Annual Corporate Meetings Day 01

(This is my first submission on Literotica. This is planned to be a five to six part story involving multiple partners. I hope you enjoy, and please provide feedback so I can improve the quality.)

When I was a younger guy, I had a pretty active and varied sex life. One high school girlfriend was bisexual, and actually loved to watch me have sex with other girls. Another girlfriend gave me my first MMF threesome. A young man's dream...

But, as I got older and kinda settled down, those days were in the past - fond memories that I would call up when I needed a little self-release. Today, most of my sexual activity is of the self-love type. A loveless/sexless relationship can force that on you. I am okay with that because I have a great job and a great kid.

Like pretty much every human being on the planet, when I am masturbating, I may think about people I know. Sometimes I feel a little weird about it, but it is all in my head, so no problem, right?

There was this one girl - Jennifer - that I had known for a couple years. Our company is in a lot of different states, and she was on the other side of the country. We had met in person a few times at annual company meetings, but had not hung out together much. We talked about work and every once in awhile politics or something like that. When I first met her, I thought she was cute as hell. She had a beautiful smile, great blonde hair, and (in the back of my head) I admired her breasts. A great ass, too.

But, I always kept things professional. I will admit that when I was practicing a little self-love, she had popped into the image a few times.

Now, even though I am older, my sex drive has not diminished at all. To tell the truth, I usually masturbate a couple times a day. If I do not, I get really antsy. Kinda sucks when you are in a sexless relationship.

A few months ago, I was a bit horny when I was talking to Jennifer about something innocuous via chat. I let something slip that was a wee bit inappropriate. I was mildly horrified, but she was actually cool about it. After that time, we would chat periodically, and things started getting more steamy. I learned that she likes masturbating too. She has fantasized about being with two guys. She told me about how she had needed to buy a vibrating toothbrush on one trip because she was nervous about bringing her vibrator. By the time that the conversation got this direct, we had moved it off the corporate network and onto our phones.

I had told her about a threesome experience and a foursome experience I had when I was younger, and in the telling I got so horny that I was stuck with a monster erection in the office. She was pretty pleased with herself when she convinced me to go in the bathroom to get a little relief.

All of these conversations definitely made her a regular in my fantasies. I would remember her discussing giving blowjobs and picture it being my cock cumming in her mouth while she was looking up at me.

It seemed like she was like me in her views on sex. As long as everyone is a consenting adult and nobody is being hurt, people should do whatever feels good. No regrets. I loved thinking about, well, fucking her. I loved picturing her having an orgasm. I felt mildly guilty because she was a coworker, but I think she was enjoying picturing me masturbating to her (I had told her about that).

The company was having another annual meeting and we were both going to be in Chicago at the same time. I was looking forward to seeing her because she really was a great coworker, but I was nervous because there was this part of me that just wanted to ravish her, and I didn't want her to think bad about me because of that.

But man, I wanted to fuck her.

The first day of our annual meeting was about what you would expect. Everyone was greeting coworkers they hadn't seen in a year. Corporate house-cleaning stuff for the most part. When I saw Jennifer from across the hall we were meeting in, I smiled. She looked so good. She was smiling as she was talking to another coworker, and I could not get out of my head how damned hot she looked.

I made my way over to her and she gave me a big smile as I approached. I really was happy to see her as she is a great girl, but I could also feel myself starting to get hard as I walked up to her.

She wrapped her arms around me and gave me a tight hug. Her gorgeous tits were pressing into my chest, and her hug was full body. I was a little bit nervous she would feel my hardening dick. Well, I knew she did when her pelvis subtly pressed harder into mine. Barely perceptibly, she moved her hips back and forth. Yeah, she could feel my dick, and I was pretty sure she was enjoying teasing me.

As we stepped back, she whispered in my ear "later". I was already hard, but now I was glad I was wearing pants that were a little loose on me, as I was getting rock hard.

The rest of the day was pretty normal corporate stuff. I gave a couple presentations and collaborated with my colleagues in planning meetings, but in the back of the mind, I kept hearing her whispering the word "later".

By the end of the day, I was pretty exhausted. I had been up late the night before preparing for a week of meetings, and flying always sucked the life out of me. A bunch of colleagues were heading out to dinner and drinks after, but all I wanted to do was head up to my hotel room, take a shower and relax in bed.

Walking into my room, I smiled to myself. I had left a small box at the front desk for her. I had not left a note, but I was sure she would know who it was from.

I shut the hotel room door and then laid my briefcase on the desk. Sitting on the bed, I kicked off my shoes and pulled off my tie. I was beat.

I hung my coat up in the closet, quickly stripped the rest of my clothes off and headed into the bathroom. Climbing in the shower, I could not resist thinking of Jennifer while gently stroking myself. The feeling of her breasts pushing against, her gentle grinding was in the back of my head all day.

I stopped stroking myself and washed myself, thinking about her and wishing she were with me.

After shutting off the shower, I climbed out and dried myself and walked out naked. Pulling the covers back from the bed, I flipped on the TV. It was warm, so I didn't get dressed.

I idly flipped through the channels until my phone beeped. It was a text from Jennifer.

"Guess what I am doing."

"What?" I typed.

"The present you left for me..."

I got a thrill in my stomach. "You like it?"

"Oh yes. I am sliding it in and out of me right now."

I was instantly hard. I knew she would not bring her vibrator to the annual meetings, so at lunch time I had found an adult store, and bought her one - leaving it in discrete packaging at the front desk. "Oh man. How does it feel?"

"So, so good. I am imagining you sliding it in and out of me."

Oh god. I started rapidly stroking myself. "I would go down on you while gently pushing the vibrator in and out of you."

"In and out of my...what?"

"In and out of...you know"

"Say it"

This was so hot. "It would be going down on you while thrusting the vibrator in and out of your pussy."

"Yessss. What are you doing with your tongue?"

"I am licking you."

"No. What are you DOING with your tongue?"

"I am circling your clit - around and around. And then I am dragging my tongue down the the entrance of your pussy."

"I am so close."

I can imagine her face as she is getting close to orgasm, her mouth open and little pants as she thrusts the vibrator in and out. "I wish I could see you right now. I am so hard right now." Being on edge all day had me ready to go any second.

"Oooh. Are you jerking off?"

"Yes. I am leaking precum and so hard."

"So close..."

"I am imagining you licking my cock while I am licking your clit."

"Oohhhhh..."

"I am really close to cumming, Jen."

"Same. I want u 2 cum w me..."

"God yes so close jen"

"Cum with me dan. Cum with me now"

Oh god. I started stroking really fast. "I'm gonna cum!"

"I am cumming dan!"

"Me too, jen!"

I had always cum a lot, but it seemed like gallons of cum came out, and landing all over my chest and stomach. Eventually, i stopped cumming.

"That was so good, jen."

"Mmmmhhmmmm. Me too. I love this vibrator."

"I love that you love it, that I was able to make you cum."

"Mmmmm. Want to see your cock. Soon."

"Soon. I want to taste you.

"Mmmm...yes. Good night, lover."

"Good night, Jennifer."