----
After a successful “meet and greet” on a patio in August, D and I decided to invite Sir to join us for a play time in person. Due to busy schedules, and his desire to acquire a few things for the event, we set the date for early September.
The day arrived and I was quite nervous. It was my first “first time” with someone new in a while. On top of that, it was a different type of play date than I had tried before.
I am quite independent and don’t do well at being told what to do. My husband knows this about me from our BDSM play, and Sir and I had had enough “wench breaks” that this shouldn’t be a surprise to him either, but I still didn’t want to disappoint anyone if I couldn't stay in "sub" mode the whole time.
In addition, I didn’t know exactly what would happen, or how long it would last. In regular life, I am a planner and like to be in control.
There was something exciting and arousing about trusting someone else in a situation like this -- to just go into an evening and only worry about enjoying the experience of what was being done to and with me -- but it was also nerve wracking.
I had to remind myself that D was going to be there the whole time. He would participate, but would also make sure things didn’t get out of control.
It was also helpful that Sir and I had spent many months chatting. He understood my desires and my limits, we had discussed safe words, and I genuinely trusted that he had my best interests at heart.
After a brief pep talk from some of the VHW’s in the ladies lounge, I took a deep breath and got ready to head to the hotel.
Sir had asked that I wear a specific outfit. It is somewhat hard to explain (and no, I won’t post a picture
) but I’ll try. It is an Esty purchase from a BDSM crafter. It consists of two pieces, both made out of strips of two inch elastic band that are sewn together. The bottom part pulls over my waist. The strips crisscross around my waist and the top part of my ass. There is a strap that goes about halfway down the side of each leg, and there are two straps that circle each thigh.
The top is a strappy chest harness. The breasts are completely exposed, but the elastic frames each one nicely, and there is a halter-type collar with an o-ring at the neck.
The outfit covers absolutely nothing, but does provide some good visual stimulation to those who get to see it
I put it on and threw a dress over top. D and I also packed a bag to bring with us. It contained lube, condoms, some nipple clamps, and a few different toys that Sir had requested. We also brought a bottle of wine to share.
Sir had booked the hotel room because he wanted early access to it. He had spent a couple of hours setting it up for our time together. We texted him to see if he was ready.
“As ready as I’m ever going to be,” he responded. We should come on over.
The hotel room was on the first floor and had patio door access from the parking lot. He told us the room number and met us at the door when we arrived.
He smiled at me as I approached and it eased my worries. He’s handsome and sexy, and the thought of playing with him was very exciting. I smiled back...until I got through the door.
The room was filled with sex toys...I mean, entirely filled! Across the dresser/tv stand there were dildos of every shape and size; leather restraints and padded restraints; paddles, canes and riding crops.
The drawers of the nightstands had nipple clamps, padlocks, and things I couldn't recognize. The bed was covered with a blanket but I could tell that something had been done there as well. It was a lot to take in.
Sir admitted that it was a bit over the top. He laughed and said that he can’t help himself when it comes to purchasing toys. Then, when a play time comes up, he doesn’t want to risk leaving something at home and wanting it in the moment.
I chuckled but also warned him, “You’d better be careful or some woman is going to take one look at this type of set-up and high tail it right out the door.”
As D poured us all a glass of wine, Sir told us a story about one woman he had played with a few years ago. They had chatted for a few months online and built up a good repartee. She didn’t want to do a public meeting. Instead, she wanted to jump right into going to a hotel room.
When she arrived, she was so nervous that she was visibly shaking. Sir told her that she clearly wasn’t ready. They ended up just having a glass of wine together and chatting for an hour. Then she went home.
They chatted some more over the following weeks but never did play together because he wasn’t convinced that she was mentally ready to do this type of play.
I appreciated the story and the fact that he would never push someone to do something they didn’t want, or even that they said they wanted but weren’t prepared for.
“Well I’m nervous, but not shaking,” I said, holding up a steady hand.
Sir asked if I wanted a second glass of wine to calm the remaining nerves “or to act as truth serum, if you feel like confessing any fantasies or secrets,” he teased.
I rolled my eyes and shook my head.
“I think that what I need is to take this dress off and then my nerves will go away,” I said.
Both men agreed that was a great idea. I stood up and had to figure out which way to face for my strip show.
D was sitting on the bed in one direction and Sir was sitting on a chair in the other. I decided to do a little spin as I slowly lifted the dress over my head. I did my best to be enticing and arousing. I could see tents in the men’s shorts so I figured I was doing a good job.
I folded the dress and then laughed because there was no surface to put it down on. I bent down to put it on top of one of Sir’s many luggage bags. When I stood back up, Sir had come up behind me.
“Let’s begin the wench inspection,” he suggested.
I replied with a simple, “Yes sir.”
His hands reached around and grabbed my breasts. His hands were firm, but not hard, as they groped me and played with my nipples.
It is hard to explain, but I had been curious about the intensity level of what would happen. His groping of my breasts assured me that he wasn’t out to hurt me. I relaxed a bit more.
D was in front of me and kissed me once as he lifted my arms and told me to hold them behind my head while they took me in. Four hands then stroked and explored my body: a hand on my clit, one on my ass, another on my breast. It was extremely arousing. I could feel myself getting flushed -- and wet -- as the play continued.
Sir reached between my legs and began to massage my clit. It was soft and rhythmic and I could quickly feel my orgasm building. D leaned forward and whispered in my ear that I was a beautiful wench and that I was going to have a fun evening. I came soon after.
Sir then led me to the bed and had me bend over. It was time for the internal inspection, he explained. We had talked about this before, so I knew what to expect.
“Yes sir,” I said.
My face was near the bottom edge of the bed, so D brought his cock to my mouth for me to suck as Sir put on a latex glove and came to sit next to me. He groped my ass a bit and asked if I was ready for an anal probing. My “yes sir” came out a bit muffled around D’s cock.
(Side note: I so appreciated how the men sought my consent for each aspect of the evening. If I didn’t give a “yes sir” -- or a nod when gagged - they didn’t move forward. If I said a safe word, they stopped and let me take a break until I was ready for more. It made me able to let go and trust them throughout the experience).
Sir commented on how tight I was, and he got extra lube to slide his finger in. Soon a second finger joined.
I do really enjoy anal play, and combining that with a cock in my mouth and my clit grinding against the hotel bed was a lot of sensation all at once. I began to moan in pleasure.
Sir grabbed a toy from the nearby dresser. It was long, hard, and looked like it was made of glass crystals. It was also already covered with a condom (all the toys had been prepared like this in advance so that I wouldn’t have to worry about sanitation).
With my ass already warmed up, the toy slid right in. It was pretty long. Whenever it was fully inserted I let out a little, “oh!” The men seemed to enjoy that.
D took his cock out of my mouth and told me that I might get more of it later. He wanted me to focus on my own feelings for a while. I was moaning and grinding myself against the bed as Sir fucked my ass with the toy. It didn’t take long before I came again.
I won’t recap all of the evening’s details here. I will say that there were some times that I masturbated while the men watched. There was a bit of spanking and a lot of toys inserted.
I will also say that we attempted to have Sir fist me. We got very close, but I couldn’t take the last little bit. With that said, when he had four fingers inside me and he moved them around, I got lost for awhile in the feeling.
I will also tell you that under that blanket on the bed Sir had rigged chains across the sheets and mattress. With leather restraints on my ankles and wrists (and later with a different restraint holding my knees up and back), I was locked in place on the bed and couldn’t move. It sounds scary, but it was amazing.
Riding crops and floggers can be very enjoyable, especially when wielded by men who want your sexual pleasure.
While I was restrained, Sir took out his electro-stim machine. I had told him that I was curious about it and that I was hoping it would be used during our play time.
He told me that I was “a very special woman” because many were intimidated by the prospect of electricity in their bodies. The fact that I was even willing to try was impressive to him. I'm of the mindset that you never know what you might think about something until you try it. And I really wanted to try it.
Sir chose an anal and a pussy probe. Both were inserted and connected to the control device. He then tried out a series of programs.
Sir started at a very low intensity and gauged my reaction. I was asked to describe the feeling. For those unfamiliar with it, I think the best description is that it is like a warm vibrator massaging you internally.
As the intensity increased, the vibration could pinch a little. There was never a shock or jolt of electricity, and nothing was truly painful, but at full strength the feeling was intense.
We played a game where I had to guess what the preset program was called.
"Describe the feeling. What's a word you'd use?" Sir asked me.
Depending on the strength of the current, I sometimes found myself a bit incoherent. I correctly identified "wave" and "rhythm."
D helped prompt me to guess "orgasm" ("Think about what it just made you do"). And "intense" was identified as a pure stroke of luck as I arched my back and struggled to speak.
"I don't know! But it is really intense!"
There were rolling orgasms and times where I had to tap out and ask for some water (or to stretch my arms and legs after a long period of restraint). There were also tender moments where D would kiss me, check in, and tell me how amazing I was.
By the end of the evening I was sweaty, sated, and exhausted. I must have cum 30 times and I physically couldn't take any more. I say that, but before we left, D asked me to stand in my inspection position one last time. I stood with my hands behind my head, elbows out and breasts raised. He dipped his fingers inside my pussy and stroked my g-spot. He started gently, but picked up speed until I squirted all over his hands and the hotel carpet (sorry cleaning crew).
Then we said our goodbyes and went home to debrief and cuddle. As I write this, I realize that this type of play won't be for everyone. I know that it is far from vanilla, but I had a great time.
The aftercare from D was wonderful as well. All in all, a two thumbs up vote from me on my first sub experience with another man.
You are making me blush. Your comment is now one of my favorites on this thread, so maybe we can have a mutual appreciation society. 
