Online Adventures Vol. 01: Monica

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.

Despite the dirty conversations, we had shared via text, our in person conversation was not so brazen, save for a few clever teases on both our parts. A few times there was that awkward silence that happens from time to time. Each time, we'd make eyes at each other until someone said something.

Aside from this flirtation being so intrinsically hot to begin with, there was something so illicit about this for me. I hadn't told anyone about this, nor was I planning to. I liked this feeling. A lot.

We got up from the table and walked outside.

"This was nice. We should do it again sometime." I said as we walked towards the subway station on the corner.

"How does 8pm tonight sound?" she replied, smiling. "I'll text you."

"Can't wait." We hugged and kissed on the cheek as I walked down into the subway station.

I was home by about 3. I was jittery, excited and immensely horny. It took everything I had not to squeeze my cock.

Monica texted me a half hour later. I don't have the text, but it read something like this...

"Well Mister =) I was not expecting you to be even sexier than you are in your pictures and such a nice guy (Dare I say gentleman?). Thank you again for lunch! I have early dinner plans tonight with some family. But perhaps you'd like to come over afterwards for dessert...

How could I refuse?

"It was my pleasure and I should say the same of you too Ms. Monica. Or is it Doctor? =) I'd love to join you later, if you hadn't already figured that out!"

"Lol. One more thing... thong or g-string?" she asked.

I wasn't certain what she meant by this. For me? For her? But I just went with it... "G-string, for sure" I answered, pretending I understood.

She replied with the blow a kiss emoji face. Someone was wearing a g string tonight. I suppose it only added to the intrigue tonight.

Monica gave me her sister's address, which wasn't more than about 20 minutes on the subway and a five minute walk.

It was 5pm and I figured I'd better shower up and do a little manscaping. I trimmed up all around my cock, using electric clippers and cleaned up my balls as good as I could. In our conversations, Monica had told me she likes the pornstar shave, so I took it as short as I could. I definitely have an above average sized cock, not huge, at just around eight inches hard and reasonably thick. I've never had any complaints. But my balls... a normal size and shape, but they hang LOW. Low enough that most of my sexual partners seemed surprised and/or commented. Some loved my low hanging balls, but most women I've encountered would tend not to pay them much attention. I told Monica about my cock in our conversations but I hadn't told her about my low hanging balls. I figured, she'll like 'em or not, but let's not give her a reason to back out now.

With my trim complete, my cock looked even bigger than usual, and because I was BEYOND horny. It was definitely not limp. I admired myself in the mirror. I felt sexy. I swung my cock and my balls around, admiring myself. I never thought of myself as an exhibitionist, nor did I have any sort of stripper fantasy (at least that I was aware of) but dancing around in the mirror, letting it all shake, I felt HOT. And I knew I wanted to do this for Monica. That is of course if watching me pose or dance naked for her is something she'd even enjoy in the first place

I jumped in the shower and took extra special care of myself, leaving no crevice unscrubbed. I scrubbed myself head to toe, taking extra special care of my asscrack and of all my goodies. If Monica were as oral as she claimed to be (or even as oral as I am) I had a feeling she'd have her mouth everywhere and I didn't want to disappoint.

Squeaky clean, I got dressed. Boxers, jeans, a clean shirt and I was out the door just after 7:30. I was a bit in shock. Was this really about to go down? If tonight were going to be even half as hot as the conversation we had yesterday, how does one mentally prepare? Years of vanilla sex with Amanda passed through my mind. I smiled as I boarded the subway.

When I exited the station, it was go time. It was 8:03 and I was just fashionably enough late that it wouldn't look like I had shown up early and waited till 8 on the nose. I walked three blocks and there I was outside her sister's brownstone. I knocked on the front door. It opened. And there stood Monica in a white terry cloth bathrobe, the kind you get a nice spa or hotel. Immediately I could smell her. Fresh out of the shower. Delicious. Her hair looked dry, so perhaps she had been out of the shower for sometime, but regardless she hadn't gotten dressed.

"Hi there" I said to her, trying to disguise my nervousness.

She pulled me inside without saying a word. With the door closed behind me she wasted no time leaning in and sliding her tongue down my throat. She put her arms around me and we sucked face. Monica was a great kisser. Wet. Passionate with just the right amount of sloppy. Those lips...

"Hi baby" she mustered, breaking our kiss.

"You smell fucking delicious" I told her, trying to sound sexy.

"I taste even better", I'm told.

Monica took me by the hand and led me from the entrance hallway into her sister's living room.

"Sit." She instructed me, pointing to one of two sofas in the room. I sat.

She walked across the room and turned back to face me. "The g string you voted for earlier?" She undid her robe and it dropped to the floor.

Monica stood there in nothing but a skimpy g string and a smile. Her big beautiful tits staring me in the face and those areolas big as coasters. Her g string barely visible, hidden even more so in those tree trunk thighs of hers. She had a big stomach, but not too big, accentuated nicely by her g string, showcasing a VERY plump pussy. Though she was several feet away, it was clear Monica packed a meaty cunt.

"Your move" she said.

I stood up and was stripped down to my boxers in seconds. "I have something for you Monica".

And with that I dropped my boxers and stood there naked for her.

"This is YOUR cock". I lifted it and showed her my balls, which were so heavy at this point, they hung almost halfway to my knee. Inside I hoped she liked them. Knowing what I did about her, I had a feeling she would. And did she ever.

"Holy shit" she said. She had this googoogaga look in her eyes like a child who just saw a toy she absolutely needed her parents to buy for them.

"Your. Balls. Are. Fucking. Perfect" she remarked. "Ohhh am I going to have some fun with you" she went on.

"As I was getting ready, I was getting so turned on thinking about you seeing me naked, and here we fucking are" I said to her, giving her a nasty look.

"Oh yeah?"

"Oh yeah", I replied. With that I put my hands behind my head and began to gyrate my hips slowly in a circle, swinging my cock and balls around for her. She immediately grabbed her pussy and that's when I realized as much as I wanted to put on a show for her, I had to fuck her right this second...

I walked over to Monica. I grabbed both her tits with both hands and squeezed as I put my tongue in her mouth.

Her hands found my cock and she squeezed. And there we were making out like two horny fucks, hands squeezing each others parts. Her tits felt so fucking good in my hands. I pinched her big fat nipples, lightly at first and then with growing strength till I got a whimper out of her.

I broke our kiss and picked up one of her giant breasts with both hands. Her giant areola, big as a drink coaster, maybe bigger. I stuck my tongue out big and flat and gave her areola and nipple a big, broad lick. I licked it up and down and took her fat, sausage-thick nipple in my mouth. As if my dick couldn't have gotten any harder, her nipple felt so good in my mouth. I suckled it, bit it just a little and went for a nice hard suck, increasing pressure till again I got that same whimper.