Online Adventures Vol. 05: Monique

"You gonna lick me clean? Or are we doing the sticky, sweaty snuggle thing?" I asked.

"You already know the answer to that, baby." =)

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Things went on like this. We continued to communicate, daily for the most part. Photos and sexting galore, swapping links to porn videos we had come across, some insanely hot phone sex a few times a week. Monique and I still had our lives. I would obviously still date and flirt and fuck if it got to that point and I assumed Monique was as well. I had intentionally tried to keep our conversations from getting too personal, not for my sake, but for hers. From our chats, it wasn't super clear what her exact relationship was with the aforementioned boyfriend but at 47, Monique was clearly "having fun" as she put it. She was "over the bullshit" and "not taking a single thing in life any more seriously than necessary." I got the sense that Monique got dick (and perhaps some pussy too) whenever she wanted, but she was over the whole dating game.

"I have a couple of friends I can call if I'm ever feeling the urge, but most of the time I'm just happy to go online and play with my clit." She had said at one point. "At 47, the dating game is silly. And I am just exhausted."

And as much as I enjoyed all the dirty talk, it was the real talk, just like this, that was making me feel the way I was about her.

I told Monique a decent chunk of my life story. And she seemed interested and asked interesting and flattering questions. And it felt good. It even felt a bit cathartic having an honest conversation with her about my ex-girlfriend and the circumstances that had brought me into the whole 'let's get nasty with a total stranger from the internet' chapter of my life I was currently balls deep in.'

"Something I've come to live by at this point..." She had said amidst one of these conversations... "You can't spend your life getting in your own way. I swear... the number one thing that prevents most people from enjoying their life to the fullest... is themselves and the obstacles they create for themselves. And people do this because of what they think life is supposed to be. That's why you stayed with your ex as long as you did. Because you thought that's what life was supposed to be."

Monique made a tremendous amount of sense. And while Monique was not my therapist, I found some of these conversations to be immensely therapeutic. There didn't seem to be anything I could say to her, for which she didn't have some sort of supportive or nurturing response. She made me feel really good.

Monique's life story was pretty darn impressive. From very humble beginnings, she worked her ass off, stayed humble and hungry. And now she was the owner of three very successful beauty salons. She even owned the buildings. And it was at this point I realized that while this woman oozed sexuality, the sexiest thing about her BY FAR... was her self-made success.

What started as lust became a legit friendship. We had become super comfortable with each other. We'd talk about our days, about her favorite and (more entertainingly) her least favorite clients. She'd tell me about the "annoying bitches" who worked at Monique's salon (though she did love her employees very much and treated them very well) and just generally all the silly daily shit we all deal with from time to time. She knew about my bigger days at work and would wish me luck and ask me how things went afterwards.

The elephant in this room, however, was always the distance. As into each other as we seemed to be, the whole idea of traveling several hundred miles just to hook up with someone from the internet (while not that unusual these days) felt more transactional than organic And we felt that our 'relationship' deserved something more organic. We kept the idea of ever getting together very open and we'd talk and flirt on and on, not about what we would do if we ever got together, but what we are going to do WHEN we get together. This open-endedness of this situation kept our 'relationship' in a constant state of arousal. And there was a certain safety, and a boldness that seemed to accompany this safety. Being so far apart, and without any pressure or plans to ever meet or act on anything we've spoken about, fostered a level of closeness I didn't think I could ever experience with someone whom I had no specific plans to ever meet. This somehow, made things even hotter.

"I love how comfortable you are with me, Jay... and I hope you've realized that I feel the way with you as well. I've chatted with and done plenty with plenty of men and a few women, as you know... and you are a rare find, I must say." She texted me, one evening amidst one of our filthy conversations.

I had recently opened up to her about my experiences with Tamara and with Kristin (See Volumes 3 and 4), the fake cocks, the kinky cock play, the naked kinky dancing, the buttfucking. All of this of course was something that I had kept entirely to myself (with the obvious exceptions of anyone who has read my stories so far) and had no plans to likely ever share with anyone. But Monique was different.

"Honestly, Monique..." I wrote back to her. "It's different with you. It's easy. With you, it's like...it's like..." What was it like? I struggled for a moment and really thought.... "It's like I'm at my most comfortable and very aroused when I'm being vulnerable with you in some way. Does that make sense?"

"I think you just stumbled onto something." She wrote. "It's something we all share, but most people won't ever allow themselves to experience the full weight of their own vulnerability. I'll bet it's been fun as fuck to let yourself go, meet all these bitches online and get filthy... Hasn't it?"

"You said it, babe."

"Here's an example. How good did it feel... How much fun was it to tell me how much you loved Kristin's big dick? How did that feel to say? How did that feel to say to me? =)"

I was speechless. My cock was at full mast.

"It felt really fucking good."

"Good. It usually does." She wrote. "Call me after dinner and let's see what other things make you feel good to say to me."

Monique definitely had a way with words.

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I climbed into bed that night, exhausted from the day, but never too exhausted to chat with Monique-- even if that meant having a deep conversation-- or a filthy one, till one or both of us fell asleep, phone in hand.

"Hello Jay." She sounded horny.

"Hi Monique." I responded. Even in just this quick greeting, there was depth, feeling, tension. Monique and I had been talking for nearly two weeks, though it felt longer. To say that there may have been something resembling feelings emerging would not have been false on my end. It seemed that it was true for her as well.

"I'm in bed, Jay... Are you?"

"I am."

"Whatcha doin?" She asked, knowing full well the answer to come.

"Shuffling through your photos and squeezing my dick."

"Mmmmm good.... Keep squeezing... And while you're squeezing, baby, why don't you tell me more about all the things that make you feel so deliciously vulnerable in front of me..."

My heart raced. The vulnerability. I thought about it for a moment.

"I wanna dance around naked for you. I wanna swing my penis around for you and show you my butthole and just be so nasty for you, baby."

"Ooooh... and you like to dance naked, huh? You got the moves?"

"No, baby... I just think it's fucking hot. Especially because you'd be so loving and supportive."

"You gonna dance for me like you danced for Kristin?" (See Volume 4)

"Fuck yes, baby."

"Mmmmm... good... You might enjoy some of my dance moves too, baby."

"I absolutely melt at the thought of watching you shake your ass and titties for me." I replied.

"And I wanna hear more about all that fat strapon dick you were talking about playing with earlier."

"Ohhhhhh.... I had a feeling you liked hearing about that..." I jumped in quickly for lack of what else to say. "About how I worshiped Kristin's giant strap on cock... About how Tamara buttfucked me... while I gagged on her wet panties... I know you liked that shit baby..." I continued understatedly.

Monique whimpered on the other end of the line, as she played with her clit. "Mmmmmmmmm Jay... This is more of that vulnerable shit baby... keep going baby..."

"And how I danced with Kristin and we held cocks... or how I crawled over to her on all fucking fours and asked her permission if I could please suck her big fat dick? Is that what you wanted to hear more about baby?"

"Gahhhhh...." She groaned, my words bringing her nearer to orgasm. "More..." she panted, breathed and whimpered.

"I took Kristin's big fat dick in my mouth, Monique... I looked her in the eyes and I sucked her dick. I sucked her big fat fucking dick, baby and it felt so fucking good in my mouth, Monique... You hear me, Monique? I sucked her fucking penis and she came in my mouth and it was heavenly baby..."

We both came. Like crazy.

"Mmmmmmmm... baby..." I moaned, coming down from an absolutely lights-out orgasm. "I. Just. Came. HARD." I went on, taking a look around at the giant mess I had made.

"Lord." She said. "That was a good one."

"Fuck...." I panted.

"You gonna suck my big dick, baby?" She asked.

"I can't wait..."

"You ever suck a real dick? Or just fake ones strapped to freaky bitches? You haven't struck me as being gay or even the slightest bit bi... So this intrigues me... and it makes my pussy wet."

"No...no real dicks for me. And I can't imagine that ever changing. But I think for me it's just always been the oral fixation, having something in my mouth, something fun to suck on and feel with my lips and tongue. The sensation drives me wild."

"I guess that makes sense. But that's all part of the whole getting in your own way thing. You'd love the feeling of a big fat cock in your mouth. Trust me. A warm, fat, throbbing penis massaging your throat, ready to burst and fill your mouth with all that warm milk..."

"Well when you put it like that, Monique." I chuckled.

"Sounds nice... doesn't it?"

"It does." I felt my cock hardening again.

"Feels good to be so vulnerable with me. Doesn't it, baby?" Her voice sent chills through me.

"It feels very good, Monique."

"It'll feel even better when you're on your hands and knees, drooling all over the fat, black dong strapped up to my pussy..." She trailed off, groaning.

"Baby... you keep talking that shit I'm gonna cum again."

"Good... And to help you along, you can have a look at this..." She paused for a moment. A photo came through.

Laid out on her bed was the most realistic looking fake black cock I had ever seen. Dark brown, rippled, muscular, veiny.

"Maybe we can play with this together, baby? You can dance around with it like a fucking perv and put on a filthy little show for me with this juicy dick. If you want... I know I'd like that."

And with that, I came once again.

"Mmmmmm.... You LOVE that shit... don'tcha, baby?" She went on. "And the only ones who know are me, you and those freaky bitches you meet online."

"Baby... the spell you have me under..." Was all I could muster; the orgasm subsiding.

"I know. And I love it... And you love it."

"Love it."

It was late. I was spent, drained. My cock was sore.

"Talk tomorrow, baby?" I asked.

"You gonna dream about my big black dick?"

"You might have to let me know where I can get myself one of those." I joked.

"Baby... You wouldn't even know where to start with a dong like this one."

"Well, maybe if I'm a good boy, you should teach me?" I asked shyly.

"I can't wait..."

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As the days went on, as did the sexting and photo sharing. I especially loved sifting through the various porn links Monique would text me throughout the day. We had somewhat similar tastes and would often circle back to how wonderful it would be to throw some filthy porn on the big screen in one of our bedrooms and indulge to no end. Sometimes accompanying the link would be a note Monique wrote for me like "check out how creamy her pussy gets around the 5 min mark." Or "This bitch knows how to ride a face, what do you think?." Or even "I know you say you're not into real cock... but tell me you wouldn't LOVE the feeling of this dude's giant dong filling up your mouth..."

She knew this drove me wild; and I loved returning the favor-- especially anytime I came across some meaty black penis (my lust for this seemed to turn her on to no end) and shared it with her to admire with me; or any video of some lucky white boy with his tongue buried in some big, beautiful black woman's asscrack.

"The way she presents and just feeds her asshole to him, drives me absolutely wild, baby."

"We can do way better." She replied.

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It had been nearly a month since Monique and I had begun chatting. Our friendship seemed to grow stronger by the day, which in turn seemed to make the nastiness all the more steamy. And finally, nearly a month to the date of our first chat, it seemed we'd finally have our chance to walk the walk, and not just talk it.

"So listen to this, baby." She began. "You familiar at all with what salons look like on the inside? You ever see the shelves of products and stuff we sell there?"

"I've probably been in a salon at some point. But yeah, I definitely have a vague picture of what you're talking about."

"My salons have contracts with various companies and every once in a while, I get contacted by a sales rep here and there from one of these companies, asking me to do some demo or street team type stuff. Sometimes, I'll send one of my girls. Once in a while, I'll go myself. Usually it's local, sometimes I'll do a quick drive and a hotel, but get this-- you ready baby?" She paused.

I had a feeling I knew what was coming next.

"They're sending me up to Manhattan to some expo at the Javits Center and puttin' me up in some swanky hotel downtown for three nights!!!" She was so excited she could barely get the words out.

"Oh my goodness! That's fucking awesome!!" I responded excitedly. When?"

"The 14th-17th. Not this weekend, but the next. Thursday to Sunday."

"Nice! I know you'll be busy with the expo and all, but maybe you'd make a pencil in a little time for your favorite New Yorker?" I asked.

"Well... I will have this hotel suite all to myself. I suppose I might see myself getting lonely... Do you think you know anyone who might be interested in a steamy, hotel fuckfest?"

"I think I know just the guy..."

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The days leading up to Monique's NYC visit were anticipations galore. Monique and I chatted daily about all the usual stuff-- the filthy and the non-filthy; and among other things, the plan for her trip to New York. Monique would be arriving late Thursday night and then working the expo all day Friday and Saturday through about 6:00pm. While I absolutely could not wait to be naked with this woman (and the feeling was assuredly mutual), there was no way I wasn't taking Monique out for a nice dinner and perhaps a stroll too. That said, I told Monique to meet me at 8pm Friday night at the Essex House restaurant, not more than four blocks from her hotel in the Lower East Side of Manhattan. Dinner, drinks, ambiance, and best of all-- Monique.

With our plan in place, the magnitude of the moment hit me. Sure, I had been hooking up with all these women I had met on the internet. To that degree, this was nothing new. But this thing I had going on with Monique definitely felt different. Aside from the fact that we had shared countless back and forths in the past month about all sorts of very personal stuff, I felt something for her. Here and there I found myself reminding myself that these types of interactions between people are pretty typical, and it is not unusual to develop feelings in such a capacity. I wouldn't say I felt nothing for the women in the previous volumes of my stories, but Monique was definitely different. And now the reality of being naked with Monique-- touching and tasting her, being deep inside her... it was a lot to process.

By the time Friday finally rolled around, I had gotten my shit together. I had never stopped being excited about this from the start, but I had never been in a situation in which I had built so much sexual tension over such a long period of time. Obviously, I could not focus on shit at work with my cock hanging at half-mast all day. The hours slowly passed, but they passed.

With work done for the day, I shot straight home. I was restless. I had time to kill. I went for a run in Central Park. I don't normally do that, but I had energy and like I said, I was restless. Home by 6:00pm, I took a very relaxing shower and began my pre date ritual of meticulous manscaping. When all was said and done, all that was left was a thin layer of stubble and some nearly hairless balls. I quickly threw on some deodorant, a very tiny dab of cologne, jeans, a button-down and even a sport coat this time; and I was out the door by 7:30.

I passed one of many bodegas with a beautiful floral display outside and made the on-the-spot decision to buy flowers for Monique. I selected two sets of tulips, one yellow and one pink and had the cashier mix them into a single bouquet. They looked perfect and I couldn't wait to give them to Monique. Shit. I couldn't even believe I was about to meet her.

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All I remember about the subway ride downtown was being excited. Between the sport coat and flowers, I clearly looked (and felt) like someone who had a big night ahead. This felt fun.

Twenty minutes later, I surfaced in Manhattan's Lower East Side. With flowers in hand, I began what would end up being a very quick walk to the restaurant. My watch read 7:59 and I was only seconds or minutes from a highly-anticipated night, which I suppose could end up going in any number of directions. I popped into the restaurant to let the host know I had arrived and would likely be ready to sit soon. When I walked back out, there she was.

At what had to have been just over 6ft (in heels), there stood Monique in a dark green sundress and matching heels. Her hair flowed down past her shoulders, long, lustrous and wavy. Her breasts-- brown, round and big, sat supported very nicely in what had to have been a very strong bra. Her cleavage was intentional. Most noticeably, and I cannot stress this enough... for a woman of (what I estimated to be) in the neighborhood of 225lbs-- this lady was not fat. She was tall, built, strong, thick... perhaps even bursting at the seams in the sexiest possible way. But for sure-- there was a very nice proportion to her height and weight. Monique was in fact MzAmazonia.

She smiled as she spotted me... and then she saw the flowers. "O.M.G!" She said, clearly impressed. "All of this for me? Come here, baby..."

Rather than handing her the flowers, I placed the bouquet on one of the benches out front so that I could go in for the whole embrace. I slowly placed my arms around Monique's waist and we came in together for a kiss. I couldn't believe this was actually happening. My mind was going bonkers.

We kissed on the lips. Once. Twice. We pulled back. We looked at each other.

"Hi." I said timidly.

"Hi." She said right back after a brief pause. She smiled at me. I smiled back. Our smiles said it all.

I lightly placed both hands on the back of her neck and pulled her in for a real kiss. Our mouths opened, our tongues came out and met for a brief moment before our lips closed on each other's. She smelled yummy, wearing a scent it seemed must have been engineered to make men horny. Her lips were big and soft and full... and her broad, wet tongue nearly filled my mouth. Monique knew what a sucker (literally) I was for tongue play and was clearly getting started early.