Greetings readers!
Two years ago (shortly after my 30th birthday), I got out of a (too) long relationship with my ex girlfriend Amanda. I had spent the better part of my twenties with her. There were plenty of good times, but as the years went on, our sex life became less and less eventful. Sadly, it wasn't particularly eventful to begin with. When we ultimately broke up, it took a few weeks for me to get my head (and the whirlpool of emotions spinning around therein) back on track. With Amanda in the rearview, I had realized that I had YEARS of good sex to catch up on. In particular, I realized that it wasn't just sex I was looking for but some reasonably light kink, intrigue, adventure- something different from the vanilla I'd been living with for nearly a decade.
I had discovered the personals section of a popular online classifieds while selling a guitar Amanda had bought me a few birthdays back. Out with the old, I figured. For anyone who's ever browsed this section of the classifieds, you know there is quite a range of listings. Some with photos, some that get right to it, some a little less aggressive. I had never been on an online date but as I had been in the market for a little excitement and intrigue, Online personals seemed like a good place to start. As a New Yorker, there was no shortage of listings.
In the two years which followed my breakup from Amanda, I met approximately 15 different women of various backgrounds and ages (ranging from 27-58). I discovered a lot about myself during these encounters, particularly that I have a seemingly bottomless appetite for BBW.
What follows are true accounts of my favorite encounters with 8 of these women. Names and certain details have been changed, but the plot of each of these stories is accurate or VERY close. I hope you all have as much fun reading these accounts as I had writing them. Enjoy!
Volume 2: Kimmy
"Cougar seeks cub!"
My previous experience with 41-year old Monica left me with a delightful taste in my mouth when it came to older women, so when Cougar Kimmy emailed me back after sending a very carefully crafted message to her, I was pretty stoked.
Kim (or Kimmy as she insisted I call her) seemed to be in her late 40's, maybe early 50's but I didn't find it polite to ask. If she wanted to tell me, she would. We exchanged the customary photos and she got right to it with two topless pics.
Kimmy was SUCH a MILF. Average height, perfectly overweight, DD cup breasts (she told me the size) with a very round ass. My favorite thing about her (so far at least) was her face. There was no other way to say it. She simply had a VERY beautiful face. She looked a bit like Vanna White, I had thought. In her photos, she was always smiling (which intrigued me about who was taking these photos for her) but as far as I was concerned, she was she was smiling at me.
We started exchanging emails on a Monday evening, texting by Tuesday and the plan was for me to come up to her townhouse in southern Connecticut on Friday night, assuming we were still into each other by the weekend.
Kimmy seemed pretty cool. Former hippie, very into classic rock, The Grateful Dead in particular, and music of that genre.
"Maybe we'll throw on some Dead, roll an enormous joint and dance around my house naked like it was Woodstock" she had suggested in one of our conversations.
None of that sounded like a bad idea to me. We chatted about our interests, likes and dislikes. Kimmy wasn't into anything outlandish.
"If it feels good, and we're both comfortable, go with it" she spoke like a true flower child I thought.
Kimmy seemed super chill, as most Deadheads tend to be and that put me at ease. I was done with uptight bitches like my ex girlfriend. Kimmy seemed like anything but.
I'm definitely not a dick-pic kinda guy but since she opened with some sexy shots, I sent her a photo of my cock at it's hardest.
"Such a BIG boy" she texted back."Friday can't get here soon enough," I replied with an emoji kissy face. Sending the photo was hot. Made me feel a bit sleezy. But maybe that's what my life was missing...
Kimmy and I stayed in pretty consistent contact via text, keeping the energy going, which made an otherwise stressful week of work, way better.
A very pleasant distraction. She'd text me during work asking me how it was going. And when I hit her with the sad face or angry face emoji, she'd reply with something like: "Remember Jay, Woodstock is only a couple of days away." I knew what that meant and by Friday morning, I was beyond stressed out and in need of something to take my mind off work.
"Tonight's the night!" I texted her.
"You ready for our playdate?"
"Never been more ready. I've even been listening to The Grateful Dead all week!" I replied. She liked that.
She texted me her address and suggested I take Metro North up to her station in lower CT. From there I could walk to her house or she could pick me up. I didn't want to put her out, so I told her I'd walk from the station, and hopefully arrive by 8.
"Oh, one more thing hun" she texted before we ended the conversation. "I'm not like those young bitches you're probably used to."
I already knew this, of course, by now. I tried to say something flattering. "Oh I know, you seem way cooler."
"Thanks babe, but there's something else, which doesn't always jive with everyone... I have a big fat bush that I am VERY proud of..."
I wasn't surprised to hear this. She was a 60's/70's flower child through and through it seemed. And she was right about what I was used to. Most women I had been with were somewhere between completely shaven and very nicely trimmed. I was SO into Kimmy at this point that if her hairy pussy were a problem for me, it didn't register at the moment. My mantra throughout this whole online dating thing was that I could walk anytime I wanted, so let's roll the dice on Kimmy's "big fat bush" (as she so delightfully referred to it).
I thought to myself as I responded to her text with something along the lines of: "Oh yeah? Well if you're so proud of it, I can't wait to see you strut yourself and show if off for me tonight."
"My my Jay, you have all the right answers. Don'tcha?. See you at 8"
"Can't wait, Kimmy."
After a quick shower, the usual grooming and a quick strut in the mirror, I was out the door and on my way to the train. I grabbed an express train, which still took an hour. I hadn't taken the train to Connecticut before and was pleasantly surprised to see that this particular line had a bar car because I definitely could use a drink at this point. I purchased a tallboy and nursed it the entire way there, arriving just before 8pm.
I took out my phone and began following the directions Kimmy had provided me to her house.
At just after 8:15, I rounded her corner and found the house. "I'm here" I texted her. Just as I stepped up to the front door, she opened it.
"Jay!" Kimmy said, throwing open her screen door.
