Nothing Ventured Nothing Gained Ch. 02

We all go through stages in life and my metamorphosis into a liberated woman is by far the most exciting and satisfying.

Before I relate my recent experiences, there was an event that startled me. It had to do with our maid. Both my husband, Jack, and I work so we hired Monika to come in once a week to be our housekeeper. Monika is older than I and has been in the country from Poland for a dozen years. Monika, I would say, is not beautiful but has a way about her that is endearing, even sexy.

To make this incident short and without too much drama, Jack was in bed with Monika when I came home from the airport where I work as an airline agent. It wasn't so much that I was upset because we had already agreed on an open marriage. I was just astonished. It never occurred to me that Monika was the kind of woman that Jack would want to screw. He liked the young girls that he brought home from the college where he is a drama coach.

When we were alone, I asked Jack, "Why Monika?"

"Well, it just happened. Monika and I drank some vodka to celebrate her birthday. The next thing I knew she was giving me a blowjob, except it didn't end there."

"But Jack, her birthday was last month!"

"She didn't say when it was, only that her husband gave her a nice birthday present and she showed me a picture. It was a sexy nightgown that she loved. I'm sure her husband loved it even more."

"Should we fire her? I mean do you think we can keep her as our housekeeper?"

"Oh Signy, I think it was a one-time thing. Let's not dwell on it."

"When are you bringing over one of your drama students that you are so keen on mentoring? You were going to let me watch you directing one of your girls."

"Funny you should mention that. I know just the girl that needs special attention. She isn't as pretty as you but horny as hell and willing to try anything."

"How do you know that Jack?"

"Rumors get around and so does she. This girl is the college slut."

"Have you fucked her?"

"No, but there's always a first time. Should we invite her to join us?"

Jack laughed when I said, "Sounds like the right thing to do."

Two nights later, Jack brought home Angela, a nineteen-year-old girl with enormous tits and nearly six feet tall. My God, her legs were like stilts. I welcomed her to our home and helped her out of her dress giving her a sheer nightgown. I was making it clear that I approved of her visit and our motives were not entirely honorable.

I was also dressed for the occasion and my new remote-controlled vibrator sat on the bedside table in easy reach for my own satisfaction.

"Why don't you girls get to know each other while I get us something to drink."

I hugged Angela who was a responsive girl, exchanging deep and passionate kisses. Lying on the bed with our mouths interlocked, her hand found my pussy; her fingers caressing my clit. My mouth devoured her lusty nipples until she went down on me sucking in all the right places. I reciprocated. Jack watched while sipping his martini.

Jack took his time stripping down, finally joining us in bed as if on a mission. My knees straddled his face as he found my clit with a snake-like tongue, flickering and licking me into a frenzy while I watched Angela at the other end hungrily slurping at my husband's zealous cock. When she mounted him, I crawled off the bed to enjoy her youthful exuberance.

Jack can get pretty wild and noisy when he's having a good fuck and this was one of those times. After a while, he turned the girl on all fours and pounded into her doggie. One of the things I love about him is that with all of his violent thrusting, he doesn't cum too quickly giving a woman time to enjoy herself. Angela was definitely enjoying herself. I adored her uninhibited enthusiasm. She enjoyed giving pleasure as much as receiving it. I grabbed my toy so that I could enjoy pleasures of my own.

The combination of watching them fuck along with my pulsing vibrator brought me to multiple orgasms hoping Jack would have something left for me later that night.

I got my share of Jack after he took Angela back to the dorm. He lubed both my ass and his cock and plowed into my butt hole. I love anal and this time was better than ever. I fucked him like a whore that I would soon become.

Jack finished as he usually does with a growl, then a roar. There never is a doubt when Jack is going to cum.

This open marriage arrangement was working out even better than I had expected. Jack and I never had better sex and some of it was together. However, I never imagined things to turn out as they did.

The raffle adventure at a Nevada resort and the threesomes at home were just the beginning of my alternative sex life. The escapades with our neighbor, Jordan, and the college girl, Angela, were turning points. There were more fantasies from my fervent imagination that I was determined to experience.

A colleague and I had a quickie in the staff lounge where I work for the airlines. It was during the Christmas holidays and it seemed like the right thing to do. that is, naughty and nice. He came so quick I decided affairs with a little romance would be more satisfying. That realization led me to a pickup bar where I hooked up with Carl.

Carl wasn't as handsome as my husband, but he was polite with a deep sexy voice. I sat next to him at the bar with my dress hiked to midthigh wearing my best cleavage blouse. I don't have big tits like my friend Molly or the college girl Angela, but the blouse and a push-up bra made Carl think otherwise. The rest was easy except for telling a few lies like my name. I called myself Cyndy, with a double 'y.' That's what I told him and that my husband was a creep who was an alcoholic. I try to be honest but it's not a good idea in situations like this. I'm not a very good liar but he believed me.

Carl didn't say much except he was on a business trip and offered to buy me a drink. I accepted and told him how one drink makes me giddy. So, I acted giddy and had a second drink acting flirtatiously. Carl was getting the message and put his hand on my thigh. I just giggled and gave him a peck on the cheek. We left the bar and he fucked me in his motel room a short walk from the bar.

Carl wasn't the best lover a woman could want. He was nervous. I was impatient. We began with a kiss and romanced like teenagers on our first date. He helped me off with my clothes and spent a few minutes sucking my nipples.

"Do you masturbate?" he asked me.

"I do," was my answer.

"Show me while I get undressed."

I gave him a show for almost ten minutes while he took his time getting naked. Finally, he joined me in bed. I gave him a quick blowjob and he spent even less time eating me out,

He had me on my back, and we did it missionary. He asked where I wanted it. I told him I prefer it in my pussy. So, Carl came inside me and that was the best part. The man must have been storing up his semen for weeks or even months. After he filled my insides, Carl fell asleep. I cleaned up in the bathroom and left.

Jack asked me where I was that night. I said, "I went to a bar and fucked Carl in a motel."

He laughed and said, "Yeah, and I am Tom Hanks."

It was exciting being with a stranger but I hadn't achieved an orgasm so that was disappointing. Jack helped me get the satisfaction I missed with Carl before I fell asleep.

That piqued my imagination. Sex with strangers became my goal, so I went online. Again, I used my pseudonym, Cyndy, that I'd used with Carl. The biggest challenge of hooking up with strangers online is finding someone close to home. There was no limit to the number of guys willing to fuck me, but very few were within fifty miles. Persistence pays off when I found Teddy.

Teddy and I arranged to meet at a motel halfway between our two towns. I had to drive twenty-three miles in a driving rainstorm fearing the whole time that he wouldn't show up. He texted me five minutes after I parked in the back of the motel. "C'ya in room 147."

It was a little after eight that night when I knocked on the door soaking wet and shivering. His handsome face and broad smile welcomed me inside. He was naked except for wearing briefs covering a large bulge between his legs. He offered me a drink. I accepted. "On the rocks or straight up?" he asked.

Scotch is not my drink, but I told him, "Ice for the drink but I want you straight up."

Teddy laughed at my joke and give me a passionate kiss. "We've got to get you out of these clothes before you freeze to death," he said. I sipped my drink while hanging my clothes in the bathroom. Teddy was a pleasant man and liked to talk. He was easy to be with helping me relax. I knew this would be better than being with Carl.

A half-hour later he said, "I've been looking forward to getting to know you close-up and personal. You know, intimately. To be honest, you are more beautiful and sexier than most women I know."

The scotch and compliments put me at ease when he said, "Stand over by the TV, Cyndy, and let me see you."

I moved a few steps away from him and turned slowly giving him a tantalizing smile.

"Let me see your tits, Cyndy," he said, so I took off my bra lifting my breasts to make them seem larger.

He turned on more lights in the room and said, "Oh, that's nice. Now the thong."

I turned my back to him and seductively slid off the thong leaving it on the floor.

"Bend over dear and show me your ass."

I did what he asked.

"Now turn around and show me your pussy."

I did. He had removed his briefs while I modeled for him. Teddy's cock was straight up like I joked, erect, almost as long as the iPad tablet he was holding. Teddy was taking pictures.

"Oh great. You're shaved!"

"I'm not here to fill your iPad with dirty pictures so you can stop it right now," I grumbled.

"Don't get upset. You are a beautiful addition to my gallery. Come here I'll show you."

We sat on the bed together and he gloated over the women he had fucked. Some pictures were graphic and pure pornography. Most of the women were my age, two were no older than eighteen or nineteen. To be honest, I was excited to be included.

"Let's get it on and make some memories," he said softly nipping at my nipples.

We rolled in bed together and he went down on me for our first memory. Teddy knew what he was doing and was good at it. I was hot and he responded with a groan when I engulfed his stiff dick trying my best to get it down my throat. I gagged when he pushed my head down forcing it into my neck. I couldn't breathe.

He pulled out just in time. My face was flushed, and I was gasping for air while he turned me over on all fours. Teddy leaned over my back hugging my tits and drove his hard dagger to the hilt.

Teddy didn't cum right away, but I did. During my second orgasm, he finally let it flow, firing spurt after spurt deep inside me. It felt so warm and soothing intensifying my gratification. Like in the Beatles's song, "Happiness is a warm gun."

Our tryst wasn't over. I was a little stunned when he picked up his iPod to take pictures of cum oozing out of my pussy. I was still floating in air and didn't care what he was doing.

Teddy recovered quickly. He had me on my back with my legs and ass pointing to the ceiling. He was above me drilling my pussy up and down like a butter churn. Cum was still squishing out of me from the first time until he decided to fuck my ass. He seemed to go on for hours before satisfying himself for a second time.

"Okay, darling," he said. "I'm through. We've been at it for a couple of hours. It's getting late. This was fun but I've got to get back home. My kids are waiting for daddy to kiss them goodnight."

It was after midnight and I wondered what kids stay up that late.

At home, I woke my husband, Jack, and he asked where I had been. I told him I had been fucking Teddy for two hours. He laughed and said, "Did you have a good time?" and went back to sleep.

Well, I thought that was the end of it. There just didn't seem much left in my sex fantasy. That would have been true if it hadn't been for Ricardo. I was browsing again on my favorite website where people post sex stories and chat. I decided to write a story about me and Teddy with a lot of exaggerated details that didn't actually happen. and send it to the website

The website monitors approved it and posted my story. Now I was an author and I felt very good about myself, even encouraging me to write more in this memoir. It led to several people writing nice things about my story. Ricardo was one of those who gave the story five stars.

He sent me a message and right away I could tell Ricardo was a cool guy. We wrote back and forth. He always added a joke at the end. They were not the kind of joke I could share with my grandma. The first one was, 'What's the difference between a G-spot and a golf ball?' Answer: 'A man will actually search for a golf ball.' The jokes became more obscene as time went on. I loved them and was getting turned on by Ricardo.

Eventually, I agreed to what he called RP which I found out meant role play. So, Ricardo started by writing about two strangers who met online and became friends. Soon they realized there was a mutual attraction and the man asked, "Do you think we should meet?" like in the movie 'You've Got Mail.' So, they met and hooked up for a one-night stand.

I'm leaving out most of the erotic details but during the next two weeks, the woman in our RP met him for more sexual liaisons until she was invited to a private party at his house. Well, without getting too graphic here, she became the central character in a gangbang with five men. I imagined being that woman, and it made me as horny as hell.

I told Ricardo how much fun it was doing RP to fantasize about pleasuring five men at a party. He asked, "Have you ever thought about doing it?"

I wrote, "No. I never thought about it until now." I changed the subject and wrote, "Maybe we should exchange pictures, without our faces of course."

He sent me three pictures. Ricardo was impeccably dressed looking like any wealthy man you might pass on a city street. I was disappointed. It wasn't the kind of picture I had hoped for. I decided to send him two pictures of me wearing my sexiest lingerie remembering how Monika had seduced my husband. He liked what he saw and upped the ante showing his hairy chest and a generous bulge under his briefs. I laughed to myself thinking he had stuffed something in there to look bigger.

I sent a side view of my naked body. All he said was, "Wow," and attached a selfie of him naked from the rear. I fell in love with his tight ass.

I didn't think I was brave enough to send a frontal nude, however that became my next picture. He sent back a picture of his amazing cock. Obviously, there was no need for him to stuff his briefs like I had imagined. I asked to see him hard and drooled over his next picture.

Ricardo said I had a nice body and wanted to see me masturbate. "You're kidding," I wrote. He said we could do it together. So, we got on FaceTime and had virtual sex together. God how he could cum.

That led to Ricardo inviting me to lunch. After sexting for a week, the timing was right.

I knew something about his body but not his face, so I wasn't sure how to recognize him. Was he Mexican or Spanish? I didn't know and thought it was politically incorrect to ask. We decided not to use the movie cliché of a red rose and a copy from "Pride and Prejudice," like in the movie.

"I'll be at Starbucks in Middleton (an hour from my home) with a cup of espresso reading the Wall Street Journal." Ricardo said he would be there at eleven the next morning.

I didn't sleep well that night imagining all the things that might go wrong but in case they didn't, I was freshly shaved anticipating an after coffee arrangement.

Two men came into the coffee shop while I pretended to be studying the Journal. Neither looked Hispanic. Finally, a handsome guy with a nicely trimmed beard spotted me and asked with a warm smile. "May I join you?"

"Are you Ricardo?"

"I am. And you are Cyndy with two y's?"

I nodded that I was. "Please excuse me while I order coffee and a blueberry muffin. Would you like a muffin too?"

"That would be nice. Thank you, Ricardo."

After a half-hour of small talk, Ricardo took me to a Mexican restaurant for lunch. The salsa was hot and got even hotter as our conversation began to heat up.

"You know, Ricardo, after our RP, I had these dreams. I was walking naked while shopping for a hat so I wouldn't get cold. Imagine that! Shopping for a hat to keep me warm. There was a nice shop that had a beautiful, knitted hat in the window. So, I went inside. There were only men in the store, and all were dressed in tuxedos except for wearing open crotch leather pants. They wore the hat I wanted hooked onto their erections like a hat rack. I tried to ask about the hat, but no one paid attention to me. I started to cry and woke up in tears."

Ricardo nodded and said, "Yes, dreams are like that. We never are sure what they are telling us. Maybe you wanted a warm cock, not a hat."

When lunch was over, I waited for Ricardo to suggest we go someplace private. He began by saying, "I'm so sorry your dream was upsetting. I'd like to continue our time together but I'm due to coach a soccer team this afternoon. You know, in Mexico it's called football. We'll be in touch. I'd like to make that dream of yours turn out to be a happy ending."

It sounded like a brush off and instead of a happy ending, it looked just like an ending. With that, he paid the bill and walked me to my car.

Ricardo didn't write for over a week. It occurred to me that I wasn't his type. But perhaps I had misjudged him when he e-mailed an invitation to a party. It was at a hotel not far from me on Super Bowl Sunday.

Ricardo ended his message with a joke like always. He wrote, "Speaking of a party, the penis tells the balls: 'Tonight you are going to a party!' The balls reply, 'You fucking liar, you always get inside and leave us hanging!'"

I'm not much of a football fan whether it's the American kind or soccer. Jack arranged to see the game with his buddies and he wasn't surprised when I told him I wasn't going with him. The guys get drunk and Jack will need to be nursed back to health the next day. He always expects me to be the nurse.

With that said, I had the evening free. Anyway, I was curious to find out what Ricardo had in mind although I was sure we would not have a problem entertaining ourselves without watching the game. I was game for something else. After all, we were meeting at a nice hotel.

Okay, here is what happened, and it wasn't what I had expected. When Ricardo greeted me at the door, I immediately realized we would not be alone. Three men, all of Hispanic heritage, looked at me like I was an alien. Maybe it was because my skin was too white, and my eyes are blue.

Ricardo welcomed me and said, "I'd like you to meet some of the guys on my team. This is Mateo, and Diego, and Marcos."

They all gave me a quick hug with Diego handing me a drink. "What are we drinking today?" I asked.

"It's called a 'Mexican Mule.'"

"What's in it?"

"Tequila, señora," Marcos answered.

"I like tequila, Marcos, thanks."

The game was starting but no one was watching. They were checking me out and not too discreetly. I was tonight's entertainment, the mark, the score. My mind was swimming with curiosity. Who would make the first move? Who would I fuck first? Who had the biggest dick? I would have my answers in the next few hours.

Ricardo sat next to me. Not just next to me but he sat so close I could feel his breath. "Cyndy, I never forgot your dream and promised myself to make it better for you. My friends are here to help. I want you to enjoy yourself. My friends and I will do that for you. I'm sorry that Juan couldn't be here. His wife made him watch the game at home."