Tony's Visit to the Resort Ch. 01

Widowers in retirement homes don't get as much sex as you've heard reported or you might think. Most women seem to be glad to be done with sex when they reach a certain age. As they got older, they only got naked and climbed into bed (and only occasionally) for their husbands because they loved them and they were trying to keep them happy -- God bless them. So, widowers went to senior apartments or retirement homes not only lonely but horny (if they were lucky). Many of them didn't need the "blue pill", but it didn't matter since they didn't get any opportunities.

Tony had taken early retirement; he was only 55. After his wife died he was just burned out with work. He liked to work, but he had had his fill of that job. He had never really been a standout or very important, but he was a hard worker. He had gotten a substantial termination package so was unconcerned about finances. Tony and his wife had never had children and had always been careful with money. Tony's friend James told him if he had enough money (which he did), he could have a very good time for five days at a "resort" he knew about. No, none of the staff were sex slaves. Each of them had their own story. Tony wasn't proud of it, but he had been with prostitutes. That was a business transaction, and that wasn't what he was looking for. James finally convinced him that wasn't the case. It was more like an extended girlfriend experience. OK. What does he need to do? Sign the application, allow them to investigate his past, give them a significant amount of money, fill out a questionnaire, and provide an STI-free report. They would also provide STI-free reports for all the "service providers". James warned him that they would do a comprehensive background check on him. They wanted no felons, no sex offenders, no dishonorable discharges -- basically only upstanding citizens.

OK. Tony did all that, and within two weeks he was notified his application was accepted. James said to show up at the executive airport with clothes for five days. They would transport him to the location of an upscale gated residence. No problem.

Check-In Sunday Afternoon

Tony arrived Sunday afternoon. A very pretty late 20 girl, Annie, greeted him. Annie wore what looked like two-piece shorty pajamas. She was Hispanic with lovely mocha skin, dark eyes, and short, pixie black hair. She was very beautiful.

Annie asked him to fill out forms. The first form was an NDA (non-disclosure agreement) and confidentiality form covering both them and himself. After she and Tony signed the form, he was given a form for him to indicate preferences. He had already done this, but Tony guessed they wanted to make sure he had no changes after he had time to think about it. It was quite lengthy: did he like anal intercourse as a giver, as a receiver, did he like spanking, was he a voyeur, and on and on. He was quite aroused just filling out the form. He had to surrender his phone, all electronics, and all cameras. Even though everyone had signed a confidentiality agreement, they were extra careful. The only cameras that could be used were the ones the resort provided.

He filled out the form figuring what the heck, what does it matter? Annie asked, "Are you ready for your fantasy week of sucking screwing, pussy-eating, spanking, and anal fucking?"

Tony was surprised but said, "Yes, I am really looking forward to it!"

Annie took his luggage and suggested he have dinner in the restaurant before a brief orientation in his suite. Annie joined him for dinner, and they talked, mostly about Annie. Annie worked here as a "counselor" only part-time. She was studying to be a nurse and was nearing completion. Her days as a counselor would soon be history. Tony thought Annie was a beautiful, intelligent young woman, and he didn't want to miss the opportunity to visit with her. They shared a nice bottle of wine and lingered for a while.

Tony did notice a gentleman at a nearby table. He seemed to be alone. He wasn't eating and had his head tilted back. "Annie, is something wrong with him?"

Annie looked over and said, "No, it's fine - just wait a minute"

The man's eyes opened wide, he inhaled, held his breath, then closed his eyes and slowly exhaled. A lady came out from under the table wiping cum from her mouth and sucking on her fingers. He had just gotten an under-the-table blow job! She smiled at Tony and winked.

Annie asked, "Did you want one of those, Papi?"

"No, I don't think I'm ready for public sex, or semi-public, I guess."

The blowjob girl walked behind Tony, ran her hand along his shoulders, and wrapped her arms around him. She then unbuttoned the top two buttons of Tony's shirt, slipped her hand in, and pinched his nipple. "I know you like that. See you later Sweetie."

Finally, Annie said, "it's time to go to your suite."

Annie then took him to the suite that would be his home for his five-day fantasy. Someone had already placed his toiletries and pills in the bathroom. His clothes had been unpacked in the closet and dresser. Annie said, "you won't need them unless you leave the suite.". She left a lovely set of silk pajamas. The sitting room had a large screen TV with a remote. One of the available options was a selection of porn -- all kinds -- female/male, girl/girl, threesome, something for everyone. Tony put on the pajamas, sat on the bed, and clicked through the porn.

Annie came back in with a beautiful 50ish lady, Mary, a 40ish dominatrix-looking woman, Donna, and a 30ish man, Alex. Tony tried to quickly turn off the porn, but everyone saw what he was watching. Donna said, "that's a good one, Tony, but this one is better." She switched the TV to a different lesbian porn movie. "This one gets all the girls wet."

Annie tried to take charge, "I'm Annie, but you've already met me." She then stepped to Tony and kissed him tenderly on the cheek."

Next was Mary. "Hi, I'm Mary." Mary had long blonde hair and was wearing a cheerleader outfit. She, too, kissed him on his other cheek. Tony recognized Mary -- she was the lady under the table! Mary was about 5' 7", 130 pounds. She had shoulder-length wavy blond hair. She was beautiful.

Donna introduced herself and kissed him full on the lips. Donna was Asian with black hair cut in a page boy. She was dressed in a black, vinyl-looking short dress with a zipper from top to bottom. The top zipper was down to just below her breasts.

Alex introduced himself, reached into Tony's pajama bottoms, pulled out his dick (which was starting to get hard), and licked the head. Alex was shirtless wearing lounging pants and no shoes. He had a swimmer's body and no hair on his chest.

Mary said, "shit, I didn't know we could do something like that now! I'm going to have to step up my game." With that, she pulled up her top and flashed him. She shook her tits and said, "More later, Sweetie."

Annie tried to regain some semblance of control. "We are your fantasies for the next five days. We are going to do everything on your wish list. We won't do anything we don't want to do. You've paid for this, but we really aren't whores. Expect us to enjoy this as much as you. We might even tell you to do something that will make the experience better for us. There is a session in the morning and another in the afternoon with Wednesday morning off for recovery. You can spend the evening, including sleeping, with the afternoon session person, should you like. You'll have breakfast probably by yourself and lunch with your morning session person, either in your suite or the restaurant, and dinner with your afternoon person. Wednesday you'll probably be alone."

Annie told the other three that they could leave. After they left, Annie said to him "do whatever I say; don't say anything". Tony started to ask a question, and she lightly slapped him. "Did you not hear me? Don't say anything. Now, strip. I'm not tomorrow's session; I don't have you until later in the week, but we need to get some preliminaries out of the way, mostly for the benefit of the other girls...and boy."

Tony quickly undressed. "That's an awfully small dick, Tony. I hope it gets bigger when erect." Tony knew his limp dick was small, but it did grow to about average when erect. He wasn't concerned. He had a tongue and fingers to make sure everyone was happy. Annie laid a towel down on the bed. "Tony, lay down on the bed with your ass over the towel. I'm going to use this electric shaver to give you a nice trim. That way the other girls won't get pubes in between their teeth when they blow you." Annie closely trimmed Tony's shaft, groin, and surrounding area. "I'm also going to pluck the hairs around your nipples. Donna, especially, likes to suck and bite nipples, so I want to keep hairs out of her mouth."

"You marked sex with a strap-on on your fantasy list, so I need to make sure your ass can handle it. First, I'm going to use an anal douche to clean out your bottom. I don't want to stick my fingers in there and have them come out nasty. Let's go into the bathroom. Now, bend down on all fours and spread your ass cheeks." Tony did what he was told -- he didn't want another slap, although it didn't hurt that much. He knew Annie only did it to get his attention, not to hurt him. Annie lubed the douche tip, gently inserted it into Tony's rectum, and squeezed. "Now, go sit on the toilet and squeeze out the liquid. We'll do it one more time, and we're done!"

Annie then told him to get on the bed on all fours. "Spread your cheeks, so I can lube your rectum, see how tight you are, and use an appropriate butt plug." Annie gloved her hand, lubed the glove, and inserted first one finger, then slowly a second. She didn't try a third. "You are tight, but not

so tight that you can't handle a small strap-on. I'm going to insert a butt plug to stretch you a bit. Leave it in until you go to bed."

Sunday Evening -- Annie, hand job, cunnilingus

Annie explained, "usually, we leave you to your own devices on Sunday evening, but I haven't had an orgasm in more than a week. I'm going to offer a trade, but just between us. Don't tell anyone. If you bring me off with your tongue and fingers, I'll give you a hand job. You didn't mark that on your fantasy list, but I give very good hand jobs. I promise you'll enjoy it." Tony didn't say anything, merely smiled. Annie took off her shorty pajamas, laid a towel on the bed, and laid over it. She then spread her legs. "Now don't worry Tony. If you aren't doing what I want, I'll coach you. I'm very orgasmic, so this should be a good introduction for you."

Tony crawled between Annie's legs, kissing the inside of her thighs as he worked his way up. He didn't stop at her pussy, but worked his way up to her breasts. He slowly kissed all around her right breast, then moved to her nipple. He licked and then took the entire nipple in his mouth sucking and gently biting. Annie's moans told him he had guessed right -- her nipples were a direct path to her pussy. Tony then moved to her left breast and repeated his approach. Annie took Tony's head and started pushing him down to her pussy. Tony got the message and kissed his way down, kissing her tummy and thighs, finally getting to her pussy lips. "Annie,, you have the prettiest pussy and asshole."

"Thank you, Papi. I get anal bleaching to keep me pretty."

Tony went back to focusing his tongue on her pussy. He took long strokes. After licking her clit, he slipped two fingers into her pussy and made the come hither motion. It didn't take long and Annie was saying, "Oh, Papi. Fuck me with your fingers and make me cum." Tony did, and Annie did cum.

Once Annie recovered, she said, "Tony, I need to hurt your nipples. I know you'll be with Alex tomorrow, and I want your nipples prepared for him, just in case. The easiest way to do this is to use nipple clamps on you. I don't mean decorative clamps, I mean strong ones, so you may still feel it tomorrow. I'm going to suck, pull, and bite your nipples before I put the clamps on them so they stick out nicely. Just lay down." Annie started on his right nipple -- sucking, pulling, and biting. Then she put a clamp on his nipple and tightened it until Tony complained. She tightened it a bit more. She then did the same with his left nipple. A chain connected the two clamps. Annie pulled on it until Tony cried out. "Annie, that's too much."

Annie took mercy on Tony. "I think that's good, but I want you to remember this. When I take off the clamps, I'm going to pinch your nipples cross-ways to the clamps and twist. That's going to hurt, but you'll love it." Annie smiled while she did it and giggled softly. Tony groaned, but Annie could tell he liked it. "Just don't expect Donna to be so lenient if she attacks your nipples. I do want Alex to find you sensitive. Now, just be quiet while I give you a loving hand job."

Annie then straddled Tony's legs and drizzled lotion on his cock. She took her left hand and grabbed his cock at the base. She took her right hand and spread the lube all over his shaft. She used her thumb to rub the underside of the top of his cock. "Oh, Papi, your dick is small limp, but it is very nice when hard. It's a lovely cock." She then used all four fingers and thumb vertically to massage the head of his cock. It didn't take much of this for Tony to shoot cum over her hand and his stomach. Annie smiled, licked his cum off her fingers, bent over, and licked the rest from his stomach. She then moved up and kissed him fully on the lips. It was the first time that Tony tasted his cum, but it wouldn't be the last.

Sunday night

Annie then dressed in different lingerie. Tony's questionnaire said he enjoyed seeing women in different outfits -- costumes. "I'll sleep with you if you'd like. I don't want you to be lonely."

"That would be great. Thank you. And thank you for a hand job."