This is the tenth story of my series about my post-marital sexual journey. Read the first story (Babysitter Lauren) or my profile, for any background needed. You may see references to prior stories/people, but for the most part each story stands on its own. There is a second part to this that will be published in a few days.
Not everyone likes me or my stories. That's OK.
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Gabby
About a month or so after I had ended a three-month relationship with Susan, I received a text from Gabby, a mutual acquaintance of Susan and mine. We were all members of the same country club.
Gabby was very formal and proper. Her demeanor was one of constant sophistication, the personification of high class. Perfectly manicured, impeccably dressed, well-spoken and courteous at all times. Always a perfect hostess whenever she entertained, and she expected similar treatment as a guest. First class, high-society all the way.
She was married to one of the wealthiest guys at our club. Her husband had started and sold several tech businesses, and he was worth a fortune. He was about 25 years older than Gabby, who was about 40 (to my now 44) at the time of this story.
Gabby's text said something along the lines of "Hello Philip. I've come to hear that you and Susan ended things. I'm sorry to hear this. If you need someone to talk to in your time of grief, please do not hesitate to contact me. I would be privileged to discuss with you matters of the heart."
To be honest, the break up didn't bother me in the least. Susan was a great lay and we had fun in bed together, but she was one of a fairly long line of women I'd fucked over the prior three or so years since my divorce. It was no great loss and not anything that I lost any sleep over.
But the offer from Gabby was appreciated, and she was a striking, beautiful woman, so I offered for her to meet me at the club a few nights later for a drink or two.
Gabby was knockout gorgeous. Tall; jet-black hair; perfectly round, full tits; slim waist; and a nice, full round ass. Ten out of ten. Except for when she wore bulky sweaters, you could see that she had huge nipples. Her high beams were always on, and she always wore the tightest and skimpiest bikinis to the club pool to show them off.
Her hips were a bit wide and her ass bigger than normal, the result of having children twenty years ago from a first marriage. But she carried it well thanks to her height, and she looked great.
The morning that we were scheduled to meet, Gabby texted and asked if we could just meet at my house to avoid any perceptions of impropriety in being seen together.
This struck me as slightly odd, mostly because it wasn't like her to invite herself somewhere. She would have considered that unsophisticated and rude.
Nonetheless, of course I accepted her offer to bring a bottle of wine to my house.
She arrived as scheduled with a bottle of some ridiculously expensive red wine. She looked fantastic. Fingernails and toenails perfectly manicured, high heels and a tennis skirt with a button-down blouse. Her simple outfit probably cost thousands.
"Good evening, Philip," she greeted me rather formally. "Your home is quite lovely, and your decorating has a perfect touch. It is splendid."
(By this time, I had moved out of my rental house and into a nice, big townhouse about a two miles or so from my ex-wife. Still in the same town and convenient to her house, the schools, parks etc.)
I thanked Gabby for the compliments and offered her a chair in my front living room, and we chatted as friends do, catching up on our kids and what they were up to.
The topic rolled around to Susan, and I explained the reason for the break up and expressed that I wasn't all that upset about it, having been through multiple relationships over the years.
Out of the blue, Gabby said, in her formal, lady-like tone, "Pardon me for being rather blunt, but Susan shared that you are quite well-endowed."
I almost spit out my drink.
I looked at her and raised an eyebrow, unsure how to react.
Gabby's tone changed, now a little bit more "normal" as she clarified, "She said you have a really big dick."
"Did she now?" I asked, starting to sense that Gabby's visit was going to be more than a friendly-shoulder-to-cry-on situation.
"Yes. Biggest she's ever had, she told me. 'A cock as big and hard as a baseball bat' I think were her exact words," Gabby replied, her formalness continuing to give way to full-on trashiness.
"Well, that's a nice compliment, I guess. But what does that have to do with our breakup?"
"Nothing." She stared me in the eye, all pretentiousness now gone. "It has to do with the fact that my husband has a little dick and I really, REALLY need a big dick."
"Why'd you marry him then?" I asked.
"Money. He has a lot of it and I like it."
At least she's honest about it, I thought.
"He likes to show me off, it validates him as a big-shot businessman. I'm his trophy. And in exchange I get to buy clothes and shoes and jewelry, take trips. Whatever I want. But his little dick is pathetic, plus he's older and on a bunch of medication, so he doesn't get it up much anymore. So, every now and then I need to get fucked by a nice, big cock."
Gabby kicked off her shoes, got up and started walking toward me. She stood in front of me for a moment as if waiting for me to give her permission.
"Is this one of those times?" I asked.
She nodded, "It is. It's been over a year. Do you mind?"
"Not at all," I answered, unable to believe my good luck.
I nodded, and she dropped to her knees in front of me as I sat on my couch. Gabby started unbuttoning my shorts, then pulled down the zipper. She grabbed the waistband and pulled off my shorts and boxers. My cock was about half hard, laying sideways onto my leg, and growing as Gabby grabbed it.
"Wow!" she proclaimed. "Susan wasn't kidding. And she didn't say a word about these big balls or the giant golf ball-sized head you have. Holy fuck."
"What else did she tell you?" I questioned her as she stroked my cock to full hardness.
