Questions Answered

Story Info
His girlfriend finally reveals her steamy past.
12.6k words
4.23
57.8k
14
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My girlfriend Marie and I enjoyed reckless getaways from our homes, from our jobs, from our lives. Life should be fun, right? We really knew how to ditch work and other realities. We'd go away, fuck until we were sore, then we'd rest, fuck some more, and go back home to recuperate and deal with the rest of life. Quite unexpectedly, our last getaway had turned into a frat-house orgy, and it brought out a side of Marie that I'd never seen before. For one, it was evident that she had a lot more sexual experience with guys than I had previously thought. She had technique that would rival a pro, and she had stamina. How naïve I'd been to think that she was an innocent, inhibited intellectual. She had demonstrated a bi-side of her that I never would have dreamt was there. Marie was always a highly assertive woman, but she had acted quite the submissive to a dominatrix.

I had always known that Marie kept personal secrets very, very well. On the other hand, she made no secret of the fact that she had always been attracted to older guys – like me, for instance, I'm fifty-two. She boasted that at seventeen she was dating a thirty-two year old guy. Beyond that, she told me nothing, other than that the twenty-plus year difference between us was "nothing" to her. How old had her lovers been, I wondered.

I tried my best to contain my questions. She was very private, and she would have resented it if I had tried to pry information out of her. Instead, I mentally reviewed every scrap of information that she had ever given me. I constructed a profile, so to speak.

She was raised by an unassertive mother, an alcoholic father, and a drill sergeant grandfather that overcompensated for his ne'er-do-well sons. One was an alcoholic, the other was a perpetual adolescent, ever enthralled with cars. No, she had not been sexually abused, but she had been the only girl among lots and lots of male energy. They had lived on a ranch, and she was surrounded by lots of crude jokes and stories. She had seen animals of all kinds (and a few humans) copulating.

She was extremely bright, and she learned from everything she encountered. She gave up her virginity at seventeen thanks to her older suitor, but she had experienced sex in other ways even before age eleven. She had played with herself, and, of course, she had watched the animals. She knew male and female rutting behavior like the back of her hand. She raised dogs until the hormones hit in adolescence. Then, the alpha dog on the ranch would aggressively try to mate her. She said he would growl at any human male that came near her day or night. She was having increasing difficulty keeping him from mounting her, and his ever-ready dog cock was beginning to tempt her more than she'd like. That was the end of male dogs for her, and they literally had to put that dog down.

Although she had great rapport with animals, she had lost all respect for parental authority when her drunken father jacked off the family dog in front of her and her mother. Her mother would have ignored it, but my girlfriend knew it was time for a divorce. They continued to live with the paternal grandfather (the real alpha male of the household) and my girlfriend was subjected to military discipline. This included a lot of barked orders, and discipline that was merciless. Marie got several pants-down spankings when she was way too old -- like, age fourteen. (I can only imagine what the old man saw between his granddaughter's legs as he reddened her ass.) Kinky as that was, I thought it was a significant key: She was used to submitting to older male authority during astoundingly intimate moments.

That probably accounted for my luck with her. I didn't think that I would have had a chance with a twenty-eight year woman when I was hitting fifty. Still, I had nothing to lose from asking. My line wasn't much better than,

"You wanna fuck?"

I didn't know it until later, but Marie had already been trying to seduce me, so she was way ready. She said, in that meek, coy voice she gets when she's sexy,

"I guess."

And the rest was history. Marie was prudish and demur during the day, and really, really sexy in bed. She did everything: Oral, anal, bondage, etc., and she did it really well. She didn't drink too much or smoke. She was brutally honest. On the other hand, she didn't say much. I always knew that there was lots, and lots that I didn't know about her.

So what had I seen at the orgy? I had learned four things. One, that she would participate in an orgy. Previously, I had thought her to be a very private and modest person. Two, that she seemed very experienced at getting guys to cum. She could use her hands, mouth, cunt, or ass – once, she even used her feet on me. Three, she demonstrated a technique that was new to me. When the guys were screwing her ass, she had reached behind and she had masturbated them while they pumped away. Four, she could get it on with women, in particular, she did a great job as a Sub to a Dom mistress. Normally, she had little respect for persons of her own gender.

I wanted to ask questions and learn more about her history, but I knew not how. I waited and waited. I never lost my curiosity. One day, I saw an opportunity. Something we had talked about prompted her to say,

"You know me -- I like older guys."

We were relaxed. We had time.

"Like, how old?"

"How about thirty-two when I was seventeen?"

I knew about that one.

"That's only a 15-year's difference. I'm twenty year's older than you."

She thought about it, and decided to give a serious reply.

"Probably, say, forty-years. I'd have been about twenty, they were in their late fifties and early sixties."

I was astounded -- not just at the age difference -- she had said, "they," as in plural. Just what-the-hell was she doing when she was twenty? I tried to keep cool.

"Any women?" I said in my most nonchalant voice.

"No. I was never attracted."

I was relieved, but then she continued,

"Until, you know, that time at the hotel. You were going to take me back there, remember?"

She made it seem so matter of fact. She wasn't joking. She was serious.

"I remember. I will."

I didn't want this to distract me from my earliest questions: How old? Where? What? When? So I said,

"Did you say, 'they' were in their sixties? How did you meet guys that old? Were they college professors?"

She laughed, and said,

"You really want to know, don't you? Well, sit tight, this ought to be one of the Canterbury Tales!"

What Marie told me knocked me on my ass. My sweet, sheltered, prim and proper girlfriend had been introduced to swinging when she was twenty. It suited her very well because she was among mostly couples in their late thirties on up, and they were, in her words, "housebroken." They were mature. They made no demands on her. She didn't have to date. She wasn't tied down, and she was always the center of attention because she was young but socially mature.

What my girlfriend didn't say was that, at age twenty, she must have looked like sex-candy. Marie always had a girlish figure – she still did. She knew all the tricks of animal husbandry from the ranch, and she was squeamish about nothing sexually. She liked older guys, and she liked male energy in general. I wondered: Had she learned all of that through swinging?

Swinging at age twenty with couples in their thirties was only a ten to twenty-year difference, not a forty-year age difference, so I asked her to work out the math. In that matter-of-fact tone she adopts when serious, she said,

"When you're single and swinging, you don't want to get stuck with the same couples. You mix it up, and it turned out that the real die-hards of the club were older, like, couples in their forties and fifties. There were few single women in that category. Most of us single women were younger."

Listening to this, I was beginning to get worried. I just had to ask the question that should never be asked:

"How many guys do you think you slept with?"

The question didn't even faze her. She started to do think out loud.

"About ten ... "

I was greatly relieved.

"... yeah, about ten at a party."

Oh, shit! Sleeping with ten guys at a party, and she probably went to more than one party.

"And about one party a week ... "

I interrupted, and said,

"Right, once a week."

"Well, sometimes you'd jump to another party, so, maybe, say twice a week."

This was agony. How long had she kept this up?

"I didn't do it for that long," she said, "I was done with it when I was twenty-two ... twenty-two or twenty-three."

Shit! That was a hell of a lot of guys in two or three years. That meant, if she slept with those guys, then, indirectly, I had slept with a hell of a lot of guys.

"But not every week, right?"

"Of course not, I got sick once, and I was laid up after an accident – that kind of took me out of commission for a while."

Fuck! What kind of sick? STD? What kind of accident? From something kinky? Rough sex?

"Relax. I spun out in my car and banged myself up pretty good, and once I got pneumonia. What's with the paranoia? You wanted to know. This was before AIDS, and people that are into swinging tend to watch out real carefully for STDs, if you know what I mean. You'd use condoms until you got to know someone."

Okay, I thought, settle down and listen to her. Let's just say, conservatively, that she had sex with ten guys a week, maybe just forty-weeks a year, for two to three years. That's 800 to 1200 guys! But wait, some of those were repeats. So, let's make it roughly, say, oh I don't know, maybe 200 to 600 different guys. Shit! I had no idea! This is more than I had ever expected to hear. I'm never going to sleep with her again! On the other hand, I've been sleeping with her for years, why stop now? Okay. Okay. I had to calm myself down. I had more questions to ask about this age thing and her technique.

"You were telling me about the older guys?"

My girlfriend sighed. Now, as she talked, she seemed nostalgic.

"Yeah, I definitely gravitated toward older and older guys. They take really good care of you. They take their time, and they appreciate you. It makes you want to do anything for them. They're sweet!"

Sweet for you, I thought, but they look like wrinkled raisins to me, even if I'm one of them. It seemed so perverted -- a twenty-something and a sixty year old -- but I listened to my girlfriend. Okay, right, she found them, "sweet."

She continued on. She was really getting into it.

"I guess I fell for them when I was sucking on this guy's shriveled cock until it got hard, and then it came in my mouth, and the guy was so touched that I took the time and hadn't moved on and hadn't given him a hard time – it didn't hurt that he reciprocated and went down on me, and that he kept going down on me after I came and came, like, ten times! Guys like that would give you money, too. They had lots of it, and I had none. It wasn't prostitution, just money to help you get by. There were times, though, when guys would ask for something special and were willing to pay big bucks – I always turned them down, though."

"Ask for something special? What do you mean by that?"

"You can be so naïve sometimes! Like, enemas, shitting on a plate, getting pissed on. Stuff like that. There's worse stuff, like rough sex and snuff, I guess."

Here, I had just gotten to thinking that swinging was just a bunch of middle aged people having vanilla sex, and I hear my girlfriend describing stuff only a whore would have to put up with.

"I didn't do that stuff, well, a guy gave me an enema once, but that's practical. I didn't take money. The only big money I took was when these really old guys took me away from a party to a private party and wanted me to spend the whole night. I told them I had to get home because it was the last day to pay my rent on time. They drove me to my apartment, peeled off $500 for the rent. Boy, were rents cheap in those days! When I got back the next day, I noticed that one of them had left another $500 on my kitchen counter. There was some fooling around at my apartment, but they didn't want to party at my place, so they drove me back to an expensive hotel, which turned out to be a good idea."

"Who were 'they'?"

"Well, that was my first and last time with those guys, so I don't know their names, but what you really want to know is how old they were, right?"

Busted!

"Yeah, right. Tell me."

"Those guys were easily over sixty, but not seventy."

"Those guys?"

"I told you, I don't know their ... oh, how many ... about three or four. I thought it would be easy taking on three -- no, I guess it was four old guys -- but I was wrong."

"Why? Did you get hurt?"

"No, no! I told you, guys like that are so appreciative and considerate. The only inconsiderate thing was that I was the only woman. That was good on one hand because they didn't ask for any girl-girl stuff, but I didn't get any sleep. You know, a lot of old people are insomniacs, and they kept me up with them. One or two of them might doze off, but then the others were up. I, on the other hand, never got to sleep. They fucked me until I was upside down -- probably literally."

Her talk about old people having sex with a young woman was making me sick. I'm an ageist. She's not. But, I was the one that had asked, and it was only fair that I listen respectfully.

"Would you mind telling me what guys like that do with a twenty-year-old?"

"That's a funny question coming from you! Think about it: Not much different than what you do."

That was fair, now all I had to do was think: What do I do in bed? Well, I do just about anything I can get away with. But, I thought, they might have done something I had never done.

"What else, besides what I do?"

"Well, they wanted me to dance a lot. I've never done that for you. And they liked to watch me masturbate a lot. And one of them liked me to call him "Daddy" -- you wouldn't like that. And, oh, when we were still at my apartment they had me shave my cunt while they watched – you really wouldn't like that!"

That's true. Making a woman look like a prepubescent girl was a real turn off for me, even if I had never seen it, except in porn.

"Any kinky sex?"

She thought about it seriously for a while, and that worried me, but then she said,

"Just the usual kink. Fingering me in the butt, one in my ass, one in my butt – their cocks, I mean, not their fingers. Licking my butt – I wouldn't lick them, but one guy kept trying to get me to do it. Oh, and a couple of the guys liked to jerk off on my face so that they could see it -- so that I could "wear" it for them, they said. I wasn't supposed to wipe it off. Usually, I don't like that, but they were so sweet. All of this took a really long time, by the way. You know, old guys and retarded ejaculation. This was before Viagra, and it took these guys a long time to get it up, and then a long time to cum. I jerked a lot of cock that night! It must have taken a half-an-hour each for those guys to cum on my face, and then I wasn't looking, and one guy got it right in my eye so I had to wipe it off,"

"Before the night was over they had to send out for – actually, they had the concierge bring up – more lube. You know me. I always like lots of lube – lots and lots of lube. I did feel like a whore, though, when the bellboy brought in three tubes of lube and I was in a room with four old men, but this wasn't whoring – I had a friend that did whoring, and that's a whole world different. I'd never do that!"

Remind me, I thought, just what the difference was, because I really didn't know. She had pretty much convinced me that she was a whore when she was twenty, at least on that night. Let's face it, the guys might have been "sweet" but they had paid her a thousand bucks a night to use her as their whore. But the goal of tonight's discussion was to find out about her predilection for old guys – and about that sexy, obscene, jerking off technique -- so, I asked about her "technique."

"Oh that! I didn't think you'd noticed."

She was obviously referring to the frat house orgy.

"Yeah, I guess I did learn that from the old guys. I only did that when I was sore and they were taking too long to cum – same thing that night at the party."

She called it a party. I called it an orgy.

"At the party I was getting pretty sore by the third or fourth time I got screwed in the ass."

I had only counted twice but, then again, she had started ahead of me.

"A long time ago, I figured out that if I jerk guys off while they're doing me, they cum faster. It's really important when they're doing my ass. I guess it works with young guys as well as old."

I don't think she realized that it was also a highly pornographic sight. The sight of a woman jerking off a guy into her own asshole was, well, pornographic. It was real whore-slut-skank type behavior.

"Was there any downside to swinging?"

My girlfriend thought about it, and said,

"I guess there was, because I stopped and I never did it again."

"What happened?"

"Nothing, really. Well, the last time was a pretty weird experience."

Uh-oh, I thought, I'm not sure I want to hear this, but I had asked for it.

"What happened that time?"

"It was the last few times, actually, that got pretty weird. I was getting tired of the same old couples, and they were trying to hook me up with new couples or single guys, but it's a pretty tight circle, and there wasn't much new out there,"

"One day, this guy calls me up and invites me to this swinging party that I used to go to a lot but hadn't been to in a while. He comes over to pick me up. He wasn't my type. Probably about fifty, fifty-five, and definitely not sweet, but I was looking forward to seeing old friends at the party. Only we didn't go that night. He said he couldn't take his eyes off of me, that he couldn't keep his erection down to go out in public, and that he just had to have me right now, and blah, blah, blah. We'd 'play' some, and then we would go to the party. I had some misgivings, but he said to consider it as sort of a warm-up,"

"So, I let him grope me, and then I thought we'd get going, but he had other plans. He pushed me to my knees and had me suck him to 'get us wet.' He meant get him wet -- I was definitely not getting wet! Then he had me get up from my knees, take off my panties, and get on the couch. He stuck it in and screwed me for a while. Pretty standard stuff. Fortunately, he stopped pretty quickly, but then he said, "Get up, and bend over the couch." I was still in my black dress, and I started to take it off as I got up. I was pretty sure I knew what he wanted, and I didn't want to get it dirty. He said, "Leave it on!" I hiked up my dress, and I bent over the couch. Sure enough, he started to shove it up my butt. That's when I realized he was really large! Not long, but really thick. I said,"

"I don't think it's going to fit."

He said something like,

"Don't try to flatter me, Bitch," or "That's what they all say."

"No, really, it's not going to fit. I'm pretty dainty down there."

"Well, it's going to fit tonight!"

"I thought, I better get some lube and I better get it quick! Fortunately, we were still at my place, so I said,"

"Yeah, it'll fit if we lube it up real good. My hands will feel great, too."

"Frankly, I was trying to avoid having to take something that thick, but he was no dummy."

"Yeah, your hands will feel great, but it's still going up your butt!"

(About this point in her story, I was really confused about what made this different than rape, but my girlfriend hadn't couched it in those terms, nor did she do so as she continued.)

"I began to realize that I didn't like him, but that I liked his commanding ways. He was going to get what he wanted, whether I wanted to or not. It was the same with the boys at the party the other night. Under those conditions, I don't have to think, all I have to do is follow directions and I'm going to get screwed. None of that game playing and posturing like at swinging parties,"