Straight Crossdresser

"I'd love to see that," she said, as I slid my cock into her from behind and she used a tree for balance.

"You want to see your boyfriend with a cock in his mouth?" I asked, as I began fucking her.

"Oh yeah, I bet you'd look so hot with a big fat cock in your mouth," she moaned, this turning her on, just like my hearing her talking about eating pussy turned me on.

"I'm a natural," I said, again admitting the confirmed truth.

"Maybe you can teach me a thing or two then," she moaned, as I fucked her hard, knowing this was going to be a rather short fuck session. My recent cock sucking experience, mixed with all this double entendring had my balls boiling in no time.

I grunted, not even a couple minutes into the session, and deposited a load inside her.

"That was quick," she said, obviously not gotten off yet.

"I'll finish you off another way," I said, pulling out, spinning her around, and burying my face in her cream pie. My cream pie. I hadn't really noticed how Superman's cum had tasted as it rushed down my throat, but mine tasted pretty good.

She seemed startled at first that I was eating her pussy right after coming in it, but after a few seconds of aggressive licking while I retrieved my cum, she moaned, "That's it, baby, eat that cum."

I did just that, licking her cream pie for a few minutes until she came on my face.

Once she'd recovered, she pulled me up and said, "That was new."

"I couldn't let you not get off," I said.

"Did you like how you tasted?"

"Oddly, I did," I admitted, before adding, "a lot." I then asked, "Did you like my doing that?"

"It was pretty hot," she agreed. "You're just a little cum slut," she added, kissing me.

She got dressed, I pulled up my pantyhose, and we returned to the party hand in hand.

We danced.

We drank a bit more but didn't go crazy.

My ass was grabbed by both guys and gals.

I lost track of the time.

It was a couple minutes after one when I looked at the clock.

I panicked!

I needed to go meet Superman.

I needed more cock.

I said, "I need to get some fresh air."

"I'll come along," she offered.

"No, I meant I need to go pee, and the line-up in here is likely brutally long."

"Likely," she nodded, a strange look on her face I couldn't read.

"I'll be back soon."

"Hurry back."

"I'll try," I said as I rushed out of the crowded party and hurried to my secret rendezvous.

"I was beginning to think you wouldn't show," he said from somewhere in a tiny grove of trees.

"Sorry," I apologized. "The dance floor was pretty full."

"Your girlfriend is pretty cute," he complimented.

"Yes, she is," I agreed, not liking the reminder I had a girlfriend in this context, even though I was usually happy I did.

"Hungry for more cock?" he asked bluntly.

"Yes," I admitted, his question making my cock grow.

"Well, come and get it, slut," he said from the shadows.

I went to him, between the trees, not too far away from where I'd fucked Amber less than two hours ago.

I dropped before him and fished out his cock, knowing time was of the essence. I didn't want her coming out here looking for me!

"What a cock hungry slut!" he laughed, as I eagerly went for his cock.

"I don't know why I can't say no to this," I said to him and to myself.

"Because deep down, you're a natural cock sucking bottom," he answered as I took his cock in my mouth.

I didn't know what he meant by bottom, but I didn't care. I just loved having this cock back in my mouth. Crazy how my entire life could change in just a few hours.

I bobbed hungrily for a couple minutes before he said, "Time to make you into a real girl, sweetie."

He pulled out, pulled me up, spun me around, pulled down my pantyhose and bent me over.

It happened so quickly I barely had time to process his obvious intent.

I stammered, even as I felt his cock rub between my ass cheeks, "I-I-I'm not ready for this!"

"Sometimes a girl needs a good fucking," he said, ignoring my protests as I felt his cock at my backdoor entrance.

"But I'm not a girl," I protested, even as once again I didn't try to stop him. Why wasn't I trying to stop him? I didn't want a cock in my ass.

"You're my slut girl," he insisted, as he pushed forward and his cock entered me.

"Oh my God!" I squealed, actually sounding like a girl, as an intense pain struck me.

"Just relax, slut," he said, as his cock slowly went deep inside me. "Your cunt needs to get used to a big dick in it."

"It hurts," I whimpered.

"It will for a bit," he said, "but soon it will feel amazing, especially if you can relax down there."

"Okay," I said through gritted teeth.

I closed my eyes and just breathed, doing my best not to tense up against the pain as he slowly began to fuck me.

"Oh yes, what a tight pussy," he said, not calling it an ass. This wasn't gay. This was simply role playing, since I was a girl tonight.

I didn't say anything.

I just let him fuck my pussy.

Slowly.

Ever so slowly.

My cunt began to relax.

The pain began to fade.

And oddly, my cock, which had shrivelled up as I was entered, began to harden again.

Oddly, I began to moan.

Oddly, it began to feel good.

"There you go, slut," he said as he began stroking slightly faster.

A couple more minutes and the pain had dissipated completely, replaced by pleasure.

I began to moan.

He began to fuck me faster.

"Oh fuck," I moaned, my cock again throbbing, the pleasure now consuming me.

"You like it, slut?" he asked.

"Yes, fuck me," I answered.

"You love my cock in your virgin pussy?" he asked.

It occurred to me it wasn't virgin anymore, but that seemed irrelevant at the moment as I replied, "Yes, I love your big cock in my pussy."

"I'm going to fuck you hard now," he announced, before he began slamming into me.

"Oh yes, fuck," I groaned, as nothing, not even fucking Amber, had ever felt as pleasurable as this.

"Take it all, slut," he said as his body slammed into mine and I took all seven plus inches deep inside me.

"Oh yes, fuck me," I moaned, becoming a girl, "pound my pussy."

"I'm going to breed you, slut," he said, just seconds before I felt his hands tighten on my hips and he exploded his second load inside me.

"Oh yes," I trembled, as he filled me with cum.

"Such a slut," he said weakly as he slowed down.

"Oh fuck," was all I could muster, quite disappointed it was over.

He pulled out, and I could feel his cum leaking out of me. I wondered if this was what Amber felt like when my cum leaked out of her.

"You're one hot fuck," he said, as I rested against the tree.

"Thanks," I said, thinking that was the weirdest compliment I'd ever received.

"Ben!" Amber called from not too far away.

"Oh shit," I said, standing straight up and feeling a gush of cum leak out of me.

"Your name is Ben?" he asked.

"Yeah," I said, as I pulled up the pantyhose again.

"Well now you're Ben Dover," he laughed.

"Ben!" she called out again.

"If you ever want my cock again, I'm at the Everdeen Dorm, room 121," he told me.

"Okay," I whispered, as I looked and saw she was looking every which way for me, but thankfully not walking this way.

"And I have a few friends who'd be more than willing to give you a few loads," he continued, frustratingly not at all worried about my girlfriend.

"Okay, okay," I whispered, before asking, "Will you stay in here for a couple minutes?"

"Sure," he shrugged. "I suppose you'd better keep up the charade for now."

"Charade?"

"You're a cock sucking bottom, Ben," he informed me. "You'll be craving cock forever."

"I don't think so," I said before walking away.

"There you are," Amber said. "Where have you been?"

"I was bent over a tree," I answered honestly.

"Sick?" she asked.

"I may be," I answered, although I wasn't sick in the way she thought, but rather sexually sick; more perverted than she knew. Guiltily, I glanced back to the area where I'd just been fucked.

"Let's go inside," she said, all concerned.

"Okay," I nodded, feeling cum still leaking out of my ass.

She took my hand and said, "You look a little flushed."

"I feel fucked up," I said, unable to not talk in double entendres.

"Poor boy," she said. She took my hand and led me towards the house.

"Don't you mean poor girl?" a voice from behind us asked.

She laughed, looking at the guy who unbeknownst to her, had just fucked her boyfriend's ass, "I guess I do."

"I bet he'd be a great fuck," he continued, as for the first time my cheeks burned with shame. I just knew I was about to be outed to Amber, and there was nothing I could do about it.

"He definitely is," Amber said.

"I wonder which of you is better," he smiled.

"I don't know, Jim," Amber said.

What? She knew his name?

She then asked, shocking me to the core, "You've fucked us both, which of us is better?"

"Amber?" I gasped.

"Ben this is Jim, Jim Ben," she introduced us informally.

"Jim, as in your ex-boyfriend?" I asked.

"The one and only," he said, before adding, "and Ben's ass is definitely tighter than yours."

"What's going on here?" I asked, the puzzle pieces not coming together for me.

"I was curious whether you were dressing up as a girl for fun, or because you actually wanted to be a girl," she said.

"I don't understand," I said.

"So I invited Jim over and asked him to try and seduce you," she revealed.

"He or she took no seducing at all," Jim said. "He's a complete sissy."

"Says the guy who loved my fucking his ass with a strap-on," she said.

"What?" I asked, completely bewildered.

"Jim likes being pegged, and I imagine you will too," Amber said.

"You set this up?" I asked.

"I laid the foundation," she shrugged. "Jim made a few moves on you, and you went along with it."

"Are you angry?" I asked.

"No, you silly girl! On the contrary, I loved watching you in action both times, and I particularly loved being upstairs and hearing you tell him you were his 'slutty girl'," she smiled.

I asked, completely stunned, "You saw me."

"I hid in the closet the first time," she revealed.

"Oh," was all I could utter as I tried to process her revelations.

"You're as big a slut as me," Amber said with a strange sense of pride.

I was still speechless as she pulled the strap-on from her purse and added, "and now I get to use this on you."

"And on me," Jim added.

"Yes, and on you too," Amber said. "Let's all go back to your dorm."

"I'm still confused by all this," I finally spoke.

"I like to fuck guys, and you guys both like getting fucked," she said matter of factly. "I can't see what there is to be confused about."

"He also likes sucking cock," Jim added.

"So do I," Amber said, as she took both our hands and led us to Jim's car.

As I gazed up at the full moon, our long night was apparently just getting started. I was about to participate in my first threesome, although not one at all like I'd ever envisioned. Not two girls and a guy where the guy had limits who he could touch, but by one girl with a strap-on, and two guys who by now were fully bisexual and delighted to prove it, and everyone free to do whatever with whomever.

Once we reached Jim's dorm, I sucked his cock while Amber sucked mine.

Later I fucked Jim in the ass while Amber fucked mine, in the wildest sex sandwich imaginable.

We double penetrated Amber, and her screams of joy summoned an audience of about a dozen guys living in Jim's dorm, as I realized he left the door wide open, who all crowded into the room with their cocks out.

I took my first facials, more or less simultaneously from about a dozen guys, while Amber crooned over and over what a dirty girl I was (I never did get around to removing my wig or my cheerleader costume, although my makeup and my pantyhose were in ruins and tatters).

Thus I began my bisexual journey that night... one that thirty years later I continue exploring to this very day.

THE END