My Life Pt. 02

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Continuing story about a young trans girl and her teacher.
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Part 2 of the 7 part series

Updated 06/08/2023
Created 09/01/2016
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ShyTammy
ShyTammy
455 Followers

So this is part two of my life story. All the stuff from Part 1 still applies. As before all characters engaging in sexual acts are over the age of 18. This story is chronologically linked to Part 1, which won't necessarily be the case with other stories in this series.

*****

Decisions, Decisions

It had been two days since my encounter with Mr. Moran in detention. I had given him my first kiss and first blow job. Since that happened, there was like ZERO communication between us. I tried catching his eye on a number of occasions, but he avoided me like I had the plague.

Rationally I get it. We had crossed a line that could get him in a lot more trouble than me. Teachers having sex with their students in high school was generally frowned upon. He could lose his job, I was over 18 and the whole thing was enthusiastically consensual so I didn't think he needed to fear any kind of legal issues. Anyway rationally I get it.

Emotionally I was dying inside. I wanted to talk to him so badly it ached in my chest. I still didn't really know what was up with him, if he was gay, did he just like my cock, or did he like the whole package of me? Was this going to be a one-time thing, or did he want something more? I was dying to ask him these questions and more, but again he was avoiding the hell out of me.

I also had other big things on my mind. I had become best friends with two cis girls Kelly and Theresa (for those of you not up on the Trans lingo CIS means born genetically the sex you identify with). So far I had managed to keep my little secret from everyone, but I was getting really close with Kelly and T and my continued deception was starting to feel like a betrayal, so I had a decision to make on what kind of person I was going to be.

On one hand I was really enjoying my "normal" life and the fiction I had manufactured. Namely that I was a pretty, but not extraordinary 18 year old high school senior with aspirations for college. This on the surface was true, but underneath I was also a Trans girl with a penis. Some people, most people, find that kind of thing to be an important detail. I don't really, but I understand why others do.

I've always wanted to be out and accepted for who I am. That is just the way I am. My Mom on the other hand worried for my safety, and with good reason. If you're not familiar I encourage you to look up the sexual assault, suicide and murder rates against trans people. It's a bleak picture, but I still feel honesty is better.

Here I do have to give major props to my Mom. Having the support of a loving parent really does make all the difference in the world.

The truth of the matter is that I was one of the lucky ones who have the privilege of passing. My Mom helped me transition younger than most and as a result my body, my face and my voice are all very feminine. If you don't get into my panties you'd never know. It is a seductive thing to be accepted, even if it isn't for who you really are. To my knowledge at that time only two people knew, my Mom and Mr. Moran. I was starting to feel really guilty about it. I decided I was going to come out to Theresa and Kelly that weekend. I needed to tell my Mom first.

Confiding

My Mom through some supernatural Mom power seemed to know I needed to get some things off my chest. She came up to my room one night, brush in hand. I sighed when I saw her. We both know that when my Mom brushes my hair everything comes pouring out of me. I just can't keep anything back, again that Mom super power.

I sat in my chair at my vanity and she stood behind me brushing my hair. It was about shoulder length at this time, dark, thick and wavy. It was a challenge to brush for sure! After she got the worst tangles out we started talking.

"How are things at school?" She asked as she brushed and stroked my hair.

"Good," I replied "interesting."

"Oh?" she responded "and would this interesting have anything to do with that teacher you were crushing on, what's his name?"

"Mr. Moran" I replied, damn she just seemed to know everything.

"Tell me about it."

I did, I told her everything right down to giving him head. She listened without judging.

"Well," she said, "you're becoming quite the young woman."

"You're not upset?"

"No Sweetie," she replied "why would I be? I've already told you I thought he was a good choice, just don't get too attached. It won't be your last and it won't last forever."

We chatted for a while about the lack of communication. She said that he's probably scared and has a lot to work through, but he'd eventually come around. Her experience always makes me feel better.

"So what else is going on?" she asked.

"Well, I was wondering if I could spend the night over at Kelly's this weekend?" I asked meekly. I could see her frown of concern in the mirror. I cringed.

"I guess that would be OK." She said after thinking for a moment.

"Really?"

"Yes Really."

"Thank you, thank you, thank you!" I said turning to give her a big hug, pressing my cheek against her big boobs. She laughed and we went back to brushing my hair.

"So are you going to tell them?" Damn she was good.

"Yes, I think so." again the frown, she didn't like me being open. Not because she was ashamed, but because she worried about me getting hurt.

"They are good people Mom." I replied, "Theresa was even talking about starting a GSA at our school."

A GSA is a Gay Straight Alliance club to foster tolerance and acceptance of LGBT people in case you weren't aware of things going on with high school kids these days.

"Is she Gay?" my Mom asked.

"Theresa?" I replied laughing "NO WAY! She's uber boy crazy, but she does like gay boys probably a little too much."

We both laughed at that. My Mom said she was the same way in high school and that not all effeminate boys were gay.

"You're becoming quite an amazing young woman and I am proud of you." my Mom said with affection "You do what you think is right, I'll be here to support you if you need it, but I won't stand in your way anymore."

Self-Exploration and Missed Communications

So after my Mom went to bed I was feeling a ton better about things in general. I was still anxious about Mr. Moran, but I could live with it. I was also super horny, like all the time since that day. I wanted more.

Now the thing is I wasn't terribly sexually experienced, I mean I had really just given my first blowjob, but I wasn't exactly a novice either.

I watched a ridiculous amount of pornography. Like a lot. I watched all kinds, gay male, straight, lesbian, and especially "shemale" porn. I don't care for that word but if you want porn of people like me it is something you have to get used to typing. I was fascinated by all of it. I was just plain omnivorously sexual. In today's language I was, and am, pansexual.

I also had some sex toys that my Mom bought me for my 18th birthday. I had a butt plug, a small thin anal safe silicon dildo, a small vibrator (which Mom cautioned me never to insert as it is too small and doesn't have a flared base), and lots of lube. I was no stranger to anal sex and I loved it.

Now I know what you are thinking, "what kind of Mom buys these kinds of things for her kid?" My answer to that is the best kind! My Mom and I were very open with each other about sex. I obviously came out to her and discussed many of my sexual interests and she answered all of my questions. She was a very knowledgeable person.

Now I was horny on a level that no mere quicky would satisfy. I needed to put my toys to some use. I got out my dildo and some lube. I put on some music and locked my door. I lit a couple of candles and killed the lights.

I wanted to feel sexy so I put on a lacey pair of boy short style panties with matching bra. They were a purple stretchy lace that looked fantastic against my somewhat dark skin. The bra wasn't padded which I liked a lot. I love the scratchy feel of lace against my sensitive skin and my nipples are definitely sensitive.

I lay back in bed and closed my eyes, just listening to Tricky thump out his sexy rhythm and letting my mind wander. I trailed my fingers lightly across my belly. I have a really flat belly, which I work hard for and I'm proud of. My finger nails tickling my skin. They were long and painted purple with little black stars that I did myself.

My fingers traveled over my hips and then down one thigh and back up the other. I was hard in my panties and I liked the way my cock looked, head just poking out of the waist band. I let the tips of my fingers ever so lightly tease my cock. Every so often a tingly feeling would move like a wave through my whole body.

I love how soft my skin is to touch. I love the little hills and valleys of my body. These are the sorts of things I think about when I get really into my sexuality. Maybe it is narcissistic, but I like to think about how other people see me, how some of them might desire me. Right now I am thinking of Mr. Moran desiring me. I know he might not actually, but this is my fantasy.

With one hand I continued to tease myself, pinching my nipples through the lace of my bra, fingers exploring up to my neck and back down to my legs in a slow lazy pattern that matched the trance music. My cock was achingly hard and begging for attention, but I ignored it mostly, focusing on just feeling really good.

My other hand took up my dildo and traced a line with the head between my small breasts, over my collar bone and up the side of my neck. Then it found my mouth and played along my lips, teasing and begging me to let it inside. Taking it between my lips I started to suck and nibble it, feeling the shape with my lips and tongue as I slowly pushed it deeper between my soft wet lips.

I moaned when I felt the need, I let my body squirm and arch and beg for more. I did what felt good.

I thought about the dildo I was sucking on, was what I was doing going to give pleasure to a real one. I tried to remember every detail of what it felt like to suck a real cock, the heft, the softness and taste. My body was really responding now, back arching and moaning and begging myself for more.

I took a moment back to reality to wedge the dildo between the wall and my bed so it was sticking out. I got my book and opened it to the page that Mr. Moran had showed me that day. A drawing I had made of him standing behind me and kissing my neck and massaging my cock.

Then I opened the bottle of massage oil/lubrication and covered my hands in the velvety smoothness of it. Lying back and spreading my legs, my hand finds its way under the waistband of my panties, coating my cock with the oil warmed to my hands.

Oh my! I sometimes forget how good I can make myself feel.

My back arches pushing my breasts toward the ceiling, my ass down into the bed. I moan as my fingers slip further between my legs, probing my tight little ass. Getting it wet with the lube. My other hand finds my nipple. I gasp in pure ecstasy.

Oh god!

My mouth finds the dildo. I am imagining it's him, sliding between my lips. I suck him remembering how it felt two days ago. This urgent feeling building and building in my body. My finger presses harder into my ass, penetrating. My hips buck as if controlled by someone else.

"Oh fuck!" I cry out loudly.

And then my whole body is convulsing, pulsing with pure energy and pleasure. I realize that I am moaning much louder than usual, but I can't stop it. Something warm hits the side of my face, then another across my chest and then a warm trail down my belly. My body is still pulsing and moving.

Then I collapse, tremors pulsing through me every few seconds as I come down. I blush as I hear my mom giggling in her bedroom. The walls are really thin here. "Good one" she calls out, the acknowledgement that she knew exactly what I was doing making me blush even more.

Coming back to my senses I realize I am absolutely covered in cum from my left cheek down to my lower belly. Damn that was good. More importantly I have this relaxed floating feeling. Pushing the cum from my cheek into my mouth I savor the taste.

Then I need to clean up so I can get some sleep. I strip naked and wipe myself down with a cloth. Put on some comfortable cotton panties and laid out a t-shirt I was going to put on. I cleaned my toy and set it on my dresser to dry. As I was picking up my book to put it away, something fell out. It was a paper note with the following written on it:

JMrnXXXXX (changed for privacy of course)

9-11 pm

I looked up at the clock. 10:45 PM. I scrambled to my laptop and flipped it open, knocking over a cup of pencils and making a huge racket.

"Shit!"

"Come on, come on, come on!" I yelled at it to boot up.

My Mom came in just as I was booting up the Instant Messenger.

"What's going on in here?" she asked, seeing my frantic state.

I turned to look at my Mom and holy shit. She was wearing a black slinky nighty with cream lace at the breast and hem. You have to understand that my Mom is absolutely the sexiest woman in the world and here I was topless in nothing but panties. All of a sudden those panties started to get really crowded with my growing erection. Fuck I really didn't need that right now.

OK, so I know what you are thinking and yes I was turned on by my Mom. It happens sometimes. Well lots of times but you see my Mom is really, really hot. She is the definition of the word "voluptuous". Long dark wavy hair like mine, sultry dark eyes and the rest is all curves, she is gorgeous.

She gave a slight smile at my discomfort and then ignored it.

"What's going on?" she repeated.

I handed her the Post It without saying a word. She looked at it and looked at the time.

"Oh," she said coming to stand behind me, "you better hurry then."

I typed my password and hit "Sign In" then it was connecting. It was taking forever.

Then it connected and I immediately pulled up a an IM window and typed in the address at 10:49 PM.

SxyVixen1> OMG hello?

SxyVixen1> R U There?

SxyVixen1> Please be there

JMrnXXXXX> your spelling is atrocious

My Mom stifled a giggle behind me and gave me a comforting squeeze of my shoulders. I was painfully aware of not having a top on for some reason.

SxyVixen1>Oh wow, uhh hi

JMrnXXXXX> hi

SxyVixen1> I am so sorry I just found the note

JMrnXXXXX> I'm glad you did

SxyVixen1> me too :-D

JMrnXXXXX> So

SxyVixen1> So... yeah

JMrnXXXXX> We can't do that at school anymore

SxyVixen1> oh

JMrnXXXXX> I mean, I could get in a lot of trouble

SxyVixen1> I know

JMrnXXXXX> I'm not sure what to say

SxyVixen1> do you regret it?

JMrnXXXXX> No, no, please don't think that

SxyVixen1> ok...

JMrnXXXXX> do you?

SxyVixen1> I loved it

JMrnXXXXX> oh god me too

SxyVixen1> but you don't want to see me anymore?

JMrnXXXXX> I do, but I don't know how

SxyVixen1> I'm 18

JMrnXXXXX> You're a student

SxyVixen1> I guess so

JMrnXXXXX> I don't know what to do

SxyVixen1> what about outside of school?

JMrnXXXXX> I guess we could

SxyVixen1> do you live alone?

JMrnXXXXX> Yes

SxyVixen1> You could invite me over, I mean if you wanted to

JMrnXXXXX> You'd really want to come?

SxyVixen1> Yes!

JMrnXXXXX> How about Friday?

SxyVixen1> Yes!

JMrnXXXXX> OK.

My Mom kissed my cheek and left. We stayed up chatting until nearly 1 AM. We were just learning about each other. I asked him if he was gay. He told that he was really confused about his sexuality. He normally wasn't too attracted to women, but some really turned him on. He also really liked men, but was afraid of them. As a result of all of this, he was still pretty inexperienced, almost as much as me.

I also learned that he was 28 and that he loved teaching, that he wished he was better looking and that he was more socially adept. He asked me all kinds of questions about what happened after the seventh grade incident.

We also made some plans for Friday. I would come over to his house, which turned out to be only a couple of miles down the road from where I lived. He would cook me diner, all I had to do was show up at around 7:30.

Big Date

School let out early on Friday. I rushed home and practically dove into the bath. I don't know why, I wasn't in any kind of hurry. I shaved my legs, arm pits and everything else. I like being completely smooth.

After my bath I rubbed myself down with a strawberry vanilla lotion that makes my skin silky and soft. I smelled so good I wanted to lick myself, but I didn't because I knew from experience the lotion didn't taste as good as it smelled. Then I started to get dressed. I went through a bunch of outfits and before long my Mom came home from work and started helping me put together my look for my big date.

We settled on an outfit that really emphasized my best features. We chose long sleeved, deep red, strapless crop top that left my shoulders and midriff exposed. I am thin and fairly toned so this really emphasized parts of my body I feel comfortable showing off.

The top crisscrossed over my chest so gave me the illusion of having bigger boobs without being ridiculous. For the bottom we picked a cute plain black pleated skirt that really showed off my butt. We added some black satin and lace panties. I didn't need a bra so decided not to wear one. I did put the bra into a bag along with some other things I hoped I would need for later. We finished off the look with some cute black patent leather pumps.

I sat down and did my makeup and then my Mom did my hair up. It was a really elegant look, with some pretty silver flower pins holding it up and several tendrils of my hair left loose to spiral down and frame my face. I used a dark natural eye shadow and a dark red, almost burgundy lipstick.

Accessories we added a small clutch bag that my Mom lent me, some gold hoop bracelets and little gold stud earrings (I have four holes in each ear). My Mom also lent me a really beautiful ribbon choker with a pretty pendant with the bust of an elegant Victorian lady.

Looking in the full length mirror at our handiwork I was blown away. First thing is that I looked older, much older and very elegant. I hoped it wasn't too much. I mean he invited me over for dinner, not a night on the town. The second thing was that the outfit was elegant but also really comfortable. Once I took the shoes off I could hang out in it for hours without feeling put out. The third thing was I looked fucking hot and was not changing a damn thing.

So on the drive over I was feeling pretty confident, but as I pulled onto his street my heart started pounding like crazy. I was really doing this, my first date. Who knew what else the night could bring?

So the thing is it was still important that we not get caught. When I pulled up to his house the garage door was open as we had planned and I pulled right in. I crazily wondered if I had the right house when I got out but soon the garage door was closing and the door to the house opened and there he was.

"You look beautiful!" he said with genuine enthusiasm.

So my man, what can I say? He tried for me; he was awkward and unstylish but absolutely lovely. He had on a nice pair of pants and a button up shirt that didn't go well together, some kind of product in his hair and he smelled of aftershave. Clearly he went a lot of effort on his appearance, which made my heart swell with affection. We could work on his style later; he was absolutely perfect right now. As I approached he brought out a bouquet of fresh red roses from behind his back. Wow, he was making me feel amazing!

I took the roses and greeted him with a nice, passionate but not full on make out kiss. Then he led me into his home. It was tasteful but sparse in furnishings.

He ushered me into his small dining room where I was greeted with a candle lit table set for two. Wow, I was not expecting this much romance. He served me a nice light diner of pesto pasta that was really well prepared. As he was serving he opened a bottle of red wine.

ShyTammy
ShyTammy
455 Followers