From Nerdy Terry to Lovely Teresa Pt. 04

Part 4

Boy, did we open up a can of worms by having sex for the first time. We were like a couple of rabbits. We made love every time Kenny came over. Mostly in my bed, but I think we ended up doing it in every room of the house. I made sure that when he was there I was always in thigh highs or suspender hose, so he had easy access to by bottom. I made sure to wear skirts too, so I could just flip it up, whenever the mood struck us. I even had to go so far as to buy more panties, because I had to change them after each session after they soaked up the cum dripping out of me. Mom suggested I start wearing feminine pads, so I wouldn't ruin all of my panties. Something a "real" girl should have thought of. I was disappointed in myself for not thinking of it. I also had to keep everything back there clean and shaven, as there was no telling when Kenny was going to plunge his cock in me.

Every time he came inside me, I felt closer to him. Every time he made love to me, I felt more and more like a woman. The idea of having the man of my dreams making love to me was something I dreamed of for such a long time, and now it was all coming true.

He would fuck me in the kitchen when I was making dinner. He'd bend me over the sink or the table and ravage my tight little ass. Once we were on the couch in the family room watching TV. I decided to climb up on top of him. I sat facing him as I slid down his pole, so I could kiss him while we made love. It just so happened that mom came home early that evening and caught us in the act. When I heard her keys in the door I jumped off of him and sat back down on the couch and pulled a blanket over our naked bodies. I'm sure we looked suspicious, because she asked why the blanket was pulled all the way to both of our necks.

She asked what was going on and I just giggled. She just rolled her eyes and said.

"Dear god, can't you too ever get enough?"

I grinned and said, "Nope."

"Well, take it downstairs. I'd like to watch TV." She said.

And we did.

Now don't get me wrong. I was in no way, shape or form bored with all the sex Kenny and I were having. It was beyond amazing and I loved every second of it, but I thought it would be fun to spice things up a bit. I ordered some sexy (if not slutty) negligee and a new blonde wig to surprise Kenny one evening. My real hair is auburn, and the wigs I currently had were auburn as well. I just thought it might be fun to go blonde... Like they say blondes have more fun. I found it hard to imagine that I could have MORE fun, but I wanted to find out.

It was red spandex with black leather woven into the bodice. It had a low neckline and spaghetti straps. It came with red sheer thigh high stockings. It was soooo hot.

I watched a tutorial on some "sexy" eye make up. Very dark and mysterious. I added the brightest red lipstick I could find. That night, I prepared for an evening of pure unadulterated dirty, nasty, sweaty sex. I put on my new blonde locks and styled it just so. When I took a look at the finished product, I was quite pleased. I looked like a whore. Kenny was in for a wild ride. I snapped a quick pic and sent it to my mom. She was curious to see how the outfit and new wig looked. I got a one word text response: "Slut!"

Just before he was supposed to come knocking, I placed a kitchen chair in front of the door. Sat down, crossed my legs as my black stiletto dangled above the floor, lit a cigarette and waited.

When he knocked, I said with the most alluring voice I could muster: "Come in."

He just stared for a few seconds before uttering:

"Holy shit! You look so hot! I mean, like you always look pretty, but goddam!"

I grinned and said. "See anything you like?"

"Ummm yeah. Like EVERYTHING." He exclaimed.

He took me by the hand and helped me up. We embraced in about as passionate a kiss as we've ever had. Then without a word he took me by the hand and led me towards my bedroom.

"What about dinner?" I joked.

"It can wait." He said.

He guided me onto my bed as he undressed. I went to kick my heels off and he said:

"No. Leave them on. You look perfect just the way you are. Please leave them on."

I was about ready to suck his dick to get him hard, but he told me to get on all fours. As kneeled behind me, I fully expected to feel his lubed manhood enter me. Instead I felt his hands on each of my cheeks as he began to kiss my ass cheeks. A subtle sigh came out of me as it felt so nice. Then without warning he spread my cheeks apart and he started licking my hole. I trembled with delight as he dabbed his tongue in and out of my rear end.

He was like Picaso painting a picture with his tongue on my little "pussy". My eyes were closed and I savored every time his moist tongue went inside me. I wanted to bury my face in the pillow and scream, but I had no intention of messing up my make up.

I whispered to him, "How did you learn how to do that?"

"I watch videos too hon." Was his response.

As he continued pleasuring me to a degree that I'd never been pleasured before, I dreamed that my lover was actually licking my "real girl" vagina as I let out consistent little moans each time his tongue passed over my "pussy".

After he concluded, I was anticipating feeling him rise up and enter me with his throbbing cock. Instead, he asked me roll over, as he stood and retrieved the lube from my night stand. Once fully oiled up, he moved between my legs and dipped down to put my ankles over his shoulders. He placed a pillow under my hips as he rose up to his knees. I felt the tip of his dick slowly but surely enter my bottom. He maneuvered his way in until his hips were firmly against my ass cheeks. Then he began to slowly thrust his cock in and out of me. Slowly at first, but he started going faster and faster. When he's inside me, I'm not able to maintain an erection, but the feeling of his member moving back and forth inside me fills me with a feeling of pure delight. As he fucked me in this position, I could feel his dick touch me in just the right spot every time he thrust into me. The way he had me positioned as he ravaged me made me feel like I was going to orgasm. I could feel my body tense as a flood of semen spilled from my limp little penis until I felt a puddle of my own juices running onto my abdomen. He didn't stop fucking me though. I begged him to continue for as long as he needed to fill me with his seed. As he came, he banged his hips against me with each blast of cum. Once he'd finished, he collapsed on top of me and kissed me.

I whispered. "More videos?"

"Um hmm." He answered between breaths.

We were both exhausted and we just laid there with him on top of me for a few more minutes. After he rolled off of me we fell asleep with his cum in me and my cum on me.

Words cannot express how much I love waking up next to him each time he spends the night with me. What started as a friendship of having him spend the night on the couch in my room, has blossomed into a love affair with him lying next to me in bed. I adore feeling his naked body against mine as I wake up in the morning.

No time for breakfast today. Kenny had to go home and get ready for work. I didn't bother getting cleaned up yet. I just slipped into some tights and put on Kenny's sweatshirt that he left. I held it to my nose so I could smell the sweet aroma of his cologne as I went upstairs. I put on my "normal hair", but still had on my "slutty" make up from last night (albeit a bit smeared after last nights events).

Mom was sitting in the kitchen enjoying her morning coffee. She looked at me and greeted me with, "Hellllllloooo slut" as I poured a cup of coffee for myself.

"Morning mom." I replied as I grabbed one of her cigarettes and joined her at the table.

"So how did Kenny like his evening with a prostitute?" She asked.

"Oh. He liked it just fine." I said before telling her all of the details from our little role playing escapade. I explained to her what he had done to me and that he was able to make me achieve orgasm just by making love to me.

After I told her everything she asked if I ever get sore "down there" from all of the sex we were having. I explained that it never hurts at all during sex, but sometimes in the morning it's a little tough walking.

She asked me if it was worth it. All she got was a bit ol' smile from this trannie tramp.

Mom asked me what my plans were for the rest of the day. I shared that I needed to take a shower because I hadn't cleaned up from last night. She was a little grossed out and asked if I let him cum in me every time. I told her that he always cums inside me. Neither of us have been with anyone else, so it's safe. She laughed and joked "No, I just meant that you have so much cum in you that it might change your insides into ovaries and you might end up pregnant."

I laughed at the preposterous notion, but said "As long as it's Kenny's baby, I'm okay with it."

She sent me on my way, but said asked me not to "feminize" myself. She wanted me to go to the mall with her. She needed to pick up a few things and could use a woman's point of view. How could I say no to that?

As we drove to the mall, she could tell something was on my mind. As you know, she could always get me to tell her what was going on in my head.

I told her how much I appreciated her acceptance of my alternative lifestyle. I thanked her for letting me be myself at home and for her allowing me to have Kenny spend the night. I mean what traditional mother would let her son to be a girl, much less let him have a boyfriend, who spends the night?

I told her how happy I was and how much I loved the "new" me, but I sorta felt like something was missing. Something I hadn't even shared with Kenny yet. I told her that I wanted to know what it would be like to be Teresa out in public. I wasn't talking about coming out as trans (yet). I just thought about maybe driving around to a secluded area not too far from home and just going for a walk after dark. I told her that at some point, I did plan on coming out completely, but I don't plan on doing it anytime soon.

She didn't seem too surprised, but she also didn't seem too excited about it. She did say she figured this time would come, as she could easily see how comfortable I was becoming as a woman. She said she'd have to think about it and we could discuss it more later.

I didn't want to badger her anymore about it and figured I'd bring it up another time.

Shopping went really well. I love shopping. What girl doesn't. I love looking at all of the cute outfits. I even held up a few tops and dresses to ask mom if she thought they'd look cute on me. I know she wasn't loving me doing it in public, but no one else in the store seemed to care. We went into Lululemon for a quick peak. I always wanted a pair of Lulu leggings. I saw a pair I really liked. I asked mom if I should buy them. She told me that if I wanted to spend that kind of money for a pair of leggings, to go for it. Then I tried my next ploy to get her to let me try to do something feminine in public. I told her I loved them, but wouldn't spend $100 on them unless I could try them on. She shot an evil stare at me as I grabbed them and headed for the dressing room.

As the attendant let me into the dressing room he gave me a smile. We chatted for bit. He was clearly gay, and I can guarantee from his reaction, I wasn't the first biological guy to go in to try on a pair of leggings.

I got undressed and put on the Lulu leggings. Now I know why everyone loves these things. They feel like wearing a cloud. I love any and all leggings, but there was something about how these felt. No wonder they were so expensive. I was definitely buying these.

I changed back into my yucky boy pants and headed to the counter with my purchase. I walked up and proudly put them on the counter. The girl at the register didn't bat an eye. She held them up to find the tag to scan.

"Oooh. These are cute. I love this color." She said as she folded the hunter green leggings and put them in the bag.

"Yeah. I know. I love that color." I mused.

Grabbed my Lulu bag and headed towards the door. Mom was out on the concourse waiting for me. She shook her head as I caught up with her.

"What?" I asked.

She replied. "For 17 some odd years you wouldn't even buy your own underwear at a store, and now you've got no issues buying girl's clothes for yourself."

"I know. Crazy isn't it? I just can't describe the way I feel anymore. I just don't give a shit what people think about me now. The "real" me just has this weird overwhelming confidence. I just so comfortable with myself these days" I said.

"You've come a long way baby." She joked.

I just gave her a big smile as we walked to the exit.

On the ride home, mom asked. "So I saw you talking to that boy back by the dressing room. Did you think he was cute?"

I replied. "Yeah. He was cute, but he was way too gay for me."

"How can someone be too gay?" she asked.

I responded. "He was very flamboyant and effeminate. I'm going to be the girl in ANY relationship I have with a guy. I want a more manly man."

"Like Kenny?" she asked.

"Exactly like Kenny." I replied.

The following week was a little rough. Both Kenny's and my work schedules conflicted a lot. I only saw him one day that week, but we took full advantage of it. I wore my new leggings for him to see me in them. He liked them, but I wasn't in them for long. We were both pretty horny since we hadn't been together in a few days. We started making out as soon as he walked in the door. I could feel his dick getting hard as he grinded against me. I dropped to my knees and pulled down his sweats and started sucking his cock right in the foyer. My god, I missed having him in my mouth. His dick was buried in my mouth. I just held it there and let my tongue play along the underside of his delicious pecker. Before he was ready to cum, I took it out and led him to the couch in the family room. I took off my leggings and kneeled backwards on the couch and leaned forward onto the backrest. Kenny utilized the lube I had already put on the end table. As he approached, I reached back and guided him inside me. He held onto my hips and started banging my tight little backside. We got into rhythm as his penis slid in and out of me. I could tell he was as horny as I was when he came in about 3 minutes. As usual, I let him fill my ass with his hot white juice.

I laid back onto the couch and started playing with myself to get my own dick hard. I was going to have Kenny watch me jack off, but instead he kneeled beside me and took me in his mouth. He was getting quite good at pleasuring me that way, and he was starting to do it a lot more often. When I was ready to cum, I gave him fair warning, but he didn't stop. For the first time in our relationship, he let me cum in his mouth. To my surprise, he actually swallowed every drop. After I caught my breath, I pulled him closer to me and kissed him and enjoyed the essence of my cum on his breath.

As I held him close, I whispered. "I couldn't love you anymore than I do right now."

He responded. "I love you too. I just figured you do so many things for me, I thought I should do something for you. I hope it was okay."

"Better than okay. It was amazing." I told him.

In hindsight, flopping onto the couch with an ass load of cum was not a great idea. Unbeknownst to me, I left quite a mess on mom's couch. Needless to say, she was none too happy when she saw it the next morning. Fortunately for me, I know from experience that dried cum is water soluble. It cleaned up pretty easily with soap and water, but still the thought of her couch cushions doused in semen, didn't sit too well with my mom.

I guess this wasn't the best time to revisit the discussion about Teresa making her first public appearance. I was really planning on asking her about letting me take a walk one evening as a girl. I did bring it up to Kenny, and he was all in favor of accompanying me for an evening stroll. I was pretty much hell bent on doing it, whether mom agreed or not, so Kenny and I decided that it was going to happen. What mom didn't know, wouldn't hurt her, right?

So, it was decided that we'd do it on a weekday evening, in an effort to avoid running into too many people during our adventure.

We picked a Wednesday night, that neither of us had to work. I came home and immediately did my homework foregoing my usual routine of adorning any kind of feminine attire. Once I was finished and it started getting dark, I went into full girl mode. I started with make up. I absolutely adore putting on make up. I know most girls are averse to the process, but I just love doing it. I love the idea of completely transitioning from a geeky nerd to a pretty young lady. I've really gotten very good at applying make up, if I do say so myself. I just love trying new techniques and different colored eye shadow and eye liner to complete my transformation. Mascara is my favorite. I love the way it makes my eyelashes look so long and luxurious. I feel like it really brings out my eyes. Same goes for styling my hair. It's just so much fun trying out new and exciting hair styles. Tonight, I was going to keep it down and straight. I kind of wanted it to hang down to partially cover my face as to not attract any unwanted attention.

Once my hair and make up were complete, I got dressed. I went with my green Lulu leggings and a black oversized Nike hoody. I also bought a new pair of Nike sneakers, just for the occasion. One thing I don't do a lot is "tuck my junk". There's never much of a need to conceal my manhood, when I'm at home, but going out in public, I didn't want to have an unsightly bulge in my leggings. I discovered a wonderful accessory on crossdressers. com. A gaffe. It's essentially a pair of panties with a stiff front panel that helps in concealing one's parts. After I got dressed, I took a look in the mirror and admired my smooth crotch that didn't give any indication that I was hiding anything. I was really very pleased with how the whole outfit came together. The pretty girl looking at me in the mirror looked more than ready for her coming out party.

Kenny wasn't due to come over for a few minutes, so I grabbed my purse and headed out to the back porch for a quick smoke. The thought of actually going beyond the porch as a woman was so exciting. I stood there just thinking about how wonderful it was going to be to be with the man I love taking an evening stroll as the person I was meant to be.

Kenny got there just as I was putting out my cigarette. I greeted him at the front door as usual with a long passionate kiss, despite the fact that I'd have to go and fix my lipstick before we headed out. Once I reapplied, we began our journey. We decided Kenny would drive my car for a couple reasons. First, it was in the garage, so I wouldn't have to go out in plain view of any nosey neighbors. Secondly, I didn't want to smoke in Kenny's car.

Of course, being the ditzy girl that I am, I forgot that I needed gas. I was so focused on getting ready, I overlooked that necessity. We agreed to drive to an area we didn't think we'd know anyone and Kenny would pump the gas. As I sat in the car, while he re-fueled, I couldn't help but wonder if subconsciously that I purposely forgot about getting gas, so I could be out in public at a gas station as Teresa. There were people milling about at the gas station, filling their cars, but no one paid much attention to the woman in the car. One lady did glance at me, but paid little attention.

We arrived at our destination and parked in a secluded spot away from any streetlights. Kenny took my hand and asked, "You ready, hon?"

At that moment, the geeky nerd reemerged. The confident young woman momentarily took her leave. I told him I was scared, and maybe this was a bad idea.

He squeezed my hand tighter and said, "Teresa, you've been wanting to do this for a while. You've got nothing to be afraid of. You are pretty and petite. No one is going to suspect anything. Hell, you are more feminine and lady-like than just about any girl I know. You can pass as a girl anywhere at any time. It doesn't matter if it's day or night. You are a girl as far as I'm concerned, and I'll be right there with you."

That was what I needed to hear. I felt the blood come back to my face, and my heartbeat returned to normal. My confidence started to return as tears started to well up in my eyes. I didn't want to ruin my make up by crying so I wanted to lighten the mood.

"You are getting the best blow job of your life tonight." I told the love of my life.

He got out and came around and opened the car door for me, and took me by the hand and helped me out. And so it began. We walked hand in hand down the street. No one really paid any attention to us. Several cars passed us and we saw a few people out walking their dogs. A few nodded hello, but no one seemed to notice or to care about a tranny and her boytoy walking the town streets. I loved how it felt to have the breeze blow my hair gently off my shoulder and how Kenny's hand made me feel so safe and secure.

I really had no inhibitions about how I would handle myself in public. It didn't even cross my mind that someone would notice that I didn't "walk like a girl." That was because I did walk like a girl. I did everything like a girl, because that's exactly what I was.... a girl. Being a girl was what I did best (except for giving blow jobs). As I've said before, I've always been a bit effeminate, so it was very easy for me to perfect all of the mannerisms of a woman. Well, that and I've been practicing for years. In fact, as a boy at school, I had to make an effort to act more masculine. I had to try to walk "like a boy". I couldn't cross my legs like a lady... you get the idea. I was really a girl trying to act like a boy for most of my life. I was just so happy to finally be out and about as the person I was born to be.

Our walk around the neighborhood ended without incident and I was very pleased with how I felt about being in public. I felt very satisfied with how everything went and how I felt about it. So much so, I was already thinking about the next time we could do it. Maybe when it wasn't dark out.

On the ride home, I was smoking a cigarette with one hand and playing with Kenny's cock with the other. I wanted him excited when we got back so I could give him his well deserved celebratory head job.

We got back to my house and went down to my room. It was getting a little late, but I still needed to reward my young stud. I told him to take his pants off and get in bed. I laid between his legs and put my red lips over his throbbing dick. I did my normal tongue gymnastics on his cock, but then decided to spice it up a bit. I reached under and started to tickle his butt hole. Lightly at first, but then began to insert my finger a little deeper. He didn't seem to mind at all other than saying, "What are you trying to do, turn me gay?"

I took his cock out of my mouth and said, "Too late sweetheart. That ship has sailed."

I went back to work and finally got him to cum while my finger was still in his tight behind.

I've sucked his cock so much and swallowed so much of his cum that I never have any issues with choking or gagging anymore. I'm pretty much of a head artist. For me, sucking dick and swallowing cum, is just another day at the office. And I really love my job.

After I accepted every last drop, I climbed up to kiss him. We made out for a while before I walked him out. I thanked him again for taking me out and told him how much I loved him.

I went back downstairs and got ready for bed. I just wore some panties and one of Kenny's t-shirts that he gave me. I still was coming down from the high of being out in public, so I didn't want to remove my make up. I'd take care of that in the morning before school. I laid on my back in my bed and started playing with myself through my panties. I reached into my panties and gently tickled the underside of my shaven balls, which always gets me aroused. I kept thinking of how much fun I had earlier being out of the house as a girl. I couldn't wait to do it again. I started to plot the next adventure. I wanted to be around more people to see if I could really pull off being a girl with no on noticing.

The more I thought about it the more I wanted to do more than just walk around. I thought it might be fun to go to a gay bar. It would be a lot of fun to be around people like me. Maybe find one not too far away, but not close enough to run into anyone who might recognize me. I could try to find one that had a drag show, so it would all but guarantee there'd be other crossdressers and transsexuals there. The more I thought about it, the more vigorously I stroked my now erect penis. The thought of being around others like me made it hard to contain myself. I came all over my stomach. I rubbed it around like it was a soothing lotion before licking the tips of my fingers enjoying the taste of my own cum for a change. I wasn't about to get up and clean myself off. I just fell asleep with the streaks of semen on my belly. Hell, it cleans up easily with soap and water.