Cruising Ch. 01

Taking my hands she stood me up and moved me to the foot of the bed where there was the most floor space. My first request was to explore her body. In her boots she was now much taller than I was which was fine since it lifted everything up closer to where I wanted them. We stood nearly toe to toe and I reached around behind her legs and placed my hands on the back of her legs just above her boots. Taking my time I moved upwards to feel her magnificent ass. It was nice and firm and I enjoyed exploring the curves. Moving up I felt her waist and fairly flat stomach on the way to her tits. With the first feel I found the implants. It was a good boob job with the sacks under the muscle but it was easy to find. I don't know any hormone therapy that could make triple D's so I was expecting to find augmentation.

I played and explored her body for several minutes until Monica went into action forcing the next step in our session. She turned me around so I was facing away from her and she threw her left arm over my left shoulder and under my right arm pit drawing me against her body. Her right hand located my prick and began several strokes while she ground her crotch into my ass. I could feel my erection hardening up even more.

Monica ordered me to lie face down on the bed and spread my legs. She was playing the whole Domme thing out even though I didn't ask for it. I didn't mind, I was enjoying it so far. Monica crawled onto the bed and pulled my ass cheeks apart. She gave one quick sniff and released me immediately.

"The bathroom is down on the left. Give your ass, cock and balls a thorough cleaning and dry off with the blue towel before we go any further." She said as she stood back up.

I stood and went to the bathroom. Standing in the tub/shower I washed myself off completely. Having showered in the morning I thought I was relatively clean but between the flight and walking around in the hot sun I guess I was a little gamey. After I was clean I returned to the play room. Monica was standing up leaning against a dresser stroking her dick which was sticking out of the side of her panties.

"I hope you did a good job. Now lay back down as you were." She commanded.

Once I was back in position Monica climbed on the bed and gave me the sniff test again. Apparently I passed since her tongue began tickling my ass. This wasn't discussed and I wasn't expecting it but it was very enjoyable. She relaxed my ass and eventually let her tongue probe inside. This relaxed me even more and I was looking forward to a good ass pounding.

Let me do some explaining. I do not consider myself gay, bisexual at best. The male body does nothing for me. However, in my late teens, during an affair with an older (married) woman, she taught me the joys of anal play, both giving and receiving. So I have enjoyed tongues, fingers, and toys in me for some time and then I was introduced to transsexuals. They look like women (hopefully) so they do turn me on but they have a cock. I soon learned that a real dick attached to a real person feels much better that a hard piece of plastic or silicone. So, on occasion, when I get the anal itch I will meet a transsexual for a session. So if that makes me gay, then so be it. In my opinion I'm not but think of me as you like.

Monica withdrew from my butt and went to cover her cock in latex (a deal breaker for me) and get some lube. After watching her prepare I was ready. She instructed me to turn over so she could watch my face as she fucked me (her words). I lay on my back and she lifted my legs. The head touched my sphincter and she eased on inside. It had been a while since I had any anal stimulation and I had to force myself to relax and let this happen. Usually I look for ladies with less than seven inches of cock but I learned that length isn't the issue, it's the girth that I have trouble with.

Monica was a comfortable size for me and soon was inside. We repositioned a bit and she began to give a good steady butt fucking causing my dick to drip precum a bit. She reached for my erection and gently stroked it. I was pretty turned on and told her that I wanted to turn over. Once on my knees Monica began to slam me pretty hard causing more drips. I held on enjoying the ass ramming until I wanted to up the game.

I turned to look over my shoulder and said, "We're not done until you cum."

This must have surprised her. She placed her hands on my shoulders hanging her big boobs on my back and proceeded to pound me hard and deep. Her breathing pace increased as she got closer.

She said between her panting breaths, "I'm close, do you want me to pull out?"

"Hell no! Shoot your load inside of me." I said.

Monica couldn't last much longer. One last hard thrust, one long groan and I felt her cock unload in my ass. She let out one long satisfied sigh and I felt her white knuckle grip on me loosen up.

She pushed herself upright and withdrew carefully saying, "Thanks, that was nice."

I lay down on the bed on my side since my hardon wouldn't allow me to lie face down. Monica was off the bed and in the bathroom in a flash to clean up. After I heard the water running she returned to the bed and positioned herself with her head at my crotch level. She leaned in to suck me.

"Hey, wait a minute. Take a minute and chill. You gave me a good hard humping. Relax and catch your breath." I said.

Monica smiled, "Thank you. It's nice that you are thinking about me. Not many clients do."

"I know that after I have an orgasm I need a little time to relax and enjoy the sensations. If you need to finish me off because you have another appointment I understand but if there is no need to rush then take your time."

We lay in bed together and talked for about 15 minutes. I explained that I had been cyber stalking her and been planning on meeting her the next time I was in town. Monica seemed a little disturbed by that until I went into greater detail listing all her attributes that I enjoyed and why I wanted to meet her. That seemed to make everything all better.

With the atmosphere more relaxed I was rolled onto my back and Monica kneeled between my legs. She used both hands and her lips to work my dick back up to its full length. Watching her work she took her time and worshipped my cock with her lips, tongue and mouth. Unfortunately for me the head was very good and I was already on the verge from the ass fucking that I didn't last very long. Catching Monica by surprise I called out that I was cumming. She pulled back so only my head was in her mouth and used her hand to pump a big load of cum out of me. Once I was spent she raised her head up and opened her mouth displaying my spunk in her mouth and played with it using her tongue. This was not a turn on for me and I turned my head away. She quickly swallowed and went back to the bathroom to clean her mouth. I was pretty well spent and when Monica returned from the bathroom I asked her to hand me my phone from my pants pocket.

"Calling the wife?" she quipped.

"Nope, don't have one of those any more. I'm happily divorced. Calling for a cab." I explained.

"Where are you headed?" Monica asked.

My hotel is well known and Monica replied that she could give me a ride if I could wait for a bit. I was grateful since it was later in the afternoon, almost rush hour, and I thought there would be a long wait for a taxi. Monica turned to dress and I lay on the bed enjoying the satisfaction of a good session.

After a while I rose and went to the bathroom to clean up. Monica's bedroom door was open and she was standing naked in front of a full length mirror brushing her hair and admiring her body. Apparently she wasn't shy. After washing up I went to stand in her doorway and watched as she got dressed. We chatted some more and I admired her body now that I got to see all of it. She pulled on a larger style of panties stuffing her prick down in the front. A nice white bra, a sundress and sandals and she was ready to leave. I went back to the playroom and quickly pulled on my clothes. She led me through the kitchen to the garage. She had a mid-level BMW that looked brand new. I sat in the passenger seat as she started up the car and opened the garage door with the clicker. Carefully backing out we were on the way.

I believe that Monica is practicing for the Grand Prix. She drove overly fast, cutting corners on her turns, shifting the manual transmission like a pro and scaring the living shit out of me. At one point when she was forced to stop at a red light I was able to pry my hand of the 'oh shit' bar and pulled out some cash.

Handing over $150 I explained, "The hundred is a tip for services well done. The fifty is for the ride."

Monica looked dumbstruck saying, "I appreciate the generous tip but the ride is no big deal."

"I would have had to pay for a taxi. Besides riding with you is much more exciting."

She laughed at that and we discussed another meeting when I returned after the cruise. She offered to pick me up as long as I gave her enough notice. She dropped me off in front of the hotel and gave me a kiss on the cheek thanking me for my generosity and that she was looking forward to seeing me again. She insisted that I fuck her ass next time. I explained that it wasn't really a thrill but we could discuss it.

Monica was off and went back to the room. I was alone so I took the opportunity to shower and dress for dinner. While I was pulling on my shoes and socks the happy wanders arrived fairly drunk carrying a few shopping bags.

Ronnie said, "We had the best time today!"

They stammered out all that they had done and I reminded them that we needed to get ready for dinner. Bob was the only one that took the hint and gathered his things before heading to the bathroom. The two ladies proceeded to tell me all their day while I sat in the chair and listened. Then Ronnie began to undress.

"Ronnie! Please don't do that!" I said honestly embarrassed.

Ronnie looked around puzzled. "Why the hell not? You've seen me naked. Bob knows it. I don't care if Laurie sees me. So what's be big deal?"

I had to agree with the logic but I was still embarrassed by the situation. Ronnie stripped down to her panties and her oversized sports bra as Laurie began stripping as well.

"Now hold on a second missy. I do have a problem with you being undressed in front of Bob." Ronnie stated.

"I'll be quick. I still hear the shower running. I'll bathe after dinner. Relax, I'm no exhibitionist." Laurie replied.

They both changed into more appropriate attire. After Bob emerged the ladies went into the bathroom one at a time to freshen up. Four people sharing one room was definitely a challenge and required a great deal of patience.

Once everyone was ready we went to the lobby and I asked a valet for a cab to the restaurant I named.

"Why?" he asked.

"For dinner." I replied.

"No, it's closed. They closed down a few years ago." The valet informed me.

"Oh. I have not been to town for a while, I didn't know that." I said.

"It's a shame, their food was excellent."

"Do you know of another place with excellent Cuban food?" I asked.

"Low price, average or top of the line?"

"Where ever the best food is, the price doesn't matter." I explained.

"Do you mind a little hole in the wall family restaurant?" the valet asked.

"Not at all. Some of the best food I ever had was in those kind of places."

The valet wrote down an address in the heart of the Latin area of Miami on SW 8th street. It was a little family owned restaurant that was tough to find. We made our way in to the tight eating area and had to wait 25 minutes for a table but believe me it was worth the wait. We had sangria and the rest was just a blur of food. The wife of the owner didn't speak very much English but she made it clear that she loved Ronnie and Laurie's size since she was a larger lady too. She kept ordering food for the table insisting that we try this and that. We had a thin steak covered in lime juice, a fish (we never found out what type of fish it was which was a shame because it was delicious) that was deep fried (the whole fish), roasted chicken that fell off the bone and slices of pork shank that had been marinated for days. Everything came with delicious shoe string potatoes and lots of side dishes. The wife was practically force feeding Ronnie and kept hugging her as she kept talking about more food. Eventually her husband, the chef, came out to greet us. He spoke much better English than his wife and explained that the wife felt that all American women are too small and she loves meeting big ladies who like to eat since eating is so much of a great joy of life.

We were all fairly drunk and absolutely full but the wife insisted on bringing out four individual portions of flan that were on the house. We accepted one and the four of us each took a bite. To me flan is flan but Ronnie attacked it finishing it off. She always did have a sweet tooth. We asked for the check and the wife seemed almost embarrassed to give it to me. The bill was $78. I've paid more than that for one meal for myself and it wasn't as good as this was and I wasn't as full (and drunk) as I was here. Everyone at the table offered to take the bill sight unseen as a thank you but I had already said that I was taking everyone out. I pulled out $160. And left it on top of the check.

Bob looked at me and said, "Wow, looking at this place I didn't think it would be that much."

I took the bill out from under the cash and handed it to Bob.

Bob's eyes popped out of his head and he said in too loud a voice, "Holy fucking shit! Is this for real?"

Ronnie snatched the check from Bob's hand and looked at it. Without a word she handed the check to Laurie.

Laurie summed it all up with one word, "Seriously?"

We all leaned in and had a quick discussion about how good everything was and how they couldn't believe that the check was so low. Not to cause a scene I suggested we make our way outside leaving the money on the table. The wife hugged both ladies as we made our way to the door and warmly shook both of the guy's hands thanking us and hoped we would come back. Outside I had to adjust my pants since I was so full. I would have been happy going for a walk to let everything settle and work its way through my system but everyone was tipsy and tired. Then the ugly reality hit me right in the face. We need a taxi. Again, none could be seen.

Just then the wife came crashing outside holding the check and the cash crying, "Too much money! Too much money!"

We all had a good chuckle over that. I tried to explain that it was worth the money to us and everything was excellent. I wanted her to take the cash but she kept trying to push three twenties back at me. Eventually I won the fight and earned us all hugs. Fortunately I had the foresight to ask about a taxi. She reached into her bra and plucked out a cell phone. She dialed a number from memory and spoke quickly in Spanish.

"Five minutes." She said after she hung up.

It took three. A gypsy cab pulled up blasting some type of music (I am being generous when I use the term music, to me is sounded like 30 drums battling to the death) with the windows closed. The wife went over to the window and spoke quickly to the driver and handed him one of the twenties.

"He take you. You no pay." The wife smiled.

I wasn't going to argue. More hugs and we loaded into the car. Ronnie in the front seat and Laurie in-between Bob and I. We told the kid driving where we were going and begged him to turn down the drum massacre.

Back at the hotel I wanted to walk for a bit. Laurie joined me while Bob and Ronnie went up to the room. I thought they might appreciate a few minutes of private time together. Laurie and I walked near the water's edge in the hot, sticky night air. We chatted about the cruise when I heard a fart.

"Oh! I'm so sorry. That was supposed to be a quiet one. I'm really embarrassed." Laurie said.

I replied with one of my own.

"That's why I wanted to walk. To free the gas. I figure its better outside than in a room with three other people."

"Good point." Laurie replied.

We walked around for about half an hour but we were both tired, buzzed and gassed out. At the room door we knocked and waited before coming in just in case they were going at it. Bob was sitting on a bed reading and Ronnie was in the bathroom.

Laurie gathered her things together for her turn in the bathroom. It dawned on me that I don't have anything to sleep in. I had boxers on so that would be my sleep wear. Following Ronnie's logic, the two women have seen my goods and I don't care if Bob sees me in my underwear. Ronnie came out of the bathroom and was wearing an oversized tee shirt which is kind of her signature look. I've either seen her dressed, naked or in a tee shirt. She can't find a bathing suit so whenever she goes in a pool or hot tub she wears the tee shirt and (I'd like to hope) something underneath.

Ronnie had showered and was brushing out her hair. She asked if I minded her turning on the TV which I didn't. She put on some cooking reality show with some super chef screaming at some real chefs. I just ignored it. What I did do is take the paper from the valet and programmed the address of the restaurant into my phone so I could find it again. Laurie came out wearing a tee shirt as well (I guess none of us planned on wearing any sleepwear this trip). We all chatted for a few and then climbed under the covers and said our goodnights.

Once the lights were off Laurie and I spooned together with my balls pressed against her butt facing the other bed. We relaxed as we drifted off to sleep. I could hear Ronnie and Bob talking very low and kissing. I could hear them moving around like they were touching each other and I felt Laurie's hand reach behind her and locate my dick.

Laurie repositioned onto her back next to me and kept rubbing me as she said to me softly, "Hearing them fool around is so fucking hot. I can't believe how turned on I am right now."

"You could always go to the bathroom and rub one out." I said.

"Not when I have a perfectly good dick right here." Laurie insisted.

"Nope, count me out. I real uncomfortable playing like this. It's weird for me since I've been with Ronnie and she's fooling around with her boyfriend five feet away."

Laurie released me and turned back onto her side. I knew she was disappointed but didn't push the issue. We could hear more playful movement from the other bed with more kissing. Things quieted down but then I heard a rhythmic rubbing of the sheets, like Bob was getting head or jacked off. Bob's breathing patterns became uneven and I wondered if he was going to blow his load. After a minute the rubbing sounds slowed down and stopped. Bob's breathing returned to normal. More kissing, a few words and the show was over. We all fell asleep.