From Nerdy Terry to Lovely Teresa Pt. 02

Part 2

School started the next week and I was back to only being able to be Teresa after school and on the weekends (when I didn't have to work). I'd thought a lot about what mom said about Kenny. I wanted to tell him about Teresa, but wasn't sure how to handle it.

A little about Kenny: He's a bit of a nerd too. Not as bad as me (as a boy). He's got short brown hair and a super cute smile. Kenny is a lot less awkward and a lot more confident than Terry. He's taller and far more masculine than me. Not what you'd call classically handsome by any means. His personality makes up for any physical shortcomings he might have. He's one of those guys who you may not look at twice, but when you get to know him the more attractive he becomes. That being said, Kenny is my kind of guy. I just need to figure out a way to tell him that I have the hots for him.

Well, a few weeks later, unbeknownst to me, I'd get my chance.

I had to work a lot that week and had very little time to be myself, so when Friday came, I told Kenny I was just going to hang tight that night. Maybe we could game online later. He was cool with that and said we could hook up online in a bit.

Since I hadn't dressed all week, I decided to get all dolled up. My make up was on point and my hair looked cute, as I slipped into my little black dress and black panty hose. My new breast inserts rocked in that dress. I stood in front of the mirror and was very pleased with the girl staring back at me. I didn't see the dorky guy who I'd known, but saw a really pretty girl who I wanted to know more.

I just sat around for a bit occasionally getting up to look in the mirror to admire my handy work for the evening. I jumped online to do some gaming and to see if Kenny was on there.

Sure enough he was and we played for a bit. After some time, I decided it was time for a smoke break. I sneaked out on the porch and hid in my little corner to enjoy a Virginia Slim.

As I was relaxing outside, I received a text from Kenny:

"Dude, who's the chick smoking on your porch?"

"What are you talking about?" I texted back. My legs started shaking with nerves.

"T, I know your mom is working and your sisters aren't there, and I damn sure know you don't have a chick there." He responded.

What the hell was I going to do? What should I tell him? As they say, we are all braver behind our keyboards, so I figured now was as good a time as any to come clean to my best friend.

"Kenny" I typed "Something I wanna tell you, but you HAVE TO promise me you will never tell a soul."

"What's up bro?" he responded.

"PROMISE!!" I replied

"Sure dude. Of course" he typed.

I've known Kenny long enough to know that he'd keep his word, so with my new found feminine induced confidence I told him it was me and that I've been cross dressing for long time via text.

"What the?! Dude we gotta talk. I'm coming over."

I took this as a positive and told him to come to the back door.

I ran inside to make sure my hair and make up looked okay when I heard him knock at the back door.

I opened the door slowly, looking down sheepishly.

He was like "Bro. I don't know what to say. I never woulda guessed. Why didn't you tell me about this? How long you been doin' this?"

I looked up at him. He had such a puzzled look on his face. I just prayed he'd keep my secret. I invited him in and closed the door.

I just spilled my guts to him. I told him everything about my dressing as girl, but didn't tell him about having a crush on him.

He listened intently as I choked up a couple times when I told him that I love being a girl.

He let me talk and didn't interrupt as I told him just about every detail about how I've been dressing the past couple of years.

When I finished, he was silent for a short time, before saying.

"Dude. You're my best friend. It's cool you told me. If this is what ya wanna do, I'm cool with it. We still gonna game together?"

A huge sense of relief came over me as I said. "Of course we're still gonna game together, and maybe NOT call me dude."

"What should I call ya?" he asked.

"Can you call me Teresa?" I asked.

"Yeah. Sure...... Teresa." He responded.

"Dude... a.. Teresa, does your mom know?" he asked

"Yep. She bought me this dress." I answered.

We went down into my room to game. He was asked me a zillion questions about Teresa, while we played. I answered honestly and confidently, but he did shy away from asking me the one question I was still nervous about answering.

We sat next to each other on the couch in my room in front of my 55" TV as he continued to pepper me with questions about Teresa. I sat with my legs crossed and the skirt of my dress showed a lot of my freshly shaven panty hose clad legs. Mom was right. I am so much more confident as Teresa than I ever was as Terry. I felt completely at ease as a girl hanging out with my bestie, as I answered what some may consider embarrassing questions. I noticed Kenny frequently looking over and sneaking peaks at me. At one point, when I adjusted my headphones my hair draped over my eye. Kenny reached over and brushed it out of my face.

At that point, I thought maybe, just maybe he was going to ask me THE question. I got a little flustered and decided it was time for a smoke break. I stood up, took my headphones off and told Kenny I was going out for a cigarette.

"What the? When did you start smoking?" he asked.

"Teresa has always smoked." I said as I winked at him before heading off.

My legs were shaking as I smoked my cigarette and contemplated what could happen next. Then I thought that this could be the moment I'd been waiting for. I decided that I'd just go back down and let whatever happens, happen.

Back in my room, I noticed Kenny had moved more towards the middle of the couch, so when I sat back down we were very much closer to each other. Before I put my headphones back on, he took his off and looked at me.

"What?" I queried.

"So. I get how you wanna be a chick. And how you've felt like that for some time now. I understand why you feel that way and it makes sense, but there's one other thing I wanna ask." He said.

"Go ahead." I replied, knowing full well what was coming next.

Kenny continued. "So, you've been spending a lot of time as a girl and you plan on continuing to spend time as a girl... I just wanted to know.... Are you like, into dudes now?"

There it was... THE question.

I responded with a sort of confidence that I didn't expect to have when answering THAT question.

"Like I told you. I feel like I am a girl. I'm comfortable as a girl. I enjoy being a girl. It only makes sense for a girl to be attracted to guys.... Right?"

"Well yeah." He replied "It makes sense. So........ are you like into..... me?"

I stammered a little bit, but found my voice. "Do you want me to be into you?"

"I dunno. I mean like, you actually, I mean like you look good as a girl. I mean like, pretty." Kenny said.

It was nice to see someone else nervous as hell for a change, because I was loving how things were going.

"So you think I'm pretty?" I gushed.

"Yeah. You look good as a girl." He said.

I put my hand on his and looked at him and said. "Yes, Kenny. I'm into you. I have been for a while. You're so cute and sweet and funny. I'm so into you."

"So what do we do now?" he asked "Should I kiss you?"

"Do you want to kiss me? I asked.

Without another word he leaned in and kissed me. Only a peck at first, but I put my hand on his face and pulled him closer and kissed him with an open mouth. We just sat there on my couch and made out and I fucking LOVED it. Our tongues danced in each other's mouths as I felt such a wonderful feeling inside me.

I don't know if we were doing it right, but I didn't care I was kissing a man and I was so happy. I don't know how long we were kissing before I felt his hand on my leg. The more we kissed, the further his hand went up my skirt. Soon he had his hand on my completely erect penis. He tried to reach under my pantyhose, but they were too tight, so he just rubbed it through my nylon covered cock. Before I felt myself begin to orgasm, I grabbed his hand and took it from under my skirt. I had something else in mind.

"What's wrong?" he asked

"Absolutely nothing, honey" I answered finding it a little weird that I called him honey.

I laid him on the couch and tried unsuccessfully to take his pants off. He was more that eager to assist me though. He laid in front of me on the couch in nothing but his cute little tighty whities and t shirt. I kneeled down on the floor and started to caress his cock through his underwear. He was already so hard. I leaned over and kissed his penis, unwittingly getting lipstick on his undies. I pulled them down to reveal is cock in all its splendor. It was perfect. Not too big. Not too small. This was the moment I'd been waiting for. My first blow job. Obviously, I'd never done it before, but I'd watched enough porn that I was fully confident that I knew what I was doing.

I took him in my mouth. Just the head at first. I took it back out and kissed the head of his divine member. I kissed and licked it again before taking it back into my mouth. I was actually surprised at how easily I was able to take the whole thing in my mouth until my lips were all the way down to the base. Again, I watched a lot of videos. I bobbed up and down on it taking extreme care not to let my teeth get in the way. I pursed my lips and went up and down enjoying the moans I was invoking from my willing partner. I must have been doing a pretty good job because before too long I could feel his body tighten as if he were about to cum. I think he tried to warn me, but I didn't relent. I continued on my quest. Moving my mouth up and down until I felt the first wave of semen whitewash my tonsils. I easily swallowed the first round, but wasn't able to catch my breath before the next blast. I gagged a little, but managed to gulp it down. When Kenny's body stopped convulsing, I continued to hold him in my mouth savoring any and all remaining cum he could provide. I then took him out of my mouth and kissed the head of his cock and licked one last drip from the tip.

"OMG! How did you learn to do that?" he whispered through bated breath.

"I watched a lot of videos on how to please your man." I responded.

I wasn't worried about swallowing. I already knew I liked the taste of cum. I tasted my own so many times.

I wasn't sure if I should go back and kiss him. Ya know since I had cum breath, so I decided I would just smoke a cigarette. I grabbed my purse from upstairs and came back to my room. Kenny was sitting up on the couch, so I sat next to him.

I crossed my legs and lit my cigarette. He looked at me and told me that I looked pretty sexy sitting there like that. I draped one of my legs across his lap and reached under my skirt and started playing with myself as I took a long deep draw from my Virginia Slim. As I exhaled, he reached under my skirt and helped me fondle myself.

As I leaned back, he was able reach under my pantyhose and grasp ahold of my hard penis. Within minutes I felt a wave of complete satisfaction come over me as Kenny made me cum.

As I laid there with a puddle of cum in my lap, I couldn't help but think of how happy I was at that moment and how this was a wonderful "cumming" out party between Kenny and me.

He stood up and kissed me as he started to get dressed.

"Where are you going?" I asked.

"I'd better get home." He responded.

"Why"

"Well, doncha think it will be weird if I spend the night and your mom comes home? With you dressed like that she's gonna think something is up." He said

"She has no idea that you know about me. I'll take my make up off before she gets home. She'll just think we spent the night gaming. I want you to spend the night with me."

"Okay" he said "Just promise you'll be Terry by the time she gets home."

"Deal" I said.

I cleaned myself up and put on some clean panties and t shirt and crawled into bed. Kenny went over and laid on the couch.

I said. "What are you doing?"

"Going to bed" he said.

"Oh no. I want you to sleep with me."

I guess he couldn't resist my feminine charm and he laid next to me. I climbed on top of him and kissed him more. I couldn't seem to get enough of that man. We didn't do anything but make out, but it was enough. I was so happy. After some time, I rolled off of him and we laid there spooning until we fell asleep. Feeling his body against mine as we dozed off was just what this girl needed.

When we heard my mom come home, Kenny jumped back onto the couch and I changed into some boy boxers and t shirt. I went into the bathroom and took off my make up. I was in there when she came down. I was finishing up. I flipped off the light as she came down to check on me.

"Hey mom. How was work?" I asked.

"Okay. What's up with you?" she replied.

"Oh nothing. Just taking a leak. Kenny and I were gaming" I said as I nodded to the couch letting her know he was there.

"Okay. Goodnight" she responded unsuspectingly.

The next morning, we awoke to mom cooking breakfast. Despite working nights, she was still an unusually early riser. She yelled down that breakfast would be ready in a few minutes.

Kenny and I got up and went upstairs for some well deserved bacon and eggs.

Mom asked. "So, did you two have fun last night?"

In unison we responded. "Yep" without looking up from our plates as to not arouse any suspicion.

She was looking at me quizzically and I didn't know why. I just kind of shook my head at her as if to ask her why she was staring at me. Maybe because she hadn't seen me as a boy in the morning for a while.

Kenny was acting a bit squirrely so I was glad when he said he had to leave right away after breakfast. I didn't want him to give us away.

After he left, I was still sitting at the table about ready to head down to put on something more fitting a young lady.

Mom was at the sink facing away from me when she asked.

"So, what all did you two do last night?"

"Just played video games." I responded.

"Anything else?"

"No. Why?" I asked

"Well, little princess. In your haste to get your make up off before coming up you completely missed half of your lipstick." She retorted.

"OH SHIT!" I exclaimed completely avoiding eye contact.

She sort of chuckled before saying.

"Well, I'm assuming you told Kenny. I'm guessing he was okay with it."

"Yeah. He knows. I guess he was okay with it. He hung out with me and played video games." I said

She asked. "What made you decide to tell him last night?"

Before I went into further details, I told her that I needed to go down and change back into my girl clothes. I couldn't very well tell her about my first 'date' with Kenny dressed as a boy.

I put on my bra and panties, tights and leggings, tunic sweater, wig and make up. I was now much better equipped to discuss this with my mom.

I strutted back upstairs. I began:

"He saw me smoking a cigarette out on the porch." I said "He came over and I told him that I wanna be a girl. I told him the whole story about my dressing and how I've known I'm trans for a long time.

She asked. "So, I'm assuming he was okay with it."

"Yeah. He even said I looked good as a girl." I replied.

"Oh. That must've made you feel good" She said with a smile.

"You have no idea mom." Was my response. "He was so sweet and so understanding. I was so scared telling him. I was afraid I would lose my best friend. He just stood there and listened to me telling him how I felt. I don't think it could have gone any better."

"He's a really good guy." She said.

"He really is." I responded. "He just said if that's how I feel, then that's how I feel. We're best friends and he accepts me for who I am, as long as I'm happy. He just kept telling me that I looked good as a girl. He even called me pretty."

"He's so sweet." She said. "So did you tell him anything else?"

"Like what?" I pretended not to know what she meant.

"Girl, you know! Did you tell him you liked him?" she exclaimed.

"I did" I said with a sly grin.

"AND?!" she asked excitedly.

"Well, he didn't leave, did he?" I said.

She was getting excited. "Well, what happened?"

I explained to her how the conversation went and how he brushed my hair away from my face when my hair was in my eye. That's when I knew things were going well. I told her about the kiss and how wonderful it made me feel. I told her that the way he kissed me let me know that telling him was the right thing to do. I purposely neglected to mention his hand up my dress.

That wasn't enough for her. She kept badgering me for more details.

"So you just made out with him all night?" She asked.

"Pretty much." I told her.

"Teresa, you've been honest with me about so many things these past months. Do you honestly expect me to believe you spent the night with a boy and all you did was kiss?"

"Mom! It was the first time I ever kissed anyone. What did you think we were gonna do?" I asked.

She gazed at me. "You told me how you feel about him. I just think you're leaving something out."

I grabbed a cigarette and lit it. Without looking at her, I quietly said "Well, I might have given him a blow job."

"You did what?!" She exclaimed.

"OMG MOM!" I yelled. "You wanted more details. I gave you more details. I gave him a blow job. And you know what. It was great! It made me feel more like a girl than I ever felt before!"

She started laughing at me. "I was only kidding Teresa. I knew you had to do more than just kiss him all night. I know how you feel about him. I figured there was something you weren't telling me. So what did you do with his cum?"

Mom and I had grown amazingly close these past few months. Almost more like sisters than mom and daughter, so I didn't feel bad saying:

"I swallowed it, like any good girlfriend."

"Did you like it?" she asked.

"Actually, I didn't mind it at all. What was even better, I think he liked that I swallowed it as much as I did." I said.

"Well, looks like Kenny won't be spending the night anymore" she joked.

"Why not?" I asked.

"Well, I didn't let any of your sisters' boyfriends spend the night. Why should I let yours?"

I came back with, "Well, Kenny can't get me pregnant!"

"Touche" she said. "Honey, I'm teasing you. I can see that you are happy now. The happiest I've ever seen you. If having your boyfriend spend the night is what makes you happy, who am I to stand in the way? You are my youngest daughter and I feel like I'm just getting to know you for the first time in your life. There is nothing more that I want than for you to be happy."

I told her how much I love her and how much I appreciate how she accepts me for who I am.