Derby Day
by PolyOldFart
Copyright© 2024 by PolyOldFart
True Story Sex Story: An unexpected request leads to a voyage of sexual discovery by a 40-something Southern belle.
Caution: This True Story Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual True Story Sharing Anal Sex Pregnancy .
I was a bit taken aback when Lola invited me over for a drink, then asked me to fuck her.
We’d been friends for a couple of years, since she’d lived right across our narrow residential street with her husband in our small Southern college town. I’d always been kind of surprised at them being a couple. She was an interesting, opinionated grad student in English, who had returned to grad school after some time out teaching English in a small religious college with her Master’s. She’d returned in a PhD program to try to get qualified to move to a bigger (and hopefully better paying) school.
Her husband, Harry, was totally different. He was in his early 30s, a junior college dropout with what seemed like little skill, little ambition, and--the real surprise--little personality. She was one of those people that most people will remember after they’ve met her: Opinionated, as I said, quirky, but bright. He was one of those who didn’t show up on your radar if there was anyone else in the room, even a corpse.
He’d had several fairly unskilled jobs. His one try at an Electronics Assembler job hadn’t gone well; he’d managed to break the machine that they were testing his assembly skills on. Needless to say, he wasn’t asked back for a second interview.
So, I’d always wondered what had attracted them. Maybe, I thought, the old saw about “opposites attract” had more validity than I’d observed among my other friends. I figured there must have been something that had attracted her to him in the first place.
Lola was in her early 40s. She was at that age when women who are marginally attractive at 30 start losing that and begin to become frowsy. That was certainly true of her face. It looked every one of her 41 or 42 years. Her hair, which was fairly dark and nondescript, without much body, didn’t do anything to enhance her face. Rather, it sort of hung lankly. Her body, on the other hand, was quite a different story. She still had a magnificent figure, with only a trace of a middle-aged pot belly beginning to show. Otherwise, she still had excellent legs, a lush--rather than small--ass, and lush tits. She was about 5’5” tall and average weight, but her tits were about a 34C. They’d begun to sag a bit from their own weight, but that gave them movement under her clothes--even with a bra, which, being a proper Southern girl, she almost always wore.
My wife and I had been to the local lakes, picnicking with Lola and Harry, a few times, which had given me a chance to become rather familiar with Lola’s lush body. I’d caught myself staring more than once at her luscious boobs in her barely-modest bikini, and had once caught just a glimpse of some chestnut pubic hair peeking out the leg of her bottoms, something I’ve always found a turn on with most any woman.
I thought I’d been reasonably discreet in my appraisals of Lola’s body. I hadn’t looked up from admiring her tits to find her looking at me or anything. So I didn’t think she was particularly aware of my interest.
A little about me in those days. I was in a graduate program in a different department at the same university. Having come to it directly out of undergraduate school, I was by now in my mid-20s. While I didn’t work out or anything, I was active. I did some softball with the other grad students and a little running twice a week. I wasn’t fanatic about it, but I was in pretty good shape, at about 5’9” and 160 pounds. My wife told me I was very good looking and sometimes I could almost see that in the mirror.
We were in a small, rather conservative town in the South, and Lola was from a neighboring Southern state, of old Southern Scots-Irish stock. I was the oddball, as I’d come from a fairly progressive Western state, for a specific program offered at this school. Adjustment to the South can take a while. This was particularly true then, not long after the Civil Rights struggles of the ‘60s, but I thought I was doing pretty well. Getting to know Lola and talking politics, religion, and social customs (all those forbidden topics in polite society, but which are often the subject of discussion in grad school) had given me some insight into the Southern mindset. That day, Lola had a further initiation planned--into the way modern, progressive southern women deal with their own problems. Or, at least, how she planned to deal with hers.
She’d invited me over to their new rental house, which was a couple blocks away--a charming cottage in a somewhat quieter neighborhood, a little further away from the “student ghetto,” and more secluded on its larger lot. My wife had been promised elsewhere all afternoon, as I told Lola when she called. She said that was fine, as Harry was out of town for the weekend, too, visiting his parents about 75 miles away, anyway, and she was lonely. “We’ll keep each other company,” she said, as we said goodbye.
I thought nothing of it particularly. It was the middle of the Spring term, early in May. Spring Fever was rampant around campus. And class work and research weren’t particularly pressing at the moment, so I had some free time. She’d discovered she liked California wine. I usually picked up a case or two when I passed through in the summers, as I liked them, too. We’d gotten together periodically to share some of the wine and talk and it had been fun. As I said, she was opinionated, as was I. I’d offered a bottle from my precious stash this time when she called, and she’d said it was “Derby Day,” and that was a time for mint juleps, so let’s save the wine for next time. That sounded fine to me, so I wandered the few blocks over to their house an hour or so later, after finishing up some note taking for a paper I was working on for the following week.
When I got there and knocked, she called to me to come in. She was in the kitchen, she said. I started toward the back, where the kitchen was, and she came through the door before I got there, with a little tray with some crackers and a little wheel of Edam cheese. She was dressed in a pair of old pants and a mostly-opaque white blouse, with some open lace cutouts at the side, which gave a slightly “peekaboo” view of what was--and wasn’t--underneath. This was unusually risqué for Lola, but I put it down to the heat. I could see the pneumatic swaying of those magnificent tits. In fact, they seemed to sway rather more than usual, which, of course attracted my attention. Several sidelong glances later, I realized one of the things that I wasn’t seeing was the band of a bra in the peekaboo sides, which was pretty unusual for her. I did say she was Southern. Those who know that mindset will know that one doesn’t “flaunt” one’s body in that society, unless one is overtly flirting.
She went into the kitchen and brought back another tray with a couple of tall glasses with sprigs of mint sticking out. “Harry’s folks gave us a bottle of Bourbon for Christmas,” she said, “so I thought I’d put it to its highest and best use.” Being a Westerner, I found the drink a bit sweet for me, like southern iced tea, but I liked the bright, spicy, vegetal scent of the mint and the sharp bite of the Bourbon, offset by the sugar. It also had a pretty fair kick. I had a feeling Harry wasn’t going to get a lot of this bottle of Bourbon.
We talked about our usual array of topics for probably a half an hour, warming to them as the Bourbon warmed us. She insisted we turn on the TV long enough to see the race, which was won handily by some horse named Riva Ridge. We were through with the race and into our second round when Lola put her glass on the table and looked at me seriously. “Will you fuck me?” she asked.
I didn’t quite snort my last sip of julep through my nose, but I did cough a bit. Suddenly sober after her query, despite being into my second julep, I sensed this was a “Big Question,” not just an invitation to a casual romp. So I thought that, instead of just saying “sure, which way’s the bedroom?”--which would have been my inclination for casual sex--I ought to perhaps explore where this was coming from. Lola was too old-fashioned to just decide she liked the cut of my jib and want to jump my bones. There had to have been a lot of thought behind her offer. After all, she did have a husband, and she knew I had a wife, whom she appeared to quite like, so the usual motives of horniness or revenge didn’t seem likely. But while I was still hemming and hawing, trying to come up with a good line of approach to the question, the answer came spilling out of her.
“Harry doesn’t want to fuck me any more,” she said despondently, “and I really want a baby. I don’t have too much more time left to have one. I know I like you and I find you very attractive, even if you are one of those liberal westerners,” she winked at me. “I’ve been thinking about this for months, and I think you would be a wonderful father for a baby.”
“I’m very flattered,” I said, stalling for time and cudgeling my brain for a way to say what I wanted to. “But you know I already have a wife, and you have a husband, uh, what...” and my voice trailed off. “Fool,” I thought to myself, “that was really smooth. Why’d you bring that up? Now she’s going to get cold feet and have second thoughts about the offer!”
“I know. It makes it a bit more awkward. Frankly, I don’t think Harry and I are much longer for coupledom. I married him four years ago because I was desperate to have a child and he was the first one to ask when I was sorely feeling my biological clock ticking. He kind of indicated then that he understood that children were part of the marriage package. Now, too late, I know that he doesn’t want a child, not really. He’s too set on being the child in our relationship. He’s a Mama’s boy--look where he is today!--and was looking for a Mother to take care of him. Well, I’m looking to be a mother, but not to a grown man! I want a baby to raise into a real person, not some imitation.” Her voice was rising a bit as she warmed to her topic. Obviously, she’d been giving this a LOT of thought. And probably been keeping up with me on the juleps.
“I guess my concern is that I’m married to someone else, and I love her a lot,” I said. “It wouldn’t stop me from making love to you--we don’t feel we need to have a sexually-exclusive relationship--but it would make it hard for me to be a Father to your Mother. Besides, there are all sorts of legal hassles I could get in, and wind up responsible for paying child support until the kid’s grown. I don’t think I’m ready for that. I’m not even ready to have kids of my own with my wife. I can’t afford it until I’m out of school and have a career started.”
“I know,” she said. “I’ve thought about all of that, too. But all I’m really after is someone to give me what I need to conceive a baby. I fully expect I’m going to have to raise it by myself, even if Harry and I stay together, which I don’t think is too likely. I think my being pregnant would be the final thing to drive him away permanently.”
“Then why do you want to do that?” I asked.
“I don’t, but I see it as inevitable, if I’m to have a child,” she said, a bit despondently. “I’ve just come to the realization that I want more to have a real child than I do to have a man-child. Particularly one who won’t even fuck me. I mean, I know he doesn’t because he’s got enough sense to understand cause and effect: having sex makes babies. And he has some visceral realization, even if not at a conscious level, that he doesn’t want that, that it would take away his status as the child in the family. I don’t think I love him anymore, if I ever really did. I think I had him in mind more as a sperm donor, rather than a real husband and father. The way I was raised, good girls got married to the fathers of their babies. But he won’t even do that. Did I screw up?” she looked at me, not really expecting a response, then answered her own question, “yeah, probably. I felt I was too good for men who were interested when I was younger. They were too immature, or not well enough educated. Or, the ones that were, put on too many airs. Then, as I got older, the men stopped being as interested and I realized I might never get married, and might never be able to have my own children. I love children. My nieces and nephews are the lights of my life, and the realization that I might not have any of my own, I think, panicked me into saying yes to Harry without really thinking it through. That’s why I’ve thought and thought and thought about this. I didn’t want to make another mistake by doing this. I realized I’d have to do this alone, but I’d rather do the part that needs a partner with someone I know, and like, and find attractive, and think would produce amazing babies. Besides, I think that’ll make this part a lot more fun.
“If you’re OK with the idea of not having any responsibility for any child we produce,” she went on, “I’m OK with it, too. I don’t want your money or moral support, really. I don’t even require your presence for the child.” She added quickly, “now I’m not saying I won’t welcome any time you want to spend. I’m not saying that. I’m just saying I won’t require you to be a Daddy in any sense but the biological.”
She momentarily ran out of steam and took a pensive sip from her julep. She looked up at me and looked me in the eyes. “When I look at you, I see someone who is handsome, educated, bright, and, maybe even more importantly, is kind and thoughtful. But I’ve also seen how you look at my body when you think I’m not looking. I flatter myself that the attraction isn’t entirely one-way.” Oops. Caught! I actually blushed a little and took my eyes away. When I looked back, she was smiling a slightly triumphant smile. “Yeah, that’s what I thought.”
She looked into my eyes again and said, “the other thing I suspect, from some of the things you’ve said in the past, is that you’re probably a very good and kind of experimental lover. Until Harry came along, I was really pretty picky about who I’d sleep with, so, considering how old I am, I really don’t have very much experience. There were a couple of rather fumbling guys in college and a couple more in the 15 years after that before Harry and I got married. Can’t say my marriage has provided a whole lot more variety of experience. Harry’s sort of like vanilla ice cream in bed--good enough, but rocky road or chocolate might be nice some time.” She blanched a little after saying “chocolate” and became a little pensive. “No,” she said, “no ‘chocolate.’ That one was drummed into my head early on. Black men scare me. Excite me ferociously, too, if I want to be honest about it, but they scare me.” She thought a moment more, “the thought of fucking you scares me, too, but not the same way. And it makes my panties wet as well. I’d like to try some new things I’ve only read about, if you’re willing, but there may be things you want to try that I’ve never done before. I’m kind of willing to try ... um, most anything, I think.” She looked at me a bit apprehensively, “But I kind of don’t even know how much I don’t know, if you understand what I’m sayin’. So I’m also kind of terrified of what I don’t know. Do you promise to be gentle and take it slow with me?”
“Lola...,” I started. Then I stopped for a minute to let all the thoughts and bawdy images swirling through my head kind of settle down, and my prick to go down a little in my pants. “I do find you attractive, both mentally and physically. I think ... no, I AM willing to magnanimously help you out with your project,” I said with exaggerated pomposity, bowing in a parody of a Southern gentleman, then breaking the image by winking at her. “I’ve actually fantasized about fucking you for a long time, but I never thought it would go beyond fantasy. And yes, I can be gentle. And yes, I’m willing to try all sorts of interesting and kinky and perverted things with you, as long as you promise always to give them a try. It only has to be once, unless you decide you like it. If you don’t, we do something else. OK?”
“Sounds like a deal, kind sir,” she said, and offered her hand with exaggerated grace. I took it and, instead of shaking it, I brushed the back of it with my lips, Rhett Butler-style. “So, how’s about it?” she said, with a mischievous grin, “You want to find out how big my tits really are? And whether I’m really braless?” She winked at me, then quickly got up off the couch and bolted for the bedroom, me following in hot pursuit, slightly slowed by stopping to pick up our glasses.
When I got there, she’d thrown herself onto the big queen-sized bed (their one extravagance, she’d told me, when they moved into the new cottage). She was lying there, face down. I put the glasses on the nightstand, took off my shoes, and tucked them under the foot of the bed. She rolled part way over on her side so she could look at me. She smiled. I walked around to her side of the bed and pulled her up to stand in front of me. No words were needed now. I leaned down and kissed her. She tasted of mint julep, with a back bite of her cigarettes. I tickled her lips with my tongue and she opened them just a fraction. I insinuated my tongue through them and into her mouth. She probed my tongue with her own, giving it little licks, then opened her mouth wide, and relaxed a little in my arms, putting hers around my back and one up over my shoulder, behind my head. If my instincts were right, she had probably just flooded her panties.
We kissed like that for several minutes. She was a pretty good kisser--her mouth was mobile and her tongue would seek out mine, rather than just being passive. Meanwhile, the closeness of our bodies rubbing together gave me a tactile sense of her “high points.” Her breasts pillowed against my chest, with her nipples quite apparently hard. Her pubis sought out my left thigh and rubbed a little against it, my cock meanwhile was just barely getting any friction out of her left thigh, which was a little too far away. Everything pointed to her being a rather horny partner.
She’d made me the offer of her tits, but I’d only felt them pressing against me so far. I drew out of our kiss gently and said, “OK, that was a nice appetizer, but you were going to show me how big your tits were. How about we find out?” With that, I held her out at arms’ length and looked at her blouse with an eye to how best to remove it. Being a woman’s blouse, it buttoned on the “right” side for her. And facing her, it meant it was on the “right” side for me to unbutton easily, too. But the buttons, though dainty, were heart-shaped, and the button holes were too small for easy negotiation. I struggled through the top two buttons, then asked her if it would be OK to just raise it over her head. “If you do, you’ll find out pretty quick what size they are; I’m not wearing a bra.” “I didn’t think you were; they were moving too enticingly.” She dimpled, then reached for the bottom hem of the blouse. I put my hands on hers and said, “let me ... I want to do the unveiling.” I raised the hem quickly to mid-belly, then slowly over the undersides of her peaks, finally revealing her large orbs, with silver-dollar sized areolae in a lovely dark brown color, and fat, crayon-sized nipples, already crinkled, as I’d felt, with both the cooler house air and excitement.
I got the blouse over her head, and she raised her arms to take it off. Then I had a thought. While her head was still trapped in the blouse, but her tits were naked, I reached up, took both her raised wrists in one of my hands, then leaned down and captured one of her nipples in my mouth. That got a sort of combination groan and hum from her, which told me I’d found a good spot. I sucked and licked on the nipple for a couple of moments before releasing her wrists and helping her remove the rest of the blouse.
Then she was standing there, topless, with her large breasts where I could feast my eyes. They were probably a large C or small D in size, and quite soft, with definite teardrop droop. That big and in her forties, they weren’t the pert mounds of a 19 year old. But they weren’t down around her belly button, either. They definitely had mass and sat nicely on her chest. The nipples, too, were very appealing, still pointing outward, somewhat wall-eyed, to either side.
Smokey-eyed, she looked at me. “Like what you see?” She twisted a little bit, setting her mammaries gently in motion, which was quite delightful. From my smile, she could tell my response. “You know, what you did just now, with the sucking and licking? I’m so hot at the moment that I think I nearly came from that. Better not do to much more of that, or I may be done for the night.” “You know,” I said, “men sometimes have that problem of ‘one and done,’ but many women have orgasm after orgasm and can keep going until they have to stop from exhaustion. But some can only have one big one, then they have to stop. Do you know which kind you are, or is it dependent on the situation?”
Lola looked at me thoughtfully. “I’m not sure I know. I haven’t come very often, though there have been a few times when that HAS to be what happened. Harry’s not a very great lover. Mostly--when he actually DID make love to me--he’d use me, um, ‘down there,’ to stroke himself until he got off, then he’d roll off and go to sleep. A few times, when I was in a mood, that would be enough to excite me until I’d have something that seemed like the buildup and climax he was having. Felt mighty good, too, but it wasn’t something that happened all the time. And once was all it ever was, because he was asleep before I could get there again, if I could have.”
“You didn’t ever do yourself, then?” I asked.
She had the good grace to blush furiously. “Good girls don’t; and I tried to be a very good girl.” Her expression got a little sour, “You see where it got me?”
“Well, let’s try a few ‘bad girl’ things that I think may make you feel very good. I really like your tits, so I’d like to have another go at them. But I also love eating pussy.” I stopped and thought a second. Some women are very sensitive to the words you use to describe their genitals, and I didn’t know Lola’s preference. “Are you OK with the word ‘pussy’ for that lovely spot between your legs? I know some girls prefer ‘cunt’ or ‘vag,’ or even the clinical ‘vagina,’ and others are totally turned off by those terms. What’s your preference?”
“I hadn’t really thought much about it, but when you said ‘pussy’ just now, I know I wasn’t turned off by it. So I think ‘pussy’s’ OK. I’ve never heard ‘vag’ and it doesn’t do anything for me. I’ve heard ‘cunt’ a lot, but usually only as a cuss word. I think it would make me feel dirty.”
“‘Pussy’ it is then. Though, in the heat of passion, ‘cunt’ might work to make you feel dirty, when you really want to feel like you’re being fucked down and dirty. Ya think?”
She thought about it a second, after the shock wore off her expression. “You might be right. Don’t use it right now, when we’re kind of being tender. But if it came out of one of us when you were pounding me, it might work. Maybe try it some time and we’ll see?”
“That sounds good. Alright then, back to the question. Have you ever had your pussy eaten?”
She blushed a bit again, and was very slow responding. “Only once, but it was pretty embarrassing. And definitely NOT a ‘good girl’ thing.”
“How so? The actual pussy-eating, or the situation?” I asked, puzzled.
This time, she reddened from the top of her brow to the middle of her tits. She cast her eyes down and mumbled, “the pussy-eating was good. Umm, actually, better than good. But...” She paused and looked at me in a slightly pleading way, “you won’t think I’m terrible, will you?”
Hmm. What have we here? “Whatever two people do that they both enjoy is pretty much OK by me, so no, I won’t think you’re terrible, pretty much whatever you did,” I said gently. Let’s see. Probably not a husband whose been characterized as unadventurous, at best. So, what? Ex-boyfriend? That probably wouldn’t make her blush that way. Hmm? Ah! “A girl?” I asked quietly.
This time, the blush was a quick flush from head to toe. Then a slight nod. I was right!
“We were roommates in college. She’d brought a boyfriend from high school along, but the relationship had fallen apart. She was devastated. She and the boyfriend had been all but engaged and she’d felt she could allow him pretty much anything but her... ‘pussy,’” Lola blushed a bit again, “she told me he’d been eating her for some time, which she said she really loved. When they broke up, she’d gotten very horny and frustrated and shared that with me. She told me how good the pussy eating had been and how much she missed it. Finally, she asked me if she did it to me, would I do it to her? I was sort of horrified and told her I wasn’t a lesbian. She said she wasn’t either, but we were all we had at the moment and that she was sure I’d like it. She’d made it sound so forbidden, but so delicious, that I decided I’d try it. We only did it the once, and I wasn’t sure how I felt about licking her, but I loved the feel of her mouth on me. I think she came; I didn’t quite get there, but it was still luscious. But I was embarrassed around her ever after. The next semester, she quit college and went off and got some salesclerk job. I lost track of her after that, and was kind of glad, too. You know, ‘bury the evidence’ and it never happened? None of my boyfriends ever offered and Harry’s so unimaginative, I don’t think he’s even thought of it.”
“So, it sounds to me like doing it with a boy...” I looked at her expectantly. “Might be very nice indeed,” she responded.
“What about the ‘other way,’ I asked? You sucking me?”
“I’ve done that with boyfriends. It usually kept them from pushing for sex. I offered Harry, but he didn’t want to ‘dirty my mouth,’ I think was the way he put it.”
“So you’ve done it. Did you like it?”
She looked thoughtful for a minute. “ A couple of times, when I really thought I maybe loved the boy, it was really fun. I felt like I was giving him, hmm, like a gift. It felt OK to do and I learned to keep my teeth out of the way. But I wasn’t sure what to do with their cum. If they warned me, I usually stroked them out onto my tits. They didn’t seem to mind that too much.”
“That’s not too bad,” I said, “but the best gift is to take all of his gift in your mouth and swallow. That’s what a really good blowjob is all about. Then if feels like you’ve taken his gift and accepted it.”
“I never thought the dribs and drabs I got in my mouth tasted all that good--though I think it actually varied some from time to time and boy to boy, and it wasn’t all that bad, either. But, when I think about it, I didn’t spit out what I did get. I must have swallowed it. So I guess it’s not too awful.”
“For me,” I said, “sex between two people who like and respect each other and want to share pleasure with each other should always have a degree of mutuality. Both should be trying to help their partner have the best time possible and the most enjoyment they can have.”
“Now I know I picked the right guy for this,” Lola said, and reached up to pull my T-shirt loose from the belt of my slacks and pull it up over my head. She quickly reached for my belt buckle and undid it, grabbing my slacks and underpants together and sliding them down in one quick motion, where they stopped, snagged on my sandals. “All this talking has gotten me excited,” she said, “I can’t wait much longer.” I sat on the bed and unbuckled my sandals, which allowed her to rip the pants off over my feet and toss them in a corner.
Kneeling on the floor in front of me to remove my pants, she was in an excellent position to get a good look at my cock. She licked her lips and leaned over me on the bed and took me in her mouth. Just a few sucks and I was at full extension. She pulled her mouth off for a moment, looked at my cock, then up at me, and said “you’d make about two of Harry. You’re pretty big, in my somewhat limited experience.” “Not too big to have lots of fun,” I said, “but you’ve still got too many clothes on. Stand up.”
Lola did as ordered and stood in front of me, between my legs, as I sat on the bed. Her pants had a drawstring closure with a bow in front. I untied it and slid her pants to the floor. Surprise! No panties!
“I thought good girls always wore proper undergarments,” I teased, looking from her furry crotch to her eyes. “I’m sure that’s true,” she responded, her eyes twinkling, “but good girls also don’t ask their friends over to knock them up. It seemed like panties would just get in the way, and you have no idea how sexy it made me feel to be sitting across from you with no bra and no panties. Ummm.”
“Oh, really?” I said. I reached out to her crotch and gently stroked the fur over her lips. It was already matted with moisture. “Seems like it did. You’re a very wet girl. And not a good girl at all.” I pressed a finger between the soaking lips of her pussy and stroked from her hole to her clit, gently rolling my now-wet finger around her nub. She quivered. Yes, actually quivered. “I guess I better not do that anymore while you’re standing up, or you’re likely to fall down.” Lola didn’t respond, only bit her lower lip and nodded.
I removed my fingers from her pussy and pulled her on top of me, pulling her over onto the bed. My lips sought hers and we disappeared for a small eternity into a very sensual and exciting kiss. The position, half on and half off the bed, wasn’t one we could hold for long, though. I rolled her onto her back, stood up, and pushed her a bit further up, so her ass was on the edge of the bed. She spread her legs, probably expecting me to go into her. Instead, I got down on my knees beside the bed and began kissing her thighs, first one, then the other, working from her knees toward her center. Surprised, she stiffened a bit, but, when she felt the kisses and licks on her thighs, she groaned a bit, then relaxed completely.
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