Trap or Treat: Halloween

”What the actual fuck was I thinking?” I exclaimed as he walked flustered through the park on a specially cold Halloween night.

For the longest time, I had a crush on my best friend since childhood, Joey Cochrane. However, he would never have known it. My parents are not opposed to my sexual orientation, being the only son in an ultra-liberal family. However, the predominantly conservative town we live in makes it all but impossible for me to simply come out to Joey. It was this reasoning that led to the hatching of a plan involving seduction and cross-dressing. This meant that not only was this plan a failure, but I was now taking the long shameful trek home in heals.

My name is Alexander Sloan, but I have always been known as Xander. I have been gay for as long as I can remember, however, I have been with only two guys in my life. Both of which were creeps that I met on Craigslist. Tonight was the first time that I have ever dressed like a girl. I have always been something of a feminine guy, but I work hard to hide it with a carefully rehearsed interest in sports and a constant talking about smashing pussy. For some time I have found that not only was this charade obnoxious, but it is also exceedingly exhausting.

I was especially fortunate to have a girlfriend like Sam. Like me, she had a distinct appetite for the same sex, yet was too afraid of the backlash that coming out would bring. She was the Pastor’s only daughter, and as such had to be publicly outspoken when it came to the sins of homosexuality. We had the arrangement of being the couple that would bang all the time, as far as, our friends were concerned. In private we could be openly gay around each other, and even on occasion act as an alibi for our not so heterosexual encounters. 

I was also lucky to have Sam because otherwise, I will likely be single. I am only 5’7” tall and about 156 pounds with a five and a half inch cock. My physical features we’re never meant to attract the attention of the girls at my school. For as long as I could recall, I felt like I should have been born a girl but by some twist of fate was instead born male. Aside from my pubes, my body is hairless. I have never grown a single facial hair in all of my eighteen years of life and thanks to the bottle of Nair in my bedroom, my legs are completely bare.

One feature that I have always been fond of is my perfectly round ass. Soft but firm, it would have been the perfect cushion for Joey’s pushing. However, after the cataclysmic debacle in the park, I don’t know if I could ever speak to him again. My only source of solace during my long walk was that he never actually saw me. I was all but crying out loud as I exited the park. The mascara was starting to burn my eyes and a kept stumbling like a drunken whore in my stupid two-inch heels as I recalled the evening events.

It was Samantha that originally came up with the idea of me dressing up like a girl and seducing Joey. She felt that he had some sugar in his tank and would probably give in if he were gradually coaxed into it. I couldn’t imagine that a star athlete like him would be interested in men, seeing as how he cycles through girls as most guys do socks. I also didn’t like the idea of strolling through town in women’s clothing. In this area that would be social suicide. She then suggested that we carry out her plan under the veil of Halloween.

 At first, I thought it was the dumbest thing that I ever heard, but I was desperate to feel Joey’s strong arms around me, if even for one night. Thanks to our mutual interest in cosplay, anime, and gaming, she had a whole assortment of sexy outfits that would allow me to look convincingly like any other girl on Halloween night. Once dressed I would nonchalantly tell Joey about a place in the park where ”some chick” would suck him off and maybe more. If all went well then I would tell him the truth and we spend the rest of the night in my bed.

If at this point you are thinking that the plan sounded too good to possibly work then you would be correct. Just as we had planned, I bailed on the last great Halloween party before we graduated. I told Joey that I had to stay with Sam because she needed it badly. I also mentioned a rumor that I heard from one of her friends about a girl dressed as Raven from the Teen Titans who wanted to suck him off at the gazebo in the park. The statement immediately dominated our conversation for the next ten minutes.

At first, he was skeptical, suggesting that the myth was that only gay guys hook up in the park at night. I knew it to be a matter of fact since both of my sexual encounters occurred in the very spot where I was telling him to be. However, after a good bit of lying about the source of the rumor, he told me that he was going to check it out after the party. This would give me at least two or three hours to get ready for our secret rendezvous. I told him to text me and let me know if she showed. He quickly agreed before ending the call.

Samantha was sitting next to me excited to prepare me for my date. My parents allowed us to use the basement to get ready and even went so far as to give me a first full of condoms before they left to attend a Halloween party of their own. I was at first embarrassed by how corny and open my parents were when it came to their gay crossdressing son trying to get some dick on Halloween. However, the same reminded me of the alternative. She pointed out that her dad only allowed her to leave the house because my parents were kind enough to lie and tell him that they would be with us the entire evening.

As far as Pastor Davis knew, we were all having a family game night with Sam and her friend Lisa. Lisa, who happens to be Samantha’s girlfriend. They met at church, believe it or not, and now they were both in my basement helping with my hair and makeup. They had added some dark purple temporary dye to my soft blonde shoulder-length hair. They used a fine powder to make my face pale lick a porcelain doll. My lips we’re given a glossy black coat of lipstick. I glanced at the mirror after the addition of the mascara and eyeliner and was utterly amazed by the pretty girl I had become.

I had picked out the Raven costume since it came with the hooded cloak and lacked the opening for cleavage. It was a one-piece bathing suit with long sleeves and a loincloth. However, Samantha had made several provocative alterations to achieve the level of sex appeal that she felt was necessary for the plan to work. By the time I went to put it on, she had transformed the simple costume into something that a porn star would blush while wearing. 

A dark purple sateen corset had been stitched over the spandex material of the suit to make my natural curves appear more feminine. The long sleeves had been removed and turned into a set of elbow-length gloves, leaving my slender shoulders bare.  My chest was still covered with the original material secured by a buttoned choker around the base of my neck. However, it was left open in the back for what Lisa called a more approachable look. The bottom which I had already felt may have been too revealing we’re altered into a thong cut with tightly knit fishnet stockings added.

I could feel the slight bounce in my butt cheeks and the thin material sinking within my crack as I walked into the room to model the outfit for Sam and Lisa. Their smiling and whistling as I did my little spin did nothing for the overwhelming anxiety that I was feeling. I couldn’t possibly have felt more ridiculous. At least she left the loincloth, I thought to myself. Lisa had a white hat-box on the couch with some things that Sam had ordered for me to go with the costume, but I was already past my threshold.

”Listen, Sam, I have some concerns about the costume here. I mean, it is a bit much.” I anxiously protested.

”I don’t know Xander, you look fucking hot. I mean, If I didn’t know any better I would swear that you were a girl.” Samantha replied with bright eyes and a big smile.

”Yeah, but you can’t think that Joey freaking Cochrane would be interested in me like this. I just can’t imagine this working.” I said almost shaking where I stood.

”Hey, Xander, if I may, I’d like to offer you some wisdom that I think will put you at ease.” Lisa chimed with a smug expression on her face.

”And what would that be Lisa?” I asked visibly irritated.

”It’s quite simple. You like a dick. When you go to a Mexican restaurant you usually gravitate towards the enchiladas or better yet a big thick burrito. Sam and I, on the other hand, we like pussy, so we just have to get a taco. Joey also likes tacos. So if you want to persuade him into filling you with his burrito, then it is best to get your advice from people who have the same tastes.” Lisa replied as she ran her long skinny fingers through her long flowing brown hair.

”I know it sounds vulgar, but Lisa is right. Hooking up with Joey will be harder for you than if you were trying to pick up a random girl. You not only have to seduce him, but you also have to convert him. It’s senior year and he will be heading to UCLA after graduation, so this may be your last chance to win him over.” Sam said before taking a deep breath and continuing. ”I am pretty sure if you can get him to come at least one good time, then he may be open to doing more once he realizes how good you can make him feel.” She finished, her face mirroring her serious compassionate tone.

”Xander, aren’t you tired spending your nights scouring the Internet for forty-year-old guys who just wanna cheat on their fat wives? I never heard about the first guy, but Sam told me that the second guy throat fucked you for what could only be two minutes then left you stranded on the side of the road. You have the chance to be with the guy you want. Isn’t that worth wearing that one good time?” Lisa asked as she stood from the couch with the hatbox.

I had only seen Lisa four or five times since she and Sam started their fling. I never had a problem with her, however, she did tend to be excessively blunt. I hated to admit that I was a little jealous of her. Of the three of us, Lisa Hardwick was the only one who was out and openly gay. Every day at school and in the community consisted of one barrage of slurs after another. Yet, she was ultimately free to be who she wanted to be. 

Lisa was right, I wanted to be with Joey more than anything. Even if it meant that I would have to wear a big pink poodle costume for Joey to want to do it doggie style, or dress like a skank to make him like me. If it could work then I had to try it. After all, what other night aside from Halloween could I possibly dress this way and hope to blend in?

”What’s in the box, Lisa?” I asked with a defeated sigh.

”WHAT’S IN THE BOX?” Sam shouted with a shit-eating grin.

Both Lisa and I paused to look at Sam who was looking for some kind of reaction from us.

”You know, it’s from Seven…Oh, fuck you guys, that was funny.” She said with a disappointed look on her face.

Lisa flipped the pale white lid to the hat-box. I was utterly stunned by the box’s contents. Within the box were one pair of purple knee-high leather boots with two-inch heels, a Fannie-pack with a gold chain for a strap, a bottle of lube, and last but not least, two fake latex breasts. I was rendered speechless at the sight of the set of fake tits staring back at him. 

”Fucked up, I know. But it’s all to complete the ensemble. The boobs are size B at best, but you will be more convincing with boobs. The Fannie-pack will act as a belt. I thought it would come in handy since the costume doesn’t have any pockets. I am sure that I don’t have to explain to you what the lube is for.” Sam said with a snarky grin.

There was nothing I could say in response to all the help that Samantha and Lisa had given me. After a little bit of struggle learning to walk in heels and an uncomfortable experience with the body adhesive, I was all dressed for my big date. I was surprised by just how well I blended in the crowd as I strolled through town on my way to the park. Just as Sam had predicted, no one had suspected that I was a guy. They had transformed me into something of a hottie. Even with the cloak and hood concealing most of my body, I could still feel the lustful eyes of passers-by as they were checking me out.

I made it to the gazebo around 10:00 p.m. and started to wait for any sign of Joey’s arrival. I had been waiting for more than an hour, keeping myself occupied by watching the other secret meetings of the night. I didn’t see any of the sex acts. However, I recognized the signs. Two cars park, one flashes its lights, the other driver gets out of his car and into the other, finally anywhere between ten and thirty minutes later both cars pull off again. It was the same way with the park’s public bathroom. One guy goes in a few minutes after another guy and like half an hour later they both leave in silence.

What I was attempting was far bolder, but with its advantages. We would be exposed in the gazebo with only the cover of darkness to hide us. Yet, we couldn’t easily be cornered and would be better capable of seeing anyone approach. If after learning the truth, Joey was into it, I would bring him home where he could fuck me to his heart’s content. Sam and Lisa would be there, however, in exchange for all their help, they would have dibs in my parent’s room all night. My parents wouldn’t be home until morning making the evening possibilities all the more tantalizing.

Unfortunately, it was about that time when the entire plan backfired. Joey sent me a text, just as he promised, except he wasn’t on his way to get a blowjob. As it turns out, Joey never abandoned the idea that he may have been meeting up with a guy. After a few hours of drinking with the rest of the basketball team, he was now on his way with the whole team to ”beat the sissy’s ass”. I quickly fled the park, being careful to stay off the path. I also called Sam to give her a heads up.

So now here I am, doing a piss poor job of walking home in these Goddamned heels and hoping to hell that I don’t see Joey. What was worse than the intense fear, was the overwhelming feelings of shame and heartbreak. I couldn’t believe that he was the type of man that would rather grab ten to fifteen of his friends to jump a guy who only wanted to give him pleasure than simply say no thanks. I had never felt so pathetic or alone. Deep down I knew that this was how I came out, beaten to a bloody pulp by my best friend and crush.

Suddenly, a bright red pick-up truck jumped the curb mere inches in front of me. I dropped to the damp dew-soaked grass below me and shielding my heap from the impeding beating that I was about to receive. I listened in terror as the vehicle’s door swung open and thunderous footsteps approached. I shuddered as I heard a man’s voice shout for me to get up. I couldn’t move, I was too afraid to even think. Even when I felt the two muscular arms of my attacker as he seemed to effortlessly scooped me off the ground, I didn’t move.

I felt a hard thud when he dropped my petrified body in the upholstered interior of the truck. Within seconds he was in the truck with me as we pulled out at high speed.  I still can’t tell you how he got the door open with me in his arms why I even afraid, I did not attempt to escape him. I soon realized that he wasn’t trying to beat me up. I began to wonder what he wanted from me if he wasn’t among Joey and his friends. I then wondered if I was being kidnapped, or on my way to getting raped. What if he was a rapist and didn’t know that I was a guy? It would be a death sentence.

”Oh God, please don’t hurt me!” I begged with a shrill voice.

”Open your fucking eyes, Man. By the way, if I wanted you hurt, I would have just left you where you were. Cochrane and his friends would have been happy to inflict as much pain as possible.” The man said with obvious irritation.

As instructed, I slowly opened my eyes to see that we were already out of town heading towards Front Royal. It was then that I discovered the identity of the drive. His name is Jake Dougan, and he was half the reason why I never came out. He was the school bad boy and the guy who had shoved me at least once a week for the past five years. Joey had always been there to watch my back when it came to bullies. However, Jake was the guy who broke the quarterback’s jaw while he still had his helmet on. He was by all rights the alpha male for all four years of high school.

I was out of the frying pan and into the fire. Jake was feared and respected by all but he seemed to hate most everyone, me above all. Yet, here I am, in a slutty Halloween costume with fake tits in Jake Dougan’s pick up. It struck me as strange, that for as much as I was afraid, I was also excited. I couldn’t explain it. I learned to be held passionately by a gentle lover, but the thought alone of a cruel dominating bully taking me by force had made me harder than I have ever been. 

I kept catching myself stealing glances of his body while he drove with a fierce look of determination on his face. He looked like he had just jumped out of bed. His solid unshorn chest protruded boldly through his open button-up short-sleeve shirt. The toned arms that had been carrying me only moments earlier looked almost mythical as I fixated on their every subtle movement. However, it was the occasional glances from Jake that was driving me crazy. Oh my god, he’s checking me out, I thought.

”What are you doing?” I asked, unsure of what to say.

”I’m driving, Dumbass. What do you think I’m doing?” Jake fired back.

”What I mean is why did you grab me, and how did you know about Joey?” I asked, part of me wondering if he knew who I was or that I was a guy.

”Lisa Hardwick. She called me and said that some Queen was going to get killed in the park. I nearly drove by you thinking that you were a chick, but then I saw you trying to walk in heels.” Jake said laughing.

”Hey fuck you. Don’t you think I had enough shit for one night without you teasing me?” I snapped angrily.

”You should be saying thank you. You’re the one who was trying to trick a straight guy into fucking you. If he didn’t bring his friends, I would have liked to let him kick the shit out of you.” Jake pause becoming visibly angrier. ”No instead, I get called right out of Bekah Stratford’s bedroom in the middle of the fucking night to save your fake ass.” Jake shouted with a large protruding vein in his neck.

”I’m sorry, Jake. Thanks for saving my ass. It probably won’t change anything. I’m sure that he will just get me to school.” I said both afraid and aroused by his rage.

”Unless you told Joey, nobody else knows that Xander Sloan is a fag. It’s not my shit to share, so your secret little tranny escapades are safe with me.” Jake responded as he appeared to calm down.

”Is that why you have been so hateful towards me? Because I’m gay?” I asked.

”I honestly could care less about who you are trying to hook up with. I don’t like you because you are a liar. I don’t care about gay or straight or all of the shit in-between that seems to update every other week.” Jake replied as put a cigarette to his lips before lighting it.

”Like you don’t hate gay people, I’m sure. Also, how am I a liar.” I replied with righteous indignation.

”Well, aside from getting a straight guy you call your friend to unknowingly fuck you, there is the way that you come to school every day talking about banging bitches when you are very obviously gay. I don’t hate anyone for what they are. I may not understand how or why but it ain’t my life to live. It’s the shit people do that pisses me off. For example, we’ve been around each other for years, and I don’t know a fucking thing about you, aside from the fact that everything I know is part of a disguise.” Jake stated, his words cutting me like a knife.

” Then why help me? I mean, you said Lisa asked for your help, but clearly, you don’t like me.” I asked.

”No one deserves to get jumped by ten plus guys just because they enjoy wearing girls’ clothes. I would hope that if it were me, you would have done the same thing.” Jake answered as he took another drag off of his cigarette.

It was a side of him that I had never seen. As far as everyone else was concerned, Jake Dougan was a violent psycho. Yet, as I listened to the words coming out of his mouth, I couldn’t help but feel attracted to this new heroic version of a man who yesterday was my nemesis. I then found myself somewhat disappointed with his answer. I guess that a part of me wanted him to want me. With as terrified, humiliated, and ashamed as I was, I wanted him to ravage me like a gladiator and his prize. Unfortunately for me, Jake was not mutually interested.

”By the way, I don’t like to dress like this. This is the first and only time that I ever wore women’s clothing.” I said trying to keep the conversation alive.

”That’s a shame. I mean you look, it’s a good look for you.” Jake replied with a smile on his blushing face.

” you like this? I kind of feel silly.” I added while casually opening my cloak, revealing some of my fish netted thighs.

”You pull it off. Not trying to sound any kind of way, but you’re very pretty like this.” Michael added somewhat nervously.

The ride was quiet for a moment. I noticed that we had already been to and left Front Royal. My mind quickly filled with erotic thoughts and fantasies. I wondered if he was simply stalling until he got up the nerve to make his move. After all, he did say that he was in bed with Bekah Stratford when he got the call to come to get me, so it’s not likely that he got to finish. Bekah was about as interesting as dish-rag. The only reason a guy would put up with her constant pointless babbling, was because she almost always put out.

”So…where exactly are you taking me?” I asked coyly, trying to sound cute.

”Hell if I know. What ask me?” Jake asked looking at me with a puzzled expression on his face.

”I don’t know. I just figured that you had something in mind otherwise you would have brought me home.” I replied.

”I could take you home, assuming I knew where you lived. Oh, and what the fuck do you mean by something in mind?” Jake asked sharply.

”I’m sorry, I didn’t think that I mean I didn’t realize that you were waiting for me to tell you where to go. I just… I’m sorry. My house is on Teavis Street.” I answered with somber embarrassment.

”It’s fine. Let’s just get you home.” Jake said with a stern tone.

”God, I’m so fucking stupid.” I muttered under my breath, as I felt my eyes begin to fill with tears.

”Don’t do that! Don’t you start with self-pity?” Jake snapped.

”Why? Huh… I mean, I let myself get talked into dressing up as some ugly tranny whore, my best friend would rather beat the shit out of me than fuck me, and all I can do is beg losers to let me blow them.  I am nothing but –” I sobbed before I harshly interrupted by a swift slap in the face.

”Shut the fuck up! You listen to me. Joey ain’t your friend. If he was, you wouldn’t be afraid to tell him that you are gay. He damn sure wouldn’t have tried to jump you. Sam and Lisa, they’re your real friends. Dumb ass friends, but friends. Secondly, you don’t ever beg for something that others should be begging you for. Shit, dude, or not, I’d fuck you.” Jake roared before realizing what he had just said.

The cab of Jake’s truck fell dead silent as we were both stunned by his words. The muscles in Jake’s jaw were clenched tightly and his face was beet-red. I could see that he was embarrassed by his remarks. However, I, on the other hand, was feeling excited. I knew he had been eyeing me ever since we started driving. I somehow instinctively knew that if I ever had a chance of getting laid tonight, this was it. Jake had just, in his way, said that he wanted me. It was then that I remembered Samantha saying that if I could get him to come at least one time then he’d be open to more.

”I didn’t mean to say that.” Jake said with a low voice.

”It’s ok Jake. I get it. You were probably in the middle of fucking Bekah when you came to save me. Now, here I am dressed all slutty with fake tits and all. It just popped out.” I said with an effeminate voice while resisting the urge to be direct.

”Well, we weren’t having sex. She was just… um, stroking it a little. You do look like a girl right now.” Jake added nervously, his eyes carefully studying every inch of my body.

”I know. Sam and Lisa outdid themselves. Although I am kind of jealous.” I said with a sly grin as I watched the bulge in his pants grow.

”Of Sam and Lisa?” Jake stammered.

”No, Silly, of Bekah. I would give anything to have held a big hard cock like that in my hand. She is so lucky.” I added while delicately licking my lips.

”Yeah but you will always be Xander to me. I don’t know if I could ever do anything with a guy.” He said with a shaky voice while trying to adjust himself without me seeing.

”693.” I said, sliding just a few inches closer to him.

”What?” Jake asked in a nervous sweat.

”My house number, 693. It’s just up ahead.” I replied, realizing that I had him on the ropes.

”Oh, ok.” Jake stammered as his truck pulled into my driveway.

”You know, I owe you big time for the rescue.” I stated, yet again, inching closer.

”You don’t owe me anything.” Jake said almost whispering.

”Just hear me out before you say anything. You said I looked like a real girl, so why don’t we just pretend that I am. I can be Xander tomorrow, but tonight on Halloween, maybe Lexie can give you some relief.” I suggested going all in.

”Man, I uh. I’ve never been with a guy.” He replied with beads of sweat forming on his forehead as he shut off the truck.

I somehow instinctively knew that if I had a legitimate chance of getting laid tonight, this was it. Once more I inched closer to Jake. I was now so close that our shoulders nearly touched. My full painted lips were right next to his ear teasing it with my hot breath. I couldn’t help but love how very cute he looked while he was resisting the urge to look at me with all of his might. I have never felt as powerful or in control as I had at that moment. His whole body shuddered when I placed my hand on his thigh, gently massaging the muscular flesh mere inches from his groin.

”As far as anyone is concerned, Jake Dougan doesn’t fuck with dudes.” I whispered as I slowly began to slide the zipper on his jeans. ”How about if you let me take care of you. If you don’t like it or it gets too weird, you tell me to stop, and I’ll get out of the truck. We will both just pretend that it never happened. So, Baby, what do you say?” I asked with a sultry tone as I slowly brushed my hand over the top of Jake’s swollen groin.

”Yes, Lexie.” Jake uttered with a defeated whisper.

My heart was racing when I leaned forward to undo the button on his jeans. It was then that I discovered that Jake wasn’t wearing any underwear. I wrapped my fingers around the rock hard shaft of his throbbing cock. As I raised his monolithic rod from the confines of its denim prison, I was awestruck by its sheer size. It was the first time that I had ever held a dick in my hand without my fingertips touching. The shaft had to be at least nine inches long with a bulbous mushroom-shaped head at its peak. Not one of my many toys could dare match it in length or girth. Yet, for how intimidated as I was by its size, I was more excited than I had ever been.

The combination of sweat and Jake’s natural musk filled my nostrils causing me to begin salivating. I lowered my hungry mouth onto the soft rubbery flesh of Jake’s cock-head. I could hear the deep gasp come from his as I was twirling my tongue around his tip. I took his cock deep into my mouth, pausing briefly to savor the moment his thick head struck the back of my throat. Gradually, I began bobbing my head up and down the length of his shaft. With my left hand, I started to gently stroke his meaty pole, while I was cradling his heave balls with my right. Jake’s entire body was writhing in delightful agony with every passing second of my working his massive cock.

My full lips felt overstretched and my law was starting to ache as I sank deeper and deeper on Jake’s dick trying to get more and more of him into my greedy mouth. His strong masculine hand was intertwined with the soft strands of my hair while he was guiding my head up and down his pole. I gave his balls a gentle squeeze as I finally felt the shaved skin of his pelvis graze the tip of my nose. Jake was moaning loudly with the sensation of my wet spongy tongue massaging his veiny shaft.

I brought my head up, struggling to catch my breath while I vigorously began jerking his cock. I didn’t know if it was the girl’s clothing or how good my mouth was making Jake feel but never before had I felt so sexy. I was sucking a hot guy’s cock, and he was loving it. I was sure that somewhere deep down it was Jake who thought that he was the lucky one. However, I had never felt so alive or so natural in my skin. I dove back into his crotch, this time taking his balls in my mouth. I was shifting from sucking one testicle to the other while continuing to stroke his cock with increasing speed.

”Holy fuck! This feels so good.” Jake groaned as he suddenly jerked his hip from the pleasure I was giving him.

”Thank you, Baby.” I replied with enthusiasm, dragging the tip of my long tongue up the entire length of his swollen shaft before taking him back into my mouth.

I resumed sucking his long pulsating member with gusto as Jake had begun thrusting his hips forward. His deep moan was becoming louder with increasing bass. His shaft was now thoroughly covered with a slick layer of my drool and black lipstick. The sounds of my crude slurping and lewd lustful moans seem to echo within the truck’s cab. It was then that I felt the sudden surge in Jake’s shaft. At first, he tried to pull me off of him, but I wasn’t about to be denied the privilege of swallowing his load. 

I clung tightly to both his rod and thigh until finally his cock erupted, filling every space in my mouth with his seed. His cum was thick and creamy with an ever so slight salty taste. I could feel his gooey essence escaping my mouth with a second equally powerful stream of semen surging into me. I then went on to swallow his load while I was furiously pumping his shaft for every last drop of his cum. He sent two more ropes of cum into my mouth before I had to come up for air.

My mouth was still full of his warm thick seed as I sat up to see the look of satisfaction on Jake’s face. He looked at me with a warm affectionate smile. However, his eyes grew wide when I briefly opened my gullet, showing him his load before I swallowed it all in one glorious gulp. I could see that somehow he was still hard and his twitching cock seem to be calling to me. My tummy was now a bit upset from the sheer volume of seed that I had just ingested. I pulled down the visor to check my make-up in the vanity mirror. Just as I had suspected, I looked like a hot mess.

My eyes were teary and bloodshot with dark black streaks of mascara running down my cheeks. The glossy pitch-black lipstick that had once accentuated my beautifully pouty lips was now smudged all over my mouth, chin, and nose. I grabbed the corner of my cape and began trying to clean myself up. After a little bit of spit and a lot of scrubbing, I had managed to get most of the makeup off of me. It was then that I saw Sam and Lisa standing in front of the truck, their eyes fixed on Jake and me. The pair didn’t look to be upset or concerned, rather Sam, in particular, had a smile of amusement.

”I should probably get going.” Jake said nervously.

”Nah, you should come in and have a beer with us. No parents no supervision and a 100% safe place to chill.” I interjected.

”You sure, that I won’t be in the way?” Jake countered.

”For real, I liked what just happened and would like to do more. We would be a lot less likely to get caught if we went inside. Don’t you want to fuck Lexie? I know she wants you to.” I said, removing the cloak and getting out of the truck, all the while, trying to give Jake an eye full of my pert round ass.

We weren’t even to the front door when I heard the driver’s side door open and close. Before I could turn around I felt Jake’s arm as it wrapped around me pulling me close. I glanced over to Sam who was in a similar embrace with Lisa. My heart skipped a beat as Jake removed his arm just long enough to grab a firm handful of my right ass cheek and giving it a brisk squeeze. It then dawned on me that someone I considered to be my worst enemy was the reason for the best night of my life.

We had spent the next two hours drinking beer and recapping the evening events, except for our moment of intimacy in the driveway. As promised, I kept those details between the two of us. How could I possibly out someone who had done so much to protect my secret? I wasn’t sure if Lisa knew what had happened between Jake and me, but I was fairly confident that Sam had seen or deduced enough to figure it out. Yet, despite all the fun, we were having, I could not stop thinking about Jake. I wanted to do more with him, but I was afraid that if too much time passed, he would lose his nerve.

It was not until Samantha had said that she was going to the garage for more beer, that I saw my chance to seal the deal with Jake. I offered to come with and help, which has always been our bathroom code. This was not a secret to Lisa who I was sure had some notion of my intentions. I was sure that if I could get Jake alone, he would be comfortable enough to finish what we had started. I had caught him eyeing my legs and ass a couple of times since we had come in. However, to my surprise, it was Sam who approached me when we had arrived in the garage.

”Oh my fucking God, Jake Dougan! You slut.” Samantha said with an excited laugh.

”I know, right? Why did you guys even call him?” I questioned with a girlish grin.

”He’s Lisa’s ex. He was the first one she came out too. Weird I know, but he’s a very good guy. So, tell me what happened.” Sam replied taking my hands in hers.

”What do you mean? I told you the whole story.” I replied.

”Bitch, you know damn well what I mean. How about the part of the story where Lisa and I saw your head pop up from behind the steering wheel. Or, you can tell me why you are still wearing those clothes.” Sam snapped playfully.

”Oh shit! You guys saw that?” I asked embarrassed and horrified.

”Oh yeah, I did. You even showed him his cum before swallowing it. I never thought you were like that.” Samantha said, her pleasant smile reassuring me.

”I’m sorry, I don’t know what got into me.” I responded.

”Jake’s dick, I imagine. Is that why you are still dressed up?” Samantha asked again, this time without a hint of sarcasm or humor.

”Okay, I admit it, I like dressing up!” I snapped in disbelief from my own words. ”I look sexy, all the guys that were staring at me tonight wanted to fuck me, and I wanted to get fucked by them. So make whatever comments about it you feel like making, but please help me to get with Jake.” I pleaded.

Sam looked at me with a stunned expression. I knew that I had shocked her with all that I had said, however, the strange smile that had begun to form on her face had left me at a pause. She reached into the passenger side of Lisa’s tan Ford Taurus and removed the box that had all of the makeup they had earlier applied. I didn’t know what to say as she sat the case down on my dad’s workbench, so I simply opted to remain silent. She pulled her phone from her back pocket and swiftly dialed a number on its touch-screen. I heard the dialing on the other end before a lady’s voice had answered. Greenlight, was all that she had said before she abruptly ended the call.

She pulled out the stool from underneath the workbench and patted it gently, signaling for me to sit down. I did so without hesitation or question. She began by wiping away all of the older remaining with an alcohol pad before drying my face with a cloth napkin. Even though we had done this all before, this was different. Samantha may have been silent while she was applying my foundation, however, she was giving off a strangely maternal vibe. I remembered the bit of truth that Jake had bitch-slapped me with in regards to who my real friends were. It then occurred to me that Sam may have only been in the closet for my sake. Unlike me, she had a hand to hold when she went out to face the world.

”You know, I have about a million jokes I can make about the new you, but then I’d be a hypocrite.” Sam paused before continuing. ”I’m gonna let you in on a little secret. If you tell anyone, not only will I deny it, but I will also fucking kill you.” She said while applying blush to my cheeks.

”I own a strap-on. I sometimes like to pretend that I am a guy when I am with Lisa, and when I wear it, I expect to be called Sir. I also used it on Tony Ominsky before you and I started dating. I like girls, always have, but just like everyone else, I have my weird kinks. My point is that if you are happy with you, who the fuck cares what you like. Just don’t ever come to me with a foot fetish.” Samantha added with a smile.

”We are the perfect couple. I dress like a girl for boys and you pretend to be a guy for girls. Thanks, Sam. I didn’t know it before tonight, but you have always been the best friend a girl could ask for.” I said, taking advantage of the tender nature of the moment.

”All done. Now we will go down to the basement together. Lisa is down there right now giving her pep talk to Jake, so knowing her, he’ll be DTF when we get there. You promised me the master bedroom for the night, and I intend for Me and Lisa to use the hell out of it. It will be just you and your man, let’s go get laid.” Samantha said as she stood and started for the door. ”Oh, yeah, don’t forget to grab the beer, Bitch.” She added as she swung open the door to the kitchen.

”Yes, Sir!” I replied, with a snarky tone and a smirk when Sam scowled back at me.

We made it back downstairs where Jake and Lisa were both awaiting our arrival. Neither Sam nor Lisa said a word before the two of them headed upstairs leaving me with Jake. He sat up at attention as I carefully descended the stairs, seductively swaying my hips with every step. I could see the hunger in his eyes as I drew closer to him with a newfound confidence in my sexuality. For as much as I wanted him to jump up and take me right then and there, I was also enjoying how very worked up my appearance was making him. I did a slow and suggestive little spin for him making extra certain that he got a good look at the ass that I was offering him.

”Do you want me?” I asked with a sultry voice.

”Oh my God, Yes.” He panted 

”Hmm, if I’m a good girl, will you let me ride your giant dick?” I asked, getting on my hands and knees as slowly crawled toward his lap.

”Well, Lexie, since I only have you for tonight, I guess yes is the only thing I can say.” Jake said with a cheeky grin as he stood up, his crotch only a few inches from my face.

”Baby, you can have me anytime, anywhere, and in anything you like.” I said, yanking his pants down only to be struck in the chin by his enormous hard cock.

I immediately took him into my mouth and began worshipping his stiff member. His legs became like jelly within seconds of me bobbing my head on and off of his cock. I could still taste the remnants of cum from the last time I opened my throat to him. I then guided him back to the couch where I continued to deep-throat his hard dick. He took a fist full of hair with one hand and started petting my raised ass with the other. I could feel his middle finger massaging and teasing my little dirty star while he was aggressively fucking my face. 

Jake then stood, pulling me off of him by my hair and slung me face down on the over the arm of the couch. I quickly shouted for him to use the lube in my fanny-pack. In a frenzy, he ripped it off of me breaking the chain. Seconds later I felt his strong rough hands squeezing and kneading my plump round cheeks. Then in one sharp animalistic move, he tore a large hole in the seat of my outfit. I breathed a sigh of relief when I heard the cap to the bottle of lubricant snap open. It sounded as if someone was blowing a raspberry when he was applying the lube to both his cock and then my eagerly awaiting ass.

”Please be gentle, I’ve never had anything as big as you in me.” I whimpered as I felt the head of his cock pressing against my anus.

I soon felt intense pressure followed by a pop, then even more pressure while the tip of his manhood breached my anus penetrating me. The pain was almost unbearable as he slowly pushed inch after bitter inch deeper into my bowls. I could feel the tears flowing freely down the sides of my face while I was doing everything in my power to remain to lose enough for him to fill me. Finally, I was able to feel the bristly hairs from his belly on my spread cheeks. After a brief pause, Jake then started sliding in and out of me with short slow strokes.

At first, I felt as if Jake had been driving a wedge deep within me, splitting me in two like a piece of firewood. However, after a few excruciating minutes, I could feel my body beginning to relax while my insides were contouring to Jake’s member. The pain was subsiding, giving way to that strange pleasure that could only come from anal sex. My meager little dick had once again become rock hard, awakened by the stimulation to my prostate. I felt little a series of tingles radiating throughout my entire body with each short powerful thrust of his pelvis.

His hands were clamped firmly around my delicate hips as he was pumping his cock in and out of my little he-pussy over and over again. I would let out a slight feminine whine each time his solid muscular groin crashed into ft supple little ass. I then began to throw my ass back into him in tandem with each of his steady potent thrusts. It was then that Jake began fucking me harder with an ever-steadily increasing pace. My dick was swinging wildly back and forth from the momentum and power of Jake’s thrusting hips, even occasionally smacking up against my soft flat belly.

”Ummm, yes, harder Jake, fuck me harder.” I cooed as his massive pulsating organ was rapidly sliding in and out of my overstretched ass hole.

”That’s what you want, you little slut? You want me to treat you like a dirty little whore?” Jake growled with his cock plunging in me.

”Yes, please!” I begged in between his deep burrowing thrusts. ”Use me, make me your little whore. I want to be your private sissy cum-dumpster!” I shrieked as Jake began to plow into me with all he had.

It was strange, I never really cared for dirty-talk before that night. I always found that it either felt demeaning to me personally or distracting, as I would struggle to think of something sexy to say. However, the combination of my night as a slutty little girl along with the fear and excitement I felt while dressed up, had awakened something lewd and primal within me. At this moment, it felt like Jake’s dick was on the verge of punching a hole in my stomach. My hips and thighs had never been so sore, and I realized that I loved it.

The walls were ringing with echoes of the intense clapping sound from Jake’s hips rapidly colliding with my ass. On the verge of sheer overwhelming ecstasy, I spat on my hand and began frantically jerking my dick. It was only a matter of seconds before I shot a seemingly endless rope of cum onto the side of the couch, creating a mess that even my super tolerant parents would have freaked out over. I was screaming as I felt like razor blades were passing through my swollen urethra.

Jake, again grabbed a first full of my hair while at the same time wrapped his dense muscular arm around my waist, forcing my face into the large glob of cum that I left oozing down the side of the couch. I could feel my slime-covered face grinding into the cheap upholstery of the couch as he was viciously pounding my ass, driving me like a nail from behind. Out of pure lust, I began to lick and slurp up my remaining semen from the course wooly fabric.

”Yeah, that’s a good girl! Clean up your mess.” Jake jeered, his fat meaty dick pumping my ass hole harder and harder.

With one hard thrust, Jake yanked his cock from within my abused sphincter. He then spun me around with my back to the side of the couch. He was standing over me with his cock in his hand, postured like he was taking a piss on me. He was pumping his rod with it angled directly at my face. Jake let out a mighty roar as an explosion of cum shot out from the head of his cock. He saturated my face and belly with three powerful streams of his pungent seed. I then sat up and eagerly took his cock back into my cum drenched mouth, polishing his rod clean with my tongue.

Drained and exhausted, I fell back, gasping for air. To my surprise, Jake knelt in front of me and gently leaned forward for a kiss. I could feel myself melting into him as our tongues passionately danced in each other’s mouths. I was overcome with the aroma and flavor of our combined spunk. I could have lived forever in this his bizarrely romantic embrace. However, as our lips parted and our eyes locked, I accidentally said that I loved him. His face took to shock as he heard these words. I then feared that I may lose him forever as a result of my haste.

”Me too, Alex.” He said softly almost whispering.

”You mean Lexie, I said doe-eyed.

”I like Alex better.” He quickly replied.

It was just before noon on November first when I woke coiled in Jake’s manly arms. I can’t begin to describe how wonderful it felt to not have woke up alone for the first time. I quickly got up to begin cleaning up before my parents got home. I had never been so sore in my life. It felt as if I had broken my hip while I was clearing the trash and wiping clean all of the dried cum that Jake and I had left in the night. We had fucked to or three times in the night before we finally passed out in the night from exhaustion. I was reminded of our many rolls in the hay by the squishy sensation of cum and lubricant in my sore ass. 

However, despite the immense pain that Jake’s cock had left me in, I knew that I had discovered who I was. It would not be the last time I dressed last night would be the last time I ever went by Xander. I had been reborn a sissy slut, baptized in cum, and used to my greedy heart’s content. It was then that I realized that Sam and Lisa had left sometime in the night. However, a suitcase had been left on my parent’s bed with a note.

Alexander,

I think we should see other people. From what I heard last night, you either had a blast or you were murdered. Whichever one it is, I don’t think that you will need a fake girlfriend anymore. Lisa and I are both happy for you. I am hoping that you can have with Jake, what I have with Lisa. This isn’t goodbye forever, not even really a goodbye. I still want to hear all of the juicy details, so feel free to call me anytime for make-up advice or just for some good old fashioned girl talk.

-Best friends forever, Samantha Davis.

I couldn’t help but smile and laugh as I opened the suitcase. Sam had left me with a bunch of girls’ clothing, sexy underwear, her make-up case, as well as wet wipes and KY. This was going to be the first gift of nothing but nut November. As I lugged the heavy suitcase to my bedroom, I managed to catch a glimpse of myself in the hallway mirror. My make-up was all kinds of jacked, replaced by several layers of dried spit and semen. My clothes were tattered, leaving me to walk around the house with cum and lube oozing from my bare ass.

”This is a sissy slut, in her natural habitat. ” I whispered chuckling to myself and knowing that this is only the beginning.

End.