Nothing Ventured Nothing Gained

I haven't written a diary since high school and although this is more of a memoir, it is a way of telling how life gets so much better as a liberated woman than being stuck at home reading romance novels. This is just the beginning of what was an ordinary sex life and has become much more.

It all started with a raffle ticket. The winner was given a weekend for two at a Nevada resort. I'm a member of Bid and Trump, BAT for short. We are a women's organization meeting twice a month playing bridge when we're not raising money for charities. The restoration of our town's auditorium was one of our projects. Auctions and raffles are painless ways to accomplish our goals. My husband, Jack, wasn't happy when I bought $100 worth of raffle tickets for a Nevada all-expenses-paid vacation. I explained to him it was for a good cause. I also thought it would be great for us to get away for a while.

I can't say the drawing was rigged but I won! That's the good news. It gets better. Jack wasn't interested in going, so Molly and I packed our bags and flew to Vegas where we were met at the airport, then chauffeured to the resort. We were settled in our room by late afternoon.

Whoever picked the resort didn't do their homework or they did the research hoping to win. My guess is it was Molly who booked the resort because she begged to go with me when she heard Jack wasn't going.

Let me say something about Molly. Molly is my best friend and our BAT secretary. She is a year or two younger than me, divorced, curvaceous, a risk-taker, outspoken, and liked by everyone. So, a girls' weekend with Molly would be fun. Okay, we're not girls but that's what we like to call each other. Oh, one more thing. Molly is a shutterbug. She uses her cell phone like clockwork taking pictures of anything moving or not.

The resort sign pointing to the 'clothing optional' swimming pool was our first clue that this wasn't your ordinary Ma and Pa lodge. The second was watching young girls, according to my middle age eyes, parading around in skimpy bikinis accompanied by older men with silver hair. Then there were the other amenities that I'll get to in a moment.

Our first stop after unpacking was at the bar. The drink of the day was piña coladas. We both ordered one as our free welcoming drink. On the day we arrived, everything else was half price, so we didn't stop drinking until dinner. The thing about piña coladas is you never taste the rum, hardly knowing you are drinking alcohol until it's too late.

Both Molly and I were a little tipsy when we went to the buffet. There was nothing special about the food, but we were hungry enjoying the shrimp and salad bar. I treated myself to Chocolate Mousse for dessert. Molly had ice cream topped with a cherry.

The cherry brought us to a conversation from our past. "When did you lose your cherry, Signy?" Molly asked.

"I've never talked about it before. What made you ask?"

"I don't know, curious I guess. It just popped into my head when I saw the cherry on top of my ice cream. It looked sexy like a nipple on a woman's tit. You are very pretty, Signy, so guys must have been lining up to get into your pussy."

Like I said, we were a little tipsy, so this kind of conversation seemed almost normal. "I don't know about guys lining up," I said, "but I had a boyfriend. We started dating my junior year in high school. We fooled around a little, but it wasn't until our senior year that we did it on his eighteenth birthday. You know, a girlfriend's birthday present."

"Were you jailbait?"

I laughed. "I haven't heard that expression for years, Molly. No, I was a few months older than my boyfriend. Everyone called him Charlie, but his real name was Ackerley Charles Pennington."

"How was it, I mean your first time?"

"I don't remember much about it except it was over so fast. We were in his car listening to Elvis sing 'Love Me Tender' and neither of us knew what we were doing. He couldn't get the condom foil opened and my panties got stuck on the seatbelt. Then I had to help him get it in. It was over before the song ended. When I got home, my panties were stained, so I washed them out fast before my mom noticed. How about you?"

Molly took a minute before answering. "I was about your age, but it was quite different for me. I was a cheerleader in high school and dated a lot. There was never a time when my date didn't try to feel me up and get into my panties. I wanted to be a good girl and wait, but the truth was that I really wanted to have sex.

"One night after a basketball game," Molly continued, "the coach asked if I needed a ride home. He lived in the neighborhood, so it seemed like a good idea. He told me a little about playing at Duke and asked me if I'd like to see some pictures from college. I said okay.

"He introduced me to his wife, Charlotte, and the three of us sat on the couch looking at his photo album. Charlotte was friendly, maybe too friendly when her hand touched my leg. After all, a cheerleader's dress is short, so it wasn't until her hand moved up my thigh that I became alarmed.

"Charlotte told me, 'You have such a beautiful body, Molly. I wish my tits were as full as yours.' I started to squirm when she put a hand on my breast and kissed me. Of course, now I knew this wasn't going to be about Duke basketball. They seemed to sense that I welcomed their attention and wanted sex.

"Then the coach said, 'Charlotte is right. You have a terrific body, Molly. It would be such a shame to leave it hiding under that uniform. Let's take off these silly clothes so you can show us?' Charlotte wasn't waiting for me to object. She pulled off my panties and was on her knees kissing and licking my pussy. Meanwhile, Coach was pulling the top over my head and unhooking my bra. My heart was pounding, and I was so aroused that it felt like a dream.

"I was overwhelmed with passion while Charlotte was giving me head and Coach was nibbling on my tits. 'Are you a virgin, honey?' Charlotte asked. 'My husband wanted me as a virgin, but he wasn't my first. Now I think he will get his wish in your tight virgin hole,' she purred giving me a friendly smile.

"Except for my shoes, I was naked and totally ready for Coach to pop my cherry. But first, Charlotte had her own desires and took Coach's cock in her mouth. That took only a minute to get him hard before he mounted me and squeezed inside my eager virgin cunt. God, it was everything I'd hoped it would be. I loved it from the first and it certainly wasn't my last before graduating. The only thing that scared me was that Coach came inside me. I was sure he knocked me up. I got lucky. From then on, I always made the guy use protection."

"Wow, Molly, that's an amazing story and got me all excited. I could use a man right now!"

"Let's go to the floor show tonight, Signy," Molly suggested. "Maybe that will help."

"What show?"

"Didn't you read the daily schedule at the bar? Tonight, the Nasty Boys are giving an all-male review for the 'discriminating woman.' That's what they called it, anyway."

"And that means?"

"It means male strippers!" she enthusiastically declared.

I had been to a strip club for my sister's bachelorette party. It was disappointing. There were hardbodies but no hard cocks. The dancers were not fully nude and left on their G-strings. Molly assured me this time it would be different.

Each of five round tables sat four of us in front of the stage. Most of the tables were filled with women our age although one table had the grandmother types and another with college girls. Sitting with us was Tiffany and Samantha, both were mothers in their forties from out of town.

All of us ordered Mai Tais so we bonded immediately. The show wouldn't start for a few minutes, so they talked about their kids and we told them how I won the BAT raffle.

Loud 'Star Wars' music introduced a half dozen actors parading before us dressed as 'Star Wars' characters. There was Chewbacca, Obi-Wan Kenobi, C-3PO, Luke Skywalker, Han Solo, and of course, Darth Vader. They strutted ominously back and forth making lewd remarks about the audience. I was singled out as the fuckable whore Princess Leia. Molly was the seductive slut Rey Skywalker who was given a lightsaber to hold in the shape of a penis that changed colors when it was squeezed.

The lightsaber was passed around with every woman in the room getting caught up with the act and began shouting vulgar invitations to the actors. The music softened, the lights dimmed, and the men slowly left the stage. There was a moment of silence before C-3PO came on stage still in character wearing an erect mechanical penis pulsing like a strobe light. He asked for a volunteer to accompany him on stage. There was no shortage of volunteers. The lady who was chosen fell to her knees to give the automated cock a blowjob. She gave a convincing performance that ended when C-3PO pressed the round button on his chest spraying the woman with a milky facial. We all cheered.

Each Nasty Boy followed in character asking volunteers to simulate various sex acts. Act One ended with an impressive firework display that exploded from large erect plastic cocks. By intermission, the audience had lost all inhibitions. Women were shouting obscenities as the men returned to the stage for the second act.

'Star Wars' outfits were replaced by sleeveless shirts with bowties showing off muscular biceps and sexy tights like those in a ballet that exhibited massive bulges. To the delight of everyone, they danced, wiggled, and stripped off their shirts and pants that showed off their toned bodies but none of them went full monty. They still wore G-strings. The women were screaming at that point. "Take it off. Take it all off!"

Each performer in turn followed a similar routine by turning their backs to the audience, slipping off their thong, throwing it into the crowd, then bending over to show their tight ass and dangling balls. They danced off the stage teasing us pretending to keep their manly organ private.

Of course, this was met with howls of indignation from us. We all chanted, "We want cock. We want cock." My guess is most of the audience had wet panties by then. I know mine was soaked and Molly was stuffing a napkin inside hers.

But the show wasn't over. There was an encore. All six performers boogied on stage to disco music completely nude. There was no coverup this time, some with their masculinity as stiff as a board, the others wagging back and forth like a dog's tail. It was very much like a fashion show but without the fashions. We weren't disappointed with their physical attributes. A few women, including me and Molly, rushed to the stage reaching to touch their disco sticks. The men obliged and let us touch and taste. Molly had one halfway down her throat while I was testing for firmness. I found one guy that surpassed all the others with a dick so hard it stood straight up like a soldier at attention. I expected it to go off at any moment.

It was seconds short of an orgy when the lights went out, the music stopped, and the Nasty Boys disappeared. We were left in the dark for a minute giving us time to catch our breath and straighten our hair.

"Oh my God. I need a man now more than ever," I told Molly.

"Me too. Let's go upstairs and help each other get through this."

What she meant was helping each other get off. I hadn't had a cunnilingus with a woman since college and had forgotten how much I missed it. Molly was the perfect partner. I must have cum three times before going down on her. She came early and often and both of us slept like a log in each other's arms.

We slept late before going to breakfast. I dressed modestly. Molly not so much. She wore short denim cutoffs and a deep cut blouse with spaghetti straps holding a top that barely kept her breasts from falling out. "Did you look at the entertainment guide? Molly asked.

"No. Anything interesting?"

"Well, yes. They have a full-page ad on the Nasty Boys and at the bottom of the page, there is one for an adult bookstore down the street. "Have you been to a porn shop?"

"No. Have you?"

"Of course. We ought to check it out. It will be fun. I've been looking for a new toy. My rabbit doesn't hold a charge anymore."

The store wasn't just down the street. We walked for a half-hour before finding it tucked away behind a mall. There was a woman behind the counter and three or four men browsing the merchandise. There was everything from porn magazines and videos to sex dolls along with vibrators of every size and shape.

"Oh look," Molly whispered, "they have a glory hole," pointing to a sign stating there are discounts for women.

"A what?" I mumbled.

"It's very simple. We go in the booth over there and a guy on the other side sticks his dick in a hole. Then we suck him off or fuck him if you want."

"How do you know?"

"My ex took me to one before we got divorced."

"Who did you suck off?"

"That's the fun part. The guy was a stranger. It's all anonymous. Let's do it!"

"What's the discount for?"

We asked the store lady who told us that there was a ten percent lady's discount for each man she gets off. Two men twenty percent, up to thirty percent off.

"Come on. Let's do it!" Molly pleaded. So, we both ducked into the booth.

There was a video screen showing porn videos and ads for sex toys. On the wall was an oval hole. Molly explained, "When you are ready and want a cock, just put a finger on the rim of the hole. It's like an invitation."

"Are we supposed to take off our clothes?" I asked.

"You don't have to, but guys like to reach in and feel your boobs or pussy to make sure a female is doing him. If you like the cock, you can fuck it."

"Is that what you did when you went?"

"No. I was with my husband and he fucked me while I blew a couple of guys."

"Okay, you go first," I exclaimed.

Molly dropped the top of her blouse. There would be no doubt a woman was servicing him. Molly rimmed the hole with two fingers; nothing happened. We waited and watched the video of a woman DPing two very well-endowed men.

Molly tried once more and a cock at half-mast appeared.

Molly grinned and said, "Looks like he needs some straightening," and she gently touched it.

The man pulled out and reached in with his hand finding her tits and pinching her nipples. Then he put his mostly hard cock back through the hole and Molly went to work. She was good at it having no trouble taking his entire shaft down her throat. The whole spectacle made me horny and I was hot to be next. It was time for me join molly and take off my blouse and bra.

My turn wasn't until watching Molly get a facial. The stranger on the other side had given her an impressive load. I thought it was a waste of fresh cum. She should have taken it in her mouth. I've always liked cum since my first boyfriend made me swallow, so that is what I was aiming for.

I rimmed the hole and waited. It was a short wait and a long cock. A hand reached in feeling my tits followed by his steely hard prick. I wanted to show off to Molly and demonstrate that my technique was as good as hers, but she was distracted by the video.

The man I was doing had incredible endurance. I kept licking and sucking and was about to pull down my panties and stick his cock in my dripping cunt when he exploded in my mouth, He just never seemed to stop cumming. Some started to drip onto my chin that I scooped back on my tongue before it dripped on my skirt.

"You really got into it. You're an amazing cum sucker," Molly said, "and I think I've found my perfect vibrator."

We dressed leaving the booth to look for the toy she had seen on the video screen. Molly bought a bullet egg-shaped vibrator that had a tail attached. Molly rationalized the cost by saying, "It was kind of expensive but with our twenty percent discount, it was worth it." Back at the lodge, she downloaded the app on her cell phone and charged the battery before we had lunch.

Molly explained that her new vibrator was Bluetooth and controlled by an app on her phone. She said I could be added as a contact and control it from anywhere there is the Internet. "You know, maybe I can call you and say I need you to turn me on. You start the app, then you can do me with any of the modes. I love the idea that it can be worn anywhere, and nobody would know I was getting off at Starbucks."

The rest of our afternoon was spent in the outdoor pool with umbrella drinks getting in some sun and relaxation until we went back to the room and played with her toy. It worked as advertised. After Molly had played for a while, I put the fat end in my vagina and pressed the button on the tail to turn it on. Molly was at the controls. God how I loved it and couldn't wait to order my own from Amazon.

We met Tiffany and Samantha, the women we met the night before, for dinner and talked about our day. Molly had the vibrator on the whole time, so she was somewhat distracted.

"Have you been to the nudie pool?" Tiffany asked.

I looked at Molly who shook her head. She said, "We were getting tanned outside today. Have you been there?" Molly asked.

Samantha grinned and said, "Oh yes, and a lot more."

"A lot more?" I asked.

Tiffany took a sip of her margarita before saying, "Well, after last night we were pretty horny. I think we all were. Anyway, this afternoon we met a couple of guys at the nudie pool. They were young and you know, they were hard, I mean hard to resist," and she giggled like a teenager. "So, they invited us up to their room and that's where we spent the afternoon. I guess you could say they quenched our thirst," and she giggled again. "Maybe you two should go to the pool after dinner."

"Thanks for the suggestion. By the way, if you are free tomorrow, you two might stop by the mall. There's an interesting adult bookstore there," Molly said. "It's called the Adult Fantasy Store."

Samantha asked, "What made it so interesting? It's just a porn shop, right?"

I looked at Molly who was busy taking pictures with her cell phone. "Oh," I answered, "the glory hole for starters."

"You didn't!" Samantha cried.

"We did," Molly answered, and she showed them a photo on her cell phone. That pretty much ended our dinner together.

Molly couldn't wait to get to the pool. I wasn't so sure about being naked in a public place. She talked me into it. We wore only terry cloth robes and sandals and followed the sign pointing to the clothes optional pool. It was smaller than the outdoor pool and nearly empty. Without many people around, it was easier for me to take off my robe and slip into the pool naked.

The feeling of being naked in public gave me an overwhelmingly sensual feeling, unrestrained and tranquil. I just laid on my back as if floating on a cloud. I had never felt more relaxed.

An older couple joined us followed by a tall young black guy. I couldn't help noticing that he was really well hung and completely shaved. I'm no authority on penis size but I can say this guy was big. Hanging limp, he was bigger than my husband's erection.

At first, I thought he might be one of the Nasty Boys from the night before, but Molly learned later that he was a basketball player at the state college. He wasn't in the pool two minutes before he had spotted Molly's voluptuous tits and made waves swimming next to her.

I held back as an observer pretending to do laps in the pool but keeping an eye on my friend and her soon to be lover. Before I finished my second lap, they had gone from strangers to acquaintances to friends with benefits. The way they smiled at each other it was hard to tell who was seducing whom.

When more people joined us in the pool, Molly came up to me and said, "It's getting crowded. Jalen and I are going upstairs to have a drink."

That was the first time I had heard his name and guessed having a drink was a euphemism for fucking because the pool had a swim-up bar if they needed a cocktail. More likely she was after his cock and Julen wanted tail. Anyway, I spent over an hour at the bar before going up to the room. I figured that was plenty of time for them to finish their drink.