From Nerdy Terry to Lovely Teresa Pt. 03

Part 3

Later that day when Kenny texted me. I told him that my mom figured out what we did, and he was mortified. I told him not to worry about it, and that she was 100 percent fine with us being a couple. Regardless, he felt very uncomfortable about being around her.

Needless to say, Kenny had become a fixture at my house when my mom wasn't home. We spend so much time together. I love spending time with him. We still did a lot of gaming, but now we do more couples things together (even if it is still behind closed doors). I made dinner for him, we worked on homework, we watched a lot of TV together. We hold hands and kiss a lot. And yes, I suck his dick quite a bit. At least once every time he's over. So much so that my mom has started calling me a cum dumpster and asks if my jaw is sore every time I talk to her. I don't mind at all. I know she does it in fun. I love pleasing him. I think I love sucking his cock so much because I'm in control. I decide when he cums. I suck his dick so much that it takes quite a while to get him to cum. I don't mind though. I consider it a challenge, plus I love doing it. I love to think of new and innovative ways to suck him off and get him to cum. He loves when I suck on his balls and play with is dick at the same time. One time, I was lying on my back and he was basically fucking my face and I begged him to cum all over my face. Then I wiped the cum off my face with my hand and licked my fingers clean.

Kenny has even resorted to reciprocating on occasion. He won't let me cum in his mouth, but he's getting better at the art of felatio, which I greatly appreciate.

Since he found out that my mom knows about us, he's been very reluctant about spending the night. He usually sets his alarm and leaves before she gets home. He said he can't look at her knowing that she knows he's getting his dick sucked by her daughter.

To that point, we still hadn't actually had sex. We really didn't talk about it. I was happy sucking cock and he was happy getting his cock sucked. Maybe he thought it wasn't something I wanted to do. I can tell you for a fact that it IS something that I wanted to do.

I decided to ask my mom how to approach the subject. She was a little shocked to hear that we hadn't had sex yet. She asked what we do all evening when we're together. When I told her how much I blew him she just laughed and said that I really was his little cum dumpster. She suggested I invite him over for a romantic candlelit dinner. After dinner, get him into bed go down on him for a bit, and when he's good and hard just climb on top of him. That way you don't have to talk about it and you can just do it. But she also advised that I buy some lubrication or it wouldn't be enjoyable for either of us.

I decided to face time him and invite him for dinner on Friday night. Mom was close by when I was talking to him and grabbed my phone. She tried to be funny and told him that she knew what he was doing to her daughter and she was absolutely fine with it. She told him she missed seeing him at breakfast and that he should spend the night and she'd make us all breakfast on Saturday morning. She really wasn't going to accept no for an answer so he finally relented.

In addition to buying some lube, I had to find another dress that would arrive by Friday. It was only Monday, so I was good. I found a really pretty blue and white sleeveless dress with a v-neck and short skirt. I also ordered some suntan thigh high stockings, so I could leave them on when I was getting fucked for the first time.

Everything arrived on Thursday. On Friday, when I got home from school, I immediately jumped in the shower and shaved everything from top to bottom. I don't really have a lot of pubic hair, but when I was finished, I had none. I spent an extraordinary amount of time on my make up. I wanted it to be perfect. Once I felt that I looked presentable, I got dressed. The new dress looked really cute and I matched it with a pair of beige heels. I decided to go panties free for the evening. I added some clip on earrings and a necklace that my mom let me borrow.

Kenny was going to be here any minute. I ordered a pizza online for delivery (no time to cook) and lit the candles on the dining room table. I sat down to have a smoke before my man arrived.

When he got there, I opened the door. He came in and looked at me and smiled.

"Wow! You look so pretty." He said.

"Aw. Thanks babe." I said as I went in for a kiss.

I don't have anything to compare it to, but Kenny was such a great kisser. I tingled inside every time our lips met. Guess that means something, but we'd yet to use the "L" word.

"So what's with the candles and the new dress? Special occasion?" he asked.

"I'm just excited that you're going to meet my mom for the first time as my boyfriend." I quipped.

He was still nervous about that, but I assured him it would be fine and that it was her idea for all of this.

Pizza came, and I unwittingly answered the door. I didn't even stop to think that I was answering the door as Teresa, but the delivery guy didn't bat an eye at the sight of a pretty young girl grabbing her pizza.

We chatted and enjoyed our Italian fiesta. I started to clean up. Kenny grabbed me from behind and started kissing my neck.

"Teresa, you look so fucking hot tonight. I can't keep my hands off of you." Kenny exclaimed.

I put the dishes down and put my arms around him and thrusted my tongue into his mouth. As we made out he grinded his cock up against me. He lifted up the skirt of my dress and squeezed my bare ass. We were both getting hard as we kissed more aggressively.

I pushed him away gently and asked him to go downstairs and wait for me in bed. I was going to quickly clean up and I'd be right down to join him.

As I straightened up, I was getting nervous about what was going to happen. Would he want to have sex? Would it hurt? Would I be any good at it?

I knew for a fact that I wanted to try it, so I decided to pull up my big girl panties (that I wasn't actually wearing) and headed downstairs and hoped for the best.

Kenny was already naked in my bed. Looks like he started without me as he was fondling in cock and giving me a "come hither" look.

I slipped out of my little dress, kicked off my heels and moved towards him as seductively as I could. I planned on keeping on my thigh highs and my bra so I still looked like a girl and not a gangly boy.

I laid down on top of him and we kissed. His rock hard dick poking into my groin. I was hard in a matter of seconds. I love the feel of his naked skin pressing up against me as our tongues intertwined. I could feel his heart racing the deeper we kissed.

I slid down his body and let his raging cock enter my ever awaiting mouth. As I performed my woman duties to the very best of my abilities, I decided it was time to move onto the next step in my plan. I slowly lifted myself off of the bed and kissed the head of his dick for good measure. I went to the nightstand and withdrew the lube and my newly acquired dildo. It was still in the package, as I'd chosen not to try it out just yet. I wanted Kenny to be the first one to enter the forbidden zone.

Kenny had a bit of a quizzical look on his face, but didn't say anything. Nor did I. I unpackaged the 8 inch pleasure device and sat at the foot of the bed between Kenny's legs.

I slowly squeezed some lubricant from the tube. I applied a generous amount to the toy and even more to my virgin bottom. I laid back, lifted my legs and began to insert it into my ass. I was sure to take my time and allow the lube to do it's job. As I glanced up at Kenny, he was once again stroking his manhood. I was getting the results I had hoped for. After a bit, I was able to insert the entire thing inside me. Once inside, I began to slowly pull it out and back in to simulate getting fucked. The more I did it, the better it felt and the more I liked it. I let a few little moans just to show Kenny how much I was enjoying myself. He sat up on the bed and asked.

"Whatcha doin' there, hon?"

"Just getting myself ready." I replied.

"Ready for what?" he asked.

"Ready for you to fuck me." I answered.

An enormous smile came over his face as he motioned me towards him. I removed the dildo from my backside and crawled up to him. He laid back and I climbed on top of him.

I reached back and guided his cock into my awaiting backside. It went in so nice and easily. My body shook as I sat back allowing him to fully enter me. I just sat there for a moment enjoying the feeling of having my lover inside of me.

I started rocking back and forth as my body shivered with delight. I shifted my weight to my knees, so I could move up and down on his throbbing member. I cannot begin to describe the pleasure I was feeling from his dick sliding in and out of me. The more I did it the better it felt. I kept going. Faster and faster until the muscles in my legs were burning, but I couldn't stop. It just felt too good. Kenny in turn was rhythmically thrusting his hips in perfect unison with me. I continued riding my man like he was a bucking bronco until he exclaimed.

"I'm about to cum baby!"

"Cum inside me!" I begged.

With that, I felt his whole body convulse as he shot his load in me. Once... Twice... Three thrusts of his hips as he filled me with his sweet juice. After the final blast, I collapsed on top of him as he kissed my neck. I was breathing so heavily it was hard to catch my breath as I lay almost lifeless on top of Kenny. After I recuperated a bit, I took his face in my hands and kissed him tenderly.

"That was amazing." I whispered.

He didn't say anything, but he kept kissing me, as we laid in silence, except for the sounds of kissing.

After a few minutes, I sat up and slowly rose from atop my lover, taking time to allow his cock to recede from my ass. I flopped down on the bad next to him and announced.

"I've never needed a cigarette so bad in my life."

I stood up, still with the feeling my rearend being stretched out, and grabbed my purse.

As I walked back the bed, after lighting a cigarette, I could feel a stream of semen running down my leg. I've known that I've felt like a real woman for a long time, but now I felt like a complete woman. I sat up in bed next to Kenny and took a long draw of my cigarette. After a long exhale, I looked over at him. He smiled and asked, if it was everything I hoped for.

"Everything. And MORE." I replied.

"Good. It was amazing for me too. Why haven't we ever done that before?" he asked.

We both agreed it was because both of us were nervous about bringing it up to each other. We promised to tell each other everything from now on, so we'd never again miss out on something so wonderful and special.

We were both pretty exhausted, so we cuddled up next to each other. Kenny was behind me spooning me with his arm around me. I loved feeling his naked body against mine.

What happened next wasn't something I planned, but it just sort of came out.

"Can I tell you something without you thinking I'm all weird, and you freaking out?" I asked.

"Of course. Didn't we just agree to share everything" Kenny responded.

"Well, having you in my life has been so amazing. I mean, you were my best friend and now you're my boyfriend. I've never been happier in my whole life. I just wanted you to know that.... I love you Kenny."

There was a momentary pause, that scared me for a second until he said as he held me tighter.

"I love you too, Teresa."

I absolutely just melted in his arms. I was in heaven drifting off to sleep with the thought of that in my mind.

I can't begin to describe how amazing it was to wake up next to Kenny the next morning. Sure he'd spent the night a zillion times before, but never in bed with me... all night.

I'm certain I woke up with a smile on my face when I realized it was real and not a dream.

He was already awake when I rolled over.

"Hey baby." I whispered.

"Morning sweetie." He replied.

I could hear my mom already making breakfast in the kitchen. It was a big day for all of us. Mom was finally going to see Kenny for the first time as my boyfriend. That being the case, I need to get cleaned up and put my face on before heading upstairs.

I jumped in the shower and shaved everything that needed to be shaved (which wasn't much, as I think puberty passed me by somehow). I told Kenny to get in the shower, while I put on my make up. He walked in the bathroom with his hot naked little body and grabbed me from behind while I was looking in the mirror. He squeezed me and pressed up against me, kissed my neck and whispered. "Last night was amazing." before getting in the shower.

I just about finished my make up as he got out. I styled my wig and fluffed it up a little with the hair dryer, since I slept in it all night.

Usually, Saturday morning with Mom was a leggings and sweatshirt kinda thing, but I wanted to look pretty. I wore a little skater skirt and a sweater with tights and my UGG slippers.

Kenny was dressed and ready way before me... Surprise. Just as I was about finished I heard from upstairs.

"Are you two lovebirds about ready? Breakfast is served."

I took Kenny's hand and asked him if he was ready for this? He nodded, but seemed pretty nervous. For some reason, I was a little nervous too, but I have no idea why.

We went up and walked into the kitchen hand in hand.

Mom turned around and said, "Aww don't you two look so cute. Kenny, how have you been? Haven't seen you in a while."

"I'm good. How've you been?" Kenny asked.

"I'm fine thank you." Mom responded.

We all sat down at the table as mom served us.

"Now Kenny," mom continued. "I'm going to get this out of the way, so no one feels uncomfortable. I've known for quite some time about Teresa and I can only say if she's happy as a girl then I'm happy for her. She's really grown as a person since she told me about her feelings. When she told me that she had feelings for you, I really wasn't all that surprised. I know you two were close before, but I'm really happy to see you two together now. I really don' t think she could have chosen a nicer young man to date. Just know that you are welcome here anytime."

Kenny thanked her. I was so glad she said what she said. I think it put both of us at ease.

After breakfast, Kenny said he needed to get going, because he had to get to work. I walked him to the door. I could see mom peaking around the corner, when I leaned in to kiss him goodbye. It was more than a peck but less than a tongue exchange.

When we broke our embrace I whispered, "Love you."

"Love you too." He whispered back.

I shut the door and turned around. Mom was standing right behind me.

"Love you?" she asked

"Yeah" I said beaming with delight.

"Oh wow." She said "Who said it first?"

"Me" I replied.

Then she asked. "So how did last night go?"

My face lit up and she knew without me saying a word.

"OMG. Tell me everything!" she yelped.

I giggled and said "Girl, grab a cigarette and sit on the couch. I've been dying to talk about this."

I told her every last detail of the greatest night of my life so far. She was only too happy and excited for me. She said I was absolutely glowing as I told her about mine and Kenny's first time making love.

Then she asked. "So you really love him, huh?"

"Yeah, mom. I really do." I said with a smile from ear to ear.