But I worked damned hard to get to this position.
This position being doggie style, of course.
She was a Twitter follower that reached out wanting an adventure. I’m not normally one for anonymous play, but something about this one. She was very shy in her manner, and I had to push a little to find out just what it was she wanted.
Her idea was for one time only with no names.
It didn’t quite work out that way, as we have played a few times since then, but I still don’t know her name.
There was an initial concern that she was a lonely guy talking to me, posing as a woman just for the connection. Wouldn’t have been the first time. When she accepted my proposal to meet her and her husband, that went away.
She’ll be reading this and she is aware I had that brief concern. Likely that will bring a cute dimpled smirk to her face.
The same smirk I first saw on meeting her and her husband at a nearby hotel pub.
She was in a red, almost-erin sweater with a thick turtle neck that left her curve-less and was large enough it was almost a skirt over her black leggings. She wore no makeup, not that she needed it. A brunette ponytail cascaded over her shoulder and I felt my hands twitching just to give it a pull.
Best description I can think of for her was a smallish BBW.
Her husband, a bowling ball of a man in an Incredible Hulk T-shirt, was at the table with her.
I’m a large man, myself, but he made me feel small.
As we talked, I found he was just a teddy bear there to encourage his wife. He was a retired offensive lineman in Canadian football, so his instinct was to protect, not attack. He was nervous when I showed up, as well.
She had trouble making eye contact and I did get short glimpses of smiles when I complimented her on her looks.
After her husband paid their bill, he excused herself to go to the washroom, something I later found out was a signal to her husband.
Once she left, he rose from his chair and looked at me sternly. “Don’t be gentle, but don’t hurt her.”
I nodded at him. “Absolutely.”
He dropped a hotel room card key on the table, turned to walk out.
She returned and, seeing the keycard, blushed. “I can’t believe I’m going to do this.”
I stood, picked up the card, and took her hand. “Room number?”
In the elevator, I was informed that her husband was listening from the adjoining room. He was not so much listening to get off, in fact I think I could hear the voice of Bob Cole calling the Maple Leaf hockey game on the TV of his room as we passed in the hall, but he was listening to make certain she was safe.
On the 23rd floor, our position was confirmed. She was on the bed on all fours while I knelt behind her with my erection wrapped in rubber. I could feel her shaking as I wrapped my left hand in her hair and pulled back while my right hand opened her up and guided my cock into her.
Her shaking of nerves ended. Shaking leg orgasms took their place and I lost track of how many she had. It happened at least twice during that first doggie style position. Then I fucked her missionary. Next on the small hotel room love seat with her riding. Then I even bent her over against the floor-to-ceiling window so she could make eye contact with the city lights as she came again.
A few times I made her scream and call out enough that I was surprised her husband didn’t burst into the room. I’m certain he was tempted. But her laughter usually followed.
This was about six years ago.
Two years ago was the most recent time I got to play with her, and it was a similar scenario in concept of meeting her and her bowling-ball husband at the same hotel bar. This time, her boyfriend was also there.
As we talked, I discovered how the experience as a Hotwife has helped drive her confidence skyward. She was no longer the meek shy woman I fucked looking out over Toronto on a July night four years before. I doubt the word boyfriend would have even crossed her mind the first time we met.
I have always believed that this lifestyle can increase confidence, but it is the most pronounced change I’ve seen. I also know that I am not personally responsible for her growth, but I’m so pleased I was even a part of it.
This time her husband gave no instructions this time. It was a cheaper evening for him, as well. He only had one room where he watched hockey with one eye, and us with the other.
I think the Leafs beat the Avalanche that evening, but he turned it off early, so not fully sure. First, he turned it off to watch her boyfriend and I help her in her first threesome experience before his clothes hit the floor for him to join us.
It is a funny circle. The lifestyle builds confidence, and confidence builds the lifestyle.