The Real Kasey Ch. 01

Lisa had been the exception to that. I'd met her on my own, a chance encounter at the apartment complex we'd both lived in, that led to me writing her a goofy note. One thing led to another and a year later we were sharing an apartment. Now, it seemed, Marco was taking her as well, and while I'd ignored or failed to see the signs along the way, I was now submitting to him in the ultimate way.

Lisa had gotten up and was now sitting on the couch alongside Marco. "You're doing so good honey," she told me with a smile before she kissed Marco passionately. "You are doing it so good. Are you sure you've never done this before?"

Marco's cock was so hard and felt like it was getting even harder as I kept sucking. My head bobbed up and down steadily as I tried to find just the right pace to keep going, and to keep him going. At one point I came completely off it, needing to catch my breath, and found myself panting out the words, "You... have... such... an... incredible... cock..."

Lisa laughed and kissed Marco again before he could say anything in response to my passionate utterance. I found myself staring at his big cock, my eyes widening, and I realized I was drooling. I wiped the drool off my lips and chin and rubbed it onto Marco's cock, continuing to stare at it, my heart pounding and my hand shaking as I stroked it adoringly.

I leaned forward and kissed and licked Marco's cock, up and down the shaft, licked his balls, and then came slowly all the way up and took the fullness of his cock head into my mouth.

Lisa was kneeling on the couch alongside Marco, and as I resuming sucking his cock, he pulled the straps of my girlfriend's teddy down her shoulders and exposed her breasts. He was running his hands over them, gently squeezing them, as I sucked his cock. Each time I looked up and saw him touching her breasts I got more excited and sucked faster, trying to tighten my mouth around his cock, as I slid up and down, now taking almost three quarters of it each time.

"Fuck, this is so good," Marco told Lisa as she straightened her body so that her breasts were in front of his face. "You've got such perfect tits."

He slipped one of her nipples into his mouth and bit and licked it. As he did so, my now fast paced, eager sucking caused his six foot six inch body to tense up. It took me a moment to realize I was about to make my friend cum. I could feel his balls tightening underneath where my hand was holding onto the base of his erection. As he built up, I came off his cock, terrified of the thought of him coming in my mouth. As I did so, holding onto his cock and stroking him the rest of the way, I watched with a mix of horror and delight as my best friend ejaculated a huge load into the air.

I ended up sleeping on the couch that night, basically passing out soon after making Marco cum, while Lisa shared our bed with him. I would occasionally wake up to use the bathroom, and I could hear them fucking behind the closed bedroom door. I didn't even consider interrupting them. I felt ashamed and humiliated by what I had done and already didn't know how I would deal with it in the morning. Walking in on them would only add insult to injury. Was I going to tell my best friend to stop fucking my girlfriend after I'd just sucked him off in the living room?

In the morning I woke up with a horrible hangover and no desire to get off the couch. I didn't even realize Marco had left before I woke up until Lisa came out of the bedroom and began making coffee. She brought me a cup, sat it down on the coffee table, and sat down at the end of the couch by my feet. She also brought me a couple aspirin, which she put down next to the coffee, and started gently massaging my feet.

"Your nails look good pink," she remarked, referring to the hot pink toenail polish I was wearing.

I said nothing, feeling ashamed and wounded by the events of the previous night. As Lisa went on massaging my feet, my thoughts got the better of me and I choked up. I started to cry, slowly at first, and then sobbing uncontrollably.

Lisa did everything she could to soothe me, and eventually I was sitting up, sipping the coffee, choking down the aspirin and just staring into space. My feelings of regret and shame were amplified by the fact that I couldn't deny I had enjoyed what I had done, perhaps more than any other sexual experience I'd had before or during my relationship with Lisa. I just had no idea how to process that realization.

"Honey, there's nothing wrong with what you did," Lisa told me calmly, stroking my bare thigh. "You let out a part of you that you've kept inside you for a long time."

Over the next couple of weeks I avoided taking or making calls to Marco. He seemed to react almost casually to what had happened, leaving me messages about hanging out at our favorite bar or doing the usual things we did. I couldn't bear talking to him or seeing him. There was distance between Lisa and me as well. We didn't have sex, I was cold to her despite her best efforts, and I spent most of my time going to work and coming home and moping around the apartment.

Two weeks into my brooding and self-loathing, I came home to find Lisa sitting in the living room with a man who looked very familiar. At first I was horrified by the thought that she was screwing around with this guy and was making no efforts to hide it from me. Then I realized he was one of the men who had been hitting on me and buying me drinks at the club two weeks earlier. He had given his phone number to me and apparently to Lisa as well, looking to hook up with me. I had brushed it aside, thinking it absurd at the time, and now I was surprised and caught completely off-guard by his appearance in our living room.

His name was Gary and Lisa introduced him as if we were all old friends. "Kasey, you remember Gary, don't you? You two met at the club."

I was dressed in my clothes from the office and therefore I wasn't looking anything like Gary may have remembered from the club.

"I almost didn't recognize you, Kasey," Gary said. He stood up and walked over to me, and I extended a hand to shake his, but instead he gave me a completely unexpected hug.

"Um, okay," I said as he hugged me and tried to nonchalantly disengage.

"Lisa invited me to have dinner with the two of you," he said after releasing me.

"You should get changed," Lisa said with a wink. "Put on something sexy."

I was already uncomfortable, and now I just wanted to walk out, get in my car and drive off somewhere. For some reason, I didn't, and instead made a dramatic sigh. My desire to dress feminine and sexy was strong, and even stronger was my need to show off in front of men. Gary had already made it clear he liked me that way, and with just the three of us, my discomfort was soon overtaken by resignation and a building level of excitement. The fact that I had just gotten my legs waxed made me all the more willing to show them off.

"It will take me a while," I said.

"That's okay," Lisa said. Then she whispered to me as she followed me down the hall to the bedroom, "You've just been so unhappy lately, I wanted to cheer you up."

As I got dressed I found myself feeling more and more comfortable in my female guise than in my regular, humdrum male persona. I truly loved putting on a skirt and heels, snapping on my padded bra, putting a satiny blouse over it, doing my makeup and putting on my long platinum blonde wig. While as a man I was always a quiet, sheepish, wallflower of a guy, when I dressed this way I felt vibrant, sexy and alive.

By the time I finished getting ready, Lisa was almost done making dinner in the kitchen. Gary was sitting in the living room, drinking a glass of wine and listening to CDs from our extensive music collection. When I walked into the room he smiled broadly, got up, and hugged me again.

"Now there's the sexy lady I remember," he said.

He wanted me to strut back and forth in front of him. I acted like I was exasperated and embarrassed about the request, but I loved it. Strutting back and forth in front of him in heels and a miniskirt, my smooth tanned legs looking their gorgeous best, I got aroused to the point of a full erection in my panties.

Luckily, my erection rose upward, not outward, and was mostly concealed by my thong panties and miniskirt. The awkwardness faded as Lisa announced dinner was ready and told us to have a seat at the dining room table.

The table seated four people. I took my usual seat with my back to the picture window behind the table. Gary sat down to my left and Lisa set her own place across from mine. Lisa had made Chicken Marsala with vegetables, garlic bread and the little red potatoes she often obsessed about.

Once the food was on the table, we helped ourselves, and ate while chatting. It was mostly small talk, and plenty of compliments from Gary about Lisa's cooking.

Gary's hand at one point found my left thigh, and he began stroking it while saying, "Now that's what I call delicious." I froze up at the comment, which he tried to make sound like he was talking about the dinner, but mostly it was the way his hand felt on my thigh. The way his touch felt on my smooth leg felt so good that I started breathing heavily and gasped when he took his hand away to resume eating.

"Don't be so nervous," Gary told me after we finished eating and adjourned to the living room. "I'm not here to pressure you into anything. I just wanted you to feel more comfortable being yourself around men. So, we just hang out, talk, and listen to some music or whatever."

After some time I felt completely comfortable. We talked about movies and music and where we'd gone to school. We shared amusing stories, laughed, and had a good time. I almost forget how I was dressed until Gary put his hand on my knee. I just smiled at him in response.

"I really like you, Kasey, and I'm very attracted to you," Gary told me as he kept his hand on my knee and looked into my eyes. "But I should leave for now. If it is okay with you I'll call you again and maybe I could take you out somewhere."

"Maybe," I said noncommittally.

For the first time since the night with Marco, Lisa and I had sex that night. We began by making out in the living room after Gary left and then she told me to meet her in the bedroom, but not to change out of my outfit. She ducked out to the bathroom for a moment and came back wearing nothing but a big strap-on dildo standing at attention from between her legs.

It didn't take me even a full minute to get down on my knees in front of her and take hold of the dildo. I'd never seen her wear it before, or even know that she had it, but when I saw it I had to have it. I had to play with it. And once I had touched it, stroked it, simulated jerking it off, I playfully bit the rubbery head of it and giggled.

"I thought you'd like my new friend," Lisa said. "Now we can really play the role reversal game."

The dildo was bigger than Marco's cock, thicker and longer, and I could barely get the head of it in my mouth. My jaw hurt from stretching so wide, but I managed to take the head and suck back and forth on it while looking up at Lisa. She was smiling, enjoying herself, and then she pushed forward, forcing the giant dildo deeper into my mouth.

"Look at you taking all that cock," Lisa laughed. "And you want it, don't you? Oh, you want it so bad, don't you sexy girl?"

It wasn't as if I could respond, but my eyes answered her in their own way. For most of the night I had fought back thoughts and fantasies about sucking Gary's cock. I pushed the thoughts down, tried to get them out of my head, but the more I tried, the more powerful the thoughts became.

I didn't want to want cock, but I did. When Lisa appeared, naked with just the dildo, it no longer felt gay. She was a beautiful woman, with no clothes on, and if she happened to be wearing a dildo, it wasn't a homosexual act. It was a man and a woman, but with me dressed the way I was, who was the woman and who was the man?

The pain that resulted from my jaw being stretched to its limits from the dildo jamming into my mouth, pulling back, and then jamming back in again eventually made my jaw and mouth go numb. The resulting sensation was like being barely conscious and not feeling the cock thrusting into my mouth. I reached down, almost instinctively, towards my cock. I was hard as a rock and started jerking myself off while the cock rammed back and forth into my numb mouth.

It didn't take me long to get off, at which point Lisa pulled the dildo out of my mouth. My jaw was sore for days after that, but I tried not to mention it to Lisa or anyone. Explaining the cause to anyone other than Lisa was a daunting task, and complaining to her might make me seem ungrateful for the experience.

I was at a point of total confusion. I wanted to write off the threesome with Marco as a crazy experience that would never happen again or even be mentioned. I wanted to consider how I felt during dinner with Gary to just be "weird." I wanted to think of Lisa and the dildo as just role playing between her and me and therefore totally heterosexual. Yet, the more I dressed, the more I experimented, and the more outfits I acquired to expand my wardrobe, the more I wanted to be noticed by men. And the more I wanted to be noticed by men, the more I wanted them to desire me, to get aroused by me, and the more I wanted to satisfy them with my mouth.

Lisa and I played with the dildo several more times, each time with the same result. After three weeks I decided to swallow my pride and call Gary and take him up on his offer.

"I think I'd like you to take me out sometime," I told him on the phone in my most feminine sounding voice. "Where would we go?"

"There is a hotel out on the coast that is very friendly and open minded about girls like you," he told me. "They have a great restaurant there, and a bar, and dancing, all that kind of stuff. I'd love to take you there on a real date."

I dithered back and forth on the proposition, talking about other things, purposely taking him off the topic at hand. The truth was that the date felt like a true fantasy to me and I wanted to agree. Lisa had already given her blessing on "whatever you want to do with Gary is fine with me." I imagined an enchanted evening at this seaside hotel and eventually I bit my lip and agreed.

Gary paid for two adjoining rooms, both with a king size bed, and being private except for a connecting door. I brought my girl clothes and makeup with me, intending to change once I got there, and was relieved to find I had my own room.

I met Gary for a drink at the hotel bar before getting changed. I needed to get a feel for the place and to understand why Gary told me it was "friendly and open minded" about girls like me. We were halfway through our drinks when two women sat down at the bar several seats away from us. They appeared to be middle-aged women wearing elaborate dresses and hats, but upon further inspection I realized they were not genetic girls. They dressed to appear female, identified as female, and after Gary greeted and exchanged pleasantries with them I learned they were intending to transition into being full time female. They regularly came to the hotel to spend a weekend relaxing and being their true selves, as they put it, and while this put me at ease I felt uncomfortable when they talked about being on hormones and looking forward to fully transitioning.

They were like me, but they weren't. They weren't into dressing sexy, into showing off their legs, into getting the attention of men. Their dresses were long, conservative and not very revealing. They wore opaque pantyhose and shoes with low heels. They looked more like my sixty year old spinster aunt than they did like me when I was dressed.

"They're not like me," I told Gary after they'd left to go and sit on the veranda.

"You have your own style, your own identity," Gary told me calmly. He went on to tell me about how the hotel had developed a reputation as welcoming to people with gender identity issues, mostly in the form of men who crossdressed or who were looking to transition into being fully female. The hotel, which was remotely located, had been on the verge of bankruptcy before agreeing to host a transgender conference two years earlier. Such folks were very much underground in those days, not much talked about, but had sought out a place to get together and share stories and experiences. The hotel owner's brother considered himself transgendered and had arranged the first conference, after which the hotel began a renaissance of sorts by becoming a destination for crossdressers and transgendered from around the country.

I didn't have any girl clothes that were remotely conservative. When I changed I put on my black leather miniskirt, one of my standard satiny blouses, and my new five inch heels, which put my newly pedicured feet on display. They had two straps around the lower part of my foot and a small piece behind my heel for support that had laces which wrapped around my ankle. I didn't wear nylons, having become obsessed with showing off my bare legs that I put so much effort into. I did my makeup carefully, trying not to use too much, put on my long platinum blonde wig, and they summoned up the courage to make my appearance.

I had gone out dressed in public before, but only at the club, where it was fairly dark and loud and filled with people. The hotel was quieter, with a number of people, including the two women we'd met at the bar. It should have been more relaxed and more comfortable, but for me it induced a sense of anxiety. Would I be accepted in this environment? Looking at myself in the mirror I thought I looked slutty compared to those other two women.

My entrance into the main part of the hotel was greeted with a lot of long, lingering looks from men and women, many of which I was having a hard time figuring out whether they were genetic girls or not. I came to realize it didn't matter. They were who they were and I was who I was, but unlike most of them, I quickly became a center of attention. The way other men were looking at me caused me to almost cling to Gary, hoping that seeing me with a man would keep them from approaching me and talking to me.

It was uncomfortable, and yet it wasn't. Once I settled down, I enjoyed the attention and didn't feel threatened or afraid. Gary was pleasant and relaxed, reminding me that I loved getting the kind of attention I was getting when I was dressed. He went on to tell me I was by far the sexiest girl in the place, that I had the longest and sexiest legs any of these guys had ever seen, and that everyone in the hotel was wishing they were him.

We had dinner, during which I noticed everyone kept staring at me, and especially my legs, which I couldn't help showing off once I saw the attention they were getting. I sat somewhat sideways at the table, crossing my legs and keeping them out in the open rather than under the table. After dinner we went to the bar and I sat the same way, sideways on my stool, and acting like I wasn't trying to show off and let everyone have a good look, but knowing what I was doing the whole time.

A number of people came up to us at the bar to say hello. Some of them made a point of telling me how "beautiful" I looked. Some told Gary he was "a lucky guy" and I found out that most crossdressers are straight, while everyone assumed I was gay because of the way I clung to Gary. Even though it was more about hoping that people seeing me with him would keep them from hitting on me, it actually had the opposite effect. The way I stuck to Gary's side caused them to assume I was with him and that we were in some kind of relationship.

As the night went on we developed a sort of following, a group of men who sat with us, stood around us, and talked back and forth with us as we drank. The conversation was mostly trivial, talking about sports teams and where everyone was from, and as much as I tried to relax, I ended up drinking too much, as I tended to do whenever I was nervous or anxious.