A Little Character Building

The woman started lifting bottles to my mouth to check. I felt a couple of people watching us. She must have lifted a dozen before she found one that matched. "This one is perfect," She said holding something called 'Cotton Candy Pink.' "You are going to look incredible in this color dear. Your nails are going to pop. Anything else?"

Hector smiled at her, "Well we could use some KY, my little princess here is losing her virginity today." I looked at him. Was he kidding me? Everyone around us heard and smiled or snickered at me. I felt myself getting so small, I wanted to crawl under the shelves. He was being such a jerk.

The woman brought us to another aisle. "Here you go," And she handed Hector the KY. "Also get this for afterward." And she gave me a bottle of hand lotion, then winked at me. "Have fun you two." And then she left me alone with Hector again.

"Wow, that was fun, lets go." He paid the cashier and then we walked to the food court. "You can paint your nails right here." There was one empty table. I looked around we were surrounded by teenage boys and girls.

"Can't you just take me home? Please I don't like being here in this outfit." He didn't even look at me. I figured I had no choice so I pulled out the nail polish from the bag and painted my ten nails in the perfect pink. He rubbed my legs the whole time. He even put one of my legs in his lap, his cock was pressing against my heel. He was staring at me as he pushed it against his hard cock, people were so close to us, watching. He then made me hold up my nails and blow on them. The girls next to us told me my dress was very pretty and it made me smile. I told her I loved her heels. I was starting to enjoy myself for the only time today. But then I wasn't.

Hector stood, "Okay bye girls, me and Wendy are going to our own personal party tonight." They said bye and we moved more into the middle of the mall. I was starting to relax, I'm sure the customers didn't think I was a crossdresser. Then we were standing in front of Macy's.

"Next stop," He said as he pulled me in. I knew where we were going. "Let's show off you in that outfit, come on." He pulled me into the juniors section where I bought this dress only a few hours ago. "There she is," He said, and we walked over to the cashier I saw this morning. "Hi, remember us?"

She looked up from her counter, "Um, no, how can I help you?"

"Well my little girlfriend here bought this dress in here today and she wanted to show off."

The woman looked at me and then I could feel the recognition hit. She smiled, "Wow you look very nice in that dress, I never would have imagined..."

Hector made me walk around and show how feminine I moved. I had to tell her about my heels and then about how I had to paint my nails for Hector. We were there so long, I couldn't wait to leave I was so embarrassed that she knew I wasn't all girl. I wanted to hide in the car and cry, even though she was being nice and supportive of me.

We then left, the woman told me to come back, she said she would find some outfits for me. I thanked her and Hector dragged me away.

We walked to the back of the store and he pulled me into a handicap restroom. "Come on, you better check your lipstick." We walked in and he locked the door. "Go ahead check!" He told me. I bent toward the mirror, I still looked like the slutty prom queen. I heard him behind me, I turned around he was sitting with his pants down around his ankles, on the toilet. He smiled as his dick got harder. "Well?"

I was stunned, I was completely unprepared for it. He wiggled his fingers at me to get closer.

"Come now, don't tell me you never sucked dick before princess. Look at those lips of yours."

It took a lot of convincing but unsurprisingly, I got on my knees. His cock was red and mean looking, was I really putting this in my mouth. He started to rub my face with his cock getting closer to my lips. I was starting to get a little excited myself, but I didn't want him to know that. I put him in my mouth and sucked. I couldn't get too much inside me. I kept my eyes closed the whole time. He started bucking as he sat and going deeper into my throat I had to pull off and cough. There was also a lot of knocking on the door.

"Be right out!" He yelled. "Keep going they'll wait. You better get in some practice, maybe we should fuck instead." He then pulled out the KY. "Turn around." I was shaking as he pulled down my pantyhose and panties. "Mmm gold panties, your pussy must go for a fortune sweetheart." He pulled me closer as I held my dress up, I didn't think I was ready for this but he started to put KY inside of me. It was cold and wet. He slathered his dick with even more. He then grabbed my waist and I hovered over his hard cock, I could see us in the mirror. Me in my princess prom dress about to sit on a man's lap with his pants down by his ankles. I was going to watch myself lose my virginity. I struggled to stay upright. I was about to fall back so he gripped me harder and I eased down onto his manhood. I felt him at my opening.

"This might hurt a little bit, but you can yell, no one will care, haha." As he laughed he eased me down onto him. I felt him inside me, it was so painful, I closed my eyes again. I didn't want to watch the girl in the mirror getting raped, just in case she liked it. "Push down," He told me and he went in a little more. It took about ten minutes to ease down onto his cock. Soon I was completely sitting on his lap, his cock completely buried inside me. "God, baby you are so tight, I'm not going to last too long."

Just as I was getting used to him he slightly pulled me up. "Oww," I let out a little yelp as my eyes opened. I saw him kissing my bare shoulder in the mirror. The sight was all of a sudden exciting to me. I started to move up and down on his cock, standing and then squatting in my golden heels, my tight pantyhose keeping my legs close together. It didn't take long for him to cum in my ass. He was groaning and holding on to my waist, he was moving me up and down. I felt myself cum, my little 'clit' started pulsing while still soft and a little cum started dribbling out of me, unlike the onslaught of cum he was shooting inside me.

When we were done, I sat completely on his lap exhausted until his soft dick slid out. I felt his cum trickle out.

***

"And that was it, my first time with a guy. God, are you happy I told you?" I shivered. "It was terrible."

"So what happened after that?" Lita asked me, she was sitting on the edge of her chair.

"I got cleaned up and used the hand cream on myself that the woman in CVS made me get. She was a genius. He left me in the bathroom. A woman in a wheelchair pushed in as I was bent over lotioning. I had to call car service to take me home and then run into the house to get some money. The driver followed me. I thought he was going to use me the same way Hector did. I was nervous of men for a while."

"And you never saw him again?"

"Well, I saw him two more times. two weeks in a row. We would go pick out a dress at the mall and I would put it on for him in the dressing room. He didn't like it as much, I was already dressed as a girl, and he only got off on humiliating me and then fucking a virgin. "

"And then the third time his girlfriend suddenly showed up while he was screwing me in my bathroom. I was leaning on the sink and he had his hands on my waist. We heard her screaming and banging on the door. She waited until he went inside me to answer it. He was a jerk, he put my address on his collectible car calendar at home. It was next to a big heart on a quiet Saturday. We let her in and she threw my little beige wrap at me from weeks ago, and then started to hit him over and over again. She grabbed his hair and pulled him out of the house. I think he was crying."

"Thank you! I yelled as they got into one of the cars. I forgave him for everything after watching that. Thank god I never saw him again. Good riddance, though suddenly he was very nice when he emailed me afterwards. I used to send him pictures 'cause I had a feeling his girlfriend was probably beating the hell out of him."

"You sent him pictures, god you are such a slut." She shook her head.

"Well he was my first, I still have a weird connection to him. Plus I always hoped his girlfriend saw one of my pictures and then cut off his dick. She was quite scary, and I figured I could dream. Can't I?"

"Now I know why you have that wall of mirrors in the bathroom."

I did they looked great. What did she think before, that I wanted to watch myself tinkle?

"And after that, I went to the mall no problem, it was a learning experience. I save all my prom dresses for myself. Marie in the juniors department at Macy's still saves me the ones she thinks I would like." I shrugged. I wished I was talking to Marie now instead of Lita.

She was looking on her phone again, "God there were so many fucking guys in your contacts and I don't know any of them. Wendy has a lot of friends." She then laughed, "Mike, Ian, Hal, Roman, god the list goes on. I was up all night finding some interesting items on your computer. You didn't even hide them."

"Why would I hide them? It's my computer."

She smirked at me, checking her phone again. "First of all, You have some freaky high heel obsession. I can't believe what you spend on them, and how many you have."

I loved heels, what was the problem, I spent so much money on her too, I never heard her complain about that. "I feel bad for you, knowing you can't experience a great pair of heels." I told her, lifting my red heels with the little bows, they were exquisite. They made me so happy. "A lot of them I didn't even buy, they were gifts," I told her.

"Bullshit, from who?"

***

Lita had started dating a black man named Tyler. I was very happy for her, she didn't tell me, her father did. Tyler was very nice looking, but he was loud. He made me nervous, so I stayed away from the house for a while. She didn't know that her father told me she was sleeping with him too. I didn't care, I was just waiting around for her to leave me for good. My mother would push us back together. But in the meantime, I started dating a bunch of men again. I was having fun.

Mike was a real estate agent who I met, that liked to make out with me in his car. Ian had a huge cock, I noticed him at my gym. I just wanted to feel it, he was very happy to let me. Hal was a quiet guy that talked to me at the coffee shop. And Roman had a thing for feet, so did I, of course, I was always looking for something that would make him hard and me excited.

I was driving around LA one Saturday morning, I was wearing This little peach-colored mini dress. It had little straps and I wore my chicken filet falsies in a strapless bra and put on a little tape for some cleavage. My hair was starting to get long, so I parted it in the middle and it fell a couple of inches below my shoulders. I had on peach lipstick and the same color on my long nails. My peach-colored toenails peaked through my five-inch white sandals. I had a nice mosaic necklace around my neck and a matching watch. I was ready to show LA my new look.

I drove near a park I had never been to before and took a bunch of pictures. I looked so good posing with a view behind me. I then got coffee from the little cafe I went to, and started to make my way around the suburbs of LA. I saw a sign, 'TURN HERE LOTS OF DESIGNER SHOES.' My heart started beating twice as fast. Designer shoes, I must be in heaven. There was no one around, it was a very nice neighborhood. In front of the house, there were shoeboxes all over the lawn and on tables, dozens and dozens of them. As I got closer a man came out of the house.

"Hello." He smiled at me.

"Hi, I saw your sign."

"Ha you are the only one, I have been out here since eight am." It was only around eleven but I was glad I was the only one here.

"Do you have any size eights?" He did, he had four of them all-new and totally sexy. I was very excited.

"Don't give me any money she told me to give them away."

"She?"

"Yeah, she is my wife, she works for the Shoe Warehouse in La Brea, these are last year's samples." He told me. I was excited they were all new to me. He picked up a notebook that was on one of the tables. "You know at the store they have over two dozen size eights and eight and a half's. Must not be a popular size."

"Maybe not popular, but it must be a lucky one for me." I had a big smile on my face.

"Hehe, yeah you're right, do you want to take a ride. I'll give my wife a call, they will be happy they are going to a good home." He said this as he glanced at my white sandals.

"Really? Okay."

***

"So they gave them to you?" Lita asked.

"They did, they still do. Tom and Laura, I see them all the time. We go to dinner, the movies, I'm constantly babysitting their two kids."

"You babysit, do they know you're a sissy?" She spat that out.

"I'm not a sissy, obviously you don't know anything, are you done I'm getting tired of this?"

"We're not done, I'm finding this fascinating. I now want to know about Hudson. You send him only shots of your face. You sent him over fifty this year alone. That seems weird."

"It's not, that's just his thing."

***

I met Hudson on Instagram, he liked my lips. He always commented on them. He saw that I lived in LA and he wanted to get together. We DM'd for a while and finally, we talked on the phone. He worked a couple of blocks away from Lita's father. I met him at the little coffee shop on Sunset that I like. I told my friend the barista about him, and he said he would keep an eye on me just in case.

I was a little nervous at first but Hudson turned out to be pretty nice, we talked for about an hour. "I like your glasses." He told me. "But I really like your lips they are so perfect."

I smiled I liked when a man gave me compliments. "A woman, Sonya, at a salon told me how to do my lips, I have been doing them wrong up until then apparently." I giggled.

"Can you," He then spoke a little quieter, a little quiver in his voice. "Put on some lipstick, I would love to watch?"

I smiled, "Sure, why not." I felt extra sexy today anyway. I had on my D cup breast forms and a tight beige sweater dress. It came to my knees. I wore nude pantyhose and low boots, I thought I looked quite cute for a coffee date. I had on my long red wig. It was the one I never wore but I knew Hudson seemed to like the pictures that I took while wearing it. I also had on black-rimmed glasses. I looked like I just got out of class.

First I took off what I could of my old color with a tissue. Then I pulled out my new red lipstick, it was Velour Liquid Lipstick, it was expensive and sexy. I started by holding my compact and then I glanced at Hudson. He was enjoying himself already. I went back to look at myself and turned the lipstick tube. When the color touched my lips Hudson made a slight groan and it made me turn around.

"Keep goin' Wendy please."

I smiled and finished my top lip, slowly following my lip line. Sonya at my salon used to make me practice until my lips looked full, plump, and thick, I have gotten very good at it. They were my second best feature after my legs. I then started on the bottom. Hudson made another groan as I finished and started to put away the tube. I looked at my lips to check and then he moaned once more. I pursed my lips at him and he started to double over, he was having an orgasm. I was puckering up and blowing kisses at him as he tried to keep quiet from the rest of the coffee drinkers. I just smiled at the barista so he knew everything was okay. When Hudson was done cumming, I put my compact away, I was a little excited myself.

"Wow, thank you that was so incredible." He told me, he had such puppy dog eyes.

I started to play with my hair and fix my glasses, I could tell he was liking the show. I blew him one more kiss and I giggled.

"You know most women freak out when I ask them to do that for me."

"Well, I'm not most women. Whenever you need some release call me." I giggled again, I was such a slut.

The next time we met I went to his home, he lived about thirty minutes away. He had been begging to see me for the last month and a half since the time in the coffee shop.

When I got to his house I was a completely different woman. I had on tight jeans, heels, and a white tank top. My D cup breasts held tight behind the ribbed top. I had just bought a new wig, it was a much brighter red. I had on red lipstick, red nails, and big round clear framed glasses. I looked too sexy to be visiting on a Saturday afternoon. When he opened the door, his eyes grew wide. He didn't say anything as I walked past him into the apartment.

"Well?" I said as I posed. His hand went down to his crotch. "Um, Hudson, Maybe you can wait until you offer me a drink before you play with yourself." I cooed. He laughed and then poured us two glasses of wine. He showed me his place, it was nice, it had lots of great collectables. As he walked around the apartment he did nothing but push on his hard cock. I thought it was cute, good thing we weren't in public..

"I'm sorry," He said, "But you look amazing, and your perfume, god I love it. I have never had such a hot girl in my apartment before." I was glad he knew I was a CD from Instagram, and I smiled at him.

He wanted me to kneel down and he would jerk off on my face, he wanted to cum on my lips. "Is that okay?" He asked.

"Sure, right here?"

He seemed a little taken aback, things were running a little too smooth for him. "Um, ah, yeah." His smile was so big.

I got my compact and lipstick and kneeled. he watched me putting on color again, even though my lips were already perfect. He then moved over to me as I smiled up at him. I started to rub my breasts as his dick got harder and closer to my lips. He took hold of his manhood and started jerking off. My tongue was sticking out waiting for his cum. He shot in less than two minutes. His sperm landed mostly on my chin and neck, missing my mouth completely, with most of it on my tank top. When he calmed down a little he took a picture of me with his cum on me. He was loving this. As he watched I used my finger with my long red nail and moved all his cum into my mouth. He grabbed his cock again and came before I even finished cleaning myself off. He was so worn out.

He gave me a bottle of Hibiki Japanese Harmony Whisky for the ride back, he said it was his favorite. "Okay, bye," And I drove away.

***

"We saw each other a couple of more times after that. We didn't have too much in common but he was very nice. I have a huge collection of Hibiki in my bar now, ha."

"I guess that explains why you have more red lipsticks than any other color, you have so many of them. I found them all in that locked closet of yours, you have to learn to hide that key better. You know that's fucking disgusting." Lita said.

I just shrugged, "Imagine that's all Hudson wanted. He just wanted a girl to be nice to him and fix her lips, no big deal. He wasn't asking for anything crazy. He wasn't dragging me into a handicap bathroom." I shrugged again then I pulled out my compact and checked my lips to Lita's annoyance. "He's getting married in another month, I'm invited." I shrugged again. "I made him very happy. He told me I gave him the confidence to meet someone. Making people happy makes ME happy. Do you want to try that whisky?"

"No. You let a guy cum on you it's totally disgusting."

"Maybe for you." I stood up. "Are you done? I never realized you were this tedious and nosy. Plus it's after eleven."

"You know I didn't find one picture of ME on your computer. Not one."

"Mmm." Of course not I was thinking, her I wanted to forget. I thought of her as more of a curse not a blessing, not something I really had to see.