Pretty Chris-tine

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Young couple experiment with feminization.
6.2k words
4.58
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Part 1 of the 3 part series

Updated 06/08/2023
Created 05/23/2017
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jealouscuck
jealouscuck
2,592 Followers

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.

We both stayed in the dorms at school. We spent as much time together as we could. Sharon was a perfect Dean's List student. She had a track and was studious enough to finish her undergraduate degree in less than three years. She went straight to the master's program and finished that early, also. I was more traditional, but I did well. With our parents help we got married during our third year. She was close enough to her BS and things were going well, that we just decided to make the step.

We did have sex before we got married and that was probably one of the reasons we decided to marry. We felt an obligation to our family to keep things on the up and up. Of course sex was very formal at first. After marriage, we learned to relax and enjoy it more. Sharon was always a little self conscious about her breast size and she only let me caress her occasionally.

After graduation, I got a job with a small manufacturing company as a junior engineer. My starting salary was just over 60 K. Sharon was recruited heavily and ended up accepting a position with an IT personnel firm. They recruited IT professionals and matched them up with specific client's needs. Her personality, smile and sharp intellect made her a natural. She travelled to colleges frequently as well as client's locations. By the end of her first year, she was making over 200K plus bonuses. We were so happy and very quickly bought a lovely three bedroom home.

Our sex life had gotten to the point that we talked about everything. Starting out with no experience meant that we pretty much learned together. I guess you could say we were very unexciting the first year. As we progressed, we shared ideas about sexual positions, oral sex and just the normal variations that young couples learn. By the time we purchased our home, we talked openly and kidded each other casually about sex topics. While I am not well endowed, she had no experience otherwise. I matured so late that I was always embarrassed by the size of my cock. I always tried not to be undressed around other guys, even in Phys Ed classes. Consequently, I did not notice other guy's cocks either.

With her job being so high profile, Sharon needed to make a certain investment in clothing to be up to date and fashionable. She most always asked me to clothes shop with her. Early on, she was having trouble getting fitted. Dresses were too average in size. Skirts and tops seemed out of sync. She tried on more that she bought. I learned what her likes and dislikes were.

One evening when we got in bed, Sharon said, "Chris, I want to ask you something."

I was quite concerned and told her to just ask.

"I have been thinking of getting breast augmentation. I have noticed how well some of my clients dress as well as some of the women I place. I think that if I were better proportioned, I would have an easier time finding appropriate clothing. What do you think?"

This was something I never would have guessed about Sharon. Her personality and general healthy good looks would have led me to believe that she was satisfied with her body. She made a good, logical case. I had to agree that she had a great job and was well compensated. The money was not a reason for me to object. Anyway, she made much more than I did, so I certainly could not hold that over her.

We talked very casually about it. She was practical, not emotional. It did not take me long to see her point. Neither one of us viewed this topic as a sexual item. Once we were in agreement, she found a plastic surgeon and set up an appointment for us to go.

I accompanied her to the office. After arriving and filling out paper work, she was taken back. I waited. After about forty-five minutes, the nurse came out and asked me to come back to the Doctor's office. We met and talked casually for a few minutes.

Finally, the doctor said, "Chris, I evaluated Sharon and she is the perfect candidate for breast augmentation. She is a young professional. Appearance is at a premium in her job, as I am sure you know, her body type is ideal for any range of augmentation. She has a nice set of hips, wide, with a lovely backside."

During the discussion, I mostly listened. Sharon and the doctor looked at the computer generated pictures from every angle and finally decided on a radical size. Since she was already more bottom heavy, larger implants could be utilized to bring her into proportion. What they finally agreed on was the equivalent of an F cup. The pictures were very dramatic. The doctor asked me what I thought about the size. He mentioned that couples need to decide together about these things. It would make the transition less stressful to be sure the husband was in total agreement.

I agreed that it was as radical change. I was not, however, concerned about the sexual implication due to the experiences I had shared with her shopping for clothes. She was scheduled for an appointment the following week at which time our decision to proceed and the sizing would be finalized. He gave her a bra and some foam bust enhancers to wear at home to help with the decision.

We discussed the implant size over the next week. There was no question that she was going to have the procedure. It was just the size that she decided. Wearing the prosthesis gave her a good idea of what some of her clothes would look like on her. Of course, most of her existing clothing would never fit her after the surgery. I deferred the final decision to her. She decided to go ahead with the large implants to totally balance out her figure. I agreed to support whatever she decided. She said that she just did not want to be a sideshow.

We returned to the doctor the next week. She told him of our decision. The procedure was going to be the ultimate method leaving no visible scars and done with the latest technology. What they finally decided on was a certain amount of fill in the implants. The doctor said it would turn out to be somewhere from a large F cup to a full G cup. The following week we went in for the surgery. It went off without a hitch and she was able to wake up and go home afterward. She was wrapped tightly and her loose clothing covered everything. I could not get a sense of how she was going to look until much later.

She was off work for about a week and then wore more loosely fitting clothing for several weeks afterward. We knew that a new wardrobe was going to be slowly added. There was no need to go on a huge shopping spree after paying for the procedure. She wore the bra provided by the doctor for several weeks until things healed up properly.

After about six weeks, she was ready to do some shopping. We spent some nights and weekends looking for suitable clothing. Her only problem now was that most of the dresses and tops had to be altered to fit her new figure. We went to one of the larger department stores on Saturday afternoon so she could try on some bras and lingerie. With every fitting, she had me give my opinion on the item. I loved looking at everything. She finally bought several bras, but some of the ones she wanted did not come in her size. The sales staff took all the measurements and placed the orders for her. The two bras she did get were different in color, but the style was pretty conservative because of her work.

The lingerie was a little different. She had me step inside the dressing cubicle while she modeled some night shirts, camisoles and nightgowns. I was erect the whole time. She invited me to feel the material and give an opinion. I got in quite a lot of touching including her new breasts as well as that beautiful ass. She seemed to enjoy my special attention to her big breasts. I stroked all around, ran my hands down her new cleavage and tweaked her nipples through the sheer material. By the time we paid for her purchases and made it home I was hot as could be for her. As soon as we got back into the house, I began taking her clothes off.

Sharon said, "Did all that lingerie shopping turn you on?"

"I guess so."

"Well, keep going and we will need to do something about that erection."

Now she could remove the bra. I admired her very big, very round breasts. They are marvelous. After the pain was gone, she loved them. She said that she felt so feminine and attractive. I assured her that it was definitely true. She pulled my face to her breasts and I carefully cuddled them and then kissed her nipples. I was afraid I would hurt her, so she began massaging her boobs to assure me that it was ok.

I was so turned on that I came in just a few strokes. I could not help it and I apologized to her. She was frustrated because she had not cum yet. I began kissing her and fingering her wet pussy. My cum was running out as I felt for her clit. I massaged the hard little man and she moved her hips and moaned. She held my hand and guided me to the right places before she began breathing more rapidly and then moaning louder. When she came, she arched her butt off the bed and squirted her girl cum over us both. I had never seen this before and I had no idea what had happened.

"God, that was good, Chris. Thank you for helping me get off like that."

"Honey, what was the liquid squirting out?"

"That was just the same as when you shoot your cum out, only the girl cum is very thin. I read where some people think it is pee and consequently are repulsed. Don't be. I can assure you it is not pee. To be honest that is only the second time that has happened to me. The first time was when I was masturbating years ago. I read up on it and found out that some women are able to do this if stimulated properly. I did not know that it was going to happen and I hope I did not gross you out."

She dipped her finger into a drop of the liquid and passed it under her nose. Then she passed it under my nose. "See, it is not like pee and it does not smell like pee."

I was still overwhelmed, but we talked about it some more. She asked what had turned me on so much. We agreed that shopping for lingerie must have done the trick. I really got off on all the sheer, sexy feeling as I had stroked her breasts and ass through the lingerie.

"So you like that sexy girlie stuff, do you?"

"You are so hot, I could not control myself."

"What turned you on more, my lingerie or my big breasts?"

"Yes."

"Oh you like it all do you? Well since I have never cum like that before, I guess I like it too. Thank you, Honey"

We had been married long enough to find out that we both really liked sex. Now the air of sexuality hung heavy. I sensed that the good was going to get even better. My cock size did not seem to bother her, but we began finding out that if I came before her, we needed a little digital or oral attention. Also, she came much stronger if I fingered her or licked her to orgasm.

Our shopping together continued to be the norm. I was the dutiful husband waiting on the attractive wife. She always asked my opinion on the outer wardrobe. Occasionally she would shop for some more lingerie. Her new bras came in and we went to the store to try them on. Of course, she had me look at each one when she tried it on. I was totally turned on when a couple of the bras were sexier and skimpier that her work bras. I complimented her on her taste.

She said, "If you like these, I have a little treat for you."

After getting the rest of the bras, I wondered why she did not buy some more panties. She told me that it was a good suggestion and that we were going to address that now. We walked down to Victoria's Secret. I was very turned on by all the really sexy lingerie there. Sharon made her way to the panties and started looking and feeling the material.

She asked, "Honey do you like these?" She showed me everything on the shelf and referenced the mannequin displays. With each panty, she asked the same question. Then she began holding the panty up and saying, "Feel this material. Fell the lace. Do you like this style?"

My cock was already hard imagining her nice ass framed in the sexy panties. She took a few pair to the dressing room and tried them on. She tried on boy shorts, thongs, bikinis, just every style they had. I really liked the fit of the silky thong. It framed her pussy, but she would have to remove all of her pubic hair to wear it. The tiny material up the crack of her lovely butt flared to the wider back portion of the thong. The front was tiny and the breadth of her hips made it look even smaller. The high waist made her legs look longer. I loved the thong the best. I told her that and she pulled it off and rubbed it on my cheek.

When she did, she noticed the little bulge in my jeans. "Oh, gosh, someone is having a good time," she remarked. When she tried them on, she had me feel her ass and wondered aloud if the panty line would show.

jealouscuck
jealouscuck
2,592 Followers
12