The Boss’s Wife

by Small Penis


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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

These stories are the artistic expression of the authors who wrote them. 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 post, 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.
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by anon

My wife’s Christmas party was later in the day so we spent the first half of the day getting ready. After her admission to me that, after speaking with her boss, she not only was convinced that I was under-endowed, but also felt it would be a major turning point in our relationship, I had a very hard time hiding my increasing arousal at her thoughts. What’s more, she had revealed all of these facts to her Terry, her boss, and Terry was apparently anxiously awaiting to see me again at the party.

I normally wear pants with a 36 waist, but in our travels during the day, my wife went out of her way to buy me a pair of 30-32 boxer brief underwear. She said she wanted to see what effect it would have on my package. I told her I’d do it, but only if we also bought her a training bra that she would have to wear at the party as well. She agreed, saying that while Terry knowing about me and my size was exciting to her, Terry actually being able to see how inadequate my wife’s chest size was even more of a turn on for her.

Once we were home, I watched her getting ready for the party. The training bra had pictures of little girls on them, little girls that were fifteen years younger than my wife and still developing. But when she slid the bra on, it fit snugly, pushing her A-Cups flat against her chest. Once she slid her cocktail dress on over it, a cute little red number that covered her chest completely, but was short in the skirt, she turned to face me, flatter than I had ever seen her before.

“You like?”

“I do,” sitting on the bed, I was touching myself through my underwear.

She smiled at me and ran her hands over her flat chest. “Your turn!”

“I don’t think they’ll fit,” I said, holding them up in front of me.

“Now, Honey, we said we were going to stop pretending and be honest, didn’t we?”

“No, you’re right.”

Even with the growing hard-on in my pants the small underwear fit snug and comfortable.

Once we were both prepared, and properly turned on, we took the short trip in my Charger over to the party. It was a small affair, her company wasn’t that many people, and the lady’s house who was hosting it was a half retired kind old thing who was hard of hearing. I found a corner, as I always did at these things, and tried to blend into the wallpaper with my beer and plate of half-frozen shrimp as she mingled with her co-workers. I kept shifting uneasily though, as the tightness of my underwear rubbed, pulled, and tugged me every which way. Occasionally my wife would look over and wink at me when she saw me move, happy in my discomfort.

Terry and her husband Bill didn’t arrive for another hour. Terry walked in and took off her full length fur coat to reveal a form hugging red dress, with tight straps around her taught, slim waist and loose top over her nicely formed breasts. Her hair, as always, was pulled tight into a pigtail, the streaks of dyed blonde mixing perfectly with her real black hair below. My wife waved for me to come over and say hi, but I was already on my feet and making my way there, the anticipation and embarrassment already growing.

“Hi Terry, I’m so glad you could make it,” my wife kissed her cheek.

“You too dear,” Terry kissed her back and stepped away to examine my wife’s outfit. “You look ravishing. Doesn’t she look great Bill?”

I noticed Bill for the first time, leering at my wife like I had never seen before. “Does she ever,” he nearly whispered at her.

“Why thank you,” my wife said wrestling with his eyes.

They stared at each other for an uncomfortable amount of time until Terry turned to me and said, “Oh, hi Tom, I didn’t even see you standing there.”

“Hey,” my voice cracked when I said it.

“Your wife just looks so incredible tonight, doesn’t she?”

“Yea, great,” is all my stupid brain could come up with.

Terry laughed at that as Bill offered his hand.

“Long time no see Tom.”

I shook his hand. He looked bigger since the last time I saw him.

“You have been working out? You look good.”

“Thanks, been hitting the gym pretty hard lately.”

“It shows.”

Terry leaned into his chest and tickled the bottom of his chin. “Boy does it.” She nestled her head against him and stared at my wife, “I swear I think he’s getting bigger all over.” She smiled and pulled his face close for a kiss. “Isn’t that right my big strong man?”

He didn’t look the least bit put off by her comment. He kissed her and looked at me with his hot wife on his side.

“They say working out increases blood flow throughout the body. So I’ve definitely seen improvement everywhere.”

“Everywhere?” My wife suddenly spoke up, again trying to capture his eyes with soft, sexy looks.

“Everywhere, sweetie,” Terry answered for him, running a hand down his shirt to his belt. She grabbed his belt and pulled up with strong hands, “Everywhere.”

My wife was mesmerised and it was like I wasn’t even standing next to her. Her nipples perked up through the soft material of her dress and her face became slightly flushed.

“It helps,” Bill said still staring at my wife, “Every little bit helps, right Tom?”

Now it was my turn to blush. My God, had Terry told him about her and my wife’s conversations? Did he know about me? This conversation was already leaning that way, but now it seemed incontrovertible.

“Sure.” I nervously laughed.

They excused themselves to say hello to everyone else and my wife came up close and began whispering to me.

“I can’t believe how much better he looks. He was always an attractive guy, but now he’s pretty ripped.” She said still staring at them as they walked around the room. “Honey, do you think that’s true? Do you think you could, you know, get bigger, if you worked out?”

“That’s crap. It doesn’t happen that way. He’s just saying it to get a rise out of you.”

“If you only knew.” She smiled and sipped her drink.

“What?”

“Nothing.”

“No, what?”

“You don’t want to know.”

“Know what?”

“Trust me.”

“What are you talking about?”

She huffed and finally managed to rip her eyes away from them and look at me. “Terry has told me about Bill and sweetheart, TRUST me, he doesn’t need the help from working out.”

“Is that so?”

She took a long, slow sip from her drink, looking over it at Terry and her husband, “Is it ever.”

After they had said hello to everyone Terry and Bill came back over to us and the four of us spent the better part of the night together. Thankfully, nothing else came up about sex and I started thinking maybe I was a little too hasty in my thoughts earlier. The party began to wind down and before long we were all getting ready to go. I had to go and get our coats from the bedroom. I headed up the steps and down the hall to the room. It took me a minute to find ours and when I went to turn and leave, Terry was coming in the door.

“Oh, hi.” I had been staring at her chest for almost the whole night. Her chest, and those lovely long legs of hers, firm but shapely. Even the way she sat, she just exuded confidence all the time. She was, to me, the epitome of a strong woman.

“Hey, I’m glad I caught you, I’ve been meaning to talk to you.”

“Oh?” Like a little kid on his first date, the nervousness washed over me at her mere sight, let alone her wanting to talk to me. I tried to think about my wife downstairs, and tried to think of all the ways I loved her, just in case. I needed to keep my guard up.

“Your wife and I were talking and well,” she looked around the room and then caught my eyes, “well there’s no easy way to say this. I like your wife, a lot. I think she’s a great woman and I think she deserves the world.”

“Of course, so do I.”

“That’s the thing,” she smiled at me and I could see the pity behind it, “you really can’t give her what she needs.”

“Excuse me?”

“Don’t take it too personally. You’re a great husband to her.”

“Yea, and I’ve known you forever and you always said that we were perfect together.”

“You are, Tom, you are. I don’t mean you should get a divorce or anything. But after talking with her, I honestly don’t think you can give her what she needs, you know,” she smiled and pushed her legs together like an obnoxious little girl, “down there,” she pointed to my crotch.

I tried to look insulted. I tried to look appalled and upset. I tried to look anything except embarrassed because I knew if I acted that way, she’d know it was true. Of course I was unsuccessful in all attempts.

“I don’t know what she told you but…”

“Relax, it’s okay,” she moved close to me and put a hand on my chest. “I already knew before she told me.”

“What?!”

“Tom, I’ve been with a lot of men in my time and I have to tell you, you always acted like you were small.”

“That doesn’t even make any sense.” But I couldn’t push her away. Just seeing her this close, touching me, was driving me crazy, I dared not to push.

“Men with small ones tend to act differently. I can usually tell within a few minutes. Why do you think Bill and I got married so quickly? We were only going out for a few months before we got engaged. I knew almost from the first second I met him that he was anything but small. And with you, all those years we worked together before you left the job, it only confirmed what I already knew, that you were under-endowed.”

She moved her hand over my chest and to my belt. Her fingers somehow managed to grasp my zipper without actually touching anything else, and she slowly tugged it down.

“I can’t do this, my wife.”

“It’s okay, Tom, I spoke to her before I came up here.”

“You what?”

She tugged the zipper all the way down. Because of the tight underwear I was wearing, nothing came out of the hole.

“I told her she needed to experience a big man. She needed to know what it really feels like to have a man inside of her.” She laughed as her hand slipped into my pants. “I told her she can have Bill, that she NEEDED Bill. And she said she couldn’t cheat on you unless you did it first.” Her hand pressed into me, “I told her that wouldn’t be a problem.”

I breathed in sharply as she worked in small circles.

“She would never cheat on me.”

“You’re right Tom, that’s why you’re going to be there. But just to make sure you know your place, I’m going to prove to you why you’re a small man and he’s not.”

“Why would you,” I was having a hard time talking, her breath, her smell, just her presence was crumbling my will. “Why would you want Tom to be with another woman?”

She laughed so loud that I thought someone else might hear. She was still chuckling as she began to talk, her hand still buried in my pants. “See?! You act the small man all the time. Bill is a real man. A very big man who knows what he wants and gets it. I can’t say no to him, and I don’t want to. Seeing my man, seeing him take control and act like the stud I know he is turning me on. Turns on any woman. That’s why your little wife down there can’t take her eyes off him. That’s also why he’ll be fine giving it to her with you in the room. A little man like you? You wouldn’t even be able to get hard. Now,” her thumb pulled away the waist of my tight underwear and slipped in, “where is this tiny guy hiding?”

“No,” was my futile protest.

“See, one more reason you’re just a small dick little man. I’m telling you your wife is going to be with someone else, and just because my hand is wrapped around your pathetic pee pee, you don’t say anything to defend her. How can I not give her what she wants?”

She ran her other hand around my back and pushed my pants to the floor. Then she pulled the underwear down too. I was totally exposed, but I didn’t move.

“This is too funny. See what I mean, what man would let a woman do this to him?”

She took a step back and for the first time got a full look at my penis.

“All those years and I was wrong. It is SO much smaller than I ever thought.”

I, for my own part, was as hard as I have ever been. I was speechless, embarrassed and turned on more than at any time in my life. I was utterly willing to let this woman do whatever she wanted to me. Even the threat of my wife being ravaged by her husband did nothing to dissuade me from doing anything to make this woman happy.

She bent over and smiled at my rock hard small member. She took it between her thumb and forefinger and began to stroke it.

“You know what’s so cute about the little ones? They stand up straight. A real dick stands out and proud, but these little ones poke up.” She stroked a little faster and giggled at me, “Tell me Tom, how big is it?”

“I–,” she pressed with perfect pressure on my head, just her two fingers were enough to massage my whole shaft when she pulled a full stroke. “I don’t know.”

“Oh please,” she laughed again, “No man with one this small didn’t measure it at some point.”

She pinched the head again and I jumped in pleasure. I couldn’t believe she was doing this all with two fingers. A true master.

“Tell you what, you tell me what size and I’ll put this little nub in my mouth.”

“Really?!” I blurted out.

“Mmhmm.”

“Almost four inches!” I nearly yelled it, so eager was I to have her blow me.

“Ha! Spoken like the true baby dick you are. See what I mean about small men? So eager, it really is cute. You do have your uses, I’ll say that much.”

“Please put it in your mouth.” I asked humbly.

“Awwww! That was too cute.” She smiled and got on her knees. “Come here. Give me that little boy dick. That’s what you have, right?”

She knelt in front of me and I was already about to come. Her intense two finger job was in every way perfect, rubbing and stroking and pulling me with just two dainty fingers to the point of explosion.

She breathed hot air and it mingled with the precum on my cock. My cock twitched as it got ready.

“Say it, say you’ve got a little boy’s dick. I’m pretty sure my thirteen year old nephew has a bigger one Tom. Say it.”

“Ahhh,” she picked up her pace. She was trying to get me to go and I couldn’t do anything to stop it. “It’s a little boys dick, I have a little boys dick, please blow me.” I rushed through, trying to get her to hurry up before I finished.

“Ha! This is even better than I thought. I’m offering you, a pathetic little nub like you, a masterful bj and you can’t even hold it in long enough for me to start, can you? Can you little boy.” She jerked faster and I was in trouble. “You want to see my man fuck your wife? Do you? You want to see her take a real dick?”

“God, yes!” I would say anything at this point, anything to get her to not stop.

“Good boy! Good boy. You’re going to let her have him to her heart’s content aren’t you? You’re going to let her do whatever she wants right?”

“Right, right.” I winced, I was almost done.

“And why is that? Why is that little boy?”

She pinched, and cum charged up my shaft to the head.

“Because he’s a real man and she deserves a real man!”

Terry doubled her speed and I started shooting as hard as my small cock would let me. She tipped her head back and laughed as I spurted, only twice this time. She cupped her left hand and milked me with her right, pulling out one more half squirt. The watery mix barely filled her small hands.

“My god you even cum like an infant!” She examined her hand and its contents. “Your poor wife! She is in for the ride of her life tonight.”

“Tonight?”

“Oh, didn’t I tell you? We are going back to my place tonight. Don’t worry, you’re coming remember? Little men always like to watch don’t they?”

“Yes, yes we do.” Even more so than with my wife earlier in the week, this woman had defeated me. She crushed my spirit. Her masterful technique and unrelenting badgering had awakened in me a need to serve her, a need to serve my wife. I not only understood what she meant about small men, I wanted to fulfil it, to embrace it. Terry had made me realize that I wasn’t giving my wife what she needed. I was pathetic and she enjoyed that. And that turned me on even more.

“Hold out your hand,” she said.

I held it out.

She tipped her hand into mine and dropped the little pool into my hand. Then she wiped her hand clean on my chest, scraping cum all over my shirt.

“Now go clean up and get presentable for your wife. She’s going to want to see you at your best, so she knows exactly how short you come up.”

I went to pull up my pants.

“No, no, no. Shuffle in there like the little boy you are. Shuffle into the bathroom with that thing and lean up. Okay?”

“Okay.” I hung my head and tried to justify in my head a way to resist her. I couldn’t, I just couldn’t.

“And bring our coats down too. Make sure you grab Bill’s too. Real men wear leather.”

“Okay.”

“Oh, and Tom?”

I turned around to face her. My pants were around my ankles. My little embarrassed dick was even smaller now, shrivelled and useless, and my hand was cupped, easily holding what she had milked out of me. I stood before a woman who turned me on more than anyone ever totally defeated.

“You really are a good husband. Knowing your place will only make you stronger as a couple.” She smiled. “Okay, go, go, go!”

I did everything she said as fast as I could do it. Before long I was downstairs and warming up the car, desperately needing to see my wife.

The End.

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