Meeting Dwade - an extremely dominant gentleman

We began chatting with Dwade about two weeks ago. As i mentioned in my last post, he contacted me through SLS. Since he was from Chicago, i was very skeptical.  How could this work? Wouldn't the distance just doom the whole episode?

In our chats, he seemed perfectly suited for us. He was mature, educated, good looking, deftly conversational, and, last but not least, very dominant. He wasn't some guy who wanted to be dominant, he lived his dominance.

We spent about 2 weeks chatting, and it was refreshing not to have a guy want so many pictures. i have found the more pictures they want, the less real they probably are. He knew we were real, he could sense it.

i knew he was real, i could sense it. i didn't need confirmation. His actions proved he was in it for the long haul and i liked that.

I know she needs this...and am willing to search for her. 

Within about 3 conversations, he insisted i refer to him as "Sir." He saw it as a sign of respect and my submissiveness. i respected that.

As you know by now, Syd wants me to vet prospective dominants and so many have been time wasters in her experience. So far, he seemed like the real thing and i was keeping Syd abreast of all our discussions. She was intrigued by our texts.

i had to go on a trip to St. Louis for business and was routed through Chicago. While at the airport, i texted him that i was in his city for a layover and it was too bad we couldn't meet. We laughed it off and continued our back and forth texting.

Once i got to St. Louis, he told me he was at O'Hare and was himself on his way for a business trip. i asked him where he was headed and he said, "i have to go to St. Louis for a conference."

i told him, "You won't believe this, but i am in St. Louis!"

We talked about the chances of this coincidence and that we should meet one another. i am sure he wanted as much to see if i was real as i wanted to see his bona fides.

Our conversations in text and in voice to this point were all very smooth. There wasn't a red flag strewn into the field of our many conversations and that is very very rare. i'd say someone can fool me maybe for one chat, maybe even for two, but sooner or later, the real person comes through sooner or later. i am thankful this is true.

We decided we would meet that night if we could both get away from our respective clients.

It is weird how much anxiety builds up in these types of situations. There are a lot of emotions built around hopes and security. Hoping that everything works out and the guy is a good person and not a prick. And, feeling uneasy as you know somewhere in the back of your mind, if this is the right guy, everything could change in your life.

This is me.

Meanwhile, during all this, Syd has had me caged since about a month ago. The only time i have been let out has been about once a week to take a shower with it off. i can’t tell you how good it feels to have the water running on to my little dick. It's as if my nerve ending become super sensitive. It almost feels like i could orgasm from the experience.

So, Dwade and i talked throughout the day and it appeared we were both able to make our meeting. He asked me if we could meet in the lobby of his hotel. Given the implied hierarchy, i consented.

On my drive there, it seemed my little dick was straining its confines, so compact, so tightly caged.

i let him know i was there and waited for him in the lobby. i sat on a couch which looked very comfortable and also faced the elevators. Soon, he was exiting the elevators and i knew it was him immediately.

He was very good looking and walked with a confidence befitting a dominant in this regard.

He walked over to me and i got up to greet him and we shook hands. We sat down and chatted about all kinds of subjects from where we lived, personal stuff, and obviously sexual things. He seemed very interested in us and our story. Our story is wholly unique.

So, as i have written before, in these types of meetings, i am looking for signs of warmth or signs pointing to red flags. There were no red flags with this guy. Okay, one, he was shorter than me and that was something Syd has always said was an important asset for her. Of course, i knew he was almost three times bigger than me in other metrics, so i thought it was a hurdle she may be willing to overlook :)

He asked a lot of details about our sex life and i was being honest with him about everything. i sensed he was trustworthy and knew that it was best to be open and honest so that he would know what he was getting and so would we. In fact, i let myself be a lot more vulnerable with him than usual.  Maybe it was because he was from another city, maybe i felt comfortable with him. But, i told him things i'd never tell some people on a first meeting.

It was extremely late at this point and we both were pleased at what we had learned from the other.

He is going to be in a nearby city to us in about 2 weeks. We plan on the three of us meeting then.

Going to Chicago on business

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Meeting Chris for drinks...

Tonight, Syd and i went out for drinks to meet a guy who contacted us.  We get a lot of guys wanting to meet us, and i'm sure most of that is due to Syd of course. We do have a lot to offer and we have become even more discerning in or choices these days.

The guy who contacted us is a 28 year old black guy who is a grad student from one of the local colleges. He was very intrigued by our profile on a site. From the moment we began chatting, he seemed enthralled with us, especially Syd of course.

Searching for gold can be tedious...and rewarding.

i sat in the car waiting for them to come out and after about 20 minutes, they came through the exit doors together. We then drove him to his car.  The drive home was delightful recanting the episodes we just experienced.

So, after chatting for about two weeks, we finally set up a time to meet for drinks and tonight was that night.

Mind you, during those two weeks, every chat i was on the lookout for some red flag.  You see, so many times these will pop out as a warning signal and i have learned to trust my instincts regarding potential suitors. 

i believe that a lot of guys might be able to carry on one conversation and fake it, but over the long haul, they just can't help exposing their Achilles heel. Once exposed, they don't get another chance with us.  And because so many guys try to contact us, i have learned to be very discerning and Syd is so appreciative. She knows how difficult a task it is to sift through "candidates" to find the gem.

So, tonight was long anticipated by us because we hadn't met with a "candidate" in a while.  Chris was young, but demonstrated a maturity that impressed me.  You know someone is serious about you when they don't want or need myriad pictures.

Syd dressed for the occasion and i so wish i could show her to you. You would see an incredibly sexy blonde vixen with piercing blue eyes.  Her body is so ravishing. She is tall at 5'8" but when she wears 5" heels like she did tonight - 5" heeled boots - she is 1" taller than me.  It is so fucking hot to see her walk into a room and watch all the heads turn.  And the beautiful thing is she doesn't even know she does it. With her boots and skin tight pants and her blouse which so seductively pulls your eyes to her voluptuous cleavage, she makes me, her husband of 20 years hard when I see her.

Well, at least kind of hard, as I really can't get hard confined in the Queen's Keep she loves to lock me in. More about that some other time.

So, we walked into the hotel lobby where there is a great bar we enjoy. It's an exclusive hotel with a lobby that just oozes charm and class. We found a nice little nook where we could sit, but also be served drinks from the wait staff. Traffic was crazy so I thought Chris might be late.

And if you have ever done this, you're never sure the guy is going to show up. It is beyond me why some people engage only to disengage after receiving pics. I mean with ubiquitous porn on the web, who needs personal pics to get off?  Really? I'm not sure i'll ever understand the motivations behind such time wasters.

Anyway, part of me was hoping Chris was not in this camp. i emailed him where we were sitting and it was about 20 minutes past the time we were supposed to meet.

But again, traffic was as snarled as i have seen it in a long time here. i decided to walk around and the lobby and into the bar. i recognized him right away. He was sitting at the bar very well dressed and already drinking what looked like a whiskey drink.

He smiled an easy smile when i inquired, "Chris?"

He stood up and shook my hand, firm and looked me in the eye.  So far so good, i thought to myself.

He looked like his pictures, which is no small statement. He is very good looking and towers at 6'4" with the body of a soccer player. His nude pics he sent us would be the envy of most women, in all respects.

We walked over to where Syd and i had been sitting with our drinks waiting for him. She stood up when we got closer and shook his hand in a very businesslike manner. Clearly she was sizing him up.

We all sat down and the waitress came by to see if we needed anything. We all had drinks so we didn't order any more, but she clearly looked at the three of us with subtle bemusement. The thought that she knew what was going on was intoxicating to me.

The three of us began to chat about our backgrounds, and histories, and own personal stories. He was very engaging and was genuinely interested in getting to know us better. Again, he was very mature for being 28 year old.

As an aside, how hot is it that my newly turned 46 year old wife is the object of desire for a handsomely virile young man.

He told us about some of his previous relationships and how his most favorite have been cuckold relationship is which lasted on the long-ish side.  Long for him meant 6-8 months.  And given his perspective and youth, we understood.

He clearly was dominant, not because he told us that, but because that was how he held himself. He was comfortable in his own skin.

i can't tell you how many guys will contact me and say they "can be dominant" or they are "sometimes dominant." That is definitely not what we are looking for.  We want a dominant who is dominant because he is dominant.

We talked for about 2 hours over drinks. We knew beforehand that he had a previous engagement with a couple he was meeting at a hotel. We knew our time was limited but time was also flying as the conversation weaved so effortlessly from personal to sex to whatever came up. It was a fun.

i excused myself to go to the bathroom. Don't get me wrong, i did have to go to the bathroom, but i also wanted to give them some alone time perhaps to say some things they might not otherwise say with me there, particularly Chris.

When i returned, Chris told me that he wanted Syd to take off her panties and hand them to him but she wasn't wearing panties! We only knew him 2 hours, and he was giving tasks.  Sometimes tasks can be exhausting, he seemed to know how to make them fun.

He thought for a while and then asked Syd to go upstairs in the lobby and sit on the couch near the bathrooms and that he would be up in a couple minutes.

Believe me, if i could get erect, i would have been. i was on hyper alert in a very good way. After she left us, he leaned closer to me and confided that he intended to go up and direct her to go with him into the men's room. He said there wasn't anyone in there and wanted to kiss her. He asked how i felt about it. i told him i thought it was not and exciting. He said "good" and proceeded to get Syd.

There i was sitting alone where just minutes ago my wife was sitting with me and our new black friend. i was so turned on. It seems everyone who walked by looked in my direction as if they knew exactly what was going on. Of course I know they didn't really, but I do think at least our waitress knew. The combination of arousal and humiliation was so raw for me at that point.

i looked at my watch and realized they were gone about 20 minutes. It seemed like an eternity. Finally, they descended the marble staircase together in a not-too-subtle display that they were together. They walked over to me and both smiled so broadly.

He told Syd to tell me what they did. She told me he directed her into the men's room and they went into a large handicap stall and began kissing. He then went down on her and then unbuttoned his pants and guided her head to his cock. She later told me he was very big and had a lot of fun with him in those few minutes.

Guys were coming in and out of the bathroom while they were in there. They had fun knowing they were bucking convention by being in there. He then suggested as there was a guy in the bathroom washing his hands that they walk out so he would see them exit.  They did. They talked about how exhilarating it was.

Remember, this was my wife who a year ago never watched porn and didn't know the word cuckold...with a 28 year old!

Soon after relaying the events to me, we realized Chris had to go and so we all stood and i shook his hand and he warmly hugged Syd and kissed her on the cheek saying he couldn't wait till we see one another again. He asked if we could share cell phone numbers and we did.

So, that was it. He left and Syd and I talked about how much we liked him and enjoyed his company. We decided we would go to one of our favorite restaurants in the city, a place where we can get amazing food and a quiet atmosphere so we could talk.

On our way to the restaurant, I received a text from Chris, "Great meeting with you guys tonight. i hope we can plan something in the future so you can be included in the fun we had in the bathroom."

It felt good to receive that from the guy who was vying to be our dominant.

And, no sooner did we get seated and i received another text from Chris saying the couple he was supposed to meet with backed out and he wondered if he could meet us for some more talk.

We asked him if he wanted to join us for dinner. The quickest response ever came back saying he definitely did and that he could be there in a couple minutes.

We told our waitress that we were expecting a friend in a few minutes.

He came into the room of the restaurant in which we were seated and it was like an old friend just joined us. He took off his coat and sat right next to Syd. i was seated across from Syd. We talked about how comfortable we all felt and good our evening was with him earlier. We all agreed that the couple backing out with him was a good thing...for us, all of us.

We all looked at the menu and finally ordered. As we sat there and talked, Chris casually put his hand on Syd's leg. Right there for everyone to see, he had his hand on my wife's leg. And he would look me in the eye and smile and I'd smile in return.  We both were loving it. And, i know Syd was loving it.

i also noticed that when our waitress would come by, he would keep his hand there. i am quite sure she noticed and the thought they she knew was something hard to describe, but i'll tell you it was thrilling.

After a little while, i excused myself to the bathroom. Again, i thought i'd give them some alone time. On my way back from the bathroom, i noticed i could see our table from an interior window and it was likely they couldn't see me. i stopped and watched them and thought to myself how erotic this all was.

Then, amazingly, i saw Syd look around the restaurant and then she leaned over to Chris and they kissed. Again, right there in the open and if anyone was looking, they would have seen everything. i was looking, even though they didn't know i was looking, and was so turned on. Probably precisely because they didn't know I was looking made it even more of a turn on.

i didn't say anything to them upon my return and would only later tell Syd i saw them kiss. She loved the fact that i saw it.

We continued through dinner and by this time we were the only ones left in the restaurant except for a few waiters. When it came time to leave, Syd asked me to go get the car and i knew that was code for giving her and Chris some alone time. i left the restaurant for the car and saw them head off to a very dark section of the restaurant.

i am sure there will be more posts to come about Chris.

Stay tuned...

She's with her Boyfriend…overnight

i am writing you tonight as i lie in our bed, alone. Syd is with her boyfriend for an overnight visit which started around 5pm and will go to sometime tomorrow morning. i will continue to write as i go along these next hours.

He called her earlier this week and told her he wanted her to come over and stay the night with him. She loved being asked and it was clear to me she really wanted to do it.

In situations like this, even though i may feel a little uneasy about it, i try to be extra supportive to her and make her feel very good about going. i know ultimately that she loves me and she loves exploring her sexuality.

I wonder if Syd feels this way now.

The day before, she asked me to get a bottle of wine for her and her boyfriend. This made me feel a little tortured, in a good way. i made sure it was a part of my daily calendar for i didn’t want to forget. i walked into the liquor store and found what i thought would be a great bottle of wine for them. After all, i wanted to please Syd as well as Ryan. As i checked out with the female clerk, i thought to myself, if only knew what this purchase was all about.

Leading into all this, Syd instructed me that she wanted me in the Queen's Keep for an indeterminate amount of time. She talked about how pleased she is when i am caged and how she prefers to have me that way, it makes her happy.

It is odd i know, but to hear her say that made me incredibly aroused and excited to know she liked me caged. It is so counter intuitive and i'm really not sure why, but i know i like that she likes it.

It feels good inside to wear it as i know i am pleasing her and serving her as well as her boyfriend.

So, not only was my wife going to stay with her boyfriend overnight, but i was going to spend that time caged. Normally, i'd love to j/o or even edge if i wasn't allowed to cum, but not even being able to touch my little dick was excruciatingly titillating.

The morning of her overnight, she teased me so much in bed. She killed me by touching my cage and rubbing my testicles and whispering how her boyfriend was going to fuck her that night and how much he wanted her alone. She knew she was driving me crazy but she loved it.

All day at work, all i could think about was how she was going to go to his house around 5pm, which was before i would get home. So, i wouldn’t see her all day.

And all day, i knew she had planned to have her hair styles and also to get a manicure and pedicure. He loves when she does all this for him.

Syd was also very good to me by texting how much she loved me and how i was her number 1. It felt reassuring to hear her thoughts in this way.

She texted me when she got to his house.  She also added how much she loved me which again felt good.

When i got home, i took the kids to dinner and we had a great time. Having such a fun time with them sure took some of the edge off my otherwise preoccupied evening. i tried not thinking of them together, but it was inevitable.

Amazingly, i didn’t hear from her until the next morning. The only text i got from him was to say i picked out a good bottle of wine for them.

i was so expecting to hear from them, whether it was pictures or little texts throughout the night, i was expecting they would want to share their experience with me if only to tease me. Alas, that wasn't the case.

i wanted to sleep long and hard, but i wasn't able to very much.  Plus, i wasn't even able to get hard with the cage. All in all it was a very frustrating evening.

The next morning i took care of the kids with breakfast and school, and then went off to work. All day all i could think about was wondering what they did and were doing.

So, i write this not to tell you about all the sex they had, they surely did, but mainly to say i realize now that this is the life of a cuckold. This is the life i wanted and fantasized about. And, i am happy. And,it isn't easy. i suppose i never thought it would be. Yet, i look forward to being able to convert my feelings into a new spiritual awareness. It excites me for what is to come, the pleasure and the pain.