Continuing My Education Ch. 01

"You... like me too?" Her voice was very low and soft, and it quavered.

"Yes, quite a lot, and that was before the gifts you sent," I responded. Cassandra didn't speak for a few minutes as we continued to hold hands. She squeezed my hands once and then removed hers, and I didn't stop her, but smiled to let her know it had been appreciated.

"I'm really glad. So glad. But there... there are some things you should know about me. Important things," She stood up and started to pace, wringing her hands. I had never seen her this agitated in class, or even before an exam. She placed her hands on the counter, facing away.

"You've probably figured that I'm older than you are by now. I'm 44. I don't know if that makes a big difference to you. I've had a lot of ups and downs," I sensed there was more and I didn't want to interrupt. She turned around, and leaning back against the counter, gripped the edge hard enough to turn her fingertips white.

"I'm transgendered."

"Oh."

The word came out, as though the news didn't matter or change things for me. At least that's how I intended it.

"Oh? That's not the response that I expected, or usually get. Not that I've shared with many people," She looked a little frustrated, so I took a breath and explained my response.

"Well, I guess it makes sense to me, based on what I know about you and how things have unfolded. I know that you were vice-President of the LGBTQ club on campus, from my committee work. The pictures you sent me showed you from the side and back, as if you were hiding something from me. You slammed the door in my face when you weren't completely dressed," As I finished, Cassandra nodded, but was still frowning.

"That's coincidence, but not proof," she muttered.

"Maybe, but I didn't tell you about something that happened more than a year ago. I overheard those two jocks that sat in the front of the class. They were discussing you, trying to decide if you were worth hitting on. One of them, I won't name names, said some very derogatory things that suggested you were... well, I won't use the words they did. They suspected you were were transgendered. I don't normally interrupt such conversations, but I stopped them and told them to keep their ignorance to themselves, or leave my class," Cassandra looked surprised, and rather embarrassed.

"You did that?"

"Yes, I certainly did. I made sure that they never said a word of it again. For my part, I thought there was something vaguely androgynous about you, but it added to your beauty. These days, with fashion choices, make up and a variety of other things, who really knows anything about true gender? I wasn't about to make any conclusions just because of some observations," I stood up, seeing that Cassandra was trembling. She hugged herself with her arms and looked away.

"None of this changes what I think of you, Cassandra. You are still beautiful, intelligent, warm, kind and amazing,"

Cassandra looked up, tears in her eyes.

"Really?"

"Mmhm," I smiled and nodded. Cassandra rushed at me and embraced me, sobbing into my neck. I held her tightly, closing my eyes and breathing in her hair. Everything about that embrace felt so right to me, and my body couldn't help responding. Cassandra could obviously feel my erection pressing her hip, because she pulled away slightly with a little smile on her face.

"Wow, it really didn't change anything did it?" she said with a little giggle.

"Uh, no, obviously. I guess that's pure honesty for you,"

"Well, um, you aren't the only one Jason," My eyes widened, only comprehending what she was saying for the first time. I finally let my eyes wander downwards.

"You are doing a good job of hiding it then," I whispered.

"Well, I've had a few years of experience," she said.

"I thought transwomen had trouble with... you know... that," I said, rather sheepishly.

"Let's sit down and I'll tell you some of my story. Hopefully then there won't be any more surprises,"

Cassandra refilled out iced tea glasses and began to tell her story.

I could tell there was more than what she was telling, but I didn't ask for more. Until junior year in high school, Cassandra lived as a boy, but like many, never felt comfortable in her own body. She tried wearing women's clothes, both her sisters and her mother's and felt much more comfortable. She slept with boys and girls, liking both. Once in college, and able to be more free, Cassandra tried drugs, many sexual partners, and as many kinks as she could, but still couldn't find happiness, because she still couldn't be herself, whatever that was.

At this point in her story, Cassandra started to cry and I took her hands and held it tightly.

Between sniffs, she told me that after an incident where a man tricked her into a dangerous situation where she was almost gang-raped, she gave up her female persona and tried living as a man. She even got married for a short time. Ultimately, she became depressed, started dressing in her wife's clothes, and was caught. When her wife demanded divorce, Cassandra tried to commit suicide. Cassandra showed me her right wrist, and the large scar there.

It was Cassandra's wife, now ex-wife Kristin, who saved her, just after Cassandra started cutting her wrists. Kristin convinced Cassandra to seek help, and to live as she needed to, to feel whole. After years of soul-searching, and a move a thousand miles away, Cassandra began her real transition. She donated all her men's clothes, changed her name, and thanks to an inheritance, had several surgeries.

"I thought about complete gender reassignment, but honestly, I didn't want to lose my penis. It took a long time to find a level of hormones that allowed me to maintain most of it's function, and to help with some of my physical features. I still can't get erect sometimes, but it's better than nothing. I know that makes me different than a lot of other transwomen. Many of them have to deal with severe dysphoria and don't want anything to do with their penis. I certainly don't mind when a lover touches me there. I feel comfortable in my own body finally, and I can be happy with lovers. If I could find one,"

Cassandra got up and wiped her eyes and nose with a tissue. I sat at the table taking it all in. Though I knew it was a little insensitive, I observed her body more closely with this new information. I suppose that there were signs that she had been born male. None of what I saw changed how I felt about Cassandra, nor what I now knew was between her legs. Though I had never acted on any attracted to men, I had felt them from time to time, and I wasn't afraid of other dicks.

I stood up and walked towards her, making eye contact. Her eyes were wide, nervous, and as I approached she gripped the counter harder, as if expecting the worst.

"It's most important that you are happy. Nothing else really matters, does it?" I said quietly. Tears started streaming down her cheeks as she nodded, and I reached out to place a hand on her hip.

"I knew you would understand, Jason. I should have told you before,"

"No, there wasn't a reason to tell me. It doesn't change anything," I grasped her other hip, and she shifted away from the counter, closer to me. Our faces were very close now, and I could feel her breath on my lips. She lifted her hands and placed them on my chest. For a moment, I thought she would push me away. Instead, her hands slid around my torso, and she held me with her head against my shoulder.

My arms slid around Cassandra to hold her as well, and we stayed that way for a long time, just breathing together. She felt so perfect in my arms. The scent of her. The way she moved her fingers along my back. Not surprisingly, my arousal became rather obvious, and I was uncomfortable in my jeans. Cassandra had to have known. In fact, she pulled back and looked into my eyes.

"You're hard, Jason," Her eyes were twinkling and her cheeks were flushed.

"Yes, I am. Because of you," I smiled and felt flushed also.

"Even though..." I put my finger on her lips before she could finish her statement.

"I said nothing had changed, and I meant it," I pulled away my finger, but not before she had kissed it.

The movement of her lips made the decision for me. I leaned in, a little quickly and captured her mouth with mine. Her little whimper as our lips connected was perhaps the sexiest thing I had ever heard. The kiss started slow, but as we explore each other, the pressure increase, our tongues touched, and our embrace became tighter. My erection was now almost painful and it pushed hard against her hip. She pulled back suddenly, with a slightly anxious expression.

"I'm... wow... that was amazing but... I haven't ever..." she mumbled.

"Ever what?"

"I haven't been intimate with someone since I transitioned," she said as he eyes again filled with tears, "I really want you, Jason, but I'm scared of..." She didn't complete the sentence.

"I really want you too, Cassandra, but we don't have to rush. I didn't come here expecting to jump right into bed with you. Hoping? Perhaps... a little," I admitted, red faced. She smiled.

"Well, I didn't expect to, or even hope to. But now that's changed," She looked down at my bulging jeans, and her smile widened, "and I couldn't let you go home with that. I wouldn't be a good host."

"I've gotten used to taking care of myself. You shouldn't feel obliged. We've only just had our first kiss, anyway."

"Are you a romantic, Jason? What am I saying, of course you are. I knew that the first time we talked in your office. It's in your eyes," I looked surprised, and met her eyes again, "but still, I've been thinking about being with you for more than a year, and I don't think I can wait that much longer, whether that includes more kissing or not."

"Well, there's still no reason to rush. Come with me," I took her hand, and led her to the living room and closed the blinds. The sunlight faded and we were in semi-darkness. Cassandra had a confused look on her face, but fell into me as I grasped her hips and kissed her again. This kiss was much longer and more passionate, and this time, both sets of hands explored more freely.

Cassandra spent a lot of time running her hands over my chest and shoulders, whereas I was caressing her back, hips and bottom. She seemed to love my hands on her firm cheeks, because each time she moaned into the kiss. At one moment, I started to lift up her dress, but she suddenly stopped me.

"Wait... I... not yet. I want to see you first. Then... I'll show you... all of me," She bit her lip, but I took a step back and nodded. I could tell how nervous she was, and I didn't want to push at all. Her hands trembled as she reached out and lifted up my shirt. I lifted my arms and she pulled it completely off, then ran her fingers along my chest, through my chest hair.

"God, I love a hairy chest," She moaned, and not content to wait, fumbled with the buttons on my shorts, then pushed both my shorts and boxers down as my erect cock sprang up. She groaned again, grasping my shaft as she stood kissing me again.

"It must be my birthday," she cooed softly.

"Um, I'm not that impressive," I muttered, unable to take the compliment with grace. She slapped my arm playfully.

"None of that, Jason. I think you are beautiful," she smiled, then stepped back, suddenly nervous. "I guess it's my turn."

Standing there completely naked in front of a gorgeous woman didn't give me the clearest head, but I tried.

"You don't have to do anything you aren't ready for, Cassandra. Seriously," She shrugged, but slowly and steadily lifted her dress. She exposed lace-trimmed black boyshorts, then a flat stomach. Her breasts were encased in a black bra, and as she tossed the dress aside, her long, brown hair cascaded down her shoulders.

"Can I help?" I asked, eager to see more. I think my desire and enthusiasm came out in my voice, because her lips curled up a little and she nodded. She turned around pulling her hair forwards, over her shoulder, a sign that I could unhook her bra. I did so, as the head of my penis brushed her right buttock. She pushed back a little as I slid her bra straps down. She pulled it off the rest of the way, showing me the flawless skin of her back.

Unable to help myself, I leaned over and kissed her shoulder, letting my lips linger against her skin as I slid them up her neck, ending with a slight suck below her ear. She moaned quietly, reach back behind her to grasp and squeeze my cock.

"Don't stop now Jason!"

I pulled back, and knelt down behind her, slowly pulling her boy shorts down. I stared at her perfectly firm and shapely bottom, kissing each cheek. She swayed her hips playfully, then stopped.

"Would you like me to turn around?" she whispered, a note of anxiety in her voice. I knew why. She was going to show her whole self to me and wasn't sure how I would react. I stood back up and stepped back.

"Yes, Cassandra. Please turn around. I want to see all of you,"

She reached back and teased her hair, then slowly turned to face me. Her head was down, likely not wanting to meet my eyes. My brain was buzzing, making it difficult to think straight. I didn't look down immediately. I reached up and lifted her chin so that she could look me in the eyes. I smiled, and then she did. I felt it was okay now to look down, over her breast and flat stomach.

Her penis was a darker color than her skin, almost brown, and her smooth balls were the same color. She curved down towards the floor, partly aroused.

I searched my thoughts, wondering why I wasn't scared, or repulsed, or even shocked. She told me about this, and I wasn't nervous. She had shown me her entire body and I didn't hesitate. I pulled her against me and kissed her deeply, aware that at the moment our lips reconnected Cassandra whispered, "Oh... Jason,"

I felt our two cocks touch as we kissed, both of us growing as our lips and tongues played. She clutched me hard, as if worried that I would try to escape at any moment. We both became fully erect as the kiss grew more passionate. I broke the kiss reluctantly and looked down. Her fingers slid around my length and squeezed. Without another word, I reached out and slide my fingers around her shaft and squeezed in the same way.

"Is this your first time touching another cock, Jason?" Cassandra's voice was breathy, but the nervousness from before was gone.

"Um, yes, I guess it is. It's..." I hesitated, looking for the right word.

"Soft? Hard? Weird? Scary?" she went through word list in rapid fire, almost laughing.

"Beautiful," I whispered.

"Ohhhhhhh..." she murmured softly, releasing me from her grasp. I gently put her hand back where it had been. Then I groaned and started to let myself go and enjoy the pleasure, but Cassandra suddenly stopped again, and I opened my eyes, sighing in disappointment. She kissed me softly.

"Don't worry, honey, I won't leave you like that for much longer. But there is something that I've wanted to do for a very long time, even longer than I've wanted to make love to you. Come with me." She grasped my hand and led me to the hallway. My erection didn't fade as she led me into one of the spare bedrooms. Only it wasn't set up like a bedroom. It was a small studio for photography, complete with standing lights, a changeable background, a table full of cameras, and a futon.

"I want to take a few pictures of you, just for me, I promise," She added the last part after I looked down at my naked body, and back up to her with a frown. I hesitated in the doorway, finally growing soft.

"Please, Jason. Think of it as a trade for the pictures that I sent you. You don't have to be fully nude if you aren't comfortable. In fact, it will be sexier if you aren't. Don't go back to get your underwear, I have a better idea. Please sit on the futon and relax," I did as she requested, though it was difficult to get comfortable. To distract myself, I looked out the window. The clouds were dark and ominous, and I thought I saw a flash of lighting. The sound of distant thunder rolled past and my eyes returned to Cassandra.

She was looking out the window as well, frowning as the thunder boomed, and stopped just as she had lifted the camera lens. She whispered something indistinct, then returned to her work. After getting her camera ready, she pulled a white sheet out of a drawer and casually draped it over my legs as I laid down, facing the camera. She adjusted the sheet until she was satisfied, then snapped a few pictures with me looking at the camera. After the first two, I relaxed a little and focused on trying to make the right poses and faces.

After the fifth or sixth picture, a louder clap of thunder sounded, and Cassandra head swiveled toward the window so fast, I thought she might have whiplash.

"Is something wrong, Cassandra?" I asked, concerned.

"Um, I... don't like thunderstorms much," she mumbled, not looking at me. There was a flash and quite a loud clap of thunder. I could tell that she was shaking.

"I don't think many people do. I certainly don't. Are you afraid of them?" I got up, the sheet falling away and I walked over to her. Her eyes were wide, and she looked very pale. She didn't need to answer. She looked petrified. I took the camera from her and put it down, then put my arms around her. She leaned into me a little, and I could tell how much she was shaking. I was just about to speak when I hear sirens blasting. A severe weather warning.

"We need to get to the basement honey. Right now, okay? Do you have flashlights down there? Water?" My brain automatically shifted into action. I was typically afraid of severe storms like this, but living alone for so many years had trained me to deal with that type situation and not be panicked. She nodded, and I guided her back out to the main part of the house. It wasn't raining yet, but the trees were getting whipped around by the window. There wasn't enough time to get dressed, so I grabbed a blanket from the couch and went downstairs.

The basement of Cassandra's house was partially furnished, with a couch, chair, shelves and television, but my eyes noticed the small windows near the ceiling. Cassandra weakly pointed towards a door that was slightly ajar.

It's a three-quarter bath," she muttered, and I steered us right into it, grabbing a flashlight along the way. I shut the door, sat down on the toilet, guided her to my lap and pulled the blanket around us both. The storm seemed to hit it's peak right as we sat down, with the wind raging and hail pelting the house. As Cassandra started to sob into my shoulder, I heard a distinct booming sound, as if something very heavy fell nearby, but I didn't hear any noise from above, telling me that the house had not been hit.

The boom seemed to completely unravel Cassandra and she fainted. All of a sudden, her body was very heavy and limp, and it became an effort to support her. I could only hold on tighter and not let her fall down to the tile floor. For another twenty minutes, I could hear the storm outside, though the sounds gradually faded, until there was no more thunder, and no detectable rain. Mercifully, the power flickered a few times, but never went out completely.

Cassandra eventually stirred and her grip returned, although she still trembled, and in the light of the bathroom, she looked very pale. The sirens signaling the end of the storm warning sounded a moment later.

"I'm... I'm so sorry, Jason. What you must think of me for falling apart like that," she muttered into my neck. I started to stroke her back, "I've been terrified of storms since I was little and my sister was struck by lightning. I usually come down here and cry while the storm is happening, but I don't usually faint."

"It's alright. Some day, I'll tell you about my fears. It's a long list," I whispered, "anyway... we should go out and see what fell, although I'm guessing it was a large branch. The power is still on, so I don't think anything fell on the wires. Are you good enough to come upstairs?"