Married Female Politician has an Affair with her Staff Member

Rebecca is a 45-year-old white woman with long auburn (reddish-brown) hair. She is tall, slim, and married. She was running for a local political office in our state. Phil is 40 years old and had a part time position on her staff as he helped her campaign. He is white with a shaved head and average height / body type. She won her election. He became a full time staff member and left his other job. Rebecca and Phil became closer to each other because they had spent a lot of time together. However her campaign and new political position put a strain on Rebecca’s marriage.

Both Rebecca and her husband worked long hours and didn’t see each other often. One time Rebecca and Phil traveled for some meetings. He was wearing a shirt and tie. She was wearing a white and pink striped button down shirt with gray pants. They had dinner after the meetings were over and returned to his hotel room. Phil removed his tie. They had some drinks while watching TV. Rebecca was telling him about her marital problems. She was a little bit sad and angry at the same time. Phil gave her a warm embrace.

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Sex with a Hotwife

I had resumed using a sex/swingers website called sls after a long covid break. I had used sls off and on for several years in the past. I began talking with a woman from sls named Kate. I agreed to meet Kate and her husband at a bar. She was around 55 years old, about 5’ 6” with brown hair. Her face had some natural wrinkles. But she had a very athletic/fit body. She was wearing a sweater and jeans. Ron was somewhat overweight and was about the same age as Kate. We were sitting in a circular booth with Kate in the middle. We talked about our experiences with sls and sex/swinger clubs.

They had started out as a traditional swinger couple. However Kate gradually turned into a “hotwife”. Ron would watch her have sex with (often younger) men. Or Kate would have sex with other men when Ron was not present. But with his knowledge and consent. Usually their first meetings with someone just was talking to see if there was a connection. We paid the bill after we finished our drinks and walked back to our cars. Kate gave me a hug. They told me to contact them so we could set up plans for a more intimate encounter.

Latina Cougar at a Sex Club

I was around 30 years old when this happened. I had joined a sex/swinger website called sls. A sex club had listed their events on sls. I signed up for one of the events and was approved by the host(s) or people in charge of it. I had attended a few sex clubs before and quickly realized that sls/sex clubs can often be tough for single men. I knew that I needed to be patient and have thick skin.

A woman that had also signed up for the same event contacted me on sls. Her name was Christine. We emailed/texted each other and agreed to meet each other at the event. I arrived at the sex club on a Saturday night. I was wearing a sweater and jeans. The sex club was at a converted 3 floor colonial house. The first floor had a room for food / drinks and a socializing room. The second floor had a dance room and a few sex rooms. The top floor had more sex rooms.

Sex with My Roommate (MF)

My friend cousin’s had been temporarily relocated for her job. Her name was Amy. She was 25 or 26 years old, very tall, with long blonde hair, and thin. I had already known her from some of my friend’s family gatherings. We had flirted before and even kissed a few times. But nothing more had happened between us. My friend (who had moved away from my area) asked she could stay with me because my house was very close to her job.

I said yes for the following reasons. It was a favor for a good friend. I was in my late 20s at the time and had recently purchased my first house. I figured some rent money would help me pay the mortgage. Last but not least, I felt there was an outside shot that we would have sex. Amy and got along well. There were no major problems between us.

Sex with a Colleague on a Business Trip

I was about 35 years old at the time. I was on a business trip for my job. It was for a seminar that lasted about a week. I was the only person from my branch attending. There were other people from my company, but different branch locations present. I was hanging out with a woman named Sam fairly often during the trip. I had previously communicated with her by email for work related matters. This was the first time I had met her in person. She was in her late 30s, a little bit older than me. Sam was thick white woman with long black hair. She had some curves and meat on the bones, but not fat.

The last day of the seminar was on Friday. My flight home was the next day. Sam’s flight home was also the next day. Sam and I went to a restaurant/bar near the hotel we were staying. I was wearing a black sweater with jeans. She was wearing a black floral dress. We had some food and drinks while talking. There was a connection between us. We were also somewhat in the same situation. I had recently ended a relationship. She was separated and was in the process of getting divorced. I removed my sweater because it was warm. I had a T-shirt underneath.

My Friends Join In Blackmailing My Mother Best Friend

Please see previous Blackmailing My Mother’s Best Friend posts for background info. I had told Paula our deal had been completed. But that changed when I found out she was still cheating on her husband. This time my girlfriend Nicole saw Paula walking into a hotel with the same man. (Nicole had been at the same hotel for a work related event) I came with up an idea for more blackmail. I told with 2 of my friends, Jim and Rick about Paula. Both men were about 30 years old. Jim was slender and Rick had a more muscular body type. They were both interested in having sex with Paula.

Jim, Rick, and I went to Paula’s house. Paula was wearing a yellow dress. Jim and Rick were wearing a T-shirt and jeans. Paula was wondering why I was there with 2 men that she didn’t know. I told Paula that Nicole saw her cheating again. I told Paula she would need to have sex with Jim and Rick. In order for me to continue keeping her affair a secret from her husband and other people. Paula protested and said “I thought this was over with.” I said “It would have been if you had learned your lesson.” Paula knew I had leverage and agreed to go along with it.

Hand Job at an Outdoor Swimming Pool (MF)

I was about 35 years old at the time. I was on vacation with about 10-15 people. I didn’t know some of these people that well before the trip, including a woman named Tammy. She was a 37 or 38 year old thick white woman with long black hair. She had some curves and meat on the bones. But she was not fat. I was hanging out with Tammy fairly often during the trip. There was a connection between us. We were also somewhat in the same situation. I had recently ended a relationship. She was separated and had filed for divorce because her estranged husband had been cheating on her.

Tammy and I did some sightseeing during the afternoon before we used the outdoor swimming pool in the hotel. There weren’t any lifeguards so it was “enter at your own risk.” There were originally some other hotel guests at the swimming pool. But they left. Tammy was wearing a 1 piece swimsuit. I was wearing swim trunks. Tammy was impressed with my muscles and was touching my body. I don’t have the physique professional bodybuilder, but I worked out and was in good shape.

(M)y First BJ

I was a “late bloomer” compared with my friends. Many of them claimed they got their first BJ (or more) in high school or their first year in college. My first BJ happened when I was a junior in college.

I was at a party in my friend’s off campus apartment. I was talking with a woman named Darlene. We had known each other from mutual friends. She was white, had long black hair, and average body type. I think Darlene was wearing a blue button down shirt with white pinstripes. She was about a 5 in a scale of 1-10 in terms of looks. She did have a great personality though.

We left the party and I agreed to walk home with her. My on-campus apartment was very close to hers and she didn’t want to walk home alone. We bought some late night food at a restaurant that closed late during the walk. She invited me inside her apartment. It was just the 2 of us. Her roommate was away for the weekend or was in her boyfriend’s apartment. We ate the food, had a few beers, and talked. She thanked me for walking her home and paying for the food.

My Girlfriend Joins in Blackmailing My Mother’s Best Friend

Please see Blackmailing My Mother’s Best Friend for background info. I showed my girlfriend Nicole the pictures of Paula cheating on her husband. I also told Nicole about how I blackmailed Paula. Nicole wasn’t upset as we had an open relationship. Nicole was about 30 years old, average height/body type, and has red hair. Nicole was also bisexual and was sexually interested in an older woman like Paula. I told Nicole we can make that happen. Nicole and I went to Paula’s house. Paula was wearing a purple dress. Nicole was wearing an orange button shirt with jeans. I was wearing a sweater with jeans.

Paula was wondering why I was at her house with Nicole. Paula and Nicole didn’t know each other that well. I told Paula “You will soon find out.” Nicole kissed Paula. Paula initially protested and said she was not a lesbian. I countered with remember our deal. Paula agreed to go along with it. Nicole resumed kissing Paula. Paula began to enjoy it. They were kissing each other for 15-20 minutes. All 3 of us went inside Paula’s bedroom. Nicole removed Paula’s dress and bra. Nicole and Paula laid down on the bed. Nicole began touching and sucking Paula’s breasts. Paula liked the soft touch of a woman.

Blackmailed a Prosecutor

Paula was a thin white woman with short dark brown hair. She was about 50 or 55 years old. She was also a prosecutor in my area. I had been falsely charged with robbery and other crimes. Paula was the prosecutor in my court case. I was acquitted. But it damaged my reputation and I lost money from the days I had to take off from work. I filed a lawsuit against Paula. We had a meeting so we could attempt to settle the lawsuit.

Paula was wearing a multistriped button down shirt with beige pants. I was wearing a white button down shirt and tie with black pants. She begged me to drop the lawsuit as it could ruin her career as a prosecutor. Paula said she would do anything. I came up with an idea. I unzipped my pants and exposed my penis. Paula said “This is unethical and inappropriate. I am married.” I told her I would continue with the lawsuit if she refused.