Bill and Jeans Adventures Ch. 09

I could tell Leon was about to lose it, as my instructing Jean had aroused him greatly.

He cleared his throat and said, "Well, I will let you ladies continue with your work. I need to go check on how Gene is doing up front."

I knew in reality that if he had stayed one minute longer, he would be fucking Jean, and nothing I could say, would be able to stop him.

Jean stood up very proud of her newfound skills and was taking another sip of her drink when another cock appeared in the hole. The man had a bit of a belly and some gray hair around his balls. As I knelt down and started stroking his semi-hard cock, I knew he might take a little longer than the younger guys. Jean knelt beside me and whispered in my ear, "Marie, he looks like someone's grandfather," as if she was surprised he would be at a glory hole. I just whispered back to her, "A man's a man; they never outgrow their love of a good blowjob."

Jean watched my approach of more slowly stroking his cock, and sucking around the head; and in a few minutes, he had a very nice hard erection poking out of the hole. I felt his cock start to twitch, as I took him in deeper, too deep because he surprised me with a massive load that gagged me; I reached for the cup and spat out a huge load of cum.

Jean was amazed, "Wow, gramps shoots a load!"

I heard a chuckle from the other side of the wall, as the old guy said, "I sure do, especially for ladies as lovely as you," as he dropped a twenty-dollar tip through the hole. I told him to reload and come back for another one.

I said, "You know Jean, we don't know any of these guys and they don't know us; that is why the glory hole is so erotic. You take this last guy, for example; maybe his wife doesn't give him blowjobs anymore, or he might very well be a lonely widower, who we just made very happy and helped him; for a moment at least, recapture his youth."

Jean said, "Aaaw, that's sweet," and surprised me with a hug, as another similar cock came through the hole.

"You take this one, Jean."

She was a little hesitant, seeing gray pubic hair; but, she thought of how this might be a lonely man, and how she could really make his day. She moved over and started sucking his cock and stroking it, just as I had. About five minutes later, she received an equally large load of cum that she let puddle up on her tongue and then spat into the cup. "Wow, what a huge load!" she said, loud enough for the guy to hear.

You could just hear the pride in his voice as he said, "Why thank you, little lady," and yet another twenty-dollar tip fell to the ground.

"You're learning fast, Jean; the male ego is key. He will brag about you for years to his buddies."

Just then, we heard a knock for the first time from the opposite wall -- the fucking side -- as Mary referred to it; and we saw five one hundred dollar bills fall from the hole, and a large cock follow them through the larger hole in the wall, with a hand in one of the smaller cut-outs.

Mary looked at me with cum dripping down her chin from the guy she had just finished with and said, "I will give it a go."

I nodded to her and tossed her a tube of lube and said, "Go for it."

Jean watched as Mary knelt in front of the hole and gave a couple of quick sucks to the guy's cock and said, "Wow, babe, it looks like you're ready."

"Oh yes, I am ready. I have been watching your ass for a long time, Mary."

Mary said, "Why John, is that you?"

It turns out, John was a truck driver that had flirted with Mary for a long time. Mary lubed his cock, and then standing, she presented her ass through the hole, as John eased his cock into her pussy for the first few strokes. Then, reaching through the hand holes, he grabbed her waist tightly and started fucking Mary really hard with a built-up lust and intensity.

"Holy fuck, John, you're making me cum already," as he bounced Mary on his cock like a rag doll.

Jean and I were so caught up in the intense fucking, we had forgotten about the two cocks that had appeared in the holes in front of us, until an urgent knocking sound caught our attention.

"Jean," I said, "it's up to you and me now," as she took the hole I had been working and I moved over to the spot Mary had been in. The sounds of Mary moaning and cumming so hard, echoed through the rooms, and invigorated the guys we were giving blowjobs to. They pretty much were just fucking Jean's and my mouths now, and they would shoot their loads very quickly. Jean and I would barely have a chance to either spit out the load, or swallow before the next one appeared.

We each had done five different guys, before we caught a break and could rest for a moment. That whole time, John had been pistoning his cock in and out of Mary's cunt, and Mary was having a very intense orgasm and struggling to stay on her feet. I pulled one of the chairs over, so she could lean across it and support herself. John's hand reached up and grabbed her boobs as he fucked her with such intensity.

Jean whispered to me, "How can he last for so long?"

I told her, "With some guys, when they get really fired up, it is like they can fuck forever before they cum."

Jean picked up her mojito and gulped it down. She was showing the effects of it, as she sat down in the chair, tossed her legs over either arm of the chair, and started fingering herself, intently watching the show of John and Mary fucking.

John then pulled out and said, "I need your ass now, Mary."

Mary stood up on unsteady legs, turned to lube John's cock, then spun back around.

"Easy at the start, babe. You have a damn big cock." John did take it easy at first, pushing just the tip of his cock into Mary's tight ass, stretching her until he popped inside causing Mary to moan, "Fuck, it's been a while since I have had one that big in my ass."

John eased in and out a little more each time, until he bottomed out and Mary started panting now as he picked up the pace. In a few minutes, he was ramming into her ass as hard as he had been her pussy. Leon who had been watching us on the monitor, now came back into the room; his eyes opened wide, watching Jean fingering herself, staring intently at the ass fucking Mary was taking. I had another cock come through the wall, and I was on my knees sucking and then stroking it, so I could turn and also watch the show.

Leon was smiling so happy with how well his room was working.

John picked up the pace and started slamming even harder into Mary's ass.

She was screaming, "Oh fuck, I'm cumming so hard! Oh fuck! Oh fuck! I can't take much more, baby!"

Mary cried out; but, John kept pounding away even harder. Leon stepped closer, I thought he was going to call a halt to the pounding; but instead, he just held Mary's shoulders, so John could fuck her even harder!

Leon said, "You got this Mary, you can take it. When they pay the money, they get to fuck you as long as they want, 'til they cum."

Mary stopped screaming and was just moaning, as her head dropped down and swung from side to side.

John's knuckles on his hands were almost white from his grip on Mary's waist, as he pummeled her ass. You could hear him gasping for air trying to catch his breath. Finally, he roared, "I'm cumming!" and shot a huge load of cum deep into Mary's ass.

Mary's head came up and said, "Oh fuck, yes. I feel it pumping inside me, fuck! It feels like a garden hose jammed in my ass. Oh thank god, you finally came, John."

Jean was stunned now, as Mary spun around dropped to her knees and sucked his cock clean, fresh from her ass.

"Oh Christ, Mary, you're great," John said, as two more hundred dollar bills fell from the hole as a tip.

Mary leaned back against the chair wiping the beads of sweat from her face and saying, "Oh my god, John brings it strong."

Then from the other fucking hole, another hand appeared and dropped three crisp one hundred dollar bills.

"I got this one," I said, as I stepped over to the hole and knelt to suck on a semi-hard cock. You can just tell sometimes from the body language, when you have a rookie, as I was stroking a young, twenty-something cock.

As I started sucking him, he grew to a nice eight-inch erection. I was bragging on his cock and asking him if he would give me a good fucking with his nice big cock; I could tell I was building his ego, and his nerve.

He answered, "Oh yes! I will fuck you good ma'am. Umm, are you the brunette, with the huge tits and the... umm... umm--"

I called out, "The big ass!" I could tell my young stud was too polite to say it. "Yes, I am," I said, as I sucked his cock down my throat.

"Oh god, I love women with a big ass," he said.

As I pulled his cock from my mouth with a plop sound, I stood up and pushed my ass up against the hole, and said, "Well, baby, you paid for a ride on this one, so let's get started." I felt him slide one finger, and then two, deep into my cunt from behind; my shy, young man was getting bolder by the minute.

He fingered fucked me with a flurry until my pussy made a very wet and swishy sound and I was starting to feel a powerful orgasm building, when he withdrew his fingers and slammed his hard cock deep into my cunt, going balls deep on the first thrust.

"Jesus, cowboy, you can take your time," but, he was too fired up now, as he proceeded to thrust into me as hard and as fast as he could. Going as fast, and as furious as John had with Mary; but, of course, I had no idea who this young guy was.

I felt an orgasm starting to build and it was such a wild scene. Here I was, taking a hard pounding, as I watched Jean start yet another blowjob, and Mary had returned to duty at the wall, sucking down another cock.

My young cowboy then pulled out, and I thought he was trying to pace himself to make it last; but, he had other ideas, as he pulled my ass into the hole as tight as he could. So far in it, I was nearly stuck and I braced myself for what I thought would be the final round; when I felt his cock head press hard against my asshole and without any lube, he was trying to fuck my ass.

"Hey!" I cried out. "That's the wrong hole there, cowboy," but he pressed again and, without or with lube, his cock head thrust through my tight sphincter into my anus. It hurt like hell without any lube or stretching. "Jesus Christ, you're in my ass! Pull out. You need lube and two hundred more dollars, hun."

Jean and Mary both spun around now, as Leon raced to the door and into the other room. I felt the guy's cock pull back out of my ass.

Leon shouted at him, "No free ass here, motherfucker! It is five hundred to fuck her in the ass, not three, and you lube it up first!" Leon finished his lecture, "You follow the rules or you get the FUCK OUT!"

"Oh, I am so sorry, it's just, Jesus... she is so hot and I was so excited." The young guy was apologizing like mad. "Let me check my wallet, uh, I get paid tomorrow."

I just kept leaning across the chair, my ass stuck in the hole, listening to the drama unfold. My ass felt better now, and I went from being pissed at the kid, to kind of feeling sorry for him; Leon can be very intimidating. I could hear him pulling bills from his wallet and counting out to Leon.

"Uh, uh, oh fuck. I got a hundred and eighty and here," he said, "let me check my other pockets."

I nearly giggled at the thought of the sight playing out for Leon, as this young man was so desperate to fuck my ass, he was giving Leon the last dollar he had in his wallet.

Leon, held pretty strict to his rules. "One hundred and eighty, you're twenty bucks short, kid. If you want to play a man's game, you earn your money before you earn the pussy. Now, get the fuck out!" Leon growled.

I felt sorry for the guy, as Mary and Jean were now also looking concerned for the guy. They, too, could hear the desperation in his voice.

"Oh hey!" the young man said eagerly, "I have my class ring. It's gold, it's got to be worth two hundred dollars."

Okay, I thought, this has gone on long enough. I won't let this guy give up his class ring to fuck my ass; although, I took it as a great compliment. I pulled my ass from the hole and knelt down to look through it, extending my hand to the other room, I pointed to the young guy and said, "Okay, you. Get down here."

Leon did not say anything. I am sure he was curious if I was going to yell at him for trying to fuck my ass without lube.

It took my cowboy a moment; I could tell he was as nervous as he was horny. Then, his face appeared; he looked like he could have been Brad Pitt's younger brother.

Mary leaned over and when she saw him, I heard her whisper, "Hell, he could fuck me for free."

"Now then, young man," I said. "You are keeping your class ring, and you are going to give the hundred and eighty to Leon, and then I will let you fuck my ass. But... you are going to do it the right way, like a gentleman; and you are also going to promise me that when you visit here again, or a place like this, you will bring enough money with you. You might not always have someone as nice as Leon to deal with, and you could get your ass kicked, and you're way too cute for that." I finished by asking, "Do you promise?"

"Yuh, yuh, yes ma'am. I promise," he stammered out.

"Alright then," I replied.

But being young, dumb, and full of cum, he stood back up and tried to start thrusting his cock back through the hole and into my mouth.

Flabbergasted, I said, "Leon, bring him around to our room, so I can learn this boy some manners."

"Move!" Leon said, as I heard them scramble to the door and back into our room.

He looked on, amazed, at Jean and Marie, kneeling on the floor sucking the cocks poking through the wall.

I said, "We have company, girls," as he seemed suddenly, very shy.

I said, "Hello, my name is Marie, and this is Jean and Mary." The girls gave a quick wave, not removing the cocks from their mouths, and just then Mary pulled back as a large black cock shot a load of cum into her mouth. Our cowboy looked stunned, is the only way to describe it.

Again, I said, "My name is Marie."

His eyes went from Mary, back to my boobs and he just stood there. I was not sure if he was even breathing.

"Hello!" I said again, shaking him from his trance, "and you are?"

He paused, as if he had forgotten his own name; then his brain started working again, and he mumbled, "Brad, uh, it's Brad."

Mary was still wiping the cum from her mouth when she said, "No fuckin' way!"

Which caused him to look puzzled, and say, "Yes, I am Brad; and no, I don't think I look like a young Brad Pitt. I don't know why everyone says that."

Just then, a tapping sound could be heard on the wall by Jean, and she was receiving a large load of cum in her mouth by an upward curved white cock, which she promptly spat into her plastic cup. She smiled and said, "Oh wow, this cup is half-full, already!"

This outburst caused Brad to ponder the thought of how many cocks we had blown.

I remarked, "Oh, you should not let that bother you, Brad." I caught Leon smiling big; he knew I was going to have my way with young Brad. "You should just consider it a compliment; now, let's see if we can give you some training."

The whole time I was talking, his eyes were still staring at my boobs; I could tell he had never seen a pair as large as mine.

"Oh for god's sake," Mary said, as she stepped over and took Brad's hand and pressed it against my boobs, "Touch them, before you have a stroke."

Mary then pulled her hand away, as Brad muttered, "I have never seen any so big!"

"Well, baby, they are special. How many girls' boobs have you seen?" I asked him.

"Do you mean like girlfriends?" he asked.

"Yes, baby, like girlfriends."

His fingers started slowly squeezing, releasing, and squeezing again on my boobs; then his left hand came up and he was playing with both my boobs still in a trance-like state. "Two. Well, two that I could touch, you know; I mean, I have seen lots of boobs in porn movies."

I held back a giggle, but Mary didn't, and fortunately for Brad, a cock had reappeared for Mary to take care of; or she would have been teasing the hell out of him.

"Well, there is much I could teach you, hun; but as you can see, we are pretty busy here today, so we will just touch on a few subjects," I said. "First of all, I do appreciate the compliment that is your staring at my boobs like you're hypnotized; but, my eyes are up here, hun; so glance at them once in a while."

He looked quickly and blushed, taking his hands away from my tits.

"And now baby, my eyes are down here," as I gave him a quick kiss on the lips and slid down his body and started stroking his cock. I gave it a quick suck and looked up at his eyes. I knew this was a sight that always freaked a guy out, a woman's eyes looking up at them with his cock in their mouth.

His hands grasp the top of my shoulders, steadying himself, as I sucked him down my throat and held him there for a while. I could taste the pre-cum from his cock and I pulled back; as I didn't want him to shoot his load down my throat, since he had paid up for my ass. His cock was rock hard again as I stood back up and gave him a quick kiss on the lips. I knew he could taste his cum on my lips.

I said, "So baby, would you like to fuck my ass now?"

"Oh god, yes," he said, and surprised me by spinning me around and leaning me across the leather couch, as I felt his cock thrust against my ass cheek.

"Brad!" I exclaimed. "Stop! Now step back and take that lube bottle there," I instructed, pointing at the lube, "and lube up your cock. You have a big cock, baby, and you have to go slow at the start, when you fuck a woman's ass." Looking him in the eyes, I asked him, "You have never been in a girl's ass before, have you?"

"Na- na- no," he stammered, "how can you tell?"

"Oh just a hunch, Brad; now put some lube on one of your fingers and ease your lubed finger into my ass, very slowly."

"In your ass?" he asked.

"Yes, baby, that is where your cock is wanting to go, isn't it?"

"Um, yes," he said.

God the inexperienced ones can be so much fun.

A moment later, I felt Brad's lubed finger very tentatively start to slide into my ass.

"Oh god," he said, "it is so hot and tight."

"I know, baby," I said, "that is why you are going to love fucking it. Now, pull your finger out, and lube up two fingers this time, and do the same thing."

A few seconds later, I felt the added pressure of two fingers working their way into my ass. Brad was starting to feel more at ease with his fingers in my ass; I felt him start to move them around, touching me inside. I looked back over my shoulder and smiled at him, "Are you looking for your car keys, baby?"

Brad suddenly pulled back and said, "No, they are in my pants pocket over there."

Mary exploded in laughter, cackling at me playing with this young stud; and wishing she was me. I saw Jean had finished off her guy, and was giving Brad a very lusty look, as well.

"Okay, baby," I said, standing back upright, "I will get on my hands and knees here on the couch and I want you to get behind me."

Brad said, "So, I should kneel behind you?"

"Yes, baby, kneel behind me, between my legs."

"Not standing up?" he asked. "No baby, kneeling is more comfortable and we want this to last as long as we can, don't we?"

"Oh god, yes, I want to live in your ass."

Even Leon chuckled at this, as I told Brad, "Well, we will see about that."

I expected Brad would try and slam into my ass as hard as he could, but the young man was learning. His hands were just stroking back and forth on my ass grabbing and releasing my ass cheeks causing them to bounce.

"Oh my god, your ass is so fuckin' big!"

"And you like that, baby?" I asked him.

"Oh god yes," he said, as I felt the tip of his cock start to enter my ass; but, it slipped down and pushed into my pussy. "Oh Jesus, it feels just like your pussy," Brad said, with a moan as he started fucking ever faster into my cunt.