tagTransgender & CrossdressersA Halloween to Remember

A Halloween to Remember


Saturday morning I woke up feeling strangely euphoric. I remember thinking about it for a moment, and then realizing: it was Halloween. Cheryl and I had been invited to a party! The next morning (and for many, many mornings thereafter), I would remember that Saturday as one of the epic erotic encounters of my entire life.

The party was going to be at the house of some friends of ours, members of a rather exclusive campus sorority. I'm quite sure the sorority had no actual written membership criteria, but the fact was that all of the sisters had three things in common: they were excellent students (not one of them with a GPA less than 3.7), they were athletes, and they were all stunningly beautiful. I knew this to be true because I was lucky enough to have been invited to last year's bacchanal. Oh, there was one other thing: costumes were mandatory, and skimpy was the rule. Many of the sorority girls were artists and active in campus theater productions. Body paint had been very much in vogue last year.

Cheryl, my girlfriend, would be coming as Diana, Goddess of the Hunt. It was obvious that she had given serious consideration to her choice: Cheryl was on the school archery team and Diana's weapon of choice was the bow. Diana was well-known as the Virgin Goddess and Cheryl was a virgin herself—depending on how strictly one defined the term. Also, images of the Goddess in art and literature immediately evoked Cheryl's appearance: slender, slim hips, long legs, generous breasts. I couldn't wait to see her costume. So far, she had been quite evasive as to what exactly it would involve. She assured me though, that "You will love it." Knowing her, the wait would be worth it.

Cheryl and I first met during summer vacation. She had just moved here, leaving her former university in the process, in response to some intensely personal issues. She wanted to be in a place where nobody knew her, where she could begin anew. We became very good friends. One sunny afternoon while holding hands on a park bench, Cheryl kissed me. It was a moment we had both eagerly anticipated. But then she pulled back, saying she had something important to tell me. What followed was an unusual, and very unexpected revelation concerning her former life and her reasons for leaving. Cheryl, I discovered, was rather more than the person she appeared to be.

What she said forced me to reflect deeply on the nature of love and sex, but especially on myself and who I thought I wanted to be, as a person. What I realized was that I was falling in love; I wanted Cheryl despite—or perhaps even because of—what she told me. We went back to her apartment and Cheryl and I spent the afternoon making love. It was a truly remarkable experience. She introduced me to a side of myself I never knew existed. We had been together ever since. It was quite an uncommon summer romance.

I showed up at her apartment at around 10:00. Being a guy and having somewhat of an affinity for ancient history, I chose to wear a knee-length Roman kilt made from wide, overlapping leather strips attached to a thick leather belt. A loosely woven circlet of oak leaves wrapped around my head, and a short sword rested in a scabbard. An insulated leather flask with a screw cap that I had filled with a potently frozen mixture of Absolute vodka, Rose's lime juice and Triple Sec hung at my hip. I wasn't really a drinker, but I liked the idea of bringing it along. I didn't know it at the time, but it would come in quite handy. I wore nothing underneath the kilt. As usual, I had waited until the last moment to work something up. I thought I did alright, considering.

But Cheryl! I watched her putting the finishing touches on her outfit: a very short, leather mini-skirt with matching leather belt. A quiver of arrows hung from her back on a leather strap. Her light blonde hair was tied back in a loose ponytail with a thin green ribbon. She would carry her bow in her hand. The rest of her trim young body was completely nude except for a pair of very sexy leather sandals. Her breasts jutted enticingly from her slender frame. Her areolas were large and brown and her thick, dark nipples pointed slightly upward.

I started to regret my commando status. I glided toward her and kissed her on the lips. She was stunningly beautiful: A Goddess, indeed. I dropped to my knees in front of her, clasping her tight ass with one hand, slipping the other up under her mini-skirt and inside her loose cotton panties. I brushed her gently with my fingertips. I desperately wanted to taste her, but she was too quick for me. Twisting her hips out of my reach she said mischievously, "You'll just have to wait for it, lover! We have a party to go to."

I was aching. I wanted her under me on the floor, right now! There were, I had learned, advantages to patience. She turned towards the mirror and applied a small amount of light colored lipstick. She draped a loose shawl over her shoulders; it might be a long walk from the car to the party. We headed downstairs.

The sorority house sat on approximately five acres of partially wooded land on the outskirts of campus. Bright lights shone invitingly from the windows of the impressive three story structure. The doors were flung open, offering an expansive view of the festivities within. A pair of very large bouncers were stationed outside checking for invitations and costumes. We were quickly admitted.

"This is incredible," Cheryl exclaimed. It was true. The room we were in was huge, much bigger than a typical living room. Chandeliers suspended from high ceilings provided subtle illumination. Lurid red and green strobe lights and dry ice fog added to the effect. Tables were set with food and large bowls of green, effervescent punch. There were elaborately carved Jack-o'-lanterns, dusty tombstones, and a large, open sarcophagus containing a mouldering corpse. There must have been fifty couples frantically bumping and gyrating to music generated by a dreadlocked DJ stationed under a low canopy in the corner.

The decor wasn't what Cheryl had been referring to. It was the costumes. For the most part, they were erotic and stunningly elaborate. The theme seemed to be Greek and Roman Classical, although nothing had been mentioned in the invitations. There were fauns and satyrs; a couple of green, long nailed harpies' taut breasts bounced as they gyrated on the dance floor. Two beautiful, entirely nude young nymphs, their bodies elaborately painted, kissed passionately beneath an acid green strobe light. A golden-skinned Apollo was holding court in a corner, wearing leather sandals and little else. His cock was impressive and becoming even more so as he chatted up the ebony-skinned, magnificent breasted Amazon next to him.

Cheryl was drawing quite a few stares herself. She hadn't been at school long enough to have met many people—she only transferred in a few months ago—but her self-possessed confidence and uncomplicated beauty blended in well. I was very happy to be with her.

We mingled, ate some of the deliciously spicy food, sampled the green punch, and danced. It was like being in the circus, or performing on stage. What a bacchanal! We danced to one of the few slow numbers, our bodies grinding together eagerly. We kissed. I remembered my fingers inside her panties earlier in the evening.

Over the course of the last hour or two we encountered a few friends. Melanie, who was also in Cheryl's archery club, was an exotic West Indies girl with a wide mouth and a quirky sense of humor. She had a very open-minded approach to life and was completely unselfconscious. She could often be found doing homework on her laptop, sunbathing in the nude. Her eye-catching thatch of kinky, black pubic hair lent her slender, athletic body a brazenly erotic touch.

Claire and Melissa, a couple who belonged to the sorority that threw the party, were drama aficionados and had come as Oberon and Titania, their Shakespearean royalty an exception to the unofficial theme. Both were conspicuously bare-breasted, and Oberon had an imposingly large rubber phallus extending lewdly from her loose pants. I could only imagine what they would be getting up to later, after the party.

It was getting warm inside, so our little group decided to visit the grounds behind the house. Cheryl was still carrying her bow. The rear of the house opened out onto impressive, almost formal gardens. There were shallow pools and partially enclosed arbors, some of which offered tantalizing glimpses of naked couples taking erotic advantage of the shadowy darkness. Tiny lights decorated many of the small trees interspersed throughout the backyard. Somebody had put an astonishing amount of effort into the landscaping: it was truly an enchanted fairy land. The garden sprawled for some distance until it met the woods that bordered the property.

Cheryl and I walked along holding hands with Melanie. Melissa and Claire were close behind. The strong punch made us all a bit tipsy. We meandered through the garden and on into the woods. There, we discovered a love seat set under a large tree. A lamp mounted on a tall pole gave out a soft light, just enough by which to see, and to cast pale shadows.

We sat down in a circle on the cool, dry grass. For some reason the landscape, the gardens, the trees appeared surreal: brighter than usual, almost hyperrealistic. It was as if we had somehow crossed into a dreamlike state of otherworldliness and enchantment. Melissa sighed, "It's all so incredibly beautiful. As if Puck cast a spell on us. I can totally imagine him flitting past, 'Like an arrow from a Tartar's bow.'" Titania's quote was eerily prophetic.

In addition to that dreamlike quality there was also a pervasive, steamy eroticism. My kilt barely covered my aroused state and the girls, all of whom were bare breasted, sported enticingly erect nipples. The atmosphere was charged with sex.

Then, apropos of nothing: "Hey, speaking of the Tartar's bow, what do you guys think about a little archery demonstration?" Melissa was looking at Cheryl and Melanie. They turned their heads and glanced at each other. "Sure, why not?" they agreed.

Claire jumped up and with her lipstick drew a large circle about six feet high on the trunk of the tree rising over the love seat. She marked the center with a bright, red "X". Melissa meanwhile had paced back approximately twenty-five yards and marked with a small branch the spot from which they would shoot. Everything was ready.

"So, five arrows each?" Melanie asked.

"Sounds good to me," Cheryl answered. They were about equal marksmen so it would be a good contest.

"What shall we shoot for? I mean, there should be some kind of bet or something, don't you think?" asked Melanie.

There was general agreement. Several ideas were suggested. "How about the loser gives the winner head?" I asked unthinkingly.

There was a half second of silence. "Oh, my god," Claire gasped. "I'm getting wet just thinking about it."

Suddenly my face paled. I had just stupidly and unwittingly put Cheryl in a terrible position. If she lost, she would have to slide in between Melanie's thighs and lick her pussy. I was pretty sure that Cheryl had never done that before. On the other hand, if she won she would have to put herself on display for all the world to see. I didn't think she was ready for that either. Shit! I had fucked up royally.

Cheryl looked at me like she was going to kill me. "You know," I managed to get out, "Maybe that's not such a great idea after all. How about we just do what Melissa suggested, that the loser does the winner's laundry?" I was ready to die. She must have seen the anguish and remorse written across my face. The others, seemingly ignorant of the glance that had just passed between us, ignored my remark.

Melanie looked at Cheryl, her eyes wide: "I'm game if you are..."

Cheryl stood up, her face a blank mask against the dark sky. "Okay. Let's do it."

The girls walked excitedly back to the place where Claire had dropped the branch. Cheryl picked up her bow and took my arm. "What the fuck do you think you're doing?" she whispered agitatedly. "Do you realize what you just did?"

"Oh god, I am so sorry!" I exclaimed anxiously. "It's just that with all this sex in the air, the party, the punch, I didn't think! I know—I fucked up! You don't have to go through with it—just call it off. I'll give Melanie head if you want. I'll do anything to make it right!"

I was really worked up. Cheryl noticed. "Mark," she said, "You're not going to give Melanie head. Do you have any idea how that would make me feel? Fortunately these girls are my friends, especially Melanie. I don't think I've met anyone besides you since I moved here I feel so comfortable with. But yeah, this is going to be a bitch. The bottom line though, is that I agreed to do it: I made a choice and I'll have to accept the consequences. If I need to learn how to eat pussy I'll do it with a goddamn smile. I'm more worried about what's going to happen if I win."

"But...," I stammered in panic.

Cheryl interrupted me. "Mark, be quiet. I'll get through this. I still love you. I'm not exactly sure why, but I do. Whatever I do, just back me up."

We rejoined the girls. Claire had already confiscated Cheryl's quiver and removed ten arrows. Five of them she marked with bright red lipstick. "These are for you," she said to Cheryl. She gave the others to Melanie. "Let the games begin!"

Cheryl agreed to shoot first. This was only fair: it was her bow and Melanie would get the opportunity to take the final shot. Melanie and Cheryl stood side by side; the rest of us gathered a few paces behind. What a pair they made! Cheryl, in her leather mini-skirt and sandals and Melanie, lavishly painted and otherwise stark naked.

Taking a deep breath, Cheryl knocked an arrow to the string and let it fly. Whoosh! It hit well within the red circle but not within Claire's inner "X". Melanie drew next. Her arrow also fell within the big target but managed to nick one of the arms of the "X". Point to Melanie. We cheered excitedly. It was Cheryl's turn: her arrow quivered from the bulls eye, dead on. There was no question who won that point! The girls continued to trade shots, sometimes winning a point and sometimes not. They were both excellent archers.

The two girls were dead even. It was time for their last shots. I could only imagine what was going through their heads. We spectators were practically panting with excitement and pent up sexual frustration. Cheryl drew and shot: almost a bulls eye, but not quite. It was Melanie's turn. She took a deep breath, drew and fired. Thwok! Not quite in the bulls eye either, but a finger's breadth farther out than Cheryl's. "Shit!" Melanie yelled. Cheryl had won.

What a contest! We passionately applauded, whooping and hollering like freshmen spectators at a football game. I had just about forgotten Cheryl's predicament when Melanie stepped forward, breathing hard. "Well Cheryl, I guess it's time to claim your prize!" Her eyes were bright and she had a slight grin on her face. I had the feeling she was going to enjoy this.

Cheryl turned away from us, though. "Come with me," she said. "All of you." We returned to the love seat and into the dim light. "Take my hands," she said. We stood in a circle and held hands. "I want each of you to promise me something. What has happened, what is about to happen here in this glade is for us only. No one else can know and you can't tell anyone. Ever. This is very important to me. So important that if you don't agree I'm just going to walk away. No winner, no prize, nothing. Will you swear?"

I was halfway hoping someone would disagree thereby letting Cheryl off the hook, but Claire, Melissa and Melanie solemnly nodded their heads. "Mark?" she asked. Reluctantly I nodded my head as well. "OK. This is what I want you to do. Come stand in front of me. One at a time. You first, Mark." I moved towards her. She seemed totally in control. "Give me your flask," she said. I had completely forgotten about the freezing Kamikaze mixture hanging from my belt. I gave it to her. "Drink," she commanded. I took a long, cold swallow. "Now say: 'I swear' and kiss me."

"I swear," I said and I kissed her.

Melanie was next. "I swear," she whispered emotionally. She drank from the flask, gently put her hand to Cheryl's cheek and kissed her. It was a long kiss. Melissa and Claire followed suit, each receiving a drink from the flask and a deep kiss after repeating the oath. It was like participating in some ancient, Druidic ritual in which Cheryl was the mystical high priestess.

"Now," said Cheryl, "The rest of you sit over there on the grass. Melanie, I want you here in front." We did as we were told. Melissa, Claire and I formed a rough semicircle facing Melanie in the center. Cheryl had backed off a few steps towards the love seat. She stood in the cone of gentle illumination given off by the high lamp. We waited expectantly.

Cheryl's bow and quiver were on the ground. She removed her belt and kicked off her sandals, tossing them next to the other things. She reached under her leather mini-skirt and removed her cotton panties. She tossed them on the pile as well. She was now completely naked except for her brief skirt. She languorously arched her back and gazed serenely up at the sky. The moon was waning. She cupped her breasts in her hands, slowly caressing her stiffening nipples with her fingertips. We sat watching, entranced. Nothing could have enticed us to look away.

Cheryl turned her back to us. She slipped out of her skirt and tossed it aside. Her ass was perfect: tight, high, defined. It shone palely in the silver light. She turned around, her arms spread wide, hands facing upward in a gesture of supplication. The moon glittered in her eyes. She was a Goddess in truth: slender, slim hipped, bare breasted. Her cock was long and hard and pointed out from her trim belly like a Priapus in a Greek garden. She waited.

Someone gasped and whispered emotionally, "She's so incredibly beautiful! I had no idea she..." Then Cheryl spoke to us in a soft but clear voice: "Supplicants! I am Diana, Goddess of the Moon and of the Hunt. Mortal, I bid you approach. The time has come to fulfill your oath!"

Melanie covered the few feet that separated them. Her mouth hung open with surprise and not a little fascination. Cheryl held out her hands. Melanie hesitated for a second and then took them, raising herself up. "Kiss me," Cheryl commanded. Melanie's eyes grew big. Their mouths met in a soft but intensely charged kiss. "Now lick my nipples," whispered Cheryl. Melanie did, gently flicking one and then the other with her soft, pliant tongue. Cheryl had positioned the two of them such that we would be witness to every detail. Cheryl placed her hands gently on Melanie's shoulders and applied a soft, downward pressure.

Melanie sank down onto her knees, cupping Cheryl's high, firm buttocks in her hands. Melanie licked her lips, gazed up into Cheryl's soft, green eyes and leaned forward. She opened her mouth and gently took in Cheryl's thick, bulbous cockhead. It was slick with pre-come. Then, in one smooth motion Melanie engulfed the whole of Cheryl's impressive length, stopping only when her nose bumped up against Cheryl's soft, blonde pubes. Cheryl's eyes rolled back into her head. She gasped.

Melanie began to move her head with a slow, sensual rhythm over Cheryl's saliva slickened cock. She took in the entire length time after time, pulling back slowly, coming up for air, and then swallowing deeply again. Melanie's breasts bobbed enticingly with each stroke.

God, this girl was good! I have to admit I that felt a twinge of jealousy as I witnessed my girlfriend receiving such lavish and intimate attention from someone other than myself. But I quickly got over it: my own cock had become hard as a rock and was poking up through a gap in my kilt's leather strips. I did nothing to hide the fact. Melissa's hands had wandered up to her lovely, bare breasts. She began to breathe heavily as her fingers flicked her sensitive nipples. Claire's fingers had found her own stiff flesh, but then she shifted one hand between her long legs and began massaging her slippery entrance with a glistening finger.

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