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 1: Monica
"In for the weekend. Latina BBW seeks company!" the advertisement read.
Online personals is all about the law of averages. Lots of fake ads. Lots of BS, scammers, what have you, so for every 10-15 ads I replied to, I'd be lucky to get some type of response.
I had come home from happy hour on Friday afternoon a bit tipsy as I normally would after a Friday happy hour with my coworkers. I opened my email and was delighted to see that I had one reply to over a dozen emails I had sent out over the past couple of days. As I opened it, I hoped it wasn't fake. Latina? BBW? Both would be a new experience for me. The vast majority of sexual encounters I had in my life had been with skinny, uptight girls, so this would be something new. I had found that a lot of the porn I had indulged in recently had been BBW porn, not exclusively, but I found that I definitely enjoyed it a whole lot. I NEEDED to find a big, sexy, jiggly woman to play with, and when I opened my email, I could not believe my luck.
"Hi Jay! So much bullshit in my inbox, but you came across as probably the most normal person to reply (maybe the ONLY normal person?). Also pretty cute. I've attached a couple of pics. Message me back if you think we might be a good fit" - Monica.
Monica was a stunner and at least from the photos was VERY much up my alley. She had attached two photos from the shoulders up. Monica had long, dark black hair, perfect teeth and a gorgeous smile. I couldn't see much of her body from the photos, but it was clear she had a big frame. I began imagining a giant pair of breasts and matching ass, thick thighs the whole deal. I emailed her back immediately, crossed my fingers and hoped for the best. As her posting referenced being in for the weekend, perhaps this was time sensitive?
Ten minutes later, my crossed fingers paid off. She emailed me back. Maybe I was getting ahead of myself, but I could feel my dick hardening.
We emailed back and forth a few times and pretty much figured out that we were both looking for something similar. Some no strings attached fun and as Monica lived in Philly, this would likely not be a regular thing, but who knew. After being reasonably confident that neither of us were psycho, we exchanged numbers and began texting.
We exchanged a few more photos. I was in luck. Monica did in fact seem to have the giant breasts I had hoped she would, though I was not able to see what she was working with in the rear. The photos were G-rated but her rack was unmistakably large. After bombarding her with compliments, she felt comfortable enough to send me a slightly more scandalous photo of her on the beach in Cartagena, wearing a lavender bikini that was a bit too small for her. She had quite a tan and her thong bikini bottom was all but swallowed up by the juiciest thighs I had seen in awhile. I was hard. I was drooling. I was sold.
I sent Monica a beach picture as well. At 5'11'', 180lbs, I'm in decent shape and certainly wasn't showing off a man-candy, beefcake physique, but she seemed to be into me so far. I expected her to reply with something like "cute!" or "sexy!" but Monica was clearly done with tact.
"Can I bite your nipples?" was her reply.
Gahhhhhhhhhhhhh. I wanted to say everything to her all at once. But I wasn't sure where to start.
"Can I bite YOURS? =)" I replied back, hoping this would kick our conversation into higher gear. And it did.
We spent the next hour or so texting back and forth about turn ons, curiosities and the like. I was delighted to find that she LOVED that I was very much into bigger women and that we were both insatiably oral, among other things. She was also 41 years old, which was something new for me. But at 41, I had a feeling she knew exactly what she was doing, what she liked and how she liked it. That only added to the intrigue for me.
When we had exhausted this part of our courtship, it was time to discuss the weekend. Monica was in town till Monday morning, at her sister's brownstone in Morningside Heights, birdsitting her sister's parrot. A bit of an unusual circumstance, but that was the last thing on my mind at the moment. We decided to meet at a cafe a few blocks from her sister's place the following afternoon for a few drinks, meet face to face and see if we really did want to have the kinky fuckfest we had been texting about for the past hour or so. If that went well, we'd meet up later that night.
My mind was swimming. From her pictures, Monica was sexy as hell and she was into me.
"See ya tomorrow", I wrote. She replied with the lipstick/kiss emoji.
At this point, I absolutely had to jerk off. Having such a sexually charged conversation with such a beautiful woman, combined with that photograph of her in that lavender bikini was enough to have me on the brink for the past hour. I pumped my shaft for like three seconds before I came all over my hand. With my post-nut clarity, I had a minute to think about if I were really ready for this. Again, having not had any sort of similar experience, I felt a bit in-over-my-head, but THIS was what I had been deprived of for YEARS, in my dead-end relationship with my loser ex-girlfriend. Within minutes, my cock was hard again and I had my answer.
I showered, got dressed and met a few friends in the upper west side for dinner and a couple of drinks. My mind was elsewhere. My friends seemed to notice and asked more than once if everything was ok. In reality, everything was MORE than ok. I brushed them off and tried not to be so wrapped up in the raunch that I was anticipating 24 hours from then. I kept taking out my phone because I wanted to text Monica telling her how I was thinking about her, but we had such a nice end to the chat earlier, I didn't want to bother her or risk coming across as too eager. But as I went to put my phone back in my pocket, she texted me. As I went to open my messaging app, I had hoped that it wasn't her cancelling on me. Much to the contrary. Monica had sent me a close up photograph of her giant breasts. And they were everything I had hoped they'd be. They were ENORMOUS and they looked fucking DELICIOUS. Monica's areolas were the size of drink coasters-- easily the biggest I'd ever seen. They were dark purple with little dots and wrinkles and I was speechless. And at the center of each one, Monica's big, fat nipples stuck out, what appeared to be an inch or so from her massive breasts. A mouthful to say the least.
"Did you say you wanted to bite these, baby?" the accompanying message read.
"Yes please!!" was all I could muster up.
Monica was a Goddess. And she had me hook line and sinker. We exchanged a few more texts and confirmed the plan was still to meet at a cafe for lunch around noon tomorrow and take it from there.
"How was I going to make it till then?" was all I could think, until my friend Paul snapped me from my reverie, calling me over to the bar for a round of shots. My brain was soup at this point. Drunk, horny, excited. At the moment, I was in overload and nothing had even happened yet.
By midnight, I was a bit too drunk and began making my way back to my apartment. I collapsed in bed with plans to jerk my cock one more time but I passed out instead.
I woke up at 10am with a hard dick. No surprise there. I'm usually pretty horny in the morning, but today I was ready to GO. My lunch date with Monica was two hours away and I could not have possibly been any more excited. I wanted to jerk off, but I held off, fantasizing about cumming buckets when Monica and I finally got it on. Even if I were going to cum quickly with her, I knew from our conversations that she claimed to LOVE heavy cummers and I certainly didn't want to disappoint. Plus, if this worked out, I had a feeling we'd be up a better part of the night, having multiple rounds. So as much as it left me in discomfort, I would not be cumming until later, one way or the other.
I showered up, threw on some nice jeans and a button down shirt and hopped on the subway. I figured I'd get there a little early, get a table and just mentally prepare for what was to come. Fortunately, the cafe wasn't particularly busy and the host told me to grab any available table. I chose a booth in the corner, out of the way as I figured it'd be a bit more private; and a few minutes after I sat down... there she was.
I saw her enter and raised my hand and waved. She saw me, smiled and walked over. I got up to greet her and suddenly became aware that I wasn't sure whether we were hugging, shaking hands, kissing? I went for it. We hugged and kissed on the cheek.
"Hi Monica" I said, attempting to sound comfortable.
"Hi Jay" she replied, perhaps a bit shy herself.
Everything about Monica was big. Perhaps even larger than life for a skinny white boy like me. She was wearing a purple blouse and dark jeans, which fit her perfectly.
At 5'10'' and what I guessed to be about 225lbs, Monica was way bigger than any female I'd dallied with in the past. Her long, dark black hair looked like it had been straightened and her smile was even more perfect than it was in her photos. Her lips though. I had perhaps gotten so drunk on thoughts of her gigantic breasts that I hadn't even paid much mind to how big and full her lips were.
And speaking of her breasts. There they were. Big and round. I knew what was inside that blouse. I had seen a picture of them. I wanted to touch them. To hold them right there at the restaurant. But we weren't there yet and I had a good feeling I'd be doing that and more with her titties all I wanted later if lunch went well.
"It's very nice to meet you. I'm very glad you wrote me back" I told her.
"Well I'm very glad you wrote me." she smiled, as the waiter came by to take our order.
We spent almost two hours at lunch, enjoying some pretty normal date conversation-- what we do for work, for fun, our annoying families, while we're still single, and such. Monica was a professor of education at a prominent college in the Philly area. She had her PhD. which I thought was pretty cool. Monica had it going on, both physically and intellectually.
