Dickless

—Part 3—

The night of nights had arrived. The night of the swingers party, at which I would or would not buttfuck my friend Adam’s mom, for the honor of my sister and to avenge my other friend, Jeff. It was his idea. I was in it for the sex, but also because I resented Adam sleeping with the girl of my dreams, Christine. My life was a soap opera, with anal. Jeff expected me at his place well ahead of party time, so that his fuck buddy, my sister’s new bestie, and the daughter of my date, Heather, could dress me.

Also, for last-minute pep talks and whatnot. For my part, I was preternaturally calm. Compared to how I felt before my big night with Christine, for instance, I felt like I was headed out to play mini golf (which is a simile I’ve used before). No nerves, no desperation, no instinct to get on the highway and light out for the territories. I wasn’t sure I could make it with Adam’s mom. But I was confident in myself and my newfound capabilities, as explained, in embarrassing detail, by Heather’s Uncle Mitch, a fellow member of the Small Dick Club.

When I descended the stairs to Jeff’s basement at 6:40–the party started around 9:30, and my date and I would be fashionably late at 10–I was met with a curious sight. Jeff was seated with his back to me on his couch, with Heather’s puffy hair bouncing up and down on his lap. They knew to expect me, so there was no excuse. I wasn’t embarrassed and figured they almost wanted me to catch them. Unfortunately, the step squeaked when I shifted my stance. Heather’s face popped into view, and she blushed, red as a tomato. Jeff glanced over his shoulder and shot me a wry smile when he saw who it was. He didn’t pull up his pants until after he got up and turned around, so I got a good look at his monstrous member.

A better look than I wanted or deserved. I’d seen it in gym class, and of course had heard the rumors. But nothing can prepare you for an erect Jeff. I think he wanted me to see, although he should have known it might put a damper on my spirits. I was supposed to seduce one of the hottest women in town on his behalf in a few hours, and here he is putting my little dickie to shame with his King Kong cock. The three of us managed not to discuss what just happened. Sex lingered in the air, however, especially on Heather’s face. She had fallen for Jeff, and brick house body or not would inevitably be disappointed. I was outfitted by Heather in a stylish ensemble of her assemblage.

The names of the hip articles of clothing, I couldn’t tell you. She began with the foundation of my fancy, European bikini briefs, which I wore from home. It was embarrassing: my lack of bulge plain to see, after Jeff’s display. She continued, constructing a passably cool teen look on top of them. All the while, Jeff summarized the advice he had given me over the past several weeks, with updates here and there. I wasn’t going to be able to retain it all, and would probably end up winging it like I did with Dara and Farrah. But every little bit helped. We headed over to pick up Heather’s mom at 9:15 in my dad’s Porsche. Jeff thought that was the right touch.

Pulled my car into the driveway near her shack, as I perhaps unfairly thought of it, to find Mrs. Sweaten and her brother Mitch waiting out front. She wore a sheer, summery thing. Like on the night we fucked, only relatively upscale and no doubt more expensive. He was in his usual, shabby clothes. I could see why she was invited to these things, despite her status, as if I didn’t know from our time together. Her body had nowhere to hide in that dress, and everything was exactly where it should be. We exchanged pleasantries. I thanked Mitch for putting in a good word for me with his sister.

This might not have been possible without him. Uncle Mitch told me to remember what he said about novelty. Mrs. Sweaten told him to leave me alone and let the two of us go. I made small talk on the drive over, but Mrs. Sweaten seemed more interested in the party than me, which was just as well because we had agreed to leave each other free and unencumbered after we got there. I couldn’t help thinking I had fucked this middle-aged woman not long ago. What that would have meant to me at the beginning of summer, before The Wrong End.

Oh, boy. But now, it was an experience, something that connected us, nothing more. It didn’t mean I couldn’t abandon her as soon as we hit the welcome mat. The party was at the house– a mansion, more like–of one Roger Stone, who was in the real estate game. You’ve seen his name all over town, on this building project or that. It wasn’t the biggest place in town, but it had the most beautiful setting, next to the Byerly Golf Course, secluded in the Greendale woods. Perfect for its function in the secret world of elite, underground swinger parties. We had to pass a gate to get to the drive, quite a departure from the Sweaten Shack.

There were valet parking and a doorman. I gave my key to the attendant, who didn’t seem to speak any English. He handed me a slip, as his colleague helped my date out of the car. We made our way to the heavy, wooden front door, which the gentleman doorman opened for us. I don’t know what I was expecting, but the foyer was empty. Two hallways on either side led to different rooms, and a grand staircase loomed before us. I could hear party noises in the distance. Mrs. Sweaten had informed me the action was on the second floor, so up the staircase, we went. We passed room after room full of mingling people, as we walked down the main second-floor hallway. No one was in the swing of things, so to speak.

No masks or incense, either. Just a bunch of boring, old people like I might find at one of my parents’ parties. Except here the women were better looking, I must admit, and every once in a while you saw the young studs and bimbos I was ostensibly impersonating. Mrs. Sweaten recognized a Mr. Greenstreet from behind in one of the rooms and skipped into see him. He put his hand on her ass instantly. I recognized him for his family’s chain of grocery stores but knew nothing else. Apparently, he and Mrs. Sweaten had been together. She excused herself, very sorry, but she and Greenstreet had caught up to do. I was no longer needed as an escort, and by prior arrangement wasn’t obligated to drive her home.

I was free to track down Adam’s mom. From the terrace overlooking the pool area at the end of the sex gauntlet hallway, I saw her: Ms. Seaver, holding court. She sat on a ledge with a semicircle of adoring men hanging on her every word, competing for attention. She wore a short, black dress and long, white gloves. The scene looked like something out of a classic movie. I immediately made my way down the hallway and staircase, heading for the back of the house, getting lost twice.

Finally, I found a door opening onto the pool. I approached the Seaver crowd, then held back. Best not to appear overeager. Not that I should be a wallflower; stand out from the rest is what Jeff had told me. Let her come to me, if possible. So I hung around the crudites, plating myself some carrots. Behind me boomed the last voice I expected to hear.

“Bend-Her-Over! Who let you in?” asked Mike Stanton!

The bully who pantsed me in junior high, effectively revealing my shortcoming to the whole school! Because of him, to this day I was marked as a small dicked nobody among our crowd. Of all the people in the world to bump into at a sex party. Mike was impressive in his suit, the sort of young stud you’d expect at a party like this. He was bulkier than I remember, and very fit. His tone was friendly, though his volume was aggressively high. His words could be interpreted as a joke, but I knew what he meant.

“Mike, hey. Got here same as you, I suspect.”

“Sugar momma? Yeah, aren’t they the best? But how did you snag one with your…you know.”

Mike was loud enough that he caught the attention of half the nearby crowd. I hoped he’d settle down before Adam’s mom noticed. I decided to meet Mike head on. That’s what confident men do, right?

“You’d be surprised, Mike.”

“Yeah, I would,” he cut me off and leaned in closely. “Tiny dicks don’t usually get invited to these things, ‘less they’re above a certain net worth,” he said, loud enough to be heard by anyone who was really listening.

But thankfully not so loud as before.

“Ladies like all kinds,” I said, borrowing a line from Uncle Mitch. I wasn’t getting anywhere, based on his smirk.

I realized I was playing into Mike’s game simply by responding. He got louder.

“Just that I been to a few of these, and I never seen a guest like you before, Bend-Her-Over. Could be fun, I suppose. How about I introduce you like I did on the soccer field?”

Always the bully. He held his hand out, indicating Ms. Seaver. I noticed for the first time she was looking our way. Mike had turned our conversation into a spectacle.

“Naw, just joshin’. Lighten up, Bend-Her-Over,” he said, hitting my arm, which smarted. I had to rub the pain away.

I was suddenly aware that Adam’s mom was by my side. I hadn’t seen her make her way over.

“Boys, boys, don’t let’s make a scene. Come, we’ll settle this inside.”

Oh, wow. It was happening, but not the way I planned. An invitation to alone time with Ms. Seaver, but Mike had to be there. Damn!

“This way, don’t toddle.”

Her words were belittling, but who cared? Ms. Seaver was gorgeous up close and smelled of lilacs. I couldn’t have spoken had I anything to say, which I didn’t. My mouth was paralyzed by fear. Mike went with her through the sliding glass door, and I felt like a tag-along sibling. Her ass was like two inflated balloons rubbing against each other. She obviously knew her way around and led us to the west wing. Through a rich, oak-lined library lay a cozy backroom, our destination. None of us said a thing on the way. Mike and I were completely spellbound. Once arrived in the room, she busied herself at a drink cart. Mike flopped down in a leather chair, and I stood awkwardly at the door.

“You’re Beverly’s boy, aren’t you,” she said to Mike, handing him a drink. Mike’s mother was named Ruth, so I surmised Ms. Seaver was referring to Mike’s date. “Strapping. I’m impressed. And you?”

She turned to me and handed me a glass of brown liquor. “Mrs. Sweaten,” I managed to get out.

“Judy Sweaten, you mean. Popular girl.”

Was that a dig? No, I think Ms. Seaver was impressed by my date.

“Wonder how he tricked her into bringing him,” said Mike.

“Hush, boy. I was speaking to…what did he call you? Bend her over?” Ms. Seaver laughed sweetly.

However domineering she came off, there was motherly compassion in her. Repeated use of “boy” brought that to mind.

“Yeah, but that nickname is ironic-like,” Mike said. I wouldn’t have guessed he knew about irony.

“How do you mean?”

“He’ll tell you, won’t you, Bend-Her-Over?”

Mike had the confidence of the naturally superior man, who assumes he can best me in this little room. My only chance was to flip the script on him. Couldn’t be a head-on attack, like before. That hadn’t worked. The honesty ploy, as Uncle Mitch taught me, was my move. I steeled my nerves and pretended to know what I was doing.

Mike means my small penis,” I said.

Mike couldn’t believe what he heard.

“Oh, my. You boys.”

“Dude, what the hell?”

“I told you, Mike, you’d be surprised. Small men have their uses.”

“Care to elaborate?” asked Ms. Seaver, with genuine curiosity.

“Bullshit,” Mike interrupted, cutting off the rapport I was building with Adam’s mom. “I bet he’s still a virgin.”

Once again, I went against my instincts and refused to hit back directly. It was now or never, and to win I’d have to be the kind of person I never thought I’d be. I chugged the rest of my drink.

“Now, boy, don’t be rude,” Ms. Seaver scolded Mike.

“No, it’s true. I am a virgin, ” I admitted.

“Oh.”

“Ha! See what I mean? What are you even doing here, John? Can’t you find any kiddie parties to go to?”

“Just because I’m still a virgin doesn’t mean I haven’t done stuff. I’ve probably done more than you, Mike.”

“Bullshit, again.”

“Language, boy!” Mike wanted to keep talking, but her rebuke shut his yap. “What sort of ‘stuff,’ John?”

“Well, did you see that movie, The Wrong Way?”

“My, my, so that’s what you mean. I won’t say that’s not intriguing, but I’m here for something else.”

“Which he can’t give you,” added Mike.

“Shush, Michael, you’re as incorrigible as my son. Good boys who behave themselves get treats.”
“I’ll be good, ma’am,” said Mike, mock-sheepishly.

“I like that. I can only stand your bickering so long,” said Ms. Seaver, who sighed and slapped her pretty, thin arms on her sides. “This is how it’ll be. A lady has her standards, and I’d like to play with you both, but I need men to play with, not boys. Anything under 7.5 inches won’t do it for me; I know from experience. And I think only a certain level of manhood deserves this,” she said, indicating her whole body. “That’s my rule.”

So that was it. I wouldn’t be fucking Ms. Seaver. Bye-bye, revenge.

“Michael, if you’re tall enough for this ride, then we can have playtime. Johnny-boy can watch if he likes. Otherwise, I’ll be on my way.”

There was a chance Mike wouldn’t get her either, which would be a relief. I didn’t want to stick around to be the loser watching them fuck. Plus, I knew I would stay, despite myself, if he measured up. A chance to watch Adam’s mom fuck was too good to pass up. Mike shot me that wry smile of his. Damn. He unzipped, reached in with his big mitt, and pulled out a fat, semi-erect cock. I couldn’t tell exactly what it was in inches, but it was enough.

My pride splashed down the inside of my body and spilled out my shoes. Adam’s mom retained her coolness (tempered by motherly tenderness) but was apparently impressed. She sauntered over and stroked Mike’s cock a few times, stood on her tippy toes to bite his left ear, and smiled broadly. Mike was in heaven. I was turned on, sad to admit. That humiliation that my sister informed me I crave.

“John,” she said as she turned to me, “be a good boy and take off your clothes. Show me how small we’re talking.”

She stared at me, delicate hand on juicy hip, waiting. I had never been more afraid in my life, but I told myself to keep up the false confidence, no matter what. Too late to go back. And who knew? Maybe I’d get something, anything, out of her yet. So I stripped with moderate haste, getting it over with, down to my fancy underwear. Mike laughed out loud, fat cock sticking out, now hard. Ms. Seaver shushed him. She showed no reaction. The point of no return, yet again. I hooked my thumbs into the waistband and pulled down. My hard dickie popped out and stared at them. She was first to speak.

“You really are small, aren’t you? Judy got something out of this?”

“Naw, he proudly roofied her.”

“Michael! Don’t be a sore winner.”

“Ask Mrs. Sweaten yourself. I know she enjoyed herself,” I said, my dickie still precariously exposed.

“I think it’s cute. Reminds me of bathtime with my son.”

Great, my dick brought to her mind a prepubescent version of my friend Adam.

“Well, you get comfortable, John. Your treat is to watch us; Michael’s treat is me.”

She proceeded to disrobe as quickly as anyone I’d ever seen. Whoosh, and it was off. Underneath was nothing. Diane Seaver was naked in my presence. All of her, plain to see. Her shoulders and arms were slender and girlish. None of that muscle tone you see on older women who compensate for diminishing youth by living at the gym. She wasn’t youthful, obviously, but she also wasn’t overripe. She was ripe; let’s say that. Skin a tad tan for my taste, but not leathery. Large, natural tits, pretty pink nipples, taut stomach, a copper-colored wisp of pubic hair, wide hips, and the ass I admired earlier, in the flesh.

Mike was fully nude by the time he embraced her. They made out heavily. Her hand was on his now fully engorged clock, his fingers first stroking then penetrating her pussy. It was so quiet that I could hear her juices squishing. I could also hear their mouths smacking, and their skin slapping. It was gross but hot. I stood there, taking it in. My fight or flight response was almost triggered, but I stayed put. Mike placed Ms. Seaver over the arm of the chair and positioned his condom covered cock to enter her. No blow job, no eating her out. They skipped to straight fucking.

He thrust into her, hard. She groaned, but the rest of the time was less involved. They went at it pretty hard, doggy all the way. She seemed accustomed to it. Her flesh gave into his but wasn’t saggy or floppy. It wasn’t as tight as Christine’s, but how could it be? It stayed in place, for an older woman.

Mike shouted, “I’m cumming!” about 10 minutes in.

Not bad, considering whom he was fucking. He pulled out and finished on her back. They hadn’t discussed that or anything. I think maybe Mike wanted to impress me.

“Good boy. Grab a towel and clean it off, would you?”

“Sure.”

Mike did as told, still nude, cock bobbing. She looked at me with sweaty, bedraggled hair.

“Thanks, Michael. You may dress and leave. John, stay as you are.”

“Baby dick [had Mike been talking to my sister?] gets to stay and I have to go? But…,” Mike started.

“Shush. You’ve had your treat. I have something else in store for our Johnny-boy ”

“Okay. Thanks, Ms. S.”

He acted like the boy he nearly was, regardless of his recent display of manhood, following Ms. Seaver’s lead. Mike dressed and left, not without shooting me a ‘sucker’ grin. Adam’s mom dressed as well and fixed her hair in the mirror by the door. She showed no sign of wanting to leave. I didn’t know what she had in mind, but I didn’t think it’d be what I came for, which was a Wrong Ending.

“John Benderson, did you really think I wouldn’t recognize you?” She knew, all along! “You think I wouldn’t recognize my son’s friend, not to mention Ruth Stanton’s son, Mike? It’s not that big a town.”

“I dunno. But…but why’d you go through with it?”

“For a good fuck, why else? And to give you a show. I believe you’re a virgin, and virgins are in want of experience, by definition. The rest of it, I don’t buy. Let’s say you could use some real action, even as a mere spectator.”

My confidence shot up for real. I could counter Ms. Seaver’s supposition with the truth.

“I wasn’t lying about the rest. Ask Mrs. Sweaten. Ask Heather Sweaten, for that matter.”

I was betraying trusts in a last-ditch effort.

“Mother and daughter, eh? Quite the feat,” she said skeptically.

“Ask Jayden, Dara, Farrah, my sister, Jeff, your son, or…”

“My son? You share the adventures of your little guy with my son?” I was all in emotionally, so I couldn’t hold the last bit back. “…or Christine.”

That one hit her as hard as Mike.

“My Adam’s Christine? You mean she…like the movie?”

“Yes, before she and Adam were together, but yes.”

Somehow, Ms. Seaver believed me. I sensed preexisting distrust of her son’s girlfriend.

“How many, altogether?”

“Five. All of them satisfied. I could do the same for you. You won’t forget it.”

“I’ve been there before, you know. I’m not some neophyte teenager.”

Her thoughts were somewhere else, I could tell. Most likely on Christine.

“Neither was Mrs. Sweaten.”

“That’s true,” she said. “If what you say is true, that is. John…if we do this, I don’t want it to affect my relationship with my son. He must never know. Promise.”

Such a promise would defeat my purpose in being there. Then again, fucking one of the most beautiful ladies in town is a purpose unto itself. So I promised. We went at it. She had all the necessities in her bag. We didn’t kiss or grope deeply, but there was foreplay. I didn’t acquit myself well, and she wanted to get to the main event. The dress stayed on. She hiked up her skirt and bent over the arm of the chair, as with Mike. I positioned my well-lubricated, condom covered little dickie at her entrance, and admired the curve of her ass. I pushed in easily, past her ring, into the void. There I remained, one thrust. I didn’t even think of Christine this time, but I came immediately.

“Uh, ugh,” I let out.

“Did you cum?”

“Uh, yeah, sorry.”

“Oh, honey. You’re too much for words. A liar, apparently, but an adorable liar,” she said in a motherly way, scolding with comfort.

She took it as a trick. Well, I suppose it was. At least I got in there.

“You got me. Let this be a learning experience for us both.”

“Sorry, I…”

“It’s okay, I understand. But I have to get back to the party,” she said, tidying herself up. “There’s a washroom behind us. I’d like you to leave so I can use it in peace.”

She seemed disappointed, not sexually so much as a friend’s mom who caught me up to no good.

“Okay.”

“Remember your promise. Not a word to anyone. I don’t want to end up on a list you use to convince foolish older women like myself.”

Oh, shit! The promise! What would I tell Jeff and Heather if I kept it a secret? Could I go through with lying to them, after all that build-up? I’d have to fake failure, and I didn’t get off on the kind of humiliation that would bring. What about my sister? Where’s her revenge? But I couldn’t betray Ms. Seaver’s trust; not after what she let me do.

As I chewed on my dilemma, Ms. Seaver went on, “And that Christine. I don’t know if I want a girl like that around my Adam. Oh, nevermind.”

What was this? A means of achieving my goal of pulling Christine away from Adam? A meddling mother was better than any schemes I’d hatched. Ms. Seaver went to the washroom, which appeared from the wall as if out of nowhere. I thought as I dressed. Christine could be mine, at least for a night, to finally lose my virginity. It could be done. In any case, though my promise would be kept, news of my time with Ms. Seaver would nevertheless slip out, beyond my control. When Bend-Her-Over fucked Adam’s mom, he became Johnny Buttfuck. Soon the world would know. Now, where’s that valet slip?

 

The End.