Chicago - My Kind of Town

"Yes, play with me. It feels so good. Make me cum, make me cum," she would repeat over and over.

And cum she did soaking my hand with her female juices. She had to cover her mouth to muffle her moans of ecstasy. Then after she composed herself she would have me stand up and she knelt in front of me. Catherine unbuckled my belt and lowered my pants to the floor. Then she slowly pulled my boxer shorts down my legs. She loved it when my erection got caught in the waistband of my boxers and my cock would spring forward as it cleared my shorts. Catherine would then suck my cock until I came in her mouth.

We also revisited the bar near her place and after a burger and a few beers it was sex in her car again. Sometimes we fucked and sometimes she just sucked my cock while she fingered her pussy. She would unbuckle my belt, unbutton my trousers and pulled them along with my boxers down to my ankles. As Catherine pulled my boxers down over my balls she would lick and suck them before kissing her way up my shaft. Looking up into my eyes, she would slide her lips over my bulging head with her hand still wrapped around my shaft. Her tongue would swirl under the ridge of my crown as she sucked me deeper into her mouth. She would test her gag line and take my cock down her throat.

She would pull me deeper into her mouth, pressing her lips tightly against me and sucking hard. The feel of my hard cock sliding between her lips and over her tongue would have me on the verge of a huge orgasm. Catherine would often slip her hand into her spandex and finger her dripping pussy. The smell of sex would be rampant in her car.

When I felt my cock swell and I told her that she was about to receive my load. Muffled moans would escape from her throat as she eagerly sucked my dick awaiting my release. She would move her lips up and down over my shaft in rhythm with my thrusting motions. She would be drooling like crazy and I could feel the wetness running down my pecker onto my balls.

My breathing would become more erratic as I was about to lose control. Catherine would look up at me with those big eyes and nodded her head, letting me know she wanted to taste me and then she would cover my cock with her mouth just as I lost it. I always let out a soft grunt as I pumped stream after stream of hot cream into her mouth. She would move her hand under my scrotum to squeeze out the last few drops and then Catherine would have her orgasm. The feel of my throbbing cock in her mouth, the taste of my seed and her hand in her cunt was just enough to set her off. The pressure in her lower tummy would gush out through her pussy and soak her fingers.

My cock would fall from her lips and cum would drip from her lips and chin as her body would jerk and shudder in orgasm. Catherine always looked up at me when she was done, blotches of cum glistened on her lips. The smell of pussy in the car was powerful. I would take Catherine's hand and licked her fingers clean. I would then pull my shorts and trousers back up and dress the best I could in the confines of her car.

One night when we were having a burger we discussed getting together in bed and being completely naked when we had sex. Catherine didn't know it but I was very hot for her ass and I wanted a shot at it. She had a roommate so we couldn't go to her place. I lived in an area where other corporate executives lived and I couldn't risk Catherine being seen at my place. We discussed hotels and motels but I was leery of them as many of our vendors stayed at the ones near the office. That's when Catherine suggested a romantic interlude motel called La Chateau.

THE ROMANTIC INTERLUDE

On our first trip to La Chateau Catherine arrived before me and parked her car in the private spot adjacent to the room. I had given her my credit card to pay for the room. I parked in the lot which was secluded from the road and walked to the room. Catherine was already naked when I arrived. She told me that this was the only room available as the ones with the Jacuzzi tubs were all taken.

I looked around as I undressed and spotted the water bed, mirrors on the ceiling and walls. There was a TV with a porn station and a small mini bar in the room. Catherine was naked in bed watching me as I undressed and I could tell that she liked what she saw. I liked what I saw too as it was the first time that we were completely naked together. I moved to the bed and I was anxious to get at her ass all the while wondering if she would let me fuck her in the ass. I loved anal sex and fucking beautiful shapely asses. I had always tested the water with the women with whom I went to bed. I moved her to all fours with her ass elevated and she placed her head on the mattress turned to one side so she could see me. I started playing with her pussy and her curvy ass lubricating her asshole with her own cunt juice. Catherine moaned and cooed as I fingered her pussy and her asshole simultaneously. I tried to get her asshole wet enough with her juices and my saliva so that I could fuck her ass.

Catherine had not objected to the ass play so I knelt behind her and tried to insert my cock in her ass but it just wouldn't go in. Afraid of hurting her I tried more pussy juice and saliva for lubrication but to no avail. My 8" long and 5" around cock just would not go into her tight ass. There are times when my cock feels bigger and this was one of those times. I was fingering Catherine's ass when she spoke.

"Use some cream," she said urgently, "There is some in my purse."

I got off the bed and retrieved the body lotion from her purse. As I did I realized that Catherine was going to let me fuck her in the ass. I returned to the bed and put an ample of amount of lotion in her asshole coating the tiny puckered opening of her anus and lubricating the rim. I added my saliva to my lotion covered cock and nestled my dick against the entrance of her anus momentarily before easing it inside her ass. I could feel my cock struggle to stretch the resistant muscles. My dick head burrowed in and her rigid passageway soon yielded to the determined action of my cock. Catherine moaned as my penis filled her hole.

"Go slowly at first it has been awhile," she said sexily.

I fucked her with long and deliberate strokes until my cock was sliding easily in and out of her ass. I caressed her shapely buttocks as I watched my cock move in and out of her rectum worming around inside of her curvy ass. I caressed her small tits and tweaked her nipples as I leaned over her body and whispered in her ear, "Catherine you have one hot ass, I love fucking you in your hot ass."

My hands freely roamed over her body and I pulled on her hips drawing her backwards impaling her on my inflated member. I reached for her pussy to finger fuck her and diddle her clit but I found Catherine's hand already buried in her womb. She was frigging herself frantically working herself toward an orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping faster. Within minutes I knew that Catherine felt the warm fluid being squirted inside her anus and she immediately started to cum herself. Her cunt walls convulsed around her own hand fucking her cunt as her anal muscles squeezed every drop from my spurting cock. I grunted as my whole body became stiff and I slammed my cock harder into her. Catherine writhed around and her body arched off the bed as a climax of massive proportion tore through her loins.

My cock slipped from her ass with an audible pop and I flopped down on the bed next to her. She surprised me when she covered my cock with her mouth and sucked any remaining cum from my tool. Catherine then lay on her back, splayed her legs and pulled back the folds of her vagina.

"I need to cum again. Eat my pussy, please eat my pussy," she pleaded.

I rolled over and got between her legs. I put her thighs on my shoulders and lowered my mouth to her pussy. I took one slow lick as I flattened my tongue on Catherine's mound. It felt so smooth and warm and I knew I had achieved the desired effect from her moan I know that Catherine enjoyed it. I always enjoyed the taste of her and I kept licking and eating her. I pointed my tongue and burrowed into her pussy as it parted her labia my tongue was rewarded with the exquisite taste of her juice.

Catherine was obviously enjoying what I was doing as she reached down with both hands and spread herself wide making it so much easier for my tongue to explore her pussy. Catherine was breathing rapidly and she moaned softly whenever I got near her hard clit. As I searched out her hard clit still just barely hidden she tensed and began to quiver. After I felt like I had teased her opening as much as I could with my tongue it was time to see her reaction when my tongue finally touched that treasured pearl.

I burrowed my tongue as deep into her as I could and then I just sort of licked and sucked my way up. When I got to her clit I used the very tip of my tongue to push back the little hood. I flicked my tongue over it once and then used the tip to explore the folds of flesh on either side of it. Catherine was now moaning and she used her fingers to pull her hood back as she arched herself so that her clit stuck out even further like a little cock. I nuzzled it with my nose taking in her scent and I licked it once more before I took it between my teeth and gently nibbled it.

Catherine went wild and started bucking and moaning loudly. She let go of her own fleshy hood and pulled my head to her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth as I could and Catherine humped my face for all she was worth. I was excited that I was able to get her that excited and I sucked harder and played with her wonderful clit with my lips, tongue and teeth. I don't know exactly how many times Catherine came but finally she collapsed on the bed, her body in spasms. I lay next to her and stroked her body my hands moved freely over her tits and pussy mound. She rolled toward me and embraced me and yelled for me to hold her tight.

"Hold me, oh please hold me," she pleaded as her orgasm and spasms continued.

Once she calmed down, we lay there for awhile making small talk and then Catherine started stroking my cock. Catherine added some body lotion as she kept stroking me cock and soon had me hard again.

"I like playing with your cock. You have a big cock," she told me.

"It's not that big," I replied although I was very comfortable with my manhood.

"It's the biggest I have ever had," she said with a sultry tone.

"Well there are plenty bigger than mine," I assured her.

"If I had a cock I would be playing with it all the time," she giggled.

We continued our conversation as Catherine continued to stroke my cock. I learned that she had first been ass fucked before she was married and divorced. Catherine had been working downtown Chicago at the time and she went out with two guys from the office. They took her back to their place and one fucked her ass as she blew the other guy. She took to ass fucking after that but she was very selective about who allowed in her ass. I shared with her my love for anal sex and some of my encounters.

"All this talk and playing with your cock has got me hot again. I need to sit on your dick," she announced.

Catherine straddled my body and lowered herself onto me as she held my tool and aimed it at her vagina. My hard cock slid easily into her womb and she emitted a small gasp as it filled her hole. Catherine rocked back and forth on top of me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm buttocks in my hands as she picked up the pace fucking herself on my dick. Catherine started moaning as she fucked faster and faster. I sensed her pending orgasm and then she yelled out.

"I am going to explode. Oh, Oh hold me, please hold me tight," she screamed.

Catherine collapsed on top of me her body quivering from the intensity of her orgasm. I could feel her juices coating my cock as it remained buried in her womb. It took a few minutes for her to regain her composure and she just lay on me and cooed. Eventually she rolled off of me and lay on her back next to me. I was still hard so I took her ass again and fucked her until I released my second load into her rectum. After that we showered dressed and left the motel.

A week later we revisited La Chateau again and this time Catherine had gotten a room with the Jacuzzi tub. We entered the room and wasted no time taking off our clothes as the Jacuzzi filled with hot water and bath gel. Catherine and I showered together before entering the Jacuzzi. We soaped each other up and played with each other's bodies being careful we didn't cum in the shower. Catherine then douched both her pussy and her asshole. It was the first time I had ever seen a woman do that and it was kind of erotic.

After showering we entered the Jacuzzi armed with a bottle of wine. I turned on the jets and we kicked back enjoying the bubbles and our first glass of wine. After awhile Catherine leaned back into me and I reached around and stroked her cute titties tweaking and rolling her nipples in my fingers. I slid one of my hands down across her firm abs over her little tuft of hair and found her vagina. I played with the folds of her labia and then inserted my fingers in her pussy. I found her hard clit and rolled it between my fingers as I continued to tease her nipples with my other hand.

As Catherine got turned on I moved her to the other side of the Jacuzzi and I had her lean over the edge presenting her shapely ass to me. Her ass always looked good but this time it glistened with water and bath gel and looked so sensual. I leaned over and licked Catherine's pussy from behind driving her wild. Then I had the urge to tongue her beautiful ass so I swiped my tongue from her pussy up and over her bung hole and back to her pussy. She gasped out loud when my tongue touched her asshole. I really got into it and grasped both of her curvy ass cheeks and pulled them slightly apart so that I could get my tongue in deeper. I probed her pink aperture with my tongue as I inserted three fingers in her pussy. She started whimpering, gasping and directing the action.

"Oh my God, do it again. Lick my asshole; stick your tongue in there. Eat my pussy, tongue my ass, oh yessssss," she cried out.

I grabbed the bottle of wine and poured some in the crack of her ass letting it trickle down over her anus and pussy. I placed my mouth on her and drank up the wine swabbing her pussy and ass in the process. I repeated this several more times until Catherine seemed to go into convulsions with her first orgasm of the evening. She collapsed back into my arms and I stroked her smallish tits as she recovered from the intensity of her orgasm.

"Not in my wildest dreams did I ever think that you would ever tongue my ass or did I know it would feel so wonderful," she uttered in an exhaustive voice.

"I surprised myself by going after your ass. I have never done that before but it just looked sexy as it glistened with water. Of course I remembered that you had douched and it looked so clean. It's a great way to drink wine," I told her.

We decided to get out of the Jacuzzi before we turned into prunes. We dried off and flopped down on the water bed. Catherine began to stroke my cock into an erect state and then proceeded to suck on it. She loved to stick her tongue in the little hole and nibble on my cock head. This always made her hot and then she needed my cock in her pussy. She straddled me and aimed my cock in her hole and rode me until she achieved another orgasm.

It was time for me to fuck her in the ass so I had her kneel on all fours with her gorgeous ass in the air. She always put her head on the mattress and turned to the side so that she could watch. She had the added benefit of mirrors on the wall and ceiling and so could clearly see the penetration. I broke out the lube and put an ample amount in her asshole. I fingered her ass and pussy at the same time.

"I love the feel of your fingers in my ass and pussy together," Catherine exclaimed!

If there was one thing I liked besides fucking a beautiful ass it is preparing an asshole for a good reaming. After several minutes of finger fucking her pussy and asshole I couldn't wait any longer and I had to get my cock in her beautiful ass. I removed my fingers and lined up the head of my cock at her moist puckered ring and pressed forward slowly. My cock head strained to pop through and she let out a little groan as the pressure from my iron hard dick forced her little ring to open like a flower and suddenly my large mushroom head slipped past the ring and into her ass. Catherine let out a groan as her rear passage was stretched to accommodate my ample girth.

"Oh you are going to make me like this more than the regular way," she gasped and shivered as I filled her fully and withdrew my penis slightly.

I felt her ass tighten around me and I continued to slowly stroke in and out of her tight ass until all eight inches were tightly packed up her ass. Catherine really began to moan and her whole body shook in anticipation of what she knew was coming. I began to slowly fuck her but soon picked up the pace as I penetrated her with long hard strokes that used the entire length of my thick cock. Catherine was going wild as she loved the feel of my cock as it pulled out and then came crashing back in as my big heavy balls bounced off her clit. Catherine was thrashing around uncontrollably, gasping and moaning with pleasure. When I reached underneath her to stroke her clit she exploded with her third orgasm of the night.

I continued to hammer her ass with long strokes then suddenly I felt that familiar tension in my balls and I knew I was close. I began to piston my raging cock harder into her searing ass in search for my release, which also increased the intensity of her orgasm. She was yelling and moaning, clawing and scratching at the cover of the waterbed begging me to cum.

"Give it to me, give it to me, give me your cum, cum in my ass," she begged.

I felt powerful and dominant with my impressive dick stuffed up the beautiful ass of a woman who could not get enough of me. Catherine lay submissively before me on all fours as I towered above her like some untamed animal with a strong sexual hold on her. I took firm hold of her hips and slammed once more full force into Catherine's ass. I did that three or four more times and then I let out a loud groan as I emptied my seed deep into her bowels. I couldn't believe how much cum I produced as my dick continued to hammer into her ass.

When I was finished I pulled out of her ass as Catherine collapsed on the bed utterly spent. I slumped down next to her quivering body. I looked over at Catherine and I noticed my seed oozing from her asshole. It resembled a natural spring as the semen just seemed to bubble up as she tried to relax her anal muscles.

Catherine and I got up, showered and returned to the Jacuzzi where we soaked our aching muscles. After the Jacuzzi I offered her a massage which she gladly accepted. I had her lay face down and worked her back, legs and buttocks. Not so surprisingly I got an erection as I massaged and fingered her ass again. Very surprisingly I came a second time that night when I fucked her ass again. After the ass fuck I rolled Catherine over on her back and continued the massage this time working her tits, abs, legs and pubes. I finished her off with another thorough pussy eating which had her screaming my name and humping my face with her volcanic orgasm. After that we were really spent and had just enough energy to shower, dress and drive home.

RISKS AND REWARDS

Catherine always wore long loose fitting skirts in the work place so I decided she needed to shed the panty hose and wear something more appropriate for sex in the office. I brought a Victoria's Secret catalog into the office one day. Catherine stood by my side as we looked at the catalog on my desk. As she paged through the catalog, I stroke her legs and ass again through the pantyhose. Then I lowered her hose and panties and played with her naked ass and pussy. Catherine came on my fingers again and then she gave me one of her wonderful blow jobs.