Emerald Ch. 03

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Emma begins sex-filled weekend in the Windy City.
4.8k words
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Part 3 of the 6 part series

Updated 09/22/2022
Created 07/24/2003
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emerald37
emerald37
16 Followers

Chapter 03: The Trip to Chicago

The trip to Chicago was uneventful. I took gathered my bags and took a taxi to the downtown hotel John was staying at. I checked my voice mail on my cell phone and had a message from Jason saying he had made it to his father's safely.

I had a note from John waiting for me when I checked in at the hotel desk. I settled in our room and read the note. John said to be ready for dinner about 6:00. We would be meeting the client for dinner and drinks and maybe some dancing afterwards.

"Hmm dinner and dancing," I thought to myself. "I am sure I will end up as someone's dessert tonight." I giggled.

I looked at the time it was almost 1:00 so I had some time on my hands. I found the hotel directory and sat down reading it. The hotel offered a gym, sauna, and massages. A work out and a massage sounded good so I changed into some workout clothes and headed down to the gym.

There were a couple of attendants on duty at the desk. I showed them my key and a very handsome well built young man handed me a towel and offered his assistance if needed. I smiled and told him I was unfamiliar with their equipment and just might need some.

The attendant's name was Thomas. He showed me the various machines and said he doubled as a trainer and a masseur. We made small talk, both of us stealing admiring glances each other's bodies, as he helped me through my workout.

Thomas told me the gym was usually pretty quiet on Friday afternoons, as most of the guests were headed home for the weekend. He said they usually left about 3:00, just leaving the exercise area and locker rooms open, but he would be happy to stay as long as I wanted to use the facility.

I smiled and thanked him telling him that was very thoughtful of him.

He left for a moment and told the other attendant to go ahead and leave and lock up.

Thomas showed me the proper use of each machine, sometimes placing a strong and on my arm or back. A few times I felt his hands slide down to my bottom and linger there.

I was nearly completed with my workout and asked Thomas if I could get a massage. He told me certainly and directed me to one of the massage rooms off the main part of the gym, telling me there was a small bathroom that doubled as a changing area inside.


I went into the massage room and found the bathroom he had told me about. There was a stack of big fluffy towels so I undressed and wrapped one around me.

I went back into the massage room and Thomas was already waiting for me, warming the massage oils.

Thomas pointed to the massage table and told me to lie down, he would be ready in a moment.

I opened the towel allowing him to see my naked body for a moment as I climbed up on the table. I lay face down on the table with the towel just draped over my bottom.

Thomas came over to the table with a warm bottle of oil and asked if it was ok to remove the towel.

I smiled up at him and told him "Sure, we don't want it in the way."

"A lot of my female clients enjoy being massaged fully nude," he said.

Thomas lifted the towel and laid it to the side. I felt the warm oil dribble on my back and shoulders as his strong hands began to work my body.

"You have beautiful skin and muscle tone," Thomas said.

"Thank you, your strong hands feel so good," I replied

His hands worked lower on my back and sides. I felt his fingertips touch the sides of my breasts a couple of times as he worked the oil into my skin.

He worked his thumbs along my spine down to my lower back. He stopped just short of my bottom and asked if it was ok. I nodded approvingly and felt his strong hands begin to massage my ass cheeks. I spread my legs a bit knowing he could probably see my shaved labia from his angle.

Thomas worked his way down and began to work the upper thigh muscles of my left leg. He then bent my leg at the knee and massaged the calf muscles and foot. He moved around the table and repeated the same procedure on my right leg. I smiled knowing he was certainly able to see my pussy the way he was bending my legs.

Thomas lowered my leg then placed the palm of his left hand on my sacrum and began to massage it. I moaned slightly as I felt the nerves from my lower back shooting waves of pleasure straight to my pussy.

I felt myself becoming highly aroused. My nipples hardened and my pussy began to moisten. I spread my legs wide in a silent invitation to him. I raised myself on my elbows a bit, knowing he could see my breasts, and smiled back at him.

Thomas looked up at me and smiled as I felt warm oil dribble over my ass. Then his strong right hand began to massage my ass cheeks. I moaned with pleasure as I felt his oily fingers run down the crack of my ass over my tight anal bud to my very wet pussy lips.

Thomas ran his fingers over my labia for a moment as I raised my hips off the table some to allow him access. His expert fingers found their mark as he pulled back the hood from my clitoris with two fingers and massaged it with a third, his left hand still working my sacrum.

I felt my body tighten as my first orgasm began. Thomas inserted a well-oiled finger into my vagina and sent me over the edge. I came hard, my pussy contracting on his finger, as he worked it in and out of me. I was moaning as I came down from my orgasmic bliss.

Thomas turned me over on to my back and stopped for a moment to remove his shirt, exposing his hairy well muscled chest. He dropped his shorts and briefs and kicked off his shoes and socks moving back to the head of the table, his hard cock inches my mouth. I looked up at him and smiled, licking my lips in anticipation.

I reached out and stroked him pulling him to my mouth. I let my tongue swirl around the head, licking off a drop of precum before taking him into my mouth. I began to suck him in as he held my head in is hands. I made sure he was hard and ready and pulled his cock from my mouth.

Thomas pulled my ass down to the bottom edge of the table and spread my legs wide.

"Tell me what you need massaged next Emma," he said.

I looked at him as he retrieved a condom from his bag and moved between my thighs. "I need you to massage my pussy with that big cock of yours and fuck me hard," I whispered

Thomas smiled up at me unrolling the condom onto his cock. He rubbed his raging erection up and down my pussy lips before finding my entrance. He pushed slowly into me filling me with his hard cock. I cried out in pleasure as I wrapped my legs around his waist. He began to stroke in and out of me as he leaned forward kissing me. Our mouths intertwined as his hands came up and began to pull and twist my hard nipples.

"Oh Thomas," I moaned, "it feels so good."

"Yeah Emma, you feel so hot," he grunted between thrusts.

Thomas quickened the pace of our fucking as he kissed lower on my neck and shoulders, finally sucking in my nipples. I felt his heavy balls slapping against my ass as he pummeled me with his cock.

"You like that baby?" he whispered between mouths full of tit.

"Oh god yes, don't stop," I moaned.

I thrust my hips up to him, lifting my ass from the table, wanting him as deep as possible. His big cock felt wonderful as he rammed it deep into my needy pussy. We both began to moan as our orgasms approached. I felt his body stiffen and his cock expand inside me as he came hard, his sperm filling the condom deep inside my pussy. I wrapped my legs tighter as my pussy exploded in a gush of girl cum, my body shaking and trembling as orgasm over took me.

He held me in his arms kissing me as we came down. "Mmm that was a pretty good massage," I said smiling up at him.

"My pleasure madam," he replied, grinning down at me.

I felt his cock soften and slip from me. I slid off the table kneeling before him and pulled the condom off his deflated cock. I laid the sperm filled condom aside and took his cock into my mouth sucking and licking him clean.

"Do you always give your female clients such full service?" I asked, grinning up at him.

"Only when they express a need for it," he replied, smiling back down at me.

"Hmm, must have been dropping the towel that gave me away," I giggled.

I looked at the clock on the wall and told Thomas I had better get going, as I had to meet my husband soon for dinner.

Thomas laughed and replied, "A very lucky man."

I giggled and ran off into the bathroom, rinsing off in the shower before getting dressed.

I came out and Thomas was dressed and had finished tidying up the massage room. He gave me a kiss and a wink as he let me out the front door of the gym.

"Wow," I thought to myself, "I think I am going to like Chicago."

I returned to the room and ran a hot bath. I would have enough time to bathe and start getting dressed before John arrived. I undressed and sat and soaked in the hot water for a while.

I was relaxing in the tub when I heard a knock at the door. I wrapped a towel around me and went to see who was at the door. Looking through the peephole I could see it was it was John. I opened the security lock and told him to hurry. I closed the door letting the towel drop as I wrapped my arms around my husband giving him a sensuous kiss on the lips.

"Hmm," he said, "I could get used to my sexy little wife meeting me at the door naked in these hotels."

I giggled as I undid his jacket and tie. "I missed you," I whispered.

"I missed you to baby," he replied as he helped me remove his clothing.

"I think we have just enough time for a quick one and a shower before dinner," I laughed.

I dropped to my knees and helped John lower his pants and remove his shoes and socks. I pulled down his underwear, helping him step out of them. I stroked his cock up and down sucking him into my mouth. I noisily sucked and slurped John's cock as he grunted approvingly.

"So has my slutty little girl behaved herself this week?" he asked.

I looked up at him and shook my head in a negative response.

John's cock was nice and hard by now from my sucking so I removed it from my mouth and led him by his erection to the bed. I lay back on the bed spreading my legs wide pulling my husband on top of me.

"I was a nasty girl this week Daddy," I said, as I guided his cock to my entrance.

"Oh, I see," he replied, sliding his cock into me, "Just how many men did you fuck this week?"

"Four men and one woman, Daddy," I moaned as John's big cock filled my pussy.

"Oh, you have been a naughty little slut," John said as he lifted my legs to his shoulder and began to stroke in and out of my pussy.

"Yes Daddy," I cried out, "fuck me hard for it."

John slammed his cock in and out of me without mercy. I moaned with pleasure as I told my husband of the week's sexual adventures. It felt like his cock grew harder inside me the more of my slutty story I told.

I began to cry out as my orgasm overtook me. I felt John's body tense as his cock head expanded inside me filling me with his seed.

John let my legs down as he leaned over kissing me. His hand came down playfully popping me on my ass as he did.

"Ouch!" I cried out.

John grinned down at me and said we had better get our shower. He led me to the bath where we soaped and caressed each other's bodies under the warm spray. John watched as I shaved my legs, underarms and pussy, making sure my skin was silky smooth.

We dried off and I went to the vanity and started doing my hair and makeup. John got dressed as we talked back and forth. John explained that the negotiations with Allen and David, the client, had went well and they should sign the contract tomorrow after the golf match.

He was tying his necktie in the mirror and grinned slyly as he told me how two of David's personal assistants had entertained Allen and him last night.

"Hmm, so I wasn't the only one that was bad this week?" I giggled.

"Far from it lover," John said, moving behind me kissing my neck, "I think you may have the opportunity to be very bad again tonight."

"Oh, is he handsome?" I asked.

"I don't think you will be disappointed," John replied, "and he does have an eye for married women."

"Mmm sounds like fun," I laughed.

I piled my hair on top of my head and went about getting dressed, slipping on a black lace thong. I had chosen a black halter dress, with an open back and plunging neckline, and a pair of 6-inch heels. My legs were nicely tanned so I decided against hose.

I turned and faced John and asked, "How do I look?"

"Absolutely delicious," he replied.

I gathered my purse and we headed out the door to the elevator. John kissed me in the elevator and told me to have fun this evening.

Allen and David met us at the entrance to the restaurant. Along with them were Ginger and Ashley the two personal assistants John had spoken of. Introductions were made all around and we headed to our table.

Dinner was delicious and we shared a few bottles of wine. The conversation started out the usual business talk but I noticed David began talking more to me as the evening progressed. John and Allen seemed engrossed in the two personal assistants as well.

With dinner finished, David suggested we retire to the lounge for some dancing. We all agreed and walked over to the lounge, taking a seat in a horseshoe shaped both. I ended up next to David with Ginger, a tall blonde, next to Allen, and Ashley, a striking brunette, next to my husband.

David asked me to dance a slow one with him. I agreed and moved to the dance floor with him. The others soon followed and we were soon separated in a sea of couples as people got up to dance.

David and I made the usual small talk at first. I could definitely feel the growing electricity between us as well as his erection pressing against me a few times. His hand drifted from my back down to my ass a few times and I would smile up at him each time, letting him know it was ok. We returned to the table to rest for a moment and were soon back on the floor. The second dance he not only caressed my ass but a couple of times held our hands between us and brushed across my left breast a few times.

We danced several more dances, David holding me tighter each time letting his touches linger a bit longer. His touches became more brazen, cupping my breast thru my dress a few times and even sliding his hand under my dress once, feeling my bare ass cheek. Our conversation had moved from formal to flirtatious and I knew he was interested in more than dancing.

David asked me if I had ever seen the city at night. I told him not really, but it sounded fun. He told me he would have his driver take us on an evening tour of the city. I told him I would enjoy that very much.

We returned to the table and, as if on cue, Allen, John, and the two women announced they were ready to leave. David wished them goodnight and asked John if he minded him taking me on a drive around the city for a couple of hours. John smiled and told him not at all. I had the feeling this was a setup but I was not really minding it at all.

John kissed me and told me to enjoy as David called for his driver.

We left the lounge and David and I headed to the front door of the hotel as the others head toward the elevators.

I had to stifle a giggle, only guessing what lay in store tonight.

We walked out the door of the hotel just as a sleek black stretch limousine pulled up. The hotel doorman opened the car door for us and David helped me inside and climbed in after me. I snuggled next to David on the plush leather seat as he wrapped his arm around me.

The limo pulled away from the hotel and David was soon pointing out the sites of Chicago to our left and right as we rode.

We looked into each other's eyes and our lips met in a few soft, shared kisses as we rode along.

David opened the moon roof and asked me if I would like to take our tour up top. I smiled and told him yes.

David removed his jacket and tie and helped me to the open moon roof. I was enjoying the night breeze as we glided along the city streets.

I felt David's hands go around me momentarily before sliding into the halter of my dress encompassing my breasts. I rubbed my ass back against him, showing my approval. His hands were playing on my breasts as I felt his hot mouth on my neck nibbling and kissing. I pushed my ass hard against his crotch feeling his stiff member rubbing against my thong-covered bottom.

I reached back fumbling with the zipper of his slacks trying to free his cock. David let go of my breasts and unbuckled his pants letting them fall to the floor of the car. He reached under my dress sliding his hand inside my thong, touching my wet pussy lips momentarily, before sliding the thong down. I kicked off my high heels and pushed my thong the rest of the way off.

David was kissing my neck as I felt his hands undo the halter and lower it, exposing my breasts. I spread my legs as David moved slightly under me, lifting the back of my dress, aiming his cock for my entrance. I gasped as I felt the head of his cock penetrate me.

I held on to the edge of the moon roof as David pushed slowly into me. My breasts were below the opening so no passersby could see I was nude above the waist. My dress was bunched up around my waist as David began to slide his cock in and out of me. His hands were back up fondling my breasts as I pushed myself against the rising thrusts of his cock.

I felt David's hot breath on my neck as he whispered in my ear, telling me how sexy I was and how much he was enjoying fucking me. I was so swept up in the moment all I could do was moan. It was so incredibly sexy being fucked by a man I had only met a few hours before, on a wild limo ride through the streets of Chicago.

My body began to shake as I felt his cock slam deeper and harder into my vagina. "Oh god, I cumming," I cried out.

David began to grind his cock into me from behind, lowering me back down into the car, as my pussy contracted on his cock.

I had not even recovered from my first orgasm when David pulled my dress the rest of the way off and laid me back on one of the seats. My right foot was planted on the floor; my left hung over the seat back, as David moved over me. David fed his stiff cock to my mouth, letting me suck him for a few minutes, before he decided it was time to take my pussy once again. His erection showed no signs of flagging as he moved between my open thighs and entered me again.

I felt his hairy chest against my erect nipples as he slammed his cock in and out of me. I cooed and moaned as wave after wave of orgasms came over me.

David kissed down my neck, his mouth finding my nipples, sucking, and biting them as he fucked me.

I lost count of the number of orgasms I had after five. David's stamina was amazing. I was brought back from the fog of my pleasure with the sound of David's voice.

"Emma, I am going to cum inside your little married cunt," he announced.

"Yes, fill me with your sperm," I moaned.

"I am going to send you back to your husband, well fucked, with my seed dripping from your cunt," he announced, as he drove hard into me.

I felt his cock head swell inside me as the first bursts of his semen shot into my pussy. I screamed in pleasure as I felt him fill me with his sperm.

"Oh god," I moaned, "give it to me David."

David moaned and grunted as he emptied his sack inside me, our lips locked in a passionate kiss.

David pulled his cock from my well-used pussy and I felt the juices of our coupling seep from my pussy and run down my ass onto the leather upholstery.

David leaned and kissed me asking, "How did you enjoy your tour?"

"Mmm best site seeing tour I have ever had," I said grinning up at him.

"I guess we had better get cleaned up and get you back to you husband," he said.

David opened a small cabinet and pulled out a container of wet wipes. He began to wipe up our juices from between my legs and the seat. I reached and took his cock in my hand, pulling him toward me, and began to suck and lick him clean as he wiped me up.

emerald37
emerald37
16 Followers
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