It was January 2004. I’d been invited by my boss to accompany her to a conference in Atlanta. Translation: she needed a wingman/sidekick/bad girl to hang out with her at this boring 3-day conference. I was happy to oblige. I enjoyed any opportunity to let my hair down and sow some oats.
Her name was Jane and she was simply beautiful. She had the facial structure of Angelina Jolie, with dark auburn hair. She was tall and statuesque. Men noticed her. And you put us together with my long dark wavy hair, full lips and hourglass body, and we caused quite a stir. On our first night there, we sat at the hotel bar chatting over happy hour drinks, when we were approached by two older gentlemen. They sat down with us and struck up a conversation. Before long, we were having dinner with them. They were from Boston, there on business with large expense accounts and even larger…egos. We grew tired of their posturing and excused ourselves soon after dinner.
We were both tired from the day’s events and retired to our room. Since I was not a paid attendee of the conference (I was just there for Jane) I had to share a room with her. It was no big deal, as there were 2 queen beds and a bathroom mirror large enough to accommodate us both getting ready at the same time. It was all good. We put on our pajamas, cracked open a bottle of wine and had cocktail confessions. It was like a grown-up sleepover. We laughed and giggled for hours. Jane was just as wild as me. We shared stories of our escapades, as we finished up the wine and moved on to a fresh new bottle of gin. We were both sauced when Jane spilled an entire drink on her bed. It was soaked.
“Guess I will just have to bunk up with you tonight!” she exclaimed. And we laughed and drank some more. It was approaching 2:00 am, when we finally ran out of mixer and decided to go to sleep. She and I said our good-nights and crawled into my bed. I was beginning to dose off when I felt her hand on me. I had my back to her, but felt her playing with my hair. At first, I didn’t know what to do. I’d been with women at different times in my life, but it had been years…and this was my boss. I began thinking about how she would feel, how she would taste and I slowly rolled over to face her. She looked at me and stroked my face.
“You know me spilling that drink was no accident, don’t you? I’ve wanted you since I hired you. But I don’t want you to do anything that would make you uncomfortable. I just want you to know the door is open.”
And without thought, or hesitation, I leaned over and kissed her soft mouth. I don’t remember the specifics, but I do remember that we flung off the covers and sat up in the middle of the bed kissing while we undressed each other. She pulled me into her body, facing me away from her as she massaged my spot, making me cum almost immediately. I could not wait to taste her as I opened her legs and found that she was dripping wet with anticipation. I made her wait for it, teasing her by kissing her inner thighs, avoiding her sweet cunt, until she could not stand it any longer. We fucked all night. No inhibitions. No limits. Insatiable. We finally collapsed as the sun rose, getting about 2 hours of sleep before we had to wake up. I heard her in the shower when I shuffled into the bathroom for a drink of water.
“Good morning, you.” she said from behind the shower curtain, “how did you sleep?”
“I didn’t get much sleep, but I feel rested,” I replied.
“Yeah, me too.” she snickered. She soon made her way out of the shower and I jumped in. We went about our day as if nothing had happened. There was no awkwardness. No shame. No difference in how we were than before it happened. I was glad. I didn’t want there to be any strangeness.
That evening she had made plans for us to go to a local night spot for dancing. We ate a quick dinner and hopped a cab to the club. We danced for hours. She found a “friend” and went back to his place. He was a strapping young lad and I knew she was in for a good time. I’d met a few fellas, but no one that really interested me, so I went back to the hotel. As the cab approached the door to the lobby, a man that was standing out front opened my door, “Good evening. Let me help you out.”
I smiled and said, “Thank you. And they say chivalry is dead.”
He said, “I am proof that is not true. Let me show you. Come have a drink with me.”
And I thought…what the hell. Why not?
Over some very dirty Martini’s I found out he was from Ohio and was attending the same conference that we were. He mentioned seeing me during one of the workshops and wanting to ask me to dinner, but not having the opportunity. He was nice looking and smart. And married, like me. He was charming and I’d already made up my mind to fuck him senseless before the night was over.
After several drinks, I excused myself for the evening. He insisted on walking me to my room. I knew the routine…we would kiss…our clothes would end up in a pile on the floor….we would fuck…he would leave and that would be that. But when we got to my room, he froze. No kiss. No move. Nothing. I didn’t make a move either, I was expecting him to. Before I knew it, he was walking away to his room. I shrugged it off. I would have liked to have had wild, crazy sex with a stranger, but if it was not in the cards…that was okay too.
I had just gotten undressed when I heard a tap at the door. I peered out of the peep hole and saw him standing there. I answered the door with nothing on but a towel, wondering if he had finally gotten up the nerve to seal the deal. He saw me standing there barely covered and it was on.
We kissed as we made our way to the bed. I still had the towel on, but he reached up and pulled it off of me. I began taking off his shirt and pants. When I pulled down his boxer briefs, I was in shock. I was not expecting him to be packing. He seemed so unsure of himself. But this fella was hung like Seabiscuit. I was in awe. Regardless if he had skills or not, I knew exactly what to do with that. I could not wait to have him inside me.
After he fumbled with the condom, I finally got my wish. His cock was so large that I felt a tinge of pain as he pushed himself inside. I loved it. He wasn’t aggressive enough for me, so I took the lead and mounted him. I don’t remember how many times I came, but I loved fucking him. After a couple of rounds, he got dressed and left, just as Jane came in. I told her about him and she told me about her night. She’d had a great time with a young cowboy. He was not as well endowed as my guest, but she had lots of fun.
And although her bed was in pristine condition, no drinks spilled on it that night, she chose to sleep with me. We didn’t do anything but sleep…tangled up and naked, both of us sated. The morning came and we were back to business as usual. We maintained a great working friendship and never crossed that line again. And although we work in different states, we are still friends, and Jane is just as beautiful.
(Photo credit, Pinterest)