Continuing My Education Ch. 02

Once again, I want to thank the wonderful joscelyn2tg for editing my story.

Disclaimer: My stories contain descriptions of consensual sex between adults. All characters and situations are fiction. Any resemblance to real people is strictly coincidental. All stories are property of the author.

Comments are welcome!

I've tried to keep the story as realistic as I can, while holding a level of fantasy.

*****************

The summer was already passing by quickly, and I should have been starting to prepare for the fall semester. Instead, I was spending almost all of my time with Cassandra. By the middle of August, we had a regular routine. First we would decide who's home we would spend our time, and get together around 11am to have sex for an hour and then have lunch. After lunch, we'd spend several hours reviewing material necessary for the PCAT pharmacy exam, which Cassandra now planned on taking in November, instead of at the end of the summer. After studying, we would cuddle and talk, as we were still getting to know each other. We always ate in, and the owner of whichever house we were in had to cook dinner. We developed a little competition as we both loved to cook, trying to outdo the last meal of the other.

Evening would find us sitting outside, again cuddling and talking quietly over wine or beer, and we would end up starting some foreplay outside, before having sex inside. Cass insisted that because of her hormone treatments she wouldn't always be in the mood, but there never came a time where she didn't want to do something. If she couldn't get herself erect, she'd spend a lot of time giving me pleasure. How could I argue? Well, I did argue quite a bit, insisting that we should really only have sex when we could both enjoy it. I thought that as we grew together as a couple, we would eventually find other ways of pleasuring each other that didn't involve sex, but not until some time later.

Cass convinced me that I should relax and just enjoy it, because she derived a lot of pleasure out of seeing me happy. After a few refrains of that argument, I finally gave in completely, convinced that I was not taking advantage of her.

Neither one of us had mentioned going any further in our sexual intimacy. I had wanted to have sex, but knowing that Cass has a long and twisting sexual history, didn't want to push things. She had made it clear through our conversations that I was her first lover since fully transitioning, and I wanted to give her the opportunity to set the pace. Cass had also hinted at some flexibility, when meant to me that either one of us could be the top and the other the receiver. I know from my own experience that I was interested in trying both ways, but I wanted a full discussion about the subject. I just didn't know how to bring it up.

Two weeks before the start of the fall semester, Cass and I had our first real date out. Both of us were nervous to present ourselves as a couple to the world, in part because of our previous professor/student relationship. Since nothing happened until after she had left the campus, there was no violation on my part, though there would always been some questions from the rest of the staff that knew of Cass. Cass felt some justifiable nerves at being singled out as transgendered in the event we might come across some idiot homophobe, as she had done in my class. I tried to assuage her fears as she did mine, but we were both still nervous as we set out that night.

We decided on a restaurant just outside of town, which had a good reputation. It didn't look like much on the outside, or the inside for that matter, but the service was exemplary and the food delicious. We spent a long time eating, talking, and holding hands over the table. There was something very freeing about being together in public, unashamed of showing affection. We had a corner table, and no one but the waitress bothered us. By the smiles that she was giving us when she approached, she seemed to approve of our affection for each other.

Our date was going so well that we decided to get a drink at a nice lounge not to far from our neighborhood. I had been there a few times when I wanted to watch a baseball game that I couldn't get at home. I knew one of the bartenders, Brian, and fortunately he was there when we entered. I waved, and made a gesture for two pints of my usual beer, and he brought them right over to the table. Brian hadn't met Cass before but I gladly introduced him. They were chatting amicably as I sat sipping my beer, when something caught my eye... two guys visible in the window outside, apparently ready to enter.

The wouldn't you know... it was the two jocks from my class two years before, the same two that had said some very derogatory things about Cass. Inside, they went right to the bar and my friend disengaged himself to serve them. My apprehension must have shown on my face because Cass immediately took my hand.

"What's up, Jason?" she asked, her eyes full of concern.

She understood very early on that I wore my emotions on my face. Without speaking, I nodded in the direction of the two jocks, who seemed to already be in an inebriated state, based on their awkward gaits. She looked over at them in confusion. I recalled that she wasn't even aware of what the two jocks had said. She knew the story only from my perspective. I leaned in to her to explain.

"Those are the two guys from your first year of class... the ones that had said such awful things about you." Her confusion changed into a very dark look and she took several sips of her own beer. I started to hope that they wouldn't notice us, but one turned around and saw me.

"Hey, Dr. E!" I tried to recall their names as the first came over, followed by the second. Chris... and Eric, those were the names alright. Chris was the real jerk and he flanked Eric, as Eric spoke to me.

"How are you doing, Dr. E? It's been awhile. Is this your date? She's pretty hot... I mean for you..." Even a jerk when trying to pay a compliment, I sighed realizing these guys were truly a piece of work.

"Date? Woman? She's the tranny dude. Remember from class?" Chris said with a drunken leer. "I guess it turns out that Dr. E's a fag!"

The entire bar froze. I could see Brian frown, and he started to move out from behind the bar. I knew that he wouldn't stand for any of this kind of thing in the bar. Cass was looking down, obviously horrified at the situation. I had a split second of indecision, but in the end, I stood up, almost getting in Eric's face, since he was closest.

"Excuse me? I'm not sure how you were brought up, but I don't think it's polite to use that kind of language in mixed company. Especially to your elders." I have some vague sense of how stupid and condescending I was sounding, but I was also seething. I never yelled when I was this angry. Eric was leaning in as if he had trouble hearing me.

"Come on, man. She's got a dick. If you're into that, you're a fag, pure and simple. I don't care if you're a professor... or not," Chris said with another drunken chuckle. I wanted to look to Cass, knowing she must have been in a worse state than me, but I didn't want to show any weakness at that moment. My heartbeat was pounding in my head, and subconsciously I was wondering if I could take on both of them at the same time.

"What I'm into is no business of yours. Frankly, you saw her first as a beautiful woman, which is what she is. What else is involved doesn't really matter, does it?" Cass made a small, unidentifiable noise. I still didn't look in her direction. Now both guys were essentially on top of me, and I was starting to feel fear mixed with anger. Two on one gave me little chance, and I certainly didn't expect Cass to get involved.

"Does she bend over for you or is it you who takes it up the..." Chris began, but suddenly both guys were being pulled back. Brian had somehow managed to find a local off duty cop outside, and before I could say another word, Eric and Chris were being unceremoniously banned from the bar and escorted out. I was still standing there with my fists clenched, my ears ringing, when I felt delicate fingers enclose my wrist.

"Jason," she whispered and took my hand. I finally looked at her and there were tears streaming down her face, her lip trembling. My anger broke at that moment and I took her into my arms. She was sobbing into my neck.

"Take her home, Jason," Brian said, patting my shoulder, "I'll make sure those two never do anything like that again around here."

"I'm glad you didn't try to fight. But good for you standing up to those clowns," Cass pulled away from me enough to give Pete a watery smile. He moved back behind the bar and I guided Cass out to the car. Our drive home was short, but Cass had resumed crying on the way. Without thinking, I helped her out of the car and picked her up, carrying her into her house. When I set her down, she kicked off her heels and went right for some tissues. At this point, her makeup was rather a mess.

"I'm sorry for all that, Jason," she mumbled, not looking me in the eye. "It's my fault for being..."

"No!" I almost screamed the word and Cass jumped, looking at me afraid. My fists were clenched again. "It's isn't your fault for being... you! It's them. Fucking idiots. They ruined our beautiful night and made you cry. I would have fought them if I had any chance. It would have been worth it to teach them a lesson. It wouldn't have sunk in though, just like the chemistry I tried to teach them. No one insults someone I love in front of me."

Cass gasped. I didn't understand what I had just said, though the feeling was true. Without acknowledging it, I had fallen in love with Cass. True, it had only been a month now since beginning our romantic relationship, but quite a bit pf emotional connection had built up before that.

"You... you..." was all she could say, her entire body trembling. I thought she was going to faint, so I came to my senses and scooped her up again. She held me lightly around the neck. "You... I... please take me to bed, Jason. Please."

I didn't move for a second. My words had come back to me, and I began to understand Cass' response.

"Oh... um, okay," I laughed a little and kissed her nose. I walked slowly back to her bedroom and placed her gently down on the bed. She opened her arms for me, then suddenly touched her face and got up.

"No... not like this... let me freshen up first." She went right to the master bathroom and shut the door, leaving me alone, and a little confused.

"I love you," I whispered to the dark room. I turned on one of the lamps and unbuttoned my shirt. I heard the water run, then the toilet flush a couple of times and then the water run again for a few moments. Cass opened the door, with a clean face, hair teased and looking incredibly beautiful as always. She had a bottle of lube in her hand.

"I... want to make love tonight," she whispered as she walked over. She tossed the lube on the bed and put her hands on my bare chest.

Though I knew my answer, I couldn't help but ask, "Why tonight?"

She hesitated for a moment as she looked into my eyes.

"Because you stood up for me. Because the last month has been the happiest time of my life. Because you are the one I've been looking for. Because I love you too." The words poured our of her mouth in a rush, her lip trembling. I grabbed her and pulled her against me kissing her deeply. While she was in the bathroom, I had wondered if I would be able to get aroused because of my anger. But all of that had melted away into passion, and within a moment I was hard and ready for Cass.

She pushed me down on the bed all of a sudden, and went right for my pants, which she managed to pull off with surprising speed. My boxer briefs came down almost as quickly, though my hardness made that a little more difficult. Her lips were on my cock instantly, swallowing me almost completely, my shirt forgotten. She was moving her lips over me with such pressure that I knew I wouldn't last long if she kept it up, but she suddenly stopped. She grabbed the lube and poured it over my cock, making sure my shaft and head were completely covered in it.

"What about..." I started, but she stopped me mid sentence.

"No, we won't need it. I know we're both clean. And I, um, did a quick cleanse..." I didn't get her meaning until she pointed at her butt, and then my eyes went wide. She smiled and nodded at my comprehension. She put the bottle away and laid down on the bed, looking over at me. I flipped her back over, and climbed right on top of her, my slick cockhead nudging her smooth balls, which made her moan.

"It's been a long time, but I'm ready," she whispered and we kissed deeply. I didn't trust my aim, so I leaned back, lifting one of Cass' legs, and between her cheeks, could see her hole was already slick with lube, something she must have done in the bathroom. I held the base of my cock and rubbed the head into her crease, until it rested against her hole.

"Please, Jason... please!"

I looked into her eyes and pressed. There was a surprising amount of resistance, something I didn't remember the few times I had been with a woman previously, though I hadn't had anal sex with them. I pulled back and looked at Cass. She bit her lip and I could see the emotions overwhelming her.

"I'm sorry. It's just nerves. I really want to... but I know it will hurt a little. Just... keep going. I'll relax,"

I pressed again, but I let her leg down and reached up to caress her cheek. This little sign of love seemed to do the trick because her anal ring finally relaxed, and gave in. I entered feeling a sudden and delightful pressure around my cockhead. Suddenly she grabbed my arm and I froze, waiting for her cue to keep going. It was a long moment, in which she took a few deep breaths. Eventually, she released my arm and nodded. Once I felt like I could spare both arms, I placed them next to Cass' shoulder and used my leverage to push deeper. I kept it going very slowly, trying not to let the pleasure of her tight channel consume me. It felt so incredibly good and tight, and while I saw Cass wince a few times, she didn't stop me anymore.

At one point, I pulled back, then stopped, giving us both a moment to breath again. She beamed at me, and her body relaxed more. Then I continued until I was completely inside, and I wrapped my arms around her. I felt her breasts against my chest, her soft cock squeezed between us. I kiss her just as passionately as I could, not really wanting to move anymore. For a moment, I felt that if I moved at all, I would instantly cum, but I tried to put that energy into the kiss, and it seemed to work. I felt my body move away from orgasm, and I pulled my hips back a little, then thrust.

"Yes... yes, just a little at a time, go slow, make it last. It's so good now. The pain is gone. Oh fuck, I missed this," she hissed in my ear. "I don't care when you cum. Fast or slow, I just want you to enjoy it."

I leaned back a little, and relaxed, remembering our discussion about enjoying pleasure together.

"But... I want us both to..." I started.

"Oh shut up," she was laughing, but then just a little seriously added, "I've already told you I'm loving this. But it isn't about making me cum. It isn't about you cumming either, you know. It's about being together."

I nodded. She was quite right, and I kissed her deeply as I started to move my hips again. She moaned into my mouth. We really were making love. As terrible as the scene in the bar had been, this more than made up for it. I didn't go too fast or even pull back to much. I craved as much body contact with Cass as I could. Her hands stayed on my back and ass, to encourage me, but she really did let me do what I wished. I wanted to make it last, last the whole night if I could, but instead of the physical sensations pushing me to orgasm, it was the emotional connection with Cass that triggered my release, and as the orgasm hit, I buried my face in Cass' neck, moaning loudly as she held me. I was sure I heard crying again, but this time, it was the good, happy kind of crying. And it wasn't just Cass. I was crying myself, after the release of my anger, the acceptance of love.

We held each other for a long time, even after I softened, but as I slipped out, I could tell that we were making a mess of the comforter. I made a move to get up, ready to clean up, but Cass held me fast.

"No, honey, not yet. I don't care about the comforter. It can go in the wash. I'm not ready to let you go yet." She kissed me softly and for a good ten minutes we kissed and nuzzled, until finally Cass sighed, then pushed me up. "Okay, I guess we'll just have to get up. Let me get a wash cloth."

She did so, and cleaned up both of us quickly, before throwing the washcloth on the comforter, bundled it up and took it down stairs. I stretched a little and looked out through the window. The sky was clear and there were many stars twinkling in the night sky.

Suddenly I thought, 'which house are we going to move into?'. My brain was always four or five steps beyond where it should be, but I couldn't help but feel right about the situation. I knew that there would be more evenings like this one, full of prejudice and hatred. But I was ready to face those thing with Cass, and for Cass. I heard her steps behind me, but I didn't turn around. She wrapped her arms around me from behind and put her head on my shoulder.

"This wasn't the evening I expected," she whispered, and put my arms over hers as we held each other tight, "I'm glad of how it ended, though. I really do love you, Jason."

"And I love you, Cass." I turned finally and kissed her, holding her close and strong.

******************************

We decided against moving in together for the time being, since the semester was starting for me, and Cass was going to be doing some free lance photography. I got the sense through several long conversations that Cass wasn't sold on a late-blooming career in Pharmacy. Though she was talented, and I knew she would be able to do well on her PCAT exam, she didn't hold the same kind of enthusiasm for the career path as many traditional aged students. I didn't push her on the issue, largely because we were doing so well as a couple, and I didn't want to force her into any decision. If she did decide on that path, the nearest school was an hour away and that was not a good commute for a graduate school student.

Cass seemed far happier when she was in the role of photographer, focusing on that craft. Her mini studio was perfect for short sessions, and when I sat in on one of them as her assistant, I could see she was a natural at getting the right poses, getting kids to stop fidgeting, and finding the right lighting. She had said several times that her profit from doing a few sessions every month wasn't large enough to live on, but I felt that if she did a little more marketing, took on a few more clients, she could make a living, and be happy doing it. Her house was paid for and it seemed like she still had decent savings.

As the semester progressed, I had a lot less time to spend with Cass, as I didn't always have time to go over every day, so we had to be content with short phone calls on some days. We spent every weekend together, and those were the highlight of fall. Long walks through the colored trees, a picnic at a local park, even a lovely warm Saturday canoeing. I had never really thought of committing to someone before, but as we held each other after making love one Friday night, I gave serious thought to looking for a ring. I needed to discuss it with my mother first. Not that I sought her approval, but I was always open with my mother. She should know the whole story before I moved forwards. A quick phone call the next day reassured me that my Mom was simply happy for me regardless of who I was with.