This is a true story. I changed the names of all and many details to 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.
Recap: In Part 1 I wrote about the initial night that my former boss Jessie and I spent together on a business trip. She was 38, married with two children. She was fairly short, chubby and had a big head of perfectly done copper colored hair, very busty and was always well dressed. I was 40, single and seeing several women. We did not have sex that first night but did play with each other before falling asleep in each others arms.
They sex stuff is after the —— line.
When the phone rang with Jessie’s wake up call, we were intertwined in the bed. She answered the call and then rolled to me, burying her face into my neck. I told her I how much I had enjoyed our time together. She apologized for not taking care of me but promised she would remedy that oversight that night. I got up, dressed, kissed her and told her I would see her in the hotel restaurant for breakfast. As we kissed she touched my face and said “Thank you”.
She entered the restaurant wearing a black skirt, white frilly blouse and high heels. Her blouse was typical of those she often wore – a little low cut that gave a glimpse of her cleavage. I noticed several men watching Jessie’s boobs bounce as she made her way me. We ate quickly saying nothing about our time in her bed that previous night.
We had a productive day at the vendor’s office getting them on the right track. At the end of the our day the most senior of the attending managers invited Jessie and I to dinner. We begged off claiming residual jet lag. But we really just wanted to spend the evening together. When we got back to our hotel we went to our respective rooms to freshen up and change into more casual clothes. We met in the lobby and took a cab to a well known restaurant a few miles away. As it was fairly early we were able to get a table in the back of the patio that gave us privacy.
As we dined Jessie told me more about the state of her marriage. She loved her husband but his health and the drugs he took made sex impossible for him. Jessie was close to tears several times as she talked but she never broke down. By the time we finished our meals our conversation had changed over to sexual banter and innuendo.
We returned to the hotel and she told me to come to her room in 90 minutes. We kissed good bye and went to our individual rooms. I showered, shaved again and dressed in jeans and a T-shirt. I made sure I had a few rubbers in my pockets before heading to Jessie’s room.
When I got to her room I found the door cracked open and could hear her talking. I quietly walked in and locked the door. Jessie was sitting on the bed wearing a hotel bath robe. I heard her say ‘Charlie’ so I knew she was talking to her husband. She looked at me and patted the bed next to her. My dirty mind engaged; I could not resist.
——
I gently got on the bed, opened her robe and bent down to lick and suck her nipples. Jessie never missed a beat in her conversation. She put her right hand on the back of my head as I moved from nipple to nipple. At one point I pushed the phone to the side and gave her a full on tongue kiss as Charlie continued to talk. She kissed me back for several seconds before grabbing my hair to pull my face away from her. She smiled but shook her head. She pushed my head back down to her chest and resumed talking to Charlie in a normal voice.
She got more nipple and tit play but I wanted her pussy. I untied the robe’s belt and opened the robe to exposing her pussy and upper thighs. Jessie tried to stop me and was shaking her head but I was on a mission. I moved between her legs and pried them open. She kept covering the mouthpiece and whispering ‘No’ or ‘Not now’ but I wanted to eat her pussy while she was talking to her husband. Because I am a pervert.
I began to kiss and lick her thighs and tease her pussy with my finger tips. Jessie continued talking on the phone to Charlie and then with each of her daughters. I started to slowly finger fuck her as I licked her pussy, slit and clit. Jessie began to push up her hips rhythmically to help my tongue reach her favorite spot. In short order she was soaking wet and my face was covered with her pussy juices.
I stopped enjoying her pussy and moved up to kiss her mouth. Each time she stopped talking we kissed. Whenever she needed to talk she would turn her face to the hand set and I would kiss her neck and ear. Just for the sake of variety I would sometimes slide back down between her legs to lick and suck her clit. A few times she lost her train of thought when she was speaking. I loved causing her to do that.
When Jessie finally put the phone down she mock scolded me for distracting her. I told her I didn’t care, I just wanted her. She replied simply “Fuck me now”. I got off the bed, undressed and grabbed a condom. I got back on the bed, pulled her down on her back, grabbed a pillow and put it under her ass. I lifted her legs and told her to hold them wide for me. I put the condom on and then rubbed my cock on her pussy lips a few times. (One of my rituals before fucking a woman.)
I put the head of my cock at her entrance and told her to look at me. I pushed my cock in her slowly, watching her face as my dick went in. Jessie never closed her eyes she just gave an “Umm”. I left my cock in her for a brief moment and then began to fuck her at a leisurely pace. I intended this session to last for a while.
But that is not what happened. Jessie began asking me to ‘hurt’ her. !!??!! I had previously had rough sex but never had a woman asked me to hurt her.
I asked her what she wanted. She told me to slap her tits. No problem, I had done that with other women. I started to slap them but she said “Harder”. I began to really smack them; I watched red marks start to appear on both tits. Jessie let go of one of her legs and grabbed my left hand and moved it to her neck. I lightly squeezed but she whispered “Choke me” so I squeezed rather hard (I thought) as I continued to wail on her right tit.
Jessie’s face turned pink and then red, her mouth opened and I could tell she was having a hard time breathing. This whole scene ignited a lust inside of me. I stopped choking her and started hitting her tits harder. I slowed down the fucking rate but increased the power of each thrust. Hard thrust, hard tit slap. Hard thrust, hard tit slap. This went on for a few minutes with each tit slap causing her to grimace.
Eventually Jessie got to her release. She yelled “Oh God” and began to shake and roll her head from side to side. I stopped the tit slapping and leaned down to stick my tongue in he mouth (as I love kissing a woman while she orgasms). Jessie let go of her legs and wrapped them around me. She whispered “Cum now”; I could not last any longer and let my cum go into the rubber.
We kissed for a while and then we each got cleaned up before snuggling in bed to get some sleep. As we held each other in the dark she told me she wanted this to happen; she had been thinking of sex with me since I had first worked with her. I was honest and told her I had thought of fucking her but until the previous day I never thought it would happen. We soon drifted off to sleep.
We spent the next morning at the contractor’s office to finalize our work before flying back to the east coast. Jessie and I never talked about our sex session that morning while at breakfast or while on our return flight.
When we landed Charlie was there to greet her. As we waited for our luggage Jessie told me we would have to prepare a report about the trip the next day. She emphasized we had some ‘important’ things to discuss and had to make ‘firm’ plans for the future. We said our goodbyes and we went our separate ways. I watched Jessie and Charlie walk off hand in hand.
Source: reddit.com/r/sexystories/comments/uxhxvx/my_exboss_jessie_completes_her_seduction_of_me