I had been chatting on an online erotic site for months with Paula when I accidentally replied to an innocent question and gave away my general location. Not a big deal, but over a week or so, she put two and two together and realized we lived closer together than either of us thought.

We have had lots of fun, erotic chats, exciting cybersex and what we could be doing sexually to each other if we ever met. Lots of simulated oral sex and teasing of the genitals were a weekly gratification for us both--- very sensual at every chat. I found myself looking forward to every planned chat with her.

We probably described every part of our bodies to each other online and enjoyed describing how we could make one another explode in delight by fucking or whatever. I know I exploded quite a few nights and she sounded like there were orgasms on her end.

She claimed her avatar was her and I knew mine was me, so we could visualize every moment as we typed merrily away to each other. But now there came a twist I wasn’t expecting.

“How far from the Gulf are you, Jack?” she typed innocently during a chat.

“Oh, about a quarter mile, why do you ask?” I replied, wondering how she knew about my proximity to the water. Did I screw up and inadvertently give up information? It didn’t matter as I was divorced as was she, according to her.

Paula typed back, “Well, I think I may have seen you playing guitar at one of the casinos a few days ago. I remember a guy that looked like your avatar in a nice blue shirt, playing a red guitar and singing up a storm by himself. He was very entertaining.”

I thought, “Really, Paula?” She thinks she really saw me! I knew it was a good possibility, but never thought it could happen.

“Yeah, I was with friends and pretty high, but I was too surprised to do anything.”

“Oh, oh!” I thought, then typed, “It’s possible, I’m not quite sure.”

I did do a single act at the Rock in Biloxi several weeks before as I work the coast casinos regularly, especially the pool area as I’m big on Buffett, Taylor, and Eagles. “Do you remember which one?”

“Yes, it was the Rock; you were playing in the evening. I thought it looked like you but wasn’t sure so I didn’t come up, plus you had a constant thing going on with some older women who kept talking to you between songs. You sounded great!”

I didn’t know what to type. I waited. I remembered the three women well!

“Was that you, Jack?” Paula typed. “Did I blow a chance to meet you face to face? I was in a second-floor room with a balcony overlooking the pool party. I’ve been hoping it was you, so man up, was it you?”

I couldn’t believe that happened. I thought we were states apart in our many chats. What were the odds? We had some fun evenings having chat sex for an hour or two; Paula had an imagination and a dildo that I had pictures of. We had some very hot comments on what we would do to each other sexually and I think we both were extremely explicit in 'what if.'

I decided to go for it. “I believe it was, Paula; those women thought I was their own private band; they bought me enough cocktails for a three-piece band. Tell me the truth, did I really sound good to you?”

I was trying to change the subject of the cougars stalking their prey. I fondly remembered the three girls'-night-out group. All attractive, well built and uninhibited ladies having a good time. I actually got my brains screwed out later that night and woke up in their room with a cutie under each arm!

“Yeah, you did sound great, did you get lucky? LOL.” Paula paused and then, ”They all had the hots for you… just like me.”

The pause went on until I typed, “ Really? I mean, were you excited?”

“What do you think after all we’ve shared online? I started dreaming of us fucking as soon as I got to bed." Paula paused. “I used my dildo twice that night just thinking it was you and we could actually spend real time together. I’m getting wet just thinking about the opportunity now.

"Hey, Jack! I know you’re the person in the avatar and we have shared everything online, so I’m sure we should discuss it. Besides, you’re always chatting about how you would like to eat my pussy! This could be the chance!”

I thought for a few seconds then typed. “If you’re serious, I’m playing next weekend, both nights at the same place from six to nine o’clock. Why don’t we think about it for a day or two? If you want to just stay online lovers, we can go that route; if you really want to meet with me, we can have a drink at the pool. I get a comp room when I play so it’ll be there if we want private time.”

“Good idea, Jack; you think this over and chat about it tomorrow night. I like the idea. Same time tomorrow okay with you?”

“Same time, beautiful!” I signed off the website, sat back and breathed out heavily. I had heard that these things happen and it looked like it might happen to us…

***

Well, it was the weekend and I was set up near the pool for the adults-only party (kids have to use the other pool). We agreed that we would finally meet at the pool and take it from there.

My guitar was tuned and I started off with some ‘Brown-Eyed Girl,' Buffett-style, to set everyone's mood. I like the calypso feel to the song and it helps me get a good feel for the crowd. I looked to see who was tapping their feet or hands to the beat and I was pleased that most of the small crowd was already into the song. I kept playing my set for the next forty-five minutes.

The sun was still up, throwing long shadows as I watched two cuties in big sunglasses and floppy hats walk through the entrance and get a table not too far away.

The table next to them had three guys who immediately started their line of shit that seems universal in bars the world over. I could see the girls smile and nod at the guys, so I knew their first drinks were bought. The second round would depend on their availability for dancing, chatting, and more. I’ve seen this mating game played so many times that I’d miss it if it didn't occur.

My song ended and I spoke to the audience, ”Hi everyone, I’m Jack the Kat, and I do requests so if you have a song you like just write it down on the back of a ten or twenty and send it up to me. I don’t do Eagles, but I do sheep, goats and the occasional pig!" Always get a lot of laughs. But occasionally a ten or twenty in my tip jar. I love the tips! Sometimes I get invited to do private concerts in ladies' rooms; that’s even better than the tips.

I continued playing my set and watched as several couples danced and several others just sat and wiggled to the beat. One of the two cuties was dancing with a couple of the guys sitting next to them every other song and she finally gave out and sat down next to one of them. She seemed the life of the party.

I stopped for a breather and grabbed my bourbon and Coke. Taking a long pull, I surveyed the crowd.

An older lady with a very attractive figure in a red one-piece came up and handed me a five and asked if I did a certain slow song as it was one of her favorites. “Of course I can,” I said and strummed the intro chords to ‘Lady In Red’ for her. As I was singing, the second of the cuties walked up to me with a one-dollar bill in her hand and set it, writing up, on my little music stand. I almost jumped when I saw the request: ”Do you eat pussy?”

Paula!!

I looked at her face as Paula slowly removed the sunglasses and there she was. Beautiful blue eyes, black hair to her shoulders, and braless complete with swollen nipples, exactly like her avatar and our chats. She was wearing a great yellow, short, tight, sundress that accented her body. I noticed my cock getting bigger in my shorts and actually felt a drop of pre-cum ooze out; she looked better than her avatar. My heart was beating faster!

She stood there smiling as I finished the song and when I turned to talk to her, she planted a passionate kiss on my mouth that stretched me out to my toes. I thrust my tongue into her mouth and played hunt-and-suck with her.

I tried to talk but her kiss lingered into several moments. Not enough to turn many heads, but long enough that my cock poked out into the guitar and strained to get out of my shorts.

“Hi, beautiful,” was all I could manage to get out of my mouth as I wanted her back in there. ”I’ve dreamed of this all week long! Can’t believe you showed up and with a cute wing-woman! My mind has been working overtime on things we can do. If you want!”

“Well then, we’ll have to see that you’re not disappointed, won’t we?” she said over her shoulder as she walked back to her table where her friend now awaited her.

I played two more songs and announced a break, putting on my own songs to play while on break. Lots of mixed slow and easy listening stuff.

Looking over at Paula’s table, I saw her friend had returned and had one of the guys sitting next to her.

Paula smiled at me and beckoned me over with her index finger outstretched with that come-hither motion. I gleefully walked her way.

“Hi! Have a seat, honey,” Paula said, patting the chair right next to herself. “Been saving this one for a stud like you! By the way, this is my friend Terry. Terry, meet Jack”

“Thanks, don’t mind if I do!” said I, nodding towards Terry. “Hi, Terry, singing is hard work! And the guitar playing, whoo! Makes a man horny! I mean, thirsty!”

Turning to me, Paula put her arms around my neck and kissed me lightly on the lips. "How long a break do you get?”

“Oh, about twenty minutes, what you got in mind?” I drawled.

“Well, that’s not time enough for what I want, but it’s a good start. Can we dance to a slow tune?" Paula drawled in a breathless voice. "I’ll make it worth your while!” She arose and pulled me to my feet.

We walked arm in arm to the dance area. The sun had set and a slow song was playing; we wrapped our arms around each other and began to dance.

Fortunately, we were in a shadowy part of the floor as it quickly resembled a grind of lips, tits, penis, and vagina, rather than a dance. I hoped management wasn’t watching as I needed the gig. Of course, I wanted the pussy more.

As the song ended and a fast tune began, Paula looked at me and asked,” Anyplace private we can go for a couple minutes, Jack?” What? She couldn't hold out for a couple hours until I finished my gig? Did she need some right now?

“Hmm, yeah, there's a sorta alley behind the stage that no one goes to at night, it’s got boxes and stuff stacked up.”

“Great! That will do! Can you take us there?” Paula’s blue eyes sparkled with mischief and promise.

“Okay with me, come on!”

I took her hand and we walked behind the stage area, looking back to see if we were noticed, I saw her friend Terry looking straight at us with a big smile on her face. I smiled back as Paula pulled me into the dark, private enclosure.

She put her arms around my neck and pulling me in for the kiss said, “I’ll only need a couple minutes, sweetheart, then you can return to work. I just needed a private moment with you to show my appreciation for your honesty online and making tonight possible.”

We kissed deeply and she ground her pussy into my nice hard cock. “Wow, Jack! I think your friend needs some appreciation too!” Her right hand deftly pulled the zipper down on my shorts and pulled out my dick in a continuous motion. I shivered from the hand squeezing me and the night air.

“Oh, boy, Jack! You haven’t been fibbing about your dick size! It’s huge! Just right!”

And with that, Paula dropped to her knees and placed her lips on the tip of my dick. Her tongue tickled the underside of my cock and then took me inside. Her mouth was warm and wet as she sucked me into her as far as I would fit. She slid her mouth off me long enough to say, “What a delicious cock, Jack, you have quite a mouthful!”

After a few more licks on my dick, she looked up and said, “Sorry! I couldn’t resist, Jack! I’ve really dreamed about sucking you off like this."

She sucked me back into her mouth and my knees got weak and I started to tremble. This was one of our online fantasies. We pretended we had just met.

I was getting so close, so fast, the delight of her wet mouth had taken control of me. She was in charge and knew she had me where she wanted me.

Paula massaged my scrotum and sucked up and down, licking my frenulum with each outward suck. I could feel myself getting close to cumming and, reaching out to the walls, braced myself for support.

I needed to cum so bad I was shaking. My balls slammed upwards, my ass got rigid as statues and I came into Paula’s mouth so deliciously. I began to moan harshly as I felt ribbon after delightful ribbon of my fluids exploding outwards from my cock into her mouth, each pulse more pleasurable than the last.

I came down slowly from my euphoria, breathing deeply and deeply drained. My eyes started to focus and I croaked to Paula, ”Just wait until I can return the favor.”

“Gulp!” was all I heard for a moment as Paula finished her chore.

She looked at me and said, “I hope that’ll hold you until we can get to your room, honey. But if necessary, I’m available next break. I am so looking forward to your turn!

“Now, let's get you a drink so you can sing me a pretty love song!”

We walked back to her table, arm in arm, where her friend waited.

I hoped I had energy and voice left to sing for two more hours…
 

Thanks for reading! Okay, I want to write about my career as an entertainer over the years in segments like this. I think it will be fun and probably take ten to twenty chapters to just get it going. They won’t be in any chronological order as I remember old situations in random flashes. Hah! Hope you’ll enjoy and score and comment. Again thanks! Jack