Yes I’am a lipstick girl, from the very beginning I was mesmerized by my mom’s lipsticks and at that time all the magazines had pretty women with amazing makeup and of course amazing lipstick lips, this is a little embarrassing but as a very young boy 5 or so I would find myself kissing those pretty models in the magazines and enjoying it very much so I guess that was one of my fetishes to be forever in my life, lipstick kisses that is lol.
As mom introducing me to properly applying lipstick she knew I was fascinated with lipstick and having me kiss my Barbie Doll with the 3 pucker up kisses that I still love too do even to this very day, and thank baby Jesus as I got older now 65, yes 65 amazing how time fly’s I look better than I should and still a full head of hair kinda lol wearing it a little longer the older and younger girls love it when I kiss them like that well most do other’s give that what the hell look lol, yes I can’t even believe I still do that naughty crap but anyway on with it.
After mom’s lipstick introduction it took me about 3 seconds to fall in love with lipstick practically wearing it 24/7 or whenever I can that didn’t take long after mom’s first coat of lipstick on her new daughter, I was truly a kissing fool I mean it started out very conservative at first and it just snowballed as time went on.
Mom was my first victim lol and as you can guess she was a little surprised as was I, but it had to start somewhere with someone and all in all that was a safe bet with mom no rejection I was hoping and it also gave me a little confidence too, funny thing about that mom and I became more close on a girl to girl connection with loving kisses, I think I fell in love with mom on a mother daughter relationship level even more, I think she enjoyed kissing too she never turned away and always gave me 3 nice kisses back, as time went on we would kiss maybe a couple times a day hello in the morning with a good night kiss too and some days we would find ourselves kissing a couple of dozen times it just felt natural for me nothing sexual I didn’t think so but it did make me feel good inside, mom would even kiss me on my lips in boy mode I liked that too.
Now with auntie and my little nephew that was a little different, after the first time they came over it broke the ice for everyone after that it came quite easy and really natural for the most part giving kisses to my auntie and my nephew, auntie I think loved kissing as much as me or she just loved kissing girly boys, I did notice auntie liked kissing her son more when I put lipstick on him so maybe the latter.
Sometimes me and auntie would sit on the couch and she would put different lipstick on the both of us telling me she just wanted to see if it was a good kissing lipstick, yea right but I was really loving it too, it did turn me on not realizing it was a sexual turn on I’m sure it was, for auntie guaranteed she was sexually aroused but that’s as far as it went between us.
For auntie’s son I kinda treated him like my Barbie doll, I would put lipstick and earrings on him with little pigtails carrying my purse he looked so cute but that was it, I would kiss him a lot but just sweet girl kisses I got a thrill out of it but not as much as I anticipated and I’m sure he felt pretty much nothing but I loved my nephew so much, but auntie would kiss him like a girl friend to a boy friend kinda thing I can’t say really anything but I did notice it so it was something, good or bad who knows, but they seemed really happy so that what matters most.
I’m sure I mention this before when I’m in girl mode all dressed up I really feel and act as a girl it feels so natural and absolutely wonderful I wouldn’t change that feeling for anything, I remember being 9 or 10 and fantasizing when I was in my girl mode running up to a older guy and giving him a big naughty lipstick kiss then pulling back and saying your not my daddy and just skip away kinda weird don’t you think.
One more good thing that came out of this I had this awesome knowledge over all the other boys, that I knew how to kiss a girl and wasn’t afraid to use it and when your a 11 year old boy that’s a big advantage, I spent a fair share of my time behind the classroom buildings kissing girls and as the word got around it was way too easy but so much fun I loved those times at home and school, I never got caught by a teacher but a few times came really close there was even a few teachers I fantasized about too but when your that young that’s all you can do.
My relationship with my auntie we where always close and loved each other she treated me like her son but when she met sissy things changed from that first weekend, it was kinda like love at first sight all over again but would definitely be going down a different path.
It was that first lingering kisses at the front door that kick started it and then the play date at aunties house was interesting too, at first kissing auntie on the couch and just kissing her was very nice but it was a lot to take in I think she could see that in my look the first few times, I always have worn my emotions for everyone to see I could never hide it, at least she loved me enough to tell me that if kissing made me feel uncomfortable we didn’t have to kiss anymore, she said I would never make you do something that you didn’t want to do, I think I didn’t say anything.
The next few get together’s where a little slow in the kissing department and funny thing I was really missing all the kissing it just grew on me I really liked it a lot, a couple three weeks later she asked me again about kissing this time I looked at her and said I truly love all the kissing and I didn’t want it to stop, I think I shocked her a little but her big smile said it all and just melted me too, we became even closer something funny started to happen after that.
We started to gravitate towards each other, like we would kinda find each other and just give each other a little soft touching and some loving kisses, we never really never did anything but lite touching and kissing and we never french kissed or open mouth kissed we were just happy with sexy pucker up kissing and as far as the lite touching one of our favorites was having our legs touch each other at the dinner table where no one can see it was very naughty but we both loved it, can you imagine a 40 year old lady playing footsie with her 10 year old niece how crazy is that lol.
But truthfully that’s as far as it went, I was totally happy with that we had a great time together, we definitely where two girls who love kissing and yes the kissing did increase almost to the point if we ran into each other at either house more than not we would do the 3 kisses and sometimes a little more.
As far as her son went, auntie always loved it when I dressed him up as my little niece and I loved it too I guess I have this mother gene also, loved treating my little niece like she was my little girl, auntie encouraged it going as far as telling him that he will listen and do what sissy wants as if I was his mother too, when auntie said that I had the biggest smile and felt kinda tingly inside too.
This was just the norm, it was wonderful times going from a five year old boy hiding my girl side to this and in the long run auntie’s house became my fun spot, after my dad passed years later mom found a new husband I was about 13 years old and pretty much sissy was nonexistent at home and auntie’s house was my girly place but it was just not the same, it was really hard on me and I went through a little depression and it didn’t help that we had no bond between us what so ever but he made mom happy, I ended up leaving my house at 16 I just couldn’t be there anymore and never to lived there again I was on my own, oh well all good things usually end at sometime.
So be it, on with sissygirl’s journey.
I just wanted to touch on this and see if anyone else has had a similar experience.
When I was in the 2 or 3 grade I was walking down the classroom isle towards the front of the class probably heading to my desk when a boy said to me you walk like a girl, that was the first time I heard someone saying that to me, well it stuck in my head even to this very day and a funny thing it really didn’t bother me or upset me it just made me aware that yes I’m walking like a girl, that was the first time I was kinda outed in public lol.
I guess we just pick up on habits sometimes we are just not aware of and then some we have learned or we've been taught them, I’m sure for me it was all three, early on mom of course new about my love for her lipsticks and her purses but not yet my sisters Mary Janes that was soon to change.
As my need to always show or express my inner feelings or thoughts at one time or another I just can’t help myself, while mom was tucking me in I just couldn’t keep it in any longer my mouth just started talking before my brain could stop it, mom I love sis’s little girl shoes, when you crack the door just a little open with mom she will have it wide open in the end and sure enough I told her everything.
Going into sis’s closet and touching them and playing with them, they where just a marvel of pure girlyness and so pretty I just couldn’t help myself and being the easiest of one of my deep down desires to play with, I told mom I would take them back to my room and try them on and when nobody was home I would walk around the house in those black patent beauties just looking down at them totally in love.
She intently listened to me with a smile, probably not to detour me from telling her everything, it worked because I told her everything even when sis was gone for a sleepover I would sneak into her room and take those beautiful little girl shoes bring them back to my room and wear them to bed until sometime in the middle of the night I would take them off because my feet would get too hot and uncomfortable again telling mom everything.
Mom being her usual mischievous fun way looked at me and said, I’ll be right back and left my room a minute later mom came walking back with those beautiful black patent Mary Janes saying you young lady will be wearing your little girl shoes to bed and sissy you will wear them all day tomorrow too and you better not take them off tonight or tomorrow missy or you’ll be wearing them to bed for a month and it won’t be as fun as you think, I was speechless just swimming in a pool of excitement and happy disbelief, I could only shake my head yes, having me sit on the edge of bed mom buckled me into those beautiful little girl shoes saying they fit pretty good, sissy your a very lucky little girl tucked me in saying sweet dreams with a little wink, wow.
To be continued…
I think at this point in my girlhood experiences mom was accepting it and enjoying it, seeing how I was really enjoying it too mom probably realize that I didn’t have a need to be a girl but just loved girl things and the fact that my sister was a tomboy jock mom was just happy to have a new daughter to have some girl fun with.
Inheriting my sister’s Mary Janes I would have never believed it until mom referred to them as my little girl shoes or something like that, i do remember mom saying that my sister wouldn’t miss them and I really never seen her wear them too, she diffidently didn’t care for anything girly but I did lol.
So when I came walking into the kitchen wearing my Mary Janes with my night slip I felt like a girl inside and out, it was wonderful and I had moms loving approval I felt so good inside but still I was lacking proper etiquette for a girl just doing simple things.
As mom would point them out, as I sat down in my boyish usual way mom looked over at me and said, sissy now that you’ll be wearing your pretty little girl shoes a lot from now on it just doesn’t look right the way you’re sitting, try putting your knees and ankles together and let’s see, mom really liked that look and it did look and feel very girly but I just couldn’t hold that position very long unless I just concentrated on sitting like that.
To be continued…
Keeping my knees and ankles together was difficult for me, holding them together in a upright position worked the best for me and to have my legs at a angle looked better and more feminine but it was even harder to sit in that position for any length of time.
Mom could see this so she had me cross my legs and wala that was the answer for me, it really felt way more comfortable and natural crossing my legs, so that became my sitting position from that morning on, plus I really kinda loved it.
It felt good and I could move my legs around to make it feel more comfortable, switching my legs back and forth made it work even better, the two things that I loved the most is one I could look at my pretty shoes enjoying how they looked and two I could rub my patent Mary Janes on my lower leg down by my calf and it felt wonderful I was definitely getting sexually aroused by it but didn’t really know at the time, to me it just felt really really good lol.
As time went on I came to realize that boys young and old liked pretty shoes too especially on crossed legs, not all but for sure some enjoyed it, even my little nephew seemed to notice them we’ll I kinda helped him, on a few occasions I gave him a damp cloth and had him wipe those beauties down and then had him dry them with a soft dry cloth all the time wearing them of course, I could see a little bit of wonderment on his face especially when he was done and I would stick those beauties right under his nose almost touching his lips and thanked him asking him don’t they look so pretty and shiny just to see what he would say or do, he really didn’t say or do anything but he seemed a little intrigued with them in a cute nervous kinda way that I created that was one of my first times doing a little bit of teasing and to tell you the truth it was kinda fun.
With mom it was on to another girly lesson, the girl walk pretty much on the mornings my sis was gone, as I was heading into the kitchen wearing my girl shoes knowing I was to wear them for breakfast and the coast was clear, mom informed me early on that if I found my little girl shoes on my nightstand that was the ok to wear them or that she wanted me to wear them either way I got the message.
The girl walk, while mom was fixing breakfast she would have me walk from the kitchen down the hallway and back it was simple and just a few times back and forth, the first time she showed me how to put the one shoe in front of the other shoe like heel to toe and after 3 or 4 times a couple of minutes each time I was getting the hang of it and it felt pretty comfortable too, I even was starting to get a little sway that also that made me feel a little naughty or at least a good feeling inside probably both lol.
She added little stuff to my girl walking lessons, like not to hunch over hold my back a little straighter thing’s like that but mom saved the best for last and that was carrying my purse like a young lady as she put it.
At first I was a little shy and unsure but with mom’s loving and fun way she did it I was getting into too just as much as she was, I carried my purse with my left or right hand by my side the most common way a girl would carry her purse I guess and if I stopped I could hold my purse in front of me with both hands and mom even showed me how to carry it like a clutch purse, but my favorite and the one I love the most even to this very day and how mom would carry hers was inside her arm at the elbow the crook of her elbow, I always loved watching mom carry her purse that way it was just so girly and feminine I just loved it and it felt as girly as it looked I was hooked.
I would carry my purse like that for hours and loved every minute of it, it just made me feel so good inside and feel like a more mature girl too, I must say that was one of the best things ever and enjoyed so much I loved it, just watching me mom had a big beautiful smile, it was great.