by Gavin Atlas
I swallowed hard and thought about it. If I said “no,” then something like this might never happen again. I realized I’d miss it.
“Yes, I did,” I said. As soon as the words were out of my mouth, I remembered that I wanted love, and that’s not what I’d just asked for. But it was too late.
“I’m glad, baby.” Mike kissed my cheek.
I was so confused, but grateful Mike was nice to me. The night had been the hottest sex of my life, but I shouldn’t love humiliation, should I? No. I swore I’d never let myself get tricked again.
* * * *
In no time, the video appeared on the internet. The whole city watched me get gangbanged. I watched it myself, and sure enough, you could see who I was, but the penises marauding me were safely anonymous. Still, everyone knew. I went to Godfrey’s once, and Lou and Al walked in. Everyone applauded. Considering how many people had seen the video, they might as well have tied me up and fucked me right there on the bar’s pool table.
For the most part, I was too embarrassed to go out to the clubs and meet people. It wouldn’t help my reputation, for one. But try as I might not to be promiscuous, guys still got my ass. One guy claimed he had a flat tire and needed to make a phone call from my apartment. As soon as the door closed, he whipped out his dick. It was beautiful, and it didn’t take much convincing that I wanted it in me. When he was done pumping my rump, I noticed he never made a call.
Another guy said he needed to borrow a wrench. I had just gotten out of the shower, and when I bent down to retrieve the tool box from under the sink, he stripped off my towel and started massaging my ass cheeks. Again, I got horny, and he was in my ass in no time. When he left, he patted my bare butt and said, “You’ve got the best ass in town, Derek”. It was then I realized I hadn’t told him my name. Tricked again.
As sex crazed as I was, I told myself I wasn’t going to let myself be the dumb, easy bottom everyone accused me of being. I wanted a relationship, and that meant I had to go slow. Someone would want to be with me for my personality instead of my hole sooner or later.
Over the course of the next week, I chatted online with a man named Ron. I saw his picture. Nice looking and, although he was in his late forties like the other men who had been in my ass, he didn’t seem to know them. He never once mentioned anyone fucking me. I’d taken the word “bottom” out of my profile, and I had clothes on in my new picture. It was a good sign when he’d complimented me by saying, “you have such beautiful dark hair” instead of “you have such a hot ass.” Maybe he’d treat me with respect.
He asked me out a couple of times, but I claimed to be shy and had to know him better before I’d meet. The truth was if I met him out at the bar, there was a chance someone would see me and say something humiliating that would ruin everything. He eventually told me he had a little group of friends who got together to do something goofy, like watch a Disney cartoon film. That sounded harmless. I agreed to go with him.
The night of the get-together I found myself feeling super horny. My drive to find something meaningful meant I hadn’t been fucked in almost two weeks. I found myself donning my tightest jeans without any underwear, hoping Ron would notice.
What am I doing? I thought. I’m not an easy bottom. I’m not going to let him fuck me the first time I meet him. I started to change just as Ron knocked on the door. I’d just have to wear what I had on and control myself.
Ron turned out to be charming. On the drive over, he talked about music and his dogs. Nothing sexual. I didn’t catch him looking at my crotch once.
His friends, Vic and Tom, were a different story. They were nice enough, but they kept grinning like they were up to something. Still, it started off the way we planned. Vic made popcorn, and we settled in to watch cartoons. Ron held my hand the whole time. I looked at Vic and Tom once in a while. Vic was obviously a leather daddy. I could tell from his boots, his beard, and his photos of Harleys he had on the wall. Tom didn’t seem as rough around the edges. In fact, from his conservative gray hair and plaid sweater he seemed mild-mannered. On the other hand, he had a diamond earring and a tattoo on his wrist of a missile imprinted with the words “target acquired” in red capital letters.
Ten minutes into Pinocchio, Vic announced he was bored, and they shut off the TV.
“Let’s play poker,” Tom suggested.
“Uh, I don’t know,” I said. “I can’t play poker.” I had a vague recollection of telling someone recently that I couldn’t play poker. Maybe it was Ron.
“Yeah, yeah. That’s what they all say,” Ron said, chuckling. “I know, we’ll teach you to play without betting money. Vic, you must have some M&Ms or some toothpicks around.”
“That’ll be just as boring as that video. How about raising the stakes a bit?” Vic’s pitch black brows rose with mischievous mirth. “It won’t be interesting without at least a little money.”
Ron sighed. “Well, what about strip poker? That should keep us awake at least.”
“Excellent.”
“That’ll work.”
“Wait, what?” I asked.
“Let’s start off without shoes,” Vic offered. “Keep on your socks for warmth, if you want, but you can’t bet them.
“Don’t worry,” Ron said. “It’s just for fun.”
I held two aces in the first hand dealt to me, which I thought was good enough to win. I felt relieved. After all, if socks and shoes didn’t count, all I had was my shirt and pants. I cursed myself for being too horny to wear underwear.
“Do we have to say what we’re betting?” I asked.
“Uh, isn’t that obvious?” Tom smirked.
“No, I know what he means,” Ron quickly cut in. “Okay, I’ll bet my sweater.”
“I’ll bet my sweatshirt,” said Vic.
I saw he had another shirt on underneath. This was unfair. All I had was my t-shirt because Tom had taken my jacket at the door.
“You’ll bet your shirt, Derek?” Ron asked with a sweet smile.
“You could bet your pants if you want to, of course,” Tom added. They all laughed.
“Nah, I’ll bet my shirt.” They all asked for more cards, and I had no idea what to ask for. When they showed their hands, it looked like I won.
“You lose, Derek. Off with your shirt,” said Vic.
“But wait, I have two aces, and you only have two jacks.”
“Nah, we said eights are wild. So, I really have three jacks. Your shirt, please?” Vic held out his hand.
I started pulling my t-shirt off. “Shouldn’t it just be whoever has the worst hand has to give up his shirt?” I asked.
“Sometimes,” Ron said with a nod.
“Nah,” said Vic. “Not how we play. Winner gets one item from the loser of his choice.”
I handed Vic my t-shirt.
Tom’s face lit up with lust. “Ooh, very nice, Derek.” He stroked my stomach. “I like tan and muscular.”
“And smooth,” Vic added with a devilish glint in his eyes.
“All right, don’t embarrass him,” Ron said. He placed his arm protectively around my shoulders. “Though you do look great shirtless.” He gave me that sweet smile again.
Vic and Tom exchanged a look that said, he’s going to look even better naked.
When the second hand was dealt, I got three tens and an eight. I wondered whose shirt or sweater I’d pick. They were all good looking guys in their forties or fifties, especially Vic with his sexy beard. I decided it would be best if I asked for Ron’s shirt. After all, he was my date, and I was sure it would turn him on if I chose him to be the one I most wanted to see naked. I’d have a better chance of getting lucky later. What am I saying? I’m not going to have sex on the first date!
When everyone showed their hands, I was sure I’d won.
“You lose again, Derek. Looks like I won your pants,” Tom said.
“But wait! I have the best hand. Don’t you have the worst hand?”
“Derek, we said `low hand wins.�
�� Don’t you remember?” Vic grinned.
I could have sworn they’d said nothing of the sort. I was also pretty sure they hadn’t said anything about eights being wild in the first hand either.
Tom started unzipping my jeans. I looked helplessly at Ron, but he just shrugged.
“Don’t worry about it, Derek,” he said. “You’ll get him next time.”
Tom tugged my pants far enough down that he could see my penis.
“Whoa! No underwear on you, boy? This game just got interesting!”
“Nice shaved crotch,” said Vic, reaching over and caressing my dick. I tried to think about the Periodic Table from high school chemistry class, so I wouldn’t get hard while Tom stood me up to finish removing the pants I’d lost. Vic’s left hand reached around and gently played with my ass. Ron pushed his hand away, and swatted Tom’s fingers, too. However, his own hand lingered on my rump.
“God, you are beautiful,” he said.
“All right, all right. I surrender. I lost. I’m nude. Now can I have my clothes back, please?”
“Nope,” said Tom. “You have to win them back.” Ron’s fingers delicately trailed down my ass crack, his index finger fondling my pucker. I wished it was his dick so much I almost purred.
“Win them back? But I have nothing to bet!” I argued. Vic had already dealt each of us our cards.
“You have to bet your ass, Derek,” Vic said. “Whoever wins this hand gets it.”
That did it. Now I had a raging hard-on. I tried to cover it with one hand while sitting back down, but I couldn’t keep Tom from sneaking his left hand under mine and pushing my thighs apart so he could finger my hole.
“No…no way,” I stammered as everyone picked up their hands. “This can’t be how strip poker normally works, can it?”
“No, not normally,” Vic said. “But those are the house rules, and it’s my house.”
I looked at my cards and frowned. “Does low hand win this time?”
“No, not this time,” they all answered.
“Okay, so we know what Derek is betting,” Vic began. “So let’s say that if I win, I get his ass to fuck all night.”
Tom pounced. “Okay, I’ll see that, and I’ll raise you. If I win I get to fuck his ass for a week.”
“What?” I yelled.
Ron laughed and gestured for the guys to settle down. They didn’t.
“All right, Tom,” said Vic. “I’ll take Derek for a full month.”
“No,” I said half-heartedly. I was so turned-on, but I was determined I wouldn’t worsen my reputation in Richmond by letting someone win my ass for a month in a poker game. “That’s crazy,” I said, feeling myself hyperventilate.
“Okay, okay. We’ll compromise.” Vic’s forehead creased in thought. “The winner only gets you for the full night.”
By now, Tom was finger-fucking me. I was almost at the point of agreeing to anything.
“After the winner fucks me, do I get my pants back?” I whispered.
“No.” Tom pushed his finger in farther. “We’ll play another round to see if you win your pants back then.” His calloused hand felt like sandpaper against my shaved crotch.
“No, no. Be reasonable.” Ron smiled at me. “Yes, sweetie, you’ll get your pants back.”
They turned their hands over, and it was immediately clear I had lost my ass, and Ron had won it. His hand replaced Tom’s between my legs, and he started to insistently press a digit inward.
“Oh, yeah. This is the best thing I’ve ever won,” Ron said with a triumphant grin.
I couldn’t understand how this happened. All I did was come over to watch a Disney movie, and somehow I lost my ass in a game of poker instead.
Tom and Ron stood me up and bent me over the table. Vic pulled a bottle of lube out of his pocket and some condoms. What? He knew all along we’d be playing strip poker for my ass! Knowing I’d been set up only made my dick harder.
Tom started lubing my hole. I found myself arching my back to help him slide in deep and feel everything.
“Instead of a poker table, now it’s a poke-him table.” Vic chortled.
That turned me on, but I knew I had to fight my horniness to keep a shred of my dignity. “No,” I said, trying to stand up. “Not in front of everyone.”
“Yes,” Vic argued. “My house. My rules.”
Tom bent me over the table again and started in and out motions with his fingers. “Share and share alike,” he said.
“Please,” I begged. “I would let you guys all fuck me, but I’d be embarrassed. Maybe you don’t know, but my reputation is that I’m really easy. I don’t want people to think I’m a slut. If my reputation gets any worse, no one will want to date me; they’ll just want to fuck me.”
“What’s wrong with that?” Tom purred in my ear.
“No, Tom.” Ron gently pulled Tom’s fingers out of me. “He just said he’s embarrassed. Sweetie, I’ll take you in the bedroom.” He wrapped one arm around my chest to help me get up. I hadn’t realized I had obediently stayed bent over even after Tom stopped fingering me. Ron cupped my ass and led me to a bedroom. I could see Tom’s look of disappointment, and Vic appeared pissed off, but they didn’t say anything.
Ron kissed my face and my chest as he carefully pushed me down on the soft bed.
“I love every inch of your smooth body,” he murmured as one hand reached my crotch and the other, my hairless hole. He put my legs in the air and started to undress himself. “Shaved boys like it rough, don’t they?” he said.
That was weird because I was sure a guy like Ron was going to be kind to me. I was getting stiffer at the idea that he was a nice guy on the outside who was actually a lust monster out to nail me.
“Be gentle with me, though.” I hadn’t been fucked in a couple weeks and I didn’t want him to injure me.
“Mmmm, nice and tight,” he said as his penis entered my ass. I noticed he’d left the bedroom door wide open. It was too late for me to get up and lock it. After feeling Ron inside me for a minute, I didn’t care at all. His dick was perfect for right now. If he had been bigger, he would have hurt me, but he was definitely big enough that I felt every stroke. I moaned and spread my legs wider to make my ass more accessible to him.
All of a sudden, Ron started hammering my hole unbelievably hard. I gasped in shock and involuntarily tried to wriggle my ass away from the attack, but he didn’t let up nor miss a stroke. He fucked harder than Manuel. Harder than Mike. I started moaning louder than I’d ever moaned before.
“Oh, my God. Oh, my God. Oh, my God!” I repeated as I felt his dick penetrate and pummel me in merciless abandon. I could hear Vic and Tom laughing. “Oh! Oh! Oh, my God!” I gasped over and over for what felt like an hour, while Ron continued his unrelenting attack on my hole.
“Damn, you’re a good bottom,” he said. “Most guys would have broken by now.”
The truth was that I was about to cry, but his compliment made me harder, and I wanted to service him more. I pulled my legs farther back. I was shocked when Ron somehow increased his pace. Sweat beaded on his forehead.
“Yesssss!” He hissed as he came, thrusting the deepest he could. “Yes. Yes. Yes.” He panted, exhausted. “You did it, Derek. No one can hold on until I come.” He shook his head. “God, you’re amazing. I can’t believe I get this ass all night long.”
I lay there, breathing hard, feeling my ass throb with soreness and heat. I loved that fucking. God, Richmond tops were all fantastic. Ron lay next to me for a while catching his breath. He spent about a quarter of an hour kissing and fondling my body. His hands felt wonderful.
“Now I’m going to fuck you doggy style,” he said with a smirk.
I couldn’t believe he was ready again! He flipped me over and spread my knees apart, so my hole was level with his dick. “You know what? I’m going to blindfold you.”
I moaned. I knew what that meant. They say I’m dumb, but I’m not that dumb. Vic and Tom were going to slip into the bedr
oom and fuck me. I hoped they’d figure out a way to get in my ass without me feeling like I’d agreed to be public pussy. I stayed passively on all fours while he tied a black handkerchief around my face. I could see light around the edges, but I was effectively blinded overall.
Ron started fingering my hole and lubing me up to be re-penetrated. I felt surprised at how rough he was being. It was then I realized his fingers were much more calloused than I remembered. Unless Vic was really calloused, it had to be Tom’s hand.
The rough hands squeezed my cheeks and played with my hole for several minutes while I remained on all fours, patiently arching my ass and moaning softly.
I felt hands spreading my knees farther apart. One palm slid up my thigh and spread my hole, while a dick that was definitely larger than Ron’s entered me with difficulty. When it was in me to the hilt, I heard a low voice whisper “yeahhhh.” It was Tom. He started long, slow strokes. He pulled almost all the way out of me and then all the way in, his hands firmly squeezing my hips. He ground away at me for a long time, fucking me with a round and round motion that was completely different than Ron’s style. Doggy style makes me sore more quickly than other positions, and I started grunting from the effort. I found myself pulling away from Tom’s dick so he couldn’t get it all the way in. Each time I did, he gently, but firmly, pulled me right back, so his hard-on continued to hit my prostate.
“C’mon, sweet bottom boy,” Ron whispered in my ear. “You can do it.” Again, the encouragement helped and for a short while I found new resolve to take the fucking until I could make Tom come. After another five minutes, I started pulling away again, and this time I could tell my struggling turned Tom on. His pumping became more insistent, his grip on my hips tightened, and his nails dug into my skin. I suspected if I suddenly gave in and started to push back on his cock, he’d come. I did just that.
After a few final thrusts that brought me to tears, I heard Tom try to suppress a groan and whisper, “Oh, Jesus.” He pulled out slowly, his rough hands fondling my ass. Someone softly kissed the nape of my neck, causing ripples of pleasure to race down my back.
“You’re the best, Derek,” Ron said. “Stay in that position just like that for me.” A hand played with my hair, but I knew Tom’s two hands were still on my ass cheeks.