Holding Caitlyn's Hand Ch. 01

I briefly looked through the many panties that Caitlyn had in her dresser before pulling out a tiny plain white cotton pair. She had lots of cute panties, but I decided that simple was the way to go. As I handed the panties to her, she commented that they were awfully plain.

"I think he'll like 'em," I said, "...besides, you're probably not gonna be wearin' 'em long anyway."

She let out a short nervous laugh before replying, "I can't believe we're really gonna do this."

I asked her if she was having second thoughts and she admitted that she was, but said that she still wanted to go through with it. I watched her pull on her panties and realized that when those panties came off, I wouldn't be the only one looking at her pussy. I hadn't even touched her pussy in days and now someone else was in line before me. It would be the first time in years that someone besides me delivered Caitlyn's birthday fuck.

We didn't talk anymore about what was going to happen until we were in the car heading for the rendezvous. I asked her if she was excited.

"Yeah, I'm excited... but really nervous too," she answered, "I'm trying not to think about it too much."

After that I decided not to say anymore about what was to come. Our only stop was at a small café for a quick lunch and then we were off to the hotel. As we neared our destination, she checked her email on her phone.

"Room 162," she announced, "...he says it's on the backside... just drive around back and look for a white Lexus."

It wasn't until we were exiting the interstate that Caitlyn mentioned Anthony by name for the first time all day.

"Do you think Anthony will like me?" she asked with an apprehensive smile.

I assured her that he would absolutely adore her.

"You two have been writing back and forth forever," I said, "...and he's seen lots of pictures of you... he knows almost as much about you as I do... just try to relax and don't worry, he's gonna love ya."

There was an uneasy silence as I pulled into the hotel's parking lot. Neither of us said a word as I drove around the hotel looking for the white Lexus. When I spotted it, I parked next to it and turned the car off. Caitlyn looked at me with eyes full of uncertainty and anticipation. We got out of the car and I walked around it to take her by the hand. We walked slowly, hand in hand, across the parking lot to room 162.

Anthony answered the door with a smile on his face. He shook my hand before kissing Caitlyn on the cheek and then giving her a hug. The room was more like a suite than hotel room. It was much nicer than I expected and had two separate areas. In the center of the front area was a glass table with a large pull-out sofa and two chairs positioned around it. There was a kitchenette on one side and the entrance to the bathroom on the other. The back area had a king size bed centered against the back wall and an armchair in the corner. There were nightstands with lamps on each side of the bed and a television rested on a long dresser that sat opposite the bed.

What proceeded to happen was incredible. Though Caitlyn was nervous about the whole experience, Anthony quickly put her at ease. Everything that he said and did was perfect. It seemed like he had known her all of her life and was able to do exactly what each situation called for. He began by putting to rest any doubts that Caitlyn or I may have had. For almost two hours there was no mention of sex and he was a perfect gentleman.

Anthony and I hit it off from the very beginning. He obviously understood that he needed my endorsement for his hopes to be realized. We talked for awhile about our jobs and sports. It really seemed like he and I had been friends for years. After he sensed my approval, he turned his attention toward Caitlyn.

The birthday cake that he brought out from the kitchenette was the first sign that he understood Caitlyn. He made a big deal about how it was her special day and about how she should be treated like a princess. He even gave her a stunning crystal tiara that said "birthday girl."

As Caitlyn sat there wearing her tiara and eating a piece of cake, I could tell that she was starting to loosen up. After we all had small pieces of cake, Anthony pulled out a bottle of her favorite wine. After a glass, she was giggling and chattering away. Just as he had done with me, Anthony had succeeded in assuring Caitlyn that he was sincere and worthy of her trust.

At exactly the right time, Anthony changed the mood in the room. He stood up, took his phone out of his pocket, and asked Caitlyn if he could take a few pictures of her. Caitlyn popped right up and stood with her back to the door while he snapped a few quick pictures; a couple with the tiara and a couple without. Caitlyn was completely at ease. I had no doubt that the big smile on her face was real and not just for the benefit of the camera.

As I've said before, she loves attention and loves being in front of a camera. I wasn't sure if Anthony really wanted fully clothed photos of my wife or if he just took the pictures because he knew how much she would enjoy posing. It was exactly the perfect thing to do to get Caitlyn's motor running.

Anthony looked at me and said, "I'd also like to get a few of the two of you together."

Caitlyn seemed to like the idea and I didn't mind, so I walked over and stood next to her. Anthony took one picture of us holding hands, one of her in my arms, and one of us kissing. He then put the phone back in his pocket, but I was pretty sure that he would try to take more pictures before the end of the evening.

Up to this point, Anthony hadn't broached the subject of sex and had been careful not to allude to any potential future sexual events. However the moment was now right to switch gears and he did it flawlessly.

"How 'bout you show me that dance now," he said to Caitlyn.

He was referring to a dance routine that she had, in an email, promised to perform for him. She had been on the dance team in high school and still knew how to do one of the routines. It was a dance that I'd seen several times and it was definitely an attention grabber. Knowing how Caitlyn likes attention, I wouldn't be a bit surprised if all of her past boyfriends have seen the dance as well.

"Okay," Caitlyn replied, "...just let me clear some space and get the music set up."

While she retrieved her iPod and a pair of tiny speakers from her bag, Anthony pulled the glass table out of the way. He then took a seat next to me on the sofa and Caitlyn cued up the song she needed for her dance. For the next three and a half minutes, Anthony and I sat transfixed while my wife showed her moves. I wish I could describe the moves better, but I'll only say that there was more hip shaking and ass shaking than you'd expect from a high school dance team routine.

Caitlyn definitely still knew how to work it and seemed to be glowing when she finished. Anthony applauded and Caitlyn's smile grew wider.

"That was incredible," he said to her.

Caitlyn was positively beaming with pride at Anthony's words. Everything he had said and done had worked to get her into the state he wanted her. Though he didn't need any help from me, I saw that Caitlyn was ready for the next step and therefore let her know that it was time to take off some clothes.

"Do your dance one more time," I said to her, "...but this time, do it like you do at home."

She blushed, her face turning the cutest shade of red. She knew what I meant, but still asked what I was talking about.

"This time in your panties," I answered her, "...and just your panties."

The red color of her face told me that she may have been a little embarrassed, but her big smile indicated that she wasn't overly uncomfortable with my suggestion.

She stood silently looking at me for a moment before saying, "Okay... if that's whatcha want."

She took a seat on the sofa between me and Anthony and began to untie her shoes. I'm not sure if she was stalling for time or if she was trying to tease us, but her shoes and socks were removed at an agonizingly slow pace. After she had pulled off the second of her socks, Anthony stood up and faced us.

"I just wanna take a second to say a couple things," he said with a gentle, yet serious, voice.

Caitlyn put her hand on mine and we gave him our undivided attention. After he took a deep breath, he went on.

"First, I wanna thank both of you for inviting me into your marriage," he said, "... I know it takes a lotta trust and I'm very grateful to be Caitlyn's first."

It was refreshing to hear that he was thankful. He came off as a truly humble man and my trust for him grew even more. However, it was a little strange to hear him say, "Caitlyn's first." It was as if he was implying that my wife would soon be sleeping around. Caitlyn and I had never talked about what might happen after this experience, but I had assumed that this was a one-time exception to our marriage vows. I wasn't able to think any more about it before Anthony continued talking.

"Second, I wanna say I have a lotta of respect for women," he said, "... and I've tried to treat Caitlyn like a lady so far today... but I've found that most girls don't wanna be treated like a lady in the bedroom. So, I might say or do some things that seem kinda... outta control. But I think you'll like it... I think we'll all like it. But if either of you feel like I cross the line at anytime... or if you're uncomfortable in any way... just let me know."

I wasn't sure what to think about Anthony's words and I could tell that Caitlyn was unsure as well. We looked at each other for couple seconds before I nodded my approval to Anthony. This was going to be interesting, but at least I felt like we had some degree of control.

"Okay then, where were we?" he said as he sat back down next to Caitlyn, "...oh yes, you were about to do that dance for me again."

She then rose to her feet and turned to face me and Anthony. Her eyes met mine and she stood motionless for a few seconds. At that moment, time seemed to stand still and her eyes were saying to me, "unless you stop me now, I'm gonna take my clothes off." I knew she was about to start undressing when Anthony spoke again.

"I have an idea I think all three of us will like," he began before turning to me and continuing, "...stand up there next to her."

I wasn't sure what he had in mind, but I did as he asked. Once I was standing next to her, he told me to kiss her. I kissed her quickly, anxious to hear Anthony's idea.

"Now, I want you to undress her for me," he said, "...like you're presenting her to me."

It seemed like a weird request at first, but as I thought about it, I realized that there was something really erotic about it. My pulse raced as I thought about actually peeling off my wife's clothes for the viewing pleasure of another man. I imagined that it would feel similar to the way a father would feel as he gave away the bride at his daughter's wedding.

Caitlyn lifted her arms, inviting me to pull her blouse over her head. For a brief second, I felt like I couldn't move. Despite the fact that I was starting to get turned-on, I was suddenly uncertain about proceeding. However, my hesitation only lasted a moment. I knew that we had come a long way to make this happen and I also knew that it was way too late to turn back. Besides, Caitlyn's raised arms signaled that she had overcome any doubts that she'd had.

I moved in close to her and grabbed the bottom of her blouse. I took a deep breath and then pulled it over her head. She was wearing a plain bra that pushed up her little B-cup titties. I knew that I shouldn't think too much at this point, so I just quickly unhooked her bra. She stood up straight, waiting for me to pull the bra off of her.

As I removed the bra, she stared straight at Anthony and let out a little giggle. She covered her tits for a moment before dropping her arms and letting him drink in the sight of her topless body. She looked amazing with her small perky tits on display. Though her titties aren't real big, she has large pink puffy areolas that make her chest much more appealing than most girls'.

"Beautiful," Anthony said as he admired her, "...stay like that for a minute."

He then pulled his phone back out and took two pictures of topless Caitlyn. She arched her back and proudly presented her chest to the camera. Her smile left no doubt about how much she was enjoying the experience. I guess that I must have also liked it because I could feel my dick starting to stiffen. After Anthony sat his phone down, there was a brief period of awkward silence.

Caitlyn looked at me and said, "Take my skirt off, so I can start dancing."

At that point, I could hardly wait to have the rest of her displayed to Anthony, so I was happy to comply with her request. I unzipped the back of her skirt and let it fall to the floor. She was beaming with pride as she just stood there wearing only her white cotton panties. For several seconds she stared down at Anthony with a huge grin on her face.

It only took an instant for Caitlyn to cue up the music this time and she was soon prancing around in her panties with her little titties bouncing up and down. All signs of nervousness were completely gone. There were two times that she turned her back to us, bent over, and gave her ass a good wiggle. She was clearly ready to take it to the next level.

"Unbelievable," Anthony said when the dance was over, "...you are so cute."

My dick was hard and I'm sure that Anthony was well on his way to a raging hard-on as well. When Caitlyn looked at me, her face was easy to read. It was saying, "I guess you better get over and take these damn panties off of me."

Anthony looked at me and said, "I think she's ready for you to pull her panties down."

All three of us were ready. Everything had built to this moment and there was electricity in the air. I got up off the couch and walked around to behind Caitlyn. I put my fingers inside the elastic waistband of her panties and slowly began to slide them down.

"Don't take 'em all the way off yet," he said, "...I just wanna see her stand there for a minute with her panties 'round her knees."

Caitlyn took a deep breath as I slowly pulled her panties down to her knees and exposed for her smooth pussy. For the first time in years, someone new had their eyes on her cunt. She must have been very aroused because the smell of her pussy was extremely strong. Anthony looked her up and down for a long time without saying a word. He eventually picked up his phone and she flashed a cute embarrassed smile for the camera.

After taking several pictures, Anthony had me put the tiara on her. She looked so adorable standing there with her shaved pussy on display and wearing her 'birthday girl' tiara. I couldn't help but feel proud that the beautiful angel in the center of the room was my wife. Anthony must have thought she looked pretty good too, because he snapped lots of pictures of her. I had never seen her look quite as mesmerizing as she did at the moment when she bit her lower lip and gave her best pouty face.

He had already taken a ton of photos when he said that he wanted Caitlyn to pose with me standing next to her and holding her hand. It seemed odd that he wanted pictures of her standing next to her fully clothed husband, but I did as he asked.

He only took one picture before he put his phone down and walked over to us. Caitlyn looked up at him and he kissed her on the mouth. It was a long passionate kiss and I could tell that she loved it. My heart was beating like crazy, but it felt a little bizarre to stand there with a hard-on and hold my wife's hand while she kissed another man with her panties around her knees.

After Anthony broke away from the kiss, he told her to turn around. Caitlyn happily did as she was told and he spent a minute checking out her ass. Her cute little butt looked absolutely delectable.

Anthony then suggested that we head to the back area where the bed was. After pulling up her panties and taking off her tiara, Caitlyn ran to the back and jumped onto the bed. Anthony and I followed. Caitlyn was lying on the bed face down, but he instructed her to get up and pull off the covers.

"Now get back in the bed," he said to her after she had thrown the covers onto the floor, "...prop yourself up with some pillows and open your legs."

There were six pillows on the bed, so Caitlyn had no problem doing as she was told. After she had stacked a few of them against the headboard for support, she was lying there with her legs spread, just like Anthony wanted. He took a minute and eyed the delicious piece of eye-candy that was laying spread out for him on the bed before he turned to me.

"Take off her panties," he said.

Those were the words that I wanted to hear because I couldn't wait to have my wife's pussy back on display. I could tell that Caitlyn was also happy to hear those words by the big smile on her face. As I put my fingers into the elastic waistband of Caitlyn's panties, she raised her ass up off the bed, making it easy for me to follow Anthony's instructions. A second later, her panties were on the floor and Anthony was once again enjoying the sight of my wife's shaved twat.

Caitlyn had a wicked grin on her face as she spread her legs for her two man audience. Anthony seemed more than happy to just stare at the beauty that was being presented to him.

"She's pretty cute, huh?" I asked Anthony.

He replied without taking his eyes off her, "Yeah... I'm speechless."

He took another moment to admire my naked wife before taking off his shirt and walking to the side of the bed. He grabbed one of her ankles and spun her around ninety degrees to where she was facing him. Without letting go of her ankle, he softly kissed the bottom of Caitlyn's foot and proceeded to deliver delicate kisses to each of her toes. She has extremely sensitive feet so I wasn't surprised when she let out a little laugh.

Anthony rubbed, kissed, and licked his way slowly up Caitlyn's leg, from her foot to her ankle, to her calf, and to her thigh. He pulled her legs wide apart and concentrated his attention on her inner thigh, his mouth only inches away from her pussy. She began to tremble with excitement and then closed her eyes and moaned. When she opened her eyes, they focused on me. We looked at each other, both knowing that it might only be a matter of seconds before Anthony's tongue was in her pussy.

Though a wave of jealousy washed over me at that moment, it wasn't able to wash away my arousal. My dick felt like it was about to burst through my pants. Part of me wanted to pull Caitlyn out of the bed and take her home, but another part of me wanted to pull down my shorts and start jacking off. Both impulses were strong, but at that moment, they cancelled each other out.

Anthony continued to work his way up the inside of Caitlyn's thigh until he was eventually sucking on one of her outer pussy lips. As she let a loud sigh, she held up her hand and beckoned me to take it. I stood there beside the bed, holding her hand while she enjoyed the treatment she was receiving from Anthony. When he finally planted a kiss on her cunt, she squeezed my hand tight and moaned in pleasure. He licked up and down the entire length of her cunt several times before pulling her lips open and sliding his tongue into her.

I consider myself to be really good at giving oral to a woman. Because my cock is fairly small, I figured out long ago that I needed to compensate with an excellent tongue. Every girl who has ever been kind enough to allow my face between her legs has been rewarded with at least one orgasm. Caitlyn's favorite part of sex with me has always been the oral sex and I've made sure to never disappoint her. That being said, Anthony made my wife squirm like I'd never seen. You might think that a guy with a cock like his would rely solely on it to please ladies, but that was not the case.