A Lost Bet Turns into a Fun Night

"You lost the bet." Lindsey said.

"I know. I still can't believe they blew a three-run lead in the ninth inning though. I'll get the next round of beers." I replied.

"No- let's make it more interesting. I have a girls' night this weekend for Emily's birthday and you know she recently broke up with her boyfriend. What if you were a stripper for us?" Lindsey countered.

I shrugged at the suggestion and said, "I don't know...those stakes seem kind of high and I've never done anything like that before."

"Tell you what, I'll do the same for you and your friends if you win." Lindsey said smiling and raising her eyebrows.

To give you an idea of what Lindsey looked like she was a petite brunette with medium-sized boobs and a nice round ass. In this exact moment, she was wearing a low-cut top that showed off her cleavage and a pair of jean shorts that left little to the imagination. Lindsey's smile and light green eyes turned head as did her long flowing brown hair reaching just down beyond her shoulder blades.

"I'm in!" I said without hesitation.

Unfortunately for me, the second game of the doubleheader did not go any better for me and now I was stuck performing for Lindsey and her friends. As we walked out of the bar, Lindsey said she would be sending me a package containing my outfit for the weekend and she would be providing the music for my show.

On Friday, the package showed up and contained a g-string, a pair of tearaway pants, and a tight cut-off shirt. As far as muscles go, I'm not the most muscular person but I do work out multiple times per week, have a four-pack of abs, and a six-inch cock. I did need to manscape I quickly found out after putting on the g-string. I didn't shave completely bald but my pubes were quite short upon completion. I watched a few videos online to get some ideas for how to dance.

Ahead of meeting the ladies on Saturday night, I took a few shots of whiskey to loosen up and then changed into my outfit. I drove to the address Lindsey had sent me that day. I went up to the door and knocked. The loud noise coming from inside quickly quieted down upon the ladies hearing me knock. That noise turned into giggling and I heard movement inside. Lindsey opened the door and smiled at me, "You ready?". I took a deep breathe and told her I was as prepared as I could be. She continued smiling and grabbed my hand and led me into he living room.

"Ladies...I present the entertainment for the evening. I've seen him in a speedo before. Let's just say you are in for a treat." Lindsey exclaimed to much cheering and with that she pressed the play button on the speaker hooked up to her phone. "Take it away, Jeff!"

Music began playing and I slowly started moving around the room gyrating my hips back and forth. Four women were in the room- two brunettes (Morgan and Lindsey), a blonde (Emily), and a redhead (Donna). I described Lindsey earlier but the others were equally attractive.

Morgan was the first girl I arrived at. She smiled and leaned forward running her hands down my thighs and then squeezing my butt. Her large round breasts were perky and, based on the fact I could see her nipples through her shirt, not covered by a bra. I enjoyed the view as she leaned forward and winked at her. I put one leg up next to her on the couch and swung my hips forward so my semi-hard member got close to her face. As I sauntered away, she gave me a hard slap on the butt and laughed.

The next person I came to was the redhead, Donna. Her boobs were on the smaller side but she was incredibly attractive with a short haircut down to her shoulders and bright green eyes. Her smile was radiant and she lifted my shirt slightly to see my abs and gasped as she ran her fingers along them. I sat down on her lap before thrusting my hips forward. Donna reached down and cupped my now very hard shaft and whispered in my ear that I needed to start shedding clothes. Without even responding, I pulled my shirt up over my head and threw it behind me to raucous applause. I stood up and moved on to the next person but not without one last wink back at her. She responded by licking her lips.

Lindsey was next in line and I saw a look of desire in her eyes that I hadn't previously seen. I danced over to her, turned around and sat down on her lap grinding my butt against her. She immediately reached around front and began stroking me. I leaned back with a deep breath and she whispered in my ear that she had always wanted to fuck me and didn't plan to let me leave until I did so. I stood up knowing that if I stayed long I would certainly blow my load. I winked as I walked away and she bit her lip with that same expression of desire on her face that I had seen walking over.

The blonde I arrived at next was the birthday girl, Emily. I knew Emily through Lindsey but had only actually met her twice. However, I had not seen her since she got a boob job last year and to say I was impressed was an understatement. She had always been slightly flat-chested but now she had perfectly round C-cup sized boobs that complemented her fit figure. I knew I needed to do something special for her as the birthday girl and I had a plan for this. I grabbed her hands and pulled her into a standing position in the middle of the room. I strode into the adjoining kitchen and grabbed a chair. I had her sit down in the chair and then I put my foot up on the chair between her legs and began thrusting my hips forward. She clapped excitedly before I sat down on her lap and grabbed her hands. I took her hands and ran them down my chest to my hard cock. She looked over at Lindsey mouth agape before i took one hand and turned her attention back to me.

I stood up, took a step back, and ripped off the tear away pants revealing my g-string which was straining to even hold my cock in at this point. The room erupted with applause and cheers and I turned around to shake my now uncovered ass at all of them. I went around the room shaking my cock at everyone before returning to Emily whose head had been moving to keep me in view the entire time. I leaned down and whispered in her ear before she broke into a huge smile. She then put one finger on each side of the g-string and pulled it straight down letting my cock finally be free. The loudest round of applause yet greeted this move. I went back over to Emily and stood over her lap and shook my cock. What happened next took me by surprise.

Emily leaned only slightly forward and took my cock into her mouth. I gasped and a look of surprise came over my face which quickly changed to satisfaction. Her head was bobbing up and down my shaft and she had a hand on each of my hips. One of my hands was on the back of her head while the other hung by my side. At this point, I know that I was going to cum in my her mouth if this continued my longer. I leaned down and whispered this into her ear. She stopped blowing me and told me to take a step back and keep stroking myself for the enjoyment of everyone.

I did as I was told and soon found myself at the point of climax. All the women had stood up and moved to the middle of the room to watch me. I moaned that I was about to cum and they clapped as I blew load after load into a cup that Donna had gone to get. Without even saying anything, Lindsey dropped to her knees and took the length of my cock into her mouth to suck me dry.

I collapsed onto one of the couches. The ladies began to tell me that for a first-time stripper, I had done really well. Morgan and Donna left soon after but Lindsey and Emily moved from the couch they were on to sit down on either side of me. They suggested that the three of us have fun. As a single man, I was not going to argue.

Lindsey got down onto her knees between my legs and began to suck my cock to get it hard again. Emily began to make out with me and ran her hands along my chest. My hands went to her chest and started to untuck her shirt to pull it off. She pushed my hand away and told me not yet.

After about five minutes of this, Lindsey stopped sucking and asked Emily if she wanted a turn. Emily responded that she would but asked that I stand up. I did so and she led me up to the bedroom with Lindsey following behind her. Emily went to the closet and came back out with handcuffs. She told me to put my hands behind my back and, when I complied, she handcuffed them together behind the bedpost at the foot of the bed. She hiked her skirt up, bent over, and took my hard cock and rubbed it against her wet pussy. This is when I found out she hadn't been wearing panties the whole time. I slid right in and gasped deeply at the pleasure I felt.

Lindsey had come up beside me and was kissing my neck and rubbing my butt with her hand. Emily was moving back and forth but seemed to tire within a few minutes and told me to begin thrusting. As disappointed that I was that she still clothed in her skirt and blouse, I was determined to cum inside her and complied instantly. Lindsey now moved into the armchair int he room and began touching herself at a slow pace to start before speeding up. Her moans increased as she did this and began to combine with the moans Emily was making as I fucked her. I came inside Emily within minutes of starting to thrust. When I did so, she turned around and adjusting her skirt. She walked over to me and grabbed my cock hard. Emily smiled and told me that not only was I a good stripper but also a good ride. She reached around and took off the handcuffs.

In my concentration on the task at hand (fucking Emily), I hadn't noticed Lindsey got off and sat panting heavily in the chair. Emily had gone to the restroom so I went over to Lindsey to check on her. She smiled and said that she was exhausted tonight but would be sure to fuck me as soon as possible. I told her that the blowjob she gave me was phenomenal so I couldn't imagine how good she would be in bed. Lindsey laughed and said, "Only if I get a show again first."

"Deal."