NOT Your Grandma's Book of Progressive Erotica: Vol 3

MTT

My friend and I went way back to when she had already started her transition to becoming a woman from the man she was born as. I was never one to judge others, or exclude them for being different – I included everyone in my life. There were, are and always will be things that I don't quite understand, but my curiosity helps me construct questions so that I might be able to better understand things in this world. Being a transgender woman is one of them.

I had only met up with my friend on a few occasions due to our busy lives, so our friendship had mainly been an online one. We have shared a lot with each other over the years from heartbreak, struggle, to even one night of wild, hot sex.

It was the first night we had agreed to meet, which was after talking online for several months and getting to know each other. She was a sweet girl and I supported her throughout her transition to a full-time woman. If someone wasn't comfortable in their own skin, they had the right to change that so they were. Giving my friend support was something I would have done for anyone because that's just the guy I was.

When I picked her up from the bar she was at, she was with her friend, who was also transgender, but I had no idea until later that night. She had a bestfriend who I expected to be with her, but instead a rather attractive girl hopped in the back of my car. We were introduced and then we went back to my place for some drinks.

They had stuffed bottles of vodka in their purses and revealed them to me as we walked into my kitchen. I was surprised and rather impressed all at the same time – I also learned why women have such large purses.

After mixing a few drinks and playing some drinking games with a deck of cards, everyone wanted another round. Once we hit our fourth round, all three of us were getting rather loose and I soon found myself being led to my own bedroom by her friend. As I laid down on my back, her friend straddled me and then told her to join us.

"So, are you ready for some fun tranny chaser?" she asked.

"Tranny chaser?"

Yup, I couldn't even tell that her friend was transgender until then. I knew there was something different about her, but I honestly had no idea. Seeing as I was drunk enough to loosen up, I figured what the heck, I'll go for it.

Her friend smiled at me and then started making out with me. Again, I would have never guessed she was born a guy by the way she kissed me. She was smoking hot, slender, had nice eyes and long brown hair. My friend was a bit bigger than average, with rather large breasts and dark features. I had the best of both worlds in front of me – both physically and sexually.

My friend sat down on the bed as her friend undid my jeans and pulled them down to reveal my semi hard-on. She immediately started sucking my cock and in a matter of seconds I was rock hard and in her mouth. She continued sucking me off as my friend sat timidly beside her and watched.

"C'mon, he's your friend after all," she said to my friend, placing her hand on my cock. Slowly she jerked me and then worked up to going down on me. My friend's lips felt amazing as they wrapped around my cock. She wasn't as good with her tongue as her friend, but she definitely made up for what she couldn't offer me with those big lips of hers.

Soon they were sharing my cock in their mouths and licking each side with their tongues as well. I was having the time of my life thanks to vodka and when her friend got naked and whipped out her cock, it didn't faze me one bit.

As she stroked her own cock, my friend continued to suck mine. Eventually her friend then laid down next to me, sticking her cock next to mine and forcing my friend to suck on both of them.

Her friend kissed me and whispered, "You wanna fuck me?".

I nodded to her and she then straddled me once more, sliding my cock into her tight ass as her cock dangled in front of me. She rode it better than most girls I had been with, but I was slightly distracted by my friend who seemed left out. I tugged at her clothes and gave her a wink. She got the hint and stripped down as quickly as she could. Getting back onto the bed next to me as her friend rode my cock, I grabbed her and started making out with her. Not only were her lips good for sucking cock, but she was a great kisser as well. I began to stroke her cock as if it were my own and grabbed onto one of her breasts at a time with my free hand. Her breasts were so big I probably could have titty fucked her if I wanted.

"I want to fuck you now," I whispered into my friend's ear.

She smiled and then waited for me to get up. I had her bend over doggy style and then gently entered into her ass. It was so big and round that it was perfect for the position. Her curly black hair was then pushed back and her friend stuck her cock into her mouth as I fucked her from behind.

I had never planned for my friend to be in the middle, but I was kind of glad that it wasn't me. Despite being drunk, I didn't think I was ready to take it in the ass just yet.

Fucking my friend in the ass for quite some time, I found myself getting closer and closer to cumming. Her juicy ass was doing the trick and seeing her suck her friend's cock was actually quite arousing as well.

A few minutes later, I announced to them, "I'm gonna cum."

My friend quickly turned over as I pulled out and then knelt beside her as I shot hot cum all over her lips and into her mouth. She licked at the drops that landed outside her mouth as her friend then made out with me. Soon her friend was cumming onto her face as well, but missed badly and shot cum into her hair and on her forehead.

"I'm sorry," she laughed. "I honestly didn't mean to."

My friend rolled her eyes and then sucked on my cock a bit more in appreciation of me not cumming so close to her eyes.

"Nobody is ever going to believe me about this night you know."

Her friend then grabbed her cell phone from her purse and knelt on the bed again next to her as she continued to suck my cock.

"We can take a few happy ending photos, then they will!"