A Much-Needed Second Vacation

It has been about a year since Claire and I took an amazing trip to Cabo, where we discovered Jackie and her amazing talents in amazing surroundings. In the months since, Claire and I have managed to visit some very romantic B&B's up and down the East coast and spent some quality time in the South looking for a vacation home that we might retire to someday. Just recently, we visited Florida to view some properties and had another incredibly sexy experience. Enjoy....

Claire and I have managed to evolve into serious businesspeople in our own rights. Both of us have earned our way up a level of income that combined, qualify us as 'quite comfortable'. This status was also noticed by my boss, who suggested we seek serious professional financial advice before the IRS raked us over the coals. We did. One suggestion we looked upon favorably was to consider purchasing a vacation home. We could enjoy it whenever we were able to get away, and rent it out when we couldn't. Too many positives! So onto the internet we went.

We found ourselves very interested in the Gulf Coast of Florida, between Sarasota and Naples. We looked at numerous properties, multi-million dollar condos, single-family beachfront homes, townhouses overlooking canals, all of it. We then needed to get ourselves down there to personally view some of the more interesting properties for ourselves, so off we went.

First stop was Naples, Florida. A mix of middle class all the way up to super-rich! We found a realtor online who helped us greatly with our search, and her name was Jill. Jill is a 35 year old single mom whose husband walked away the day she told him she was pregnant with his child. She has turned herself into a very successful realtor who was very good at what she did despite living in the worst real estate market in the country! Claire and I liked her and thought she was smoking hot!

Jill stands 5'-1" and weighs about 125 pounds. She has shoulder-length blond hair, a nice even and deep tan, a great figure and killer legs. She also has a great smile and a southern drawl that makes me hard! We met Jill at her office in Naples and Claire elbowed me as soon as Jill emerged from behind her desk to greet us. I also sensed Jill's attention to Claire, her eyes taking in every inch of Claire's incredible figure, especially the amount of cleavage Claire was displaying.

We spent the day together in the warm Florida sun checking various properties, and admiring the view from the many high-rise condos. After a few hours, Claire suggested we stop for lunch. Jill made the recommendation and off we went to Campiello. We sat at their outdoor patio and enjoyed martinis and a delicious lunch. As we sat finishing our drinks, I noticed Claire and Jill really getting along well. Jill excused herself to powder her nose and when she was out of earshot, I asked Claire what was going on. She told me she thought Jill was hot and wanted to seduce her as soon as she could. She said she was sure Jill was interested in her and she said she also noticed Jill checking me out several times. I was flattered and now also interested. I told Claire to go for it provided she didn't think it would screw up our professional relationship. Claire understood and agreed. When Jill returned to the table, we paid the bill and left to see more properties.

Jill informed us that she only had one more condo to show us that afternoon, saving the best for last. It was right on the beach and on the 20th floor facing out over the Gulf of Mexico. It was spectacular. Jill led us through the condo, showing us all the features. While I was interested in the condo, I was also interested in Jill and watched Claire as she began to work on Jill. Claire immediately asked to see the Master Bedroom which Jill gladly jumped on. As we entered the room, I noticed that the room had its own balcony facing the gulf. I watched as Claire opened the balcony doors and stepped out with Jill right behind her. In the direct afternoon sun, I could see right through the sundresses of both ladies, a very sexy view indeed.

Claire and Jill were now talking but I could not hear what was being said. All of a sudden, both girls looked at me, Claire was pointing and Jill was smiling. The very next move put me on edge. When Jill turned to focus back onto Claire, Claire leaned in and kissed Jill on her lips, holding the kiss for as long as Jill would allow, which was about 10 seconds. Jill pulled back and gave a startled look to Claire, but Claire stood her ground and waited to see what Jill would say. Jill shot me a look and licked her lips at the same time. I smiled back at Jill and licked my lips as well. Jill raised an eyebrow at me and turned to face Claire again, only this time she leaned in and kissed Claire on her lips. Claire immediately put her hand behind Jill's head and held her firmly in place as the two women now had each other's tongues out and dueling with each other.

Watching the girls making out through the glass doors was fun, but I wanted desperately to join in. This was a very sexy picture in front of me and I was getting firmer by the minute. I noticed Claire now had her other hand on Jill's back, seemingly pulling Jill into her and closing the gap between them. Jill responded by putting her hand on the back of Claire's neck and really getting into the kiss. The scene unfolding in front of me caused my manhood to stir on its own. I reach down to make an adjustment for comfort and was caught doing so by Jill as she peeked from her kiss to see where I was and how I might be reacting.

Jill broke the liplock on my wife and shot me a smile that made me even harder. With her left hand, she used her finger to summon me to the balcony to join them while sliding her right hand down onto my wife's breast. As I emerged out onto the balcony 20 floors up, I admired the view out over the gulf as well as the spectacular view right in front of me. What was blocked from my view inside was the fact that my wife Claire had her left hand under Jill's dress and onto her hip moving it so that it circled over the perfectly formed globe of Jill's ass. I moved in behind Jill, my erection making a nice home for itself between Jill's perfect ass cheeks, and began to kiss and lick Jill's neck and ear lobe, causing her to moan softly into Claire's wide open mouth. I dropped my right hand down to meet Claire's and together we massaged Jill's ass. Within seconds, Claire's hand left mine and ventured to Jill's mound. I knew this simply by the way Jill threw her head back onto my shoulder and moaned quite audibly into my ear.

Together, Claire and I worked Jill into a frothy, quivering, sexy mass whose needs were about to be met and exceeded. Jill slid her hand down onto my now-protruding bulge and massaged its length which caused me to moan right into Jill's ear! At this point, I had enough of this kissing/groping session. I grabbed Jill's hand, looked into Claire's eyes and nodded to her into the direction of the bed inside and led the two women back indoors. Once the balcony door was closed, the air conditioning cooled us down somewhat, but the heat in that room was awesome!

I pulled Jill into my arms and kissed her very deeply, our tongues wrestling inside and outside each other's mouth. Claire got right in behind Jill and I could hear the zipper on the back of Jill's dress being lowered. As Claire moved the spaghetti straps off of Jill's shoulders, I moved back away from Jill far enough to allow her dress to simply pool around her ankles. I was in awe! I stood and admired Jill's form as I studied Jill standing before me in a beautiful white lace matching bra and thong set. The demi bra barely supported her perfect breasts. Perfect in symmetry....perfect in size.... and in their level of perkiness. In a very cool pirouette, Jill spun on her toes and reached for Claire's straps as well, and in no time, Claire was down to just her turquoise lace boy shorts and white thigh high stockings.

As I stood drooling over the two gorgeous women, they immediately turned their attention onto me, Jill unbuttoning my shirt while Claire undid my belt and pants. Within seconds, I stood before the gals in my black mesh boxer briefs, with my cock straining for release. Jill dropped down to her knees and got up close and personal with my cock, kissing and massaging it through my briefs, driving me crazier and even managing to make me harder than ever before.

As Jill was driving me crazy by rubbing my cock and kissing it through my underwear, Claire hopped up onto the bed, started pinching and rubbing her nipple as if it could possibly extend itself any further than it already did, and her other hand snaked over her mound, rubbing her pussy through her boy shorts. I could watch Claire masturbate all day every day as I believe there is no hotter scene to be viewed by man or woman. Meanwhile, Jill now had my underwear waistband in both hands and she started to drag them down over my thighs....my knees, and finally over my feet. My cock pointed slightly up above 90 degrees which allowed Jill to run her tongue up the underside without pushing me up higher.

While Jill was lubricating my cock with her tongue, I looked over to Claire, still writhing and moaning from rubbing her clit and fucking herself with two fingers. Claire's panties were now hanging off one foot and her stockings were at different levels on her thighs as she drove herself completely insane with lust manually.

I reached down and gently guided Jill up to her feet so we could join Claire on the bed. Jill crawled onto the bed and in between Claire's widespread legs, her juices smeared all over her thighs. Jill reached in and gently separated Claire's outer lips and rubbed the tip of her tongue all around Claire's clit. Claire immediately buried both hands into Jill's hair, trying to force Jill's head completely inside her cunt. I leaned over onto the bed and grabbed Jill by her hips and steered her up onto her knees, her gorgeous ass presenting itself to me at the ideal angle. While still holding her by her hips, I leaned forward and began kissing her ass and the backs of her thighs. Her aroma was incredibly intoxicating and her juices were almost sweet-tasting. I kept kissing and licking all around her most sensitive area, but Jill was getting impatient, constantly thrusting her ass back into my face so I would finally hit the spots she wanted me to.

On my next pass of kisses, I gently kissed her right on her beautiful pink puckered asshole. Instantly, the goose bumps all over her body told me she enjoyed that. I did it again and again until I finally heard her moan directly into Claire's pussy. Next I leaned in further and licked at her lips and clit, her juices practically dripping from her pussy lips onto the bed below. I tried to capture all that I could but she was leaking more than I could ever hope to suck in. As I continued to lick and suck on Jill's clit, I started to get a little bolder, running my tongue completely from her clit all the up to her asshole, and as if I were punctuating my efforts, I speared her asshole with my tongue. This caused more goose bumps and produced a full-body shudder that shook the bed. She moaned louder than Claire ever had and her level of wetness exceeded my wildest fantasies. Claire held Jill's face to her pussy, using Jill as her personal vibrator as I continued to make her moan from my oral skills.

Jill managed to free her face from Claire's clit long enough to demand that I now fuck her. I pulled back and looked directly at Jill's pussy and ass, not one foot in front of me. Her pussy lips were completely engorged, a deeper red than the original sexy pink as when I started, and her asshole was drenched with a combination of my saliva and her vaginal juices. Just the view in front of me made my cock throb in anticipation of how fantastic she was going to feel from the inside.

I maneuvered myself behind Jill as she went right back to eating Claire. I held my cock close to its base and teasingly rubbed my tip along her slit, from her clit to her asshole. Whenever I passed over an opening, I'd gently insert about a ½ inch to an inch, getting an incredible reaction from Jill each time. I quickly realized that this little move was also driving me crazy, so on my very next pass over her pussy, I stopped and slid myself in slowly and gently, relishing how Jill's drenched cunt molded itself to my length. Once I was completely inside Jill, I held myself still, enjoying the intense sexiness of the scene in front of me. After about a minute, Jill's ass started to grind itself against me, reminding me of the task I had I front of me. I started to withdraw from Jill only to re-enter firmly. After about 7-8 strokes in and out, my cock was ready to explode inside this incredibly sexy woman.

Claire had Jill by her hair and was squirming all over the bed underneath Jill as her orgasm completely overtook her, making her moan and curse loudly. Jill was also moaning loudly as I was now slamming my cock into her warm, wet, wonderful cunt. I also managed to match my strokes into her pussy with my finger into her ass. This was sending Jill over the edge and her orgasm was far more violent than Claire's. It was all I had in me to stay inside Jill as my own orgasm rose through the shaft of my cock and literally exploded inside Jill. I'm no teenager, but at that very moment, I came harder and with far more volume than I had in the last 15 years. Jill screamed as I filled her pussy with cum and Claire was still feeling the after-effects of her orgasm from Jill's talented tongue.

My cock had reduced itself to about half its size before being forced out by Jill's vaginal muscles. Once out, Jill immediately rolled over to prevent my cum, now mixed with her juices, from flowing freely out of her beautiful pussy. Claire seized this opportunity and quickly dove head first in between Jill's spread legs and began to lick and suck at Jill's drenched opening, gathering all that she could in the process. The deeper Claire tried to go, the louder Jill's moans grew. After just 2-3 minutes, Claire leaned up on her elbows as Jill leaned in to kiss Claire, sharing all those wonderful, juices amongst themselves. As I just sat on my heels and watched, Claire grabbed my hand and pulled me in to join the kiss, which I did eagerly. We managed to be very equitable with the kisses, the tongues, and the fluids passed from one to the other two, which reignited all three of us to a near-orgasmic state all over again. But I was spent. Jill's cunt literally sucked my cock dry, and Claire, I found out later, had squirted her orgasm into Jill's mouth, thus zapping her of any residual energy. And Jill just looked fantastic with her "freshly fucked" body semi-reclining on the pillows, almost begging for either a nap or another round of hot wet sex.

We all took turns freshening up in the bathroom and rearranged the bedroom to seem as if it were untouched before we were all dressed and ready to leave. As we rode the elevator down to the lobby, Claire spoke up and asked the price of the condo, but Jill replied by asking us to come to her home that night to further discuss the day's events and see if we are interested in making any offers based on what we had seen that day. Before the elevator reached the lobby, Claire kissed Jill and cupped Jill's mound at the same time as Jill cupped my package and turned to kiss me goodbye as well. We exited the building just as we had entered it, professionally.

Once in our car heading back to our hotel, Claire told me to hurry up so she could fuck me into oblivion as she said she could not remember ever being so horny before in her life. I raced back to the hotel, parked, and we both ran up to the lobby. The girl at the front desk stopped us by saying she had a message for us. I took the note and read it. It was from Jill:

"Thank you for a wonderful afternoon. My address is 281 Gulf Shore Blvd. Cocktails on the patio at 7:00, with dinner to follow. We'll discuss all your needs after dinner. See you then. Dress casual."

I handed the note to Claire who after reading it just licked her lips and we headed for the elevator to our room.

To be continued.....