The Real Kasey Ch. 01

Two of the men who had hung with us most of the night, and were acting like they were with us when others stopped by, were the ones who made me most nervous. In between standard conversational topics they would make remarks about how sexy I was, often pausing in the middle of their conversation with Gary to say things like "Have I told you yet that you have amazing legs?" Such comments were so frequent I ended up sighing and saying "Yeah, like two minutes ago."

I was getting tired, and drunk, and wanted to just go to bed and be by myself, but then the two men, Mike and Neil, asked Gary if we'd be interested in stopping by their room for "some party favors." They were talking about smoking pot, which I hadn't done since I was a teenager, and Gary deflected the offer at first, telling them "we need to get back to our room," implying we were sharing a room. I said nothing, ignored the comments, and nursed my latest drink while continuing to think of a polite way to excuse myself.

Gary eventually agreed, after Mike and Neil asked a second and third time, and I told them I was just going to go back to my room, emphasizing "my" in the statement, and told them to "have fun." Gary began chiding me, calling me a "party pooper" and to "loosen up." I didn't want to go, but I had always been a follower, who went along with the crowd, and eventually those tendencies got the better of me and I reluctantly agreed to go with them.

The look on my face when we got to Mike and Neil's room radiated annoyance and tedium. I was tired of all the conversation and even the way the men were looking at me was getting tiresome. All I really wanted was to go back to my room, call Lisa and let her know I missed her, get out of my girl clothes and go to bed.

In the end, Mike and Neil grabbed their stash and followed Gary and me back to Gary's room, where Gary assured me I could go to my room and lock the door if I felt the need to leave the party.

It having been four years or so since the last time I'd smoke a joint, the marijuana had a powerful effect on me. I became incredibly relaxed, my tension and discomfort melted away, and I didn't even blink when Neil took off my heels for me, pulled my feet up on his lap and started giving me a very relaxing foot massage that betrayed years of experience in doing them.

I started to feel like a princess with three men doting on me. As Neil massaged my feet, eliciting quiet moans and sighs from me that I was barely aware of, Mike lit up a second joint and began passing it around. Gary just sat smiling, deeply affected by the marijuana himself, and watched as I reclined in my chair, my feet on Neil's lap, completely relaxed and feeling at home with the situation.

I was getting the kind of attention from men I'd long craved and needed. I didn't even think of it as sexual until Neil switched from my right foot to my left and laid my right foot down on top of his crotch. My bare foot could feel his erection growing beneath it and I quickly pulled it away.

Gary had somehow come up behind me, and in the state I was in I wasn't paying very close attention to anything other than staring at Neil while he massaged my feet. Gary began gently rubbing my shoulders, which felt good, so I didn't say anything. I was in an almost dreamlike state, high as a kite and loving the way these men's hands felt on my body. We kept smoking and talking, always just simple small talk punctuated by the occasional comment about how sexy I was.

My belief that Neil and Mike were two strangers and our meeting with them was completely by chance was part of my youthful naivety.

While I have written many wild and bizarre stories, my true story may have had more bizarre twists than my fictions. After Gary had convinced me to go to the hotel for the weekend he had contacted his friends Neil and Mike, who he knew from an online chat room for admirers of crossdressers. They had spent a great deal of time in online discussions about how to best seduce me and then see how far they could get me to go.

I was now totally relaxed, completely at ease, and even when Neil had placed my bare foot down on his erection, I had merely moved it away and hadn't said anything or reacted defensively. I was smiling, laughing, and having a great time.

The seduction was slow and very effective. The compliments mixed in with general conversation, the marijuana and drinks, and the touching and massaging of my legs, feet, and shoulders all led to me being very relaxed and open.

I tilted my head back as Gary massaged my shoulders and looked up at him. As I did, he leaned down and kissed me on the lips. I hadn't expected it, and responded with a look of shock. Then he leaned down again and I brought my lips up to meet him and just like that I was making out with a man for the first time in my life.

Once our lips parted, I turned to find Mike crouching beside me. I was breathless from my kiss with Gary, but when Mike leaned in to kiss me, our lips locked and we were soon making out as well.

The moment caught me in such a way that the room was spinning and I was seeing all sorts of colors and lights, as if the room had melted into one surreal painting. I was panting, trying to catch my breath, trying to understand what was happening, but everything just felt weird and wonderful.

Neil was still massaging my foot, but as I looked down and focused on him, I could see his hard cock was out of his pants and he was rubbing it against the arch of my foot as his hands continued massaging me. I had to do a double-take to make sure I was seeing what I thought I was seeing.

"Oh wow," I gushed, "you have such a nice cock."

Mike stood up and dropped the shorts he was wearing. "What do you think about mine?"

"Damn, you have a really, really nice cock," I enthused after I got a good, long look at his thick, eight inches of veiny cock with a big mushroom head.

There were no demands, no domination, or any of the usual humiliations I often write about. The true story was quite different. The three men, after getting me relaxed and in the mood, simply showed me their cocks and told me that I had gotten them as hard as they were. It felt incredibly flattering, like the greatest compliment imaginable, having three men getting rock hard from looking at me in my miniskirt and touching me while I was all dressed up like a woman.

Mike cock was so close to me. It was right there, and so I reached out and stroked it with my long fingernails, running them along the bottom of his cock from his balls up to that succulent mushroom head. I gasped as I did so, and while the men watched silently, I leaned in towards him and slid my lips over his cock head until I had the full head in my mouth. It tasted like pure heaven.

After I let it go, falling back on my chair with a look of satisfaction on my face, I looked up to see Gary had his cock out as well. It was a bit on the small side, but quite hard, so I smiled at him and took a quick taste of his cock head as well. Then Neil let go of my foot, got up and brought his cock over to me, pushing Mike aside. I did the same for him as I did for the others, and then fell back into my chair giggling like a schoolgirl.

We continued talking while all three of the men slowly took off all their clothes. Soon I was sitting with three naked men, all with very hard cocks, and I couldn't concentrate on anything we were talking about. I just kept glancing back and forth between their cocks and smiling wickedly.

I don't remember how I got there, but I ended up on the bed with my three naked fans. Another joint was lit and passed around while all three men ran their hands over my legs, feet and ass. I was so high that I just started moaning and sighing almost constantly. It all just felt so good, even as Neil slid his finger under the back of my thong panties and began rubbing my asshole, eventually working his finger into me very slowly.

While he did that, Mike knelt down in front of my face. I was on my stomach with his legs on either side of my head. His hard cock was throbbing, pulsing, and jumping around in front of my face. He slid in closer until his cock was right in front of my face.

Neil was using some kind of lubricant on his finger now, which felt very cold as his finger now easily penetrated my asshole. I moaned loudly. "That feels so fucking good," I squealed as he buried his finger inside me and worked it back and forth. He then worked a second finger in and did the same as I shrieked with pleasure. Then he withdrew his finger and I reached out for Mike's cock and put it slowly into my mouth.

I'll never forget the way Neil tossed the condom wrapped down alongside my face so that as I sucked Mike's cock I could see it out of the corner of my eye. He then pulled my ass up towards him, ripped off my thong panties, grabbed my hips firmly and began to push his hard cock into me.

Just like that I was getting fucked by a man for the first time.

I arched my back and let go of Mike's cock completely, forgetting about it completely as Neil's cock pushed into my ass. It was the most incredible feeling I'd ever felt in my life. It hurt, but it was such a good kind of hurt that I pushed my ass back against him wanting to get more of him inside me faster than he was feeding it to me.

I moaned and screamed loud enough that the whole hotel might have heard me. It was so intense, so all consuming, as I beat my hands against the bed. This felt like what I had been waiting to feel my entire life but had never known what it was. It was this.

"You've got a tight little butt, Kasey," Neil said as he fucked my ass slow and deep. "You are a real nice fuck... a real nice fuck... damn..."

When Neil came, he came inside me, with the condom on. He yelled out "Yes, yes, yes!" over and over again as he came in a long orgasm with multiple spurts and jerks. When he was done, I felt another pair of hands grab my ass. Mike took a turn, and with his cock being bigger and thicker, I could quickly feel the difference even when he just started to penetrate me.

Mike would fuck me hard and fast. He pounded my ass for at least twenty minutes relentlessly while I moaned, screamed, wailed and at first begged him to stop, then to slow down, and finally yelled out "Yes! Fuck me like that! Fuck me like that!"

By the time Mike was done and had shot his full load across my ass cheeks and let it run down along the crack of my now well fucked ass, I was completely exhausted. I collapsed and all but passed out face down on the bed. I heard Gary saying goodbye to Neil and Mike at the door, laughing and saying "let's do it again sometime."

Gary returned and proceeded to gently run his fingertips along the length of my back. He went up and down until I let out a quiet sigh. Then he turned me slowly onto my side. He was still naked, fully erect, and smiling down at me as he slid the tip of his cock back and forth along my lips, leaving wet and sticky traces of his pre-cum as he did so.

"Now, how about a goodnight kiss before we call it a night?" he asked.

Almost instinctively and completely willingly, my mouth opened and took the head of his cock inside. I sucked back and forth on the head for a few seconds before Gary turned me so I was crouched down on my knees and facing him. As we squirmed around looking for the right position, I ended up on my knees on the bed with Gary standing alongside the bed and eventually I was kneeling in front of him on the floor, looking up at him with very tired eyes.

"Just let me make love to your mouth," Gary said as I struggled to find the energy to suck his cock. He took hold of the back of my head, tilted it down, and began thrusting up into my mouth. He held my head almost motionless as he thrusted upwards, then down, then up again. My whole body jerked in response to the thrusts. I gagged, I struggled to breathe through my nose, but mostly I just let him do what he was doing to me.

It was like he was fucking my head, just holding it in place and fucking it hard and fast with powerful thrusts. He grunted, he moaned, and started calling me "slut" and "faggot" and "cocksucking whore."

It got so intense I began crying, sobbing uncontrollably as his words cut into me and reminded me of what I had done that night. When he was done, overfilling my mouth with cum when he finally reached orgasm, I fell forward onto the floor with tears streaming down my face. I crawled back to my room on my hands and knees, locked the door, and passed out before reaching my bed.

In the morning I didn't wake up until almost noon. I dressed in the male clothes I'd arrived in and started banging on Gary's door.

"I didn't think you'd ever wake up, sunshine," Gary said when he opened the connecting door.

"I want you to drive me home NOW," I said angrily. "Get me the fuck out of here and take me home."

I'd never see Gary again, and I wouldn't dress again for over five years. The experience and how I had acted, how I knew I had in fact enjoyed it, made me feel sick inside. I couldn't cope with it and so I stopped dressing completely.

I went into therapy for a long time, broke up with Lisa when I found out she was carrying on an ongoing affair with Marco, stopped talking to Marco for the same reason, and had to find a new life for myself. I quit my job, moved to a new city, and tried to start a new life.

Of course, I could never completely stop dressing, at least not for long.