Jessica Meets the World!!

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Jessica gets a surprise!
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It had been weeks since I had my first experience and encounter with Ty. Amazingly, I was still on a high from it. I couldn't believe how much fun it was. Just imagine, here I was thinking I was home alone in that sexy new black dress only to be surprised by Ty the maintenance man. I went from scared, to be embarrassed, to turned on all in a short period of time. When it was all over with, I had completely turned on Ty and had taken all 8 inches of him in my mouth.

This whole experience had given me a whole new sense of confidence. Now when dressed, I was Jessica. Anytime spent at home was spent as Jessica these days. Summer season was in full effect now. So everyday after work I take a nice shower then I slip into a small pair of shorts and tank top. Even though, I didn't think I was completely ready for outside world interaction as Jessica, I wanted to step out and see how it felt. So it was on this random Saturday night that I decided Jessica should go outside for a walk figuring how bad could it be. Just a quick 15-minute walk down to the deck overlooking the lake and back upstairs to the apartment. It would be so dark there that no one would be able to get a great look at my face. And I could avoid a lot of interaction, as I hadn't completely perfected my voice.

An excitement came over me as I started the transformation to Jessica. First to the kitchen to pour a tall drink then back to the living room to turn on some music. A quick shower was in order then I took a seat in front of the mirror to apply my makeup. Since it was late, I decided not to do too much. Just a tweak to the eyebrows and a soft red lipstick for the lips.

The biggest question was what to wear? Not too flashy tonight...sexy but comfortable was going be the look. A black pair of leggings with a lace bottom paired with an off the shoulder grey tee. Out the closet came a black pair of 5-inch strappy platform sandals. I quickly pulled out a black thong to help tuck away my secret and a black bra to wear for effect with the off the shoulder tee. I took my time dressing as I started to second-guess if this was going to be a good idea. I took my time finishing my drink before finally deciding that I was going to do this.

Now completely dressed, I chose a short black wig to finish everything off. With the humidity of the night, I needed to stay as cool as possible. Now standing and looking in the mirror, I was satisfied with my look. I always loved the way I looked as Jessica. I checked to be sure that the lipstick was how I wanted and looked myself up and down to be sure I was completely satisfied. I turned around to see how my ass looked in the leggings. Great as usual I said to myself.

I worked out 5 days a week to keep my body exactly how it was. 5'7" with toned legs, 29" waist. But what I was most proud of was my ass. It was perfectly shaped and matched my slim frame. I was so anxious to see what kind of attention it would get just walking down the street!!

One more drink before heading out served to calm my nerves. I started for the door and first listened to see if anyone was out there. Since I didn't hear anything, I opened the door and stepped out. I walked fast and headed right for the elevator. Right now, I didn't want someone on my floor to be the first person I ran into tonight. It seemed like it took an eternity for the elevator to finally ding and open up on my floor. Stepping into the elevator my nerves began to calm...I was really doing this. I watched as the numbers passed on the display when all of a sudden on floor 5, a stop. On to the elevator walked an older guy, probably early 40's. He smelled good but wasn't my type. I flashed a smile as he said hello. As he stood behind me in the elevator I could feel his eyes on me. I wondered know if it was because I looked good or if he knew what I really was.

The second floor was my stop and as I walked off the elevator I glanced at the mirror across from the doors. I could see the man looking at me as I strolled off the elevator. His eyes firmly fixed on my petite little ass. Seeing him stare at me made my confidence shoot through the roof as I walked towards the door. There was no doubt in my mind now that this was a good idea.

Outside it was a beautiful night. The breeze coming off of the lake was so refreshing. I walked around the deck for a while then decided to have a seat at one of the tables. Listening to the sound of the water was so relaxing and the moon shone brightly off the water. I was so happy I decided to do this. All of a sudden, I heard someone say, "Excuse me." I was startled and jumped up so fast that I almost fell. I noticed that it was the older gentleman from the elevator.

"I'm sorry!" he said as I scrambled to my feet. "I didn't mean to scare you or anything. We were just on the elevator together. I just really thought you were beautiful and sexy. I really wanted to come and tell you that so I followed your over to here."

"Don't you think that is a little stalkerish?" I quipped at him.

"It may be, but I would hate myself if I let you pass and didn't approach and say anything to you" he answered.

Hearing this made me perk right up. But I was still weary of a man who decided that he wanted to follow me. I decided I would give him a few minutes of conversation but I would tread lightly. "Oh really. So what was the thing that you most like about me," I asked.

The stranger responded, "Well first thing is your smile. It can light up a room. Second, how good your ass looks in those pants. When you walked away, I couldn't keep my eyes of it. That's another reason why I stopped the elevator and came over to where you are."

I didn't know how to react to that. It was so forward and her was this man that decided he wanted to follow me. I hadn't planned on any of this. To top it all off, something about his words aroused me. I could feel my excitement growing in my pants. Thankfully it was dark out on the deck, as the leggings would not have been much concealment at this point.

"Oh really?" asked Jessica. "Well I work really hard to make sure that it looks the way it does. I'm glad that my hard work is paying off. So what's your name?" I took a seat as he answered me.

"Sam" was his response as he decided to sit down right next to me.

We continued with small talk for about 15 minutes. All the while I was becoming more and more relaxed. Sitting back on a bench, I crossed her legs so that I could see his reaction. With the wind blowing in my hair, I don't know if I could have felt any sexier.

I asked what Sam's plans were for the evening and he told me he was on his way out to meet with the guys for a few drinks. He asked if I wanted to come with him but I declined. I knew I wasn't at the point that I could pull something like that off. But I did say that maybe I would accompany him another time.

Sam asked if he could walk me back to the elevator and I told him yes. So we got up and strolled towards the elevator. I walked slowly so I could enjoy the last bit of this night breeze still feeling ever so sexy. As we got to the door, I brushed against him ever so slightly just to feel the manhood in his pants. This obviously excited him as he barely let me get through the door before moving in with me causing his own intentional body contact.

This was a different feeling for me; one I didn't know how to feel about. I wanted to be the one that was turning somebody on. Now here I was, horny out of my brain. Maybe it was the combination of my drinks earlier and the night breeze. Maybe it was the fact that I felt so sexy at this moment. I'm sure it was the fact that here I was, dressed as Jessica with minimum make-up on and this guy was still hot for me. Maybe I was more ready for the world than I thought.

My senses were going crazy. Just the sound of my heels clicking against the floor as we walked towards the elevator was driving me wild. I felt like I was gonna explode inside of myself.

We reached the elevator door and he pushed the button for me. I thanked him for the conversation as we waited. I wanted to ask him to come up, but I felt I should be a lady. Sam asked when I would take him up on the offer for drinks. As he asked, he moved closer to me, into my space and stared right into my eyes. As I looked up at him, the desire to be a lady went out the window.

I invited him up for a drink right then and there and he accepted. The ride to the 16th floor went fast. Before I knew it Sam was on my couch and I was pouring him bourbon. I sat on the couch across from him. By this point, I had more control over my senses and decided I was going to take control of the situation. I slid off my shoes and got comfortable on my couch. We continued with small talk for about 10 minutes before I got up to freshen up his drink. As I walked to the kitchen, I turned on the cd player. I made sure to sway my hips side to side with the music as I poured his drink.

Before I knew it, he was standing behind me. It startled me, but before I could even react our lips were locked. Sam ran his hands up and down my back, and then slowly he slid them down to my ass. This was the first time I was experiencing someone being in charge of me. I was so turned on, so into the moment as Jessica. I completely forgot that there would be no way at this point that I would be able to hide the bulge that was no doubt showing by this point. I was determined to take back control of the situation.

Before I knew it, Sam had me lifted in the air. I had never been so scared and so excited at the same time. I knew that any second now he would see what my leggings could no longer hide. The prospect of that happening made me even harder.

As he sat me down on my counter, I closed my eyes and held my breath. I didn't know what to expect. After a moment that felt like forever, the next move surprised me. I felt his hands on my cock. I opened my eyes and found Sam pulling down the top of my pants to expose my rock hard cock. Before I could say a word, his mouth was around me. I could feel the strength in his jaws and he worked up and down my cock. I couldn't help myself and I took my hands and rubbed the back of his head and he ran his mouth up and down and around my throbbing cock.

It felt so good. I had never experienced this from a man before. I was so turned on that I didn't have much of a chance of lasting too long in his mouth. I felt myself getting close to that point. I lay back on my counter and threw my legs on top of his shoulders.

I shot load after load into Sam's mouth and he never moved his mouth off of my throbbing cock. I had never cum so much. I felt physically spent when I finally shot my last load. My gratification was short lived, as I knew we would have to talk about what just happened.

As I sat up and got ready to speak, Sam just smiled at me and thanked me for the drink. He then kissed my cheek, turned and left out. I sat on my counter an eternity trying to process what happened before I was finally able to move. I was still so horny from happened that I found myself running my hands up and down my still erect cock. Before I knew it, I was cumming again all over the floor.

I walked slowly to my bathroom to start the shower to clean myself up. To my surprise, I was still hard and wanted more. I knew at that point that I would have to run into Sam again in the future!!

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AnonymousAnonymousover 8 years ago
please continue

This was a surprising story in that you didn't even get to suck his cock or get fucked. Please continue with the next chapter in which you and Sam go all the way and have hot gay sex. I too am a CD and would love to meet a "Sam" in my own apartment building. Lucky you !!!

AnonymousAnonymousover 10 years ago

"Oh really?" asked Jessica. "Well I work really hard to make sure that it looks the way it does. I'm glad that my hard work is paying off. So what's your name?" I took a seat as he answered me.

Strange slip from first person to third person and back to first person! Otherwise a well written story.

herb9930herb9930over 10 years ago
Me too.

I would certainly trade places with Sam anytime. Really a great story.

slimwun81slimwun81over 11 years agoAuthor

Thank you for the kind remarks on my story sweetie!! XOXO!!

Joannemitchell67Joannemitchell67over 11 years ago
Yes please

Mmmmmm. OK fellow CDs. Howmanyvof us would LOVE to meet a Sam. I would. !!!!

I am all dressed up, and no place to go. Lol.

Well done

Jo (Joanne) ;-)

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