Tag: Girlfriend

TL;DR This story is about cheating. If this is not your thing, please just move on. This happened many years ago, and is a true story.
Tracy (not her real name) was a friend. She was the BBW type, and a tomboy. She basically wore nothing but flannel shirts, jeans, and shit-kicker boots. And she walked like a man. But she was a super talented musician, an overall hilarious person and good soul, and I loved hanging out with her. We ended up having a sexual encounter out of the blue, and for whatever reason we had insane sexual chemistry. So we kept doing it on the regular.
Over the course of a few months of our sexual relationship, her demeanor changed. She started wearing lingerie and skirts, dresses, stockings, thongs, and heels. She started wearing makeup, and started shaving her legs and armpits. And she also started getting waxed. I didn’t ask her to do any of these things; she just did them, and with each of these incremental changes, our sex life became more and more intense. She was also extremely smart, and as a result knew which buttons to press with me, and she played that game extremely well.
She told me that she loved me, and I told her that I loved her, but this is one of those sad cases where one person loves the other person more than the other does in return. Heck, a decade earlier I’d been in a relationship with a woman where I was totally smitten, but my girlfriend at the time had her own agenda. A year into it and I hadn’t met her family or friends. It’s shitty how we all operate at times, but unfortunately it’s also a reality of life.
Tracy (and her 2 kids from a former relationship) moved in with me, and that’s when things started getting weird and bad. Her ex didn’t pay child support of any kind. I was supporting 4 people now, and she made a meagre income (she had been fired from her previous job, and was probably blackballed in her part of the industry, given what had taken place at her previous employer). And then she dropped a bombshell on me; she wanted us to get married. And this is when I got exposed, when things went to complete shit, and I ended up fucking somebody else.
One night, after the kids were in bed, Tracy and I had it out. She was basically like, “well, if you won’t marry me, then no pussy for you.” Odd strategy, if you ask me, but it was what it was. We’d been fucking at least once a day since she moved in, then suddenly there was nothing. I was going out of my fucking mind, as I am a highly sexual person, and I was also supremely pissed about the dynamic that had already taken form. Cheating wasn’t on my mind at that point, but exiting the relationship with Tracy definitely was.
Ultimately, Tracy and I were supposed to visit her family in California with her kids in mid September. Given her no sex mandate, I flatly told her that I wasn’t going. She was kind of like “fuck you”, and left for a week with her kids. I was home by myself, scheming to figure out how to exit the relationship, but also horny out of my freaking mind. Should I go to a strip club? Should I hire an escort? Should I rent a bunch of porno DVDs through the mail (I actually did)? Should I peruse the personals on craigslist?
Yup, and that’s what I did. After exhausting myself by jerking off to porn DVDs for about 3 days, like non stop, I was still hard up. So I hit up the personals (women seeking men) on craigslist full on. Casual encounters was such a shit show, so I didn’t bother with that. I looked for the personals where there was a glimmer of hope about having a sexual encounter with no strings. And finally, I found one that I liked, so I responded.
Lisa (not her real name) got back to me, and we proceeded to move from email to Yahoo Instant Messenger (YIM). Lisa had just gone through a breakup with her high school sweetheart. She disclosed that she was 19 years old, and attending a local college. She was looking to scratch the itch, and she was delighted that an “older” guy like me was willing to chat. The conversations over YIM kept getting more and more explicit. It’s not like I’ve been into younger chicks. I haven’t been, believe that or not. But six weeks into Tracy’s master plan, I need to get off in a satisfactory way. I figured that this was another vehicle to get myself off while Tracy and the kids were away. Boy, was I wrong. Very, very wrong. And sometimes it’s great to be wrong. Read on.
And then Lisa asked to exchange photos. Ah, fuck. Talk about getting exposed (twice now). It’s not like I’m a troll or anything, but Lisa? Gorgeous. Tall, blonde, amazing body, just stunning. So I sent along my ghetto-ass picture, and figured that it was done. Nope. She liked it, and asked if we could meet up on Friday (three days from our chat). I invited her to the house for “cookout”, and laid some ground rules.
I’m with someone now, and discretion is paramount
I need to see her STI tests, and I would provide mine
No means no 100% of the time
She had to be gone no later than 3pm on Sunday, should she stay that long
I stopped working at about 4pm on Friday. It was still hot and sunny out. Lisa arrived around 5pm, just after my dinner prep was complete. She was even more gorgeous in person, like that girl I’d meet when I was in high school, but my nerd stuff and awkwardness wouldn’t let me punch into another gear. But here I was, all of 38, and this 19 year old is standing before me in a white sundress, about half down her sky-high legs, and a pair of black, strappy, high-heeled sandals. She was clearly not wearing a bra, and her nipples kind of strained the fabric of her dress. I was enthralled. My god, how much more trim would I have gotten — if I had an ounce of confidence when I was young?
We hug, and Lisa compliments me about how big I am. And yes, I am a gigantic physical specimen. We trade STI results, like I’m a bouncer at a bar where she tries to get admitted as someone who’s underaged. I invite her into the kitchen where I am finishing my dinner prep, you know little cutting veggies and that kind of thing. I offer a drink, and as I am sipping wine, she asks for a glass of wine.
“House rules,” I said. “You drink here underaged, and you have to stay overnight.” That was a total fabrication, but no way I was going to serve someone underaged and have them crash their car. Plus I really, and like truly, wanted to fuck her. Both in the pussy and the ass. Was it going to happen? Mmm, maybe? Oh, actually. TL;DR it did happen. And nobody injured somebody else, themselves, or killed themselves in a car wreck. So let’s get on with it.
Lisa agreed with the rules, and I poured her a glass of white wine. And then she had a second. Now, I’m a guy who isn’t into fucking when drunk. It’s a bad optic, and it’s particularly stupid when you have sex when impaired — with someone that you barely know. That’s just me, of course.
She was kind of giggly after two glasses of wine. And I fired up the grill so that we could have some food: a little bit of steak and salad. After the meal, she asked where the nearest bathroom was, as “wine flows right through me.”
Lisa excused herself to the bathroom right up the hall from the kitchen. I was in the middle of cleanup after dinner when she returned to the kitchen, clearing her throat to get my attention, as I was in the middle of loading the dishwasher.
And there she stood before me, wearing nothing but her strappy sandals. I couldn’t believe that this was happening in my own lifetime. Somehow, I calmly finished loading the dishwasher, adding the soap into the dispenser, and clicking the start button, before washing my hands and drying them before…
Taking a good look at her. My god, her body was perfection. Tight abs. Busty and non-sagging tits. Pale skin with tan lines in the right spots. Furry bush but with a clearly waxed or lasered undercarriage. Thigh gap. So sexy. It’s that place between the pussy and mid thigh, where a woman who puts her legs together still gives you this hint of daylight. Barbell pierced nipples. I asked her to turn for me, and then I saw the “tramp stamp”. I usually hate massive piercings and tats, but she was perfect, like absolutely perfect. Why she was in my home and wanting to be fucked was beyond me.
The dishwasher started to whirr as I stripped naked in front of her. Lisa and I kissed as she wrapped her sandal-strapped foot around my leg. Hands were probing everywhere. I ran my middle finger along her crotch, and she was soaking wet. My god. We were about to fuck.
My clothing ended up as a puddle in the middle of the kitchen. We were both completely naked, well, outside of Lisa’s sexy sandals, and I forced her to lean over the island in the kitchen as my tongue snaked between her pussy and her very inviting asshole. She came the first time, and even though she told me to stop, she came a second time, squirting all over me and making a mess of the ceramic tile flooring.
I dragged her upstairs to my/Tracy’s bedroom, and threw her insanely long legs over my shoulders. And then I started fucking her. All the while Lisa kept imploring me to knock her up. This has always been a fetish of mine. Barebacking. Pregnancy risk. Dropping my seed in her. I did the same things earlier with Tracy, and while allegedly Tracy was on the pill, Tracy totally got off knowing that I was trying to knock her up. As I did as well. So here I was with Lisa, a woman half my age, fucking her with the vigor of the young man I was 19 years ago, and I unleashed a rope inside of her. I literally could not stop cumming during our first fuck. It was delightful to say the least.
Lisa knew how much I came in her, and we kissed a lot after I clearly nutted massively hard inside of her. My god, I was finally off the bubble. I just fucked a woman, and with passion. It had been weeks and weeks.
Her mouth came back to my cock, and I had no idea who taught this woman how to suck cock like that. Tracy was really, really good at it. But Lisa was better, which was odd because Lisa was a lot younger than Tracy. Lisa got on top of me, and I pinched her pierced nipples as we fucked again. This time it was a lot slower, with intense thrusts and bursts, and about an hour into it, I told her that I was going to cum, and I shot in her again, with the same intensity, but most certainly with less cum.
We dozed off for a bit, and I dreamt about what our kid would look like.
When we woke up, Lisa took off her sexy sandals. Then she asked if I had anything for her to wear. Mmm, I’ve always loved when a woman wears my clothing. It’s a thing, and maybe it’s a power thing, but I dig it. So I gave her one of my dress shirts, and she wore nothing but this collared shirt, firmly pressed, before she told me that she was hungry. I started to rummage through the refrigerator, but Lisa told me that she should make a mean omelette, and asked if there was any bread so that she could make toast.
Yeah, the omelette was amazing, and the toast was crisp. Before long, Lisa and I had a slow fuck as we watched this true crime drama on one of the cable television stations. I seeded her for a third time, and we each had another glass of wine afterwards.
Two hours later, Lisa was hungry again, and said that she wanted dessert. I pulled out my semi-flaccid cock and wagged it at her. She told me that I was an asshole, and said that she wanted ice cream, and asked where we could get it.
There was a mini mart about a mile from my/Tracy’s home. I donned a pair of board shorts and a t-shirt, and Lisa continued to wear my dress shirt, but ran upstairs to put her sandals back on. What a sight to behold we were. Lisa’s endless supply of hair, wearing nothing but my shirt, and her sexy sandals. Me wearing board shorts, a t-shirt, and my Adidas sneakers. I literally saw these people twice a week. They were my cheapest hookup for gasoline, as I had to fill the tank multiply, given my regular treks into Boston. And frequently I’d be in there with Tracy and/or her kids. So now I’m there, buying a pint of Chunky Monkey, with Lisa, and the regular employees were curious. I didn’t give a fuck that they saw, but most certainly, they saw.
We returned to the house, and she fed me a spoon or so of ice cream. I fucking hate Chunky Monkey, and I admit it. But it was cool that this young woman was feeding me shit, as she wore my dress shirt, and with those sexy sandals. We switched the tv to repeats of Seinfeld, and she basically fell asleep in my lap. I was fucking near old at that point; how did this young chick fall asleep ahead of me?!
I carried Lisa upstairs, and we fell asleep in my/Tracy’s bed. Saturday was a lot like Friday, but then Sunday happened. Lisa wanted to shower, and I joined her. Fucking in the shower is one of my favorite things, and I pumped her full again. And, as I recovered, my tongue found its way to her newly clean asshole. And she told me that she was curious about ass play, so… yeah, we did that too.
Lisa and I just kept fucking and fucking and fucking. I have no earthly idea of why it played out like this, but from my end of things, I was enjoying it immensely. I think that Lisa enjoyed it as well, as she kept going with it, but then again I didn’t care. Yeah, I was such an asshole. And I kinda still am.
Sunday morning was a blur. Lisa and I had a couple of slow fucks, and I took her asshole again. Then we showered together, and next thing you know it’s 2pm. Tracy was going to be home at 3pm. Holy fucking shit. Lisa got dressed in her sexy sundress, white thong, and high-heeled sandals, and we were about to say our goodbyes when she asked me to fuck her again.
Was I going to say no? Nope. I peeled her white thong off from underneath her dress, and started fucking her in front of a open window in my/Tracy’s bedroom. I did the deed yet again, and Lisa drove off about 10 minutes before Tracy returned home with her kids.
I was in the shower when Tracy arrived back, and I came out in a towel. Tracy was holding this white thong in her hands whilst asking me if I had a nice week when she was away. Oops! But that’s a story for another time.