Boy meets boy, boy meets girl

This story was written some years ago. Today I would probably have written a more condensed story.

LISA
Hi, I’m Lisa. Most people still know me as Tony. I’m waiting for my boyfriend John to pick me up to go to the mall to get me some proper clothes.

It all began on the first really warm day in spring. John and I have grown up next door to each other. Since the next house is over a mile away it was only natural that we became very close. John is two years older than I am and much bigger. 190 pounds of muscles and a star football player at school. While I’m much smaller I’m all muscles as well, being on the swim team. I had just beaten John swimming across the small lake at the back of our houses. We lay in the grass relaxing and basking in the sun. Since we live isolated we never bother about swimwear. Turning my head lazily to John I saw that he had a massive erection. Since I’ve never seen him with a girl I asked him who he was shagging in his dreams. I wasn’t prepared for his answer: ME.

He shocked not only me but himself as well but once it was out in the open he told me that he was gay, that he loved me (aren’t guys supposed to avoid saying that word?), that he had loved me for a long time and that he hoped this wouldn’t destroy our friendship. He’d never do anything to me that I didn’t want and so on and on. To shut him up I kissed him.

No, I didn’t fancy him but he was my best friend and I was afraid of losing that if I didn’t calm him down. As we talked he made clear that he loved me partly because we were such good friends and enjoyed doing things together and partly because he found my body extremely hot. He wanted to fuck me (my ass not his). I asked for some time to think and do research.

I soon found out that I probably wouldn’t appreciate the first time. I also wanted to give John a fair chance so what I offered him was three attempts with time to recover in between. If I didn’t like it then we would remain friends only. No further pushing from his side. John accepted eagerly.

We decided on Saturday night. Mother would be away for the week-end (Father died four years ago) and we often slept over on nights like that.

John was the most attentive lover possible. Telling me how lovely I was. Caressing me. Sucking me to get me horny. Preparing the penetration very carefully with lube and playing with my anus for a long time. In every way he made sure I’d be comfortable.

It hurt like hell!

I had promised him three attempts and no way I was going to back out of it but I dreaded the next week-end when my mother would be away again till Monday.

John was even more careful, even more loving. It hurt less when he entered me but it still didn’t feel right. As he slowly pumped in and out I just wanted to get it over with. Then I started to think of myself as a girl making love with her boyfriend. All of a sudden everything felt just right and I started enjoying myself. Of course, THEN the bastard came!

John was very happy I wanted to cuddle afterwards. Feeling his arms around me made me feel very secure and loved. When he asked if I had liked it this time I told him, not entirely truthfully, yes but that we would try something new next time and that it would be the next day already.

Next night John was not pleased that I was wearing my mother’s bra (filled with her tights) and crotch-less panties (she’d die from embarrassment if she knew I knew). He went at it manfully though. Very manfully and the little girl (i.e. I) exploded too soon. I didn’t pass out but it was close and John became worried. I told him not to worry and to go on. My second orgasm triggered his. Wow, those sheets really needed cleaning afterwards.

During the following weeks I grew more and more certain that I was meant to be a girl. Not just sexually. Being a girl just felt right! I had always felt that something about me was wrong but never realised what. However, I had no intention of being a stereotypical girl interested only in boys, clothes, make-up and, eventually, being a good house-wife. OK, I did check out the hunky boys in school, I did check up what the competition was wearing and cooking is fun! No way I’d be stuck at home though. I wanted a career of my own. Glass ceiling here I come! I started spending more time with the girls at school and some of my friends commented about me acting like a girl. To myself I became Lisa. I also started to think about what I’d do when I’d be 18.

John and I began dating. At first we drove far away to avoid meeting people we knew. It was always boy-boy. I wanted to be his girl but every time I tried bringing this up I saw how upset he’d become. Of course we soon became the school’s official gay couple. We avoided telling our parents though.

At home John and I fucked like rabbits every time we had the opportunity. I insisted on wearing bra and panties whenever I could get at my mother’s stuff.   The first day of summer break we finally got caught. We were doing it cowgirl style and my steed was really bucking as mother came into my room. She told us to go on since we obviously were having a great time and left at once. When John left my mother and I had the TALK.

The bottom line was that I’m going to live as a girl for the summer! She even used my true name from the beginning and not once did she slip. I’m her daughter Lisa! She insisted that I have to replace her crotch-less panties though.

When I told John he took it better than I expected. He even offered to take me shopping! He’ll be here in a couple of minutes.

JOHN

We drive to the mall. Tony is thrilled about finally going shopping for girl’s clothes. He goes on and on about showing the real “her” at last. Since it’s Saturday and we are late we have to park at the edge of the parking. The day is way too hot and we sweat just from walking slowly. Tony starts talking about whether he should get a bikini or a one-piece, he had seen the cutest little tiny bikini but wouldn’t a one-piece with high leg cuts be more feminine? Is this the boy I fell in love with?

It’s cool in the mall and we go to (shop name deleted). Tony is practically jumping, he's so excited. We find a shop assistant and Tony tells her:
“Hi. My name is Lisa and I need some help to get my measurements right.”  
The shop assistant recoiled, her face disfigured by disgust and hate.
“PERVERT, go away we don’t want your kind here and take your faggot abomination boyfriend with you” she screams.

Tony runs away. I catch up with him only because he collapses on a bench a hundred meters away. I sit down and put my arm around his shoulders. He lets his head fall on my shoulder. We sit there for a couple of minutes without saying anything. Finally Tony sobs
“I just want to be myself. Why can’t people accept me as I am?”
“Don’t think about her. There will always be bigots. Forget her. We’ll go to another store and I’m sure you will find that this was an exception.” I try to comfort him.

I finally coax him to follow me to (shop name deleted). At the entrance I ask him to wait there while I get an assistant. Actually I don’t have to look for one as a young lady, called Josephine according to her badge, says welcome to me and asks if she can help me. I immediately feel better because she’s one of those rare people that you can’t help but feel comfortable around.
“Please listen to me and if you find what I have to say disgusting don’t scream and let us leave quietly”
Josephine smiles encouragingly.
“My boyfriend over there is discovering his feminine side and we need help to get him a new wardrobe.”
“You say he’s your boyfriend. Is this your idea or his?”
“Oh, it’s his idea. I hate this. I love Tony the boy and would love to go away and forget all about this. However, this is what HE wants. I love him too much to tell him no. Oh, please don’t tell him I said that”
“Don’t worry. Stay here and I will take care of Tony”

I see her walk over to Tony. They talk for a while, looking at me every now and then. I can see how Tony relaxes. They start giggling and Josephine takes him away, for measuring I suppose. Ten minutes later they come back and start working through the lingerie section. I hear short parts of their conversation: “ … virginal white” “But I’m not ..”, “I have yet to see a boy who doesn’t …. suspender belt”. Giggle, giggle, “…hunk…”, “ …lipstick…mascara…”

What have I done? I’m 100% gay. Nothing feminine ever turned me on. I thought this would be just a case of dressing up. I could live with that but now I see someone else emerge. The boy I love is disappearing! I guess I have seen it coming over the last few weeks but refused to acknowledge it.They vanish into the changing rooms with a handful of sexy lingerie including stockings.

Soon after Josephine emerges again and I lose sight of her as she walks to the shoe department. After a while she reappears carrying a pair of VERY high heel shoes.

After an eternity Josephine comes out and approaches me.

“SHE is a lovely girl. HER name is Lisa don’t forget it. She’s really sexy in her lingerie. Go in there! She’s in cabin 5, it’s at the end. I will make sure that you aren’t disturbed. Please be careful. She’s very vulnerable.”

I enter the corridor with the changing cabins. I hesitate. What if it’s really a girl in there? If it is, will she go all the way? What will this mean to us? I stop. Total silence. I hear a soft sob. I make my decision and open the door to cabin 5. Josephine was right. It’s Lisa who’s standing there. Lisa is an extremely lovely girl and in her virginal white lingerie and high heels she’s the wet dream of any red-blooded guy. Josephine was right about her being vulnerable too. I can see fear of rejection in her eyes.

I tell her softly “Lisa, you are the most beautiful girl in the world” and embrace her.

I loved Tony. I care immensely for Lisa. How can I ever tell her that I will never be able to love her like I loved Tony? Will my ache ever go away?