the-alluring-stranger
GAY SEX STORIES

The Alluring Stranger

The Alluring Stranger

by Bassytian
19 min read
4.75 (19100 views)
femboycross dressinganalfrottagehalloween
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All characters are 18 or older, enjoy! Comments and feedback are welcome!

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My name is Eric; I am a 24-year-old forklift operator in a warehouse. This is a tale about the night that changed my life. It happened last year on Halloween night.

So, a bit of backstory. I was never popular in school or good with women, I used to drown my sorrows in alcohol while I watched my buddies pick up the same women that turned me down moments earlier, though they were "not looking" when I asked them out. Things like that killed my self-esteem. I became convinced that I was a genetic failure of a man, a practical joke created by God or nature because they had a fucked-up sense of humor. I eventually gave up and quit trying altogether, I even stopped hanging out with that group of friends because watching them succeed was too painful. As the years passed, my life had come down to going to work, coming home, eating dinner while watching TV, going to bed, rinse and repeat. I had fallen into deep depression, but my energy was sucked out of me to such an extent that I had not fight left to do anything about it with.

One evening, I was at home binge watching B-movie horror flicks, the kind where you could tell the special effects budget was incredibly low, you could see the zipper on the monsters. I had cooked a TV dinner and was sitting on my recliner with a beer in my hand when my phone rang. It was Nate, one of my old buddies that I no longer hung out with, but he was the only one I still talked to. I answered.

"Hey man, what's up?"

"Yo Buddy! I just wanted to check in with you, how have you been?"

"Same old same old, working and drinking myself to death. What about you?"

"Same as always! Listen Eric, I have a proposition for you."

"What? If this is another 'get-rich-quick scheme..."

"No, nothing like that! What are you doing on Halloween night?"

"I'm off that night so I was just going to stay here, watch a horror flick or two, and get so drunk that I'll think it's real."

"Forget that noise! I'm taking you to a Halloween party where there will be lots of chicks for you to meet!"

"Dude, are you nuts? I've always been utterly repulsive to women, what makes you think that has changed?"

"I'll make you a deal. If you come and don't get any action, I will give you $1,000! That's how convinced I am you'll land a hottie!"

"I'm hanging up."

"I'm serious! I saved up for this bet! I've got fifty twenties that say you'll dip your dick into someone's hole on Halloween!"

He then texted me a picture of two stacks of twenties side-by-side, he was telling the truth.

"Fine, but you'd better be willing to pay up if I'm still a virgin after Halloween!"

"Alright, alright. So, you're coming?"

"Yeah. It'll be the easiest grand I've made. What do I have to lose?" Other than another chance to humiliate myself, nothing.

"Awesome! You won't regret it! Everyone will be in costume, so pick something spooky! Go to "Spooky Side of Hell", they have the best costumes in town. Oh, and go on Wednesday, I know the woman that will be working that day. I'll tell her to give you a discount!"

"Yeah, yeah, talk to you later Nate."

"Bye Eric! You're so getting some that night, I promise! I'll pick you up at 7:30, later man!" With that, he hung up. Me, getting laid, was he stoned? I'd die a virgin if I was the only male left on the planet. Oh well, who could turn down $1,000? "Spooky Side of Hell", huh? How corny. It was probably going to be more of the same, me being the only guy leaving the party still a virgin. Seriously, why the fuck did I have to be exposed to that again? I continued the rest of the evening as I usually did, finishing my dinner, watching a movie, taking a shower, and going to bed.

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On Wednesday, I took up Nate's suggestion and went to that tacky store. It was what you would expect, "spooky" music played, displays of various costumes draped over mannequins were spread throughout the salesfloor, Halloween-themed party supplies stacked on shelves, there were no surprises here. All the costumes were on a wall on the right side of the store, so I went to take a look. I'll give them this, some of them were very well made, I understood why Nate hyped this place up so much. However, the true reason for his enthusiasm was about to speak.

"Hi there! Can I help you?" a cheery blonde chirped as she approached me from the side. Her name tag said "Jade", she was quite attractive. I thought she was an easy 10 and way too hot for me. But who was I kidding, any woman was too hot for me.

"Oh, I'm just looking, thank you though." I told her.

She smiled. "Okaaay, but don't hesitate to come find me if you need anything!" She happily walked off with her arms straightened behind her back. She had a cheery disposition, I found myself thinking her boyfriend, or maybe girlfriend, was lucky to have her.

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I looked through the costumes, I was looking for something that wouldn't be hard to put on or take off. It took a few minutes, but I found exactly the kind of outfit I was looking for; a Gomez Addams suit, complete with a fake mustache. I could buy hair gel to style my hair to complete the look, this one would do. I removed the costume from the rack and brought it to the counter. Jade came from the back and stood behind the register.

"Will that be all for you?"

"Yeah. Say, do you know someone named 'Nate' by chance?"

"Mhm! I've known him for a little while. He said a friend of his was coming by and told me to give you a discount. Is that you?"

"Yep, that's me." I felt all my insecurities well up in my throat.

"Awesome! I can do... 25% off?"

"Wow, that's quite a discount." She giggled and rang my costume up, applied the discount, and gave me my total. As I slid my debit card into the slot, I glanced at her and she looked away. Was she looking at me? No way in hell, a cute girl like her wouldn't be caught dead doing that. After the payment was approved, she folded my costume and placed it into a bag, then handed it to me.

"Thank you very much! Can I help you with anything else?"

"No, that will be all. Thank you, Jade."

For some reason, she blushed and smiled shyly when I used her name, like I had made her day. "Okay then, have a good evening and Happy Halloween!" she waved as I walked out, I waved back before the automatic doors closed.

Something was strange, she looked and sounded familiar to me, but I've never known anyone named Jade. My old buddies and I never went to school with anyone going by that name. I spent the rest of the night trying to place her, but I couldn't figure out where I had seen her before. Oh well, it didn't matter, I wasn't going to see her again anyway. I went to bed determined not to give her another thought, which only led to me dreaming about her.

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On the evening of Halloween, I pulled my costume out of my closet and put it on, then dipped a comb in the hair gel I bought on my way home and styled my hair back. The mustache was the finishing touch, and with that I looked like the classic character, or some lame guy pretending to be him anyway. I sat on the recliner and waited for Nate to show up and take me to the party. He finally knocked, fifteen minutes later than he said. I opened the door; he was wearing a dirty hockey mask with torn clothes and a fake machete. He raised it as if he was going to attack.

"Cara mia!" I said, stepping forward and reaching for his face.

"Knock it off!" He recoiled; I would have been grinning from ear to ear if it was physically possible. "A little too into character, don't you think?"

"Says the guy standing there silent and pretending he is going to 'kill' me. Come on, I want my $1,000!"

"Yeah yeah, but I'm keeping my money!" He was as sure of my success as I was of my failure. Something about it made the bet kind of exciting, I was determined to prove him wrong. Once we were outside, I got in the passenger's seat of his car. For whatever reason, Nate felt the need to leave skid marks where he was parked before flying off, idiot.

The ride lasted a little more than half an hour, we rode to the football field of the college we attended together on the outskirts of town. This was an annual event, a chance for hundreds of people in our age group to get drunk and laid in costume. As we parked, I could see that the field was getting full quickly. There was a stage set up in the middle with a band dressed as horror movie monsters and villains tuning instruments. The concession stands were open, and lines were already forming.

"Do you see that, Eric? You can't tell me you won't find someone in that crowd to mingle with tonight!"

"All I see is hundreds of chances to prove you wrong. Let's get my humiliation and payday over with." We got out and closed the doors, then made our way into the crowd.

"Nate!" said Chris, one of Nate's friends. He was dressed as a zombie football player, he was too dumb to think of anything else. Chris and I got along well, so long as we didn't speak to each other. We used to be friends, but when we entered high school, he became a different person, the type who claims to be an "alpha male" with nothing but a football between his ears that likes to assert his fragile dominance over those he viewed as weaker than himself. I guess he saw me as weak because he would try to push me around, which led to us getting into fights. I would win some and lose some, but I never once backed down from him. He was with his three cronies, also dressed as zombie football players and just as dumb, always laughing at everything he said and did like they had no thoughts of their own. These four hadn't changed at all.

"And if it isn't 'Eric the Incel'! Don't shoot!!" He raised his arms mockingly, then laughed as he high fived his buddies. "Eric the Incel", he always said that like he had just come up with it. Then again, he had the intelligence and memory span of a goldfish.

"And I see you still have a single cell organism for a brain. Tell me, is your dick also the same size?"

He got in my face and pressed his forehead against mine, I pressed back and started into his eyes.

"You never did learn your place, byotch! Want me to drop you right here?"

"You can try; it'll be like old times!" I didn't care if we got into it and went to jail or the hospital, one more chance to knock this prick on his ass would have been worth it. Nate stepped between us and pushed us back.

"Guys, we're not in school anymore! We're adults now, act like it!!" Nate was right. Though I never backed down from Chris, he always brought out the worst in me.

"You're right..." I backed away, then looked around, one of us was missing. "Where's Jayden?"

"Jay is... gone..." Nate responded rather cryptically. The others shared the same expression, did Jay die? Jayden, or "Jay", was the best of us. He was smaller than the rest of us and had a demur personality compared to the rest of us boisterous assholes. There were rumors that he was gay, but he scored his fair share of phone numbers and nights with women I could only dream of. Jay was the only one of my former friends that never once teased me about my invisibility to women, in fact he tried to encourage me and give me advice. The last time I saw him; he told me that I was a better person than most people he knew and that he wished that everyone could see what he saw in me and would give me a chance. And the last thing he said has always stuck with me.

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"If I was a woman, I would happily sleep with you, Eric..."

I never saw or spoke to him again after that. Of course, I broke ties with all of them at that time, I was tired of them throwing their ability to get laid in my face on an almost daily basis. I feel bad for it now, but that night, I wished that Chris or one of his lackies had died instead of Jay. But no one said he was dead, maybe he moved somewhere far away?

"That freak made his choice and now he has to live with it." Chris said angrily. That confirmed he was still alive, but what was the "choice" he made? "Let's get some drinks, food, and later some pussy! Or in Eric's case, just food and drinks." I would have loved to punch him in the face, but calming down made me realize that I really didn't want to risk going to jail that night.

"You're killing me, Chris. If being a moronic asshole like you is what it takes to get laid, then I'll happily die celibate." He didn't like that answer.

"Hey, hey! He's gonna get laid tonight! I have $1,000 that says he will!" Nate stepped up, being the only person in the world certain of my "victory."

"Shit man, if you want to throw that much money away, you might as well give it to me and not this beta loser!" He was wearing my patience thin...

"Stop that, let's give him a chance! I wouldn't put this much money up if I didn't believe in him!" Nate interjected. I had never seen him that confident about anything, did he pay a prostitute to sleep with me that night?

"Whatever, I'm ready to get some grub! Come on!" He walked off with his lackies, who turned to make faces and some kind of gestures at me. They had no minds of their own.

We got in line at the concession stands, Nate and I went to a different one than Chris and the others. We chatted about the good old days that involved things I was also good at, like basketball. Not to brag, but I believe I could have gone pro, too bad depression broke my spirit. Oh well, I was a decent forklift operator at least. When my turn came, I bought a couple of hotdogs with some fries and a can of Coke, breakfast of champions. After that, we gathered near the stage as the lead singer began to address the crowd. His attempt to sound scary was laughable at best.

"Good eeeeeevening, you Hellions! Tonight, we're gonna rock until the dead rise out of the ground and jam out with us! Let's be sure to give them a concert they'll be talking about in Hell for eternity!!" This was just sad; it was a good thing he was wearing face paint because I couldn't imagine him being able to show his face in public after that. Thankfully they began playing, I've heard worse but better too.

As they played, something caught my attention in the corner of my eye. I looked to my right and noticed a woman dressed in a black dress that exposed her cleavage but covered most of the rest of her body. She was wearing makeup and had long black hair. She was Morticia Addams, how ironic. Some guy was chatting her up, I couldn't hear the conversation, but I could imagine it. He was asking her to sleep with him that night and she was either going to accept his offer or shoot him down. Based on the way she waved her hand, and the look on his face as he walked away, the latter happened. She shook her head, then her eyes met mine. I couldn't take my eyes off her, was she stunning! She smiled at me, keeping her gaze on me as she turned and disappeared into the crowd. How strange, someone dressed as my "wife" was at the party. I was sure there was some other Gomez Addams lurking around somewhere. I would probably see her with him sooner or later. There was something familiar about her though, I had seen her somewhere before, and recently.

After a few songs, Chris and the others walked off to hit up some women. I stayed behind, I couldn't watch history repeat itself again. I was convinced I had wasted my time, so I decided to get a beer or... three, call a tab, and go home. I didn't even want the goddamn money anymore; all I wanted was to escape from this bullshit party. I made my way back to the concession stand when I noticed "Morticia" in the other line next to me. That time, I was close enough to get a good look at her. She noticed me and smiled.

"You make a handsome Gomez Addams! I knew you would!" She giggled. When I heard her voice, it hit me like a haymaker from Mike Tyson.

"Jade? I didn't expect to see you here! You look great as Morticia, or should I say, 'Cara mia'?" My Gomez couldn't have been more off, but she was amused.

"That was horrible! Your accent sounded more French than Hispanic!"

"I... don't get much practice." Fucking up already.

"Well, you get an A for effort." I don't know if it was extreme loneliness, but her smile cut through my heart and not in the usual painful way either. It was then that it hit me. Nate knew Jade, he told me to buy an outfit from the store she was working at, and now here she was dressed as my "wife". At that moment, I'd decided that I was going to buy that guy a drink after this was over, no matter how this ended. What a guy!

"So, did you come here alone?"

"No, I'm here with some friends of mine, but they're chatting it up with some guys. I would join them, but there's someone that I've always liked, and I don't want to be with anyone else. I was always too nervous to tell him how I feel, let's just say I wasn't exactly his 'type'."

"How could you not be? You're very attractive, and you have a great personality. Any guy in his right mind would have you." I didn't know how effective that would be. Me trying to cheer someone up was like the blind leading the blind. She smiled a little, so progress?

"Thank you, what did you say your name was?"

"It's Eric."

"Eric, that's a nice name, I've always loved it. So, do you think I should tell him how I feel?"

"I do. Tell him everything the next time you see him." She smiled and blushed a bit. Even though I had likely screwed my own chances with her up, it felt nice to make a woman smile for once. God, was I really that pathetic, that something so simple would made me feel like a stud? No wonder I was such a failure.

"I will! I have the courage to do it now, thank you very much! I know how I want to do it too! Bye Eric! I'll see you later!" With that, she stepped out of line and disappeared into the crowd again. I felt too humiliated to accept Nate's money at that point. I had screwed his elaborate plan up, as I knew I would. I got to the stand and was disappointed to see there was a one can limit. Oh well, there was a gas station a block away from my apartment, I'd buy a pack there, I felt like I needed to drink every can, I wanted to forget that night ever happened.

With beer in hand, I waded through the crowd of costumed partygoers, determined to get out of this nightmare. I pressed through on my way toward the parking lot when I felt someone's hand on my arm. It wasn't just someone's hand accidentally touching me, this was deliberate. I looked and saw who it was attached to; it was Jade!

"Catch me if you can, Mon Cher" she winked and disappeared into the crowd once again, she had a real talent for that. I don't know what it was, but something made me want to play whatever game she was playing, maybe I hadn't screwed up after all. I followed the direction she had disappeared in. I looked around and saw her near some more people. She waved, wiggling each finger as she smiled and moved behind the other group, which was the closest to the parking lot. I pursued her again and saw her standing between two cars. She bounced slightly, causing her breasts to jiggle, then vanished behind an SUV. This chick must have had a great grandfather named Houdini. I followed her out of the parking lot and across the road. After following her for three blocks, she entered an apartment building, I went in behind her. She was standing at the top of some stairs in the lobby.

"Hey, wait..." I said breathlessly, it was a struggle to keep up with her.

"Almost theeeeere! Don't give up now, Mon Cher!" she chuckled as she ascended the stairs. I assumed she was leading me to her apartment, but would I be too tired to make the most of it when I got there?

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