My Evolving Transition Ch. 01

My Evolving Transition - 1. The Beginning

Introduction:

I had lived in a loft behind my mom's subdivided house. Until I met my girlfriend, I didn't know whether I was a Jack or a Jill or both, while also being a shy virgin. Here begins my journey.

(Originally posted as known as Teasin' Pleasin 01 under my old Profile)

The Story:

I was not long out of school at eighteen, and my girlfriend for the past few months was twenty, almost twenty-one. I was athletically built and, rather good-looking, most girls flirted with me at school, but I didn't take the hint and finished school alone as a virgin. Then you have my Tiffany, a girl every red-blooded dude with a cock would stare at if she walked by them. She had reddish-blonde dreadlocks, a seductive smile, blue eyes, and reasonably sized breasts. I thought I won the lottery when I first hooked up with her. There was a downside, if she told me to do something, I would do it. Little did I know, she was grooming for something more.

What began with a whirlwind romance where we had sex at least every day or whenever we could. In the beginning, we fucked like rabbits but then after three months, it started to feel stale. It was around that time I'd started thinking I was a girl trapped in a man's body, and I lost the thrill of normal sex.

It looked like it was over, between us. Although I was straight by nature, I started to stroke my cock while watching bisexual, or tranny porn, in secret. I also suspected that I wasn't the only guy she was screwing.

We both held secrets.

Once Tiffany suspected I knew and she also found out about my secret fantasies on my computer, she decided to try to spice our life before we couldn't.

She never denied the fact, she plays the field and left it up to me if we were to continue. So, after some research, she drops me an idea, about pegging. She thought she'd spice up our love life, by pegging me with a strap-on and killing my curiosity with trannies and gay sex.

"That's gay, I'm not gay," I said.

At first, I was cold to the idea before giving it some thought.

We debated it, then she convinced me.

"Yeah right, I've seen your secret of websites, you may not be gay, but you've fantasized about it," She snapped at me with a smirk.

"I've heard from my friends, that it feels amazing, just think about it before closing the door on it, pretty please," she said compassionately. I was still weighing up the pros and cons.

"It's not gay, it's just what couples do in straight relationships and relieve guys of prostate pressure," She sounded convincing. I didn't know why I was fighting against the idea, which I was curious about anyway.

"I will go shopping tomorrow and Friday night, we'll have some fun," she said with a smile. She seemed more into it than I was.

The next day after work, Tiff came over to my loft. She was all smiles and quickly entered my open door. We went upstairs to my bedroom, and she showed me what she bought. I watched her struggle to unpack the plastic cover, my cock grew watching her. Once she unpacked the strap-on, I was mortified once I saw the size and thickness of the item.

She then left the item in my loft until Friday, which gave me time to inspect it.

When Friday came, I stood there watching her attach the harness and then tease me with it. I acted annoyed but deep down I was nervous.

"Now, come over here and lie down," she pointed. I sat down on my bed and then lay on my back, while she climbed on top of me. Then we started kissing while wrestling each other's clothes off.

After a few minutes of kissing, fondling, and teasing, she suddenly stopped and stood up. By now we were both naked. She walks to the bathroom wearing her new toy.

"Now, turn over onto your stomach," she commanded, while in the bathroom. So, I rolled over onto my belly, I was grinning on the inside and soaking in her commands.

When she returned, I felt her caressing up and down my inner legs before spreading them apart slightly and repositioning my legs off the edge of the bed. She began kissing my ass before rubbing liquid over my ass crack with her hands.

Tiffany then jammed the bottle into my asshole's entrance and squirted the liquid inside. She gently rubbed it around my butt before slipping a finger or two inside, the sudden entry made me tense up. The lube felt good sliding in with her fingers. She slowly started finger fucking my ass with them, then a third finger, all in rhythm. My ass was starting to feel a bit numb, but her fingering felt so good. I let out an odd moan.

Watching someone on video performing and experiencing it, were two different things. I realized then, they were actors, and the feeling I felt was something unworldly. I was arching my back and pushing my ass into her fingers, wanting more. By now I had a big hard-on hanging off the edge of my bed, and pre-cum was beginning to flow out freely.

I was moaning more and more. It was then that Tiffany stopped and started rubbing lube onto her artificial cock.

When had finished, she shoved my head down into the mattress, while jerking her fake cock.

"Stay the fuck down, I am going to fuck you like a dog," she said and started rubbing her fake cock up and down my ass crack. Almost teasing me with what was coming. Soon she was guiding her makeshift cock into my ass entrance. It slid in easily enough to a point until it went fully inside. It made me groan slightly in pain.

The excitement had transformed into pain, as that fucking toy ended up splitting me open deep inside my ass. My ass and lower back felt the torture, as her fake cock resided inside me. She held it deep inside my ass for a good minute and a bit, while telling me to relax.

"Damn, you're so tight," she said, as I was still grimacing. "We need to stretch that ass of yours before we start anything," she said. I said nothing, just absorbing the pain and grinding my teeth.

This wasn't how the video actors reacted. I was tempted to call it off.

In time, while the dildo was jammed up my ass, I started to relax, and after around 20-30 seconds, the irony absorbed the pain.

"You want me to fuck you, now, or aren't you man enough?" she said with tongue in cheek. "You want to be fucked like a bitch and dream of sucking some cocks?" she kept going.

All these insults kept coming from her lips, I hadn't noticed she was already had slowly started to buck and grind into me. Tiffany was slowly thrusting into me, as my ass had loosened up by now. My cock twitched a bit as she made me moan out with pleasure. She giggled at me.

"Busted," she smirked. That was the green light for her to start fucking me harder with her dildo strap-on. "You're going to get your ass bred tonight, bitch," she continued to fuck me and talk nasty. My legs were now dangling from the edge of the bed, and I was losing myself in pleasure, as she fucked into me harder.

I had never felt so much pleasure in my life, I was moaning the whole time she fucked me. After what felt like an eternity (maybe five minutes), she pulled out and ordered me to lay on my back.

From the tone of her voice, I quickly responded. She lifted my legs up and onto her shoulders and raised my ass to meet the strap-on. Then she slid it back inside, which felt glorious as it slid back in deep. I moaned with pleasure. My cock by now was limp but would jump around, every time she thrust inside me.

Tiff gave me a good old pounding for another five minutes before I felt a build-up in my stomach and balls. She kept thrusting into me and making me moan. That feeling in my stomach was electrical, as my balls emptied and I cum all over my stomach.

"Oh god, oh god," I kept groaning out. She slowed her ass fucking me and looked at the mess over my stomach and my cock still pulsing. She rubbed the cum over my stomach while I watched her continue to grind slowly into my ass.

While she kept grinding into me, she leaned forward and feed me her cummy hand. I instinctively licked it.

When she had enough, she fell on top of me and then we kissed passionately before she went home.

The next day I felt so embarrassed, but she came over and wanted to have another go at me. I ended up relenting and she fucked my ass again, and I blew my load again. She then fed me my cummy from her hands.

From that day, we started the pegging game as a weekly event, as a bonus for fucking her every night she turned up at my loft, (which was daily).

I was too young and naive to realize that she was grooming me. Tiffany fucking my ass, went from weekly, to a daily event, until it was multiple times a day. I was now hooked on getting my ass fucked by her. At first, I felt emasculated and embarrassed, I no longer felt that. All I dreamed about all day was getting my ass slammed over and over, repeatedly.

The End, for now.