Author: EastbayGentleman

Sleeping with the News Anchor [MF]

When I came home after several years working in Europe, the Trustees of my University alma mater reached out to me and invited me to sit on the Board of Trustees. I had demonstrated some modicum of success. I had taken my company public and my name was in the news (in a good way). I was flattered they thought I might be able to assist my school for which I deeply cared. So, I started a five-year term as a university Trustee.

One of the other Trustees on the Board was a local news anchor. We’ll call her Linda. Linda and I went way back. She interviewed me back when my business was first getting started and we had stayed in touch, albeit remotely, over the previous 10 years or so. Linda was tall, lightly Hispanic, shapely and about five years younger than me. Linda was well known in her market, had gone through a difficult time over the previous few years. She had children some years back and had an ugly divorce with another newscaster. Still, you couldn’t tell as her personality remained bright and optimistic. I always admired that about her and I had occasion to share that with her at our first Trustee meeting. Her light mocha skin blushed at my compliment and she demurely looked down. I followed her gaze and quietly admired her thin, muscular legs all the way down to her spiked heels. Read more »

Fucking Aunt Kathy [MF]

(Names have been changed to protect the guilty, but it’s all true)

This story takes me back to my college days. My friend, Bill, was going to be celebrating his 21st birthday, and he invited several of us to his family’s home just outside of Bakersfield to help him celebrate. His folks had quite a spread – large house, resident housekeeper and cook, great yard with a pool, pool house and spa.

Bill and I and two friends piled into his car in the Bay Area, and headed off to Bakersfield. We were great friends, and we laughed and cajoled one another all the way to Bakersfield. A few laws were probably broken, but we arrived there safely the day before Bill’s birthday and party.

The house was large enough that we all had separate rooms, which was, as it turns out, exceptionally convenient. Whenever we went to Bill’s house, we were spoiled rotten by the housekeeper, a large African American woman who seemed like she could cook anything at a moment’s notice. We had a feast of a meal that night and, the next morning, the day of Phil’s party, was non-plussed about making sure we all had a good breakfast as the day got started. Read more »

Sleeping with a Gold Medalist [MF]

Redditors seems to be enjoying the recollections of my past, so I thought I’d offer another one – and I will try to be very careful to not give away who I’m talking about. If you do reach out to me privately, it’s unlikely I will confirm the identity of my friend.

This happened in the middle 90’s. I was on a flight from San Francisco to Palm Springs. I had been invited to play golf at the PGA West TPC Stadium Course with Jack Nicklaus. I was seated in First Class on the Boeing 727 in an aisle seat on the left side of the aircraft. Back in the day, I used to read Sports Illustrated cover-to-cover. I had settled into my seat, not paying attention to the person next to whom I was seated. I opened up my SI – which on the cover had Dennis Rodman in a wedding dress – and started to read. Read more »

Making love to a celebrity [MF] (long)

As I look back on the truly wonderful people I’ve come to know in my life, one of the more memorable people was Colleen. For obvious reasons, I’ve changed her name, but I wanted to use a name that matched her fiery redhead Irish nature. She was exquisite – an actress, former supermodel and, it turned out, just a really nice person.

My company was launching a new line of products and we had worked with Colleen’s agent to use her as a celebrity endorser. I was the CEO and we had selected Colleen after working through our PR firm, her agent, working out the commitments, dollars and, of course, the contract. Read more »

My continuing adventures with gorgeous women [MF] – Ciara

My continuing adventures…this one is about Ciara. I met Ciara at a bar in San Jose. I had been there with some buddies and had shared a drink (I was driving) and a lot of laughs. As I had a long day at the office and was still up for some work that night, I switched to something less strong and went up to the bar for a refill. As I leaned onto the bar, the very buxom lady beside me turned quickly and I felt the unmistakable feeling of boobs pressed into my back.

She immediately apologized and I assured her none was necessary and that it had been the best feeling I’d had all night. She laughed and introduced herself as Ciara. She was a tall, shapely woman with shoulder length dark brown hair, long legs that ended in heels and was wearing a white flowered dress. I guessed she was 5-10 years older than me and probably was mixed race. Her brown almond eyes were stunning. Her plentiful breasts tested the strength of the fabric to some degree. We chatted for a couple of minutes and I bought her a refill on her margarita. She was considerate and sophisticated, and noted the fun I was having with my friends. She mentioned that she had been stood up this evening and that if I wanted to chat with her, she’d wait for me. I thought it was wrapping up with my friends and that, yes, I would like to get to know her better. Read more »

My manslut adventures with gorgeous women [MF] – Part IV

I was fortunate to attend a trade show/convention in San Francisco a few years back. Andrea was attending for her company as well. She worked for a media rating company and was at this show in a professional capacity. She had heard me interviewed as part of this show and came up to me to talk about my experiences.

She was short, well dressed and a bit goth-y. She had short black hair, was wearing black leggings and had a gold print top on that, despite having a high collar, did little to hide the fact that she was not wearing a bra. She knew her stuff and I was surprised/impressed with what she knew of my background. We kept running into each other at the cocktail reception despite the fact that I was dragged away, time and again, to meet someone else. I needed to stay for most, if not all of the reception, given I was kind of the guest of honor. Read more »

My manslut adventures with gorgeous women [MF] – Part III

Julie was another person I met on AFF. She freely shared pictures and was fucking gorgeous. She advertised herself as 42, but I think she was a few years older than that. I was 54 at the time. We met at a yacht club for drinks and light appetizers. She arrived a bit after me and I watched her walk toward me with her tanned skin, 38DD bust and short sundress. Her skin was a beautiful golden tone, but not so dark that it covered her light freckles on her upper chest. As I knew from her pictures, the freckles extended down her body.

We had a wonderfully open and alluring conversation about AFF, what she liked in men, what I liked in women, our sexual experiences and favorite positions. It was great fun as we got to know each other and playfully teased one another with our words. After a couple of drinks each, we wrapped things up and headed out without yet mentioning if we were going to practice what we just preached. I kissed her deeply at her car and she started massaging my hard cock in my pants and said, “Follow me home”? Of course I agreed. Read more »

My manslut adventures with gorgeous women [MF] – Part II

What’s the word for a man slut? I think that probably would best describe me. I have slept with more than 100 women in my life and have shared some incredible and memorable experiences. As I am inspired by many of your stories, I thought it well to document some of my experiences and unforgettable pleasures.

I am pretty seasoned executive and have been in positions of control of both public and private companies.

It’s now time to share a memory about Susan.

I had occasion to travel quite a bit with my work and I found Adult Friend Finder a great way to meet people across the country and, perhaps, to meet up with them when I came to their town. Such was the case with Susan, who lived just outside of Phoeniz, AZ. Susan was in her early 40’s, tall, thin, and beautiful. We had chatted for some time on AFF before I made a trip to Arizona. We had agreed to meet for dinner, together with her son, a kind young man who was developmentally disabled. Susan had commented that it was difficult for her to meet people because so many people were turned off by her son. I found that truly a shame, as she loved and cared for her son deeply, and that should never get in the way of her happiness. Read more »

My manslut adventures with gorgeous women [MF] – Part I

What’s the word for a man slut.? I think that probably would best describe me. I have slept with more than 100 women in my life and have shared some incredible and memorable experiences. As I am inspired by many of your stories, I thought it well to document some of my experiences and unforgettable pleasures.

I am pretty seasoned executive and have been in positions of control of both public and private companies. Most, if not all, would find my behavior and passions quite surprising. In any event, the first story I’ll share is the one about Ellen (not real name).

I had been living and working in London running my company’s European operations. Ellen was an Executive Assistant supporting one of C level executives back home. I got promoted and flew home to begin my transition to the States. My first day back, I met Ellen and she was stunning. She was about seven years older than me, huge breasts, broad hips and a very curvy figure. She dressed stylishly and had an incredible sense of humor. Our conference room had a view of the elevator lobby and at the end of the first day, we wished each other a good evening as she leaned back out of the elevator and expressed that she looked forward to working with me. She was going to be my assistant! My heart and my cock leapt a bit. Read more »