Lovers Once Again

Lovers Once Again

After escaping a long, boring and sexless marriage, I met up with my friend Stacy who I dated many years ago but kept in touch with over the years. After being married so long, it felt a bit naughty to be meeting up with a woman other than my wife, but we just went to dinner and caught up on our lives.

Stacy has never been married and isn't currently dating anyone. She is an incredibly beautiful woman and I was dumbfounded as to why she's never found the right guy. At some point in our conversation, I realized that she's still single because she has a certain type of guy that she is attracted to and will not compromise. Whether it be their look, job or attitude, she is quick to toss them aside. I've told her many times that there is no perfect man out there and that she should focus on their good attributes and accept their less than perfect ones.

"Stacy. You're going to have to pick one or you'll be single your whole life."

She said, "A few times I've thought I found the right guy, but then find out they aren't into my lifestyle."

"What do you mean? They don't have the same interests as you?"

She said, "No, they want a monogamous relationship."

I paused for a brief moment of confusion.

"Wait. You don't want a monogamous relationship?"

She smiled and said, "I can't have just one dude for the rest of my life."

This definitely piqued my interest. She had never expressed this to me when we were dating, but maybe our relationship didn't get to the point that she felt comfortable revealing this to me.

"You never told me this when we were dating."

She giggled, "You and I never dated."

I sarcastically replied, "Oh, we didn't? I've been telling people that we dated, but apparently that never happened."

She smiled, "Dinner, drinks and dick is not dating."

We both laughed.

I asked, "You really don't want a husband and a big house on the corner with a white picket fence?"

"Oh, I do. I definitely do. But I want that husband to share me and allow me to share him as well."

Now I was really interested. One of the issues my ex-wife and I had in our marriage was sex. After our love life dwindled down, we read all the marital help articles and bought all the sex toys in an attempt to rekindle our intimacy. I even suggested we role play or go to a swinger's club and watch people fuck, but she turned it all down. Unfortunately, our intimacy eventually died completely and we divorced amicably. I'm only 51 years old and still in pretty good shape, so one of the main factors in divorcing my wife was that I became extremely concerned that sex for me would end so early in life.

"Hey!" Stacy's voice woke me out of deep thought.

"Oh sorry. I was just thinking about the times I talked to my ex-wife about having an open relationship."

Stacy said, "Most women don't want an open relationship. They don't have the stomach to see another woman touch their man."

"Yep. Exactly. That was her answer when I suggested swinging."

I was still intrigued by Stacy's requirements in a man and wanted to dive deeper into it.

"So, how did you first get interested in open relationships?"

She said, "I never said I'm interested in an open relationship. That is definitely not what I'm looking for."

"Oh, I thought a non-monogamous relationship is the same thing as an open relationship."

She sighed and rolled her eyes, "OK, I'll explain it to you. There are a few types of non-monogamous relationships. The main one's are open, polyamorous and then the swinger's lifestyle."

"OK, so you're not interested in an open relationship. This is interesting, so explain further."

She said, "Open means you can go on dates with anyone at any time, outside your marriage. Polyamorous means bringing a third person into the relationship both emotionally and physically."

I said, "So, basically that is a live-in threesome."

She giggled, "Yeah, basically but with emotions involved. That gets too complicated, so I am only interested in the swinger stuff. But if I found the right guy, I wouldn't rule out having a girlfriend as well."

I spent a few moments trying to process all of this. Watching Stacy with another girl? I could easily get on board with that!

Stacy spoke up, "You look confused."

"No, I'm not confused at all. You explained it well."

She said, "So, that's what I'm looking for and very few guys are willing to share me."

For some reason, I have always been fascinated with the swinger's lifestyle. I've read books and articles, read erotic stories, watched shows and even looked up swinger websites. Most of my curiosities revolved around watching how someone else makes my wife orgasm, whether it be a male or another female. I think I am more of a cuck and fucking the other man's wife is just the cherry on top.

I've always been extremely attracted to Stacy and this meet up was purely intended to catch up with an old friend, but these revelations really made her even more attractive in my eyes. Stacy is a couple years younger than me, but in much better shape than I am. Being single, she is really into fitness and looking after only herself, where I have been more focused on just trying to stay in shape rather than making it a priority in my married life. Her body is toned, her above average sized tits are nicely shaped and her little ass always looks perfect in whatever clothes she wears.

During dinner, I couldn't help but check her tits out as we sat across from each other. I have always thought that Stacy was the one woman in my past that I should have put more effort into, so the desire to date her has always been in my mind. But it had only been a month into my divorce and still had mixed feelings about asking Stacy on a date so quickly. However, her non-monogamous requirement is really what I want too and I at least wanted to let her know that I'm on board with this arrangement. So, with a little nervousness, I decided to plant the seed.

"I love your mindset."

She asked, "What mindset?"

"I'm not one for monogamy either."

Stacy's eyebrows lifted and she said, "Oh, really."

"I've always had the desire to share my wife or girlfriend, but always seemed to fall in love with a woman that has no interest in it."

Stacy simply said, "Interesting."

We continued with small talk after that, almost like she was trying to process my comments but didn't know how to ask more. We finished dinner, gave each other a deep hug and went our separate ways.

The next few weeks were pretty standard for me, but now with the addition of occasionally texting with Stacy. Our texting conversations were very surface level, but one day I received an interesting text message.

"Wanna go out Friday night?"

I looked at her text message for a couple minutes before responding, "Dinner again or is this a date?"

"I want you to take me on a date like you did years ago."

I responded, "I thought we didn't date :)"

"LOL. OK, we dated."

I didn't respond right away and decided to think this one through. Was I ready to move on from my 10-year marriage so quickly after being separated from my wife for not even 2 months? Do I need more time to repair myself before jumping back into the dating scene? Would this start the ball rolling with Stacy on more than a friendship level?

I decided that I wasn't getting any younger and whatever happens is meant to be, so I responded.

"I would love to take you out."

She instantly responded, "Great! See you Friday."

Later, we texted back and forth and I agreed to pick her up at 7pm.

Friday came, and I felt a little nervousness and butterflies in my stomach as I drove to Stacy's condo. It had been a long time since I was a single man and taking another woman on an official date seemed so foreign to me.

When I arrived, I rang the doorbell and waited for Stacy to open the door. Anticipation began to build, but she didn't leave me hanging for very long. When the door opened, I was met with Stacy's beautiful smile which instantly calmed my nerves.

Stacy was wearing a tight white dress and red stiletto heels. I stepped back and said, "Whoa! You look amazing" and took this time to look her up and down from head to toe. Stacy's long brown hair was flowing down the sides of her face beautifully and she was wearing only a small amount of make up as she always does. Her tits looked bigger than yesterday, her nipples poked ever so slightly through the tight material and the dress accentuated her slender waste and hips perfectly.

"Man, you're a knock out."

She smiled and said, "Thanks. You look great yourself. Are you ready to go?"

"Absolutely!"

When Stacy went back inside to grab her clutch purse, it gave me a moment to relax and shed the guilt I felt earlier about taking her on a date, or anyone else for that matter. I decided to just enjoy my time with Stacy, which got me excited about the night ahead.

Stacy came out, locked her door and we walked to my pickup truck. I opened the passenger side door and quickly realized my truck is a little too high and it will probably be hard for her to get in, especially with the tight dress she was wearing.

"Do you want me to lift you up into the truck?"

"No, I can do it. But don't look, I'm not wearing panties."

I chuckled and watched her climb into the passenger seat. Of course, I was looking but unfortunately Stacy didn't expose herself.

On the drive to the restaurant, our conversation was great. I felt a new and relaxed attitude with her and it almost felt like the good old days. As we pulled into the parking lot of Fleming's Steakhouse, I could see Stacy's eyes light up with excitement. I pulled into the valet lane and giggled because my Chevy pickup truck was now amongst a bunch of Ferrari's and Lamborghini's that were parked and on display.

As I stopped the vehicle, one valet walked toward my door and another started walking toward Stacy's door. I said, "Looks like your guy is going to get a peek before I do."

I got my valet ticket and walked around to find Stacy waiting for me. She looked so amazing and I was really excited to spend more time with her.

I said, "Let's go have a great meal."

As I began moving toward the door, Stacy said, "Are you going to hold my hand?"

I caught myself and remembered this was an official date. I walked back to Stacy, held her hand and we walked into the restaurant as one. It felt so nice holding Stacy's hand again and gave me a warm feeling inside. After being sat at our private table in the rear of the restaurant, we ordered drinks and began to make small talk.

"So, did you give the valet a little peek?"

She giggled, "I pulled my dress up, but I don't know if he saw anything."

I smiled, "I guess we'll find out when we leave."

"How will we know?"

"If the same guy comes running to help you, that's your clue."

We both started laughing, clinked our water glasses together and blood instantly filled my cock at the voyeuristic thought of a stranger looking at Stacy's pussy.

She said, "He was cute, but definitely a baby rattlesnake."

I couldn't quickly figure out what "baby rattlesnake" means, so I asked.

She giggled, "You don't want to get bit by a baby rattlesnake because they can't control themselves. They unleash all of their venom when they bite you."

"Oh, I get it now. No young ones for you, huh?"

She said, "They are satisfying to look at but not satisfying to fuck."

I thought for a moment and was interested in learning more, so I decided to keep pressing the questions.

"Really? I figured they had stamina for days."

"They do, but young guys are inexperienced and cum too fast. Then I'm left unsatisfied and hoping I'm not pregnant."

Sarcastically I said, "I highly doubt at 48 you'll be pregnant."

Stacy smiled.

Just then, our server came and brought our drinks. I held my glass up and said, "Here's a toast to two longtime friends on their first official date in 15 years." We looked into each other's eyes and touched glasses.

I said, "Your eyes are so beautiful. I love that look you just gave me."

Stacy asked sarcastically, "What look?"

"You know the look I'm talking about. It always gets me excited."

She reached under the table, found my semi erect penis and softly rubbed her hand across the front of my pants. I looked her directly in the eyes, leaned in and gave her a quick kiss. Stacy smiled and brought her hand back to the table.

I asked, "What was that for?"

"I just wanted to see how excited you really were."

I asked, "What is your diagnosis?"

Stacy took a sip of her drink and said, "I'm no doctor, but I may have to take a closer look later."

My face and penis both smiled at that comment. The server came by and we both ordered filet mignon and a shared side.

After the server left, I smiled, "So you're assuming you can get me in bed on the first date?"

"I'm pretty sure you wouldn't turn me down."

I laughed, "I'm pretty sure you're right."

Our conversation shifted away from flirting and on to other subjects. Our food and another round of drinks arrived as the conversation continued effortlessly.

When we finished dinner, I paid the bill and we walked out toward the valet stand. Stacy's new buddy saw us exit and was instantly at her side. He asked if we were ready to go and went to the kiosk to grab my keys. As he ran toward the parking, I said, "That kids working really hard. You should probably give him a better peek."

Stacy got a huge smile on her face.

It wasn't more than a few minutes when the kid drove up in my truck. As he jumped out of the driver's seat, I handed him a $20 bill and asked him to help "my girl" into the truck. He ran around the back while I jumped into the driver's seat. I saw him hold onto Stacy's hand as she put her foot onto the step and then sat down on the passenger seat with her knees pointed toward the valet. She said something undiscernible, cracked her knees open for a long moment and then swung both of her legs into the truck.

Stacy had a devious smile on her face and the valet kid looked like he had just seen a ghost. He said, "Thank you ma'am. Please come see us again." He then softly closed the passenger door and we drove away.

I said, "That was great! I couldn't hear what you said to him though."

Stacy said, "I told him he didn't have to sneak a peek this time."

Watching Stacy expose her vagina to the valet was a real turn on and my cock was now completely hard and laying down the inside of my right pant leg. I knew right then that Stacy's lifestyle is fun and something I could really come to enjoy.

On our drive back to Stacy's condo, she asked if I had any plans this weekend.

"No. Just chores around the house."

She asked, "Do you want to spend the weekend with me instead?"

Of course, I did but I had to ask, "What do you have in mind?"

"Well, I was going to go lay out and get some sun tomorrow if you're interested."

I agreed and it wasn't long before we pulled up to Stacy's condo.

"Do you want to come in?"

I absolutely wanted to, but decided I should go home instead.

I said, "Thank you for going out to dinner with me, but I should probably go home."

The look of disappointment on Stacy's face was saddening. I'm sure not many guys would decide to go home in this scenario, but I was pretty certain we would be having sex if I stayed. It had been over 10 years since being with another woman and I still had some nervousness about being naked with Stacy. To be honest, I was also a bit intimidated by her incredible fitness level and had some insecurities about my married guy body.

Stacy leaned across and gave me a kiss on the lips as she grabbed her purse and reached for the door handle. I turned my truck off, opened my door and ran around to open the passenger door for her. As I opened the door, she swung her knees toward me and opened her legs just enough to show me a quick look at her beautiful bald pussy.

With that devious smile on her face, she said, "Tomorrow... you and I will be naked together, guaranteed."

Stacy closed her legs and climbed out of my truck. She pulled her dress down and we walked hand in hand to her front door and stopped.

Stacy said, "I'll pick you up tomorrow at 10 am."

I asked, "We aren't laying out at your pool?"

"No. We are going to my favorite place to get sun."

"Are you sure you don't want me to drive?"

Stacy said, "No, it's closer to your house. I'll drive."

"OK."

I leaned in for another kiss, we embraced and began softly tongue kissing. Stacy dropped her purse to the floor, grabbed onto the back of my head and pulled my face deep into hers. Our kiss became increasingly more intense and the sounds of our lips smacking rang through the air. Stacy reached down and felt my hard cock through my pants, slowly running her hand up and down my shaft.

She softly moaned as our kiss continued, but then suddenly broke off and gave my cock one final squeeze. "Mmmm....I can't wait to see this tomorrow."

Stacy sure wasn't making my decision to go home any easier. The feeling of our bodies together and her amazing kiss had me wondering if I should just park my truck and spend the night. But as hard as it was to do, I kept my initial plan and wished her a good night.

As I walked away, I turned around and asked, "So are you going to tell me where we are going tomorrow?"

Stacy just smiled, walked into her condo and closed the door.

During my drive home, all I could think about was Stacy and the incredibly tough decision I just made. She looked and felt so good that I really wanted to turn around and go back, but I kept driving home with my eye on tomorrow.

My cock was still hard and showed no signs of going soft, so I softly rubbed my shaft through my pants as I drove. It was such an incredible make out session with Stacy and visions of her gorgeous body and bald pussy flooded my thoughts. It took all of my concentration not to drive off the road as I just wanted to get home and masturbate to the thought of Stacy, but I really needed relief immediately.

I unzipped my pants and wrapped my hand around my hard, bare cock. I stroked it ever so slightly and knew right away that it wouldn't be long until I exploded. I popped open my glove box to look for a napkin and luckily found one inside. I turned my attention back to my cock and my attraction to Stacy caused me to cum almost instantly as I exploded into the napkin. I crumpled up the napkin and threw it on the passenger seat.

I finished the rest of my drive home thinking about how I could've been giving that load to Stacy right about now, but for some unknown reason I was on this path to my house and not laying in her bed. I eventually made it home and tucked my pitiful self into bed.

I awoke the next morning, took a shower and touched up my manscaping. I texted Stacy about 9 am, "Good morning. I'm ready when you are."

Stacy replied, "Make sure you wear swim trunks, bring a beach towel and lots of suntan lotion. I'll be there in an hour."

"OK."

I spent the next hour getting my stuff together and was genuinely excited to see Stacy again. I was a little nervous, but the butterflies in my stomach only reaffirmed how much I really like her.

When Stacy pulled into my driveway, I grabbed my stuff and headed outside. Stacy was getting out of her car and walking toward the front of it. She told me that her car started overheating on the way to my house, so I popped her hood open and saw that steam was coming from the radiator. Stacy showed a little concern and stress, but I gave her a hug and reassured her that I would handle it for her.

I asked, "Do you still want to go sun tanning?"

"Shouldn't we get my car towed or something?"

I explained to her that there's nothing we can do today because repair shops aren't open on Saturday and that I'll have it towed to my mechanic on Monday morning.