri? Have you found anything you like, yet?”

I groan internally, as I watch Vicki strap on the towering shoes.

Mom smiles and hands me a pair of shiny black shoes. They are wedge-shaped and clearly women’s, but after she has me put them on, I have to admit, you can’t really tell—other than I am two-inches taller. Mom says, “This will work well with your new pants, they are designed to be worn with at least a little heel. More would be better. We can get you some real heels to practice in at home…”

When all is said and done, we leave the store with ten pairs of shoes. I have the shiny black ‘wedges’, a pair of new (girl’s, but not plainly) sports shoes, and a pair of red, three-inch ‘pumps’ to ‘practice’ in (there was no way out of that one…). Mom has two new pair of heels, including one pink pair that Vicki convinces her is ‘perfect’. The rest are Vicki’s…

On the way home, I get the next ‘big’ shock of my life. Vicki looks at Mom, sitting in the passenger’s seat, up front, and asks, “Claudia, you don’t mind if Gerri sleeps over at my apartment, do you? Mom wants us to come by tomorrow and it would be easier.”

I want a hole to appear in the back seat and swallow me up. I know Mom is going to go ballistic. I nearly explode from my complete surprise when she says, “No, not at all! That makes perfect sense! Gerry, please remember to tell Dr. Langdon hello from me and behave yourself…” Then she giggles and says, “I keep forgetting that you are eighteen and I don’t have to treat you like a little child anymore. You can make your own choices now…and I have raised you to stand by them…”

The message is clear… I have made my choice and promised to stand by it… Don’t embarrass her; especially with a client.