During the summer of last year, I signed up for a bachelorette party that was unlike the typical group of party girls. First off, the customer was the husband. That's not so strange in and of itself, but he requested pics with my company before proceeding with the booking. With my permission, the company complied and sent him pics, to which he responded that I was "perfect." Great... He also wanted to talk to me on the phone a week ahead of time, which is very unusual. I had a hunch where this was going.
The following phone conversation confirmed my suspicions.
"I want to give her a good surprise," he said. "and I figured a male stripper would be perfect for her." He rambled on about how hot she was despite being in her forties. According to him, she taught classes at a local gym and was in great shape.
"Do you think she'll like this surprise?" I asked, wary of the outcome.
"Oh, she'll love it... Put it this way: I would be happy if both of you walked away from this satisfied. Do you catch my meaning here?"
I did. But I was still skeptical about surprising the wife. Given my experience in the profession, some women really hate such surprises from their husbands, especially having a complete stranger come over to strip. It makes them feel very awkward.
Surely enough, the husband called me back a few days before the so-called "bachelorette party." He told the wife and she was not pleased. "We may have to cancel," he said, sounding completely disappointed. "She said, 'absolutely not.'"
I wasn't surprised. However, I had a solution. "Instead of telling her there's a male stripper, why don't you tell her that you booked a private massage session for her?" I suggested. "That sounds much more appealing and less appalling. It'd be like a nice trip to the spa, but a home delivery type of service."
A brief pause. "You know, that's a good idea. I'll do that." He reiterated that despite the massage, he wanted me and his wife to walk away from this encounter satisfied.
Apparently, the wife did not object to the idea of a private masseuse. The next night after performing for two bachelorette parties, I arrived at their condo, which was on the beach. I wore a three-piece business suit to look professional. I carried a bag with extra clothes, a portable speaker for music, massage oil, and several condoms.
A fierce storm raged outside as I knocked on the door to the condo.
The husband answered. He was tall, standing a few inches above me. Although his hair was white and close cropped, his face had a younger look. He still looked like an older man, just not quite that old. He greeted me and gave me a firm handshake. His upright posture and matter-of-fact demeanor gave me the impression that he was former military. "Come on in," he said. "She's in the living room."
I entered the living room and saw her sitting on the couch. The wife was blonde, tan, and wearing only a bath robe. She was very attractive and the slit of the robe revealed her well-toned thigh muscles. She stood up to give me a hesitant handshake, but quickly sat down and said nothing more.
The husband said, "Here, you two get to know each other. Do you want me to leave the room?" I knew she felt awkward. Hell, I felt very awkward.
I flashed her a smile and said, "Your husband was right. You look very attractive and fit. Do you work out a lot?"
That broke the silence, as she politely answered me, even telling me about her workouts. I continued conversing with her in the most outgoing and carefree tone possible. The husband offered me a beer, but I declined. Finally, I asked the wife if she was ready for her massage. She stood up and said, "lead the way."
As we entered the bedroom, lightning flashed through the windows followed by a loud thunderclap, and suddenly the electricity was off. It was complete darkness, save for the occasional lightning flashes.
"Goddammit!" the husband swore in the other room.
"I guess we're doing this in the dark," I said to the wife.
"I might as well take off my robe," she said, "since it's going to get in the way of the massage."
I agreed. Her robe fell to the floor and she climbed in bed. I stripped down to a thong, even though she couldn't see me in the darkness. I used the light of my cell phone to navigate the room. I pulled out the massage oil and started with her back.
She was tense, but quickly relaxed as I worked my way towards her legs and down to her feet. Then I placed her foot upon my bare chest as I started on her other leg. I eventually kneaded her muscles and made my way back up to her ass, which was round and firm.
"You must train a lot," I said. "Your ass feels amazing."
"Squats," she replied. "And thank you."
I spent more time than necessary pressing my thumbs into her glutes. After that, I had her turn over onto her back, so I could focus on her shoulders and arms. Her round breasts, augmented with silicone, were barely visible in the darkness. My hands began rubbing them, eliciting a moan from her. They moved down to her inner thighs. She parted her legs slightly as if inviting me to go further. I did.
She was very wet.
Several minutes passed. Her moans became louder. Her hands began caressing me.
"Do you want more?" I asked her. I was quite sure she did, but I wanted verbal confirmation.
"One second." I retrieved a condom from my bag. I climbed atop of her and her legs parted to embrace me as I slowly entered her. She was very sensual. I thrust slowly back and forth as she ran her hands along my arms. She squeezed my muscles, and then traced her fingers across my chest. Finally they found my ass where she took a firm hold. The occasional lightning flash illuminated her breasts and her face, as though providing a teasing glimpse of the view.
The massage had already heightened her senses. It didn't take her long to climax. She grabbed my hair as she shuddered, gasping my ear. I did not last much longer. I turned her over and entered her from behind, grabbing her round firm ass. It was one of the most muscular ones that I've felt. The sensation of being inside her combined with the feel of her ass sent me over the edge. I pulled out, took the condom off, and painted her ass with warm cum. Some of it shot onto her back. The rest I rubbed onto her ass cheeks with my cock.
"I need to get a massage from you every time," she purred. "Did you enjoy yourself?"
I told her that I did. I meant it.
Before I could get too comfortable, her husband barged into the room. "I forgot to pay you," he said, handing me a wad of cash.
I didn't know what to say. It's a strange feeling when you just shot a load on a girl's ass, and her husband walks in and gives you money while your cock still on her ass. I guess he wanted to see the aftermath before the towel wiped it all away, not that he could see much with the power being out.
"Did you two have fun?" the husband asked.
"Yes," the wife said.
"Can I get you two anything? A coke? Beer? Water?"
"No thanks," I said.
"Okay, let me know if you need something," he said, shutting the door behind him.
I sat there hovering over the wife from behind her ass, holding a wad of cash in my hand. Some of the bills fell onto the bed. It was too dark to count it. I assumed it was the appropriate amount.
"That was awkward," she admitted.
"Somewhat," I agreed.
We both got dressed. Ironically, the power came back on. The husband wanted me to stay longer. "Go have your way with her again," he offered. "She can't get pregnant, so fill her up."
I politely declined, stating that I had to wake up early in the morning, which was true. But really, I was worn out. This whole event was stressful. There was high expectations that I would satisfy the wife, and a good amount of money was involved. I felt obligated to do a good job. It wasn't a regular hook-up where I could relax. I had to perform, and it had to be great.
The wife thought so.
She sent me a text the next day. Her husband gave her my number. She wanted me again for her next vacation. So far, nothing has materialized yet, but she periodically contacts me with provocative pictures (sorry, I'm not going to share them here). Unfortunately, I've been too busy to follow up, but we'll see what the future brings.