Tony Starts Retirement

[We first met Tony in "Disciplined for Peeping." He was 25 at that time. He is now 56.]

Tony was moving into a retirement community. It had been more than a year since he buried his wife, Molly. Molly had died of cancer. She was only 56. Tony buried her next to Ronnie, their long time lover. On the other side of Ronnie was Walter, her husband. There was one space left in the family plot. Neither couple had had children.

Tony had waited a full year before he made any major decisions in his life. He sold their main house and their vacation cottage near the water. Tony and Molly had saved quite a bit of money and had looked forward to travel in their retirement. In addition, Ronnie had left them half of her estate, which was millions. The other half went to charities that Tony had helped her select.

Tony's new home was expensive. One of the reasons it was expensive was because of the services provided - all his meals, maid service, laundry and dry cleaning, fitness center, transportation, among others.

Tony was slowly getting used to his new life with little to worry about. He didn't have much interest or energy. On a weekday afternoon, Tony had a visitor. She introduced herself as Emma St. Clair, "Just call me Emma." Emma was very attractive, mid-30s. She was dressed in a brightly colored, button up, spaghetti strapped, summer dress. Emma worked for the facility as social coordinator and was part of the welcome committee. She was sent to interview Tony to see how he was fitting in with the rest of the community. Tony was happy to speak with her. He was lonely and had never really learned how to make friends.

"How are you doing, Tony? Is the food to your liking? What amenities have you taken advantage of?"

Tony answered, "I'm fine, I guess. The food is fine. I haven't done much here, yet."

Emma frowned. "Tony, that's not good. Do you miss your wife?"

"Yes, I do. We were married almost 30 years. I miss her smile, talking with her, and her physical presence."

"Did you have an active sex life, Tony?"

"Yes, we did. When we first got together we had a close, loving relationship that included an older woman, Ronnie. I miss everything about both of them."

"Have you met any of the widows living here? Many are very friendly, and some are as lonely as you."

"No, I have pretty much kept to myself."

"Tony, you have to get out. You'll slip into deep depression."

"I'll be OK."

Emma knew Tony had a problem. She left him that afternoon with a promise to return in a week. Emma was especially attracted to Tony because he remind her of her husband. Her husband had been much older than she but a loving, caring man. Unsurprisingly, he had died while Emma was still young. Emma felt she had to help Tony. The difficulty was that he had to let her help him. She went back to him in a week, as promised.

Tony answered the door. "Hi Emma, I've looked forward to our visit."

"Has anything changed, Tony?"

"It's all about the same. I consider myself an incompetent extrovert. I want to meet people, but I don't seem to have the skills."

"OK, I have a multi-part plan. I was told that decision making and planning was your consulting area of expertise, so I thought you would appreciate a plan. First, I've selected several group activities, and I have signed you up - exercise for seniors, movie night in the meeting room, and game night. Second, I have signed you up for a writing class held here in the community. This will give you an outlet for your creativity. Your application stated that you had always intended to write a book about how you had helped all your clients. This class should help you get started. Third, I've enrolled you in dancing lessons. It's good exercise and will give you something to do on your dates. Finally, I have picked out several lovely woman who are good candidates for you to date. Take them off campus for dinner and a movie, maybe dancing once you have a little confidence."

"I don't know what to say, Emma. I'm not sure I can do all that."

"You don't have to be sure; I am sure enough for both of us. But you better get a move on. Your first date expects to be picked up at 6:00 for dinner. Her name is Mandy. She is in apartment 611. I've made reservations at Tony Mandola's." With that, Emma reached up and kissed Tony on the cheek. "Good luck and have a good time." And she was gone.

Tony didn't know what to think or do. "Oh, heck, what could it hurt. I can always back out after dinner." Tony cleaned up and dressed in business casual - like he was meeting with a client.

Tony picked Mandy up right at 6:00. Mandy was attractive, fit, in her mid-50s. She was dressed conservatively in an expensive pants suit. They Ubered to dinner. Dinner was delicious. They ordered oysters Rockefeller for a starter, Texas Red Fish Pontchartrain as main course, but skipped dessert since mature folks need to watch their weight. They shared a bottle of wine but didn't finish it. There was quite a bit of conversation at the table, but the vast majority of it was on Mandy's part.

Once Tony had paid - he refused to let Mandy pay half - Mandy said, "Let's skip the movie and get you home. We need to work on your small talk skills and brighten you up."

Tony was a bit taken aback but didn't really argue. He knew Mindy was right. They went to Tony's apartment. Mindy sat Tony down. "Tony, I know you are a recent widower. Emma briefed me on your marriage. You seem like a nice guy, but you are emotionally blocked. We are going to work on that. However, first we are going to get sex out of the way."

"What? What do you mean?"

Mandy was not to be denied. "You aren't opening up to anyone because of your feelings. You aren't really sexually repressed, but you will be if you don't let yourself go. Your deceased wife, Molly, doesn't want you to be unhappy or celibate. I'm going to start to address that now. Take off your pants and underpants. Then sit down on the couch"

"What?"

"Don't think, just do it. I promise I won't hurt you. No one will ever know what we do. I feel a connection with you and want to help you. I don't normally do this, and certainly not on a first date. I want to help you. I want you enjoy your stay here. I certainly know some woman who would like to enjoy you. Few, if any, of us want to get married, but we don't want to give up any aspect of a happy life - and that includes sex. And, we are not selfish. We are happy to share to keep our men happy."

Tony hesitated for a moment and then took of his shoes, pants, and underwear. "Let's get that shirt off you, too. No sense in getting it messy."

Mandy took a packet of tissues and lube out of her purse and placed them on the coffee table near the couch. She then unbuttoned her blouse and pulled her breasts out from the confines of her bra. "This should help you get turned on, sweetie." She knelt in front of Tony and bent over, and took his limp cock in her mouth. She gently sucked on him until Tony became erect. "Oh goody, you can still get a good erection without a little blue pill. But don't worry, I wouldn't have minded if you needed a little help."

Once Tony was hard, Mandy poured lube on his cock started to pump. Tony had stopped masturbating after Molly had died, so it wasn't long before Tony started to moan and come. He didn't squirt much, and it all landed on his cock and stomach. Mandy looked at Tony and smiled. "That's lovely. Let me clean you up." With that she took tissues and cleaned up Tony's cum. When she was done, she took the tissues into the bathroom and flushed them.

When Mandy returned, Tony had put his shirt and underwear back on. "Well, this wasn't how I expected the evening to end. Thank you. That was, uh, enjoyable."

"You're welcome. We're going out again. Next time, I expect you to be a bit more attentive to me."

"Yes, I will be happy to. How about next Thursday for dinner? I'll make a reservation. Do you like Mexican food?"

"What Texas girl doesn't? I look forward to it."

To be continued