The Adventures of Lexi Ch. 01

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Getting caught leads to the night of his life.
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Part 1 of the 5 part series

Updated 10/28/2022
Created 10/17/2010
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Chapter 01 - The Transformation

It's not easy being a college freshman. After my eighteenth birthday last week, my parents told me that they were cutting off my allowance. It didn't take long for me to realize that I needed a job, and fast.

Since I needed a job with flexible hours, due to my full schedule of classes, my choices were limited. After responding to several want ads, the only call back I got was from a babysitting company. The hours were flexible, but were also usually on weekend nights. I guess this was a sacrifice I had to make.

It didn't take long for me to get my first assignment. I was given an address and told to be there promptly at 8pm. Mr. Johnson greeted me when I arrived.

"Hello, you must be the sitter. I'm sorry that we're in such a rush, but my brother-in-law had a last minute emergency and had to drop off his kid for the night. Unfortunately we couldn't cancel our plans. He dropped off everything that you should need to get you through the nigh. Feel free to call us if you have any problems."

He seemed a little anxious that Mrs. Johnson wasn't ready for the party yet. Seeing that he had some time, Mr. Johnson briefly showed me around the house.

They lived in a posh neighborhood with large properties and plenty of privacy. Their house has five bedrooms and six bathrooms, I couldn't believe how much space they had. After a brief tour, Mr. Johnson introduced me to their 1 year old nephew, Aaron. Since I have two younger brothers I already knew the ins and outs of taking care of a baby.

It wasn't until 8:30 that Mrs. Johnson flew down the stairs and rushed to get her coat on. I only caught a glimpse of her tight red dress, but she look spectacular. She couldn't be any older than 30 and was obviously much younger than her husband. She had bright red hair that flowed over the top of her bare shoulders. I'm six feet tall and she looked to be about as tall as me but its hard to tell since she was wearing heels what must have been at least four inch heels. I could barely keep my eyes from following her incredible legs as her thighs disappeared under her tight red dress.

I snapped out of it as she ran over to the door.

"Honey, this is the babysitter the company sent over. His name is Michael."

I extended my hand and said "Hello Mrs. Johnson." But was abruptly cut off.

"Don't be silly, call me Jessica. We should be back by midnight."

She briefly shook my hand as they ran out the door.

I never expected that this is what my Friday nights would be like now that I'm a college man, but I guess I had to make the best of it. After a quick feeding and diaper change Aaron was already asleep and it was only 9 o'clock. I had some time to kill before they got home so I decided to watch some TV.

After about a half an hour of trying to get their home theater working I decided to pop in a movie instead. Their entertainment center had two large DVD drawers under the TV. The first one I looked through was filled with cheesy romantic comedies and chick flicks, not exactly what I had in mind. The second drawer was much more interesting. There were several porno DVDs, but what really caught my eye was the stack of unlabeled VHS tapes.

Curious, I popped one in and could tell that it was a home movie. It looked like the camera was propped up in the corner of a large room filled with plush velvet furniture. The picture quality wasn't very good and the room was dark, but I could see that there were about a dozen people in the room and all appeared to be paired up. The women were all in various states of undress and I thought I saw Jessica making out with someone who was definitely not Mr. Johnson. In fact, it looked like she was making out with another woman.

I've heard about parties like this, but I never would have guessed that the Johnson's were into this. I was starting to get horny just thinking about Jessica with another woman but the video quality was just awful. I tried several other tapes and they all looked like they were filmed in the same room. Each tape must have been a different party, but I noticed that Jessica was always with another woman. I noticed Mr. Johnson in some of the tapes, and he was always with a different woman each time too.

After getting bored of the grainy videos I decided to explore the house a little. I wandered through the main floor of the house, poking my head into each room. Their house was huge but seemed a bit boring, especially given the types of parties they liked.

Eventually I made my way down to the basement when I immediately recognized the room from all of the tapes. There was a large room filled with couches and seats that were all upholstered in red velvet. There was a bar in the far corner surrounded by several more large chairs. The walls were relatively bare with some mirrors and large metal rings positioned throughout the room.

There was a small oddly shaped room with a thick leather door against one wall. I poked my head in for a closer look. The room was quite cramped and appeared to be about three feet long by two feet wide and was tapered at one end. There was a padded bar on the floor on one end of the room and a strange piece of furniture in the middle. I couldn't figure out what it was, but it looked a little like one of those ergonomic chairs with no back that you use your knees and lean forward. It was also covered in the same red velvet as the rest of the furniture. I couldn't resist running my hand along the fabric. It was incredibly soft and the padding seemed very firm.

There didn't seem to be anything else to see downstairs so I made sure I put everything back the way I found it before heading back upstairs.

I looked at the clock and saw that it was only 10:30, so I continued my exploring upstairs.

Each of the bedrooms upstairs was well decorated and appeared to be reserved for guests. The last room I came to was the master suite. I have never seen anything like it before. The room was gigantic with a king size bed in the middle. The bed had a red velvet canopy draped over four poles at each corner of the bed. The bed was covered in red satin sheets and a light blanket was folded at the foot. I couldn't resist lying down in the bed, I've never felt satin sheets before.

As I lay down in their bed I couldn't stop thinking about Jessica in that red dress and what she must be doing at that party.

The master suite had his and hers walk in closets on opposite sides of the bathroom. I slowly crept into the closet on the left side and saw a pile of dirty clothes on the floor. I realized that I must be in Jessica's closet when I noticed a pair of silk panties on top of the pile of clothes. Nervously I reached down to pick up her panties and brought them to my face.

I was getting incredibly horny as I smelled her scent on the panties. I noticed that there was something wet and sticky in the crotch. I brought her soiled panties to my mouth and licked the wet sticky cream off the crotch of her panties. My tongue and lips were coated with her stciky juices. I was overwhelmed by her sweet taste and I licked my lips clean.

Looking around the room I saw an entire wall dedicated to silky lingerie. She had another wall dedicated to shoes, almost all high heels. The third wall was filled with dresses.

I don't know what came over me, but standing in her closet surrounded by her lingerie I got a twisted idea. I ripped off my clothes and pulled her moist panties up my legs. The silky material felt so good against my skin. She must have a smaller waist than me because her panties felt tight around my cock, but it felt so good to feel her moist panties pressed against me. I noticed that the snug fit of the panties kept my cock in place and prevented me cock from getting erect.

I reached for one of her nighties and pulled it over me. My head was swimming as I rubbed my cock through the silky fabric. The feeling of the silky fabric rubbing against my skin and my cock sent waves of pleasure through my body.

Finally I took a pair of her high heels and put them on. I've never worn heels before and was a little wobbly at first. I started to get the hang of walking in heels as I practiced walking around her bedroom.

All of a sudden I heard the bedroom door open. I didn't know what to do. My pulse was racing. I was frozen in place. The next thing I know, Jessica is standing a few feet in front of me.

"Well, what do we have here?"

"I..."

"I'm guessing you didn't expect me to come home this early did you."

All I could do was feebly shake my head no. She reached into her purse and pulled out a small digital camera. before I could react she took several pictures of my standing their in her lingerie and high heels.

"I never would have guessed that you were a sissy. I guess you have the body for it. Tall and thin, you could make a very convincing woman."

What was she saying? Sissy? Not me, I was just having fun.

"Stay here."

She disappeared into her closet and came out with a blond wig. I pulled back as she reached out to put it on me.

"Your not putting that on me. I'm not a sissy. I'm a man!"

"I don't think you understand. If you don't play along with me I can put those pictures of you all over campus."

I was shocked. What did I get myself into.

"If you play along with me everything will stay between us. How does that sound?"

I couldn't believe what was happening to me, but I would do anything to keep this from getting out. I slowly nodded my head in agreement. But I must have looked scared because she added "And don't worry about Mr. Johnson coming home anytime soon. He decided to stay behind at the party."

"Now that we have a deal, come over here so I can put this on you."

She adjusted the wig and took a few steps back to get a good look at me. She lifted up the nightie and roughly grabbed my semi hard cock through her panties. The tightness was still preventing me from being at full attention.

As she released her grip she said "This will do just fine. Have a seat over here."

Jessica motioned for me to sit down at her makeup table. After 20 minutes she had given me a complete makeover. I could barley recognize myself. Jessica disappeared into her closet again as I stared at myself in the mirror. She returned with a bra in one hand, matching the panties I was already wearing, and in her other hand she had something that I didn't recognize.

She came up behind me and pushed the nightie straps off my shoulders. Taking each arm she slowly put the bra on me. Looking at myself in the mirror I thought I looked ridiculous wearing a bra with no boobs. After getting me strapped in she pushed something into each cup of the bra and instantly I had breasts. After pulling the nightie back up to cover the bra, I realized that she was right and I did make a convincing woman.

"You look beautiful. But I don't know what to call you. Mike certainly won't do. How about Lexi? Do you like what you see Lexi?"

"Yes Mrs. Johns.."

"Jessica dear. Call me Jessica. Now lets see just how much you like being a girl."

Jessica moved over to her bed pulled off her dress and tossed it to the floor. I couldn't believe what was happening. This gorgeous red headed beauty was standing in front of me wearing nothing but a pare of panties.

She turned her back to me as she rearranged the pillows on her bed. She jumped on the bed and propped herself against the pillows with her legs spread apart facing me.

"Now come over here and lick my pussy."

I didn't hesitate. I ran over to her as fast as my heeled feet allowed. I ripped off her panties and started to lick her pussy. She was already very moist and I loved the sweet taste of her pussy. I wrapped my arms around her legs grabbing a thigh in each hand so that I could pull her pussy closer to me. It took me a few sloppy passes of my tongue before I started to be more methodical.

I started at the bottom of her pussy and slowly brought my tongue up parting her lips as I worked my tongue from side to side. I could taste sweet juices I passed over her hole. When my tongue made it way to her clit I would apply more pressure and make slow circles. I could tell that she was enjoying this as she moan with every one.

"Oh yes, Lexi. Don't stop, don't stop." Jessica quickly went from moaning to screaming as she came. I could feel her entire body shudder as I continued to lick up her juices.

After she settled down she reached over and opened up her night stand. She grabbed something and stood up. I couldn't quite tell but it looked like a dildo. Before I knew what she was doing she turned around and had a large cock strapped to her pussy and a tube of KY jelly in her hand.

"Now it's your turn Lexi. Turn around."

I slowly complied, unsure of what she had in mind. Then I felt her push me over the edge of the bed. I stood there with my panty covered ass sticking out. As she spread my legs spread apart I had to clutch on to her bed to that I wouldn't fall over. She didn't give me a chance to resist and quickly pushed one of her fingers into my ass. I've never felt anything quite like it before. I never even thought about trying anal sex but this felt good.

After several seconds of her sliding her finger in and out of me I felt something cold pressing against my backside. Slowly it dawned on me. She was going to fuck me like a woman, and I was going to enjoy it.

Fortunately she moved slowly. I felt my insides filling up as she slide her fake cock into me. I couldn't believe that she was going to get that whole cock inside of me. It looked huge. At first it was uncomfortable but then I started to loosen up. After a few minutes of her fucking my ass I could tell that I was going to lose it. I let out a loud scream as I came in her panties.

She must have known what happened because she then pulled her cock out of me. I was exhausted and fell to my knees.

She sat down on the bed and straddled her legs on either side of my head. She lifted my head and placed it on her thigh. I was again staring right into her beautiful pussy. Her short red hairs were matted down from sweat and fell into crimson curls around her lips.

"Not bad for a first time. Now I need to ask you for a favor."

At this point I would say yes to anything.

"We are having a party tomorrow night and one of my friends had to cancel. Cassie was scheduled to be in the box but since she can't make it we have an opening. Would you like to join us?"

What could I say, who wouldn't want to join Jessica for one of her parties.

"Ok"

"Perfect. Now let me get you an appropriate outfit to wear."

Once again she got up and disappeared into her closet. When she returned her arms were full. She picked out a simple floral print dress that would only come halfway down my thighs. She handed me a matching blue silk set of bra and panties. She also gave me a black garter belt and sheer stockings to go with the four inch heels.

She also handed me and trench-coat and said that I certainly couldn't go home looking like I did.

I was starting to feel like I might be part of the entertainment instead of just a guest. I didn't care. As long as I could taste Jessica's sweet pussy again I would do anything.

She told me to be back there tomorrow at 8pm and to shave my entire body.

She handed me a bag to carry my new wardrobe and I put on the trench-coat. I felt ridiculous walking back to the dorms dressed like this. I could only hope that nobody would recognize me.

As I walked back to campus I could feel my cum dripping from Jessica's panties and running down my leg. I was afraid that I would draw more attention to myself if I left a trail of cum in the dorm so I reached down and used my finger to wipe it off my thigh. Now what? Since I didn't have anything to wipe it off on and I was clearly not thinking straight anyway I put my finger to my mouth and licked my own cum off. I don't know why I did it, but I didn't mind the taste. It was salty and musty, and when mixed with the taste of Jessica in my mouth it made me even hornier. I used my hand to wipe the rest of my juices from my cock and legs and licked up every drop.

I was so exhausted when I got back to the dorm that I took off the trench-coat and flopped onto my bed. It was already 2pm when I finally woke up. It took me a little while to remember what had happened last night - it still felt like a dream. Once I realized that I was still wearing Jessica's nightie and panties it all came back to me. I looked at the clock and realized that I didn't have anytime to mess around. I didn't want to be late for the party.

I felt silly wearing the outfit she gave me without any makeup on, but I didn't have a choice. Jessica answered the door wearing a short silk robe that barely covered anything.

"Right on time. I like that in a girl."

She gave me a quick peck on the lips and pulled me inside.

"Don't worry, Mr. Johnson is out running some errands before the party. We have plenty of time to finish you up before the guests arrive."

She led me back to her bedroom and proceeded to give me a full makeover. This time she added a pair of fake eyelashes. After she was done I couldn't believe the gorgeous blond that was staring back at me. I would have fucked myself if given the chance!

She told me to make myself comfortable while went to her closet to her herself ready. I headed straight for the nightstand to get a closer look at what she fucked me with last night. It was a large realistic looking cock attached to a leather harness. There is no way that this fit inside of me...

When Jessica came back into the room she was only wearing a black garter belt and black high heels. Her firm breast looked incredible. I couldn't wait to get my hands on her again.

"I see someone wants another round with my strap-on. You're a naughty girl, aren't you. Don't worry there will be plenty of time for that later. First, I need to loosen up before the party."

She took a seat on a plush armchair on the far side of the room and motioned for me to come over. I dropped the fake cock and quickly ran over to her. She pulled my face down to hers and gave me a deep kiss. Her smooth lips tasted like candy. She then pushed my head down to her waiting pussy. I took my position on my knees between her stretched out legs. I could already smell her and could see the moistness of her pussy in her glistening curls of hair. I licked her with everything that I had. I loved the taste of her juices and couldn't get enough. When she finally came her cum dripped down my chin. She used her finger to wipe it off my chin and then licked it off herself. She pulled me back up for another kiss and then told me to wait for her in the living room downstairs.

Shortly after I sat down in the living room I heard her husband come home. He headed straight upstairs without noticing me. I was getting about what might happen if found out what I had done with his wife. After about 15 more minutes of waiting Jessica appeared in the doorway. She was a knockout. She was wearing a silky green dress that fell loose on her chest. I could tell from he cleavage that if she leaned forward at all you would be able to see both of her firm breasts clearly. Her dress was tight around her flat belly and opened up again at her waist. It was so short that it barely covered her sweet pussy that I could still taste on my lips.

She came over to me and gave me another deep passionate kiss. As she kissed me I could feel something thick in her mouth. I felt her pushing it into my mouth with her tongue and started swallowing it without hesitation. I could tell that she must have just given Mr. Johnson a blow job. His cum still felt hot in my mouth as I tried hard to swallow it all. Some of his cum dripped out of the side of my mouth and down my chin. I used my finger to wipe it up and proceeded to lick my finger clean

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