tagTransgender & CrossdressersFeminized by My Girlfriend

Feminized by My Girlfriend


About 6 months ago I joined a gym because I have never had a very masculine body and now that I just turned 21 it was time to finally get off my butt and try to build some muscle. That is where I met my girl friend Brook who stands 5' 9", has a fantastic body and a gorgeous face. She looks like Tia Carrere who was in Wayne's World and True Lies but in my opinion much hotter. I have always had a thing for hot asian girls so when she walked up to me, my jaw almost dropped. I could not believe she walked up to me and started a conversation. Not only did she approach me, she asked if I wanted to grab a bite after working out. I agreed to meet her in an hour and could not help but to stare at her tight ass as she walked back across the gym. She turn and looked back and caught me staring and gave me a smile. Now I had the energy to lift more weight than I had ever lifted before. It still was not very much weight since I was a still a novice at working out but at that moment I felt like an champion body builder.

After working out I quickly showered and I met her in the lobby of the gym. She said she knew the perfect place to go so we got into her BMW convertible and we went to a quiet restaurant with very few customers. That was nice because we were able to talk and get to know each other. Since we were really hitting it off I asked why she approached me and not the big guys at the gym. She gave an evil smile and said, "Guys with long hair turn me on and I prefer guys who are lean. They are more flexible and are much more fun in bed." I could not help myself from blushing and when she noticed that, she smiled even more and said, "I am so glad we met, I am gonna have so much fun with you." Being naive, I had no idea what she meant but I was having such a good time, I really did not care. We did not sleep together that night but with in a week we were dating and started an exciting sex life. I have always been shy so even though I had just turned 21, Brook was my first girl friend. Also I do not have a lot of confidence since my dick is smaller than average only being a little over four inches fully hard.

Before I mentioned I did not have a masculine body. The truth is, I actually have kind of feminine features and had been teased most of my life for my looks. I love having long hair and would never change that but I was sick of being called a girlie boy and almost every other name they could come up with. Along with wanting to build muscle, I also hoped I might meet a girl at the gym. I just never dreamed I would actually meet someone so quickly.

Not before long I moved in with Brook. She is only 25 and already has her own Internet based business. I don't fully understand what the business does, but it is successful enough that she owns her own 4 bedrooms, 3 baths rooms house with a hugh back yard. If anyone would have bet me a year ago that I would be living with a beautiful girl in a real nice house and was extremely happy, I would have bet what ever I had and told them "No way, that will never happen."

Brook is really into eating healthy and working out so she put me on a very healthy diet and works out with me. I was surprised at the exercised she has me do. Mostly she taught me yoga and pole dancing. When we did any other exercises, they were the same exercise most of the girls were doing instead of the stuff I saw the guys doing. At first I resisted the yoga and especially the pole dancing but she told me that since I was new at working out, I had to build a foundation and work on my flexibility prior to getting into the heavy workouts. At first I felt really silly pole dancing especially since she made me wear heels for the extra tension it puts on the leg and ass muscles. It was really good workout and I could definitely feel I was getting in shape so continued to do what she said.

Not only did I do what she said when it came to eating and working out, she really took charge our relationship and our sex life. I am so in love with her, I will do anything she wants. She is very kinky and we experimented with many different fetishes. We tried a lot of different roll playing scenario's and sex in public places. She turned me on to anal play where she made me wear a butt plug or she uses her strap-on on me. She even made me suck on her strap-ons and dildos. At that point she had not dressed me up yet except for the heels she made me wear when I pole danced. We both like BDSM and I tried being in charge by tying Brook up, teasing her and spanking her but it was quite obvious that I was not very good at that. She knows how to and loves being dominate. I now truly believe I was born to be submissive.

One day Brook inserted a medium size pink vibrating butt plug in my ass, sat me in a chair and tied me up securing my arms and my upper body to the back of the chair. Then she secures my legs to the legs of the chair. She started to give me a slow sensual hand job. Her hands and my cock was covered in lotion and she was messaging my balls switch off from stroking me and gliding her palm in circular motion around the head of my cock. She would also vary the speed of the plug. She kept me close to cumming for almost an hour and was driving me absolutely crazy. Every now and then, she would get me so close, she would let go and just watch my dick twitch and ooze out a little pre-cum. Then Brook told me she was going paint my toes before she would let me cum.

Even though I did not have a choice, I agreed to letting her do it. I knew it would make me feel silly but I trusted her and knew kinky things pleased her. I figured no one would know and we had already tried so many different things, I thought, what the hell. As Brook placed a foam separator between the toes on my feet, she told me she had a bunch of different colors and I had to pick the color she would use. If I picked the same color she had in mind, I would get a special treat. I looked at the colors and figured she either had the bright red or the pink in mind so I told her I picked either of those two colors. She smiled and advised me her choice was one of the colors but since I did not pick one color, I would have to beg her to paint my toes in the color I chose. As I thought about it she started to tease my dick again but this time with her mouth. She sucked just the head of my dick in and swirled her tongue around it. I let out a moan and she stopped and said if I didn't beg soon, she would tease me for at least another hour before I could cum. I suddenly started begging her to paint my toes Pink and she asked why I wanted her to paint my toes pink. From some of our past roll plays I thought I knew what she wanted to hear. I started saying, "Pink is a cute color and even though I am already cute, pink toes will just make me even more cute." Brook then made me promise to do what ever she wanted if she would paint my toes. Once again, being putty in her hands, I did just that.

Brook whispered in my ear that while she did my toes, she wanted me to tell her how much I have wanted her to do this and how horny it makes me to have my toes painted. As she started to paint my toes, she asked me guiding questions. I found myself saying how I have never really felt masculine and painting my toes has been a dream of mine for years. She took her time doing my toes and commented how she could tell how much this was turning me on. As I was agreeing with her I started to realize it did turn me on a little bit since I never lost my erection.

As I look back, a lot of our pervious sex and experimentation with roll plays has conditioned me to say what she wanted to hear but obvioulsy at the time, I had no clue. I also had no idea how much things would change over the next few months. After my toes were painted a dried, she said she had something that would be a perfect accompaniment to my toes. She told me to closed my eyes as she walked away. When Brook returned, she untied me, removed the plug and slid something over my feet and then up my legs. I felt like it was a pair of underwear. She had me raise my hips off the chair and she slid them fully on. I opened my eyes and looked down to see I was wearing a pink pair if women's panties that matched my pink toes. This is the first time she has feminized me and I did not think she would be into doing that. Suddenly I had some very mixed feelings. I felt silly and embarrassed yet at the same time it was made me horny and naughty. Brook asked me to walk across the room to a pole and dance for her. Now I felt really silly but I placed my hand on my hip, placed my left foot directly in front my right foot and walked crossing each foot over the other like that down to the pole. Then I started to some of the dances she had taught me. I looked at Brook and could see how happy this made her which made me want to give her a real good show. After a few minutes she applauded and threw a dollar at my feet. I slid down doing a split which was easy after all of the yoga a dancing classes and picked up the dollar. Brook then clapped her hands and then she handed me my jeans. She told me we were going away on a trip right now and to get dressed. When I started to look suprised and started to speak, she placed her index finger on my lips and giving the "Shhh" sound. Her finger stayed on my lips, leaned forward and she said whispered in my ear, "You picked the right color and I have a big suprised for you. Keep the panties on and finish putting your clothes on so we can go. We are going on an adventure and you are going to cum harder than you have ever before." I tried to find out where we were going and what was going on but she just smiled and said it would ruin the surprise. As I was getting dressed Brook left the room for about ten minutes. While she was gone I got dressed and walked over to a full length mirror and looked at myself trying to see if I had panty lines showing. As far as I could tell, nobody would have a clue I was wearing panties and pink toes to match. Brook returned, kissed my very passionately and then walked me out to her car. I was wondering where we were going on and then I realized we were pulling up to the airport. She pulled into long term parking and I asked what was going on. "You will see so trust me. I have taken care of everything. You are about to be pampered like never before and take our relationship and sexual fantasies to a whole new level."

I started to get worried that since she had just painted my toes, made me wear panties and then go out in public, she might completely feminize me. Then I thought if she did, it would be in a hotel room in private. She would never do anything to hurt or embarrass me.

She got out of the car and went to the trunk pulling out 2 medium size rolling suitcases. She handed me one handle and told me to follow her. I kept asking questions and finally she stopped in her tracks, started straight into my eyes and sternly said, "I love you and want to give you this adventure more than anything. I have gone way out of my way to plan this so if you care anything about me, you will quit with the questions and just enjoy the trip." She had never talked to me like that. It made me feel small the way she spoke to me but also made me feel bad I was ruining her plans. As she continued to walk I lowered my head and followed her.

As I started to catch up to Brook, she stopped walked and turned to me. "I'm sorry about how I talked to you but I have put a lot of thought and time into making the best and wildest few days of your life. You should know by now, I know what you truly want and I plan to give you an experience you will never forget. I love you and I will never let you get hurt. You have to trust me and you will end up doing some things you might think you don't want to do at first but if you trust me and do what I say, you will find you will love it. Will you promise me you will do what I say no questions asked?"

I looked her and said, "I have to admit this all scares me but I do love and trust you with all of my heart so yes, I promise." I still had no idea how wrong I was when thought I knew how far she might take this.

Brook smiled and said, "Thanks, you won't regret it. Now stay here while I check our bags." As she walks away I wonder what she has planned but I figure she is just gonna take me to a new place and have crazy sex in a hotel room. What I don't know is where and for how long. She comes back and said, "I will hold

The tickets and we are about to fly first class to San Francisco. I told you that you were gonna be pampered baby so let's go to the through security so we can go to the lounge and have ourselves a drink."

I followed her to the security line and suddenly got real nervous. I have never been on a plane and had heard but completely forgot they make people

removed their shoes going through security. I see the security officer picking people at random and I turn to Brook and asked, "What if they pick me? Everyone will see my painted toes."

Nonchalantly she said, "Everyone is not here and who cares if they see your toes, you don't know them and you will never see these people again of god sake."

Even though she is right, I become real self conscious and pray as I walk through the line I don't get picked. When I don't get picked and just walk through, I am completely relieved. We walk down the hall see lounge. We walk in and she has obviously done this before. She tells me to grab us a couple of seats and she goes to the unmanned bar and pours us each a whiskey. I'm in awe watching how comfortable she is at all of this. Like I said before, I have never been on a plane much less traveling first class. As she handed me the drink I told her how I could get use to this. She smiled, clinked our glasses together and took a big drink. I sipped mine and she just looked at me and told me to quit acting like a girl and drink up. I'm not sure how to take that but I follow suits and gulp down the rest.

Brook leaned into me and asked, "Now, how did it make you feel when you thought people would see your pinky toes?"

"Terrified." I replied.

"But you got through it didn't you. You did not let the fear hold you back. I find that would help bring you out of your shell which I find real sexy. Almost as sexy as your toes and matching panties." Brook let out a big laugh and a wicked smile. " I'll get us another drink."

I started to think I'm over my head here but after my second drink I started to loosen up. We heard the call for our flight and she led me out of the lounge and past all of the people who have booked a coach seat on the plane. We sat in the comfortable seats and relaxed as the rest of the plane filled up. I was relaxed from the drinks and enjoyed being there when we got the pre flight instructions. They mentioned that we were flying to Atlanta and advised us how long it should take. I asked if we got on the wrong flight and she replied, "I didn't book a direct flight and we switch flights in Atlanta but don't worry, we are flying first class the whole way."

The flight and landing went real smooth. We exited the plane and walked into the main portion of the airport. We walked around for a while and I kept picking at my ass trying to adjust my panties. Brook laughed and said, "That's not very lady like so go into the rest room and adjust yourself. I found a stall and even though I'm in a stall, I got nervous that someone might see throughout the small crack by the stall door as I undid my pants. A humiliating feel came over me and I quickly adjusted my panties and pulled my pants back up as quickly as possible. Feeling relieved no one saw, I walked back to Brook who was waiting outside. As we headed to the next terminal to catch our connecting flight, I realize we now have to go through another check point. My heart started to speed up again once again hoped I would not get picked to take off my shoes. This time I did get picked. I started to freeze but Brook grabbed my hand and said, "Who gives a fuck what they think. Show your toes and be proud." then she lead me towards the security guard.

What she said did not take away the fear and humiliation but gave me enough courage to remove my shoes and socks and walk through. I heard gasps and snickers and I walked through security. As I passed through I felt completely humiliated. Brook kissed me and told me she is proud of me and advised me that even though my face looked upset, the bulge in my pants said otherwise. I suddenly realized that getting humiliated turns me on and as I thought back to when I adjusted in the bathroom, I was hard then too. I just did it so fast I didn't realize at the time. My mind struggled with the new realization that it turns me on to be humiliated. As we walked to the next lounge I figured out that Brook is right. She knows more about what I want than I know. I can't believe a few hours ago I was getting one of the best hand jobs I had even gotten and now I'm wearing pinky panties and just took my shoes off so a bunch of strangers got to laugh at my pinky toes nails. Now I thought that my perception about her feminizing me privately in a room might be an under estimation.

I looked at Brook trying to figure all of this out in my head. She looked back at me and could see I was angry and confused. Sweetly she said, "Look, it was about a one in five chance you would have to take off your shoes. Like I said before, you don't know them and they don't know you. Your confused because you feel I did this to you even though I have told you that I would never hurt you. Well at the same time you got angry, your dick got hard as a rock. You were teased and humiliated all your life but this is very different. You are being humiliated by someone who loves you and in a sexual way. You love it when I give you pain but would hate it if someone just came up and punched you. What you have to realize is I know what you don't. I know what you truly want but if I didn't force you to do it, you would be too afraid to see it for yourself. Like I said earlier. Trust me and do anything and everything I say." That is when she leaned across the table and once again passionately kissed me. Once again I melted and started to feel bad I was even mad at her.

From that moment we started to hold hands and I started to relax again. We got on our next flight and from all of the drinks and emotional ups and downs, I dosed off. I was woken up by Brook with a soft kiss and I was still buzzed from the earlier drinks. We got off the plane and got our luggage. As we were walking out of the airport we were met by Linda, a close friend of Brooks that I had never met. She was almost as hot Brook. She had long blonde hair, a tight body and huge boobs. She smiled, shook my hand but then grabbed Brook and hugged her. They started to walk out talking and I just followed. We walked up to a stretch limo and the driver took our bags and placed them in the truck. Linda and Brook climbed in first and sat on the back bench seat. I climbed in and sat on one of the side bench seats. Linda handed each if us a shooter and made a toast. "To old friends, new friends, and to new experiences. What a wild ride it will be." We clinked glasses, slammed our drinks and then they both laughed. As I wondered what the toast meant, Brook whispered something into Linda's ear and they both laughed. Thats when Linda smiled at me and said, "Okay, let me see em."

Feeling defensive I looked at Brook and asked why she said anything. She gave me a stern look and reminded me I that agreed to do was to do what ever she said. I could tell she was getting pissed so I tried to play it off by telling her she has not told me to do anything. She looked at me a said, "I will not stand for you to making me look bad in front of any of my friends. You will do anything I say and anything Linda says. She is like a sister to me and by not doing what she says is an insult to her and to me." She then turned to Linda and said, "He is all yours."

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byTrinni69© 0 comments/ 390144 views/ 178 favorites

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