Author: AmongThePlanet

Hotel Bar. 29 (m) older (f). Can’t figure out if she was a swinger or cheating….

I was at the hotel bar with a bunch of my friends. We had golfed during the day, come back to the hotel to shower, and then met at the bar before heading out for the night.

I was younger. Around 29 at the time. Tall, 6’3, shaved head, goatee, relatively fit and had just gotten out of an engagement.

I think the latter made me resent relationships.

I approached the crowded bar with one of the guys and about to order a drink when I felt a hand on my smooth head. I turned quickly to find an attractive woman smiling. She exclaimed “omg it’s Mr. Clean!” I stood there puzzled for a second and smiled back. She then introduced me to her husband. And to make things even more bizarre some 30ish year old guy and another woman then walked up. The guy says “hey, hey are you hitting on my mom?” Before I could reply the Mr Clean lady jumped in and said “no I’m hitting on him”. The woman was attractive, 5’4”, short red hair and hazel eyes. I guessed she was late 50s maybe early 60s. She wore shorts and a short sleeve top. She just kept smiling me and eyeing me. Read more »

Coworkers giving in pt4 (MF)

Coworker giving in pt4 (MF)

I arrived at the convention hall for dinner and after getting a drink at the bar, I sat at one of the large round tables reserved for our company. Tim, Tony, and Lori were already there. We made small talk about the workshops we had attended during the day when all of a sudden Tim says “Holy shit, look”.

We all turn to see that Tim’s focus was squarely on the woman at the bar. That woman was Cheryl. As a matter of fact I think every eye in the place was on her. She wore a form fitting red dress and dark 4 inch heels. The cut of the dress was low enough to show her ample cleavage and her accentuated her calves and legs. Who knew she had legs like that! We al sat there a little stunned. Tony and Tim who were in their early 30s sat Lori their mouths wide open as they gawked. Erin, who was 28 and was a stunning young woman in her own right, said “good for her” and smiled. I glanced at Cheryl and looked away wondering if our past encounters had contributed to this sudden change in Cheryls appearance. Read more »

Coworkers give in pt 3

Cheryl couldn’t believe what happened. Her coworker, Mark, had left to go back to his room.

She lay there replaying the days events on her mind over and over. Her mind spun. “What did I just do? How will this affect work? How will this affect her life? Would it be awkward to see him again?” And of course “oh my god that was AMAZING, I feel so alive!”

She woke up, got dressed. She put on a conservative blouse and pants suit and headed down to the hotel restaurant for brunch before the days conferences began She sat alone and watched the convention goers coming and going. She knew she’d have to face Mark at some point and wondered how it would all play out.

She saw Mark enter the room. He wore jeans, shoes, a polo shirt and sport coat. He always had this presence about him. Seemed to know everyone and seemed to genuinely enjoy people in general. She caught his eye and he made his way over to her table. “May I sit with you?” He asked. She kinda smiled. The Mark before her wasnt his usual confident self. They started to talk when they were joined by other people they knew from work. Read more »

Coworkers giving in part 2 (MF)

Cheryl’s body stopped quivering. I then positioned myself between her legs. I took my long thick cock in my hand and slid it along her sopping wet slit, teasin her. She looked up at me pleadingly. “Please take it easy “ she asked “it’s been a while for me” I confidently looked back at her and nodded. Slowly I slid the tip of my cock inside her. I locked eyes with her again and as I started to feed her wet pussy my thick hard cock, her eyes squinted and a soft moan escaped her lips. slowly I pulled my cock back and then slowly drove it back in. Again I slowly withdrew my cock and then slowly slid it back in. Each time I bottomed out I could feel her muscles clench me.

Her legs wrapped around my waist and I took that as a sign that she wanted more, so I would slowly withdraw my cock and then plunge back inside harder now. Over and over slowly withdrawing my cock and then plunging hard back inside. I took her slowly and deliberately. Savoring each stroke.

Each time I now thrust into Cheryl she now thrust back and I knew she wanted even more. Read more »

Coworkers give in (MF)

I’m 50 years old. I’m tall, I’m strong and I’m flirty. I’m the one that jokes and teases but you know is harmless. I’m also respectful and kind.

I was sent to a work conference down the Cape.

So Cheryl, my coworker, and I made our way from just north of Boston to our destination. Cheryl was older than me. She was 60. She was curvy. She always dressed well, nothing over the top. She was always professional but not aloof. She has shoulder length brown hair and a great smile. She was someone who I respected so our banter at work was more professional than flirty.

We get to the hotel and my room is ready but hers is not. I suggest we put her bags in my room and then when her room is ready we can move them to hers.

We get to my room and I’m kinda nervous. Not because I’m worried about anything sexual at this point, but, I just don’t want to do or say anything stupid.

We go to the room and freshen up. We made some small talk, as there was this uneasiness in the air, and decided to fo down to the hotel bar for a drink. Read more »