Enticed and Humiliated Ch. 15

Part 15 - Hustling at the Gay Bar

I couldn't believe that I had received $50 for giving a blowjob, the previous night! If I could do that a few times a week I would be set financially. I could finish my senior year and then do a Masters program, with no worries about where my beer money would come from!

I decided to check out this Buddies gay bar. I was a little sore from last night so I took a long hot bath. I then went and got an amazing massage, with a large portion of that $50 I had received. I could get used to this! After the message I went to Targets and bought an orange mesh wife beater T-shirt. I figured orange would be easily seen.

At 4pm I stuffed a few condoms and a little tube of lube in my front jeans pocked and left for Buddies. I wanted to get there as the after work crowd arrived for happy hour.

I arrived at Buddies, which is not too far from Choker's sex shop at four forty. The place already had a nice size crowd. Most of the clientele were in their mid to late sixties and a lot of them were eating. I got a beer and just sat at the bar.

In no time the gentleman sitting to my left started talking to me. He was in his late sixties, good looking, with silver hair and told me that he owned a small steel mill, that his son now manages. After just a couple minutes of small talk, he came right out and asked me if I would follow him into the bathroom for fifty dollars.

I agreed and he pushed his finished meal away. I followed this gentleman into the bathroom and we walked into the stall and locked it. He took out a fifty, gave it to me and guided me to my knees by putting his hand on my shoulder.

I quickly undid his buckle and fished out a nice sized semi hard cock. I stuck the head into my mouth and wiggled my hand into his underwear so I could fondle his balls while I sucked. He gave a content sigh as I went to work. Soon I had both of his nuts in my hand and was tugging on them gently as his cockhead stretched my gullet. I could feel his head entering my esophagus every time my nose mashed against his pubic hair. I loved it, and would hold it in messaging it by swallowing. In only a few short minutes this classy man grabbed my head tight and started to cum in my mouth.

I thought to myself how lucky I was making money by doing something that I love so much! I swirled his cum around in my mouth and continued licking the underside of his cock. Soon he pulled out by pushing my head back. I guess he reached that supper sensitive stage. I swallowed his load down and made sure his cock was clean, before he put it back into his pants and buckled up.

"That was great!" My patron exclaimed. "I come here a few times a week for dinner and conversation." "If you are around I will always have a fifty for you." "By the way, my name is William."

I shook hands with William and told him that I planned to start coming to the place more often.

We then left the bathroom and William went home to his wife and I went back to the bar to spend some of that fifty on a beer. For the next few hours I sat at the bar getting to know the bartender. His name was Allan and he was very friendly towards me. The place filled up. with many more people coming in, now that the workday was over. Most of the people walking in were younger than the original crowd that was there when I had arrived. By younger I mean late thirties to early sixties. I had a few men make small talk with me, and I did take one back into the bathroom for another fifty dollar blowjob.

It was now past seven thirty and the crowd started thinning. I was getting ready to leave and visit Choker's sex shop. I finished my beer, left a nice tip and started walking towards the exit when I felt a tap on my shoulder.

A small man about 5'5" asked me why I was leaving so early. I told him that it seamed like the evening was winding down.

"But the night is about to begin!" He replied. "My name is Rick and I would like to buy you a beer."

"Sure." I answered, while sizing him up. Rick was probably in his mid forties very slim and clean shaved.

He ordered two beers from the bar and led me to a small table in a more secluded area.

I took a sip and Rick mentioned that he saw me go in and leave the bathroom with my last John.

I started getting nervous about where this was going but he allayed my fears by asking if I liked crossdressing.

I told Rick that I loved being dressed in sexy clothes. He now asked if I was a top or bottom. I let him know that I was pretty new to the scene and had only been on the receiving end. I did not know what it was like to penetrate another mans hole. I let him know that I loved fucking women though.

"That's good Kid." Rick said. "How would like like coming back to my place and having a dressing session?"

"What's involved in that?" I asked. "What would be expected of me?"

"We will both dress up in sexy women's clothing." Rick explained. "I would also want you to fuck me." "Would one fifty be enough to convince you to spend the night?"

"It's plenty." I replied. "I would love to dress up with you and I will try penetrating you." "I don't have anything planned so I can stay the whole night."

With that Rick took me out to his car and we drove about twenty minutes to a nice suburban home. Rick told me that he lived there alone. His ex-wife actually made more money than him. When he confessed to her that he was gay, she let him keep the house and most of her wardrobe. She wanted out and since they had no kids she left even before the divorce was finalized.

Taking me to his bedroom, I was in awe of the two full walk in closets full of woman's clothing. There was also a large dresser filled with lacy silky intimates! Beside the dresser there was a make-up table full of make-up and a large mirror.

Rick got us some beers out of the fridge and said, "Let's get dressed!"

As we stripped I noticed that Rick was totally hairless from the neck down.

"How did you get rid of all your hair?" I asked.

"I naired it all off." He replied. "I still have almost a full bottle if you want to take yours off."

Since it would be three weeks before Sandy returned, I quickly agreed, figuring my hair would grow back before then. Rick applied it all over my legs, scrotum, lower abdomen and ass crack. I have a hairless chest so I did not need to nair it. We finished our beers and he told me to get in the shower and rinse all of the cream off. When the water hit me it seemed as if all my body hair just melted away!

I couldn't believe how smooth my legs were. All of Rick's ex-wife's panties and stockings felt so great on my newly smooth skin! I loved it!

We spent almost an hour trying on all sorts of stockings, garters, panties, bras, corsets and baby dolls. Rick then took out two gorgeous evening dresses. When we put them on I couldn't believe how hot we looked!

For the next twenty minutes Rick applied make-up on both himself and me. He then put on a wig and blow dried my long hair. We were both very passable! I knew that I would be back to visit Rick again even if he didn't pay me next time.

I admired myself in the mirror once Rick was done with my hair. I grabbed his head and kissed him passionately to thank him. Rick kissed back and started groping my ass cheeks. I could feel the precum soaking my panties I was so turned on. In no time we made it to the bed.

I knew that Rick wanted me to fuck his ass so I took the initiative and pushed him onto his back on the bed. I then jumped on him, pinning him under me. We made out like teens and I felt him up under his dress. Soon the dresses were gone and we were grinding. My hairless scrotum and cock loved the silk panties. It was so hard that the condom was easy to get on. Rick had slid his panties off and laid down in front of me in the fetal position.

"You can just shove it in!" Rick said. "My hole is pretty loose from all of the but plugs that I wear."

I put some lube on my condom covered cock and held the head between his cheeks. Thrusting forward my cock slid right in. I held rick tightly and started fucking him in the spooning position. It was awesome! He was made up so well, so totally smooth and sexy smelling with the perfume, that I could not tell that I was holding a man!

Fucking Ricks ass was no different than fucking Sandy's and I easily got into it. Soon Rick was pushing back hard to meet my thrusts and I was working up a light sweat. I could see that Rick was stroking his cock in time with my thrusts. However sometimes he stopped.

"I'm going to blow soon!" I warned him.

"Go for it!" Rick moaned, as he started stroking his cock really fast.

In just a few more thrusts I blew my load into the condom. It was a satisfying orgasm and I just lied there holding Rick tight, in the spoon position. It felt so good that I must of drifted off.

At seven fifteen the next morning I felt Rick leave the bed. He took a quick shower and I drifted back to sleep. I next woke at ten and got out of bed this time. Rick was gone so I found a towel and took a shower. I loved my smooth skin!

On the way out I saw $170 and a note on the kitchen table. It read:

Dear Ron,

I had so much fun last night and hope to have many more such nights with you!

I have included an extra twenty dollars for cab fare. Please help yourself to breakfast.

My cell phone number is 555-1234. Please call me when you can play with me again.

Kisses,

Ricky

I did help myself to some breakfast. Rick's refrigerator was well stocked and he had left coffee percolating. When done, I put the dishes in the dishwashers and wiped down the table. It was now almost eleven and I had nothing planned, so I decided to head over to Choker's sex shop. Buying some new toys with the two fifty that I made last night seemed like a good plan.

To be continued . . .