NOT Your Grandma's Book of Progressive Erotica: Vol 1

Training Day

Being single for five years had made me unaware of how much the dating scene had changed. I had made several accounts on dating sites, or apps on my phone, but every time I found a nice woman, something would always go wrong. It was like I was cursed– cursed to never find happiness in this vast world. I saw my thirty-two year old aging self as unwanted, unattractive and no good for anyone. Woman would see me as a sweet, caring guy who was funny, but when it came to love, things never worked. I felt like an outcast, as if I was broken, severely different, or incapable of connecting with someone on such a level that I could settle down and spend the rest of my life with another individual.

Coming home to my farmhouse late at night, I would drive roughly thirty minutes to get there from where I worked in the city as an editor for a small publishing firm. I enjoyed my work, but my life never felt fulfilled. I had my cat, Felix, to come home to every day and an abundance of novels and old vinyl records, as well as CDs. I had a small garden on the property, which allowed me to save money and eat organically whenever I pleased. The rest of my property was littered with saplings, which I intended on growing up so I wouldn't have so much grass to cut. Riding on the lawn tractor every Saturday afternoon wasn't difficult, but I enjoyed the idea of privacy from a sprouting forest and I would much rather invest my time and energy into projects of my own than trimming mother nature's bush.

Bringing my glass to my lips to take a sip of the dessert wine a friend of mine had bought me for my birthday, I sorted through my mail on the kitchen island. Most of the letters were late birthday cards, presumably because they dropped it in the wrong mailbox again. I rarely got mail, so this was one of those nights where I actually got out my fancy letter opener to make the task simple. The wine was quite flavourful and I had thanked my friend, hinting that I would appreciate another bottle at any time in the future. After opening my last birthday card, I fed Felix his last meal of the day and then made my way to my bedroom. It was Friday night and it had been a long week for me, so I was planning on sleeping in and then going out by myself Saturday night to revisit the dating scene at a club in the city.

Arriving at the club in my tight fitting navy blue pants and white, long-sleeved shirt with the sleeves rolled halfway, I sat in my car to check myself over in the mirror. I wasn't concerned about my hair, but I felt like I needed to give myself a pep talk so I could be more confident if I left alone, or without a phone number.

Oddly enough, I bumped into an old friend from college who was visiting from out of town. We sat together at the bar and had a couple of drinks as she told me about her new job at a cosmetics retailer. I had been introduced to her by a friend of mine and had shown interest in dating her, but it never went further than a first date for coffee. She admitted to me shortly after the date that she wasn't like every other woman.

Being a transgender woman never bothered me, but we never really had any chemistry, so we just stayed friends over the years. She had gone through many transformations over the years with procedures to get the body she felt most comfortable in. I stood by her side through it all and supported her no matter what like a friend good is supposed to do.

As we continued to have drinks, she divulged that she had yet to be with anyone sexually and so I probed her a bit with some questions. It seemed that she just hadn't found the right guy yet, just as I hadn't found the right girl to settle down with. I told her how things were working out for me and she spoke encouraging words about keeping my head up and that one day the person would come into my life when I least expected them to. She had been there for me through my other breakups and always said that I deserved better. She was right, but I was having a hard time finding love and not dating for five years wasn't helping.

Many drinks and songs later, a rather attractive woman walked up to my friend and whispered in her ear. Little did I know at that moment, they were friends and had come to the club together. My friend introduced us and then we spent the rest of the night in a booth that opened up, drinking, laughing and sharing stories.

By the time last call was announced, we were already well into our second coffees at the coffee shop across the street. My friend told me that her and her friend had arrived by taxi and that they would need rides home. I didn't remember where my friend's mom lived, but she was the first one to be dropped off at the end of the night.

As I waited for her to go inside her house, her friend got in the front seat and buckled up. We both waved to her and then I backed out of the driveway. As I headed down the road to the main street, I looked over at her and smiled. She was more attractive than my friend, but I wasn't sure what she thought of me.

During the conversation over drinks I had pieced together that she was a transgender woman as well, but I honestly couldn't tell. If my friend and her hadn't dropped subtle hints all night long, I wouldn't have known any better until we tried to have sex.

"Do you want to go somewhere?" she asked, as I came to a stop sign. I looked over at her and smiled. I hesitated for a moment as I bit my lip and thought about where we would go and what we might end up doing together.

"Yeah," I finally replied, with a bashful smile.

"Turn right, I know of a place." As I followed the rest of her directions, I found myself driving to a part of her town that I wasn't familiar with. Our destination was a parking lot near a beach that was completely deserted at night. I parked somewhere near the middle and then shut the car off so that we were in complete darkness. I undid my seat belt and then waited for her to do the same.

Looking over at her, I really wanted her to make the first move, but I knew that it probably wouldn't happen. If I wanted to kiss her, I had to make the move to initiate it myself and then see how things unfolded from there. I leaned over to her, placing my fingers under her chin and then gently kissed her. Her lips were soft and it felt so natural. It wasn't awkward and unless told beforehand, I would have never guessed she was born a guy.

We continued to kiss for quite some time until she reached over and started groping my dick. I was hard the second I started kissing her, so I pulled her hand back and guided it down my pants. She eagerly went all the way down and began to squeeze my dick. I stopped kissing her, undid my belt and then unzipped my pants for her to have complete access.

She looked over at me and asked, "Are you sure?"

"Yes," I replied quietly as I kissed her once more. She leaned forward and then stuck my dick in her mouth. It was warm like any other woman's I had had before and after a few minutes of her using some tongue techniques, I'd swear she was probably the best one too. I played with her long blonde hair a bit as she sucked and jerked my dick, then I noticed she was playing with herself. I pulled my dick from her mouth and then slapped it against her mouth a bit. "Do you want me to fuck you?"

"Yes," she replied, sitting up to look at me. "But I don't have any condoms, so I'll suck you off until you cum in my mouth. If I knew I was going to be seeing you tonight, I would have came prepared." She then dropped her head back down and began to suck my dick again.

"Could we fuck next time?" I asked. She stopped sucking my dick and pulled it out of her mouth.

"Make sure you get my number before you drop me off and I'll show you just how good a transgender woman can be."