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Introduction:

I was living in a loft behind my parent’s subdivided house.
I was just out of school at eighteen, and my girlfriend for the last six months was twenty. I was athletically built and, rather good-looking, most girls flirted with me at school, but I didn’t take the hint and finished high 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 blonde dreadlocks, a seductive smile, blue eyes, and reasonably sized breasts. I was hooked on her, if she told me to do something, I would do it.

We began with a whirlwind romance and had sex every day or whenever we could, but after six months it started to feel stale. In the beginning, we fucked like rabbits but then I lost the thrill of normal sex. Although I was straight by nature, I often stroked my cock while watching bisexual, gay, or tranny porn, in secret. I think she had a secret girlfriend on the side.

Once Tiff (Tiffany) noticed it or found out, she thought she could spice our relationship up. After some research, she drops me an idea, pegging. She thought she’d spice up our love life, by pegging me with a strap-on. At first, I warmed to the idea before acting stunned but then I had to quickly think of the right answer.

“What! that’s gay,” I said. “Yeah right, I’ve seen your secret stash, you may not be gay, but you’ve fantasized about it,” She snapped at me with a smirk.

“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, that I was interested in.

“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. “I will go shopping tomorrow and tomorrow 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 the 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. Even though I tried to hide it and act like I wasn’t interested.

I stood there watching her as she teased me with the item, I acted annoyed but deep down I was curious.

“Now, come over here and lie down,” she pointed. I sat down on my bed and then lay on my back, 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 with her new toy.

“Turn over onto your stomach,” she commanded. So, I rolled over onto my belly, I was grinning on the inside and soaking in her commands. I soon 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 ass entrance and squirted the liquid inside. She gently rubbed it around my butt before slipping a finger inside my ass, the sudden entry made me tense up. The lube felt good sliding in with a single finger. She slowly started finger fucking my ass with that finger, then a second finger, all in rhythm. My ass was starting to feel a bit numb, but her fingering felt so good.

Watching someone on video performing and experiencing it, were two different things, the feeling 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, and pre-cum was beginning to flow freely down the side of my bed.

I was letting out small moans when Tiffany stopped and went to the bathroom. She claimed her wrist was cramping. What she was doing was attaching the strap-on harness and applying lube to it.

When she returned, I tried to see what she was up to, but she shoved my head down into the mattress. What I saw was she had the strap-on harness attached and was jerking her fake cock.

“Shut up, 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 and when it did go inside full tilt, it made me gasp in pain. The excitement transformed into pain, as that fucking toy ended deep in my ass. My ass and lower back felt both pain and pleasure, as it bottomed inside me. She held it deep inside my ass for a good half minute and told me to relax and enjoy the moment.

“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 going with the flow.

This wasn’t how the video actors reacted.

While the dildo was jammed up my ass, I relaxed and after around twenty 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 fuck like a bitch and suck some cocks?” she kept going.

All these insults kept coming from her lips, I hadn’t noticed she was already slowly bucking and grinding into me. Tiffany was slowly thrusting into me, as my ass had loosened up now. My cock jumped a bit as she made me moan out. She jiggled.

“Busted,” she smirked. That was the green light for her to start fucking me harder with the dildo strap-on. “You’re going to get your ass bred tonight,” she continued to fuck me and talk dirty. My legs were now dangling from the edge of the bed, 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 (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 in deep. I moaned with pleasure. My cock by now was limp but would jump, every time she thrust inside me.

Tiff gave me a good 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, as looked at the mess over my stomach and my cock pulsing. I rubbed the cum over my stomach while watching her grind slowly into my ass.

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. From that day, we started the pegging game as a fortnightly event.

I was too young and naive to realize that she was playing me. Tiffany fucking my ass, went from fortnightly to a weekly effort, to daily then to multiple times a day. I was now hooked on getting my ass fucked by her. All I dreamed about all day was getting slammed in the ass over and over.

The End, for now.
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