The Trip Pt. 01

Walter was sitting in the big conference room for the monthly meeting. Bill, the head of the office, was recapping what had happened at the regional office summit but Walter was barely listening. He was gazing dreamily at Veronica, or Ronnie as he was instructed to call her, who was sitting on the opposite side of the large oak conference table and more towards the front where Bill was seated. She was concentrating on Bill's presentation and had not looked back at where Walter was seated.

Walter was remembering what had transpired after last week's summit. How he met Ronnie at the Airport Hotel. How he had stripped for her, and sucked her tits and her pussy. How she had cum twice from his oral stimulation of her boobs and her pussy. How she had sucked his dick and then mounted him and fucked him until she orgasmed again. How he then fucked her in the missionary position and had filled her with his semen, while she had a final orgasm.

Four orgasms she had that afternoon. He had never been with a woman who could cum so often, and so easily.

Bill ended the meeting by reminding everyone that Walter would be away starting on Wednesday and would not return until the following Tuesday. He was attending a national conference in Key West to gain some new expertise and to do some networking. Bill also told everyone that, because their office performed so well at the regional summit, they would all have the day off on Friday.

As the meeting broke up Ronnie slinked up to Walter and surreptitiously tugged at the sleeve of his sportscoat. She gave him a knowing look, winked at him, and said, "I hope you have a productive trip."

Walter replied, "I hope so, too."

A short time later Veronica walked into Walter's office and shut the door behind her. "You know I have never been to Key West and I've always wanted to go. Perhaps I should join you."

"I do not think that Bill will approve the expenses for you to accompany me on this trip," Walter replied.

"I'm not talking about a business trip. I was just given a three-day weekend. I have the money saved up. I think I'll go to Key West and relax and get some sun. Who knows I may meet a handsome man with a big dick down there," Ronnie smirked.

Walter was astonished at her suggestion. "Really? You want to fly down to Key West with only three days off? That's not enough time to see the island and enjoy yourself," Walter remarked.

"Who's talking about seeing the island? I have all the sights I want to enjoy right here." Ronnie then brushed her hand across the front of Walter's pants and gave his dick a quick squeeze. Ronnie turned to leave Walter's office, looked back at him, smiled and said, "I need to go see if I can get a room at the Resort and book airfare. Wish me luck."

Friday.

It is just after 12 noon and Walter had left the last morning presentation. He was walking through the lobby of the Resort on the way to his room. The Resort was located in the Old Town section of Key West. It was situated on the water at the end of Duval Street, a short walk from the iconic Sloppy Joe's Bar. As he was passing the front desk, he spotted Ronnie standing in line, waiting to check in. "I cannot believe that you arranged this trip on such short notice and that you're actually here. In Key West. With me."

"You need to learn that when I set my mind on something I reach out and grab it," Ronnie answered. With that she reached out and grabbed his arm. "And I have set my mind on you." She gave Walter a mischievous smile and handed him her rollaway suitcase. "Let me finish checking in and then you may escort me to my room."

The room that Ronnie managed to book was a deluxe with fantastic view of the water, a king-size bed and a small sitting area. As they entered the room she said, "I must use the restroom to freshen up after that flight. Grab a seat and then we can get lunch and go to the pool together."

Walter did not sit but stood by the window looking out over the waters of the Gulf of Mexico. He couldn't believe that Veronica had traveled down here with her own money to join him on this business trip and to spend the weekend with him. She was definitely adventurous, and in more ways than one.

When Ronnie was finished in the bathroom, she approached Walter from behind, she put her hand on his shoulder and said, "This view is gorgeous. I think it is worth what I had to spend for it. This is going to be a glorious few days."

Walter excused himself to use the bathroom and when we came back into the room, he saw that Ronnie had stripped down and was only wearing a pair of teal bikini panties. She was bending over the dresser putting her clothes in one the drawers. Her dazzling 34 C breasts were dangling down and swaying as she moved about. Walter thought to himself, "She really knows how to get my motor started."

As Walter approached her, she turned to face him and threw her arms into the air. "Let's get started," she exclaimed. Walter lifted up her 5-foot, 3-inch, petite body and gently placed her on the bed. He rapidly removed his own clothes and laid down on top of her. They immediately kissed and their tongues began dancing between each other's mouths. Walter's right hand was massaging Ronnie's left tit and both Ronnie's hands were sensuously scratching Walter's back with her long, painted nails.

Walter broke their kiss and lowered his mouth to her left breast while still squeezing her right breast. He then began to kiss and lick his way down her body. He paused at her navel and kissed it for a few seconds. He proceeded lower still, kissing his way to her panties and planted several kisses through the fabric of her panties on her mons pubis. He then grasped her panties with both hands and started to slid them down. Ronnie lifted her ass to assist him and when he had completely removed her panties, he tossed them to the side with a flourish. Ronnie opened her legs to expose her inner most parts to him and Walter slid himself further down the bed so that he could comfortably lick and kiss her pussy.

He started slowly licking around both her outer and inner lips. He eventually penetrated her vagina with his tongue and relished her taste. He had found that each woman has a distinctive flavor and aroma and Walter was savoring hers. He finally began stimulating her clitoris with slow yet firm licks from his tongue. He gradually increased the tempo and within minutes Ronnie was breathing rapidly and began a crescendo moan. Her body trembled and suddenly she clasped her thighs together trapping Walter's face. He continued his licking and slurping until she relaxed and pushed him away. "Okay. Okay. No more. I cannot take anymore," Ronnie murmured.

Walter ceased his mouth action but gently inserted one of his fingers past her swollen lips and into her vagina. She cooed as he did this and he felt her vagina contract around his finger. He removed the finger and started rubbing it around her ass and tenderly pushing inside her backdoor. "You told me once I could stick my dick anywhere I wanted," Walter whispered. "Does that include here?"

"Of course, my lover. Just not right now. I must be properly prepared. Relaxed. So that we both can fully enjoy the experience. Perhaps tonight, after a romantic dinner and several glasses of wine," Ronnie answered.

At this point Walter was fully engorged and hard as steel. The unexpected, yet hopefully expected, fulfilment of seeing Ronnie in the Resort lobby checking in, and escorting her to her room, and seeing her nude, and tasting her pussy, and making her cum, and playing with her ass, and having her confirm that she would engage in anal sex with him tonight, had Walter as horny as he had ever been. He abruptly mounted her and penetrated her warm, moist, and velvety soft vagina. He began thrusting. Deeply and hurriedly. Within one minute he felt the pulsing and he exploded into her.

Ronnie, realizing the state of excitement that she had induced in Walter, opened her legs wide and flexed her hips to allow him maximal entry. She wrapped her arms around him and rubbed and scratched his back. She accepted his frenzied attack as a consequence of her teasing and tempting him. She felt gratified that someone could find her so desirable. She laid there and enjoyed his frenetic performance.

In and out and in and out he plunged, with ever increasing vigor. Even though she had just had a huge climax, the thought that she caused so much desire in him, coupled with feeling him fill her with his seed, caused her to have another small orgasm.

Walter's hot, sweaty, and spent body collapsed upon her and he rested after such an overexcited display. After a minute he realized he must be crushing her and lifted off her and rolled to the side. "That was intense," Walter said.

"Indeed. I've only been with you a short time, but that was your most passionate lovemaking yet."

I guess, you inspire me," Walter responded. "Anyway, we should get dressed and head to the pool. I'm famished and I'm sure you need to eat, too. I'll go to my room and get changed. Come and pick me up there."

When Ronnie arrived at Walter's room, his eyes almost popped out of their sockets. Yes, he had seen her naked several times. But in the coral-colored string bikini she was wearing he thought she was the most alluring woman on the planet. "Wow. You look hot," he exclaimed.

"Thank you, my good man. You look pretty sexy yourself." Walter was wearing a short aqua and forest-green tropical print swimsuit. "I usually see you in a full suit ... or nude," Ronnie chuckled. "But scantily clad may be the most captivating. You know there is a quote about statistics that I have always fancied, 'Statistics are like bikinis: what they reveal is suggestive, but what they conceal is vital.' I think that sums up the situation we are in at this moment." Walter nodded his agreement.

They went to the pool and ordered lunch. They both ordered tacos. Walter had a blackened grouper taco with a local craft beer and Ronnie had a grilled shrimp taco with white wine. After eating they cooled off in the pool. They were clutching each other and swimming about the pool like newlyweds. During their conversation Ronnie convinced him to stay in her room at nights. He had a small room with only a double bed. While she had a larger, deluxe room with a king-size bed and a better view of the Gulf. And there was no point in sleeping in separate rooms if the purpose of her traveling to join him was to be together. After a while they went back to their respective rooms to shower and to get dressed for dinner.

Walter arrived at Ronnie's room wearing khaki slacks and a Hawaiian shirt that featured sailboats. Ronnie was wearing a loose, flowing, ankle-length, tropical-print, backless halter dress with a spilt thigh and three-inch heels. "Oh my God, you look incredible," exclaimed Water. She smiled and took hold of his arm and they walked the few blocks to a romantic restaurant on Duval Street. After a delicious seafood meal and sharing a bottle wine, they went back to Ronnie's room.

"I am not sure whether I want you to remove that dress or leave it on. You look amazing in that outfit," Walter said.

"Oh, you definitely want me to take it off. I promised you something earlier and I need to prove to you that I am a lady of my word." With that, Ronnie began to slowly and sensually remove her dress to reveal that she wasn't wearing a bra but was wearing lacey, black bikini panties. She removed her heels and laid down on the bed, beckoning Walter with her finger. "Come here my lover and take your prize."

Walter quickly shed his clothes and underwear to reveal that his dick was erect and ready for action. He laid down next to her and their lips meet and their tongues commenced their familiar battle. She wrapped her arms around his neck and he proceeded to massage and squeeze her right breast. He moved his mouth to her tit and began to suckle while his hand moved down and removed her panties and started to finger her pussy. She was already wet and he slid one finger into her. He easily inserted a second finger into her and used his thumb to rub her clit. He continued his sucking on her tit and started gently biting the nipple. Within several minutes he felt her twitch and tense up. She let out a long, slow groan and began to tremble under his expert stimulation. Her orgasm lasted a full minute.

Walter removed his fingers from her vagina and moved his mouth from her tit back to her mouth and they once again began their passionate tongue jousting. "That was wonderful, my love," Ronnie said. "But now I think that it is my turn to please you. How would you like to do this? Which position do you want me in?"

"Roll onto your left side. I want to spoon you."

Ronnie rolled onto her side and reached over to grab some lubricant that she had strategically positioned on the nightstand. She squeezed a generous dollop into her right hand and reached back and lubricated her butthole. She squirted more on her hand and then lathered it all over Walter's cock. "Gentle now, lover. I haven't done this in quite a while. So, go slowly, please."

Walter guided his dick to her ass and gently started to push. She gave a little yelp and he immediately stopped and pulled back. "You're okay," she said. "Keep going." He pushed a little more and felt the head pop past her sphincter. "Ahhhhh. That's it," she said. "That's the feeling I remember. Now start slowly, while I adjust."

He cautiously began moving his cock in and out of her butthole. A little deeper each time. Ronnie gradually adjusted to the increasing fullness in her ass, as Walter drove his dick in deeper and deeper. At first, it was uncomfortable. But as her butt accommodated to the fullness, it began to feel pleasurable. Now she remembered why she didn't mind anal sex. She knew that it was incredible for her lover, a gift that not many women would give their male partners, and that it was also satisfying for her.

Walter wrapped his right hand around her and started to finger her pussy. He dipped his index finger into her vagina to moisten it, found her clitoris, and began making circles. Initially, he lightly traced wide, slow rings around her sex button. He gradually tightened the circles and increased the pressure until finally he started to rub the clitoris itself.

"Oh my. That feels wonderful," Ronnie panted. "You're gonna ... make ... me ... cum. Ahhhhhh." She started to shudder and Walter was pleased with himself that he brought her to another climax, so soon after the last one. When he thought she had finished he moved up his hand to cup and hold her right boob. He loved the firm, squishiness of her breasts. They felt heavenly.

Eventually, he pushed his dick all the way inside of her rectum, so that his groin was against her ass. It was tight, but different. Much tighter than her pussy. But still, only tight at the entrance. A single ring of compression from the sphincter, rather than the enveloping snugness of her vagina. Regardless, it was overwhelming to be buttfucking someone for the first time.

Soon after Ronnie's orgasm, Walter started to feel a mounting pressure in his balls. His back-and-forth movement became faster and more forceful. His right hand started to rhythmically squeeze her tit. His body started to tense up. His thighs began to tingle and the pulsing grew more intense and surged up his cock. He growled loudly. He ejaculated one, two, three, four times deep into her bowels filling her rectum with his semen. Two more minor spasms and he was done.

As his orgasm subsided, Walter's body relaxed. He let out a deep sigh. His hand dropped from her tit. His softening dick slipped out of her butt. He laid there panting and enjoying the euphoria of post-orgasmic bliss.

Neither of them moved nor said a word for several minutes. Enjoying the feeling of their hot bodies pressed against each other in the spoon position. Savoring the ecstasy of the moment. Finally, Ronnie turned around to face him and wrapped her left arm around him. "I hope that was everything you imagined it would be."

"It was exceptional. I have never had anal sex before," Walter replied. "The anticipation of doing it, the sensation of being inside your ass, and the eventual release were all beyond words. It was magnificent. Wonderful. Superb."

Ronnie beamed a smile. "Indeed. I'm glad I could be your first. I guess this means we will have to include it during our future sessions."

They both closed their eyes and fell asleep in each other's arms.