Legal Assistant

Mrs. Swanson was a very successful attorney who specialized in the defense of women who were sexually harassed in the workplace and women who were abused by their male boyfriend or husband. I was her very first male employee. It was her plan to hire a male assistant, knowing the older woman who had long worked for her would someday retire.

She had interviewed dozens upon dozens of young men. After hiring me, she shared the reason why I'd been chosen. She explained that many of her clients were afraid of men due to what they'd been put through. She wanted her clients to be in the presence of a 'man' that wasn't intimidating, overly masculine or a threat to them whatsoever. But she felt strongly that the harassed and abused women needed to be exposed to a man, a kind, gentle, young man. She had hired me because I was short, skinny, polite, dressed nicely and treated women with respect.

Mrs. Swanson was a tall woman, made even taller by the block heels she wore each day to the office. She was mature, easily old enough to by my mother. She had an exaggerated hourglass figure with wide hips, thick thighs, and enormous breasts. Her hair was gracefully greying and her face exuded the supreme confidence which was the first thing I noticed about her. She was the type of woman who always got what she wanted. I had no doubt about that.

Every day at work, she wore tasteful slacks, matching jacket with a silk blouse beneath. She was always very careful never to expose the slightest bit of her cleavage. I always tried to look her in the eye like my mother had taught me too. But I was barely in my twenties and she was so pretty. I often struggled not to take quick peeks at the impression her enormous breasts made beneath the blouses he wore. During my first day in her employ, she caught my eyes dropped to her chest.

Mrs. Swanson called me by name and asked, "Chris, what were you just looking at?"

Biting my lip and lowering my chin, I replied, "I'm sorry Mrs. Swanson."

Even while looking at my shoes, I could tell she crossed her arms under her chest. "Young man, you didn't answer my question."

I squirmed where I stood. I moved my hands behind my back which was a nervous habit I had. I suppose it was due to the many spanking I'd received from my mother. Tears welled up in my eyes as I whimpered, "I-I-I was looking at your blouse."

Her voice was firm when she asked, "Is my blouse stained? Or was it something else about my blouse that attracted your attention?"

The tears that had formed in my eyes were now rolling down my cheeks. "I'm so sorry, Mrs. Swanson. I-I-I was looking at her breasts. Please don't fire me! I promise it'll never happen again!!"

She rose up from the chair she'd been sitting in. She stepped right in front of where I stood. In a soft but firm tone, she said, "Chris, the women I defend have been treated like objects by men."

I whimpered, "I know and I feel terrible for them."

She laid her hand on my shoulder while I continued to look at my feet. "The way you just looked at my chest..."

I interrupted her and looked up into her eyes, "I know! I'm so sorry!" Tears were rolling down my cheeks. I was a blubbering mess.

Mrs. Swanson took hold of my hand and lead me to a couch that sat along one wall of her office. She put her arm around my shoulder to console me. My emotions often got away from me and while I sobbed, I began to babble, "My mom would be so disappointed! She never allowed me to do things like I just did! If she found out about this, I wouldn't be able to sit down for a week!"

She rubbed my shoulders while asking, "Your mother used to spank you for looking at girls inappropriately?"

I looked at her through tear-filled eyes, "She-She-She still does!"

She didn't sound surprised at all. She honestly sounded very pleased, "Chris, do you still live at home with your mother?"

I nodded my head while I began sobbing anew.

She went on to ask, "Just the two of you?"

I bit my lip and explained, "Yes, it's always been just the two of us. My dad left before I was born."

She removed her arms from my shoulder and scooted back a little so she could turn to face me. "Chris, I forgive you for staring at my chest. But I don't want it to happen again." She paused to see the relief begin to appear on my face. "I know you're a young man. But the only chest you should be looking at is the chest of your girlfriend."

Nibbling on my lip, but forcing myself to look into her eyes, "I don't have a girlfriend."

She looked a little sad when she asked, "Have you ever had a girlfriend?"

It took all the strength I had to keep looking into her big brown eyes, "No, not ever. My mother won't allow it."

She smiled and said, "If every mother raised their sons in the same way you're being raised, there would be no harassment in the workplace or spousal abuse. Men would be treating women with the respect they deserve." She hesitated for a moment before asking, "You didn't drive yourself to work this morning, did you?"

Nibbling on my lip, I answered in a soft voice, "No, my mother brought me. I don't have a license." I sobbed softly for a few moments before offering, "She even waited in the car during my interview."

She smiled warmly and said, "I know you'll never be late!" I smiled then and felt my emotions calm down. She went on to say, "When your mother comes to pick you up today, I'd very much like to meet her. Considering that you'll be spending a good bit of your time in this office, I think it would be best if she and I got to know each other."

My lips began to quiver when I asked, "Are you going to tell her what I did?"

She then did something I never expected her to do, she pulled me into her arms and gave me a hug! While holding me in her arms, she said, "No, I will not tell her that you were staring at my breasts today. I forgave you for that. I promise I won't mention it to her." She squeezed me against her soft body and if I had turned to face her, my chin would have disappeared in her cleavage! But I didn't. I kept my head turned to the side and tried not to think about her breasts.

She spoke in a soft voice when she said, "I want to talk to your mother and learn what I can do to help."

I whimpered softly, "Help, what?"

Laying a hand behind my head, she pulled me more firmly against her breast, "Why, help raise you to remain such a good boy." She ruffled my hair with her hand and went on to say, "And I would like to get her opinion on the dress code I've been thinking about implementing for you."

Pulling away from her, I looked up into her eyes and asked, "My mother decides the clothes I wear. She is going to get upset if you question her."

She smiled and pulled me back into a warm embrace. "I'm sure she'll understand. These silly dress pants and sports coats aren't the image I'd like you to project to our clients."

She held me in her arms for a good long time. When she released me, my penis was very stiff in my underpants. I needed to get away and calm myself down. Looking up into her eyes, I timidly asked, "Mrs. Swanson, may I please use the restroom?"

She grinned at me before saying, "Yes you may."

When I turned to walk away, she patted my butt with her open palm! I glanced back at her and know I was blushing. Before I took my next step, she patted my butt again! I jumped that time and giggled as I made my way to the restroom.

The rest of the day went by quickly and before I knew it, the day had come to an end. I was sitting at my desk while my mother and Mrs. Swanson got to know each other behind a closed door. When they finally came out of Mrs. Swanson's office, they were talking to each other like they were old friends. And I was very worried about the topics they may have been discussing.

Both women stood side-by-side and smiled down at me while I sat, perched on the edge of my chair. When my mother offered her hand, I reached up, took it and rose to my feet. When she spoke, she didn't sound upset at all. I silently prayed that Mrs. Swanson had kept her promise and not told my mother about how she caught me staring at her chest. "Come along, Chris. You and I need to go shopping for your new work clothes."

That evening, my mother took me to several different stores in three different shopping malls. Mother picked out an entire new wardrobe of work clothes for me. She would pull articles of clothing from the rack and after gathering an armload, she sent me in to try on each piece. Thankfully, she didn't join me in the dressing room like she had so many times before. But she did insist I step out of the dressing room and into the store so she could approve the fit of each item.

I would never think to question her choices or decisions. But the clothing she pulled from the racks weren't at all what I would have thought was appropriate for a lawyer's office. Even on the television shows I'd watched, the men all wore dark suits with ties. The outfits my mother chose were in pastel colors or bright whites. There were no sport coats or ties at all. The shirts had short sleeves and the pants weren't pants at all, they were shorts! When we got home that evening, she and I unloaded all of the packages and moved my new work clothes into my dresser and closet.

The next morning, I stepped into Mrs. Swanson's office wearing bright white tennis shoes, a matching white, short-sleeved shirt, and shorts in a pastel yellow color. The shirt was just long enough to meet the hem of my shorts. The shorts rode very low on my hips and were cut shorter than any other shorts I'd ever worn. They closed with a button and the zipper was no more than an inch long. The shorts hugged my body and my mother decided I would go without underpants to avoid lines showing.

Mother had told me to show Mrs. Swanson my new look the moment I arrived. So, I crossed the office and timidly tapped on her already opened door. Mrs. Swanson looked up from her work and a wide grin spread across her face. She slowly rose up from her chair and approached me. She had dressed differently that day, she was wearing a stylish blue dress with white trim. The neck of the dress was cut slightly deeper than the blouses I'd seen her in before. And that slight plunge in her neckline drew my eyes to her enormous chest. When she stood just a few feet away from me, she lifted one hand and made a stirring gesture, "Turn around for me."

Biting my lip and raising my arms up out of the way, which caused my shirt to rise up, exposing a ring of the pale flesh of my stomach and back. When I'd turned all the way around, Mrs. Swanson stepped closer and embraced me once again. While pressing my head into the depth of her cleavage, she said, "Oh Chris, your mother has outdone herself. You look exactly how I wanted you to look."

The musky perfume she wore along with the warmth of her chest, made me dizzy with desire. One of her hands held my head firmly against her chest while the other caressed my back. She whispered, "There isn't a woman alive who could ever be intimidated by you. You're just too cute!"

Taking my hand in hers, she led me to her desk. After she'd sat back down, she rested her hands on my hips and turned me to face away from her. She sounded very happy when she observed, "Your butt cheeks are peeking out of the bottom of your shorts. Running her open palms over my cheeks, she asked, "You're not wearing anything underneath these shorts, are you, Sweetheart?"

I whimpered softly while moving both hands to cover my fully-erect, penis. "No, ma'am. Mother didn't want me to have lines."

She replied, "And I think that was a wonderful decision. It would be a crime for panty-lines to distract from your cute little butt." She squeezed my cheeks and said, "I trust none of your shorts are longer than these."

My hips were squirming from side to side while Mrs. Swanson, my busty, full-figured boss groped my behind. I whimpered, "Yes, ma'am. All of my shorts are this short. Mother had to take me to the junior's sections to find them in my size."

Her big, soft, warm hands slid across my cheeks to my hips. She slowly turned me around so I was facing her once again. When I stood in front of her, I struggled to look into her eyes and not down her dress. She smiled while asking, "So Chris, you're wearing girl's shorts? Is this a girl's blouse too?"

Before I could answer, she took a gentle hold of each of my wrists and slowly pulled them away from the petite bulge my erection was making. My voice cracked hard and it was very squeaky, "Yes, ma'am, girl's shorts, top and shoes."

She continued to look up into my eyes, "And I think you look very stylish in girl's clothes." Reaching up, she gently dragged the back of her fingernail along the length of my petite erection. "And I think you enjoy wearing them too."

Biting my lip, I squeaked, "May I be excused? I need to use the restroom?"

Dragging her fingernail along my overly excited penis once more, she asked, "Chris, what are you going to do in the restroom?" A shiver shot through my body and before I could respond, she said, "And Chris, be honest with me. I'd hate to have to tell your mother that you've been lying."

Biting my lip, I was afraid and ashamed to admit was I intended to do. While the battle raged on inside of me, Mrs. Swanson looped one of her arms behind my leg so she could hold that butt cheek in her hand. She continued to drag her fingernail along the length of my desperate erection.

Looking into my eyes, she prompted me, "Chris, what are you going to do in the restroom? Are you going in there to masturbate?"

I know I was blushing from head to toe. My hips were squirming around in circles and my voice was squeakier than ever before, "Yes, ma'am."

She continued to grope my butt cheek and tease my petite erection with her fingernail. After raising an eyebrow, she asked, "Yes, what?"

I moaned, "Yes, I'm going to the restroom to masturbate."

She smiled and never stopped touching my inexperienced body. "That wasn't so hard, now was it." She sighed while her fingernail left my erection and slid down my nearly hairless leg. "Even with your strict upbringing and as delightfully timid as you are, I understand you still have urges. So, Chris, whenever you feel the need to play with yourself, simply come into my office and ask for my permission."

My voice cracked when I asked, "Mrs. Swanson, may I please go to the restroom so I can masturbate?"

Reaching around my body with both arms, she kneaded my cheeks as if they were bread dough. "Yes, you may." As I moved to step away, she pulled me back. "But before you go, I need to explain something to you." She glanced down at the moist spot that had formed on my shorts near the squishy head of my penis. "You are a young man with needs. You're in your sexual prime. And I know your mother has denied you any contact with a girl." Her hands slid to my hips and while spreading her knees apart, she pulled me closer to her. Her voice was soft and raspy sounding, "But I'm no girl. I'm a woman. And I have needs that are just as strong as yours."

She leaned forward so her face was dangerously close to my throbbing erection. "Sweetheart, as my assistant, one of your new duties will be to take care of my needs."

I shivered and mumbled, "H-H-How?"

She grinned up at me, "You will be spending part of each workday under my desk. Sweetheart, you're going to learn to pleasure me with that sweet little mouth of yours."

I began to panic, "B-B-But mother! What will she..."

Mrs. Swanson cut me off, "Sweetheart, your mother is aware of the additional duties I've assigned to you. She agrees it is time for you to learn how to properly please a woman. And lucky for me, she believes I'll be the perfect teacher for you."

Her hands slid slowly around to the front of my body. While staring up into my eyes, she popped the button open on my shorts. "Sweetheart, when I give you permission to masturbate, I want you to use the restroom here in my office."

I gasped and another shiver shot up my spine when she lowered the tiny zipper on my shorts. She hooked her thumbs under the waist of my shorts and began to wiggle them downward. "And Sweetheart, when I give you permission, I'm going to undress you first. I would hate to have you squirt onto your clothes by accident. What would your mother think?"

A high-pitched squeal left my lips when my skinny, little, pink penis popped out in front of Mrs. Swanson's face. I felt her warm breath on my naked erection and it throbbed before her eyes. She had that raspy sound to her voice again, "Oh my, you are simply adorable." After staring at my throbbing prong of a penis for several moments, she went back to work and lowered my shorts to my ankles. I moved to cover myself with my hands at one point. Mrs. Swanson looked up at me and shook her head from side to side. I moved my hands back to my sides and tried to deal with my humiliation.

Looking up into my eyes while holding one of my hands, she said, "Step out of your shoes and shorts for me, Sweetie."

After I'd done as I'd been told, she bent over and picked everything up. She set my tennis shoes down on her desk. She then folded my shorts neatly and set them beside my shoes. Rising up from her chair, she looked into my eyes while unbuttoning my shirt. I stood there terrified and embarrassed. My boss was undressing me in her office! She was going to send me to the bathroom in her office so I could masturbate! If my mother knew what I was doing, I would surely not be able to sit for a week!

When Mrs. Swanson slid my shirt off my arms, she began to fold it neatly while I stood before her completely naked. When my shirt was set down on top of my shorts, Mrs. Swanson hiked her hands under her dress and wiggled her huge panties down her legs. Sitting back down in her chair, she pointed at her panties on the floor and said, "Be a dear and pick those up for me."

I squatted down and when I touched her panties I felt the warmth of her body and I moaned softly. Standing back up, I folded her panties neatly and set them on top of my clothes. "Sweetheart, seeing you like this has gotten me quite aroused. Before I release you to go masturbate, I'm going to need you to crawl under my desk."

My hips squirmed and my skinny penis throbbed. "But, Mrs. Swanson, I'm naked."

"Chris, you don't need clothes to spend time under my desk. It's not your body I'll be using. I only need your sweet little mouth with your cute little tongue."

I whimpered softly, "I don't know... I mean... I've never..."

She smiled while hiking her dress up, "Don't worry, Sweetheart. I'm going to teach you all you need to know." She then lifted her dress up and I laid my eyes upon a pussy for the very first time. Her bushy dark pubic hair was trimmed into a large triangle. When she scooted her bottom closer to the edge of her chair, I saw the dark pink lips of her pussy were peeled open like a delicate flower.

She didn't need to tell me what to do. I knelt down between her spread thighs. She used her fingers to point out all the important parts of her enormous pussy. While kneeling a little more than a foot away from her, I could smell her arousal and see the moisture on her lips. When she introduced me to the opening into her vagina, she held my hand and guided my finger inside of her. It was so warm and wet and slippery. I squirmed while I knelt before her.

After fingering her for a short time, she had me remove my finger and lick it clean. She watched me closely while I cleaned her juices from my very lucky finger. After I finished that task, she used her fingers to spread her lips wide apart and introduced me to her clit. She told me that is where my lips and tongue would spend the majority of their time.

She smiled while drawing lazy circles around her clit with her fingertip. "Chris, Sweetie, it's time for you to crawl under my desk. I'll tell you what you're doing right and wrong."