Sharon and I got married when we were twenty. It was the magical fulfillment of our life-long friendship. Our families are very close, going back to our grandparents. On family outings, we were always together, for neither of us had siblings. We learned to play together and were comfortable from the beginning.
To digress, Sharon was classic in some ways also. She seemed to have the most bubbly and positive personality. She understood herself more than anyone I have ever known. She was a perfect cross of positive thinking and realistic expectations. Her intellect overshadowed her growing pains. She thought everything through and had a more adult understanding of problems than I did. In some ways, I always felt inferior to her.
Our junior year in high school, we went to the prom together as "friends". Our senior year, we went as boyfriend-girlfriend. Sharon was and is my best friend.
We had both turned eighteen early in early in our senior year. We were very comfortable with each other's families. Sharon told me that her grandmother was very happy. She shared that ever since we were growing up together that "Granny" always said that Chris was too "pretty" to be a boy. She did not call me handsome, just "pretty". Sharon got a kick out of that, but I was a little put off. I did not know whether they were attacking my masculinity or not. Sharon sensed my discomfort and said, "Oh, Chris, I did not mean to hurt your feelings. That is actually a compliment."
She explained that her grandmother said that adolescent boys can be terribly unattractive during puberty. Skin problems, voice problems, etc. Granny was just complimenting me on how neat and clean cut I was. We just left it at that. Sharon was always attractive, but as she matured, she had more curves. She kept her deep black hair is a short cut and cute was too mundane for her overall aura.
Near graduation time, her parents were away and Sharon stayed with our family. This was not at all unusual. Both our parents had almost viewed us as siblings, since neither of us had siblings. When we started dating, everyone was happy. We were over eighteen, responsible, trustworthy kids and always obeyed the rules, so we had plenty of freedom from supervision. Saturday evening, Sharon told my mom that she needed to go home and get some clothes and things because we were going out to a school play later. Mom told her "You should take Chris, just in to be safe."
This was also not unusual and we didn't think anything about it. We had kissed and necked, but had not had sex. When Sharon collected her things, we were about ready to leave when she remembered to get her favorite shampoo out of her bathroom. I walked up with her to her room. She was talking about shampoo, makeup, shoes, etc. just doing a mental check list.
While she was packing some makeup, I sat on her bathroom chair and was looking into her big lighted makeup mirror. She absent mindedly flipped on the light and I searched for an imaginary zit on my face. She shoved me playfully and told me, "Yes pretty boy, you look good."
Then she reminded me what her grandmother had said about me being too "pretty" to be a boy. She playfully wondered aloud if grandmother was right. She turned me toward herself and pulled out her lipstick and began trying to put some on my lips. I was laughing and she told me I better stop resisting or she was going to get some on my shirt. For some reason, I dropped my hands and she continued to dab her lipstick on my lips. She looked at me and said, "You are a pretty boy."
I looked in the mirror, but of course I did not agree with her. She said, "No, really, I wonder what you would look like with full makeup?" I was blushing and begged her to stop. I was looking to wipe it off and she was about to hand me a Kleenex, when she said, "The play we are going to tonight is short. I will let you wipe the lipstick off if you will let me make up your face before we go back to your house. Deal?" I just grinned and blushed some more. She helped me wipe the lipstick off, kissed my lips firmly, and then we went back to my home to get dressed for the play.
Sharon always dressed smartly, but very appropriate for her age. We went to the school play. Instead of hanging out we went directly to her house. She poured up some soft drinks and grabbed some chips before heading upstairs. When we got up to her room, she took off her dress and put on some old shorts and a tee shirt. She gave me an old baggy tee shirt to put over my shirt. I thought that the makeup thing was just a joke, so I told her she was really funny.
To which she replied, "Oh, no buddy boy, you promised. Besides, I want to see if my grandmother was right."
"Sharon, come on, that is just something your grandmother said as a compliment, you said."
"Yes, Chris, it is a compliment, but I have wondered about this for a long time."
She sat me down in her vanity chair and clipped my hair back away from my face. She then took some wipes and a cleaner and swabbed my face. Next, she applied some foundation. She smoothed it all over my face and dabbed any moist spots with a little sponge. She used an eyebrow pencil to accentuate a curve in my brows. She lined my eyes with liner and used her mascara to do my lashes. The eye shadow was next. She painted my eyelids with a light blue color and added a white highlight. My face was dusted with a fine powder. She added an orange blush to my cheeks. Finally a touch of light purple lipstick. Then she let me look in the mirror.
I could not believe the transformation. The makeup looked very professional. It was stunning. Sharon said, "How do you like it, Chris?"
I had no idea how to react. She had me stand up and look in a larger mirror. She was giggling uncontrollably, but not in a way that I felt she was laughing at me. She said, "Chris, my grandmother was right, you are prettier as a girl. She kissed me on the lips. My heavy makeup seemed to have an effect on both of us. She kissed me again. She slid her tongue into my mouth and encouraged me to french her back. She placed my hands on her ass and moved slightly as we embraced and kissed. She licked my earlobe and nuzzled my neck. I felt her panties through her thin shorts. I rubbed the elastic band and smoothed my hands all over her beautiful ass.
Finally, Sharon placed my hands on her waist and put her arms around my neck. We danced to the music of unheard soul. Just as quickly, she kissed me again and then pulled back. "We need to get you cleaned up and get back to you house before your parents yell at us for being late."
She got more Kleenex and cleaner and removed the makeup. All the while, she was telling me how gorgeous I was. I did not know how to respond, but there was certain tightness in the pit of my stomach and my little cock was standing at attention.
We decided to attend the same college about one hundred miles away. Our relationship grew. We both turned eighteen early in the school year. Sharon was taking mostly college courses her senior year. She convinced me to take some pre-college courses also. I was interested in engineering. I was good in math and science and my father is an engineer.