School had been tough for me. I was the weird boy who always seemed confused about who he was. I dressed in a girl's skirt sometimes. Other times I'd just wear a little make up and a cute pink T-shirt. Everyone seemed to know how different I was. Most of the time I was left alone. The teachers tried to ignore me. Sometimes the kids would tease me. But mostly, everyone just stayed away.
I spent most of my time drawing and working on projects for art class. I went to Cal State on a art scholarship. An advertising company I interned with last summer hired me full time. I made $300,000 my second year there. One of the other artists there, who I realized was a transexual, suggested I check out a gender clinic. I guess my strange behavior and habits stayed with me, all the way down in California.
I went nearly all out. 6 months of hormones and a little breast enhancement. I worked out, losing a few inches in my waistline. I grew my hair out and had it bleached and trimmed in a girly way every few weeks. My artist friend introduced me to a few people. I had my first sex when I was 24. He was an older guy who was into trans girls. He taught me how he liked to have his cock sucked. He was nice. He bought me pretty clothes, and I posed in them for him before we would have sex. I finally felt like I belonged somewhere. And someone actually liked me. I guess he moved on as we drifted apart after a few months.
I got a call from one of my teachers from high school. He said there were rumors I'd made a transition of some sort, and he wanted to know if it was true. I barely remembered him. Science class or something. He was polite and seemed really interested in what I was doing now. I sent him a current picture of me. I was in a tight sun dress and heels. My hair was blonde and flowing in a light breeze. He liked the picture a lot. He said I should come back to town and show people what I've been up to. That wasn't an option at all for me. No thanks.
A few months later my grandmother finally died. She had been struggling for a long time. She was the only one who didn't completely shut me out because I was so different. She left me her house, her old car, and some money. I didn't want any of it, but I needed to come back and sign off to sell everything. I quietly flew into town and met the lawyers the next morning. No one else was there. There was a little confusion with my ID and proving I was really me. But we got that worked out. I didn't fly out until the next day, so I was stuck there overnight. I made a hotel reservation. I checked in, and spent the rest of the afternoon in the restaurant and bar. It was pretty boring. I scanned through my phone and guess whose name popped up?
Jerry met me in the bar. He was a young second year teacher when I was in school. Now he seemed a more mature, early 30's. He was amazed at how pretty and feminine I looked. I blushed and gave him a little hug. He held my hand and didn't let go. We sat at the table together with him staring at me as I recounted my last 5 years. He wouldn't let my hand go. Finally, he admitted he had always had a little crush on me when I was his student. It wasn't appropriate then, but he wanted to tell me now.
He was still single and had a house outside of town. He invited me to come out for dinner. He was a great cook, he bragged. I was pretty nervous. But he was really nice and seemed interested in me.
He gave me directions and started to leave. I was wondering if he would ever let loose of my hand. Just at that moment, when he should have let go and headed for the door, he pulled back, looked me in the eyes, and gave me a little peck on the lips. Before I could respond, he quickly turned around and was out the door.
The house was nice. But not too special, as he was a schoolteacher on a schoolteacher's salary. He had some pasta and meatballs going. We split a bottle of red and talked small talk for a while. After dinner he invited me to sit and chat on the couch. He was right next to me, sitting very close. His hand slipped over my shoulder, and he leaned in.
"I've always wanted to do that. Kiss you. Ever since I first saw you at school. I'm glad you answered my call and looked me up today. If you'll stay for here a while longer, that would be a dream come true for me."
A little shiver ran up my back. His hand was warm, caressing my arm. "Well, if you liked kissing me so much. I suppose we can try that again."
H kissed me and felt me up for a little bit, exploring my perky little boobies in my sexy lace bra. Eventually he slipped his hand up between my legs. I jumped a little, surprised at his boldness. He was moving his hand over my soft nylon panties and wouldn't stop. I hesitated kissing him, looking him in his eyes. I know he could tell I still have a cock, and it was getting bigger by the minute.
I politely said: "You know what you are doing. You're getting me pretty excited here"
He replied: "I was hoping I would. I'd like you to stay longer, if you want."
I relaxed and laid my head back on the side of the sofa. He continued kissing me, rolling his warm wet tongue around inside my mouth. I felt my cock pop out from under my panties. He stopped kissing me, looked me in the eyes and said:
"I'll be right back."
His whole body slid down between my open legs. His face rubbing my skin between my open blouse on down below my naval. He was kissing and licking me all the way down. My skirt lifted up as his mouth engulfed my hard cock. His hands were up cupping my cute little boobies. Pushing the bra up so he could caress and pinch my erect, pink nipples. I heard him moaning in pleasure as he gently kissed, licked and sucked my cock.
I put my hands on his head, holding it as he moved up and down, sucking my cute little cock. I gripped a handful of hair as he excited my cock. He put one of his hands on mine. Encouraging me to continue. I felt a burst, a throbbing and release. I grabbed his hair and his head hard. I heard myself squeal like a little girl. "Eeeeek!"
He never wavered. he kept sucking and caressing me. He took all my squirting load and seemed to want more. Sucking and swallowing. Another little moan of pleasure. He kept going until I was done, flat out exhausted, my eyes rolling back in my head.
He whispered to me: "That was fucking great. I hope you liked it too. I'll be back in a minute. I've got something to do."
He had cum in his pants. He was a little embarrassed. He came back out in some sweatpants and clean t shirt. He took my hand, motioning for me to get up and follow him. In the bedroom he laid me on my back and started kissing and groping me again. I was in heaven, I thought.
I offered: "I think maybe it might be my turn, sir."
We quickly got him undressed. I began to kiss and rub and stroke his big hairy man cock.
Before I knew I said it, I said something so surprising. "If I can get you hard enough, I want you fuck me like a bitch. It will be my very first time. Can you do that for me, please?"
He replied: "I was hoping you'd say something like that, sweetie."
Before I knew it, I was on my back, legs up in the air, getting ramrodded by my old science teacher. He was grabbing my tits, squeezing them hard with every forward thrust inside me. He had already cum pretty good in the other room, so it took him a long time for his second orgasm. That was just fine with me. He seemed to have all the necessary items for tonight. Plenty of baby oil, some extra slippery anal lube, and a 12 pack of condoms. Every few moments he would lean down and kiss me. I think I even heard him whisper that he loved me a couple of times. Then back up for more perfect angle entry butt fucking. When he finally came, he was exhausted and shaking. But he made a point to ask me if I was OK, taking a break. I tried to catch my breath, but I couldn't. I just nodded. He said he had really enjoyed it. And of course, so did I.
The next morning, he asked if I'd stay a few more days. I did think about it. But I had projects at work. Before I left, he asked me to pose in my bra and panties for him. After a few pictures, he dropped to his knees in front of me and started eating my panties off me. Well, I couldn't disappoint him. I gladly let him lick, kiss and chew my pretty panties until he was sucking me off again. I noticed him jerking off while he was doing it. I offered to suck him too, but it was too late. We both came and needed to shower and clean up quickly or I would have missed my flight back home.
We text now and then. I just feel more complete and satisfied with my choices to become more of a girl. I've had 2 real men nearly fall in love with me.
That's all a girl really wants anyway, isn't it?
Billy
