Kasey's Legs

I had been crossdressing for close to ten years. It started as a Halloween costume gag where I shaved my legs, put on a cheerleader outfit and wore a scary mask. After I kept getting compliments on how good my legs looked I continued shaving them and experimenting with dressing in a variety of women's outfits, skirts, high heeled shoes, panties and bras.

It had just been a private thing, and something I shrugged off, telling women I was intimate with that I was straight and it was just something I did for fun. That always seemed to work until Darcy.

I had known Darcy for years. We had been close friends but never intimate or romatically involved. I had pursued her a number of times, but she always told me she didn't feel that way about me. Then she found out about my crossdressing and how people said my legs looked great in a skirt and heels. She told me she wanted me to dress up for her so she could see for herself.

Most of my efforts had been spent on my legs and keeping them as smooth and tan-looking as possible. I loved that look, and I loved the effect combined with painted toenails and open-toed heels.

Darcy was speechless at first, going on about how she couldn't believe how good my legs looked and how they looked better than hers. Then she told me I needed to work on the rest of me. My efforts at makeup were sloppy and my upper half didn't look feminine at all. She tried to help me with both and as it went on, we ended up sleeping together for the first time in our decade long friendship.

We began seeing each other regularly and eventually I moved into her place. She was very enthudiastic about my crossdressing and told me she was bisexual, which in her words meant, "With you I get the best of both worlds."

One night she began asking me if I'd ever thought about going out dressed. There was a gay club in the next town that had a regular "drag queen night" and she thought it would be fun to go. I finally agreed after a lot of coaxing.

When we got there I felt a bit out of place. Most of the guys who were dressed in drag wore excessive makeup and looked like men in a costume. I was there in a leather miniskirt and heels, with bare legs, a pink shirt that wasn't much more than a t-shirt with three-quarter sleeves and a bra with what looked like small breasts. My makeup was just enough to make me look slightly feminine and my hair, which I normally wore long and straight was curled in waves.

Men were hitting on me and buying me drinks. I kept telling them I was straight and "just out for a little fun." Still, I received all kinds of compliments and propositions. As I sat at the bar, more than one man put his hand on my thigh and I didn't push him away.

I told Darcy it was fun, but I didn't really think it was my thing. One the drive home she told me, "You know, I have this fantasy about seeing you suck cock."

I laughed and said, "Well, that's a good fantasy but it will never happen. I'm completely straight."

The next Friday night she told me she had a surprise for me. She wanted me to get dressed up completely, did my makeup and hair and then made a very nice dinner. We ate a romantic, candlelit dinner and I asked if this was the surprise. She didn't often cook, so I imagined it could have been.

"You'll just have to wait and see," she said with a smile.

She opened a bottle of wine and poured us each a glass. We went into the living room where she lit more candles and put on music to create a very nice ambiance. I was just starting to relax when the doorbell rang.

"Are you expecting someone?" I asked.

"Maybe." She giggled and told me to wait while she got the door.

When she opened it I heard a man's voice. He made a joke about not being sure he was at the right apartment and then asked "Are we still on?" She told him "yes" and they came back to the living room together.

"Kasey, this is Dan," Darcy told me. "Do you remember him from the club?"

I recognized him immediately as one of the men who had been hitting on me on my night out dressed. I quickly went from feeling relaxed to feeling awkward. I had almost forgotten I was sitting around dressed the way I was, until I recognized him and Darcy made the introduction.

"Uh, hi Dan," I said and stood up to shake his hand, forgetting I was in heels and almost falling over in the process.

"Relax, sexy legs," he said with a big grin. "You're amongst friends."

"Okay then," I said after regaining my footing and standing up tall.

"Why don't you get me a beer?" he asked. "It's been a long day."

"Okay," I said. His tone was rather sharp and almost rude, but I tried to ignore it. I didn't feel I was in a position to say anything given the way I was dressed.

I paused in the kitchen after opening the refrigerator. What was this guy doing here? Apparently Darcy had given him our address and probably our phone number. I knew he was hot for me, with all he had said at the club, but I had set the record straight. I went back to the living room, handed him his beer and asked him, "What brings you by?"

"Heh," he snorted with a grin. He patted the spot on the couch next to him. "Have a seat, sweetie."

I started stuttering and spitting out words that didn't make sense, so I sat down next to him, crossed my arms and sighed. I looked at Darcy and then at him and asked, "What is this all about?"

Darcy sat down next to me and started running her fingers though my hair. "Honey, I've told you about my fantasy. I just want you to try. If you don't like it, you can stop."

She always looked adorable when she bit her lip and pouted, and at that point she did managed to make it more adorable than ever before. "Please? For me? Just... try it. Dan's nice, don't you think? And he thinks you have really hot legs."

"You do have great legs," he said and ran his hand up my thigh and over my knee. "So smooth and perfect. You are going to look so good on your knees tonight."

He took my hand, which was shaking nervously like the rest of me, and placed it on his crotch. "See how turned on your legs have gotten me?" He was rock hard.

A shudder went through my body and my demeanor started to change. I could hear how pathetic my voice sounded when I said, "Really? You got that hard looking at my legs?"

"Well, you are a very sexy girl," he said and started unbuckling his belt. "Why don't you do a sexy little dance for me? Darcy says you love to so dance sexy when you're all dressed up."

Darcy went over and changed the music. She put on a club mix I made that I put on when I was dressed and came back over to the couch. "Go ahead, dance for Dan."

Feeling awkward and foolish, I got up and started prancing around goofily to the music. Dan continued taking off his belt and then removed his shoes. It wasn't long until he was naked from the waist down and stroking his incredibly hard and very big cock. I couldn't take my eyes off it.

Darcy stood up and took my hand. "Come on, honey. You always said you wanted to try different things. If you don't like it, no big deal, but don't knock it without trying it first."

"Okay," I said in a feeble voice, "but just this once." I kept repeating it out loud in a whispery voice. "Just this once... just this once..."

"On your knees, sweetie. That's how I like it." Dan was grinning like a Cheshire cat.

I slowly got down on my knees in front of him, looked up and asked him, "Do you really think my legs are sexy?"

"Sweetie, any girl with legs like that belongs on her knees. Yours are the sexiest I've ever seen."

Darcy crouched down next to me. "Let me talk you through it, honey. Take it slow."

"Okay." I was shaking.

"First, take it in your hand, nice and easy. Think about how you like it when I do this for you."

"Okay," I said and gently put my fingers around his solid shaft. Another shudder went through my body.

"Lean down and gently kiss the tip. Use your tongue, just enough to give him a little tease."

I nodded and leaned in and did as she asked. I took it very slowly, and then at her instruction I ran my tongue around the head and then slid the head into my mouth. As I did so I lost control and began sucking it, up and down with my head bobbing and my drool dripping down every side of his cock.

"Oh my God," Darcy gasped. "He actually likes it!"

"Look up at me, cock sucker," Dan ordered. I looked up at him, continuing to suck his cock, and he said, "Yeah, he definitely likes it. I can see it in the eyes."

Darcy reached up under my miniskirt and grabbed my dick, which was now rock hard. "Oh my, he really, really likes it!"

I kept going, trying to do what I liked when Darcy and other girlfriends had gone down on me.

It wasn't all that long before Dan moaned loudly and yelled out, "Fuck yeah!" He grabbed my head on both sides and pulled me down hard on him, jamming his cock against the back of my throat and making me gag as he shot his load into my mouth.

I coughed and gasped. His semen was pouring out of either side of my mouth as he relaxed and slowly slid his cock out and slumped back onto the couch.

Darcy had been slowly stroking my dick as I sucked Dan, and after Dan fell back on the couch she picked up the pace.

"That was really good, baby," he said. "You sure that was your first time?"

With Darcy stroking me, I looked at his cock, wet with cum and my saliva and leaned forward and started kissing and licking it.

"Can't get enough now, can you?" he laughed.

Seconds later I came as Darcy finished stroking me and collapsed with my head in his lap.

"Now we just have to teach him to swallow."