A Date with Carla Ch. 02

I am posting a series of true stories about my encounters with "providers" around the country. I totally respect these women and in these stories have no intention of demeaning them.

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This story goes back almost a decade. It occurred about a month after my first date with Carla in Cincinnati. This story is basically a continuation of my "A Date with Carla" story earlier. I thought that visit was about as good of a "date" as I could expect anywhere. Boy was I wrong!

I have to admit that this was a unique experience because, for the first time as a "hobbyist", I was forced to decide whether to proceed with my date.

As soon as I had my travel plans to Cincinnati finalized, I contacted Carla to set up our second date. I actually got a bit of a stiffy writing the email. I told her my schedule and asked if we could meet again. Within an hour, I got a reply that she was happy to hear from me and couldn't wait for us to be together again. I was humbled.

Her email went on and then she almost knocked me over. She had a request. Before continuing, I knew that I would do whatever she wanted. However, I came to realize that it was not that simple.

She said that her best friend, Debbie, would like to discuss joining us. I was gobsmacked. I've never had that request. I knew nothing about Debbie, but if she was a friend of Carla's, she was friend of mine.

I asked Carla what the story was. I could not make up this answer. Debbie is a long-time friend of hers. Six months ago, Debbie lost her husband in a terrible car accident. It took her awhile, understandably, for Debbie to start getting back to real life without the love of her life. Debbie and Carla were more like sisters than friends. They both confided in each other on everything. Debbie knew that Carla had been seeing other guys as an escort with the permission of her husband, Larry.

As I was reading the email, I wondered where this was going. It seems that Carla had told her all about her date with me a month or so ago. Debbie wanted to know every detail and Carla shared the entire story. That fact didn't bother me in the least. In fact, I was kind of proud. Carla assured Debbie that I was a very nice guy who had totally respected her during our wonderful time together.

Carla knew that Debbie and her husband had enjoyed a very rich sex life, but it was just between the two of them. Debbie also knew that Carla's husband, Larry, was not the least bit interested in sex, which is why Carla saw other guys, to put it delicately.

Debbie asked Carla what it would be like if the two of them went on a "date" with a guy Carla trusted. It was about this time that I emailed Carla. My timing was perfect! I was beginning to think I should go out and buy a lottery ticket.

To kind of cut to the chase, Debbie asked Carla if she would be interested in joining her for a date with me. Of course, Carla and I did not talk about this topic when we were together previously, so Carla couldn't speak for me. Now, here was an email from me asking Carla for a second date. Kismet!

I replied to Carla telling her that I would be beyond excited to see both of them. I didn't even ask Carla what Debbie looked like. I didn't really care. I trusted Carla implicitly.

I emailed Carla asking if I could call her and discuss what she was proposing. She agreed and sent me her phone number. A day later, I called her mid-afternoon. She spent some time telling me about Debbie and her situation. I told her that, in general, I would trust her implicitly, but I was concerned that Debbie might be in a fragile state and could make a bad decision about joining us. Carla assured me that the two of them had talked at length about what would most likely happen and the Debbie was totally all for it.

To be honest, my head was swimming. I had never been in a threesome let alone with a "virgin" in the hobby. Carla talked me off the ledge and I agreed to proceed, but I wanted to meet both of them in the lobby bar to make sure everything was out in the open. I told Carla that I would respect any decision that Debbie made, including calling the whole thing off at the last minute. Carla thanked me for my understanding and compassion.

Finally, we settled on a night the following week for four hours, starting at about 7:00 p.m. when I would meet them in the hotel lobby bar. I told Carla that I'd hand her two envelopes with $800 in each one and asked her to take them to her car before rejoining Debbie and me in the bar. She agreed and the countdown had begun.

I debated whether to ask Carla some specifics about Debbie appearance, but decided it would be more fun to be surprised.

Time proceeded at a snail's pace. What would Debbie look like? What would it be like to be with two women? Would I live to tell about it?

I boarded my plane to Cincinnati with plenty of anticipation, not to mention a stirring in my groin area.

I got to my hotel about 3:00 p.m. and began preparations for that evening's date. I ordered a couple of chilled bottles of a nice Chardonnay and a charcuterie board to be delivered at 6:30 p.m. I tried to take a nap, but it was fruitless.

The wine and snacks were delivered right on time. I headed to the shower to get cleaned up and shave both my face and cock. Gotta be clean for the ladies!

I got down to the bar about 6:50 p.m. and found that it was pretty deserted. Maybe half a dozen people. Carla knew what I looked like, so I found a booth near the back of the lounge area and waited.

All of a sudden, I began to have doubts about this being a good idea. Obviously, I didn't know Debbie. Were we pushing her to do something that she would later regret? Should I have spent more time talking to Carla about the whole idea? Was I being a dirty old man who was selfishly considering my own sexual gratification? Because of these doubts, I decided to spend some time with the ladies in the bar telling them of my doubts.

Not surprisingly, at precisely 7:00 p.m. two lovely women walked into the bar and Carla spotted me immediately. She waved and both of them headed my way. Carla is in her mid to upper 40s, about 5-2, and has wonderfully large breasts. She looked great and it was thrilling to see her again. Next to her was Debbie, obviously. Debbie is older, maybe mid to upper 50s. She's significantly taller than Carla, probably 5-9 or so and fairly slim. She has short gray hair and is quite lovely in a lady-next-door way. Not stunningly beautiful, but what I call sneaky pretty. She was wearing a conservative dress with a sweater over her shoulders. I couldn't really tell anything about her breast size, but I didn't care.

I stood up as the women made their way to my table. I gave Carla a big hug. She introduced me to Debbie and we had a bit more reserved hug befitting the fact that we'd just met.

I welcomed both of them and told Debbie that I was very pleased to meet her. I also told her that she was lucky to have a friend like Carla. Debbie said, "Indeed, I am."

I asked if Chardonnay was OK. They both agreed, so I ordered two more glasses.

After we got comfortable in the booth, I told that ladies about my concerns. I specifically addressed Debbie telling her that Carla and I had done this kind of thing before, but that I wanted to make sure that she was completely on board. I wanted to make sure that Carla and I had no hidden agenda and that we were there to proceed with an evening of sex between three consenting adults. I think I kind of caught Carla off guard with this admission. She looked at me and then over at Debbie. Debbie said, "I understand your concern and I really appreciate your thoughtfulness. I guess you'd call this a new frontier for me, but I'm 100% on board. I might need some support as things progress, but I really believe that you and Carla want what's best for me and, of course, for all three of us."

It was a beautiful moment. It was like no other encounter I had ever had and I was truly touched.

I said, "OK, Debbie, let's take the next step." I wanted to break the ice, but not to be too forward about the rest of the evening. I slid the two envelopes across the table. Maybe it's paranoia on my part, but for the past few years, I've done this with my dates. If the cops come bursting into my room later on, we're just friends having fun. Nothing illegal.

In a couple of minutes, our wine had arrived at the table. We toasted a fun evening among friends. Carla quietly got up and headed to her car with the envelopes.

I looked at Debbie. I said, "Debbie, I should have said this when we first met, but I want to express my condolences over your loss. I know it's tough, but don't be afraid to ask Carla for help, not only tonight, but going forward. It's clear that she's a good friend. I know she would do anything for you. I've only met here one time before, but I consider her to be a wonderful woman with a heart of gold. Also, I've never been married, so I can't imagine what your loss means. "

Debbie's chin quivered a bit. She thanked me for my advice and assured me that she would lean on Debbie going forward."

Then, I said, "I know this is your first time doing this. I promise that I will respect your wishes in every way. Neither one of us wants to pressure you into doing anything that you don't want to do. You are not here to take care of my wants. If you get uncomfortable at any point, you just have to tell me and I'll stop."

She looked down and said, "Thank you. I appreciate your words. I'm anxious, but not afraid. Carla has told me everything about you and how you treated her."

"Everything?"

"Well, I think so. She also mentioned that you didn't use condoms."

"Does that bother you?", I said. Again, I asked her about the condoms.

She said, "I trust Carla."

Looking Debbie in the eyes, I finally realized that she's more beautiful than I first thought. Especially when she smiles.

I spied Carla coming back to our table. I said to Debbie, "My dear, I want to emphasize both Carla and I respect you. Again, at any point tonight, if you are uncomfortable or unsure, let us know. We will stop immediately. Carla loves you and wants only what you want."

She gave me a little grin and said, "Deal."

I gave Carla a room key, told her the room number, and off they went. I waited about ten minutes. It seemed like ten hours. I signed the bar tab and went upstairs

While on the elevator, it occurred to me that Carla might be a bit bi-curious. I don't know what triggered that thought, but I wanted to keep it fresh in my memory and try to be aware of Carla's actions towards Debbie. Would there be any sexual contact between them? Well, I guess we'll see. My cock twitched a bit.

I swiped my key card and entered the room. These two lovely ladies were on the couch in the living room portion of the hotel room. They had spotted the wine and helped themselves.

I grinned and said, "Well, I must have left the door unlocked. I seem to have two intruders."

Carla said that they were curious and decided to see what was inside the room. Then she gave me a mischievous smile.

I said, "Well, stick around, we'll see what comes up."

The both groaned at my cheap joke. Rightfully so.

I topped off their wine glasses and noticed that Debbie had taken the sweater off her shoulders. I noticed that her breasts were, shall we say, modest. Especially compared to Carla's. Not that it mattered.

I announced that at this point I was going to take charge for a bit to break the ice. Nobody argued.

Carla was wearing a peasant dress similar, but not the same, as the one she wore last time we were together.

I said, "Carla, last time you were not wearing anything under your peasant dress. Let's see what we have tonight."

She grinned and stood up in front of Debbie, but facing me. She kicked off her shoes, shrugged a bit, and the dress fell into a heap on the floor. Yep...same thing underneath as last time. Nothing.

"Carla, we need to take up a collection and get you some undies," I suggested.

She said, "I decline the opportunity. Slows things down." And gave me an evil grin.

I tried to keep an eye on Debbie's reactions. I think I could detect a slight blush. I asked Debbie what she thought.

Her response was, "Beautiful."

Carla had her back to Debbie when Debbie did a little twirl. Debbie's glance was crotch-level on Carla and her eyes widened. She said to Carla, "I didn't know you shaved your pussy."

Carla said, "Makes it more sensitive, especially to a tongue." I was loving this.

Debbie said, "Maybe I should try that."

Carla said, "No problem. I want the three of us to shower together before things get out of control."

I was instantly hard as can be.

I held out my hand to Debbie. She took it gently and stood up.

Carla said, "Debbie and Steve, you guys are overdressed." Who was I to argue?

Carla moved towards Debbie and started unbuttoning her dress. It didn't take long and it joined Carla's dress on the floor. The difference was that Debbie was wearing a bra and bikini panties. I stepped behind Debbie and asked, "May I?"

Debbie seemed to blush a tiny bit and said, "Indeed, you may."

I undid her bra while Carla skinned down her panties.

Holy crap! Here I was gazing on two mature, beautiful women, and I was way overdressed.

Debbie did have small breasts, probably a standard B cup. She was carrying a few extra pounds, which I happened to enjoy. Her pussy wouldn't be classified as hairy. She must have trimmed it a bit as it was in a nice triangle shape of brownish-gray hair.

Carla looked at Debbie and said, "What say we do something about the hair?"

A big smile from Debbie followed by, "Lead the way."

The only problem now was that I was still fully dressed. The ladies looked at each other and then at me. They both approached me and began the short process of remedying the problem.

By the time my shorts dropped, I was sporting a major boner. Debbie looked at Carla as if to ask for guidance. Carla came over, grabbed my cock, and led me to the bathroom. I hadn't had time for a shower since I got back from my business meeting, so a shower was in order.

Now the three of us were stark naked in the large bathroom. I had requested a handicapped bathroom because I knew that there would be a very large shower with no rim. Plus those kinds of showers have adjustable height spray heads. I moved it down so the ladies wouldn't get their head wet. Carla reached in and turned on the water. The water heated up quickly and so did the three of us.

The ladies took the lead by washing me and avoiding getting their hair wet. They each made sure my cock was as clean as can be.

Finally, I said to Debbie, "You mentioned the possibility of having your pussy shaved. Are you game?"

Debbie thought a second and said, "What the hell?" Carla and I looked at each other and grinned.

I stepped out of the shower to retrieve my shaving cream and a fresh disposable razor. I asked Debbie to sit down on the shower seat and asked Carla to do the honors. Debbie grabbed a washcloth and kneeled down in front of Debbie. She grabbed a bar of soap, lathered up the washcloth, and began applying it to Debbie. Debbie squirmed a bit and gave me a quizzical look. "Never had a woman wash your privates?"

"No, but it feels nice."

Carla went to work carefully removing Debbie's pubic hair. When the job was done, she took the shower sprayer, and washed away any remaining shaving cream. Finally, she leaned down and kissed Debbie's smooth pussy. Debbie jumped a bit and then relaxed. This was clearly a first for her.

I stepped forward, led by my stiff cock, and reached between Debbie's legs. "I approve of your workmanship!"

Debbie giggled a little and stood up. I turned off the water and handed each of them a big, fluffy towel. We dried off and went back to the living room.

I had some soft jazz playing on my laptop. It was a fantastic scene. The three of us standing close together. Starkers. The ladies sat on the couch and I sat on a chair facing them after refilling wine glasses.

"I propose a toast." They both held up their glasses. "I toast nakedness." They laughed and we clinked glasses.

I put my glass on the end table and walked over to Debbie. I said, "My dear, you are a very lovely woman and I'm glad you joined us tonight."

Debbie, approached me, threw her are arms around me, and gave me a deep soul kiss. You can imagine the state of my cock at that moment.

Debbie kept up the kiss for maybe a minute with her tongue all over the inside of my mouth. My cock was stabbing her in the belly and I was afraid it would erupt.

She broke the kiss and looked at Carla.

"Are you next?" she said.

Carla said, "I thought you'd never ask."

Before Debbie and Carla kissed, Carla backed off a bit and asked, "Are you sure?"

Debbie said, "Yes".

They spent a good amount of time French kissing. I couldn't believe that this was Debbie's first time kissing a woman. Carla reached around and grabbed Debbie's ass, pulling them together.

Here I was with my dick waving around, but loving what I was seeing. Finally, they broke the kiss.

Debbie said, "This is better than I could ever have imagined."

I suggested that we sit down for a minute. I sat in the middle of the couch with one lovely woman on each side.

Debbie said, "Sorry we were ignoring you."

I made it clear that I had enjoyed the show. As conclusive evidence, I point to my stiff dick. "See what you two did."

I didn't really have a plan for how to proceed and I didn't want it to look like I was making the rules. I thought it best if I called a quick timeout to make sure the ladies knew where we were going, especially Debbie.

I said, "OK. Let's take a time out here before we proceed. Let's have another sip of wine or two while I clear the air."

I filled the glasses about half way and said, "Ladies, I want to make it very clear that this is not about me. This is about us. Debbie, you know that Carla and I have been together before. I believe that you have never been in a situation like this.

She nodded and said, "But, I've been curious."

I said, "Debbie, when Carla and I were together last month, we didn't just have sex. We didn't just fuck a couple of times. I believe, and I think Carla concurs, that we made love. That is what I see the three of us doing here tonight. And, I'm going to repeat what I said earlier. If, at any time, you are uncomfortable with what is happening or what you think might happen next, just let us know. OK?

She leaned over, kissed me quickly on the lips, and said, with a grin, "Thank you. Now will you please shut up and let's play!"

Who can argue with that attitude?

I said, "Ok, let's move to the bedroom. Debbie, I want you to lie down in the middle of the bed. Carla, you lie down beside her. I'm going to sit here in the chair."

The both did as I suggested. "Carla, I want you to take care of Debbie. Caress her. Kiss her. Play with her breasts."

Carla took her time and proceeded as I suggested. In the meantime, I was casually nonchalantly stroking my cock while I enjoyed what was happening in front of me.

"Carla, move down to her pussy. I'm going to join you in a few minutes and we'll do all we can to satisfy her with just our mouths and tongues."

The room became eerily silent as Carla did my bidding. I watched Carla really get into performing oral sex on Debbie. Debbie appeared to enjoy what was happening, but kept looking at me as if to say, "Is the what you want?"

I said, "Debbie, you keep looking at me. Don't do that. Just look at Carla. Pay attention to what she is doing to you and for you. Ignore me."

I got the impression that Debbie felt guilty that, since I was the "paying customer", I should be getting something out of this.