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Author’s Note:
1) This work contains sex of a heterosexual as well as a Homosexual nature.
2) All Characters in this work are 18 years of age or older.
3) It also features Characters from the Shade Trilogy and Red. It is recommended that you read the first two installments before beginning this one.
4) A special thanks to 1moeannie for all of your work with editing, and to AlexBailey for your insights on proofreading and additional advising.
5) Finally a very special thanks to MsNatalie99 and TessaC who are the inspiration for the Trap or Treat Trilogy.
*****
Saturday morning.
I awoke on the cheaply upholstered couch in the basement. I was coiled tightly in the heavy throw which was usually draped over the back of the couch, covering a large unsightly semen stain that Jake had left the morning after Halloween. Despite my many frantic attempts to scrub it out with everything from Dawn dish soap and water to the heavy-duty carpet cleaning solution, I could almost swear that the scent of his seed remained. I soon found myself writhing and dry-humping the cushion below me as I was imagining his impressive girth driving into me. The basement was thoroughly chilled by the cool autumn air outside. However, within the confines of my dense plush blanket, however, things were just beginning to heat up.
I woke horny, neither able to get back to sleep nor fully awaken until the hunger was satiated. Before I knew it, I was massaging my perineum through my pale-blue bikini-style briefs with my ring and middle fingers while teasing my delicate shaft with my thumb. This would hardly be enough to push me over the edge. It felt amazing, allowing my excitement to grow. I was now lying on my back, reaching for my secret toy carefully hidden in a shoe-box labeled crafts under the couch.
As tolerant as my parents were, I knew that they would be pissed off if they happened to come across anything that they knew had been in my ass. In our home, it was an unspoken rule that anything and everything sexual was to be kept in the bedroom. Their poor heads would explode if they were to ever find out how many of my make-shift anal dildos they’ve held in their hands. Before I could buy toys of my own, I had fucked myself with everything from the cucumber that ended up in the salad and the ergonomic handle to my dad’s backscratcher and on down to my mother’s favorite hairbrush. Remembering such behavior should have left me feeling disgusted with myself, but in the moment it only made me hotter.
For this time, however, I wouldn’t need some random smooth object. My all-time favorite toy was located mere Inches from my wondering fingertips.Finally, I was able to reach the box and fish out a tightly rolled paper bag. I briefly paused my self-gratification to sit up and get ready for the main course. Within the bag was a bottle of lube and Big Papa, a seven-inch long black prostate stimulator. It was the first and only vibrating toy that I had ever owned. It looked like a normal vibrator except for the wider angled bulb at its tip.
While still buried beneath my blanket, I slid my panties down leaving them on my right ankle. The bottle of lube, as well as, Big Papa were still cold from their time under the couch. I usually tucked the toy between my inner arm and chest to warm up while I applied the lubricant. This morning was no different. Before using the lube, I peeled off both of my pink girly ankle socks, putting one within the other, and then put them over my cock like a condom. I then put a liberal squirt of lube in the palm of my hand, using it to coat both my anus and the toy.
I closed my eyes imagining myself with legs spread wide for both Jake and Raven as I began to press the toy against my waiting anus. I could feel myself breathing harder as I slowly pushed the tip through my puckered opening. My heart was racing with the memory of Raven’s painted nails digging into my thighs as she filled me with one inch after another with her monstrous dick. My breathing was ragged and I was already moaning shamelessly by the time I had the whole toy buried in my greedy asshole.
“Oooh Fuck!” I groaned after pressing the button on the base of its shaft causing it to vibrate with a potent rhythmic pulse.
My entire body was shaking, overcome by the indescribable pleasure derived from the toy’s powerful vibrations. I began sliding the toy in and out of my hole with ever-increasing speed all while daydreaming of Raven and Jake taking turns fucking my ass. My lewd moans got louder and louder as the toy pumped into me. I began sucking my left thumb like it was a cock and, pressing the vibrator’s button to increase the intensity of the pulse. I bit down on my thumb letting out a loud drawn-out whine, dreaming of being thoroughly used by the two largest cocks I knew.
Then something strange happened. In my fantasy, Jake was taking his turn pounding my needy ass as Raven came up behind him, pressing his face ankarakazan.com into mine, and forcing her way into his virgin asshole. Just the thought of it was enough to send my arousal into overdrive. My entire body was rocking with the image of her plunging into him and him into me.
Suddenly, I let out a loud bellowing howl as I came hard. I could feel a slimy sensation within the socks on my cock being as they were filling with my milky seed. I was overstimulated. I tried to turn the toy’s vibrations off, but instead turned the vibrator up to higher and higher intensities. I could feel the semen oozing through the fabric of the socks onto my belly as I ripped the toy from my colon throwing it to the floor. I was struggling to catch my breath. It was as if, in my moment of ecstasy, I had forgotten how to breathe. It was one of the more potent orgasms that I had ever had.
It was almost a full five minutes before I could calm myself down. The sound of my low moaning and the echo caused by my toy vibrating on the floor filled the room. Slowly, I sat up, my legs felt like jelly, and most of the rest of my body numb. I carefully removed the socks from my softening penis. Seconds later, I was on my feet throwing the socks and my clothes from last night in the washing machine, while simultaneously disposing of the evidence of my morning activities in the rinse cycle. It was kind of sad to me that I had masturbated so much that I came up with numerous hacks.
I was still staggering when I changed my panties and put my toy away. Normally, I would wash it in the sink, but I knew that I still needed to get ready to meet Raven later. I wasn’t sure what was going to happen at the party, but I had said that I would go.
After cleaning up the mess in the basement and fixing the couch, I remembered that Lisa and Sam were still in the house. I paused, trying to be sure that everyone was still asleep before I started my day.
It was 10:00 am as I climbed the stairs. The night before, Sam and Lisa had arrived at the house. As was our custom, we were all hanging out in the basement drinking beer and gossiping like church hens. This time, however, the topic of discussion was the outrageous encounter I had with Raven at the mall earlier that day. It took me an hour just to convince Lisa of Raven’s unique gender situation. Lisa had spoken to Raven several times and even asked her out before she and Sam had begun dating. So she was especially surprised to learn the ten-inch secret that Raven was hiding. I know I was too when I first saw it.
We talked about the downward spiral I was on. Sam was somewhat hurt that I didn’t reach out for a shoulder to cry on. However, we both agreed that a phone works both ways and that no one was happy to see Jake and I split up. Nonetheless, I was relieved to be back in the company of my friends. The topic of discussion now was what to do next. I was curious about their thoughts both on Raven and her invitation, and on my bumping into Brad. I had decided that regardless of what happened last night, that I would be attending the party this afternoon.
I wandered upstairs to my room where Sam and Lisa were sleeping. In my drunken stupor, I had pretty much forced then to stay the night, even going so far as to give up my bed and sleep in the freezing basement so that they could sleep together. I didn’t even think to knock as I entered my room. In the years that Sam and I had been posing as boyfriend and girlfriend, we saw each other in all manner of compromising positions. We always felt safe around one another in the knowledge that sex would never play a part in our relationship. I had even caught Lisa going down on her the first night they were together. They foolishly thought that I was too busy with my Elder Scrolls game to notice.
To my surprise, they were both awake and staring at me in awkward silence. They were sitting up only half covered carrying on a conversation. Lisa quickly yanked the covers up over her chest. Sam left her chest uncovered with no regard for my eyes.
“I’m sorry, I didn’t think that the two of you were up. I should have knocked.” I said in a panic quickly looking away.
“Damn right, you should have!” Lisa snapped.
“It’s cool Xander, We’re in your room. Besides, it’s not like you were perving about in a nightgown just to see boobs.” Sam remarked as she playfully tugged the covers down from Lisa’s chest.
She was correct in the lack of interest I had in a woman’s body. Her breasts may have been enough to drive my classmates in school wild but to me, they were just flesh. I was more interested in where a girl acquired her blouse than what was beneath it. It was honestly out of respect for Lisa that I was looking away at all. Sam and I had spent entire days playing Mario Cart half-naked without a second thought. I don’t know if Lisa had ever had a male friend who never thought about sleeping with her.
“Can I just grab some clothes? After that, I will leave you to it.” I asked still looking away.
“Leave me to what? What do you think we’re doing?” Lisa asked, still agitated.
“Don’t know, Don’t care. I just want to get a shower so that my parents won’t see their 18-year-old son wandering around their house in a nightgown and bikini panties.” I replied.
“Lisa, calm down. Xander is gay. He sincerely has no interest in our tits or our sex life. Come on in Xander and please close the door. I don’t think your mom would be happy if your dad saw our tits.” Sam said with a stern calming voice.
Closing the door behind me, I made my way to the closet to retrieve the outfit that Raven gave me. I could almost literally feel it in the air as Lisa began to relax and recognize that my presence offered no threats. It wasn’t like I couldn’t understand where she was coming from. Lisa had always been the target of the unwanted affection of others. Either that or she would be ridiculed for her openness when it came to her orientation. She wasn’t always at the top of my list of favorite people, however, she always had my respect. She had more balls than most of the men I had ever been with.
“I’m sorry, she usually isn’t so shy. We just woke up and a dude walks in wearing girls’ lingerie. It can be jarring if you aren’t mentally prepared for it.” Sam said.
“I can see that.” I responded, making a conscious effort to keep my back to the girls in my Queen sized bed.
“Is there any way we could borrow something to wear home? I didn’t think that we would be staying the night.” Sam asked the sounds of her getting out of bed and shuffling around filling the room.
“I mean, we don’t live that far away, so it isn’t really necessary.” Lisa added.
“It’s no problem. Boy clothes on the left, girl clothes on the right, bras are in the top drawer of my dresser, but I don’t share panties.” I declared quickly.
“Thanks, Xander.” Sam said.
“Yeah, I appreciate it.” Lisa agreed. “You’re ok, Sam is right. You are a friend of mine and Sam’s. I was just surprised to see a man walk in before I was decent.” She added.
I turned to see both girls standing with their eyes on me. Sam was topless wearing only her panties and Lisa was wrapped snuggly in my comforter. I laid the outfit out on the bed along with three different pairs of shoes. All three were black and would match the dress but I didn’t know which ones would be best for the party. Without thinking, Lisa brought a pair of black leather block heeled ankle boots from the closet, taking the other shoes away.
“You’re going to a party at an undisclosed venue for an undisclosed amount of time. These are going to be more comfortable than your various heels. They will also be better if you’re outside.” Lisa said as she was carefully putting the shoes I selected away.
“Can you wear these with the stockings?” I asked.
“You can if they’re the same color.” Sam interjected.
“You should also consider a cardigan to accompany the dress. It’s going to be chilly today and I think it would add some ladylike class to the ensemble. There should be a white one in with the clothes Sam gave you.” Lisa said as she continued to rummage through my closet.
“Thank you, Lisa. Thank you, Sam.” That was all that I could say as I took my clothes and went for my shower.
“Hey Xander wait up a second.” Sam shouted, causing me to pause. “Go on, Lisa.” She added, nudging Lisa who still shield her chest with my comforter.
“What’s wrong?” I asked more confused than concerned.
“Well, um Xander. You’ve always been kind of a stand-up guy, acting as an alibi for Sam and me to be together, letting us treat your house and even your bed like a motel room, and it’s not like I was always the nicest person. I guess I just wanted to say thank you.” Lisa said, visibly embarrassed.
“It’s no problem.” I responded.
“It may not be anything to you but it has meant the world to us.” Sam countered.
We all just smiled and nodded in our strange little moment of silence. I wasn’t exactly sure where that had come from. We had all known each other for years and only recently started to coming into our own. It seemed odd to me that now when they had a place of their own and no longer required the safe space that my basement had previously provided, that Lisa chose to thank me. I still didn’t know what to make of it when I left the room. It was already 10:45 and I hadn’t contacted Raven yet.
I carefully hung up my clothes before jumping in the shower. For as nervous as I was to see Raven again, I was also becoming increasingly excited. The water wasn’t even luke-warm before I jumped into the shower, causing me to let out a bizarrely inward gasp as the cascade of cool water forced the air to evacuate my lungs. It was a small struggle to say within the downpour long enough to shampoo my hair. Fortunately, the water’s temperature had begun to rise by the time I was lathering in the conditioner.
Washing my body was a relatively quick task. However, I did need to apply my hair removal cream as well as exfoliate my skin. Less than fifteen minutes later I was out of the shower and drying off. It was then that I caught a glimpse of myself in the tall over the door mirror. I was short with a slender feminine frame and an ass that most of the girls I knew would have killed for. Yet, as I stood there staring blankly at the many small bruises on my ass and thighs, I was thinking of Raven’s body.
She was much taller than I was and her ample bust made her appear far more desirable than me. I didn’t want to change, but I couldn’t help but wonder if I was less desirable because I was incomplete. She had so much confidence that even with my lack of attraction to her, I was still powerless against her advances. Even her penis was more admirable, which made me feel as if she was both more man and more woman than I could ever hope to be. Between the two of us, she was the apex predator making me the fox to her wolf.
I began to wonder if maybe Raven wasn’t that hot but instead I was just that weak. Even she pointed out that I had allowed myself to be taken advantage of. I then remembered the sensations of her mouth on my erection along with the strange pleasure I got from having her tongue in my hole. I felt dirty, violated even, yet I was getting so hard just thinking about it. How could I be so conflicted? I decided to go out as a lady and stop allowing myself to be a cliché sex toy only to be fucked in the ass by a she-male four hours later. I knew that I could never have something real if I gave it up so easily.
The 11:30 am alarm on my phone went off, breaking my momentary trance. I shut off the alarm and took a deep breath. I knew that I had to get dressed. It was odd how much I hated myself whenever I was alone, however, when I was Alex, those feelings would return to the dark corners of my mind. I started getting dressed, putting on the pink lace bra and thong set which was a bit difficult due to my erection. I had to get in touch with Raven by noon, so I was already out of time to take care of it. After I put on the black garter belt and sheer stockings I again paused to look myself in the mirror.
I couldn’t help admiring the difference in my appearance. The combination of the lace thong, garter belt, and stockings gave my ass an irresistible look. I could almost feel my confidence soaring as I studied my accented curves and contours. Next, I put on the black strapless dress. It was snug around my waist and chest but roomier in the skirt that sat just below where my cheeks met my thighs. I was impressed by how the boots and cardigan Lisa recommend complimented the outfit Raven had given me. Despite the lack of work on my hair and makeup, I was truly feeling like a lady, sexy strong, and confident.
I was still trying to put my makeup on when I made the call to Raven. It only took a few seconds of conversation to lay out the plan. She was only about five minutes away from me so I would have to hurry to meet her in the driveway. I was saddened to see that Sam and Lisa had already left by the time I made it back upstairs. However, I at least had the knowledge that I could still call them and that we were all still friends. I didn’t know if it was the night I spent hanging out with them or the new outfit, but when I got outside I was feeling reinvigorated.
I didn’t have to wait long for Raven to arrive. She pulled into my driveway driving a black Mini Cooper with a lime green racing stripe. The music in the car was playing so loud that I could feel the vibrations coming up in my from the concrete below. I was bombarded by the combination of the loud punk music and the overwhelming skunky scent of marijuana when I opened the passenger side door. Suddenly, I felt overcome by nervous energy. I quickly got in, trying my best to act casually even with my palms sweating and heart racing.
Even as anxious as I was feeling, I couldn’t help but notice how very cool Raven was. She was wearing nothing but a black wife-beater and a pair of green basketball shorts. I was taken aback by this, considering the clothing that she had picked out for me to wear to the party. I wanted to ask her about it, but no sooner did the thought go through my mind, she whipped out of the driveway like a stunt driver and sped off.
“I’m so glad that you called.” Raven said, her voice barely audible over the loud music.
“ME TOO!” I shouted over the radio.
Raven burst out in boisterous laughter as she turned the radio down to a low murmur. She reached over my lap to the glove box causing me to flinch. She didn’t acknowledge my flinching as she removed a tin box that was large enough to hold a paperback book. As I closed the glove compartment, Raven was opening the tin box in her lap. Inside the box was a blunt and a flask.
“Sorry about the noise. The Misfits are meant to be played at bone-shattering volume. Are you a fan?” She asked as she brought the hand-rolled blunt to her lips.
“Not really. Sorry.” I replied as I watched her lighting up.
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