Am I the Asshole?
Copyright© 2025 by RickSands
Chapter 32
Erotica Sex Story: Chapter 32 - A young man looks back at his life and lusts. Considering each of the girls and women he's known, he smiles as memories come to mind, relishing the connection and ecstasy that came with each conquest and every ounce of semen he poured between their legs. And so as his past relationships are recounted to himself and the reader, he only slowly comes to realize that maybe he really is the problem after all. Codes will be added as the story progresses.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft mt/Fa ft/ft Teenagers Coercion Consensual Reluctant Lesbian Heterosexual Fiction Brother Father Aunt Light Bond Gang Bang Oriental Female Hispanic Female Indian Female Anal Sex Cream Pie Oral Sex Water Sports Teacher/Student
It was incredible luck for me to meet Cheryl. A woman, older and sure of herself and very willing to accept my masculine attention. Only one day of talk, jousting back and forth about who we were, and after a long lonely night of indecision, we both knew the other was absolutely worth opening our arms and hearts to.
Arms, certainly, and legs, but that bit about hearts was all me. I was taken by her in the first minute. But what did she feel and want? Really hard to say, but if that long morning and following night of sex was any indication, she was at least curious and open to further exploration.
Cheryl was no girl playing games and pretending things she’d later regret. Older, like in her early 30s to my barely and not quite 20. She was the first partner I’d ever seen as first a wonderful and amazing person before thinking of the cock-holding sheath between her legs. Well, maybe not quite that given that I couldn’t get my eyes off Cheryl’s ass and tits from the first moment I stepped into her house. But her wry smile and sarcastic wit and invasive barbs and seriously intuitive insights into my personal place put my cock in a backseat while I tried to keep up with her conversation.
The woman was tall and full bodied with fine firm tits that matched her physique. She enjoyed me playing with her body, everything from fingers tickling her denim-covered ass to soft kisses on her neck while making dinner. The woman liked being played with, certainly could appreciate a much younger man being in lust with her body, but she demanded respect. More than once told me to get back to work, be it doing trim or washing the dishes or lapping at her clit until an expected orgasm caused her to scream and lock her legs around my head. I liked that about her.
First half of our second day together was spent in bed or rolling around on the floor or getting to know one another’s bodies in the shower or kitchen. Then came a lull, resting with a glass of wine and talking about life and death and everything between. I was more nervous talking with her than any other time. I wasn’t worried about how the woman was willing to have me over for the night and expecting me to perform with twice the stamina I’d put forth that morning and afternoon. No. I was hot for Cheryl and could hardly wait to rip her panties off and fuck the woman for another two hours.
No. My only worries came from my own insecurities. The woman was unlike any other female I’d ever been with. Girl. Woman. Hot demanding pussy with a fine body, beautiful face, and a brain that made me question everything. Kind of scary, but I couldn’t turn away from her. Saw Cheryl as a challenge and, pushing away my fear that rose up in the face of a strong and capable woman, I dedicated myself to gaining her own respect of me.
Sounded good at the time as the words rolled through my head, but the woman seemed to know all my weak spots and she sure knew when to make use of them.
That night Cheryl got down to asking for a detailed list of all the girls I’d screwed around with over the previous six months. Mostly Sandy but a couple of others as well, and never with a condom. That last part bugged her, partly because it showed me to be an asshole of a selfish guy willing to pump my raw seed into any and every fertile womb available to me, but also because I just showed myself to be more than likely carrying and passing on to her a dozen different kinds of sexually transmitted diseases.
Sure, I tried to turn it around and question her about her own sexual activities, but she batted my question away and simply informed me that she’d have to check her cabinet for condoms.
“Kind of late, given what we did most of today,” I said a little too smugly, thinking of the total of four fantastic wild streams of cum I’d poured into the woman’s lower body.
“Which is what kind of pisses me off,” Cheryl said without any hint of a smile. “I’m sure you’re as clean as the girls you’ve mentioned, all of them in high school and without a lot of other outside activity, but let’s stay safe. Are you still seeing any of these girls?”
I felt guilty while bringing up girls like Brenda and for lying to Cheryl about Sandy. Told her Sandy was only sixteen and having to stay at a friend’s because of an abusive father. Not wrong, but without mentioning Sandy’s international renown for sexual exploits, fucking and sucking the cum out of everything from grown men to women to canines of indeterminate form or size. I lied, but I was truthful in saying no other woman shared my bed or my interest. Just then, Cheryl was everything to me.
The following morning there was more sex, albeit very safe sex. Didn’t mind that so much. The woman rode my face for a while but didn’t even flinch when I used a condom that happened to be in a kitchen drawer to cover a cucumber and fuck her while tonguing her clit to a second orgasm. Her worries about my state of health didn’t prevent her from sucking my dick for just as long, though I swear she covered my face in more liquid than I ever pumped between her legs.
She dug around and found a half-full box of condoms. Used that second raincoat for me to fuck the woman for another half hour until my balls were pretty much emptied for that part of the day. Wish she’d have let me push that cucumber into her ass while I was filling her pussy, but Cheryl said one dick at a time was plenty for her.
For the rest of the morning I tried to figure out how to tell her I wanted to move in with her and fuck her ass and fill her pussy a half dozen times a day. I was more flowery than that when I brought it up at lunch, but Cheryl told me to pull my mind off my cock and pay more attention to the bad job I was doing at edging the bedroom windows. She was just a little less direct in reminding me that she loved having me around, but not as much as she loved her privacy and her space.
I was deflated, in more ways than one, but Cheryl was nice enough to walk over, unzip me, haul my cock out for a nice taste test, and let me know that I was still in the lineup for her most favorite of activities as soon as we’d finished off the bottle of wine she still had chilling in the fridge.
All was good until towards midnight. Cheryl had done wonderful things with me. We talked about my interest in electric cars, she told me of her one year spent in Italy before going for her MS in Business, and then she made a deal with me. Cheryl told me that she wanted to suck my dick for a full five minutes while she sat on my face and rode me the entire time. I had no problems with that.
Thing is, only if I could keep from cuming in her mouth would she allow me a second try up either of her two lower holes. My choice. This is when she came out with one of her few limitations when it came to sex. She hated blowjobs. She’d suck and lick and orally love a guy, including me, but no cuming in her mouth and no swallowing. This didn’t bother me much at all given how much Cheryl liked to fuck and be fucked. If I could just get a doctor’s note and toss the need for condoms, I’d be a happy man, pumping every ounce of semen my balls could produce into her very lusty snatch.
Finishing off a last half-glass of wine I accepted her challenge, but only if she would give me not five but ten minutes of face time between her legs. She laughed and softly slapped my face, telling me that if I didn’t give her at least two orgasms she’d kick my ass onto the curb. I chuckled, but then stood the woman up, kissed her, undressed her, and kissed my way down her body. With great attention to her magnificent breasts, of course, enjoying her moans as my tongue and lips devoted themselves to bringing both of us joy.
Then lower, to her thick bush. Thick lips, thickly furred if nicely trimmed, and full with her own brand of cum. Delicious. But in a deviant act of my own making, I rolled her hips up, legs over her face, my cock only inches above her mouth. Fighting my own lusty needs, I forced Cheryl to watch as I held her hips up, pussy to the ceiling, and then tipped the wine bottle up and emptied the last half-glass or so of white wine into her already delicious snatch.
She yelped a couple of times and struggled and swore at me, but then moaned in pleasure as I dipped my mouth into her cup of goodness and drank deep. Both wine and her own secretions dripped down to her face and chest, and within ten minutes I had given Cheryl all she needed to keep me and care for me another night. Only two full orgasms, but each filling her thick fleshy lips to overflowing.
In the middle of all that, my mouth literally sucking the woman’s clit into a frenzied state, Cheryl was able to pull me down low enough for her mouth to start on giving me a good mouth job. Mouth and hand, sucking and licking down my ongoing flood of pre-cum while tonguing my balls and finally bringing me close to an orgasm. But I held back, Cheryl knowing to pull back when I warned her about my balls being close to exploding.
With Cheryl’s twat filled with her own cum and my cock twitching and throbbing with need, we quickly rearranged ourselves. Wound up in one of my favorite positions. Lying close, Cheryl’s thigh over my hip, my balls pressed into her ass, my cock deep into her rectum as I filled the woman of my love and lust just as I had the first time we’d been together. A condom sheathed my cock, the principal reason why I’d chosen to ream her ass again. If she’d have allowed me to go wild, I would have rolled on top of her chest and pounded into her pussy for a good half hour before pouring tens of millions of my minions inside of her. I longed for the day.
But, no, a condom was demanded, and so I went slow and sweet, trying to bring Cheryl to another rise and another orgasm.
Not all girls or women in my past liked anal. For me it was fun only as a novel way to take and control a girl, to make her mine. No way would I ever want to know that some other guy had blown a load into her ass when I hadn’t. All parts of a girl were a turn-on for me, a part worthy of being fucked and filled and laid claim to.
Cheryl’s openness to anal was fine with me, and as we lay there and fucked and kissed and moaned, I tried to go further by giving her a little extra with my fingers. Not just a finger to her clit. This time a couple of fingers into her open vagina, reaching deep and curling up, trying to excite the woman’s g-spot and having her set her bed even more than we had the night before.
This finger thing wasn’t a sure thing. Not all girls liked fingers, on clits or up twats or even around the anus. Every girl was different, but Cheryl was into everything. Only five minutes of slowly filling her ass and massaging her pussy Cheryl erupted like Italy’s own Mount Etna. Wild and wet, her mouth latching onto mine while her entire cunt flooded my hand with cum and filled her ass crack with enough lubrication to last us a month of butt-fucks.
When the climax was over and Cheryl lay back in exhaustion, I lovingly and patiently rolled onto her ass and fucked her like a horse in gallop mode. Lifted the woman’s ass up and ground my cock as deep into her rectal depths as I could. The violent ride only lasted a couple of minutes before I reached my own climax, but it felt good to hear Cheryl grunting and shrieking as though some demon from hell had truly taken her over.
Me having to cum inside a rubber tube was no fun, but loosing all of my violence on and inside of the goddess of love and sex and lust was absolutely one of the highlights of my life.
Good sex. Hard and lusty and without a single apology.
And then came the post-lust anti-climax, if I can call it that.
Lying there with Cheryl, very awake because that’s how sex affected her. Some girls, and most guys, are ready for a long night’s sleep after an evening of hot and heavy sex. Cheryl had the opposite happen to her. She was buzzed and ready for a snack and perhaps a little more painting in a corner just above the shower area. Fortunately, my post-sex treatment of kissing and massaging kept her within arm’s reach as we enjoyed each other presence on a cum-soaked mattress. Unfortunately, I couldn’t keep my mouth shut.
“So. When can I go wild inside of that very tasty pussy of yours? It felt so good letting go inside of you the other night. The condom was okay, but you said you’ve got protection. There’s something special about flooding you with my own special juices. Really want to do that again.”
“Yeah,” murmured Cheryl, her soft voice belying her sarcasm. “Really love knowing some male wants to douse me with his scent and maybe have a thousand of his sperm gang-bang one of my eggs.”
“Hey. Didn’t mean...”
“Don’t be so sensitive, Louis. I get it. Hot wet sex is the best. Just need to be careful right now. Do that thing done with the doctor. Let me know the results. I trust you.”
“Yeah,” I whispered, trying to think of the last time I’d seen a doctor. “Will do. Hot and wet with you twice a day will never be enough.”
In an effort to stay connected but change the direction of the conversation, I gave a long lap of Cheryl’s sweat soaked right nipple and drove myself off a bridge.
“Speaking of wet and wild, there’s some wild caught fish at the market. I can pick some up to bake tomorrow night. Maybe with rosemary. Sound good?”
“Nice, Louis,” murmured Cheryl as she rose and reached for her panties. “But I’ve got a busy weekend. Leaving super early Saturday. Spending two days at a friend’s near the beach. Won’t even be back until late Sunday night. Don’t have anything planned for the following weekend, though. You practice your grilling skills and maybe we can have a raincheck.”
Ouch. Nice, but that hurt. She walked out of her darkened bedroom and on to the kitchen, and nice little lapdog that I was, I followed. Then I stopped, realized what a weak little pussy of a boy I was and forced myself to back off. I did, but not enough, and Cheryl’s little lecture sure took me down to size.
Walking behind Cheryl, I tried to stay neutral, giving her notice about both my preferences and her total power to make decisions. I wanted to seem strong and independent with a clear indication of where I wanted to go without backing her into a wall.
I pressed my half-hard and very willing dick into Cheryl’s panty-covered ass and put a hand on her hip, saying, “Hey. I’d like to stay, all night. Even if it’s just to sleep. I’ve got a day off on Tuesday. How about I come back then. Do some painting and baking. Maybe finish off another bottle of wine.”
Strong but suggestive. Didn’t ask about who she was spending the weekend with. Nothing wrong with what I put out to Cheryl, but she heard more than my words and she sure let me know it.
“Listen. I really need to have a full night’s sleep. You wake me up in all the best ways, but I’ve got some work to do tomorrow before I leave. And maybe Tuesday is too soon. Keep your eye on next weekend. Text me and we’ll make plans.”
Then I did the stupid thing, leaning down to kiss her neck and saying, “But...”
She heard that one word and it was all she needed to lay it all out for me.
“Really, Louis. It’s been nice, but I’m worried you’re getting too carried away. I like this. I’d like more of this, I think. That’s something we both have to mull over. But no way I’m ready for you to move in or for me to start seeing you every night. Maybe not even every other week. The sex is good, but your attachment to me is starting to scare me. Do you get that?”
And so a woman with my cum still crusting on her tits tossed me from her house and did everything but slam the door on my bare ass.
Almost spent the weekend painting the rest of Cheryl’s rooms. Knew where her spare key was hidden and thought it would be a kind and yet strong gesture on my part. Not asking for anything, just doing everything she needed her man to do. I was sure she’d love me for it and ask me to stay forever. Thank god my housemate Jack talked me out of it. He saw, as I couldn’t, that Cheryl would get doubly paranoid and do everything but call the police in an effort to keep me a lot further than arm’s distance.
And that’s pretty much how our hot relationship turned into something that had a distinctive ‘friends with benefits’ feel. Still hot, but only occasionally. I’d drop by or text, maybe even an e-mail about a movie, and maybe we’d get together for longer or maybe not. Long lust-fueled nights were rare, afternoons into evenings in her bedroom maybe once every couple of weeks. It was good sex, a wonderful new relationship, and yet it killed me because I wanted more.
Maddening and frustrating, but no way do I have anything bad to say about Cheryl. I could go on for hours and pages about all we did together and talked about and, of course, the very fine sex we experienced. Sure. But something happened while I was off getting a go-ahead from a doctor to pump another dozen loads of raw semen inside of the woman over the next weekend. Got that. Did that. But something else came up that still rides in the back of my brain.
Tried to get a blood test but was firmly told by some office assistant that, given my age and etc., the doctor wanted me in for a physical as well. No physical, no sense in getting checked for stuff like cholesterol or syphilis. Stupid, but then it took me ten minutes of whining and arguing to see a doctor before the following week.
Got to see the doctor on Tuesday. Lost work hours but it was worth it. I was a fine physical specimen, in perfect health, until the geriatric doctor told me to drop my shorts. No need for a prostate exam, but this guy took a good five minutes playing with my balls. Weighed them with both hands as though he was juggling them. Hefted my dick, which thankfully stayed soft, and then went back to checking my balls. Then his pronouncement.
“Nice set of balls you’ve got there, son.”
“Um, thanks.”
“Any pain or discomfort? You’ve had sex before, I see. Any problems?”
“Um, no.”
And then the medical expert goes on to tell me that I’ve got a larger than average pair of testicles, even given my good physical size. Told me that dicks didn’t matter as much as a man’s testicles when it came to sex or having kids. He’d been a little worried that I might have extra testicles but, no, just two larger than average nuts in my fatter than normal sac which also happened to be covered with a rather large amount of pubic hair.
He had lots to say and mutter, but all I heard was that I had big balls, a lot of testosterone, and probably a greater amount of semen than the average guy for each ejaculation. All sounded great to me.
“Your wife will probably complain about the mess,” the doctor said in a deadpan voice, “but it shouldn’t hinder or even help all that much when it comes to having children.”
That answered a few things, like why even girls like Lucy and Jasmine and Sandy always had trouble swallowing when giving me a mouth job. Which, in turn, is why they would always prefer turning up their ass and allowing me a quick cum-dump in their more spacious pussies. I never minded, always preferring a fuck and flooding of a girl’s twat to even the best of blowjobs.
That’s what was going through my mind as the doctor droned on, sort of proud at how even Sandy noticed not just my appreciable amount of cum, second only to Eddie, but also the strength with which I could pump it out. Not kidding here when I say I’ve been able to shoot a line of cum halfway across a room, much to my mother’s disgust when she makes the mistake of trying to clean my bedroom.
Anyway, the smile on my face was wiped away by what the doctor said next.
“Son. You ever get into fights at school? Any problems with hitting people or getting angry? How about road rage or pissing off your friends with your bad attitude? Anything like that?”
“Um, no sir. Friends think I’m a nice guy.”
“Well, good. Keep it that way. And what I mean by that is as you get older you might have problems keeping your temper. It’s not pre-ordained, but hormones don’t just affect the women. Men go through changes too. Up to you to hold your temper and count to ten, or maybe to a hundred, before going off half-cocked if you’ll forgive my use of the phrase. If a friend ever backs up and says you’re getting out of hand or being scary, listen to them. You understand what I’m saying?”
“Um, yes sir. I should watch my temper.”
“What might bother another man might become a burning rage inside of you. It’s up to you to control it. Keep that in mind.”
Had to wait a few days for the results of the blood work, but I didn’t care. On the way back to work all I could think of was how I was an above-average guy with enough sperm in one shot to fertilize very woman in America. Kind of a real ego boost. Didn’t go around bragging about my balls to the other guys, but it sort of made sense. Girls had mentioned how hairy my chest was and how they could feel my balls bumping into their ass or thighs when I was literally going balls-deep into them during a fuck.
But then the words of the old geezer when he warned me about sudden rises in anger. Lucy had come right out and told me to my face how scary I could be during sex. I didn’t think much of it, but with the doctor’s words guiding my thoughts, I was able to picture all the things I’d done to girls over the past handful of years.
Never hit a girl. I’d never even gotten into a real fist-fight with another guy. But during sex, when my cock was up and the scent of a girl and all her sex was in the air, I tended to blank out and let my rougher desires take control. More times than I cared to remember I’d tear a bra strap, rip a girl’s panties, force her legs wide, crush a hand into her throat, and penetrate her and fuck her and cum inside of her with hardly a thought to the real consequences of my actions.
Sure, always with an apology after the fact, but with little regard to how my lust and need to fuck and cum wild and free inside of a girl always took precedence over going slow and talking it out. All through that day of work and on through to the weekend my mind kept remembering events and girls and women and times when I lost all sight and thought, the need to fuck and cum taking me over.
Yeah, kind of scary. I almost started digging for Lucy’s contact info, then started thinking about the nameless girl I’d forced myself on in her car just a month or so before. And just two weeks before that, a high school acquaintance had allowed me to drive her home. I’d talked my way into her bedroom and while she seemed somewhat willing to give me a mouth job, I wanted just a little more.
I was sitting on her bed, the girl half-standing with a knee up, her face pushed into my crotch with one hand, my other pulling up her blouse and getting a good feel of her tits. Before I even knew what I was doing, I had a hand down her pants, and when she tried to pull away, I pushed her pants down and rolled her chest down on the bed. It was an easy thing, even with her pants around her knees, to push my throbbing cock between her pussy lips and then inside of her. Rode her bouncing bed to a fast climax, my feet planted firmly on the floor and my cock pushed deep inside of the girl’s wet and cock-sucking twat.
My balls were still pulsing out a stream of cum when the girl begged me to stop and to please not cum inside of her. She was afraid of getting pregnant and wanted me to pull out of her. Too late, my balls were already a few ounces lighter, but if she didn’t know that, it didn’t bother me.
With my cock still hard, I pretended to hear her concerns and told the girl I’d pull back but only if she’d let me take her up the ass. She seemed astounded by my request, but before she could come up with any objections, I hauled her ass up high and made good use of her.
I thought I’d been the nice guy, pulling out of her very warm pussy and splitting her anus. I would have preferred a longer fuck of her pussy and pumping another load of cum to marinate in that secret garden all women had between their legs. A girl’s fertile snatch was always my first choice, but, being the nice guy, I went on to ream this girl’s ass and ride her for a good ten minutes before pumping that second load of cum safely into the depths of her rectum.
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