Dickless

—Part 1 (Adam’s Mom)—

I’m back: the Greek Bandit, Master of Ass, Backdoor Man. By now you’ve probably figured out that’s hyperbole. I can’t get inside any girl’s behind at will. ‘Johnny Buttfuck’ is an honorary title only slightly less ironic than Bend-Her-Over, my friends’ oh-so-clever reworking of my last name, Benderson. I have been inside precisely three girls’ backsides: Christine, the modelish beauty; Heather, the buxom waitress; and Jayden, the punkish friend-zoner. But only because a popular movie about teen girls losing their anal virginity, The Wrong End, put ideas in their heads, and because my small penis was the perfect means of easing their way into the world of anal sex. And because my small penis was useful for easing them into the world of anal sex.

My buddies set them up for me, so I couldn’t even take pride in having picked them up. Not altruistically; they had ulterior motives. One such motive was Jeff’s planned revenge on Adam for stealing his ex, Christine. I agreed to participate partly to make up for my part in Adam’s humiliation of my sister, but also to get a piece of the intended vehicle for revenge: Adam’s mom. That’s right, I was to Wrong End Ms. Seaver, the hottest MILF in town. Jeff’s plot would earn me the nickname Johnny Buttfuck, and it was far beyond anything I’d done before. But don’t get your hopes up. I didn’t turn into the ‘Don Juan of the Rear’ or anything. This was as much a set-up as the others, and the nickname would be an ironic reference to my small penis as much as anything. But it did make me famous in our little town.

Ms. Seaver, Adams mom, was out of my league. Despite my family having nearly as much money, and my parents occupying a firm position in leading social circles, we weren’t anywhere near Seaver status. My mother was a prosperous career woman, worked with charities, and sat on boards of foundations. My father was the CFO of a prominent regional corporation. Both belonged to the town’s fashionable club, attended notable parties, and vacationed with the best people. Adam and I were friends and hung out together regularly. At least until our group’s recent shake-up. His mom was a class apart. She was like a local Kardashian. (Not physically, otherwise Johnny Buttfuck could never get in there.) Famous for being famous, and all men’s eyes were on her. I told you about her exes: the Wall Street guy and the NFL player. Well, there were plenty of men where that came, confirmed or merely rumored. She dressed in high style and had all the money you could want.

She gently mixed outward chic with implied sexuality. Big, natural-looking tits, full hair, and lips, pretty face, ample ass. How could I ever get to her? Jeff had an answer. He knew what most townsfolk did not: Adam’s mom was a swinger, and we had an elite underground swinging culture. Not an ‘Eyes Wide Shut’ type of thing, but a collection of like-minded (and sex minded), powerful, and influential people, who get together with some of the most attractive and desirable people in town. I was neither powerful nor desirable. Jeff had an answer for that, too, involving our co-conspirator: Heather. About Heather. She was in on our little conspiracy because Adam had burned her, too, and because she was my sister’s friend. But mostly it was because she was infatuated with Jeff. The two of them were already sleeping together. I know because Jeff told me.

“Her tits are so awesome. I could stare at them all day,” he told me.

Jeff knew Heather and I had Wrong Ended, but he didn’t know she kept her bra on. I hadn’t seen her melon tits, not for want of craving. “Yeah,” was all I said.

Heather never stopped making goo-goo eyes at Jeff the whole time the three of us were together. Just like I saw Christine make at Adam, only Christine and Adam had a chance to be a real couple. Heather would only ever be sex to Jeff. I wasn’t told whether Jeff managed to stuff what I knew was his large cock in Heather’s ass, which I had assumed was his purpose for having me pop Heather’s anal cherry (even though Jeff and Chris were still dating at the time). I didn’t care to find out, frankly. The three of us were in Jeff’s basement, Grand Theft Auto paused on his tv screen as usual. He played that thing whenever he wasn’t out getting pussy. We were deep into him telling me exactly how it would go down with Adam’s mom. He had planned things to the final detail. Heather was present not because she and Jeff were plowing, but because of her mom, Mrs. Sweaten was vital for my entry to the forbidden world of underground sex parties.

“Oh, yeah, she doesn’t even keep it secret,” Heather said.

Her mom had been invited to sex parties before. Besides a string of very public boyfriends, every one of which Heather and her sisters resent, Mrs. Sweaten was a known party girl. She resembled her daughter, who was as hot as any girl in town, and she had been Homecoming Queen, head cheerleader, and Miss [name of our town] back when. Age hadn’t been as kind to her as it had to Adam’s mom, but enough of the right sort of men–and women–fancied her.

“Why would your mom agree to bring me along? I thought you said they only occasionally invite outsiders and in that case mostly young studs and bimbos. I’m not one of those,” I said to Jeff.

“They don’t know that. You’re good looking enough. We can dress you up and show you how to act,” Jeff explained.

He was right enough. They wouldn’t know about my tiny penis (hopefully, neither would Mrs. Sweaten), and I wasn’t ugly or fat or anything. My personality we could work on.

“Heather, how do you know your mom would bring me?” I asked.

“She flirted with you, or didn’t you notice? She also respects you. Thinks you’re smart and a good influence, or whatever. Plus, she owes me one. I promised to watch my sisters every day I wasn’t working this summer, with no allowance. I know she’d bring you if I asked.”

“I can’t believe you two talk about stuff like that. If it were my mom…”

“But not your sister. You should hear how she talks about your little dickie, and how you spied on her fucking Adam.”

I blushed. Heather had me there. My sister made fun of my ‘baby dick’, as she called it. I saw her and my soon-to-be former buddy doing it. We had an unusual relationship.

“Okay, but flirting is one thing. Your mom might think I want something more from her.”

“That’s not a bad idea,” said Jeff.

“What?” asked Heather.

“Maybe he should do your mom. Might be less awkward asking her to bring him to a party afterward.”

I was speechless.

“I don’t see why not. That’d probably be better,” said Heather, to my surprise. I started to get a hard-on at the thought.

Seeing the vintage version of Heather’s tits would be a good substitute for Heather’s. Plus, I could finally lose my real virginity.

“Don’t get too excited, Bend-Her-Over. You’d have to seduce her. I couldn’t outright ask ma to fuck you.”

Challenge accepted: sleep with Mrs. Sweaten to get a chance at Ms. Seaver. Not impossible, at least the first part. Heather’s mom had flirted with me, as Heather said. It was just a matter of seeing her again, saying the right things, putting on the right moves, picking the optimal time. Jeff put me through instructional sessions. What to say, what to do, what image of myself to project. He said it was all about framing: keep the encounter on my terms. She should want me, not the other way around. I can’t show desire. Get her to chase me. Easier said than done, but at least I had a routine. Just a matter of putting it into practice. Our plan was for me to show up at Heather’s house Saturday afternoon to move furniture. Heather promised her mom I’d help; lazy, unemployed Uncle Mitch couldn’t do it alone.

Heather wouldn’t be home, her sisters would be at a birthday party, and the uncle was leaving shortly thereafter. This was my chance. I showed up at their little rambler around 4 pm. Mrs. Sweaten and her brother were on the front lawn, mildly arguing. I was intrigued by his apparent submission. That might be expected since he lives in her house rent free. But he seemed to like it, or at least took it lightly. Mitch Sweaten was in his 40s, same as his sister, but not nearly as well-kept. The Sweaten look only worked with Sweaten girls, I supposed. Mrs. Sweaten waved hello when she saw me coming, welcomed me, and went inside to fetch a drink. Mitch nodded my way and sauntered over. He was overweight, already out of breath, balding, and smiley.

“Hey, we haven’t met. I’m Mitch,” he said, extending his hand.

“John,” I reciprocated.

“I understand your friends with my niece,” he said, devoid of implications.

“Yeah.”

“And you’re here to help my sister.”

“Uh-huh. Glad to be of service.”

“Okay. She can be a fun one, sis, and she likes all kinds.”

What was this guy getting at? Did he have ideas about us? Heather told me her mom asked about me a few times. Had Mitch overheard? Did he think his sister had designs on me? Of course, he knew about her loose ways. How could he not; the whole town knows. But was it common for her to bed 18 year-olds? Mitch hadn’t said much, but it was how he said it. He was all nudge-nudge, wink wink. Or was I reading into things? I decided to drop it. Mrs. Sweaten came back out with a pair of glasses. She handed one to me and one to Mitch. She was wearing a thin sundress, which in that light was nearly transparent. I couldn’t help but be reminded of Heather: same melon tits, only droopier. Same big hair, same thick make-up, same coffee table ass, same overall pornstar look. I was excited already, but per Jeff’s advice played it cool.

“Mrs. Sweaten, looking nice…for an older woman. I should stop by more often.”

“Oh, John, you flatter me. Enjoy your mojito. I thought it’d be good for a hot day like today, and you kids shouldn’t have to wait til you’re 21.”

“I think so, too. We drank with our friends in high school all the time. Didn’t we, sis?” said Mitch.

“Don’t go telling stories about the old days, Mitchy. Now, go open that side door, make sure everything’s clear for the couch.”

The couch I was there to move. I got the feeling she wanted her brother out of the way for a bit.

“So, I haven’t seen you around Heather lately. An old broad like me scare you away?”

“No, nothing like that. Heather and I are just friends, and I was helping her with college stuff like we said. I have plenty of other girls to see.”

“Uh-huh,” she said, with suspicious overtones. “That’s not what I heard.”

“Heard what? From who?”

“I mean what I heard when you were in my house. We don’t have thick walls here. Heather has brought boys home before, and I know what things sound like.”

“Oh,” I said. This might be harder than I thought.

“College indeed. I know what you boys see in my Heather. They used to see it in me, too, you know.”

“They still do, Mrs. Sweaten, believe me.”

“You flatter again, John…Here’s Mitch; let’s get started.”

So we were flirting again, this time with a more firmly sexual basis. She wasn’t offended that I had had sex with Heather under her roof, and she even seemed turned on, a little, confronting me about it. In the very least she was being playful. I don’t know if I was making her chase me, as Jeff advised, but we were on the subject of sex, which was a good sign. Mitch and I moved the couch. He went back inside to wash up, while Mrs. Sweaten and I sat on her porch swing.

“Mitch is nice, a good, loyal brother. But I don’t see his life going anywhere. ‘Course, I expected bigger things for myself. I was going to marry up, you see. But Heather’s father came along, and here I am.”

“Here is pretty good, Mrs. Sweaten. Heather is a great girl, and you have a good family.”

“Here is a step up from a trailer park. Don’t kid me. Coming from where you do, that mansion on Evergreen Terrace, you know better. Heather is an attractive girl, I love her going to college, and I pray she doesn’t make the same mistake.”

I didn’t know how to respond to that, exactly, so I didn’t. I didn’t say anything. Our conversation hung in the air until Mitch opened the front door. “Okay, party people. I’m off. See you tonight, sis. Keep her company, why doncha, John?”

“Have fun, Mitchy. See if your deadbeat friends have any work for you,” Mrs. Sweaten said, light-heartedly.

“Will do, boss-lady,” Mitch added, with mock sincerity.

When we were alone, Mrs. Sweaten invited me to supper. She was drunk. I hadn’t followed Jeff’s advice very well, but things were going according to plan anyway. She grilled hamburgers outside. Told me Mitchy (as she called him) usually took care of that, and I’d have to put up with her version. I didn’t mind. We had maybe three more drinks before dinner, which we ate on the nearby picnic table. In addition to the hamburgers, we had store-bought potato salad and chips. I wouldn’t call it a sexy meal, but Mrs. Sweaten looked at me all night in a certain way. We lingered in the evening sun, as she smoked and I nursed my current mojito.

“Something about nights like this reminds me of my first boyfriend,” she said. I feigned disinterest.

“Not one of those ‘how I lost it’ stories, I hope.”

“No, it wasn’t like that. We were 12. The furthest we ever got was kissing under the deck in his backyard. I didn’t ‘lose it’ til I was 14. Whaddya take me for?” she said and laughed, loudly.

I liked how open she was being.

“Oh, well, 14 is still young. I haven’t lost it, and I’m four years older than that,” I let slip.

How could I have said that? (Mojitos) I was supposed to impress her, not confess my virginity.

“Come off it, John. I know about you and my daughter, remember?”

“That was different. We only… never mind.”

“No, tell me.”

“I can’t. It’s too embarrassing.”

“Now I have to hear. You can tell me. I know all about Heather, by the way. We don’t keep secrets. Not big ones. I know she’s seeing that other one right now, what’s his name? Jeff.”

“Oh, but she probably hasn’t told you everything.”

“Nobody knows everything about another person. Mitchy and I used to have a total honesty pact. Not anymore, but used to. I didn’t tell him everything, let me tell you.”

She was majorly slurring her words at this point. Any more alcohol and I might not have been able to go through with it if by some miracle she wanted to go all the way with me. But it was interesting, what she confessed. That could explain Mitch’s forwardness earlier when he told me Mrs. Sweaten likes all kinds. Was Mitch still privy to his sister’s love life?

“You don’t want to hear it.”

“Try me, young fella.”

“Okay, well, Heather and I did stuff, yeah, but not all the way.”

“All the way? You’re such a teenager. Whadja do, then?”

“Other stuff…private stuff.”

“I see. I know all about private stuff, you know, hun. You can use your words.”

I went all in. This would make or break the night, I thought. “Have you seen that movie, The Wrong End?”

“Seen it? Three dates have brought me to it since it came out in June…What of it?”

“Heather…”

“Wait, you’re not saying what I think you’re saying…Oh, my God.” She was laughing, which I took as a good sign. “But why with you? Why not one of her more serious boyfriends?”

“There’s something everyone on knows about me. Something which has come in useful for girls like Heather.”

“What? What do you mean, hun?”

“Well…” The point of no return. “I’m small. Down there.”

Her eyes spread wide. She interrupted me, stood up, and extended her hand. “Come with me.”

Without another word, we sprinted toward the house, through the family room, into her bedroom. Which wasn’t much bigger than Heather’s, but had a water bed. She didn’t say a word; she just pulled her sundress up over her head. I saw a large white bra and mom panties. She hadn’t been planning on a man seeing her tonight, I surmised. Her skin was very tan, and she had several tattoos. Her tits stretched the fabric of her bra. All her parts stayed in place but moved loose and free compared to Heather’s tighter body. I barely had time to admire her before she was on her knees and at my pants. My little dickie sprang out, fully hard, after she pulled down my jeans and underpants simultaneously.

“Just like Mitchy,” she said, unexpectedly. “He could never get a girl, either, until I helped him out.” I couldn’t believe what I was hearing. “Not like that. I set him up with some of my less experienced girlfriends. They were happy to start off with something easy like my poor Mitchy had between his legs. That’s when we first started our total honesty pact.”

I thought about my sister Sarah, the similarities and differences between our situations. Sarah knew about my shortcoming, too, but she didn’t offer to set me up. I got that from my guy friends. Sarah made fun of me, calling me ‘baby dick’. I wish I had the relationship Mrs. Sweaten had with Mitchy. Before I could respond to her story, she had a junior in her mouth. All of him, without a problem, naturally. I watched her hair billow as her head pumped up and down.

In no time the bubbling came up. I warned her, “I’m gonna cum.”

And I did.

She didn’t let up, and swallowed it right in front of me, smiling.

“There’s my good little boy,” she said, stroking my thigh. “I know small dicks can’t control themselves. Mitchy couldn’t, either.”

I didn’t like her talking about Mitch now, but I did like her talking down to me, for some reason. My sister told me that I’m turned on by domineering girls, and I was learning more and more how right she was. She only said it because she was jealous of the first girl I buttfucked, Jeff’s ex and Adam’s girlfriend Christine. Whom Sarah referred to as the Ice Princess. But Sarah was correct, even if she only said it to hurt me. Mrs. Sweaten had me lie on the bed as we made out. She kept her bra and panties on, she told me because a woman her age has her modesty. Damn, was ever going to see a pair of Sweaten tits?

She knew how to kiss better than Heather, I noticed. Very slow, deliberate, sensual. She softly bit my lip, played with my ears, and explored my body with her hands. I assumed we were building up to something special. The cigarette smell was much stronger with her than with her daughter; that was the only turn-off. Otherwise, her older, less glowing skin, her droopier body, and her scattered wrinkles didn’t bother me. I had pictured being intimate with an older woman as being if not unpleasant at least less pleasant, especially after experiencing the beauty of Christine and the hotness of Heather. But Mrs. Sweaten didn’t put me off at all. Even after cumming and losing some of my drives, I was as into it as I had been with the other girls. Plus, this time I figured I would definitely lose my virginity.

“You’re still hard. I love young cocks. Even little ones, like yours. How about we do the Wrong End?”

Not again. She wanted me to put it in her ass. I didn’t want to risk the mood, though I wished she remembered I’m still a virgin and might have the Right End on my mind. I forgot all about it when she got on her knees and pulled down her panties. My first view of mature pussy. As bald as Heather’s, but not so meaty. I didn’t have time to linger, as she grabbed lube from her nightstand, took care of business, and assumed the position, in Jayden’s terminology. I got up, stood next to the bed, and closed in on her. Like the others, she was on all fours near the edge. I had a harder time pushing into her than with Heather, and Heather was the most difficult. Giant Sweaten asses were a challenge, and moms were bigger than daughters. But I got in there, like always, and pushed forward. I safely assumed Mrs. Sweaten wasn’t an anal virgin, and her ring definitely was more elastic than the young ladies’. I popped in there easily. The void met me for the fourth time. She moaned in her deep, mature voice. Her sounds were spacey, possibly because of the booze. I felt more into it than expected, under the influence of mojitos and having cum a mere 15 minutes prior. My mind undulated with the waves of the waterbed and Mrs. Sweaten’s covered tits. They moved more than Heather’s had. It hit me, how similar were mother and daughter, right down to keeping their bras on while getting fucked in the ass by small-dicked guys. I thought back to the other girls I’d fucked, neither of them very into it, ending on Christine. There it came, the bubbling. Christine had pushed me over the line again. I was about to cum in Mrs. Sweaten for the second time in half an hour. She was still moaning away. I wondered if she’d be disappointed. Too late.

“I’m gonna cum.”

“Okay, hun. Fill up mommy’s ass.”

Mommy?

Nevermind, I came. We collapsed into each other.

“Gotta get up, hun. The girls should be home by 9.” She got up unsteadily, and not just because it was a water bed. “I’d sure like to fall asleep right now, but a mother’s work is never finished.”

“That was great, Mrs. Sweaten, if we could—,” I began.

“Think nothing of it, hun. I enjoyed myself. I know fellas like you and Mitchy have a hard time. Now, here’re your clothes, you gotta scoot.”

Once again, no afterglow. No pussy, either. Mother and daughter both sucked me off, at least. I felt less used, less like a science experiment. Mrs. Sweaten wasn’t in a rush to lose her cherry, and she genuinely wanted to show me a good time. But it was over as perfunctorily as with the others, and with as little prospect of a repeat performance. Then I remembered my reason for being here: Adam’s mom. Was Mrs. Sweaten more or less likely to help me out? More, I figured. But maybe she’d think an elite underground swinger’s club wouldn’t be a good place for a baby dick like me. Surely she didn’t bring Mitchy along. Heather would have to smooth that part out for me.

On the drive home I got to thinking about Christine. Of all the girls I’d buttfucked, she was still my obsession. How would she react, should I pull it off with Adam’s mom? If Adam and she were as serious as I guessed, would she ever forgive me? Not as if I could win her over, but I wouldn’t want her to hate me. It wasn’t too late to stop. Then I pulled into my driveway and saw Sarah through the front window. She was zoned out on the couch in front of the tv. Vacant. I wondered if we could have a relationship like Mrs. Sweaten and Mitchy. Open, honest, helpful. Sarah didn’t have to score my pussy, but we could be closer. That settled it. I chose my sister over the Ice Princess.

 

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