Fun with the Waiter and His Manager

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We meet up with the waiter again, and his manager comes along.
4.2k words
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Part 2 of the 2 part series

Updated 10/16/2022
Created 06/08/2010
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ARTG
ARTG
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After our threesome with the waiter, we realized that we didn't know his name. We called the restaurant after he left our hotel, but by then it was after closing time. And the next day, Sunday, they weren't open.

"He told us his name when we first sat down in the restaurant, but who ever really listens to that?," I said as we lounged around on Sunday morning. Sunlight seeped into our hotel room through the sheer white curtains. The smell of coffee filled the air as the coffee maker made its final gurgles.

Your hair was in a ponytail on top of your head with several loose strands falling down on your forehead and neck. You were wearing glasses, and studying the crossword. Not looking up you said, "It started with a J. Or maybe a G." Your gaze never broke from the puzzle. "American painter, William 'blank' Chase....seven letters.... third letter is R?"

"Merritt?" I replied. It must have been the right answer, because you quickly scribbled something down.

Still engrossed in the crossword, again you spoke without looking up. "Especially after all that happened that night. I'm just drawing a blank." An answer to the puzzle must have come to you, and your pencil pounced on it. Then, placing the pencil and the folded up newspaper on the end table, you stretched. Your short, white nightgown rode up and your little patch of pubic hair was visible through your sheer panties. You sat forward and stretched your back like a cat. Leaning over to me, you put your hand on my bare chest, kissed my cheek and nuzzled your head under my chin.

"Tell you what," you said. "Tomorrow I'll call to find out." And then your hand slid down into my pajama bottoms...

So it was Monday before we were able to find his name.

The phone rang and a voice came on the line. "Dolce Vita."

"Yes," you began, "My husband and I were in Saturday night, and we had a tremendous time, thanks to our waiter. He really took care of us." You shot me a mischievous look that said, he really took care of us, all right. "We just can't remember his name. He was tall, muscular, blonde....yes, that's him...Jack...that's right. We wanted the manager to be aware of a job well done." You winked at me.

The person on the other line responded, then you said, "Can you have Jack call us? Here's our number." You gave the person your cell number, and then added, "When do you expect him to work again?...okay, great...Thanks. You too. Bye" And you hung up the phone.

"And?" I asked. I was trying not to betray my excitement.

"She says he's on the schedule for tonight," you said, "The person who answered was the manager working that night. Her name is Trudy."

"Trudy," I repeated. "It's funny, I don't picture her as a Trudy. But you know, under those glasses and plain clothes, I see a very beautiful girl," I said as I thumbed through the hotel copy of the tourist guide.

"You were really taken with her, weren't you?" you teased. After all this time together, we seldom pulled punches.

"Well...I guess," I pretended to hedge. "Weren't you?"

You paused a moment and laughed. Swatting me playfully with the folded paper, you blurted out, "Well yeah! You know what a sucker I am for blue eyes!"

**************************************

Jack called later that evening.

"Of course I remember you two. How could I not?" he said. "No regrets?" he added quietly. I could hear the busy noise of the restaurant in the background. He must have been starting his shift.

"None whatsoever, except we didn't get your name right away," I replied. "In fact, we'd like to get together again. Tonight, maybe?"

"Um...sure." He seemed surprised. "But I don't get off until ten."

"That's okay," I replied, and I reminded him of the number of our hotel room. "One more thing," I added. "Your manager..."

"Trudy? he asked.

"Yes, Trudy. Do you think she would be interested in coming? " It was a stretch, I know, but I had to give it a shot.

"I don't know," he trailed off. "I'll see....I'm not sure I really know her well enough to ask...she is pretty cute....worth a try, I guess," he said. "But I'll be there after I get off, with or without Trudy."

"Actually, you'll be here, and then we'll all get off," I joked. He gave a polite chuckle at my meager joke.

Later, we got another call from Jack. We could hear the bustle of the restaurant in the background. "Here's the deal, he said, "Trudy said she'd like to come. That's really something, because I'd thought she'd turn me down flatly. I thought it best to tell her what we would be up to, but she said she only wanted to watch. She has no desire in participating. Are the two of you okay with that?" he asked.

I spoke for both of us and said, "It won't bother us if it doesn't bother you or her."

"Good," he said. "I can't tell if she's on the fence about this or if she's excited. She's a hard one to read. Gotta go. See you tonight."

This encounter would be more planned, not spur of the moment like the first one, so we were both more nervous. We changed clothes several times before we settled on what to wear. You wore a pair of stretchy black yoga pants and a white cotton camisole. I decided to go barefoot with jeans and an untucked short sleeve collared shirt. It was, after all, getting near the end of our trip, and we were running out of clean clothes.

We had a couple of bottles of wine sent up. We were having a glass in the sitting area of our suite, passing the time finishing the crossword when there was a knock on the door. I looked at my watch. Thankfully, they were a little early and the suspense had been killing me. I opened the door and was pleased that Trudy had decided to come with Jack.

"Come in, come in. Good to see you," I said. We introduced ourselves to Trudy, and you gave Jack a peck on the lips, which lingered and turned into a more passionate kiss. Breaking off the kiss, you smiled and winked at Trudy and asked her if she would like a glass of wine.

Trudy really looked good that night. I guess the first night we saw her must have been an off night for her. She was about 5-2 or 5-3, and what most would agree to be voluptuous, but not fat. Her sapphire blue eyes contrasted nicely with her porcelain skin and black hair, which was wavy and shoulder length. She wore gray slacks and flats, and the white button-down work shirt could not keep from displaying her breasts which were probably a C, maybe a D cup, in proportion with the rest of her figure.

"I'll take a glass," she said as she looked around and had a seat. When everyone had a drink, we settled in for a little conversation. You sat in my lap with your arm around me. Jack sat on the other edge of the sofa from Trudy.

"So , Trudy, how did you end up in the city?" you asked, making small talk.

"I came out of high school to study art, and just sort of stayed ever since," she replied. We kept eye contact, but one of my hands was stroking the inside of your thigh through your yoga pants, while the other lightly found your nipple through your camisole. The touch made you close your eyes, but you tried to continue with the conversation.

"So are you still in school? " You smiled and kept your eyes closed as my hands caressed your body.

"No, not right now..." she said. We were obviously distracting her. She looked to Jack, who sat with his head propped in his hand, maintaining eye contact with her. "But I ...plan to go ....back in the fall," she hesitated, looking from you and me, and back to Jack. You unbuttoned my shirt and ran your hand inside, while opening your legs wider. The tight black yoga pants created an obvious camel toe effect, and I moved my hand up to feel it. My other hand disappeared under your camisole. As I stroked you through your pants, you ran your fingers through my hair as you turned your face back to kiss me. You couldn't stand it anymore, and wiggled out of your yoga pants and camisole. Now completely naked, you unbuttoned my shirt and took it off.

And that was officially the end of the small talk.

You unfastened my jeans and pulled them off. I hadn't bothered with underwear. As you got down on all fours to suck my cock, I slid off the chair and got on my knees in front of you. I gently stroked your back as you worked your way up and down the shaft, pausing occasionally to lick my balls and stroke me.

Jack hurriedly was unbuttoning his white button down work shirt. He threw it off and slipped down his black work slacks and boxer briefs. His shaved cock was ready, the head purple and swollen. He got on his knees beside me and stroked himself right in your face, hoping you would work on his cock too. You kissed the head, tasting his clear precum on your lips. Stroking Jack's dick, you resumed sucking and licking mine, concentrating on flicking your tongue on the underside of the mushroom tip. Then your own sexual tension must have gotten the best of you.

"Jack, I need you to fuck me with this thing," you purred as you stroked his cock. Jack went behind you, got down on his knees and, looking down at your engorged pussy, slid his cock into it. You kept sucking me, and I leaned forward to watch Jack's cock travel in and out of your wetness. Jack was so big that the inner lips would get pulled slightly, first in and then out, with each stroke. I pulled your cheeks apart to get a better look, and placed a finger into your ass.

"Ooh!" you exhaled, closing your eyes. "Keep it up, that's it." I knew that you couldn't keep sucking me right then, so I slowly stroked my cock, making sure that Trudy could get a good view of me. Jack was ramming you pretty hard, and your tits swayed with each thrust. He increased his pace and finally pushed deep and held it there. The base of his smoothly shaven cock pushed my finger a little deeper into your ass. His whole muscular body seemed to twitch, and I could feel his cock spurt his cum deep inside you. Finally he pulled out with a shudder. He rolled over on the floor, exhausted. I caught Trudy staring at his big, glistening, though now flaccid, cock.

You had your ass in the air, and Jack's cum was seeping out onto the lips of your pussy. Your chest and the side of your face were buried into a throw pillow on the floor, but you managed to mumble, "Now you, baby. Put your cum in there with Jack's." You were reaching back to rub your pussy, smearing Jack's cum around.

I positioned myself behind you and slowly slid the whole length of my dick in and out of you, turning one hip slightly so that Trudy could see. She wasn't crossing her legs anymore, and I could see a dark shadow at the crotch of her gray slacks. If she had been less inhibited, she would have been rubbing herself.

As my dick pushed into you, some of Jack's cum leaked out, dripping down onto my balls. It wasn't ten strokes before we both came. You muffled your groans into the throw pillow on the floor as my cock shot my seed into your pussy with Jack's.

You turned over onto your back, and our cum rolled out onto your ass and then the floor. Leaning back on one hand with your legs opened toward Trudy, you took a finger and dipped it into your pussy to retrieve our cum. You showed it to Trudy and cooed, "What do you think?" She was speechless, so you offered a few finger fulls to Jack and me. Holding it up to our mouths, we looked at Trudy as we tasted our collective cum, sucking her fingers to get all of it. You got up and moved to the edge of a chair, and Jack and I ate your cream filled pussy.

Jack began concentrating on your clit, and when I started tonguing your asshole, you came again, crying out with your orgasm. Trudy had to shift her position on the couch. She was clearly getting aroused, but still too shy to touch herself in front of us. The three of us, Jack, you, and I, rested for a moment.

I got up to refill everyone's glass.

After she'd had a another glass of wine, you persuaded her to change into one of the plush white hotel bathrobes. Of course, being so shy, she went into the bedroom to do it. She emerged from the bedroom with her oversized purse, where she had presumably stowed her clothes. Placing her purse on the end table, she curled up on the couch with her feet under her. Little by little, she seemed to be loosening up.

"Another glass?" you asked her, but you were already pouring it. Taking a seat right next to her, you suggested, "Maybe we can get you boys to put on a show for us girls. How about it?"

Jack seemed to know just what you wanted, and leaned back on his knees and hands to show me his large, semi erect cock. I leaned forward to tongue his nipples, feeling them harden as I licked them. Out of the corner of my eye, I made sure you and Trudy could see. As I reached down and grasped him, his cock twitched to fully erect. As I stroked it, I asked you, "Do you like that?"

It was Trudy who responded. "Yes," she exhaled. It was the first thing she'd said in a while.

"Do you want us to continue?" I asked coyly.

"Yes," she said, breathlessly. You had begun to stroke your pussy. Trudy was still wrapped up in the robe.

"Do you want me to suck his cock?" I asked her.

"Yes," she said a little louder.

"Then open your robe," I directed her. She hesitated for a moment, but then slowly undid the tie and opened her robe. She was still wearing her bra and panties.

"Those, too," I insisted.

You stopped stroking yourself and impatiently pulled at her panties, "Just do it, Trudy." You were ready for the show to continue and sounded a little exasperated.

She reached around her back and undid her bra and tossed it to the floor. Then she lifted her hips and shimmied out of her panties. Her breasts were round and creamy with puffy pink nipples. Her bush, though full, was trimmed enough so that her engorged, pink inner lips were pouting out. All she was wearing was the open terry cloth bathrobe.

"Now, play with yourself, and I'll start sucking his cock," I said.

She began languidly rubbing herself with two fingers. "That's it sweetie, rub that pussy," you encouraged her in a low voice as you sat right beside her and rubbed yours. I waited to begin sucking Jack. I wanted to hear her say it, to ask for it, to beg for it.

"Go ahead," she said meekly.

"Go ahead what? What do you want? Say it. Tell me what you want me to do," I insisted.

"Suck his cock. I want you to suck his cock," she gasped.

"Until when. How long should I suck his cock?," I continued.

"Until he cums. Until he cums all over you," she managed.

Satisfied with her answer, I ran my tongue up and down Jack's cock. He had gotten soft again, and his cock had drooled a trail of clear precum down the shaft. I touched my tongue to it, and pulled away a clear strand before taking the rest of him in my mouth. The two of you were working steadily at yourselves, watching us. Jack straightened up and put one hand on my shoulder, and ran the other hand through his wavy blonde hair. My mouth was moving up and down on his cock, while my tongue moved side to side on its dusky, engorged tip. It was really starting to leak his sweet-salty precum now.

"That's it, honey," you said with a gasp, "Suck that cock. Suck that beautiful cock. It gets me so hot to see you suck him." Your finger was working little circles over your clit.

You leaned over and took one of Trudy's pink strawberry nipples into your mouth as the two of you stroked your pussies. Jack saw you do it, and suddenly came, grunting with each spurt as his cock jetted his cum in my mouth. I struggled to keep up, hurriedly swallowing each hot burst. When he was finished, he withdrew and we straightened up, kneeling face to face. He began kissing down my chest, licking and sucking my nipples, licking and kissing my lower stomach, down to the smooth base of my hairless cock. I leaned back against a chair, making sure that you girls could see what he was doing to me.

You moved down from Trudy's breast, kissing her pale white stomach, slowly moving down to her black triangle of hair. She had shed any notion of not participating, and withdrew her hand from her pussy to allow you access to her swollen lips. She slumped down on the edge of the couch as you positioned yourself between her legs. She ran her fingers through your hair.

Jack stopped sucking my cock long enough for me to sit next to Trudy. I settled in on the couch beside her, and Jack walked over on his knees and resumed stroking, licking and sucking my aching cock. Next to me, Trudy was pulling on her nipples while your tongue worked up and down her engorged pussy. With her hand nearest to me, she caressed my firm lower stomach, feeling the smoothness of my pubic region. Jack firmly but slowly popped the head of my cock in and out of his mouth, causing me to groan each time he did.

"Lick his nipples, Trudy," you hissed. "If you want to see him to cum, lick his nipples." From experience, you knew.

Trudy tried to roll over toward me, but the bathrobe restricted her movement, so she shrugged her arms out of it. Now able to roll over to me, her breast pushed softly into my shoulder, and she firmly tongued my nipple. That did it, and as Jack pulled my cock out of his mouth and Trudy kept tonguing my nipple, I shot my cum all over my stomach. Jack moved up to lick up the warm, salty spunk from my skin.

Trudy stopped tonguing my nipple and moaned. I was exhausted, but I looked down to see that you had two fingers in Trudy, fucking her pussy while you licked her clit. Her panting increased, and she ran her fingers through your hair feverishly. Suddenly, she came, leaning her head forward and closing her eyes tightly, whimpering sweet sounds with each wave of her orgasm.

You planted sweet kisses in her little black triangle as she panted in the afterglow and stroked your hair. But you sank down to the floor when you realized that Jack had gone around behind you to get in position for you to sit on his face. You leaned back a little and pulled your pussy lips apart so we could see Jack's tongue flicking your little pink pearl.

"Do you like watching that?" you murmured.

"Mm-hmm." I assented. My cock was soft and spent, but I was still enjoying the show of another man eating my wife's pussy.

Trudy had put her head on my shoulder. I leaned forward, and with a sideways glance, could see her smiling, engrossed in what Jack was doing to you and your pussy. We watched as you rode Jack's face, making small thrusts with your hips. Grimacing, you dug your fingers into Trudy's upper thighs as you climaxed all over Jack's mouth and cheeks.

When you were done, you dismounted Jack and leaned forward to rest your upper body on the couch between Trudy and me. The four of us were completely relaxed, and no one said anything for what must have been a very long time. When you and I could no longer keep our eyes open, we stumbled off to bed.

We woke the next morning in our king-sized hotel bed. The soft morning light was streaming in. Your eyes opened to mine as we felt the bed shaking. We looked over at the same time to see Trudy riding Jack's cock next to us on the bed. Her full, white ass was shaking back and forth. Her perfect ivory breasts were elongated and swaying down in Jack's face.

They were too engrossed in each other to notice us. Trudy leaned forward to kiss Jack, her jet black hair falling off her neck and down around their faces. You and I got out from under the sheets, and came around to the foot of the bed to get a close up view of Jack's thick cock plunging in and out of Trudy's tight little pussy. Her white juices were trickling out of her, and running down onto Jack's thick veiny shaft, more with each stroke. Jack's thrusts became less frequent but more urgent, and he exploded inside her.

After his cock had stopped twitching inside of her, you put your arms around her waist and whispered in her ear, "Come sit on our faces and feed us that cum."

ARTG
ARTG
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