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.
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I've tried to keep the story as realistic as I can, while holding a level of fantasy.
Most students that come across my path represent the typical college student stereotype: young, entitled, and more interested in fun than learning. Of course, there are always the bright, driven, amazing students who rise quickly to the top of the class. Working at a community college also means that I get to see a lot of returning adult students, who often are working on a change of career path.
One such student spent two years with me in class. I have taught a two year science sequence as my main teaching load, and she was required to take it for her new career goal as a pharmacist. With the recent upsurge of prescribed drugs, pharmacy was a popular major, especially among the typical college-age students. The major courses are very demanding and most students drop out before the end.
Cassandra managed to not only survive, but thrive in the sequence, getting well-earned As in each semester. She also led study groups, and generally keep the rest of the students in check. Despite her talent and intellect, she would often come to my office hours to ask questions, or even just work outside my office at the table to study and get my input if necessary. Always bright, outgoing and sweet, her presence was always welcome.
I've been attracted to students before, typically the cute and sweet, next-door type, but as the second year went on, I developed more than a simple attraction to Cassandra. Part of it was her age, just slightly older than myself, and the other was her deep brown eyes. I was always drawn to her in some way, but I kept it professional and friendly, as least outwardly. She was incredibly attractive, and I did notice more than one of the freshman guys eyeing her.
After the final exam of the end of her second year, I though that was it. She smiled at me as she gave me her exam booklet and paper and whispered, "Have a great summer." I smiled back and whispered the same, and thought to myself that I would never see her again. Two hours later, I heard a knock on my office door just as I pick up her exam to grade. When she opened the door and stepped in, I'm sure that my face registered happy surprise as I stood, because she blushed.
"I wanted to thank you for helping me these last two years. You are an amazing teacher, probably the best that I've ever had, and I brought something for you." Her voice wavered slightly as she finished and handed me a medium-sized gift bag, tissue paper rising up from the top. I took the bag and started pulling on the tissue paper, but she reached out a hand and placed it on mine to stop me.
"No, please, wait until you get home. You'll understand." Our eyes met and a look in hers I had never seen was there. Vulnerability, sadness and even a little fear. Her fingers caressed the back of my hand for only a split second, then with renewed redness of her cheeks, she muttered a hasty goodbye and I heard her heels on the floor as she left the building. I was in such a state of shock about the entire encounter that my fingers were still gripping the tissue paper. I was sorely tempted to see what my gifts were, but I reluctantly removed my hand and placed the bag on the side of my desk.
I struggled through the rest of the exams, including Cassandra's, but late in the afternoon, I finished, and completed my final grades online. My heart was beating quickly as I filled my briefcase, grabbed the bag from Cassandra and sped home. I didn't have anything prepared for dinner, and forgot to stop on the way, so as I walked in the door, I cursed to myself. I knew then how much Cassandra had affected my life.
I threw a frozen pizza in the oven and sat down in my living room, staring at the bag for a moment. What was inside that she didn't want me to see at work? Or was it that she just didn't want me to reveal the gifts in front of her?
I pulled out the tissue paper and reached inside without looking. Wrapped in another piece of tissue paper was a polo shirt, identical to one I had lost to a lab accident a year before. I gazed at it in shock, since I knew that they were no longer available for sale. Putting aside my surprise and the shirt, I reached in and pulled out a pound of my favorite coffee. It was as though she had written down the things that I love to have at work. I pulled out one more piece of tissue paper, and then found an envelope in the bottom of the bag, sealed.
I opened the envelope and picked up the small note first.
"Dear Jason, ÿA simple thank you isn't enough for everything that you have done for me these past few years. I came to your class very unsure if I was doing the right thing in returning to school. You showed me that I did make the correct choice. You showed me that I could learn and grow and understand new things that enrich my life far more than anything had before. You gave me confidence. You gave me hope for a new career and for the years to come.ÿ I adore you for all of it. These are pictures I took for you last month. You will probably want to contact me after you see, but I'll be away for two months visiting family for the summer. It's better that way, since I know anything between student and teacher is against the rules. Have a wonderful summer. You deserve to have a nice long break and enjoy yourself. Love, Cassandra"
I reread the note two more times before putting it down on the coffee table. Emotions ran through me so fast that I could not separate them. Frustration, joy, sadness, pride. With my brow furrowed, I pulled out the pictures from the envelope. The first picture showed Cassandra smiling at the camera with a beautiful sunset over the lake in the background. The next showed the same scene but Cassandra sitting and facing the water, fingers in her hear. Her long, flowing skirt seemed to be fluttering in the lake breeze, showing her smooth legs up to the knee. A third picture showed Cassandra dipping her feet into the water, holding her skirt up slight, again showing her legs up to the knee. The pictures only reinforced what I knew about Cassandra: she was graceful, elegant and utterly beautiful. Dark flowing hair, olive skin, slender but with subtle curves.
I felt my own arousal as I revealed the last picture.
Fuck me.
Cassandra was in a bedroom, hers I would imagine. She was lounging against the pillows, head tilted back, and spraying herself with perfume. She wore only black panties and a polo shirt. The polo shirt that lay on my coffee table. My eyes flicked to it and then widened. I pulled the shirt to my face and breathed in.
Cassandra. Her perfume. Her skin. Her hair. The hints of scent that I had detected over two years mixed together and flooded my nose. I grew hard very quickly, and I was tempted to drop my shorts and masturbate right there, but I got hold of myself and went through the situation in my mind.
A beautiful, intelligent former student had sent me a lovely gift, and a provocative picture. There could not have been an innocent reason for the picture. It oozed sex, so she must have been hiding attraction for me. Though her note suggested that she wanted no response, I couldn't let that stand. I only had her school email, and I would have to be discrete, but I was determined to write an email to her.
I put the folded shirt aside and went to get my laptop. I had to shift to adjust for my erection as I satÿ back down on the couch and brought up my online class roster. I found her email and started to type, choosing my words very carefully.
"Cassandra, Thank you for the replacement polo shirt. I cannot think where you found one exactly like the one I lost in lab, but I'm truly grateful for it. You are an amazing student and I wish you the best in all your endeavors. If you ever need advise or assistance, please don't hesitate to contact me. Regards, Dr. Hansen"
I reread the email several times, making minor changes, and I knew that it was completely inadequate for the gift Cassandra had given me. I knew, though, that emails were sometimes monitored by the campus administration, and it was best not to include anything that suggest more than a student-teacher relationship.
I hoped that Cassandra would see the email at some point over the summer, and respond. Putting my computer away, I picked up the shirt again and unfolded it, planning to try it on. Something fall from the folds and hit the floor.
Panties. The panties that Cassandra wore in the picture.
Fuck me. Twice.
My hand was shaking as I leaned over and picked them up. The photo was one thing. The panties were something else. I lifted them, feeling the fabric, soft and satiny, then breathed in the scent. More of Cassandra's perfume, mixed with something more earthy, musky, perhaps her arousal. It had been so long since I had smelled a woman's scent that it seemed foreign, though still very exciting.
I couldn't resist now, so I unbuttoned my shorts in the middle of the room and pushed them down along with my boxers. I grasped my cock and started to stroke still breathing in the panties. I didn't hold back in anyway, so it wasn't more than a minute or two before I groan and felt my warm cream flowing over my fingers, along with the scent filling my nose. Something in the scent of my own cum made me take another deep breath of Cassandra's panties. There were similarities in the scents, enough that I was a little confused. I shook my head and decided that each person was different and that I must have been smelling mostly myself. I quickly cleaned up, and put the shirt in the hamper, but left the panties unwashed on a shelf in my closet.
The next new months went by quickly, because I suddenly had family matters to attend to, and what hours I didn't spend with family, I spent working on the landscaping around my house. I loved being outdoors as much as possible, even in the hot, sticky July weather. I checked my email everyday for work purposes, but nothing from Cassandra appeared. As August approached, I decided that she much have decided to move on. I was disappointed, but I understood on some level. She had admitted her attraction, given her thanks, and didn't put herself out too far.
On a Friday, a particularly hot one, I worked out at the edge of my yard, mulching around some cedars trees that I had planted the year before. I was sweating so much that my eyes stung, and after an hour's work, I was feeling light-headed. Not wanting to pass out or be sick in the middle of my yard, I retreated inside to towel off and have a couple of glass of ice water. I pulled my laptop to my at the kitchen table as I sat, sipping water with lemon, and saw an email from Cassandra with the subject line "Summer Greetings and a Request."
My eyes bulged, as well as something else, and I opened the email.
"Jason, I take it from your response that you opened you gift and enjoyed it. Long ago I taught myself to make clothes, and although it was a challenge to replace your favorite polo, it was well worth it. On a different note,ÿ I was hoping that you would be able to tutor me for my entrance exam coming up in six weeks. I have spent most of the summer relaxing and clearing my head after tow year's hard work, but now I have to focus again. Please let me know as soon as possible if you would be willing to spend time preparing with me. Perhaps a few hours a week? I would truly appreciate it. Sincerely, Cassandra"
My mouth hung open as I finished reading the email. Tutoring? Of course I would agree to that, but Cassandra wouldn't need several hours a week to prepare. She was too intelligent and talented for that. She had an ulterior motive, I was sure of it. I checked and she included not only her phone, but also her address. I couldn't believe that she lived only a few blocks from me. I could walk there in a matter of minutes.
My mind buzzing with many thoughts, I rushed upstairs to shower, shave and make myself look presentable. Though I would have preferred to wear something nicer, like that khakis and polo shirts I preferred at work, the weather wouldn't permit it. I pulled on khaki shorts and one of my nicer t-shirts, checked myself in the mirror, slipped on sandals, and went outside. It had not occurred to me to call first, I was so excited to see Cassandra again. My thoughts kept drifting back to the picture and the smell of her panties. Helping her with her exam was very much in the back of my mind.
After only four or five minutes, passing by two Mormons on the way, I stood in front of her house, a small ranch-style home that I had passed by on the short runs I took to stay in shape. I checked her address once more on my phone to be sure, and then I walked up and rang the door bell. From inside I heard an angry voice.
"For fuck's sake, will you leave me alone! I have no interest in being a Jehovah's Witness! I'm a..." The door opened and Cassandra looked at me with a furious look until she saw who it was and then her face registered utter shock.
"Oh no..."
SLAM!
Suddenly the door was inched from my nose. Cassandra had slammed the door in my face. I knew that I had come without warning, but I didn't expect this kind of reception. I listened closely, and heard sniffling from the other side of the door.
"Cassandra?" I said quietly.
"Jason? I'm... sorry. I didn't expect you like this. They were just here. I... I'm not decent. Could you... go around back and wait on the deck? I'll only be a few minutes, I promise. The gate is open."
I heard steps moving away from the door quickly, so shrugging to myself, I went around the side of the house, through the high wooden gate, and into the backyard. Neatly trimmed grass with small pockets of beautiful flowers greeted me as I slowly walked along the path and up onto the deck. I chose to sit on a patio chair facing away from the sliding glass door.
The deck had shade from a tall silver maple tree that swayed in the gentle summer breeze. I chided myself as I waited, planning on apologizing as soon as Cassandra emerged. I really should have called first. The damage was done now, and despite what had just occurred, she invited me to stay. That was something. I didn't have to wait all that long before I heard the sliding glass door open. I turned around and stood up.
Cassandra stood before me in a yellow sundress, dark hair around her shoulders, large brown eyes gazing at me, half scared, half reproachful. I had a difficult time not looking at her from head to toe, but I figured that I hadn't earned that kind of look yet.
"Cassandra, I'm really sorry, I should have called first. I was just so happy that I you responded to my email that I didn't think properly. Please forgive me." As I spoke, her eyes softened, and her painted lips curved into a smile.
"It's alright, Jason. I don't blame you, I blame the Jehovah's Witnesses for bothering me two days in a row. I don't normal get so angry, because they are so nice and polite, but I guess the heat got to me." She brushed hair behind her ear and looked away for a moment. Neither of us could speak, with the lingering question of the picture and what it meant hanging in the air. "Why don't you come in now? I should give you a little tour of my home, if we're going to study here," she said quietly, and beckoned me to come in. As she turned, I allowed myself a quick full view of her body from behind.
Slender, almost willowy, with long smooth legs, feet in simple sandals with a slight heel. She moved with such grace, I wondered if she had training as a dancer. And such a rounded bottom that I loved on women. It teased and swayed in such away that I had to think about baseball just to prevent myself from walking inside with an erection.
The tour was brief, since her house was small and she avoided her bedroom because, "I just tossed off my other clothes, so it's a mess". We ended in the kitchen and she poured us iced tea in the glasses, and we sat, looking at each other again. I could have started with her request for tutoring, but I couldn't just let the tension linger. It was starting to put a knot in my stomach, and I couldn't have that.
"Cassandra, before we to any review, we should talk about your gift first. I didn't get to say or ask anything in the email that I wanted to, because it could have been read." I tried to speak as calmly as possible, but this was a sensitive subject, and my voice was nervous. Cassandra nodded slowly, also nervous. I took a breath and continued.
"First, I haven't received such a thoughtful gift from anyone in quite sometime. The polo by itself was amazing. I would have worn it today, but it's in the laundry now. I've worn it quite a bit over the last few months." Cassandra blushed and smiled, but didn't interrupt. "As for the pictures..." I paused. I wanted to choose my words very carefully, but on thinking about them, all I could imagine was the scent of Cassandra's panties, and how incredibly sexy she looked then and now.
"Jason, you don't have to say anything about them. I took them on a whim, just because I have a passion for photography, and thought I could give you something to the remember me by." Cassandra's voice was almost detached, as through she didn't mean a word of it.
Her last sentence struck me as odd, as well as her tone. It gave me resolve to get to the heart of the matter.
"Cassandra, that last photo was incredibly sexy and provocative. Just that was enough to arouse me, but you included the panties too. Please don't tell me those were a parting gift." Cassandra seemed surprised at how direct I was, and looked flustered. She tried to say something, but closed her mouth, shaking her head. I noticed that she had balled her hands into fists. This wasn't how I wanted this to go, so I reach out and took her hand, prying open her fist. Her eyes looked right at me, and she tried feebly to pull her hand away.
"I've been attracted to you since the first day you walked into my class, Cassandra, even if it was subconscious at first. I liked having you around my office so much, and I think you are beautiful, intelligent, talented, warm, kind and a dozen other things. The only thing that prevented me from showing real interest in you was the fact that I was your professor." As I spoke, Cassandra's lips parted, looking surprised.
"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.
"I'm really glad. Really glad. But there's 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, 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'm a recovering alcoholic for one thing, though I've been sober for about 9 years." This was a surprise to me, but it didn't change anything, so I didn't respond. I sensed there was more and I didn't want to interrupt. She turned around, now leaning back against the counter and gripping the edge hard enough to make 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 did. I made sure that they never said a word of it again. For my part, I though 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?"
"Mmm hmmmm," I answered 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, really comprehending for the first time. I finally let my eyes go 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 that 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 told me her story.
I could tell there was more than what she was telling, but I didn't ask for more. Until age sixteen, Cassandra lived as a boy, but like many, never felt comfortable in her own body. She tried on women's clothes, her sisters and her mother's and felt much more comfortable. She slept with boy 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 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 slide around me torso, and she held me, with her head against my shoulder.
My arms slid around Cassandra to hold her 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 filled with tear. "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 her expecting to jump right into bed with you. Hoping? Maybe a little," I admitted, red faced. She smiled.
"Well, I didn't expect to, or even hope. But now that's changed." She looked down at my bulging jeans, and her smile widened. "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, more kissing or not."
"Well, there is 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 to herself. Apparently not content to wait, she fumbled with the button on my shorts, then push both my shorts and boxers down to the group, my erect cock springing up. She groaned again, and grasped the 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 sway 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,ÿ 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 become 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 rapid fire, almost laughing.
"Beautiful," I whispered.
"OhhhhhhhÉ" she murmured softly, releasing me from her grasp. I pulled her hand back to where it was.
I groaned and started to let myself go and enjoy the pleasure, but Cassandra suddenly stopped, and I opened my eyes, sighing in disappointed. She kissed me softly.
"Don't worry, honey, I won't let 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 send 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.ÿ 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 also, frowning, and had stopped just as she had lifted up a 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 would have whiplash.
"Is something wrong, Cassandra?" I asked, concerned.
"Um, I, um, 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 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. Now. 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.
"Half 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 blanked around us both. The storm seemed to hit it's peak right as we say, with the wind raging and hail pelting the house. As Cassandra started to sob into my shoulder, I hear a distinct booming sound, as if something very heavy fell nearby, but I didn't hear any crash from above telling me that the house had 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 and kissed her cheek. She chuckled. "We should go out and see what fell. I'm guessing it was a large branch or even a tree. The power is on, so I don't think something fell on the wires. Are you good enough to come upstairs?" She nodded and slid from my lap, holding the blanket around her shoulders. I led us back upstairs and pulled on my clothes as she went to the bedroom. Still holding the flashlight, I went to the patio door and looked outside. The patio was covered in small branch, but I couldn't see anything large. When Cassandra rejoined me, dressed, I opened the door and stepped out.
Focusing the beam of light on the far corner of the yard, I saw a large branch cutting across the grass, perhaps more than a foot in diameter at it's widest, and at least thirty feet long. The very end of the branch fell feet from the patio, but cause no damage beyond divots in the yard. Cassandra made a quiet noise next to me.
"Pretty lucky that it didn't hit the house. A different angle of falling and it would be in the kitchen," I said quietly.
"Don't say that. I don't want to think about it," she responded and grabbed my hand.
"I have a chainsaw that I can get in the morning, and I'll be able to cut this up. It will save you the cost of calling a tree surgeon." I took a few more steps out, checking the rest of the yard. Nothing else large had fallen, but it would be a big job cleaning the yard the next day.
"You would do that for me?" Cassandra asked, trying to pull me back, obviously not wanted to go out into the grass when it was so dark.
"Well, of course," I said, rather surprised at the question. "I want to help in any way that I can. You are, at the very least, my friend, and maybe..." I stopped knowing what else to say at that moment. Cassandra moved close and kisses my cheek.
"Maybe," she whispered. "Let's go inside and deal with it in the morning. Will you stay with me tonight? I knew we were about to... be intimate, but I don't think I can manage that anymore."
"It's alright. I don't think I could either. It's early, but we could get some sleep."
"Yes, let's."
We went back inside, and Cassandra led us to the bedroom. I only then noticed that she was wearing just a robe. She opened up a drawer and grabbed a cami and boyshorts and went into the bathroom. I heard more sobbing, so I went back out to gather all my clothes from the living room, giving her privacy. I put on my boxers, and she eventually appeared, eyes down. She grabbed my hand and pulled me onto the bed and under the sheets.
"I'm so sorry about all of this, Jason. I'll be better tomorrow I promise. I can't tell you how glad I am that you are here with me tonight." She kissed my cheek then cuddled up to me, head on my shoulder. I kissed her forehead.
"I'll be glad to stay with you through any storm, Cassandra," I whispered. She squeezed me.
"Call me Cass," she murmured, and a moment later, she was fast asleep. It took me much longer to fall asleep, and I processed everything that happened that day. The sheer weight of so many thoughts pressed on my brain, and actually made me sleepy. I contented myself with knowing that I was holding a wonderful woman in my arms, and that she liked me.
We both slept in late, though Cass was up before me, and I awoke to see 9:34 am on the clock, and Cass gone. After stretching and using the bathroom, I walked towards the kitchen and found Cass staring outside the patio door, holding a cup of coffee. I didn't want to scare her, so I tried to make heavy enough footfalls. She turned her head and smiled weakly. Looking out the widow myself, I saw the real size of the branch that had fallen. It looked like a small tree, and it would be significant work to get it cut up and removed.
"It's big, but with the chainsaw I think I should be able to cut it up into small enough pieces that the city will take it away." Cass nodded, but still stared outside, lost in thought. I placed by hand on her shoulder, and she covered it with her own. "Why don't I go home, get breakfast and come right back with the chainsaw." I kept my voice quiet, but she didn't respond for several moments.
"Why don't you come back after lunch? I think I need a little time to myself this morning." I pulled my hand back from her shoulder, a little nervous that I had overstepped some boundary. She turned slowly and kissed my cheek. "Don't worry, Jason. It's not anything you did. I just need to gather my thoughts after last night. I want you to stay for dinner tonight. I'll cook. You can shower here after you are done working." She smiled and so did I. Knowing now she wanted time alone, I didn't linger, and went home as quick as I could. My own thoughts were churning as I gassed up my chainsaw, checked that it was in good order, then I went inside to take a quick shower.
Never in my life had I thought I would be attracted to a older, transexual, former student. It all seemed so strange, so unlikely, yet I wasn't scared of what any of it meant. The conversation had been so natural, holding Cass in her most desperate fear had come by instinct. After my shower, I packed a bag with a change of clothes and shower supplies, then made a quick breakfast. I hadn't even considered that there was damage to my own home, so I made a thorough inspection of the house and the yard. There were many small branches down on my grass, but nothing serious and nothing that couldn't wait for another day.
The rest of the morning went slow, and I didn't have much appetite for lunch, though I did eat something. I had consumed a lot of water during my time at home knowing I'd be sweating a lot deal with the tree at Cass' house. At 1 pm, I put the chainsaw, a bow saw and work gloves in my car, put on old clothes and work boots and drove over. Rather than knock on the front door and disturb Cass' privacy, I went right to the backyard and got to work. I used the bow saw on the small branches to save gas. I kept checking the patio door to see if Cass was there, but I didn't see any movement. I was certainly making enough noise to announce my presence, so I decided to just focus on my work, and forget everything else. Manual labor had a way of focusing my thoughts so I could ignore stress and anxiety and other negative thoughts.
In less than 30 minutes, I was sweating profusely and cursing that I didn't bring a water bottle with me. I was covered in saw dust and dirt, and didn't want to bring any of it into Cass' clean home. Just as I began on the main branch with the chainsaw, I notice the patio door open out of the corner of my eye. I turned off the chainsaw and looked properly. Cass came out, carrying a large glass full of iced lemonade, wearing a bikini top and matching boyshort-cut bottoms. Her hair was down over her shoulder, and she walked deliberately, swaying her hips slightly. None of the shyness and hesitation from the morning was present. She was a Goddess.
"You've been working hard, haven't you," she purred, handing me the glass and smiling. I took several grateful sips before pausing to speak.
"Thank you, Cass. It's swampy out here. I think I should be done in another half-hour. You will probably have to hire a tree company to haul the logs away. They'll be too thick for the city.
"I'll do that. I would like some of it for firewood for the firepit in the corner." she pointed and I saw the firepit for the first time. It looks cozy and perfect for summer or fall evenings.
"I'll make sure to put some brush and logs over..." I stopped in mid sentence, as my shorts were being unbuttoned. "What the...?" Cass was on her knees before me, unzipping my shorts and pulling them down, along with my boxers. "Cass..."
"Hush now. Drink your lemonade and enjoy, Jason." She smiled up at me, and then grasped my cock, starting to stroke. The look in her eyes told me to be quiet and that she really, really wanted to do this. I was completely hard in a moment, and she wasted not time in sliding her lips down most of my shaft. I groaned and closed my eyes, letting my being focus on the feel of her lips and mouth. I could tell that she was an expert in this, moving up and down without hesitation, using her tongue to explore, and using her hands and fingers to squeeze and to pull slightly on my balls.
My brain became fuzzy with pleasure, barely remembering that it had been so many years since I had a blowjob, and it was the first time for such a good one. As I felt that insistent pressure building, and I tried to fight it, Cass seemed to slow down, squeeze the base of my cock, and shift her focus on other areas. She pulled her mouth away from the head and shaft of my cock, pointing it up and licking and sucking my balls into her mouth. She did not mind my generous sweat in the slightest. I saw her nostril flare, and her eyelids flutter.
In the briefest of pauses, she told me "Spread your legs more," and I complied immediately. Her smile widened and after licking a finger, she started to rub behind my balls, right against my asshole. I tensed, feeling suddenly anxious, but she didn't say anything, or stop the movement of her finger. The sensation distracted me just enough to prevent my orgasm, and after a few moments, it felt like a massage and I relaxed. She must have been waiting for the opportunity, because as soon as my muscles relaxed she pushed with her finger and it popped in to the first knuckle. The sudden sensation, along with renew vigor by her mouth pushed me over rapidly and with a howl I erupted. She took my orgasm in stride, swallowing, leaving her finger tip still until I felt back against the tree branch, panting.
She withdrew her finger, but she kept kissing and licking my softening shaft, her eyes sparkling, her face radiant. When she finally pulled back and stood up, her voice was full of happy laughter.
"Oh, Jason, it's been so long since I've done that for anyone, and you lasted a lot longer than I expected. I'm pretty good you know." She giggled, unabashed, and I laughed softly, still trying to catch my breath.
"You surprised me a bit, you know, with your finger," I muttered. "I haven't had anyone do that to me. I've just done it myself." She winked.
"Once you didn't push me away or really object, I knew I was in the clear. We might have to have a talk about that after you are done working." She leaned forwards and kissed me, sharing my own taste with me. I didn't mind at all, having tasted myself or more than one occasion. I was a little surprised at how strong the taste and smell of sweat was.
"You obviously didn't mind me being so sweaty. It's really hot out here," I said as my eyes start to look down her body. I noticed that her bottoms were tenting prominently with the length of her erect shaft.
"Oh no, I didn't mind at all. If it's fresh sweat. And after watching you working so hard to help me, I just couldn't resist. Besides, I had been hoping to do that last night before..." Her sentence end with a blush, and she looked away. I pulled her into a deep kiss and she melted into me. She pulled away after a moment and turned back towards the house.
"Come in for a snack when you are finished. You can get a shower too." There was a definite sway to her hips as she walked away and I was staring. She looked back over her shoulder, as if to catch me, and I didn't avert my eyes. She smiled delightedly and winked.
I found it a little difficult to restart the chainsaw after Cass went back inside, but I managed and did my best to focus on the task. Though my thoughts were on Cass and the blowjob she had just given me, I had the general focus that comes after an orgasm.
The logs that I didn't think would be useful for the firepit I moved towards the side of the house, in case the city decided to pick it up. Very sweaty, and tired, I retrieved my bag from my car and went into the kitchen. Cass was in front of the sink, humming along with the radio. She turned and grinned.
"Use my shower. You aren't just a regular guest. And take your time. I'm still working on the salad." I nodded and retreated into the house. I did my best not to touch or bump into anything, since I was quite dirty. Not wanting to spend too much time away from Cass, and from lunch, I showered quickly. If it wasn't for the blowjob, I probably would have been tempted to masturbate, but my level of sexual tension was low, for the moment.
I dressed quickly, in tshirt and khaki shorts and returned to kitchen. On the table were fresh cut vegetables, dip and two glasses of iced tea. Cass stood at the sink washing her hands, still humming, though I saw her head tilt in my direction, signalling that she had heard me. I walked up behind her, a little nervous, and kissed her bare shoulder. She sighed softly, and reached behind to cup my cheek.
"I was wondering what your reaction would be when you finished working. I know I surprised you with that blowjob," she whispered.
"Well, a random blowjob doesn't change how attracted I am to you, how much I want to kiss you, how much I trust you," I responded, realizing that my word came out a little awkward. Cass turned rather quickly and stared at me.
"Trust? How can you trust me already?" She looked genuinely surprised. "How do you know that I can trust you?" It was a bit unnerving at how bright and piercing her eyes were. Her hands were on my hips and I sensed that she was ready to push me away. A word that was supposed to be positive suddenly created significant tension. I gathered myself, not looking away, and chose my words with more care.
"We've know each other for almost two years. I've taught you, helped you, listened to you. I've held you in the dark during the storm, and in the middle of the night afterwards. You've trust me with your very personal story, and I recognize how big a deal that is, even after our time as teacher and student." I paused, then continued. "I feel comfortable with you. I have no better way to say it. I normally panic the first time I'm intimate with someone, but in the last 24 hours I was ready to go to bed with you, let you photograph me, and I let you give me a blowjob without hesitation. I TRUST you instinctively. And I know you trust me enough to let me care for you when you are at your most vulnerable, like last night."
I couldn't find anything else useful to say, so I went silently, letting her process my words. Her gaze didn't waver for for several moments, but I saw the softness slowly return to her eyes, and then she was kissing me so hard I nearly fell over backwards. Her mouth devoured mine, and I was barely able to keep up with how quickly her lips and tongue moved. Suddenly, the kiss was broken and she held me very tightly.
"You're right. Completely right. I've had my trust broken so many times that when trust is mentioned, I tighten up inside. I'm sorry. Being open sexually is much easier for me than being open emotionally. It's always been the case." I held her as tight as she held me, until she relaxed. She sniffed, then smiled.
"I might need a nap after all this." She went to the table to wipe her eyes and nose on a napkin, then sat. "Dig in, I'm starving and I'm sure you must be too."
Our snack was pretty quiet, except for a small discussion of the tree and the logs that I left for the firepit. She wanted to have a fire that evening if the weather held up, and I agreed. I helped to clean up and then we went outside to inspect my work. When we were both staring up at the spot on the birch where the branch had split away, Cass took my hand and shivered. No doubt she was remembering the storm from the previous evening, and my arm went around her protectively.
"I didn't sleep well last night, and I'm sure you're tired from getting rid of the branch. Would you like to take a nap this afternoon?" She turned to face me with wide eyes, almost pleading. "With me?" she added, as if wanting to make herself perfectly clear. I nodded. She kisses my cheek and led me by the hand into the house and into the bedroom. Without a word, she undressed me down to my boxers, and then she changed out of her bikini into black boyshorts. She wasn't shy about being nude, so I was curious as to why she wanted to keep us both slightly covered. She sensed me question, and answered it as we fell into bed.
"I usually sleep naked, but I guess I wanted this to be a chaste nap. A restful one for both of us. Some days I can go back and forth wildly between horny and not. I guess today is one of those days. I guess you'll just have to get used to me that way." she said quietly.
"It's alright. I could use the sleep and there is no rush to get into bed," I stopped and we both laughed." You know what I mean," I finished and she kissed me.
I reclined, head on the pillow and Cass rested on her side, head on my shoulder, one leg over mine. The way our bodies fit together was almost magical and I was immediately comfortable. Both of us drifted off to sleep in a matter of moments.
Several hours later, I woke, feeling warm and groggy. I hadn't had a nap like that in years, and I did not want to get up quickly. We somehow switched positions while sleeping, and Cass was behind me, spooning me, her arm over my side. Her hand rested on my belly, and her fingers were moving. I could also feel her cock pressing up against my ass, very erect. That would take some getting used to.
"Wakey, wakey," I heard Cass purr close to my ear. "I was wondering how long I would have to lay here before you finally woke up." I turned and face her and she surprised me with a passionate kiss.
"How long have you been awake?" I asked, breaking the kiss and looking into her eyes.
"Oh, about twenty minutes. I thought about getting up, but laying with you is so comfortable and relaxing, I couldn't give it up. Beside, I love the feel of your hairy chest and belly." She placed two hands on my chest.
"I'm not complaining, though I'm surprised I didn't wake up for being poked," I laughed and looked down at her tented boyshorts. She blushed.
"Well, I can't help it. You're wonderful, sexy and a great cuddler. That turns me on." One of her hands left my chest and slid around her cock, then her balls, showing off to me. "I may have to take care of this soon."
"You will? Isn't that for me to do?" I asked, rather surprised. I was a little nervous, since I had never touched another person's cock before, but I wanted to please Cass in a big way.
"Ummm... I guess... you don't have to..." she muttered. "I know it's new for you and I didn't want to rush..." I cut her off by pulling away and moving down by her feet. I pushed them apart, and reached out, tugging at her boyshorts until they started to come down. I had them off in and instant, and I grasped her shaft without hesitating. The skin was surprisingly soft and very warm. She sat up, looking shocked, but a big smile grew on her lips.
I moved forwards, still stroking, then I leaned it for a better look. I had seen her the previous evening, but the light wasn't very good, so I didn't take in all the details. Up close, she felt and looked bigger than she looked, especially the head. I licked my lips nervously, but after a deep breath, I opened my mouth, careful of covering my teeth, and took her head into my mouth. A deep groan from Cass told me that she was happy where this was going.
I was instantly in love with how her smooth cockhead tasted, and how the skin gave to the pressure of my lips. I moved my tongue slowly around the head, finding the slit, and then gently sucked again. All the techniques I remembered watching in porn, and what little I had known from actual blowjobs came back to my head. I decided to put all of it aside and just find out what Cass liked. I reached down a little further and held her smooth ball sac in my fingers. I was completely devoid of hair, soft and wrinkled. As I continued to pleasure her cockhead, my fingers explored, not only her balls but also her inner thighs and her asshole.
I could tell that Cass was loving the blowjob so far, but my head was focused on how much I was enjoying it. I had thought of giving blowjobs before, perhaps hooking up with a guy, but as with women, I was far too scared to initiate. As I start to take some of the shaft, and feel the head of Cass' cock sliding along the top of my mouth, I felt very comfortable, even eager to do more.
"No need to force yourself. It's your first time, I gather," purred Cass. I made some kind of grunt, but I continue to bob slowly up and down, each time letting the head hit the roof of my mouth. My finger dove down between Cass' soft cheek and found her hole. A subtle shift of Cass' weight and move of her legs told me she approved. I just let my fingertip caress and push a little at the entrance, rather than push inside. I knew it would be rough without any kind of lubricant, and my mouth was far too happy to take a break.
As the moments passed, I was aware that Cass' breathing was faster, her body moved more, and her cock seemed to grow slightly in my grip, so I knew her orgasm was close. I felt a little disappointment in the back of my mind, thinking that it would be over, then I reminded myself that Cass and I were just starting as lovers, and I would be getting a second chance. I quickened my pace, and after several more moments, Cass grunted," If you don't want to taste yet, I..."
I silenced her with a look and though I pulled my lips back around the head, I pressed them sealing, telling her I was ready. Her hand on the top of my head, she screamed and I got my first taste of cum. I was swallowing before the first jet hit my tongue, so at first, I didn't get a proper taste until she released more. I expected a stronger, more unpleasant liquid, but her cum was slightly salty and musky, but otherwise nondescript. As I swallowed I must have looked lost in thought, because Cass was suddenly stroking my cheek and asking me if I was okay. A few more licks of her head and I pull back, licking my lips.
"No, I'm fine. In fact, I'm great. That was wonderful and intense and erotic, and I was happy to do that for you." She pulled me up hard and kissed me passionately, then broke off.
"Oh my, you really did enjoy it, didn't you." I was confused at first to what she meant, but when she looked down my body, I understood. My own cock was achingly erect, and had been the entire time, thought I hadn't paid attention to it. I smiled rather sheepishly. "No, don't be embarrassed, honey. Be happy and proud."
She quickly flipped me over and then considered me for a moment. She retrieved a bottle of lube from beside the bed and poured some on her hands.
"Just relax. Completely relax." She kissed the very tip of my cock, then then started stroking with both her lubed hands. The feeling was exquisite, almost as good as sex, and I really did relax and enjoy it. I didn't think I would be able to last, as aroused as I was, but Cass had an instinct on when to slow down and ease me back. I had closed my eye when her fingers began to squeeze and massage my balls, but I opened them again when her wet finger probe further down, against my anus. She just massaged there and push slightly until I really relaxed, and then she slid her finger into me, without hesitating. I could feel the digit moving, twisting, until there was a sudden intense sensation inside and I felt like I was going to erupt that instant. I didn't, but I stared at Cass, who was beaming.
"You can just let go, now." The way she spoke, with experience, and with a gentle tone, helped me trust her completely. Cass started moving her finger again, but not in a thrusting motion. Her finger flicked back and forth over my prostate and I could barely stay in place. I was surprised when my penis started to soften for a moment, enough that I panicked a little bit. Cass smiled reassuringly, but didn't start stroking my shaft again.
"Don't worry about that. You are just reacting to having my finger inside, and the intensity of the experience. Sometime when I'm over aroused, I soften, just because my body doesn't want to release yet. Trust me, honey, don't worry." I tried to relax as much as I could, but I really did feel like I was going to explode if I didn't orgasm. I saw clear fluid starting to leak out of my slit. Instead of stroking, Cass squeezed, as though trying to milk me. More of the fluid streamed out as her finger again moved inside me. My hands reach out and gripped the bed, and I felt like I couldn't stand much more of this, even though Cass had only begun.
She placed soft kisses on the head of my cock and on my belly as she massaged my prostate, before eventually taking me back into her mouth. It seemed like an eternity, but I grew erect again, and before long I was aching to erupt. I couldn't control my muscles any more and I thought that I was going to tear Cass' finger off. She knew exactly what she was doing, and gave me a simple look letting me know it was okay to orgasm. I felt afraid to really let go, but my body took over, and I tensed, with such a powerful orgasm that I thought I might pass out. My eyes closed and my back arched, making it difficult to keep my hips in place. I did so, just barely, for Cass' benefit. I figured that I had released a fountain.
When I finally looked down and saw Cass licking her lips, not a dribble of cum spilled, I took a deep breath. Her finger was still inside me, but I could tell that it was slowly being drawn out.
"Stay here, don't move, and breath deeply." She went quickly to the bathroom, and I heard the water running for quite sometime. I did focus on breathing, processing what had just occurred. I felt empty, and slightly uncomfortable, but I didn't really mind it. I guessed that everyone who had been taken in the ass felt similar afterwards. And this was only Cass' finger. I began to wonder what it would be like to take her cock, when Cass came back out with a towel and a wet washcloth.
"It takes a long time for the hot water to get going, so I apologize. You haven't felt any... urge to go?" she asked softly as she knelt before me.
"Um... no, not really. Just empty, and a little soreness," I responded getting up on my elbows. Cass slowly cleaned my cock, thighs, balls and ass. She also seemed to be checking for any bleeding.
"That's very good. I was as careful as I could, but anal play can be a little risky. I've done it with gloves before, but with you, I didn't want that barrier." She smiled up at me, took the washcloth back to the bathroom, then came back to kiss me.
"And how do you feel emotionally?" Her eyes locked onto mine, and I felt a little tension in the moment. Her fingers stoked my face, and I realized that I would have to pick my words carefully again.
"I feel very close to you, and not just physically. I know it takes a lot of trust to let someone do what you just did. I do trust you." She nodded, but keep that steely lock on my eyes, wanting more. So I continued, telling her exactly what I had been thinking. "Just before you came back out with the washcloth, I start to imagine you fucking me there, and not just with your fingers." Her eye brows raised, and I saw her lips twitch a little. "With your cock," I added, with conviction, trying to emphasize it enough for her. She broke into a grin.
"I'm really glad, Jason. It's not a requirement, despite what the smile on my face might say, but I've enjoyed fucking boys in the past, and it something I would want to do with a partner I really loved." She put her head down on my chest and snuggled me. "To be honest, I prefer to take rather than give most of the time. But I want... no I need variety." She sat up suddenly and stared at me with a slight frown. "Not that I mean other lovers, or anything. I'm not like that. I just like sex, different kinds of sex and..." I stopped her with a kiss, and held her tightly.
"I get it Cass, and I want the same thing. You'll probably have to teach me a lot, but I'll be a willing student, to be sure." I whispered and kissed her forehead.
"Turnabout is fair play, as the say?" she asked demurely and nipped at my chest.
"Um... yeah."
We rested in silence, as the afternoon faded and soon it was dusk, and I could tell from various rumbling sounds that we were both hungry.
"Chinese?" We both said at the exact same time, and then laughed.