Kasey's Confession Ch. 06

I had drawn my blinds closed and changed into my short, terrycloth bathrobe. I knew I had another date scheduled for eight o'clock that night and part of me wished I hadn't made it. There were errands I needed to run, and my apartment needed a good cleaning, all of which sounded like an excuse not to meet another man.

Then, as I was sitting back drinking a cup of tea, the phone rang.

"Hello?"

"Kasey, this is Ted."

"Hi Ted, how are you?"

"I'm good, but I'm sorry. I won't be able to make it tonight. Something came up and I won't be able to get out of it. Can we make it another time?"

"Sure, just give me a call and we can try to work something out."

I had gotten out of my evening date without any effort. I relaxed and decided I didn't want to clean or run errands. I just wanted to kick back and watch a movie or listen to some music.

I saw my "tranny" porn movies where I had stashed them and popped one in. The first movie started with someone who had obviously been taking hormones of some kind, since she was very feminine looking despite having a very obvious set of male genitals in her panties. She was just hanging out in her apartment, like me, when her phone rang. She talked to the man on the other end of the call and invited him over. It was hitting a little close to home and I was getting very aroused.

The man showed up with two of his buddies, which got me on the edge of my seat. They started kissing and fondling her, stripping her naked and then pushing her down on her knees, at which point they all pulled out very big cocks and pushed them in her face.

I started stroking myself as I watched her go back and forth between the three men, then I got my dildo and started sucking on it in my best imitation of her obvious cocksucking skills. Then they got her down on all fours and one of the men got behind her and started pushing his hard cock into her ass.

"Oh wow," I said, "that is so hot..."

I got the bottle of baby oil that Bob had rubbed my legs with and poured it on the dildo. Watching the movie, I leaned back and started pushing the oiled dildo into my asshole. I was surprised at how little resistance I felt. My asshole seemed to open very willingly and welcome the dildo inside.

As the man in the movie pushed his whole cock into the tranny's ass, she moaned out, "Yeah baby, I needed to get fucked so badly. Give it to me. Give it to me hard and deep!"

I pushed the dildo into myself hard and started working it back and forth in my ass. I moaned and cried out, "Oh yeah, I need to get fucked so badly. I need to get fucked. I need to get fucked."

I was jerking my cock so hard and fast it felt like I was going to pull it out by the roots, all while I kept pounding the dildo back and forth in my ass. "Oh wow... she is getting it at both ends... oh wow... she has TWO cocks in her mouth and one in her ASS... oh wow... that's what I NEED..."

I then I came, my body shaking and bucking like I was having a seizure. I leaned forward and sat down hard on the dildo, driving it deeper inside me as cum shot out of me.

I collapsed, falling backwards and staring up at the ceiling. I was exhausted and feeling sick to my stomach. I felt the dildo sliding out of my ass and falling onto the floor. I sighed.

I used to just shave my legs and show them off. Then I started tanning them and doing everything I could to make them look sexy. Then I started fantasizing about going down on men. Then I was going down on men. Now I was not only fantasizing about getting fucked up my ass, I was acting it out by using a dildo.

In four days I had gone down on six different men. Thinking about it made me sick and turned me on at the same time. I was freaking out about the idea of it turning me on. I was disturbed that I liked it. Over and over the same thought went through my mind.

"I don't want to be like this."

I took a shower and changed into jeans and a plain black t-shirt. I put on my regular men's sneakers and walked out to my car. I fought off the impulses that told me to change into shorts, the same impulses that kept telling me "let's go get some cock" and drove off.

I decided to go to the mall. I would just be a regular guy out shopping. I needed to get a couple of new shirts for work, so that became my mission.

As I walked through the mall, with barely anyone paying me any attention, I found myself missing the stares and the curious, sometimes confused, looks. There were women in shorts and I found myself feeling jealous of them, especially the ones with very attractive legs. In the past I would have stared and wanted to get with the women they belonged to, but now I just felt jealous of them for being able to show their legs off freely without anyone thinking it was strange or unnatural.

I walked past women's clothing stores. Since it was summer, there were plenty of shorts on display in the windows and I paused in front of them, wanting to buy a pair of short cut-offs or some other sexy pair on display. "Half-off all juniors' shorts" screamed one sign at me with a display of several different styles I really wanted to be wearing.

I walked away and headed to the men's clothing store where I usually bought the collared shirts I wore to work. I found two shirts I liked in my size and walked up to the counter. The salesgirl was friendly and, since it was her job, she complimented me on my selections. Then she talked about the weather and how hot it had been lately.

"Let me ask you something," I said. "I was thinking about buying my girlfriend some shorts, as a present more or less. Would that be weird?"

"Well," she said with a smile, "most women prefer to buy their own clothes, but I think it would depend on how well you know her. Have you been together long?"

"We've been together a long time," I said. "I just, well, I like seeing her in shorts, and I don't want to seem like a pervert or something."

She laughed. "Well, if you've been together a long time I'm sure she already knows what you like. I had a boyfriend once who bought me some lingerie that really wasn't what I liked and it was totally the wrong size. I mean, do I look like a size 16 to you?"

"Oh gosh, no," I laughed back. "I know her size, so I don't have that issue. I'm pretty sure she'd like these shorts, the ones I saw in the window of the store across the way, but I keep going back and forth wondering if it would be too weird."

"Go for it," she told me and handed me the bag with my shirts. "Women love when men buy them presents, even if they're a little weird. Shorts aren't that weird. I've just never had a guy buy me any clothes other than lingerie and underwear, and that can get pretty weird."

I took my bag, thanked her, and walked back over to the store with the shorts in the window. As I found myself browsing, looking for shorts in my size, the salesgirl there approached me.

"Can I help you find something?"

"I really like your shorts," I said. "I kept walking by imagining my girlfriend in them and thought I'd see if you had them in her size, but your sizes seem to run too small."

"What size are you looking for?"

"A woman's size 12 or 14," I told her. "She's tall and has really long legs..."

She helped me find a stash of shorts that were in my size, or what I claimed was my girlfriend's size. I went through them, selecting three different pairs while constantly talking about my imaginary girlfriend and then told her I was ready to make my purchases.

"Would you like to try them on first?" she asked, catching me completely off-guard.

"What? Oh gosh, no, why would I..."

"Sweetie, you keep holding them up to yourself and looking in the mirror. Go ahead and try them on. Our dressing rooms are very private and you want to make sure they fit, right?"

I nodded silently, looked around to see that no one else was in the store, and took the three pairs of shorts into the dressing room. I sat and stared at the shorts, deciding that I was just going to pretend to try them on, waited a few minutes and started walking back out into the store.

The salesgirl was on the phone with someone. "Yeah, Derek, I swear, there is this guy trying on girls shorts in the dressing room. Get someone to cover for you and get over here, I'm telling you he's just the kind of guy you were looking for."

I backed up and ducked back into the changing room. I couldn't decide what to do. I could go out and quickly pay for my three pairs of shorts, or even say I didn't want them and just leave, and take off. Part of me was just really curious about who Derek was and why the salesgirl thought I was "the kind of guy" Derek was "looking for."

"I came here to be a regular guy and stay out of trouble," I told myself as I looked at the three pairs of short shorts and then at the men's jeans I was wearing. I thought about how I used to walk through a mall like this one, checking out women, especially women with legs in short shorts. Now whenever I saw a woman like that all I thought about was how I wanted men to look at me the way I did at her.

After a long few moments sitting and staring into space, I muttered to myself, "I am who I am," and took off my sneakers and jeans and tried on the first pair of shorts. I stood up and looked in the full length mirror on the dressing room door and smiled, "Damn, these shorts are HOT."

I tried on all three pairs and they all fit nicely and they all looked very sexy on me. I thought about putting my jeans back on, but I didn't want to be ashamed, I wanted to be who I was, so I kept the third pair of shorts on. I wasn't sure if I'd wear them home or not, but I wanted to show the salesgirl and maybe "Derek," if he was there.

"What do you think?" I asked as I came out of the dressing room.

I was standing in the entranceway to the back of the store where the dressing rooms were, avoiding being seen by people walking through the mall. I figured I could at least play it off as a joke, depending on the reaction, and then I saw the salesgirl standing there with a young guy, who looked like he was barely of legal drinking age, in a uniform shirt from the pretzel kiosk, standing next to her.

"Okay, damn, those are some unbelievable legs," said the salesgirl. "No wonder you wanted those shorts."

Derek just stared with his mouth open, his eyes fixated on my bare thighs. His erection was clearly visible as it grew in his pants after he saw me. I smiled.

"Honestly," the salesgirl said as she took the two pairs of shorts I wasn't wearing up to the counter and led me back into the store, "I figured you would have guy legs and just be into wearing the shorts, I didn't think you'd have legs like that."

"I guess I'll take that as a compliment," I said, feeling more relaxed. Then I turned to Derek, "Hi, I'm Kasey."

Derek stuttered back his name and kept staring at my legs and my ass. It felt good to have a guy get as fumble-tongued as I used to when I'd work up the courage to try to talk to a woman in short shorts.

"Derek likes to wear woman's clothes," the salesgirl told me.

"Shut up! I don't do that!" he shouted at her.

She shrugged and said, "Oh well, my mistake."

Derek took another long look at my legs in my new super short jean cut-offs and then started walking angrily out of the store. I turned back to the salesgirl to pay for my new shorts.

"Derek is really shy and like totally in the closet," she told me. "I could tell he totally digs you, though."

I shrugged and nodded, and she said, "Wait, aren't you going to change back? You aren't going to walk through the mall like that, are you?"

"Yeah," I said with a smirk, "I am."

I walked out feeling proud. I felt annoyed at myself for going out in jeans and then being jealous of girls being able to strut about in shorts getting all that attention. I got looks, and some of them weren't exactly flattering. A group of teenaged boys called me a "fucking pansy" as I walked past them but I didn't stop, I just kept walking.

I found the pretzel stand where Derek worked and saw him behind the counter with a young woman. I walked up and ordered a pretzel from her and then stood there eating it while Derek ignored me. Then I sat down on a bench directly in his view, crossed my legs and slowly ate the pretzel, breaking off pieces and wrapping my tongue around them as I pulled them into my mouth. He tried to look like he didn't notice me, but his eyes stayed on me.

I realized that all the times I had followed a woman around trying to look nonchalantly at her legs that she probably knew, as I did when a man checked me out.

I finished my pretzel and walked over to where Derek was standing inside the kiosk and grabbed a napkin. "Can I borrow your pen?" I asked him.

Looking down and away, he slid a pen across the counter to me. I wrote my name and phone number on the napkin and slid the napkin, along with the pen, back across the counter at him.

"Call me sometime," I told him and walked away, feeling his eyes on my legs and my ass the entire time, until I went around the corner and left the mall.

When I got home there were six messages on my answering machine. One was from J.J. wanting to get together again. Bob had called "just to say hi." There were two messages from guys I didn't know, one wanting to "hook up sometime" and another who said he wanted to buy me a drink. There was a hang-up after some heavy breathing on the fifth message, and the sixth was Derek.

"Hey Kasey, um, this is Derek from the mall. I don't know... like, maybe you want to hang out some time? I know you just left the mall and shit, but, well, I had your number here and I don't know... if you want, you could give me a call. I'm going to be home after like seven o'clock if you want to like call me or something."

It was the most flattering phone message I'd ever gotten. All the other guys were very masculine and sure of themselves, basically telling me they knew I'd give them head after I met them. Derek was like a nervous schoolboy calling a girl he liked for the first time, and I was the girl!

It wasn't yet seven o'clock but I called Derek back at the number he left and got his answering machine. "Hi Derek," I said in my feminine voice, "this is Kasey. I know you said you would be home after seven, but I was about to take a bubble bath and well, I have the rest of the night free. If you're interested, you could come over and we could hang out. Give me a call if you're interested."

I did, in fact, take a bubble bath, and after I was done it was after seven o'clock. I looked at the pile of men's phone numbers next to my bed and smiled. I liked feeling popular after so long as a bashful wallflower.

I thought about all the times I'd waited to hear from a girl I liked and how many times I'd been blown off in favor of someone more handsome or muscular, or for someone who had a flashy car or a lot of money to buy a woman expensive things. I remembered all the times I'd been told, "You're just not my type" or "I think we'd be better off just being friends." Thinking about those experiences kept me from calling any of the other men whose numbers littered the nightstand by my phone. I had told Derek I had the rest of the night free and unless he called me back and said he wasn't interested or couldn't get together that night, I would keep my night free.

When my phone rang, I hoped it was Derek, and not just because I didn't want to tell someone else I was busy that night. When I answered it and said "hello" there was silence on the other end. I said "hello" a second time and Derek said "hello" back quietly.

"Is this Kasey?" he asked.

"Yes, it is."

"This is Derek, from the mall."

"Hi Derek, I'm really glad you called."

"I was wondering if maybe you could come over here. We could watch a movie or something and just hang out?"

"I guess I could do that," I said.

"Could you, like, I dunno, wear high heels and a skirt or something? You know, if you have stuff like that you wear or is it just the shorts, because that would be cool, too."

"I can bring a few different outfits," I told him, smiling. "Is that's okay with you?"

"Oh yeah, that sounds awesome."

I heard a man's voice in the background as Derek gave me directions. I asked who it was and he said it was his roommate.

"He's going out," Derek explained. "He won't be here when you get here."

I wrote down the directions and told Derek I would be there in about a half an hour. He wasn't too far away, but I wanted some time to get my outfits together and fix my hair and makeup. While I got ready there was another call. I let my machine get it and listened as yet another man left a message wanting to meet me.

Derek lived in a house at the end of a very quiet street. As I pulled up in front of the house, a very tall man, at least six-foot six was walking along the road towards a black BMW parked across the street. I waited for him to walk past before getting out of the car in my short shorts. He smiled and winked as he walked by and I pretended I didn't notice.

He got into a car and drove off, and once he was out of sight I got out of my car and walked towards Derek's house. I went up the stairs and knocking on his door. For a moment I worried that he'd punked me and sent me to a random address, but then he came to the door.

"Hi," he said, "glad you found the place okay."

"The big tall guy that just left, he isn't your roommate by any chance is he?" I asked after stepping inside Derek's apartment.

"Yeah, that's Mr. Smith," Derek said.

"Mr. Smith?"

"Yeah, that's what he insists I call him," explained Derek before changing the subject. "Do you want something to drink?"

"Just some soda, or even water if you have that."

"You don't drink?"

"I had a few too many this afternoon," I told him. "Water would be perfect."

Derek went into the kitchen and came back with a glass of water for me and a bottle of beer for himself. There was some kind of action movie playing on his big screen television and the speakers set up around the room made it feel like a movie theatre.

I sat down on the couch and left room for Derek to sit next to me, but he sat down on the recliner across from me after handing me the water.

"Nice set-up," I said as I drank the water. I finished it quickly, not realizing how thirsty I was and Derek immediately offered to bring me another.

"Most of this is Mr. Smith's stuff," Derek explained. "I couldn't afford this shit working at the mall and going to school."

"Where do you go?" I asked, suddenly worried that Derek was in high school or something equally frightening.

He explained he attended the local college and was only able to go part time because he needed to work full time. He said Mr. Smith allowed him to stay at his house rent free as long as Derek "did work around the house like cutting the grass and cleaning and cooking dinner." We talked for a while, and it felt comfortable, sort of like the way it was when I hung out with Bob.

Then Derek asked if I'd put on a skirt and heels for him. I tried on several different combinations before he settled on one he liked, my strappy pink heels and pink miniskirt, which barely covered my ass cheeks when I walked.

"I do love wearing pink," I told him with a smile. I asked him to sit next to me, but he declined, saying he 'liked to watch' and kept looking back and forth between the movie and my legs for the next half hour.

I started to feel lightheaded and tingly all over. I became amused at the goose bumps that were breaking out all over my legs. During a part of the movie when the action heroes went into a dance club and there was music playing, I got up and started dancing, it just felt good. As time passed the buzz I was feeling intensified until I realized this wasn't normal.

"Did you... put something in my drink?" I asked Derek.