This is a true story. I changed the names of all and many details to further disguise the identities of those in this story. The dialogues are to the best of my memory. It has been more than 30 years since this happened so I hope you will cut me some slack.
Warning! There is no sex in this post. I am just going to introduce you to Jessie, the primary character in this post, and describe how she and I got to the cusp of our affair.
Jessie was a supervisor in another work group. She had been my direct supervisor for six months but had moved to lead another related team prior to the events in this post.
She was 38, 5 feet tall, about 140 pounds. She was chubby with an slightly above average face, big boobs with beautiful copper colored hair that always looked perfect. Jessie was outgoing with a bubbly personality, always smiling and cheerful. Her work area had many pictures of her, her husband Charlie and her two girls. Everyone loved Jessie.
Me? I was 40, single but dating several women at the time.
In late 1990 Jessie and I were sent on a business trip to meet some vendors and straighten out several problems. In the week before the trip she seemed very excited and mentioned several times how much she was looking forward to the two of us ‘getting to know each other better’.
Jessie and I flew to the west coast, leaving the east coast at 5 AM (uh!), and got to our hotel in late afternoon. We were starved so we freshened up and walked to the restaurant next to the hotel. We each had a drink with the meal and an after dinner drink in the bar. While enjoying our drinks she asked me about a particular woman I was dating. She made some risque comments about her which took me by surprise. I never would have thought Jessie would utter anything like that.
She then abruptly confided she had not had sex with her husband Charlie for more than 5 years. I knew Charlies was quite a bit older than Jessie; he had had several heart attacks and had retired on disability. I did not know how to respond to that and politely said that was too bad. She looked at me for a few seconds but dropped the subject. We finished our drinks and headed back to the hotel.
When we got to the hotel lobby Jessie said she was going to call her family and asked me to come to her room in an hour so we could discuss the next day’s meeting. I went to my room took a quick shower, shaved, brushed my teeth and changed into shorts and a T-shirt. And grabbed a few condoms. Just in case. You never can tell. (I had learned that lesson in college!)
When I got to Jessie’s room the door was partially open. I entered and found her leaning back on the head board while talking on the phone. She pointed to the area next to her on the bed, indicating where I was to take a seat. The room lights were off but the TV was on with the sound was muted. The curtains were closed as well.
Jessie had changed into a sleeveless V neck top and loose shorts. She smelled great. Her makeup had been freshened up and she was not wearing her glasses. Jessie finished talking to her husband and told him she loved him. She put the phone down and told me how much she loved Charlie and her girls.
She went to the mini-bar fridge and got us each a beer. We started talking about work but gradually began doing a little flirty talk. Jessie said I would never guess but she really liked sex starting from a young age. (Hmm. Interesting.) She told me how young she was when she lost her virginity and that she had multiple sex partners in college.
She got a second beer for each of us. We were soon talking about our sex partners in detail. She told me when she first got out of college she ‘dated’ a lot of men at work. And she named names. Including one of the bosses in her chain of command. (More interesting.)
Jessie got up to get us our third beer. When she returned to the side of the bed she asked if I liked her breasts. I told her all the guys in the office loved them. We especially how they bounced when she walked in her high heels. She smiled, put both beers on the side table, got on the bed and straddled me. She asked if I liked how they bounced. I looked into her eyes and told her I sure did. Jessie did not move, she just grinned at me.
I took that grin as an invitation to touch them. I ran my hands up under her top and gripped her melons. Jessie whispered “Yes” and pulled her top off and threw it on the floor. Jessie put her hands over mine and closed her eyes. I massaged them for a just a minute or so before reaching behind her to unhook her bra. I dropped the straps over her shoulders and pulled down the cups and pulled the bra away.
I had a religious moment when I saw those big round orbs drop down in front of my face. Her nipples were sticking out and were just begging for some attention. Jessie opened her eyes as I started to pull on them. She made low “Um” sounds, smiled and then began to run her hands through her perfect hair. I leaned forward and began to lick her nipples. She said something like “Yes that’s it”. Her hands went from her hair to mine. She held my head as I licked her nipples and I began to suck them into my mouth.
As I sucked Jessie began to move her hips forward and back slowly. She was rubbing against the full length of my erect rod with each hip movement. She gave a few low moans and then pulled my face up so we could kiss. We started slow but she picked up the intensity. Her hips started going faster; her breathing got louder and she put her head back. She let out an “Ooh” as her body began jerking. I gently bit the nipple I had in my mouth; she said “No more” and dropped her head down to give me a deep kiss.
When we finished kissing Jessie said nothing but she rolled off of me and headed to the bathroom. I fell asleep within minutes of her leaving me. She shook me awake and asked if I was going to stay the night. I told her “Yes” and she said I needed to get undressed.
She helped me out of my clothes and sneakers. She pulled down my briefs and gave my cock a few strokes and kisses. Jessie told me she would take care of that but we both needed sleep. She turned off the TV and called down to the desk for a wake up call.
She was naked and looked very sexy and I was still fairly hard. But neither of us could stay awake, it had been a long day for both of us. Before she dropped off she said “I hoped this would happen”. We fell asleep in the spooning position.
Source: reddit.com/r/sexystories/comments/tvgo8p/jessie_my_exboss_wanted_to_seduce_me_part_1_str8