An adult stories – The Confessor: MILF Gone Wild by CabotDeWine,CabotDeWine Call me Edward. Or if you really want to know me, call me Edward the Confessor. Not to confuse me with the pious English monarch. I mean confessor like the priests who hear confession. But unlike kings or priests, I don’t help people absolve themselves of their sins, I help them indulge.
I’m an otherwise average looking guy — decent enough looks, generally sociable, but never really the life of the party. But what my special skill is making people, especially women, feel comfortable enough to confess things they might otherwise not. I can’t explain the gift, but I’ve learned how to use it.
I have many stories, and this is but one of them. Well, one series of stories, which all starts thanks to Girls Gone Wild.
#Chapter 1: MILFS Gone WildI was born at the divide of the Millennial/Gen Z generations. The year I was born was when Girls Gone Wild came out, and the series had shut down, under legal and other issues, before I was old enough to see the ubiquitous late-night ads. I was aware of it, in the sense that anyone is aware of old TV shows or other media from prior generations.
Videos from then circulate around the tube sites, but I didn’t watch my first one until college, when I had a part time job at one of the video stores that still hung on thanks to a dedicated local film community and its exhaustive selection that Netflix couldn’t match. Like all Mom-and-Pop video shops, there was the back room behind the beaded curtain where the porn was. Along with the new titles, they kept a backlog of classic porn films for the aficionados of old men who weren’t tech savvy, didn’t have broadband, or preferred the old ways. I would of course take some home with me, out of mere curiosity. I found a few Girls Gone Wild DVDs, and even some VHS ones. Luckily I had an old VCR and could watch them. I liked them well enough, and laughed at how many young men going to college probably thought this was what it was going to be like all the time.
I graduated, moved on, and didn’t think too much about it. Until I went to a business conference out of state to a new city.
#I’ve always had a thing for older women, and luckily that has been reciprocated. This isn’t an exclusive thing, but my confessor skill has led to many an older woman being able to confess to things that they have done, could have done but didn’t, or wish they had the chance to do. Every older generation starts to get to the point where they think the younger generation is doing all the sex that they didn’t get to do when they were younger.
Tonight’s older woman was across the hotel bar. We made eye contact and I knew we were going to sleep together. I could already tell from her look she was desperately single, and probably a divorcee. She had that Mom air to her. Whatever kids she had no doubt made dating hard, and this business getaway was her chance to just get laid without worrying about logistics. I was more than happy to oblige her needs.
I went over and we got to talking. Her name was Julie. After the ice breakers we slipped easily into flirting, I made a risque comment about the low cut of her blouse.
“You’d never guess that I was the daughter of a pastor,” Julie said.
“I might have to praise your maker for his work,” I said.
“You wouldn’t be the first to exclaim ‘Dear God’ when you see them,” Julie said.
When she said that, something clicked in my mind. I had a mild sense of familiarity with her, but I had originally chalked it up to her being the type of woman I had slept with before. But suddenly the line “Dear God” brought me back to the video store, to a copy of the Girls Gone Wild back catalog. There was a young co-ed with ample breasts who is goaded into flashing the camera. As soon as she does it, a homeless man walking by shouts “Dear God!” before crossing himself.
That was Julie. And she was here in front of me!
But I don’t say anything right away. No matter how innocent it is, recalling porn in perfect clarity is a turn off. Besides, as a rule, the confessor’s best move is to let your companion be the one to lead the confession. They want to unburden, and like a good strip club patron you need to let them expose themselves at their own pace.
“I would be happy to join this congregation,” I said.
She looked at me, and not seeing any judgment or hint of knowledge of her secret, relaxed and leaned in.
“If I told you a secret, could you keep it?”
“I can. I’m quite good at it, too good to give you any references,” I said.
She laughed and put a hand on my arm.
“Have you heard of Girls Gone Wild?” she asked.
“Sure. A bit before my time, but I remember seeing the ads on the old episodes of South Park my cousin recorded,” I said.
“Well I… I don’t think starred is the word, but I was featured in one of those videos,” Julie said.
“So, you had a small brush with fame?” I asked.
“More like infamy,” Julie said, “It’s not something I like to tell many people.”
“I’m honored to be among the few,” I said.
“I wish ‘like’ could be the word for it. If it had turned out better, maybe,” she said.
“What’s the story behind it?” I asked.
She sipped her drink before beginning her story.
#Like I said, I was born a pastor’s daughter. For the most part I was well behaved, but I obviously had the normal desires. My parents weren’t the worst of the conservative religious types. No purity balls and all that. But the no sex until marriage thing was held up high, and the town I grew up in was small enough that I couldn’t get away with sneaking out, meeting up with boys, or even things like smoking weed and not have someone spot me and notify my parents.
My parents wanted me to go to the Christian college where they met, but I convinced them the local state college was a better choice. It wasn’t the big party school in the state, it barely ran a tailgate at the Division II football games. It was chaste by most college standards, but for me it represented freedom.
Obviously when I went there I went wild. Again, based on my terms. I felt dirty buying a pack of cigarettes, even if I only smoked half of them before giving up the habit. Hookah was more fun, since it was socially done in mixed company and there were a few guys bold enough to use it to flirt and blow smoke in my mouth, before turning it to making out.
I was slow to drinking, thinking I was being responsible. But what I wasn’t ready for was when my roommate invited me to Spring Break. Her mother worked for an airline and her uncle owned a condo in Miami he was willing to let her use.
I wasn’t ready for Miami, not really. Hell, I brought a one-piece swimsuit! Luckily my friend was more than happy to help me choose more appropriate attire.
We went bar hopping on fake IDs. I had mostly sipped cheap beer and wine coolers, so I was not used to the sweeter liquor drinks. I was drunk off my ass before long.
My friend and I walked out of the bar, and heard some cheering going on. We see these guys with cameras out and think they might be MTV. I had only just started watching it, and this was back when it was mostly music and their Spring Break coverage. We decided to head over, thinking there might be a celebrity.
Girls Gone Wild had not come out yet, they were still in their collection phase. So when we got there and saw girls lifting up their tops, we had no context for it.
Between the drink and the novelty, I didn’t have a real idea of what was going on. What I knew was a lot of hot guys were cheering for those girls, and I was still a virgin and deeply wanting male attention.
So when the guys spotted me and my friend they turned the cameras our way.
“Hey babe,” the camera man shouted, “Why don’t you show us what you got?”
Again, being so naive, I thought he just meant for us to dance sexy. And ‘sexy’ for a sheltered white girl means cringey everywhere else. We got a few laughs, but I was too drunk to know the difference.
“What about your top?” the cameraman asked.
I looked down at my top and grabbed my boobs. That got the right reaction from the camera guys, so I jiggled my boobs a bit. This tiny bit of exhibitionism gave me a real thrill.
“Take your top off, show us what you got!” the camera man said.
I knew what he wanted, and I was nervous. Not because of the camera or anything, it was because I wasn’t comfortable yet with thinking I was sexy enough for guys. But the cheers from several guys and some women got me encouraged, so untied my top and showed my tits.
This homeless guy walking by yelled “Dear God!” and I laughed. I felt a little sexual power at that moment.
Newbie that I was, somehow I got the idea to jump up and down to let my tits bounce. It was really fun in the moment, and when my friend joined in I was having the time of my life. I had no attraction to her, but I liked sharing the moment with her tits out. The cameraman was trying to get us to kiss, but we turned him down.
One of the girls he had just been filming, she must have been jealous and ran into the frame for more attention.
[I suppressed a smile. I only gave you readers only a partial description of the video. There was more. I’ll let her tell this story].
“Play with each other’s tits!” the cameraman said.
I was too nervous about that, still grossed out by the lesbian thing. But the other girl went and grabbed both our tits, and was really mugging for the camera. I was hoping she would leave, but then the camera man told her to make out. She moved in on me, but I put a hand up to block her, but that left my chest open. She leaned in and licked both my nipples for the camera, and started sucking on the left one.
I was shocked! Too shocked to realize how aroused I actually was. I push her away and put my top on.
A producer comes by with a release to sign. Now I was drunk, so I shouldn’t have been able to sign anything. I tried to read it in the dark, but the guy said just sign. He offered us free drink tickets to a nearby bar, and being naive and drunk, I just signed, took the tickets and we went to have more fun.
Sobered up the next morning, I regretted the decisions, and was confused about the arousal from having my tits licked, but I hoped it would just be some local pervert’s personal porn stash.
It wasn’t until junior year that I was even aware that Girls Gone Wild was a thing. I learned from a guy friend, who asked if I had ever been in Miami on Spring Break. He said a frat brother had the video and they were all watching, and he recognized me.
He was a nice enough guy, and if he had just asked me, maybe it wouldn’t have been so bad. But he was so excited to see me in it that he blurted it out. Soon, a whole frat of guys knew a girl from their school was in a porn tape. The whole point of watching the tape together was to try and plan their own sort of party where they hoped they could get girls to show off their tits and make out. I became a fetish object for them, and it was gross and possessive. It went beyond them and spread across campus.
We didn’t have the word incel then, but some angsty incel, who I had never even met, let alone turned down, felt the need to call my parents and let them know. That caused a whole host of issues for years.
#I nodded when she was done with her story.
“That’s terrible how it ended,” I said, “I wish you could have enjoyed it as much as when you did it.”
“You know, I really wish I could have. I did get a thrill from exhibition. I even thought about doing nude modeling for art classes. And of course the arousal from the random girl licking my tits, along with the permissive pro-gay atmosphere, got me considering trying stuff out. But the outing really hurt me for a while after,” Julie said.
I took her hand.
“I hope you did get to explore some of your interests,” I said.
“I did eventually have a fling with a woman,” Julie said.
“And you could still make a great nude model,” I said.
She blushed a bit.
“You haven’t seen me nude yet,” she said.
“I’m sure I could find some pen and paper to sketch you,” I said.
She smiled.
“We could be like Jack and Rose,” she said.
“Did you see that film in the theater?” I asked.
“Three times,” she said, “God, does that age me?”
“Like wine,” I said.
The moment was right. I’d known from first glance we were going to sleep together, but now we had a plan. Her exhibitionist fantasy was out there, and there was no way we weren’t going to do that. However, as happens sometimes, these confessor things bring out even more confessions.
“Pardon me,” said the bartender, a cute 20-something, “I couldn’t help but overhear you.”
Julie looked a bit shocked, but I kept a cool demeanor. I sensed by the bartender’s nervousness that this was a leap on her end to make this interruption. Again, as a confessor, you sense when someone has something they want to say, and I can only imagine what our discussion sparked in this cute bartender.
“What can we do to help you?” I asked.
“Sorry, it’s just I’m a human sexuality major, and you mentioned Girls Gone Wild. I’ve been doing a study on OnlyFans and other sites, and I am interested in predecessor adult content,” she said.
“What’s your name?” I asked.
“Harper,” she said.
I already mentioned she was an early 20s college student. She had black hair, dyed no doubt, short length with bangs. She had piercings on her ears, nose, and an eyebrow. I could see the edge of a tattoo on her forearm peeking out from under a sleeve, and no doubt more to be seen. And while she wore nothing directly saying it, I got the feeling she was bi or pansexual. Her interest in human sexuality wasn’t merely academic. And I didn’t think for a minute her interest in Julie was merely academic either.
“What do you want to know about Girls Gone Wild?” Julie asked suspiciously.
“Well, I am interested in the change from the early exploitative stuff, to the more empowered stuff of sex workers on OnlyFans and other cam sites,” Julie said, “I wonder, maybe, if you’d be up to talk for a paper I am writing? I could change your name, of course.”
Julie looked to me. But now wasn’t the time for me to give her encouragement. She needed to desire this for it to work, and I needed to make her comfortable to expose herself to this stranger. Luckily, I had the sense there was something Harper wasn’t saying to us yet.
“What’s your OnlyFans handle?” I asked.
Harper breathed in, somehow surprised and excited that I figured out she was more than just an observer. She told us the name and pulled out her phone.
“Here,” she said, “This is my page.”
She had to step away to deal with some customers because her boss was on the floor, and Julie and I scrolled through her list. It was generally tame stuff, no hardcore stuff, no men, just a few pictures with some other female models and implied lesbian stuff. In this she did look different, as she would don a pink-and-blonde wig and wore makeup that made her look like an anime-manic-pixie Dream Girl.
“I never quite got the anime girl look,” Julie said.
“Luckily she’s much cuter in her natural state,” I said, “Wouldn’t you agree?”
Julie shot me a look.
“She might like you, but I’m not exactly her type,” Julie said.
“You think that other model is her type? I mean, they may have fucked, but there isn’t real feeling there,” I said.
“She’s so young,” Julie said.
“Older than you were in your video,” I said.
“Still…”
I took her hand.
“Don’t add this to your list of life regrets,” I said.
Harper returned with free drinks for both of us. We chatted about her photos.
“So, I’m being very basic with this. It was just to see how it all works,” Harper said.
“But then the money came in,” I said.
“Well… it’s nice to be able to pay for college without loans,” Harper said.
“But you still work here,” Julie asked.
“Bartending pays well with tips, plus it provides a good cover for having money,” Harper said.
“I wish I had gotten more than a T-shirt for my video and the problems it caused,” Julie said.
“That’s what I am interested in. My professor is saying my thesis needs to expand beyond just OnlyFans, and I think Girls Gone Wild was one of the early brands that started embracing female sexuality outside the porn studio system, and just as the internet was liberating things,” Harper said.
Harper looked and saw her boss giving her a look.
“Is there an after hours bar for service people around here?” I asked Harper.
“Sure, the Salted Cod, near the docks. Open until 4AM,” Harper said.
“Could we meet you there after your shift?” I asked.
“Of course. The hotel bar closes at 12PM, I get out about 1AM after cleaning up. Meet you there at 1:30?” she asked.
“It’s a date,” I said.
Harper no doubt caught the meaning of my statement. Julie and I finished out drinks, I paid, and we headed up to my hotel room.
“You always double-book dates on the same night?” Julie asked.
“Not often, but this isn’t my first,” I said, “Most of my threesomes have been planned in advance.”
“You seem sure that’s going down,” Julie said.
“As sure as I am that you will be,” I said.
I kissed Julie as we stepped inside my room. She leaned into it.
“I’ve never done a threesome,” she confessed.
“Luckily you’re in good hands,” I said, feeling her up.
“I suppose Harper’s done things like that as well,” Julie said.
“You’ll both have things to teach each other,” I said, “Fair trade.”
We started making out for a few moments, then Julie broke it off.
“If we do this with Harper…” she began.
“When we do it,” I corrected.
“When we do it… could we start with just her and I? I want you to watch. I hate what Girls Gone Wild was, but I definitely found those lesbian hookups kind of hot. A hookup with a strange hottie on Spring Break would have been a great first time story.”
“We’ll make it all up,” I said, “Your Girls Gone Wild story doesn’t have to end with embarrassment. You can take control and make it your ending.”
I paused and saw the hotel stationary on the desk.
“I believe I owe you a nude portrait,” I said.
“Do we have time?” Julie asked.
“It’s only 11. We have plenty of time to do a lot before our date with Harper,” I said.
She went over to the bed. She got out of her clothes and got on the bed. I walked around, looking for her at all angles.
“Like what you see?” she asked.
“I love it,” I said.
I took a moment to pose and position her on the bed, letting my hands feel all over her nude body. I gave her breasts a firm squeeze to get her nipples hard.
“I love that I get to draw these, play with them, then share them with Harper later,” I said.
Her hand went to my crotch.
“I could say the same about this guy,” she said.
It took a lot for me not to start up with her then and there. But I had a duty as a confessor to meet her desires. So I took my pen and paper and began drawing her.
I’ve done plenty of nude drawings in my day. I actually took a course back in the day (I had a crush on a coed who was part of the class, though we never hooked up. I did hook up with the teaching assistant, but that is a story for another day). I’m not a great artist, but I have enough skill to impress many a woman who has wanted to see themselves captured like that. I know I have a few dozen drawings that are tucked away in many memory boxes, hidden in books, and on display in a few homes.
One thing is, I almost never do just one drawing. One can’t fully capture someone, and I really get off on doing the different angles. With Julie I did five, to emphasize her tits, ass, legs, face, and torso. I could have done a whole book off her. Her body was a nice thing. It was no longer the young perky body of her Spring Break self, but there is a beauty to it. Her breasts had grown, as often happens after motherhood. She didn’t have many wrinkles, nor the sign of too much sun, or the damage cigarette smoking did. She must have moisturized and kept to the gym. I don’t know why she and her ex-husband broke up, but he’d be a goddamn fool for leaving her for someone younger. Most of those young fast women men leave their wives for age poorly after too much drinking, sun, and poor nutrition.
Julie adored her pictures. She probably looked at herself critically in the mirror, looking for and exaggerating flaws. I didn’t go out of my way to hide her flaws, but I had a knack for keeping them in context of the whole of her body.
“These are amazing,” she said, “You could almost make me believe I look this good.”
“I only draw what I see. I don’t lie when I do this,” I said.
I took the drawings from her hand and put them safely on the desk. I returned to the bed. I pulled her in for a kiss and my hands started all over her body. It had been a torturous time for me sitting there, drawing her whole body, but not being able to enjoy it fully. But it was the good sort of torture, the denial and temptation. It wasn’t like I was being teased or used. I could have stepped in at any time and she would have welcomed me. But discipline is the key to my role, and now that we were both wound up, it was time to show her how desirable she was.
I took charge, of course, as that is what she needed. I kissed her deeply and took her in my arms.
“Unbutton my shirt,” I commanded, playing with her ass while he undid my shirt.
She stripped the shirt off me, then lifted my undershirt. Her hungry hands fumbled with my belt as she anticipated unleashing my cock from its confinement. She unzipped me and pulled down my pants. I kicked them off, leaving only my boxers.
“Lick it through my boxers,” I said.
This is a trick I’d learned, and I guess a kink of mine. The thin wall of fabric dulled the physical sensation of her oral play on my cock, but it more than made it up with heightened anticipation, especially on her end. Even through the fabric she could feel my cock throb, and a small wet spot of precum started to form, mixing with the light moist saliva she left. I reached down and undid the button fly in one quick move, exposing the underside of my cock. She quickly pulled it out and started sucking and licking my shaft and tip.
After a few moments her fingers found her way to the waistband of my boxer, wanting to pull them down, but wanting permission. I took a handful of her hair, then pulled gently so she was looking at me.
“Pull them down, then lick my balls,” I said.
She did, pulling my boxers down to my knees and kissing and licking my balls, while one hand stroked and played with my cock. This was a great feeling, and I knew I could push her further than I figured she had ever gone.
“Have you ever licked a man’s ass?” I asked.
She looked up at me, the expression signaling that she had not. But not that she would not. I looked at her and she looked at me. I said nothing, and didn’t even bother to give a look of begging or cajoling. I just waited with quiet confidence. And she finally looked down, lifted by scrotum, and gave my asshole a lick. And not a tentative little one, but a full lap. Then another, and another. Her hand continued to stroke my cock. A leaned back and let her go to work on that. She was game for anything I asked. I wouldn’t even need to use my commanding voice. She was bought in for whatever tonight. Not just with me, but with Harper as well.
After a few minutes of asslicking I felt satisfied, and moved her up. I played with her tits for several moments, enjoying them with my hand and mouth. I then told her to wrap her tits around my cock, and started titty fucking. We hit a rhythm together, Me thrusting and her going up and down. Her tits were warm and enveloping my cock. I wanted to yell our “Dear God”, but held my tongue. This was no time for a callback.
I felt myself nearing climax and stopped. I wanted to finish so much, but that would be a sexual favor for later. Now it was time for the show.
We moved up on the bed, and I slid a pillow under her back to arch her pussy in the right angle. I kissed her pussy and did a few minutes of oral to get her nice and wet. I stuck my finger deep in, pulled it out, and put it by her mouth. She sucked my finger clean.
I slid inside her and started slowly thrusting in. I felt up her breasts and started kissing her neck as I built up speed. As I started going faster her legs wrapped around me.
“Tighter,” I ordered, and her legs tightened.
I liked the tightness of her grip. I only wish she was still wearing her high heels so they could dig in my sides a little. I know, a small kink of mine, but it was too late right now. The rhythm was going, and I couldn’t interrupt it.
Within a minute she was building to climax. I thrust harder, and took one breast in my hand and pinched the nipple. Her back arched and I knew she was on the edge. I went straight for her neck and kissed the spot I knew was getting her most horny. Her neck bent toward me and a final loud moan came out.
“OOOOHHHH!” she climaxed.
She came, and for several moments lay there, giving small grunts as I continued to thrust inside her. Her eyes opened in the post-coital haze. A hand reached up and touched the side of my face. I felt a surge of adrenaline in my body. I’d finished her off, now it was my time to come.
I let the restraint I held go, all attempts to delay orgasm. Now it was time to culminate the night’s flirting, foreplay, and romance in one big go. I grabbed her head and pulled her deep in for a kiss. My tongue went deep in her mouth, and I breathed in deep, taking the air out of her lungs. This caused her legs to tighten up again, after having gone limp after orgasm. Her fingers dug into my back and the air left her lungs. I held on for a second longer, then let her face go as the orgasm hit my body.
I never really know what I sound like when I come, I am usually so lost in pleasure I can see or hear almost nothing. But I did hear Julie’s gasps for breath after I let her go, and those deep breathes excited me as the second, third, fourth, fifth pumps of cum came out of my cock.
“It felt like you were trying to suck my soul out,” Julie exclaimed as I pulled out of her.
I didn’t answer that, just put my cum-and-pussy juice soaked cock by her face, and she sucked it clean.
“Come,” I said.
I walked her to the shower, giving her ass a smack. She showered and cleaned off our bodies.
“You’re good,” she said.
“Thank you,” I said, kissing her.
“I mean it. Like, men my own age, the ones that aren’t married, they don’t have what you have,” she said.
“So date men my age,” I said, “Though not before our date with Harper.”
“How is it that I get two young people into me after years struggling dating post-divorce?” she asked.
“We hadn’t met before tonight,” I said.
“I don’t want to be just another lay for you after what you’ve been to me tonight,” Julie said.
“We still have a ways to go to make this memorable,” I said, “We’ve got our date with Harper.”
“Which you arranged,” Julie said, “You’re doing so much more for me than I could do for you.”
“Trust me, Harper has something she wants to do that she can’t do without you. She and I couldn’t do what she is going to be able to do with you and I,” I said.
Julie smiled. I knew she didn’t believe it yet, that she could play the role of a sex goddess tonight. But at least now she was beginning to believe that it could be possible. And the truth was this was memorable. I might have had more, and certainly more exciting sex, than most, but a generation-bridging threesome with a Girls Gone Wild model and a part-time OnlyFans was a first for me (and as of this writing, still the only time for this very specific scenario). And that threesome would lead to even more adventurous sex.
But let’s not get ahead of ourselves. We still have the date with Harper to attend.
(To Be Continued)