I'm Mike, a typical horny high school Sophomore. I'd been dating girls for about a year but just haven't figured them out. They're different, some of which is good, but they can take offense so easily! Most are pretty open to kissing, and after a while feeling their tits, but it takes a lot to get further than that.

There was a boy in my class who was kind of effeminate. He was thin with girlish features and wore shoulder-length hair. Besides that, he walked kind of like a girl, with his ass swaying back and forth. His name was Terri – not Terry, the way a boy would spell it.

Anyway, we all thought he was gay, which was alright with me – I just wasn't interested. There were times however, when the thought crossed my mind that Terri might make a pretty nice girl. It was a stupid thought, and I didn't dwell on it, but it was amusing to consider from time to time.

A lot of the guys picked on Terri, calling him a sissy, and sometimes pushing him about. I never did – with his looks he had problems enough without other people giving him a hard time.

Sometimes we would talk, so we knew each other, but weren't close enough to be friends.

There was a park near my house with a paved trail and benches placed throughout. I enjoyed walking in the woods and one day stopped to rest. In a few minutes Terri approached, with a light backpack – the kind that we used for our books in school.

"Mind if I rest here?" Terri asked.

"Go ahead," I said, and Terri took off the pack and sat down.

Without even thinking about it, I found myself staring at Terri. The fine facial features actually looked pretty, though that isn't something a boy would want to hear.

Terri noticed me looking and asked, "Everything okay?"

I realized it had been rude to stare, and replied, "I was just noticing what pretty hair you have."

I spoke before my mind had a chance to hold me back, and Terri shot back, "I didn't expect to get abuse from you, Mike."

"I'm sorry," I said, "I didn't mean that."

"I think maybe you did," Terri shot back.

"Okay, I admit that I did mean it," I said, "But didn't intend to actually say it – it just slipped out."

"So you were thinking nasty thoughts about me, but knew you shouldn't say anything," Terri responded.

"This isn't coming out right, Terri," I said, "I meant it in a nice way."

"You told me my hair is pretty, and that's supposed to be nice?" Terri asked.

"I better just shut up now," I said.

"Mike, I'd really like to know what you meant," insisted Terri.

"I was just having a crazy thought that you would femme up really nicely," I said, expecting Terri lash back.

Instead Terri was silent for a bit, then said, "Really?" and I nodded.

"Mike, if I femmed up, would you kiss me?" Terri asked.

"Maybe," I responded, again without thinking – where was this going?

"How femme would I have to be for you to kiss me?" asked Terri.

"Oh, I don't know," I said, fumbling to get out of the mess my words had gotten me into, "more than you are now."

Terri opened the backpack and took out a small zippered bag. Opening the bag he took out a mirror and some makeup items. I watched with wonder as he transformed before my eyes. The makeup accented the feminine features and much more than the hair looked pretty. After a little eye shadow and lipstick, Terri took out a brush. I watched as a girl brushed her hair in a lovely fashion.

Terri put the makeup back in the bag and into the backpack. Turning to me, Terri said, "Femme enough?"

I pulled Terri to me and we kissed. It felt like I was kissing a girl, and threw myself into it, parting Terri's lips and feeling her tongue gliding along mine. My head was reeling, and I was also aroused – aroused in a way I hadn't been before.

"Mike, you got me all turned on," said Terri, continuing to kiss while holding me tightly.

"Then I guess I better take care of your need," I replied, once again speaking before thinking.

I realized that I was going down a path that I never intended to take.

"Mike, you're a really swell guy," said Terri, "And I would be so glad for you to take care of me."

I felt so confused, with a lot of strange thoughts mixed with unfamiliar feelings of desire. Finally, I said, "Tell me how I can help."

Terri stood up an unbuckled his jeans and slipped them down to reveal some pretty royal blue panties, with a very obvious bulge in front. I reached for the bulge but stopped myself before getting there. Terri pulled the panties to the side, releasing a fully erect cock. It wasn't very big, but Terri was clearly aroused!

I was also aroused, and definitely not thinking rationally. In my fog I leaned forward and took Terri into my mouth and I liked it! It was all so confusing but Terri was moaning and urging me on, and before long Terri came in my mouth.

The shock of the strong taste brought me back to reality. I'd just given a blowjob and as far as I could tell I liked it. This was nothing I ever intended to happen and was about to spit, when I heard Terri say, "Oh Mike, you are so different than other boys – thank you so much!"

It somehow just didn't seem right to spit, so I swallowed.

Terri noticed how silent I was and asked, "Mike, do you regret what happened here?"

"Terri, I really don't know what to think," I replied, "I never intended this, but it just happened."

"You've been so good to me," Terri said, "Not like the other boys. If you want we can just pretend this never happened."

"Oh, it happened alright," I insisted, "But I just need to figure this all out."

"I better be on my way," said Terri, "Thanks for being such a great guy, Mike."

Terri left me to struggle with my feelings.

I started to walk home, reflecting on what had occurred. I considered myself straight, and yet I'd just given a blowjob, and kind of liked it. That sure wasn't very straight at all.

I wasn't at all homophobic, so it didn't really trouble me, but I needed to figure things out. I was really attracted to Terri's femme side but didn't hesitate to go down on her – it was all so confusing.

The next time I saw Terri at school he said he'd like to talk. We didn't have any classes together, so I suggested we talk at lunch. Since our encounter I'd jacked-off three times thinking about Terri, and it was really clear that there was an attraction I didn't fully understand.

We got our lunches and found an empty table off to the side where we wouldn't be disturbed. Terri began, "Mike you were nicer to me than anyone has ever been, but I don't want that to be trouble for you."

"None of this is your fault, Terri," I assured him, "It’s still a bit confusing, but I wanted this – I think."

"So you don't want me to just get lost and never bother you again?" Terri asked.

"Definitely not!", I said, "I'd like to get to know you better and figure out what is going on in me."

"Would you like to see me even more femme?" Terri asked.

"You mean clothes and all?" I asked, to which Terri nodded.

"Why don't you come over to my house after school?" Terri said, "But give me an hour to get ready."

I agreed and Terri gave me the address. I couldn't wait for school to get at out 2:30. I rushed home and cleaned up. I put on some of my dad's aftershave – it felt like I was getting ready for a date.

It was just a short walk to Terri's house, so I got started. Upon arrival I was greeted by Terri's mom, Mrs. Blanchard, a friendly woman who welcomed me warmly, saying, "Terri has told me what a nice boy you are. Terry has difficulty making friends – I'm so glad you can accept Terri being different."

The truth was that I liked Terri being different – I wondered what that said about me. Mrs. Blanchard went to tell Terri I had arrived and gave me a lemonade, seating me on the couch in the living room. She took a chair across from me.

Soon Terri arrived and my jaw dropped. Terri was wearing a ruffled green blouse with a matching skirt. Hair and makeup were beautiful and I reached my hand to her. Terri took my hands and said, "It's okay to kiss me if you want, but you don't have to."

"I want!" I affirmed and took Terri into my arms and we kissed deeply as Mrs. Blanchard watched and smiled.

I led Terri back to the couch and we sat close together.

Mrs. Blanchard said, "I can see that you've figured out that Terri isn't just one of the boys."

"Terri is very special," I said, "And I appreciate that, though I'm trying to figure myself out."

"Life has been confusing for both Terri and I as we tried to figure things out, but I can see that it could be even more confusing for you," she replied, "Tell me Mike, do you like the girl part of Terri best or the boy part?"

"I'm not entirely sure," I confessed, "I suppose both." She asked if I could stay for dinner, so I called home and cleared it with my mom.

"I want to get to know you better Mike," she said, "But there's time for that. Dinner isn't for another hour, so why don't you go up to Terri's room for some private time?"

I didn't need to be asked twice, and Terri took my hand and led me to the bedroom.

It seemed really strange that Terri's mom was okay with me being alone with Terri in the bedroom. Now that I was here, I didn't really know where to begin. If we got to the point of Terri being naked, could I really handle that? She sure looked like a girl now, but maybe not with her clothes off.

"Terri," I began, "I like being with you and want this to be right for us, but I'm really unsure of myself. At school you're a boy, but here you are more like a girl – a lot more! Would you be insulted if I considered you to be a girl?"

Terri wrapped her arms around my neck and pulled close as we kissed. "I would feel flattered to be a girl for you," she said, "In fact, I hope that I can become your girlfriend!"

I hadn't thought of that. I just thought of Terri as a boy playing dress up – but Terri was really more like a girl, though her anatomy didn't exactly match. We lay on the bed and kissed, and then Terri unbuttoned her blouse to reveal a black lacy bra. She took off her blouse and turned away from me and said, "You unhook me – that's a man's job!"

I fumbled with the bra hook. This was new to me. Other girls had just pulled their bras up when I felt them. Of course, they had something to feel – I was sure that Terri would be completely flat chested.

I was surprised when she turned to me and revealed a pair of perfectly formed breasts! They were small – I suppose an "A" cup, but definitely breasts. I touched them and she moaned. "Suck my nipples, Mike," Terri said and I took one small nipple between my lips and sucked, as she urged me on. In a few minutes she told me to move to the other, which I did.

I pulled back and asked, "How did you ... " I couldn't find the words.

"I've been taking female hormones for a couple of years. That give me the femme features you've noticed and made my breasts grow. They'll get bigger in time.

"I love them!" I said, "Thanks for sharing."

We were called for dinner and had a nice conversation during dinner. Mrs. Blanchard explained that Terri was legally a boy which is why he went to school as a boy, but was a girl in so many other ways, and was a girl the entire time she was home. Mrs. Blanchard switched gender pronouns with ease, but it still felt a little confusing to me.

I learned that Terri was in the process of getting her gender legally changed, at which time she would be a girl at school as well but wasn't sure how that transition would go - it seemed like it could be awkward.

It was getting late, so I had to be leaving soon, but there was one thing I wanted to ask of Mrs. Blanchard.

"You seemed to be okay with Terri and I having private time in her bedroom," I asked, "But most parents would never permit that."

"Mike, that's an outdated attitude," she said, "Besides, there's no danger of a pregnancy."

We laughed and I bid them both goodnight.

As I walked home I considered the prospect of Terri being my girlfriend. I was really attracted to her, but felt a little odd about her actually being a girlfriend. Friend, quite definitely – lover, very possibly – but girl? I wasn't so sure.

I thought about sucking her nipples and kissing her – definitely a girl. Then I thought about sucking Terri off the other day – definitely not a girl! Of course I willingly sucked Terri – and liked doing it – so did it matter? I was confused – darned confused!

The next day I had lunch with Terri again. "Terri, I really like you – especially the way you were last night," I said.

"I like you too, Mike," Terri replied, "You make me feel like I've never felt before."

"I was thinking about what you said about wanting to be my girlfriend," I said.

"I meant that," Terri affirmed, "Is that something you think you might like?"

"It's confusing with you going back and forth between genders," I said.

"It's tough on me as well," agreed Terri, "You see me as switching genders, but I see you as the boy I like all the time – but I have to behave differently, depending on the situation."

"I can see that could be difficult for you," I concurred, "I'd like to take you out on dates and see where this goes."

"On dates?" said Terri, "Really?"

"Of course," I said, "It's what I would do with any other girl I hoped to be my girlfriend."

Terri was clearly pleased with this and said, "Where did you want to take me?"

"I have some limitations," I said, "I don't have much money, so it can't be a fancy place, and I don't have a car – but my situation will get better in the future."

"Mike, I'd love to kiss you right here," Terri said, "But won't embarrass you – I'm fine with dinner at McDonalds, and a walk afterwards."

We agreed to go out Friday night, and would work out the details before then.

On Friday evening I walked to Terri's for our date. Mrs. Blanchard said she would drive us, drop us off and pick us up when we were ready to come back. She was so thrilled about my dating Terri that she gave Terri money for dinner and said she would take us to a restaurant suitable for a gentleman and his lady.

Terri was wearing a beautiful peach colored dress that she got just for this occasion. It almost felt like I was taking her to the prom – but maybe I would when we were older.

Mrs. Blanchard drove us to a nice Italian restaurant and told us to enjoy our time together – that was sure easy enough to do! We had a nice romantic dinner together and held hands a lot across the table. Simple as it may seem, I had never held hands much with girls, but when Terri initiated it, I found that I really liked it.

As we were finishing dinner, Terri texted her mother to come pick us up. When we left the restaurant, her mother was parked outside, and took us back home.

"How about that walk?" I asked and Terri quickly agreed. We walked, hand-in-hand just enjoying being together. We walked down the sidewalk from Terri's house and soon saw some guys I knew from school.

Terri squeezed my hand as they approached, and whispered, "What if they recognize us?"

"Just leave this to me," I said, now getting nervous myself.

The guys approached and greeted me and asked, "Who's the hot babe?"

"My date for tonight," I said, "I very special lady."

"I see," my friend replied, "So you're keeping her to yourself – is that it?"

"You got it!" I affirmed as they walked away.

Terri turned and kissed me, just in time for my friends to see as they turned to look back. "I was so scared," she said, "And you were so wonderful!"

We walked on and soon came to the park where we’d first kissed. We followed the path, and soon were away from the street lights, but the moon was full and provided plenty of illumination. By now we were both in a very romantic mood, and when we arrived at the bench where we first kissed, we sat down. After a few more kisses, Terri surprised me by reaching under her dress and pulling her panties down to her ankles and then over her feet. She handed them to me. That was a really clear green light, and soon my hand was up her dress, fondling her as we kissed. As I touched her, she became so passionate I knew I wanted it to be like this all the time!

Finally she said, "Time to finish what you started, and she knelt on the bench, leaning on the back, and raised the back of her dress up, showing me her incredibly beautiful ass! Other girls I'd dated didn't mind if I squeezed their buns, but anything more than that was off limits – maybe Terri was more open.

I knelt down and kissed her cheeks, alternating from left to right, slowly moving toward the center. I kissed her crack – nothing too serious – just a playful kiss, but I heard Terri let out a little moan. I grew bolder and licked her crack and Terri urged me on. I licked deeper and felt her warmth, and Terri reached back and spread her cheeks, revealing her tender rosebud in the moonlight. I'd never seen anything like this in real life but had jacked-off to many pictures and I quickly followed Terri's lead and brought my lips to her tender pucker. Now moaning louder, I extended my tongue slightly into her. "Deeper, oh deeper," she pleaded, and I quickly responded, pressing back against me, as if to force me deeper into her.

In a saner moment I would never consider putting my tongue in a place like this, but I was lost in passion, and perhaps not in my right mind. I tongued her for a couple of minutes. My tongue was not accustomed to this, and was getting tired, but I kept going.

Terri began to shift her position and I backed off. She turned around, held the front of her dress up and plunged into my mouth. She felt wonderful in my mouth and I put my hands on her soft, round buns to pull her to me. She put her hands on my head and pulled me close, forcing herself all the way into my mouth. She wasn't very big, so she didn't fill my mouth, but she was very aroused. I loved the way she felt there and ran my tongue all over her and soon she climaxed.

It was a heavenly moment and I now realized that I wanted Terri to be my girlfriend, and wanted her just the way she was – she was exactly the right kind of girl for me!

  To be continued . . .

Feel free to contact me with your comments or requests.
    –Bill Beaumonte (oral_guy_2000@yahoo.com)