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Lindsey Looks Back
By RogerGirl

 I am sitting in the kitchen drinking coffee one morning with my sister Sharon and my ex-girlfriend and now best friend Vanessa.  Having recently finished a case I had been working on, it feels nice getting a day off to relax.  While we are talking, my daughter Emily comes into the kitchen carrying some papers.  She is now 8 years old and has grown into a very beautiful little girl.  As I look at her, I see not only my features, but the features of my ex-girlfriend who volunteered to be the surrogate for our two children.  I admit it does feel weird sometimes and makes me wonder what life had been like had I stayed a man and started a family with Vanessa.  As such, Vanessa is very close to both our children and is almost a second mother to them.

"Mommy?" Emily asks me.

"Yes, sweetie," I say with a smile.

"Can you help me with my family tree project?" she asks.

"Of course," I reply trying to hide my nervousness.

 I look at her list of questions and a wave of fear spreads through my body.  While she's often asked me questions about myself in the past, I have always done my best to avoid giving a direct answer.  Now, not only did I have to try and answer honestly, but she wanted a picture of me as a young girl as well.  Of course our children don't know that I was born a man and we aren't really sure how or when to discuss the issue, if ever.  

"Mommy, what were you like as a little girl?" Emily begins.

"Well, I think I can help with that one," my sister Sharon replies as she pulls a photo out of her purse.

 She hands me the photo and I look at it closely.  In the photo I see my three sisters, who ranged from 8 to 16 at the time, posing with another girl who looks to be around 13 years old.  As I look at this girl, I suddenly realize that this girl is me.  I suddenly remember the time my sisters dressed me up as a girl when my mother went out of town for a weekend.  Growing up I was never the most masculine guy, but I was afraid of being seen as different and went out of my way to act as much like the other boys as possible.  I played sports, even though I wasn't very good, and often got in trouble for picking fights.  

 On this particular weekend, my mother had gone out of town to help my grandmother, who was sick at the time.  It was nothing life threatening and  my grandmother is still alive today, but with her illness she needed some help around the house.  My sister Sharon, who was 16, was left in charge of watching us.  

"Lindsey, you have to help your sisters clean the house," Sharon said to me, "Mom left me in charge and you have to listen to what I say."

"Come on," I argued, "Why doesn't Miley do the dishes?"

"You know they are too heavy for her," Sharon responded.

"But dishes are a girl's job," I complained.

"Oh really?" Sharon asked with a smirk.

 I could tell I was in trouble and tried to make a run for it.  My sister Becky, who was 14, blocked the door as I attempted to escape.  The girls surrounded me and forced me into their bedroom.  I began to struggle as they removed my clothes and dressed me in one of Becky's school uniforms.  Underneath, I was forced to wear Becky's training bra, which they stuffed with socks, and a pair of panties.  Being only 13, I didn't have any body hair and my voice was still pretty high.  Sharon began applying makeup on me and they added a wig that she had used for Halloween.  At the time my hair was very short so the wig was necessary.  Finally, they let me go and I saw a cute girl staring back at me in the mirror.  I could hardly believe my eyes.  

"Now that you're a girl, Lindsey," Sharon said as she took some photos of me, "It's time for you to do the dishes.  You wouldn't want these photos getting out at school."

 Realizing I had been defeated, I went to the kitchen to do the dishes.  While at first I sulked the entire time, I soon found myself enjoying the feeling of the skirt on my bare legs and the long hair on my shoulders.  After the dishes, I did the laundry and made up the beds.  After a while, I had gotten used to being dressed as a girl and Sharon began going easier on me.  We were all getting pretty hungry and Sharon forced me to out with her and my sisters to the mall to get some pizza at the food court.  I was scared out of my mind at being discovered, but surprisingly nobody could tell I was a boy dressed as a girl.  

 After taking some silly photos in one of those photo booths, we went to the food court and ate our pizza.  I kept my legs close together since I didn't want anyone taking a look up my skirt.  I began to panic when a group of boys from my school came by our table.  Surprisingly, they didn't seem to recognize me.  Most likely since I was never very popular and never really stood out in school.

"Hi Becky," one of the boys said, "Who is this?"

"Hi Luke," Becky replied thinking quickly, "This is our cousin Lisa.  She's in town for the weekend."

"It's nice to meet you Lisa," Luke said with a smile, "Would you like to hang out for a while?"

"She'd love to," Sharon said before I could say anything.

 I shot her a look and she just smiled and told us to have fun.  Becky and I got up and went with the boys while Sharon stayed with Miley at the table.  Becky and a boy named Dylan walked off together leaving me alone with Luke.

"You're very pretty," Luke said as we walked around the mall together, "Where are you from?"

"California," I lied wanting to pick someplace as far away as possible.

"Oh, that's too bad," Luke said a little disappointed.

 Looking at Luke, I thought he was pretty cute.  At the time, however, I wasn't ready to face the fact that I was bisexual and tried to fight off my feelings toward boys.  We walked around a while and stopped to take some photos in the photo booth.  We took a couple silly pictures, then Luke surprised me and kissed me on the lips.  The kiss felt pretty nice, but I was afraid of what it all meant.  Without saying anything I ran out of the photo booth and hid in the girl's bathroom.  Eventually, my sister Sharon found me crying in a stall and took us all home.  

 When we got home, she let me change out of the girl's clothes as long as I promised to help out the next day.  I agreed, but she could tell something was bothering me.

"What's wrong?" she asked concerned, "Did Luke do something?"

"I don't want to talk about it," I said defensively.

 Sharon left the room, but could tell something was definitely bothering me.  After that day, however, my sisters never brought it up and never tried to dress me as a girl again.  Of course I often thought about sneaking into their rooms and dressing up on my own, but I was afraid of getting caught and tried to forget the experience.  

 While I can't tell Emily the entire story, I try to tell her a version of the story that will satisfy her questions.  I tell her that I was sort of a tomboy as a child and that Luke was the first boy I kissed.  Sharon and Vanessa seem a little shocked at this last piece of information since I had kept it a secret all these years.  Emily thanks me for helping out and I give her the picture of me as a 13 year old girl.  She goes to the living room to ask Dave for information on the next part of the project.

"You kissed Luke?" Sharon asks in surprise after Emily is gone.

"No, Luke kissed me," I answer honestly.

"So that was what you were so upset about when I found you in the bathroom," Sharon continues, "Did you like the kiss?"

"I did," I reply, "That's why I was so upset.  I knew I liked girls, but I was afraid to admit that I also liked boys.  And I was also ashamed that I liked being a pretty girl.  Could you imagine what mom would have done if she found out?"

"Yeah, she would have been pissed," Sharon replies, "She was always a little overbearing."

"I think it's probably what drew day away," I joke.

"Did you ever dress as a girl again after that?" Sharon asks with great interest, "Before the road trip I mean."

"No, I was afraid to,"  I respond, "I wasn't ready to admit that I liked being a girl."

"Well, there was one other time," Vanessa interjects, "Remember the Halloween party?"

 Oh yeah.  The Halloween party.  During our senior year in college, Vanessa convinced me to go to a Halloween party with her dressed as a girl.  At the time I had just turned 21 and was in the habit of keeping my hair long.  Looking back, it was probably my Halloween costume that gave my friends the idea to dress me up as a chick and leave me in the desert.  

"I bet you'd look cute," Vanessa said as she held up the devil girl costume she had picked out for me to wear.

"I'm not dressing as a chick," I argued, "All of our friends are going to be there.  It'd be humiliating."

"Please, do it for me," she pleaded with a cute little pout.

"That's not working this time," I said.

 Vanessa was very persistent, however, and did something she knew I couldn't resist.  She went up under the covers and gave me a blow job.  Now while I love being a woman, there are times I miss certain things about being a man.  Vanessa's blow jobs is probably near the top of that list.  Being able to pee standing up would be another, but I digress.  

 After the blow job, I knew I was defeated and reluctantly gave in.  The truth was, since being dressed as a girl when I was a kid, I had secretly longed to dress up again.  Finally I would get that chance.  Vanessa instructed me to remove all of my body hair and attached a pair of breast forms and a prosthetic vagina, the same ones my friends would later leave me stuck with in the middle of the desert.  I put on a sexy red bra and matching thong and a short, tight-fitting red dress.  Vanessa went to work painting my toe nails, applying press-on nails, doing my makeup, and styling my hair.  When she was finished she placed some devil horns on my head, had me put on a pair of red 5" heels, and handed me a trident.  

"Wow, you look amazing, baby" she exclaimed.

 She helped me over to the mirror and I saw a gorgeous woman staring back at me.  It was quite an improvement over the time my sisters had dressed me up and it felt amazing to see myself as a girl again.  Of course, I didn't want to let Vanessa know how I really felt so I just sulked.  She left me alone to change into her angel costume and I began to pose in front of the mirror when she was out of the room.  When I heard Vanessa coming back, I went back to sulking again.  

 At the party, my friends could hardly believe my eyes when they saw me.  I even caught the attention of a hot guy, who was well aware of who I really was.  Afraid of what I would do if I found myself alone with him, I stuck close to Vanessa the entire night.  At the end of the night, we went back to our apartment and Vanessa helped me change back into a guy.  

 After that night, however, things became tense between us.  I wanted so desperately to dress as a girl again, but was still afraid.  Vanessa could sense I was hiding something and grew angry when I continued to blow her off.  Eventually it led to us breaking up.  

"I have to admit something," Vanessa says after the story finishes, "I've always felt bad about this, but I'm kind of responsible for your friends playing that prank on you."

"What do you mean?" I ask in surprise, "You weren't even there."

"Well, I was pretty mad at you after our break up," Vanessa begins, "The guys came to me one night and asked if they could borrow the stuff I had you wear on Halloween.  I gave it to them thinking they were just going to dress you up for a night in Vegas.  I didn't know they were going to take it so far.  I hope you can forgive me."

"Of course I do," I say taking her into my arms and kissing her on the cheek as tears run down both our faces, "If you hadn't done that I would have never come to terms with the real me.  It was probably the greatest thing you could have done for me."

"Get a room you two," Sharon teases, "I've always wondered something.  If you hadn't met Dave, would the two of you have gotten back together?"

"Well, yes," I reply honestly, "I've never stopped loving Vanessa and she will always have a special place in my heart.  Not only is she my best friend, but it is because of her that I have two amazing children.  I don't know how Vanessa would have felt entering a lesbian relationship though."

"Honestly," Vanessa says, "I would have considered it.  Even after you announced your transition, I still had feelings for you.  I would never come between you and Dave, but if we had stayed together, I would have loved you no matter what decision you made."  

 We hug again as Dave comes into the kitchen to get a beer.  He looks at us with concern when he sees that we have been crying.  He comes over to the table and puts his arms around me.

"What's wrong baby?" he asks.

"It's nothing," I say as he dries my tears, "We were just sharing some memories.  Does it ever bother you that I used to be a man or that I'm bisexual?"

"Of course not," Dave says as he kisses me softly on the lips, "I knew exactly what I was getting in to when I met you.  I could have left you behind at any time and continued on the road trip on my own, but I didn't.  I love you and will be with you forever."

"Thanks baby," I reply, "I love you too."

"As for the bisexual thing," Dave jokes, "I don't want to sound crass, but I think it's hot.  It's also led to some pretty amazing threesomes."

 We all laugh, and if you're wondering if what he said is true, it is.  Before the kids were born, I often found myself missing the sensations of being with a woman.  It wasn't too hard to convince Dave to bring Vanessa into our bedroom for a little fun on occasion.  It was shortly after I had completed my transition and before Vanessa volunteered to be our surrogate.  I guess you could say that Vanessa has always been an important part of our marriage and although we had planned to get married when we were dating, she has felt no ill will toward me.  Of course we no longer have threesomes with her, but she has become my best friend and I couldn't imagine my life without her.  Just as much as I love my husband, Vanessa also holds a special place in my heart.  

 There is a knock on the door, and my other sisters arrive with their families.  Becky actually ended up marrying Dylan and they now have a 6 year old son.  My little sister Miley came out as a lesbian after I announced my transition and credited me with giving her the courage to come out.  As you can imagine, our parents disowned her too.  Today she is married to a woman named Irene and they recently adopted a baby girl.  Sharon was married for a while, but she recently got divorced and never had any children.  Despite not having any children of her own, she has been a very good aunt to each of our children and is always there to babysit them whenever we ask.  Vanessa never got married, but occasionally she has a boyfriend.  I admit I feel somewhat responsible for her still being single and I hope one day she will find a man who will make her happy.  

 My kids come downstairs and we all head out to the patio for a barbecue.  As I look around at my family, I can't imagine my life having turned out any other way.  I have an amazing husband, two wonderful kids, the support of my sisters, the best friend a girl could ask for, and an amazing job.  Do I ever miss being a man?  Sometimes, but I know this is how my life was meant to be.  

"Mommy, come swim with us," Emily says as he splashes with her brother and cousin in the shallow end of the pool.

"I'll be right in," I say with a smile as I strip down to my swimsuit and walk toward the pool.    
It has been over a decade since Lindsey transitioned into a woman, as you can read in my story "The Hitchhiker."  When her daughter is assigned a family tree project for school, Lindsey is conflicted on how to handle her daughter's questions.  With the help of her sister and ex-girlfriend, she is reminded of her earlier experiences being dressed as a girl.  
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Submitted on
January 21, 2014
Mature Content


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