My Story Ch. 01

(Writer's Note: My story is a bit long, I admit, but I felt it necessary for this first installment of what I hope will be a great story. What I plan to do with each future Part is to fit each Literotica story category/theme. It will be challenging to do so in the categories I have no interest in, such as Gay Male, Sci-Fi, etc., but I will give it the old college try. Thanks in advance for all feedback. Hope you enjoy my tale.)

I was doing quite alright financially for a 20 year old. While most of my friends were struggling to collect enough dough to pay for college or buy a car, or even just some pocket change to take a girl to a movie, my evening job had me dressing in the latest and most popular clothes, I had just bought an almost-new Jeep YJ, and of course I was smart enough to put some money away for college. Dating on the other hand, was something I had to sacrifice in order to make this money.

I had never had trouble meeting women and in fact, still had sex on a fairly regular basis, but I couldn't commit to a girlfriend due to my job... the lucrative one I mean, not the job at the video store that my family and friends knew about.

It all started innocently enough a year and a half earlier. It was a hot summer day and I decided to go for a long skate on my Rollerblades. After a couple of miles, the heat forced me to remove my shirt. Playing on the school football, baseball and hockey teams, along with my regular visits to the gym meant I was pretty cut physically.

I stopped at a park bench for a rest and was soon joined by a very attractive, 30-ish woman. She sat next to me and said hello, to which I responded in kind.

"How old are you?" she asked. I had not expected that kind of question, so I hesitated before responding that I was 18.

"Do you know how to dance?" was her next query. I thought perhaps she was asking me on a date, to which I would have very happily accepted. "Sure, I love dancing," I lied. I truly did know how to dance and had received compliments on my moves, but in all honesty, I hated dancing.

"Great!" she responded enthusiastically, before she went red and was clearly uncomfortable with what she was about to ask. "I am throwing a wedding shower for my friend and need to hire a male stripper. Everyone I've called wants over $200 for an hour and I don't feel comfortable hiring a guy I've never seen, he might be fat or bald or ugly. So I'll give you $250 for the entire party, which would be about four hours.

Compared to my $6 per hour job at Video Village, this money was too good to pass up, even if I couldn't actually do the work. I wasn't a stripper! I said yes without really thinking about what I just agreed to.

"Be here tonight at 8, and be dressed in a suit and tie when you arrive," she said handing me an address written on a sheet of paper. "Oh, and ask for Kerri," she said putting her hand out for me to shake.

Sensibility finally began to sink in as I shook her hand and I told her I couldn't do this, I didn't know how to be a stripper! She should find someone else.

"Don't be silly, you'll do just fine," she encouraged. "I'll make it $300, but you will have to more than just strip... and there's the possibility of a lot more money in it from you if you play your cards right."

She winked and walked away as I sat there dumbfounded. I must have sat there for about an hour after she left, just staring at the address, wondering what the hell I was thinking by agreeing to this. I crumpled up the paper and threw it away, then began skating home.

I was about halfway when my thoughts on this got the best of me and I returned, hoping to find the crumpled ball of paper where I tossed it. Luckily there was virtually no wind so it had only moved slightly from the spot it landed. I picked it and went home to shower and change.

As I tightened the knot in my tie, the doubts again creeped in. I decided I would arrive at the door and make a final decision then whether or not to knock on the door or get away from there as fast as I could. Luckily no one was home at my house when I left, so explaining why I was so dressed up would not be a problem. I hailed a cab and headed for the address Kerri provided.

Now my mind-games had taken a different approach, rather than nerves of whether or not I could go through with it, I now began to doubt this was legit. "Fuck her!" I almost said out loud in the cab. If this is all bullshit, then it's a lesson learnt not to believe everything you hear, especially when it involves an attractive woman and money. And if this was legit... then I was fucked! What would I do then? Best not to think about it until I get there, I convinced myself.

I noticed the homes we past seemed to get nicer and nicer before slowing to a gorgeous house with a number of cars in the driveway. The cabbie said this was the address I was looking for, and the number certainly matched.

"Look," I told the cabbie as I paid him, "I might not actually enter. If I do, then you can drive off, but stick around until then because I might come back." He grunted his agreement.

As I walked towards the door debating whether or not to make a break for the taxi, the door opened and Kerri was smiling, holding it open.

"Glad you could make it, come on in cutie," she said. Caught off guard, I entered and heard the cab drive off. I was a dead-man! "What's your name, anyway?" she asked. I could see she had been enjoying a few drinks by the glazed over look in her eyes, and the confidence she displayed compared to the awkwardness she demonstrated earlier. I answered her and she took my hand. "You look fantastic Eddy, nice tie." She led me past a room with a bunch of noisy women into the kitchen.

"Eddy, I'm the only one who knows you are here as the entertainment. You are to act as if you're just a cute, naive waiter who will then be talked into taking your clothes off, got it?"

Well, I had the naive part down, but expressed my hesitations to Kerri. As I did, she poured some Jack Daniels into a glass. "Drink this," she ordered. I didn't think she heard a single word I had just said and in frustration gulped down the whiskey before trying to explain again. I was met with another glass and a peace offering.

"Tell you what Eddy," she began negotiating, "Just do the waiter thing for now. Have a couple more drinks to loosen you up, and when the time comes for the entertainment, I will check with you first. If you can do it, then you've got at least $300 in your pocket and I won't look like a jackass who failed to get my friend a stripper. If you can't do it, then you're free to go at the end of the night, but you get nothing. Here's a $100 advance, but I get that back if you bail on me, deal?"

Her offer was fair I thought. I had no intention of stripping, but figured I at least owed her the waiter end of the bargain. She instructed me to just begin taking drink orders from the ladies and serving them, which I concluded would be easy enough. It proved to be much more difficult than I expected.

As I walked into the room, the women quickly stopped their little conversations to size up the male who just entered. They were visibly disappointed when Kerri introduced me as, "Eddy, who will be happy to take your drink orders." As one much older woman said, "Kerri, we thought this handsome young man was going to put on a show for us." As the room erupted with laughter, Kerri just winked at me while saying, "Perhaps if we're lucky Eddy will be so accommodating."

I took a few orders, nothing too complex, especially for someone with no bar-tending experience like me. Each time I entered the room I felt the gaze of the women, eyeing me as I took their orders, and I could hear their little remarks about my butt, and what a "strong, young buck" I was. I probably would've found it degrading without the four shots of Jack Daniels I had had by this point. Instead I found it arousing and even began to play it up, flirting with the women who had by now started putting tips into my pocket.

A woman named Shirley then stood up and announced, "It is time, ladies." I instantly looked over at Kerri terrified that she'd betrayed me, but she waved her hand in a manner that eased my concerns that this had nothing to do with me. As it turns out, Shirley was from a local fantasy company and goes to such gatherings to sell sex toys, lotions, lingerie, and other sexual products.

As I continuously walked from the kitchen to the room (gulping another glass of whiskey every so often), Shirley's sales pitch went from amusing me to exciting me with some of the sexy outfits to the somewhat awkward, yet strangely arousing display of sex toys. I watched, enjoying a good buzz from the Jack Daniels, and feeling my cock get harder as the ladies passed around small, egg-shape vibrators up to big, black rubber cocks as thick as my muscular forearm.

After the products had all been shown and explained, Shirley took her wares into another room where the shower guests would see her alone to confidentially buy any of the items they wanted to purchase. During this time, Kerri came to me and was happy to see that I was now as drunk as she was, if not more.

"How are ya, Eddy?" she asked coyly, knowing what my answer would be. I gave her the familiar stupid grin most people smile when they've had a few too many.

"And how are you feeling about being the stripper for your pal Kerri and her friends?" she said in her most seductive voice, grabbing the lapels of my jacket and pulling me close to her. Between the money, the close proximity of her body to mine, the hard-on I had from watching the women with the sex toys, and of course the who-knows-how-many-drinks, the most intellectual thing I could say was, "Fuck it! Why not?!"

Kerri was delighted and then explained the set-up. I was to take drink orders as normal, but when I got to Jamie (the bride-to-be), Kerri would tease me about not having a stripper for Jamie and would I just take off my shirt so that she could see my muscular chest. I would act shy, but willing to do so after Kerri's pestering. From there, Kerri would continue to hound me to remove the rest of my clothing before I would eventually be naked and she'd play some music for me to dance to. Pissed-drunk as I now was, it all seemed like the easiest thing to do.

Sure enough, after everyone had made their purchases from Shirley, I took another round of orders, coming to Jamie last. Kerri sitting next to her, was lamenting to Jamie that she is a terrible friend for not having got a stripper. Jamie shyly told her it was okay, while the other women pretended to be distraught by this.

"Eddy, could you please, please, please help out a terrible maid of honour and just show Jamie your bare chest, it's the least I can think of after failing so miserably at my most important task," Kerri asked dramatically, as if she might just die if I refused. As planned, I chuckled in an "awww, shucks" shy little boy manner and told her I didn't have a very nice body and Jamie wouldn't want to see my bare chest.

"Sure she does," Kerri interjected, a statement that was echoed by some of the other women. As Kerri prodded on, I pretended to waver, as if I was debating it, which just drew more cheers and urging from the others. "Just my chest, right?" I asked Kerri? "Of course!" she replied, before saying a loud whisper before laughing, "Maybe..."

I removed my coat and after the urges of her friends and guests, Jamie helped remove my tie and slowly unbutton my shirt.

By now my hard-on was pushing against the fabric of my slacks and this did not go unnoticed by the women who made a number of crude comments alluding to it.

As Jamie pulled my open shirt down over my arms, my bare chest was welcomed with cheers and whistles. Kerri stood applauding then put my neck tie back on me, before saying, "Eddy, you'll notice your tie almost appears like an arrow pointing downward... to what we'd like to see you remove next."

This drew more boisterous noise from the women, and once again, I played the shy kid who wouldn't dare do such a thing. More pestering from Kerri and the others, plus an offer of $100 from Stacey, Jamie's smoking-hot M.I.L.F. of a mother, got me agreeing to wear nothing but my boxers, and the agreement to dance for Jamie.

As the music played I began dancing, very awkwardly at first but the cheers encouraged me to really get into it. Soon I was grinding my very evident hard-on into Jamie's chest, as I slid my body down on to hers. I then worked my way around the room, dancing a bit for each woman, occasionally being groped by the more out-going ones. When I got to Kerri, she placed her hands on my ass, as if just to cop a feel of my buns, but she very quickly yanked my shorts down to the loud approval of the others.

I feigned embarrassment and covered up, but quickly agreed to finish my dance in the buff at the almost instant offer of another $100 from Kelly, a friend of Jamie's.

My engorged cock was exposed as I danced around, drunk and loving the attention. Shirley jokingly said that I too should meet with the women one-on-one in the bedroom. This playful suggestion led to a very interesting offer of yet another $100 to jack off. Some of the more reserved women took that as their cue to leave, but that wasn't going to stop me from making another $100 to do what I did for free all the time anyway. I agreed, but kept dancing while Jamie and Stacey and Kerri thanked the guests who were departing at the door.

When they returned, Kerri had already gotten some baby oil out of the bathroom and passed it to me to use for the next part of my show. I slowly and sensually poured the oil onto my chest and rubbed it into my skin while slowly grinding to the music. The crowd was pretty quiet by this point and simply watched me.

I squeezed the bottle onto my stomach and allowed the oil to pour down onto my cock and balls. My hands slid down my chest past my stomach and down to my hard shaft. I began rubbing the oil into my foreskin with my right hand as my left rubbed my balls. The spreading of oil turned into slow, rhythmic stroking as my right hand slid up and down my length.

The oil glistened off my chiselled body and my pace accelerated. The women were watching me intently and were clearly aroused by my performance. I then got down on my knees followed by arching my back, pumping furiously on my hard cock. The women seemed to move closer and closer to me.

Up to this point they were very quiet, but as they saw me nearing my impending peak, Kelly was the first to break the silence with a plea for me to cum. The women concurred that this was what they wanted to see, and so with the vocal encouragement, I found myself panting, my breath rapid and shallow as my oiled hand slid the foreskin over the head of my cock and then back down again until it exploded with my hot white lava, shooting onto my abs and chest. A round of applause and cheering demonstrated my audience's enjoyment.

As the women filtered out, I showered and got dressed, $780 richer (including tips). I wished Jamie well in her marriage, and gave Kerri my number so that she could reach me for any more parties.

I have been dancing since and putting on jack-off shows whenever someone would pay me to do so, averaging one party for every two weeks, though admittedly the lucrative debut I enjoyed had yet to be matched. An ad in the local newspaper help to attract enough business to keep me happy, however.

My goal was to keep doing this for a few more years, at least until I graduated college and had a full-time job, but that all changed at last night's party... now, my whole life was turned upside down and I had no idea what my future had in store.

To be continued...