Date: Fri, 14 May 2004 21:13:17 -0700 (PDT) From: Dan R Subject: My first time crossdressing part 4: The College Years chapter 2 As Jill dragged my by the hand towards the door, I became more and more scared about going outside. I didn't really have a choice so I just kept my mouth shut and silently hoped that it would go ok. Luckily her car was parked out back of her apartment building, so we wouldn't be seen from the road as we went outside. This put me at ease and I just followed her out. My heels clicked on the pavement as we quickly walked to her car and climbed in. My skirt rode up my legs as I sat in the passenger seat. I swung my legs into the car and noticed how high my skirt was sitting, but no amount of adjustment would change it. I knew that anyone in truck would be able to get a good glimpse of my panties, and the thought turned me on a little more. She started the car and we quickly pulled out of her apartment complex and jumped onto the highway, and quickly we were several towns over. I realized where we were going and quickly I was more at ease than I had previously been. The town we were headed for was well known for having a large gay community, and an equally large transgendered community, so the thought of being there dressed as I was wasn't nearly as scary as it had been earlier. We rode almost in silence, listening to the radio as I kept taking glimpses of her smooth thighs under her skirt, and I noticed that she kept glancing at mine, which made me smile some more. After about 20 minutes in the car we got off the highway and pulled into a large parking lot, and I realized that we were at the mall. We parked quickly and climbed out, and again taking my hand Jill, lead the way into the mall. I don't even know how long we were there, it must have been hours, but to me it was one long blur of activity. Several times I did notice people looking at us, but not in any weird way just looking at the two nicely dressed women shopping. By the time we walked out of the mall I had at least 5 bags of stuff. I had bought 4 new pairs of shoes, 3 dresses, 2 skirts and 5 different types of tops. I also had a bag from Victories Secret with a wide assortment of bras, panties, and stockings, and a couple full pieces of lingerie. Walking around in the mall we even got a couple of wolf whistles that made me blush, and I think I even wagged my butt at the people whistling. Walking out of the mall the sun was going down, and I felt my stomach rumble. She asked if I was hungry and I said yes, so she told me to put my bags into the trunk, then grabbed my hand and pulled me towards the Applebee's that was next door. Inside I noticed the hostess look us up and down and smile a little, probably knowing I wasn't really a girl, but she sat us politely and we ate an unhurried dinner. She told me that back at her apartment she had a surprise for me and I felt my cock twitch. I had gone through almost the entire time in the car and at the mall in a semi-erect state and I was doing everything I could to keep myself from getting fully hard, but she wasn't helping as I felt her rubbing my calf with her foot under the table. After dinner we drove back to her apartment, the entire way with her hand on my thigh. I tried to concentrate on something else but her hand was massaging my smooth skin and driving me nuts. Back in her apartment I put my bags into the bedroom as she told me and sat on the couch. She went into her bedroom and closed the door behind her, and I wondered what she was doing on there. Shortly she came back out, wearing the same clothing. I had thought she was going to change but I guess she was doing something else. Again she dropped to her knees in front of me and I leaned forward. We began to kiss harder and harder, till out faces were pressed tightly together and our tongues wrestled together almost roughly. I felt her hands again moving up my thighs and her thumbs hook into the sides of my thong. She tugged it down and my cock sprung free and was again creating a tent in the front of my skirt. She pulled her lips from mine and dropped her mouth to my hard cock. She licked her way up and down my shaft and my cock twitched every time she moved. Finally she engulfed my cock with her hot mouth and began to suck up and down my shaft, as her tongue played with the bottom if my cock. Too soon I felt my cock swell with my cum and she looked up into my eyes as I exploded into her mouth. As my orgasm subsided, she brought her head back up to mine and kissed me. Before I knew what she was doing she had emptied her mouthful of my warm cum into my mouth. Not sure of what to do I just accepted it and swallowed. I felt her smile as I swallowed, and she pulled her head back and looked into my eyes. "Are you ready for your surprise now?" she asked me. I told her yes and she stood up before me. She reached under skirt and pulled her pink panties down to her feet, and kicked them across the room. Then she reached behind her and unzipped her skirt. Dropping it to the floor, she smiled as I saw for the first time the 8" strap-on dildo that she was wearing. She smiled at me as she told me that she wanted a blowjob too. I leaned forward and gingerly took the blue dildo between my lips, slowly licking up and down its shaft, and with every stroke I took more and more into my mouth. Jill moaned as the back of it pushed against her clit, and I worked it harder as a result. After a few minutes of my blowing her new cock, she pulled it back and told me it was time to experience sex as a woman. I was a little scared as she pulled me off the couch and led me towards her bedroom, her erect dong pointing the way. She walked me down to the end of her high bed and told me to face the bed. I turned and as I did, she kicked my feet apart towards the posts of the bed, till my feet were spread so far apart I teetered on my shoes, and had to lean forward against the bed to stay standing. Before I knew what she was doing, she had tied each on my ankles to the bottoms of the bedposts, ensuring my legs would stay spread no matter what. I tried to turn and look back but from my extreme angle I couldn't see much. I felt cool air rising up under my skirt and knew that my bottom was exposed for her. I felt her fingers probing at my puckered anus, and she told me to relax a little as she spread a handful of lube on my hole. Then I felt the tip of the bottle gently penetrate me as she squeezed even more up inside of me. She lifted my skirt the rest of the way off my butt leaving me completely exposed and then I felt it; The tip of her new cock pushing gently at my hole. I relaxed as much as I could and I felt the head slide in past my rim. We moaned in unison as she gently pushed it further in. As she pulled back I felt empty inside and begged for more. Gingerly she began to put more and more of it inside me with each stroke, until she was burying the entire thing inside me with each stroke, and almost completely withdrawing it pulling back. She gloriously fucked me like that for about 10 minutes, until I felt my cock begin to well up again. Through the moans I told her that I was going to cum, and she immediately stopped with the dildo buried inside me. "Not until I do Hun" she told me, and gently withdrew the dildo from my ass. I felt her bend over and unstrap my ankles, and she told me to turn around. As I turned, she pushed me back on the bed, then reached out and grasped my hips. Sliding the dildo back into my ass, I wrapped my legs around her hips and hooked my feet behind her. Holding myself up with just me hands, I began to ride her. She bit her lip as I ground the back of the dildo against her clit, and as the head of the dildo pushed against my prostate I felt my orgasm building again. I shouted out that I was going to cum, and she said she was too. In unison we moaned, as I shot my load past my head and onto the bed, then as it slowed it landed on my chest and stomach. I could feel her shaking as we collapsed onto the bed together. Caressing each other as we lay on the bed, I told her that it was the best day I'd ever had, and she smiled. After what seemed like too little time, She told me to take a shower and clean the cum off me, and as I undressed she took my clothing and put them in the sink along with her panties to soak. Climbing out of the shower I found a box sitting on the toilet seat. Inside was a sheer powder blue babydoll nightgown with matching panties. I slipped it on and then stepped into the blue high heeled slippers that were sitting on the floor, and went back in the bedroom. Jill whistled as I walked in. She was lying on the bed in a pink satin nighty. I kicked off the shoes and climbed onto bed with her. Talking about the day, she assured me it was only the first of a lot of more fun. Then we climbed under the sheets together and fell asleep... Even more coming soon I would appreciate anything you would like to send me, feedback, stories, pictures, anything at all. My email is Vtcarfanatic@yahoo.com. Danielle