I will Remember

[High school graduation dance]

"This is the last time we'll all be together," Martin laughed.

"There's always reunions," Tim chuckled. "What do you say, Brian?"

I grinned. "I won't be attending any, so Martin's right."

"I'll miss you two," Tim sighed. "We've spent four years hanging out."

"I will too," Martin added.

"As will I," was my remark. "There's always mail."

The bell rang, signifying the dance was over. We all headed out.

[20 years later]

Of course, none of us kept up with each other. We all went to colleges far away from home, and met new friends there. And then we graduated, got jobs, and life happened. Unless you and they stay in your hometown, you don't keep up with your high school friends.

I did see Tim's obituary. He had joined the Army and been sent to Iraq. An IED did him in. I realized I hadn't thought about him in years. And for five seconds, I idly wondered about Martin, then returned to my life as it was.

And then I got transferred back to my old hometown. The company was starting a plant there because they could get cheap labor, plus the state and city had offered tax breaks.

I bought a house - living on a big city salary for 15 years and being frugal, I had a lot saved up, especially because I was now a senior manager, and real estate was cheap in the old town. A house that would have easily run me 800 grand in the city was 150 grand back here. I paid for the whole thing with half my savings.

One thing I was a bit concerned with was finding romance. Not that I had had much luck in the city, because I had been focused more on advancing up the career ladder. When I needed a release, I found women whose charms could be rented, as it were. But I was pushing 40 and it looked like I was going to be out here for a long while. It might be time to settle down. And small towns have a smaller population, hence less choice, than big ones.

I therefore placed an ad on a dating site, mentioning my location. There were in fact several women in the town on the site, and after exchanging electronic correspondence back and forth, I narrowed the candidates down to one. Tina was a slim brunette, with a decent but not ginormous chest, brown eyes, and straight shoulder-length hair. She was close to my age and had lived here until graduating high school, then made a huge amount of money as a government contractor - she wasn't allowed to say more - and moved back three years ago after retiring. She had enough in the bank to live off the interest if she lived here, where the cost of living is much less.

I didn't remember a Tina with those physical characteristics from my high school days, but then again, it's not like I paid close attention to every single student. Maybe she was in different classes than me and was kind of shy, so I didn't notice her.

We agreed to meet at a local cafe on Saturday morning. I walked in two minutes early, ordered my beverage, and looked around. Tina was already seated at one of the tables. I settled in across from her.

"Nice to meet you, Brian."

"Likewise, Tina. You look pretty."

"You're decently handsome yourself."

"So when exactly did you graduate high school?"

It turned out to be the same year I had. But I didn't remember her being up on stage.

"That's because I went by a different name then."

"I would have remembered such a pretty girl walking up on that stage to get her diploma."

"I wasn't as pretty then."

We chatted for half an hour, then agreed to meet again the next Saturday. This time it was for lunch at a good sit-down restaurant. We again hit it off, and we split the bill. I had offered to pay it all, but Tina laughed it off. "I'm richer than you are. If anything, I should be paying it."

The next Saturday we attended a free concert in the park. I suggested we return to her house, but she said we should go to mine instead. "But that doesn't necessarily mean you'll get sex from me, Brian."

"We'll have sex when you feel comfortable with the idea, Tina, and not an instant before."

"You're a good man."

We got back to my house, and I brought out my senior yearbook from high school. I really wanted to see what Tina looked like back then, and why I hadn't noticed her.

"There's me," I said, pointing to my picture. "And my two best buds, Martin and Tim." I pointed them out as well. "Tim passed on a few years back. Being an Army grunt was always going to be a risky career."

"Tim was cool," Tina agreed. "I was sorry to hear that he died, too."

"Martin was always a fun, and funny, guy," I grinned, switching the subject away from the sadness of Tim passing on. "I do wonder what happened to him. In fact, you kind of have a similar personality. I think that's why I selected you to date."

"I should," Tina chuckled. "So you think I'm fun and funny?"

"And pretty. Let's not forget that."

"You have a silver tongue."

"So where's your picture in here? You were part of my graduating class."

"See if you can guess."

I looked carefully at all the pictures. There wasn't a single girl named Tina in the entire graduating class.

"Did you change your name, too?"

"Yes."

I smacked my forehead with my palm. "Oh, right. You already mentioned that, didn't you?"

"Yes, I did."

I looked again. Didn't have a clue.

"I give up."

She pointed to a picture. "This one."

My jaw dropped.

"No wonder you..."

"Yep."

"So when did you... transition, that's the term, right, old buddy?"

"Yes, it is the term, old pal. After retirement."

"So..."

"I know what you want to ask. Yes, I still have it, though it's a couple inches smaller now. It still works, but it's not as easy for me to ejaculate."

"So..."

"Call me Tina now. Don't ever use my deadname, even though you know it."

"So..."

"I had a bit of a crush on you even back in high school. You've only gotten more handsome. But it's up to you, now that you know I have a cock and not a pussy."

I gently pulled Tina into my arms. Our lips met for a soft kiss.

"Let's go to my bedroom."

We got there, after each making a pit stop en route, and kissed again. I wanted to be extra sure.

"Tina, you're certain you're OK with engaging in sexual activities? I think you're quite beautiful and definitely am willing and eager to get it on, but it takes two to tango."

"Thank you for asking. And I'm glad you think of me as beautiful. Brian, I'm also very willing and very eager. Let's get naked and in that bed."

I thought that was an excellent suggestion. Two minutes later, there were two piles of clothes on the floor and two eager people naked and in bed. We kissed yet again, and this time we twined tongues. Eventually we had to break for air.

"Whew! You're a good kisser, Brian."

"So are you, Tina."

I kissed my way towards her firm chest, and she smiled.

"They're in between a B and a C cup. Go right ahead."

I kissed through her cleavage, and she shivered slightly. Then I kissed my way up to one of her nipples before giving her other breast the same treatment.

"Mmmmmm."

I took a nipple in my mouth and suckled. Tina wrapped her arms around my head and gave a contented sigh.

"That feels very nice, Brian."

I alternated between her breasts for a bit.

"Let me do the same for you." Tina unlocked her arms, disengaged my mouth from her nipple, and lay me on my back.

"Sounds like a plan, Tina."

She kissed from my neck down towards my chest. Her tongue felt very nice on my skin. It felt even better when she flickered it over the tip of my nipple. I moaned quietly and shivered.

Tina's hands were caressing my legs while she teased my chest. Her long nails felt good against my skin. My body instinctively reacted to her touch, and she looked up and smiled.

"Glad you like."

"I've, um, never been this intimate with a transgender woman before. You may need to help guide me."

"Cisgender women often think men need guidance during intimacy, too. Just follow my lead and pay attention to how my body reacts, just like you would with any partner you're being intimate with for the first time."

That made sense. "Cool."

"Are you ready to escalate the action?"

I nodded. "Definitely."

Tina pivoted her body 180 degrees and adjusted her position so that we would be in a 69. "Just do what I do. If you're liking what I'm doing, I'll probably like what you're doing. And if not, the way my body reacts will clue you in."

I smiled. We both parted our lips, and Tina lowered herself downwards. Her mouth took in just the head of my pole, and my mouth did the same for her. We both began using out tongues in a circular motion to stimulate each other.

After that warmup, we both slid in a bit deeper. Now we were actively sucking and using our tongues to run up and down the shaft. Tina's body shivered in an appreciative way, and her tongue on me was making me feel quite good.

We stayed that way, licking and sucking, for long enough for my pole to throb and pulse a bit. Tina noticed. She lifted herself off of me.

"I'm sure at some future point I'll use my mouth to finish you, Brian. But I haven't been fucked in a while, and I want you inside me."

"That's great for me. I'll blast off within you. What about making you climax?"

"I much prefer receiving than giving. Trust me, you'll leave me very satisfied."

"As you wish."

Tina got on her hands and knees and shook her sexy ass at me. I leaned down and kissed both her cheeks before getting myself in position. She giggled.

I carefully eased my way into her back-channel. It was incredibly tight.

"Like I said, it's been a while."

I moved back very slowly, then eased forward again. After a few repeats of this, I was able to get a slow rhythm going. Tina shuddered and let out soft, pleased moans.

Encouraged, I continued to gently pump her. She pressed backwards, trying to get all of my rod within her. I grasped her hips so I could get leverage to assist. Holding her, I found I was able to speed up a bit.

"That's great. Hard and deep. Fuck me."

I hilted myself inside her with every thrust, and moved as fast as I could. My pole twitched with excitement.

"Tina, I'm..."

"Fill me up."

I did exactly that, painting her insides white with jet after jet of cum. When I was finished, I pulled out, with an effort, and rolled onto my back.

Tina eventually managed to get up. There was a wet spot where her cock had been lying against the bed. I guess I really had satisfied her. I rose to my feet and we cleaned up in the shower.

After we dried off, Tina and I returned to the bed and crawled under the blankets for cuddle time.

"Thanks, Brian. I really needed that."

"Can we do it again soon?"

"I say we should do it again every weekend. I'm not sure where this relationship is going, but I like your company."

"And I like yours."

We sealed our deal with a kiss, and I turned out the lights...