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 Mason-Dixon Line I couldn’t cross. No Southern access.
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 up 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. It wasn't as neat as losing my cherry would have been, but it was still a 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 she could come over to my 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 naivety, 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 better. Instead, Alison was serious. “We need to talk.”
I just sort of shrugged. I’m a guy. “Okay,” I said still not knowing what was going on.
“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. Our football line coach was gay but about as macho as you can get. Scary macho, like don't want to meet him in the dark. 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. I suspect that most of the rabid anti-gays out there are actually worried they are gay, like that fundamentalist preacher who got caught with gay escorts while he led a big anti-gay movement sucking cock himself.
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 prejudice. 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?”
“Can you drive me home?” she asked.
I ran out of the room to ask my mom. I told her I wanted to take Alison out for ice cream then drive her home which Mom said was fine.
I was nearly dancing as I went down the hall. “Mom said okay.”
Alison had gathered up her things. As I started the car, Alison said, “Let’s go park at our place.” I had trouble driving I was so excited. When we got there, Alison slid over and we started kissing. Her hand found my cock and pulled it free. But this time, she didn’t bend over and take it in her mouth. Instead she reached into her purse and pulled out a tube. She squeezed out some goo and slathered it over my cock. It was cold and slimy but quickly heated up. It felt good as she stroked my cock with the stuff.
“Slide your butt forward,” she said.
Then she reached under her dress and slid off her panties. I was getting more excited by the moment and just kept thinking, I’m getting laid for real. Alison put some of the goo on her fingers and reached under her skirt for a few moments. Then she turned her back to me, sidled over my legs, took my cock, and led it under her skirt as she sat down.
It’s lucky my cock was stiff as a board because it was difficult getting it inside. Alison moaned as it slowly opened her up, then with a pop, my cock slid up inside. She let out her breath as I gasped from the heat and pressure on the head of my cock. Alison was still for a moment, then she started moving slowly then a little faster and farther until she was sliding up and down my cock.
As Alison picked up speed sliding up and down my cock the pressure built in my balls. I couldn’t believe how good this felt, the soft warm walls of her ass massaging my shaft. I tried to hold back but the newness of all this, just knowing that I was really having sex for the first time overwhelmed any possible control I might have had. I felt the explosion coming and cried out, “I’m cumming…”
Alison ground down one last time and I felt her ass squeeze my cock. That did it and blast after blast of cum jetted up my cock and spilled into her tight behind. My whole body seemed to spasm in time with each cum, until I was completely wasted and fell back onto the seat.
Alison lifted herself off my quickly deflating cock. It popped as it came free. She lay next to me on the seat. “I love you.”
I had to struggle to say over the lassitude, “I love you. You’re the sexiest girl in the world.”
She snuggled into my side. “Thank you,” she said. “It was better than I thought it would be.” I was too wasted to wonder about that. Soon, Alison reached into her purse and brought out some Wash and Dries she had for this purpose. She cleaned me up and herself. Then she put her panties back on as I zipped up. She put away the things.
“How long have you had the stuff?” I asked.
“A couple weeks,” she said. “I was reading on those websites and I’ve been practicing, you know, getting the muscles to relax and they said I would need the astroglide.”
“I’m glad we finally got to use it,” I said.
“Me too. I can’t wait to use it again,” she said. I smiled thinking the same thing.
We talked about it the next day and she admitted that she had kept her skirt on and turned around because she was still leery how I would react to her having ‘those things.’ I was pretty sure it wouldn’t be a big deal since to me she was a girl. But I knew I had to get her over this. That Saturday, her folks were away for a party. Normally, they didn’t want us alone when they weren’t home. I convinced Alison it would be okay this time.
We were in her room when I told her I wanted to see her naked, with the lights on. She was instantly nervous. I held her in my arms and kissed her. I slowly took off my clothes as we kissed and touched each other. She got into it and helped strip me as I stripped her blouse and bra. She pulled off my shorts and jeans so that I was naked. I pulled her up and knelt in front of her. She looked like she was going to cry. I smiled reassuringly and unbuttoned her skirt.
“Turn around,” she said.
“Alison, I thought we settled this,” I said.
“I’ll get naked. I just want to do it myself,” she said.
So I stood up and turned around. I heard her slipping off her panties, then another few sounds. Finally I heard her say quietly, “Okay.”
I looked her up and down. She was beautiful. I have to admit, it did seem funny that my girlfriend had this cute little dick and balls, but I still thought of Alison as 100% girl so it was just one of those things. So she’s a little different. So what? I stepped forward and took her in my arms kissing her. I could tell that she was trembling, but quickly she settled down and started kissing me back.
We fell onto her bed which I found sexy. My girlfriend’s bed. I was going to do it in her bed. Alison turned over with her butt in the air and asked me to hand her the tube of lube. I turned her back over and her hands went to cover her equipment. Slowly but firmly, I took her hands away.
“Alison, I love you the way you are. Quit hiding from me.”
She sort of sniffed, but then smiled bravely and lay back, letting me admire her beauty. It was the first time I actually got to see her naked. It was still a little jarring seeing my girlfriend with male equipment but it quickly became something I just took for granted, like a mole or something. It wasn’t her.
I wanted to do it regular, but quickly realized I couldn't just lay on her like a regular girl. So I knelt in between her legs sitting on my heels. I grabbed the lube and squished it all over my cock as she watched intently. Then I squirted some between her cheeks and worked it into her butt. She was quickly moaning. Next, I pulled her hips up onto my thighs and pointed my cock straight at the goal. It slid into her tight hot ass and I started fucking her. Alison held her equipment out of the way as I fucked her. It was so cool looking in her eyes as I felt my cock sliding deep into her hot tight ass.
God, the pressure built so fast, me watching my cock slid into her, that my climax washed over me before I was ready. One second I was pumping and the next my body went stiff and I arched my back shoving my cock all the way up her butt. Then spasm after spasm wracked me as I emptied my balls into her. Alison felt it and was moaning. A few last spurts and I was empty.
I slowly withdrew from her and lay beside her. We kissed a little as I recovered.
“I love you,” she said.
Smiling, I said, “Love you.” Having just cum, I remembered something that had been on my mind. “Alison, do you cum?”
“Of course,” she said.
“How?” I asked.
She looked at me like I was being silly. “The usual way.”
“There’s nothing usual about you,” I said.
She started to look like she was mad, then she looked confused, finally she smiled. “I think that might be a compliment.” I laughed and nodded. “In that case, I mean the usual way, like I get hard and stroke it and a little stuff comes out. I don’t really cum like a guy because I’m taking estrogen.”
“So I’m not making you cum?” I asked disappointed.
“Allen, I like making love with you. I want to make love with you,” she said. “Whether or not I cum isn’t important.”
I saw her small piece, sort of like an extra long clit. It was a lot like mine when it’s soft and I know what to do then. I wrapped my fingers around it and started playing with it like I would my own. Alison gasped and her eyes went wide. I smiled and continued playing with her. She laid back and closed her eyes.
That’s what I wanted. I bent over and started sucking on her tits as I played with her big ‘clit.’ It never got totally hard like my cock, but it did grow and stiffen. Alison was moaning as I played with her and sucked and licked her tits. It’s funny, but I felt like I knew exactly what to do as I played with her. I could sense her excitement and stroked her just like I would have myself. She finally got stiff and big enough that I could really wrap a hand on it and stroke.
Alison was panting now and I saw the trembling belly. It was funny, so like I was playing with myself, but different. She went stiff just as I had done and a little juice dribbled out as she fell back against the bed.
“Thank you,” she said dreamily.
Now it was my turn to be happy, because I had pleased my lover.
I thought about it later that night and wondered if I were queer. But that didn’t seem right. Alison is a girl so how could it be queer? It couldn’t. And with that understanding I never worried about what she and I did. There are a million ways of having sex, just look at the books, and as long as I was with Alison it would be right.
Alison and I were now officially girlfriend and boyfriend as well as lovers. I don’t know how, but I think both moms kind of figured it out. Alison’s mom told her it was okay one night when they were going to be gone if I came over. I found out why Alison always kicked her brother out. Tommy, her brother made a pest of himself one time even saying Alison wasn’t a real ‘girl’ which pissed me off and made Alison furious. We finally locked ourselves in her room. I gather he squealed to her mom as soon as they came home and got a scolding for bothering us so much we had to lock ourselves away from him. I suspect when mom found out about the real girl comment she blew up too because she actually gave him a month’s TV restriction for being a pain to us. Tommy got the idea. And I noticed my mom didn’t come in to check up on us the way she used to in the beginning. I guess they accepted that we were serious about each other and treated it that way.
I was happy as a guy could be. Alison was fun to be around in school. Being an outsider the way she was, she had a biting sense of humor and would make fun of the beautiful people, the popular crowd. She brought me out of my shell. Somehow, having her as a girlfriend made me surer of myself around others. I think it was because if Alison could like me then I was worth something.
And when we were away from school I had so much fun. It wasn’t just the sex although that remained wild. Alison knew all kinds of things from her reading and she was willing to try anything. I kind of got that from her. I suppose many would consider what we did as perverted but I didn’t care and neither did Alison. We just knew it was fun and I suppose that some of the fun came from knowing we were doing bizarre sex.
I remember the day it got even more bizarre. It was a Saturday and like usual, my dad was golfing all day. Alison and I got home from shopping around noon intending to have mom fix us some lunch. Instead was a note saying she had gone shopping and wouldn’t be back before three. We looked at each other and I could see she had the same thoughts as I. We had the place to ourselves.
We raced back to my bedroom and threw off our clothes. We fell onto the bed and kissed. Alison pushed me onto my back and fell between my legs. She grabbed my shaft and started licking and sucking me. Alison was the best because I could tell how much she liked it when she was giving me head.
I reached into the drawer by my bed and pulled out the tube of lube. We both had some right beside the bed. She saw me with the tube and sort of crabbed around so that she could keep licking me while I squeezed some onto her butt. When she was all lubed and I had fingered her some, she grabbed the lube and lathered my cock with it. Then she stuck her butt in the air and begged, “Do me.”
I knelt behind her and slowly pushed my cock into her tight little ass. God but it felt good, sliding into her hot butt. She moaned as I filled her up. Then I started fucking her. We didn’t often have the house to ourselves when we fucked and Alison let herself go. “Fuck me,” she moaned. “I love your big cock.” Hearing her say those nasty things spurred me on.
That’s when I heard from the doorway, “Oh my God!”
I looked over to see Tracy standing in the door in her pjs with her hand over her mouth and her eyes glued to the scene in front of her. I pulled out of Alison like I was on fire. There I was with my cock sticking straight out pointing at Tracy. Alison looked up and saw Tracy. She rolled onto her back, and then tried to get under the covers. But she couldn’t get them loose because we were both kneeling on them. “Get off!” she yelled at me.
I jumped off the bed, my hard-on bouncing, as she finally got under the blanket. I realized I was standing there naked with Tracy looking at me and jumped back in the bed and crawled under with Alison. If it wasn’t so terrible I’m sure it would have been hilarious in a Keystone Kops kind of way.
Alison and I looked at each other, then at Tracy. She was staring at the bed. Finally, my mouth worked. “I thought you went shopping with mom.” Tracy never missed an opportunity to go shopping.
“She went too early. I didn’t want to get out of bed,” Tracy said. Then, like she just realized what she had seen, Tracy sort of gasped.
Alison took a deep breath. Luckily she regained her wits. Me, I was in a complete panic just imagining Tracy describing in lurid detail everything she had seen not only to our folks but to all the neighbors and kids at school.
Alison sat up, “Tracy, do you understand what you saw?”
“Of course, I know about sex,” Tracy said a bit diffidently although I could tell she wasn’t as sure of herself as she was trying to pretend. “But Alison, I thought I saw you… um, have a… Are you a boy?” she finally asked.
Alison let the blanket fall down enough to show off her nice breasts. “Do I look like a boy?” Tracy shook her head. “Tracy, you have to promise no to tell anyone about this, not anyone.”
“Duh,” she said and rolled her eyes. Then more seriously, she said, “Yeah, I promise.”
Alison took a deep breath. Then with amazing calm she told Tracy about her being a t-girl, what that meant, the tests everything. I began to calm down just listening to her calm rational voice. I even started breathing normally again. Tracy came into the room and sat on the bed as they talked… girl to girl, Tracy asking questions and Alison explaining.
I was shocked by my little naïve sister being there since I was buck naked with my naked girlfriend. But Tracy wasn’t so naïve. In fact, for the first time, Alison and Tracy actually got chummy. Don’t get me wrong, Tracy had always been nice to Alison but they never seemed chummy. Now they talked like girlfriends.
The conversation worked from general to specific and got a little uncomfortable for me. Tracy asked, “Alison, if you have a dick do you have a puss?” Alison shook her head. Tracy looked puzzled, “But I was sure I saw Allen…” Tracy paused looking for the word and I blushed.
Alison told her, “We use the butt.”
“I’ve heard of that but it always seemed it would hurt,” Tracy said.
“You have to use a good lubricant,” Alison said as Tracy’s eyes flicked over to the tube lying on the bed, as Alison continued, “And you have to go slow at first. But it can feel really good.”
Tracy sort of nodded as she looked at my lap like she was trying to see through the blanket. Then she looked back at Alison, “I’m sorry I interrupted. I mean, I bet it is hard to quit. If you guys wanted to finish…”
Alison looked at me. “I know he’d like to finish.”
Tracy looked pleased, “That would be cool.”
That’s when it hit me. Tracy sat there on the bed with no intention of getting up. She was obviously thinking she would stay and watch. I was about to say ‘No way!’ when Alison pushed the blankets off her. Tracy stared unabashed at Alison’s equipment. Alison grabbed the blankets and pulled them off me. Tracy’s eyes went back and forth between us. Alison was almost laughing at Tracy’s attempts to watch both of us as she leaned down and grabbed my cock. “Hello,” she said. “I need you to get all big and hard for me.”
I don’t think Tracy’s eyes could have gotten any wider as Alison took my cock in her mouth and started sucking. I had lost all stiffness during those moments of panic. But it had responded to seeing both girls, one half naked and the other naked in my bed. It only took a little before I was full staff and ready and willing to go.
Alison leaned forward, sticking her butt in the air inviting me back. She was still lubed as I knelt behind her and slipped into her hot tight ass. Tracy gasped as she watched the head of my cock first split Alison open then disappear inside. It didn’t take long for me to forget I had an audience and begin fucking my sweetie good and hard. Alison was soon moaning as I worked my cock deep into her. Once again I felt the pressure build and I didn’t try to hold back. The rumble started deep in my balls and blammo, I was spewing my cum into Alison’s pulsing butt.
I fell to the side and Alison snuggled back into my arms. Tracy was still staring wide eyed, then she jumped up and ran from the room.
“What’s wrong with her?” I asked.
Alison giggled. “Wrong? Nothing. What would you be doing if you had just watched two people screwing?”
I knew what I’d be doing, jerking off like crazy. “Tracy?” I asked.
“She’s human you know my glorious lover,” Alison said laughing.
‘Tracy?’ I thought. Who knew my little sister was getting all grown up.
Copyright Rod O'Steele © 2009, 2012