A Year of Living Dangerously Pt. 01

(All characters are aged 18 or older in all described scenarios. This is Part 1 of a five-part story.)

"... and once he dropped his pants, holy fuck! He had the biggest one I've ever seen! That thing was HUGE, and there was no way I was gonna let him put it in me. It would've wrecked me for life!"

The girls all rolled with laughter. "So, what did you do?" Rachel asked Summer.

"About the only thing I COULD do was jerk him off. No way that monster was gonna fit in my mouth either, so I just put my lips around his tip and used my hands. He only lasted about ten seconds anyway." Again, the group roared as they raised their glasses.

"Here's to enormous dicks with quick triggers!" Vicki toasted. Six glasses clinked together, and another level of inhibition fell away.

Vicki picked up on the theme. "Okay okay, my turn! I have a blowjob story. Remember that movie, 'There's Something About Mary?' One time, I was giving head to this guy in his car at the end of a date and he came so fast and hard that it got in my hair and all over the front of my blouse! Made a total mess! I had to sneak back into my apartment so that I didn't wake my roommate, or she would never have let me forget it!"

"Ewww..." the group said together, giggling nearly in unison at the thought of being covered in cum. "Yuck! Was he your boyfriend or just some guy you went out with?"

"Just a guy who asked me out. He paid for dinner, so I figured I should at least give him something. But what a mess! And I had to sit covered in it while he drove me home." More laughter as the friends enjoyed each other's crazy sexual experiences. More alcohol. Less inhibition.

Rachel moved forward in her seat. "I gave a guy a blowjob in the restroom at the bar once! I won't tell you who he was, because I think some of you might know him. Anyway, he'd been hitting on me all night and so I figured, what the Hell! But once I had his pants down, his dick was so small that I almost had no choice but to use my mouth on it. I don't think I could've given him a hand job if I'd wanted to. Maybe a two-fingered one. He thought I was deep throating him, but there wasn't anything 'deep' about it!" she laughed, her thumb and index finger spread at a gap of about two inches. "Really thin too. Poor guy."

Emily was silent, and grateful that Ashley was also sitting very quietly next to her, looking down nervously at her folded hands in her lap. Ashley was as shy as a church mouse, and neither of them had said a word once the conversation moved toward the explicit. Their friend, Becca, hadn't said anything either. Thank God she wasn't the only one who didn't have anything to share!

And then, quiet little Ashley took a long drink from her refilled wine glass, followed by a deep breath. "I once got picked up by an older couple at a bar in Cincinnati and went up to their room with them," she said barely above a whisper, her eyes looking at the floor and her face turning a bright shade of red.

"WHAT?!?" the girls gasped in amazement; their attention now laser-focused on the story of the century. Ashley loved being a part of this group of outgoing, gregarious, and confident women! She was anything but, and honestly, the group all thought that she was as virginal as a cloistered nun. All eyes and ears in the room were now directly on her, demanding that she share every juicy tidbit with them in painstaking detail.

"I was on a trip for work. I went down to the hotel bar for a cocktail after my boss's boss chewed me out for something earlier in the day that wasn't my fault. While I sat there with my second Cosmo, a nice older couple sat down next to me and ordered drinks. They were about fifty, I suppose. Really friendly! We got to talking and one thing led to the next, and pretty soon I was heading to their room with them to have another drink. But once we got up there, things just sorta started and I guess I liked it! Before too long, the woman and I were on the bed kissing... and things just happened." Ashley stopped, hoping that she had shared enough.

"Oh no! You can't leave it there! We want the juicy details! All of them!" Summer demanded for the group.

Ashley took another big gulp of wine for some much-needed courage. "You all know how shy I am. That's been the story of my life. Back in college, though, I had a stretch where I pushed myself to do things that were WAY out of my comfort zone. It worked for a while, but once I got out of school, I just ended up right back to the way I'd been before. But there were a couple of pretty wild years. Maybe I'll share those with you some other time. For now, let's just say that my freshman roommate was bi and leave it at that, okay?" The girls gasped, the realization that Ashley had a serious wild side just starting to settle in. "Anyway, I hadn't been with anyone for a couple of years when I was in Cincinnati that night, and I guess the Cosmos had loosened me up. So, when the Olsons approached me, I figured, 'why not?' They were really nice, and I was attracted to them both. When they invited me to their room, I knew what they were hoping would happen. I guess I hoped it would too."

"I can't believe what I'm hearing!" Rachel said out loud but directed at no one in particular, her words echoing what all of them were thinking.

"When we got upstairs, we each had a glass of wine and John put some smooth jazz music on the radio and Kate and I just started to dance. Pretty soon, she kissed me. I kissed her back, and we fell onto the bed. John sat down in a chair and watched us. We made out for a while and pretty soon we were both naked. She really knew her way around a woman's body! But so do I." Ashley's eyes dropped once again, embarrassed by her admission to her stunned friends. "So, we... pleasured each other, and it was awesome! When I finally looked up, John was sitting there naked, stroking himself. I motioned for him to join us, and I think you probably know what happened after that. He was gentle and it was actually a very beautiful experience!"

"Holy shit, Ashley! You win! I thought my story was bold, but I never would have guessed that one from you!" For the first time in her life, Vicki was actually more than a little jealous of another woman's sexual experience.

"Wait a minute! We haven't heard from the others yet. How about you, Emily?" Rachel demanded.

"What about Becca? You didn't ask her!" Emily was silently praying that Becca might not have a story to share either. She was very wrong!

Becca shook her head. "I can't ladies! You're all gonna think I'm a total slut!"

The group erupted with encouragement! "Tell us! Tell us!" they chanted in unison.

"Okay. I warned you! Last year, I... had three dates with four different guys in twenty-four hours."

"And...?"

"And yes, I had sex with each of them."

Again, the room exploded as the friends demanded details!

"This guy I knew from work was pretty cute and had been pestering me to go out with him. I usually try to avoid dating people from the office, but I hadn't had sex in a long time, so I decided to make an exception. We went out for dinner and dancing and one thing led to another and pretty soon we were heading back to his apartment. By the time we got through his door we'd already started making out. Before we even got into the living room, I was down to my panties and was pulling at his belt. He led me to his bedroom, and I was really ready for some fun! Once he was naked though... let's just say that he was more impressive with his clothes on. I'll give him credit for trying, but there was no way that I was gonna get there. Once he came, that was it. He fell right to sleep and left me laying there frustrated. I got up to go to the bathroom to clean up and literally bumped into his roommate in the hall."

"That guy was gorgeous! He was in his underwear, and I was naked and horny as Hell, so I just basically attacked him! We didn't say a single word to each other. It was pretty animalistic, actually. He really knew what he was doing too, and I got there twice before he did. Don't judge me, girls!"

"The next morning, I took an Über home. While I was in the car, I got a text from my old boyfriend who happened to be in town on a business trip, and he asked me if I wanted to meet for coffee. We had dated for about a year, and it was pretty clear that we weren't compatible. His tongue was magical, though, and the sexual tension was still there. We ended up in my apartment and... well, he hadn't forgotten where my buttons were! He curled my toes so hard that I didn't think I'd be able to walk again! He'd always known how to get me there and how to keep me there, and so he just kept going and going! I almost blacked out! He'd always really gotten off on making me cum! Then, he finished in me and left me on the bed in a puddle without even saying goodbye. He was great in the sack, but this just reminded me about what a jerk he is and why we broke up in the first place. But man! He really knows how to get me going!"

The ladies were stunned as they listened to her story, but so far that was only three guys, and she had said four.

"So, I'm feeling like a total slut and my head was really screwed up again, so I decided to go to the gym to work out. I was doing laps in the pool when I saw this guy coming out of the locker room. Great body, and I could see this enormous cock in the front of his swimming suit. He probably saw me staring at it. We started a nervous conversation, and he asked if I wanted to get a late lunch. I really needed to see what that monster looked like, and OMG! He was huge! Probably like the guy you had Summer, but he definitely didn't have a hair trigger!" The girls all laughed. "We got as far as his car and then started making out in the parking lot. Once I had his pants open and saw him erect, I just had to have him inside of me. We had sex right there in his car. It hurt like Hell at first, but he was patient with me until I finally adjusted to his size. After a few minutes, he told me that he was close, so I got off of him and let him cum in my mouth."

"So, there's my confession. Secrets stay right here, right?"

The silence in the room was deafening! Each of the girls was stunned at what they had just heard from Becca, and each was more than a little wet! And five of the six couldn't wait to get home to their fingers, vibrators, or a nice juicy cock. Five of the six that is.

And so, there was only one terrified friend remaining who hadn't shared a story yet, and Emily's mind was racing. A hasty escape was her last option. Emily allowed her full glass of Cabernet to spill onto her white skirt, and made a quick run to the bathroom to try to rinse it out before a stain set in. What she did might have been a little obvious to her friends, but it was a legitimate exit strategy and saved her from the embarrassment of not having anything to share. Nothing. Not one single story. For most of her life she had prided herself on her self-control. Of being 'moral.' Of keeping herself 'pure' for her future husband. But at that moment, she was feeling more than a little embarrassed that her sex life had been painfully vanilla.

It wasn't that she was a prude. She had had a lot of dates and even had a couple of steady boyfriends before she met her husband. Most of the guys had been given access to her tits while they made out of course, and a few of them had even been allowed to grind themselves against her enough for them to cum in their pants. She had regularly gotten naked with those two steady boyfriends, but never let it get past fingering and hand jobs with them, even though both of those guys had begged her for more, and probably broke up with her partly because she wouldn't give it to them. Nothing that she had done with them would be considered 'crazy.' It was all normal things that two normal people in a normal relationship would do with and for each other. But no stories worthy of sharing with friends ever happened. They were her own very personal and very private memories of early romantic moments of sexual discovery before she was with Mike. Memories that she had no intention of sharing with him or with anyone. But she had committed herself to being a 'good girl' and had been determined, for her own personal reasons, that until there was a ring on her finger, she wasn't going to go any further.

Then she met her husband. She just assumed that his past sex life had been pretty typical and that he had probably gone a lot further with other girls before they started dating, and she really didn't want to know anything about that. No reason to create any insecurities or self-doubts. That old stuff from their individual lives really didn't matter to her anyway, so the two just didn't talk about their sexual past.

But sadly, they actually didn't talk much about sex at all, and so both just assumed that the other was getting what was wanted in the bedroom. Mike had tried to push the envelope a few times early on in their relationship, but Emily's body-language had told him that he was clearly asking her for too much, so he backed off and eventually kind of gave up trying. Emily interpreted this to mean that he had lost interest in any sexual variety, even though that was actually far from the truth. And Mike took her reluctance to mean that she didn't find him as sexually interesting as she had the guys before him, even though she clearly loved him. Both assumed and neither shared. Big mistake! Consequently, their sex life was very bland and far from adventurous. Missionary position two or three times a month worked just fine for them, whether they needed it or not, and they never explored or even suggested trying anything new. Mike got his occasional orgasm with her, which he supplemented with regular masturbation when he was alone, and Emily took care of her own needs while in the shower or with her fingers in the middle of the night as he slept. Neither asked for more from the other, so with the passage of a few years of marriage, their sex life had gotten very predictable. And it worked for them both. At least as far as either was willing to share.

+++

Mike knew the look. He had been dozing on the sofa after watching his favorite team get hammered during an away game and woke up to the sound of the garage door closing. When he saw the expression on his wife's face and the stain on her wet skirt, he knew it would be best if he just gave her space. Emily's eyes told him that there was a story and that she would share when she was ready. No words were spoken. Mike stood and took her hand in his as they climbed the stairs to their bedroom. Emily was shaking. Whatever it was had hit her pretty hard.

"Will you just hold me, Mike?" was all she could make herself say as her body pressed up against his in their bed. A few moments later, Mike's breathing was slow and steady as his arm draped over her. At least one of them would be rested in the morning.

+++

In every couple there is always one who is the gatekeeper -- the one who is more reserved, the one whose limits are lower than the other's, the one who is most likely to say 'no.' She had always been the gatekeeper and was content in that role. That is until she heard all of her closest girlfriends sharing their wild sexcapades and realized that she had denied herself from exploring an entire side of her sexuality. Not completely of course, but almost. Worse yet though, was the realization that she had also denied Mike from exploring that part of his humanity as well, and she wondered what he really thought about what he was missing was her. Emily felt a slight pain in her gut, wondering if there was a buried part of him that resented her, if even a little, and it hurt.

From the time she had her first make-out session, Emily's attitudes about sex had always been very reserved. Those naughtier things were going to be saved to do with her future husband, but only if she had to. It had always puzzled her, though, that even the "good" boys wanted to do stuff with her that they had all been taught was sinful. But as 'dates' became 'boyfriends' she finally justified in her mind that hand stuff below the belt wasn't really 'sex' anyway, so she always made sure that her boyfriends had gotten their release before they parted for the night. She had felt really guilty, especially the first time, when a boyfriend's exploring hands found just the right spot and sent her body into orgasm. It didn't take very long for that guilt to go away though, and she learned to enjoy having occasional orgasms too, as long as it was only from their fingers! But Emily was always much more concerned that her boyfriends were satisfied than she was about her own pleasure. And she always knew where her limit was, and she never crossed it.

Over time, Emily had silently wondered if what she believed was really true, though. She kind of envied what her friends were doing when they went out on dates -- especially when they talked about some of the things that the guys had done to them in their dorm rooms or in the backseat of their cars. And she envied that her friends weren't afraid to get naked with their dates whenever they felt like it and that they didn't seem to feel shame or guilt or embarrassment when they did. Sometimes she regretted that she had limited herself so much. 'Good girls' weren't supposed to get horny or ask for anything sexual, right? Maybe she was wrong.

Emily's best friend had started way too early and had made a man out of too many guys to count. She had been lucky to avoid pregnancy or catching any STI's, and she somehow got through those years unscathed. Once she was free of her restrictive parents, she really went wild in college and did some crazy things with both guys and girls that Emily didn't even know was possible. But in her final year of college, she got religion, closed her legs and mouth, and after graduation, moved away to start a new life. She married a nice guy, and they had a happy life together. Emily always wondered how her friend's husband could accept the life that she had left behind. Even though her friend had been very promiscuous, they seemed like the perfect couple, and he didn't seem to be bothered at all by her past with others. Maybe she had never told him. Maybe his past had been similar, but she doubted it. Or maybe their relationship was a whole lot more colorful than she realized. Regardless, her friend had found happiness in her marriage AND had enjoyed a whole lot of sex along the way to the altar, too. Maybe she and Mike owed it to themselves to find out a few things as well.

Around 4:00am, Emily gave up on the possibility of falling asleep. She quietly exited the bedroom and fired up her search engine, determined to see for herself some of the forbidden fruit that she -- they -- had been missing. She wasn't really sure what search terms to use, but within a few minutes had landed on a porn site that seemed to have most of the answers to her questions. An hour or so later, she had seen more sexual variety than she ever thought possible, and her feelings of dread at what she had denied Mike over the years became even stronger. Suddenly, she realized that she had always been the one to resist and that she was rarely -- okay, never -- the one to initiate with him. She saw a bunch of things on her screen in close-up detail that they weren't doing but that she was pretty sure he had thought of and probably wanted to try. Maybe things that he had already gotten from the girls before her. Some were even things that he had asked for early on in their relationship and that she had denied him. Things he just never asked for from her anymore. Things that her friends had all talked openly about doing with their dates and with their husbands without reservation. Things that were absent from the bedroom for Emily and Mike.

As the morning sun peaked over the horizon, Emily realized that a long-overdue conversation needed to be had. If he was actually wanting more from her, scared as she might be, damn it, he was going to get it. The germ of an outrageous idea was starting to take shape in her very tired brain, but she was going to have to wait until she knew where his mind was really at for it to go any further. In the morning twilight, the stories that her friends had shared and the images that she had seen on the web played over and over again in her head, and she silently hoped that she wasn't too late.

(To be continued soon: Part 2 -- Unlocking the Gate)