Beginnings with Miss... Part 2, the neighbor

OK, back to the fun you've been waiting for!

What happened between Miss's neighbor and I? Did I loose something? ;-)
I was walking over to Miss's house to see if she was there and to hopefully hang out with her for the evening. I'm sure I was being cautious to also see if her mother or brother were there, as I probably would have passed if they were, certainly if her mother was there. Yes I was that shy!

No one was home. These were 4-plex apartments, with Miss on the bottom floor, and her neighbor directly across the courtyard on the 2nd floor. Their patios, front doors and living room windows faced each other across the courtyard.

Her neighbor must have noticed me, and she probably tried to be helpful and called down from her patio to me about when she last saw Miss. I am sure that the 3 of us hung out at least a few times prior, maybe even had some wine or beer together. At this point in time I was probably a Sophomore, 14 years old? Miss would have been 17-18, and her neighbor was mid-to-late 20s I think. Basically she was twice my age, with a 6 year old to boot.

She must have invited me to come up, maybe to allow me to wait in case Miss might return soon.

I digress... watching TV, early porn
Her neighbor and I hung out, and I remember watching T.V. We were watching a really bad conservative politics talk show show called Wally George (on a UHF channel). It was so bad it was good! I'm sure I found it thanks to trying to catch naked ladies in soft porn movies on one of the very early pay-UHF TV stations - ONTV.

Of course I was watching this on a 13" black and white TV, with no decoder/descrambler  box. At the time it felt like if you kept adjusting the tuning knob you could "improve" the scrambled picture, but I never got more then a few seconds of any discernible boobies. This is what I would get off to (but would have been black and white):

Finally getting to the point - Her neighbor
So we are drinking a little bit, getting some laughs. I have no memory of any attraction to her neighbor. I'm totally hot for Miss all day long, every day. Her neighbor is in a dress or skirt I'm sure. That's always what she seemed to be wearing. I wish I could remember what broke the ice...

What I do remember is sitting on her couch. It was a really low couch, where my knees seemed to be too high, at chest level with my feet flat on the ground. She is walking towards me. She seemed very tall due to that couch. I remember feeling nervous and intimidated as she approached me (submissive, and yes at 14 I am a virgin still, but that's going to change). The hem of her skirt seemed a little higher than I had ever previously noted, maybe also due to the low couch. It was just above her knees, and I noticed her legs, probably for the first time since I'd known her.

She stood in front of me as I sat on the couch, somehow we had already broken the ice. She then straddled me on the couch, her on top, her basically kneeling on top of me. I think I still had my clothes on. I was afraid to put my hands on her. I probably felt like if I made a mistake she would get upset with me and I'd get into some kind of serious trouble, she'd kick me out, who knows?

My next memory is of being in the same position with her on that couch, but my clothes were off. She was still straddling me in the dress, but she did not have any panties on. She was teasing my crotch by rubbing herself (her va-jay-jay) over my boy parts. I had no clue what to do! But I tried to press up to her as she was rubbing me as it obviously was feeling good. And I absolutely was not going to put my hands down between her legs - I'm totally afraid if I do anything like that I will ruin this. I had no clue what to do with them anyway, and as you will read next, I didn't know at all what to do with my boy part either :-|

She is still on top, we're basically dry humping. Sorry but I don't know how to better say that! Eventually my boy part seemed to find the girl part place it should try to push into. We are both "working it", and since she hasn't reacted badly yet, I decide it's time to push it all the way in. As I do so it's more difficult than I expected. A VERY short time passes and she knows I'm not going to figure it out. She says something like "Is that where you like it? It might be easier if you try starting up higher instead." OOOOPS! Wrong hole! I was mortified. She takes the bull by the horn so to speak and guides me into the proper place. That is the end of what  I remember that night.

So there we have it - my first time. We continued to have fun for a while longer, but I think she had a boyfriend the whole time that I wasn't aware of for a while. Maybe she dumped me?

Epilogue
Miss and her neighbor were good friends for a while. In fact, Miss was in her wedding years later. She married the boyfriend I just mentioned!

While this will be the subject of a future post, Miss and I did end up getting together when I was about 18. She told me recently that leading up to that her neighbor had told her that I was really good with foreplay, and Miss just had to check that out I guess ;-)

Miss eventually lost contact with her, but did find her on Facebook and sent her a message that we got back together. Her old friend and neighbor didn't reply, probably not wanting to risk her husband learning about her little distraction from the past.

I hope you've enjoyed this post! I've certainly enjoyed reminiscing.

Take care!

First recognition of sexuality & kink?

Let me detour a little bit before I get back to what happened with Miss's neighbor... ;-)

My shyness and insecurity about never making a move on Miss definitely shows a  part of my submissive personality. I think swiping her panties from the laundry and how nice I felt wearing them are one of my earlier clues about being transgender, but I have a few other memories about my sexuality and submission that I'd like to share.

First recognition of sexuality? 

My first sexual memory I think was before I was in preschool. Maybe 1970-71? It wasn't really sexual at the time, but when I think back about it now I feel it was. I remember being at a neighbors house watching TV, and maybe playing a game like Chutes and Ladders, or Candy Land. There was a girl my age there. I'm thinking I was being baby sat while my parents were working or something like that. 

The memory I have is only a few seconds long,  and I have point out that I have no reason to think anything inappropriate was going on. But I think in my own mind, over time, I finally processed how I felt about it. This memory has come to mind a few times in the past that I can remember, so it was/is significant to me. But until it came back into mind recently, I never resolved how I should feel about it. It was like the experience was not complete yet. I think this event must have been bothering me subconsciously for about the last 40 years or so :-) 

Here is the memory. The girl and I were on the floor. I seem to remember her leaving for a few minutes. When she returned I noticed that she was now wearing what I later knew to be fishnet stockings. But in my memory they don't look exactly like fishnets, they looked to be made of a thicker material, like yarn. I think I may have asked "what are those?" 

I remember an adult (or could have been an older sibling), making a comment or asking something like "don't they look pretty on her?" So maybe they were stockings and it was "dress up play time"? When I told Miss this story she suggested they may have been tights. I think she's probably right. Maybe this girl was in a toddler ballet class or something? 

If you show me yours, I'll show you mine!

I was in preschool at this time, 4-5 years old? I as at a neighbor's house again, probably my mother was off having whatever kind of life she was able to have as a single parent. We were playing things like Chinese Checkers. 

There was a girl in the house, my age, maybe a bit older. I know it was her idea - more submissiveness? :-) We went into a closet, I remember feeling awkward about what to do. I think I was paralyzed with fear. She had to prompt me to take my clothes/pants off. As I started to she did too. I think she might have touched the tip of my pee-pee in a curious manner. She asked me "What do you do with it?" I replied with embarrassment at my self-ignorance, "I don't know." I looked down at her groin and didn't see anything. I don't think I had the courage to even think about touching her. I remember feeling like I got the short end of the stick because she had nothing to show ;-)

On the playground, 1st/2nd grade. Trying to get girls attention, or just acting out?

In elementary school I was most definitely not an alpha male in any sense of the word. I only had one friend until probably Jr. High. I was afraid to approach people so I was usually alone during recess and lunch. I remember times where I had to "hang around" the teachers on the playground often, because "bullies" would pick on me.

I can remember being on the playground one day. I had no friends at all at this time. For whatever reason I put my arms straight out and started spinning around. I remember doing that and while spinning I moved in the direction of a group of girls that were together on a grassy area. I wasn't trying to touch them, I think I was just using that as a cover to move closer to them and maybe get their attention. I have no interpretation of what that might mean, maybe absolutely nothing. But it was my first memory of having any interest or curiosity about girls. I do know I didn't feel threatened by them like I did boys,

Next stop, straight to kink? BowWow?

The next sexual memory I can recall was probably 2nd/3rd grade timeframe. Like the neighbor girl memory, at the time I had zero awareness of anything sexual. My mind simply hadn't any notion of sexuality yet. But this was definitely sexual on the other person's part. 

I was home alone, maybe sick from school, or spring break. The phone rang and I answered it. A female voice was on the other end. Of course it was so long ago I don't remember exact details of what we said on the phone, but basically she started asking me questions. 

At the start I think she was trying to gauge how much sexual experience I had. Questions like "Do you ever play with yourself?" "Do you like it?" "Have you ever been/played with a girl?", etc. I probably stumbled on my answers, and I don't actually remember much anything about what I might have said back to her. 

I'm sure it didn't take her long to figure out I was young. Maybe she already knew me. A babysitter, or a relative or friend of a babysitter, or a friend of my mothers. 

At some point the conversation moved to a hands-on experience for me. I ended up taking my clothes off. She asked me if I ever played with my pee-pee. I probably said no I hadn't. She then told me to play with it, that it would feel really good if I did what she said.

Anyway, I wanted to do what she was asking. I probably started rubbing my pee-pee from top to bottom (doing it wrong), and I certainly wasn't "feeling" anything good (if you know what I mean). I'm sure I told her that it felt "ok" in an unconvincing tone. But she knew that wasn't what it probably should feel like if I was "doing it" right. I would have started moaning and getting into it, but wasn't.

She probably was a little frustrated that I wasn't getting off, and asked me how I was doing it, and I tried to tell her, and she told me to put my fingers around it and move my hand up and down. She kept asking if it was starting to feel good. Out of guilt I told her yes, it was starting to feel good. Of course... I was not feeling anything. She kept encouraging me to keep stroking, and kept asking if it felt good in a very sexy seductive, heavy breathing kind of voice. Just this very second I realized that she was probably masturbating on the call! Anyway, the call ended. 

There was one more call. I remember her asking if I had ever worn a dog collar. I said no. She asked if I had one, or maybe she knew we had a dog. She told me to get it and put it on. She told me to put it on tight, and I did what she asked. I was naked again, and she had me start to play with myself. She was again asking me things like "Does it feel good?" "Are you getting off on this?" "Do you like the way the collar feels"? But basically the same result for me, I felt nothing really pleasurable.

Spin the bottle

We were at a friend of my mother's house, and there were older kids there. It must have been 4th grade for me. The adults were doing their thing in the living room, and we were in a bedroom. The older kids started a game of spin the bottle. This was the first I had heard of this game. I don't remember how the game actually went (but there was some kissing, not me), and I remember feeling uncomfortable because I didn't already know how to play, so I thought I wouldn't be very good at it. When it was explained, I felt like I wouldn't actually be wanted in playing the game (I didn't know any of these kids before this day). I certainly didn't want to kiss anyone!

Mom's pantyhose and silky slips - first dipping of toes into girl clothes.

OK, this shouldn't be anything unique for us trans people. I was home from school, mom worked. I started going through her dresser and discovered pantyhose. I remember I put a pair on and boy was that a challenge. They felt absolutely wonderful. The tightness around my legs, crotch, and butt. It was captivating. I then tried on one of her 3/4 length slips. OMG! The way that felt! So teasingly gentle, almost a tickling feeling. Then I ran my hand over the slip, moving it gently over the pantyhose. The feeling was the most sensual/sexual I had ever had. I liked the pressure of the pantyhose on my groin, but it wasn't enough pressure, so I put on several pairs of my tidy-whitey underwear until the amount of pressure felt right. No idea what that means (probably nothing), but it's what I remember doing.

This was my first sexual feeling and experience that I recall feeling in the same moment that it happened. But as I sit here writing this, I realize it was much more. In that moment I felt good (yes there was guilt/shame too). But really emotionally good. This was different than other kinds of good feelings I had up to that point. 

Only today do I think I can translate the emotional feelings into words. I wanted to be able to wear those clothes! I wanted to be the person that could wear those clothes! 

I never got into her clothes again. I think in part because somewhere inside "I knew" that it was impossible for men to become women, so I just plodded forward as a male. For 40 years I've made the best life I could as a male, but I'm so much happier and content when I'm not.

OK, that was a boatload to write. I'm probably alienating some who might read this blog, but it is set to "Adult" after all :-D

Beginnings... with Miss

Where to start?

Miss and I met in high school in the early 80's. I was a Freshman (13 years old), she was a Junior. I was still a virgin. She was dating a guy that I was in the same theater class with. He and I both did behind the scenes work, and we became casual friends, which is how I came to meet her.

I was very attracted and turned on by her. More than anyone ever. At some point her and her boyfriend broke up. She eventually transferred to a different high school, and her boyfriend left too, but I don't recall any details this many years later about where he ended up.

I eventually learned where she lived (this while she was still with her boyfriend if I remember), which was on the same street that I lived on! Well, that was lucky for me, and I started stalking her. But NOT for bad purposes!!!

I was obsessed with her, but my insecurity and shyness was equally as large as my obsession. Between a rock and hard place - I was a wreck inside for years because of this. Blissful agony?!!!

But she did accept me as a friend. Well, technically I was in the "Friend Zone." Her single mother was often away all weekend with her boyfriend, so Miss had their apartment to herself often.

I don't remember how I broke the ice to become her friend, but probably I was sneaking around one weekend night to make sure she was home and alone, and got the courage up to knock on her door. I'll have to ask her what she remembers.

At that point I looked for every opportunity to hang out at her place. Given my age, I was sneaking out my bedroom window after I figured my mother was asleep in order to do this. She never knew as far as I know.

If Miss was home I'd stay with her until well after midnight. This went on for 2 years maybe. Miss knew I was hot for her, and she did tease me from time to time which just made me so horny. One time I stole a pair of her panties and I'd wear them and play with myself, masturbating now and then while wearing them.

That reminds me, my first wet dream and the dawn of my sexual self-pleasuring all started at this time, so she gets credit for that too :-P

She dated other guys in this time too. I think I only remember that fact coming up once, and of course I was so jealous and devastated.

Probably a year or more into this, she moved to an different street, still very close by. She made friends with a next door neighbor, a single mom with a 5 or 6 year old child. Eventually I met the neighbor.

Of course I'm still stalking Miss, looking for every opportunity to hang out with her. I think her neighbor "caught" me one evening, saw me walking, so I said I was just stopping by to see if Miss was around. She might have said that she thought Miss might be back later, and I probably said I'd check back, and I think she offered to let me hang out and wait up at her place.

Well, I was in for a completely unexpected surprise that night... more later!