As an older divorced man in my mid-fifties, I have found it easier to “rent” a young woman every four to six weeks to satisfy my urges. Yes, I hire a prostitute. A whore. Or, as they like to be called these days, a “provider.”
There are many websites where a man can run a search for such ladies. They have typical dating site features where you can filter things like age, miles, ethnicity, and even the services they offer. Most listings include a price, but some ask that you text them.
Having been involved with this “community” for about five years, I have met my share of ladies. Several women have invited me to attend social events held at local bars where the men and ladies can mingle. I’ve been to one woman’s house the past three Junes for her annual birthday BBQ and pool party. I have also been to several Silicon Valley parties at a restaurant and bar where the organizer supplies a DJ for karaoke and then dancing after the restaurant closes.
At the last party, I was talking with three other men when from behind me I heard a female say, “Hey, Danno.” My friend Dan smiled and said hello to a woman named Crystal, whom I could not see. I turned to see who it was and was shocked at who I saw.
“Sierra?” I exclaimed.
The look on her face was pure panic. “Tony!”
I could see the confusion in Dan’s face. “You two know each other?” he asked.
Both Sierra and I stuttered. Neither of us knew what to say.
I quickly looked at the men and told them, “Yes, we know each other in real life.”
One of the other guys asked, “Do you two work together? Crystal, aren’t you a paralegal?”
Sierra, or “Crystal,” is a paralegal in her real civilian life but the others have no clue as to what I do for a living since I am super private about my real life with my friends in the “hobby.” They didn’t even know my name was Tony until that moment since I go by a handle.
I quickly took control of the situation, telling the men that we know each other in real life, but not from work. I told them we’d be back in a few minutes as I interlocked my arm into Sierra’s and walked to an empty spot near the pool tables.
“What the fuck?” was all I could mutter.
“You can’t tell anyone that I do this,” she begged, referring to being a lady of the night.
With a serious look on my face, I told her, “Who am I going to tell? My kids? Your dad?”
Sierra whispered, “Why are you here? You should be getting a ton of pussy since you’re divorced.”
“You’re right, I should be, but this is easier,” I laughed.
The backstory is that Sierra is one of my twin daughters’ best friends. They have all known each other since middle school, attended church youth camps together, etc. Her parents had an ugly divorce when she was age ten and she lived with her father as her mother was a raging alcoholic. In fact, my ex-wife and I would joke that she was our fourth child because she was at our house so much. I bet she ate dinner with us twice a week. In return, her dad would take all four girls (I have three total) to Santa Cruz for a week at a beach house that he rented every July. My ex and I would escape to Mexico or Hawaii for a kid-less vacation.
I started to piece things together as she and I stood there in disbelief. My girls knew that Sierra became a paralegal after graduating college, worked at a Sunnyvale law firm, owned a nice condo, bought a new BMW last year, and had all of the designer handbags and fancy shoes a thirty-year-old woman would desire. Sierra, or Crystal, was working as a provider as a side hustle.
I had stumbled across Crystal’s online ad a few times, but she never showed her face; it was always blurred out. Her reviews were good, and the men said she was attractive, skilled, and a lot of fun. “Now I understand why you don’t show your face in your ads,” I said. I remembered that she worked only by appointment in the evenings, and weekends needed to be booked two days in advance.
Sierra came clean to me, “Tony, I only do this for extra cash. I see maybe four or five guys a week.”
I stopped her. “You don’t need to explain it to me. I will never say a word to anyone. Let’s just tell these guys that we know each other from your office. They don’t know what I do or where I work.” The community did not need to know that I owned a successful insurance business with seven offices, or that I lived an hour plus away.
She quickly gave me a long five-second hug and whispered into my ear, “I’ll give you a free session to keep you quiet.”
I was surprised. “Oh, you don’t need to do that. Besides, wouldn’t it be kind of weird?” I said.
Sierra smiled, “I’ve wanted to fuck you since high school. I was so jealous of Missy (my ex).”
This is where my little head started thinking for my big head. Sierra was a cute girl in high school and college. I have to admit, I enjoyed having my daughters' friends over to our pool during the summertime and checking out their tight little bodies. But, now, as a thirty-year-old young woman, she was looking very attractive.
She was now about five-nine tall, plus her high heels, a slender size six, and was blessed with big full tits like her mother, probably thirty-four DDs. On her thin frame, her boobs looked even bigger. Sierra had light brown hair with golden highlights and brown eyes. She wore classy makeup, luxe lashes, and had perfectly shaped brows. She looked amazing. Now I understood why “Crystal” was getting $600 per hour for a “date.”
I fessed up, “I will admit I enjoyed seeing you girls in your bikinis at the pool.”
She laughed, “Yeah, we saw you checking us out. The older we got, the more we wanted to tease you.”
“I’d be lying if I said I didn’t beat off thinking about you, Miranda, and Ximena,” I said as I made the motion with my hand. “OK, we better get back to the group.”
Sierra and I joined the men I had been talking to and she told them that we had met several times at her law firm. None of the guys asked more about it. I did learn from “Buddha” that he has had four sessions with “Crystal” and that she is amazing.
Then he added, “So your name is Tony and hers is really Sierra?”
“Yes, but only call me Doc,” I told him and the others in a serious tone.
The party proceeded for several hours, and I kept my distance from Sierra but kept an eye on her. I did catch her looking at me several times too. I’m sure we both were a bit nervous.
I mingled with other guys and gals that I’ve met at these social events during this time too. It is a nice way to see if you have any chemistry with a working girl before you drop a minimum of $400 to over $1,000 on a multi-hour “date.” It was not unusual to see a pair leave the restaurant together and then return an hour later. A lot of the attendees book a hotel room next door. Or you might notice that someone has left the party and then magically they show back up. The men always have a smile on their faces.
As the party was winding down just after midnight, I wanted to say good night to Sierra and reassure her of my promise to not tell anyone of her side hustle.
As she saw me approaching her and two other ladies, she took a few steps away from her friends. I gave her a nice hug, which I have done hundreds of times over the past fifteen years, and a simple kiss on the cheek.
“My lips are sealed. Your secret is safe with me,” I told her as our eyes locked.
“Same,” she said. “Why don’t I come back to your hotel room?”
“I don’t know…” I slowly said.
“C’mon, let’s get naked. As I said, I’ve wanted to fuck you since I was sixteen,” she whispered as we stood inches apart. “What do you like?”
“I like it all,” I said, laughing.
Sierra grabbed my hand and started walking toward the backdoor and to the hotel. I did not protest and simply let her lead the way. We didn’t say much on our short walk across the parking lot, but once in the elevator she pressed against me, started rubbing my cock through my chinos, and licked her lips.
“I can’t wait to have your dick in my mouth,” she giggled. She then pulled my head down and French kissed me until the elevator doors opened.
We were soon in my hotel room and making out like a couple of teenagers in the back row of the movie theatre. After a good minute we broke and she said, “Take off your clothes,” as she unzipped the back of her red mini-skirt.
I watched her every move as I quickly undressed and tossed my polo and chinos on the dresser. Sierra turned on the tv and put on a music channel with low volume.
“Sit on the edge of the bed,” she directed me. She grabbed a towel from the bathroom and placed it between my legs, and kneeled down on the floor. She reached out and started stroking my already erect cock. “Nice, you shave your balls.”
Laughing, “I’m old, not dead. Of course, I shave my balls, I love having them licked and sucked.”
With that she lifted my manhood high and licked from the bottom of my sack to the top of my mushroom head. Sierra had locked eyes with me. She then swirled her tongue around my helmet, causing me to moan.
“Ohhh, that feels so good,” I whispered.
Sierra licked back down my shaft, and quickly licked my balls about five times, making me giggle. She then took one testicle into her mouth and sucked on it, pulling away from me and stretching my chicken skin sack. As she released my ball it made a nice “pop” sound. She repeated the same on my other jizz filled orb. All this time she was slowly stroking my dick.
