Madeline; Pleasing My Girl
Janet and I had only been together for a little over a month. It was a college romance that started in my freshman year. I made my awkward introduction when she dropped her books due to a clumsy oaf running down the hall. I was close and helped her gather her books up. I was thanked and she asked if she could buy me a soda. I agreed immediately, she was gorgeous and so out of my league, but hope does spring eternal.
The nearest place was a block away, so she led the way as I followed behind. I was getting an enjoyable view of her rear end as she made her way to the malt shop. The malt shop was one of the busiest places on campus, almost always packed with students between their classes. I loved their drinks, very glad she chose this place to have our drink at.
We ordered our sodas and then found a table near the front.
“Did you enjoy your view of my butt?” I, of course, turned numerous shades of red, being caught red handed. When my face color returned to a more normal shade I told her yes it was quite enjoyable.
“Do you do other things besides help females pick up their books and then stare at their butt?” Another blush of color spread throughout, even my ears felt hot and red. I decided the truth is the way to go.
“No, only very attractive ones. I also blush a lot, especially when the female in question is so pretty.”
“Good save.” That pretty much broke the ice and we had an interesting conversation for the next hour. She was somewhat quiet, had opinions and expressed them but let me do most of the talking. She asked for my cell phone number, after entering it in her phone I asked for hers. I got a smile but no phone number.
“I will call you when I need your services again, until then just keep thinking about my butt.” I did get a kiss on the cheek, but way to brief. As she walked away she was sporting quite a smirk though.
We passed each other in the halls several times, I always turned to watch her walk away, her butt swaying to and fro. She would always wiggle a little more, knowing that I was transfixed with her actions. It was three weeks later when she called, asking me to a dance that her dorm was putting on. I readily agreed to take her, but insisted that she let me buy dinner before the dance. “Okay, you twisted my arm, but at the dance you have to do what I request of you.”
I couldn’t think of anything I would refuse doing, especially at a dance. We agreed on a time and a place for dinner, with her meeting me there. I dressed nicely, although Sherry told me it was not formal. I bought her a corsage for her wrist hoping to impress her a little. I managed to arrive twenty minutes early at the restaurant, mostly because I couldn’t wait to see her again and be with her.
I had picked a restaurant that served a variety of different foods, since I was not familiar with what foods she liked. When she showed up she looked ravishing, a LBD that was stressing the little part. We were seated by the hostess, a quiet booth near the patio. Our drinks were brought out then we placed our orders. Both of us got Italian dishes, her choice lasagna while I got spaghetti and meatballs with tomato sauce. We chatted about our lives, a little about our backgrounds, but mostly about college and the courses we were taking. The food was great, both of us full and content.
We drive our cars over to the college gym, where the dance was being held. I parked next to Janet, taking my corsage with me. I gave her a hug as she got out of car, and then handed her the corsage. I got a big smile from her, but then as I took the corsage out of the plastic box, she held out her hand, taking the corsage and sliding it on my wrist. Since I never thought she would do something like that I was totally unprepared. I just stared at the corsage, then back at Janet. She took my hand that was sporting the corsage and led me into the gym.
Since speech was impossible at the moment, I didn’t say anything as she paid for our tickets and then led me into the gym. She got me a glass of punch then introduced me to some of her fellow dorm residents. The band started playing the first number and she took my glass setting it on our table, then led me out to the dance floor. She took my one hand and then placed her other hand around my waist just like you would hold a female. I stood there not knowing what to do, one of her friends came over and took my left hand and placed it on her shoulder. My right hand was held in hers as she led off the dance. I stumbled a little then followed like she seemed to expect.
It was four songs later when we took a break from dancing. She asked me if I wanted something more to drink, I nodded no. I was still tongue tied, every time I looked at my wrist I saw the corsage, then I thought to myself why I had danced the last four dances as a female would. No quick answers came to mind, even now I didn’t know how to bring up the subject with her. A few of her friends came over telling me how good a dancer I was. I just nodded, all of this throwing me completely off track.
Janet had taken her purse and freshened her lipstick, and then to my horror put lipstick on my lips. Again I just let her, even moved my lips as directed to smooth out the lipstick. Another of her friends came over, Sarah, and asked me to dance. I didn’t get a chance to respond before I was being led to the dance floor. Just like with Janet she led and I followed, not just this dance but five more, each with a different one of her friends. I doubted I could come up with the resolve to say anything to anybody. Ten dances and I was still doing the female part, the corsage still proudly displayed on my wrist.
Janet did eventually rescue me, taking me to the rest room with her. Yes, you guessed it, right into the ladies rest room. I looked down right away, not wanting to see anything I was not supposed to. When I saw an empty stall I headed into it right away, locking the door behind me. I quickly dropped my pants and set down on the toilet. Until I got to the bathroom door I was not aware of my need to go. From the amount of liquid that was released, I was lucky to get there in time. I wiped and then redressed, making sure my pants were buttoned and my zipper was all the way up. Then I left the stall, joining Janet at the mirrors. She handed me her lipstick, expecting me to reapply it to my lips. As she waited she released my ponytail and ran a brush through my hair several times. My image in the mirror as I applied the lipstick was now predominantly feminine.
I have no idea why I re-applied the lipstick, I am aware that Janet has some type of control over me, just not sure what and how. I was led back to the dance floor, spending the rest of the evening in her arms. I can’t say it wasn’t where I wanted to be, it did feel so good to be held in her arms. Nobody made any remarks about my appearance or me dancing the female role, I am sure it crossed a lot of people’s minds that evening, not every dance you get to see a guy wearing a wrist corsage and dancing as a female with bright red lips. By the end of the evening I was laying my head on her shoulders, cuddled close to her not even thinking of what I was doing. Lucky for me she was several inches taller than me, a necessity if I wanted to lay my head on her shoulder.
We rode back to her dorm in her car with her leading me up to her room. As we entered her room I was kissed sensuously, leaving me out of breath and panting when she finished. Quickly she removed my clothes, then slipped a pair of panties up my legs and then a nightie over my shoulders. I was pushed back on the bed and soon she joined me, naked as the day she was born. Needless to say I was ravaged by her, no part of my body escaping her attention. I just lay there experiencing the feelings as my nipples and male organ were played with. When she nibbled hard on my nipple after teasing it to death I erupted, Janet catching most of it in her hands, then feeding it back to me making me swallow. I can’t say I enjoyed it, but it was not that repulsive.
She slid a large t-shirt over her body and then cuddled up behind me. I started to close my eyes, looking at my wrist one last time seeing that damn corsage still there. I hope tomorrow things might get better, a return to the normal I have been used to for most of my life. Surely things could not get any worse.
I woke up having to use the bathroom badly. I sat to pee, it just seemed to be the proper thing to do. As I finished up I saw my image in the mirror, still some lipstick, the nightie with the panties peeking out from underneath. Then you have the corsage, still on my wrist and looking fresh and pretty. As I made my way back to bed I was pulled down next to her and kissed hard on the lips. I started to say something to her, but her finger on my lips stopped that thought. It ended up with her playing with my nipples as I laid there trying to figure out what has happened to me.
“I have seen the expression on your face, total bewilderment most of the time. I have an effect on some people, getting them to obey me without anything being said. I knew when I met you that you would do as I asked without questioning me. Now as to our relationship. I like guys, but gals are a lot more fun. If you want me to be a part of your life, you will have to be the female in this union. Last night you did well, no one thinking you were anything other than a tomboyish female. If you can live with that we have quite a future. If not it has been fun, but I want what I want and have always managed to get it.”
“I have given you a glance of what I like, now it is up to you. Show me what you can do to convince me that you are the one that I want to share my life with. It is all up to you now. Get dressed and get out of here, I have a class in an hour and I have to get ready. I will call you in a couple of days to see when you might want to meet. Don’t disappoint me.”
I slipped on my clothes, somehow they didn’t feel right now. Since I had ridden back with her from the dance, I had to walk back to the gym to get my car. Janet offered to drive me before her first class, but I needed the time to figure out things. One, what the hell happened to me and two do I continue on to win the affection of Janet. I too had two classes this morning, but figuring out what happened is more important at the moment, so I ditched both classes. I took the long way back, stopping often to take in the surroundings as I made my way back to my car, then to my house.
I did eventually get there, still wondering about her power over me. That is the only thing that I could think of causing me to act that way. Everything she asked I obeyed quickly and in a positive manner. How else would you explain a male wearing a corsage for almost a day, one originally bought for his date? Looking at my wrist the corsage was still there, all the way across campus and I still wore the damn corsage. Even now I was reluctant to take it off, Janet had not told me to remove it, but she was the one to slip it on my wrist. I eventually got it off since I had to attend a couple of classes that afternoon, but I am very happy they were only lectures. If I would have had to participate in the class I would have utterly failed for the day.
That night I did a lot of thinking, her last statement ‘Don’t disappoint me’ still bouncing through my head. How can I make her happy if I don’t know what will do the trick. I tried to list in my mind what happened last night. She put the corsage on me, I had to follow in dancing instead of leading, the panties, the negligee, the lipstick. Oh Gawd, she wants me to be the female in the relationship. Then it all came back to me, the last words she told me before I was sent out of her room. ‘If you want me you will have to be the female in this union.’ It all makes sense now, after thinking about it I was treated as a female date all night long. Okay, it takes hitting some males on the head repeatedly before they catch on, and I will admit it, I fall into that category quite easily.
If I want a future with her I am going to have embrace my feminine side quite a bit and from her last words I have until later in the week to show her I am willing and able to do it. Now other than wearing a wrist corsage all the time, how am I going to accomplish that? Females, pretty clothes, beauty salons, that’s it I need to find a beauty salon to help me make the change. I looked at yesterday’s newspaper, I thought I saw an ad for a beauty salon, something about a contest for the longest fingernail.
I found the ad and called the number, wondering if I have lost it completely mentally. I am calling a beauty salon to get made feminine for my girl. A girl that I have only known for parts of two days. Maybe it is already too late for me.
The salon answered and I asked about beauty treatments to make me look feminine. I was expecting laughter or a quick end to the call. I got neither. She suggested that if I came in, a specialist could appraise me, giving me ideas on what they could do and how I will look afterward. That included a picture of how I would look after all the treatments. It sounded good, I made an appointment for two hours later surprised that they could take me so soon. The fact that it was after five P.M. another huge surprise.
I made several more calls to see if any other salons would help me. I got laughed at one salon and the next two hung up right after I finished my request. That left me with the Turnabout Gurl Salon as my only choice. I changed clothes and made the trip. I was expecting a small neighborhood beauty shop like my mother used when I was growing up. Instead was this huge shop as big as some super stores, their parking lot jammed with cars. I could see in through some of their windows, customers and employees everywhere. Then right next to the salon was this huge clothing store, the sheer femininity of it oozing out of the doors.
I took the first step, in through the doors and met with my technician that would be helping me today. Beverly introduced herself, then asked what I was looking for. I blurted it right out, my soon to be girlfriend wants me to be the female in the relationship and I know nothing about how to accomplish it. I did manage to tell her that I wanted to ease into it, maybe something different every week until I see if this is what she wants me to do. No problem, may I suggest long nails to start with, very feminine and since they require a period to get used to them, a wise thing to start with.
I swallowed hard trying to get the frog in my throat to budge, but it was stubborn. I ended up nodding my approval and was led to a treatment room at the side of the salon. Beverly looked at my nails then went to a side counter and removed what she would need to complete the task. My mind was telling me that this was idiotic, but all I could see was Janet’s face and how I felt when she held me as we danced, then thinking of being cuddled in her arms last night seemed to make the decision for me.
When Beverly returned and started on my nails, I closed my eyes. If I can’t see what is being done than it can’t be happening. It is funny what the mind tells itself when faced with something so out of character for a male. I guess Beverly saw my eyes closed, squeezing my hand causing my eyes to burst open. She engaged me in conversation for the rest of the time, making me answer her and stay engaged in what she was doing.
It ended up with me being fascinated with my new nails, ten gorgeous nails extending from the ends of my fingers painted in a bright red polish. It made my fingers look longer and more delicate, and yes more feminine. When she finished she thanked me for the opportunity to work on me, then suggested a manicure for my toes, to match my feminine nails. I shook my head up and down, my eyes riveted to my new nails and how pretty they looked. Words escaped me, my total being fascinated by my new fingernails, not ever something I have even thought about before.
The manicure on my feet was delightful, so relaxing that I drifted off to sleep for a while. She squeezed my hand again, with me waking up greeted by ten pretty toes in a matching polish. We talked for a while as she made sure my polish was dry before I slipped my socks back on. As I was starting to gather my sock to slip it on she handed me a sandal, cute and feminine with little rhinestones encrusted on the straps. She helped me put them on, I wiggled my toes looking at how nice they looked in the sandals. I paid her for her services and the sandals, gave her a nice tip and made my way back to my car.
I was out the door and almost to my car before I realized that anyone looking at me could see the extensions and the bright red polish. As my former self that would have bothered me, now I raised my head and continued on, proud to be pretty and feminine. I made it home, and had settled in for the night when someone knocked on the door. I got up to answer the door and as it opened Janet spotted my nails and attacked. I soon found myself on my couch with her lying on top of me. There I stayed for over two hours while she showed her appreciation for what I had done. Maybe I can get my hair styled next week, wondering what rewards that might get me.
The next day reality stuck up its ugly head. I had to attend classes, with prominent long red fingernails. Since it was late spring it was warm, wearing gloves would stand out worse then the red nails. I had nothing to get the polish off, even a trip out to procure something would expose me to the general public. I called Janet hoping to get her to let me come by and help me remove the polish. She giggled at my request, suggesting that I if did show up an application of lipstick and maybe a bow for my hair would solve the problem. I decided to take my chances without swinging by her place.
I arrived at my next class, looking around to see how many people were staring at me. Surprisingly no one was looking in my direction. During the class a few of the females looked in my direction smiled and returned to listening to the teacher. After the class was over, several of the females complimented me on the nails, asking where I had them done at. Other than that it was a non-event.
Janet had homework she had to do tonight, so I was left by myself to wile away the hours. I spent the whole time reading some assigned reading and staring at my nails. As I got ready for bed, I kind of wished I had gone out and purchased a nightie, remembering back to the first night, the feel of it making me an easy convert to feminine sleepwear now. Oh well, I did rub my fingers over the polished nails, the slick feeling quite intoxicating. That is the last I remember as I drifted off to sleep.
The next two days were a repeat, I was beginning to wonder if Janet was already tiring of me, since she made excuses for both nights. At least she did not give me the excuse of having to wash her hair. I made another appointment at the salon, this time I decided on a feminine hairstyle, if this does not work out I could always go back to a short male hairstyle. I guess in a way I was getting desperate, wanting Janet back in my life all the time, and the heck with possible consequences of the feminine things I was subjecting myself to.
The hairstyle definitely put me over the top on apparent femininity. Loads of curls and even highlights to make the female in me stand out. After a look in the mirror I decided to purchase a feminine pair of jeans and a blouse, since my male clothes I had worn to the salon looked so out of place. The image was like a female trying to wear her younger brother’s clothes. Once in my new feminine apparel, the image turned to a young female trying to impress her BFF. I hoped Janet would be more than a BFF, but at this stage I will take whatever I can get.
When I arrived back home Janet was waiting for me, her big smile and her licking of her lips the look I was hoping to get. She apologized for standing me up three nights in a row, but she was behind in her studies, a certain new girlfriend consuming all of her thoughts and feelings. Now that she was caught up, she can turn her attention back to me. With one push I was led to my bedroom, another push as my new pants were sliding down my legs and I was laying flat on the bed as she attacked my face and breasts. She was mumbling something about nothing to play with, as she bit my nipple making me yelp.
I would imagine that breasts would have to be something that I looked into in the future, since she spent about an hour fondling, biting and sucking my little nipples till they were sore and red. It is amazing what I would consider doing for her, a male getting breasts a biggie no matter what the reasons or circumstances.
Over the next few weeks a number of feminine attributes were embraced, pierced ears, feminine eyebrows, a body free of any hair and me now wearing high heels for almost any activity. The current pair with five inch heels, and cute as can be. The stiletto heel, and the ankle strap, in an ivory colored leather making the shoe really stand out.
I presume my fellow classmates have gotten used to me dressed as a female, hardly any comments other than where I bought the item they were admiring. Yes, I did make my own purchases of clothing and shoes, Janet telling me that I would appreciate them more that way. Now when I see something in the shop window, I immediately turn to go in, making sure that I don’t miss out on something so pretty and cute.
Janet did eventually move in with me, after I agreed to her demands of me. I even changed my major, now I am a home economics major, Janet feeling that would better suit me, since I will be her wife, the training necessary to take care of her and our home. Our home that she went and purchased right after we graduated. I did get the breasts, sucked from my body, more than normal for my body size, but just right for Janet to grab a hold of in her opinion. Believe me she puts in the hours manipulating them, my nipples always a little tender from her constant attention.
On the second anniversary of me helping her pick up her books, I was surprised with a quick trip to Vegas where I was asked to marry her and the ceremony was performed. So now Madeline is married, a wife and play toy for Janet. She picked my name, then after we returned she made it official getting all of my I.D. changed to the new name and gender.
I will always remember the wedding night fondly, Janet’s dildo exploring my body till the wee hours of the next morning. I did walk funny as we made the trip to the airport to head back home, but the smile on my face made it all worth while. I never did release my grip on her arm, not going to let her get away ever. Pleasing my girl, that is what it is all about.
© 2016 thru 2024 Fran Cesca Walker