The sexual high of Halloween weekend came crashing down three weeks later when Missy stopped by my house unexpectedly. She was in tears. I assumed the worst, thinking something had happened at school. It was far worse. Missy’s brother and I had grown apart. I was a jock by day, diva by night kind of guy. He was kind of a stoner who had abandoned our friend group. So while it wasn’t surprising he wasn’t the one delivering the news, having a tearful Missy show up at my front door was.

“My family is moving to London. They are making us all go with them.”

The words hit me like lead brick. Surely Missy must be pulling a prank. She was not.

“My dad took a promotion with his job and they asked him to relocate to London for the next three years. This sucks.”

It took a moment for the reality to set in. My mentor and confidant would be leaving me. My guide to a very alternative world I was exploring was going to be an ocean away. I felt deflated. Missy started to cry again. Life suddenly sucked in a big way.

Less than a month later, Missy and her family were gone. My spirits deflated.

****

Without Missy, my explorative drive disappeared. With no one to push me and no real direction, I purged the small collection of attire that I had accumulated and swore off my alternative lifestyle. My final year in high school was relatively uneventful and what I would categorize as predictable. Football and baseball came and went, as did homecoming and prom. It was by all measures, a standard high school senior year.

My decision to go to a large public university was in very many ways a chance for me to blend in and perhaps recapture even a small part of what I had. I wanted to experiment again and was motivated when I arrived on campus. That didn’t exactly work out as I planned. Freshman year was a drunken blur and sophomore year was a giant party. Trust me, good times were had but nothing along the lines of what I had experienced in high school. The big move for me heading into my junior year was landing in a sweet apartment with a very open minded and mature roommate named Sal. His girlfriend Sophie was a frequent visitor and very cool as well. We all spent the summer taking classes and had plenty of time on our hands for drinking and conversation.

On one particular evening, with more than a few drinks involved, I revealed that I in fact had not only had sex with a man but also that I had done so crossdressed as a girl. Both Sal and Sophie were intrigued and we literally spent the rest of the night talking about my experiences as a girl. Eventually I was asked if I would ever do it again. By the end of the night, while Sal had made it perfectly clear that while he didn’t see a future for he and I to hook up, he was perfectly cool if I ever wanted to venture into dressing again. He even went so far as to say I was welcome to do anything I'd like in the apartment. Sophie was taking it all in and I wasn't really sure where she stood until she blurted out that she couldn't beleive what she was hearing and one hundred percent wanted to help me! It wasn't long after that a day out shopping was set up for the next day.

I woke up slightly hung over but with a renewed energy. Staring up at the ceiling, I was trying to grasp the concept of what day of the week it was. Realizing it was Friday and I didn’t have any classes, I jumped out of bed, took a few aspirin and started my day. Sophie was sitting on the couch sipping a cup of coffee. Sal was at class.

“OK. Absolutely mind blown by our conversation last night. I would have never thought that you would be bisexual and a crossdresser. Never.”

“Well we all have our little secrets don’t we?”

“Little secrets? I would have never in a million years. Seriously, though, I want to hear so much more. And my offer does stand. I would love to shop with you. Are we still on for today?”

“Yeah, that would be great. I literally threw everything away a few years back. I have nothing. So let me wrap my hands around things again and figure out everything I need. And makeup. Oh man, my friend Missy always had me covered on that front. That’s really what I need help with.”

Sophie had gone and pulled out a note book and began writing a list. We talk about clothes that would work and what wouldn’t. We covered make up, accessories, shoes and maybe even a wig. To say she was into helping me was an understatement. It was about an hour or so later that Sophie proclaimed us ready to roll and off we went to the mall.

We returned a few hours later with a few outfits to start with and an array of makeup to get me started again. One of my first purchases of the day was a lacey blue and white bra and panties set that I immediately went and put on in the restroom. I forgot how much I loved the feel of silk rubbing against my cock and covering my ass. Once we got home, it was time to try things on and while I hadn’t purchased a lot, the fashion show had taken over hour. Now it was make up time.

Sophie was not quite the wizard that Missy was but she was more than proficient in not only making me up, but also giving me a little tutorial while she worked her magic. While my hair wasn’t quite as long and flowing as my high school locks, Sophie was able to work a few well placed curls in while styling it. It had a subtle feminine look. A new look. It was minutes after we had finished that Sal came home. His stunned silence told me one thing. Jenni was back.

****

Fall semester had rolled around and I had written a short story for an English class whose main character was a crossdresser. I thought it was cleverly written with the big reveal being that the two main characters were actually the same person. I thought it was great. There were fourteen students in the class and to a person, everyone loved it. Everyone loved it except my professor. He didn’t get it at all. He gave me a “C-“, calling my work confusing and complicated.

My professor was surprisingly conservative for an English professor. The idea of a male dressing like a woman and actually seducing another male was a foreign concept to him. My meeting with him was cordial but frustrating. While he was complimentary about my writing style he conceptually couldn’t get over the thought of a man being that convincing that he could fool anyone. The grade was meaningless at this point. It wasn’t like I was failing the class by any means. I took it as a challenge to convince him. I suggested he meet a “friend” of mine and perhaps she could convince him. If she could, he would change my grade to an “A”. He agreed to meet but wouldn’t make any guarantees about the grade.

The meeting was set for 8pm on a Tuesday night, his one night with evening office hours. Typically, not many students would be venturing out to meet their English professor on a Tuesday night, so that would give me time to work my magic. The idea was that my “friend” Jenni and I would be coming to talk about my paper. In reality he would just be meeting Jenni. I started thinking about what to wear from the time I left his office. He was conservative, so I couldn’t go overly sexy. Under dressing might not be effectively convincing.

Sophie and I spent the weekend shopping and trying out different looks. I had things planned out until an early snow fall and twenty degree temperature drop changed my plans. The final decision was a cream sweater over a long skirt with a cute pair of boots. It was a very collegiate look. Tuesday came and Sophie came over to help me get ready. She and I had bonded nicely and she was insistent that she was there to do my makeup. Sal was so into things that he blew off his Tuesday class to check me out before I left. With my hair styled and a killer set of fake nails, I was off.

As I was driving over to his office, I started to think what I should even say. I hadn’t put much thought into that part at all. I just figured I’d walk into his office, his jaw would drop and he’d give me my ‘A’. But it suddenly hit me that he was going to want more than that … and he thought it was me and my friend Jenni coming to meet him.

I parked in the student lot and had to walk a block or two to his office. I certainly blended right in with my back pack over my shoulder and a cute collegiate look. When I got a smile and “hi” from a guy I walked past, I knew I was looking good. I made my way into Wooden Hall and up to the second floor that was primarily all professor and teaching assistant offices. A few office doors were open including his. As I approached his office, a woman who had taught two of my classes the previous year, walked out of her office and closed her door behind her. She and I had a great relationship and I instinctually said hello. She casually said hello and kept walking. I knew I was in good shape if she didn’t recognize me.

As I approached the professor’s open door I could feel that confidence I had coming back in full force. I peeked my head around the door while knocking.

“Professor Lambert?”

“Why yes. Oh you must be Jenni, right?” he said as he got up from behind his desk and approached me. He had no idea. He reached out his hand and said it was great to meet me.

“So I thought you would have come over with your friend? He's pretty convinced you will be able to convince me that his story he wrote was better than I believed it to be. Come in and sit down.”

“Maybe he’s just running late,” I said as I sat down on an aged wooden chair.

Part of me was wondering if he knew and was just messing with me. However, as our conversation continued I realized that he honestly had no idea it was me. He said he was surprised I was late I was and that it was quite rude it was to keep such a cute friend waiting. He had no clue.

Our conversation continued for about ten minutes before I figured it was time to break the news.

“Well Professor, I know the grade doesn’t mean much but if I were you, I would change the grade to the 'A 'you know I deserve.”

“I’m sorry, what was that?”

“My grade. It should be an A.” I paused. “Professor Lambert, it’s me. I am Jenni.”

He stood there in stunned silence, uncomfortably adjusting himself in his old leather desk chair. I explained to him that the story I wrote was really based on a real like experience that I had had. I went on and on, probably talking too long and after about five minutes of me rambling, he was still speechless. I wasn’t sure if that was a good thing or a bad thing until he broke his silence by saying that I was right. He was amazed. He followed up with several generic questions about crossdressing and my experiences and then his questions got a little more personal.

“So, how does it feel to have a man look at you and know he is turned on?”

“Let me ask you,” I quickly countered, “how does it feel when you flirt with a cute girl and find out she’s not completely a girl? The way you were talking to me? Admit it, you think Jenni is cute. Why else would you take your wedding ring off?”

His face was turning red.

“I’m sorry,” I said as I stood to leave. “I shouldn’t have said that. But I hope I proved my point.”

“No, no. Sit down,” he said as he got up quickly, motioning me to sit back down. “Do you mind if I close the door? I have another question or two for you, but maybe they may be a little more private.”

I went back to sit down as Professor Lambert closed the door, turning the lock as he did. He sat down on the chair next to me.

“Now first, for the record, I am divorced. I just wear the ring to wear the ring. I have many students who come in to the office. Cute girls and, well, I guess cute guys. And yes, I admit, I find you to be more than cute. You’re adorable. Quite frankly, I like Jenni quite a bit.”

The professor paused for a moment and appeared in deep thought.

“You wrote about several intimate moments in your story. Did you really have those experiences? I mean, have you really been with other males?”

I explained to him that I everything I described in my story was real life. I told him so many of my experience were really about self discovery. 

“Until you’ve lived the experience, it is sometimes hard to understand. Some people feel kissing is the most intimate connection two can have, for others its sex.” With a laugh, I told him “If it wasn’t so inappropriate I would show you.”

We both laughed. He then stood and walked to his office door, open it to look outside and closed it again. He hesitated before locking the door again then turned back around.

“I’m inclined to give raise your grade to a ‘B’ only because it might seem suspicious if I raised you two letter grades. It also appears that there aren’t any more students looking to meet so my office hours are officially over.”

“Thank you so much” I said as I was standing up to leave. He motioned to wait.

“If I said I was curious and that it was ok, after all it is after office hours, would you like to show me what you mean by ‘intimacy’? Just how convincing can you be?”

I asked him again if he thought it was a good idea. He said that it was completely up to me. And then repeated himself as he walked toward me. I looked and felt conflicted.

“Let me make this easier for you. I would you like to show me,” he said softly.

This was not the direction I thought the meeting would take but I was curiously aroused to the point where I stepped toward him, touched his face and moved my lips toward his to kiss him. Our lips met briefly before I pulled away and apologized.

“OK. I’m sorry. This was not my intention when I came to meet tonight.”

“There is no need to apologize. Your honesty was very believable and quite charming,” as he pushed my hair away from my face. He walked back toward his desk and started putting things into his bag to leave.

“Please remember to tell your friend that his C- is now a B. Have a nice evening. It was wonderful getting to meet you, Jenni.”

I was free to leave but I didn’t. Maybe it was the pent up frustration. Maybe it was the moment or just that it felt good to be Jenni again. Or maybe it was that I was just really horny. There was something about the situation that I couldn’t resist. I looked at the locked door and then turned to him.

He took his glasses off, set them down on his desk. I made eye contact with him as I walked around his desk and very assertively put my lips on his again. This time I didn’t pull away. His hands made their way toward my ass, rubbing and squeezing it gently as we kissed. He quickly introduced his tongue to our kiss and I did as well. This was definitely not how I thought this would go but I was enjoying myself for sure. By the bulge I could feel growing in his pants, he was enjoying it as well.

I asked him how far he really wanted to take this. He said there were limits as to what could happen in the office but he was curious to see what else I could offer. I looked down between his legs and let my hand slowly slide over his pants, outlining his cock. I didn’t say anything, figuring he would stop me if one of his limits was crossed.

I went to loosen this belt, undo his pants and carefully take his zipper down. His cock was pushing the fabric on his tight fitting briefs out enough to see that he wasn’t long but very thick. I reached down, pulled his briefs back and freed his cock. It was five inches and maybe the thickest dick I had ever seen.

I admired my work for a moment. Our lips met again, our kiss was deep and passionate. I slowly stroked his cock while we kissed. I was standing in front of my professor with his pants at his ankles and his thick cock pulled out over his shorts. I knelt down in front of him pulling his briefs to the floor. I took his cock in my hands and started to stroke it. It was thicker than it looked for sure. His balls were the biggest I had ever seen. My other hand started to fondle his sack, softly rubbing his balls. His groan let me know I was doing just fine. I told him to sit.

I took his head in my mouth and felt his cock start to twitch. It grew even more as I took more of it in my mouth. His hands made their way to the top of my head and slowly pushed my mouth down on his cock. My mouth was wide open and it filled it nicely. I worked as deep as I could go and then slowly licked back to the tip. My saliva was dripping from his dick. My tongue licked back down to his balls. I took one in my mouth and let my lips kiss it as I released. I repeated this on his other ball before trying to take both in my mouth.

“Oh fuck, yes!!” was all in needed to know that the Professor was more than enjoying himself.

I went back to his cock, completely enjoying its unique size. I was lost I the moment working my mouth all over his cock. My tongue would lick up and back, lick the tip and then my mouth would engulf his cock again. It was after a few minutes, the Professor hands were on the back of my head again, this time forcefully pushing my head down on his cock and holding it there until I gagged.

I had never been so aroused. My own cock was rock hard, but well hidden. After about ten minutes of the most intense blow job I had ever given, I tasted a little pre-cum and just seconds later streams of cum started filling my mouth. I swallowed after about the third or fourth shot. Another three or four followed. I swallowed it all.

I took a few moments to lick him clean and rub his cock all over my face. I couldn’t resist sucking on his balls a few more time either. I stood up and very casually adjusted myself, reached for my purse to put a little lip gloss back on and powder myself before I left. The professor seemingly had other plans.

“Don’t go just yet,” he said, pulling his pants up and putting himself back together. “That was incredible and I am just in awe. I …” Professor Lambert went speechless.

I walked back to him and started to kiss him again, rubbing his cock as I did. He was a damn good kisser for sure and his cock was coming back to life very quickly.

“OK, as much as I loved your cock and I could swallow your cum all night, maybe we should figure out another time and place to meet again,” I suggested. “Because you’re horny and I’m horny and that just means at one point you’re going to want to stick that inside of me.”

“So why don’t we agree on a different setting. No strings attached. And we can have a little more private time to, shall we say, research the topic of intimacy.”

The Professor agreed. He had an apartment just off campus and asked about this Friday night. He said it was the single most amazing blowjob he had ever experienced. Words could not describe it, according to him. And yes, he definitely wanted more… research.

We put our coats on, grabbed our bags and were heading out the door. Before he turned the lock on the door he turned and kissed me again. This time it was a simple kiss, lips on lips.

“So is Friday a date?” he asked.

“Friday is good. But don’t call it a date. Call it extra credit.”

“That sounds good to me,” he replied.

I walked to my car in a euphoric state that I hadn’t experienced in quite some time. I replayed everything in my head that had happened, laughing out loud a few times and curiously wondering what I had gotten myself into along the way. At the apartment, Sophie and Sal got the entire scoop and for the first time in a while I felt fully emerged into Jenni.

In bed that night, I started my preparation for Friday by pleasuring myself with the larger of my two dildos. I heard Sophie and Sal making love in the other room as I longed to join them. It was feeling I had never really had before but laying in bed that night things were different. I stroked myself to two of the most powerful orgasms I had experienced in years all while fucking myself with great pleasure and listening to my roommates ravage each other for over an hour. My own cum had never tasted as sweet as that night as I fantasized taking every last drop from the Professor just hours before. I fell asleep fantasizing about Friday, wishing it were tomorrow, but happy to have a few days to prepare.