TL;DR A pushing 60 widower tells you about the time when he not only slept with a much younger woman but also enjoyed a spur of the moment threesome with her female roommate.
Disclaimer: This story, while completely true, is over the top and I can’t apologize for it. I’m just telling a story is all. Also this story is LONG. I hope you enjoy a wasted day at work as much as I’ve spent a vacation day from my end of things writing it. I’ll be retired soon and can write more of this trash over time. *bwahahaha*
This long-ass story all happened just over 20 years ago and was pretty much a summer romance, but who’s kidding who? Lots and lots of fucking was the order of business, and I wouldn’t call any of this romantic in the literal sense. It was my last fling, as history would play itself out, as a bachelor/divorcee. The interpersonal aspect of this all was maddening, but to this day the sex that we shared puts a smile on my face.
Recently on /r/gonewildstories someone posted something about having sex with a guy because he was tall. This is my confirmation that her take on tallness is… true. It’s not that I’m a bad looking guy. It’s just that I’m not hot, or at least not the kind of guy that everyone covets. :-)
I used to love USENET and was subscribed to probably 100 or more groups. Most of them were nerd stuffs related to computer programming or Star Trek, but a few were for erotica and personals ads. Before USENET became a total cesspool, which was in full effect by 2001 or so, the personals ads were a great read. Heck I’d even post my own and to this day when I re-read some of the responses I’d received: the responses were absolutely priceless.
I came across this one ad that was pretty fun/funny. Plus as a tall guy (6’6″+ back then) she stating that she was 5’11” didn’t hurt. This was long before catfishing or any of those other horrible things that make the internet a dangerous place so I had zero compunction about sending her a response. My response was short and somewhat witty (eye of the beholder?) and I essentially asked her for more information.
And that’s when it happened. The first sentence of her response as sent from her .edu email account was, “tall is super hot. Older is hot too. I’m glad that you’re tall (and older). You could be ugly as fuck but tall goes a long way. Older is the icing on the cake.” She further disclosed that she was 18 years old, finishing her freshman year of college, and recently had gone through a breakup with her high school sweetheart that had thrown her for a loop. This all came from the mouths of babes.
In retrospect I should’ve never, ever carried on a correspondence with an 18 year old girl. You can believe this or not but I’ve always dated in my age group or older. Chasing young girls around, frankly, seemed exhausting, and I remembered the odyssey of dating in my teen years — so I avoided dating substantially younger women like the plague. This one time, though, I got sucked in. I admit it. She was smart and playful and crass and I found it all to be charming beyond belief; plus it piqued my curiosity about what it would be like to be with her sexually and otherwise. So I kept writing her back. And she kept responding. Each of her emails was edgier than the last.
She invited me to take our conversation over to ICQ (that’s how long ago this happened!) and I obliged. Bear in mind that when this happened there was no texting, digital cameras were new on the market and expensive, and most people didn’t have scanners or other means to digitize their pictures. While we both painted pictures of how we looked through words, we could be literally anybody as it used to be such a pain in the ass to send a digital image of yourself to somebody else. This meant that we had to take things on faith. Since I figured that we’d never meet in real life, in particular because we lived four hours away from one another, I just went with it. She obviously had other plans.
As soon as we started corresponding over ICQ she changed the topic and tone of the conversation over to sex. And she was super explicit about it (not that I minded). Her jaw dropping claim was that not only had she started having sex when she was 12 (12! WTF!) but that her first time was when she seduced her cousin. I didn’t even have to (or want to) ask her more questions about this odd-to-say-the-least event; she would talk about it repeatedly, and would always explain that, “you know how some people just want to get fucked a lot? I like to get fucked a lot. I’ve always been like this…” Oh. My. God. What on earth was I doing?! Scratch that. I knew exactly what I was doing. This was all so depraved and I was getting off on it in spite of myself.
We had a ton of virtual fights. For someone who was super sexually submissive (her claim) she certainly knew how to stir shit up. Shortly before she was going to take her finals, I guess I failed one of her myriad shit tests, and she became absent from ICQ for two weeks. She’d been super angry, and memory escapes me about what, but next thing you know she’s not on ICQ and she’s not responding to email. I figured that was the end and admittedly 4 weeks of her disclosures, whether true or not (oh, they were definitely true!), had been a fun ride to say the least. Plus my lack of production at work was beginning to show; my boss was concerned because I’d fallen behind on a couple of major projects. It was probably good that this all was coming to an end. Or was it?
I’d gotten back on the wagon as far as work was concerned and my formerly behind schedule projects had gotten back on track. My boss was off my back and this woman, Anna (not her real name) and I had recently started chatting, ostensibly because she thought that I might need some support after my divorce or something. She was super sexy and age appropriate, but she had a boyfriend. At the time I’d thought it was serious. I think she thought it was serious with her boyfriend too. Plus she’d been good friends with my ex and all. So, after finally returning to a state of exercising good judgment, I didn’t ask Anna out during the course of our correspondence. Anna was going to marry that guy and that would be the end of it.
Oops! No sooner did Anna and I start emailing back and forth that Em (not her real name) sent me an email with her phone number and a date and time I should call her to setup our “date.” I shouldn’t have called. But you know what happened, reader. I did call. You knew I was going to call because you are Very Smart. Em invited herself over for the next day, a Saturday, and wanted me to cook her some dinner. She settled on spaghetti and meatballs (I do make a killer meatball!) because at that time my cooking repertoire was highly limited. Sexually I’d been in a dry spell, and I also admit that at the time I was attracted to drama like it was a magnet and that makes sense because I was always rock hard like a piece of iron. What better to do then to invite an 18 year old girl to my house, four hours away from her college, for sex and Italian food? Okay, so I was very stoopid about this. I own that. I just needed to know what it would be like, or if it would be anything at all. As I re-read my last sentence I wonder if I should’ve been born in California or if I’m some acolyte of Deepak Chopra. Fuck.
I’d just formed the meatballs and put them in the freezer. I don’t use any breading in my meatballs, so to firm them up before I put them in the pan I freeze them for a bit. If you don’t do this, pro tip if you are trying to cut down on carbs. No sooner had I closed the freezer door that the phone rang. I picked it up and to my surprise I had a collect call. It was Em. I was sure she was going to cancel and that I’d made enough meatballs for a carnivorous army. The sauce I’d fabricated wasn’t too shabby either and it had been simmering since the morning. To my surprise she was only an hour away and stressed to me that she couldn’t wait for our date to start.
The doorbell rang shortly after I’d popped the baking dish with the sauce and meatballs in the oven. When I opened the door my jaw dropped for sure. Hers’ did as well. “What a lovely girl,” I said to myself as I not-so-discreetly eyed up and down her 5’11” frame. Her blonde mane of hair went down to her ass. Her blue eyes. The perfection of her skin. Her wide hips and perfect bubble butt. Her flat tummy. Her rack. Attire wise it’s what I would’ve expected from a college student, and I say this with respect. I dressed like shit through college and I really didn’t start dressing better until I hit 35. Her bell-bottomed jeans, they with embroidered rose designs up and down each leg, her baggy blouse (it did show a lot of cleavage which I assume was by design), her Birkenstocks… I would dress for dates like a guy who wanted to get some, and I had been at a point in life where women would play the same strategy with their short skirts, heels, and cleavage displays. This was different though. A lot different. I enjoy the smoke show of a woman who dresses and smells great, and yet Em presented herself in a way that… well… still I wanted to fuck her with all of my might.
“You are SO BIG,” she stressed, crushing me in a hug. “How did we get so lucky?!” She was so tall. So pretty. She smelled good, but in a “I’m so young and smell good naturally” kind of way (that was creepy. sad. I bring to you this Trumpian story. Hope that you’re enjoying it, reader.). I didn’t offer any compliments (I’m a bad, bad motherfucker, but not literally) and I stole a peck on the lips from her. Then our tongues started wrestling for supremacy and my index finger and thumb reached up to her nipples to pinch them. As we continued hard hugging and frenching, she unbuttoned and unzipped her bell-bottomed jeans and they fell to the floor before she stepped out of them. She wasn’t wearing panties and her nether regions were well cropped. Nobody, or I assume I’ll make an air quotes around nobody here, was shoring up like that at the time. This was also before the tattoo craze and her skin was unblemished. I don’t get crazes. Who am I?!
I knelt down on the runner in my foyer and ran my tongue up and down her slit. “Holy FUCK,” she exclaimed. “No guy has eaten me out like this before FUCK something I don’t remember what she told me now FUCK!” As my tongue explored her, and I was very pleased not to have my tongue’s explorations be thwarted by hair in her pubic region, she came hard, locking her thighs around my head. I had stripped practically naked as I ate her out and my own pants were puddled around my ankles. I was hard and ready and was dripping precum onto the ceramic tiles of my foyer and I worried about passing out or of losing my hardness or of cumming too soon.
I’d bought this huge pack of condoms and yet I used none of them. As she came down from her orgasm I laid her down and we started fucking on the runner in the foyer. I couldn’t believe how wet and ready she was. She was a little bit tight but her hot and wet hole loosened up as we fucked. Then I bent her over the carpeted stairs going upstairs and took her doggy with my hands knotting her impressive mane in my fist and pulling her head back towards me. She came again and her cunt was squeezing me for all it was worth. I had never been held that tight in a cunt before. I’d started thinking about how I needed to start the pasta soon and how I feared that the meatballs would get over done in the oven. That kept me from shooting a venerable load into her most sacred area inside of 60 seconds. It had been some time since I’d shot into a women and I really wanted to shoot into Em. Not only did I want to do it once. I wanted to do it all night if at all possible. She was willing and I was able. I could not believe how we had this sexual chemistry which, if you’re read what I’ve written, would be 2 for 2 in recent time. This shouldn’t have happened at all, right? She was so young and I was recently accepted into the middle aged crowd. Why were we fucking like this? Why were we fucking at all? I just wanted to savor it, and thankfully my body didn’t betray me. I just kept fucking and fucking and fucking.
“Holy shit!” I exclaimed.
“Are you ready to cum?” she asked.
“No,” I bowed my head. “I have to start the pasta water.” (This really happened. My powers of seduction are unparalleled.)
“That’s cool and I am kind of hungry,” she said, trying to catch her breath. “Mmm, maybe you can start the water and… mmmm” Her voice trailed off.
I decoupled from her and slipped off my shoes so that I could get my pants and my underwear off from around my ankles. I was totally naked now. She was still wearing her baggy shirt. I’d started to run the sink to fill the cauldron that I used to cook pasta. I could see her reflection in the kitchen window and she shed her shirt as the sink was slow to go about its duties. Her body was spectacular. “Youth is wasted on the youth,” a barb from the mother of a former girlfriend had once told me echoed through my head. “No,” I thought to myself. This is going perfectly. Absolutely perfectly. I’d just filled the cauldron and put it on the stove top after having fired the burner. Em’s mouth was on my dick after I put the pot on the stove top and I realized that I was already ready for another round.
I set the timer on the stove for another 10 minutes and we fucked on the kitchen floor, missionary style. I heard a beep that told me that the timer would sound in 60 seconds.
“Oh god. Oh god. I’m getting close,” I said. “Where?! …”
“In me,” she said, locking her long legs around my back so that I couldn’t pull out even if I tried. “Please. I want to feel you in me.”
I started hammering her harder and you could hear our bodies slapping together as the sounds echoed through my mostly undecorated house. She started making these delicious high pitched cries and I forced my pelvis onto hers’ as I pumped what I surmised to be a huge load in her.
There was no time for an afterglow unfortunately. The timer beeped and I pulled out of her, some of my cum falling on the tiling of the kitchen floor. I gently drained the pasta and took the sauce and meatballs out of the oven.
“Are you hungry?” I asked, totally un-ironically.
“Yeah, I’m hungry,” she said, totally nude now, picking up my dress shirt from the floor of the foyer and putting it on as her only garment. “Very hungry.”
“This woman was 18 when this took place?” you ask. “You’re shitting me.” No, I’m not shitting you. About any of this. I tell this story since it’s (maybe?) unique. Or I suppose it’s a unique story given when it took place.
Seriously I fumbled through a handful of sexual experiences at around the age of 18. How could this girl take a dick like that, take my first load of cum, and still want more?! I need to talk to more parents. Her parents made her like this, didn’t they? MOTHER FUCK, WHAT?!
Right after I’d plated our dinner I went searching for my boxers. I’d left them in the foyer and had started to feel cold because I’d had the A/C on full blast that hot and humid summer. Plus I grabbed my t-shirt as well as Em had stolen my dress shirt.
As we sat on the couch and ate our dinner Em was making these super annoying eating sounds and she subvocalized with each bite. However, what got my interest was her critique of our sex.
“Dude,” she said with a full mouth of food as she broke the silence of our meal. “You can really fuck. Holy shit. The way you were going I didn’t think you were going to cum… EVER.”
“Well, I did,” I replied sarcastically and also with a full mouth of food. “How did that work out for you?”
“It feels good in my pussy, no lie,” she said (her exact words). “But what this meal needs is some cheese.”
“I don’t have any cheese,” I said. “Sorry about that. I just can’t…”
“No, not cheese… CHEESE,” she replied straightly. “Maybe you can put some more of yourself into what’s on my plate.” (Her exact words again.)
“Oh, and how would I do that?” I asked.
She looked at me, looked at my crotch, looked at her dish, and shrugged her shoulders.
I stood up and after having set my plate on the table to the right of the sofa took off my boxers. I started to jerk off. Soon her mouth was on me again, and I should say that a mouth that’s been eating hot food is doubly hot. I was getting close. I told her that I was ready and she took me out of her mouth in time to jerk me into her food. This whole event had a “Silence of the Lambs” vibe to it. Had I owned a basket, maybe some lotion (or my cum) would’ve ended up in it.
“That’s more like it,” she said, stirring my spunk into her meal. “You should taste this.” Again, this story is depraved. I didn’t really want to taste myself in my well-executed Italian meal. Still she ate every bite. I recall sitting there watching her as she consumed her dish with vigor.
The whole weekend played out the same way. We barely wore any clothes until we disembarked on Monday morning after I’d pushed her legs to the headboard of my bed during a last minute fuck before she had to leave. She dressed and headed out and it was like that for many weekends after that. She didn’t want me to come to her place, and I suppose that was fair since I was a guy who was way older and not someone that she was proud about being with. She repeatedly told me that she wanted me to put a baby in her. We shared this same weird and hot bareback fantasy, and yes, it was an utterly stupid idea. As I look back we enjoyed one another physically but we literally hated one another on a personal level.
Things changed a second time, and after yet another one of our arguments and long patch of silence, when my friends Dan and Kelli (not their real names either) decided to get married after a decade-long courtship. Dan had asked me to be his best man.
“What are you doing next weekend?” she asked during a phone call following yet another period where we’d not been in touch.
“Next weekend? I’m best man at a wedding,” I replied. “So I’m out of town.”
“And you didn’t invite me? Fucker!”
I politely (I’m not sure that I was polite back then but let’s go with it, shall we?) told her that we weren’t together and that I was more than happy to go stag to my best friend’s wedding. Our conversation didn’t go well, suffice it to say.
The phone rang on Tuesday night and before I could say “hello” Em asked me, simply, “what do I have to do… you know, for the wedding?”
“I’m not taking you to the wedding,” I told her in a completely blunt fashion.
“Well, fuck you then!” she replied angrily, hanging up the phone.
Dan had invited me for drinks that Thursday and as he wasn’t one who enjoyed the bachelor party stereotype we just drank a lot and ate a bunch of appetizers. I’d known the guy since we were 4 years old. I could’ve forced a party on him, but then again he would’ve been mad. No, he would’ve been steaming about it.
“Why are you so distant tonight?” he asked after our third round of booze. I’d been half way through a jalapeno popper which I suppose was a perfect excuse for my delay in response.
“I’m not distant,” I replied.
“That’s bullshit. I know you.”
“You’re going to play the ‘I’ve known you since we were 4 years old’ card, aren’t you?”
“You’re seeing someone, aren’t you? And she’s trouble, right? I know you better than…”
I took a long drag from my cigarette because at that time you could still smoke in bars. “She’s 18, and this is incredibly fucked up.”
“Dude, you bagged an 18 year old?!” He held his hand up for a high five.
“I wouldn’t say that I put her in a bag literally.” I didn’t return his high five.
“Puns. I get it. Sounds hot. Tell me about it.”
I told Dan that I didn’t want to ruin his bachelor party, and he forced the issue by telling me that it wasn’t a bachelor party — which was totally fair. I told him all about USENET and the fucking and the breeding fantasies and let it all out. That’s when he dropped the bomb on me.
“You totally have to bring her to the wedding,” he insisted. “It’ll be fine. Show up, give the speech, be nice to Kelli as you always will, then tell me about it later.”
I’d mentioned my jaw dropping earlier. This is the moment when I became a slack jaw I suppose. “I can’t do that.”
“Why?”
“She’s 18! Come on, Dan!”
“No, no… Kelli has been on my shit about this not being a memorable wedding, but finally? I have ammunition to disagree.”
“Your ammunition is me bringing along a hostile 18 year old to your wedding and that would be fine?”
“It’s my wedding and I, well we, would know what would be fine.”
In short Dan had Kelli outfit Em for their wedding and I felt like a shit, like a hot and runny shit because of that. Kelli was effusive in her praise for Em, and again, I felt even runnier and shittier than ever before. Making matters worse Kelli made Em a last minute addition to her wedding party. Kelli told me that I would not believe what Em would be wearing and while I protested that it was their wedding — Kelli insisted that since she had her own bun in the oven (True Story) the wedding talking points would be as they may.
True to form Kelli outfitted Em in a really sexy dress and heels (but not sexy enough to have upstaged the bride). Em had been very vocal about her disdain for heels, and yet here we were. Em had flirted with some of the younger guests and I was fine with it, Dan and Kelli had been given their due, my toast had gone off with a few chuckles but no other drama, Em and I danced for a bit as she teetered in her heels, then we headed up to the hotel room and fucked til late the next morning.
Following our next Great Fight (TM), it on the way home from the wedding, Em told me not to call her anymore. I was all like, “well, yeah,” and that made her madder. We were non verbal when I chucked her suitcase out of the trunk and into her front yard when we got to her rental house. I squealed the tires as I was backing out of the driveway, and maybe I’m off base here but I think that it made her hotter for me (KIDDING!).
After the wedding Anna and I had started hanging out in the flesh more and I’d told her the story of Em. “You must be fucking virile, dude,” she laughed. “How else could you deploy your cock that way?” (More true dialog, and no, I had not thought of a cock deployment until that point in time.)
The phone rang at my desk at work. The reason why I was in the office that day during lunch is because the weather had been terrible, and I hadn’t felt like braving the rain and wind during my short lunch break. So I’d just gotten some trash from the cafe in the office and was gobbling at it as my phone made its noxious sounds.
“Hello?”
“Hey, it’s me,” she said.
“Oh, hey. How are you?”
“The weather is shit,” she replied and blah blah blah. I kind of tuned it all out so I forget exactly what she said. “Hey. If it’s not too much of a trouble for you, can you come by… later? Like after work?”
“Four hours seems like a long drive just so we can hang out.”
“Hang out? Well…”
“Well, what?”
“I miss you,” she said. “I want us to, you know… like we used to.”
“I don’t think that’s a good…”
“Well, I do. Here’s my address <she told me the address>. See you later.” *click*
Did I do the right thing and ignore her invitation? No, reader, I did not. As you’ve read by now I was incapable at that time of thinking outside of what my dick wanted to do. My dick at that time wanted to Dick Em Down. Little did I know what would be on the menu that night.
Weather had been worse than I’d thought. it took 5 hours to get there. Like my old college rental, the place was a dump. I’d turned my body 90 degrees just in case I’d ended up at the wrong place and needed to run the hell out of there.
Em answered the door finally. She was wearing a terrycloth robe and was pulling it together with her hand. She apologized for being late to the door and ushered me in. That’s when I met Velma for the first time. Of course Velma is not her real name, but she closely resembled Velma from the Scooby Doo cartoon, and frankly, I was never a Daphne guy. I’d always wanted to fuck Velma. She too was wearing a terrycloth robe and her hair was soaking wet just like Em’s. “Did they shower together just now?” I asked myself. “Nah, that would be too Cinemax. No way they did that.” Oh, reader, but just wait. Wait. We are a couple of hand jerks from crescendo. Thanks for bearing with.
Velma and I exchanged some pleasantries and laughs and I felt pretty good because not only was she eyeing me, she wasn’t doing so in a way that said, “this 22 years older fucker is laying pipe to my friend… and it’s gross.” I liked Velma instantly. My god. I’m a fucking child.
Em ushered me into her room, dropped her robe, stripped me, and I was about to unfurl a condom when she asked me what I was doing. She wanted to go raw again. Uh oh. Well, but then again I was stupid and went with it. Em was LOUD that night. The bed was slamming against the floor and I fucked her harder than I had since the very beginning. When we were done she rolled out of bed and went into the hallway nude. She had to pee apparently.
I’d kind of dozed off when I heard whispering in the hall. Velma and Em were having an emphatic chat. Then they both appeared at the foot of the bed. I’d gone soft and my shaft was flopped near my hip. Em crawled up in bed next to me and played with my nipple (which I supremely enjoy to this day).
“So,” she purred in my ear. “Velma wants to have sex with you. Do you think you can do that?”
“Get a condom. Left pocket,” I whispered back.
“But she-”
“No ‘but’,” I said. “Just get it.”
“I like it when you’re brash with me. It’s super hot.”
Em motioned to Velma who dropped her robe. Her nude and rubenesque figure graced my presence. Em fluffed me with her mouth before she put the condom on. Velma got on top and we had a surprisingly slow fuck. Velma kept begging me to take the condom off because it would feel a LOT better (of course it feels better. Jesus! I’m not chaste!) but I just wan’t into it on that night. Then she and Em started making out during our tantalizingly slow fuck. O. M. G. So hot. So hot. That’s why I wrote it twice. SOOOOOO HOT. See what I did there? Then Em started trying to make tongue contact with Velma’s clit when she lifted off me.
Eventually I filled the condom, and I didn’t really check on Velma’s status. Did she cum? DON’T KNOW! She and Em joined in a 69 and I wish I could tell you more. I got dressed and left. Em left me a series of angry voice and emails but I had to break free. At some point Em got married to Bill (who I gave the super secret nickname of BillDo) and she stopped calling. Anna and I were heating up and 20 years later I can tell you that being married to Anna was *thumbs up emoji*.
Source: reddit.com/r/gonewildstories/comments/bj8beu/mfmff_fucking_young
Wow!