The Internship 1

I was out of school for the summer. Being a 20 year old college student, I always needed money to pay for school. Fortunately, daddy was able to find a job for me at this real estate investment company. He was friends with one of the people who worked there. Apparently, I was going to be an administrative assistant for a woman named Jan. I didn't know much about her other than the fact that she had just started working for the company as well. Needless to say, I was a little nervous meeting her. I wanted to make sure that I made a good impression on my new boss.

I decided to wear a knee length black skirt, a pair of open toed pumps and a red short sleeve blouse. I came to work early on a Monday morning. I was probably there at around 7:45 AM. I walked in the building and told the receptionist that I was Jan's new assistant.

The receptionist, a middle aged woman, said "Oh, I see. Well have a seat, she should be in shortly."

I didn't know what that was all about, but I decided let it go. I didn't want to get into the office politics thing yet. So I took a seat over at the couch in the lobby and proceeded to wait for my new boss to arrive an hour later.

At around 8:45, a person walked through the door, wearing a white button up long sleeve shirt, a pair of blue jeans and brown penny loafers. The person had short white hair, a husky yet muscular body with broad shoulders and what looked like breasts. To be honest, I wasn't sure if it was a man or a woman until she spoke to the receptionist in a deep but definitely female voice.

"Hey Susan, is my new assistant here yet?" said Jan.

"She's right over there." Said the receptionist nonchalantly.

The woman with the short white hair and masculine body walked over towards me. Just by the way she walked, I could tell that she was a confident person, a go-getter, she knows what she wants and gets it. I was already intimidated by her and she hadn't even said a word yet!

As Jan came to the couch, I stood up to meet her. I was 5'6" without shoes on, and even with my heels, she was still a little bit taller than me. When she extended her hand to shake mine, I couldn't help but notice how different we both were. She had a stout, masculine frame compared to my slender, tight, young feminine body. She had short white hair and I had long sandy blond hair. She had to be in her mid to late 50's and I was 20. We were definitely opposites.

"Hello, you must be my new assistant Carli. It's good to meet you!" Said the Jan as she smiled and shook my hand with a firm grip. "Let's go to my office and get to know each other."

As we walked to her office, I could see that Jan was checking me out. I've had plenty of guys ogle me before, but I was uncomfortable having my boss, an woman, leering at me! I decided to let it go though. She was going to be my boss for the summer and I didn't want to start if off on the wrong foot. I would just have to subtly let her know that I was not interested and unavailable.

Jan sat behind her big desk in her plush office. She told me what she expected from me as her assistant. She said that she could be demanding and a "hard ass" at times but she promised that it wouldn't happen very often and that she could be a fun boss too.

Along with job expectations, Jan told me more about herself. I found out that she was 55 years old, a mother of two fully grown daughters, one of which was married with children, the other was a Marine. She also told me that she was a butch lesbian and was in a relationship with a woman in her 30's. For a woman in her 50's she looked like she could take care of herself.

Even though Jan told me that she was in a relationship, I wanted to make sure that she knew that I was unavailable just in case. I told her that I was 20 years old and had a boyfriend, who went back home in another state, that I was deeply in love with. I also told her that I was going to be a senior in college and planned to be a teacher. Then I went on to tell her that I was working over the summer to get money to pay for books and tuition for classes.

I had to admit that I was nervous and uncomfortable sitting there knowing that I was going to be working for Jan. I had lived a sheltered life and had never been exposed to a butch lesbian before. I know that my parents would've freaked out if they knew that their little girls was working for a lesbian. My dad especially since he's the one who found me this job.

They wouldn't have wanted me to consort with a woman like Jan. They would've been afraid that my new boss would try to take advantage of their little girl. And in a way, that made it a little thrilling to me, knowing that it was something they wouldn't approve of.

The first week of work was great. Jan got me up to speed and showed me what I need to do. It was a lot of fun working for her actually. The more I got to know Jan the more I enjoyed working for her. She was down to earth, funny and charismatic. Honestly if my dad got to know her, I think he would have liked her too. Even though she was like 35 years older than me, Jan had a boyish charm about her and she was able to make me laugh a lot. She had a devilish look in her eyes and cute dimples whenever she smiled.

I wasn't gay, I liked boys my own age not women who were older than my dad. I didn't want to have sex with her, but I think I had developed a bit of a crush on my boss. I found myself becoming flirtatious with her. It was hard to explain. It was exhilarating being around her. I didn't know if it was because I just got to know her better or if it was because because it was something else. Maybe part of it was the thrill of knowing that I could be the object of lust and affection to both sexes. Feeling the rush of something that was taboo and knowing that this was something that society and my parents in particular would disapprove of. Whatever it was, it made me feel sexy and dirty at the same time and I loved the feeling.

I had begun to wear tighter, more revealing clothes at work in an effort to really get Jan's attention. Whenever I walked past her, I would sway my hips a little more. It seemed to work too. I would catch Jan staring at me more often than before. She would give me all sorts of projects that required me to be in her office.

Then it happened. On one particular Friday I was feeling really playful. I put on my skimpiest black thong panties and a matching black bra. I then slipped into a black mini skirt that had a slit running part way up my left leg. I also put on a skin tight white button up blouse, leaving a few buttons undone to accentuate my full breasts. Then I put on a pair of open toed stilettos. I even put on an ankle bracelet and my favorite toe ring.

I knew that I would get Jan's attention when I saw every guy in the building checking me out as I walked into work. I felt sexy and naughty all at the same time. I couldn't believe that I was doing this just to gain the attention of my boss, a woman, an older woman! It was crazy, but it was also arousing to me too!

I walked into Jan's office and knew right away that she approved of my choice of wardrobe. Her eyes were fixed on my tight little figure and her mouth was agape. The first words out of her mouth were, "that's a lovely outfit you're wearing today Carli. I'm surprised your parents let you out of the house wearing that."

I giggled and said, "well they're out of town right now. Besides I'm a big girl."

The entire morning I was working in Jan's office I caught her eyes checking me out. It was such a thrill to see her lusting after me as she was. I noticed when Jan came back from lunch that there was something different. But I couldn't tell what it was. I thought I saw a bulge in her crotch, but wasn't sure. I had just assumed that the fabric was just bunching up there.

At around 4:00 in the afternoon, Jan came up to me and said, "Hey Carli, we've got this emergency project that I've got to work on. I need you to stay and help me work on it. You'll get double time in a half."

Part of me was excited at the prospect of hanging out with Jan after hours, but another part of me was tired and just wanted to go home and start enjoying the weekend. In the end, I couldn't pass up the money, so I said, "sure, that would be great!"

At 5:00, everyone started to clear out of the building. By 5:30, no one was left at work other than me and Jan. The cleaning crew wouldn't be in until Saturday afternoon. We had the building completely to ourselves. I was in the copy room making some copies of documents when my boss came in, standing behind me. She said to me, "you are one beautiful girl. You know that Carli?"

I just smiled and said, "thank you."

Jan stood into me, I could feel her hefty body pressing into me. She leaned her head over to my ear and said, "no baby, I mean it! You are fucking gorgeous! I fantasize about you all the time. I fucking want you so badly it hurts!"

For a moment, my body tingled with excitement when she said that. Then fear took over. I wanted Jan to want me. I wanted to tease her and have her chase after me, but I didn't want to be with some 55 year old butch lesbian. I realized that I put myself in a bad position. I turned around, facing her. Just as I was about to get away from her, Jan leaned in close. She wrapped her strong right arm around my tiny waist and pulled me into her stout body and put her left hand on my neck. She closed her eyes and moved her head in to give me a kiss.

I was so shocked. I didn't know what to do. I could feel Jan's soft, moist lips against my own. Jan's tongue probed my lips, trying to part them. But I wouldn't let her tongue in my mouth. Jan stopped kissing me for a moment and said, "don't worry baby. I'm not going to hurt you. I know you've been flirting with me lately. I'll treat you better than any man could. And I'll make love to you better than any man can."

With that, Jan started to kiss my neck, working her way up to my ear, nibbling on it. She also ran her hands up and down my body. The only response I was able to let out was "oh my god!"

Jan ran her hands down my back and cupped my ass, grasping my buttocks firmly and pulling my body into her masculine figure. I could feel something hard coming from her crotch that was rubbing up against me. I wasn't sure what sure what it was exactly.

My boss turned me around and pushed me against the copy machine, pinning me to it. I put my hands to either side of the copier just to keep myself propped up as Jan pushed her body harder against mine. She pulled my hair to one side and started to kiss the nape of my neck. At the same time, she began to grind her crotch against my round ass. I could feel her hardness grinding against me. I still wasn't entirely sure what it was, but I had a good idea. Then I felt Jan's strong hands unbuttoning my blouse.

Once Jan had pulled my blouse off, breathing heavily I was able to let out, "Jan please stop. I'm not that kind of girl. I don't want this. Please!"

My boss wrapped her arms around me as she continued to grind her crotch into my ass. She nibbled on my ear lobe and breathed into my ear, "Don't worry baby. I'm not going to hurt you. I know you've been flirting with me. This is something I think we both need. I want to make love to you, I want to take care of you baby. I'm gonna make you mine."

I was nervous, scared and somewhat excited. She was making me feel sexy, dangerous and yet at the same time, safe. And as Jan unhooked my bra, my body started to tingle with a bit of sexual arousal. I never expected that some butch 55 year old woman could have that kind of effect me.

As my bra fluttered to the ground, I could feel Jan's strong hands cupping my breasts. She gently squeezed them, rubbing them in a circular motion. I felt Jan's thick fingers sliding between my nipples. My body was starting to betray me. Feeling her body pressing up against mine, having her crotch grinding into my butt, her warm mouth nibbling on my ear lobe, and strong hands caressing my breasts was becoming too much. My body was giving into the sensations. And my mind was giving into the thrill of doing something so taboo. My nipples were becoming erect under Jan's expert touch. And I slowly started to grind my butt against Jan's crotch, matching her gyrations.

Jan kissed my neck and whispered in my ear, "That's it baby. Enjoy it! I'm gonna make love to you. I'm gonna fuck you and make you all mine."

I couldn't believe it, but I was starting to give myself to this 55 year old woman. There is something so sexy about a person who knows what they want and takes it. That kind of self confidence, the kind that only comes with age and experience was a major turn on for me.

In an instant, Jan turned me around. Now face to face. She pulled in and kissed me on the lips. Her hands were running up and down my body again. This time, when Jan's kissed me, I willingly let her tongue enter my mouth. Her skilled tongue caressed mine. My white haired lover was such an amazing kisser. We kissed and kissed and kissed. My mouth craved her kisses. I loved feeling her tongue inside my mouth while her strong hands ran over my body, caressing my breasts.

Jan was making me feel wanted in a way few men ever have. It was so crazy. I was so aroused and so confused all at the same time. I thought I was straight, but this woman was making me question my own sexuality. The scary thing was, I knew it was wrong but I didn't want her to stop!!!

I put my arms over Jan's strong, broad shoulders and wrapped them around her neck. As we continued to kiss, I could feel my lover's hands move down my body. They traced the outline of my body, moving down to my waist, then back to my butt. Her big strong hands grabbed hold of my ass, squeezing my butt tightly and pulling my crotch into hers. Again I could feel something hard as our bodies came together.

Before I could think too much about that, Jan's hands moved again. They were up to the waist of my skirt, and fumbled for the zipper in the back. It didn't take her long to find it. Before I knew it, my skirt had fallen to my ankles. I stepped out of them. All that I had on were my open toed black stiletto shoes an ankle bracelet and a really tiny pair of thong panties.

My boss lifted me up in her strong arms as we continued to kiss. I wrapped my legs around her hips as she carried me over to the counter. Jan took one of her arms and flung all junk on the counter to the floor. Then Jan sat me on the counter. She smiled at me devilishly and then she kissed me on the lips one more time. Then she took my right foot, lifting it up and removing my shoe. It fell the the floor. Jan kissed each of my toes, sucking on my big toe before taking off my other shoe.

Jan came up again, kissing me on the lips, sliding her tongue into my mouth. She ran her hands up my legs and hooked her fingers around the straps of my thong panties, slowly tugging them down. I still couldn't believe that I was letting my boss do this to me. She pulled my panties down, exposing my freshly waxed pussy to her for the first time.

My boss looked up at me and smiled, telling me. "You are so fucking hot baby. I wanna taste your pussy so bad!

With that, Jan kissed me deeply again, letting our tongues linger for a moment. Then she kissed her way down. Kissing my neck, then my collar bone. Moving down further, she kissed my left breast and fondled my right breast with her masculine hands. Jan circled my nipple with her tongue before she took it in her mouth. I couldn't believe that I was letting her suckle from my breast. She was so good at it! Her tongue flicked at my erect nipple as she sucked on it. I caressed Jan's face and combed my fingers through her short white hair as she suckled my breast. My pussy was starting to get wet and throb in anticipation of my older lover. I wanted her to take me.

Jan seemed to sense that my body was craving her. She kissed her way down, kissing my stomach. Her tongue circled my belly button, then she kissed my belly button ring. From there she gave me butterfly kisses down even further. I could feel her warm breath on my bare pussy. I waited for her to kiss my pussy lips but instead she began to kiss my inner thighs. She was driving me mad. I looked down at Jan as she looked up at me. Our eyes locked on each other. My boss gave me a devilish grin as she pulled my butt to the edge of the counter.

Our eyes were still locked on each other as my boss lowered her head. I spread my legs wide open in anticipation of her. I could feel Jan's hot breath on my pussy. My body was on fire, I was tingling with curiosity and sexual desire from head to toe. Then I felt Jan's warm moist lips kiss my pussy. She kissed my sex as if she were kissing my lips. She started off so softly, so tenderly kissing my pussy. At first they were butterfly kisses. Then Jan flicked her tongue at my clit. It was driving me wild, my juices were started to flow for her.

I still couldn't believe what I was letting my boss do to me. Here was this white haired woman who was making out with my pussy and I was enjoying every minute of it. Maybe I wasn't as straight as I thought. Then I felt Jan's mouth envelope my pussy. My body tightened for a moment feeling this new sensation. She started to suck on my pussy and slip her tongue inside my body. She was making me so hot! I felt like such a dirty girl.

I stared deeply into Jan's eyes as she went down on me. One hand caressed her cheek as the other combed through her short white hair as my boss used her mouth to make love to me. As her adept tongue penetrated and pleasured me I felt an intimacy and a connectedness with her that I hadn't felt with anyone before. She was becoming one with me. With Jan's hands caressing my breasts and her mouth suckling my pussy I could feel myself getting ready to cum. My hips ground into Jan's mouth in a steady rhythm, attempting to get my lover's tongue as deep inside me as I could. My body soon began to spasm, cumming for my older lover as she lapped up every little bit of my juices. Jan continued to lick my pussy for several more minutes until I had finished cumming.

When my body slowly stopped spasming, Jan started to kiss her way up. She kissed my flat stomach, my nipples and neck. Then we embraced, wrapping our arms around each other as we kissed passionately. My older lover had taken me to another world. I kissed her with wild abandon, tasting myself on her lips.

Then Jan took me in her arms and carried me over to an office with a leather couch. She sat me on the couch. Then, standing above me, she took off her shirt, leaving her tank top under shirt on, covering her broad chest. Next Jan unbuckled her belt, took off her shoes and socks and pulled off her slacks. Then my boss pulled off her boxers. My eyes widened as I saw for the first time what Jan was grinding against me with. She was wearing a strapon! Her cock was 7 or 8 inches long.

There she was, standing above me, wearing only an undershirt, a strapon and a devilish grin. Standing directly in front of me, with her strapon inches from my face, Jan caressed my cheek with her right hand and said, "I want you to suck it baby."

"What?" I said.

Jan replied, "I want you to suck my cock. C'mon baby, suck it for me."

I was a little apprehensive about sucking on Jan's strapon, but before I could say another word, she had pulled my face closer to the head of her surrogate cock. I complied, opening my mouth and taking Jan's cock in my mouth. At first, I only sucked on the tip of her strapon. Then Jan took my blond hair in both her hands pulling my head down on her cock and started to gently thrust her hips at the same time. I couldn't help but deep throat her stiff phallus. I nearly gagged on it, but somehow I was able to take it all in, going to the very base of her shaft. I couldn't believe I could do it! But for Jan I was able to. My head bobbed back and forth on my boss' long hard cock for several more minutes.