~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

This fictional story is the artistic expression of the author who wrote it. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this story, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~

by smallercuck

I think it was her tattoos that started the obsession for me. Of course, they were hidden under her conservative office outfits, for the most part, but those rare glimpses of the ink on her shoulder, her calves and -heaven help me- her cleavage, had a profound effect on me. I spent hours obsessing over the rare glimpses of artwork I’d seen on Samantha’s body.

What kind of woman decorated herself in such a bold way, I wondered? Would such a self-assured woman have time for someone like me? I doubted it. I was plain. Chubby. I lacked sexual confidence. Samantha was alluring. She wasn’t a stereotypical beauty but she had her choice of confident and attractive men. I never saw her at a company function alone. Men clamored to be around her. Samantha didn’t have a model’s build, but fashion models don’t ooze sex appeal, either. Samantha was the hottest woman I knew. Samantha was out of my league, and she dated guys who were richer, more attractive and surely better lovers than I was. I had no chance with Samantha, but the sight of her was a powerful aphrodisiac. The busty brunette was an unreachable ideal and her unattainable status was part of the attraction.

I was transferred to her department out of the blue. Could I really work for a woman who made me shake with excited arousal and whose mere presence precluded my ability to form intelligible sentences? How would I concentrate? Even as my heart raced with the idea of seeing her every day, I worried that the constant stimulation would be too much. I was sure that I wouldn’t be able to do my job.

She caught me staring several times during the first week. I would blush and turn away like a school boy. Samantha’s wide hips and generous ass made me so aroused that I often worried about becoming visibly erect in the office. Her perfume chilled me. I would sneak away to the men’s room to catch my breath and to touch myself. I spotted another tattoo. This one was on the small of her back, just above her panty line. I wondered what it was and I tried to think of some way to get a better look. I considered following her after work on the off-chance that she might leave her apartment in casual attire. I was a wreck.

By the time I had been in Samantha’s department for a month, the existence of my crush was obvious. I had been caught looking at the V in her blouse countless times. I constantly strained to see the sexy curve of her breasts and it was difficult to be subtle. I found excuses to walk by her office and if I heard her heels as she walked down the hall I would rush to my office door to look at her backside. I was tongue-tied around Sam and my work was suffering. When she talked to me I would stare at her lips and would miss what was being said. I began to worry that she would fire me. I wondered what it would feel like to be rejected by her. Could I bear it?

Samantha called me to her office on Friday afternoon just before the office closed. Everyone was filing out and I realized we were alone for the first time. My throat was dry and I found myself shaking nervously. I was certain that I was about to be fired.

She looked at me sternly. “We need to sort this situation out, you and I.”

I tried to play it cool and failed. “What do you mean, Miss Samantha?” My voice croaked like a teenager going through puberty.

She undid the two top buttons on her blouse and tugged the fabric apart. Her deep cleavage was mesmerizing and I could see the top of her breasts all the way down to the black lace brazier. The tattoo was a fiery sun. It was marvelous. “Is this what you want to see? Is this why you are completely useless in this office? Do you think it’s okay to ogle women who want nothing to do with you? Why shouldn’t I fire you, you lecherous piece of shit?”

I tried my best to speak, but I couldn’t. I sat blushing and staring at her chest as Samantha eyed me menacingly. I tongue felt thick and my penis was hard. I comically tried to find the right words -any words to placate her.

Samantha chuckled, “Tomorrow afternoon at four o’clock, I want you at my apartment. Do you know where I live?”

I nodded meekly.

“Somehow, I thought you did. Plan to spend the night, and buy me some wine. Red. Expensive.” She dismissed me with a wave of the hand.

——-

I knocked on her door at three fifty-five. She opened it and my voice caught in my throat. Sam was wearing a white T-shirt, green shorts and flip flops. Her hair was pulled tightly back in a ponytail and she wore no makeup. I was dumbfounded by how attractive she was in her casual attire. The light fabric of the T-shirt meant that I could really see her round curves for the first time. Samantha’s nipples were visible through the shirt and I found myself starting unabashedly at her chest. She took the wine from my hand and examined the bottle. “This will do. Put it in the kitchen, and then run me a bath.” She sat on the couch and picked up the remote control. She crossed her legs and began clicking. The tattoo on her calf was orange and black and I stared for a moment as I tried to commit it to memory.

I found the kitchen and put the wine on the table. Did she ask me to run her a bath? Did I hear that correctly? I started to doubt myself. I couldn’t just go to her bathroom and start the water. Samantha would think I was crazy.

“Um, Miss Samantha. I put the wine…” I was blushing furiously.

“The tub is through my bedroom on the left. There is bath oil in the cabinet. Hurry up; we have a lot to do.”

Her bedroom was a mess. The large queen-sized bed was askew on its frame and the red silk sheets were tangled furiously. The room smelled of Sam’s perfume and my penis immediately stiffened in my slacks. Her clothes were strewn about on the floor. Samantha’s suit from yesterday was piled in the corner and I was immediately drawn to the skimpy black underwear and matching bra lying on the plush carpet nearby. I found myself moving to touch her undergarments before I found the resolve to look away. My heart was pounding as I moved through the bedroom into Samantha’s bathroom.

I turned on the faucet and adjusted the water temperature. I noticed some half-used candles on a shelf near the tub and wondered if I should light them. It seemed that Samantha wanted to take a romantic bath with me. My penis was hard with anticipation.

She had entered the bathroom as quietly as a cat as I sat there daydreaming. I jumped with a start when I saw her and she chuckled at my awkwardness. Samantha lifted her T-shirt over her head and I tried to catch my breath. Her breasts were large and round and I felt myself struggling to breath at the sight of them. The tattoos on her cleavage were mesmerizing and her large areola topped by pencil-eraser nipples made me shiver with arousal. She was perfect.

I stood to caress her before Samantha stopped me with a slap. “What do you think you’re doing? Do you think I invited you here to have sex with me?” She was chuckling now -amused by the idea. “You’re here to get me ready for my date, little man. I wouldn’t be caught dead with you. Understand?” I nodded as I rubbed my stinging cheek. She smiled again to herself.

Samantha shucked her shorts and my eyes feasted on the sight of her pussy. Sam obviously kept her pubic hair trimmed short and I could see the lips of her cunt and the pink folds underneath. I wondered what it would be like to taste her there but I knew better than to move towards her. Samantha’s hips were wide and soft and I found her body irresistible. She was large and womanly and impossibly sexy. I found myself shaking once again as I stared at her body, but Samantha didn’t seem to notice. She kicked her shorts and panties towards me and directed me to dispose of them in the laundry. I nodded eagerly.

After exiting Samantha’s bedroom I stopped for a moment. I looked down at the used underwear in my hands and raised them to my face. I inhaled Samantha’s scent and felt myself shiver with arousal. As I searched for the laundry room, I briefly considered masturbating before returning to Samantha. I was sure I could come quickly enough at this point that she might not notice the delay. I decided against it, out of fear of upsetting her. She might ask me to leave. So, I remained aroused and erect as I disposed of the clothing and headed back to attend to Samantha in the tub.

She had me wash her back. There was a tattoo between her shoulder blades which I had no idea existed. My hands were shaking as I cleaned her. I made a conscious effort to remember as much of this moment as vividly as possible. I felt like I was unlikely to be fortunate enough to see her body again and I felt overwhelmed and dizzy in that heady moment.

I watched as she shaved her legs and her thighs then up to her pubic area. My erection became painful as she carefully used the razor to remove the peach fuzz which I had not noticed when she initially disrobed. When she completed the delicate job she looked up at me and laughed. I must have seemed silly staring in shock at the unbelievable display of Samantha’s sexuality. I gawked at the smooth lips and her smallish clitoris where they came together. The pinkness underneath the plump lips made my mouth water and again I struggled to catch my breath. I realized that I was hyperventilating. “Maybe I’ll give you a taste,” she chuckled, “but not until the morning when I get back from Bruce’s.” I gulped and nodded submissively. It wasn’t until later in the evening that I realized that my “taste” was likely to take place after she had made love to her boyfriend. To my surprise the thought did not deter my urge to kiss Samantha’s smooth pussy.

We moved into the bedroom -she splendid in her nakedness and me following like a puppy. She instructed me to retrieve her stockings from the dresser drawer and I attempted to roll them up her smooth legs. My shaking hands rendered me useless at the task and Samantha swatted me away in frustration. She was gorgeous in the lace and I was only too happy to retrieve a pair of black panties which were cut high on the leg. I watched in awkward silence as she pulled the panties on and I sighed as she completed the task. Samantha looked at me and burst out laughing. “Christ,” she said “Your eyes are bugging out of your head.” I looked away in embarrassment.

She let me bring her a stunning black dress and I shuddered as she pulled it on. Would I ever see her nakedness again, I wondered? I was lost in thought when she snapped her fingers to get my attention. I eagerly zipped the dress for her and reveled in the opportunity to be so close to her. The act of zipper her dress seemed so intimate that I relished it and took as much time as I dared without annoying her.

“Get my lipstick,” she said “the dark red shade on the dresser.” Samantha had me hold a small hand mirror for her as she painted her lips. It was the sexiest display of femininity I had ever seen and I became aware of the fact that I had been painfully aroused for over an hour already. Still, I wouldn’t dare have missed a second watching Samantha primp and prepare herself for another man. I was completely enthralled. “Do you think Bruce will like it?” The question was completely rhetorical. There was little doubt what I thought. I couldn’t imagine a man resisting Samantha’s charms.

Forty-five minutes later the doorbell rang. I had helped Sam put on her blush and eye shadow and I had brought her various earrings and necklaces as she settled on the correct combination for her date. She never asked my opinion but she enjoyed teasing me and laughing at my reaction. I was completely smitten with Samantha and she was undoubtedly completely aware of the fact. She had also surely noticed that I had been on edge since the moment the ordeal started, and my ongoing state of arousal seemed to amuse her greatly. Several times she slapped my hand as I attempted to rearrange my penis inside my underwear and other times she laughed at the small, but visible erection.

Bruce looked at me with a questioning look as I opened the door and ushered him inside. He was big and strong looking. His perfectly tailored suit flattered his broad shouldered torso. Bruce was the kind of guy who seemed to have everything going for him -an alpha male.

Samantha smiled at Bruce as she made her entrance. “Do you like?” she said as she showed off her sexy dress. The plunging neckline displayed the sunburst tattoo on her breast and I gulped anxiously.

“Fuck yeah, I do”. Bruce looked at her hungrily. “I think we should skip dinner. We can order in.”

“I like the way you think,” Samantha said. When Bruce nodded towards me, Samantha just shook her head “Don’t worry about him. He’s just the maid.” She snaked her hand around his elbow and the exited the apartment. I sighed and, finally alone, I relaxed for the first time since I entered her apartment that afternoon.

The door was thrust open again and I jumped, startled. Samantha walked past me through the living room. She returned from the kitchen having retrieved the bottle of wine that I bought her. “I want you to clean this place while I’m gone. It needs to be immaculate. If I’m not satisfied in the morning you’ll be looking for a new job by Monday, understand?”

“Yes, Ma’am,” I nodded, and she was gone.

******

It was perhaps the strangest night of my life.

With the house empty I sat and reflected on the surreal afternoon. I had spent several torturous hours with Sam getting ready for her date, and now she was gone. I immediately decided that I had to relieve myself of my pent up arousal. I crept into her bedroom like a thief in search of relief. I was paranoid. Was Samantha testing me? Perhaps she was somewhere watching. I looked over at the pile of laundry in the corner and briefly wondered if she would be horrified to see me masturbate in her bedroom?

My arousal soon outweighed my fear and I began rummaging through the clothing. I found a pair of used red panties and with shaking hands I brought the gusset to my face and inhaled deeply. I had never been so turned on. Somehow I managed to navigate the buttons and zipper on my slacks so as to lower them to the ground. I hurriedly began to play with myself and the knowledge that I was in Samantha’s room along with the sight and scent of the underwear pushed me over the edge. Within a minute I stood in front of a small fresh stain on Samantha’s carpet. My cheeks reddened from embarrassment as I imagined her watching me from a hidden location.

My guilt was replaced by a sense of panic as I looked at the mess I had left. I found Samantha’s cleaning supplies downstairs and began scrubbing the carpet, desperate to remove the traces of my ejaculate. Soon it was obvious that the carpet had been recently cleaned in that one particular location so I found myself scrubbing the entire room. The fear of displeasing the object of my infatuation inspired me to work doggedly for the two hours. I cleaned her dresser and stripped her bed. I organized her closet and wiped-down the walls. I smiled to myself as I imagined Samantha’s approval as she evaluated my work.

I found her laundry room and I carefully sorted the clothes for washing. Despite coming across several pieces of sexy under things I had managed (barely) to continue working without stopping to obsess over them. Later, while cleaning under her bed, I happened across a glass dildo and the knowledge that Samantha had used the toy to pleasure herself was simply too much for me to take. I masturbated for the second time that evening -this time in Samantha’s bathroom where the cleanup was greatly simplified.

Once I had finished in the bedroom, I worked feverishly in Samantha’s kitchen and living room until I was sure that my tattooed goddess would be pleased with me. The floors were vacuumed, the counter tops sparkled and I was exhausted. I dragged my feet to the laundry where I retrieved Samantha’s silk bed sheets. I decided that I would have to take a break after making her bed.

Sam’s sheets were a slick black silk. I couldn’t help but imagine her naked body under the cool fabric and I again felt a surge of arousal. I was somewhere between exhaustion and arousal and somehow, against all sound judgment, I found myself -still clothed- slipping into Samantha’s bed. In my muddled state, I told myself that I would rest briefly before finishing up my chores. I closed my eyes and quickly fell asleep.

I had a disturbing dream. Samantha was crawling on the bed looking over her shoulder at me. Only I wasn’t myself. My poorly defined arms had been replaced by those of an athlete and my chubby physique was gone. I was taller and stronger and my naked body was that of a sexy alpha male. Most shocking, my small penis had been replaced by a large powerful cock -the hard and thick penis of a porn star. I reached down to grip the solid member and I briefly felt myself amazed at it’s proportions. I had always wondered what it would be like to be well-endowed and now I was huge. I looked up at Samantha and noticed that she too was enamored by the big dick. The look in her impossibly-blue eyes assured me that she wanted me to fuck her with my fantastic new endowment.

My dream girl smiled, “I’m so ready for you.” She motioned for me to get behind her and she giggled girlishly when I slapped a round ass cheek. I was confident and self assured. I placed my large hands on her hips and began to guide the magnificent cock inside her wet pussy. I had never been so alive. Soon I was fucking Samantha and for the first time in my life a woman responded to my technique with ecstatic moans of pleasure.

My dream-self had a staying-power in bed that I had never known before. Sam purred like a cat and moaned in delight as I fucked her deeply. We fell into a lustful rhythm and I felt like I had finally become the man I’d always wished to be. I would be successful and well-liked and rich. I was a sex god. For a brief moment I thought about my real life and my own undesirable body. Was that the dream or was this? I caught my reflection in a mirror and I saw the reflection of Bruce looking back at me. A flicker of reality interrupted the dream. It wasn’t me fucking Samantha -she was on a date fucking Bruce. I became confused and unsure of myself.

Samantha’s cries of pleasure began to quiet, then cease. She looked back at me and her expression changed from ecstasy to disappointment. I looked away from her in confusion and horror. I felt my confidence leaving me and the strength fleeing my body. I continued pumping my cock inside Samantha from behind but my confident technique was replaced by a desperate desire not to embarrass myself. Bruce’s athletic physique was changing into my pudgy office worker body. I was sweating and wheezing and to my horror my penis was shrinking before my eyes. Soon the wonderful porn star cock had been replaced by that of a merely average guy and it continued to shrink. The penis in my dream became the small cock that I was so used to and continued to shrink until all that remained was a miniature dick about two-inches in length. Samantha was furious, “What do you think you are doing? You’re fucking pathetic.”

I continued to hump Samantha’s gorgeous round ass but my penis was now too short to reach her pussy. I was rubbing the tiny nub between the cheeks of her ass, but no deeper. “Get off me,” she said and I began to ejaculate. My semen covered over Samantha’s butt cheeks as she pushed me away from her body in disgust.

I woke sweating and horrified. A wet feeling told me that I had cum inside my underwear and my pants. They were both stained by the semen as were the silk bed sheets. I was shocked at my own depravity.

Once again I stripped the bedding off the bed. In the laundry I stripped out of my clothes and piled them in the washing machine. I realized that I had nothing to wear and I began to worry that Samantha would walk in on me. Was it close to morning? I had no idea of the time.

I found a pink terrycloth robe hanging on the back of the laundry room door. I wrapped myself in it despite the fact that I probably looked ridiculous and that if Samantha were to return home anytime soon I would have no explanation for my attire. I just couldn’t think of another alternative.

I was scrubbing under the kitchen sink when I heard her voice. “I must say, I am impressed. You make a good maid.” Startled, I banged my head on the drainpipe as I scrambled out from under the sink. Samantha began laughing and I realized that I must have looked absurd sitting on the kitchen floor wearing a woman’s robe. “Christ. What the hell are you doing? Wait, I don’t even want to know.” She was more bemused than angry. I blushed furiously as I sat looking up at her.

Samantha’s hair was mussed and her makeup was out of place. This was the visage of a woman who had spent a busy night with her man. She had removed her stockings and her dress was wrinkled. I assumed the clothing had spent most of the night piled on the floor in Bruce’s bedroom or on a chair. Samantha smelled of alcohol and sweat and a more primal odor that I found arousing. The top of her dress hung loosely over her chest as she had neglected to secure several buttons. The two tattoos on Samantha’s breasts immediately caught my attention and I found myself staring at her as she looked at me with contempt. Samantha was bra-less and I could clearly see the outline of her nipples under the black fabric. My penis stiffened. There were small red marks on Sam’s neck and collarbone -evidence of Bruce’s kisses and bites. I was jealous and embarrassed and completely speechless.

Samantha shook her head as she left the kitchen. I watched her walk toward the staircase dangling her heels in her left hand. Samantha’s generous ass was displayed beautifully in the tight skirt and I realized that she was definitely not wearing the underwear that we had picked out for her date. I imagined her freshly-fucked pussy and I couldn’t help but touch the head of my aching dick as I watched the sway of her behind. I felt close to cumming for the fourth time in the last few hours and I was forced to sit and compose myself for several minutes.

I had no idea what I should do now. Should I leave? I ended up following Samantha upstairs and I peaked in her bedroom to see Samantha lying exhausted in the soft chair next to her bed. Despite my best efforts at stealth, she heard me. “Why isn’t the bed made? Jesus. Am I going to have to sleep on a bare mattress?”

“I was cleaning the sheets. They’re almost ready.” She was only half awake and ignored my excuse-making.

“I’m exhausted. You need to wait for those sheets and make the bed before you leave.” Samantha seemed to be sleeping by the time she finished the sentence.

I was at the top of the stairs when she called me back to the room. “Get the lotion. My feet are killing me.” I began massaging Samantha’s feet as she drifted in and out of consciousness.

Samantha responded to the foot rub in her own amazing sensual way. It was terrifically arousing for me to watch her moan contentedly as I rubbed her feet. She smiled slightly and I was sure I had never seen anything so beautiful. Samantha was undoubtedly tired, but she had a satisfied glow about her. I watched her enjoying the massage and I felt my penis stiffen again as I rubbed the lotion into the underside of her foot. Samantha’s feet became the latest object of my lust and I examined them carefully as I worked. Samantha’s toes were red from her shoes and the nails were painted with a very dark red polish. I paid special attention to the sounds Samantha made and I noted when she sighed with pleasure as I found the correct spot. I rubbed her feet until my hands ached while my cock remained painfully hard.

Samantha sat up and smiled at me, “You’re good at that. Wow.” I felt a swelling of pride for the first time around her. “My legs now, please.” She smiled sweetly and I felt my small penis jump slightly inside the terrycloth robe.

Samantha continued to doze as I lovingly massaged her calves. I found myself tracing the vine-like patterns in the ink with my fingertips. After a few minutes she opened her eyes and when I returned her glance she smiled coyly and whispered “higher.” I was ready to burst as I lovingly rubbed the lotion into her thighs. Samantha sighed happily and I felt flush with arousal. I may have looked ridiculous sitting at her feet in a pink bathrobe, but Samantha was enjoying my touch.

I worked on her beautiful legs for several minutes. Sam’s breathing told me that she was half-asleep much of the time, but the sounds of contentment also told me that she was pleased with my ministrations. When she caught my eye again, Samantha smiled wickedly. She licked her lips sensuously and spread her legs. My heart leaped in my stomach as she revealed her shaved pussy. I think I must have done a double take or I may have had trouble catching my breath because Samantha started to laugh. “Calm down, little man. Take it slow and easy. You can taste it, but be gentle. I’m sensitive right now.”

Her scent was a powerful aphrodisiac. I rushed to taste her wetness and I found myself overwhelmed by the moment. I was shaking and my little penis was leaking. As I tasted Samantha for the first time I thought that she her flavor was stronger and muskier than the other two women I had gone down on. I adored the taste and felt dizzy with arousal. It wasn’t until my face was coated in her juices that I realized that I was probably tasting both Samantha and her lover, Bruce. For a moment I considered whether I should stop -I was a heterosexual man after all- but if anything the thought aroused me further. Without touching myself I teetered on the edge of orgasm, and I was determined to bring Samantha over the edge with me.

I listened carefully to her coos and whimpers and I enthusiastically licked Sam’s pussy. I felt like I had reached a kind of synergy with her where I could anticipate how much pressure she would like and where she wanted my tongue. Samantha began moaning and I could tell that she was getting closer. “Oh god. You are good for something. Oh, just like that, my little clean-up man. I think I’ll keep you. Uhh.”

Her orgasm was magnificent and I had my own small orgasm without touching myself. We shuddered together, each lost in our own bliss.

When I regained my senses Sam was sitting up and looking at me. She looked amused and again I felt ridiculous in the pink robe. “You do entertain me, you really do. I like you in pink with a face full of cum. It suits you. How does Bruce taste? Oh, don’t answer that. I definitely know what Bruce tastes like.” I blushed as she continued, “Now, make my bed then get out of here. I’m tired. Lock my front door when you leave.”

I did as my goddess asked. I felt drained and ashamed. I wondered what it would be like to face Samantha at work on Monday morning and whether she would ever want to include me in her sex life again. I was embarrassed that I had tasted Samantha’s lover’s discharge and that I had, frankly, been excited by it. I was sure that she sensed that it was a turn on for me.

I put the robe in the washer and changed into my freshly cleaned clothes. Samantha was sleeping quietly and I took the liberty of sneaking into the doorway of her bedroom for one more look before I left. As I turned to leave I heard her tired voice, “Don’t make plans for Friday night. You need to be here at 7 o’clock. I’m going to have some clean-up for you to do.”