Connie Goes to College Ch. 01

Disclaimer: The following story is not intended for minors. Any resemblance to actual persons is purely coincidental. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with my stories that are a combination of true life encounters and fantasy.

*

Let me start by introducing myself. My name is Connie and I am a 40-something transgender woman. I live part of my life as a man, but I enjoy spending most of my free time practicing the art of female illusion. To me there is nothing more exciting than taking a long bubble bath, shaving from head to toe, carefully applying makeup, selecting the right outfit for the day/evening, and going out to take on a new adventure.

I have been a fan of erotic stories for many years, so I thought I would contribute a few myself. Let me start with an early adventure when I was much younger and very inexperienced.

I first discovered the joys of cross-dressing in my early teens, trying on my sister's clothes and pantyhose. It wasn't until I got to college that I was able to enjoy the freedom of getting dressed en femme. I kept a small stash of panties and nylons hidden away in my closet and would wear them to classes whenever I could. The feeling of nylon kept me in a constant state of arousal.

As it turns out, my freshmen year was going to be the beginning of many wonderful experiences for me. Halloween was fast approaching and I always wanted to take the opportunity to dress up in some feminine costume. My circle of friends that first year consisted mostly of guys and girls from my high school. So one night after classes I was hanging around a few of the girls and we started talking about the Halloween parties that were planned in the dorms. I started "hinting" that I had no idea what my costume would be, and we started tossing around different ideas. Everyone mentioned all the typical costumes like ghosts, ghouls, witches, cheerleaders, pimps and hookers, etc.

During one point in the conversation, I mentioned how much I really liked Elvira and how sexy she was. I couldn't believe my ears, but my good friend Lynn suggested that I dress up as Elvira! Trying to hold back my excitement as best I could, I of course pretended that it would never work. She eventually convinced me that she had a few ideas on how to make me look like Elvira and how much fun we would all have. So we decided that we would go to the local Goodwill store that weekend and find the necessary items.

As you can imagine, it took forever for the weekend to come. I went over to Lynn's dorm room early on Saturday and we headed off to town. At the Goodwill store we had a lot of fun looking through all the clothes and shoes trying to find something to fit me. Lynn decided she was going as a "Flapper" girl and found a really great dress and some gaudy cheap jewelry. Finding things for me was a little more difficult, but we finally found a long black dress and some black high heels. It was a little embarrassing trying them on in front of her, but she really put me at ease with a few encouraging words.

After getting the bulk of our costumes at Goodwill, we were off to the drugstore. Here we found all the makeup she needed and the black pantyhose I would need. Yes, that was another embarrassing moment. To complete the costumes, we needed wigs, so we stopped at the mall on our way home. We were able to find a funky orange-red bob style for her and a long black one for me at one of those kiosks. They were a pretty decent quality and didn't cost too much either.

We finally got back to the dorms and Lynn offered to keep everything in her room. Halloween was still a couple weeks away and it couldn't come to soon. Finally, on the morning of Halloween, Lynn called and told me to meet at her room around 4:00 so we had plenty of time to get ready. She also told me to bring my shaving kit. When I arrived, her and her roommates were already getting dressed. She handed me a couple bottles of Nair and told me to go in their bathroom and cover my entire body from the neck down. I was to wait for 10 minutes and shower everything off.

I got in the shower and proceeded to take a wash cloth and remove all the hair. When I was finished, I noticed she had laid out a bra, panties, and pantyhose. There was also a black robe hanging on the door. She peeked in the door and told me to shave very close and put everything on so she could start applying the makeup. I asked her if the bra and panties were necessary, and she said I needed a way to hold my breasts in place and a proper girl should wear panties.

She had me sit down in front of the mirror and started to work on my makeup. She did an incredible job making me look very sexy with dark eye shadow, lots of mascara, blush, and bright red lipstick. After the makeup was finished, she placed the long black wig on my head. I still remember desperately trying to hide my "excitement" as her roommates teased me.

Then Lynn had me take off the robe and handed me a couple of water balloons for my bra. They felt so heavy and really jiggled when I moved. Next came the dress which I noticed Lynn had altered. She was very proud of the high slit she added to the dress which showed off my long legs. I put on my shoes and practiced walking in them awhile. Lynn added a necklace, clip-on earrings, and surprised me again with some sexy press on nails. Before we left, one of the girls loaned me a little purse to hold my lipstick, driver's license, and money. Lynn and her roommates were proud of their work and really wanted me to play the part.

Soon we were all off to the party. I had a little trouble walking in the shoes at first, but quickly got used to them. The music was loud and the beer was flowing. I was very self-conscious about being dressed like this, so I stuck pretty close to Lynn. As the night wore on, more and more guys starting grabbing my butt and making lewd comments. I often wondered how many knew I was a guy and how many I fooled. I suppose more knew I was a guy than didn't, but I really started to loosen up and have fun. I started dancing more, even though the heels started to bother me. The more I danced with Lynn and her friends, the more feminine I felt. Fortunately, I didn't run into many of my guy friends. The ones that I did see couldn't believe how good I looked, but I could tell they were a bit uncomfortable and didn't know what to say. I also ran into my roommate, but I realized I didn't tell him about my costume beforehand. He was really surprised it was me and couldn't stop staring, but I found it strangely arousing (more on him in later chapters).

The party started to die out around midnight, so a group of us decided to head downtown to one of the bars. One of Lynn's roommates offered to drive even though it was just a few blocks away. Lynn and I sat in the back seat and she showed me how to apply my lipstick to keep it looking fresh. The bar was pretty crowded, but not as many people were wearing costumes. I felt a little out of place again, but Lynn quickly found us a table and I took a seat to rest my aching feet. Before I knew it, guys were buying us drinks and asking us to dance. Now instead of just dancing with Lynn and her friends, I found myself dancing with a few different guys, and I really started to enjoy myself. One guy who seemed like he had a few too many drinks even asked me to dance to a slow song. I could feel his hard on rub against my thigh and I had to do my best to hide mine. More than once I had to slip off to the bathroom and try tucking it away. I even practiced putting on my lipstick.

I glanced over at Lynn and noticed she was getting to know one of the guys better. I went up to her and whispered that she didn't have to worry about me and she should go for it. Before I knew it, most of the gang had either left the bar or were in the process of hooking up. Since it was almost closing time, the crowd was getting pretty thin, so I took a seat at the bar. The bartender came over and asked me what I was drinking. He was a little older, maybe 25 or so, tall and pretty good looking. I was feeling a little flirtatious, so I asked him what he recommended. He said, "a sexy girl like you should be drinking a mixed drink instead of beer from the bottle." He introduced himself as Jeff and said he had the perfect drink for me. He quickly mixed a few liquids into a shaker, poured it into a cocktail glass and said, "It's was on the house!" I don't know what was in the drink, but it was sort of sweet and made me warm all over. I had a few more and before long it was last call. By this time I had trouble sitting on the bar stool and still trying to play the part of Elvira. He noticed my predicament and offered to drive me home. Not wanting to walk all that way in heels, I quickly took him up on his offer.

I sat at the end of the bar while he closed up. I had trouble staying awake, but Jeff was done pretty quickly. Soon we were off to his car and he had his arm around me, helping me walk. When we got to his car, he offered to open the door for me, just as any gentleman would for a lady. As he reached for the door, Jeff got very close to me and I don't know why, but I put my arms around him and gave him a kiss on the cheek.

Jeff looked a little shocked and responded, "why you sexy little devil you!" He then proceeded to kiss me on the lips and I felt this surge of emotions running through my entire body. We began to make out right there next to his car. His hands were all over me and I could feel my pantyhose expanding. After about 10 minutes of heavy petting, he suggested we go back to his place. I was pretty drunk and horny, but up to this point, I had never been with a man. I told him I was embarrassed for kissing him, but I didn't think I was gay. He explained he was bisexual and had a thing for feminine guys and cross dressers. He put me totally at ease as he held my hand and explained what I was feeling was completely natural. Jeff promised we could just talk and he would take me home whenever I wanted.

I don't know why, but I felt very comfortable with Jeff. It was almost like he was an older brother, but I was attracted to him on some level. We drove to his house and I made myself comfortable on the couch. Jeff offered me a drink, but I thought I had too much already and asked for some water instead. He sat next to me on the couch and casually placed his hand on my thigh. Before I knew it, I was looking into his eyes and we started to kiss again. I did my best to kiss like a lady and I could tell he was enjoying it.

I was getting very horny again and I just couldn't help myself. I started rubbing his crotch through his jeans. It felt so good to feel his hard on and I think I actually started to drool with lust. Jeff asked me if I wanted to give him a blow job and I think I barely said "yes" because I was so nervous. He told me not to worry and he would guide me. He stood up and took off his jeans. I got on my knees on the floor and stared at his white briefs with this raging hard on trying to get out. I kissed his cock through his underwear and then pulled them down to his knees as his cock sprang to attention. Jeff had an average size cock, but I was fascinated by how another guy's dick looked up close and slowly massaged it with my hand.

Jeff rubbed my cheek and said, "go on baby, suck it like a lollipop"! That was all the encouragement I needed as I started suck the head and lick the entire shaft starting at his balls. For a beginner I thought I was doing pretty good and I felt my panties getting wet as I continued to suck Jeff's cock. Before long he starting moaning and I knew what was coming next. I was afraid to have him come in my mouth, but for some reason I just kept sucking. Then Jeff said, "Oh baby, I'm coming!" and I just closed my eyes and hoped for the best. I felt his cock explode as his balls tightened and the cum shot hit the roof of my mouth. I remember it tasted salty, and had a thick consistency. I almost gagged, but for some reason I just started swallowing it. He shot a few more squirts then pulled out of my mouth and sat down on the couch.

As I sat there on the floor with the taste of Jeff's cum in my mouth, I felt ashamed, excited, sexy and somewhat confused. I also noticed my panties were completely wet as I must have cum quite a lot myself. I got off my knees and joined Jeff on the couch. He put his arm around me and we actually cuddled for awhile. Jeff assured me that I did a good job pleasing him and hearing that made me feel good. We ended up falling asleep right there on the couch, with my head on his chest and my hand on his crotch.

(To be continued)