Just a Gigolo

"No really!" I hurriedly followed, as I could not stop the eruption.

"Give it to mamma, baby," she announced while tilting towards me, but not for a smooch. She wanted to watch me cum!

That made it so much hotter, and I shot 3 ft in the air with a powerful jet! If you were watching a porno you would say to yourself,'no way that's real'.

"Now that's what I call shooting your wad!" Cindy cooed.

"Well you wouldn't stop! Sorry if I got any on you," I apologized, though I did not feel sorry.

"No, Sailor, that one's on me," she said, smiling. "I bet your recovery time is good too," she brazenly responded. "Are you really in construction?"

She's better at poker than I am, so she knew the answer before I could admit it.

"I do construction still, but I've cut my hours down to the lowest that I can," I confessed.

We sailed for a while. If you know what an 'uncomfortable pause' is, you might understand what it's like to have your limp cock hanging out, while your date realizes that you are a gigolo.

Was she wondering if I'm clean? Would she think I'm a deviant? Was I going to need an Uber to get home?

She brought the vessel to an easier line against the wind, so that we could shift ourselves inwards.

"You can service me, while I think about this," she demanded, while she reached down and pulled the bit of fabric that concealed her labia, over to one side. Her legs spread in invitation.

Of course I shifted onto my knees where I belonged. She leaned back and pulled a towel over me.

"I don't want you to get a burn," she explained.

The blood was already rushing back to my cock! Her moist vagina was the most incredible sight that I had ever beheld! She was clean shaven with puffy, lust plumped labia! I went in for a gentle caress with my tongue.

I have refined my technique after the many times I have been denied entry into a woman's vagina.

She spread her legs just that little bit more, signifying the lust for intrusion. I would not deny her, thrusting my tongue into her love tunnel. I bump my chin and nose to her body as I probe deeply, wiggling my tongue for the maximum exploration that my small tool can provide.

"Yep, right about... Oh..I won't say no to that...yep,yep,oh,oh..."

I could tell the difference in taste right away, it's like, well,... I don't think that my cum tastes much different.

I was not done though. I settled in with a slow roll up into the clit, then back down, I pierced her again pushing as deep as I could then pulling up and out across her clit, then a quick puff of my breath, and repeat.

She shifted our direction, bringing me harder into her muff.

I shifted to rapid lapping of her clit, and two minutes later she had another orgasm.

"Okay," sit with me Tim. My beauty commanded me.

"Tell me about being a Jigelo," she mispronounced the word so sweetly.

I described everything to Cindy. Even the sex, she wanted it all. She understood the idea of a wealthy older woman wanting a fling with a handsome young stud. We even discussed the use of condoms, and a close inspection for other signs of std's. I told her about Juanita and having a website where a lonely woman can order an evening of entertainment. She did eventually ask if I had any condoms, and we made sweet love, as I always do.

It took five minutes just to get me deep inside her. She was full!

I felt myself bump into her cervix, and she finally opened her eyes.

They were big like saucers.

"Oh yes you are big...slow please," she cooed while leaning in for a kiss.

Usually this slow sex didn't effect me that much, but I was so aroused that I probably would have cum just from being inside of this gorgeous woman.

I closed my eyes and spasmed into the condom, deep inside of her tightly stretched pussy.

Now I could get some strokes in, as my cock lost some of its rigor. She raced her tongue around my mouth as I found a pace and a stroke that she was happy with. Her pleasure was all that mattered now.

This time my cock didn't shrink as much as it normally does. I held my own, while I stretched her second or third orgasm.

"Oh, my God! I can't believe that you can do this to me!" Cindy moaned with another shudder of bliss.

I came in the same rubber!

"Fuck,... Sin,...Um, I have to pull out, or I will leak into you...."

"Oh! Okay, let's be careful with that I guess," she recovered her composure, and I slowly pulled out of her.

"Can you go again?" She asked.

"I have lots of condoms," I answered, and she smiled as she reached for one.

It was midnight before I got home. I made enough noise, so mom would know that it's me, but not so much that it would have woken her if she was sleeping.

I had my alarm set, but my raging hardon woke me up first.

I lost whatever image had my heart racing, during a sexy dream. Then the music came to my ear, announcing the start of my work day.

I snagged my backpack and I was out of the door before Luigi came to a full stop.

He was looking chipper. His girlfriend works late, so he gets to sleep about 8 p.m. every night now. His fun time was from shower time till Juanita had to take care of her clients.

"She's moving in tonight," Luigi announced as soon as we got on Concord.

"That's great, Lou!" I was really happy for my bestie.

"It means an early day for me again. Is that okay with you Tim?" He didn't want to leave me stranded again.

"Let me see about a ride, Lou," I replied as I picked up my cell. "I did meet a girl..." I trailed off.

"Yeah, it's me...I need a ride," I left it for her to ask if I was calling for her business or her accompaniment?

"I'm on the way," is all I got.

When she picked me up we decided just to have a swim in our pool, then she could meet the folks. Wow! It was like we were rounding second base in the relationship cycle.

Mom was out, but left a message that she was bringing home pizza, and to text her if we wanted anything else.

The lack of cars meant no one was at home, but we still put our swimsuits on.

"Don't you have a speedo?" Sin teased me.

"I gave up on wearing briefs a long time ago, girl," I told her. "Most people do not want to see my winkee at the bottom of my shorts," I replied. It would be like you wearing a child's bikini top.

"I don't get many negative comments about my girls," Cindy showed me her pouty face.

I did a low dive into the pool, to get my waist below the water, and out of public sight.

Sin must have dove right behind me. She came up on me fast, and ripped my Hawaiian shorts down and off with a sweep.

The lights came on in the kitchen just as mom and dad came in with pizza boxes in their arms.

The only thing I could do was to move in close, and let the wall hide my nakedness. Cindy stashed my shorts behind a lawn chair as she climbed out of the pool.

"Oh, who do we have here?" Mom asked sweetly.

"Hi Mrs. Bradley. I'm Cindy Lestor, she said, without revealing any relationship.

"Hi, you can call me Zetta," Mom dropped her first name on the first visit!

Why don't you kids join us for pizza? It's Tim's favorite. Double meat, double cheese.

"Oh, yes, Tim, come join us," Sin coaxed me. "It's your favorite," she teased.

So I went to the ladder, and climbed out to have naked pizza with mom dad and my girlfriend. I was the only one to follow the naked part, while mom and dad kept their eyes up, but they all laughed a lot. Especially every time someone dropped a piece of meat off their heavily laden slice.

After two pieces mom decided that her and dad were full.

"You'll have to take care of the mess out here son. We did make dinner," dad said, laughing, but he took a third piece with him.

"Goodnight Cindy. It was great to meet you," mom hurriedly added just before their bedroom door shut.

"Thank God Kalli didn't come home for dinner!" I finally declared.

"Well, we might as well have that swim now," Sin suggested.

We met in the middle of the pool.

I was just untangling the string on her top when we heard mom start moaning.

"Is that your mother?" Cindy whispered in my ear. I wasn't going to get lucky. I should just resign myself to forever being disappointed. The moaning got louder and closer spaced.

"Sounds like your dad knows what he's doing," Sin whispered, but not too quietly.

I found the strings and pulled them.

"Oops," I said, but not contritely.

She went under to get my shorts again, but I went down too and caught one of her last strings. So she went to the spot that all women go to, when they're desperate.

She grabbed me by the balls.

When we came up for air, I had her bikini bottom in one hand, while she had my balls and she started to squeeze.

That's when Kalli showed up.

"Couldn't you send me a text about them going at it Tim?"

Then she saw that I was not alone and she stopped to see who it was.

"Oh, wow, this is awkward, Kalli said, or maybe Cindy said it? They were both uncomfortable.

"I'm off to my room now," Kalli demonstrated her adult qualities, and she surrendered the back yard to us.

We did not want to push our luck, so we found our clothes and ended the fun.

"Same time tomorrow?" Cindy asked, as she collected her stuff.

"Sure. I'll text you," I promised my ...girlfriend!

It only took a week to find a place downtown, though we couldn't get the keys for 60 days. We made the decision over dinner at the Green Frog Tavern. Juanita and Luigi had been cohabitating for a week, and they fit together now like peas in a pod.

Juanita spends some time on her laptop, even at 4 in the afternoon, making moves with her dozen men, and the horny women of Las Vegas. Most of whom are in their hotel rooms, between seminars and sales meetings, just cruising the ads. Juanita depends on word of mouth for most of her clients.

"I was hoping that Tim could do an 'incentive' party on Friday, but that will require me to be there, for safety reasons," my agent directed me.

"Security? From whom do I need protection? A room of women?" I wondered, feeling like there was a joke hidden here.

"They use bondage, and someone has to make sure that they follow the condom rules, and, well, you've never seen how heated these women can get," Juanita emphasized her concerns.

"What about using me?" Cindy suggested. "I can do driving and security for you, and I would not make them feel as uncomfortable as some muscle guy would"

Her argument was sound, and Juanita agreed to leave it with her.

They had a costume for me. I had to jump out of a box, wearing a rip-away tuxedo. Juanita assured me that I didn't have to dance or act, just jump out of the box when they started to sing "happy birthday".

We had an office to set up in, while the party was already underway. The lady in charge came back to make sure that we knew our part.

"Cindy and Tim? Right? I'm Phyllis," Phyllis exclaimed, shaking Cindy's hand and ignoring me.

"The winning ladies have been here before, and they will not be buying you dinner and bringing you chocolates," Phyllis instructed us.

"They will tear your suit off, which will leave the cuffs on you, and they will use those cuffs to attach you to the fucking table in the middle of the room."

"They will not want to hurt you, but they will want to grab your cock, and shove their pussies in your mouth, just as quickly as they can," She finished.

"Tim has never done more than one woman at a time," Cindy cautioned Phyllis.

"Well, I did have a foursome with a cousin and her girlfriends, but no one was restrained," I corrected my assistant. "...and I did sisters once, does that count," I asked, to Cindy's obvious irritation.

"Okay, I guess he knows what he's doing," Sin concluded.

"Do you think I have enough condoms?" Cindy wondered, looking at her backpack, with 6 boxes of extra large Trojan's. "Remind me to buy these in bulk."

Phyllis returned to the office, to help Cindy wheel in the trolley with the giant gift box.

When I popped out of the box, it was just like Phyllis said. These lusty women grabbed me, and pulled me out of the box. The suit was torn off of me and they dragged me to the fucking chair. They were not gentle, as four of them buckled me in and 2 of them handled my cock.

With no introductions, one of the nimbler ladies climbed up to my face and pushed her naked cunt onto my mouth.

I had just pushed my tongue in deep, when my cock was engulfed in someone's mouth. Hands were pulling on my testicles making it impossible to focus on the vagina on my face.

"Ladies, can we have a little order?" I heard Cindy talking civilly to these poor deprived women.

The one with her puss in my mouth started to cum, and the order was lost as the other horny ladies realized that they were not getting their share.

"Okay! Who wants the big cock in their vagina?" Cindy announced. "Who here is woman enough," she challenged them.

"He's mine first," a heavy 50 year old put her hand up and stepped forward.

"Make room ladies. The winner rides first," Cindy jubilantly announced and everyone roared with their approval.

"Don't worry big guy, I've had 5 kids, and the last one slid out after only 22 minutes of labor," she bragged.

She lifted her skirt, and I saw the same underwear on her that everyone in that room was wearing...none.

She straddled me, and Cindy helped to make sure that the marriage was a safe one.

"Oh, my! This one is bigger Kathy," she informed her friend. "Oh, I think this will work," she claimed as she started to lift and lower herself onto my pole.

I found her lust to be very attractive, even if she was a bit saggy and flabby. Lust can be a powerful aphrodisiac.

She came down hard, but my legs were spread so she didn't slam into my balls. This was one of the deepest fucks I'd ever been a part of, as the entire shaft appeared then disappeared with every long stroke. When she was ready to cum, she shortened to a six inch blast that kept my cock head well buried.

Her orgasm started, and I wanted to play with her tits, but my wrists were buckled down. It wasn't until I emptied into our winner, that I felt the hands on my ass and chest. A dozen women were all around my raised platform, enjoying my body. When the first one was off, Cindy had another condom ready, but offered it to the next woman to install.

This one smiled, and put as much of my limp cock into her mouth, as she could cram. It was covered in my own cum, but she did not care. As it plumped up, she let it slide out and she moved up and down the shaft with her tongue and her lips and her hands.

She covered the tip, then used her lips to push the condom over my freshly inflated head, then she had to use her fingers to roll it down to just above my balls. She was very careful about getting the last few rolls to release onto my cock, then she kissed my balls and sucked one into her mouth, swirled it around and switched to the other.

She climbed onto the shaft while another lady was moving to stand where my tongue could pleasure her.

Soon, the one jumping on my cock had her hands on the hips of the one I was tonguing into an orgasm.

Cindy called for a break after the third woman rode me to a very loud prize. It took me another minute to make the face rider cum, but Cindy had a chance to undo the buckles, while I finished with my tongue magic.

"So, do you want to make out on your break time?" Cindy asked, making us both laugh. She was taking this very well. I had to pee, so she held my juice, while I went to the men's room, wearing only a towel.

There was another party across the hall, and these guys wore suits.

"Hey, what kind of party are you at?" one guy wondered as he pissed.

"You should be able to figure it out, buddy," I replied, shifting my eyes to my limp, but still very large cock.

He left without washing his hands!

I didn't go complain at the front desk, figuring that they would just laugh.

Cindy clipped my ankles in while I drank more thin orange juice.

"Hey, can I use some ice honey?" My next tongue customer asked.

"Sure, I guess," Cindy offered a cup of ice to my next best friend, and she slipped a nice piece into my mouth.

I pushed it into her snatch as soon as it was close enough. She pushed it back out and into my mouth, so I shot it back, deep into her vagina. We played back and forth until she lost focus and came for me.

I hadn't even noticed that the next one on my cock was having trouble getting it all of the way in.

"Is that the bottom?" she wondered, but only the head was inside.

"If you can get the head in, you've got to be able to get 4 or 5 inches more, sweety," Phyllis advised the younger lady. "You have had children, Sarah? Haven't you," Phyllis was getting a little worried.

"It's starting to hurt," Sarah complained. "...and, I don't think... Oh my, I don't think that I can lift off either! Oh no!" Sarah was starting to panic, but she was impaled, and had nowhere to go.

"Should we use ice?" Cindy wondered quietly, not wanting to panic the herd.

"Yeah, pack it around his balls," Phyllis instructed her. "Karen, get off his face, we have a problem girl!"

Karen was not paying attention to anyone but me, as I licked her into bliss.

With Karen off my face, and ice around the 7 inches of pole that protruded out the bottom, the blood started to drain from my cock.

Poor Karen hugged me, too embarrassed to look me in the eye.

Finally, she was able to lift off of me.

"Thanks anyway, Big Guy," she whispered in my ear, and nibbled a bit on my ear before she pulled away. She was not to be denied though. She climbed right up into the tongue spot, and I didn't leave her waiting. I knew that Cindy would take care of my rod.

Three 45 minute segments is as far as they go, and my balls were hurting almost as much as my tongue by the time we were done.

Karen was the only one that I had to be careful with, but even she managed to grind all of the way down on her third try. It was not my fully erect cock, but she was stretched tight, so I had to go slow.

When we were all done, Phyllis and Cindy wheeled me back to the office / change room.

"I thought that you might go for a ride, Phyllis," Cindy asked as I stepped out of the box again.

"I always wait until the party is over," she responded. Don't worry, I will only need 10 minutes.

She unzipped her dress and stepped out of it wearing nothing but a smile.

"I hope you don't mind, but I love to have my tits sucked while I fuck," Phyllis explained as she straddled me.

"Customer first!" I smiled and leaned in with my mouth, while I felt Cindy putting a fresh condom on my shriveled love tool.

She helped to keep me solid enough to get it into Phyllis pussy, but by the time she was settled all of the way into my lap, I was revived enough to jump into some nice big tits!

I nibbled and raced my tongue around, and pinched her nibs, while she thrust up and down, keeping a good pace going.

My attention to her nipples paid off, and she enjoyed a nice enough release, although I didn't cum myself.

"Thanks, Tim," I'll ask for you next quarter," Phyllis said, kissing me again.

"I bet that's what you tell all the guys," Sin responded, but laughed.

"I guess I have told that to a few, but I meant it with them too," she smiled and walked out of the party room.

Cindy sent a confirmation to Juanita that we were clear, and all was well. That concluded our evening. We had banked 5K for a little more than 4 hours of work. If you gauge it by the orgasm, it was probably 100 bucks a pop, which didn't sound like a bad deal for them either.

Cindy dropped me off around 5 in the morning. Mom was feeding breakfast to dad as we came in the door.

"Hey, long night you two," Mom started. I did tell her that we would be late.

"I hope my boy is a considerate lover," mom engaged Cindy in a little girl to girl talk, while I found some bacon in the kitchen.