My Gal Alison
by Rod O'Steele
Copyright© 2009 by Rod O'Steele
Erotica Sex Story: A story of unusual young lovers, but real love none the less
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft Consensual Romantic TransGender Brother Sister First Anal Sex .
I was a junior in high school when I met Alison. That's not quite right. I met her as a freshman but it was as a junior when I really noticed her. We went to Francis Drake High. It was a magnet school; students came from all over, and it was for high achieving students. That's different than genius students. Smart doesn't always equate to high performance.
I lived up in Noe Valley and had to ride the bus downtown to the campus. It was a pretty normal high school except for the homework and reading assignments. Most of the junior and senior level classes were college equivalent. In fact, the University of California accepted them as lower division work. Most kids from Drake entered college as juniors.
Other than that, it was a pretty normal school. We had sports teams and cheerleaders. The image of the bright student as nerd is really not true. A higher than normal IQ typically goes with better than normal physical ability. Sure, there are geniuses who can't throw a ball just like there are pro athletes who can't read, but it's all a bell curve. Our football team finished second in league. I was on the track team and we won our league two years in a row. Our cheerleaders were as hot as any and invoked legions of teen lust, and dad lust, at the games when they danced around in their little outfits. Come to think of it, since it was San Francisco, they might have invoked a little mom lust too.
That is enough about the school. The fact is the kids were like those in any other school, even though they were high achievers. There was this girl in my analytic geometry class, Alison. She sat one row in front of me so I was always seeing her from the side and one row behind. I could stare at her but she didn't see me. I thought about her all of the time. But she was shy. She didn't have any real girlfriends; as well, she never had a boyfriend as far as I knew. I wanted so much to take her out.
I hit the jackpot one day. My mom worked for the city Arts Commission. She would sometimes get tickets to various performances. On this fine day for me, she got two tickets to a Yo Yo Ma recital and she asked if I wanted them. Only if I could use the car to which she agreed. I had only had my license for a couple of months, so driving at night and all the way to Bezerkley was a big deal. I knew I'd have to put up with a lecture about how to drive and staying out of trouble in someplace likeBezerkley, but it would be worth it.
After class the next day, I made sure to walk out with Alison and said "Hi." She looked a little surprised that I was talking with her, but I persisted, which took a lot of fortitude. Normally, I kind of melted away from girls after getting tongue tied. But I really wanted to go out with her.
"I've got two tickets to a Yo Yo Ma recital in Berkeley this Saturday," I said.
She looked at me like, so what?
"I was hoping you would like to go with me," I said.
Alison stopped right there in the quad. "Really?"
"Yeah," I said.
"I've never been to a concert. My folks don't like classical music," she explained. The smile disappeared from her face as she said, "I don't know if my dad will let me go."
"Why not? It's not like rock concert," I said. "There won't be a bunch of people getting stoned at a Yo Yo Ma concert."
Alison smiled, "I know. But he doesn't let me date," she explained.
"Can you ask him?" As I said, I really wanted to go out with Alison.
She smiled, then a cloud came over her face and she shook her head. She put her head down and said quietly, "I'm sorry, Allen." She turned and walked away.
By the way, Allen, that's me. I'd even thought about how it would sound, Allen and Alison. It had a nice ring.
I knew Alison lived near me because she was sometimes on the same bus. That afternoon, I made sure I was on her bus. I sat in the back so I could watch. She got off at the next stop after mine. I got off after her and followed, discretely. But she wasn't watching for a spy and never even looked behind her.
It turned out Alison lived just a few blocks from me. I went home and thought. I wanted Alison to go to the concert. At school the next day she shyly smiled my way, but then looked away. She hurried from class so I could not catch up with her. That smile made up my mind.
That evening I went over to Alison's house. When I knocked, a nice looking lady answered the door. When I told her I went to school with Alison and would like to see her father, the woman looked surprised but she invited me in and had me sit down. She came back with a man. He asked me, "What can I do for you?"
"I have two tickets to a classical concert and I asked Alison. But she said you wouldn't let her date. I thought maybe if I asked you, because it's a classical concert, it's not like a rock and roll concert, you'd let her go," I said. Then I took a breath.
He looked mad but her mom was smiling. He looked over at her and saw the smile. I could see the thoughts going around. He looked at me. "No."
I was shocked and about to say something when her mom said.
"Frank," with a little emphasis.
"Oh Jesus," he said. He looked at her, "Margaret..." She just stared at him with a lifted eyebrow. He sort of hung his head for a second then looked back at me. "You know the saying 'A man's home is his castle, ' don't believe it."
"My dad says the same thing," I said. That at least brought a small smile to his face.
He looked back at Margaret. She nodded. "It sounds like Alison is going to a concert."
Margaret said, "Let me get Alison," and she went into the hall.
A few seconds later Alison came into the front room. She looked shocked, "Allen?" She also looked extremely hot wearing a pair of tight shorts and a tube top that showed off her breasts.
Her dad stood up. "Alison, it seems this young man really would like to take you to a concert. Since he seems persistent," he looked in my direction before continuing, "your mom and I decided to let him take you out."
She looked at her dad. "I can go?" He nodded. She threw her arms around her dad, "Thank you."
Her mom gathered up her dad and they went back into the house leaving Alison and me alone.
"I can't believe you did that," she said.
I shrugged. "Do you want to go?"
She nodded.
"I'll pick you up Saturday at five, if that's okay," I said.
"I'll look forward to it."
"See you tomorrow at school," I said.
Alison looked happy and she smiled demurely.
On Saturday, I drove over and picked her up. I expected the old meet the family ritual, but she was standing at the curb. She was wearing a nice dress that scooped low enough to show the beginning swell of her breasts, if you looked, and I sure looked.
Dinner was at a nice Thai place on Shattuck. Thank God I didn't have to pay for the concert because that dinner took a good bit of my ready money. My dad is a professor at SF State and he gets sent bugs from all over the world. I look them up in reference books, type up a specimen card and attach the bug, number it, log it, and put them in plastic specimen boxes. He paid me the same as he paid his graduate students, which was okay money for a kid. But this was San Francisco prices for the restaurant.
The recital was at the University and I had warned Alison to wear walking shoes. Berkeley is as bad as the city when it comes to parking. The concert was quite different being the Schubert Arpeggione in A Minor, D. 821; Shostakovich's Sonata in D Minor, Op. 40; Piazzola's Le Grand Tango; and the Franck Sonata in A Major for Violin and Piano except rescored down for the cello.
As we waited in line, Alison looked over the program. "I have always loved the Franck sonata. I never heard it on the cello."
I could tell from her breathless expression I had made a major hit. The Shubert was okay. Shostakovich was his usual ironic self. I loved the Tango. I mean, how can you not love a tango? It is sensuality expressed in dance. It is the rhythm of love. It is vertical sex set to music. I held Alison's hand during the tango and the heat of the music was reflected in the heat of our hands clasped together. I suspect that half the audience would have been naked and humping if they weren't in the middle of an auditorium.
The Franck Sonata, or as some classical djs call it, the Frank Sinatra, sounded even better on the cello. César Franck had written it using much of the lower register of the violin. Writing it down for the cello made it even more moving. Alison was floating as we left, holding on to my hand as she practically danced down the sidewalk.
"Thank you so much for taking me. My parent's don't like classical music so I've never been to a real concert before," she said.
"It was my pleasure," I answered.
We drove back to the city talking about the concert and how much she liked it. I dropped her off at her house. We stood on the front porch talking for a minute, then she said that she should go in but she didn't reach for the door. She stood looking up at me. Even I could figure that clue out. I leaned down and we kissed. It was electric.
"Thank you so much for everything," she said as she went in. I floated back down the walk to my car.
On Monday I walked with her after class. She talked about the concert and how much she liked it. So I asked her if I could see her again. She teased me for a second but then said she'd really like that. I invited her to dinner on Friday and hoped I wasn't pushing too fast. There was a pause, then she said "Alright."
The rest of the week I walked with her after class and we talked like nothing was wrong. I thought everything was fine until I got the call at 4:30 on Friday. "Uh, Allen, this is Alison."
"Hi," I said brightly.
"Uh. Allen, um, I can't come tonight. Maybe another time," she said.
I was stunned. "But Alison, I have everything planned."
"I'm sorry but I can't come," she said hastily and hung up.
What the hell was this all about? I tried calling back but if it rung, she never picked up. I got pissed.
On Saturday I went over to her house. I knocked and her mom answered. She invited me in. "I'll get Alison," she said. A minute later Alison came in looking like she was being sent to prison.
"You know Alison. At least you could have said you didn't want to see me again rather than lead me on like that," I said trying to keep my cool so I could be in right while she was the one in the wrong.
"But I did want to see you again," she said.
"You have an awfully strange way of showing that," I said.
That's when she broke down in tears. I don't know what it is but there is something deep in the genes of men so that when a woman breaks down like that, unless you have built up an immunity because she does it so often, it just fucks with your mind. Before I even knew what I was doing I was holding her in my arms soothing her, even though just seconds before I felt I was the aggrieved one. Go figure.
Through her tears she kept saying she was sorry. I finally got her to stop crying. "Let's go have some coffee," I said and led her to my mom's car that I had borrowed. I found a parking place right near Bernie's so we went there.
Alison still looked scared as we sat down with our drinks. "I'm not mad anymore I just want to know what happened," I said.
"Oh Allen, I just got scared. All the stories..." She paused to wipe her eyes. "You see, my dad never let me date before."
"Yeah, I know. Did he change his mind?" I asked.
She shook her head. "He was sure I'd get in trouble, get beat up or something. He kept telling me about ... girls getting beat up. It was scary."
"Well, you could have told me," I said. "Alison, I'd never hit you."
She nodded and looked down. "I know. I just wasn't thinking very well. I guess I'm sort of backwards when it comes to this stuff."
I was surprised. "Well, do you want to date?"
"Oh yes," she said desperately.
"Really? You won't chicken out on me?"
"No. I promise." She looked up. "I'm such a wimp," she said.
So we set up another date that night. I admit to feeling a lot less sure. But she had promised on her life and I expected her to keep that promise.
Saturday afternoon I was in total doubt. Was she just messing with me? Was this all for naught? I just couldn't get my mind off the wondering. At six sharp I showed up at her house. The door opened and it was Alison and my spirit soared. All was again right with the world.
Once again, she looked hot. I could tell she was happy so I leaned down and kissed her. She looked a little dreamy and I wanted so much to kiss her again, but I remembered her anxiety and didn't. Plus here we were standing in her doorway. Instead, I asked, "You want to watch a movie?"
"Sure," she said.
We got in the car and headed to the movie-plex. Alison snuggled into my side and I put my arm around her. She smiled as she settled in. Now this was going well. But I also realized that this girl had never dated. "Alison, I know you haven't dated but have you ever been romantic with a boy?"
She shook her head looking a little sad.
"Hey, don't be sad. Look at all you have to look forward to," I said.
That brought a smile to her face.
"I don't know how else to say this, but I don't want to do anything you don't want to, but..." I hesitated thinking and she jumped in.
"I know, but girls ought to do certain things."
"It's not an obligation," I said. "What I was going to say is if I ever do anything you don't like just let me know."
"Okay, and I won't try to be a stick in the mud," she said.
"I won't either," I said. The movie started and we sat in the back of the theatre. It was nice watching the movie all snuggled in.
After the movie, we drove to a place a couple blocks from home and I parked looking out over the city. We talked about the movie and laughed. She snuggled into my side again. I took that as a good sign and leaned down to kiss her. Her response this time was more enthusiastic. We kissed for a while. I looked down at one point and saw the swell of her breasts presented by the low cut blouse so I leaned down and kissed the base of her breasts. Alison gasped but didn't pull away. I kissed again but this time also gently cupped her breast toying with the nipple. It quickly grew between my thumb and finger.
The kisses were getting pretty hot now as I played with Alison's breasts. She seemed to be enjoying this so I moved my hand down to her leg and slid it up a bit. She grabbed it and I felt her tense up, so I pulled my hand away. That was the limit. I was okay with that. We were both pretty hot from the kisses when I pulled away.
"I want to..." Alison said and stopped. "I'm scared."
"What are you so scared of, Alison? Me?" I asked.
"I'm sorry, it's just that..." And again she stopped mid-sentence. She looked away. "I should be going home. Allen, I hope you'll understand."
"Alison, I understand. I'm kind of a little confused myself. I really liked kissing you and touching..." I couldn't say the word breasts.
She smiled at that. "No way was I going to miss out on that. I've heard the other girls talk about how much they like it when a guy touches them."
I drove her home and we sat in the car for a few minutes outside her house. "You've got me wondering, will I see you again?" I asked.
"Of course. Allen, I've never met anyone like you before. I want to ... feel comfortable. I just need a little time to be sure. Does that make sense?" she asked.
That sounded a lot more optimistic than I had been. I guess I could see that a girl who had never been allowed to date might be feeling unsure. "Sure," I said smiling. "Just don't wait too long because you are driving me crazy," I said laughing.
"Just so you know, I was going a little crazy too." She leaned over and we kissed, my hands found her soft breasts. Quickly her nipples stood up and rubbed against my hands. Alison was moaning as we broke the kiss. "Oh, Allen," she said dreamily.
"I'll see you Monday," I said.
"Please," she said as she got out of the car. I watched her walk to the door and open it. She waved as she went in.
I knew I'd have a near terminal case of blue balls when I got home. All I could think of was how lucky I had gotten. Second date and I already got to second base. What about the fourth date?
The next week at school we sort of became girlfriend and boyfriend without quite saying it. We started having lunch together. We made sure we rode the same bus in the morning and the afternoon. I rode up the hill with her and walked her home. We'd sit outside her house and talk and maybe kiss before I'd walk home. I realized I had a girlfriend, my first real girlfriend.
Wednesday my mom gave me two tickets to the Symphony. "When do I get to meet this girl?" she asked.
"Gee, I don't know," I said. I wanted Alison all to myself.
My mom looked at me indulgently and shook her head. "Here's the price for the tickets. Ask her to dinner here before the concert so we can meet her."
I'm sure I looked horrified.
My mom patted my cheek, "Don't worry. Your father and I will be on our best behavior."
"So, you want to go see the Symphony? I have two tickets Friday," I said.
"Yes, absolutely," she said. "Do they dress fancy?"
"Not everybody. You'll see a few people in jeans but they stand out like a sore thumb. You'll be happier in a nice dress," I said.
"I guess this is a good excuse to go shopping," she sounded happy about that. I could tell she was excited about the new dress and the concert.
"Um, one thing though," I said. Alison could tell by my voice that something was up and she looked intent. "My mom wants you to come to dinner at our house before the concert."
Alison looked a little concerned but took a breath and said. "I guess I knew I would have to meet your parents some time. But it should be easier than when you met my dad." We both laughed and it broke the tension.
Alison's mom dropped her off at our house on Friday. I guess she had been out shopping because she looked beautiful. I introduced her to my mom and dad and they looked impressed. My dad even said when we were alone for a second that I had done well.
Dinner went well; my mom is a good cook. Conversation was strained for just a bit until mom started in on music. Alison had recently discovered classical music and was lapping up everything to do with it. My mom was a fountain of knowledge as well as stories. Dad and I hardly got a word in.
The concert was Brahms and Nielson, a paring of brilliant upbeat works full of emotion and color. Both of us were dancing along as we left the hall. We parked again at our place and kissed. It didn't get quite as passionate as the previous time, mostly since we were both aware that our curfew was rushing up.
The next day was a bright fall day in the Bay Area. The wind was cool but the sun made it nice. My mom helped me pack a picnic and I took Alison to the local park. We ate and talked and wound up laying down facing each other. Soon we were kissing. My hand was under her sweater and feeling her breasts. Her nipples were hard and swollen as our kisses got sloppy. My hand wandered down over her belly, but she grabbed it and brought it back up. Once again anything below the belt was off limits. I tried to be patient.
Alison and I were now accepted as being an item by our families and at school. She had a younger brother who she always ran out of the room when I was over. It was almost like she didn't have a younger brother, only the back of one going out of the room.
My younger sister, Tracy, looked up to Alison and always wanted to hang around. I finally had to have a heart to heart talk with her. When I explained why we wanted to be alone, to make out, she blushed like crazy. But she was much more sensitive about leaving us alone although I was sure she was spying a few times.
We spent a lot of our out of school time hanging around with each other. Most nights Alison would be over at our house and we'd do homework together. The nice thing is our place had a den, perfect for homework, that was also separated by a hall from the rest of the house. It gave us some privacy. There were lots of times we'd be on the couch making out instead of doing homework. But the waist remained an impenetrable Maginot Line I couldn't cross.
I guess Alison was sensing my rising frustration. We had stopped at the same place we had arrived on our second date. It was a Saturday night and we were supposedly seeing a movie. Instead, we had driven up to the hills overlooking the bay and parked. We had been kissing and both of us were worked up. Once again I had put my hand on her knee and been rebuffed. I was frustrated but this time it was different.
Suddenly, Alison's hand was in my lap and I nearly jumped in surprise. She was stroking my hard cock. Shit, I was nearly cumming just from that. "Allen," she said.
"What?" I answered.
Alison was now trying to undo my jeans and I quickly helped her. I pushed them down and her hand found my erect shaft.
"It's so big," she said as her hand stroked it. "Allen, it's my first time so tell me if I do anything wrong."
My mind was whirling. I was going to get laid, just like that. I had no idea this was coming. I was going to get laid.
Her head bent down over my lap and I felt her lips engulf the head of my cock.
A blowjob! I was getting a blowjob. Her hand and mouth were moving in unison on my cock. My head fell back against the seat and my universe was centered on my cock. The sensations were beyond description. In just seconds I could feel the pressure building. I tried to warn her but nothing coherent came out, just a moan of pleasure.
Then like a cataclysmic explosion, my balls erupted spewing my cum into Alison's waiting mouth. She moaned as blast after blast of my cum exploded down my cock and into her swallowing mouth. My whole body had gone stiff as I experienced the most intense climax of my life. A few last spasms and I was drained.
Alison's lips were still lightly sucking on the head of my cock and it was so sensitive it almost hurt.
"Stop," I moaned. "Too sensitive."
She lifted up off my cock which was wilting now. "Did you like it?" she asked.
"Oh my God," was all I could say. "Alison, I love you."
"I love you," she said and leaned forward to kiss me. Our tongues danced together. There was something different about this kiss and I soon realized what it was. I could taste the leftover cum. I nearly pulled away in horror, but then thought, No, I don't want Alison to think there is something wrong with giving me a blowjob. So I kept kissing her and soon the feeling of weirdness passed. All that was left was the pleasant feeling of the blowjob. I had gotten my first blowjob. Wow.
I wanted to return the pleasure. "My turn," I said.
"No," Alison said sternly.
"But Alison, I want to return the pleasure."
"Thank you, Allen, but I can't," she said, "I can't explain, but I just can't. Please?"
"I don't understand," I said. But I was also filled with the lassitude that comes after an amazing climax so I didn't argue.
So a new plateau opened in our relationship. Alison was willing, no eager, to give me head. She seemed to like giving me pleasure but still nothing below the belt for her. It led to our first real argument.
I wanted to return the pleasure. Even if we weren't going to have sex, the least I could do was eat pussy. She recoiled at the suggestion. I couldn't figure out why, since I knew from reading that women really liked it. I accused her of not trusting me and I could see that hit home. We wound up not talking as I drove her home. I didn't even get a goodnight kiss. She didn't call all weekend.
On Monday, she was still frosty in class. I walked with her after class and apologized. That broke the ice. She apologized as well and then we were both apologizing and she was crying and we were hugging and all was forgiven.
The next day Alison asked if I could come over to her house after school since we needed to talk. Now I know when a woman says, 'We need to talk'; there is nothing worse in the world. But in my innocence, I had no idea, so I said sure.
We went back to the den. I was hoping for a nice make out session since all was forgiven. I should have known. Instead, Alison was serious. "We need to talk."
I just sort of shrugged. I'm a guy. "Okay," I said naively.
"Allen, do you really love me?" she asked.
"Yeah," I answered happily.
She wrung her hands, "I know you're going to hate me."
"Why?" I asked, now getting confused.
"When you find out," she said cryptically.
"Do you have another boyfriend?"
"No," she said. "It's nothing like that."
"Then why would I hate you?" I asked.
"I wish you would just guess," she said.
"You're pregnant," I guessed.
She looked shocked. "Allen, can't you see?" I stared at her trying to figure out what was going on. "Allen, I'm a transgender girl." She pulled back as if I was going to hit her looking alarmed waiting for my reaction.
I suppose for most young guys they would have really been shocked. But I grew up in San Francisco. You get used to having more than two genders. The idea wasn't especially shocking. Hell, we had openly gay and lesbians students and teachers in our school. You see two guys or two girls or a guy and a girl as a couple and it all seems pretty normal. I was comfortable that I wasn't gay so I didn't need to hate on gays.
Being from Babylon by the Bay I was aware of transgender issues. In San Francisco there are always three blocks for gender: male, female, and other. Okay, not really but there should have been. In school we had discussions about gender and gay rights like other places would about race issues. So I wasn't shocked. Surprised maybe but not shocked. And I didn't have that gut churning reaction caused by ignorance.
"You are?" She nodded still wringing her hands. "But, I felt your breasts. They're natural. And you hips, your voice," I said. I guess I still expected transgender to be more like my gay friends, they looked male.
"I always knew I was a girl in a boy's body. When I started puberty I was so unhappy my family took me to a counselor. He gave me a personality test and it said I was a girl. So he convinced my parents to put me on estrogen. I went through puberty as a girl. My voice didn't change, I didn't get shoulders or a beard, my hips grew and my breasts developed just as if I had been a girl. Do you hate me?" she asked.
"No. Alison, to me, you are a girl."
"Have you had a t-girl girlfriend before?" she asked.
"Now I get the third degree?" I asked. She blushed. "Alison, you're my first girlfriend of any kind."
"So you don't think I'm weird or perverted?" Alison asked.
"No," I said.
Alison smiled. "I was hoping ... You don't know how long I've been thinking about being able to really date a guy, a guy who would think of me as a girl. Every since I was thirteen I've been dreaming."
"And your dad wouldn't let you?" I asked.
"It wasn't prejudiced. I think he was disappointed when I decided I was a girl but he has my younger brother to be a son. He got over it pretty quick, I think. And once he accepted it, then he became really protective. He read about how some girls would get beat up once the guy found out. Some girls even got stabbed or shot. My dad was just afraid for me. I guess I got it from him," she said
"That explains a lot," I said as Alison nodded. I could see the suppressed tears, tears of worry. I leaned over and kissed her. And it didn't seem weird. She really was a girl to me. Alison flew into my arms and we kissed passionately. My hand found her knee and started moving up. She pulled away and slapped my hand.
"Hey," I said. "I know now. I want to, you know, pleasure you," I said quietly so I couldn't be overheard. I still didn't trust my little sister.
"You can't," she said. "I mean, I'm not a complete girl yet."
"Huh? I thought they did surgery," I said.
"I can't have that until I'm eighteen, even if my parents said okay. No doctor will do it until then. Something about liability insurance or something," Alison said.
"So, does that mean we can't have sex?" I asked.
Alison blushed. She leaned forward and said quietly, "We can, we just have to do it different. I have been reading these websites for t-girls and I know how." She blushed with that admission.
"Does that mean you want to?" I asked smiling.
She slapped my knee, then blushed again as she nodded. My cock went from flaccid to rock hard in seconds just thinking about getting laid for the first time. Of course, at that age a boy gets rock hard thinking about everything, but getting laid the first time really builds the pressure.
Alison saw the look in my eyes and said, "Not here."
I was disappointed but still interested. "Where?"
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