My Crazy Life 5 – Tammy, Wendy, Brenda – First Half

"One story always leads to another. Is it bragging if it's true?"

Font Size

Sometimes, egos are good things. You can ride high on the wave of a growing ego, but you better watch for the breakers at the shore! This is a long story of how I built my ego up, flaunted it around, and then crashed back to reality.

===

 

Tammy:

My wife met Michael at an infamous “Sue and Lyle” house party. He is a smaller dark-skinned man with a giant cock. At five-feet-six-inches, he was only a couple inches taller than my wife. His cock may, in fact, be longer than mine, but on his frame, it looks huge. My wife can never get enough of him.

Not to track through too many stereotypes, but Michael always seemed to be up to no good. He went through a variety of very diverse jobs in the time that we knew him, but he was always working an angle. It didn’t surprise us at all when he temporarily left the swinging lifestyle to settle down with a sugar momma.

She may have been too restrictive of him, and he wasn’t gone for long. When he contacted us again, he was with a different woman, and he was trying to get her interested in swinging. He took her to a Meet and Greet, but the guys there were too pushy, and she didn’t like it. Michael contacted my wife to see if I would be willing to chat with Tammy to give her a better impression.

Tammy was a recently divorced woman around my age with two grown kids. She admitted that she loved having sex with Michael, she was interested in exploring more with him, and she understood his need to be promiscuous.

I could sense right away in our chats that she wasn’t looking for someone to make aggressive advances toward her. She would have been offended if a guy like me, who had never met her, started gushing about how beautiful she was and about how much he desired her.

The first couple of times that we chatted, she was more interested in hearing the ‘why’s’ of the experiences that my wife and I had been having in swinging. She wanted to hear about things like, “Why are you comfortable kissing people you just met?” or “Why do you trust your wife with other men?” or “Why are you infatuated with breasts?”.

I did my best to answer her questions. She made fun of me when my answer to the last question was, “I don’t know. Ask me why I am infatuated with breathing air.” Much of the time, I don’t know that my answers helped her, but I could tell by her teasing that she was becoming more relaxed with me.

Eventually, she was the one that brought the discussions around to sex. She started with factual things, like how often, and how many partners. She wanted to know what I had done that I enjoyed, and anything I might not have enjoyed.

The question that got me into trouble was when she asked me if I had ever hurt someone. She wasn’t asking about spanking, or even accidental bruises. She was more concerned with hurt feelings or bruised egos.

We were chatting with video, and she could see that the answer was ‘yes’, and she could also see that I didn’t want to admit it. She persisted.

I tried to explain my reluctance. There were two reasons. First, the woman that I had slighted deserved it, and second, if I told the story properly, it was going to sound like I was bragging.

Tammy was very mad that I would imply that I would brag about hurting someone. I tried again. The woman had nearly gone out of her way to antagonize me. I got even by having incredible sex with someone else right in front of her to prove a point. Tammy looked at me in disbelief, and then insisted that I tell her that story.

 

Wendy:

Wendy was a regular in a text-only group chat that my wife had joined. That group liked to organize a swinger camping event late every summer at a lifestyle-friendly campground north of Madison. Several people, including my wife, cajoled Wendy into joining us at the campground.

I met Wendy for the first time late on the first night of camping.

It had been a long day for me, but I still was hoping to have some fun. During the week, I had been at a job site that was located more than five hours from home, and we had to work a partial day that Friday. I made the long drive home, raced to connect the camper to our SUV, finished packing, and then drove the couple of hours up to the campground. By the time I got the camper set up, I was ready to crash and sleep for a day or two.

About then, my wife brought Wendy around to meet me. She was pretty decent looking, with sun-bleached brown hair, and an ample bust-line. She was breathy and flirty as she asked me if I would help her set up her tent. I jumped right on that opportunity.

As soon as her tent was erected, she breathily asked me to help with her air mattress. I was very willing to breathe hard with her, but I also knew where to find an air pump. As we finished up arranging her stuff, I asked her if she wanted to try out the air mattress. I flirted that she would need to see if it felt okay on her naked skin.

She begged off. She suggested that she really needed to spend a little time meeting some of the people from the chat room before she moved on to better pleasures. I am not pushy, and so I deferred.

A group of her friends was sitting around the campfire. She asked me to join them, and then she gave me some flirty eyes as she breathily asked for a shoulder and back rub. I sat behind her and made sure I was rubbing her just right.

An hour later, there was a lull in the conversation, so I leaned down and asked if she was ready to go continue the massage in a naked way.

“Do you mean sex?” she asked sweetly.

“Eventually,” I teased.

“I don’t do sex with married men,” she said coldly, and then she turned back to the fire and her friends.

I believe it would have been a justifiable homicide. For ten seconds, I debated saying something mean to her. I really wanted to point out that I am a nice guy. A woman does not have to lead me on to get me to help with tents and mattresses and stuff. I decided that she wasn’t going to listen, and I was too tired to care. I excused myself, went to my camper, and crashed for the night.

Sometime around 3 am, a car alarm went off directly under my bed. I had seen the car that had been parked with the nose tucked in under the end of our camper, but I knew who the car belonged to, and I thought it wouldn’t be a problem.

I still wonder why the owner thought they needed to set the alarm. We were in the middle of nowhere, and nobody was going to mess with their car. I guess they were justified, because somebody reached in through the open window, unlocked the door and opened it, which set off the alarm. It almost would have been funny. The fact that the horn was inches below my head was infuriating enough. Things got worse as the alarm just kept going and going and going.

Finally, the owner made it stop, and then a loud argument ensued over why the alarm had been triggered. Listening to two drunk women argue nonsense at 3 am is almost as bad as having the alarm under your head.

Of course, the woman who set off the alarm was Wendy. She was too drunk to make sense, but she had decided she couldn’t stay at the campground any longer. Her car was blocked in by the car under my bed, and she figured that since the windows were open, the keys were probably in it. There was a lot of arguing, but somebody sane finally stepped in. They took Wendy’s keys away from her, and then locked her up somewhere for the night.

I stayed in my bed until the ruckus ended. If I had gotten up, I’m pretty sure another justifiable homicide would have occurred.

Thankfully, Wendy left the next morning, and the rest of us had a great weekend.

===

My wife is a troublemaker. Later in the next week, I got an online friend request. My wife made me accept, and then she made me accept the chat request that followed.

It was Wendy, and she really wanted to apologize for two things.

First, she apologized because she had misspoken by the fire to fend off one of the other men there. What she really meant to say was that she didn’t have sex with a married man without the express permission of his wife. She was quick to point out that she hadn’t spoken with my wife in time for camping, but she had spoken to her now, and so she would be willing to have sex with me.

Second, she wanted to apologize for getting sick and then leaving. I deferred on that because I hadn’t directly been involved in that mess.

I asked if she was going to apologize for the car alarm, and she denied any involvement in that. She said that had totally been the car owner’s fault. She felt that they shouldn’t have parked behind her, and they shouldn’t have left their windows open. She suggested that I should talk to them if I wanted an apology.

I should have ended the chat right then, and I should have un-friended her. To this day, I still can’t get my wife to explain why she insisted that I give Wendy another chance.

I can tell you why I gave her another chance. As I told this story to Tammy, she was all ears! Wendy had a breathy Marilyn Monroe quality about her, with a body to match. Even if the face and hair weren’t right at all, if there was a chance that I could take pleasure from her, I had to make the effort to try.

Wendy certainly didn’t make it easy.

First, she had a habit of only being available late in the evening during the week. She couldn’t understand why I wouldn’t drop everything and drive more than an hour up to the north side of Milwaukee at nine-thirty on a work night. She promised it would be worth the trip.

In the breathy tone that I loved, she explained to me that I would never have a lover as skilled as she was. She explained that unlike most women, she was capable of having sex for extended periods of time. She had been known to last more than forty-five minutes. I tried not to laugh.

She went on to explain that while I might not understand the term, she was probably the only multi-orgasmic woman in Wisconsin. With a straight face, and in breathy tones, she explained that sometimes she can have as many as three orgasms in a row. I tried to act suitably impressed.

The second annoying thing that she did was to make sure that I always knew I was her backup plan. She started every chat with words like ‘I couldn’t get ahold of booty-call boy, so I guess I’ll chat with you.’ That got old very quickly.

The final straw came after I had mostly decided I was done with her. She absolutely refused to meet on any normal terms. My wife invited her to a house party in Rockford, IL. It was too far away for Wendy. My wife invited her to a hotel party in Gurnee, IL, right across the border from Milwaukee. That was still too far, and Wendy said she didn’t like hotel parties.

I was still dumb enough to accept Wendy’s chats. A few weeks had gone by, and I mentioned that my wife and I were headed up to Oshkosh for a hotel party. Wendy scoffed, and then gave a detailed rundown of why hotel parties were a complete waste of money. Her three main complaints were that nobody had fun, you could never find anybody, and whatever you ended up with was disappointing.

I tried to convince her to attend as our guest. That way, she wouldn’t have to find someone, and I was pretty sure we would have some fun. She refused. All I can say is that I tried.

The next week, Wendy caught me in chat again. She was gloating as she asked how bad the party was.

I gave her a crestfallen look, and admitted it had been awful. I explained that I had agreed to help a friend out, but we couldn’t find what we were looking for, and in the end, I let her down. I did point out that I still managed to have a little fun.

I think that Wendy was starting to realize that I was making fun of her. With a dark look, she demanded details. I tried to defer, arguing that she wouldn’t believe a word of it anyways. She insisted. What else could I do?

 

Brenda:

My wife and I met Brenda at an infamous “Sue and Lyle” Party.

 

Tammy:

Tammy stopped me.

“You’re telling a story within a story?” she demanded.

“This is the part where I get to brag,” I answered. “I’d hate to spoil the ending, but I never had sex with Wendy. She called me a liar when I finished this story, and she hated how I proved that I wasn’t. Do you want me to continue?”

I don’t know if dagger stares can injure someone through video chat, but Tammy tried. She finally sighed, and said, “Go on.”

 

Brenda:

My wife and I met Brenda at an infamous “Sue and Lyle” Party.

She and I didn’t get a chance to play together, but late in the party, a small group of us were sitting around in the living room waiting on our spouses. The topic of bi-sexual women came up. My wife is very straight, but she is in the minority of women who swing. It is equally surprising how many swinging women claim to be bi-sexual, but they only want to play with other women at parties.

Brenda had never had a bi-sexual experience, but she was curious to try. On the same token, she was worried that if she tried something with one of her new friends in our group, she would feel awkward if things didn’t work out. My wife actually suggested a solution.

We invited Brenda to be our guest at a large hotel party in Oshkosh. We knew several very good looking women that would be at the party and would likely be very willing to help Brenda explore. She agreed immediately, and it was a date.

Susan saw an opportunity to get her single guy-friend, Jim, into the party. Normally the party was for couples and single women only. I was a little disappointed that Brenda agreed to pair up with him, and we all knew that he would not be helping her find what she was looking for.

I can’t tell you what it was about the Oshkosh group, but their hotel parties were awesome. They would take over the entire hotel, and they would set up privacy screens in front of every exterior door so people could wander around with the absolute minimum of clothing. Nudity was allowed in the pool area, and while sex in the pool and hot tub were frowned upon, it wasn’t forbidden.

People who liked to be watched would leave their room doors open. People who liked to watch were polite enough to take their pleasure without intruding upon the people in the rooms. Most important of all, everyone was friendly!

Sadly, a few years later, they moved to a new location farther north, and it wasn’t the same. I guess that’s another story.

As soon as we got there, my wife hooked up with another couple that we know, and they started to arrange to go get Mexican food and margaritas before the party officially started. Brenda claimed to be too nervous to eat, and my wife asked me to stay at the hotel to keep an eye on her. I’m not a big drinker, and sometimes spicy food is bad for me, so I readily agreed to stay.

I watched Brenda fidget for several minutes before I decided I should try to do something to calm her down. I asked if she wanted a massage, or if she wanted to go explore the pool situation.

She gave the floor a worried look for a few moments as she tried to decide what would help. A thought made the corners of her lips lift. She tried to force the smile and the thought away, but I don’t think she succeeded. The smile was still trying to break through when she gave me a hopeful look.

“Could we…?” she asked. She couldn’t finish the sentence, but I saw the hopeful mischief in her eyes.

I gave her body an appraising look of approval. “Yes?” I answered.

We were naked in moments, and we had a lot of fun. I was still calming the fuck out of her nerves an hour and a half later when my wife stuck her head in the room to remind us that people were supposed to be at the kick-off meeting.

 

Wendy:

“You did not have sex for ninety minutes!” Wendy insisted.

“It was very disappointing,” I replied with a straight face.

“I bet it was!” she exploded angrily.

“Yeah,” I said sadly. “Usually, I have better control, but I barely lasted an hour before she made me lose control. And then I had to make her give me a blow job to get hard again!”

“Shut the fuck up,” Wendy said darkly. “I suppose you gave her a couple of orgasms as well.”

“I really couldn’t say,” I managed with a straight face.

“Ha!” she pounced. “Typical guy who can’t even tell when a woman cums!”

“Oh no, it wasn’t that,” I answered sincerely. “Just before I lost control, we were scissored together, you know, with one leg over and one leg between. I was hitting something deep inside her and she was cumming over and over again. There was no way to keep count. She must have had a dozen orgasms just in that position.”

Wendy was just staring at me. I have no idea how I kept a straight face. I just kept talking.

“Losing control wasn’t the only disappointment either,” I said. “After we cleaned up, we went looking for my friend Shari. I knew she would be perfect for Brenda’s first experience with another woman, but we just couldn’t find her.”

I couldn’t tell if Wendy was even breathing. The only way I could tell that her video hadn’t frozen up was the building redness in her face.

“That’s when things really got out of control. Somehow I lost Brenda, but I found Shari. I talked Shari into returning to the room with me to wait for Brenda, but Brenda just never showed up.”

“So then you had sex with Shari, I suppose,” Wendy asked sarcastically.

“Well, not at first,” I answered truthfully. “Our friend Jim was in the room trying to seduce a woman, and so we took time to meet the new couple. They were Mary and John, and actually, Mary was trying to seduce Jim. He has a huge cock, and she wanted to see if she could even swallow half of it.”

“Huge?” Wendy asked.

“I could almost have cock envy if it didn’t make him such a jerk,” I laughed. “He’s not much bigger around than average, but he is over nine inches hanging, and eleven when he’s hard.”

“Did you get off standing around watching them fuck?” she asked in a tone that was meant to hurt.

“Of course not,” I answered smoothly. “I mean, Mary wanted to fuck, or at least suck, but Jim was being… well… Jim. The other John didn’t want to stand around and just watch, so he was trying to get Mary to leave. Luckily, Shari jumped in and changed his mind.”

“So you got off watching Shari and John fuck?” she accused.

“Kind of, yeah,” I laughed with a wicked grin. “Shari told Jim to stop being a jerk and to let Mary play. Then she told the other John to get naked so she could show everyone how it was done. I was going to leave, but she told me she wasn’t finished with me, either. As soon as she got John hard, she turned and bent over in front of him. As he went to town, she pulled me over in front of herself, and she made sure I was hard as well.”

“I bet that didn’t last long,” Wendy sneered.

“It didn’t…” I started to say.

“I knew it!” she pounced again.

“You can understand that I wasn’t paying much attention to Mary,” I said with a grin. Wendy frowned. “She found that she couldn’t swallow Jim’s entire cock, and then she wanted him to fuck her. Jim decided to be an ass, and he started this shtick about how condoms are too small unless he gets the right ones. He broke the first one on purpose, and then wandered out of the room to get another. He never returned.”

Wendy had a confused look on her face. She was trying to slam me for not lasting long, and I was talking about Jim and Mary. It was time for me to bring it all home.

“Mary looked at me and shrugged,” I continued. “About then, Shari did a switcheroo to suck on the other John while I fucked her. Mary asked Shari if she liked tasting herself like that, and Shari pulled Mary down to join her. I thought John was going to lose it when his wife started licking his balls while Shari deep-throated his shaft.”

Wendy was trying hard to come up with something sharp to say. I just kept going.

“Mary admitted she had always wondered what it was like to play with another woman,” I said. “Shari was quick to show her a thing or two. We tried every position possible for two women bracketed by two men. I couldn’t possibly guess how many orgasms each of the women had. I do know John lasted nearly twenty minutes before he came in Shari. I had to entertain both women for a while until he recovered.”

Wendy’s jaw just hung. I think she was waiting to see just how far I would stretch my yarn.

“My favorite moment was enjoying the intensity of Mary’s orgasm that followed,” I continued. “I don’t know if it was the angle we had as I fucked her from behind, or if it was her pleasure of licking her husband’s cum out of Shari while Shari came. I think I came nearly as hard as she did when I finally gave in. That was much later, after John joined us again.”

Wendy’s lips were pressed tightly together in a stern look.

“Shari had a great idea to end things,” I said with a lustful smile of remembrance. “She had Mary lay on her side, and then she moved into a sixty-nine position with her. Then she had each of us guys lay behind our woman to fuck her while they licked each other. Shari had her licking timed just right to stroke Mary’s clit and my cock. I swear Shari’s tongue was trying to get as far inside Mary as I was when we came. It was pretty intense.”

“You are so full of shit,” Wendy declared. “Why don’t you just admit that the party sucked instead of making up these bullshit lies?”

“Why would I lie?” I asked.

The sarcastic look that Wendy gave me would have stripped paint off the wall.

“You honestly want me to believe that you had sex with one woman for an hour and a half,” she groused, “and then you turned around and fucked two other women for another hour?”

“It was closer to another hour and a half,” I conceded, “but it didn’t take John long to join us again. I never would have survived that last forty-five minutes alone!”

“I’ve never met a guy that can last twenty minutes, and now you’re claiming there are two of you?” Wendy objected.

“I guess you’ll never know,” I answered with a smile, and then I did the video chat equivalent of hanging up on her.

Just in case she didn’t get the point, I unfriended her and blocked her.

 

Tammy:

“You really had sex for over an hour while continuously pleasuring your partner?” Tammy asked.

“It does require some self-control, which means a little bit of restraint,” I answered.

The look Tammy gave me was full of lust.

“Michael was saying something about a small party in two weeks,” she said with a flirtatious smile. “If you’re going to be there, I’ll agree to go.”

“I don’t know,” I answered with a smile of my own. “Maybe if you showed me a little something as an incentive…”

She gave me a coy look.

“Well, just thinking about meeting you is making my nipples hard,” she teased as she pulled the front of her shirt down to prove her point. She lifted one of her breasts with her hand, and her whole body squirmed as she showed off. As she settled back and brought her face back into view, her eyes directed my attention downward. She pulled her other hand up from below.

“I’m very wet, and I can’t wait to taste these juices on your cock,” she teased as she plunged her wet fingers into her mouth. Her body trembled as she licked them clean. I was so entranced with watching her lips that I almost missed when her smile turned to a frown and her brows bunched together.

“Didn’t you say something about making her watch you have sex?” she asked. “Did I miss something?”

I chuckled as I tried to get my brain restarted. Most of my blood was somewhere else.

“Do you really want me to brag some more?” I asked.

“What do you think?” she asked breathily as she caressed her own breast and her other hand disappeared downward.

Published 7 years ago

Leave a Comment