This is my first post, so here's a little introduction:
My name is Dion, and I'm a male stripper. I started stripping as a college student in 2003, and continue to do so today. I'm also one of the only male stripper bloggers around: http://malestripping.blogspot.com
Anyway, this story took place in 2004 when I was still a college student at the University of Florida in Gainesville, Florida. My company at the time was French Addiction (no longer in business), a lingerie store that also booked male strippers for customers in the surrounding area.
Most of my parties were bachelorette or birthday parties, along with the occasional sorority party. And most of the customers were female… Except this one time.
French Addiction booked a gig at a bar for me on a weeknight, and I was told to call the customer for extra instructions. The customer was an older man named Terry. “It’s our 20th anniversary,” he explained. “I bought a ring and I want you to give it to her.”
“Does she know I’m coming?”
Terry laughed. “Oh, no! She doesn’t know anything about this at all!”
“So what’s she gonna think when some complete stranger walks up and hands her a ring?”
“Don’t just hand it to her. Do a striptease for her first. Put the ring in the front of your thong and make her dig it out. I’ll leave it at French Addiction for you to pick up. Don’t lose it, now! It’s expensive.”
“Won’t she get freaked out by me doing that?”
“Only if she finds you unattractive, but I saw your pictures at the store, so I think she’ll love it!”
When I got off the phone with him, I couldn’t help but think how weird this was. Hiring a male stripper for his wife? I’d never heard of such things. He sounded cheerful enough, though. Not sinister or creepy, otherwise I would passed the gig on to somebody else.
The bar was in downtown Gainesville. Terry had already paid French Addiction, so all I had to do was show up. I called him from outside the bar. “Hold on just a minute,” he said with a lot of shuffling noise in the background. “Sorry, I had to step into the bathroom. Yeah, my wife is at the bar. Her name is Brenda. She’s the hot blonde with short hair, jeans, and nice tits. Just go up and hit on her! Then do your thing. I’ll watch from the side.”
I got off the phone and shook my head in disbelief. People spend money on the oddest things.
Terry had told me that Brenda was in her forties, but she looked ten years younger. There was only one lady matching her description, so I took a seat next to her, causing her to turn. “Hi, Brenda. You look really nice!”
Her eyes widened in surprise, and she gave a nervous smile. “And you are?”
I extended a hand. “I’m Dion, and I have a surprise for you.” In the background, I saw an older guy, whom I assumed to be Terry, give me a thumbs-up. He looked around fifty, very tall with gray hair. With his encouragement, I began dancing close to her.
“Oh my! Did my husband put you up to this?”
“Happy anniversary, honey!” he boomed from behind her. “What do you think of him?”
“He’s gorgeous,” she said, running her hands along my torso. I unbuttoned my shirt, which caused the wife’s grin to spread. She traced her hands along my abdominal muscles, surprising me with her fervor. The shirt came off.
I danced against her shirtless for less than five seconds when one of the bar’s employees ran up to me.
“Hey! Hey! HEY! What the hell are you doing?” he demanded. “Put on your shirt!”
“It’s all good,” I said, pulling out the invoice from French Addiction. “Here’s the receipt for this event.”
His brows furrowed deeper. “Put on your shirt and we’ll talk.”
With a sigh, I picked up the shirt and put it on. “Okay, here’s the—”
“Now get out!” he said, pointing to the door.
“I thought you said we’d talk.”
“We are. I’m telling you to get out.” The employee turned towards the married couple. “You two also gotta go!”
“We were leaving anyway,” Terry said. “I’m not staying in an establishment that hires little pricks.”
So there we stood outside. It was my first time getting kicked out of a bar. Terry and I were fuming about the waiter, trading scathing remarks about him. Brenda didn’t get her strip show or her ring, which was still nestled in my thong, resting next to my penis “So what do we do now?” I asked.
“Well, you showed up and tried, so if you want to go home now, that’s okay. But just throwing this out there first… We rented a hotel room down the road. If you want to finish your strip show for the wife, I’ll throw some extra money your way.”
“Sure, that sounds like a plan.”
“Just follow us, then.”
About fifteen minutes later, we entered the hotel room. Normally, I wouldn’t have felt comfortable doing this, but Terry and Brenda were very friendly and laid back.
“If you feel weird about me being here while you strip for my wife, I’ll just get in the car and drive around for a while,” Terry offered.
I felt weird about him being there, but he’d rented the hotel room, and it was not my place to send him away. “No, it’s fine,” I said. I’ve stripped when other men were present, especially at birthday parties and Jet Set. This was no different… except there were only two people.
Getting started was awkward because I had no music to dance along to. I took off my shirt slowly and danced in front of Brenda while she sat on the edge of the bed. She ran her hands up and down my torso, even helping me remove my pants. I surreptitiously stole a few glances back at Terry. I was used to dealing with young jealous guys who hated the idea of their women touching me.
“Do you mind if I take pics?” Terry asked.
“Sure, go ahead,” I replied.
“Wonderful! I’ll just be in the background.”
His easygoing attitude made me relax a little. I grabbed Brenda’s hands and placed them on my ass, which she squeezed and complimented.
“I have a surprise for you,” I said.
“Oooh—what’s that?” she purred.
“It’s inside my thong.”
Brenda caressed the black shiny material. “I love it!” Her fingers came to rest on the outline of my cock, and she slowly began massaging it. Even though Terry hovered in the background, lust jolted through me. Due to my nervousness, it wasn’t much, but when Brenda touched her lips against the front of my thong and licked, the jolt became a surge. “So am I touching the surprise now?” she asked, fondling my cock.
“Not quite.”
She withdrew her hand and frowned in confusion. “Oh? Is there something else?”
“Pull his thong down, honey, and you’ll see,” Terry said, snapping pictures at intervals.
When Brenda pulled the thong down, everything tumbled out. The ring, the only object not attached, fell onto the bed and bounced onto the floor unceremoniously. I pulled my thong up quickly because I still felt uncomfortable.
“What was that?” Brenda asked.
Terry leaned over, picked up the ring, and handed it to his wife. “It’s your anniversary present!”
“Oh, I love it!” Brenda exclaimed, placing the ring on her finger.
“Thank you so much! I love you!”
“Don’t forget to enjoy your second present,” Terry said, gesturing to me.
“You’re the best husband in the entire world!” she said, then looked at me. “May I take it all off?”
“Sure,” I answered, feeling a little uncertain. Brenda pulled the thong down.
“Feel free to get a blowjob from her if you like!” Terry said chirpily.
I didn’t know what to say. A part of me wanted to refuse because this wasn’t normal in my mind. Common etiquette dictated that I refrain from doing this. But I was 22, horny, and going through a dry spell, so I didn’t say anything. Instead, I danced in front of her. Brenda literally took matters into her own hands, reaching up to caress me. Her hands felt warm and soft. My flaccid member slowly extended. Against my reservations, I exhaled in pleasure and soon became hard. Pre-cum glistened on the head. The wife noticed it, looked up at me with her big blue eyes, and licked the tip softly before putting the head into her mouth. I shuddered.
The camera flashed several times. Terry moved around the room, taking pictures from various angles. His presence was distracting and prevented me from fully concentrating on Brenda. I wondered if guys on porn sets felt this way.
“Wanna lay on the bed?” Brenda asked. “It’d be more comfortable for me.”
I lay down on my back. She leaned over me from my left side and wrapped her lips around me, her mouth gliding down almost half my length. She used her hand along with saliva to massage the other half of my length. I leaned my head back and closed my eyes, no longer caring that Terry was taking pictures. Brenda was good. I had yet to experience a college girl who had oral skills like this! Before long, a strong force began building up, threatening to burst free.
Brenda sensed my excitement. “Let me know when you’re about to cum.”
Terry aimed the camera towards Brenda. “Yeah, I want to get a picture of the cumshot on her face.”
Upon hearing Terry’s voice, the pressure subsided briefly. Dammit, I wish he wouldn’t talk, I thought. Brenda’s workmanship was so good, though, that passion soon overwhelmed me and made me forget about Terry in the background.
I tapped Brenda’s shoulder. “I’m cumming…”
She pulled away as I came, hard. One strand barely missed my head, striking the headboard behind me. More spewed forth, spurned by a lack of masturbation and recent sex.
Brenda flinched. “Oh my… It’s in my ear. It’s in my ear!” She darted up from the bed and ran into the bathroom.
“Honey, I didn’t get a good pic of the cumshot,” Terry complained as his wife shut the door to the bathroom. She emerged a minute later twirling a Q-tip in her ear.
“It’s way in there,” she said.
“Now that’s hilarious!” Terry chuckled. Even I dared a laugh.
Now that the desire left me, a feeling of post-coital shame took over. The church I attended during my youth would have definitely frowned upon this incident. I suddenly wanted to leave that hotel room and go back to my apartment, but as I put on my clothes, Terry and Brenda wanted to talk more. I stayed out of politeness.
I was glad I did, because I learned a lot about them. They seemed like normal people. Terry was retired law enforcement, and his wife worked as a supervisor for a company contracted with the military. Over the years they developed more sexual kinks to try, this incident being one of them.
“That’s why we’re pretty discreet about this,” Terry explained. “We both have reputations to upkeep, kids at home, and Brenda’s the big boss at her company. So we can’t exactly hire a male stripper in our town. That’s why we came to Gainesville.”
“It was a pleasant surprise, I must say,” Brenda said.
I told them my brief story about going to college to become an English teacher. Then I told them about getting hired at French Addiction and working as a stripper to pay the bills.
“That’s a damn fine way to do it, too!” Terry said. “Very smart!”
After speaking with them for an hour, I no longer felt guilty. As I was on my way out, Terry pulled two hundred dollars out of his wallet.
“Here you go, friend,” he said, thrusting the bills towards me.
I was shocked. “I can’t take that!”
“Take it,” he said. “Use it for college! Trust me, I got kids. I understand. Take it!”
I thanked him and Brenda several times. After I left, I played the whole night over and over again in my head. It was strange getting a two hundred dollar tip for getting the best blowjob of my life. I felt like I should’ve paid her that much instead.
Source: reddit.com/r/gonewildstories/comments/3pw6pa/a_retired_police_officer_paid_me_to_strip_for_his
Sounds like an awesome night for you and them. Sorta surprised the husband didn’t want a 3-way / DP, I know that’s what I would have wanted. ;-)
Maybe the husband did have that in mind, but I was quite overwhelmed at the time, being 22 and all. They invited me along to a kink/fetish event at a club later on, but I passed. Believe it or not, I had never DPed a girl with another guy before. I’ve had plenty of threesomes with girls — to the point where I’m starting to lose count.