From Nerdy Terry to Lovely Teresa

Part 1

Nerdy Terry becomes the lovely Teresa

Being raised by a single mother and two older sisters may or may not be a contributing factor to me being trans, but I feel like it may have had a little to do with it. Growing up I was completely exposed to everything from a woman's point of view. I didn't know any different, as I never had a male role model. So for me, being effeminate was the only way I knew how to act.

As a child, my two older sisters would dress me up as a girl and put make up on me. They even started calling me Teresa instead of my given name, Terry. They enjoyed turning into their little sister and taking pictures of me. At the time, I didn't know any better, so I pretty much accepted that I was a girl. So much so, that I insisted that they call me Teresa. For quite a while my sisters and my mom just let me be the girl that I thought I was. They bought me dresses and I played with dolls. I wore girl's clothes pretty much everyday until I started going to school.

My sisters were quite a bit older than me, so when they got to high school, they had more or less outgrown using me as their little dress up doll. My mom had to explain to me that they were just having fun with me and that I was a little boy, who needed to understand that before I went off to start school.

It took a little time, but I soon got used to the idea that I was actually a boy. At that age, it wasn't too difficult to get acclimated to the change. I went to school. I saw other boys and I adapted pretty quickly. My sisters weren't around all that much. They spent time with friends and had part time jobs. Me being a girl wasn't even ever talked about anymore.

That was all well and good with me. I met other boys and started interacting with them at school. I really didn't think much about my past femininity all that much for quite some time. I grew up as a relatively well-adjusted little boy, despite not ever developing any "manly" qualities.

Through elementary and middle school, I did have a few friends, but mainly kept to myself. I realized I had quite an interest in computers. Doing anything with technology seemed to come pretty easily to me. With that, I became increasingly interested in computer games and emersed myself in the fantasy world of video gaming.

Right around 8th grade a boy named Kenny moved into our neighborhood and we became friends. He, like me enjoyed playing a lot of video games. We spent a lot of time at my house in front of the computer playing any number of games for hours on end. We'd come home from school, and play on the gaming system until he had to go home for dinner.

For the remainder of 8th grade and through our Freshman year of high school, Kenny and I were inseparable.

Right before my sophomore year, my mom lost her job and had to take a job working nights. That left me home alone almost every evening during the week. After Kenny would go home for dinner, I was left to my own devices.

My mom would always have something there for dinner. After I ate and cleaned up a bit, I'd do my homework, then escape into my fantasy world until it was time for bed. Some nights rather than game I would play around searching on the internet.

As I mentioned earlier, I'm pretty much a nerd. I do well in school, I love gaming, I'm good on the computer. I'm not a manly man by any means. I'm not good at sports (I don't even care about them). I definitely lean towards the effeminate. That said, from time to time I harken back to the days when my sisters would dress me as their little sister. I often wondered if there were any other boys like me out there. That curiosity opened me up to a whole world that I never knew existed.

As it turns out, I was NOT the only one who occasionally thought of what it would be like to be a girl. Not by a long shot. My eyes were wide open to the online world of transvestites and transsexuals.

I read story after story about boys who felt like they should have been born girls, and men who actually transitioned into women. My curiosity was peaked! I was so happy to find out that I wasn't the only one who had these feelings.

One evening I decided to "borrow" a pair of my mom's pantyhose and try them on. Before I even pulled them all the way up, I could feel my dick getting hard. Once I had them completely on, I was in heaven. They made my legs look so long and feminine and felt so nice and tight around my boy parts. That was when I discovered masturbation, and it felt wonderful.

The more I read and the more pictures I looked at of men dressed as woman, the more curious I became. I again went to my mom's room to find some items to help me improve my look. I'd put on make up and one of her bras to go with the pantyhose. I even watched videos to help with applying makeup. After some time, I got pretty good at it.

So for a long time, this was my evening ritual after Kenny left. After dinner, I'd put on make up and wear a bra and pantyhose around the house. I'd do my homework, play video games, or whatever else that I'd need to do. Whenever I was home alone, I'd be dressed.

All of this was fun, but I wanted more. I wanted to complete the look. I rummaged through my mom's closet to find just the right outfit. She didn't have a lot of dresses, but I did find one to try on. We were roughly the same size, as I am pretty much slight of statue. I have to say it fit rather well. Luckily she had a pair of heels that matched. They were a little snug, but I would make due.

I put on my makeup, stuffed some wadded up wash clothes in my bra and slipped on my pantyhose. I stepped in the dress and slid on my heels. I stood in front of the full length mirror and was so happy with the girl looking back at me.

Every moment I spent alone was spent in that outfit. I couldn't seem to get enough of being a girl. That lasted for quite a while, but after some time... I wanted more.

I needed to find a wig. I didn't want to grow my hair out as to not arouse suspicion. I also wanted to be able to pick out my own outfits to sort of create my own style.

Fortunately, I grew up in a world where weird little transsexual boys can shop for cute clothes from the comfort of their own homes.

I had some money saved up from tutoring to buy a few things. I found an inexpensive wig, a really cute black pencil skirt, a pink bodycon top, some black pantyhose and a pair of black heels (that actually fit). I couldn't wait for my packages to arrive.

When everything finally arrived, I was in heaven! I loved how I looked in that outfit. Having the wig really put the feminine look over the top. I was a girl again.

Looking back, I think I would have considered myself almost asexual. I really had no attraction to girls (or boys for that matter), but the thought of being a girl got me very sexually excited. That's when I fell into the rabbit hole of transsexual porn.

I watched these absolutely gorgeous transsexuals having sex, and that led to even MORE new feelings within me. The more videos I watched, the more I wanted to look like the girls I saw onscreen. My attraction was more of how much I wanted to be like them more than be with them. I strangely felt myself much more attracted to the men in the videos. I wanted to be the girl who was pleasuring the men.

As you might guess, my evening gaming time lessened and my time watching men have their way with tranny women dramatically increased. I even found myself watching gay porn. I was getting more and more turned on by cute guys. I would masterbate a couple of times every night watching videos in my girlie outfit.

You might think that during this lifestyle change, I would neglect my studies and that my grades would slip. That wasn't the case. Boy or girl, my studies came first (I came later).

After donning my femme attire for the evening, I would start my studies. Most nights while doing my homework, I would fantasize that I was an administrative assistant working at a big company and that I was working late for my demanding male boss. My homework was completing reports that needed to be completed for a big proposal before I could go home for the evening. My reward was getting to suck the boss off before leaving for the night. I even started stealing my mom's cigarettes, so I could pretend to go out with the other girls in the office for a smoke break. I would go out to a spot on our back porch that wasn't visible to anyone behind our house. I would smoke then come back in and watch tranny porn and jack off, while I imagined giving my boss a blow job. I know it sounds crazy, but that whole scenario gets me so hot.

I continued this activity for quite a while and derived great pleasure from it every night until I had to change and take my make up off before my mom came home.

Between my Sophomore and Junior years of high school, I took a part-time job at a local grocery store. It definitely cut into my dressing time and gaming time with Kenny, but allowed me to buy new outfits, make up and a much nicer wig and a new purse to put my make up in, as well as being able to buy my own cigarettes.

That's when things got a little dicey for me and Teresa. One Friday night before I had to work the next morning, I was doing my usual evening escapes as Teresa. After I was finished for the evening, I took off my make up, changed my clothes and stored everything in my locked desk drawer, or so I thought. I inadvertently forgot to put my purse securely away. It had all of my make up and my cigarettes in it. I went to work before my mom woke up.

Apparently while I was gone, she'd gone down into my room to gather up my dirty laundry. When I got home, my purse was sitting on the kitchen counter. When I saw it, my stomach dropped and I was as pale as a sheet.

My mom glared at me and asked, "Care to explain?"

I was dumbfounded and stammered. "Um. Well." I didn't have anything to help myself out.

She said. "I'm waiting."

"Mom, I'm sorry. I don't know what to say. I don't have any excuses." I responded.

She asked the standard questions when a boy gets caught with girlie things.

"How long has this been going on? Are you gay? Do you want to have a sex change? When did you start smoking?"

I really didn't have a leg to stand on. I was caught red handed.

"I've been doing it for a while. I just like the way I feel when I get dressed up."

There was some more yelling from her and tears from both of us. I tried to blame my sisters for dressing me up as a kid and her for not objecting to it, but she wasn't buying it. She stormed off, but not after saying "NOT IN MY HOUSE!!"

I went to my room and did some more crying. I was pretty humiliated. I'm not sure what I expected from her, as I should have figured that she'd find out eventually.

We didn't really speak for a few days and I didn't dress up at all during that time. Then she woke up early one Friday specifically to talk about it before I went to work.

"I thought about what you said. You're probably not wrong about how I let your sisters dress you up when you were younger, and I'm sure it didn't help that you were raised in a household of women with no male role model to speak of. "

I said. "I' m sorry mom. I never wanted you to find out like this. I would never try to hurt you."

She responded. "I'm sure you didn't. I really shouldn't blame you. So, honestly, how long has this been going on."

I was honest, even though I was nervous to say it. "A couple of years on and off, but I've thought about it a lot longer"

"Oh my. So it's not just a phase?" she asked.

"I don't think it is." Was my reply.

"Do you want to be a girl?" she asked

"I don't know, but I do know that I like feeling like one." I responded.

"Do you think you're gay?"

"I don't know." I lied.

We talked about a lot of stuff that morning and I was pretty much open and honest about everything. Before I had to go and get ready for work she asked.

"Would you ever want to let me see you as a girl?"

"I honestly would. Truthfully, I really tired of hiding it." Since tomorrow is your day off, we can do it tomorrow, if that's okay.

"Of course. I'll make breakfast in the morning and you can get ready before that."

"Great" I said with a great sense of relief.

The next morning I woke up early to get ready. I wanted to look my best, so she knew I was serious about completely looking the part of a girl. I heard her upstairs in the kitchen making breakfast.

I took my time putting on my make up and fixing my hair. I didn't want to over due the make up so she didn't think I was too slutty. I'd just gotten a new denim skirt in the mail that I hadn't worn yet, so I thought, no time like the present. I matched it with a tight little pink sweater. I put on some suntan colored panty hose and my black heels and put my "boobs" in my bra and headed upstairs.

My legs were shaking horribly as I entered the kitchen. She heard my heels click on the linoleum and turned around.

She looked for a few seconds before saying anything.

"My son has grown into a very pretty young woman." She said with a smile

"This is not at all what I expected." She continued

"I was waiting for a boy in a dress with some kind of clown make up, but I have to say, you actually look very pretty."

"Thanks mom. I'm so happy to hear you say that." I blushed.

"Now sit down and have some breakfast." She said.

I sat down and crossed my legs under the table. At which she said,

"Oh, you are even sitting like a lady."

"Of course." I grinned "How else would a proper lady sit?"

While we ate, we talked more just about everything related to my dressing.

Before we finished eating I asked the question that I'd been wanting to ask since we sat down, but just now got the courage to ask.

"Mom, would you be okay if I dressed like this all the time around the house?"

"Oh wow." She responded. "I don't know if I'm really ready for that. Are you ready for me to see you everyday dressed up like a girl?"

"Mom, I've been ready for this for a long time." Was my response.

She came back with, "Well, I suppose we can see how things go as long as you promise that you only do it behind closed doors."

"Deal!" I said with the biggest smile you could imagine.

Before we finished she said one more thing. "About you smoking."

"Ugh. I was afraid you'd bring that up." I said.

"If I forbid you from smoking are you going to stop?" she asked.

I waited for a second and said "Probably not."

"That's what I figured. Well, both of your sisters smoke, I smoke, so I guess there's not much I can say." She replied.

With that she took out a cigarette, lit it and offered one to me.

"Are you sure?" I asked.

"Sure. Go ahead." She replied.

I took one and lit it. I had never felt so liberated in all of my life. I had an overwhelming sense of confidence, so I felt comfortable asking the following question.

"So, while you're in such a good place with being a girl and with me smoking, I have one more question for you."

"Do you really want to press your luck?" she asked.

I smiled and asked, "When we're at home would you call me Teresa?"

"Do I have a choice? I can't really call the girl sitting across from me Terry, can I? Oh, and by the way Little Missy, I would suggest some more sensible shoes if you don't have them already. Wearing 4 inch heels around all day is going to be hell on your feet and legs."

I didn't want to admit that she was right. My calves had been pretty sore since I'd been wearing heels almost every day.

The remainder of my summer was spent completely en femme. Except of course, when I was at work or hanging out with Kenny. There were plenty of times when Kenny was at my house over the summer just hanging out and playing video games and even times he spent the night for our gaming marathons. As much as I liked spending time with him, I would always be happy when he left, so I could slip into something more fitting for a blossoming young woman.

On Kenny-less Saturdays, mom and I would spend the day together. Something we hadn't done for a long time. Being a girl really made me feel so much closer to her. I wouldn't always get dolled up for our days together, but always wore the essentials: Wig, make up, bra and panties. I'd also always wear pantyhose or tights no matter whether I wore a dress, skirt or leggings.

We'd spend the day watching movies, talking or I'd even help her with straightening up around the house. It was so much fun just being able to finally be myself around her. It was like starting a completely new relationship with my mom.

She even helped me shop for new outfits online. It was her suggestion that I look into some more realistic breast inserts to take the place of my wadded up wash clothes. She helped me pick out a pair. We went with a C cup. Nothing too big, but something that looked good under a nice tight top. She even offered to pay for a couple new bras.

One Saturday, she suggested that I not get fixed up and that I accompany her to the mall. She needed to get some new clothes for work and thought it would be fun for me to go with her and see if there might be something I would want to pick up for myself.

Turns out there were tons of things I wanted to buy. I'd never shopped for myself in person, so this was all so new, exciting and fun for this girl. After much deliberation, I settled on this adorable little black dress. It was a body contour spandex dress with a short little skirt and crew neck. I just fell in love with it. Mom offered to buy it for me for my upcoming birthday.

We got home and I couldn't wait to try it on. It fit like a dream. Now I just had to wait for my new boobs to come in the mail.

It was so wonderful to see my mom get excited about how I looked in a dress. Something I never thought I'd see. I really feel like we'd gotten closer than we'd ever been before. I think she kind of liked the idea of having another daughter to bond with.

I went down to my room and slipped out of my dress and put on some tights and leggings. I put on my PINK hoodie, some eyeliner and mascara and went back up to hang with mom.

She was on the couch picking out a movie for us to watch on Netflix. I grabbed a cigarette out of my purse and sat with her. She started the movie. The movie happened to have several really cute guys in it. We watched in silence for a while until she broke the silence.

"Teresa, there's been something I've been meaning to ask you."

"Uh oh" I thought.

"When I found about you dressing as a girl, I asked you if you were gay, and you said you didn't know. Do you know now?"

I swallowed hard. I figured this would come up at some point, so I thought I would be ready to talk about it, but the words didn't come out the way I wanted. I mean ever since the first time she saw me dressed she pretty much accepted me as a girl, so I figured she couldn't be too upset if I continued being honest with her.

"Yeah mom. I know. I think I've known for a long time."

"And?" she asked.

"Well" I started. "I'm definitely attracted to guys, so I guess I am gay, but on the other hand, I honestly feel like I'm a girl on the inside. So in that case, I truly feel like I'm a straight woman. For all intents and purposes, I guess being a biological male, who is attracted to men, I guess I am considered gay."

I know she knew the answer to the question, but wanted to hear me say it. She didn't act the least bit shocked.

"Yeah. Kinda what I figured." She responded.

"So next question." She asked "Are you attracted to Kenny?"

"Mom!" I exclaimed as I put out my cigarette. "He doesn't even know I'm trans."

"That wasn't my question, my dear."

Well, no time to start lying now I thought.

"I wasn't for a long time. Not until I started dressing a lot. The more I dressed the more I felt like a woman. The more I felt like a woman, the more feminine I felt. The more feminine I felt the more I started to become attracted to guys. So now, when I'm with him, I see him as more than just my friend Kenny." I said not making eye contact with my mom.

"Well, I guess I'm not surprised. Kenny is kinda cute." She said.

"Mom!" I yelled before saying...."Yeah. He is isn't he?"

"So. Do you think you're ever gonna tell him about Teresa?" she asked.

"Oh god no! I could never!! What if he thinks I'm a freak? What if he tells people about me?"

She responded. "Teresa, you two have been friends for a long time. If you're going to continue moving forward as a girl, you'll have to tell him at some point. Even if you only tell him you're trans, and not mention that you like him. I'm sure you'll find the right time. I just want you to be happy. These last couple months have been really special to me. I see you in a completely different light. You used to be an awkward boy who lacked confidence in yourself. Someone who couldn't look someone in the eye when you talked to them. Now, you are brimming with confidence. You've really come out of your shell since you've come out to me. You are a completely different person. I know a mother shouldn't encourage her son to be transgender, but in two months you've grown as a person more than you've grown in the past 17 years. So, I say be the person you want to be. If you want to be a girl. Be a girl. If you want to be gay. Be gay. If you want to tell your best friend you have a crush on him. Tell him. If you want to be my daughter, then you can be damn sure that I will accept you as my daughter, if that's what you want to make you happy."

Tears were flowing from both of us. Happy tears. Very happy tears. Even though I was 100% comfortable being a girl in front of her, hearing her say that let me know that she was 100% comfortable with me being her daughter (at least while we were home alone).

"Thanks mom. I love you." I whispered through my tears. "Thanks for ruining my make up."

She laughed and continued. "I love you too sweetheart. Now go fix your face so we can finish our movie."