The Confessor Ch. 04

Literotic asexstories – The Confessor Ch. 04 by CabotDeWine,CabotDeWine
Author’s Note: This is the final chapter of The Confessor story, though I may revisit the main character Edward in the future.

Chapter 4: The WifeGina made the call to her late lover’s wife Felicity. It was an awkward call, but with the rest of us there to support her, she arranged a meeting. We would meet at Felicity’s place early that evening.

We got there, and Felicity greeted us. We went to the living room, where she had coffee, water, and lemonade ready for us.

“I must say, getting call out of the blue from one of my husband’s ex-lovers was a bit of a surprise, let alone with a line of her lovers in tow,” Felicity said.

“I’m glad you were so willing to host us,” I said.

“I confess that when I first caught Dan having an affair with a student it surprised me, and I was thinking divorce. He apologized profusely, but didn’t deny his attraction and the desires he had. Originally, he offered to let me have one affair and shut off all future affairs, but I knew he wouldn’t be happy,” Felicity said.

“Why did you stay with him, then?” Julie asked.

“This was the 80s, after the swing 70s, but there was something of that still going on in pockets of academia. I have to confess that I had done a hookup with two frat brothers in college, and appreciated that, even if it didn’t become a full-time thing,” Felicity said.

“Did Dan’s betrayal open you up then to doing stuff like that again?” I asked.

“Yes. In fact, I had already been thinking of that, though not to act on it. It was just from the guys at my workplace talking about it,” Felicity said.

“Where did you work?” Harper asked.

“I worked for the city building inspection department, which meant going into a lot of student rental housing. I was the first woman to work at that department. I had been planning to work in academia like Dan, but when I was working on my masters I saw the limited job opportunities. There were more women’s studies departments opening, but competition was fierce and I didn’t like the politics. I didn’t want to go into governmental politics for the same reason, and the non-profit space had the same issue. I had decided that if I wanted to practice feminism I would do it by going into a traditionally male space and show a woman could make it,” Felicity said.

“So I went and got certified, and luckily the head of the department, Richard, was relatively enlightened. Being a college town, the city was under pressure to diversify, and he figured on giving me a shot. The rest of the guys were old school veterans, World War II to Vietnam. They would all trade stories about getting laid on the job. It could be girls who installed something illegally who were willing to trade sex to avoid a fine, a few women that simply liked older men, especially veterans, and a few more that were exploitative. Richard had cleaned up the worst of it, but was limited in his punishment, since he had married a young widow he met on the job. There was no quid-pro-quo, but he admitted to giving her a pass on some maintenance deficiencies. He offered to help with the fixes, she offered to make him dinner. All cute and clean, but problematic for sticklers. I think that’s why he was open to hiring a woman, to give some cover.”

“Who did you hookup with on the job?” I asked.

“Honestly, frat boys mostly,” Felicity said, “If my husband was going to bang fresh young coeds, I wanted young, dumb, and full of cum. Sorority girls had been my coworkers ‘prized pussy’, as they called it, and a threesome with two was the biggest get. Well, I figured I could practice my feminism by showing I could run with the best of them. So I did. Frat boys are easy to do, since all they want to do it fuck, and their houses have the most violations.

“It started off one by one, usually with the frat president who had to answer for issues. I never did it if he had a girlfriend. Most were quick one-a-done douchebags, but eventually I fell into a regular thing with the boys of the Gamma house.”

“It started with the Gamma president, Max. Good enough gym rat body, killer smile, cool confidence. The authentic confidence that meant he didn’t have to be a douchebag. And he was a good lay in bed. So good, in fact, we became a regular thing.

“Granted, it wasn’t exclusive. He was able to pull the hottest coeds and we would talk about that in the afterglow. I would give him some advice to get some of the girls more comfortable with doing more exotic things than mere blowjobs and missionary, while he would inform me of some of the newest sexual trends. We would even try some things out that he had read about or heard, as a safe place for both of us to experiment. I brought quite a bit of experience home with me to Dan.

“One day we’re in the afterglow and he’s talking about how much I’ve meant to him, and he gets a bit nervous. I worry the fool has gone off and bought a ring, even knowing I’m married. But luckily it wasn’t that. He just said one of the frat brothers, a friend of his from high school, was still a virgin and hung up on it. He suggested that I sleep with him and get that anxiety out of the way so he could finally take advantage of the social standing the frat brought him.

“I could have just said yet and done it. It would have been nothing. But there was something about him being so vulnerable even asking me, and his true desire to help a friend, that made me realize that I wanted more. I knew many of the frat bros knew about our arrangement. Boys brag like that. And I hadn’t forgotten my hookup in college. So, I would do him this favor, but under my own terms.”

” ‘I will do it, but you have to be there to show him the ropes,” I said.

If he was nervous before, he was more so now.

” ‘You’re both fucking me, not each other,’ I explained, ‘I’ve done this before. It can be quite the bonding experience. You want to make a man out of your friend, do it this way. You’ll never be closer.'”

“He came around to the idea and it was arranged. His friend, Holt, was the typical inexperienced virgin. The first time we did it he came too soon, but Max and I let him know that was okay. Luckily these young guys bounce back fast and he did a proper round. By then Max and I began integrating Holt it. Each time with Holt started as a lesson for something new. Different types of blowjobs, teaching him to eat pussy, a titty fucking session with both of them, both being in my mouth and pussy, then lessons in anal and finally a DP.

“The frat knew, of course, but Max had the sort of authority to keep their mouths shut. Granted, I talked about it at work, and the other guys, though initially conflicted, were impressed. Richard pulled me aside one day and did say I was in a dangerous position, that while he understood I wasn’t doing anything worse than any of the guys in the office bragged about, it would fall harder on me as a woman.

I toned down talking about it, though I didn’t stop. Eventually a few other frat members hinted at getting involved, and we would rotate a few more in.

“In fact, the first time I ever walked in on Gina and Dan I had just come back from a four-way with three of the brothers. I saw the scared look in your eye and it felt so silly. Dan was so vanilla with his hookups, so whatever hate you thought I had was long past. You were just another face in the line of people,” Felicity said.

“I was always nervous you hated me, and honestly wanted your approval,” Gina said.

“I couldn’t have given it to you then,” Felicity said.

“I know. Honestly, though, I felt the guilt. My dream was one day to have you and Dan bring me to your bed for a threesome, which I figured would signal a real approval,” Gina said.

“That’s the problem, I am straight,” Felicity said, “I did a threeway once with Max because he had a hookup who said yes. I agreed to join, on the grounds the other girl and I wouldn’t do anything together, just with him. Other than holding his girl’s tits while he titty-fucked her, and licking some cum off her neck and spitting it into her mouth, there was very little interaction between us.”

“How long did your hookups go on?” I asked.

“A few years. I moved on when Max graduated. I needed him to hold court and keep the gossip down, and none of the other frat leaders quite had that ability. Luckily the ones I fucked had the discipline to keep it on the low, and with turnover in membership I was forgotten. After a while I got to sleeping with professional men on the side. Dan let me know that when he turned 40 he was going to stop with the hookups. I think he was aging out of it, and worried it might one day catch up to him. The last few years we were relatively monogamous and fine with it,” Felicity said.

“I did notice the age range of his exes who came to the funeral,” Gina said.

“Yes. Honestly, it was a sign of his character how many came. I don’t know if the same number of men would come to mine. At least, they would have a harder time since they couldn’t tell their spouses I was a favorite college professor.”

“How many could you call up, if wanted to catch up on old times?” I asked.

“Huh. I mean, nearby there are four I think I could call. Max is divorced, though other than one late night text after his divorce was finalized, we didn’t end up pursuing anything. His friend Holt is around, but married to a slightly older woman who domineers him a bit. I think it’s the type he needs. Then there are two others, Greg and Vinny. Greg is another divorce, Vinny never got married.”

“Why haven’t you hooked up with them since?” I asked, “The three that are available?”

“I guess I worried about whether I would be the woman they remembered. I was younger then,” Felicity said.

“So were they,” I said.

“I mean, I don’t know what this has to do with the closure Gina wanted,” Felicity said.

“You were never going to do a threesome with another woman, right? But two dudes at the same time, especially frat brothers, that worked out. Suppose Gina were to join you, but by devil’s threeway rules. You share the guys, but not each other,” I suggested.

“What if we get more than one guy?” Felicity asked.

I motioned to Julie and Harper.

“We got women to spare,” I said.

“This is crazy,” Felicity said.

“Not the craziest I’ve been part of,” I said with a wink.

“Will you participate?” Felicity asked.

“I could, if I could fit in,” I said.

“Perhaps I could fit you in,” she said.

I got her meaning. Felicity was a little older than the women I preferred, I must confess. And I think I was probably a little younger for her tastes. But, of course, the confidence I gave that made her consider this crazy plan also made me attractive to her. So if she was going to do this favor for Gina, she needed something as well.

“I’m sure it can be arranged” I said.

#Felicity made some calls. As it was, things lined up. Max was in town, and it wasn’t his week to watch the kids, as they were at his ex-wife’s. The other two, Greg and Vinny, were also free. Holt she called up, even though he was married. She told him of the planned get together, and that it might end up in a swinger type event. Holt put his wife on and there was a conversation.

“Okay, so Holt’s wife Leslie wants to come along,” Felicity said.

“The more the merrier,” Harper said.

“Not to have sex. I think she wants to watch. She knows my role in taking Holt’s virginity, and she appreciates my influence on him liking older women like her, even if she didn’t participate in those antics. They might just sit and watch,” Felicity said.

The rest of the guest began arriving a short time later. We broke out the wine. You’d have thought this was just a party, with Felicity serving as hostess to two groups of friends. In the first hour, while everyone was sipping their first drinks, it was more about their time at the college than anything. Julie and I were really the outliers, the only ones not local to town or alum of the college.

The subject of the purpose of the night was broken.

“You know, when I first hooked up with you, I didn’t know where it would lead,” Max said.

“You got me at the right time,” Felicity said, “Your hot body didn’t bother me either.”

“I’ve kept it best I could,” Max said, lifting his shirt to show a strong stomach. The abs were no doubt not as cut and defined as in his 20s, but he was a great looking middle-aged man. I could only hope to look half as good.

I saw all the women, even Leslie, eye his body hungrily.

“Don’t just tease us, take the whole shirt off,” Harper said.

Max did, and gave some flexes to the joy of the women. Harper stood up and ran her hands down his body.

“How are you still single?” she asked.

“If I’m not taking care of my kids, I am in the gym,” he said.

Harper gave a sigh. I am sure Max could have made her his next wife right there. But while he loved the attention of a much younger woman, his mind was on the hostess.

Felicity came over and ran her hand down his chest. Her face got a youthful glow that cut through the years. I could almost see her as the early 30s woman that would have gotten any college-age man’s attention.

Holt gave his own sigh, and Leslie looked at him. I could sense a feeling of jealousy and fear. Older women often feel that way with their younger men they manage to get. But there was something more as well. She had come here reluctantly, but she had come. She wanted him to get something from this experience, even if it hurt her. I wasn’t sure if just watching would satisfy either of them.

Before I could figure out a solution, Max and Felicity were kissing. I’ve been at enough of these things to know that once something starts, it snowballs fast. So I went over to Felicity’s stereo, I had already scoped out some records to play from her collection. Not as cool as Gina’s, but very good nonetheless.

With the music going the orgy could begin in earnest. At first it was Max and Felicity beginning to disrobe each other. It was hot and heavy, and everyone except Leslie leaned in. Leslie seemed nervous about this.

Felicity paused the session.

“Max, I’d like you to meet my friend Gina,” she said.

She signaled Gina to come up. Gina walked up. Max took her hand.

“Pleasure to meet you,” Max said.

“The pleasure’s all mine,” Gina said.

Max leaned in and kissed her. The men smiled, while Julie and Harper watched in rapt awe. Max moved in to get Felicity and Gina to kiss.

“No, we aren’t doing that,” Felicity said.

Max nodded.

“Very well,” he said.

Instead of a full threeway, the two woman paid their attention to him. Max deftly handled it, balancing his attention and touch between the two of them.

Before long they were both pulling down his pants. His cock bulged in his boxers. Felicity moved behind Max and took the waistband on his boxers in her hand.

“Get in front,” she directed Gina, “You’re going to like what you see.”

Gina did as she was told. Felicity pulled down Max’s boxers and his cock playfully bounced out, mere inches from Gina’s face. Gina smiled wide when she saw it. She reached forward and took it in her hands. Felicity helped Max remove the boxers from his ankles, and then moved close to Gina. She whispered in her ear, to quiet for anyone else to hear. But Gina told me later what Felicity said,

“Imagine this is Dan’s cock. Show me how you pleased him,” Felicity said,

Gina went in, but instead of taking the cock right to her mouth, she moved her tongue down to his scrotum and licked up the shaft, then around the head. It was the intricate play of tongue work. Max moaned in pleasure.

“Very good,” Felicity whispered, “But Max also likes a deep throat.”

Felicity put a hand behind Gina’s head and guided her down Max’s cock.

“You haven’t forgot how I like it, have you Felicity?” Max said.

“Not at all,” Felicity said.

Gina gasped as Felicity pulled her back off Max’s cock. Felicity wiped Gina’s spit off Max’s penis and began her own work. She had her tongue out so it covered the bottom of his prick while she went down on him. Gina gave him soft kisses on his hip while Felicity blow him.

“Let’s see what you two and do together,” Max said.

She guided Gina back to his cock. Felicity took him out of her mouth and both she and Gina began to run their tongues on his cock. Then they each took turns sucking.

“This is so good,” Max said, “Why don’t you both get naked?”

Felicity, already down to her underwear, stripped off fast, while Gina followed. By now the men were all leaning in.

“What are you guys waiting for? Join in,” Max said.

Leslie put her hand on Holt to keep him back, but Vinny and Greg moved in, stripping off as they walked in.

“I think we need more women to balance this out,” Felicity said.

That was all Julie and Harper needed. They were up and ready to go. Vinny took Harper and Greg took Julie and helped strip them down.

“You too, instigator,” Felicity said to me.

I knew Felicity meant to have me to herself to start. Her hunger for younger men had been reopened, and I was responsible. I wasn’t about to disappoint her.

I let her undressed me, and she worked her way from my shirt down. I observed Vinny going down on Harper, while Gina and Julie shared their men. I was distracted when suddenly, faster than I would have imagined, my dick was deep in Felicity’s mouth.

Oh, she knew how to use the tongue while doing a deep throat. Usually I’m not the deep throat type (other than when my partner needs it), but this trick with her tongue changed the game. It’s humbling and exciting to know there is still so much you can learn from new partners.

I let my hands feel her arms and shoulders and she did her magic. Her skin had a few more wrinkles, but her body was alive.

“Let’s get on the chair,” I said.

We moved to the arm chair, and my face was in her breasts and may hands over her body. It was a new and novel thing to make out with a woman that much older. And exciting.

Before long my hand reached down and I was fingering her. She squirmed and moved with my hand, her breath getting hot and heavy. I moved to her neck, finding the sweet spot. I moved my free hand down to her ass, getting a grip and asserting control.

“This remind you of your frat boy fucks?” I whispered.

“Yes,” she said between gasps.

“You should have never given that up, you are so good at this,” I said.

The orgasm took her before she could answer. Her fingers dug into my shoulder and let out a huge gasp.

She caught her breath.

“Why didn’t you rush that frat,” she said with a laugh.

“Too busy dating sorority girls to make time for a frat,” I said.

I moved her over and positioned her on my dick.

“Let me take over,” Felicity said.

I did. Her oral skills were amazing, and so was her fucking. She got on my cock and was riding my in a rhythm. I had the idea that I could ride this out for a while and edge, but she was so damn good. With one hand she held my back and set the pace, the other was beside my head, and her mouth has on mine. I could just hold on to sides, but the feeling of her body at work alone was a turn on. My mind thought what it must have been like twenty years ago as a younger woman. The image in my mind was so vivid, so real, that I found myself cumming before I knew what hit me.

I caught my breath and noticed I was the center of attention. All the other guys seems amused.

“Well, you lasted longer than Holt did his first time,” Greg said.

“I lasted maybe a minute longer, for what’s that worth,” Vinny said.

Max just grinned.

“Let’s see how long these old guys can still last,” Felicity said with a wicked look.

She joined Harper with Vinny and Harper. I got up and made my way over to the record player to changed the record. Holt gave me a supportive grin before looking back on the show. Leslie also looked at me, then away when she saw my nakedness.

“Hey,” I said.

Leslie looked at me. Holt was too into the scene to hear. I nodded to her to follow me.

I changed the record as the song ended.

“How are you handling this?” I asked.

“How am I supposed to? See my husband’s ex gangbang his frat brothers?” she said.

“You knew his origins with her, right?”

“Yes, and in a way I owe my relationship to her. But…”

Her eyes looked to Holt, then the rest.

“Why did you come then?” I asked.

“I want him to be happy,” Leslie said, “But he needs control sometimes.”

“He’s behaving himself,” I said.

“I know. But he’d love to be part of it,” Leslie said.

“But you don’t want him to be?” I asked.

“I… would like to see him with Leslie. And Julie and Gina are my age, so it’s not like…”

“Harper,” I said.

“I’ve always wonder why he dated a bit older, if it was a phase that would pass,” Leslie said.

“If it hasn’t now, why would things change?” I asked.

She nodded, accepting the point.

“Is there anything he’s ever wanted that you would never do to him? Something beneath you?” I asked.

“A few things,” Leslie said.

“Have Harper do them. Trust me, she kinky and game. You don’t have to like her to make use of her,” I said.

“She would take direction?” Leslie asked.

“With pleasure. Vinny’s already dicking her out, being bossed around by an older woman will round out her night,” I said.

As we talked Greg and Vinny both finished. Only Max and Gina were still going, and both were close. Holt watched, hands clasped in front of him.

“Good job, guys,” he said, sadness noticeably tinged his voice.

Leslie sighed.

“You have a short window, and it’s closing fast,” I said.

Leslie looked at me and stepped away. She went over to Felicity and whispered. Felicity looked at Holt, who was watching as Max and Gina kept going at it. Felicity looked back at Leslie and nodded.

By the time Max and Gina were done, Felicity had rounded up the rest of the women. The rest of the men cheered Max on as he and Gina got up.

“Thank you everyone, glad you loved the show,” Max said, while Gina shook her head at him.

Felicity cleared her voice.

“If you all wouldn’t mind, Leslie would like to say something,” she said.

Leslie nervously looked at everyone.

“I know you all have just had your fun, but I would feel awful if Holt left here and didn’t get a chance to participate. I know I said earlier we were just going to watch, but -”

Before she could finish Max was already starting a chant.

“Holt, Holt, Holt!” he began.

The rest of the men joined in, and Holt look surprised. He went up to Leslie.

“Are you sure?”

“I’m sure we’ll regret this if it doesn’t happen,” she said.

“One important rule: Leslie directs what happens,” Felicity said.

With that Holt went to the couch and suddenly had several women on him. He went first, of course, to Felicity and kissed her.

“The woman who made me a man,” he said.

“Show her the man you became,” Leslie directed.

And so it went. Leslie directed it all, with Felicity, Julie, and Gina alternating making out, blowing and fucking him. Harper was directed to the dirty duties, like giving a rim job and fingering him. Harper understood her subservient role in all this, but with professional focus did the best job to please Holt. To this day I am sure he’s never had a better prostate massage in his life.

Meanwhile the men cheered as they watched. While I focused on the action, I took time to appreciate the male support and friendship going on. Frats can be toxic places, but under the leadership of Max these men were all brothers, in both friendship, and sharing sexual partners in a healthy, self-improving way. Leslie herself would turn to the audience of men and seemed to appreciate the status it gave her husband. In her own way she began to understand all this. It wouldn’t have been enough to make her join, but she began to direct the action as much to the audience’s interest as to her husband.

It ended with Holt receiving a triple blowjob from the older women, with Harper behind two fingers deep on his prostate. Holt was wracked by what had to be the biggest orgasm of his life. All three women in front got some of his load on them, and they laughed in joy. Leslie herself was smiling. She looked in my direction and I gave her wink.

When Holt began to recover the first thing he did was look to his wife.

“Thank you, this meant the world to me,” he said.

He kissed her and gave her ass a firm smack. Something primal has been awaken in him, cutting through the years and making him young again. I knew the next time they did it would be like their wedding day all over again.

#That was the last evening of the business trip. Julie and I snuck in one last hookup before we left, and said our goodbyes and she waited for her Uber to the airport.

“This trip was more than I could have expected,” Julie said.

“More than any of the others could either,” I said, “Thank goodness you were here or Harper would never have gotten with her professor.”

“This was all you,” Julie said.

“Not all me,” I said modestly, “If you hadn’t flashed your tits during Spring Break before a nascent Girls Gone Wild camera crew none of this would have happened.”

“Is this really so common for you that you can downplay your role?” Julie said.

“I have a lot of stories, and none of them involve me alone,” I said, “My talent is to find people with a story to tell.”

Julie shot me a disbelieving look.

“I’m never going to have week like this again,” she said.

“Fine, but you have raised the bar for what you can do,” I said, “And next time we meet I want to hear those stories.”

“I’m sure you’ll have more,” Julie said.

“Yes, but you’ll bring me something I haven’t heard before,” I said.

Her Uber pulled up and we exchanged a kiss.

“When will we meet again?” she asked.

“Soon enough,” I said.

#EPILOGUENo story is really over. The events echoed in the lives of everyone involved, all for the better.

Gina and Max got married. They found a compatibility beyond just sex. Gina confessed that she had often felt conflicted about never having children, but that the stepmother role she found herself in with Max’s kids felt right. She got along with his ex-wife well enough as well, who was probably happy that he hadn’t run off with someone young like Harper.

His ex of course didn’t know that Harper was a thing. In fact, for about a year Harper was in a throuple with Gina and Max. For her it was heavenly: Her long-time crush professor and her fit older man lover. Everything a hypersexual young woman looking for approval would want.

Harper was actually my date at Gina and Max’s wedding, which was really fun.

I happened to have a business meeting in Julie’s city, and we had a good night together. She had found some stories to tell with her revived sex life, and raved about her ongoing thing with a French immigrant woman who ran the best pastry shop in town, her first long-term lesbian relationship.

Felicity had gotten into dating again and was having a new chapter in her life. It’s serial monogamy, but she’s found a broader community than she expected.

Holt and Leslie are happier than ever. They got into the local swinger community. Leslie continued her role of just watching and directing, though she did tell me they were doing some “educational” sessions with another couple regularly. While Leslie downplayed this as “trying out a few things with a more experienced couple”, Holt joked she must be going for her PhD. I am happy for them.

Vinny and Greg are doing all right. Mostly sticking to their steady women, and enjoying it. They say going back into dating after that night gave them a new energy that seemed to attract women they would have struck out with before that night.

If there is any lesson in all this, it’s to be open to the possibilities, and to not let past mistakes define you or your future. Had Julie not opened up about her past and we had merely hooked up, none of this would have happened. My only contribution through this whole thing was merely listening and providing a way for people to be able to confess their secrets, fears and desires. If you want to break out of your norm learn to listen, take legitimate interest in other people, and you’ll discover things that were just below the surface.

Good luck. I’m pulling for you.