my mom's closest friend was her younger sister Julie they were only 18 months apart it helped that we lived only one town over and that both were single moms they were both beautiful vivacious women girly girls who loved everything feminine from Fashion to makeup to shoes and jewelry like Mom Aunt Julie had only one child but unlike mom her child was a girl Chrissy Chrissy was beautiful blondee hair blue eyes and a seemingly permanent tan she looked a little like a teenaged Christy Brinkley although mom and I had a great relationship sometimes I felt like
she was just a tiny bit jealous of Aunt Julie for one thing even though both families were comfortable their father my grandfather Mike died a wealthy man and even though most of the fortune went to Grandma they were both given enough to live comfortably Aunt Julie got a big divorce settlement and definitely lived a more luxurious lifestyle Julie could afford to go to the salon every week and always wore designer clothes also sometimes I got the feeling that Mom would have liked to have had a daughter like Chrissy Chrissy one of the most popular girls
at her High School everyone loved the beautiful blonde cheerleader she was 5 years older than me but still we were very close she was like a big sister to me partly that was because from the time she was 12 and I was 7even Chrissy was my regular babysitter Chrissy is 17 and is getting ready to head off to college in the fall lots of times I thought about complaining to Mom that it didn't seem fair that I still had a babysitter at the age that Chrissy was actually babysitting me but I enjoyed her company so
much that I never said anything I have always been a little on the slight side and I am not really into sports or anything so it was natural that our conversations would gravitate towards things that Chrissy was interested in boys fashion makeup Etc in the beginning it felt awkward mainly because I felt like I had to act like I didn't want to talk about those girly subjects but I was honored that she considered me to be a bit of a confidant okay it was more than that of course I had a crash on my beautiful
older cousin so I was always very attentive I wanted her to feel comfortable sharing with me once in a while she would affectionately refer to me as her little sis which was embarrassing but there was a part of me that liked that anyway one night my mom and Aunt Julie were out and Chrissy was babysitting I really didn't like that term I was almost 12 me her friend Britney called and Chrissy told her to come on over I had known Britney for years and I liked her a lot so it was fine with me Britney
was beautiful too but with a mass of dark luxurious hair sexy lips and amazing cat-like eyes Britney came over and the girls were chitchatting about this and that and Britney took out her lip gloss and showed Chrissy she applied it a pretty sparkly pink and said oh I just love this new lip gloss she batted her eyelashes at Chrissy and said doesn't it make me look sexy Chrissy giggled and said let's ask Sandy and Britney turned to me and started making pooching faces with her lips and flirting with me my face turned red with embarrassment
well one thing led to another and before I knew it the girls were having a little makeup party they wanted to try some new things like winged eyeliner and they decided that I would be a perfect model for trying different looks I was in heaven having these two beautiful 17-year-olds fuss over me and so the truth of the matter was I didn't object very much to being their makeup model that was where things stood when Mom and Aunt Julie walked in the door I was really embarrassed but then Mom and Julie who both might have
had a few cocktails were both gigg Ling and saying what a pretty girl I made I laughed along with them and even acted extremely girly talking with a lisp to be a good sport and join in the fun as they were getting ready to leave Chrissy said they would clean me up but Mom smiled and told her not to worry about it we'll get ready for bed and I'll give him a lesson on how we girls remove our makeup before bed I wondered if I was included in the we girls reference I got undressed put
on my PJs and met mom in her bathroom I sat at her vanity and she showed me how to use the pads to remove my makeup it was an odd moment I mean obviously I was never going to wear makeup again so I really didn't need to know how to remove it but it felt like a special moment we were sharing and I didn't want to do anything to ruin it Part of Me wondered whether this would be what it would be like to be Mom's daughter and I wondered whether she was having the same
thoughts I tried to put the thought out of my head I didn't think much about this incident but apparently it had left some impact on mom she was on the phone with Aunt Julie the next day and Julie was going on about how pretty I looked all made up Mom paused and said yes Jewels he looked adorable I wonder if there is more here though is this the first time this has happened or has my niece been busy feminizing my son do me a favor and casually ask Chrissy whether this was a one-time deal or
whether there were similar incidents is it something I should be concerned with Aunt Julie poo pooed her concerns but promised to check with Chrissy the truth was this hadn't been the first time we had done something like this but it wasn't a regular thing either there were times when she got silly and put my longish hair in pigtails and once she painted my fingernails and took off the Polish before mom got home and once she had complimented me on how long my eyelashes were telling me how she wished she had lashes that long and then
put some of her mascara on me but it wasn't like we had a Makeup Session every time she came over anyway mom seemed basically satisfied with Chrissy's explanation but her concern lingered finally one evening at dinner she broached the subject in a way that I'm sure she thought was very casual so Sandy she said did you have fun the other night when the girls put makeup on you you did look very cute I got embarrassed and of course thought I had to act manly and said no Mom I did not enjoy it I let them
do it because they pressured me into it I mean what boy likes to wear makeup mom paused before answering and then said well some boys do and you know that's okay I'm not saying that's you I'm just saying if it was you there's nothing wrong with that I was silent mom said I'll be right back and walked out of the room she came back a minute later with her laptop see this she said this is a young man named Andre padic look how beautiful he is and obviously he's wearing makeup Andre is a Top Model
he models both men's and women's clothing I'm not saying this is who you are Sandy I'm just saying if it was it would be okay she said okay and I nodded the truth was I had so much fun that night and not only that I had loved the way I looked but I was way too embarrassed to ever admit that I appreciated that mom was trying to be so understanding but I still couldn't bring myself to admit anything I wasn't even sure what I would admit to as I got up to walk out she said
remember honey if you ever want to talk about anything I am here for you in spite of myself I found myself turning back to her giving her a big hug and saying thanks Mom I was feeling very confused and I tried to put the whole subject out of my mind a week later I had an appointment with the dentist I had two cavities that needed to be filled I really hated needles especially in my mouth and the dentist agreed to give me the nitrous oxide gas before she gave me the novocaine nitrous oxide is known
as Laughing Gas but it also has another side effect it completely lowers your inhibitions and can therefore act a little like a truth serum you could say that it's unethical to ask a patient questions while he is under the influence of such a drug but Mom and Dr Bernstein had been friends for a long time so when Mom stayed in the room with me and then started to ask questions after the gas had taken effect Dr Bernstein kind of raised her eyebrows in a look of disapproval but didn't stop mom Dr Bernstein couldn't leave the
room with her patient receiving gas so she stood by mom said to me honey did you have fun last week when the girls put their makeup on you now Dr Bernstein's face turned to one of surprise and she looked at Mom quizzically Mom just looked at her and made a shrugging Motion in the meantime I smiled and indicated that I did indeed enjoy it Mom continued would you like to do it again in an almost giddy voice I said oh yes she continued would you like me to do it with you I didn't answer but
I had a contented smile on my face Dr Bernstein was not going to let this go on indefinitely for one thing she had cavities to fill mom asked one more question honey do you ever think about being a girl or maybe mommy's part-time girl would you like Mommy to buy you a pretty dress that you could wear when you got home from school once again in my drug induced State I simply sighed and contentedly said oh mommy don't be silly boys can't wear dresses Dr Burnstein shed mom out of the room but Mom already had
what she needed to know her sweet son didn't say he didn't want to wear a dress he said he wasn't allowed to Mom waited in the reception area until I was done and then took me home the gas has no lingering effects as soon as it gets turned off your head gets clear I got in the car with Mom and she shot me a meaningful look but I was oblivious I had no recollection of our little conversation mom spent the next couple of days pondering what if anything to do she wasn't even sure if she
should share her new information with Aunt Julie one afternoon they were on the phone together Aunt Julie going on about how she was getting Chrissy ready for college she said not only does that girl have more clothes than any 17-year-old on the planet I swear I think she has never thrown out a thing I have things in her closet from before she was a teenager I think college is a new start I know it's ironic for me to say I'm going to get her a new wardrobe but I think she is ready for some more
grownup choices maybe I'll just take the whole thing over to Goodwill there was a pause on Mom's end of the line and then Mom said I don't suppose there is anything in there that's some unisex that's Sandy could use now it was Aunt Julie's turn to pause of course sisters have a special bond especially two as close as they are and sometimes they can read more into what isn't said than what is Aunt Julie said well I'm sure there is but she's busy getting ready and I really don't have the time to sort through it
all I'll tell you what why don't I bring the whole pile over to you you you can take what you think he might use and you can give the rest away or just toss it Mom smiled and said that was a great idea the next day Aunt Julie pulled up in her Lexus SUV opened the back and took out four giant black Hefty garbage bags unbeknownst to me I had just inherited the massive wardrobe of a 17-year-old girl Mother wasn't about to throw anything out instead she spent two full days organizing her new Treasure Trove
she filled the guest room drawers and closets with Chrissy's clothes Aunt Julie wasn't kidding about not throwing anything out drawers were filled with bras panties and bikinis mom organized the closet in order from androgynous on the left to completely feminine on the right for example on one end of the closet a pair of blue jeans jeans snug and cut for a girl's shape next white jeans after that Capri next leggings then rompers finally a dozen cute skirts and dresses shoes followed a similar pattern from flip-flops to stilettos mother did not know how far down that
row she would end up going but for now she wasn't throwing anything out out I wasn't aware of any of this all I knew was that Mom casually mentioned to me aun Julie brought over some of Chrissy's hand me- Downs I looked at mom kind of strangely and said no offense mom but aren't you a little old for Chrissy's clothes mom giggled a little and said not for me silly for you I looked at her in alarm and said Mom what are you talking about I can't wear a girls hand me downs mom said oh
calm down I'm not about to put you in dresses although she does have some cut ones and frankly I think you would look adorable there are plenty of things that she has that are unisex shorts and t-shirts and so forth you know money doesn't grow on trees young man these clothes will save us a bundle mom then thought about sweetening the pot a little maybe with the money we will save I can get you that new PlayStation you've been asking for now she was talking mom was about to put her plan into action and she
was going to enlist a co- conspirator in the process now that Chrissy had her license she could babysit me but didn't have to stay at home with me Mom suggested that she and Britney take me to the mall maybe watch a movie got to the food court etc for Chrissy it was a good deal because she was getting paid for doing what she would be doing anyway mom said to her listen Chrissy he is going to be wearing some of your hand me downs I do not want you making him feel self-conscious do you understand
on the other end of the phone Chrissy a little wide-eyed said oh oh Auntie Emily you know I would never do that I wasn't too happy when Mom pulled out a very short pair of jean shorts that looked they had originally been pink and were bleached and a little black tank top mother knew she had to be firm especially this first time and she was I lived up to my end of the bargain and got you the PlayStation now there is absolutely nothing wrong with this outfit I'll tell you what when Chrissy comes to pick
you up if she thinks it's too girlish you don't have to wear it little did I know that the fix was in naturally when the girls picked me up they acted as if there was absolutely nothing wrong with what I was wearing I thought to myself okay maybe I am overreacting and I walked out the door with them I did have a great time at the mall they dragged me into and out of a bunch of shops like for ever 21 I acted like I was bored but I actually enjoyed looking at all the girls
outfits we went to the food court for lunch and then they wanted to go into Sephora they were busy trying on all kinds of makeup when a sales girl who was probably a couple of years older than them came over and asked if they needed any help they both said no and then the girl said how about for your little sister I think she is ready for a little basic makeup I was about to say something when Chrissy shot me a look and said you know that's a great idea half an hour later we walked
out of the store with my face adorned with blush mascara and a little pink frosted lipstick the girls were so happy they were beside themselves they insisted I leave it until we got home so they could show Aunt Julie and Mom I wasn't so sure that showing Mommy wearing makeup for the second time in as many weeks was a good idea but I went along Aunt Julie and Mom were thrilled it was pretty clear that I was totally outnumbered the next weekend was a similar scenario the girls were going to take me to the mall
except this time the top mom gave me was much more girlish it was a blue tube top that said Vegas girl on it I actually thought it was very cute but I could never wear something like that out I protested to Mom and she reluctantly let me go to the closet to find an alternative I chose what seemed to be an ordinary white button-down shirt and I breathed a sigh of relief my relief however was short-lived as mother tied the bottom of the shirt up into a feminine knot that ended above my shorts I stood
there not knowing what to do she said well well the choice is yours I didn't realize how tricky she was being getting me to choose between two feminine things I didn't want I chose the white blouse which even tied up like that was better than the tube toop Chrissy and Britney pulled up and rang the doorbell mom opened the door and kissed them both Chrissy said hi sis to me I started pouting and said I didn't think that was funny and could she please not call me that Chrissy was in a playful mood and said
I'm just quoting the sales girl from saphora and that was before you were wearing makeup anyway don't you like being my little sister I was still pouting although enjoying the attention and I said can't I be your little brother Chrissy gave me a kiss and said we'll see she grabbed my hand and started pulling calling me out the door when Mom grabbed her and said Sandy go ahead Chrissy will be right out I walked out and Mom gave Chrissy $50 she said here's 50 bucks if you can talk him into getting his ears pierced at
the piercing pagota there's another 50 in it for you when you get home Chrissy looked at her wide-eyed and said Auntie Emily what are you up to Mom smiled and said I just want Sandy to find out who he really is I'm not sure what that is yet but I have a feeling it's closer to you and me then say Andrew Luck Chrissy giggled and said W duh okay Auntie Emily this is a little evil because you know he can't say no to me but here goes and we were off needless to say Chrissy was
right by the time time we got home 4 hours later I had a little gold ball in each your lobe I lay in bed awake that night thinking about what was happening if it was just a question of mom insisting that I were some slightly girlish hand me downs it would have been one thing but the clothes seemed to be getting more girlish and why was I letting Chrissy and Britney put makeup on me I really couldn't blame that on mom she wasn't even with us and now my ears were pierced clothing and makeup you
could take off but I just knew that earrings even little gold studs would somehow Mark me as a and yet I had gone along with it Mom stood there gazing at the closet she was pleased that she had moved from the far left and was making her way towards the middle she also realized that her tactic of toddler choices that is giving me two choices that she had selected and then telling me to choose and therefore owning the choice was very successful when I had gotten home from the mall I had complained to her that
I was the only boy in the entire Mall who I saw wearing his shirt tied up at the belly and she simply said I didn't force you to wear that shirt you chose it well technically that was true because my other choice was a tube Toop the next week the process continued mom said you know honey I'm glad we haven't cut your hair all summer I like this length but I think it needs to be trimmed a little I have an appointment at my salon tomorrow I think I'll take you with and Crystal can just
clean you up a little I Shrugged and said okay mom took another half step in the closet she said you know I can't spend money like Aunt Julie but going to a high-end Salon is one of my few indulgences the women are all dressed very elegantly there and I want you to look nice too she then pulled an outfit out of the closet it was a Chanel type suit I mean it wasn't too bad really just shorts a blouse and a blazer but the shorts were a little high waited with zip pockets in the front
and mother insisted that I tuck the blouse in the effect was very is which got magnified when mother impulsively threw some of her jewelry on me she went back into the closet and took out a pair of cork old wedges with a 3-in heel the clothes I thought I could live with but I looked dubiously at the wedges I had never worn anything with a heel before Mother relented and handed me a pair of flat white sandals I came home one day from hanging out at the mall with Chrissy and Britney and found mom waiting
for me she had a bit of a sheepish look on her face I said what's up and she said come with me she took me into the guest room and opened one of the drawers she pulled out a training bra and the first thing I thought was wow Chrissy really didn't throw anything out she had to have been 11 the last time this would have fit her mom handed it to me and said just for fun why don't you try this on now I really got upset all this time I felt like mother had been
pushing me to wear clothes that were more and more feminine all with the flimsy excuse that it would be saving us money for me to wear hand me downs but what kind of money would we be saving for me to put on a bra it's not like she was about to go by one for me and now she didn't have to not only did I refuse but I started crying why are you doing this I said Mom could have backed down she could have gotten Stern and simply ordered me to do it what I didn't
expect was for her to start crying she said I'm sorry you're right I should not have asked you to do that it's just that sometimes well I get a little jealous of Aunt Julie and all of the mother daughter thinks she can do with Chrissy well it might not have been intentional but if there was ever a way to get me to given this was it I love my mom so much and it really hurt me to see her cry I gave her a hug and said well you know it's no big deal I can
put it on she said are you sure and I said sure Mom just please don't tell anyone even Aunt Julie our secret she said and she helped me put it on she couldn't help smiling and then of course I smiled too what do you think she asked and I quietly said well to be honest it actually feels kind of nice like I am getting a little hug with that mom actually gave me a big hug and told me how much she loved me it was the end of the summer and time for Grandma sades annual
barbecue and picnic at her lake house in what was starting to become a routine mother grabbed me by the hand and took me into the guest room she threw open the closet door and went right to the right hand side of the closet she gazed into the closet thumbing her way through some dresses I want you to wear a dress to the barbecue she said or maybe one of these cute skirts I looked at her as if she was crazy she paused and said well if you feel that's too girly I suppose you can wear
a romper I really became hysterical and started screaming at her too girly what would give you that idea how How could a boy wearing a dress possibly be too girly in the face of my tiate mother was very calm and quietly said well it was your idea now I really lost it my idea mother I think you have finally lost it obviously giving into to you on Chrissy's clothes was not a good idea I'm sorry that Aunt Julie has a daughter and you don't but I'm not wearing a dress why the hell would you ever
say it was my idea she said you told me you wanted to wear one oh really I said sarcastically and when may that have been at the dentist's office when you were getting the gas I was completely stunned I had no recollection I felt very defensive and said well even if I did which I'm not saying I did that does doesn't mean anything I was under the influence mother said exactly you were under the influence of a drug that lowers inhibitions and causes you to express your true feelings like it or not Sandy you told
me very clearly that you wanted to wear a dress I think those are your true feelings and I am just trying to help you find your true self now like I said if you want to wear a romper that's fine the choice as always is yours I ran from the room crying a while later mom came up to my room carrying the Romper and the skirt with a matching sweater at least there was no dress I was lying on my bed still sniffling she stroked my hair and said I want you to try these on
for me let's just take a look if you look ridiculous we'll come up with another plan that was the first sign she had given of relenting so I got up off my bed and tried on the two outfits they were both adorable and the truth was if I could have worn them in the privacy of our home I would have been happy to since Mom didn't think I was being honest with myself I thought that telling her that might get her to stop insisting on having me were girls clothes to the barbecue mom looked at
me and shook her head oh Sandy if you could see how fabulous you look like this you were really meant for skirts honey I didn't say anything and she sat there on my bed thinking finally she said I have an idea I'll tell you what look the only people we know really well at the party will be Aunt Julie Chris and Grandma most of the other folks only see you once a year at the barbecue and they probably wouldn't even miss you if you weren't there what if we got you some hair extensions for the
party a new look and you could go as Chrissy's friend I'll bet with a little help I could get you looking like Britney I thought it was a crazy idea I said okay Mom I will give it a try but if if I do not look convincing I get to go wearing normal boys clothes okay Mom smiled and said young lady you've got a deal to say Julie and Chrissy were excited with the plan would be an understatement they were both ecstatic the barbecue was on a Sunday and Saturday was to be my dress rehearsal
Crystal was happy to see me back and even happier to experiment with makeup look for me with Mom Aunt Julie and Chrissy with me I had my cheering section along for the ride I knew they would all tell me I looked great but still if I didn't really think so I would have said no but when Crystal finally put me in front of a mirror I had to admit I love the results I agreed to go to the party as Chrissy's friend I think the person who ended up having the best time at the party
was great Grandma Sadie she was thrilled to be let in on our little secret and loved the idea of fooling everyone at the party she thought it was especially amusing to see all of my male second and third cousins falling all over themselves trying to flirt with me this was a new experience for me I really didn't like boys but I had to admit it was fun being the center of attention while along with Chrissy of course who was still prettier than I was as we got ready for bed that night I followed mom to
her vanity and we removed our makeup mom giggled and said see teaching you how to remove makeup wasn't a waste of time after all I looked at her slightly and said you knew that even then didn't you she smiled and said well mothers have an intuition I laughed and said intuition is that what you call interrogating son while he's on drugs she kissed me and said yep that's what I call it Mom tucked me into bed and asked did you have fun today she knew I did and I admitted it for the first time I
really felt like her daughter what was the best part she asked I giggled a little and said I loved it when Chrissy and I took our lipsticks out of our purses and applied all the boys were pretending not to watch but I could tell they were mom looked a little surprised and she said does that you mean you like boys I thought for a moment and said no I don't think so but flirting a little and getting their attention is kind of fun I paused and then said what now Mom she kissed me and said
don't worry honey we will figure it out promise and with that she closed my light walked out and shut my bedroom door leaving me to dream of what might be
