Holding Caitlyn's Hand Ch. 01byenjoyher©
My wife, Caitlyn, and I held hands as we walked toward the hotel room. She was obviously very nervous about embarking on this new adventure. We were just a few minutes early for our meeting with Anthony who would already be in the hotel room and waiting for us to arrive.
Several months earlier, I had posted some photos of my wife on an adult website. The pictures didn't show Caitlyn's face, but they did show off her wonderful body. The first pictures of her in a bra and panties were followed by ones of her showing her little B-cup titties. The last pictures featured my wife pulling down her panties and showing her perfect round ass. The final picture was of Caitlyn spreading her legs with her pussy on display.
Anthony was one of the many men who posted flattering comments about the pictures. Caitlyn has always been a girl who loves attention and she absolutely loved reading all the naughty complements. I sent messages to a few of the guys who had left comments and asked them if they would like for me to email them more pictures of Caitlyn. It was actually her idea. She picked out her favorite comments and those were the guys to whom I sent the messages. Anthony was one of the three.
Unsurprisingly, all three guys responded that they would love to see more of my wife. One night Caitlyn and I sat down at the computer and picked out the most flattering and explicit pictures to send to the guys. They all loved the photos and responded with filthy emails saying how much they enjoyed jacking off to the sight of Caitlyn's cunt.
Of the three email responses, Anthony's was easily Caitlyn's favorite. He gave compliment after compliment and described in detail how he liked to stoke his cock while looking at the pictures. As I mentioned earlier, my princess loves attention and she really loved reading about how much the guys liked her pictures. We sent Anthony some more photos and it wasn't long before we were emailing back and forth with him on an almost daily basis.
Eventually the day came when Anthony sent pictures of his own to Caitlyn. We were both shocked; the pictures revealed that Anthony was the alpha male specimen that he had portrayed himself as. He looked to be about 6'4" and incredibly well built. There were a few photos of Anthony without a shirt, but he was fully dressed in most.
It was evident that Caitlyn liked what she saw because she slowly clicked through all nineteen pictures, taking extra time to examine the shirtless shots. As she started to click through the set of pictures a second time, I told her that she should ask for naked pictures. She turned away from the computer monitor and looked at me for a second before asking, "You wouldn't mind?"
There was a hint of excitement in Caitlyn's voice and I had no doubt that she was at least slightly aroused by the pictures of Anthony. I jokingly said to her, "I guess it'll be okay if you want to see naked pictures of your new boyfriend."
"He's not my boyfriend," she said as she playfully slugged me in my arm, "... but I wouldn't mind seeing what he looks like naked."
It only took a moment for my wife to send the email to Anthony. It was brief and to the point: "Take off your clothes! Don't be shy; I want to see all of you." I then carried Caitlyn to the bedroom and fucked her.
We didn't receive a response from Anthony until late the next night. Caitlyn looked at me and smiled when she noticed that there was an attachment; a single photo. Her reaction when she opened up the attachment was priceless. Her mouth fell open and she muttered, "Oh My God," before slowly bringing her hand up to cover her mouth.
The picture showed Anthony standing in front of a mirror with a long fat cock hanging between his legs. His cock wasn't hard, but it was still quite a bit bigger than mine in its most excited state. Caitlyn stared at the screen for several moments like she was in a trance.
"Do you like what you see," I asked her.
"Well... yeah... he looks pretty good," she answered while continuing to admire the photo.
She made no attempt to hide the fact that she liked Anthony's body. We had always been open with each other. She was well aware that I enjoyed looking at naked girls on-line and I knew that she and a couple her friends collected and shared pictures of male models.
"I can't wait to show Sheila," she eventually continued. Sheila was Caitlyn's one friend that she had told about the email exchange with Anthony.
I then told Caitlyn that she should tell Anthony how much she liked the picture. He had showered her with compliments, so I thought that she should return the favor. She didn't waste any time in composing a response email.
She had only just begun typing when she turned to me and asked, "Can I be dirty?"
I told her that she could say anything she wanted, but by the time she was finished, I was shocked. She started by telling Anthony how hot he was and even told him that he looked like "the perfect man." In his emails he was always telling Caitlyn how much he liked jacking-off to her pussy pictures, so I guess that I shouldn't have been so surprised at my wife's response.
Here's the part of the email that caught me the most off guard:
"I can't wait to have a few hours to myself, so my favorite vibrator and I can have some girl time with your sexy pictures."
I was glad that Caitlyn was getting so turned on by the email exchange with Anthony because I was, after all, benefiting from the situation. Since the exchange had begun, Caitlyn and I were having the best sex we'd ever had. However, a part of me thought that this last email was too much. How is a guy supposed to react when his wife tells another man that she's going to masturbate to his pictures?
I wanted Caitlyn to feel free to write anything she wanted because it definitely turned me on to think about how naughty she was. However, I just had to ask if she really planned on using a vibrator while looking at pictures of her new friend.
"Of course not," she answered with a smile, "I'm just playin'."
She then reminded me that I had given her permission to be dirty. I had to admit that she was right. I just sat there for a moment, trying to reconcile the feelings of arousal with the feelings of jealousy, when Caitlyn got on her knees and unbuttoned my pants. She proceeded to give me one her best blowjobs ever. I'm a fairly large man, but I have a very little dick, so Caitlyn has no problem taking all of it in her mouth. Though I enjoyed it tremendously, I couldn't help but wonder if she was thinking about Anthony's larger dick while she sucked me.
For the next few weeks, Caitlyn and Anthony emailed back and forth. Eventually it came to light that we lived only three hours away from Anthony. Of course, as soon as Anthony realized where we lived, he wanted to set up a meeting. I apprehensively asked Caitlyn if she wanted to meet Anthony.
"No," she answered quickly, "he would be expectin' to fuck me, you know."
"Are you sure you don't want him to fuck you?" I asked.
I couldn't believe that I said it. Caitlyn couldn't believe that I said it. Something had changed in the past couple of weeks. The thought of my wife getting turned-on by a well hung guy had become very arousing to me.
"I can't believe you'd say that," she said, "...you know I'd never do that."
"I don't mean you'd cheat on me," I replied, "...it's just that you've been so turned on by all this... I thought maybe it'd be fun for you if we met him."
A stunned look appeared on Caitlyn's face as my words sunk in. I was kind of surprised myself. It was like the words had just come out on their own; it wasn't something that I had thought about at all. I had enjoyed seeing the way my wife had been behaving lately and I guess that there was a part of me that wanted to see how far she would go.
"Are you sayin' you want us to set up a meeting," Caitlyn asked with her face still full of surprise.
I thought about the question for a moment, but wasn't sure how to answer. So I just opened my mouth and let the words flow out spontaneously, "I just thought we could... discuss it if you wanted."
"I can't believe you'd even consider it," she said.
I wasn't able to tell from her words or the look on her face, so I was forced to ask, "Does that mean you'd never consider it or just that you're surprised by your options?"
She was silent for a moment before answering, "I've never even thought about it...I never thought you'd consider it, so I... I never thought about really meeting him."
"I know you love me," I replied, "that's why I'm comfortable talkin' about it."
However, I wouldn't say that I actually was comfortable, but I did my best not to appear overwhelmed with uncertainty or excitement. Caitlyn continued to look shocked. She looked at me, but said nothing.
"Listen," I eventually continued in a serious tone after a deep breath, "I know he's the kinda guy that girls dream about... and I also know that we've been havin' a lot fun with him. And I was just thinkin' this might be an opportunity we'll never get again."
I could tell that my wife was hanging on every word that I said. She just listened silently.
"If you decide this is something you wanna do, I would consider going along with it," I told her.
"I don't know," she answered after a long period of silence, "...I need some time to think about it."
Less than thirty minutes later, Caitlyn and I were in bed fucking. We were both lying on our sides and my cock was entering her from behind. Her pussy was wetter than usual. I knew that she was considering what I had said and that it was having a moistening effect on her.
After a few minutes, she climbed on top of me and began to slowly grind her pussy against me in circles. She can usually climax in less than ninety seconds when she's on top of me, but this time it only took about twenty. When her body finally stopped shaking with orgasm and her breathing returned to normal, she became motionless and looked down at me.
"Do you think we should do it," she asked.
"I already told you what I think," I answered, "...it's up to you, baby."
She didn't say anything more, so I rolled her onto her back and stuck my dick in her in a standard missionary position. I can't usually make Caitlyn cum in the missionary position, but this time I noticed her breath becoming uneven and knew it was only a matter of time. She tilted her head back and closed her eyes as I fucked her as hard as I could.
As her body started to tense in orgasm, I whispered into her ear, "Do you wanna let Anthony fuck you?"
My words pushed her over the edge and she erupted into a full blown orgasm. I repeated the question three more times while she was cumming, but she only responded with moans of pleasure. When her climax subsided, she opened her eyes and looked up at me. I stopped pumping her and put both of my hands on her face while I looked deep into her eyes.
"You wanna let him fuck you, don't you," I asked.
"I think so," she answered with only a second of hesitation.
It was like a current of electricity was shot down my spine as those three little words left my wife's mouth. I resumed thrusting my cock into her at a slow pace while continuing to look into her eyes.
"You're a very naughty girl," I said with a smile, "...you know that, don't you?"
"I can be a good girl too," she replied, "...but I'm startin' to think you want me to be naughty."
As she said the word "naughty," she squeezed my cock by clinching her pussy tight. I knew she was milking me and was ready for me to cum.
"Is that whatcha want?" she asked as I slid my dick in and out of her, "...you wanna naughty wife?"
"I think I do," I answered and began to fuck her harder, "...you wanna email Anthony and set up a meeting?"
"Yeah," she answered.
"You gonna show him your pretty pussy?" I said.
"Yeah... you think he'll like it?" she responded and then squeezed my cock even tighter with her twat.
"He'll like it," I answered, "...he'll give you all the attention you crave, you naughty girl."
A large wicked grin appeared on her face and I began pumping her cunt harder. The thought of my wife showing off her pussy had me in a frenzy and I knew that it would be only a few seconds before I started empting my load into her.
"You want his giant cock, don't you?" I asked as I felt the first spurt nearing.
"Yeah, baby," she answered.
She didn't say anything else for a moment. She could tell that I was enjoying the experience even more than usual. Sex had been really great lately, but this was a whole new level. She waited until she could feel me beginning to erupt before she said anything more.
"Are you gonna let him fuck me," she asked as I started filling her with cum, "...you wanna watch your naughty wife spread her legs for another man?"
Her words were perfectly chosen and perfectly timed to make my climax as intense as possible. As I shot spurt after spurt into her cunt, she repeated the questions. I couldn't respond to her question with words; I could only let out a series of ecstatic grunts.
When I finished cumming, I collapsed next to her and we just silently laid there in each other's arms. I was completely blissed out and enjoying the afterglow, but Caitlyn seemed less at ease. She definitely had something on her mind.
"Do you think we should really do it?" she asked.
I thought about how to respond for only a second and was about to answer her, but she continued before I could, "I mean... it's a fun fantasy, but it seems crazy to do it in real life."
I then told her that if it felt crazy to her, we should probably wait. I had really started to find the idea of extra-marital experimenting extremely arousing, but I didn't want Caitlyn doing anything she wasn't comfortable with. I knew she might resent it forever, if she felt like I pushed her into it.
"I think we have a great opportunity with Anthony," I said, "...but you need to be a hundred percent positive you wanna do it."
"It just seems crazy," she replied, "...I wanna do it, but I can't help feeling like a slut."
By the time that we went to sleep that night, we had agreed to think it over for at least one more day. I was certain that I knew how I felt about the situation, but I realized that Caitlyn was feeling rushed into a decision.
It turned out to be three days before we reached a definite decision. I sat next to Caitlyn at the computer while she wrote an email to Anthony. Here is part of that email:
"I'm sorry we haven't been in touch for a few days, but we needed some time to seriously consider your offer to meet. We've never done anything quite so sexually adventurous, so it was not an easy decision. I'm sure it must be difficult for any man to allow his wife the complete freedom to experience another man's love (especially a man's love like yours). However, after many long discussions, my husband has granted me that freedom. All that remains is for us to set the time and place."
I pointed out to Caitlyn that her email made it sound like I was the one who was uncertain of expanding our sexual boundaries, when in reality it had been her who needed time to think about it. She said that she had been pretty sure that she wanted to do it from the very beginning, but was afraid to admit it.
"I just wanted to make sure you were serious," she explained, "...and give you some time to see if you'd change your mind."
After hearing that, I saw things in a whole new light. I couldn't believe that I had been so naïve as to think that Caitlyn was ever unsure about getting together with Anthony. I had seen her reaction to his pictures; I should've realized that she would have never turned down an opportunity to see his cock in person, an opportunity to take her clothes off for him.
Anthony replied to our email later that same night and his excitement was obvious. He was very eager to get to know my wife in a face to face setting. However, determining the specifics of the rendezvous turned out to be more problematic that anticipated. Caitlyn and I are both very busy people and it turned out that Anthony was no different. Over the course of the next week, we exchanged emails with him in many unsuccessful attempts to work out the specifics of a potential meeting. Every time that we thought we had chosen the perfect day, one of the three of us would have something come up.
Eventually, all three of us were forced to approach it like a vacation. The only way to make it work was for us to clear our calendars for a weekend. The first weekend that we could all make work was four weeks away. Finally it was settled; the three of us would get together at a very nice hotel on Saturday June 7th at 2:00 in the afternoon. It would only be a little more than an hour drive for me and Caitlyn, but close to a two hour drive for Anthony. He didn't seem to mind.
The fact that June 7th was the earliest date that would work for the meeting was quite a coincidence. Though it was completely unplanned, the day of the rendezvous just happened to be Caitlyn's birthday. We had no doubt that if our plans didn't fall through, it would be a birthday that she would never forget.
In the weeks leading up to the big day, the excitement grew. Sex with Caitlyn was the best it had ever been. We both used the growing electricity of the impending meeting to push the other's buttons. However, six days before the meeting was to take place, she suggested that we stop having sex for the week in order to maximize the excitement of the actual rendezvous. I knew that six days of celibacy would bring her to an absolute boil, so I agreed to her proposition, though somewhat reluctantly.
For the few days right before her birthday, Caitlyn's level of anticipation was through the roof. I was also very excited, but some small concerns were starting to appear in my mind. These concerns were mostly just jealousy issues that any husband would have about sharing his wife. I was careful not to let Caitlyn know anything about my apprehension and it wasn't too difficult because the thrill of situation easily outweighed the jealousy. I had been aware that these feelings were coming. I wasn't so dumb as to believe that my wife could be heading for the arms of another man without me experiencing at least a small degree of jealousy.
When Caitlyn awoke on her birthday, she seemed like a different girl than the one she had been in the preceding weeks. It appeared that the anticipation she had been feeling had turned into nervousness. I was feeling anxious as well, but my uneasiness was balanced by my excitement.
The plan was to arrive at the hotel at two o'clock. Anthony would get there before us, pay for the room, and email the room number to Caitlyn. We planned to leave the hotel no later than midnight so that we would be home around one o'clock at the latest. The early start time would give us plenty of time to break the ice with Anthony and then get down to business. None of us wanted to rush things.
As Caitlyn and I ate a birthday breakfast that I had prepared for her, I could sense her nervousness, but she never voiced any concerns. In fact, we ate without any conversation at all. For the morning's first hours, neither of us mentioned Anthony or what we were about to do.
After a long shower, Caitlyn stood naked, looking through her closet and trying to decide what she was going to wear. I'd seen her naked countless times, but she looked extremely beautiful at that moment. She usually keeps her bush trimmed very neat, but she had shaved it in the shower, making her pink cunt clearly visible. I was already dressed, so I just sat on the bed admiring my wife's beauty. She pulled a skirt out of the closet and then noticed me staring at her.
"Pick out some panties for me," she said, "...pick out a pair he'll like."