ONE NIGHT IN ORLANDO

I’ve probably made a habit out of this of late, but apologies are in order for the over extended hiatus. Life’s been kickin’ my butt. Between work and a slight state of depression following my surgery, I sorta lost my writing voice. But I’m good now. Currently I’m in the process of trying to reclaim my swagger – both mentally and physically.

Since I took such a long break this go round, I decided to drop a real gem on ya’ll. I really hope you folks enjoy this shit because it cost me personally to tell this tale. I won’t elaborate on that, but just know, me telling this story came with a price.

Anywho… HE’S BACK!

In order to really appreciate this story I’m going to request that you revisit and read a previous tale of intrigue entitled…The Business Trip.

It was in that story that I had a bit of an adventure in Kalamazoo, Mich. While it didn’t culminate into a carnal endeavor, it did set the stage for a later encounter. Following that trip, for next month or so I periodically remained in contact with the Chocolate Girl w/Braces. While I wouldn’t call it anything serious (I was in Detroit and she being in Cincinnatti) we chitchatted from time to time. But then one day the ante got upped.

Chocolate Girl w/Braces: (via text message) I can’t take this any more. I need to see you.

Serial Dater: (via text message) Is That right?

Chocolate Girl w/Braces: I need to see you badly. I miss you. Come see me!!!

Serial Dater: In Cincinnatti?

Chocolate Girl w/Braces: No in Florida. I have to attend a business conference in Orlando. Please come. I need you.

Serial Dater: I don’t think that’s possible. My money kinda funny. Not a good time.

Chocolate Girl w/Braces: I’ll pay your way. Get some prices.

Serial Dater: You serious?

Chocolate Girl w/Braces: Yes. I need to see you right away. Just say yes.


I didn’t know what to say about the sudden request. But how can you say no to a trip to Orlando (where it’s warm) and you in the Great Lakes state cold-as-fuck. And on top of that I could get some pussy to boot. I started to seriously consider the offer. I really started to consider the offer. The more I thought about it, the more it sounded like an adventure. And I happen to like adventures.

I slept on the offer to make sure it was something I wanted to do. Yes it was illicit, yet somehow there were elements of romance inter-mixt. The next day I hit up Travelocity for prices.

When it came down to brass tax, I was only available from Saturday to Sunday. One night and one night only. I was not missing work that Friday and I had to be back at work that Monday morning. I emailed her the quote for the one night round trip travel. She agreed to cover the cost and with that I was planning my trip to Orlando.

In actuality, I could’ve taken off that Friday night after work, but I had long standing plans with a good friend of mine. And I wasn’t breaking those plans. So I left early that Saturday morning after hanging out and drinking the night before. I hit the road, hopped a direct flight from Metro Airport and I was in sunny Orlando before you could say, “The horny happy hooker sells sea shells down by the sea shore.”

When I left Detroit, I was wearing a leather coat. By the time I got to Florida, I was trying to strip out of as much clothing as possible. It was hella hot out that joint. Ya boy was baking in his urban winter gear. Guess I should’ve paid attention to the weather forecast for Florida.

So there I was in the Sun Shine State, midday. I called Chocolate Girl w/Braces to let her know that I’d landed. She was at some sorta of conference presentation and asked me to just get to hotel and everything would be set up. A key would be awaiting me at the desk of The Ritz-Carlton Hotel. Whoa! That’s right, ole gurl was posted up at the grand-daddy flyest hotel of them all – the muthafuckin Ritz-Carlton. I was impressed.

I hopped a ride on one of those passenger vans at the airport. The driver was a chatty bastard and nosey too. Before I’d reached the hotel, I’d learn all of the personal business of my fellow companions. I also learned from my informative driver, that it was weekend of the big FAMU football game. So there’d be parties abound and out-of-state Black folk everywhere. That lil piece of information actually would come in handy.

I got to the Ritz-Carlton in good enough time. From the moment we pulled onto the property, I was in awe of the hotel and its visiable amenities. Carrying only an over the shoulder bag, I entered the luxurious hotel. Before I could reach the counter, I was greeted and /or addressed by no less than eight hotel employees. The last of which handed me a complimentary glass of cold and refreshing lemonade. I thought to myself, “so this is how the other half live.” It was great.

I acquired my key-card from yet another staffer. “Mr. Dater here is your key, you’ll be staying in the Presidential Suite.” I thought to myself, “Presidential suite…Sweet.” I really couldn’t believe ole gurl had it like that (or atleast her job had it like that). Some sort of conciere dude escorted me to the elevators. The New Orleans Hornets basketball team were staying in the same hotel. So I saw random Hornets bench players roaming about. Part of the hotel was also being used for the shooting of a movie scene, but I didn’t learn the title of the flick. They wouldn’t let me get close to anyting.

As I made my way to the door of the presidential suite, I started to become somewhat anxious. It was all very exciting. I entered the door to the unoccupied suite. It was spacious and exquisite in its décor. En route to the bedroom, I passed a bar. It had appeared that my soon to be host had taken the liberty of stocking it herself. There were two huge bottles of Absolute and several smaller bottles of cranberry juice. One of the bottles of Absolute had already been tapped. I past the bar and entered the bedroom.

Soft music poured from the CD player filling the room with ambience. I sat down my bag and finally took in the entirety of the suite. What’s a shame is that I didn’t even live that good. The suite was better than my apartment in Michigan. I wasn’t even halfway through my exploration of the room and had to take a moment.

I noticed a package on the nightstand and a note in close proximity. Lying beside what appeared to be a hotel gift bag, the hand written note read, “Thanks for coming. This is just a little something for you.” I opened the bag and inside was a pair of fancy men’s dress socks from the Ritz-Carlton gift shop. The receipt was still in the bag too - $20.00. I’d never owned a pair of twenty-dollar sox before, let alone seen a pair. I was a little taken a back.

Also next to the bag on the nightstand were several brand new crisp hundred-dollar bills. Under closer inspection what lay before me was the exact amount of the trip to repay what I had charged for my flight ticket. I pocketed the money and went to retrieve a second note from the adjacent desk. “Go take a shower, fix yourself a drink and relax, I’ll be with you soon.” I must admit, Chocolate Girl w/braces was on her A-Game with the romance and I was impressed. I didn’t even know she had it in her.

Thinking about how everything was going down, something came over me. How can I explain this…I felt like a dope bitch (lol) as my man Mike would say. I mean on the real, Serial Dater was straight on some Pretty Woman shit and I didn’t know what to think about it. But hell if I wasn’t enjoying the shit. If there were one weakness I could admit to having – that thing that knocks me off my square and confuses the hell out of me – it would have to be having a woman spoil me and give me shit. It’s not something that I’m accustomed to receiving, which in turn means I don’t know how to handle it.

I needed to get my mind right, so I went to take a dump. The bathroom was like my favorite part of the suite. It was magnificent on so many levels. Separate shower, a fancy tub, his and her sinks, a vanity table and a private room with a door for the shitter. And there was lot’s of free shit for the taking too (some of which I still got). I grabbed the complimentary book (“Common Phrases and Where They Come From” by Myron Korach) from off of the bathtub stand and went to break-in the toilet. Afterwards a hot steamy shower was definitely in order.

By the time I’d completed my shower and draped myself in the complimentary white robe, my host had entered the suite. She heard me in the bathroom and came to join me. I don’t know if it was the lighting in the bathroom, the ozone levels in Florida or a holdover from the previous night’s drinking, but Chocolate Girl w/braces was looking damn fine. I’m talkin’ “Dayum what her name is” kinda fine. I’d seen her up close and personal in Kalamazoo and I don’t remember her looking that freakin’ hot.

From head to toe she was looking kinda flawless and there was a glow about her too. Her hair was out and it was long and flowing. I peeped the toe and fingernails both freshly done. Right now the name escapes me, but she was wearing one of those pair of jean/shorts hybrids. You know the pants that stop just above the calf. And they were tight too showing off her shapely ass. I didn’t even know she had ass or breast either for that matter. To complete the look, she was wearing a pair of stylish black heals and a black top that exposed her ample cleavage. I immediately started to get wood.

We hugged and quickly caught up. I would learn the reason behind the “glow” was that she had just completed a long session at the hotel’s on-site spa. She took herself through the whole process – massage, facial, manicure and pedicure. And to top it off, she was actually happy, which was completely different from what I saw in Kalamazoo. She told me that my agreeing to come was the reason for the happiness. I didn’t know how to respond. I just hugged her and looked longing into her brown eyes. That’s when I saw it.

I looked down again at her exposed cleavage and saw something on her chest. It was big and looked like it didn’t belong. Upon closer inspection, what I saw was what appeared to be an imprint of a man-sized fist. I gulped internally and asked what happened. The happiness that was just beaming quickly dissipated and a sadness filled her eyes. There was another bruise too. I felt myself fighting back my own tears, which wasn’t my style. I don’t cry. But every since I lost my closes female friend, I’ve become somewhat emotional.

Not wanting to blow the scene that we had going or ruin what the night would bring, she asked that I not inquire about the bruises. I obliged, but I just didn’t get it. What kind of husband beats his wife? Especially a wife that was sweet and accommodating, as this woman appeared to be.

She undressed slipped into the other complimentary robe, made us some drinks (Absolute and cranberry) and joined me on the balcony of the Presidential Suite. The view was amazing. A lake surrounded the resort. It was warm out and this was sure to be one hell of night.

After talking and working up an appetite, we decided to hit downtown Orlando to see what was poppin’. We arranged for a limo to meet us at the hotel and take us downtown. The limo driver was a brotha and seeing that the two of us were black too and appeared to be on a date, he dug into his stash and pulled out his “slow jam” CD and put it on for the ride. It was all good, even though he took us the long way to get downtown. But I didn’t care, cause I was enjoying the company in the back of the car.

I felt like getting a lil frisky so I unbuttoned Chocolate Girl w/braces pants. Then I placed my hands into her pants, pulled her thongs to the side and began fingering her. I couldn’t believe how extremely wet she already was. The privacy window wasn’t up so I know that the limo driver was peepin’ some of the action. I kept fingering her and stimulating her womanhood until she closed her eyes and came. I removed the moistened finger and placed it into her mouth. She sucked all of her essence off until my finger was clean.

Despite the very intriguing appetizer, I was now ready for the main course – dinnertime. We ended up at some fancy restaurant that was owned by some entertainer. Because it was a nice night out, we decided to dine outside. The restaurant had one of those fireplace pits outside, so it was really a romantic scene. Dinner was excellent and when the bill came I was all set to cover the tab. But she stopped me. “I got this. I can write it off on my job,” said Chocolate Girl w/braces. I was ecstatic, because the meals weren’t cheap.

With the limo gone we decided to walk through downtown. We were looking for a bar to post up at and have some more drinks. We found one that seemed to be a part of some festival. There were lots of people and a huge stage with bands performing. It was right about that time that crowds from the FAMU game were starting to spill out and fill the streets of Orlando. I paid the entry fee and went into the bar. We had a great time talking, drinking and listening to the bands play. But it was getting late and there was still something we had yet to do with each other.

We walked out and flagged down a cab. Along the way back to the hotel, I asked the driver to stop at a Rite-Aid. We found one not far from the hotel, so I ran in and purchased a three pack of rubbers. By the time we made it back to the hotel, it was apparent that the shit was about to go down something major. When we hit the room it was like clockwork, we were all over each other – kissing and groping; groping and sucking; sucking and fucking – all until it culminated into one gigantic orgasm.

I was ready to end the night and go to sleep but Ms. Chocolate Girl w/braces asked me if I wanted desert. I thought she was talking about her, but she was talking about actual desert.

Chocolate Girl w/braces: Remember some weeks ago when I asked you what your favorite desert was?

Serial Dater: Yes I remember. I told you Chocolate Mousse.

Chocolate Girl w/braces: Well I checked the room service menu and they have chocolate mousse. Shall I order you some?

Serial Dater: Hell yeah.

Chocolate Girl w/braces: I’m going to get me something too.


We had desert and then we had each other for desert. It was straight animalistic. After we both had cum for a second time, I was bushed. I fell asleep with her on my chest.

The next morning we awoke to a morning smash session. It was like we were living out the movie 91/2 Weeks. I couldn’t believe how we kept going at it. I think there was a lot of build up from the night in Kalamazoo.

{Editors note: I know right now there is probably somebody reading this that knows me personally, and I know what you’re thinking – This don’t sound like the guy that I know. But keep in mind that this is what one refers to as a fling. And as flings go, this is how they go down.}

After the morning break-off we went and took a romantic bubble bath together. We later got dressed and made it down to the hotel’s restaurant for an eloquent brunch. Following brunch we walked down to the lake and sat on the bench at the pier. There we sat and talked for what seemed like forever. Chocolate Girl w/braces told me the entire story of her relationship with her husband and how the abuse started. I was a little depressed after hearing it, but I kept my happy face on, so as not to let her get depressed.

We went back into the hotel room to relax and have another drink. Thinking back on it, there was a lot of drinking in that 24-hour period (lol). As we lay up in the bed chillin’, she made it very apparent that she wanted to go another round. Normally I’m not for the all-day fucking. But this was a special circumstance. However, I was out of condoms. That didn’t stop her from indulging in me one more time. As I watched the game on TV, she took me into her mouth like there was a sense of urgency involved. Before I knew what was happening, I was unloading into her mouth.

We got our things together, straightened out the room and went to check out. Our flights were a still some time away, so we went to the bar to chill and watch the Colts play football. Two more beers later and we were in a van heading to the airport. At the airport it was kinda a sad departure. We sat together for a while until it was almost time for our flights to depart. She didn’t want to leave me. I didn’t want to leave her sad. The tears began to fall from her eyes as we walked our separate directions. One last wave good bye and with that she was gone.

Epilogue: The trip to Orlando was one of the best times I’d ever had on a get away with a woman. It was only a 24-hour period but it felt like an entire weekend. It ranks up there with my weekend getaway to Chicago with Pretty Girl. And that trip included dinner at the Cheesecake Factory, a pre-Christmas snowy walk along the Michigan Mile, a visit to Chicago’s famed museum of history and desert being consumed from off of me. Runner up trips included the weekend island getaway with my ex-wife and the Caribbean cruise with my last girlfriend.