Easing Into Swinging

It had been three weeks since My wife Analisa and I had our first threesome. It had been three weeks since I watched my wife suck and fuck a friend's hard black cock. Since that night, our sex had gotten more intense and hotter. She never asked for a repeat event. She seemed more than content with my cock in her mouth, pussy, and ass. We were having sex more often than we had before, which was a lot because we were having sex almost daily before. Now we were fucking sometimes twice a day, more on her days off.

On one of her rare full weekends off, Analisa told me that she wanted to go out and have fun. I had no jobs that weekend, so I decided to rent a hotel downtown and spoil her. We packed our bags and less than an hour later, we were in a beautiful suite over looking the city. Our window looked over one of the busiest intersections. It was full of cars and pedestrians. Analisa stripped out of her clothes and stood at the balcony door. She let her massive 38H tits sway freely, letting a cool breeze hit her now diamond hard pierced nipples. I walked up behind her and wrapped my arms around her waist. I leaned down and began kissing her neck, causing her to moan slightly. My hands moved up from her stomach and began massaging her breasts. She started grinding her ass against my cock, which was getting harder quickly in my pants. She slowly turned around and dropped to her knees. She looked up and smiled at me as she slowly undid my pants. She reached in and wrapped her hand on my throbbing member. She let my pants and boxers drop to the floor of the balcony as she took my entire cock into her mouth. She took her time, moving up and down the shaft at a very sexy pace. She would take my cock out of her mouth long enough to suck my balls and stroke me for a little while. After the fifteen-minute blow job, she stood back up and bent over the railing of the balcony.

If people had been looking and were at the right angle, they would have been able to catch me sliding my cock deep into her drenched pussy. I took my time sliding my cock in her. I slowly allowed her to enjoy inch by inch of me penetrating her. Once I got all seven inches in her, I began to pick up the pace, thrusting into her harder as her moaning began to get louder. I then began to furiously fuck her as she had hit her first orgasm. No noise came out as she was trying to catch her breath. Her big tits were flopping in the wind as I pounded her soaked pussy. I continued to fuck her until she started begging me to cum on her ass. I had been fucking her for almost thirty minutes when I finally released my load all over her sexy ass. Once I came, she turned around and kissed me softly, thanking me for the fuck.

After we both jumped in the shower, which lead to another round of hot steamy sex that ended with another load filling her tight ass, we changed into nice clothes for dinner and a night out of hitting bars. I put on my standard black on black suit that included black shirt and slacks, a pair of black dress shoes, and a red tie and vest to match her dress of the night. Her dress was a dark red that had a slit up her right leg that went to her mid-thigh. It had a plunging neck line that showed off her cleavage nicely. Her red heels completed the outfit. She allowed her long black hair to fall freely down her back. We left our hotel and walked to a nice restaurant close by. We both were entertained during dinner by our waiter, even if he didn't know he was entertaining us. He could never seem to keep his eyes away from Analisa's cleavage. While standing above us, he had a great view. Analisa would occasionally look at his crotch where she could see the bulge in his pants.

After dinner, we made our way to a small bar that she had heard about from a coworker. We walked in around 9pm. It was not very busy, but the bartender told us that it would pick up. We grabbed our drinks and found a table in the corner. We watched as people made their way into the bar. I noticed that there were very few single people coming into the bar. It was mostly well-dressed couples. The few single people or non-couples were women.

"You would think there would be more guys in a place like this," I said to Analisa, looking at the growing crowd.

"You won't find any single guys or large groups of guys in here," she replied as she took as sip of her drink.

"And why is that?"

"So, Jessica at work and I got to talking and eventually, we got to the conversation about sex. I may have let it slip about our little adventure with Dave."

"Seriously?"

"Yeah. She said she had done things like that with her husband many times. I then told her how I wanted to experiment with another woman joining us. She recommended this place. They do not let trashy people in. You notice how everyone in here is dressed very nice."

I looked around the bar again and realized that all guys were wearing a variation of a suit and the women were all in dresses or very sexy skirts. None of them looked like sluts. The outfits were revealing but tasteful.

"So, you wanted to come her to..."

"I want to find a woman to take to bed with us," she said. "We both want it, so why wait? If we can't find a single woman to join us, then we at least get to drink and enjoy the view."

"What if another couple wants to join us?"

"I don't think I am at that point yet. I still need to find out if I will enjoy being with another woman."

"If we are going to do this, then we need to set ground rules now. Rule one, we both have to agree on the woman."

"I can agree to that. Rule two, she must be willing to be with both of us, not just one of us. The more things she has in common with us regarding what she likes during sex, the better."

"Agreed. I will be wearing a condom. There is no exception to that. I don't care if she swears on a holy bible that she is on the pill or shot, I refuse to take that risk."

"Absolutely. Anything else?"

"Not at the moment. If we do get to that point, I will be standing back for the start. I want you to take in the full experience of being with another woman before I introduce the penis."

She laughed at the comment but understood what I meant. A cute waitress came up to our table as we were ending the conversation.

"Hi. I'm Shelby. I'll be your waitress tonight. If you need anything, just wave me down. What are you drinking tonight?"

"I'll have a double of Jameson on the rocks and she is having a cosmopolitan."

Shelby walked away, and I could not help but admire her tight little ass.

"She does have a nice ass," said Analisa, also checking out Shelby's ass. "She's cute. I love the red hair. Tits aren't all that big, but they match her frame."

"Possible target for the night?"

"Maybe, but the night is just getting started."

We were both checking out all the single women we could see, locating possible women to approach and possibly seduce when Shelby returned with our drinks. As I was pulling out cash to tip Shelby, Analisa decided to get blunt with the young woman

"Tell me Shelby, if a woman were looking to find another woman to experiment with, how would she break that ice?"

Shelby smiled and put the drink tray at her side.

"In this place, just have a few drinks with them and see if you click. There are those that act like they are too good for most people in her because they think they are supermodels, but once they open their mouths, you realize no hot body can make up for the nastiness inside of them. If it were me that the woman was trying to attempt to seduce, I would want to feel desired. Make me feel like I will be the center of attention. Flirt with me. Soft touches in places that are not just my tits and my ass. But that is just me."

Shelby then gave off a cute blushing smile and walked away. I looked at Analisa who simply looked at me and I knew that she wanted Shelby. The girl had a cute smile, a nice body. She wasn't thick like Analisa, but she wasn't a twig either. She had some meat on her. She had a very well rounded ass and a flat stomach. She had meaty thighs, which I loved. Her skin was milky white with freckles all over it.

Throughout the night, Analisa and I mingled and talked with many different people. Analisa found it fun flirting with different women in subtle ways. There were many women who commented on her impressive rack. She even allowed on woman take a shot from between her tits. No matter how much she flirted with others, she still made sure to give Shelby the attention that she wanted. Shelby seemed to be enjoying the attention. Anytime she came by the table, she would make sure and stand right between me and Analisa. A couple of times, she had placed her ass directly against my crotch. She would get hugs from Analisa and her head always seemed to be perfectly level with her breasts.

As the night began to come to an end, we decided to leave. We both hugged Shelby goodbye and told her that we really enjoyed her company and would love to be able to enjoy it more. Analisa then slipped her a note from the two of us. It simply told her that we both found her to be more attractive than any of the other women we had seen that night and would love to enjoy her more. We both knew that she could not leave with any of the customers. There were stupid laws against that. We left Analisa's cell number and our hotel and room number. We told her to text us if she was interested in joining us after she got off.

We left around midnight and returned to our suite. While Analisa was getting out of her dress, her phone buzzed. I grabbed it and smiled as I read the message.

"Shelby is on her way," I told my sexy wife. She squealed in excitement. She grabbed some of her sexy underwear and ran to the bathroom to change. She came out of the bathroom in her silk robe. It was almost 1am when there was a knock at the door. I walked over to the door and saw Shelby standing outside.

"Hey," I said as I opened the door. "Glad you could come."

"I was happy to get the invite," said Shelby as she walked in. She quickly noticed Analisa sitting on the couch in her robe. "That is a very sexy robe."

"Thank you," replied Analisa. "Why don't you come have a seat and relax. You looked like you were running a marathon in there tonight."

"It felt like it," said Shelby as she sat down next to my wife. "It's nights like these that I wish I brought a joint with me to smoke after work."

I laughed as I walked over to one of my bags. I pulled out a medicine bottle that I kept my weed in when I went anywhere. I also pulled out a pipe.

"I think we need to move out to the balcony," I said, making Shelby smile.

We all went out to the balcony and lit up the pipe. We allowed Shelby to take the first hit. She had a rough day at work and needed to relax. After smoking two bowls, we all went back into the suite. Shelby once again sat on the couch next to Analisa, a little closer than earlier.

"So, do you guys do this all the time," asked Shelby.

"Smoke weed at hotels? Whenever we stay at a hotel," I replied.

"No, I'm talking about pick up girls at bars and invite them back to your hotel room."

"Nope. You are the first," said Analisa.

She then explained to Shelby what her goal was for the weekend.

"So out of all the girls in that bar, you wanted me?"

"Those girls looked good, but none of them had your smile," said Analisa. "Have you done anything like this before with other customers?"

"Not once. No one has even asked. Most people do not take notice of the girl in shorts and a white dress shirt when there are women in there dressed like models. Hard to compete."

Analisa took that moment to make the first move. She pulled Shelby's face to hers and placed her lips gently on the young redhead's. The kiss was very intimate and sexy. Shelby slowly parted her lips, allowing Analisa to slip her tongue in. They kissed for a few minutes, allowing each other's tongues to explore the others mouth. Shelby then broke the kiss and stood up. She unbuttoned her shirt, revealing a very sexy white lace bra covering her 32C breasts. She looked at me and motioned for me to help her remove the bra. I unclasped the bra and released her very cute, perky breasts. He nipples were hard and pink. She then undid her pants and pulled them down. She had a white lace thong on to match her bra. Analisa then stood up and untied her robe, letting it fall open. She did not have a bra on, allowing Shelby to get a perfect view of the massive tits she had been looking at all night under the dress. Analisa had on a black lace G-string that barely covered her bald pussy.

Shelby approached her and sat her back down on the couch. Shelby spread Analisa's legs and began rubbing her hands all over her tits. Her mouth made its way to my wife's dark pierced nipples. Shelby slowly traced her tongue around the areolas. She would drag her tongue across the nipple, causing Analisa to flinch in excitement. Shelby would switch from one nipple to the other, playing with the piercings with her tongue. She then slowly began kissing her way down Analisa's stomach, rubbing her hand across the barely covered, drenched pussy lips of my wife. I sat in a chair next to them, enjoying the view. Shelby looked me directly in the eyes as she moved her head to face directly at the pussy that was begging for attention. She ran her tongue across the thin fabric, causing Analisa to gasp. She began to breath heavier when Shelby peeled the cloth to the side and ran her tongue across her slit. The tip of Shelby's tongue would hit Analisa's clit as she ran up and down. Shelby then spread open my wife's lips and buried her tongue into the well moistened sex canal. I watched with joy as Analisa was getting eaten out by another woman for the first time. Shelby must have had done this before, because she had Analisa orgasming within minutes.

After her orgasm, Analisa switched positions with Shelby. She mimicked what Shelby had done to her breasts, slowly moving her tongue around the breasts and flicking the nipples with her tongue. Analisa was nervous as she began to move down towards Shelby's pussy. As she got closer, she could smell the sweet juices coming from Shelby's hot, wet cunt. The smell was intoxicating. She decided she did not want to bother with having to hold the cloth back. She grabbed the top of the thong and pulled them off the redhead. This revealed Shelby's well-trimmed vagina. A small strip of red hair rested just above Shelby's love hole. Analisa moved her face closer to the wet pussy and ran her tongue across the slit, giving her the first taste of another woman's juices. It was not sweet like I had described her own juices, but the taste was one that Analisa wanted more of. It was not long until she had her tongue lapping up all the juices coming from Shelby. Shelby moaned as Analisa lovingly pleased her pussy.

By this point, I had removed my shirt and pants, leaving me only in my boxers. My cock was very hard and barely contained in the boxers. After twenty minutes, Analisa had finally gotten Shelby to have a very wet orgasm. At this point, Analisa motioned me to come join them. She laid down on the couch, with Shelby positioning herself to get another taste of my wife's juices. Once she started licking away, I positioned my face directly behind Shelby's sexy ass. I placed my hands on her ass, getting a squeal from her as I squeezed the cheeks. I then spread the cheeks apart and ran my tongue along her pussy slit and up to her asshole. She jumped when I hit her backdoor, causing me to believe that she was not into that.

"I'm sorry," I said, not sure what to say.

"Don't be. I love it. It is not often a guy is willing to lick ass," said Shelby, looking back at me.

"My dear, you are about to experience pleasure like you have never felt before. He is a magician with his tongue," said Analisa.

I took the cue and passionately began not only licking her pussy, but her cute asshole as well. She moaned and groaned into Analisa's pussy as I made her cum repeatedly. Analisa had cum a few times during this as well. I slowly introduced my fingers to her two holes, causing her moans to get louder. She then orgasmed suddenly. The next thirty minutes were filled with the girls switching positions, allowing me to eat them both and finger fuck all their holes.

"Baby, I need to see you fuck this sexy woman," said Analisa as she removed her face from Shelby's pussy. I went to grab a condom when Shelby stopped me.

"I am allergic to latex," she said out of the blue, halting all activity.

"Well that is problematic," I said.

"I know you probably have a rule that a condom is a must because you can never be sure if someone is on the pill. I carry proof that I am on the shot because I must due to the allergy."

I looked at Analisa. We had agreed on the rules, but she seemed to be wanting to break those rules already. Shelby directed me to her purse and the front pocket. In an envelope was a breakdown of her last doctors' appointment less than a month ago, when she had gotten the shot. That was all the proof that Analisa needed.

"Baby, this sexy young woman needs to be fucked. Come fuck her."

I aimed to please my wife, even if that included pleasing another woman. I sat down on the couch and Shelby soon straddled me. She slowly slid my cock in her tight pussy. She could not have had sex with many people, or she had sex with people with small cocks, because she was tight. It wasn't long until my cock was filling her tunnel up. She bounced up and down and grinded against me as my cock was buried in her. Analisa had come behind the couch and was kissing me. She would also play with Shelby's tits. They then swapped, having Analisa on my cock and Shelby sitting next to us, playing with Analisa's tits. At one point, my cock slipped out and Shelby quickly dropped her head down and took it into her mouth, enjoying Analisa's juices all over my cock. She then placed it back into Analisa's pussy, allowing me to continue to fuck my wife.

The finally of the night happened as I had both women bent over on the couch and took turns fucking them doggystyle. The two made out heavily as I pounded each of them from behind. Both had a couple more orgasms and were close to exhausted. I was losing my energy after a couple hours of intense sex. Finally, I could feel my load about to escape.

Analisa and Shelby both dropped off the couch and onto their knees.

"Cum on her tits," begged Shelby. I didn't even hesitate and exploded all over Analisa's tits. Once the last drop was out, Shelby then proceeded to lick all of my seed off of the tits. Exhausted, I plopped down onto the chair and caught my breath.

"That was amazing," said Analisa to Shelby.

"I agree," said Shelby. "You two helped me live out a fantasy tonight. I had always fantasized about meeting a couple at the bar and going home with them. This isn't your home, but it is close enough. How was your first experience with another woman?"

"Perfect. Absolutely perfect. What do you think babe?'

"It was amazing. We sure did choose the right woman for your first time."

The three of us took separate showers and then all passed out. Shelby joined us in the bed and fell asleep right next to Analisa. As I fell into a deep slumber, all I could think about was what was our next adventure going to be like.