Legal Assistant

Moaning softly, I slowly crawled under her desk. When I had sat on my heels and turned to face her, I watched as she rolled her chair close to me. I really had nowhere to go, all I could do was lean in and kiss her pussy as I'd been taught. I looped my arms around her immense thighs and went to work. I licked and sucked and even nibbled on her intimate parts. Over the next 25 minutes, she coached me with what to do and what not to do. After she'd nearly crushed my head between her thighs during her orgasm, she rolled back and wagged her finger at me.

"Sweetheart, if you keep this up, I know a young man who may get a nice raise during his 30-day evaluation!"

Crawling out from under her desk, my face was drenched with her love. Her taste was on my tongue. Her scent filled my nose. And the sight of her bushy, meaty pussy will forever remain in my mind. As I rose to my feet, she playfully smacked my bare bottom and said, "You've earned it, Sweetheart. Go play with yourself in my bathroom. But don't lock the door. As a matter-of-fact, why don't you leave the door wide open."

As I scurried toward the bathroom, I looked back over my shoulder I saw her dropping my clothes and shoes into her bottom desk drawer. While she began putting her panties back on, I asked, "Mrs. Swanson, are you going to peek at me while I'm in here?"

She looked up at me, "No, I am not going to peek. Peeking is sneaky, and I'm not a sneaky person. As soon as I get these panties on, I'm going to walk into that room and watch you play with yourself."

The idea of her watching me touch myself sent a naughty shiver up my spine. While still standing just outside of her restroom, my finger and thumb looped around my rigid penis and began masturbating myself in her office. It was a completely shameless act. But I couldn't stop myself. She wanted to watch me. She was going to watch me. It seemed silly to do it in the bathroom.

Once she was fully dressed again, Mrs. Swanson leaned back in her chair and observed me embarrassing myself. After watching me play with myself for a short time, she rolled back away from her desk, wagged her finger at me and then patted the top of her desk.

Nibbling on my lower lip, I began taking small steps toward her while still playing with my petite erection. When I stood between her and her desk, I turned to faced her and used my hands to scoot up on her desk. As soon as I was in place, Mrs. Swanson rolled in close enough that I had to spread my legs across the arms of her desk chair. Leaning back on one hand, I used my other hand to gently stroke my innocent penis.

At one point, Mrs. Swanson looked away from my penis to my eyes. She grinned and said, "Chris, you're a very good boy. You've done everything I've told you to do all morning. Your mother would be very proud."

A shiver shot through my body at the mention of my mother. My voice cracked when I asked, "Do you really think so, Mrs. Swanson?"

Her hands touched my bare knees and slowly slid up my thighs while still staring into my eyes, "Oh yes, without a doubt. Sweetheart, the way you stood there and let me undress you. The way you crawled under my desk and ate me to a shuddering orgasm. And how you're perched on my desk now, playing with yourself while I watch. Chris, your mother raised you to be a docile, obedient young man. And if she could see you now, she would be thrilled at how well you've behaved yourself."

My head rolled back and my penis began to throb wildly. Pulling my bare feet up onto her desk, I kept my legs spread wide apart so she would see all of me. Leaning back on my elbow, I felt my orgasm building quickly inside of me.

In a higher than normal pitch, I squeaked, "Mrs. Swanson! Mrs. Swanson!!"

Her warm hands had come to rest in the crease where my legs met my hips. Her thumbs hung down between my legs and were massaging the tender flesh. In a surprisingly calm tone, she asked, "Yes, Chris? Is something the matter?"

My back arched deeply and my little balls popped inside of my body. Goosebumps rose up all over my body in a wave. I squeaked, "I'm going to..." The muscles in my abdomen went taut and kept me from saying anything more. My toes curled into knots and my nipples stiffened. Muscles throughout my body began to spasm as the most powerful and intense orgasm of my life washed over me.

Mrs. Swanson's thumbs slid down lower until they rested on either side of my buns, immediately beside my wrinkled hole! She moaned softly, "That's my good boy. Yes, your mother would be very proud of you if she were here right now."

My skinny little penis squirted out a long line of my love, starting at my collar bone and ending below my belly button. The next few squirts painted my stomach in my creamy love and the last few dribbled out and fell from the squishy pink head of my penis. When my orgasm came to an end, I was completely exhausted and fell back onto her desk. My heels were still on the edge of her desk leaving me spread wide before her. Mrs. Swanson opened a drawer of her desk and pulled out several tissues from a box. Very gently, she began to mop up the creamy mess on my body. She started near my neck and worked her way down toward my softening penis. When the tissues became saturated, she dropped them in her trashcan and got several fresh tissues to finish the job. When she gently wiped my penis with the tissues, I felt myself trying to get stiff once again. But it was too soon.

After dropping the tissues in the trashcan, she rolled in close between my spread legs. I felt her warm breath on my bare skin when she spoke. "Chris, Sweetheart, we need to get some work done today. I don't have any appointments scheduled. So we shouldn't have any visitors. Honey, I'd like you to work at your desk naked today."

I quickly sat up on her desk and looked into her eyes, "But, Mrs. Swanson, what if..."

She got a stern look on her face when she said, "What if, what? Chris, I said I wanted you to work naked today. Now, do I need to call your mother and let her know you're being disobedient?"

Lowering my eyes to my wilted penis, I whimpered softly, "No, ma'am. You don't need to call my mother."

She placed her finger under my chin and lifted until our eyes met. She had a smile on her face when she said, "Good. Now run out to your desk and get to work. I'll give you your clothes back when your mother comes to pick you up later this afternoon."

Nibbling on my lip, I timidly asked, "Before she comes to pick me up?"

Her smile widened, "We'll see, Sweetheart. Now run out to your desk and get to work."

After Mrs. Swanson had scooted her chair back away from her desk, I slid off to stand on my bare feet. I paused to glance at the drawer that contained all of my clothes. When I looked back at her, she smiled and pointed toward her office door. When I turned to begin making my way toward my own desk, she slapped my bare butt hard enough that the sound echoed around her office. I jumped more from surprise than pain. It actually felt quite nice. After glancing back at her, I tiptoed out of her office.

As I passed into the reception area where my desk was located, Mrs. Swanson called out to me, "Chris, come back in here for a second."

Hoping she'd changed her mind about my nudity, I spun around quickly and dashed back into her office. When I stood on the opposite side of her desk, I timidly asked, "Yes, ma'am?"

Her eyes wandered over my body while saying, "Be a dear and get me a cup of coffee. And when you're through with that, I need ten copies of each of these." She then pushed a substantial stack of documents toward where I stood.

Picking up her coffee cup, I turned and walked back out toward my desk. I quickly emptied the pot from the day before and began to brew a new pot for her. While that was underway, I tiptoed back toward her office and tapped on it softly. When she acknowledged my presence, I pointed at the paperwork and said, "May I get those papers so I can start copying them?"

She grinned and replied, "Of course, Sweetheart." She watched me cross the room and when I'd reached out to pick up the stack of papers, she dropped her line of sight to my penis before looking back into my eyes. "Chris, Honey, your little penis is already stiff again."

Biting my lip while my hips squirmed from side-to-side. "I'm sorry, Mrs. Swanson. It did it all on its own."

She leaning back in her chair and I watched as her eyes drifted over my bare body. "There is no need to apologize. As a matter-of-fact, I hope your little penis stays stiff all day long. Even when your mother arrives to pick you up. Won't she be surprised to see you sitting out there naked with a cute little hard-on."

Biting my lip hard, I shivered with fear, "Please no! Mrs. Swanson, my mother can't see me like this!"

She was amused by my panic and grinned while asking, "Why not, Sweetie? I'm sure your mother would be very proud that you've been following my orders all day."

I whined, "But I'm naked!"

She grinned even wider, "Baby, be honest with me. Would this be the first time your mother will see you naked?"

Lowering my chin, while still holding the stack of documents against my naked chest, I answered in a soft voice, "No, ma'am, it won't be the first time."

She went on to ask, "Would it be the first time your mother will see you with a little hard-on?"

My penis throbbed uncontrollably and a drip of my excitement began its slow descent down my skinny shaft. Blushing from head to toe, I confessed, "No ma'am, it won't be the first time she's seen my penis when it's hard."

Mrs. Swanson was intrigued by my answers and asked, "Sweetheart when was the last time your mother saw you naked with an erection?"

I bit my lip and my entire body flushed with embarrassment, "Last night."

Her eyes wandered over my body while she asked, "What were the circumstances?"

I sounded whiney when I answered, "I was going to bed, but I needed to ask her permission to play with myself. I had to walk out to the living room naked and ask."

Her grin widened further, "You need your mother's permission to masturbate? But Sweetheart, you played with yourself on my desk just a few minutes ago. And I know you didn't get your mother's permission for that."

I dumped the papers on her desk and scrambled around to kneel beside her chair. I begged, "Please don't tell her! She would be so mad! I wouldn't get permission to do it again for weeks!"

She turned her chair to face me and spread her knees apart so I could scoot in close and lean in and embrace her around her stomach. She gently stroked my hair and asked in a gentle voice, "Sweetheart, if you don't get permission to play with yourself, what do you do?"

Tears had formed in my eyes and I sobbed my answer, "I just go to bed. I have to wait until it goes away and I fall asleep."

She continued to run her fingers through my hair, "Have you ever disobeyed her and played with yourself without permission?"

My sobbing became bawling and she waited patiently for me to calm down. When I'd somewhat recovered, "She used her belt. And... and... and the next three times she gave me permission..." I lost control of my emotions again and started bawling. It took me much longer to regain control that time. But I was eventually able to finish what I needed to say, "The next three times she gave me permission, I had to do it in front of her."

She whispered, "You poor boy. I promise today's events will be our secret. I won't tell your mother that you've masturbated without her permission. But from now on, it would be best if we called her beforehand to get her blessing."

With tears still in my eyes, I looked up at her and whimpered, "Really? You won't tell her? Thank you!! Thank you so much!!"

Mrs. Swanson reached down and slowly slid her dress up her thighs. In a raspy voice, she said, "Why don't you thank me properly by crawling back under my desk."

I didn't hesitate at all. On the one hand, I was thrilled my mother wasn't going to find out about my unauthorized masturbation. And on the other hand, I was thrilled to get more practice kissing Mrs. Swanson's pussy. After I'd disappeared under her desk, Mrs. Swanson stood up and removed her panties for the second time that morning. After sitting back down and rolling toward me, trapping me between her thick thighs with her damp pussy right in front of my face, I leaned forward and placed my mouth against her sex. I kissed her gently and licked in all her favorite places.

While I worked on her pussy under her desk, Mrs. Swanson picked up her phone and made a call to a client. They spoke about the client's case and how they were going to proceed after hearing back from the attorney of the man who had harassed her. I'm positive the client would never have guessed that I was making love to Mrs. Swanson's pussy with my mouth at the same time they spoke on the phone.

From time-to-time during that call, Mrs. Swanson reached under the desk to run her fingers through my hair. On one occasion, she pressed on my forehead to move me away from her pussy. It gave me a few minutes to rest my jaw and catch my breath while she calmed down. After a short time, I leaned back in and continued to eat her pussy. When she reached under her desk and knotted her fingers in my hair and pulled me tight against her meaty pussy, I knew she was getting close.

My hearing was muffled by her thick thighs clamped against my head, but I did hear her end the call and slam the phone onto her desk. Her pussy began to vibrate and quiver against my lips and tongue. She pulled me by my hair even tighter against her. And after bucking her hips against my face, I knocked my head against the desk above me. She held me in place with my mouth against her sex for several more seconds before pushing her chair away from me.

I was left crouching under her desk. My face was glazed with her juices and my skinny, little penis was throbbing wildly. I remained under her desk for a few seconds because I had the perfect view between her spread thighs and plump pussy lips which were peeled open like a flower, and the stiff nub of her thimble-sized clit was protruding from her lips. It was a sight I will never forget.

When I did finally crawl out from under her desk, Mrs. Swanson had left to visit the restroom to get cleaned up. I rose to my feet and gathered up the documents she needed to be copied. With her juices still glistening on my face, I tiptoed out of her office and got to work.

I spent the entire workday naked. When our lunch was delivered, Mrs. Swanson allowed me to hide while she signed for it. We ate lunch together at a small, glass-topped conference table on the opposite side of her office from her desk. Throughout the meal, her eyes rarely left my stiff penis plainly visible through the transparent table.

It wasn't until late in the afternoon that I was called into her office and sent back under her desk. With my mother scheduled to arrive in less than an hour, I ate her with a new level of enthusiasm. I needed to make her orgasm quickly or my mother would find me under her desk! Thankfully I was able to bring her to a small orgasm rather quickly.

After crawling out from under her desk, she sent me to the restroom in her office with a firm pat on my bare bottom. I washed my face for the first time since I'd arrived at work. I tidied up my hair and tried to make myself as presentable as possible. As I stepped back out into her office, Mrs. Swanson's eyes met mine. The clothes I'd worn to work that day were stacked neatly on the corner of her desk.

I tiptoed across the room with Mrs. Swanson's eyes following me the entire way. When I stood across her desk from where she sat, I bit my lower lip and timidly asked, "Mrs. Swanson, my mother will be here soon. May I please get dressed?"

She leaned back in her chair and crossed her arms under her enormous chest. With a frightening grin on her face, she answered, "I hate to say it, but yes you may." She watched me closely while I slid my clothes across her desk, closer to where I stood. As I began to get dressed, she went on to say, "I have a scheduled appointment tomorrow at 9:00 am. As soon as that client leaves, you'll find yourself naked and under my desk. Chris, you're going to eat me often enough that you'll be begging to call your mother to get permission to masturbate."

I bit my lower lip and squirmed my hips from side to side while wiggling my shorts into place. My little penis was rigid and I had to be careful with the zipper on my shorts. Mrs. Swanson grinned while watching me roll my hips backward and arch my back deeply as I closed the button on my shorts. Slipping my arms into the sleeves of my shirt, I nibbled on my lower lip while closing all of those buttons. Mrs. Swanson called me around to her side of the desk when I reached for my shoes. She had me sit on the floor near her chair while I got my shoes on.

When I was back on my feet, I stood before her, holding my hands behind my back and my legs crossed at the ankle. In a soft voice, I asked, "Mom won't be here for 20 minutes. What should I do until she arrives?"

Her eyes drifted from my new, white tennis shoes up my bare legs, over the small lump under my yellow shorts, up along my fitted white blouse to my innocent face. In a thoughtful tone, she said, "Why don't you run out to your desk and make some notes on all you've learned today." She paused before stating, "And when your mother arrives, send her in to see me."

Nibbling on my lower lip, I answered, "Yes, ma'am."

Spinning around on my toes, I made my way to my desk. I opened a new document and began typing out notes on my job responsibilities and all I'd learned that day. I was mid-sentence when my mother walked into the office. She set her enormous purse down on my desk and asked, "How was your day, Chris?"

After minimizing the document I'd been working on, I looked up into her eyes and answered in a soft voice, "It has been very... educational."

She grinned down me perched on the edge of my chair, "Of that, I'm sure. I'm going to say hello to Mary." And without another word, she stepped into Mrs. Swanson's office and closed the door behind her.

I couldn't hear what they were talking about. But I did hear them laughing together at times. I tried not to think about what my mother may be learning about the day I'd had. I went back to work on the document I'd started. Mother and Mrs. Swanson met for a very long time. It gave me ample time to thoroughly document everything about my new job.

When the two women did finally come out from behind that door, my penis had wilted and was hardly visible beneath my shorts. They both looked at me and mother spoke to my boss, "You were right, he was made to wear clothes like those."

I giggled and struck a pose, hoping mother was being kind and not cruel. Both women smiled at me before my mother said, "Well, we should be on our way. We have a reservation for dinner in 20 minutes."

Looking at mother, I asked timidly, "Do we have time to run home so I can change?"

She had a sinister grin on her face when she said, "No, we do not. Now carry my purse for me. We need to get going."

Doing as I'd been told, I picked up her huge purse by its strap. Mother often had me carry her purse for her. Often enough that it really didn't bother me too much. Looking up at Mrs. Swanson, I smiled and said, "Goodbye! See you tomorrow!"

She smiled back at me and said, "I can't wait."