Kyle in Chicago

Kyle in Chicago

My name is Kyle Eliott. My friends call me “strummer” because I have been known to strum a mean guitar. More about that later but for now these pages will tell the story of my sex life over the last 2 years. Believe me when I tell you, ever since my divorce two years ago, it has been a wild wild ride. I married young (20) and we stayed together for 19 years. One night she said she had enough and left me for another WOMAN!!! Imagine that!!! That moment I turned my life around. I started working out getting back in shape. Not that I was too out of shape I, by many accounts look good. I just needed a bit of toning up. My appeal with the woman really started when I shaved my head. Being a Black Male who is Tall, Medium Dark, Hansome and Bald seems to be attracting all types of women.…. Hope you enjoy my stories….

It was my first trip out of town since my divorce was final. I never was a chick magnet when I was younger so I felt that it would be hard for me to meet ladies. I had always been faithful to my wife. She had always told me that women were always giving me the double take. I never noticed after all I was spoken for. So this trip I thought that if I kept my eyes open I just might get some action.

I think I’m a good lookin guy. I’m tall (6’4’’) with a very athletic build. Wide shoulders and narrow waist, I weight about 220 pounds. I don’t look 43. People tell me that I look 30ish. People say I look like a taller Montel Williams, muscles and all. My wife is hot looking. Blonde, with long legs and a down right beautiful face. I don’t go for cute woman I go for sexy ones. Kathy was definitely sexy. Too bad she left me to munch carpet.

This time my trip took me to Chicago Midway Airport. I was just passing thru , I needed to change planes because I was due in Green Bay in the morning. Bad Luck would have it, my plane was cancelled and I would have to stay the night in Chi-town. I was not alone, several people were in my shoes. Two people in particular. Ellen and Stu.

Ellen was a stunning brunette with large tits that fit on a tall slender body. She had a nice walk that featured a great ass. She and Stu were in line in front of me waiting to find out where the airline was going to put us up for the night. It just so happened that we had 3 choices and the three of us all unknowingly chose the same place. I made my choice based on which hotel had a bar. I suppose that they did as well. I suspect that they had a head start on me. They were acting a little loopy.

In line we chatted a bit. The two of them seemed somewhat close though I did think that they just met on the plane up. I did not think that they were together together because of the conversation and the fact that Stu looked to be 30years Ellen’s senior. Nice guy and all but I just could not see them ever “getting busy” She turned and smiled at me a few times ( guess that the look that my ex was talking about) I didn’t think anything of it until she turned, took my hand and said “I hope to see you at the hotel bar in a few. I’m lookin for a good time tonight.” Now while married I would have considered that to mean drinks, jokes, and good night. Now, with my eyes wide open, I saw something that suggested that, if I played my cards right it would be better than a good night.

At the bar, Ellen sat between Stu and me. I noticed that Stu started to become touchy with Ellen. Touching her arm, and leg. She didn’t seem to mind but as he moved closer to her she would move closer to me. The couch got smaller and smaller and soon she was pinned between us. That lasted only a few minutes. She reported that she needed to go to the room. I slide over. She moved past me stumbling a bit. She fell right into my lap. I looked at Stu and he was not happy. He had the look of an old man chasing after some young thing. I think it was at that moment that I became the competition. Before that I was just the third wheel.

On the way up she grabbed a handful of my manhood. Held it tight for a second. Let it go and patted it twice as if to say “easy big boy I’ll be right back.” Excusing herself she went on. Stu could not see what she had just done. The table was in the way. I am sure that my face didn’t give her actions away. I have a reputation for never being surprised and having a great poker face. My cock would have given everything away as it was now beginning to swell.

When she was out of site Stu did not hesitate to tell me that he was planning to fuck this chick. “My cock is ready for this hottie” he said.

I said “Go right ahead don’t I won’t stand in you way. I’m just out for some drink and a good time.” All the while thinking, man if she fucks you, not only will she snap your spine but she will give you a heart attack as well. When she got back to the table she slid past him. I know she grabbed his piece because I could see it in his eyes. He hadn’t had that happened to him in a long time.

A minute or two later it was his turn to hit the room (probably to jax off and take his Viagra). Ellen shouted to him that he better not come back without another round. When he was out of site, she turned to me, grabbed my cock again and said “Damn that feels nice. I want that tonight.” I looked at her sharply. She continued. “ Look, I am gonna flirt with him big time. I want to get him to pay for our night. I have no plans to fuck him and his little dick.” Squeezing my hardening cock she said “ I want this in my mouth, between my legs and up my ass!!! Got that!!!

I’m not sure I heard her because at that point she started to stroke my cock through my pants. In any case, I shook my bigger head yes because it seemed to be the best thing to do at the time.

“Continue to play the third wheel and it will cum out great for both of us.” She let me go, slid over a bit just as Stu came in to view. He stopped at the bar and brought back a round.

Finish up guys. I want to go dancing. You up for that Stu?

“Sure lets go baby”

“Kyle you want to come along?”

“Well” I hesitated “ I don’t want to interrupt, but if you think it’s OK… “

Before Stu could say boo, Ellen moved in his direction, put her arms around him and said “Sure it will be a blast, and Stu won’t mind will ya Stu.” Sliding her hand down to his crotch. Stu’s eyes rolled back. It was obvious that she hit his Jack Pot.

Chicago has many Blues halls that have great Blues dance music. We hit one of the more famous places and after Stu paid the cover we continued the party. Ellen rushed to the dance floor Stu and I hit the bar. Ellen was not alone on the floor. There were a few couples doing there thing. Ellen danced by herself for a while and every guy in the place was watchin her. Seductive and hot could only explain her movements. Her shirt was buttoned lower than I remember. Her tits were all but out of her visible bra. Playing the role of the third wheel I suggested that if Stu wanted some tonight he better get out there and claim her before some shark in this tank does. He thought it was a good idea so he got up and started gyrating with her.

I knew he could not keep up. The bump and grind gave Stu a pup tent that was noticeable (if you looked hard enough). After a few dances they came back to the table. Stu collapsed in his chair. Ellen was hot and hyper. She sat down for one song and jumped up when the next one started. She was out on the floor alone when a hot little number joined her. Jill was short and built like a brick shithouse. She had a tight, well proportioned body with huge tits. I never saw Dolly Parton live but I would imagine that this is how she looked.

The two were doing a great job of clearing the floor. Everyone in the place got a seat so they could watch the show. Tits were bouncing, asses were shaking, hands were roaming and dicks were getting hard. After a few songs, including a slow, sexy, bump and grind, Ellen brought Jill to the table to meet Stu and I. Ellen jumped into Stu lap and made it clear that she was with him. Reaching under the table again. After some small talk the two went to the ladies room together. While they were gone Stu said “Man we got to go real soon she is wearing me out.”

After a while, Jill and Ellen returned from the bathroom hand in hand and smiling. Ellen announced that it was time to go and grab Stu and headed to the bar. Jill asked me if I had an extra key to my room for Ellen. I said sure and slipped it to her. A moment later we were getting together to go. Jill hugged everyone and said her goodbyes. Ellen, Stu and I went out front and caught a cab. Stu told me that I should sit in the front. I did. I am quite sure that he got a hand job on the ride home. I noticed a big wet spot on the front of his pants. Not to mention his eyes were rolled back in his head again. Once inside I said goodbye to Stu and Ellen turned to me and said with a big smile “had a great time hope to see you again soon” the hug was great. She grab my ass hard. My cock stiffened. I could tell she noticed. She moaned in my ear.

I left those two and proceed to my room. I opened my door and a female voice said “close the door and strip everything off”. I did not recognize the voice, I thought it was a mistake. She said it again. I was slow to react. A hang grab my package and that helped convince me.

“Ellen was right. You do have enough to satisfy both of us”

It was Jill from the club. Damn!!! My cock swelled to new heights. I jumped out of my clothes. She fell to her knees, took my cock in her hand and guided it to her mouth. I was surprised at how much she could handle.

“Damn, you’re so long and thick. I can’t take the whole thing.”

She had about half in her mouth and was pumping the other half with her hand. In the dark I could only imagine what a beautiful site that was. Her head gobblin up the head of my cock and her white hand wrapped around my slick black dick. I know it could not feel any better. With her free hand she grabbed my ass and then slipped a finger up my hole. I blew my wad in a hurry. This was the first time I had cum, by means other then my own hand, since my divorce and I didn’t even have the benefit of seeing it.

I found a wall to lean on. Jill found the light by the nightstand. “Ellen said you were gay and had no interest in cock” I asked

“That was until she told me that Black Cock were the biggest and the best. She said that she loved black cock and would not mind sharing.” Jill replied

“I second that emotion!!!” Ellen announced as she slipped in the door. “Lets get down to some fuckin.”

Feeling like a stud who’s just won the lottery, my mind flew back to the days before my marriage. Not that I had ever had a threesome before but I have seen many a porno.

“Ok girls, up on the bed. Tails up”

Both women got on the bed ass to the ceiling. Ellen’s ass was great and her hole a some hair around it. I slide behind Ellen and worked the head of my cock in her warm cunt. She took it well. She growled at me and I knew she was going to be a noisy fuck. I love that type of chick. I worked my head in and out. She was beggin for more as I slide behind Jill. Her ass was a bit bigger than Ellen’s but her cunt was hairless and smooth.

Easy big guy I ain’t had a cock up there in a while and never that big. “ I will take that into consideration.” Said with a laugh. My cock was wet with Ellen’s cunt juice only up to the head. So that’s all she got. I could swear that that was all she was going to get because she was tight. When I shifted back to Ellen. She wanted more and she got it. I worked my way way up that hole. Getting my entire pole wet. Ellen was moaning and groaning. She started to shake when I pulled out. I don’t think she came yet but she was right there. I went back to Jill. Told her to relax and I started to work my cock in. As I got half way in she slammed her face into the pillow and started to sob. I stopped, leaned forward and ask her if she was OK.

“Oh God that feel so great. My cunt hole is on fire. Are you all the way in yet.”


“Oh please give it to me. Give it to me slow but I want it all.”

I flexed my cock a few times to give her a chance to rest and then I went back to work. She was breathing deep. I felt that this could take a while so I put my hand on Ellen’s ass and took the liberty of sticking my finger first in her cunt and then up her butt. A low moan came from her direction. She was clearly approving this action.

Finally, I hit bottom. Jill was squirming and chanting “Give it to me… fuck me harder, Give it to me… fuck me harder” So, like a big stud I did. She came with a scream. I was still hard when I pulled out. I moved over to Ellen who was starting to beg for some dick. She said she was tied of the finger. I began to work myself back into her cunt when she stopped me.

“I need to take it up the ass. I love it that way.”

“I’m here to please, baby.”

Hot damn I was about to get my first piece of ass, literally!

I took it slow. It took a few minutes. I had my eyes closed as I was straining to get that last inch in. I only opened my eyes, I was surprised by Jill. She was on her back, between Ellen’s legs. What surprised me was her lickin my balls!!! She was taking turns lickin my balls and suckin Ellens driping cunt. Ellen was in heaven. I was giving her the long stroke treatment and Jill was giving her the small stroke treatment. I wasn’t long before we both blew. Jill must have been in that position before. She knew exactly when to roll out of the way. Ellen collapsed onto the bed Jill was not under her.

I rolled over and found myself between the two women. We were still for a bit. Then Jill reached down and started things up again. Once hard, Jill jumped on and road me like a champ. For a woman who didn’t know if she liked dick, she was putting dick thought the paces. Ellen was cheering her on to another explosive orgasm. Jill collapsed onto my chest. Ellen got behind Jill, pulled my cock out of her cunny and replaced it with her finger. She slid it in slow, Jill moaned, “I’m not ready yet”

“Relax” Ellen said “breathe deep” as she Glided her finger up and down her butt crack.

“Oh I like that”

“Hold on girl, what do you think about this.” Ellen push her finger past the brown star. Jill gasped but did not resist. ”I love it up the ass!!! You need to have some of that black dick up there.”

I couldn’t take it!!! It’s too BIG!!!

“Don’t worry I will warm you up to it. It will be fine” Ellen said as a second finger found it’s way up her butt Jill moaned again. As I heard this talk I could not believe that I was gonna get a second piece of ass and this time it was gonna be virgin butt. My dick started to rise to the occasion helped along by Ellen jaxin me off. A third finger found the mark. Jill was being slowly stretched I could see tension come and go from her face. I could feel Ellen bend my cock up to Jill’s entrance. Ellen whispered “ This will hurt if you don’t relax the head is the biggest part. Relax and breathe.” I felt the head knocking and in a second it was in. Jill was loud and tight. She wrapped her arms around me and held on tight. I didn’t move until the tension was gone from her face. I know I’m big so I wanted to be gentle. I knew that in this position I would not be able to slip my dick all the way in and I don’t know that for her first time she should have all I got. What I was giving her seemed to work. She was chanting and squirming her butt. What she was doing work for me as well. I could not hold back and I shot a load up her butt, she loved it and shook herself to another orgasm. I think she passed out I rolled her off me and once again found myself between the two women.

We slept for about four hours, When I woke up. Jill was gone, but she left a card. She was a bank president. I chuckled thinking about my late night deposit. Ellen was still with me. Needless to say we both missed our morning flight. We were busy. I was glad to have her by herself.

She told me that she did indeed jax off Stu in the taxi. She told him that that was to thanks him for all the drinks. When she got to this room and he invited her in she said no and asked him “what type of girl do you think I am”. She added “ I don’t fuck guys with tiny dicks”. We both had a laugh about that.

I still stay in touch with Jill and Ellen. I have not gotten back up that way but Ellen has been with Jill on a few occasions. They usually call me when they are together. They love to tell me how much they enjoyed my big dick. (The phone sex is great as well… They can get pretty raunchy). We are planning a get together to have a reunion soon… By the way Stu will not be invited.

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