Teasin’ Pleasin' Pt. 02: First Strike

By the Christmas holidays, I had gotten so used to her fucking me with her strap-on, that I was on the verge of craving it. She was always coming up with these ideas, so now I had to empty my balls into her before she would be fucking me with her strap-on. No problem. Our sex life was back on track, after it almost fell apart, a few months back. I fuck her, then she fucked me.

The next hiccup in our lives was coming up. Tiffany and her friends throw a reunion party each year on New Year's Eve, she started badgering me to go with her. I wasn't that big on large gatherings and apparently, there was going to be a large turn-out, there usually was, so she said. It was held at some old mansion that one of her friend's family-owned, by the bay.

So, it was the night of the party, and my heart still wasn't into going, but she insisted. Tiffany doesn't see her friends much and this was her chance to meet up with them again, but I've heard stories about these wild New Year's and Memorial Day parties before. Like usual I gave in to her badgering and agreed to go.

So, we booked a taxi and arrived at the complex's long driveway. I was gobsmacked at the enormous layout of the estate and then the mansion house itself.

There seemed to be people mingling everywhere, inside the house, outside of it, by the pool, or by the edge of the beachhead. I was awestruck looking around as the taxi slowed to a halt at the front doors.

Inside everyone seemed to be either chatting, flirting, or drinking. We started drinking once we entered the house. The music was pounding, it was so loud that it shook the windows of the house and made my heart pace. I didn't feel comfortable inside but hide it from Tiffany.

Tiff found her friends and started talking to them, it was all girl talk, so I drifted away and explored. So, I wandered around the estate, everyone ignored me.

I became bored in no time and started thinking that it was a mistake coming, it wasn't my crowd, or my music, and not my scene. I was bored and started having thoughts of calling a taxi or uber and going home.

An hour had passed and after yet another bubbly drink, I went inside the house and try to locate the restroom.

When I finally found it, I wondered to myself, why do rich people need everything so big? The restroom was slightly downstairs before the basement to car garages. It was well hidden from view, but it was massive. All I wanted was to take a piss, but this place was almost like a night club's facility. There were three urinals, two toilets, and a shower, and there still was room for more.

After I'd finished and was packing my cock back in my jeans and zipping up. I was washing my hands when the sudden noise of the door opening and slamming shut, made me turn around, as a tall guy came in to take a pee.

I couldn't help but notice from the reflection in the mirror, that this dude was packing a big cock. This would have to be the first time I looked at another man's cock or cock spotting since Tiffany spiced up our life. Was it the fact I was tipsy from the wine or was my inhibitions let free? I finished up and was about to leave, but another dude walked in. Then the guy I was watching in the mirror grabbed my arm. We glared at each other, then I broke eye contact and briefly looked at his cock dangling there, then back at his eyes.

"Not so fast," he said to me and put a finger to his lips, to shut me up. He then leaned that hand on the door hard, as it shut and then he latched the lock.

"Perv, you like looking at cocks," he growls. I glared at him. "Suck it," he said, and he waved his cock about. "No, I don't swing that way," I stuttered my reply. "Bullshit, I see it in your eyes" he snapped. He was much bigger than me and forced me down to my knees. "Suck it," he said again, this time forcing my head to his cock.

"Open up and suck it," he ordered. I was about to say something when the other guy walked out of the toilet. The distraction made it easy for him to force his cock into my mouth. "That's it, now suck it," he persisted.

I obliged and started to suck on his big cock, not knowing what the other guy was going to do. All he was doing was watching the big dude make me suck on his cock. The big dude then grabbed my ears and started to fuck my face. "That's it, suck my cock, you bitch," he said. The other dude walked to the basin and washed his hands, ignoring my predicament.

(**At this stage I knew none of their names and never did, but I will call the big guy "Nudge" and the other guy "Sam.")

A few minutes went by and now I was getting used to the rough riding of my throat. Now I know why Sam was watching, he knew Nudge and it was all a trap and I fell for it. I saw Nudge give him a slight nod, then without a word spoken, Sam started taking off his clothes. His cock sprung out as he wrestled with his jeans.

Once his clothes were free, then Nudge pulled his cock out of my mouth, and Sam's cock soon replace it. I was now sucking Sam's cock, while Nudge ripped off my shoes and then started wrestling with my clothes. I was soon buck naked with a cock in my mouth and with Nudge repositioning my knees to his liking.

He positioned my knees in a way he wanted and started licking my asshole, he almost brought a moan out of me. I now sucking Sam's cock, while Nudge was rimmed and licked out my asshole. My cock was dripping pre-cum, and I felt lost in a place between heaven and hell. Every now and then Nudge would give my semi-hard cock a tug. It was beginning to be all too much, I thought he would drive me to cum.

I was sucking on the cock in my mouth, while he licked my asshole, while it made me get hard and I had precum leaking from my cock. Then after spitting and licking my asshole until it went numb, I felt his cock rub up and down my ass crack.

Then in slid his cock, passed my entrance. It was much thicker than Tiffany's strap-on and as it went inside, it had a ripping feeling. I wanted to scream, and when I did, I gagged on the cock inside my mouth and throat.

I had a cock stuffed down my mouth and throat, while Nudge started to grind his cock deeper and deeper inside, without mercy. It hurt so much that tears ran down my face. I was getting a pounding in the ass and torture in my mouth, it wasn't until a few minutes more before they stopped.

"Look at him would you, he's getting off on it, his cock is rock hard," Nudge gloated. That's when Sam took photos on his cell phone. He took shots of Nudge standing near my backside, with his cock resting on my ass crack, and inside my ass, and then of my head with his cock inside it.

"Do you like being fucked like a bitch?" Sam then asked as he took more photos of my humiliation, with cock in my ass and mouth.

"Beg for more, like a whore, or face the consequences," Nudge remarked. I soaked in while catching my breath on my hands and knees, and panting.

"Alright, alright! Fuck me, fuck me, and fill my ass, and fuck my mouth and feed me cum," I said. I couldn't believe what I was doing but I was pleading with them to fill me with their cum. "Beg as you mean it," he ordered. "Please fuck me, please, please," I began to beg. I did and they looked at each other. Nudge slapped my ass.

With that, they started to go back to work.

Within a minute I was moaning out loudly, as they were fucking me again. Nudge knew exactly how to fuck me to flick my switch. He was fucking me with long slow methodical smooth strokes, unlike before when was ripping me apart. The more he tweaked my switch the more adventurous I sucked Sam's cock. The more they groaned and grunted the more turned on I became.

By now I was in the groove of a machine, I was the engine, and they were my pistons. Nudge had begun to grip my hips as he went for glory and started pumping into me harder once again. I was beyond resistance I was loving it by now.

"God, oh god, I'm cumming, I'm cumming," Nudge groaned out. I felt his cock spasm inside me and then explode a load inside my ass. While he slowly ground out his orgasm inside my ass, Sam pulled out and slapped my head with his slimy cock.

They took a short break before Sam went from my mouth to rolling me onto my back and putting my legs on top of his shoulders. He then started to fuck my loose ass, as I lay there watching his facial expressions as he slid into my ass. By now any resistance I had was long gone.

A short time later Nudge re-joined us. He climbed on top of my chest and slid his cock into my mouth and then he started fucking my face like that. I lay there taking it, with moans of pleasure and the odd choke. When I moaned out, with cock inside my mouth, Sam started to stroke my cock, which was ready to explode. That's what it did within a minute.

I made a mess all over my stomach, but that didn't faze them. They continued fucking me like that for at least another five minutes before they started to lose their shit inside me. I felt the twitch in my ass, and not long later I felt the explosion in my mouth. Once they'd finished, I felt euphoric and on cloud nine.

There I was laying on my back absorbing everything and thinking they were done with me.

"Get up!" I was ordered by Nudge. I was helped up by the pair of them. They lifted me up and that's when the pain began. I felt enormous pain as one cock, then another cock was forced inside my ass.

I was suspended in the air, with both cocks in my ass. They slowly fucked me, and the pain was bad at first, I started to pass out. After two minutes of this, I stopped drifting into hell as the pain turned numb. My ass felt numb once they work out a rhythm. It started to feel good, as one would grind inside slowly, while the other just poked inside me.

I was crying in pain and pleasure. Soon as one of the cum inside me, the other started to grind inside me. Then when they both had unloaded inside me, they simply let go of me, and I collapse in a heap on the bathroom floor.

So, I went from never having touched a cock, to having two grinding in my ass at once. Slowly I rose and crawled to a squat position, I couldn't help cum slowly trickling out from my ass. My back ached a little and my ass felt numb and tender.

Once they were done, they gave me a final stare while putting their clothes back on. They zipped up as Sam took more photos of me, I was at their mercy, and slumped on the bathroom floor. After at least an hour of fucking me, they left.

I cleaned myself up and gingerly went back to the party. Tiffany finally found me and asked where I was. I lied and said I got lost while investigating the grounds. She asked why I was limping and walking funny, I lied again and said I tripped and fell over.

It was almost daylight when we left via taxi. First, we dropped Tiff off, and then I went home myself. I took my shoes off and slumped on my bed and slept all day.

When I woke up, I had received several text messages from my new buddies. No words but photos of me sucking cock and taking it in the ass, and cum out of my exposed ass. Tiffany received the texts too.

My life felt awkward, I felt embarrassed and ashamed, in a panic that my life was a mess. I wasn't sure if I could break it down and explain what was ticking in my head when I made my decision, literally it was just me making excuses not to face family, friends, or enemies. Facing people in my world, and repeatedly answering questions was too much linework, that I couldn't face. I was a nineteen-year-old coward and shut myself into isolation in my loft for four days.

The next week I rang the military, and rashly joined up with the army cadets.

The end, more soon.